WO2019088799A1 - 다환 화합물 및 이를 포함하는 유기 발광 소자 - Google Patents

다환 화합물 및 이를 포함하는 유기 발광 소자 Download PDF

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WO2019088799A1
WO2019088799A1 PCT/KR2018/013380 KR2018013380W WO2019088799A1 WO 2019088799 A1 WO2019088799 A1 WO 2019088799A1 KR 2018013380 W KR2018013380 W KR 2018013380W WO 2019088799 A1 WO2019088799 A1 WO 2019088799A1
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substituted
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구기동
금수정
윤정민
김공겸
이칠원
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주식회사 엘지화학
단국대학교 천안캠퍼스 산학협력단
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Priority to CN201880055634.3A priority Critical patent/CN111094302B/zh
Publication of WO2019088799A1 publication Critical patent/WO2019088799A1/ko

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    • H—ELECTRICITY
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    • 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
    • H10K85/658—Organoboranes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • 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
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    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • 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]
    • H10K50/17—Carrier injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers

Definitions

  • the present invention relates to a compound and an organic light emitting device including the same.
  • an organic light emitting element is a light emitting element using an organic semiconductor material, and requires the exchange of holes and / or electrons between the electrode and the organic semiconductor material.
  • the organic light emitting device can be roughly classified into two types according to the operating principle as described below. First, an exciton is formed in an organic material layer by a photon introduced into an element from an external light source. The exciton is separated into an electron and a hole, and the electrons and holes are transferred to different electrodes to be used as a current source Emitting device.
  • the second type is a light emitting device that injects holes and / or electrons into an organic semiconductor material layer that interfaces with the electrode by applying a voltage or current to two or more electrodes, and operates by injected electrons and holes.
  • organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy.
  • An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
  • Such an organic light emitting device When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out.
  • Such an organic light emitting device is known to have characteristics such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, and high contrast.
  • a material used as an organic material layer in an organic light emitting device can be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions.
  • the luminescent material has blue, green and red luminescent materials and yellow and orange luminescent materials necessary for realizing a better natural color depending on the luminescent color.
  • a host / dopant system can be used as a light emitting material.
  • the principle is that when a small amount of dopant having a smaller energy band gap and higher luminous efficiency than a host mainly constituting the light emitting layer is mixed with a light emitting layer in a small amount, the excitons generated in the host are transported as a dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, light of a desired wavelength can be obtained depending on the type of the dopant used.
  • materials constituting the organic material layer in the device such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material and an electron injecting material are supported by stable and efficient materials Development of new materials is continuously required.
  • Patent Document 1 Chinese Patent Laid-Open Publication No. 106467553
  • An embodiment of the present invention provides a compound represented by the following formula (1).
  • A1 is a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle,
  • X1 is N or CR11
  • X2 is N or CR12
  • X3 is N or CR13
  • Ra to Rg, R11 to R13, Ar1 and Ar2 are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; Alkylsilyl groups; An arylsilyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted alkoxyaryl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or may be bonded to adjacent groups to form a substituted or unsubstituted ring,
  • R1 and R2 are connected to the dotted line of the formula (2) to form a ring
  • R21 to R27 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or may be bonded to adjacent groups to form a substituted or unsubstituted ring,
  • A2 is a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle.
  • a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound described above.
  • the compound described in this specification can be used as a material of an organic material layer of an organic light emitting device as a polycyclic fused ring compound containing boron (B).
  • the compound according to at least one embodiment can improve the characteristics of elements such as luminous efficiency, color purity, lifetime characteristics and the like in an organic light emitting device, and a device having a low driving voltage can be obtained.
  • Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4.
  • FIG. 2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is.
  • the present invention provides a compound represented by the following formula (1).
  • B is contained in the compound represented by the following formula (1) and is connected to the dotted line of the formula (2) to form a ring,
  • Aryl groups directly bonded to triaryl borane are bonded using atoms (W) that do not extend nitrogen or other conjugation to improve warping characteristics due to steric hindrance of aryl groups.
  • W atoms
  • the compound of the present invention improves the lifetime, color recall ratio, and charge balance characteristics of conventional organic light emitting devices, and improves the properties such as processability and material degeneration during panel manufacture.
  • A1 is a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle,
  • X1 is N or CR11
  • X2 is N or CR12
  • X3 is N or CR13
  • Ra to Rg, R11 to R13, Ar1 and Ar2 are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; Alkylsilyl groups; An arylsilyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted alkoxyaryl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or may be bonded to adjacent groups to form a substituted or unsubstituted ring,
  • R1 and R2 are connected to the dotted line of the formula (2) to form a ring
  • R21 to R27 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or may be bonded to adjacent groups to form a substituted or unsubstituted ring,
  • A2 is a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle.
  • a member when a member is located on another member, it includes not only the case where the member is in contact with the other member but also the case where another member exists between the two members.
  • substituted means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the substituted position is not limited as long as the substituent is a substitutable position, , Two or more substituents may be the same as or different from each other.
