WO2019088799A1 - Polycyclic compound and organic light-emitting device comprising same - Google Patents

Polycyclic compound and organic light-emitting device comprising same 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/en
Publication of WO2019088799A1 publication Critical patent/WO2019088799A1/en

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    • 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 System
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • 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 System
    • C07F5/02—Boron compounds
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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
    • H—ELECTRICITY
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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
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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
    • 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
    • H10K50/16—Electron 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]
    • H10K50/18—Carrier blocking layers
    • 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
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K99/00—Subject matter not provided for in other groups of this subclass
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds

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.

Abstract

The present specification provides a compound represented by chemical formula 1 and an organic light-emitting device comprising the same.

Description

다환 화합물 및 이를 포함하는 유기 발광 소자Polycyclic compounds and organic light emitting devices containing them
본 출원은 2017년 11월 6일 한국특허청에 제출된 한국특허출원 제10-2017-0146798호의 출원일의 이익을 주장하며, 그 내용은 전부 본 명세서에 포함된다.This application claims the benefit of Korean Patent Application No. 10-2017-0146798 filed on November 6, 2017, filed with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.
본 명세서는 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다. BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a compound and an organic light emitting device including the same.
본 명세서에서, 유기 발광 소자란 유기 반도체 물질을 이용한 발광 소자로서, 전극과 유기 반도체 물질 사이에서의 정공 및/또는 전자의 교류를 필요로 한다. 유기 발광 소자는 동작 원리에 따라 하기와 같이 크게 두 가지로 나눌 수 있다. 첫째는 외부의 광원으로부터 소자로 유입된 광자에 의하여 유기물층에서 엑시톤(exiton)이 형성되고, 이 엑시톤이 전자와 정공으로 분리되고, 이 전자와 정공이 각각 다른 전극으로 전달되어 전류원(전압원)으로 사용되는 형태의 발광 소자이다. 둘째는 2개 이상의 전극에 전압 또는 전류를 가하여 전극과 계면을 이루는 유기 반도체 물질층에 정공 및/또는 전자를 주입하고, 주입된 전자와 정공에 의하여 작동하는 형태의 발광 소자이다.In the present specification, 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.
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 이루어 질 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. 이러한 유기 발광 소자는 자발광, 고휘도, 고효율, 낮은 구동 전압, 넓은 시야각, 높은 콘트라스트 등의 특성을 갖는 것으로 알려져 있다.In general, 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. Here, in order to increase the efficiency and stability of the organic light emitting device, 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. 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.
유기 발광 소자에서 유기물층으로 사용되는 재료는 기능에 따라, 발광 재료와 전하 수송 재료, 예컨대 정공 주입 재료, 정공 수송 재료, 전자 수송 재료, 전자 주입 재료 등으로 분류될 수 있다. 발광 재료는 발광색에 따라 청색, 녹색, 적색 발광 재료와 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 재료가 있다.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.
또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 재료로서 호스트/도펀트 계를 사용할 수 있다. 그 원리는 발광층을 주로 구성하는 호스트보다 에너지 대역 간극이 작고 발광 효율이 우수한 도펀트를 발광층에 소량 혼합하면, 호스트에서 발생한 엑시톤이 도펀트로 수송되어 효율이 높은 빛을 내는 것이다. 이 때 호스트의 파장이 도펀트의 파장대로 이동하므로, 이용하는 도펀트의 종류에 따라 원하는 파장의 빛을 얻을 수 있다.Further, in order to increase the color purity and increase the luminous efficiency through energy transfer, 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.
전술한 유기 발광 소자가 갖는 우수한 특징들을 충분히 발휘하기 위해서는 소자 내 유기물층을 이루는 물질, 예컨대 정공 주입 물질, 정공 수송 물질, 발광 물질, 전자 수송 물질, 전자 주입 물질 등이 안정하고 효율적인 재료에 의하여 뒷받침되므로 새로운 재료의 개발이 계속 요구되고 있다.In order to sufficiently exhibit the excellent characteristics of the organic light emitting device described above, 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.
[선행기술문헌][Prior Art Literature]
(특허문헌 1) 중국 특허공개공보 106467553호(Patent Document 1) Chinese Patent Laid-Open Publication No. 106467553
본 명세서에는 화합물 및 이를 포함하는 유기 발광 소자가 기재된다.In this specification, compounds and organic light emitting devices containing them are described.
본 명세서의 일 실시상태는 하기 화학식 1로 표시되는 화합물을 제공한다.An embodiment of the present invention provides a compound represented by the following formula (1).
[화학식 1][Chemical Formula 1]
Figure PCTKR2018013380-appb-I000001
Figure PCTKR2018013380-appb-I000001
상기 화학식 1에 있어서,In Formula 1,
A1은 치환 또는 비치환된 방향족 탄화수소고리; 또는 치환 또는 비치환된 방향족 헤테로고리이며,A1 is a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle,
W는 O, S, Se, NRa, PRb, C=O, CRcRd, SiReRf 또는 P(=O)Rg이고, W is O, S, Se, NRa, PRb, C = O, CRcRd, SiReRf or P (= O)
X1은 N 또는 CR11이며, X2는 N 또는 CR12이고, X3는 N 또는 CR13이며, X1 is N or CR11, X2 is N or CR12, X3 is N or CR13,
단, X2가 N인 경우 X3는 CR13이고, X3가 N인 경우 X2는 CR12이며,Provided that when X2 is N, X3 is CR13; when X3 is N, X2 is CR12;
Ra 내지 Rg, R11 내지 R13, Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 알킬실릴기; 아릴실릴기; 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 알콕시아릴기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하며, 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 및 R2는 하기 화학식 2의 점선부와 연결되어 고리를 형성하고,R1 and R2 are connected to the dotted line of the formula (2) to form a ring,
R3 및 R12; 또는 R3 및 R13은 하기 화학식 2의 점선부와 연결되어 고리를 형성하며,R3 and R12; Or R < 3 > and R < 13 > are connected to the dotted line of the formula (2)
[화학식 2](2)
Figure PCTKR2018013380-appb-I000002
Figure PCTKR2018013380-appb-I000002
상기 화학식 2에 있어서,In Formula 2,
Y는 O, S, Se, NR21, PR22, C=O, CR23R24, SiR25R26 또는 P(=O)R27이고,Y is O, S, Se, NR21, PR22, C = O, CR23R24, SiR25R26 or P
R21 내지 R27은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하며,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,
A2는 치환 또는 비치환된 방향족 탄화수소고리; 또는 치환 또는 비치환된 방향족 헤테로고리이다.A2 is a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle.
또한, 본 명세서의 일 실시상태에 따르면, 제1 전극; 상기 제1 전극과 대향하여 구비되는 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비되는 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상이 상기 전술한 화합물을 포함하는 것인 유기 발광 소자를 제공한다.According to an embodiment of the present invention, there is also provided 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.
본 명세서에 기재된 화합물은 붕소(B)를 포함하는 다환의 축합고리 화합물로서 유기 발광 소자의 유기물층의 재료로서 사용될 수 있다. 적어도 하나의 실시상태에 따른 화합물은 유기 발광 소자에서 발광 효율, 색순도, 수명 특성 등의 소자의 특성을 향상시킬 수 있으며, 낮은 구동전압을 갖는 소자를 얻을 수 있다.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.
도 1은 기판(1), 양극(2), 발광층(3) 및 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.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.
도 2는 기판 (1), 양극(2), 정공주입층(5), 정공수송층(6), 발광층(7), 전자수송층(8) 및 음극(4)로 이루어진 유기 발광 소자의 예를 도시한 것이다.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.
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: 발광층7:
8: 전자수송층8: Electron transport layer
이하 본 명세서에 대하여 더욱 상세히 설명한다. Hereinafter, the present invention will be described in more detail.
본 명세서는 하기 화학식 1로 표시되는 화합물을 제공한다. 하기 화학식 1로 표시되는 화합물 내에 B를 포함하고, 화학식 2의 점선부와 연결되어 고리를 형성함으로써, 트리아릴 보레인[Triaryl borane]에 직접적으로 결합된 아릴기를 질소 또는 기타 컨쥬게이션을 확장하지 않는 형태의 원자(W)를 이용하여 결합시켜, 아릴기의 입체장애에 의한 뒤틀림 특성을 개선하였다. 이러한 분자들은 기존에 발명된 발광 재료에 비해 분자의 안정성이 증가하여 유기 발광 소자 구동에서 수명을 획기적으로 개선할 수 있다. 또한 분자의 안정성 증가는 증착공정 속도를 높여 공정성 개선이 가능하다.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. These molecules increase the stability of the molecules compared to the conventional light emitting materials, and can remarkably improve lifetime in driving the organic light emitting devices. In addition, the stability of the molecules can be improved by increasing the deposition process speed.
또한, 본 발명의 화합물은 기존의 유기 발광 소자의 수명, 색재현율, 전하 균형 특성을 개선하고 패널 제조시 공정성, 재료 변성 등의 특성 개선이 가능하다.In addition, 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.
[화학식 1][Chemical Formula 1]
Figure PCTKR2018013380-appb-I000003
Figure PCTKR2018013380-appb-I000003
상기 화학식 1에 있어서,In Formula 1,
A1은 치환 또는 비치환된 방향족 탄화수소고리; 또는 치환 또는 비치환된 방향족 헤테로고리이며,A1 is a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle,
W는 O, S, Se, NRa, PRb, C=O, CRcRd, SiReRf 또는 P(=O)Rg이고, W is O, S, Se, NRa, PRb, C = O, CRcRd, SiReRf or P (= O)
X1은 N 또는 CR11이며, X2는 N 또는 CR12이고, X3는 N 또는 CR13이며, X1 is N or CR11, X2 is N or CR12, X3 is N or CR13,
단, X2가 N인 경우 X3는 CR13이고, X3가 N인 경우 X2는 CR12이며,Provided that when X2 is N, X3 is CR13; when X3 is N, X2 is CR12;
Ra 내지 Rg, R11 내지 R13, Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 알킬실릴기; 아릴실릴기; 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 알콕시아릴기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하며, 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 및 R2는 하기 화학식 2의 점선부와 연결되어 고리를 형성하고,R1 and R2 are connected to the dotted line of the formula (2) to form a ring,
R3 및 R12; 또는 R3 및 R13은 하기 화학식 2의 점선부와 연결되어 고리를 형성하며,R3 and R12; Or R < 3 > and R < 13 > are connected to the dotted line of the formula (2)
[화학식 2](2)
Figure PCTKR2018013380-appb-I000004
Figure PCTKR2018013380-appb-I000004
상기 화학식 2에 있어서,In Formula 2,
Y는 O, S, Se, NR21, PR22, C=O, CR23R24, SiR25R26 또는 P(=O)R27이고,Y is O, S, Se, NR21, PR22, C = O, CR23R24, SiR25R26 or P
R21 내지 R27은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하며,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,
A2는 치환 또는 비치환된 방향족 탄화수소고리; 또는 치환 또는 비치환된 방향족 헤테로고리이다.A2 is a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle.
