WO2017073933A1 - Spiro-type compound and organic light emitting element comprising same - Google Patents

Spiro-type compound and organic light emitting element comprising same Download PDF

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WO2017073933A1
WO2017073933A1 PCT/KR2016/011421 KR2016011421W WO2017073933A1 WO 2017073933 A1 WO2017073933 A1 WO 2017073933A1 KR 2016011421 W KR2016011421 W KR 2016011421W WO 2017073933 A1 WO2017073933 A1 WO 2017073933A1
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group
substituted
unsubstituted
formula
compound
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PCT/KR2016/011421
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French (fr)
Korean (ko)
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차용범
김진주
서상덕
김정범
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주식회사 엘지화학
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Priority claimed from KR1020160130731A external-priority patent/KR102000177B1/en
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201680004811.6A priority Critical patent/CN107108408B/en
Priority to JP2017528787A priority patent/JP6443781B2/en
Priority to EP16860117.7A priority patent/EP3369719B1/en
Priority to US15/543,372 priority patent/US9960357B2/en
Publication of WO2017073933A1 publication Critical patent/WO2017073933A1/en

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • 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
    • C07C13/72—Spiro hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Definitions

  • the present specification relates to a spiro 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.
  • R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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
  • a is an integer of 0 to 10
  • b is an integer of 0 to 7
  • c is an integer from 0 to 5
  • d is an integer of 0 to 4,
  • an exemplary embodiment of the present specification includes a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound of Formula 1.
  • the compound described herein can be used as the material of the organic material layer of the organic light emitting device.
  • the compound according to at least one exemplary embodiment may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode.
  • the compounds described herein can be used as hole injection, hole transport, hole injection and hole transport, luminescence, electron transport, or electron injection materials.
  • the compounds described herein can be preferably used as the light emitting layer, electron transport or electron injection material. Further, more preferably, the compound described herein exhibits low voltage, high efficiency and / or long life when used as a material for hole injection, hole transport, and electron suppression layer.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG.
  • FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4. It is.
  • An exemplary embodiment of the present specification provides a compound represented by Chemical Formula 1.
  • substituted or unsubstituted is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amine groups; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; A silyl group unsubstituted or substituted with an alkyl group; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; And it is substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group, or substituted or unsubstituted
  • 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.
  • substituted or unsubstituted is preferably deuterium; Halogen group; Nitrile group; Alkyl groups; Trimethylsilyl group; Aryl group; And it may mean substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group.
  • adjacent means a substituent substituted on an atom directly connected to an atom to which the substituent is substituted, a substituent positioned closest to the substituent, or another substituent substituted on an atom to which the substituent is substituted.
  • two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" to each other.
  • carbon number of a carbonyl group 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 may be represented by the formula of -SiRR'R '', wherein R, R 'and R' 'are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • Specific examples of the silyl group include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. It doesn't happen.
  • the boron group may be represented by the formula of -BRR ', wherein R and R' are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • the boron group is specifically trimethyl boron group, triethyl boron group, t-butyl dimethyl boron group, triphenyl boron group, phenyl boron group and the like, but is not limited thereto.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • 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.
  • the alkoxy group is not particularly limited, but is preferably 1 to 40 carbon atoms. According to an exemplary embodiment, the alkoxy group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkoxy group has 1 to 6 carbon atoms. Specific examples of the alkoxy group include, but are not limited to, methoxy group, ethoxy group, propoxy group, isobutyloxy group, sec-butyloxy group, pentyloxy group, iso-amyloxy group, hexyloxy group, and the like.
  • the amine group is not particularly limited, but is preferably 1 to 30.
  • Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methylanthracenylamine group, Diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group and the like, but is not limited thereto.
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group.
  • the aryl group in the arylamine group may be a monocyclic aryl group, may be a polycyclic aryl group.
  • the arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
  • aryl amine group examples include phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 3-methylphenylamine group, 4-methylnaphthylamine group, 2-methylbiphenylamine group, 9- Methyl anthracenylamine group, diphenyl amine group, phenylnaphthyl amine group, ditolyl amine group, phenyltolyl amine group, carbazole and triphenyl amine group and the like, but are not limited thereto.
  • examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group.
  • the heteroaryl group in the heteroarylamine group may be a monocyclic heterocyclic group or may be a polycyclic heterocyclic group.
  • the heteroarylamine group including two or more heterocyclic groups may include a monocyclic heterocyclic group, a polycyclic heterocyclic group, or a monocyclic heterocyclic group and a polycyclic heterocyclic group.
  • the arylheteroarylamine group means an amine group substituted with an aryl group and a heterocyclic group.
  • examples of the arylphosphine group include a substituted or unsubstituted monoarylphosphine group, a substituted or unsubstituted diarylphosphine group, or a substituted or unsubstituted triarylphosphine group.
  • the aryl group in the arylphosphine group may be a monocyclic aryl group, may be a polycyclic aryl group.
  • the arylphosphine group containing two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
  • 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 monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, peryleneyl group, chrysenyl group, fluorenyl group, triphenylene group, etc., 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 including 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, carbazo
  • heteroaryl group is aromatic
  • the aryl group in the aryloxy group, arylthioxy group, aryl sulfoxy group, aryl phosphine group, aralkyl group, aralkylamine group, aralkenyl group, alkylaryl group, arylamine group, arylheteroarylamine group is described above.
  • the description of one aryl group may apply.
  • the alkyl group among the alkyl thioxy group, the alkyl sulfoxy group, the aralkyl group, the aralkyl amine group, the alkyl aryl group, and the alkyl amine group may be described with respect to the alkyl group described above.
  • heteroaryl group a heteroarylamine group, and an arylheteroarylamine group among the heteroaryl group may be applied to the description of the aforementioned heterocyclic group.
  • alkenyl group of the alkenyl group may be applied to the description of the alkenyl group described above.
  • the description of the aryl group described above may be applied except that the arylene group is a divalent group.
  • heteroarylene group 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; Substituted or unsubstituted aromatic heterocycle; Or to form a condensed ring thereof.
  • 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 a phenyl group, naphthyl group, anthracenyl group, and the like, but are not limited thereto.
  • 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.
  • Ar 1, Ar 2, R 5 and R 6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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
  • a in Formula 1 is 1 to 10, at least one of R1 is represented by-(L) m-A, L is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group, m is an integer from 1 to 10, and A is -NAr1Ar2.
  • a in Formula 1 is 1 or 2, at least one of R1 is represented by-(L) m-A, L is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group, m is an integer of 1 to 2, A is -NAr1Ar2.
  • Formula 1 may be represented by the following formula (2).
  • R11 is defined as R1 to R4,
  • L is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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
  • p is an integer from 1 to 10
  • f is an integer of 0 to 10
  • n 1 to 10
  • Chemical Formula 1 may be represented by the following Chemical Formula 3 or 4.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar1 to Ar4, Y1 and Y2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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 ary
  • y1 is an integer of 0 to 9
  • y2 is an integer of 0 to 8
  • n1 and m2 are the same as or different from each other, and each independently an integer of 1 to 10,
  • Chemical Formula 1 may be represented by any one of the following Chemical Formulas 5 to 8.
  • L 1 is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar1, Ar2 and Y1 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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 sul
  • y1 is an integer of 0 to 9
  • n1 and m2 are the same as or different from each other, and each independently an integer of 1 to 10,
  • Chemical Formula 1 may be represented by any one of the following Chemical Formulas 9 to 12.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar1 to Ar4 and Y2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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 s
  • y2 is an integer of 0 to 8
  • n1 and m2 are the same as or different from each other, and each independently an integer of 1 to 10,
  • Chemical Formula 1 may be represented by the following Chemical Formula 13 or 14.
  • R11 is the same as the definition of R2 to R4,
  • L, L11 and L21 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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
  • p is an integer from 1 to 10
  • f is an integer of 0 to 10
  • n 1 to 10
  • the L, L1, L2, L11 and L12 are the same as or different from each other, each independently a direct bond; Or a substituted or unsubstituted 1 to 5 ring arylene group.
  • the L, L1, L2, L11 and L12 are the same as or different from each other, each independently a direct bond; Or a substituted or unsubstituted 1 to 4 ring arylene group.
  • the L, L1, L2, L11 and L12 are the same as or different from each other, each independently a direct bond; Or a substituted or unsubstituted arylene group.
  • the L, L1, L2, L11 and L12 are the same as or different from each other, each independently a direct bond; Substituted or unsubstituted phenylene group; A substituted or unsubstituted bivalent biphenyl group; A substituted or unsubstituted divalent terphenyl group; A substituted or unsubstituted divalent quarterphenyl group; A substituted or unsubstituted divalent naphthyl group; Substituted or unsubstituted divalent anthracenyl group; A substituted or unsubstituted divalent fluorenyl group; Substituted or unsubstituted divalent phenanthryl group; A substituted or unsubstituted divalent pyrenyl group; Or a substituted or unsubstituted divalent crysenyl group.
  • the L, L1, L2, L11 and L12 are the same as or different from each other, each independently a direct bond; Phenylene group; Divalent biphenyl group; Divalent terphenyl group; Divalent quarterphenyl group; Divalent naphthyl group; Divalent anthracenyl group; Divalent fluorenyl group; Divalent phenanthryl group; Divalent pyrenyl group; Or a divalent crysenyl group.
  • L, L1, L2, L11 and L12 are the same as or different from each other, each independently represent a substituted or unsubstituted hetero arylene group.
  • the L, L1, L2, L11 and L12 are the same as or different from each other, each independently a direct bond; Or any one selected from the following structures.
  • A1 and A2 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may combine with each other to form a substituted or unsubstituted ring,
  • the structures are deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; And it may be substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group.
  • the L, L1, L2, L11 and L12 are the same as or different from each other, each independently may be any one selected from a direct bond or the following structures.
  • A1 and A2 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may combine with each other to form a substituted or unsubstituted ring,
  • the structures are deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; And it may be substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group.
  • the L, L1, L2, L11 and L12 are the same as or different from each other, each independently may be any one selected from a direct bond or the following structures.
  • A1 and A2 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may combine with each other to form a substituted or unsubstituted ring,
  • the structures are deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; And it may be substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group.
  • the L, L1, L2, L11 and L12 are the same as or different from each other, each independently a direct bond; Phenylene group; Biphenylylene group; Or a fluorenylene group.
  • Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  • Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group including at least one of N, O, and S.
  • Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, each independently substituted or unsubstituted 1 to 10 ring aryl group; Or a substituted or unsubstituted 1 to 10 ring heterocyclic group.
  • Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently substituted or unsubstituted 1 to 9 ring aryl groups; Or a substituted or unsubstituted 1 to 6 ring heterocyclic group.
  • Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group.
  • Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and are each independently a substituted or unsubstituted 1 to 6 ring aryl group.
  • Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently deuterium, halogen, nitrile, nitro, hydroxy, carbonyl, ester, Imide group, amine group, phosphine oxide group, alkoxy group, aryloxy group, alkylthioxy group, arylthioxy group, alkyl sulfoxy group, aryl sulfoxy group, silyl group, boron group, alkyl group, cycloalkyl group, alkenyl group, aryl group Or an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamine group, an aralkylamine group, a heteroarylamine group, an arylamine group, an arylphosphine group, and one or more substituents selected from the group consisting of heterocyclic groups Ring aryl group; Or deuterium,
  • Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted An aryl group unsubstituted or substituted with a substituent selected from the group consisting of a substituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; Or deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted
  • Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; A substituted or unsubstituted quarterphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted anthracenyl group; Substituted or unsubstituted chrysenyl group; Substituted or unsubstituted pyrenyl group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted triphenylene group; Or a substituted or unsubstituted phenanthryl group.
  • Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted A phenyl group unsubstituted or substituted with a substituent selected from the group consisting of a substituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; Deuterium, halogen group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, and substituted or unsubsti
  • Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted heterocyclic group.
  • Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted heterocyclic group including one or more of N, O and S to be.
  • Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted 1 to 6 ring heterocyclic group.
  • Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and are each independently a substituted or unsubstituted 1 to 5 ring heterocyclic group.
  • Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to tetracyclic heterocyclic group.
  • Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted 2 to 6 ring heterocyclic group.
  • Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted 3 to 6 ring heterocyclic group.
  • Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted thiophene group; Substituted or unsubstituted furan group; Substituted or unsubstituted pyrrole group; Substituted or unsubstituted imidazole group; Substituted or unsubstituted thiazole group; Substituted or unsubstituted oxazole group; Substituted or unsubstituted oxadiazole group; Substituted or unsubstituted triazole group; Substituted or unsubstituted pyridyl group; Substituted or unsubstituted bipyridyl group; Substituted or unsubstituted pyrimidyl group; Substituted or unsubstituted or unsubstituted thi
  • Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a thiophene group; Furan groups; Pyrrole group; Imidazole group; Thiazole group; Oxazole group; Oxadiazole group; Triazole groups; Pyridyl group; Bipyridyl group; Pyrimidyl groups; Triazine group; Triazole groups; Acridil group; Pyridazine groups; Pyrazinyl group; Quinolinyl group; Quinazoline group; Quinoxalinyl group; Phthalazinyl group; Pyrido pyrimidinyl groups; Pyrido pyrazinyl groups; Pyrazino pyrazinyl group; Isoquinoline group; Indole; Carbazole groups; Benzoxazole group; Benzimidazole groups; Benzothiazole group; Benzocarbazole group; Benzothiophene
  • Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted pyridyl group; Substituted or unsubstituted pyrimidyl group; Substituted or unsubstituted triazine group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted indolocarbazole group; Substituted or unsubstituted benzocarbazole group; Substituted or unsubstituted thiophene group; Substituted or unsubstituted furanyl group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted dibenzofuranyl group; Substituted or unsubstituted quinoline group; Substituted or
  • Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a pyridyl group; Pyrimidyl groups; Triazine group; Carbazole groups; Indolocarbazole groups; Benzocarbazole group; Thiophene group; Furanyl group; Dibenzothiophene group; Dibenzofuranyl group; Quinoline groups; Quinoxalinyl group; Quinazoline group; Phosphine oxide groups; Silyl groups; Bicyclic heterocyclic groups including at least one of N, S, and O; Tricyclic heterocyclic group containing two or more of N, O and S; Tetracyclic heterocyclic groups including at least one of S and O; Or a 5 or 6 ring heterocyclic group containing one or more N.
  • Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently deuterium, halogen, nitrile, alkyl, trimethylsilyl, aryl, and hetero An aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of a cyclic group; Or a heterocyclic group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a nitrile group, an alkyl group, a trimethylsilyl group, an aryl group, and a heterocyclic group.
  • Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a group consisting of a silyl group substituted with deuterium, a halogen group, a nitrile group, an alkyl group, and an alkyl group Phenyl group unsubstituted or substituted with one or more substituents selected from; Naphthyl group; Biphenyl group; Terphenyl group; Tetraphenyl group; A fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group; Phenanthryl group; Triphenylene group; Dibenzofuranyl group; Dibenzothiophene group; Carbazole groups unsubstituted or substituted with an aryl group; Or a benzocarbazole group unsubstituted or substituted with an aryl group.
  • Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; A substituted or unsubstituted quarterphenyl group; Substituted or unsubstituted 1-naphthyl group; Substituted or unsubstituted 2-naphthyl group; Substituted or unsubstituted 2-fluorenyl group; Substituted or unsubstituted 3-fluorenyl group; Substituted or unsubstituted 4-fluorenyl group; Substituted or unsubstituted 2-phenanthryl group; Substituted or unsubstituted 3-phenanthryl group; Substituted
  • Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted 2-dibenzothiophene group; A substituted or unsubstituted 2-dibenzofuranyl group; Substituted or unsubstituted 4-dibenzofuranyl group; Substituted or unsubstituted N-carbazole group; Substituted or unsubstituted 1-carbazole group; Substituted or unsubstituted 2-carbazole group; Substituted or unsubstituted 3-carbazole group; A substituted or unsubstituted a-benzocarbazole group; Or a substituted or unsubstituted c-benzocarbazole group.
  • Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Quarter-phenyl group; 1-naphthyl group; 2-naphthyl group; 2-fluorenyl group; 3-fluorenyl group; 4-fluorenyl group; 2-phenanthryl group; Triphenylene group; 3-phenanthryl group; Or 9-phenanthryl group.
  • Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a 2-dibenzothiophene group; 2-dibenzofuranyl group; 4-dibenzofuranyl group; N-carbazole group; 1-carbazole group; 2-carbazole group; 3-carbazole group; a-benzocarbazole group; Or c-benzocarbazole group.
  • Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  • Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently deuterium, halogen, nitrile, alkyl, trimethylsilyl, aryl, and hetero An aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of a cyclic group; Or a heterocyclic group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a nitrile group, an alkyl group, a trimethylsilyl group, an aryl group, and a heterocyclic group.
  • Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a group consisting of a silyl group substituted with deuterium, a halogen group, a nitrile group, an alkyl group, and an alkyl group Phenyl group unsubstituted or substituted with one or more substituents selected from; Naphthyl group; Biphenyl group; Terphenyl group; Tetraphenyl group; A fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group; Phenanthryl group; Triphenylene group; Dibenzofuranyl group; Dibenzothiophene group; Carbazole groups unsubstituted or substituted with an aryl group; Or a benzocarbazole group unsubstituted or substituted with an aryl group.
  • Ar1 to Ar4, Ar11, Ar12, Ar21, and Ar22 may be the same as or different from each other, and may each independently be any one selected from the following structures.
  • the structures are deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; And it may be substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group.
  • the , , , or May be any one selected from the following structures.
  • the structures are deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; And it may be substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group.
  • the compound of Formula 1 may be any one selected from the following compounds.
  • the compound of Formula 1 may be any one selected from the following compounds.
  • the compound of Formula 1 may be any one selected from the following compounds.
  • the compound of Formula 1 may be any one selected from the following compounds.
  • a in Formula 1 is 1 or 2, at least one of R1 is represented by-(L) m-A, L is a direct bond; Substituted or unsubstituted arylene; Or substituted or unsubstituted heteroarylene, m is an integer of 1 to 2, A is -NAr1Ar2, and at least one of Ar1 and Ar2 is a substituted or unsubstituted carbazole group, or a substituted or unsubstituted benzocarbazole group And the rest are substituted or unsubstituted aryl groups or substituted or unsubstituted heteroaryl groups.
  • a in Formula 1 is 1 or 2, at least one of R1 is represented by-(L) m-A, L is a direct bond; Arylene; Or heteroarylene, m is an integer of 1 to 2, A is -NAr1Ar2, at least one of Ar1 and Ar2 is a carbazole group unsubstituted or substituted with an aryl group, or a benzocarbazole group unsubstituted or substituted with an aryl group And the rest are substituted or unsubstituted aryl groups.
  • the compound of Formula 1 may be any one selected from the following compounds.
  • a in Formula 1 is 1 to 10, at least one of R1 is represented by-(L) m-A, L is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group, m is an integer of 1 to 10, and A is a substituted or unsubstituted N-containing heterocyclic group.
  • a in Formula 1 is 1 or 2, at least one of R1 is represented by-(L) m-A, L is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group, m is 1 or 2, and A is a substituted or unsubstituted N-containing heterocyclic group.
  • a in Formula 1 is 1 or 2, at least one of R1 is represented by-(L) m-A, L is a direct bond; Or an arylene group having 6 to 20 carbon atoms, m is 1 or 2, and A is an N-containing heterocyclic group unsubstituted or substituted with an aryl group or a heterocyclic group.
  • a in Formula 1 is 1 or 2, at least one of R1 is represented by-(L) m-A, L is a direct bond; Or an arylene group having 6 to 20 carbon atoms, m is 1 or 2, and A is an N-containing heterocyclic group unsubstituted or substituted with an aryl group or a heterocyclic group, wherein the N-containing heterocyclic group is a triazine group, a pyrimidine group, It is a pyridine group, a quinazoline group, a quinoline group, an isoquinoline group, a benzimidazole group, a carbazole group, or a benzocarbazole group.
  • a in Formula 1 is 1 or 2, at least one of R1 is represented by-(L) m-A, L is a direct bond; Or an arylene group having 6 to 20 carbon atoms, m is 1 or 2, and A is an aryl group having 6 to 20 carbon atoms; Or an N-containing heterocyclic group unsubstituted or substituted with a heterocyclic group having 2 to 20 carbon atoms containing N, O or S, wherein the N-containing heterocyclic group is a triazine group, a pyrimidine group, a pyridine group, a quinazoline group, a quinoline Group, isoquinoline group, benzimidazole group, carbazole group, or benzocarbazole group.
  • a in Formula 1 is 1 or 2, at least one of R1 is represented by-(L) m-A, L is a direct bond; Phenylene group; Or a biphenylylene group, m is 1 or 2, and A is a benzocarba unsubstituted or substituted with a carbazole group, a phenyl group or a naphthyl group unsubstituted or substituted with a phenyl group, a naphthyl group, a biphenylyl group, a phenyl group or a naphthyl group N-containing heterocyclic group unsubstituted or substituted with a sol group, dibenzothiophene group, or dibenzofuran group, wherein the N-containing heterocyclic group is a triazine group, a pyrimidine group, a pyridine group, a quinazoline group, a quinoline group, an isoquinoline Group
  • the compound of Formula 1 may be any one selected from the following compounds.
  • the compound of Formula 1 may be any one selected from the following compounds.
  • the compound of Formula 1 may be any one selected from the following compounds.
  • a in Formula 1 is 1 or 2
  • at least one of R 1 is represented by-(L) mA
  • L is a phenylene group
  • m is 1 or 2
  • R5R6 and R5 and R6 are each a phenyl group.
  • the compound of Formula 1 may be any one selected from the following compounds.
  • a in Formula 1 is 1 to 10, at least one of R1 is represented by-(L) m-A, L is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group, m is an integer of 1 to 10, A is a substituted or unsubstituted anthracene group; Or an aryl group substituted with a halogen group or a nitrile group.
  • a in Formula 1 is 1 or 2, at least one of R1 is represented by-(L) m-A, L is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group, m is 1 or 2, A is a substituted or unsubstituted anthracene group; Or an aryl group substituted with a halogen group or a nitrile group.
  • a in Formula 1 is 1 or 2, at least one of R1 is represented by-(L) m-A, L is a direct bond; Arylene group; Or a heteroarylene group, m is 1 or 2, A is an anthracene group substituted with an aryl group unsubstituted or substituted with a halogen group or a nitrile group; Or an aryl group substituted with a halogen group or a nitrile group.
  • a in Formula 1 is 1 or 2, at least one of R1 is represented by-(L) m-A, L is a direct bond; Or an arylene group; m is 1 or 2, and A is an anthracene group substituted with an aryl group unsubstituted or substituted with a fluorine group or a nitrile group; Or an aryl group substituted with a fluorine group or a nitrile group.
  • a in Formula 1 is 1 or 2, at least one of R1 is represented by-(L) m-A, L is a direct bond; m is 1 or 2, A is an anthracene group substituted with a phenyl group unsubstituted or substituted with a nitrile group; Or a phenyl group substituted with a fluorine group or a nitrile group.
  • the compound of Formula 1 may be any one selected from the following compounds.
  • the compound represented by Chemical Formula 1 may be prepared based on the preparation examples described below.
  • Ar 1, Ar 2, Ar 3, and Ar 4 are defined as in Formula 1.
  • organic light emitting device including the compound represented by Formula 1.
  • the first electrode A second electrode provided to face the first electrode; And an organic light emitting device including at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound of Formula 1.
  • 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 injection layer, a hole transport layer, an electron suppression layer, a light emitting layer, a hole suppression layer, an electron transport layer, an electron injection layer and the like as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic material layers.
  • the organic material layer includes a hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting holes
  • the hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting holes is It includes a compound of formula (1).
  • the organic material layer includes an electron suppression layer, and the electron suppression layer includes the compound of Formula 1.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the compound of Formula 1.
  • the organic material layer includes a hole suppression layer, and the hole suppression layer includes the compound of Formula 1.
  • the electron transport layer, the electron injection layer or the layer at the same time the electron transport and electron injection comprises a compound of the formula (1).
  • the organic material layer includes a light emitting layer and an electron transport layer
  • the electron transport layer includes the compound of Formula 1.
  • the first electrode A second electrode provided to face the first electrode; And a light emitting layer provided between the first electrode and the second electrode.
  • An organic light emitting device including two or more organic material layers provided between the light emitting layer and the first electrode or between the light emitting layer and the second electrode, wherein at least one of the two or more organic material layers includes the compound.
  • two or more organic material layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer for simultaneously transporting electrons and electron injection, and a hole suppression layer.
  • the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the compound.
  • the compound may be included in one layer of the two or more electron transport layers, and may be included in each of the two or more electron transport layers.
  • 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 diode may be an organic light emitting diode having an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • FIGS. 1 and 2 For example, the structure of an organic light emitting diode according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 and 2.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG. In such a structure, the compound may be included in the light emitting layer.
  • the compound may be included in one or more layers of the hole injection layer, hole transport layer, light emitting layer and electron transport layer.
  • the organic material layer includes a light emitting layer
  • the light emitting layer may include a compound represented by the following Formula 15.
  • z1 is an integer of 1 or more, and if z1 is an integer of 2 or more, the structures in parentheses are the same or different from each other,
  • Ar100 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 higher chrysene group,
  • L100 is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • R100 and R101 are the same as or different from each other, and each independently 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 heterocyclic 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 15 as a dopant of the light emitting layer.
  • the L100 is a direct bond.
  • z1 is 2.
  • Ar100 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.
  • Ar100 is a divalent pyrene group unsubstituted or substituted with deuterium, methyl, ethyl, iso-propyl or tert-butyl groups.
  • Ar100 is a divalent pyrene group.
  • R100 and R101 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • R100 and R101 are the same as or different from each other, and each independently deuterium, alkyl, nitrile, aryl, alkylsilyl, or alkyl germanium group unsubstituted or substituted with 6 to 60 carbon atoms Aryl group; Or a heterocyclic 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 alkylgermanium group.
  • R100 and R101 are the same as or different from each other, and each independently deuterium, methyl, ethyl, iso-propyl, tert-butyl, nitrile, phenyl, trimethylsilyl or trimethylgernium
  • R100 and R101 are the same as or different from each other, and each independently deuterium, methyl, ethyl, iso-propyl, tert-butyl, nitrile, phenyl, trimethylsilyl or trimethylgernium
  • Terphenyl groups unsubstituted or substituted with deuterium, methyl, ethyl, iso-propyl, tert-butyl, nitrile, phenyl, trimethylsilyl or trimethylgermanium groups;
  • R100 and R101 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a trimethylgermanium group.
  • the R100 is a phenyl group.
  • R101 is a phenyl group substituted with a trimethylgermanium group.
  • Formula 15 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 formula (16).
  • Ar101 and Ar102 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • L101 and L102 are the same as or different from each other, and are each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • R102 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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 alken
  • z2 and z3 are the same as or different from each other, and each independently an integer of 1 or 2, z4 is an integer of 0 to 8, when z2 to z4 is 2 or more, the substituents in parentheses are the same or different from each other,
  • v is an integer of 1 or more, and when v is an integer of 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 16 as a host of the light emitting layer.
  • Ar101 and Ar102 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • Ar101 and Ar102 are the same as or different from each other, and each independently an aryl group having 6 to 60 carbon atoms unsubstituted or substituted with an alkyl group, an aryl group or a heterocyclic group; Or a heterocyclic group having 2 to 60 carbon atoms unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group.
  • Ar101 and Ar102 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an aryl group or heterocyclic group; A biphenyl group unsubstituted or substituted with an aryl group or a heterocyclic group; Terphenyl groups unsubstituted or substituted with an aryl group or a heterocyclic group; A naphthyl group unsubstituted or substituted with an aryl group or a heterocyclic group; A fluorene group unsubstituted or substituted with an alkyl group, an aryl group or a heterocyclic group; Phenanthrene groups unsubstituted or substituted with an aryl group or a heterocyclic group; Or a triphenylene group unsubstituted or substituted with an aryl group or a heterocyclic group.
  • Ar101 and Ar102 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; A fluorene group unsubstituted or substituted with a methyl group or a phenyl group; Phenanthrene group; Or a triphenylene group.
  • Ar101 is a 2-naphthyl group.
  • Ar102 is a 1-naphthyl group.
  • the L101 and L102 are the same as or different from each other, and each independently a direct bond; Phenylene group; Or a naphthylene group.
  • L101 is a phenylene group.
  • L102 is a direct bond.
  • R102 is hydrogen
  • z2 is 1.
  • v is 2.
  • Formula 16 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 15 as a dopant of the light emitting layer
  • the compound represented by Chemical Formula 16 as a host of the light emitting layer.
  • 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 is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode and the second electrode is an anode.
  • the anode material a material having a large work function is usually preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the 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 the electrode, and has a capability of transporting holes to the hole injection material, and has a hole injection effect at the anode, an excellent hole injection effect to the light emitting layer or the light emitting material, and is produced in the light emitting layer
  • 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.
  • the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer.
  • the hole transport material is a material capable of transporting holes from an anode or a hole injection layer and transferring 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, benzothiazole 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 arylamine group, and include pyrene, anthracene, chrysene, and periplanthene having an arylamine group, and a styrylamine compound may be substituted or unsubstituted.
  • At least one arylvinyl group is substituted with the 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 arylamine 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 arylamine group are substituted or unsubstituted.
  • styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like but is not limited thereto.
  • 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 that injects electrons from an electrode, has an ability to transport electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a 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 included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
  • a glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 ⁇ was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • ITO indium tin oxide
  • Fischer Co. product was used as a detergent
  • distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water.
  • ultrasonic washing was performed twice with distilled water for 10 minutes.
  • ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol dried and transported to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • hexanitrile hexaazatriphenylene (hexaazatriphenylene-hexanitrile: HAT) was thermally vacuum deposited to a thickness of 500 kPa on the prepared ITO transparent electrode to form a hole injection layer.
  • the following compound 1 was vacuum deposited to a film thickness of 100 kPa on the hole transport layer to form an electron suppression layer.
  • the light emitting layer was formed by vacuum depositing the following BH and BD in a weight ratio of 25: 1 on the electron suppressing layer with a film thickness of 300 Pa.
  • Compound ET1 and compound LiQ were vacuum-deposited on the emission layer at a weight ratio of 1: 1 to form an electron injection and transport layer at a thickness of 300 kPa.
  • lithium fluoride (LiF) and aluminum were deposited to a thickness of 12 kPa in order to form a cathode.
  • the organic light emitting device was manufactured by maintaining 7 to 5 ⁇ 10 ⁇ 6 torr.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 3 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 4 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 5 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 6 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 7 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 8 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 15 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 16 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 17 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 18 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 19 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 20 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 21 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 22 was used instead of compound 1 in Experimental Example 1-1.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1-1 except for using the following EB 1 (TCTA) instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that EB 2 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device of Experimental Examples 1-1 to 1-16 using the compound represented by Chemical Formula 1 according to the present invention as an electron suppressing layer in an organic light emitting device is a comparative example using conventional TCTA. 1, it was found that the characteristics of the lower voltage, higher efficiency than Comparative Example 2 having a core structure similar to the general formula (1) of the present invention.
  • the compound of Chemical Formula 1 according to the present invention was excellent in electron suppression ability, showed low voltage and high efficiency, and could be applied to an organic light emitting device.
  • a green organic light emitting device was manufactured by the following method.
  • a glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 ⁇ was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • ITO indium tin oxide
  • Fischer Co. product was used as a detergent
  • distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water.
  • ultrasonic washing was performed twice with distilled water for 10 minutes.
  • ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol dried and transported to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 12 was used instead of compound 11 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 13 was used instead of compound 11 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 14 was used instead of compound 11 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 25 was used instead of compound 11 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 26 was used instead of compound 11 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 27 was used instead of compound 11 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 28 was used instead of compound 11 in Experimental Example 2-1.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 2-1 except for using the following GH 1 (CBP) instead of the compound 11 in Experimental Example 2-1.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 2-1 except for using the following GH 2 instead of the compound 11 in Experimental Example 2-1.