  • the term " substituted or unsubstituted" A halogen group; A hydroxy group; Cyano group (-CN); A nitro group; Silyl group; Boron group; An alkyl group; A cycloalkyl group; An alkoxy group; An alkenyl group; An alkynyl group; An aryloxy group; An aryl group; An amine group; And a heterocyclic group, or that at least two of the substituents exemplified in the above exemplified substituents are substituted with a connected substituent, or have no substituent.
  • a substituent to which at least two substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.
  • examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br) or iodine (I).
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert- And a til group, but are not limited thereto.
  • the cycloalkyl group is not particularly limited, but is preferably a group having 3 to 30 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, But are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, isobutyl, sec-butyl, It is not.
  • the alkoxy group may be linear or branched.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, But are not limited to, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, .
  • the amine group is -NH 2 ; An alkylamine group; N-alkylarylamine groups; An arylamine group; An N-arylheteroarylamine group; An N-alkylheteroarylamine group, and a heteroarylamine group.
  • the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • amine group examples include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl- , Diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenylnaphthylamine group; An N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; An N-biphenyl phenanthrenyl amine group; N-phenylfluorenylamine group; An N-biphenyl phenanthrenyl amine group; N-phenylfluorenylamine group; An N-phenyltriphenylamine group; N-phenanthrenyl fluorenyl
  • the N-alkylarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and an aryl group.
  • the N-arylheteroarylamine group means an amine group in which N in the amine group is substituted with an aryl group and a heteroaryl group.
  • the N-alkylheteroarylamine group means an amine group in which N in the amine group is substituted with an alkyl group and a heteroaryl group.
  • examples of the alkylamine group include a substituted or unsubstituted monoalkylamine group, or a substituted or unsubstituted dialkylamine group.
  • the alkyl group in the alkylamine group may be a linear or branched alkyl group.
  • the alkylamine group containing two or more of the alkyl groups may contain a straight chain alkyl group, a branched chain alkyl group, or a straight chain alkyl group and a branched chain alkyl group at the same time.
  • the alkyl group in the alkylamine group may be selected from the examples of the alkyl group described above.
  • the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, and the like, but are not limited thereto.
  • the silyl group may be -SiR 101 R 102 R 103 , wherein R 101 to R 103 are the same or different and each independently hydrogen; heavy hydrogen; halogen; Cyano; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • an alkylsilyl group means a silyl group substituted with an alkyl group.
  • an arylsilyl group means a silyl group substituted with an aryl group.
  • Specific examples include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl and phenylsilyl groups .
  • the boron group is -BR R 104 may be 105 days, wherein R 104 and R 105 are the same or different and each is independently hydrogen; heavy hydrogen; halogen; Cyano; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • 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 one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto.
  • polycyclic aryl group examples include, but are not limited to, a naphthyl group, an anthracenyl group, an indenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a klycenyl group and a fluorenyl group.
  • a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • the heterocyclic group is a heteroaromatic ring group containing at least one of N, O, P, S, Si and Se.
  • the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30.
  • Examples of the heterocyclic group include pyridyl, pyrrolyl, pyrimidyl, pyridazinyl, furanyl, thiophenyl, carbazole, imidazole, pyrazole, However, the present invention is not limited thereto.
  • heterocyclic group in the present specification, the description of the aforementioned heterocyclic group can be applied, except that the heteroaryl group is aromatic.
  • adjacent The group may mean a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom of the substituent.
  • two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as " adjacent " groups to each other.
  • the "ring” means a hydrocarbon ring; Or a heterocycle.
  • the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from the examples of the cycloalkyl group or the aryl group except the univalent hydrocarbon ring.
  • the hetero ring includes one or more non-carbon atoms and hetero atoms.
  • the hetero atom includes at least one atom selected from the group consisting of N, O, P, S, Si and Se can do.
  • the heterocyclic ring may be monocyclic or polycyclic, and may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and examples of the heteroaryl group may be selected except that the aromatic heterocyclic ring is not monovalent.
  • X1 is N or CR11.
  • R11 is selected from the group consisting of hydrogen; heavy hydrogen; A halogen group; An alkylsilyl group having 1 to 20 carbon atoms; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted arylamine group having 12 to 60 carbon atoms; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, or is bonded to an adjacent group to form a substituted or unsubstituted ring.
  • R11 is hydrogen; heavy hydrogen; A halogen group; A trialkylsilyl group having 3 to 20 carbon atoms; A substituted or unsubstituted methyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted cyclohexyl group; A substituted or unsubstituted diphenylamine group; A substituted or unsubstituted phenyl group; Or a substituted or unsubstituted carbazole group, or is bonded to an adjacent group to form a substituted or unsubstituted ring.
  • R11 is hydrogen; heavy hydrogen; Fluorine (-F); A trimethylsilyl group; Methyl group; tert-butyl group; A cyclohexyl group; Diphenylamine group; A phenyl group; Or a carbazole group, or is bonded to R 21 to form a substituted or unsubstituted ring.