본 명세서에 있어서, 어떤 부분이 어떤 구성요소를 "포함" 한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성 요소를 더 포함할 수 있는 것을 의미한다.In this specification, when a part is referred to as " including " an element, it is to be understood that it may include other elements as well, without departing from the other elements unless specifically stated otherwise.
본 명세서에 있어서, 어떤 부재가 다른 부재 "상에" 위치하고 있다고 할 때, 이는 어떤 부재가 다른 부재에 접해 있는 경우뿐 아니라 두 부재 사이에 또 다른 부재가 존재하는 경우도 포함한다.In this specification, 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.
본 명세서에서 치환기의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다.Examples of substituents herein are described below, but are not limited thereto.
상기 "치환" 이라는 용어는 화합물의 탄소 원자에 결합된 수소 원자가 다른 치환기로 바뀌는 것을 의미하며, 치환되는 위치는 수소 원자가 치환되는 위치 즉, 치환기가 치환 가능한 위치라면 한정하지 않으며, 2 이상 치환되는 경우, 2 이상의 치환기는 서로 동일하거나 상이할 수 있다.The term " 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.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 히드록시기; 시아노기(-CN); 니트로기; 실릴기; 붕소기; 알킬기; 시클로알킬기; 알콕시기; 알케닐기; 알키닐기; 아릴옥시기; 아릴기; 아민기; 및 헤테로고리기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되었거나 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 바이페닐기일 수 있다. 즉, 바이페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 도 있다.As used herein, 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. For example, " 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.
상기 치환기들의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다. Illustrative examples of such substituents are set forth below, but are not limited thereto.
본 명세서에 있어서, 할로겐기의 예로는 불소(F), 염소(Cl), 브롬(Br) 또는 요오드(I)가 있다.In this specification, examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br) or iodine (I).
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 60인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 30이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 알킬기의 구체적인 예로는 메틸기, 에틸기, n-프로필기, 이소프로필기, n-부틸기, 이소부틸기, tert-부틸기, n-펜틸기, n-헥실기, n-헵틸기, n-옥틸기 등이 있으나, 이들에 한정되지 않는다.In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 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.
본 명세서에 있어서, 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 30인 것이 바람직하며, 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 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.
본 명세서에 있어서, 상기 알콕시기는 직쇄 또는 분지쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 30인 것이 바람직하다. 구체적으로, 메톡시, 에톡시, n-프로폭시, 이소프로폭시, i-프로필옥시, n-부톡시, 이소부톡시, tert-부톡시, sec-부톡시, n-펜틸옥시, 네오펜틸옥시, 이소펜틸옥시, n-헥실옥시, 3,3-디메틸부틸옥시, 2-에틸부틸옥시, n-옥틸옥시, n-노닐옥시, n-데실옥시 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, 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, .
본 명세서에 있어서, 아민기는 -NH2; 알킬아민기; N-알킬아릴아민기; 아릴아민기; N-아릴헤테로아릴아민기; N-알킬헤테로아릴아민기, 및 헤테로아릴아민기로 이루어진 군으로부터 선택될 수 있으며, 탄소수는 특별히 한정되지 않으나, 1 내지 30인 것이 바람직하다. 아민기의 구체적인 예로는 메틸아민기, 디메틸아민기, 에틸아민기, 디에틸아민기, 페닐아민기, 나프틸아민기, 바이페닐아민기, 안트라세닐아민기, 9-메틸-안트라세닐아민기, 디페닐아민기, 디톨릴아민기, N-페닐톨릴아민기, 트리페닐아민기, N-페닐바이페닐아민기; N-페닐나프틸아민기; N-바이페닐나프틸아민기; N-나프틸플루오레닐아민기; N-페닐페난트레닐아민기; N-바이페닐페난트레닐아민기; N-페닐플루오레닐아민기; N-페닐터페닐아민기; N-페난트레닐플루오레닐아민기; N-바이페닐플루오레닐아민기 등이 있으나, 이에 한정되는 것은 아니다.In this specification, 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. Specific examples of the amine group 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-phenyltriphenylamine group; N-phenanthrenyl fluorenylamine group; And an N-biphenylfluorenylamine group, but are not limited thereto.
본 명세서에 있어서, N-알킬아릴아민기는 아민기의 N에 알킬기 및 아릴기가 치환된 아민기를 의미한다.In the present specification, 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.
본 명세서에 있어서, N-아릴헤테로아릴아민기는 아민기의 N에 아릴기 및 헤테로아릴기가 치환된 아민기를 의미한다.In the present specification, 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.
본 명세서에 있어서, N-알킬헤테로아릴아민기는 아민기의 N에 알킬기 및 헤테로아릴기가 치환된 아민기를 의미한다.In the present specification, 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.
본 명세서에 있어서, 알킬아민기의 예로는 치환 또는 비치환된 모노알킬아민기, 또는 치환 또는 비치환된 디알킬아민기가 있다. 상기 알킬아민기 중의 알킬기는 직쇄 또는 분지쇄의 알킬기일 수 있다. 상기 알킬기를 2 이상 포함하는 알킬아민기는 직쇄의 알킬기, 분지쇄의 알킬기, 또는 직쇄의 알킬기와 분지쇄의 알킬기를 동시에 포함할 수 있다. 예컨대, 상기 알킬아민기 중의 알킬기는 전술한 알킬기의 예시 중에서 선택될 수 있다.In the present specification, 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. For example, the alkyl group in the alkylamine group may be selected from the examples of the alkyl group described above.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 30인 것이 바람직하다. 구체적인 예로는 비닐, 1-프로페닐, 이소프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 1-펜테닐, 2-펜테닐, 3-펜테닐, 3-메틸-1-부테닐 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, 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.
본 명세서에 있어서, 실릴기는 -SiR101R102R103일 수 있으며, 상기 R101 내지 R103은 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐; 시아노기; 치환 또는 비치환된 탄소수 3 내지 30의 단환 또는 다환의 시클로알킬기; 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 및 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기로 이루어진 군으로부터 선택될 수 있다.In the present specification, 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.
본 명세서에 있어서, 알킬실릴기는 알킬기가 치환된 실릴기를 의미한다.In the present specification, an alkylsilyl group means a silyl group substituted with an alkyl group.
본 명세서에 있어서, 아릴실릴기는 아릴기가 치환된 실릴기를 의미한다.In the present specification, an arylsilyl group means a silyl group substituted with an aryl group.
구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나, 이에 한정되는 것은 아니다.Specific examples include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl and phenylsilyl groups .
본 명세서에 있어서, 붕소기는 -BR104R105일 수 있으며, 상기 R104 및 R105은 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐; 시아노기; 치환 또는 비치환된 탄소수 3 내지 30의 단환 또는 다환의 시클로알킬기; 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 및 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기로 이루어진 군으로부터 선택될 수 있다.In this specification, 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.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며, 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 인데닐기, 페난트레닐기, 파이레닐기, 페릴레닐기, 트리페닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to 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. Examples of the polycyclic aryl group 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.
본 명세서에 있어서, 플루오레닐기는 치환될 수 있고, 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다.In the present specification, a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
상기 플루오레닐기가 치환되는 경우,
Figure PCTKR2018013380-appb-I000005
,
Figure PCTKR2018013380-appb-I000006
등의 스피로플루오레닐기,
Figure PCTKR2018013380-appb-I000007
(9,9-디메틸플루오레닐기), 및
Figure PCTKR2018013380-appb-I000008
(9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,
Figure PCTKR2018013380-appb-I000005
,
Figure PCTKR2018013380-appb-I000006
, A spirofluorenyl group
Figure PCTKR2018013380-appb-I000007
(9,9-dimethylfluorenyl group), and
Figure PCTKR2018013380-appb-I000008
(9,9-diphenylfluorenyl group), and the like. However, the present invention is not limited thereto.
본 명세서에 있어서, 헤테로고리기는 이종원자로 N, O, P, S, Si 및 Se 중 1개 이상을 포함하는 고리기로서, 탄소수는 특별히 한정되지 않으나 탄소수 2 내지 60인 것이 바람직하다. 일 실시상태에 따르면, 상기 헤테로고리기의 탄소수는 2 내지 30이다. 헤테로 고리기의 예로는 예로는 피리딜기, 피롤기, 피리미딜기, 피리다지닐기, 퓨라닐기, 티오페닐기, 카바졸기, 이미다졸기, 피라졸기, 디벤조퓨라닐기, 디벤조티오페닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, 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.
본 명세서에 있어서, 헤테로아릴기는 방향족인 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다.In the present specification, the description of the aforementioned heterocyclic group can be applied, except that the heteroaryl group is aromatic.
본 명세서에 있어서, "인접한" 기는 해당 치환기가 치환된 원자와 직접 연결된 원자에 치환된 치환기, 해당 치환기와 입체구조적으로 가장 가깝게 위치한 치환기, 또는 해당 치환기가 치환된 원자에 치환된 다른 치환기를 의미할 수 있다. 예컨대, 벤젠고리에서 오쏘(ortho)위치로 치환된 2개의 치환기 및 지방족 고리에서 동일 탄소에 치환된 2개의 치환기는 서로 "인접한"기로 해석될 수 있다.In this specification, " 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. 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 " groups to each other.