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Abstract

The present specification provides a spiro-type compound of chemical formula 1 and an organic light emitting element comprising the same.

Description

스피로형 화합물 및 이를 포함하는 유기 발광 소자Spiro compound and organic light emitting device comprising the same
본 출원은 2015년 10월 26일 한국특허청에 제출된 한국 특허 출원 제10-2015-0149014호 및 2016년 10월 10일 한국특허청에 제출된 한국 특허 출원 제10-2016-0130731호의 출원일의 이익을 주장하며, 그 내용 전부는 본 명세서에 포함된다.This application claims the benefits of the Korean Patent Application No. 10-2015-0149014 filed with the Korean Patent Office on October 26, 2015 and the Korean Patent Application No. 10-2016-0130731, which was filed on October 10, 2016 with the Korean Patent Office. Claim, all of which are hereby incorporated by reference.
본 명세서는 스피로형 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다.The present specification relates to a spiro 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 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 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 명세서에는 스피로형 화합물 및 이를 포함하는 유기 발광 소자가 기재된다.In this specification, a spiro compound and an organic light emitting device including the same are described.
본 명세서의 일 실시상태는 하기 화학식 1로 표시되는 화합물을 제공한다: An exemplary embodiment of the present specification provides a compound represented by Formula 1:
[화학식 1][Formula 1]
Figure PCTKR2016011421-appb-I000001
Figure PCTKR2016011421-appb-I000001
상기 화학식 1에 있어서, In Chemical Formula 1,
R1 내지 R4는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 치환 또는 비치환된 아민기; 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 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있고,R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may be combined with an adjacent group to form a substituted or unsubstituted ring,
a는 0 내지 10의 정수이며, a is an integer of 0 to 10,
b는 0 내지 7의 정수이고, b is an integer of 0 to 7,
c는 0 내지 5의 정수이며, c is an integer from 0 to 5,
d는 0 내지 4의 정수이고,d is an integer of 0 to 4,
a, b, c 및 d가 각각 2 이상인 경우 괄호 안의 구조는 서로 같거나 상이하다. When a, b, c and d are each 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 제공한다.In addition, an exemplary embodiment of the present specification includes a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound of Formula 1.
본 명세서에 기재된 화합물은 유기 발광 소자의 유기물층의 재료로서 사용될 수 있다. 적어도 하나의 실시상태에 따른 화합물은 유기 발광 소자에서 효율의 향상, 낮은 구동전압 및/또는 수명 특성을 향상시킬 수 있다. 특히, 본 명세서에 기재된 화합물은 정공주입, 정공수송, 정공주입과 정공수송, 발광, 전자수송, 또는 전자주입 재료로 사용될 수 있다. 또한, 본 명세서에 기재된 화합물은 바람직하게는 발광층, 전자수송 또는 전자주입 재료로 사용될 수 있다. 또한, 보다 바람직하게는 본 명세서에 기재된 화합물은 정공주입, 정공수송, 전자억제층의 재료로 사용하는 경우 저전압, 고효율 및/또는 장수명의 특성을 나타낸다.The compound described herein can be used as the material of the organic material layer of the organic light emitting device. The compound according to at least one exemplary embodiment may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode. In particular, the compounds described herein can be used as hole injection, hole transport, hole injection and hole transport, luminescence, electron transport, or electron injection materials. In addition, the compounds described herein can be preferably used as the light emitting layer, electron transport or electron injection material. Further, more preferably, the compound described herein exhibits low voltage, high efficiency and / or long life when used as a material for hole injection, hole transport, and electron suppression layer.
도 1은 기판(1), 양극(2), 발광층(3), 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG.
도 2는 기판 (1), 양극(2), 정공주입층(5), 정공수송층(6), 발광층(7), 전자수송층(8) 및 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4. It is.
<부호의 설명><Description of the code>
1: 기판1: substrate
2: 양극2: anode
3: 발광층3: light emitting layer
4: 음극4: cathode
5: 정공주입층5: hole injection layer
6: 정공수송층6: hole transport layer
7: 전자수송층7: 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 명세서에 있어서, "치환 또는 비치환된"이라는 용어는 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 아민기; 포스핀옥사이드기; 알콕시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 알킬기로 치환 또는 비치환된 실릴기; 붕소기; 알킬기; 시클로알킬기; 알케닐기; 아릴기; 아르알킬기; 아르알케닐기; 알킬아릴기; 알킬아민기; 아랄킬아민기; 헤테로아릴아민기; 아릴아민기; 아릴포스핀기; 및 헤테로고리기로 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.In the present specification, the term "substituted or unsubstituted" is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amine groups; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; A silyl group unsubstituted or substituted with an alkyl group; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; And it is substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic 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, "치환 또는 비치환된"이라는 표현은 바람직하게는 중수소; 할로겐기; 니트릴기; 알킬기; 트리메틸실릴기; 아릴기; 및 헤테로고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환된 것을 의미할 수 있다. In the present specification, the expression "substituted or unsubstituted" is preferably deuterium; Halogen group; Nitrile group; Alkyl groups; Trimethylsilyl group; Aryl group; And it may mean substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group.
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.As used herein, the term "adjacent" means a substituent substituted on an atom directly connected to an atom to which the substituent is substituted, a substituent positioned closest to the substituent, or another substituent substituted on an atom to which the substituent is substituted. 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, 카보닐기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 40인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In this specification, although carbon number of a carbonyl group 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 PCTKR2016011421-appb-I000002
Figure PCTKR2016011421-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 PCTKR2016011421-appb-I000003
Figure PCTKR2016011421-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 PCTKR2016011421-appb-I000004
Figure PCTKR2016011421-appb-I000004
본 명세서에 있어서, 실릴기는 -SiRR'R''의 화학식으로 표시될 수 있고, 상기 R, R' 및 R''는 각각 수소; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기일 수 있다. 상기 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the silyl group may be represented by the formula of -SiRR'R '', wherein R, R 'and R' 'are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. Specific examples of the silyl group include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. It doesn't happen.
본 명세서에 있어서, 붕소기는 -BRR' 의 화학식으로 표시될 수 있고, 상기 R 및 R'는 각각 수소; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기일 수 있다. 상기 붕소기는 구체적으로 트리메틸붕소기, 트리에틸붕소기, t-부틸디메틸붕소기, 트리페닐붕소기, 페닐붕소기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the boron group may be represented by the formula of -BRR ', wherein R and R' are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. The boron group is specifically trimethyl boron group, triethyl boron group, t-butyl dimethyl boron group, triphenyl boron group, phenyl boron group and the like, but is not limited thereto.
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 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, 이에 한정되는 것은 아니다.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, 이에 한정되는 것은 아니다.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 한정되는 것은 아니다.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, 알콕시기는 특별히 한정되지는 않으나, 탄소수 1 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알콕시기의 탄소수는 1 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알콕시기의 탄소수는 1 내지 6이다. 상기 알콕시기의 구체적인 예로는 메톡시기, 에톡시기, 프로폭시기, 이소부틸옥시기, sec-부틸옥시기, 펜틸옥시기, iso-아밀옥시기, 헥실옥시기 등이 있으나, 이에 한정되지 않는다. In the present specification, the alkoxy group is not particularly limited, but is preferably 1 to 40 carbon atoms. According to an exemplary embodiment, the alkoxy group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkoxy group has 1 to 6 carbon atoms. Specific examples of the alkoxy group include, but are not limited to, methoxy group, ethoxy group, propoxy group, isobutyloxy group, sec-butyloxy group, pentyloxy group, iso-amyloxy group, hexyloxy group, and the like.
본 명세서에 있어서, 아민기는 탄소수는 특별히 한정되지 않으나, 1 내지 30인 것이 바람직하다. 아민기의 구체적인 예로는 메틸아민기, 디메틸아민기, 에틸아민기, 디에틸아민기, 페닐아민기, 나프틸아민기, 비페닐아민기, 안트라세닐아민기, 9-메틸안트라세닐아민기, 디페닐아민기, 페닐나프틸아민기, 디톨릴아민기, 페닐톨릴아민기, 트리페닐아민기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the amine group is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methylanthracenylamine group, Diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group and the like, but is not limited thereto.
본 명세서에 있어서, 아릴아민기의 예로는 치환 또는 비치환된 모노아릴아민기, 치환 또는 비치환된 디아릴아민기, 또는 치환 또는 비치환된 트리아릴아민기가 있다. 상기 아릴아민기 중의 아릴기는 단환식 아릴기일 수 있고, 다환식 아릴기일 수 있다. 상기 2 이상의 아릴기를 포함하는 아릴아민기는 단환식 아릴기, 다환식 아릴기, 또는 단환식 아릴기와 다환식 아릴기를 동시에 포함할 수 있다.In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group, may be a polycyclic aryl group. The arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
아릴 아민기의 구체적인 예로는 페닐아민기, 나프틸아민기, 비페닐아민기, 안트라세닐아민기, 3-메틸페닐아민기, 4-메틸나프틸아민기, 2-메틸비페닐아민기, 9-메틸안트라세닐아민기, 디페닐 아민기, 페닐나프틸 아민기, 디톨릴 아민기, 페닐톨릴 아민기, 카바졸 및 트리페닐 아민기 등이 있으나, 이에 한정되는 것은 아니다.Specific examples of the aryl amine group include phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 3-methylphenylamine group, 4-methylnaphthylamine group, 2-methylbiphenylamine group, 9- Methyl anthracenylamine group, diphenyl amine group, phenylnaphthyl amine group, ditolyl amine group, phenyltolyl amine group, carbazole and triphenyl amine group and the like, but are not limited thereto.
본 명세서에 있어서, 헤테로아릴아민기의 예로는 치환 또는 비치환된 모노헤테로아릴아민기, 치환 또는 비치환된 디헤테로아릴아민기, 또는 치환 또는 비치환된 트리헤테로아릴아민기가 있다. 상기 헤테로아릴아민기 중의 헤테로아릴기는 단환식 헤테로고리기일 수 있고, 다환식 헤테로고리기일 수 있다. 상기 2 이상의 헤테로고리기를 포함하는 헤테로아릴아민기는 단환식 헤테로고리기, 다환식 헤테로고리기, 또는 단환식 헤테로고리기와 다환식 헤테로고리기를 동시에 포함할 수 있다. In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroaryl group in the heteroarylamine group may be a monocyclic heterocyclic group or may be a polycyclic heterocyclic group. The heteroarylamine group including two or more heterocyclic groups may include a monocyclic heterocyclic group, a polycyclic heterocyclic group, or a monocyclic heterocyclic group and a polycyclic heterocyclic group.
본 명세서에 있어서, 아릴헤테로아릴아민기는 아릴기 및 헤테로고리기로 치환된 아민기를 의미한다.In the present specification, the arylheteroarylamine group means an amine group substituted with an aryl group and a heterocyclic group.
본 명세서에 있어서, 아릴포스핀기의 예로는 치환 또는 비치환된 모노아릴포스핀기, 치환 또는 비치환된 디아릴포스핀기, 또는 치환 또는 비치환된 트리아릴포스핀기가 있다. 상기 아릴포스핀기 중의 아릴기는 단환식 아릴기일 수 있고, 다환식 아릴기일 수 있다. 상기 아릴기가 2 이상을 포함하는 아릴포스핀기는 단환식 아릴기, 다환식 아릴기, 또는 단환식 아릴기와 다환식 아릴기를 동시에 포함할 수 있다.In the present specification, examples of the arylphosphine group include a substituted or unsubstituted monoarylphosphine group, a substituted or unsubstituted diarylphosphine group, or a substituted or unsubstituted triarylphosphine group. The aryl group in the arylphosphine group may be a monocyclic aryl group, may be a polycyclic aryl group. The arylphosphine group containing two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
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 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트릴기, 파이레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기, 트리페닐렌기 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 monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, peryleneyl group, chrysenyl group, fluorenyl group, triphenylene group, etc., 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 PCTKR2016011421-appb-I000005
,
Figure PCTKR2016011421-appb-I000006
,
Figure PCTKR2016011421-appb-I000007
,
Figure PCTKR2016011421-appb-I000008
,
Figure PCTKR2016011421-appb-I000009
,
Figure PCTKR2016011421-appb-I000010
,
Figure PCTKR2016011421-appb-I000011
및
Figure PCTKR2016011421-appb-I000012
등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,
Figure PCTKR2016011421-appb-I000005
,
Figure PCTKR2016011421-appb-I000006
,
Figure PCTKR2016011421-appb-I000007
,
Figure PCTKR2016011421-appb-I000008
,
Figure PCTKR2016011421-appb-I000009
,
Figure PCTKR2016011421-appb-I000010
,
Figure PCTKR2016011421-appb-I000011
And
Figure PCTKR2016011421-appb-I000012
And so on. However, the present invention is not limited thereto.
본 명세서에 있어서, 헤테로 고리기는 이종원자로 N, O, S, Si 및 Se 중 1개 이상을 포함하는 헤테로 고리기로서, 탄소수는 특별히 한정되지 않으나 탄소수 2 내지 60인 것이 바람직하다. 헤테로 고리기의 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, 티아디아졸릴기, 벤조티아졸릴기, 페녹사지닐기, 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heterocyclic group is a heterocyclic group including 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, thiazolyl group, isoxazolyl group, thiadiazolyl group, benzothiazolyl group, phenoxazinyl group, phenothiazinyl group And dibenzofuranyl groups, and the like, but are not limited thereto.
본 명세서에 있어서, 헤테로아릴기는 방향족인 것을 제외하고는 전술한 헤테로 고리기에 관한 설명이 적용될 수 있다.In the present specification, the description of the aforementioned hetero ring group may be applied except that the heteroaryl group is aromatic.
본 명세서에 있어서, 아릴옥시기, 아릴티옥시기, 아릴술폭시기, 아릴포스핀기, 아르알킬기, 아랄킬아민기, 아르알케닐기, 알킬아릴기, 아릴아민기, 아릴헤테로아릴아민기 중의 아릴기는 전술한 아릴기에 관한 설명이 적용될 수 있다.In the present specification, the aryl group in the aryloxy group, arylthioxy group, aryl sulfoxy group, aryl phosphine group, aralkyl group, aralkylamine group, aralkenyl group, alkylaryl group, arylamine group, arylheteroarylamine group is described above. The description of one aryl group may apply.
본 명세서에 있어서, 알킬티옥시기, 알킬술폭시기, 아르알킬기, 아랄킬아민기, 알킬아릴기, 알킬아민기 중 알킬기는 전술한 알킬기에 관한 설명이 적용될 수 있다. In the present specification, the alkyl group among the alkyl thioxy group, the alkyl sulfoxy group, the aralkyl group, the aralkyl amine group, the alkyl aryl group, and the alkyl amine group may be described with respect to the alkyl group described above.
본 명세서에 있어서, 헤테로아릴기, 헤테로아릴아민기, 아릴헤테로아릴아민기 중 헤테로아릴기는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. In the present specification, a heteroaryl group, a heteroarylamine group, and an arylheteroarylamine group among the heteroaryl group may be applied to the description of the aforementioned heterocyclic group.
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, 아릴렌기는 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 group is a divalent group.
본 명세서에 있어서, 헤테로아릴렌기는 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 group 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; 치환 또는 비치환된 방향족 헤테로고리; 또는 이들의 축합고리를 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; Substituted or unsubstituted aromatic heterocycle; Or to form a condensed ring thereof.
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 a phenyl group, naphthyl group, anthracenyl group, and the like, but are not limited thereto.
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 명세서의 일 실시상태에 따르면, 상기 화학식 1의 a는 1 내지 10이고, R1 중 적어도 하나는 -(L)m-A로 표시되며, L은 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고, m은 1 내지 10의 정수이며, A는 -NAr1Ar2; 치환 또는 비치환된 N 함유 헤테로고리기; -P(=O)R5R6; 치환 또는 비치환된 안트라센기; 또는 할로겐 또는 니트릴기로 치환된 아릴기이다. 여기서, Ar1, Ar2, R5 및 R6는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 치환 또는 비치환된 아민기; 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 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다. According to an exemplary embodiment of the present specification, a of Formula 1 is 1 to 10, at least one of R1 is represented by-(L) mA, L is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group, m is an integer from 1 to 10, A is -NAr1Ar2; Substituted or unsubstituted N-containing heterocyclic group; -P (= 0) R5R6; Substituted or unsubstituted anthracene group; Or an aryl group substituted with a halogen or nitrile group. Wherein Ar 1, Ar 2, R 5 and R 6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 a는 1 내지 10이고, R1 중 적어도 하나는 -(L)m-A로 표시되며, L은 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고, m은 1 내지 10의 정수이며, A는 -NAr1Ar2이다.According to an exemplary embodiment of the present specification, a in Formula 1 is 1 to 10, at least one of R1 is represented by-(L) m-A, L is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group, m is an integer from 1 to 10, and A is -NAr1Ar2.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 a는 1 또는 2이고, R1 중 적어도 하나는 -(L)m-A로 표시되며, L은 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고, m은 1 내지 2의 정수이며, A는 -NAr1Ar2이다.According to an exemplary embodiment of the present specification, a in Formula 1 is 1 or 2, at least one of R1 is represented by-(L) m-A, L is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group, m is an integer of 1 to 2, A is -NAr1Ar2.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 2로 표시될 수 있다.According to an exemplary embodiment of the present specification, Formula 1 may be represented by the following formula (2).
[화학식 2][Formula 2]
Figure PCTKR2016011421-appb-I000013
Figure PCTKR2016011421-appb-I000013
상기 화학식 2에 있어서,In Chemical Formula 2,
R2 내지 R4, b, c 및 d의 정의는 화학식 1에서와 같고,Definitions of R2 to R4, b, c and d are the same as in formula (1),
R11의 정의는 R1 내지 R4와 같으며,R11 is defined as R1 to R4,
L은 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 치환 또는 비치환된 아민기; 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 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있으며,Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may be combined with an adjacent group to form a substituted or unsubstituted ring,
p는 1 내지 10의 정수이고,p is an integer from 1 to 10,
f는 0 내지 10의 정수이며,f is an integer of 0 to 10,
1 ≤ p+f ≤ 10이고,1 ≦ p + f ≦ 10,
m은 1 내지 10의 정수이며,m is an integer from 1 to 10,
p, f 및 m이 각각 2 이상인 경우 괄호 안의 구조는 서로 같거나 상이하다. When p, f and m are each 2 or more, the structures in parentheses are the same or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 3 또는 4로 표시될 수 있다.According to an exemplary embodiment of the present specification, Chemical Formula 1 may be represented by the following Chemical Formula 3 or 4.
[화학식 3][Formula 3]
Figure PCTKR2016011421-appb-I000014
Figure PCTKR2016011421-appb-I000014
[화학식 4][Formula 4]
Figure PCTKR2016011421-appb-I000015
Figure PCTKR2016011421-appb-I000015
상기 화학식 3 및 4에 있어서,In Chemical Formulas 3 and 4,
R2 내지 R4, b, c 및 d의 정의는 화학식 1에서와 같고,Definitions of R2 to R4, b, c and d are the same as in formula (1),
L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이며, L1 and L2 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar1 내지 Ar4, Y1 및 Y2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 치환 또는 비치환된 아민기; 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 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있고,Ar1 to Ar4, Y1 and Y2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may be combined with an adjacent group to form a substituted or unsubstituted ring,
y1은 0 내지 9의 정수이며, y1 is an integer of 0 to 9,
y2는 0 내지 8의 정수이고, y2 is an integer of 0 to 8,
m1 및 m2는 서로 같거나 상이하고, 각각 독립적으로 1 내지 10의 정수이며,m1 and m2 are the same as or different from each other, and each independently an integer of 1 to 10,
y1, y2, m1 및 m2가 각각 2 이상인 경우 괄호 안의 구조는 서로 같거나 상이하다. When y1, y2, m1 and m2 are each 2 or more, the structures in parentheses are the same or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 5 내지 8 중 어느 하나로 표시될 수 있다. According to an exemplary embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 5 to 8.
[화학식 5][Formula 5]
Figure PCTKR2016011421-appb-I000016
Figure PCTKR2016011421-appb-I000016
[화학식 6][Formula 6]
Figure PCTKR2016011421-appb-I000017
Figure PCTKR2016011421-appb-I000017
[화학식 7][Formula 7]
Figure PCTKR2016011421-appb-I000018
Figure PCTKR2016011421-appb-I000018
[화학식 8][Formula 8]
Figure PCTKR2016011421-appb-I000019
Figure PCTKR2016011421-appb-I000019
상기 화학식 5 내지 8에 있어서, In Chemical Formulas 5 to 8,
R2 내지 R4, b, c 및 d의 정의는 화학식 1에서와 같고, Definitions of R2 to R4, b, c and d are the same as in formula (1),
L1은 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이며, L 1 is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar1, Ar2 및 Y1는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 치환 또는 비치환된 아민기; 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 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있고,Ar1, Ar2 and Y1 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may be combined with an adjacent group to form a substituted or unsubstituted ring,
y1은 0 내지 9의 정수이며, y1 is an integer of 0 to 9,
m1 및 m2는 서로 같거나 상이하고, 각각 독립적으로 1 내지 10의 정수이며,m1 and m2 are the same as or different from each other, and each independently an integer of 1 to 10,
y1 및 m1이 각각 2 이상인 경우 괄호 안의 구조는 서로 같거나 상이하다.When y1 and m1 are each 2 or more, the structures in parentheses are the same or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 9 내지 12 중 어느 하나로 표시될 수 있다. According to an exemplary embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 9 to 12.
[화학식 9][Formula 9]
Figure PCTKR2016011421-appb-I000020
Figure PCTKR2016011421-appb-I000020
[화학식 10][Formula 10]
Figure PCTKR2016011421-appb-I000021
Figure PCTKR2016011421-appb-I000021
[화학식 11][Formula 11]
Figure PCTKR2016011421-appb-I000022
Figure PCTKR2016011421-appb-I000022
[화학식 12][Formula 12]
Figure PCTKR2016011421-appb-I000023
Figure PCTKR2016011421-appb-I000023
상기 화학식 9 내지 12에 있어서, In Chemical Formulas 9 to 12,
R2 내지 R4, b, c 및 d의 정의는 화학식 1에서와 같고, Definitions of R2 to R4, b, c and d are the same as in formula (1),
L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이며, L1 and L2 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar1 내지 Ar4 및 Y2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 치환 또는 비치환된 아민기; 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 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있고,Ar1 to Ar4 and Y2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may be combined with an adjacent group to form a substituted or unsubstituted ring,
y2는 0 내지 8의 정수이고, y2 is an integer of 0 to 8,
m1 및 m2는 서로 같거나 상이하고, 각각 독립적으로 1 내지 10의 정수이며,m1 and m2 are the same as or different from each other, and each independently an integer of 1 to 10,
y2, m1 및 m2가 각각 2 이상인 경우 괄호 안의 구조는 서로 같거나 상이하다.When y2, m1 and m2 are each 2 or more, the structures in parentheses are the same or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 13 또는 14로 표시될 수 있다. According to an exemplary embodiment of the present specification, Chemical Formula 1 may be represented by the following Chemical Formula 13 or 14.
[화학식 13][Formula 13]
Figure PCTKR2016011421-appb-I000024
Figure PCTKR2016011421-appb-I000024
[화학식 14][Formula 14]
Figure PCTKR2016011421-appb-I000025
Figure PCTKR2016011421-appb-I000025
상기 화학식 13 및 14에 있어서,In Chemical Formulas 13 and 14,
R2 내지 R4, b, c 및 d의 정의는 화학식 1과 같고,Definitions of R2 to R4, b, c and d is the same as in formula (1),
R11의 정의는 R2 내지 R4의 정의와 같고,The definition of R11 is the same as the definition of R2 to R4,
L, L11 및 L21은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L, L11 and L21 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 치환 또는 비치환된 아민기; 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 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있으며,Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may be combined with an adjacent group to form a substituted or unsubstituted ring,
p는 1 내지 10의 정수이고,p is an integer from 1 to 10,
f는 0 내지 10의 정수이며,f is an integer of 0 to 10,
1 ≤ p+f ≤ 10이고,1 ≦ p + f ≦ 10,
m, m11 및 m21은 서로 같거나 상이하고, 각각 독립적으로 1 내지 10의 정수이며,m, m11 and m21 are the same as or different from each other, and each independently an integer of 1 to 10,
p, f, m, m11 및 m21이 각각 2 이상인 경우 괄호 안의 구조는 서로 같거나 상이하다.When p, f, m, m11 and m21 are each 2 or more, the structures in parentheses are the same or different from each other.
본 발명의 일 실시상태에 따르면, 상기 L, L1, L2, L11 및 L12는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 치환 또는 비치환된 1환 내지 5환의 아릴렌기이다.According to an exemplary embodiment of the present invention, the L, L1, L2, L11 and L12 are the same as or different from each other, each independently a direct bond; Or a substituted or unsubstituted 1 to 5 ring arylene group.
본 발명의 일 실시상태에 따르면, 상기 L, L1, L2, L11 및 L12는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 치환 또는 비치환된 1환 내지 4환의 아릴렌기이다.According to an exemplary embodiment of the present invention, the L, L1, L2, L11 and L12 are the same as or different from each other, each independently a direct bond; Or a substituted or unsubstituted 1 to 4 ring arylene group.
본 발명의 일 실시상태에 따르면, 상기 L, L1, L2, L11 및 L12는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 치환 또는 비치환된 아릴렌기이다.According to an exemplary embodiment of the present invention, the L, L1, L2, L11 and L12 are the same as or different from each other, each independently a direct bond; Or a substituted or unsubstituted arylene group.
본 발명의 일 실시상태에 따르면, 상기 L, L1, L2, L11 및 L12는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 페닐렌기; 치환 또는 비치환된 2가의 바이페닐기; 치환 또는 비치환된 2가의 터페닐기; 치환 또는 비치환된 2가의 쿼터페닐기; 치환 또는 비치환된 2가의 나프틸기; 치환 또는 비치환된 2가의 안트라세닐기; 치환 또는 비치환된 2가의 플루오레닐기; 치환 또는 비치환된 2가의 페난트릴기; 치환 또는 비치환된 2가의 파이레닐기; 또는 치환 또는 비치환된 2가의 크라이세닐기이다.According to an exemplary embodiment of the present invention, the L, L1, L2, L11 and L12 are the same as or different from each other, each independently a direct bond; Substituted or unsubstituted phenylene group; A substituted or unsubstituted bivalent biphenyl group; A substituted or unsubstituted divalent terphenyl group; A substituted or unsubstituted divalent quarterphenyl group; A substituted or unsubstituted divalent naphthyl group; Substituted or unsubstituted divalent anthracenyl group; A substituted or unsubstituted divalent fluorenyl group; Substituted or unsubstituted divalent phenanthryl group; A substituted or unsubstituted divalent pyrenyl group; Or a substituted or unsubstituted divalent crysenyl group.