  • X2 is N or CR12
  • X3 is N or CR13
  • X3 is CR13 when X2 is N
  • X2 is CR12 when X3 is N.
  • X2 is N or CR12 and X3 is CR13.
  • X2 is CR12 and X3 is N or CR13.
  • R3 and R12; Or R < 3 > and R < 13 > are connected to the dotted line of formula (2) to form a ring.
  • R12 when R12 is not connected to the dotted line of formula (2) to form a ring, R12 is hydrogen; heavy hydrogen; A halogen group; An alkylsilyl group having 1 to 20 carbon atoms; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted arylamine group having 12 to 60 carbon atoms; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, or is bonded to an adjacent group to form a substituted or unsubstituted ring.
  • R12 when R12 is not connected to the dotted line of formula (2) to form a ring, R12 is hydrogen; heavy hydrogen; A halogen group; A trialkylsilyl group having 3 to 20 carbon atoms; A substituted or unsubstituted methyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted cyclohexyl group; A substituted or unsubstituted diphenylamine group; A substituted or unsubstituted phenyl group; Or a substituted or unsubstituted carbazole group, or is bonded to an adjacent group to form a substituted or unsubstituted ring.
  • R12 when R12 is not connected to the dotted line of formula (2) to form a ring, R12 is hydrogen; heavy hydrogen; Fluorine (-F); A trimethylsilyl group; Methyl group; tert-butyl group; A cyclohexyl group; Diphenylamine group; A phenyl group; Or a carbazole group, or combine with adjacent groups to form a substituted or unsubstituted ring.
  • R13 when R13 is not connected to the dotted line of formula (2) to form a ring, R13 is hydrogen; heavy hydrogen; A halogen group; An alkylsilyl group having 1 to 20 carbon atoms; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted arylamine group having 12 to 60 carbon atoms; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, or is bonded to an adjacent group to form a substituted or unsubstituted ring.
  • R13 when R13 is not connected to the dotted line of formula (2) to form a ring, R13 is hydrogen; heavy hydrogen; A halogen group; A trialkylsilyl group having 3 to 20 carbon atoms; A substituted or unsubstituted methyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted cyclohexyl group; A substituted or unsubstituted diphenylamine group; A substituted or unsubstituted phenyl group; Or a substituted or unsubstituted carbazole group, or is bonded to an adjacent group to form a substituted or unsubstituted ring.
  • R13 when R13 is not connected to the dotted line of formula (2) to form a ring, R13 is hydrogen; heavy hydrogen; Fluorine (-F); A trimethylsilyl group; Methyl group; tert-butyl group; A cyclohexyl group; Diphenylamine group; A phenyl group; Or a carbazole group, or combine with adjacent groups to form a substituted or unsubstituted ring.
  • R13 when R13 is not connected to the dotted line of formula (2) to form a ring, R13 is hydrogen.
  • R3 and R12; Or R < 3 > and R < 13 > are connected to the dotted line of formula (2) to form a ring.
  • Formula 1 may be represented by Formula 1-1 or Formula 1-2.
  • W, X 1, R 1, R 2, A 1, Ar 1 and Ar 2 have the same definitions as in formula (1)
  • X21 and X31 are the same or different and are each independently N or CR41,
  • R41 is hydrogen; heavy hydrogen; A halogen group; Cyano; Alkylsilyl groups; An arylsilyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted alkoxyaryl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or may be bonded to adjacent groups to form a substituted or unsubstituted ring,
  • R3 and R4; And R < 3 > and R < 5 > are connected to the dotted line of formula (2) to form a ring.
  • R41 is hydrogen; heavy hydrogen; A halogen group; An alkylsilyl group having 1 to 20 carbon atoms; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted arylamine group having 12 to 60 carbon atoms; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, or is bonded to an adjacent group to form a substituted or unsubstituted ring.
  • R41 is selected from the group consisting of hydrogen; heavy hydrogen; A halogen group; A trialkylsilyl group having 3 to 20 carbon atoms; A substituted or unsubstituted methyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted cyclohexyl group; A substituted or unsubstituted diphenylamine group; A substituted or unsubstituted phenyl group; Or a substituted or unsubstituted carbazole group, or is bonded to an adjacent group to form a substituted or unsubstituted ring.
  • R41 is selected from the group consisting of hydrogen; heavy hydrogen; Fluorine (-F); A trimethylsilyl group; Methyl group; tert-butyl group; A cyclohexyl group; Diphenylamine group; A phenyl group; Or a carbazole group, or combine with adjacent groups to form a substituted or unsubstituted ring.
  • R21 is a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or is bonded to an adjacent group to form a substituted or unsubstituted ring,
  • R21 is a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or is bonded to an adjacent group to form a substituted or unsubstituted ring.
  • R21 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or may be bonded to adjacent groups to form a substituted or unsubstituted ring.
  • R21 is a substituted or unsubstituted methyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group, or is bonded to an adjacent group to form a substituted or unsubstituted ring.