본 명세서에 있어서, 인접한 기가 서로 결합하여 형성되는 치환 또는 비치환된 고리에서, "고리"는 탄화수소고리; 또는 헤테로고리를 의미한다.In the present specification, in the substituted or unsubstituted ring formed by bonding adjacent groups to each other, the "ring" means a hydrocarbon ring; Or a heterocycle.
본 명세서에 있어서, 탄화수소고리는 방향족, 지방족 또는 방향족과 지방족의 축합고리일 수 있으며, 상기 1가가 아닌 것을 제외하고 상기 시클로알킬기 또는 아릴기의 예시 중에서 선택될 수 있다.In the present specification, 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.
본 명세서에 있어서, 방향족 탄화수소고리는 1가인 것을 제외하고는 아릴기에 관한 설명이 적용될 수 있다.In the present specification, the explanation about the aryl group except for the monovalent aromatic hydrocarbon ring can be applied.
본 명세서에 있어서, 헤테로고리는 탄소가 아닌 원자, 이종원자를 1 이상 포함하는 것으로서, 구체적으로 상기 이종 원자는 N, O, P, S, Si 및 Se 등으로 이루어진 군에서 선택되는 원자를 1 이상 포함할 수 있다. 상기 헤테로고리는 단환 또는 다환일 수 있으며, 방향족, 지방족 또는 방향족과 지방족의 축합고리일 수 있으며, 방향족 헤테로고리는 1가가 아닌 것을 제외하고 상기 헤테로아릴기의 예시 중에서 선택될 수 있다.In the present specification, the hetero ring includes one or more non-carbon atoms and hetero atoms. Specifically, 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.
본 명세서의 일 실시상태에 따르면, 상기 X1은 N 또는 CR11이다.According to one embodiment of the present disclosure, X1 is N or CR11.
본 명세서의 일 실시상태에 있어서, 상기 R11은 수소; 중수소; 할로겐기; 탄소수 1 내지 20의 알킬실릴기; 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 치환 또는 비치환된 탄소수 12 내지 60의 아릴아민기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성한다.In one embodiment of the present disclosure, 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.
또 하나의 일 실시상태에 따르면, 상기 R11은 수소; 중수소; 할로겐기; 탄소수 3 내지 20의 트리알킬실릴기; 치환 또는 비치환된 메틸기; 치환 또는 비치환된 부틸기; 치환 또는 비치환된 시클로헥실기; 치환 또는 비치환된 디페닐아민기; 치환 또는 비치환된 페닐기; 또는 치환 또는 비치환된 카바졸기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성한다.According to another embodiment, 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.
또 하나의 일 실시상태에 있어서, 상기 R11은 수소; 중수소; 불소(-F); 트리메틸실릴기; 메틸기; tert-부틸기; 시클로헥실기; 디페닐아민기; 페닐기; 또는 카바졸기이거나, R21과 서로 결합하여 치환 또는 비치환된 고리를 형성한다.In another embodiment 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.
본 명세서의 일 실시상태에 따르면, 상기 X2는 N 또는 CR12이고, X3는 N 또는 CR13이며, X2가 N인 경우 X3는 CR13이고, X3가 N인 경우 X2는 CR12이다.According to one embodiment of the present disclosure, X2 is N or CR12, X3 is N or CR13, X3 is CR13 when X2 is N, and X2 is CR12 when X3 is N.
본 명세서의 일 실시상태에 따르면, 상기 X2는 N 또는 CR12이고, X3는 CR13이다.According to one embodiment of the present disclosure, X2 is N or CR12 and X3 is CR13.
또 하나의 일 실시상태에 따르면, 상기 X2는 CR12이고, X3는 N 또는 CR13이다.According to another embodiment, X2 is CR12 and X3 is N or CR13.
본 명세서의 일 실시상태에 따르면, 상기 R3 및 R12; 또는 R3 및 R13은 상기 화학식 2의 점선부와 연결되어 고리를 형성한다. According to one embodiment of the present disclosure, R3 and R12; Or R < 3 > and R < 13 > are connected to the dotted line of formula (2) to form a ring.
본 명세서의 일 실시상태에 있어서, 상기 R12가 상기 화학식 2의 점선부와 연결되어 고리를 형성하지 않는 경우, 상기 R12는 수소; 중수소; 할로겐기; 탄소수 1 내지 20의 알킬실릴기; 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 치환 또는 비치환된 탄소수 12 내지 60의 아릴아민기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성한다.In one embodiment of the present invention, 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.
또 하나의 일 실시상태에 따르면, 상기 R12가 상기 화학식 2의 점선부와 연결되어 고리를 형성하지 않는 경우, 상기 R12는 수소; 중수소; 할로겐기; 탄소수 3 내지 20의 트리알킬실릴기; 치환 또는 비치환된 메틸기; 치환 또는 비치환된 부틸기; 치환 또는 비치환된 시클로헥실기; 치환 또는 비치환된 디페닐아민기; 치환 또는 비치환된 페닐기; 또는 치환 또는 비치환된 카바졸기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성한다.According to another embodiment, 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.
또 하나의 일 실시상태에 있어서, 상기 R12가 상기 화학식 2의 점선부와 연결되어 고리를 형성하지 않는 경우, 상기 R12는 수소; 중수소; 불소(-F); 트리메틸실릴기; 메틸기; tert-부틸기; 시클로헥실기; 디페닐아민기; 페닐기; 또는 카바졸기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성한다.In another embodiment, 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.
본 명세서의 일 실시상태에 있어서, 상기 R13이 상기 화학식 2의 점선부와 연결되어 고리를 형성하지 않는 경우, 상기 R13은 수소; 중수소; 할로겐기; 탄소수 1 내지 20의 알킬실릴기; 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 치환 또는 비치환된 탄소수 12 내지 60의 아릴아민기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성한다.In an embodiment of the present invention, 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.
또 하나의 일 실시상태에 따르면, 상기 R13이 상기 화학식 2의 점선부와 연결되어 고리를 형성하지 않는 경우, 상기 R13은 수소; 중수소; 할로겐기; 탄소수 3 내지 20의 트리알킬실릴기; 치환 또는 비치환된 메틸기; 치환 또는 비치환된 부틸기; 치환 또는 비치환된 시클로헥실기; 치환 또는 비치환된 디페닐아민기; 치환 또는 비치환된 페닐기; 또는 치환 또는 비치환된 카바졸기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성한다.According to another embodiment, 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.
또 하나의 일 실시상태에 있어서, 상기 R13이 상기 화학식 2의 점선부와 연결되어 고리를 형성하지 않는 경우, 상기 R13은 수소; 중수소; 불소(-F); 트리메틸실릴기; 메틸기; tert-부틸기; 시클로헥실기; 디페닐아민기; 페닐기; 또는 카바졸기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성한다.In another embodiment, 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.
또 하나의 일 실시상태에 따르면, 상기 R13이 상기 화학식 2의 점선부와 연결되어 고리를 형성하지 않는 경우, 상기 R13은 수소이다.According to another embodiment of the present invention, when R13 is not connected to the dotted line of formula (2) to form a ring, R13 is hydrogen.
본 명세서의 일 실시상태에 따르면, 상기 R3 및 R12; 또는 R3 및 R13은 상기 화학식 2의 점선부와 연결되어 고리를 형성한다. According to one embodiment of the present disclosure, R3 and R12; Or R < 3 > and R < 13 > are connected to the dotted line of formula (2) to form a ring.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1은 하기 화학식 1-1 또는 화학식 1-2로 표시될 수 있다.In one embodiment of the present invention, Formula 1 may be represented by Formula 1-1 or Formula 1-2.
[화학식 1-1][Formula 1-1]
Figure PCTKR2018013380-appb-I000009
Figure PCTKR2018013380-appb-I000009
[화학식 1-2][Formula 1-2]
Figure PCTKR2018013380-appb-I000010
Figure PCTKR2018013380-appb-I000010
상기 화학식 1-1 및 화학식 1-2에 있어서,In the above Formulas 1-1 and 1-2,
W, X1, R1, R2, A1, Ar1 및 Ar2는 상기 화학식 1에서의 정의와 같고,W, X 1, R 1, R 2, A 1, Ar 1 and Ar 2 have the same definitions as in formula (1)
X21 및 X31은 서로 같거나 상이하고, 각각 독립적으로 N 또는 CR41이며,X21 and X31 are the same or different and are each independently N or CR41,
R41은 수소; 중수소; 할로겐기; 시아노기; 알킬실릴기; 아릴실릴기; 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 알콕시아릴기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하고,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 및 R4; 및 R3 및 R5는 상기 화학식 2의 점선부와 연결되어 고리를 형성한다.R3 and R4; And R < 3 > and R < 5 > are connected to the dotted line of formula (2) to form a ring.
본 명세서의 일 실시상태에 있어서, 상기 R41은 수소; 중수소; 할로겐기; 탄소수 1 내지 20의 알킬실릴기; 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 치환 또는 비치환된 탄소수 12 내지 60의 아릴아민기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성한다.In one embodiment of the present disclosure, 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.
또 하나의 일 실시상태에 따르면, 상기 R41은 수소; 중수소; 할로겐기; 탄소수 3 내지 20의 트리알킬실릴기; 치환 또는 비치환된 메틸기; 치환 또는 비치환된 부틸기; 치환 또는 비치환된 시클로헥실기; 치환 또는 비치환된 디페닐아민기; 치환 또는 비치환된 페닐기; 또는 치환 또는 비치환된 카바졸기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성한다.According to another embodiment, 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.
또 하나의 일 실시상태에 있어서, 상기 R41은 수소; 중수소; 불소(-F); 트리메틸실릴기; 메틸기; tert-부틸기; 시클로헥실기; 디페닐아민기; 페닐기; 또는 카바졸기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성한다.In another embodiment 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.