본 발명의 일 실시상태에 따르면, 상기 L, L1, L2, L11 및 L12는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 페닐렌기; 2가의 바이페닐기; 2가의 터페닐기; 2가의 쿼터페닐기; 2가의 나프틸기; 2가의 안트라세닐기; 2가의 플루오레닐기; 2가의 페난트릴기; 2가의 파이레닐기; 또는 2가의 크라이세닐기이다. According to an exemplary embodiment of the present invention, the L, L1, L2, L11 and L12 are the same as or different from each other, each independently a direct bond; Phenylene group; Divalent biphenyl group; Divalent terphenyl group; Divalent quarterphenyl group; Divalent naphthyl group; Divalent anthracenyl group; Divalent fluorenyl group; Divalent phenanthryl group; Divalent pyrenyl group; Or a divalent crysenyl group.
본 발명의 일 실시상태에 따르면, 상기 L, L1, L2, L11 및 L12는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 헤테로아릴렌기이다.According to an exemplary embodiment of the present invention, L, L1, L2, L11 and L12 are the same as or different from each other, each independently represent a substituted or unsubstituted hetero arylene group.
본 발명의 일 실시상태에 따르면, 상기 L, L1, L2, L11 및 L12는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 하기의 구조들 중에서 선택된 어느 하나일 수 있다.According to an exemplary embodiment of the present invention, the L, L1, L2, L11 and L12 are the same as or different from each other, each independently a direct bond; Or any one selected from the following structures.
Figure PCTKR2016011421-appb-I000026
Figure PCTKR2016011421-appb-I000026
상기 구조식에 있어서, In the above structural formula,
A1 및 A2는 서로 같거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있고,A1 and A2 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may combine with each other to form a substituted or unsubstituted ring,
상기 구조들은 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 치환 또는 비치환된 아민기; 포스핀옥사이드기; 알콕시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 알킬기; 시클로알킬기; 알케닐기; 아릴기; 아르알킬기; 아르알케닐기; 알킬아릴기; 알킬아민기; 아랄킬아민기; 헤테로아릴아민기; 아릴아민기; 아릴포스핀기; 및 헤테로고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환될 수 있다.The structures are deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; And it may be substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group.
본 발명의 일 실시상태에 따르면, 상기 L, L1, L2, L11 및 L12는 서로 같거나 상이하고, 각각 독립적으로 직접결합 또는 하기의 구조들 중에서 선택된 어느 하나일 수 있다. According to an exemplary embodiment of the present invention, the L, L1, L2, L11 and L12 are the same as or different from each other, each independently may be any one selected from a direct bond or the following structures.
Figure PCTKR2016011421-appb-I000027
Figure PCTKR2016011421-appb-I000027
상기 구조식에 있어서, In the above structural formula,
A1 및 A2는 서로 같거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있고,A1 and A2 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may combine with each other to form a substituted or unsubstituted ring,
상기 구조들은 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 치환 또는 비치환된 아민기; 포스핀옥사이드기; 알콕시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 알킬기; 시클로알킬기; 알케닐기; 아릴기; 아르알킬기; 아르알케닐기; 알킬아릴기; 알킬아민기; 아랄킬아민기; 헤테로아릴아민기; 아릴아민기; 아릴포스핀기; 및 헤테로고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환될 수 있다.The structures are deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; And it may be substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group.
본 발명의 일 실시상태에 따르면, 상기 L, L1, L2, L11 및 L12는 서로 같거나 상이하고, 각각 독립적으로 직접결합 또는 하기의 구조들 중에서 선택된 어느 하나일 수 있다. According to an exemplary embodiment of the present invention, the L, L1, L2, L11 and L12 are the same as or different from each other, each independently may be any one selected from a direct bond or the following structures.
Figure PCTKR2016011421-appb-I000028
Figure PCTKR2016011421-appb-I000028
Figure PCTKR2016011421-appb-I000029
Figure PCTKR2016011421-appb-I000029
상기 구조식에 있어서, In the above structural formula,
A1 및 A2는 서로 같거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있고,A1 and A2 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may combine with each other to form a substituted or unsubstituted ring,
상기 구조들은 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 치환 또는 비치환된 아민기; 포스핀옥사이드기; 알콕시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 알킬기; 시클로알킬기; 알케닐기; 아릴기; 아르알킬기; 아르알케닐기; 알킬아릴기; 알킬아민기; 아랄킬아민기; 헤테로아릴아민기; 아릴아민기; 아릴포스핀기; 및 헤테로고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환될 수 있다.The structures are deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; And it may be substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group.
본 발명의 일 실시상태에 따르면, 상기 L, L1, L2, L11 및 L12는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 페닐렌기; 비페닐릴렌기; 또는 플루오레닐렌기이다.According to an exemplary embodiment of the present invention, the L, L1, L2, L11 and L12 are the same as or different from each other, each independently a direct bond; Phenylene group; Biphenylylene group; Or a fluorenylene group.
본 발명의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.According to an exemplary embodiment of the present invention, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
본 발명의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 N, O 및 S 중 1 이상을 포함하는 치환 또는 비치환된 헤테로고리기이다.According to an exemplary embodiment of the present invention, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group including at least one of N, O, and S.
본 발명의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 1환 내지 10환의 아릴기; 또는 치환 또는 비치환된 1환 내지 10환의 헤테로고리기이다.According to an exemplary embodiment of the present invention, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, each independently substituted or unsubstituted 1 to 10 ring aryl group; Or a substituted or unsubstituted 1 to 10 ring heterocyclic group.
본 발명의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 1환 내지 9환의 아릴기; 또는 치환 또는 비치환된 1환 내지 6환의 헤테로고리기이다.According to an exemplary embodiment of the present invention, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently substituted or unsubstituted 1 to 9 ring aryl groups; Or a substituted or unsubstituted 1 to 6 ring heterocyclic group.
본 발명의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이다. According to an exemplary embodiment of the present invention, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group.
본 발명의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 1환 내지 6환의 아릴기이다.According to an exemplary embodiment of the present invention, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and are each independently a substituted or unsubstituted 1 to 6 ring aryl group.
본 명세서의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 중수소, 할로겐기, 니트릴기, 니트로기, 히드록시기, 카보닐기, 에스테르기, 이미드기, 아민기, 포스핀옥사이드기, 알콕시기, 아릴옥시기, 알킬티옥시기, 아릴티옥시기, 알킬술폭시기, 아릴술폭시기, 실릴기, 붕소기, 알킬기, 시클로알킬기, 알케닐기, 아릴기, 아르알킬기, 아르알케닐기, 알킬아릴기, 알킬아민기, 아랄킬아민기, 헤테로아릴아민기, 아릴아민기, 아릴포스핀기, 및 헤테로고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환된 아릴기; 또는 중수소, 할로겐기, 니트릴기, 니트로기, 히드록시기, 카보닐기, 에스테르기, 이미드기, 아민기, 포스핀옥사이드기, 알콕시기, 아릴옥시기, 알킬티옥시기, 아릴티옥시기, 알킬술폭시기, 아릴술폭시기, 실릴기, 붕소기, 알킬기, 시클로알킬기, 알케닐기, 아릴기, 아르알킬기, 아르알케닐기, 알킬아릴기, 알킬아민기, 아랄킬아민기, 헤테로아릴아민기, 아릴아민기, 아릴포스핀기, 및 헤테로고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환된 헤테로고리기이다.According to an exemplary embodiment of the present specification, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently deuterium, halogen, nitrile, nitro, hydroxy, carbonyl, ester, Imide group, amine group, phosphine oxide group, alkoxy group, aryloxy group, alkylthioxy group, arylthioxy group, alkyl sulfoxy group, aryl sulfoxy group, silyl group, boron group, alkyl group, cycloalkyl group, alkenyl group, aryl group Or an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamine group, an aralkylamine group, a heteroarylamine group, an arylamine group, an arylphosphine group, and one or more substituents selected from the group consisting of heterocyclic groups Ring aryl group; Or deuterium, halogen group, nitrile group, nitro group, hydroxy group, carbonyl group, ester group, imide group, amine group, phosphine oxide group, alkoxy group, aryloxy group, alkylthioxy group, arylthioxy group, alkyl sulfoxy group, Aryl sulfoxy group, silyl group, boron group, alkyl group, cycloalkyl group, alkenyl group, aryl group, aralkyl group, aralkenyl group, alkylaryl group, alkylamine group, aralkylamine group, heteroarylamine group, arylamine group, It is a heterocyclic group which is unsubstituted or substituted with at least one substituent selected from the group consisting of an arylphosphine group and a heterocyclic group.
본 발명의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 중수소, 할로겐기, 니트릴기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 포스핀옥사이드기, 치환 또는 비치환된 아릴기, 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택된 치환기로 치환 또는 비치환된 아릴기; 또는 중수소, 할로겐기, 니트릴기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 포스핀옥사이드기, 치환 또는 비치환된 아릴기, 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택된 치환기로 치환 또는 비치환된 헤테로고리기이다. According to an exemplary embodiment of the present invention, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted An aryl group unsubstituted or substituted with a substituent selected from the group consisting of a substituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; Or deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocycle It is a heterocyclic group unsubstituted or substituted with a substituent selected from the group consisting of groups.
본 발명의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 쿼터페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 안트라세닐기; 치환 또는 비치환된 크라이세닐기; 치환 또는 비치환된 파이레닐기; 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 트리페닐렌기; 또는 치환 또는 비치환된 페난트릴기이다. According to an exemplary embodiment of the present invention, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; A substituted or unsubstituted quarterphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted anthracenyl group; Substituted or unsubstituted chrysenyl group; Substituted or unsubstituted pyrenyl group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted triphenylene group; Or a substituted or unsubstituted phenanthryl group.
본 발명의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 중수소, 할로겐기, 니트릴기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 포스핀옥사이드기, 치환 또는 비치환된 아릴기, 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택된 치환기로 치환 또는 비치환된 페닐기; 중수소, 할로겐기, 니트릴기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 포스핀옥사이드기, 치환 또는 비치환된 아릴기, 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택된 치환기로 치환 또는 비치환된 바이페닐기; 중수소, 할로겐기, 니트릴기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 포스핀옥사이드기, 치환 또는 비치환된 아릴기, 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택된 치환기로 치환 또는 비치환된 나프틸기; 중수소, 할로겐기, 니트릴기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 포스핀옥사이드기, 치환 또는 비치환된 아릴기, 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택된 치환기로 치환 또는 비치환된 안트라세닐기; 중수소, 할로겐기, 니트릴기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 포스핀옥사이드기, 치환 또는 비치환된 아릴기, 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택된 치환기로 치환 또는 비치환된 크라이세닐기; 중수소, 할로겐기, 니트릴기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 포스핀옥사이드기, 치환 또는 비치환된 아릴기, 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택된 치환기로 치환 또는 비치환된 파이레닐기; 중수소, 할로겐기, 니트릴기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 포스핀옥사이드기, 치환 또는 비치환된 아릴기, 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택된 치환기로 치환 또는 비치환된 터페닐기; 중수소, 할로겐기, 니트릴기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 포스핀옥사이드기, 치환 또는 비치환된 아릴기, 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택된 치환기로 치환 또는 비치환된 쿼터페닐기; 중수소, 할로겐기, 니트릴기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 포스핀옥사이드기, 치환 또는 비치환된 아릴기, 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택된 치환기로 치환 또는 비치환된 페난트릴기; 중수소, 할로겐기, 니트릴기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 포스핀옥사이드기, 치환 또는 비치환된 아릴기, 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택된 치환기로 치환 또는 비치환된 트리페닐렌기; 또는 중수소, 할로겐기, 니트릴기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 포스핀옥사이드기, 치환 또는 비치환된 아릴기, 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택된 치환기로 치환 또는 비치환된 플루오레닐기이다.According to an exemplary embodiment of the present invention, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted A phenyl group unsubstituted or substituted with a substituent selected from the group consisting of a substituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; Deuterium, halogen group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, and substituted or unsubstituted heterocyclic group A biphenyl group unsubstituted or substituted with a substituent selected from the group consisting of; Deuterium, halogen group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, and substituted or unsubstituted heterocyclic group A naphthyl group unsubstituted or substituted with a substituent selected from the group consisting of: Deuterium, halogen group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, and substituted or unsubstituted heterocyclic group Anthracenyl group unsubstituted or substituted with a substituent selected from the group consisting of: Deuterium, halogen group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, and substituted or unsubstituted heterocyclic group A chrysenyl group unsubstituted or substituted with a substituent selected from the group consisting of: Deuterium, halogen group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, and substituted or unsubstituted heterocyclic group A pyrenyl group unsubstituted or substituted with a substituent selected from the group consisting of; Deuterium, halogen group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, and substituted or unsubstituted heterocyclic group Terphenyl group unsubstituted or substituted with a substituent selected from the group consisting of; Deuterium, halogen group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, and substituted or unsubstituted heterocyclic group A quarterphenyl group unsubstituted or substituted with a substituent selected from the group consisting of; Deuterium, halogen group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, and substituted or unsubstituted heterocyclic group A phenanthryl group unsubstituted or substituted with a substituent selected from the group consisting of; Deuterium, halogen group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, and substituted or unsubstituted heterocyclic group Triphenylene group unsubstituted or substituted with a substituent selected from the group consisting of; Or deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocycle It is a fluorenyl group unsubstituted or substituted with a substituent selected from the group consisting of groups.
본 발명의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 헤테로고리기이다.According to an exemplary embodiment of the present invention, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted heterocyclic group.
본 발명의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 N, O 및 S 중 1 이상을 포함하는 치환 또는 비치환된 헤테로고리기이다.According to an exemplary embodiment of the present invention, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted heterocyclic group including one or more of N, O and S to be.
본 발명의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 1환 내지 6환의 헤테로고리기이다.According to an exemplary embodiment of the present invention, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted 1 to 6 ring heterocyclic group.
본 발명의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 1환 내지 5환의 헤테로고리기이다.According to an exemplary embodiment of the present invention, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and are each independently a substituted or unsubstituted 1 to 5 ring heterocyclic group.
본 발명의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 1환 내지 4환의 헤테로고리기이다.According to an exemplary embodiment of the present invention, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to tetracyclic heterocyclic group.
본 발명의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 2환 내지 6환의 헤테로고리기이다.According to an exemplary embodiment of the present invention, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted 2 to 6 ring heterocyclic group.
본 발명의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 3환 내지 6환의 헤테로고리기이다.According to an exemplary embodiment of the present invention, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted 3 to 6 ring heterocyclic group.
본 발명의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 티오펜기; 치환 또는 비치환된 퓨란기; 치환 또는 비치환된 피롤기; 치환 또는 비치환된 이미다졸기; 치환 또는 비치환된 티아졸기; 치환 또는 비치환된 옥사졸기; 치환 또는 비치환된 옥사디아졸기; 치환 또는 비치환된 트리아졸기; 치환 또는 비치환된 피리딜기; 치환 또는 비치환된 비피리딜기; 치환 또는 비치환된 피리미딜기; 치환 또는 비치환된 트리아진기; 치환 또는 비치환된 트리아졸기; 치환 또는 비치환된 아크리딜기; 치환 또는 비치환된 피리다진기; 치환 또는 비치환된 피라지닐기; 치환 또는 비치환된 퀴놀리닐기; 치환 또는 비치환된 퀴나졸린기; 치환 또는 비치환된 퀴녹살리닐기; 치환 또는 비치환된 프탈라지닐기; 치환 또는 비치환된 피리도 피리미디닐기; 치환 또는 비치환된 피리도 피라지닐기; 치환 또는 비치환된 피라지노 피라지닐기; 치환 또는 비치환된 이소퀴놀린기; 치환 또는 비치환된 인돌기; 치환 또는 비치환된 카바졸기; 치환 또는 비치환된 벤즈옥사졸기; 치환 또는 비치환된 벤즈이미다졸기; 치환 또는 비치환된 벤조티아졸기; 치환 또는 비치환된 벤조카바졸기; 치환 또는 비치환된 벤조티오펜기; 치환 또는 비치환된 디벤조티오펜기; 치환 또는 비치환된 벤조퓨라닐기; 치환 또는 비치환된 페난쓰롤린기(phenanthroline); 치환 또는 비치환된 이소옥사졸릴기; 치환 또는 비치환된 티아디아졸릴기; 치환 또는 비치환된 페노티아지닐기; 또는 치환 또는 비치환된 디벤조퓨라닐기이다. According to an exemplary embodiment of the present invention, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted thiophene group; Substituted or unsubstituted furan group; Substituted or unsubstituted pyrrole group; Substituted or unsubstituted imidazole group; Substituted or unsubstituted thiazole group; Substituted or unsubstituted oxazole group; Substituted or unsubstituted oxadiazole group; Substituted or unsubstituted triazole group; Substituted or unsubstituted pyridyl group; Substituted or unsubstituted bipyridyl group; Substituted or unsubstituted pyrimidyl group; Substituted or unsubstituted triazine group; Substituted or unsubstituted triazole group; A substituted or unsubstituted acridil group; Substituted or unsubstituted pyridazine group; Substituted or unsubstituted pyrazinyl group; Substituted or unsubstituted quinolinyl group; Substituted or unsubstituted quinazoline group; Substituted or unsubstituted quinoxalinyl group; Substituted or unsubstituted phthalazinyl group; A substituted or unsubstituted pyrido pyrimidinyl group; A substituted or unsubstituted pyrido pyrazinyl group; A substituted or unsubstituted pyrazino pyrazinyl group; Substituted or unsubstituted isoquinoline group; Substituted or unsubstituted indole group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted benzoxazole group; Substituted or unsubstituted benzimidazole group; Substituted or unsubstituted benzothiazole group; Substituted or unsubstituted benzocarbazole group; Substituted or unsubstituted benzothiophene group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted benzofuranyl group; Substituted or unsubstituted phenanthroline; Substituted or unsubstituted isoxazolyl group; Substituted or unsubstituted thiadiazolyl group; Substituted or unsubstituted phenothiazinyl group; Or a substituted or unsubstituted dibenzofuranyl group.
본 발명의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 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; 티아디아졸릴기; 페노티아지닐기; 또는 디벤조퓨라닐기이다. According to an exemplary embodiment of the present invention, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a thiophene group; Furan groups; Pyrrole group; Imidazole group; Thiazole group; Oxazole group; Oxadiazole group; Triazole groups; Pyridyl group; Bipyridyl group; Pyrimidyl groups; Triazine group; Triazole groups; Acridil group; Pyridazine groups; Pyrazinyl group; Quinolinyl group; Quinazoline group; Quinoxalinyl group; Phthalazinyl group; Pyrido pyrimidinyl groups; Pyrido pyrazinyl groups; Pyrazino pyrazinyl group; Isoquinoline group; Indole; Carbazole groups; Benzoxazole group; Benzimidazole groups; Benzothiazole group; Benzocarbazole group; Benzothiophene group; Dibenzothiophene group; Benzofuranyl group; Phenanthroline; Thiazolyl group; Isooxazolyl group; Thiadiazolyl group; Phenothiazinyl group; Or a dibenzofuranyl group.
본 발명의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 피리딜기; 치환 또는 비치환된 피리미딜기; 치환 또는 비치환된 트리아진기; 치환 또는 비치환된 카바졸기; 치환 또는 비치환된 인돌로카바졸기; 치환 또는 비치환된 벤조카바졸기; 치환 또는 비치환된 티오펜기; 치환 또는 비치환된 퓨라닐기; 치환 또는 비치환된 디벤조티오펜기; 치환 또는 비치환된 디벤조퓨라닐기; 치환 또는 비치환된 퀴놀린기; 치환 또는 비치환된 퀴녹살리닐기; 치환 또는 비치환된 퀴나졸린기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 실릴기; N, S 및 O 중 1 이상을 포함하는 2환의 치환 또는 비치환된 헤테로고리기; N, O 및 S 중 2 이상을 포함하는 3환의 치환 또는 비치환된 헤테로고리기; S 및 O 중 1 이상을 포함하는 4환의 치환 또는 비치환된 헤테로고리기; 또는 N을 1 이상 포함하는 5환 또는 6환의 치환 또는 비치환된 헤테로고리기이다. According to an exemplary embodiment of the present invention, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted pyridyl group; Substituted or unsubstituted pyrimidyl group; Substituted or unsubstituted triazine group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted indolocarbazole group; Substituted or unsubstituted benzocarbazole group; Substituted or unsubstituted thiophene group; Substituted or unsubstituted furanyl group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted dibenzofuranyl group; Substituted or unsubstituted quinoline group; Substituted or unsubstituted quinoxalinyl group; Substituted or unsubstituted quinazoline group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted silyl group; A bicyclic substituted or unsubstituted heterocyclic group including at least one of N, S, and O; A tricyclic substituted or unsubstituted heterocyclic group including two or more of N, O, and S; A tetracyclic substituted or unsubstituted heterocyclic group including at least one of S and O; Or a 5- or 6-ring substituted or unsubstituted heterocyclic group containing one or more N.
본 발명의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 피리딜기; 피리미딜기; 트리아진기; 카바졸기; 인돌로카바졸기; 벤조카바졸기; 티오펜기; 퓨라닐기; 디벤조티오펜기; 디벤조퓨라닐기; 퀴놀린기; 퀴녹살리닐기; 퀴나졸린기; 포스핀옥사이드기; 실릴기; N, S 및 O 중 1 이상을 포함하는 2환의 헤테로고리기; N, O 및 S 중 2 이상을 포함하는 3환의 헤테로고리기; S 및 O 중 1 이상을 포함하는 4환의 헤테로고리기; 또는 N을 1 이상 포함하는 5환 또는 6환의 헤테로고리기이다. According to an exemplary embodiment of the present invention, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a pyridyl group; Pyrimidyl groups; Triazine group; Carbazole groups; Indolocarbazole groups; Benzocarbazole group; Thiophene group; Furanyl group; Dibenzothiophene group; Dibenzofuranyl group; Quinoline groups; Quinoxalinyl group; Quinazoline group; Phosphine oxide groups; Silyl groups; Bicyclic heterocyclic groups including at least one of N, S, and O; Tricyclic heterocyclic group containing two or more of N, O and S; Tetracyclic heterocyclic groups including at least one of S and O; Or a 5 or 6 ring heterocyclic group containing one or more N.
본 발명의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 중수소, 할로겐기, 니트릴기, 알킬기, 트리메틸실릴기, 아릴기, 및 헤테로고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환된 아릴기; 또는 중수소, 할로겐기, 니트릴기, 알킬기, 트리메틸실릴기, 아릴기, 및 헤테로고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환된 헤테로고리기이다.According to an exemplary embodiment of the present invention, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently deuterium, halogen, nitrile, alkyl, trimethylsilyl, aryl, and hetero An aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of a cyclic group; Or a heterocyclic group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a nitrile group, an alkyl group, a trimethylsilyl group, an aryl group, and a heterocyclic group.
본 발명의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 중수소, 할로겐기, 니트릴기, 알킬기, 및 알킬기로 치환된 실릴기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환된 페닐기; 나프틸기; 바이페닐기; 터페닐기; 테트라페닐기; 알킬기 또는 아릴기로 치환 또는 비치환된 플루오레닐기; 페난트릴기; 트리페닐렌기; 디벤조퓨라닐기; 디벤조티오펜기; 아릴기로 치환 또는 비치환된 카바졸기; 또는 아릴기로 치환 또는 비치환된 벤조카바졸기이다.According to an exemplary embodiment of the present invention, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a group consisting of a silyl group substituted with deuterium, a halogen group, a nitrile group, an alkyl group, and an alkyl group Phenyl group unsubstituted or substituted with one or more substituents selected from; Naphthyl group; Biphenyl group; Terphenyl group; Tetraphenyl group; A fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group; Phenanthryl group; Triphenylene group; Dibenzofuranyl group; Dibenzothiophene group; Carbazole groups unsubstituted or substituted with an aryl group; Or a benzocarbazole group unsubstituted or substituted with an aryl group.
본 명세서의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 쿼터페닐기; 치환 또는 비치환된 1-나프틸기; 치환 또는 비치환된 2-나프틸기; 치환 또는 비치환된 2-플루오레닐기; 치환 또는 비치환된 3-플루오레닐기; 치환 또는 비치환된 4-플루오레닐기; 치환 또는 비치환된 2-페난트릴기; 치환 또는 비치환된 3-페난트릴기; 치환 또는 비치환된 트리페닐렌기; 또는 치환 또는 비치환된 9-페난트릴기이다. According to an exemplary embodiment of the present specification, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; A substituted or unsubstituted quarterphenyl group; Substituted or unsubstituted 1-naphthyl group; Substituted or unsubstituted 2-naphthyl group; Substituted or unsubstituted 2-fluorenyl group; Substituted or unsubstituted 3-fluorenyl group; Substituted or unsubstituted 4-fluorenyl group; Substituted or unsubstituted 2-phenanthryl group; Substituted or unsubstituted 3-phenanthryl group; Substituted or unsubstituted triphenylene group; Or a substituted or unsubstituted 9-phenanthryl group.