  • R21 is a methyl group; A phenyl group; A biphenyl group; Or a naphthyl group, or combine with adjacent groups to form a substituted or unsubstituted ring.
  • R22 is a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • R22 is a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
  • R22 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R22 is a substituted or unsubstituted methyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.
  • R22 is a methyl group; A phenyl group; A biphenyl group; Or a naphthyl group.
  • R 23 and R 24 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or are bonded to each other to form a substituted or unsubstituted ring.
  • R 23 and R 24 are the same or different and are each independently selected from the group consisting of hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or is bonded to each other to form a substituted or unsubstituted ring.
  • R 23 and R 24 are the same or different and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or is bonded to each other to form a substituted or unsubstituted hydrocarbon ring having 6 to 60 carbon atoms.
  • R 23 and R 24 are the same or different and are each independently selected from the group consisting of hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group, or is bonded to each other to form a substituted or unsubstituted hydrocarbon ring having 6 to 30 carbon atoms.
  • R 23 and R 24 are the same or different and each independently hydrogen; Methyl group; An ethyl group; Isopropyl group; tert-butyl group; A phenyl group; A biphenyl group; Or a naphthyl group, or combine with each other to form a fluorene ring.
  • R25 to R27 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • R25 to R27 are the same or different and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
  • R25 to R27 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • A1 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; Or a substituted or unsubstituted aromatic heterocycle having 2 to 60 carbon atoms.
  • A1 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms; Or a substituted or unsubstituted aromatic heterocycle having 2 to 30 carbon atoms.
  • A1 is a substituted or unsubstituted benzene ring.
  • A1 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, A substituted or unsubstituted amino group, a substituted or unsubstituted amino group, and a substituted or unsubstituted C2-C30 heterocyclic group.
  • A1 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkyl group having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms, An arylamine group having from 12 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having from 1 to 20 carbon atoms, and a heterocyclic group having from 2 to 30 carbon atoms containing S, O, or N, An aromatic hydrocarbon ring having 6 to 30 carbon atoms which is substituted or unsubstituted with a substituent.
  • A1 is a substituted or unsubstituted methyl group, a tert-butyl group, a cyclohexyl group, a phenyl group substituted or unsubstituted with a methyl group, a substituted or unsubstituted diphenyl
  • A1 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkyl group having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms, An arylamine group having from 12 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having from 1 to 20 carbon atoms, and a heterocyclic group having from 2 to 30 carbon atoms containing S, O, or N, Substituted or unsubstituted benzene ring.
  • A1 is a substituted or unsubstituted methyl group, a tert-butyl group, a cyclohexyl group, a phenyl group substituted or unsubstituted with a methyl group, a substituted or unsubstituted diphenyl An amine group, and a carbazole group.
  • A2 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; Or a substituted or unsubstituted aromatic heterocycle having 2 to 60 carbon atoms.
  • A2 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms; Or a substituted or unsubstituted aromatic heterocycle having 2 to 30 carbon atoms.
  • A2 is a substituted or unsubstituted alkylsilyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl
  • A2 is a trialkylsilyl group having 3 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms substituted with deuterium, a cycloalkyl group having 3 to 30 carbon atoms, an aryl group having 12 to 30 carbon atoms
  • An aromatic hydrocarbon having 6 to 30 carbon atoms which is unsubstituted or substituted with at least one substituent selected from the group consisting of an amino group, an amine group, a halogen group or an aryl group having 6 to 30 carbon atoms, which is substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms, ring;
  • A2 is a trialkylsilyl group having 3 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms substituted with deuterium, a cycloalkyl group having 3 to 30 carbon atoms, an aryl group having 12 to 30 carbon atoms
  • A2 is a phenyl group substituted or unsubstituted with a trimethylsilyl group, a methyl group substituted with deuterium, a propyl group, a butyl group, a cyclohexyl group, a diphenylamine group, a fluorine or a butyl group, A benzene ring substituted or unsubstituted with at least one substituent selected from the group consisting of benzene ring and benzene ring; Naphthalene ring; Or a dibenzofuran ring.
  • the formula (1) may be represented by any one of the following formulas (2-1) to (2-7).
  • Y1 to Y14 are the same as or different from each other and each independently represent the definition of Y in the above formula (2)
  • A21 to A34 are the same as or different from each other, and are each independently the same as the definition of A2 in the above formula (2).
  • Y1 to Y14 are the same as or different from each other and each independently as defined for Y in Formula 2 above.
  • A21 to A34 are aromatic hydrocarbon rings having 6 to 60 carbon atoms, which are the same or different from each other and are independently substituted or unsubstituted; Or a substituted or unsubstituted aromatic heterocycle having 2 to 60 carbon atoms.
  • A21 to A34 are the same or different and each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms; Or a substituted or unsubstituted aromatic heterocycle having 2 to 30 carbon atoms.