본 명세서의 일 실시상태에 따르면, 상기 Y는 O, S, Se, NR21, PR22, C=O, CR23R24, SiR25R26 또는 P(=O)R27이다.According to one embodiment of the present disclosure, Y is O, S, Se, NR21, PR22, C = O, CR23R24, SiR25R26 or P (= O) R27.
본 명세서의 일 실시상태에 있어서, 상기 R21은 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성한다,In one embodiment of the present specification, 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,
또 하나의 일 실시상태에 따르면, 상기 R21은 치환 또는 비치환된 탄소수 1내지 60의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 60의 아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성한다.According to another embodiment, 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.
또 하나의 일 실시상태에 있어서, 상기 R21은 치환 또는 비치환된 탄소수 1내지 20의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성한다.In another embodiment, 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.
또 하나의 일 실시상태에 따르면, 상기 R21은 치환 또는 비치환된 메틸기; 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 또는 치환 또는 비치환된 나프틸기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성한다.According to another embodiment, 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.
또 하나의 일 실시상태에 있어서, 상기 R21은 메틸기; 페닐기; 바이페닐기; 또는 나프틸기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성한다.In another embodiment, 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.
본 명세서의 일 실시상태에 있어서, 상기 R22는 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이다.In one embodiment of the present specification, R22 is a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
또 하나의 일 실시상태에 따르면, 상기 R22는 치환 또는 비치환된 탄소수 1 내지 60의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 60의 아릴기이다.According to another embodiment, 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.
또 하나의 일 실시상태에 있어서, 상기 R22는 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이다.In another embodiment, 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.
또 하나의 일 실시상태에 따르면, 상기 R22는 치환 또는 비치환된 메틸기; 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 또는 치환 또는 비치환된 나프틸기이다. According to another embodiment, 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.
또 하나의 일 실시상태에 있어서, 상기 R22는 메틸기; 페닐기; 바이페닐기; 또는 나프틸기이다.In another embodiment, R22 is a methyl group; A phenyl group; A biphenyl group; Or a naphthyl group.
본 명세서의 일 실시상태에 따르면, 상기 R23 및 R24는 서로 같거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이거나, 서로 결합하여 치환 또는 비치환된 고리를 형성한다.According to one embodiment of the present disclosure, 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.
또 하나의 일 실시상태에 있어서, 상기 R23 및 R24는 서로 같거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 탄소수 1 내지 60의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 60의 아릴기이거나, 서로 결합하여 치환 또는 비치환된 고리를 형성한다.In another embodiment, 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.
또 하나의 일 실시상태에 따르면, 상기 R23 및 R24는 서로 같거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 탄소수 1 내지 30의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이거나, 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 60의 탄화수소 고리를 형성한다.According to another embodiment, 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.
또 하나의 일 실시상태에 있어서, 상기 R23 및 R24는 서로 같거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 메틸기; 치환 또는 비치환된 에틸기; 치환 또는 비치환된 프로필기; 치환 또는 비치환된 부틸기; 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 또는 치환 또는 비치환된 나프틸기이거나, 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 30의 탄화수소 고리를 형성한다.In another embodiment, 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.
또 하나의 일 실시상태에 따르면, 상기 R23 및 R24는 서로 같거나 상이하고, 각각 독립적으로 수소; 메틸기; 에틸기; 이소프로필기; tert-부틸기; 페닐기; 바이페닐기; 또는 나프틸기이거나, 서로 결합하여 플루오렌 고리를 형성한다.According to another embodiment, 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.
본 명세서의 일 실시상태에 따르면, 상기 R25 내지 R27은 서로 같거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이다.According to one embodiment of the present invention, 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.
또 하나의 일 실시상태에 있어서, 상기 R25 내지 R27은 서로 같거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 탄소수 1 내지 60의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 60의 아릴기이다.In another embodiment, 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.
또 하나의 일 실시상태에 따르면, 상기 R25 내지 R27은 서로 같거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 탄소수 1 내지 30의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이다.According to another embodiment, 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.
본 명세서의 일 실시상태에 있어서, 상기 A1은 치환 또는 비치환된 탄소수 6 내지 60의 방향족 탄화수소고리; 또는 치환 또는 비치환된 탄소수 2 내지 60의 방향족 헤테로고리이다.In one embodiment of the present invention, 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.
또 하나의 일 실시상태에 따르면, 상기 A1은 치환 또는 비치환된 탄소수 6 내지 30의 방향족 탄화수소고리; 또는 치환 또는 비치환된 탄소수 2 내지 30의 방향족 헤테로고리이다.According to another embodiment, 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.
또 하나의 일 실시상태에 있어서, 상기 A1은 치환 또는 비치환된 벤젠고리이다.In another embodiment, A1 is a substituted or unsubstituted benzene ring.
본 명세서의 일 실시상태에 따르면, 상기 A1은 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 치환 또는 비치환된 아민기, 및 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기로 이루어진 군으로부터 선택된 1 이상의 치환기로 치환 또는 비치환된 탄소수 6 내지 30의 방향족 탄화수소고리이다.According to one embodiment of the present invention, 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.
또 하나의 일 실시상태에 있어서, 상기 A1은 중수소로 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 탄소수 3 내지 30의 시클로알킬기, 탄소수 1 내지 20의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 탄소수 1 내지 20의 알킬기로 치환 또는 비치환된 탄소수 12 내지 30의 아릴아민기, 및 이종원소로 S, O 또는 N을 포함하는 탄소수 2 내지 30의 헤테로고리기로 이루어진 군으로부터 선택된 1 이상의 치환기로 치환 또는 비치환된 탄소수 6 내지 30의 방향족 탄화수소고리이다.In another embodiment, 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.
또 하나의 일 실시상태에 따르면, 상기 A1은 중수소로 치환 또는 비치환된 메틸기, tert-부틸기, 시클로헥실기, 메틸기로 치환 또는 비치환된 페닐기, tert-부틸기로 치환 또는 비치환된 디페닐아민기, 및 카바졸기로 이루어진 군으로부터 선택된 1 이상의 치환기로 치환 또는 비치환된 탄소수 6 내지 30의 방향족 탄화수소고리이다.According to another embodiment, 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 amino group, an amino group, an amino group, an amino group, an amine group, and a carbazole group.
또 하나의 일 실시상태에 따르면, 상기 A1은 중수소로 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 탄소수 3 내지 30의 시클로알킬기, 탄소수 1 내지 20의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 탄소수 1 내지 20의 알킬기로 치환 또는 비치환된 탄소수 12 내지 30의 아릴아민기, 및 이종원소로 S, O 또는 N을 포함하는 탄소수 2 내지 30의 헤테로고리기로 이루어진 군으로부터 선택된 1 이상의 치환기로 치환 또는 비치환된 벤젠고리이다.According to another embodiment, 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.
또 하나의 일 실시상태에 따르면, 상기 A1은 중수소로 치환 또는 비치환된 메틸기, tert-부틸기, 시클로헥실기, 메틸기로 치환 또는 비치환된 페닐기, tert-부틸기로 치환 또는 비치환된 디페닐아민기, 및 카바졸기로 이루어진 군으로부터 선택된 1 이상의 치환기로 치환 또는 비치환된 벤젠고리이다.According to another embodiment, 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.
본 명세서의 일 실시상태에 있어서, 상기 A2는 치환 또는 비치환된 탄소수 6 내지 60의 방향족 탄화수소고리; 또는 치환 또는 비치환된 탄소수 2 내지 60의 방향족 헤테로고리이다.In one embodiment of the present specification, 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.
또 하나의 일 실시상태에 따르면, 상기 A2는 치환 또는 비치환된 탄소수 6 내지 30의 방향족 탄화수소고리; 또는 치환 또는 비치환된 탄소수 2 내지 30의 방향족 헤테로고리이다.According to another embodiment, 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.
또 하나의 일 실시상태에 있어서, 상기 A2는 치환 또는 비치환된 알킬실릴기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 시클로알킬기, 치환 또는 비치환된 아민기, 치환 또는 비치환된 아릴기, 및 치환 또는 비치환된 헤테로고리기로 이루어진 군으로부터 선택된 1 이상의 치환기로 치환 또는 비치환된 탄소수 6 내지 30의 방향족 탄화수소고리; 또는 치환 또는 비치환된 알킬실릴기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 시클로알킬기, 치환 또는 비치환된 아민기, 치환 또는 비치환된 아릴기, 및 치환 또는 비치환된 헤테로고리기로 이루어진 군으로부터 선택된 1 이상의 치환기로 치환 또는 비치환된 탄소수 2 내지 30의 방향족 헤테로고리이다.In another embodiment, 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 An aromatic hydrocarbon ring having 6 to 30 carbon atoms, which is unsubstituted or substituted with at least one substituent selected from the group consisting of 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 an aromatic heterocyclic ring having 2 to 30 carbon atoms, which is unsubstituted or substituted with at least one substituent selected from the group consisting of
또 하나의 일 실시상태에 따르면, 상기 A2는 탄소수 3 내지 20의 트리알킬실릴기, 중수소로 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 탄소수 3 내지 30의 시클로알킬기, 탄소수 12 내지 30의 아릴아민기, 할로겐기 또는 탄소수 1 내지 20의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 및 헤테로고리기로 이루어진 군으로부터 선택된 1 이상의 치환기로 치환 또는 비치환된 탄소수 6 내지 30의 방향족 탄화수소고리; 또는 탄소수 3 내지 20의 트리알킬실릴기, 중수소로 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 탄소수 3 내지 30의 시클로알킬기, 탄소수 12 내지 30의 아릴아민기, 할로겐기 또는 탄소수 1 내지 20의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 및 헤테로고리기로 이루어진 군으로부터 선택된 1 이상의 치환기로 치환 또는 비치환된 탄소수 2 내지 30의 방향족 헤테로고리이다.According to another embodiment, 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; 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, a halogen group, An aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group, and a heterocyclic group, and which is unsubstituted or substituted with at least one substituent selected from the group consisting of a halogen atom,
또 하나의 일 실시상태에 있어서, 상기 A2는 탄소수 3 내지 20의 트리알킬실릴기, 중수소로 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 탄소수 3 내지 30의 시클로알킬기, 탄소수 12 내지 30의 아릴아민기, 할로겐기 또는 탄소수 1 내지 20의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 및 헤테로고리기로 이루어진 군으로부터 선택된 1 이상의 치환기로 치환 또는 비치환된 벤젠고리; 탄소수 3 내지 20의 트리알킬실릴기, 중수소로 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 탄소수 3 내지 30의 시클로알킬기, 탄소수 12 내지 30의 아릴아민기, 할로겐기 또는 탄소수 1 내지 20의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 및 헤테로고리기로 이루어진 군으로부터 선택된 1 이상의 치환기로 치환 또는 비치환된 나프탈렌고리; 또는 탄소수 3 내지 20의 트리알킬실릴기, 중수소로 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 탄소수 3 내지 30의 시클로알킬기, 탄소수 12 내지 30의 아릴아민기, 할로겐기 또는 탄소수 1 내지 20의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 및 헤테로고리기로 이루어진 군으로부터 선택된 1 이상의 치환기로 치환 또는 비치환된 디벤조퓨란고리이다.In another embodiment, 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 A benzene ring substituted or unsubstituted with at least one substituent selected from the group consisting of an amino group, 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; 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 arylamine group having 12 to 30 carbon atoms, a halogen group or an alkyl group having 1 to 20 carbon atoms A substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a heterocyclic group; 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, a halogen group, A dibenzofuran ring substituted or unsubstituted with at least one substituent selected from the group consisting of an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group, and a heterocyclic group.