본 명세서의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 2-디벤조티오펜기; 치환 또는 비치환된 2-디벤조퓨라닐기; 치환 또는 비치환된 4-디벤조퓨라닐기; 치환 또는 비치환된 N-카바졸기; 치환 또는 비치환된 1-카바졸기; 치환 또는 비치환된 2-카바졸기; 치환 또는 비치환된 3-카바졸기; 치환 또는 비치환된 a-벤조카바졸기; 또는 치환 또는 비치환된 c-벤조카바졸기이다. According to an exemplary embodiment of the present specification, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted 2-dibenzothiophene group; A substituted or unsubstituted 2-dibenzofuranyl group; Substituted or unsubstituted 4-dibenzofuranyl group; Substituted or unsubstituted N-carbazole group; Substituted or unsubstituted 1-carbazole group; Substituted or unsubstituted 2-carbazole group; Substituted or unsubstituted 3-carbazole group; A substituted or unsubstituted a-benzocarbazole group; Or a substituted or unsubstituted c-benzocarbazole group.
본 명세서의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 페닐기; 바이페닐기; 터페닐기; 쿼터페닐기; 1-나프틸기; 2-나프틸기; 2-플루오레닐기; 3-플루오레닐기; 4-플루오레닐기; 2-페난트릴기; 트리페닐렌기; 3-페난트릴기; 또는 9-페난트릴기이다. According to an exemplary embodiment of the present specification, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Quarter-phenyl group; 1-naphthyl group; 2-naphthyl group; 2-fluorenyl group; 3-fluorenyl group; 4-fluorenyl group; 2-phenanthryl group; Triphenylene group; 3-phenanthryl group; Or 9-phenanthryl group.
본 명세서의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 2-디벤조티오펜기; 2-디벤조퓨라닐기; 4-디벤조퓨라닐기; N-카바졸기; 1-카바졸기; 2-카바졸기; 3-카바졸기; a-벤조카바졸기; 또는 c-벤조카바졸기이다.According to an exemplary embodiment of the present specification, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a 2-dibenzothiophene group; 2-dibenzofuranyl group; 4-dibenzofuranyl group; N-carbazole group; 1-carbazole group; 2-carbazole group; 3-carbazole group; a-benzocarbazole group; Or c-benzocarbazole group.
본 발명의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다. According to an exemplary embodiment of the present invention, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
본 발명의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 중수소, 할로겐기, 니트릴기, 알킬기, 트리메틸실릴기, 아릴기, 및 헤테로고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환된 아릴기; 또는 중수소, 할로겐기, 니트릴기, 알킬기, 트리메틸실릴기, 아릴기, 및 헤테로고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환된 헤테로고리기이다.According to an exemplary embodiment of the present invention, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently deuterium, halogen, nitrile, alkyl, trimethylsilyl, aryl, and hetero An aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of a cyclic group; Or a heterocyclic group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a nitrile group, an alkyl group, a trimethylsilyl group, an aryl group, and a heterocyclic group.
본 발명의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 중수소, 할로겐기, 니트릴기, 알킬기, 및 알킬기로 치환된 실릴기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환된 페닐기; 나프틸기; 바이페닐기; 터페닐기; 테트라페닐기; 알킬기 또는 아릴기로 치환 또는 비치환된 플루오레닐기; 페난트릴기; 트리페닐렌기; 디벤조퓨라닐기; 디벤조티오펜기; 아릴기로 치환 또는 비치환된 카바졸기; 또는 아릴기로 치환 또는 비치환된 벤조카바졸기이다. According to an exemplary embodiment of the present invention, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently a group consisting of a silyl group substituted with deuterium, a halogen group, a nitrile group, an alkyl group, and an alkyl group Phenyl group unsubstituted or substituted with one or more substituents selected from; Naphthyl group; Biphenyl group; Terphenyl group; Tetraphenyl group; A fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group; Phenanthryl group; Triphenylene group; Dibenzofuranyl group; Dibenzothiophene group; Carbazole groups unsubstituted or substituted with an aryl group; Or a benzocarbazole group unsubstituted or substituted with an aryl group.
본 발명의 일 실시상태에 따르면, 상기 Ar1 내지 Ar4, Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 하기의 구조들 중에서 선택된 어느 하나일 수 있다. According to an exemplary embodiment of the present invention, Ar1 to Ar4, Ar11, Ar12, Ar21, and Ar22 may be the same as or different from each other, and may each independently be any one selected from the following structures.
Figure PCTKR2016011421-appb-I000030
Figure PCTKR2016011421-appb-I000030
Figure PCTKR2016011421-appb-I000031
Figure PCTKR2016011421-appb-I000031
Figure PCTKR2016011421-appb-I000032
Figure PCTKR2016011421-appb-I000032
Figure PCTKR2016011421-appb-I000033
Figure PCTKR2016011421-appb-I000033
Figure PCTKR2016011421-appb-I000034
Figure PCTKR2016011421-appb-I000034
Figure PCTKR2016011421-appb-I000035
Figure PCTKR2016011421-appb-I000035
Figure PCTKR2016011421-appb-I000036
Figure PCTKR2016011421-appb-I000036
Figure PCTKR2016011421-appb-I000037
Figure PCTKR2016011421-appb-I000037
Figure PCTKR2016011421-appb-I000038
Figure PCTKR2016011421-appb-I000038
Figure PCTKR2016011421-appb-I000039
Figure PCTKR2016011421-appb-I000039
Figure PCTKR2016011421-appb-I000040
Figure PCTKR2016011421-appb-I000040
Figure PCTKR2016011421-appb-I000041
Figure PCTKR2016011421-appb-I000041
Figure PCTKR2016011421-appb-I000042
Figure PCTKR2016011421-appb-I000042
Figure PCTKR2016011421-appb-I000043
Figure PCTKR2016011421-appb-I000043
Figure PCTKR2016011421-appb-I000044
Figure PCTKR2016011421-appb-I000044
Figure PCTKR2016011421-appb-I000045
Figure PCTKR2016011421-appb-I000045
Figure PCTKR2016011421-appb-I000046
Figure PCTKR2016011421-appb-I000046
상기 구조들은 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 치환 또는 비치환된 아민기; 포스핀옥사이드기; 알콕시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 알킬기; 시클로알킬기; 알케닐기; 아릴기; 아르알킬기; 아르알케닐기; 알킬아릴기; 알킬아민기; 아랄킬아민기; 헤테로아릴아민기; 아릴아민기; 아릴포스핀기; 및 헤테로고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환될 수 있다.The structures are deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; And it may be substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group.
본 명세서의 일 실시상태에 따르면, 상기
Figure PCTKR2016011421-appb-I000047
,
Figure PCTKR2016011421-appb-I000048
,
Figure PCTKR2016011421-appb-I000049
, 또는
Figure PCTKR2016011421-appb-I000050
는 하기의 구조들 중에서 선택된 어느 하나일 수 있다.According to an exemplary embodiment of the present specification, the
Figure PCTKR2016011421-appb-I000047
,
Figure PCTKR2016011421-appb-I000048
,
Figure PCTKR2016011421-appb-I000049
, or
Figure PCTKR2016011421-appb-I000050
May be any one selected from the following structures.
Figure PCTKR2016011421-appb-I000051
Figure PCTKR2016011421-appb-I000051
Figure PCTKR2016011421-appb-I000052
Figure PCTKR2016011421-appb-I000052
Figure PCTKR2016011421-appb-I000053
Figure PCTKR2016011421-appb-I000053
Figure PCTKR2016011421-appb-I000054
Figure PCTKR2016011421-appb-I000054
Figure PCTKR2016011421-appb-I000055
Figure PCTKR2016011421-appb-I000055
Figure PCTKR2016011421-appb-I000056
Figure PCTKR2016011421-appb-I000056
Figure PCTKR2016011421-appb-I000057
Figure PCTKR2016011421-appb-I000057
Figure PCTKR2016011421-appb-I000058
Figure PCTKR2016011421-appb-I000058
Figure PCTKR2016011421-appb-I000059
Figure PCTKR2016011421-appb-I000059
Figure PCTKR2016011421-appb-I000060
Figure PCTKR2016011421-appb-I000060
Figure PCTKR2016011421-appb-I000061
Figure PCTKR2016011421-appb-I000061
Figure PCTKR2016011421-appb-I000062
Figure PCTKR2016011421-appb-I000062
Figure PCTKR2016011421-appb-I000063
Figure PCTKR2016011421-appb-I000063
Figure PCTKR2016011421-appb-I000064
Figure PCTKR2016011421-appb-I000064
Figure PCTKR2016011421-appb-I000065
Figure PCTKR2016011421-appb-I000065
Figure PCTKR2016011421-appb-I000066
Figure PCTKR2016011421-appb-I000066
상기 구조들은 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 치환 또는 비치환된 아민기; 포스핀옥사이드기; 알콕시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 알킬기; 시클로알킬기; 알케닐기; 아릴기; 아르알킬기; 아르알케닐기; 알킬아릴기; 알킬아민기; 아랄킬아민기; 헤테로아릴아민기; 아릴아민기; 아릴포스핀기; 및 헤테로고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환될 수 있다.The structures are deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; And it may be substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 화합물은 하기 화합물 중에서 선택된 어느 하나일 수 있다.According to an exemplary embodiment of the present invention, the compound of Formula 1 may be any one selected from the following compounds.
Figure PCTKR2016011421-appb-I000067
Figure PCTKR2016011421-appb-I000067
Figure PCTKR2016011421-appb-I000068
Figure PCTKR2016011421-appb-I000068
Figure PCTKR2016011421-appb-I000069
Figure PCTKR2016011421-appb-I000069
Figure PCTKR2016011421-appb-I000070
Figure PCTKR2016011421-appb-I000070
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 화합물은 하기 화합물 중에서 선택된 어느 하나일 수 있다.According to an exemplary embodiment of the present invention, the compound of Formula 1 may be any one selected from the following compounds.
Figure PCTKR2016011421-appb-I000071
Figure PCTKR2016011421-appb-I000071
Figure PCTKR2016011421-appb-I000072
Figure PCTKR2016011421-appb-I000072
Figure PCTKR2016011421-appb-I000073
Figure PCTKR2016011421-appb-I000073
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 화합물은 하기 화합물 중에서 선택된 어느 하나일 수 있다.According to an exemplary embodiment of the present invention, the compound of Formula 1 may be any one selected from the following compounds.
Figure PCTKR2016011421-appb-I000074
Figure PCTKR2016011421-appb-I000074
Figure PCTKR2016011421-appb-I000075
Figure PCTKR2016011421-appb-I000075
Figure PCTKR2016011421-appb-I000076
Figure PCTKR2016011421-appb-I000076
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 화합물은 하기 화합물 중에서 선택된 어느 하나일 수 있다.According to an exemplary embodiment of the present invention, the compound of Formula 1 may be any one selected from the following compounds.
Figure PCTKR2016011421-appb-I000077
Figure PCTKR2016011421-appb-I000077
Figure PCTKR2016011421-appb-I000078
Figure PCTKR2016011421-appb-I000078
Figure PCTKR2016011421-appb-I000079
Figure PCTKR2016011421-appb-I000079
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 a는 1 또는 2이고, R1 중 적어도 하나는 -(L)m-A로 표시되며, L은 직접결합; 치환 또는 비치환된 아릴렌; 또는 치환 또는 비치환된 헤테로아릴렌이고, m은 1 내지 2의 정수이며, A는 -NAr1Ar2이고, Ar1 및 Ar2 중 적어도 하나는 치환 또는 비치환된 카바졸기, 또는 치환 또는 비치환된 벤조카바졸기이고, 나머지는 치환 또는 비치환된 아릴기 또는 치환 또는 비치환된 헤테로아릴기이다. According to an exemplary embodiment of the present specification, a in Formula 1 is 1 or 2, at least one of R1 is represented by-(L) m-A, L is a direct bond; Substituted or unsubstituted arylene; Or substituted or unsubstituted heteroarylene, m is an integer of 1 to 2, A is -NAr1Ar2, and at least one of Ar1 and Ar2 is a substituted or unsubstituted carbazole group, or a substituted or unsubstituted benzocarbazole group And the rest are substituted or unsubstituted aryl groups or substituted or unsubstituted heteroaryl groups.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 a는 1 또는 2이고, R1 중 적어도 하나는 -(L)m-A로 표시되며, L은 직접결합; 아릴렌; 또는 헤테로아릴렌이고, m은 1 내지 2의 정수이며, A는 -NAr1Ar2이고, Ar1 및 Ar2 중 적어도 하나는 아릴기로 치환 또는 비치환된 카바졸기, 또는 아릴기로 치환 또는 비치환된 벤조카바졸기이고, 나머지는 치환 또는 비치환된 아릴기이다. According to an exemplary embodiment of the present specification, a in Formula 1 is 1 or 2, at least one of R1 is represented by-(L) m-A, L is a direct bond; Arylene; Or heteroarylene, m is an integer of 1 to 2, A is -NAr1Ar2, at least one of Ar1 and Ar2 is a carbazole group unsubstituted or substituted with an aryl group, or a benzocarbazole group unsubstituted or substituted with an aryl group And the rest are substituted or unsubstituted aryl groups.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 화합물은 하기 화합물 중에서 선택된 어느 하나일 수 있다.According to an exemplary embodiment of the present invention, the compound of Formula 1 may be any one selected from the following compounds.
Figure PCTKR2016011421-appb-I000080
Figure PCTKR2016011421-appb-I000080
Figure PCTKR2016011421-appb-I000081
Figure PCTKR2016011421-appb-I000081
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 a는 1 내지 10이고, R1 중 적어도 하나는 -(L)m-A로 표시되며, L은 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고, m은 1 내지 10의 정수이며, A는 치환 또는 비치환된 N 함유 헤테로고리기이다.According to an exemplary embodiment of the present specification, a in Formula 1 is 1 to 10, at least one of R1 is represented by-(L) m-A, L is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group, m is an integer of 1 to 10, and A is a substituted or unsubstituted N-containing heterocyclic group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 a는 1 또는 2이고, R1 중 적어도 하나는 -(L)m-A로 표시되며, L은 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고, m은 1 또는 2이며, A는 치환 또는 비치환된 N 함유 헤테로고리기이다.According to an exemplary embodiment of the present specification, a in Formula 1 is 1 or 2, at least one of R1 is represented by-(L) m-A, L is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group, m is 1 or 2, and A is a substituted or unsubstituted N-containing heterocyclic group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 a는 1 또는 2이고, R1 중 적어도 하나는 -(L)m-A로 표시되며, L은 직접결합; 또는 탄소수 6 내지 20의 아릴렌기이고, m은 1 또는 2이며, A는 아릴기 또는 헤테로고리기로 치환 또는 비치환된 N 함유 헤테로고리기이다.According to an exemplary embodiment of the present specification, a in Formula 1 is 1 or 2, at least one of R1 is represented by-(L) m-A, L is a direct bond; Or an arylene group having 6 to 20 carbon atoms, m is 1 or 2, and A is an N-containing heterocyclic group unsubstituted or substituted with an aryl group or a heterocyclic group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 a는 1 또는 2이고, R1 중 적어도 하나는 -(L)m-A로 표시되며, L은 직접결합; 또는 탄소수 6 내지 20의 아릴렌기이고, m은 1 또는 2이며, A는 아릴기 또는 헤테로고리기로 치환 또는 비치환된 N 함유 헤테로고리기이며, 여기서 N 함유 헤테로고리기는 트리아진기, 피리미딘기, 피리딘기, 퀴나졸린기, 퀴놀린기, 이소퀴놀린기, 벤즈이미다졸기, 카바졸기, 또는 벤조카바졸기이다. According to an exemplary embodiment of the present specification, a in Formula 1 is 1 or 2, at least one of R1 is represented by-(L) m-A, L is a direct bond; Or an arylene group having 6 to 20 carbon atoms, m is 1 or 2, and A is an N-containing heterocyclic group unsubstituted or substituted with an aryl group or a heterocyclic group, wherein the N-containing heterocyclic group is a triazine group, a pyrimidine group, It is a pyridine group, a quinazoline group, a quinoline group, an isoquinoline group, a benzimidazole group, a carbazole group, or a benzocarbazole group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 a는 1 또는 2이고, R1 중 적어도 하나는 -(L)m-A로 표시되며, L은 직접결합; 또는 탄소수 6 내지 20의 아릴렌기이고, m은 1 또는 2이며, A는 탄소수 6 내지 20의 아릴기; 또는 N, O 또는 S를 포함하고 탄소수 2 내지 20인 헤테로고리기로 치환 또는 비치환된 N 함유 헤테로고리기이며, 여기서 N 함유 헤테로고리기는 트리아진기, 피리미딘기, 피리딘기, 퀴나졸린기, 퀴놀린기, 이소퀴놀린기, 벤즈이미다졸기, 카바졸기, 또는 벤조카바졸기이다. According to an exemplary embodiment of the present specification, a in Formula 1 is 1 or 2, at least one of R1 is represented by-(L) m-A, L is a direct bond; Or an arylene group having 6 to 20 carbon atoms, m is 1 or 2, and A is an aryl group having 6 to 20 carbon atoms; Or an N-containing heterocyclic group unsubstituted or substituted with a heterocyclic group having 2 to 20 carbon atoms containing N, O or S, wherein the N-containing heterocyclic group is a triazine group, a pyrimidine group, a pyridine group, a quinazoline group, a quinoline Group, isoquinoline group, benzimidazole group, carbazole group, or benzocarbazole group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 a는 1 또는 2이고, R1 중 적어도 하나는 -(L)m-A로 표시되며, L은 직접결합; 페닐렌기; 또는 바이페닐릴렌기이고, m은 1 또는 2이며, A는 페닐기, 나프틸기, 바이페닐릴기, 페닐기 또는 나프틸기로 치환 또는 비치환된 카바졸기, 페닐기 또는 나프틸기로 치환 또는 비치환된 벤조카바졸기, 디벤조티오펜기, 또는 디벤조퓨란기로 치환 또는 비치환된 N 함유 헤테로고리기이며, 여기서 N 함유 헤테로고리기는 트리아진기, 피리미딘기, 피리딘기, 퀴나졸린기, 퀴놀린기, 이소퀴놀린기, 벤즈이미다졸기, 카바졸기, 또는 벤조카바졸기이다.According to an exemplary embodiment of the present specification, a in Formula 1 is 1 or 2, at least one of R1 is represented by-(L) m-A, L is a direct bond; Phenylene group; Or a biphenylylene group, m is 1 or 2, and A is a benzocarba unsubstituted or substituted with a carbazole group, a phenyl group or a naphthyl group unsubstituted or substituted with a phenyl group, a naphthyl group, a biphenylyl group, a phenyl group or a naphthyl group N-containing heterocyclic group unsubstituted or substituted with a sol group, dibenzothiophene group, or dibenzofuran group, wherein the N-containing heterocyclic group is a triazine group, a pyrimidine group, a pyridine group, a quinazoline group, a quinoline group, an isoquinoline Group, benzimidazole group, carbazole group, or benzocarbazole group.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 화합물은 하기 화합물 중에서 선택된 어느 하나일 수 있다.According to an exemplary embodiment of the present invention, the compound of Formula 1 may be any one selected from the following compounds.
Figure PCTKR2016011421-appb-I000082
Figure PCTKR2016011421-appb-I000082
Figure PCTKR2016011421-appb-I000083
Figure PCTKR2016011421-appb-I000083
Figure PCTKR2016011421-appb-I000084
Figure PCTKR2016011421-appb-I000084
Figure PCTKR2016011421-appb-I000085
Figure PCTKR2016011421-appb-I000085
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 화합물은 하기 화합물 중에서 선택된 어느 하나일 수 있다.According to an exemplary embodiment of the present invention, the compound of Formula 1 may be any one selected from the following compounds.
Figure PCTKR2016011421-appb-I000086
Figure PCTKR2016011421-appb-I000086
Figure PCTKR2016011421-appb-I000087
Figure PCTKR2016011421-appb-I000087
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 화합물은 하기 화합물 중에서 선택된 어느 하나일 수 있다.According to an exemplary embodiment of the present invention, the compound of Formula 1 may be any one selected from the following compounds.
Figure PCTKR2016011421-appb-I000088
Figure PCTKR2016011421-appb-I000088
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 a는 1 내지 10이고, R1 중 적어도 하나는 -(L)m-A로 표시되며, L은 직접결합; 치환 또는 비치환된 아릴렌기 또는 치환 또는 비치환된 헤테로아릴렌기고, m은 1 내지 10의 정수이며, A는 -P(=O)R5R6이고, R5 및 R6는 서로 같거나 상이하고 각각 독립적으로 치환 또는 비치환된 아릴기이다. According to an exemplary embodiment of the present specification, a in Formula 1 is 1 to 10, at least one of R1 is represented by-(L) m-A, L is a direct bond; A substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group, m is an integer from 1 to 10, A is -P (= 0) R5R6, and R5 and R6 are the same as or different from each other, and each independently It is a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 a는 1 또는 2이고, R1 중 적어도 하나는 -(L)m-A로 표시되며, L은 직접결합; 또는 치환 또는 비치환된 아릴렌기이고, m은 1 또는 2이며, A는 -P(=O)R5R6이고, R5 및 R6는 서로 같거나 상이하고 각각 독립적으로 치환 또는 비치환된 아릴기이다. According to an exemplary embodiment of the present specification, a in Formula 1 is 1 or 2, at least one of R1 is represented by-(L) m-A, L is a direct bond; Or a substituted or unsubstituted arylene group, m is 1 or 2, A is -P (= 0) R 5 R 6, and R 5 and R 6 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 a는 1 또는 2이고, R1 중 적어도 하나는 -(L)m-A로 표시되며, L은 직접결합; 또는 탄소수 6 내지 20의 아릴렌기이고, m은 1 또는 2이며, A는 -P(=O)R5R6이고, R5 및 R6는 서로 같거나 상이하고 각각 독립적으로 탄소수 6 내지 20의 아릴기이다. According to an exemplary embodiment of the present specification, a in Formula 1 is 1 or 2, at least one of R1 is represented by-(L) m-A, L is a direct bond; Or an arylene group having 6 to 20 carbon atoms, m is 1 or 2, A is -P (= 0) R 5 R 6, and R 5 and R 6 are the same as or different from each other, and are each independently an aryl group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 a는 1 또는 2이고, R1 중 적어도 하나는 -(L)m-A로 표시되며, L은 페닐렌기이고, m은 1 또는 2이며, A는 -P(=O)R5R6이고, R5 및 R6는 각각 페닐기이다. According to an exemplary embodiment of the present specification, a in Formula 1 is 1 or 2, at least one of R 1 is represented by-(L) mA, L is a phenylene group, m is 1 or 2, A is- P (= O) R5R6 and R5 and R6 are each a phenyl group.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 화합물은 하기 화합물 중에서 선택된 어느 하나일 수 있다.According to an exemplary embodiment of the present invention, the compound of Formula 1 may be any one selected from the following compounds.
Figure PCTKR2016011421-appb-I000089
Figure PCTKR2016011421-appb-I000089
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 a는 1 내지 10이고, R1 중 적어도 하나는 -(L)m-A로 표시되며, L은 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고, m은 1 내지 10의 정수이며, A는 치환 또는 비치환된 안트라센기; 또는 할로겐기 또는 니트릴기로 치환된 아릴기이다.According to an exemplary embodiment of the present specification, a in Formula 1 is 1 to 10, at least one of R1 is represented by-(L) m-A, L is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group, m is an integer of 1 to 10, A is a substituted or unsubstituted anthracene group; Or an aryl group substituted with a halogen group or a nitrile group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 a는 1 또는 2이고, R1 중 적어도 하나는 -(L)m-A로 표시되며, L은 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고, m은 1 또는 2이며, A는 치환 또는 비치환된 안트라센기; 또는 할로겐기 또는 니트릴기로 치환된 아릴기이다.According to an exemplary embodiment of the present specification, a in Formula 1 is 1 or 2, at least one of R1 is represented by-(L) m-A, L is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group, m is 1 or 2, A is a substituted or unsubstituted anthracene group; Or an aryl group substituted with a halogen group or a nitrile group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 a는 1 또는 2이고, R1 중 적어도 하나는 -(L)m-A로 표시되며, L은 직접결합; 아릴렌기; 또는 헤테로아릴렌기이고, m은 1 또는 2이며, A는 할로겐기 또는 니트릴기로 치환 또는 비치환된 아릴기로 치환된 안트라센기; 또는 할로겐기 또는 니트릴기로 치환된 아릴기이다.According to an exemplary embodiment of the present specification, a in Formula 1 is 1 or 2, at least one of R1 is represented by-(L) m-A, L is a direct bond; Arylene group; Or a heteroarylene group, m is 1 or 2, A is an anthracene group substituted with an aryl group unsubstituted or substituted with a halogen group or a nitrile group; Or an aryl group substituted with a halogen group or a nitrile group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 a는 1 또는 2이고, R1 중 적어도 하나는 -(L)m-A로 표시되며, L은 직접결합; 또는 아릴렌기이고; m은 1 또는 2이며, A는 불소기 또는 니트릴기로 치환 또는 비치환된 아릴기로 치환된 안트라센기; 또는 불소기 또는 니트릴기로 치환된 아릴기이다.According to an exemplary embodiment of the present specification, a in Formula 1 is 1 or 2, at least one of R1 is represented by-(L) m-A, L is a direct bond; Or an arylene group; m is 1 or 2, and A is an anthracene group substituted with an aryl group unsubstituted or substituted with a fluorine group or a nitrile group; Or an aryl group substituted with a fluorine group or a nitrile group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 a는 1 또는 2이고, R1 중 적어도 하나는 -(L)m-A로 표시되며, L은 직접결합이고; m은 1 또는 2이며, A는 니트릴기로 치환 또는 비치환된 페닐기로 치환된 안트라센기; 또는 불소기 또는 니트릴기로 치환된 페닐기이다.According to an exemplary embodiment of the present specification, a in Formula 1 is 1 or 2, at least one of R1 is represented by-(L) m-A, L is a direct bond; m is 1 or 2, A is an anthracene group substituted with a phenyl group unsubstituted or substituted with a nitrile group; Or a phenyl group substituted with a fluorine group or a nitrile group.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 화합물은 하기 화합물 중에서 선택된 어느 하나일 수 있다.According to an exemplary embodiment of the present invention, the compound of Formula 1 may be any one selected from the following compounds.
Figure PCTKR2016011421-appb-I000090
Figure PCTKR2016011421-appb-I000090
상기 화학식 1로 표시되는 화합물은 후술하는 제조예를 기초로 제조될 수 있다. The compound represented by Chemical Formula 1 may be prepared based on the preparation examples described below.
일 실시상태에 따르면, 하기 반응식 1-1, 1-2 및 1-3과 같은 단계를 거쳐 제조될 수 있다. According to one embodiment, it may be prepared through the same steps as in Schemes 1-1, 1-2 and 1-3.
[반응식 1-1] Scheme 1-1
Figure PCTKR2016011421-appb-I000091
Figure PCTKR2016011421-appb-I000091
[반응식 1-2]Scheme 1-2
Figure PCTKR2016011421-appb-I000092
Figure PCTKR2016011421-appb-I000092
[반응식 1-3] Scheme 1-3
Figure PCTKR2016011421-appb-I000093
Figure PCTKR2016011421-appb-I000093
상기 반응식들에 있어서, In the above schemes,
Ar1, Ar2, Ar3 및 Ar4의 정의는 화학식 1에서와 같다. Ar 1, Ar 2, Ar 3, and Ar 4 are defined as in Formula 1.
상기 반응식 1-1, 1-2 및 1-3에서는 특정 위치에 특정 치환기를 갖는 화합물의 제조예를 중심으로 설명하였으나, 당업자는 당 기술분야에 알려져 있는 재료들을 이용하여, 상기 반응식을 참고하여 치환기의 위치, 종류 및 개수를 변경하여 실시할 수 있다. In Schemes 1-1, 1-2, and 1-3, the manufacturing examples of the compound having a specific substituent at a specific position have been described. This can be done by changing the location, type, and number of.
또한, 본 명세서는 상기 화학식 1로 표시되는 화합물을 포함하는 유기 발광 소자를 제공한다. In addition, the present specification provides an organic light emitting device including the compound represented by Formula 1.
본 명세서의 일 실시상태에 있어서, 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 제공한다. In one embodiment of the present specification, the first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound of Formula 1.
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 정공주입층, 정공수송층, 전자억제층, 발광층, 정공억제층, 전자수송층, 전자주입층 등을 포함하는 구조를 가질 수 있다. 그러나 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기물층을 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 injection layer, a hole transport layer, an electron suppression layer, a light emitting layer, a hole suppression layer, an electron transport layer, an electron injection 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 material layers.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 정공주입층, 정공수송층 또는 정공 주입과 수송을 동시에 하는 층을 포함하고, 상기 정공주입층, 정공수송층, 또는 정공 주입과 수송을 동시에 하는 층은 상기 화학식 1의 화합물을 포함한다. In an exemplary embodiment of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting holes, and the hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting holes is It includes a compound of formula (1).
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 전자억제층을 포함하고, 상기 전자억제층은 상기 화학식 1의 화합물을 포함한다. In one embodiment of the present specification, the organic material layer includes an electron suppression layer, and the electron suppression layer includes the compound of Formula 1.
또 하나의 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화학식 1의 화합물을 포함한다. In another exemplary embodiment, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound of Formula 1.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 정공억제층을 포함하고, 상기 정공억제층은 상기 화학식 1의 화합물을 포함한다. In one embodiment of the present specification, the organic material layer includes a hole suppression layer, and the hole suppression layer includes the compound of Formula 1.