  • A21 to A34 are the same or different and each independently represents a substituted or unsubstituted alkylsilyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, An aromatic hydrocarbon ring having 6 to 30 carbon atoms, which is substituted or unsubstituted with at least one substituent selected from the group consisting of a substituted amine group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted alkylsilyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group Or
  • A21 to A34 are the same or different and each independently represents a trialkylsilyl group having 3 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium, Substituted with at least one substituent selected from the group consisting of a cycloalkyl group having 1 to 30 carbon atoms, an arylamine group having 12 to 30 carbon atoms, a halogen group or an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms, and a heterocyclic group Or an unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms; Or a trialkylsilyl group having 3 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an arylamine group having 12 to 30 carbon atoms,
  • A21 to A34 are the same or different and each independently represents a trialkylsilyl group having 3 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium, Substituted with at least one substituent selected from the group consisting of a cycloalkyl group having 1 to 30 carbon atoms, an arylamine group having 12 to 30 carbon atoms, a halogen group or an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms, and a heterocyclic group Or an unsubstituted benzene ring;
  • A21 to A34 are the same or different and each independently represents a methyl group, a propyl group, a butyl group, a cyclohexyl group, a diphenylamine group, a fluorine or an alkyl group substituted with a trimethylsilyl group or deuterium
  • Ra to Rg are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or is bonded to an adjacent group to form a substituted or unsubstituted ring.
  • Ra is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
  • Ra is an aryl group having 6 to 60 carbon atoms which is substituted or unsubstituted with at least one substituent selected from the group consisting of deuterium, a halogen group, and an alkyl group having 1 to 20 carbon atoms.
  • Ra is a phenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of deuterium, a halogen group, and an alkyl group having 1 to 20 carbon atoms; A naphthyl group substituted or unsubstituted with at least one substituent selected from the group consisting of deuterium, a halogen group, and an alkyl group having 1 to 20 carbon atoms; Or a biphenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of deuterium, a halogen group, and an alkyl group having 1 to 20 carbon atoms.
  • Ra is an aryl group having 6 to 60 carbon atoms, which is substituted or unsubstituted with at least one substituent selected from the group consisting of deuterium, fluorine (-F), and butyl.
  • Ra represents a phenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of deuterium, fluorine (-F) and butyl group; A naphthyl group substituted or unsubstituted with at least one substituent selected from the group consisting of deuterium, fluorine (-F) and butyl group; Or a biphenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of deuterium, fluorine (-F) and butyl group.
  • Rb is an aryl group having 6 to 30 carbon atoms.
  • Rb is a substituted or unsubstituted phenyl group.
  • Rb is a phenyl group.
  • Rc and Rd are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or is bonded to each other to form a substituted or unsubstituted hydrocarbon ring having 6 to 30 carbon atoms.
  • Rc and Rd are the same or different and each independently represents an alkyl group having 1 to 20 carbon atoms; Or an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms or is bonded to each other to form a substituted or unsubstituted hydrocarbon ring having 6 to 30 carbon atoms.
  • Rc and Rd are the same or different and are each independently a substituted or unsubstituted methyl group; Or a substituted or unsubstituted phenyl group, or are bonded to each other to form a substituted or unsubstituted hydrocarbon ring having 6 to 30 carbon atoms.
  • Rc and Rd are the same or different and are each independently a methyl group; Or a phenyl group substituted or unsubstituted with a methyl group, or combine with each other to form a fluorene ring.
  • Re to Rg are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or is bonded to each other to form a substituted or unsubstituted hydrocarbon ring having 6 to 30 carbon atoms.
  • Ar1 and Ar2 are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, or may be bonded to adjacent groups to form a substituted or unsubstituted ring.
  • Ar 1 and Ar 2 are the same or different and each independently represent an aryl group having 6 to 60 carbon atoms, which is substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms.
  • Ar1 and Ar2 are the same or different and each independently represents a phenyl group substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms; A biphenyl group substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms; Or a naphthyl group substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms.
  • Ar1 and Ar2 are the same or different and each independently represent a phenyl group substituted or unsubstituted with a methyl group or a butyl group; A biphenyl group; Or a naphthyl group.
  • the formula (1) may be represented by any one of the following structures.
  • the compound of formula (1) according to one embodiment of the present invention can be prepared by the following production method.
  • the compound of Formula 1 may be prepared in a core structure as described below.
  • Substituent groups may be attached by methods known in the art, and the type, position or number of substituent groups may be varied according to techniques known in the art.
  • the organic light emitting device includes a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound of Formula 1.
  • the organic layer includes a light emitting layer, and at least one of the organic layers includes the compound described above, and the light emitting layer may include a compound represented by the following formula (1A).
  • L103 to L106 are the same or different and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar5 to Ar8 are the same or different and each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • R101 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • p is an integer of 0 to 6
  • L103 to L106 are the same or different and are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.
  • L103 to L106 are the same or different and are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.