또 하나의 일 실시상태에 따르면, 상기 A2는 트리메틸실릴기, 중수소로 치환된 메틸기, 프로필기, 부틸기, 시클로헥실기, 디페닐아민기, 불소 또는 부틸기로 치환 또는 비치환된 페닐기, 및 카바졸기로 이루어진 군으로부터 선택된 1 이상의 치환기로 치환 또는 비치환된 벤젠고리; 나프탈렌고리; 또는 디벤조퓨란고리이다.According to another embodiment, 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.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 2-1 내지 2-7 중 어느 하나로 표시될 수 있다.According to one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (2-1) to (2-7).
[화학식 2-1][Formula 2-1]
Figure PCTKR2018013380-appb-I000011
Figure PCTKR2018013380-appb-I000011
[화학식 2-2][Formula 2-2]
Figure PCTKR2018013380-appb-I000012
Figure PCTKR2018013380-appb-I000012
[화학식 2-3][Formula 2-3]
Figure PCTKR2018013380-appb-I000013
Figure PCTKR2018013380-appb-I000013
[화학식 2-4][Chemical Formula 2-4]
Figure PCTKR2018013380-appb-I000014
Figure PCTKR2018013380-appb-I000014
[화학식 2-5][Chemical Formula 2-5]
Figure PCTKR2018013380-appb-I000015
Figure PCTKR2018013380-appb-I000015
[화학식 2-6][Chemical Formula 2-6]
Figure PCTKR2018013380-appb-I000016
Figure PCTKR2018013380-appb-I000016
[화학식 2-7][Chemical Formula 2-7]
Figure PCTKR2018013380-appb-I000017
Figure PCTKR2018013380-appb-I000017
상기 화학식 2-1 내지 화학식 2-7에 있어서,In Formulas 2-1 to 2-7,
W, X1, X2, X3, A1, Ar1 및 Ar2는 상기 화학식 1에서의 정의와 같고,W, X 1, X 2, X 3, A 1, Ar 1 and Ar 2 have the same definitions as in the above formula (1)
Y1 내지 Y14는 서로 같거나 상이하고, 각각 독립적으로 상기 화학식 2에서 Y의 정의와 같으며,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 내지 A34는 서로 같거나 상이하고, 각각 독립적으로 상기 화학식 2에서의 A2의 정의와 같다.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).
본 명세서의 일 실시상태에 따르면, 상기 Y1 내지 Y14는 서로 같거나 상이하고, 각각 독립적으로 상기 화학식 2의 Y에 대하여 정의한 바와 같다.According to one embodiment of the present invention, Y1 to Y14 are the same as or different from each other and each independently as defined for Y in Formula 2 above.
본 명세서의 일 실시상태에 따르면, 상기 Y1 내지 Y14는 서로 같거나 상이하고, 각각 독립적으로 O, S, Se, NR21, PR22, C=O, CR23R24, SiR25R26 또는 P(=O)R27이며, R21 내지 R27은 상기 정의한 바와 같다.According to one embodiment of the present invention, Y1 to Y14 are the same or different from each other and each independently represents O, S, Se, NR21, PR22, C = O, CR23R24, SiR25R26 or P To R < 27 > are as defined above.
본 명세서의 일 실시상태에 있어서, 상기 A21 내지 A34는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 60의 방향족 탄화수소고리; 또는 치환 또는 비치환된 탄소수 2 내지 60의 방향족 헤테로고리이다.In one embodiment of the present invention, 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.
또 하나의 일 실시상태에 따르면, 상기 A21 내지 A34는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 방향족 탄화수소고리; 또는 치환 또는 비치환된 탄소수 2 내지 30의 방향족 헤테로고리이다.According to another embodiment, 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.
또 하나의 일 실시상태에 있어서, 상기 A21 내지 A34는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬실릴기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 시클로알킬기, 치환 또는 비치환된 아민기, 치환 또는 비치환된 아릴기, 및 치환 또는 비치환된 헤테로고리기로 이루어진 군으로부터 선택된 1 이상의 치환기로 치환 또는 비치환된 탄소수 6 내지 30의 방향족 탄화수소고리; 또는 치환 또는 비치환된 알킬실릴기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 시클로알킬기, 치환 또는 비치환된 아민기, 치환 또는 비치환된 아릴기, 및 치환 또는 비치환된 헤테로고리기로 이루어진 군으로부터 선택된 1 이상의 치환기로 치환 또는 비치환된 탄소수 2 내지 30의 방향족 헤테로고리이다.In another embodiment, 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 an aromatic heterocyclic ring having 2 to 30 carbon atoms, which is unsubstituted or substituted with at least one substituent selected from the group consisting of
또 하나의 일 실시상태에 따르면, 상기 A21 내지 A34는 서로 같거나 상이하고, 각각 독립적으로 탄소수 3 내지 20의 트리알킬실릴기, 중수소로 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 탄소수 3 내지 30의 시클로알킬기, 탄소수 12 내지 30의 아릴아민기, 할로겐기 또는 탄소수 1 내지 20의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 및 헤테로고리기로 이루어진 군으로부터 선택된 1 이상의 치환기로 치환 또는 비치환된 탄소수 6 내지 30의 방향족 탄화수소고리; 또는 탄소수 3 내지 20의 트리알킬실릴기, 중수소로 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 탄소수 3 내지 30의 시클로알킬기, 탄소수 12 내지 30의 아릴아민기, 할로겐기 또는 탄소수 1 내지 20의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 및 헤테로고리기로 이루어진 군으로부터 선택된 1 이상의 치환기로 치환 또는 비치환된 탄소수 2 내지 30의 방향족 헤테로고리이다.According to another embodiment, 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, a halogen group, An aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group, and a heterocyclic group, and which is unsubstituted or substituted with at least one substituent selected from the group consisting of a halogen atom,
또 하나의 일 실시상태에 있어서, 상기 A21 내지 A34는 서로 같거나 상이하고, 각각 독립적으로 탄소수 3 내지 20의 트리알킬실릴기, 중수소로 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 탄소수 3 내지 30의 시클로알킬기, 탄소수 12 내지 30의 아릴아민기, 할로겐기 또는 탄소수 1 내지 20의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 및 헤테로고리기로 이루어진 군으로부터 선택된 1 이상의 치환기로 치환 또는 비치환된 벤젠고리; 탄소수 3 내지 20의 트리알킬실릴기, 중수소로 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 탄소수 3 내지 30의 시클로알킬기, 탄소수 12 내지 30의 아릴아민기, 할로겐기 또는 탄소수 1 내지 20의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 및 헤테로고리기로 이루어진 군으로부터 선택된 1 이상의 치환기로 치환 또는 비치환된 나프탈렌고리; 또는 탄소수 3 내지 20의 트리알킬릴실기, 중수소로 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 탄소수 3 내지 30의 시클로알킬기, 탄소수 12 내지 30의 아릴아민기, 할로겐기 또는 탄소수 1 내지 20의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 및 헤테로고리기로 이루어진 군으로부터 선택된 1 이상의 치환기로 치환 또는 비치환된 디벤조퓨란고리이다.In another embodiment, 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; 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 arylamine group having 12 to 30 carbon atoms, a halogen group or an alkyl group having 1 to 20 carbon atoms A substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a heterocyclic group; Or 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 arylamine group having 12 to 30 carbon atoms, a halogen group, A dibenzofuran ring substituted or unsubstituted with at least one substituent selected from the group consisting of an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group, and a heterocyclic group.
또 하나의 일 실시상태에 따르면, 상기 A21 내지 A34는 서로 같거나 상이하고, 각각 독립적으로 트리메틸실릴기, 중수소로 치환된 메틸기, 프로필기, 부틸기, 시클로헥실기, 디페닐아민기, 불소 또는 부틸기로 치환 또는 비치환된 페닐기, 및 카바졸기로 이루어진 군으로부터 선택된 1 이상의 치환기로 치환 또는 비치환된 벤젠고리; 나프탈렌고리; 또는 디벤조퓨란고리이다.According to another embodiment, 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 A benzene ring substituted or unsubstituted with at least one substituent selected from the group consisting of a phenyl group substituted or unsubstituted with a butyl group, and a carbazole group; Naphthalene ring; Or a dibenzofuran ring.
본 명세서의 일 실시상태에 있어서, 상기 W는 O, S, Se, NRa, PRb, C=O, CRcRd, SiReRf 또는 P(=O)Rg이다.In one embodiment of the present specification, W is O, S, Se, NRa, PRb, C = O, CRcRd, SiReRf or P (= O) Rg.