본 명세서의 일 실시상태에 있어서, 상기 전자수송층, 전자주입층 또는 전자수송 및 전자주입을 동시에 하는 층은 상기 화학식 1의 화합물을 포함한다. In an exemplary embodiment of the present specification, the electron transport layer, the electron injection layer or the layer at the same time the electron transport and electron injection comprises a compound of the formula (1).
또 하나의 실시상태에 있어서, 상기 유기물층은 발광층 및 전자수송층을 포함하고, 상기 전자수송층은 상기 화학식 1의 화합물을 포함한다. In another exemplary embodiment, the organic material layer includes a light emitting layer and an electron transport layer, and the electron transport layer includes the compound of Formula 1.
본 명세서의 하나의 실시상태에 있어서, 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 발광층; 상기 발광층과 상기 제1 전극 사이, 또는 상기 발광층과 상기 제2 전극 사이에 구비된 2층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 2층 이상의 유기물층 중 적어도 하나는 상기 화합물을 포함한다. 하나의 실시상태에 있어서, 상기 2층 이상의 유기물층은 전자수송층, 전자주입층, 전자 수송과 전자 주입을 동시에 하는 층 및 정공억제층으로 이루어진 군에서 2 이상이 선택될 수 있다. In one embodiment of the present specification, the first electrode; A second electrode provided to face the first electrode; And a light emitting layer provided between the first electrode and the second electrode. An organic light emitting device including two or more organic material layers provided between the light emitting layer and the first electrode or between the light emitting layer and the second electrode, wherein at least one of the two or more organic material layers includes the compound. In one exemplary embodiment, two or more organic material layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer for simultaneously transporting electrons and electron injection, and a hole suppression layer.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 2층 이상의 전자수송층을 포함하고, 상기 2층 이상의 전자수송층 중 적어도 하나는 상기 화합물을 포함한다. 구체적으로 본 명세서의 일 실시상태에 있어서, 상기 화합물은 상기 2층 이상의 전자수송층 중 1층에 포함될 수도 있으며, 각각의 2층 이상의 전자수송층에 포함될 수 있다. In one embodiment of the present specification, the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the compound. Specifically, in one embodiment of the present specification, the compound may be included in one layer of the two or more electron transport layers, and may be included in each of the two or more electron transport layers.
또한, 본 명세서의 일 실시상태에 있어서, 상기 화합물이 상기 각각의 2층 이상의 전자수송층에 포함되는 경우, 상기 화합물을 제외한 다른 재료들은 서로 동일하거나 상이할 수 있다.In addition, in one embodiment of the present specification, when the compound is included in each of the two or more electron transport layers, other materials except for the compound may be the same or different from each other.
또 하나의 실시상태에 있어서, 유기 발광 소자는 기판 상에 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층된 구조(normal type)의 유기 발광 소자일 수 있다. In 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 있어서, 유기 발광 소자는 기판 상에 음극, 1층 이상의 유기물층 및 양극이 순차적으로 적층된 역방향 구조(inverted type)의 유기 발광 소자일 수 있다. In another exemplary embodiment, the organic light emitting diode may be an organic light emitting diode having an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
예컨대, 본 명세서의 일 실시상태에 따른 유기 발광 소자의 구조는 도 1 및 도 2에 예시되어 있다. For example, the structure of an organic light emitting diode according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 and 2.
도 1은 기판(1), 양극(2), 발광층(3), 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화합물은 상기 발광층에 포함될 수 있다. FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG. In such a structure, the compound may be included in the light emitting layer.
도 2는 기판 (1), 양극(2), 정공주입층(5), 정공수송층(6), 발광층(7), 전자수송층(8) 및 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화합물은 상기 정공주입층, 정공수송층, 발광층 및 전자수송층 중 1층 이상에 포함될 수 있다. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4. It is. In such a structure, the compound may be included in one or more layers of the hole injection layer, hole transport layer, light emitting layer and electron transport layer.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 하기 화학식 15로 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 Formula 15.
[화학식 15][Formula 15]
Figure PCTKR2016011421-appb-I000094
Figure PCTKR2016011421-appb-I000094
상기 화학식 15에 있어서,In Chemical Formula 15,
z1은 1 이상의 정수이고, z1이 2 이상의 정수인 경우 괄호 안의 구조는 서로 같거나 상이하고,z1 is an integer of 1 or more, and if z1 is an integer of 2 or more, the structures in parentheses are the same 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 크라이센기이고,Ar100 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 higher chrysene group,
L100은 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L100 is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
R100 및 R101은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아릴알킬기; 또는 치환 또는 비치환된 헤테로고리기이거나, 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.R100 and R101 are the same as or different from each other, and each independently 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 heterocyclic group, or may be combined with each other to form a substituted or unsubstituted ring.
본 명세서의 일 실시상태에 따르면, 상기 발광층은 상기 화학식 15로 표시되는 화합물을 발광층의 도펀트로서 포함한다.According to an exemplary embodiment of the present specification, the light emitting layer includes a compound represented by Formula 15 as a dopant of the light emitting layer.
본 명세서의 일 실시상태에 따르면, 상기 L100은 직접결합이다.According to an exemplary embodiment of the present specification, the L100 is a direct bond.
본 명세서의 일 실시상태에 따르면, 상기 z1은 2이다.According to an exemplary embodiment of the present specification, z1 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 크라이센기이다.According to an exemplary embodiment of the present specification, Ar100 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 파이렌기이다.According to an exemplary embodiment of the present specification, Ar100 is a divalent pyrene group unsubstituted or substituted with deuterium, methyl, ethyl, iso-propyl or tert-butyl groups.
본 명세서의 일 실시상태에 따르면, 상기 Ar100은 2가의 파이렌기이다.According to an exemplary embodiment of the present specification, Ar100 is a divalent pyrene group.
본 명세서의 일 실시상태에 따르면, 상기 R100 및 R101은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로고리기이다.According to an exemplary embodiment of the present specification, R100 and R101 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R100 및 R101은 서로 같거나 상이하고, 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 헤테로고리기이다.According to an exemplary embodiment of the present specification, R100 and R101 are the same as or different from each other, and each independently deuterium, alkyl, nitrile, aryl, alkylsilyl, or alkyl germanium group unsubstituted or substituted with 6 to 60 carbon atoms Aryl group; Or a heterocyclic 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 alkylgermanium group.
본 명세서의 일 실시상태에 따르면, 상기 R100 및 R101은 서로 같거나 상이하고, 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 헤테로고리기이다.According to an exemplary embodiment of the present specification, R100 and R101 are the same as or different from each other, and each independently deuterium, methyl, ethyl, iso-propyl, tert-butyl, nitrile, phenyl, trimethylsilyl or trimethylgernium An aryl group having 6 to 60 carbon atoms unsubstituted or substituted with a group; Or a heterocyclic group having 2 to 60 carbon atoms unsubstituted or substituted with deuterium, methyl group, ethyl group, iso-propyl group, tert-butyl group, nitrile group, phenyl group, trimethylsilyl group or trimethylgermanium group.
본 명세서의 일 실시상태에 따르면, 상기 R100 및 R101은 서로 같거나 상이하고, 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, R100 and R101 are the same as or different from each other, and each independently deuterium, methyl, ethyl, iso-propyl, tert-butyl, nitrile, phenyl, trimethylsilyl or trimethylgernium A phenyl group unsubstituted or substituted with a 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 서로 같거나 상이하고, 각각 독립적으로 트리메틸게르마늄기로 치환 또는 비치환된 페닐기이다.According to an exemplary embodiment of the present specification, R100 and R101 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a trimethylgermanium group.
본 명세서의 일 실시상태에 따르면, 상기 R100은 페닐기이다.According to an exemplary embodiment of the present specification, the R100 is a phenyl group.
본 명세서의 일 실시상태에 따르면, 상기 R101은 트리메틸게르마늄기로 치환된 페닐기이다.According to an exemplary embodiment of the present specification, R101 is a phenyl group substituted with a trimethylgermanium group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 15는 하기 화합물들 중에서 선택될 수 있다.According to an exemplary embodiment of the present specification, Formula 15 may be selected from the following compounds.
Figure PCTKR2016011421-appb-I000095
Figure PCTKR2016011421-appb-I000095
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 하기 화학식 16으로 표시되는 화합물을 포함할 수 있다.According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, the light emitting layer may include a compound represented by the following formula (16).
[화학식 16][Formula 16]
Figure PCTKR2016011421-appb-I000096
Figure PCTKR2016011421-appb-I000096
상기 화학식 16에 있어서,In Chemical Formula 16,
Ar101 및 Ar102는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,Ar101 and Ar102 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
L101 및 L102는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L101 and L102 are the same as or different from each other, and are each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
R102는 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 치환 또는 비치환된 아민기; 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 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,R102 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
z2 및 z3은 서로 같거나 상이하고 각각 독립적으로 1 또는 2의 정수이고, z4는 0 내지 8의 정수이고, z2 내지 z4가 2 이상인 경우 괄호 안의 치환기는 서로 같거나 상이하고,z2 and z3 are the same as or different from each other, and each independently an integer of 1 or 2, z4 is an integer of 0 to 8, when z2 to z4 is 2 or more, the substituents in parentheses are the same or different from each other,
v는 1 이상의 정수이고, v가 2 이상의 정수인 경우 괄호 안의 치환기는 서로 같거나 상이하다.v is an integer of 1 or more, and when v is an integer of 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 16으로 표시되는 화합물을 발광층의 호스트로서 포함한다.According to an exemplary embodiment of the present specification, the light emitting layer includes a compound represented by Formula 16 as a host of the light emitting layer.
본 명세서의 일 실시상태에 따르면, 상기 Ar101 및 Ar102는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로고리기이다.According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar101 및 Ar102는 서로 같거나 상이하고, 각각 독립적으로 알킬기, 아릴기 또는 헤테로고리기로 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 알킬기, 아릴기 또는 헤테로고리기로 치환 또는 비치환된 탄소수 2 내지 60의 헤테로고리기이다.According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently an aryl group having 6 to 60 carbon atoms unsubstituted or substituted with an alkyl group, an aryl group or a heterocyclic group; Or a heterocyclic group having 2 to 60 carbon atoms unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group.
본 명세서의 일 실시상태에 따르면, 상기 Ar101 및 Ar102는 서로 같거나 상이하고, 각각 독립적으로 아릴기 또는 헤테로고리기로 치환 또는 비치환된 페닐기; 아릴기 또는 헤테로고리기로 치환 또는 비치환된 비페닐기; 아릴기 또는 헤테로고리기로 치환 또는 비치환된 터페닐기; 아릴기 또는 헤테로고리기로 치환 또는 비치환된 나프틸기; 알킬기, 아릴기 또는 헤테로고리기로 치환 또는 비치환된 플루오렌기; 아릴기 또는 헤테로고리기로 치환 또는 비치환된 페난트렌기; 또는 아릴기 또는 헤테로고리기로 치환 또는 비치환된 트리페닐렌기이다.According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an aryl group or heterocyclic group; A biphenyl group unsubstituted or substituted with an aryl group or a heterocyclic group; Terphenyl groups unsubstituted or substituted with an aryl group or a heterocyclic group; A naphthyl group unsubstituted or substituted with an aryl group or a heterocyclic group; A fluorene group unsubstituted or substituted with an alkyl group, an aryl group or a heterocyclic group; Phenanthrene groups unsubstituted or substituted with an aryl group or a heterocyclic group; Or a triphenylene group unsubstituted or substituted with an aryl group or a heterocyclic group.
본 명세서의 일 실시상태에 따르면, 상기 Ar101 및 Ar102는 서로 같거나 상이하고, 각각 독립적으로 페닐기; 비페닐기; 터페닐기; 나프틸기; 메틸기 또는 페닐기로 치환 또는 비치환된 플루오렌기; 페난트렌기; 또는 트리페닐렌기이다.According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; A fluorene group unsubstituted or substituted with a methyl group or a phenyl group; Phenanthrene group; Or a triphenylene group.
본 명세서의 일 실시상태에 따르면, 상기 Ar101은 2-나프틸기이다.According to an exemplary embodiment of the present specification, Ar101 is a 2-naphthyl group.
본 명세서의 일 실시상태에 따르면, 상기 Ar102는 1-나프틸기이다.According to an exemplary embodiment of the present specification, Ar102 is a 1-naphthyl group.
본 명세서의 일 실시상태에 따르면, 상기 L101 및 L102는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 페닐렌기; 또는 나프틸렌기이다.According to an exemplary embodiment of the present specification, the L101 and L102 are the same as or different from each other, and each independently a direct bond; Phenylene group; Or a naphthylene group.
본 명세서의 일 실시상태에 따르면, 상기 L101은 페닐렌기이다.According to an exemplary embodiment of the present specification, L101 is a phenylene group.
본 명세서의 일 실시상태에 따르면, 상기 L102는 직접결합이다.According to an exemplary embodiment of the present specification, L102 is a direct bond.
본 명세서의 일 실시상태에 따르면, 상기 R102는 수소이다.According to an exemplary embodiment of the present disclosure, wherein R102 is hydrogen.
본 명세서의 일 실시상태에 따르면, 상기 z2는 1이다.According to an exemplary embodiment of the present specification, z2 is 1.
본 명세서의 일 실시상태에 따르면, 상기 v는 1이다.According to an exemplary embodiment of the present disclosure, wherein v is 1.
본 명세서의 일 실시상태에 따르면, 상기 v는 2이다.According to an exemplary embodiment of the present disclosure, wherein v is 2.
본 명세서의 일 실시상태에 따르면, 상기 화학식 16은 하기 화합물들 중에서 선택될 수 있다.According to an exemplary embodiment of the present specification, Formula 16 may be selected from the following compounds.
Figure PCTKR2016011421-appb-I000097
Figure PCTKR2016011421-appb-I000097
Figure PCTKR2016011421-appb-I000099
Figure PCTKR2016011421-appb-I000099
Figure PCTKR2016011421-appb-I000100
Figure PCTKR2016011421-appb-I000100
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화학식 15로 표시되는 화합물을 발광층의 도펀트로서 포함하며, 상기 화학식 16으로 표시되는 화합물을 발광층의 호스트로서 포함한다.According to the exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, the light emitting layer includes the compound represented by Chemical Formula 15 as a dopant of the light emitting layer, and includes the compound represented by Chemical Formula 16 as a host of the light emitting layer.
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. 이 때 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 정공주입층, 정공수송층, 발광층 및 전자수송층을 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, 잉크젯프린팅, 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 있어서, 상기 제1 전극은 양극이고, 상기 제2 전극은 음극이다. In one embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.
또 하나의 실시상태에 있어서, 상기 제1 전극은 음극이고, 상기 제2 전극은 양극이다. In another exemplary embodiment, the first electrode is a cathode and the second electrode is an anode.
상기 양극 물질로는 통상 유기물층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 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. As the anode material, a material having a large work function is usually preferred 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); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
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 정공주입층은 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 전자주입층 또는 전자주입재료에의 이동을 방지하며, 또한, 박막 형성 능력이 우수한 화합물이 바람직하다. 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물층의 HOMO 사이인 것이 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 한정 되는 것은 아니다. The hole injection layer is a layer for injecting holes from the electrode, and has a capability of transporting holes to the hole injection material, and has a hole injection effect at the anode, an excellent hole injection effect to the light emitting layer or the light emitting material, and is produced in the light emitting layer 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. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. 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 materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
상기 정공수송층은 정공주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로, 정공 수송 물질로는 양극이나 정공주입층으로부터 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 that receives holes from the hole injection layer and transports holes to the light emitting layer. The hole transport material is a material capable of transporting holes from an anode or a hole injection layer and transferring 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 정공수송층과 전자수송층으로부터 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); 카바졸 계열 화합물; 이량체화 스티릴(dimerized styryl) 화합물; BAlq; 10-히드록시벤조 퀴놀린-금속 화합물; 벤즈옥사졸, 벤조티아졸 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, benzothiazole 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 아릴아민기를 갖는 축합 방향족환 유도체로서, 아릴아민기를 갖는 피렌, 안트라센, 크라이센, 페리플란텐 등이 있으며, 스티릴아민 화합물로는 치환 또는 비치환된 아릴아민에 적어도 1개의 아릴비닐기가 치환되어 있는 화합물로, 아릴기, 실릴기, 알킬기, 시클로알킬기 및 아릴아민기로 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 arylamine group, and include pyrene, anthracene, chrysene, and periplanthene having an arylamine group, and a styrylamine compound may be substituted or unsubstituted. At least one arylvinyl group is substituted with the 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 arylamine 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 전자수송층은 전자주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 층으로 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 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. 전자수송층은 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 전자주입층은 전극으로부터 전자를 주입하는 층으로, 전자를 수송하는 능력을 갖고, 음극으로부터의 전자주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며, 발광층에서 생성된 여기자의 정공주입층에의 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 that injects electrons from an electrode, has an ability to transport electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a 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.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1의 화합물은 유기 발광 소자 외에도 유기 태양 전지 또는 유기 트랜지스터에 포함될 수 있다.In one embodiment of the present specification, the compound of Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
상기 화학식 1로 표시되는 화합물 및 이를 포함하는 유기 발광 소자의 제조는 이하 실시예에서 구체적으로 설명한다. 그러나 하기 실시예는 본 명세서를 예시하기 위한 것이며, 본 명세서의 범위가 이들에 의하여 한정되는 것은 아니다.Preparation of the compound represented by Chemical Formula 1 and an organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the present specification, and the scope of the present specification is not limited thereto.
<< 합성예Synthesis Example 1> 1>
<< 제조예Production Example 1> 1>
하기 화합물 1 의 화합물 합성Compound Synthesis of the Following Compound 1
Figure PCTKR2016011421-appb-I000101
Figure PCTKR2016011421-appb-I000101
질소 분위기에서 500ml 둥근 바닥 플라스크에 화합물 A (10.0g, 17.83mmol), 디페닐아민(diphenylamine) (3.31g, 19.61mmol)을 크실렌(Xylene) 180ml에 완전히 녹인 후 소디움 t-부톡사이드(sodium tert-butoxide) (2.05g, 21.39mol)를 첨가하고, 비스(트리-t-부틸포스핀)팔라듐(0) (Bis(tri-tert-butylphosphine) palladium(0)) (0.09g, 0.18mmol)을 넣은 후 2 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 여과(filter)하여 염(base)을 제거한 후에 크실렌을 감압농축시키고 에틸아세테이트 150ml으로 재결정하여 상기 화합물 1 (8.85g, 수율: 77%)을 제조하였다.Compound A (10.0 g, 17.83 mmol) and diphenylamine (3.31 g, 19.61 mmol) were completely dissolved in 180 ml of xylene in a 500 ml round-bottom flask in nitrogen atmosphere, followed by sodium tert-butoxide. butoxide) (2.05 g, 21.39 mol) was added, followed by bis (tri-t-butylphosphine) palladium (0) (Bis (tri- tert- butylphosphine) palladium (0)) (0.09 g, 0.18 mmol) It was then stirred for 2 hours by heating. After the temperature was lowered to room temperature and filtered to remove the base, the xylene was concentrated under reduced pressure and recrystallized with 150 ml of ethyl acetate to obtain Compound 1 (8.85 g, yield: 77%).
MS[M+H]+= 650MS [M + H] + = 650
<< 제조예Production Example 2> 2>
하기 화합물 2 의 화합물 합성Compound Synthesis of the Following Compound 2
Figure PCTKR2016011421-appb-I000102
Figure PCTKR2016011421-appb-I000102
질소 분위기에서 500ml 둥근 바닥 플라스크에 화합물 A (10.0g, 17.83mmol), N-페닐-[1,1'-바이페닐]-4-아민(N-phenyl-[1,1'-biphenyl]-4-amine) (4.80g, 19.61mmol)을 크실렌 200ml에 완전히 녹인 후 소디움 t-부톡사이드(2.05g, 21.39mol)를 첨가하고, 비스(트리-t-부틸포스핀)팔라듐(0) (0.09g, 0.18mmol)을 넣은 후 3 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 여과하여 염을 제거한 후에 크실렌을 감압농축시키고 에틸아세테이트 200ml으로 재결정하여 상기 화합물 2 (9.42g, 수율: 73%)를 제조하였다.Compound A (10.0 g, 17.83 mmol), N-phenyl- [1,1'-biphenyl] -4-amine (N-phenyl- [1,1'-biphenyl] -4 in a 500 ml round-bottom flask in a nitrogen atmosphere -amine) (4.80 g, 19.61 mmol) was dissolved completely in 200 ml of xylene, followed by addition of sodium t-butoxide (2.05 g, 21.39 mol), bis (tri-t-butylphosphine) palladium (0) (0.09 g , 0.18 mmol) was added thereto, and the resulting mixture was heated and stirred for 3 hours. After cooling to room temperature to remove the salt by filtration and xylene was concentrated under reduced pressure and recrystallized with 200ml of ethyl acetate to give the compound 2 (9.42g, yield: 73%).
MS[M+H]+= 726MS [M + H] + = 726
<< 제조예Production Example 3> 3>
하기 화합물 3 의 화합물 합성Compound Synthesis of the Following Compound 3
Figure PCTKR2016011421-appb-I000103
Figure PCTKR2016011421-appb-I000103
질소 분위기에서 500ml 둥근 바닥 플라스크에 화합물 A (10.0g, 17.83mmol), 디([1,1'-바이페닐]-4-일)아민 (6.29g, 19.61mmol)을 크실렌 220ml에 완전히 녹인 후 소디움 t-부톡사이드(2.05g, 21.39mol)를 첨가하고, 비스(트리-t-부틸포스핀)팔라듐(0) (0.09g, 0.18mmol)을 넣은 후 4 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 여과하여 염을 제거한 후에 크실렌을 감압농축시키고 에틸아세테이트 250ml으로 재결정하여 상기 화합물 3 (12.22g, 수율: 86%)을 제조하였다.Dissolve Compound A (10.0 g, 17.83 mmol) and di ([1,1'-biphenyl] -4-yl) amine (6.29 g, 19.61 mmol) in 220 ml of xylene in a 500 ml round-bottom flask in a nitrogen atmosphere. t-butoxide (2.05 g, 21.39 mol) was added, bis (tri-t-butylphosphine) palladium (0) (0.09 g, 0.18 mmol) was added and the mixture was heated and stirred for 4 hours. After cooling to room temperature to remove the salt by filtration and xylene was concentrated under reduced pressure and recrystallized with 250ml of ethyl acetate to give the compound 3 (12.22g, yield: 86%).
MS[M+H]+= 803MS [M + H] + = 803
<< 제조예Production Example 4> 4>
하기 화합물 4 의 화합물 합성Compound Synthesis of the Following Compound 4
Figure PCTKR2016011421-appb-I000104
Figure PCTKR2016011421-appb-I000104
질소 분위기에서 500ml 둥근 바닥 플라스크에 화합물 A (10.0g, 17.83mmol), N-([1,1'-바이페닐]-4-일)-[1,1'-바이페닐]-2-아민 (6.29g, 19.61mmol)을 크실렌 220ml에 완전히 녹인 후 소디움 t-부톡사이드(2.05g, 21.39mol)를 첨가하고, 비스(트리-t-부틸포스핀)팔라듐(0) (0.09g, 0.18mmol)을 넣은 후 3 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 여과하여 염을 제거한 후에 크실렌을 감압농축시키고 에틸아세테이트 230ml으로 재결정하여 상기 화합물 4 (11.01g, 수율: 77%)를 제조하였다.Compound A (10.0 g, 17.83 mmol), N-([1,1'-biphenyl] -4-yl)-[1,1'-biphenyl] -2-amine (in a 500 ml round bottom flask in a nitrogen atmosphere) 6.29 g, 19.61 mmol) dissolved completely in 220 ml of xylene, followed by addition of sodium t-butoxide (2.05 g, 21.39 mol), bis (tri-t-butylphosphine) palladium (0) (0.09 g, 0.18 mmol) After stirring, the mixture was heated and stirred for 3 hours. After cooling to room temperature to remove the salt by filtration, xylene was concentrated under reduced pressure and recrystallized with 230 ml of ethyl acetate to give the compound 4 (11.01 g, yield: 77%).
MS[M+H]+= 803MS [M + H] + = 803
<< 제조예Production Example 5> 5>
하기 화합물 5 의 화합물 합성Compound Synthesis of the Following Compound 5
Figure PCTKR2016011421-appb-I000105
Figure PCTKR2016011421-appb-I000105
질소 분위기에서 500ml 둥근 바닥 플라스크에 화합물 A (10.0g, 17.83mmol), N-([1,1'-바이페닐]-4-일)-9,9-디메틸-9H-플루오렌-2-아민 (7.08g, 19.61mmol)을 크실렌 240ml에 완전히 녹인 후 소디움 t-부톡사이드(2.05g, 21.39mol)를 첨가하고, 비스(트리-t-부틸포스핀)팔라듐(0) (0.09g, 0.18mmol)을 넣은 후 5 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 여과하여 염을 제거한 후에 크실렌을 감압농축시키고 에틸아세테이트 280ml으로 재결정하여 상기 화합물 5 (11.32g, 수율: 76%)를 제조하였다.Compound A (10.0 g, 17.83 mmol), N-([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine in a 500 ml round bottom flask under nitrogen atmosphere (7.08 g, 19.61 mmol) was dissolved completely in 240 ml of xylene, followed by addition of sodium t-butoxide (2.05 g, 21.39 mol), bis (tri-t-butylphosphine) palladium (0) (0.09 g, 0.18 mmol ) Was added and the mixture was heated and stirred for 5 hours. The mixture was cooled to room temperature, filtered to remove salts, and xylene was concentrated under reduced pressure and recrystallized from 280 ml of ethyl acetate to obtain Compound 5 (11.32 g, yield: 76%).
MS[M+H]+= 843MS [M + H] + = 843
<< 제조예Production Example 6> 6>
하기 화합물 6 의 화합물 합성Compound Synthesis of the Following Compound 6
Figure PCTKR2016011421-appb-I000106
Figure PCTKR2016011421-appb-I000106
질소 분위기에서 500ml 둥근 바닥 플라스크에 화합물 A (10.0g, 17.83mmol), N-([1,1'-바이페닐]-2-일)-9,9-디메틸-9H-플루오렌-2-아민 (7.08g, 19.61mmol)을 크실렌 220ml에 완전히 녹인 후 소디움 t-부톡사이드(2.05g, 21.39mol)를 첨가하고, 비스(트리-t-부틸포스핀)팔라듐(0) (0.09g, 0.18mmol)을 넣은 후 3 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 여과하여 염을 제거한 후에 크실렌을 감압농축시키고 에틸아세테이트 240ml으로 재결정하여 상기 화합물 6 (10.19g, 수율: 68%)을 제조하였다.Compound A (10.0 g, 17.83 mmol), N-([1,1'-biphenyl] -2-yl) -9,9-dimethyl-9H-fluoren-2-amine in a 500 ml round bottom flask under nitrogen atmosphere (7.08 g, 19.61 mmol) was dissolved completely in 220 ml of xylene, followed by addition of sodium t-butoxide (2.05 g, 21.39 mol), bis (tri-t-butylphosphine) palladium (0) (0.09 g, 0.18 mmol ) Was added and the mixture was heated and stirred for 3 hours. After cooling to room temperature to remove the salt by filtration and xylene was concentrated under reduced pressure and recrystallized with 240ml of ethyl acetate to give the compound 6 (10.19g, yield: 68%).
MS[M+H]+= 843MS [M + H] + = 843
<< 제조예Production Example 7>  7>