  • L103 to L106 are the same or different and are each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted anthracenylene group; A substituted or unsubstituted phenanthrenylene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted thiophenylene group; A substituted or unsubstituted furanyl group; A substituted or unsubstituted dibenzothiophenylene group; A substituted or unsubstituted dibenzofuranylene group; Or a substituted or unsubstituted carbazolylene group.
  • L103 to L106 are the same or different and are each independently a direct bond; A phenylene group; Biphenyllylene groups; A terphenylene group; Naphthylene group; Anthracenylene group; Phenanthrenylene group; Triphenylene group; A fluorenyl group substituted or unsubstituted with a methyl group or a phenyl group; Thiophenylene group; A furanylene group; Dibenzothiophenylene groups; Dibenzofuranyl group; Or a carbazolylene group substituted or unsubstituted with an ethyl group or a phenyl group.
  • L103 to L106 are the same or different and are each independently a direct bond; Or one of the following structures.
  • L103 is a direct bond.
  • L104 is a phenylene group.
  • L105 and L106 are direct bonds.
  • R101 is hydrogen; heavy hydrogen; A halogen group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylheteroarylamine group; Or a substituted or unsubstituted heterocyclic group.
  • R101 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • R101 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.
  • R101 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted C2-C25 heterocyclic group.
  • R101 is hydrogen
  • p is 0 or 1.
  • Ar5 to Ar8 are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
  • Ar5 to Ar8 may be the same or different from each other, and each independently hydrogen; An aryl group having 6 to 60 carbon atoms or an aryl group having 6 to 60 carbon atoms substituted or unsubstituted with a heteroaryl group having 2 to 60 carbon atoms; Or a heteroaryl group having 2 to 60 carbon atoms, which is substituted or unsubstituted with an aryl group having 60 to 60 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms.
  • Ar5 to Ar8 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted furan group; A substituted or unsubstituted benzothioph
  • Ar5 to Ar8 are the same or different from each other, and each independently hydrogen; A phenyl group; A biphenyl group; A naphthyl group substituted or unsubstituted with an aryl group; Phenanthrene; Anthracene group; Triphenylene group; A dibenzofurane group substituted or unsubstituted with an aryl group; A naphthobenzofuran group; A dibenzothiophene group substituted or unsubstituted with an aryl group; A carbazole group substituted or unsubstituted with an alkyl group or an aryl group; An alkyl group, or a fluorene group substituted or unsubstituted with an aryl group; A thiophene group substituted or unsubstituted with an aryl group; A furan group substituted or unsubstituted with an aryl group; Benzothiophene group; Benzofuran group
  • Ar5 to Ar8 are the same or different from each other, and each independently hydrogen; A phenyl group; A biphenyl group; A naphthyl group substituted or unsubstituted with a phenyl group; Phenanthrene; Anthracene group; Triphenylene group; A dibenzofurane group substituted or unsubstituted with a phenyl group; A naphthobenzofuran group; A dibenzothiophene group substituted or unsubstituted with a phenyl group; A carbazole group substituted or unsubstituted with a methyl group, an ethyl group, or a phenyl group; A methyl group, or a fluorene group substituted or unsubstituted with a phenyl group; A thiophene group substituted or unsubstituted with a phenyl group; A furan group substituted or unsubstituted with a
  • Ar5 to Ar8 are the same or different from each other and each independently hydrogen; Or one of the following structures.
  • the organic layer includes a light emitting layer, and at least one of the organic layers includes the compound described above, and the light emitting layer may include a compound represented by the following Formula 1B.
  • the host material of the light emitting layer in the organic material layer of the organic light emitting device of the present specification may include a structure of the following formula (1B).
  • L107 to L109 are the same or different and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar9 to Ar11 are the same or different from each other, and each independently hydrogen; Or a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • R102 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • q is an integer of 0 to 7
  • R102 is hydrogen; heavy hydrogen; A halogen group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylheteroarylamine group; Or a substituted or unsubstituted heterocyclic group.
  • R102 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • R102 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.
  • R102 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted C2-C25 heterocyclic group.
  • R102 is hydrogen
  • q is 0 or 1.
  • L107 to L109 are the same or different and are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.
  • L107 to L109 are the same or different and are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.
  • L107 to L109 are the same or different and are each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted anthracenylene group; A substituted or unsubstituted phenanthrenylene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted thiophenylene group; A substituted or unsubstituted furanyl group; A substituted or unsubstituted dibenzothiophenylene group; A substituted or unsubstituted dibenzofuranylene group; Or a substituted or unsubstituted carbazolylene group.
  • L107 to L109 are the same or different and are each independently a direct bond; A phenylene group; Biphenyllylene groups; A terphenylene group; Naphthylene group; Anthracenylene group; Phenanthrenylene group; Triphenylene group; A fluorenyl group substituted or unsubstituted with a methyl group or a phenyl group; Thiophenylene group; A furanylene group; Dibenzothiophenylene groups; Dibenzofuranyl group; Or a carbazolylene group substituted or unsubstituted with an ethyl group or a phenyl group.