본 명세서의 일 실시상태에 따르면, 상기 Ra 내지 Rg는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 60의 아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성한다.According to one embodiment of the present invention, 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.
본 명세서의 일 실시상태에 있어서, 상기 Ra는 치환 또는 비치환된 탄소수 6 내지 60의 아릴기이다.In one embodiment of the present specification, Ra is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
또 하나의 일 실시상태에 따르면, 상기 Ra는 중수소, 할로겐기, 및 탄소수 1 내지 20의 알킬기로 이루어진 군으로부터 선택된 1 이상의 치환기로 치환 또는 비치환된 탄소수 6 내지 60의 아릴기이다.According to another embodiment, 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.
또 하나의 일 실시상태에 따르면, 상기 Ra는 중수소, 할로겐기, 및 탄소수 1 내지 20의 알킬기로 이루어진 군으로부터 선택된 1 이상의 치환기로 치환 또는 비치환된 페닐기; 중수소, 할로겐기, 및 탄소수 1 내지 20의 알킬기로 이루어진 군으로부터 선택된 1 이상의 치환기로 치환 또는 비치환된 나프틸기; 또는 중수소, 할로겐기, 및 탄소수 1 내지 20의 알킬기로 이루어진 군으로부터 선택된 1 이상의 치환기로 치환 또는 비치환된 바이페닐기이다.According to another embodiment, 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.
또 하나의 일 실시상태에 있어서, 상기 Ra는 중수소, 불소(-F) 및 부틸기로 이루어진 군으로부터 선택된 1 이상의 치환기로 치환 또는 비치환된 탄소수 6 내지 60의 아릴기이다.In another embodiment, 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.
또 하나의 일 실시상태에 따르면, 상기 Ra는 중수소, 불소(-F) 및 부틸기로 이루어진 군으로부터 선택된 1 이상의 치환기로 치환 또는 비치환된 페닐기; 중수소, 불소(-F) 및 부틸기로 이루어진 군으로부터 선택된 1 이상의 치환기로 치환 또는 비치환된 나프틸기; 또는 중수소, 불소(-F) 및 부틸기로 이루어진 군으로부터 선택된 1 이상의 치환기로 치환 또는 비치환된 바이페닐기이다.According to another embodiment, 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.
본 명세서의 일 실시상태에 따르면, 상기 Rb는 탄소수 6 내지 30의 아릴기이다.According to one embodiment of the present invention, Rb is an aryl group having 6 to 30 carbon atoms.
또 하나의 일 실시상태에 따르면, 상기 Rb는 치환 또는 비치환된 페닐기이다.According to another embodiment, Rb is a substituted or unsubstituted phenyl group.
또 하나의 일 실시상태에 따르면, 상기 Rb는 페닐기이다.According to another embodiment, Rb is a phenyl group.
본 명세서의 일 실시상태에 따르면, 상기 Rc 및 Rd는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이거나, 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 30의 탄화수소 고리를 형성한다.According to one embodiment of the present invention, 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.
또 하나의 일 실시상태에 있어서, 상기 Rc 및 Rd는 서로 같거나 상이하고, 각각 독립적으로 탄소수 1 내지 20의 알킬기; 또는 탄소수 1 내지 20의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이거나, 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 30의 탄화수소 고리를 형성한다.In another embodiment, 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.
또 하나의 일 실시상태에 따르면, 상기 Rc 및 Rd는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 메틸기; 또는 치환 또는 비치환된 페닐기이거나, 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 30의 탄화수소 고리를 형성한다.According to another embodiment, 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.
또 하나의 일 실시상태에 있어서, 상기 Rc 및 Rd는 서로 같거나 상이하고, 각각 독립적으로 메틸기; 또는 메틸기로 치환 또는 비치환된 페닐기이거나, 서로 결합하여 플루오렌고리를 형성한다.In another embodiment, 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.
본 명세서의 일 실시상태에 따르면, 상기 Re 내지 Rg는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이거나, 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 30의 탄화수소 고리를 형성한다.According to one embodiment of the present invention, 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 치환 또는 비치환된 탄소수 1 내지 60의 알킬기; 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성한다.In one embodiment of the present specification, 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 탄소수 1 내지 20의 알킬기로 치환 또는 비치환된 탄소수 6 내지 60의 아릴기이다.In one embodiment of the present invention, 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.
또 하나의 일 실시상태에 따르면, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 탄소수 1 내지 20의 알킬기로 치환 또는 비치환된 페닐기; 탄소수 1 내지 20의 알킬기로 치환 또는 비치환된 바이페닐기; 또는 탄소수 1 내지 20의 알킬기로 치환 또는 비치환된 나프틸기이다.According to another embodiment, 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.
또 하나의 일 실시상태에 따르면, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 메틸기 또는 부틸기로 치환 또는 비치환된 페닐기; 바이페닐기; 또는 나프틸기이다.According to another embodiment, 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.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1은 하기 구조들 중 어느 하나로 표시될 수 있다.In one embodiment of the present invention, the formula (1) may be represented by any one of the following structures.
Figure PCTKR2018013380-appb-I000018
Figure PCTKR2018013380-appb-I000018
Figure PCTKR2018013380-appb-I000019
Figure PCTKR2018013380-appb-I000019
Figure PCTKR2018013380-appb-I000020
Figure PCTKR2018013380-appb-I000020
Figure PCTKR2018013380-appb-I000021
Figure PCTKR2018013380-appb-I000021
Figure PCTKR2018013380-appb-I000022
Figure PCTKR2018013380-appb-I000022
Figure PCTKR2018013380-appb-I000023
Figure PCTKR2018013380-appb-I000023
Figure PCTKR2018013380-appb-I000024
Figure PCTKR2018013380-appb-I000024
Figure PCTKR2018013380-appb-I000025
Figure PCTKR2018013380-appb-I000025
Figure PCTKR2018013380-appb-I000026
Figure PCTKR2018013380-appb-I000026
Figure PCTKR2018013380-appb-I000027
Figure PCTKR2018013380-appb-I000027
Figure PCTKR2018013380-appb-I000028
Figure PCTKR2018013380-appb-I000028
Figure PCTKR2018013380-appb-I000029
Figure PCTKR2018013380-appb-I000029
Figure PCTKR2018013380-appb-I000030
Figure PCTKR2018013380-appb-I000030
Figure PCTKR2018013380-appb-I000031
Figure PCTKR2018013380-appb-I000031
Figure PCTKR2018013380-appb-I000032
Figure PCTKR2018013380-appb-I000032
Figure PCTKR2018013380-appb-I000033
Figure PCTKR2018013380-appb-I000033
Figure PCTKR2018013380-appb-I000034
Figure PCTKR2018013380-appb-I000034
Figure PCTKR2018013380-appb-I000035
Figure PCTKR2018013380-appb-I000035
Figure PCTKR2018013380-appb-I000036
Figure PCTKR2018013380-appb-I000036
Figure PCTKR2018013380-appb-I000037
Figure PCTKR2018013380-appb-I000037
Figure PCTKR2018013380-appb-I000038
Figure PCTKR2018013380-appb-I000038
Figure PCTKR2018013380-appb-I000039
Figure PCTKR2018013380-appb-I000039
Figure PCTKR2018013380-appb-I000040
Figure PCTKR2018013380-appb-I000040
Figure PCTKR2018013380-appb-I000041
Figure PCTKR2018013380-appb-I000041
Figure PCTKR2018013380-appb-I000042
Figure PCTKR2018013380-appb-I000042
Figure PCTKR2018013380-appb-I000043
Figure PCTKR2018013380-appb-I000043
Figure PCTKR2018013380-appb-I000044
Figure PCTKR2018013380-appb-I000044
Figure PCTKR2018013380-appb-I000045
Figure PCTKR2018013380-appb-I000045
본 명세서의 일 실시상태에 따른 화학식 1의 화합물은 후술하는 제조방법으로 제조될 수 있다.The compound of formula (1) according to one embodiment of the present invention can be prepared by the following production method.
예컨대 상기 화학식 1의 화합물은 후술하는 제조방법과 같이 코어구조가 제조될 수 있다. 치환기는 당 기술분야에 알려져 있는 방법에 의하여 결합될 수 있으며, 치환기의 종류, 위치 또는 개수는 당 기술분야에 알려져 있는 기술에 따라 변경될 수 있다.For example, 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.
또한, 상기와 같은 구조의 코어 구조에 다양한 치환기를 도입함으로써 도입된 치환기의 고유 특성을 갖는 화합물을 합성할 수 있다. 예컨대, 유기 발광 소자 제조시 사용되는 정공 주입층 물질, 정공 수송용 물질, 발광층 물질 및 전자 수송층 물질에 주로 사용되는 치환기를 상기 코어 구조에 도입함으로써 각 유기물층에서 요구하는 조건들을 충족시키는 물질을 합성할 수 있다.Further, by introducing various substituents into the core structure having the above structure, it is possible to synthesize a compound having the intrinsic characteristics of the substituent introduced. For example, by introducing a substituent mainly used in a hole injecting layer material, a hole transporting material, a light emitting layer material, and an electron transporting layer material used in manufacturing an organic light emitting device into the core structure, a material meeting the requirements of each organic layer is synthesized .
또한, 본 발명에 따른 유기 발광 소자는 제1 전극; 상기 제1 전극과 대향하여 구비되는 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비되는 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화학식 1의 화합물을 포함하는 것을 특징으로 한다.Further, the organic light emitting device according to the present invention 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.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하며, 유기물층 중 1층 이상은 전술한 화합물을 포함하고, 상기 발광층은 하기 화학식 1A로 표시되는 화합물을 포함할 수 있다.According to one embodiment of the present invention, 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).
[화학식 1A]≪ EMI ID =
Figure PCTKR2018013380-appb-I000046
Figure PCTKR2018013380-appb-I000046
상기 화학식 1A에 있어서,In the above formula (1A)
L103 내지 L106은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,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 내지 Ar8은 서로 같거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,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,
R101은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,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,
p는 0 내지 6의 정수이며,p is an integer of 0 to 6,
p가 2 이상인 경우 괄호 내의 치환기는 서로 같거나 상이하다.When p is 2 or more, the substituents in the parentheses are the same or different.