하기 화합물 7 의 화합물 합성Compound Synthesis of the Following Compound 7
Figure PCTKR2016011421-appb-I000107
Figure PCTKR2016011421-appb-I000107
질소 분위기에서 500ml 둥근 바닥 플라스크에 화합물 A (10.0g, 17.83mmol), 9,9-디메틸-N-페닐-9H-플루오렌-2-아민 (5.59g, 19.61mmol)을 크실렌 220ml에 완전히 녹인 후 소디움 t-부톡사이드(2.05g, 21.39mol)를 첨가하고, 비스(트리-t-부틸포스핀)팔라듐(0) (0.09g, 0.18mmol)을 넣은 후 3 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 여과하여 염을 제거한 후에 크실렌을 감압농축시키고 에틸아세테이트 240ml으로 재결정하여 상기 화합물 7 (10.02g, 수율: 75%)을 제조하였다. Dissolve Compound A (10.0 g, 17.83 mmol) and 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (5.59 g, 19.61 mmol) in 220 ml of xylene in a 500 ml round-bottom flask in a nitrogen atmosphere. Sodium t-butoxide (2.05 g, 21.39 mol) was added, bis (tri-t-butylphosphine) palladium (0) (0.09 g, 0.18 mmol) was added and the mixture was heated and stirred for 3 hours. After cooling to room temperature to remove the salt by filtration and xylene was concentrated under reduced pressure and recrystallized with 240ml of ethyl acetate to give the compound 7 (10.02g, yield: 75%).
MS[M+H]+= 767MS [M + H] + = 767
<< 제조예Production Example 8>  8>
하기 화합물 8 의 화합물 합성Compound Synthesis of the Following Compound 8
Figure PCTKR2016011421-appb-I000108
Figure PCTKR2016011421-appb-I000108
질소 분위기에서 500ml 둥근 바닥 플라스크에 화합물 A (10g, 17.83mmol), (4-(디페닐아미노)페닐)보론산 (5.92g, 20.50mmol)을 테트라하이드로퓨란 220ml에 완전히 녹인 후 2M 탄산칼륨수용액(110ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.21g, 0.18mmol)을 넣은 후 3 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축시키고 에틸아세테이트 210ml로 재결정하여 화합물 8 (9.97g, 77%)을 제조하였다.In a 500 ml round bottom flask in nitrogen atmosphere, Compound A (10 g, 17.83 mmol) and (4- (diphenylamino) phenyl) boronic acid (5.92 g, 20.50 mmol) were completely dissolved in 220 ml of tetrahydrofuran, followed by 2M aqueous potassium carbonate solution ( 110 ml) was added, tetrakis- (triphenylphosphine) palladium (0.21 g, 0.18 mmol) was added thereto, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 210 ml of ethyl acetate to obtain compound 8 (9.97 g, 77%).
MS[M+H]+= 726MS [M + H] + = 726
<< 제조예Production Example 9>  9>
하기 화합물 9 의 화합물 합성Compound Synthesis of the Following Compound 9
Figure PCTKR2016011421-appb-I000109
Figure PCTKR2016011421-appb-I000109
질소 분위기에서 500ml 둥근 바닥 플라스크에 화합물 A (10g, 17.83mmol), (9-페닐-9H-카바졸-3-일)보론산 (5.92g, 20.50mmol)을 테트라하이드로퓨란 260ml에 완전히 녹인 후 2M 탄산칼륨수용액(130ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.21g, 0.18mmol)을 넣은 후 5 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축시키고 에틸아세테이트 280ml로 재결정하여 화합물 9 (10.47g, 81%)를 제조하였다.Dissolve Compound A (10 g, 17.83 mmol) and (9-phenyl-9H-carbazol-3-yl) boronic acid (5.92 g, 20.50 mmol) in 260 ml of tetrahydrofuran in a 500 ml round-bottom flask in a nitrogen atmosphere. Aqueous potassium carbonate solution (130 ml) was added, tetrakis- (triphenylphosphine) palladium (0.21 g, 0.18 mmol) was added thereto, and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 280 ml of ethyl acetate to obtain compound 9 (10.47 g, 81%).
MS[M+H]+= 724MS [M + H] + = 724
<< 제조예Production Example 10>  10>
하기 화합물 10 의 화합물 합성Compound Synthesis of the Following Compound 10
Figure PCTKR2016011421-appb-I000110
Figure PCTKR2016011421-appb-I000110
질소 분위기에서 500ml 둥근 바닥 플라스크에 화합물 A (10g, 17.83mmol), (4-(디페닐포스포릴)페닐)보론산 (6.60g, 20.50mmol)을 테트라하이드로퓨란 220ml에 완전히 녹인 후 2M 탄산칼륨수용액(110ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.21g, 0.18mmol)을 넣은 후 3 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축시키고 에틸아세테이트 210ml로 재결정하여 화합물 10 (11.46g, 85%)을 제조하였다.Dissolve Compound A (10 g, 17.83 mmol) and (4- (diphenylphosphoryl) phenyl) boronic acid (6.60 g, 20.50 mmol) in 220 ml of tetrahydrofuran in a 500 ml round-bottom flask in a nitrogen atmosphere. (110ml) was added, tetrakis- (triphenylphosphine) palladium (0.21g, 0.18mmol) was added thereto, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 210 ml of ethyl acetate to obtain compound 10 (11.46 g, 85%).
MS[M+H]+= 759MS [M + H] + = 759
<< 제조예Production Example 11>  11>
하기 화합물 11 의 화합물 합성Compound Synthesis of the Following Compound 11
Figure PCTKR2016011421-appb-I000111
Figure PCTKR2016011421-appb-I000111
질소 분위기에서 500ml 둥근 바닥 플라스크에 화합물 A-1 (10g, 16.50mmol), 2-클로로-4,6-디페닐-1,3,5-트리아진 (3.83g, 14.34mmol)을 테트라하이드로퓨란 240ml에 완전히 녹인 후 2M 탄산칼륨수용액(120ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.17g, 0.14mmol)을 넣은 후 3 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축시키고 에틸아세테이트 210ml로 재결정하여 화합물 11 (9.44g, 80%)을 제조하였다.240 ml of tetrahydrofuran with Compound A-1 (10 g, 16.50 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (3.83 g, 14.34 mmol) in a 500 ml round bottom flask in a nitrogen atmosphere After completely dissolved in 2M aqueous potassium carbonate solution (120ml) was added, tetrakis- (triphenylphosphine) palladium (0.17g, 0.14mmol) was added, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 210 ml of ethyl acetate to obtain compound 11 (9.44 g, 80%).
MS[M+H]+= 714MS [M + H] + = 714
<< 제조예Production Example 12>  12>
하기 화합물 12 의 화합물 합성Compound Synthesis of the Following Compound 12
Figure PCTKR2016011421-appb-I000112
Figure PCTKR2016011421-appb-I000112
질소 분위기에서 500ml 둥근 바닥 플라스크에 화합물 A-1 (10g, 16.50mmol), 2-클로로-4,6-디페닐피리미딘 (3.83g, 14.34mmol)을 테트라하이드로퓨란 280ml에 완전히 녹인 후 2M 탄산칼륨수용액(140ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.17g, 0.14mmol)을 넣은 후 5 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축시키고 에틸아세테이트 230ml로 재결정하여 화합물 12 (8.49, 71%)를 제조하였다.In a 500 ml round bottom flask in nitrogen atmosphere, Compound A-1 (10 g, 16.50 mmol) and 2-chloro-4,6-diphenylpyrimidine (3.83 g, 14.34 mmol) were completely dissolved in 280 ml of tetrahydrofuran, followed by 2 M potassium carbonate. Aqueous solution (140ml) was added, tetrakis- (triphenylphosphine) palladium (0.17g, 0.14mmol) was added thereto, and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 230 ml of ethyl acetate to obtain Compound 12 (8.49, 71%).
MS[M+H]+= 713MS [M + H] + = 713
<< 제조예Production Example 13>  13>
하기 화합물 13 의 화합물 합성Compound Synthesis of the Following Compound 13
Figure PCTKR2016011421-appb-I000113
Figure PCTKR2016011421-appb-I000113
질소 분위기에서 500ml 둥근 바닥 플라스크에 화합물 A-1 (10g, 16.50mmol), 4-클로로-2,6-디페닐피리미딘 (3.83g, 14.34mmol)을 테트라하이드로퓨란 240ml에 완전히 녹인 후 2M 탄산칼륨수용액(120ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.17g, 0.14mmol)을 넣은 후 3 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축시키고 에틸아세테이트 260ml로 재결정하여 화합물 13 (7.92g, 67%)을 제조하였다.In a 500 ml round bottom flask in nitrogen atmosphere, Compound A-1 (10 g, 16.50 mmol) and 4-chloro-2,6-diphenylpyrimidine (3.83 g, 14.34 mmol) were completely dissolved in 240 ml of tetrahydrofuran, followed by 2M potassium carbonate. An aqueous solution (120 ml) was added, tetrakis- (triphenylphosphine) palladium (0.17 g, 0.14 mmol) was added thereto, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 260 ml of ethyl acetate to obtain compound 13 (7.92 g, 67%).
MS[M+H]+= 713MS [M + H] + = 713
<< 제조예Production Example 14>  14>
하기 화합물 14 의 화합물 합성Compound Synthesis of the Following Compound 14
Figure PCTKR2016011421-appb-I000114
Figure PCTKR2016011421-appb-I000114
질소 분위기에서 500ml 둥근 바닥 플라스크에 화합물 A-1 (10g, 16.50mmol), 2-클로로-4,6-디페닐피리딘 (3.83g, 14.34mmol)을 테트라하이드로퓨란 240ml에 완전히 녹인 후 2M 탄산칼륨수용액(120ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.17g, 0.14mmol)을 넣은 후 3 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축시키고 에틸아세테이트 210ml로 재결정하여 화합물 14 (8.23g, 70%)를 제조하였다.In a 500 ml round-bottom flask in a nitrogen atmosphere, Compound A-1 (10 g, 16.50 mmol) and 2-chloro-4,6-diphenylpyridine (3.83 g, 14.34 mmol) were completely dissolved in 240 ml of tetrahydrofuran, followed by 2M aqueous potassium carbonate solution. (120 ml) was added, tetrakis- (triphenylphosphine) palladium (0.17 g, 0.14 mmol) was added, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 210 ml of ethyl acetate to obtain compound 14 (8.23 g, 70%).
MS[M+H]+= 712MS [M + H] + = 712
<< 제조예Production Example 15> 내지 < 15> to < 제조예Production Example 28> 28>
Figure PCTKR2016011421-appb-I000115
Figure PCTKR2016011421-appb-I000115
제조예 1 내지 14에서 출발물질을 화합물 A 또는 A-1 대신 화합물 B 또는 B-1 인 물질을 사용한 것을 제외하고 제조예 1 내지 14와 동일한 방법으로 상기 화합물 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27 및 28을 제조하였다.Compounds 15, 16, 17, 18, 19, in the same manner as in Preparation Examples 1 to 14 except that the starting material in Preparation Examples 1 to 14 was used instead of Compound A or A-1, which was Compound B or B-1. 20, 21, 22, 23, 24, 25, 26, 27 and 28 were prepared.
Figure PCTKR2016011421-appb-I000116
Figure PCTKR2016011421-appb-I000116
<< 실험예Experimental Example 1-1> 1-1>
ITO(indium tin oxide)가 1,000Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이 때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀러포어사(Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알코올, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 수송시켰다.A glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and ultrasonically cleaned. At this time, Fischer Co. product was used as a detergent, and distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water. After ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After washing the distilled water, ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
이렇게 준비된 ITO 투명 전극 위에 하기 화합물 헥사니트릴 헥사아자트리페닐렌 (hexaazatriphenylene-hexanitrile: HAT)을 500Å의 두께로 열 진공 증착하여 정공주입층을 형성하였다. The following compound hexanitrile hexaazatriphenylene (hexaazatriphenylene-hexanitrile: HAT) was thermally vacuum deposited to a thickness of 500 kPa on the prepared ITO transparent electrode to form a hole injection layer.
[HAT][HAT]
Figure PCTKR2016011421-appb-I000117
Figure PCTKR2016011421-appb-I000117
상기 정공주입층 위에 정공을 수송하는 물질인 하기 화합물 4-4'-비스[N-(1-나프틸)-N-페닐아미노]비페닐(NPB)(300Å)을 진공 증착하여 정공수송층을 형성하였다. Compound 4-4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) (300 kV), which is a substance for transporting holes on the hole injection layer, was vacuum deposited to form a hole transport layer. It was.
[NPB][NPB]
Figure PCTKR2016011421-appb-I000118
Figure PCTKR2016011421-appb-I000118
이어서, 상기 정공수송층 위에 막 두께 100Å으로 하기 화합물 1을 진공 증착하여 전자억제층을 형성하였다.Subsequently, the following compound 1 was vacuum deposited to a film thickness of 100 kPa on the hole transport layer to form an electron suppression layer.
[화합물 1][Compound 1]
Figure PCTKR2016011421-appb-I000119
Figure PCTKR2016011421-appb-I000119
이어서, 상기 전자억제층 위에 막 두께 300Å으로 아래와 같은 BH와 BD를 25:1의 중량비로 진공증착하여 발광층을 형성하였다. Subsequently, the light emitting layer was formed by vacuum depositing the following BH and BD in a weight ratio of 25: 1 on the electron suppressing layer with a film thickness of 300 Pa.
Figure PCTKR2016011421-appb-I000120
Figure PCTKR2016011421-appb-I000120
상기 발광층 위에 상기 화합물 ET1과 상기 화합물 LiQ(Lithium Quinolate)을 1:1의 중량비로 진공증착하여 300Å의 두께로 전자 주입 및 수송층을 형성하였다. 상기 전자 주입 및 수송층 위에 순차적으로 12Å두께로 리튬플로라이드(LiF)와 2,000Å 두께로 알루미늄을 증착하여 음극을 형성하였다. Compound ET1 and compound LiQ (Lithium Quinolate) were vacuum-deposited on the emission layer at a weight ratio of 1: 1 to form an electron injection and transport layer at a thickness of 300 kPa. On the electron injection and transport layer, lithium fluoride (LiF) and aluminum were deposited to a thickness of 12 kPa in order to form a cathode.
상기의 과정에서 유기물의 증착속도는 0.4 ~ 0.7Å/sec를 유지하였고, 음극의 리튬플로라이드는 0.3Å/sec, 알루미늄은 2Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 2 × 10-7 ~ 5 × 10-6 torr를 유지하여, 유기 발광 소자를 제작하였다.Was maintained at the deposition rate was 0.4 ~ 0.7Å / sec for organic material in the above process, the lithium fluoride of the cathode was 0.3Å / sec, aluminum is deposited at a rate of 2Å / sec, During the deposition, a vacuum 2 × 10 - The organic light emitting device was manufactured by maintaining 7 to 5 × 10 −6 torr.
<< 실험예Experimental Example 1-2> 1-2>
상기 실험예 1-1에서 화합물 1 대신 상기 화합물 2를 사용한 것을 제외하고는 실험예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2 was used instead of compound 1 in Experimental Example 1-1.
<< 실험예Experimental Example 1-3> 1-3>
상기 실험예 1-1에서 화합물 1 대신 상기 화합물 3을 사용한 것을 제외하고는 실험예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다. The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 3 was used instead of compound 1 in Experimental Example 1-1.
<< 실험예Experimental Example 1-4> 1-4>
상기 실험예 1-1에서 화합물 1 대신 상기 화합물 4를 사용한 것을 제외하고는 실험예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 4 was used instead of compound 1 in Experimental Example 1-1.
<< 실험예Experimental Example 1-5> 1-5>
상기 실험예 1-1에서 화합물 1 대신 상기 화합물 5를 사용한 것을 제외하고는 실험예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 5 was used instead of compound 1 in Experimental Example 1-1.
<< 실험예Experimental Example 1-6> 1-6>
상기 실험예 1-1에서 화합물 1 대신 상기 화합물 6을 사용한 것을 제외하고는 실험예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 6 was used instead of compound 1 in Experimental Example 1-1.
<< 실험예Experimental Example 1-7> 1-7>
상기 실험예 1-1에서 화합물 1 대신 상기 화합물 7을 사용한 것을 제외하고는 실험예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 7 was used instead of compound 1 in Experimental Example 1-1.
<< 실험예Experimental Example 1-8> 1-8>
상기 실험예 1-1에서 화합물 1 대신 상기 화합물 8을 사용한 것을 제외하고는 실험예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다. The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 8 was used instead of compound 1 in Experimental Example 1-1.
<< 실험예Experimental Example 1-9> 1-9>
상기 실험예 1-1에서 화합물 1 대신 상기 화합물 15를 사용한 것을 제외하고는 실험예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 15 was used instead of compound 1 in Experimental Example 1-1.
<< 실험예Experimental Example 1-10> 1-10>
상기 실험예 1-1에서 화합물 1 대신 상기 화합물 16을 사용한 것을 제외하고는 실험예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 16 was used instead of compound 1 in Experimental Example 1-1.
<< 실험예Experimental Example 1-11> 1-11>
상기 실험예 1-1에서 화합물 1 대신 상기 화합물 17을 사용한 것을 제외하고는 실험예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 17 was used instead of compound 1 in Experimental Example 1-1.
<< 실험예Experimental Example 1-12> 1-12>
상기 실험예 1-1에서 화합물 1 대신 상기 화합물 18을 사용한 것을 제외하고는 실험예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 18 was used instead of compound 1 in Experimental Example 1-1.
<< 실험예Experimental Example 1-13> 1-13>
상기 실험예 1-1에서 화합물 1 대신 상기 화합물 19를 사용한 것을 제외하고는 실험예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다. The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 19 was used instead of compound 1 in Experimental Example 1-1.
<< 실험예Experimental Example 1-14> 1-14>
상기 실험예 1-1에서 화합물 1 대신 상기 화합물 20을 사용한 것을 제외하고는 실험예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 20 was used instead of compound 1 in Experimental Example 1-1.
<< 실험예Experimental Example 1-15> 1-15>
상기 실험예1-1에서 화합물 1 대신 상기 화합물 21을 사용한 것을 제외하고는 실험예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 21 was used instead of compound 1 in Experimental Example 1-1.
<< 실험예Experimental Example 1-16> 1-16>
상기 실험예 1-1에서 화합물 1 대신 상기 화합물 22를 사용한 것을 제외하고는 실험예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 22 was used instead of compound 1 in Experimental Example 1-1.
<< 비교예Comparative example 1-1> 1-1>
상기 실험예 1-1에서 화합물 1 대신 하기 EB 1(TCTA)을 사용한 것을 제외하고는 실험예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured according to the same method as Experimental Example 1-1 except for using the following EB 1 (TCTA) instead of compound 1 in Experimental Example 1-1.
[EB 1][EB 1]
Figure PCTKR2016011421-appb-I000121
Figure PCTKR2016011421-appb-I000121
<< 비교예Comparative example 1-2> 1-2>
상기 실험예 1-1에서 화합물 1 대신 EB 2를 사용한 것을 제외하고는 실험예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that EB 2 was used instead of compound 1 in Experimental Example 1-1.
[EB 2][EB 2]
Figure PCTKR2016011421-appb-I000122
Figure PCTKR2016011421-appb-I000122
실험예 1-1 내지 1-16 및 비교예 1-1 내지 1-2에 의해 제작된 유기 발광 소자에 전류를 인가하였을 때, 하기 표 1의 결과를 얻었다.When the current was applied to the organic light emitting devices manufactured by Experimental Examples 1-1 to 1-16 and Comparative Examples 1-1 to 1-2, the results of Table 1 were obtained.
화합물(전자억제층)Compound (electron suppression layer) 전압(V@10mA/cm2)Voltage (V @ 10mA / cm 2 ) 효율(cd/A@10mA/cm2)Efficiency (cd / A @ 10mA / cm 2 ) 색좌표(x,y)Color coordinates (x, y)
실험예 1-1Experimental Example 1-1 화합물 1Compound 1 3.553.55 5.405.40 (0.139, 0.125)(0.139, 0.125)
실험예 1-2Experimental Example 1-2 화합물 2Compound 2 3.623.62 5.355.35 (0.138, 0.126)(0.138, 0.126)
실험예 1-3Experimental Example 1-3 화합물 3Compound 3 3.473.47 5.595.59 (0.138, 0.127)(0.138, 0.127)
실험예 1-4Experimental Example 1-4 화합물 4Compound 4 3.483.48 5.575.57 (0.137, 0.125)(0.137, 0.125)
실험예 1-5Experimental Example 1-5 화합물 5Compound 5 3.493.49 5.585.58 (0.137, 0.125)(0.137, 0.125)
실험예 1-6Experimental Example 1-6 화합물 6Compound 6 3.443.44 5.515.51 (0.137, 0.127)(0.137, 0.127)
실험예 1-7Experimental Example 1-7 화합물 7Compound 7 3.433.43 5.535.53 (0.137, 0.125)(0.137, 0.125)
실험예 1-8Experimental Example 1-8 화합물 8Compound 8 3.443.44 5.555.55 (0.137, 0.125)(0.137, 0.125)
실험예 1-9Experimental Example 1-9 화합물 15Compound 15 3.533.53 5.445.44 (0.138, 0.125)(0.138, 0.125)
실험예 1-10Experimental Example 1-10 화합물 16Compound 16 3.583.58 5.435.43 (0.137, 0.125)(0.137, 0.125)
실험예 1-11Experimental Example 1-11 화합물 17Compound 17 3.533.53 5.415.41 (0.137, 0.125)(0.137, 0.125)
실험예 1-12Experimental Example 1-12 화합물 18Compound 18 3.553.55 5.415.41 (0.137, 0.125)(0.137, 0.125)
실험예 1-13Experimental Example 1-13 화합물 19Compound 19 3.623.62 5.555.55 (0.138, 0.126)(0.138, 0.126)
실험예 1-14Experimental Example 1-14 화합물 20Compound 20 3.673.67 5.545.54 (0.137, 0.125)(0.137, 0.125)
실험예 1-15Experimental Example 1-15 화합물 21Compound 21 3.603.60 5.565.56 (0.137, 0.127)(0.137, 0.127)
실험예 1-16Experimental Example 1-16 화합물 22Compound 22 3.613.61 5.585.58 (0.137, 0.127)(0.137, 0.127)
비교예 1-1Comparative Example 1-1 EB 1(TCTA)EB 1 (TCTA) 4.564.56 4.324.32 (0.138, 0.127) (0.138, 0.127)
비교예 1-2Comparative Example 1-2 EB 2EB 2 4.254.25 4.584.58 (0.139, 0.125)(0.139, 0.125)
상기 표 1에서 보는 바와 같이 본 발명에 따른 상기 화학식 1로 표시되는 화합물을 유기 발광 소자에서 전자억제층으로 사용하는 실험예 1-1 내지 1-16의 유기 발광 소자는 종래 TCTA를 사용하는 비교예 1, 본원 발명의 화학식 1과 유사한 코어구조를 가지는 비교예 2보다 저전압, 고효율의 특성을 나타내는 것을 알 수 있었다.As shown in Table 1, the organic light emitting device of Experimental Examples 1-1 to 1-16 using the compound represented by Chemical Formula 1 according to the present invention as an electron suppressing layer in an organic light emitting device is a comparative example using conventional TCTA. 1, it was found that the characteristics of the lower voltage, higher efficiency than Comparative Example 2 having a core structure similar to the general formula (1) of the present invention.
본 발명에 따른 상기 화학식 1의 화합물은 전자 억제 능력이 우수하여 저전압 및 고효율의 특성을 보이며 유기 발광 소자에 적용 가능함을 확인할 수 있었다. The compound of Chemical Formula 1 according to the present invention was excellent in electron suppression ability, showed low voltage and high efficiency, and could be applied to an organic light emitting device.
<< 실험예Experimental Example 2-1> 2-1>
합성예에서 합성된 화합물들을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후, 하기와 같은 방법으로 녹색 유기 발광 소자를 제조하였다.After the compounds synthesized in the synthesis example was subjected to high purity sublimation purification by a commonly known method, a green organic light emitting device was manufactured by the following method.
ITO(indium tin oxide)가 1,000Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이 때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀러포어사(Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알코올, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 수송시켰다.A glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and ultrasonically cleaned. At this time, Fischer Co. product was used as a detergent, and distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water. After ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After washing the distilled water, ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
이렇게 준비된 ITO 투명 전극 위에 화합물 11을 호스트로 이용하여, m-MTDATA(60nm) / TCTA(80nm) / 화합물 11 + 10 % Ir(ppy)3(300nm)/ BCP(10 nm) / Alq3(30nm) / LiF(1nm) / Al (200nm) 순으로 발광 소자를 구성하여 유기 발광 소자를 제조하였다.Using the compound 11 as a host on the prepared ITO transparent electrode, m-MTDATA (60 nm) / TCTA (80 nm) / Compound 11 + 10% Ir (ppy) 3 (300 nm) / BCP (10 nm) / Alq 3 (30 nm) The organic light emitting device was manufactured by constructing the light emitting device in the order of) / LiF (1nm) / Al (200nm).
m-MTDATA, TCTA, Ir(ppy)3 및 BCP의 구조는 각각 하기와 같다.The structures of m-MTDATA, TCTA, Ir (ppy) 3 and BCP are as follows.
Figure PCTKR2016011421-appb-I000123
Figure PCTKR2016011421-appb-I000123
[화합물 11][Compound 11]
Figure PCTKR2016011421-appb-I000124
Figure PCTKR2016011421-appb-I000124
<< 실험예Experimental Example 2-2> 2-2>
상기 실험예 2-1에서 화합물 11 대신 상기 화합물 12를 사용한 것을 제외하고는 실험예 2-1과 동일한 방법으로 유기 발광 소자를 제작하였다.The organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 12 was used instead of compound 11 in Experimental Example 2-1.
<< 실험예Experimental Example 2-3> 2-3>
상기 실험예 2-1에서 화합물 11 대신 상기 화합물 13을 사용한 것을 제외하고는 실험예 2-1과 동일한 방법으로 유기 발광 소자를 제작하였다. The organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 13 was used instead of compound 11 in Experimental Example 2-1.
<< 실험예Experimental Example 2-4> 2-4>
상기 실험예 2-1에서 화합물 11 대신 상기 화합물 14를 사용한 것을 제외하고는 실험예 2-1과 동일한 방법으로 유기 발광 소자를 제작하였다. The organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 14 was used instead of compound 11 in Experimental Example 2-1.
<< 실험예Experimental Example 2-5> 2-5>
상기 실험예 2-1에서 화합물 11 대신 상기 화합물 25를 사용한 것을 제외하고는 실험예 2-1과 동일한 방법으로 유기 발광 소자를 제작하였다. The organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 25 was used instead of compound 11 in Experimental Example 2-1.
<< 실험예Experimental Example 2-6> 2-6>
상기 실험예 2-1에서 화합물 11 대신 상기 화합물 26을 사용한 것을 제외하고는 실험예 2-1과 동일한 방법으로 유기 발광 소자를 제작하였다. The organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 26 was used instead of compound 11 in Experimental Example 2-1.
<< 실험예Experimental Example 2-7> 2-7>
상기 실험예 2-1에서 화합물 11 대신 상기 화합물 27을 사용한 것을 제외하고는 실험예 2-1과 동일한 방법으로 유기 발광 소자를 제작하였다. The organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 27 was used instead of compound 11 in Experimental Example 2-1.
<< 실험예Experimental Example 2-8> 2-8>
상기 실험예 2-1에서 화합물 11 대신 상기 화합물 28을 사용한 것을 제외하고는 실험예 2-1과 동일한 방법으로 유기 발광 소자를 제작하였다. The organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 28 was used instead of compound 11 in Experimental Example 2-1.
<< 비교예Comparative example 1> 1>
상기 실험예 2-1에서 화합물 11 대신 하기 GH 1(CBP)를 사용한 것을 제외하고는 실험예 2-1과 동일한 방법으로 유기 발광 소자를 제작하였다. An organic light emitting diode was manufactured according to the same method as Experimental Example 2-1 except for using the following GH 1 (CBP) instead of the compound 11 in Experimental Example 2-1.
[GH 1][GH 1]
Figure PCTKR2016011421-appb-I000125
Figure PCTKR2016011421-appb-I000125
<< 비교예Comparative example 2> 2>
상기 실험예 2-1에서 화합물 11 대신 하기 GH 2를 사용한 것을 제외하고는 실험예 2-1과 동일한 방법으로 유기 발광 소자를 제작하였다. An organic light emitting diode was manufactured according to the same method as Experimental Example 2-1 except for using the following GH 2 instead of the compound 11 in Experimental Example 2-1.
[GH 2][GH 2]
Figure PCTKR2016011421-appb-I000126
Figure PCTKR2016011421-appb-I000126
실험예 2-1 내지 2-8 및 비교예 1 내지 2에 의해 제작된 유기 발광 소자에 전류를 인가하였을 때, 하기 표 2의 결과를 얻었다.When the current was applied to the organic light emitting devices manufactured by Experimental Examples 2-1 to 2-8 and Comparative Examples 1 to 2, the results of Table 2 were obtained.
화합물(호스트)Compound (Host) 전압(V@10mA/cm2)Voltage (V @ 10mA / cm 2 ) 효율(cd/A@10mA/cm2)Efficiency (cd / A @ 10mA / cm 2 ) EL 피크(nm)EL peak (nm)
실험예 2-1Experimental Example 2-1 화합물 11Compound 11 5.185.18 46.9346.93 517517
실험예 2-2Experimental Example 2-2 화합물 12Compound 12 5.265.26 45.2445.24 516516
실험예 2-3Experimental Example 2-3 화합물 13Compound 13 5.155.15 46.5446.54 518518
실험예 2-4Experimental Example 2-4 화합물 14Compound 14 5.295.29 45.1545.15 517517
실험예 2-5Experimental Example 2-5 화합물 25Compound 25 5.285.28 45.3145.31 515515
실험예 2-6Experimental Example 2-6 화합물 26Compound 26 5.135.13 46.6346.63 516516
실험예 2-7Experimental Example 2-7 화합물 27Compound 27 5.295.29 45.4245.42 516516
실험예 2-8Experimental Example 2-8 화합물 28Compound 28 5.275.27 45.5445.54 517517
비교예 1Comparative Example 1 GH 1(CBP)GH 1 (CBP) 7.217.21 35.4135.41 517517
비교예 2Comparative Example 2 GH 2 GH 2 6.516.51 39.5639.56 517517
실험 결과, 본 발명에 따른 상기 화학식 1로 표시되는 화합물을 녹색 발광층의 호스트 물질로 사용하는 실험예 2-1 내지 2-8의 녹색 유기 발광 소자는 종래 CBP를 사용하는 비교예 1 및 본원 발명의 화학식 1과 유사한 코어구조를 가지는 비교예 2의 녹색 유기 발광 소자보다 전류효율 및 구동전압 면에서 우수한 성능을 나타내는 것을 확인할 수 있었다.As a result, the green organic light emitting device of Experimental Examples 2-1 to 2-8 using the compound represented by Chemical Formula 1 according to the present invention as a host material of the green light emitting layer was compared with Comparative Example 1 using conventional CBP and the present invention. It was confirmed that the green organic light emitting diode of Comparative Example 2 having a core structure similar to that of Chemical Formula 1 exhibited superior performance in terms of current efficiency and driving voltage.
이상을 통해 본 발명의 바람직한 실시예(전자억제층, 녹색발광층)에 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 preferred embodiments of the present invention (electron suppression layer, green light emitting layer) have been described above, the present invention is not limited thereto, and various modifications can be made within the scope of the claims and the detailed description of the invention. This also belongs to the scope of the invention.