  • L107 to L109 are the same or different and are each independently a direct bond; Or one of the following structures.
  • L107 to L109 are direct bonds.
  • Ar9 to Ar11 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
  • Ar9 to Ar11 are the same as or different from each other, and each independently hydrogen; An aryl group having 6 to 60 carbon atoms or an aryl group having 6 to 60 carbon atoms substituted or unsubstituted with a heteroaryl group having 2 to 60 carbon atoms; Or a heteroaryl group having 2 to 60 carbon atoms, which is substituted or unsubstituted with an aryl group having 60 to 60 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms.
  • Ar9 to Ar11 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted furan group; A substituted or unsubstituted benzothioph
  • Ar9 to Ar11 are the same or different from each other and each independently hydrogen; A phenyl group; A biphenyl group; A naphthyl group substituted or unsubstituted with an aryl group; Phenanthrene; Anthracene group; Triphenylene group; A dibenzofurane group substituted or unsubstituted with an aryl group; A naphthobenzofuran group; A dibenzothiophene group substituted or unsubstituted with an aryl group; A carbazole group substituted or unsubstituted with an alkyl group or an aryl group; An alkyl group, or a fluorene group substituted or unsubstituted with an aryl group; A thiophene group substituted or unsubstituted with an aryl group; A furan group substituted or unsubstituted with an aryl group; Benzothiophene group; Benzofuran group;
  • Ar9 to Ar11 are the same or different from each other, and each independently hydrogen; A phenyl group; A biphenyl group; A naphthyl group substituted or unsubstituted with a phenyl group; Phenanthrene; Anthracene group; Triphenylene group; A dibenzofurane group substituted or unsubstituted with a phenyl group; A naphthobenzofuran group; A dibenzothiophene group substituted or unsubstituted with a phenyl group; A carbazole group substituted or unsubstituted with a methyl group, an ethyl group, or a phenyl group; A methyl group, or a fluorene group substituted or unsubstituted with a phenyl group; A thiophene group substituted or unsubstituted with a phenyl group; A furan group substituted or unsubstituted with a
  • Ar9 to Ar11 are the same or different from each other and each independently hydrogen; Or one of the following structures.
  • the organic light emitting device of the present invention can be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that one or more organic compound layers are formed using the compound represented by the above-described formula (1).
  • the compound may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
  • the organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers.
  • the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include a compound represented by the above formula (1).
  • the organic material layer may include a hole injecting layer or a hole transporting layer, and the hole injecting layer or the hole transporting layer may include the compound represented by the above formula (1).
  • the organic layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by the general formula (1).
  • the organic layer includes a light emitting layer
  • the light emitting layer may include the compound represented by Formula 1 as a dopant in the light emitting layer.
  • the organic layer includes a light-emitting layer, wherein the light-emitting layer contains a compound represented by the general formula (1) as a dopant of the light-emitting layer and includes a fluorescent host or a phosphorescent host, As a dopant.
  • the organic layer may include a light emitting layer
  • the light emitting layer may include a compound represented by Formula 1 as a dopant of the light emitting layer, and may include a fluorescent host or a phosphorescent host, and may be used together with an iridium (Ir) have.
  • the organic light emitting device is a green organic light emitting device in which the light emitting layer includes the compound represented by Formula 1 as a dopant.
  • the organic light emitting device is a red organic light emitting device in which the light emitting layer includes the compound represented by Formula 1 as a dopant.
  • the organic light emitting device is a blue organic light emitting device in which the light emitting layer contains the compound represented by Formula 1 as a dopant.
  • the organic layer may include a light emitting layer, and the light emitting layer may include a compound represented by Formula 1 as a host of the light emitting layer.
  • the organic layer may include a light emitting layer
  • the light emitting layer may include a compound represented by Formula 1 as a host of the light emitting layer, and may include a dopant.
  • the first electrode is an anode and the second electrode is a cathode.
  • the first electrode is a cathode and the second electrode is a cathode.
  • the structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but the present invention is not limited thereto.
  • FIG. 1 illustrates the structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially laminated on a substrate 1.
  • the compound may be included in the light emitting layer (3).
  • FIG. 2 shows an organic light emitting device in which an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 are sequentially laminated on a substrate 1 Structure is illustrated.
  • the compound may be included in the hole injecting layer 5, the hole transporting layer 6, the light emitting layer 7, or the electron transporting layer 8.
  • the organic light emitting device may be formed by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form a metal oxide or a metal oxide having conductivity on the substrate,
  • a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form a metal oxide or a metal oxide having conductivity on the substrate
  • an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer, and an electron transporting layer is formed on the anode, and a material which can be used as a cathode is deposited thereon.
  • an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.
  • the organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure.
  • the organic material layer may be formed using a variety of polymeric materials by a method such as a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, Layer.
  • the cathode material a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer.
  • the cathode 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), and indium zinc oxide (IZO); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.
  • the negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
  • Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or LiO 2 / Al, but are not limited thereto.