본 명세서의 일 실시상태에 있어서, 상기 L103 내지 L106는 서로 동일하거나 상이하며, 각각 독립적으로 직접결합; 치환 또는 비치환된 탄소수 6 내지 60의 아릴렌기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴렌기이다.In one embodiment of the present invention, 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.
본 명세서의 일 실시상태에 있어서, 상기 L103 내지 L106는 서로 동일하거나 상이하며, 각각 독립적으로 직접결합; 치환 또는 비치환된 탄소수 6 내지 40의 아릴렌기; 또는 치환 또는 비치환된 탄소수 2 내지 40의 헤테로아릴렌기이다.In one embodiment of the present invention, 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.
또 하나의 일 실시상태에 따르면, 상기 L103 내지 L106은 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 페닐렌기; 치환 또는 비치환된 바이페닐릴렌기; 치환 또는 비치환된 터페닐렌기; 치환 또는 비치환된 나프틸렌기; 치환 또는 비치환된 안트라세닐렌기; 치환 또는 비치환된 페난트레닐렌기; 치환 또는 비치환된 트리페닐렌기; 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 티오페닐렌기; 치환 또는 비치환된 퓨라닐렌기; 치환 또는 비치환된 디벤조티오페닐렌기; 치환 또는 비치환된 디벤조퓨라닐렌기; 또는 치환 또는 비치환된 카바졸릴렌기이다.According to another embodiment, 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.
또 하나의 일 실시상태에 있어서, 상기 L103 내지 L106은 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 페닐렌기; 바이페닐릴렌기; 터페닐렌기; 나프틸렌기; 안트라세닐렌기; 페난트레닐렌기; 트리페닐렌기; 메틸기 또는 페닐기로 치환 또는 비치환된 플루오레닐기; 티오페닐렌기; 퓨라닐렌기; 디벤조티오페닐렌기; 디벤조퓨라닐렌기; 또는 에틸기 또는 페닐기로 치환 또는 비치환된 카바졸릴렌기이다.In another embodiment, 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.
또 하나의 일 실시상태에 따르면, 상기 L103 내지 L106는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 또는 하기 구조들 중 선택될 수 있다.According to another embodiment, L103 to L106 are the same or different and are each independently a direct bond; Or one of the following structures.
Figure PCTKR2018013380-appb-I000047
Figure PCTKR2018013380-appb-I000047
본 명세서의 일 실시상태에 따르면, L103은 직접결합이다.According to one embodiment of the present disclosure, L103 is a direct bond.
본 명세서의 일 실시상태에 따르면, L104는 페닐렌기이다.According to one embodiment of the present disclosure, L104 is a phenylene group.
본 명세서의 일 실시상태에 따르면, L105 및 L106은 직접결합이다.According to one embodiment of the present disclosure, L105 and L106 are direct bonds.
본 명세서의 일 실시상태에 있어서, 상기 R101은 수소; 중수소; 할로겐기; 실릴기; 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 또는 치환 또는 비치환된 헤테로고리기이다.In one embodiment of the present disclosure, 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.
본 명세서의 일 실시상태에 있어서, 상기 R101은 서로 동일하거나 상이하며, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.In one embodiment of the present specification, 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.
본 명세서의 일 실시상태에 있어서, 상기 R101은 서로 동일하거나 상이하며, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 50의 알킬기; 치환 또는 비치환된 탄소수 3 내지 60의 시클로알킬기; 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 40인 헤테로고리기이다.In one embodiment of the present specification, 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.
본 명세서의 일 실시상태에 있어서, 상기 R101은 서로 동일하거나 상이하며, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 30의 알킬기; 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 25의 헤테로고리기이다.In one embodiment of the present specification, 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.
또 하나의 일 실시상태에 있어서, 상기 R101은 수소이다.In another embodiment, R101 is hydrogen.
본 명세서의 일 실시상태에 따르면, 상기 p는 0 또는 1이다.According to one embodiment of the present disclosure, p is 0 or 1.
본 명세서의 일 실시상태에 있어서, 상기 Ar5 내지 Ar8은 서로 동일하거나 상이하며, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴기이다.In one embodiment of the present invention, 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.
또 하나의 일 실시상태에 따르면, 상기 Ar5 내지 Ar8은 서로 동일하거나 상이하며, 각각 독립적으로 수소; 탄소수 6 내지 60의 아릴기 또는 탄소수 2 내지 60의 헤테로아릴기로 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 탄소수 내지 60의 아릴기 또는 탄소수 2 내지 60의 헤테로아릴기로 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴기이다.According to another embodiment, 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.
또 하나의 일 실시상태에 있어서, 상기 Ar5 내지 Ar8은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 페난트렌기; 치환 또는 비치환된 안트라센기; 치환 또는 비치환된 트리페닐렌기; 치환 또는 비치환된 디벤조퓨란기; 치환 또는 비치환된 나프토벤조퓨란기; 치환 또는 비치환된 디벤조티오펜기; 치환 또는 비치환된 카바졸기; 치환 또는 비치환된 플루오렌기; 치환 또는 비치환된 티오펜기; 치환 또는 비치환된 퓨란기; 치환 또는 비치환된 벤조티오펜기; 치환 또는 비치환된 벤조퓨란기; 치환 또는 비치환된 벤조카바졸기; 치환 또는 비치환된 벤조플루오렌기; 치환 또는 비치환된 인돌카바졸기; 치환 또는 비치환된 피리딜기; 치환 또는 비치환된 이소퀴놀릴기; 치환 또는 비치환된 퀴놀릴기; 치환 또는 비치환된 퀴나졸릴기; 치환 또는 비치환된 트리아진기; 치환 또는 비치환된 벤즈이미다졸기; 치환 또는 비치환된 벤조옥사졸기; 치환 또는 비치환된 벤조티아졸기; 치환 또는 비치환된 다이하이드로아크리딘기; 치환 또는 비치환된 크산텐기; 또는 치환 또는 비치환된 디벤조실롤기이다.In another embodiment, 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 benzothiophene group; A substituted or unsubstituted benzofuran group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted benzofluorene group; A substituted or unsubstituted indolcarbazole group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted isoquinolyl group; A substituted or unsubstituted quinolyl group; A substituted or unsubstituted quinazolyl group; A substituted or unsubstituted triazine group; A substituted or unsubstituted benzimidazole group; A substituted or unsubstituted benzoxazole group; A substituted or unsubstituted benzothiazole group; A substituted or unsubstituted dihydroacridine group; A substituted or unsubstituted xanthene group; Or a substituted or unsubstituted dibenzosilyl group.
또 하나의 일 실시상태에 따르면, 상기 Ar5 내지 Ar8은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 페닐기; 바이페닐기; 아릴기로 치환 또는 비치환된 나프틸기; 페난트렌기; 안트라센기; 트리페닐렌기; 아릴기로 치환 또는 비치환된 디벤조퓨란기; 나프토벤조퓨란기; 아릴기로 치환 또는 비치환된 디벤조티오펜기; 알킬기, 또는 아릴기로 치환 또는 비치환된 카바졸기; 알킬기, 또는 아릴기로 치환 또는 비치환된 플루오렌기; 아릴기로 치환 또는 비치환된 티오펜기; 아릴기로 치환 또는 비치환된 퓨란기; 벤조티오펜기; 벤조퓨란기; 알킬기, 또는 아릴기로 치환 또는 비치환된 벤조카바졸기; 알킬기, 또는 아릴기로 치환 또는 비치환된 벤조플루오렌기; 인돌카바졸기; 피리딜기; 아릴기로 치환 또는 비치환된 이소퀴놀릴기; 퀴놀릴기; 아릴기로 치환 또는 비치환된 퀴나졸릴기; 아릴기로 치환 또는 비치환된 트리아진기; 아릴기로 치환 또는 비치환된 벤즈이미다졸기; 아릴기로 치환 또는 비치환된 벤조옥사졸기; 아릴기로 치환 또는 비치환된 벤조티아졸기; 알킬기, 또는 아릴기로 치환 또는 비치환된 다이하이드로아크리딘기; 알킬기, 또는 아릴기로 치환 또는 비치환된 크산텐기; 또는 알킬기, 또는 아릴기로 치환 또는 비치환된 디벤조실롤기이다.According to another embodiment, 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; A benzocarbazole group substituted or unsubstituted with an alkyl group or an aryl group; A benzofluorene group substituted or unsubstituted with an alkyl group or an aryl group; Indolecarbazole group; A pyridyl group; An isoquinolyl group substituted or unsubstituted with an aryl group; Quinolyl group; A quinazolyl group substituted or unsubstituted with an aryl group; A triazine group substituted or unsubstituted with an aryl group; A benzimidazole group substituted or unsubstituted with an aryl group; A benzoxazole group substituted or unsubstituted with an aryl group; A benzothiazole group substituted or unsubstituted with an aryl group; An alkyl group, or a dihydroacridine group substituted or unsubstituted with an aryl group; A xanthene group substituted or unsubstituted with an alkyl group or an aryl group; Or a dibenzosilyl group substituted or unsubstituted with an alkyl group or an aryl group.