Claims (25)

  1. 하기 화학식 1로 표시되는 화합물: Compound represented by the following formula (1):
    [화학식 1][Formula 1]
    Figure PCTKR2016011421-appb-I000127
    Figure PCTKR2016011421-appb-I000127
    상기 화학식 1에 있어서, In Chemical Formula 1,
    R1 내지 R4는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 치환 또는 비치환된 아민기; 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 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있고,R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may be combined with an adjacent group to form a substituted or unsubstituted ring,
    a는 0 내지 10의 정수이며, a is an integer of 0 to 10,
    b는 0 내지 7의 정수이고, b is an integer of 0 to 7,
    c는 0 내지 5의 정수이며, c is an integer from 0 to 5,
    d는 0 내지 4의 정수이고,d is an integer of 0 to 4,
    a, b, c 및 d가 각각 2 이상인 경우 괄호 안의 구조는 서로 같거나 상이하다.When a, b, c and d are each 2 or more, the structures in parentheses are the same or different from each other.
  2. 청구항 1에 있어서, 상기 화학식 1의 a는 1 내지 10이고, R1 중 적어도 하나는 -(L)m-A로 표시되며, L은 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고, m은 1 내지 10의 정수이며, A는 -NAr1Ar2; 치환 또는 비치환된 N 함유 헤테로고리기; -P(=O)R5R6; 치환 또는 비치환된 안트라센기; 또는 할로겐기 또는 니트릴기로 치환된 아릴기이고, Ar1, Ar2, R5 및 R6는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 치환 또는 비치환된 아민기; 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 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있는 것인 화합물.The method according to claim 1, a of Formula 1 is 1 to 10, at least one of R1 is represented by-(L) mA, L is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group, m is an integer from 1 to 10, A is -NAr1Ar2; Substituted or unsubstituted N-containing heterocyclic group; -P (= 0) R5R6; Substituted or unsubstituted anthracene group; Or an aryl group substituted with a halogen group or a nitrile group, Ar1, Ar2, R5 and R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group, or a compound which can combine with an adjacent group to form a substituted or unsubstituted ring.
  3. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 2로 표시되는 것인 화합물:The compound of claim 1, wherein Formula 1 is represented by Formula 2 below:
    [화학식 2][Formula 2]
    Figure PCTKR2016011421-appb-I000128
    Figure PCTKR2016011421-appb-I000128
    상기 화학식 2에 있어서,In Chemical Formula 2,
    R2 내지 R4, b, c 및 d의 정의는 화학식 1에서와 같고,Definitions of R2 to R4, b, c and d are the same as in formula (1),
    R11의 정의는 R1 내지 R4와 같으며,R11 is defined as R1 to R4,
    L은 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
    Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 치환 또는 비치환된 아민기; 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 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있으며,Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may be combined with an adjacent group to form a substituted or unsubstituted ring,
    p는 1 내지 10의 정수이고,p is an integer from 1 to 10,
    f는 0 내지 10의 정수이며,f is an integer of 0 to 10,
    1 ≤ p+f ≤ 10이고,1 ≦ p + f ≦ 10,
    m은 1 내지 10의 정수이며,m is an integer from 1 to 10,
    p, f 및 m이 각각 2 이상인 경우 괄호 안의 구조는 서로 같거나 상이하다.When p, f and m are each 2 or more, the structures in parentheses are the same or different from each other.
  4. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 3 또는 4로 표시되는 것인 화합물:The compound of claim 1, wherein Formula 1 is represented by the following Formula 3 or 4:
    [화학식 3][Formula 3]
    Figure PCTKR2016011421-appb-I000129
    Figure PCTKR2016011421-appb-I000129
    [화학식 4][Formula 4]
    Figure PCTKR2016011421-appb-I000130
    Figure PCTKR2016011421-appb-I000130
    상기 화학식 3 및 4에 있어서,In Chemical Formulas 3 and 4,
    R2 내지 R4, b, c 및 d의 정의는 화학식 1에서와 같고,Definitions of R2 to R4, b, c and d are the same as in formula (1),
    L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이며, L1 and L2 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
    Ar1 내지 Ar4, Y1 및 Y2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 치환 또는 비치환된 아민기; 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 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있고,Ar1 to Ar4, Y1 and Y2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may be combined with an adjacent group to form a substituted or unsubstituted ring,
    y1은 0 내지 9의 정수이며, y1 is an integer of 0 to 9,
    y2는 0 내지 8의 정수이고, y2 is an integer of 0 to 8,
    m1 및 m2는 서로 같거나 상이하고, 각각 독립적으로 1 내지 10의 정수이며,m1 and m2 are the same as or different from each other, and each independently an integer of 1 to 10,
    y1, y2, m1 및 m2가 각각 2 이상인 경우 괄호 안의 구조는 서로 같거나 상이하다.When y1, y2, m1 and m2 are each 2 or more, the structures in parentheses are the same or different from each other.
  5. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 5 내지 8 중 어느 하나로 표시되는 것인 화합물:The compound of claim 1, wherein Formula 1 is represented by any one of Formulas 5 to 8.
    [화학식 5][Formula 5]
    Figure PCTKR2016011421-appb-I000131
    Figure PCTKR2016011421-appb-I000131
    [화학식 6][Formula 6]
    Figure PCTKR2016011421-appb-I000132
    Figure PCTKR2016011421-appb-I000132
    [화학식 7][Formula 7]
    Figure PCTKR2016011421-appb-I000133
    Figure PCTKR2016011421-appb-I000133
    [화학식 8][Formula 8]
    Figure PCTKR2016011421-appb-I000134
    Figure PCTKR2016011421-appb-I000134
    상기 화학식 5 내지 8에 있어서, In Chemical Formulas 5 to 8,
    R2 내지 R4, b, c 및 d의 정의는 화학식 1에서와 같고, Definitions of R2 to R4, b, c and d are the same as in formula (1),
    L1은 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이며, L 1 is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
    Ar1, Ar2 및 Y1는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 치환 또는 비치환된 아민기; 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 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있고,Ar1, Ar2 and Y1 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may be combined with an adjacent group to form a substituted or unsubstituted ring,
    y1은 0 내지 9의 정수이며, y1 is an integer of 0 to 9,
    m1 및 m2는 서로 같거나 상이하고, 각각 독립적으로 1 내지 10의 정수이며,m1 and m2 are the same as or different from each other, and each independently an integer of 1 to 10,
    y1 및 m1이 각각 2 이상인 경우 괄호 안의 구조는 서로 같거나 상이하다.When y1 and m1 are each 2 or more, the structures in parentheses are the same or different from each other.
  6. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 9 내지 12 중 어느 하나로 표시되는 것인 화합물:The compound of claim 1, wherein Formula 1 is represented by any one of Formulas 9 to 12:
    [화학식 9][Formula 9]
    Figure PCTKR2016011421-appb-I000135
    Figure PCTKR2016011421-appb-I000135
    [화학식 10][Formula 10]
    Figure PCTKR2016011421-appb-I000136
    Figure PCTKR2016011421-appb-I000136
    [화학식 11][Formula 11]
    Figure PCTKR2016011421-appb-I000137
    Figure PCTKR2016011421-appb-I000137
    [화학식 12][Formula 12]
    Figure PCTKR2016011421-appb-I000138
    Figure PCTKR2016011421-appb-I000138
    상기 화학식 9 내지 12에 있어서, In Chemical Formulas 9 to 12,
    R2 내지 R4, b, c 및 d의 정의는 화학식 1에서와 같고, Definitions of R2 to R4, b, c and d are the same as in formula (1),
    L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이며, L1 and L2 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
    Ar1 내지 Ar4 및 Y2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 치환 또는 비치환된 아민기; 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 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있고,Ar1 to Ar4 and Y2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may be combined with an adjacent group to form a substituted or unsubstituted ring,
    y2는 0 내지 8의 정수이고, y2 is an integer of 0 to 8,
    m1 및 m2는 서로 같거나 상이하고, 각각 독립적으로 1 내지 10의 정수이며,m1 and m2 are the same as or different from each other, and each independently an integer of 1 to 10,
    y2, m1 및 m2가 각각 2 이상인 경우 괄호 안의 구조는 서로 같거나 상이하다.When y2, m1 and m2 are each 2 or more, the structures in parentheses are the same or different from each other.
  7. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 13 또는 14로 표시되는 것인 화합물:The compound according to claim 1, wherein Formula 1 is represented by Formula 13 or 14 below:
    [화학식 13][Formula 13]
    Figure PCTKR2016011421-appb-I000139
    Figure PCTKR2016011421-appb-I000139
    [화학식 14][Formula 14]
    Figure PCTKR2016011421-appb-I000140
    Figure PCTKR2016011421-appb-I000140
    상기 화학식 13 및 14에 있어서,In Chemical Formulas 13 and 14,
    R2 내지 R4, b, c 및 d의 정의는 화학식 1과 같고,Definitions of R2 to R4, b, c and d is the same as in formula (1),
    R11의 정의는 R2 내지 R4의 정의와 같고,The definition of R11 is the same as the definition of R2 to R4,
    L, L11 및 L21은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L, L11 and L21 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
    Ar11, Ar12, Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 치환 또는 비치환된 아민기; 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 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있으며,Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may be combined with an adjacent group to form a substituted or unsubstituted ring,
    p는 1 내지 10의 정수이고,p is an integer from 1 to 10,
    f는 0 내지 10의 정수이며,f is an integer of 0 to 10,
    1 ≤ p+f ≤ 10이고,1 ≦ p + f ≦ 10,
    m, m11 및 m21은 서로 같거나 상이하고, 각각 독립적으로 1 내지 10의 정수이며,m, m11 and m21 are the same as or different from each other, and each independently an integer of 1 to 10,
    p, f, m, m11 및 m21이 각각 2 이상인 경우 괄호 안의 구조는 서로 같거나 상이하다.When p, f, m, m11 and m21 are each 2 or more, the structures in parentheses are the same or different from each other.
  8. 청구항 1에 있어서, 상기 화학식 1의 화합물은 하기 구조식들 중에서 선택된 어느 하나인 것인 화합물:The compound of claim 1, wherein the compound of Formula 1 is any one selected from the following structural formulas:
    Figure PCTKR2016011421-appb-I000141
    Figure PCTKR2016011421-appb-I000141
    Figure PCTKR2016011421-appb-I000142
    Figure PCTKR2016011421-appb-I000142
    Figure PCTKR2016011421-appb-I000143
    Figure PCTKR2016011421-appb-I000143
    Figure PCTKR2016011421-appb-I000144
    Figure PCTKR2016011421-appb-I000144
    Figure PCTKR2016011421-appb-I000145
    Figure PCTKR2016011421-appb-I000145
    Figure PCTKR2016011421-appb-I000146
    Figure PCTKR2016011421-appb-I000146
    Figure PCTKR2016011421-appb-I000147
    Figure PCTKR2016011421-appb-I000147
    Figure PCTKR2016011421-appb-I000148
    Figure PCTKR2016011421-appb-I000148
    Figure PCTKR2016011421-appb-I000149
    Figure PCTKR2016011421-appb-I000149
    Figure PCTKR2016011421-appb-I000150
    Figure PCTKR2016011421-appb-I000150
  9. 청구항 1에 있어서, 상기 화학식 1의 화합물은 하기 구조식들 중에서 선택된 어느 하나인 것인 화합물:The compound of claim 1, wherein the compound of Formula 1 is any one selected from the following structural formulas:
    Figure PCTKR2016011421-appb-I000151
    Figure PCTKR2016011421-appb-I000151
    Figure PCTKR2016011421-appb-I000152
    Figure PCTKR2016011421-appb-I000152
    Figure PCTKR2016011421-appb-I000153
    Figure PCTKR2016011421-appb-I000153
  10. 청구항 1에 있어서, 상기 화학식 1의 화합물은 하기 구조식들 중에서 선택된 어느 하나인 것인 화합물:The compound of claim 1, wherein the compound of Formula 1 is any one selected from the following structural formulas:
    Figure PCTKR2016011421-appb-I000154
    Figure PCTKR2016011421-appb-I000154
    Figure PCTKR2016011421-appb-I000155
    Figure PCTKR2016011421-appb-I000155
  11. 청구항 1에 있어서, 상기 화학식 1의 a는 1 또는 2이고, R1 중 적어도 하나는 -(L)m-A로 표시되며, L은 직접결합; 또는 탄소수 6 내지 20의 아릴렌기이고, m은 1 또는 2이며, A는 아릴기 또는 헤테로고리기로 치환 또는 비치환된 N 함유 헤테로고리기이며, 여기서 N 함유 헤테로고리기는 트리아진기, 피리미딘기, 피리딘기, 퀴나졸린기, 퀴놀린기, 이소퀴놀린기, 벤즈이미다졸기, 카바졸기, 또는 벤조카바졸기인 것인 화합물.The compound of claim 1, wherein a in Formula 1 is 1 or 2, at least one of R 1 is represented by-(L) m-A, and L is a direct bond; Or an arylene group having 6 to 20 carbon atoms, m is 1 or 2, and A is an N-containing heterocyclic group unsubstituted or substituted with an aryl group or a heterocyclic group, wherein the N-containing heterocyclic group is a triazine group, a pyrimidine group, A compound that is a pyridine group, quinazoline group, quinoline group, isoquinoline group, benzimidazole group, carbazole group, or benzocarbazole group.
  12. 청구항 1에 있어서, 상기 화학식 1의 화합물은 하기 구조식들 중에서 선택된 어느 하나인 것인 화합물: The compound of claim 1, wherein the compound of Formula 1 is any one selected from the following structural formulas:
    Figure PCTKR2016011421-appb-I000156
    Figure PCTKR2016011421-appb-I000156
    Figure PCTKR2016011421-appb-I000157
    Figure PCTKR2016011421-appb-I000157
    Figure PCTKR2016011421-appb-I000158
    Figure PCTKR2016011421-appb-I000158
    Figure PCTKR2016011421-appb-I000159
    Figure PCTKR2016011421-appb-I000159
    Figure PCTKR2016011421-appb-I000160
    Figure PCTKR2016011421-appb-I000160
    Figure PCTKR2016011421-appb-I000161
    Figure PCTKR2016011421-appb-I000161
    Figure PCTKR2016011421-appb-I000162
    Figure PCTKR2016011421-appb-I000162
  13. 청구항 1에 있어서, 상기 화학식 1의 a는 1 또는 2이고, R1 중 적어도 하나는 -(L)m-A로 표시되며, L은 직접결합; 또는 탄소수 6 내지 20의 아릴렌기이고, m은 1 또는 2이며, A는 -P(=O)R5R6이고, R5 및 R6는 서로 같거나 상이하고 각각 독립적으로 탄소수 6 내지 20의 아릴기인 것인 화합물.The compound of claim 1, wherein a in Formula 1 is 1 or 2, at least one of R 1 is represented by-(L) m-A, and L is a direct bond; Or an arylene group having 6 to 20 carbon atoms, m is 1 or 2, A is -P (= 0) R 5 R 6, and R 5 and R 6 are the same as or different from each other and are each independently an aryl group having 6 to 20 carbon atoms; .
  14. 청구항 1에 있어서, 상기 화학식 1의 화합물은 하기 구조식들 중에서 선택된 어느 하나인 것인 화합물:The compound of claim 1, wherein the compound of Formula 1 is any one selected from the following structural formulas:
    Figure PCTKR2016011421-appb-I000163
    Figure PCTKR2016011421-appb-I000163
  15. 청구항 1에 있어서, 상기 화학식 1의 a는 1 또는 2이고, R1 중 적어도 하나는 -(L)m-A로 표시되며, L은 직접결합; 아릴렌기; 또는 헤테로아릴렌기이고, m은 1 또는 2이며, A는 할로겐기 또는 니트릴기로 치환 또는 비치환된 아릴기로 치환된 안트라센기; 또는 할로겐기 또는 니트릴기로 치환된 아릴기인 것인 화합물.The compound of claim 1, wherein a in Formula 1 is 1 or 2, at least one of R 1 is represented by-(L) m-A, and L is a direct bond; Arylene group; Or a heteroarylene group, m is 1 or 2, A is an anthracene group substituted with an aryl group unsubstituted or substituted with a halogen group or a nitrile group; Or an aryl group substituted with a halogen group or a nitrile group.
  16. 청구항 1에 있어서, 상기 화학식 1의 화합물은 하기 구조식들 중에서 선택된 어느 하나인 것인 화합물:The compound of claim 1, wherein the compound of Formula 1 is any one selected from the following structural formulas:
    Figure PCTKR2016011421-appb-I000164
    Figure PCTKR2016011421-appb-I000164
  17. 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 청구항 1 내지 16 중 어느 하나의 항에 따른 화합물을 포함하는 것인 유기 발광 소자.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 comprises a compound according to any one of claims 1 to 16. Organic light emitting device.
  18. 청구항 17에 있어서, 상기 유기물층은 정공주입층, 정공수송층, 전자억제층, 발광층, 정공억제층, 전자수송층 및 전자주입층 중 적어도 한 층을 포함하는 것인 유기 발광 소자.The organic light emitting device of claim 17, wherein the organic material layer comprises at least one of a hole injection layer, a hole transport layer, an electron suppression layer, a light emitting layer, a hole suppression layer, an electron transport layer, and an electron injection layer.
  19. 청구항 17에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화합물을 포함하는 것인 유기 발광 소자.The organic light emitting device of claim 17, wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises the compound.
  20. 청구항 17에 있어서, 상기 유기물층은 전자억제층을 포함하고, 상기 전자억제층은 상기 화합물을 포함하는 것인 유기 발광 소자.The organic light emitting device of claim 17, wherein the organic material layer comprises an electron suppression layer, and the electron suppression layer comprises the compound.
  21. 청구항 17에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 하기 화학식 15로 표시되는 화합물을 포함하는 것인 유기 발광 소자:The organic light emitting device of claim 17, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 15:
    [화학식 15][Formula 15]
    Figure PCTKR2016011421-appb-I000165
    Figure PCTKR2016011421-appb-I000165
    상기 화학식 15에 있어서,In Chemical Formula 15,
    z1은 1 이상의 정수이고, z1이 2 이상의 정수인 경우 괄호 안의 구조는 서로 같거나 상이하고,z1 is an integer of 1 or more, and if z1 is an integer of 2 or more, the structures in parentheses are the same 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 크라이센기이고,Ar100 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 higher chrysene group,
    L100은 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L100 is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
    R100 및 R101은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아릴알킬기; 또는 치환 또는 비치환된 헤테로고리기이거나, 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.R100 and R101 are the same as or different from each other, and each independently 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 heterocyclic group, or may be combined with each other to form a substituted or unsubstituted ring.
  22. 청구항 21에 있어서, 상기 z1은 2이고, Ar100은 2가의 파이렌기이며, L100은 직접결합이고, R100 및 R101은 서로 같거나 상이하고 각각 독립적으로 알킬게르마늄기로 치환 또는 비치환된 아릴기인 것인 유기 발광 소자.The organic compound of claim 21, wherein z1 is 2, Ar100 is a divalent pyrene group, L100 is a direct bond, and R100 and R101 are the same or different from each other, and each independently an aryl group unsubstituted or substituted with an alkylgermanium group. Light emitting element.
  23. 청구항 17에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 하기 화학식 16으로 표시되는 화합물을 포함하는 것인 유기 발광 소자:The organic light emitting device of claim 17, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 16:
    [화학식 16][Formula 16]
    Figure PCTKR2016011421-appb-I000166
    Figure PCTKR2016011421-appb-I000166
    상기 화학식 16에 있어서,In Chemical Formula 16,
    Ar101 및 Ar102는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,Ar101 and Ar102 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
    L101 및 L102는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L101 and L102 are the same as or different from each other, and are each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
    R102는 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 치환 또는 비치환된 아민기; 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 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,R102 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
    z2 및 z3은 서로 같거나 상이하고 각각 독립적으로 1 또는 2의 정수이고, z4는 0 내지 8의 정수이고, z2 내지 z4가 2 이상인 경우 괄호 안의 치환기는 서로 같거나 상이하고,z2 and z3 are the same as or different from each other, and each independently an integer of 1 or 2, z4 is an integer of 0 to 8, when z2 to z4 is 2 or more, the substituents in parentheses are the same or different from each other,
    v는 1 이상의 정수이고, v가 2 이상의 정수인 경우 괄호 안의 치환기는 서로 같거나 상이하다.v is an integer of 1 or more, and when v is an integer of 2 or more, the substituents in parentheses are the same as or different from each other.
  24. 청구항 23에 있어서, 상기 Ar101은 2-나프틸기이고, Ar102는 1-나프틸기이고, L101은 페닐렌기이고, L102는 직접결합이고, z2는 1이고, R102는 수소이고, v는 1인 것인 유기 발광 소자.The method of claim 23, wherein Ar101 is a 2-naphthyl group, Ar102 is a 1-naphthyl group, L101 is a phenylene group, L102 is a direct bond, z2 is 1, R102 is hydrogen, v is 1 Organic light emitting device.
  25. 청구항 21에 있어서, 상기 발광층은 하기 화학식 16으로 표시되는 화합물을 포함하는 것인 유기 발광 소자:The organic light emitting device of claim 21, wherein the light emitting layer comprises a compound represented by Chemical Formula 16:
    [화학식 16][Formula 16]
    Figure PCTKR2016011421-appb-I000167
    Figure PCTKR2016011421-appb-I000167
    상기 화학식 16에 있어서,In Chemical Formula 16,
    Ar101 및 Ar102는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,Ar101 and Ar102 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
    L101 및 L102는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L101 and L102 are the same as or different from each other, and are each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
    R102는 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 치환 또는 비치환된 아민기; 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 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,R102 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine 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; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
    z2 및 z3은 서로 같거나 상이하고 각각 독립적으로 1 또는 2의 정수이고, z4는 0 내지 8의 정수이고, z2 내지 z4가 2 이상인 경우 괄호 안의 치환기는 서로 같거나 상이하고,z2 and z3 are the same as or different from each other, and each independently an integer of 1 or 2, z4 is an integer of 0 to 8, when z2 to z4 is 2 or more, the substituents in parentheses are the same or different from each other,
    v는 1 이상의 정수이고, v가 2 이상의 정수인 경우 괄호 안의 치환기는 서로 같거나 상이하다.v is an integer of 1 or more, and when v is an integer of 2 or more, the substituents in parentheses are the same as or different from each other.
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11697666B2 (en) 2021-04-16 2023-07-11 Gilead Sciences, Inc. Methods of preparing carbanucleosides using amides
US11767337B2 (en) 2020-02-18 2023-09-26 Gilead Sciences, Inc. Antiviral compounds