  • the hole injecting material it is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material is between the work function of the anode material and the HOMO of the surrounding organic layer.
  • the hole injecting material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.
  • the hole transporting material a material capable of transporting holes from the anode or the hole injecting layer to the light emitting layer and having high mobility to holes is suitable.
  • Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • the light emitting layer may emit red, green or blue light, and may be formed of a phosphor or a fluorescent material.
  • the light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.
  • Alq 3 8-hydroxy-quinoline aluminum complex
  • Carbazole-based compounds Dimerized styryl compounds
  • BAlq 10-hydroxybenzoquinoline-metal compounds
  • Compounds of the benzoxazole, benzothiazole and benzimidazole series Polymers of poly (p-phenylenevinylene) (PPV) series
  • Spiro compounds Polyfluorene, rubrene, and the like, but are not limited thereto.
  • Examples of the host material of the light emitting layer include a condensed aromatic ring derivative or a heterocyclic compound.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds.
  • Examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • Examples of the dopant material include an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, and a metal complex.
  • Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group.
  • styrylamine compound examples include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like.
  • the metal complex examples include iridium complex, platinum complex, and the like, but are not limited thereto.
  • the electron transporting material a material capable of transferring electrons from the cathode well into the light emitting layer, which is suitable for electrons, is suitable.
  • Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.
  • the electron injecting material has an ability to transport electrons, has an electron injecting effect from the cathode, an electron injecting effect to the emitting layer or the light emitting material, prevents migration of excitons generated in the emitting layer to the hole injecting layer, Further, a compound having excellent thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, 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- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.
  • the hole blocking layer prevents holes from reaching the cathode, and may be formed under the same conditions as those of the hole injection layer. Specific examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes and the like.
  • the organic light emitting device may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.
  • Fluorodibenzo [b, d] furan] (25.0 g, 0.113 mol) and aniline (11.6 g, 0.125 mol) in a nitrogen atmosphere, (1.2 g, 2.27 mmol), bis (tri-tert-butylphosphine) palladium (0), NaOtBu (27 g, 0.283 mol) and 200 mL of xylene
  • the flask was heated and stirred for 12 hours.
  • the reaction solution was cooled to room temperature, extracted with water and dichloromethane, and washed.
  • a thin glass substrate coated with ITO (indium tin oxide) having a thickness of 1300 ⁇ was immersed in distilled water containing detergent and washed with ultrasonic waves.
  • Fischer Co. product was used as a detergent
  • distilled water filtered by a filter of Millipore Co. was used as distilled water.
  • the ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.
  • the following compound [HI-A] was vacuum deposited on the ITO transparent electrode prepared above to a thickness of 600 ⁇ to form a hole injection layer.
  • the following compound [HAT-CN] (50 ⁇ ) and the following compound [HT-A] (600 ⁇ ) were sequentially vacuum-deposited on the hole injection layer to form a hole transport layer.
  • [BH-A] and Compound 1 were vacuum-deposited to a thickness of 200 ⁇ at a weight ratio of 25: 1 to form a light emitting layer. Then, [ET-A] and Liq were deposited in a ratio of 1: 1 at a thickness of 300 angstroms. Lithium fluoride (LiF) and aluminum were deposited in a thickness of 10 angstroms sequentially to form a cathode. Device.
  • LiF lithium fluoride
  • the deposition rate of the organic material was maintained at 0.4 to 0.9 ⁇ / sec, the lithium fluoride at the cathode was maintained at a deposition rate of 0.3 ⁇ / sec, and the deposition rate of aluminum was maintained at 2 ⁇ / sec. by keeping the -7 to 5 ⁇ 10 -8 torr, an organic light emitting device was produced.
  • An organic light emitting device was prepared in the same manner as in Example 1 except that Compound 3 was used instead of Compound 1 and [BH-B] was used instead of the host [BH-A].
  • An organic luminescent device was prepared in the same manner as in Example 1 except that Compound 3 was used instead of Compound 1 and [BH-C] was used instead of the host [BH-A].
  • Example 1 Compound 3 was used instead of Compound 1, and the host [BH-A] further contained a host [BH-B] in a weight ratio of [BH-A] and [BH- ), An organic luminescent device was prepared in the same manner as in Example 1.
  • An organic light emitting device was prepared in the same manner as in Example 1, except that Compound 3 was used instead of Compound 1 in Example 1.
  • An organic light emitting device was prepared in the same manner as in Example 1, except that Compound 4 was used instead of Compound 1 in Example 1.
  • An organic luminescent device was prepared in the same manner as in Example 1 except that [BD-A] was used in place of the compound 1 in Example 1 above.
  • An organic luminescent device was prepared in the same manner as in Example 1, except that [BD-C] was used in place of the compound 1 in Example 1.
  • the driving voltage and the luminous efficiency were measured at a current density of 10 mA / cm < 2 > at the current density of 20 mA / cm < 2 > and the time (T 90 ) Respectively.
  • the results are shown in Table 1 below.

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