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109456296A (en) * 2018-10-29 2019-03-12 吉林奥来德光电材料股份有限公司 A kind of luminous organic material, preparation method and application
KR102391296B1 (en) * 2019-07-31 2022-04-27 주식회사 엘지화학 Organic light emitting device
US20230084250A1 (en) * 2019-11-29 2023-03-16 Lg Chem, Ltd. Organic light emitting device
CN114539075B (en) * 2022-02-14 2023-05-05 上海八亿时空先进材料有限公司 Fluorene derivative and application thereof

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008140134A1 (en) * 2007-05-16 2008-11-20 Canon Kabushiki Kaisha Benzo[a]fluoranthene compound and organic light emitting device using the same
WO2011093067A1 (en) * 2010-01-29 2011-08-04 出光興産株式会社 Dibenzofluoranthene compound and organic thin-film solar cell using same
CN102532002A (en) * 2010-12-17 2012-07-04 清华大学 Tetrahydroanthracene compound containing terpyridyl group and application thereof
KR20140021969A (en) * 2012-08-09 2014-02-21 희성소재 (주) Novel compounds, organic light emitting device display and organic solar battery using the same
KR101560102B1 (en) * 2014-11-20 2015-10-13 주식회사 엘지화학 Organic light emitting device

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008140134A1 (en) * 2007-05-16 2008-11-20 Canon Kabushiki Kaisha Benzo[a]fluoranthene compound and organic light emitting device using the same
WO2011093067A1 (en) * 2010-01-29 2011-08-04 出光興産株式会社 Dibenzofluoranthene compound and organic thin-film solar cell using same
CN102532002A (en) * 2010-12-17 2012-07-04 清华大学 Tetrahydroanthracene compound containing terpyridyl group and application thereof
KR20140021969A (en) * 2012-08-09 2014-02-21 희성소재 (주) Novel compounds, organic light emitting device display and organic solar battery using the same
KR101560102B1 (en) * 2014-11-20 2015-10-13 주식회사 엘지화학 Organic light emitting device

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11767337B2 (en) 2020-02-18 2023-09-26 Gilead Sciences, Inc. Antiviral compounds
US11697666B2 (en) 2021-04-16 2023-07-11 Gilead Sciences, Inc. Methods of preparing carbanucleosides using amides

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