또 하나의 일 실시상태에 있어서, 상기 Ar5 내지 Ar8은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 페닐기; 바이페닐기; 페닐기로 치환 또는 비치환된 나프틸기; 페난트렌기; 안트라센기; 트리페닐렌기; 페닐기로 치환 또는 비치환된 디벤조퓨란기; 나프토벤조퓨란기; 페닐기로 치환 또는 비치환된 디벤조티오펜기; 메틸기, 에틸기, 또는 페닐기로 치환 또는 비치환된 카바졸기; 메틸기, 또는 페닐기로 치환 또는 비치환된 플루오렌기; 페닐기로 치환 또는 비치환된 티오펜기; 페닐기로 치환 또는 비치환된 퓨란기; 벤조티오펜기; 벤조퓨란기; 메틸기, 또는 페닐기로 치환 또는 비치환된 벤조카바졸기; 메틸기, 또는 페닐기로 치환 또는 비치환된 벤조플루오렌기; 인돌카바졸기; 페닐기 또는 나프틸기로 치환 또는 비치환된 피리딜기; 페닐기로 치환 또는 비치환된 이소퀴놀릴기; 퀴놀릴기; 페닐기로 치환 또는 비치환된 퀴나졸릴기; 페닐기로 치환 또는 비치환된 트리아진기; 페닐기로 치환 또는 비치환된 벤즈이미다졸기; 페닐기로 치환 또는 비치환된 벤조옥사졸기; 페닐기로 치환 또는 비치환된 벤조티아졸기; 메틸기, 또는 페닐기로 치환 또는 비치환된 다이하이드로아크리딘기; 메틸기, 또는 페닐기로 치환 또는 비치환된 크산텐기; 또는 메틸기, 또는 페닐기로 치환 또는 비치환된 디벤조실롤기이다.In another embodiment, 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 phenyl group; Benzothiophene group; Benzofuran group; A methyl group, or a benzocarbazole group substituted or unsubstituted with a phenyl group; A methyl group, or a benzofluorene group substituted or unsubstituted with a phenyl group; Indolecarbazole group; A pyridyl group substituted or unsubstituted with a phenyl group or a naphthyl group; An isoquinolyl group substituted or unsubstituted with a phenyl group; Quinolyl group; A quinazolyl group substituted or unsubstituted with a phenyl group; A triazine group substituted or unsubstituted with a phenyl group; A benzimidazole group substituted or unsubstituted with a phenyl group; A benzoxazole group substituted or unsubstituted with a phenyl group; A benzothiazole group substituted or unsubstituted with a phenyl group; A methyl group, or a dihydroacridine group substituted or unsubstituted with a phenyl group; A methyl group, or a xanthylene group substituted or unsubstituted with a phenyl group; Or a dibenzosilyl group substituted or unsubstituted with a methyl group or a phenyl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar5 내지 Ar8은 서로 같거나 상이하고, 각각 독립적으로 수소; 또는 하기 구조들 중 선택될 수 있다.In one embodiment of the present specification, Ar5 to Ar8 are the same or different from each other and each independently hydrogen; Or one of the following structures.
Figure PCTKR2018013380-appb-I000048
Figure PCTKR2018013380-appb-I000048
Figure PCTKR2018013380-appb-I000049
Figure PCTKR2018013380-appb-I000049
Figure PCTKR2018013380-appb-I000050
Figure PCTKR2018013380-appb-I000050
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하며, 유기물층 중 1층 이상은 전술한 화합물을 포함하고, 상기 발광층은 하기 화학식 1B로 표시되는 화합물을 포함할 수 있다.According to an embodiment of the present invention, 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.
본 명세서의 유기 발광 소자의 유기물층 중 발광층의 호스트의 재료로서 하기 화학식 1B의 구조를 포함할 수 있다.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).
[화학식 1B]≪ RTI ID = 0.0 &
Figure PCTKR2018013380-appb-I000051
Figure PCTKR2018013380-appb-I000051
상기 화학식 1B에 있어서,In the above formula (1B)
L107 내지 L109는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,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 내지 Ar11은 서로 같거나 상이하고, 각각 독립적으로 수소; 또는 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,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,
R102는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,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,
q는 0 내지 7의 정수이며,q is an integer of 0 to 7,
q가 2 이상인 경우 괄호 내의 치환기는 서로 같거나 상이하다. When q is 2 or more, the substituents in the parentheses are the same or different from each other.
본 명세서의 일 실시상태에 있어서, 상기 R102는 수소; 중수소; 할로겐기; 실릴기; 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴헤테로아릴아민기; 또는 치환 또는 비치환된 헤테로고리기이다.In one embodiment of the present disclosure, 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.
본 명세서의 일 실시상태에 있어서, 상기 R102는 서로 동일하거나 상이하며, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.In one embodiment of the present specification, 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.
본 명세서의 일 실시상태에 있어서, 상기 R102는 서로 동일하거나 상이하며, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 50의 알킬기; 치환 또는 비치환된 탄소수 3 내지 60의 시클로알킬기; 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 40인 헤테로고리기이다.In one embodiment of the present specification, 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.
본 명세서의 일 실시상태에 있어서, 상기 R102는 서로 동일하거나 상이하며, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 30의 알킬기; 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 25의 헤테로고리기이다.In one embodiment of the present specification, 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.
또 하나의 일 실시상태에 있어서, 상기 R102는 수소이다.In another embodiment, R102 is hydrogen.
본 명세서의 일 실시상태에 따르면, 상기 q는 0 또는 1이다.According to one embodiment of the present disclosure, q is 0 or 1.
본 명세서의 일 실시상태에 있어서, 상기 L107 내지 L109는 서로 동일하거나 상이하며, 각각 독립적으로 직접결합; 치환 또는 비치환된 탄소수 6 내지 60의 아릴렌기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴렌기이다.In one embodiment of the present invention, 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.
본 명세서의 일 실시상태에 있어서, 상기 L107 내지 L109는 서로 동일하거나 상이하며, 각각 독립적으로 직접결합; 치환 또는 비치환된 탄소수 6 내지 40의 아릴렌기; 또는 치환 또는 비치환된 탄소수 2 내지 40의 헤테로아릴렌기이다.In one embodiment of the present invention, 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.
또 하나의 일 실시상태에 따르면, 상기 L107 내지 L109는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 페닐렌기; 치환 또는 비치환된 바이페닐릴렌기; 치환 또는 비치환된 터페닐렌기; 치환 또는 비치환된 나프틸렌기; 치환 또는 비치환된 안트라세닐렌기; 치환 또는 비치환된 페난트레닐렌기; 치환 또는 비치환된 트리페닐렌기; 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 티오페닐렌기; 치환 또는 비치환된 퓨라닐렌기; 치환 또는 비치환된 디벤조티오페닐렌기; 치환 또는 비치환된 디벤조퓨라닐렌기; 또는 치환 또는 비치환된 카바졸릴렌기이다.According to another embodiment, 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.
또 하나의 일 실시상태에 있어서, 상기 L107 내지 L109는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 페닐렌기; 바이페닐릴렌기; 터페닐렌기; 나프틸렌기; 안트라세닐렌기; 페난트레닐렌기; 트리페닐렌기; 메틸기 또는 페닐기로 치환 또는 비치환된 플루오레닐기; 티오페닐렌기; 퓨라닐렌기; 디벤조티오페닐렌기; 디벤조퓨라닐렌기; 또는 에틸기 또는 페닐기로 치환 또는 비치환된 카바졸릴렌기이다.In another embodiment, 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.
또 하나의 일 실시상태에 따르면, 상기 L107 내지 L109는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 또는 하기 구조들 중 선택될 수 있다.According to another embodiment, L107 to L109 are the same or different and are each independently a direct bond; Or one of the following structures.
Figure PCTKR2018013380-appb-I000052
Figure PCTKR2018013380-appb-I000052
본 명세서의 일 실시상태에 있어서, 상기 L107 내지 L109는 직접결합이다.In one embodiment of the present specification, L107 to L109 are direct bonds.
본 명세서의 일 실시상태에 있어서, 상기 Ar9 내지 Ar11은 서로 동일하거나 상이하며, 각각 독립적으로 수소; 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴기이다.In one embodiment of the present specification, 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.
또 하나의 일 실시상태에 따르면, 상기 Ar9 내지 Ar11은 서로 동일하거나 상이하며, 각각 독립적으로 수소; 탄소수 6 내지 60의 아릴기 또는 탄소수 2 내지 60의 헤테로아릴기로 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 탄소수 내지 60의 아릴기 또는 탄소수 2 내지 60의 헤테로아릴기로 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴기이다.According to another embodiment, 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.
또 하나의 일 실시상태에 있어서, 상기 Ar9 내지 Ar11은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 페난트렌기; 치환 또는 비치환된 안트라센기; 치환 또는 비치환된 트리페닐렌기; 치환 또는 비치환된 디벤조퓨란기; 치환 또는 비치환된 나프토벤조퓨란기; 치환 또는 비치환된 디벤조티오펜기; 치환 또는 비치환된 카바졸기; 치환 또는 비치환된 플루오렌기; 치환 또는 비치환된 티오펜기; 치환 또는 비치환된 퓨란기; 치환 또는 비치환된 벤조티오펜기; 치환 또는 비치환된 벤조퓨란기; 치환 또는 비치환된 벤조카바졸기; 치환 또는 비치환된 벤조플루오렌기; 치환 또는 비치환된 인돌카바졸기; 치환 또는 비치환된 피리딜기; 치환 또는 비치환된 이소퀴놀릴기; 치환 또는 비치환된 퀴놀릴기; 치환 또는 비치환된 퀴나졸릴기; 치환 또는 비치환된 트리아진기; 치환 또는 비치환된 벤즈이미다졸기; 치환 또는 비치환된 벤조옥사졸기; 치환 또는 비치환된 벤조티아졸기; 치환 또는 비치환된 다이하이드로아크리딘기; 치환 또는 비치환된 크산텐기; 또는 치환 또는 비치환된 디벤조실롤기이다.In another embodiment, 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 benzothiophene group; A substituted or unsubstituted benzofuran group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted benzofluorene group; A substituted or unsubstituted indolcarbazole group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted isoquinolyl group; A substituted or unsubstituted quinolyl group; A substituted or unsubstituted quinazolyl group; A substituted or unsubstituted triazine group; A substituted or unsubstituted benzimidazole group; A substituted or unsubstituted benzoxazole group; A substituted or unsubstituted benzothiazole group; A substituted or unsubstituted dihydroacridine group; A substituted or unsubstituted xanthene group; Or a substituted or unsubstituted dibenzosilyl group.
또 하나의 일 실시상태에 따르면, 상기 Ar9 내지 Ar11은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 페닐기; 바이페닐기; 아릴기로 치환 또는 비치환된 나프틸기; 페난트렌기; 안트라센기; 트리페닐렌기; 아릴기로 치환 또는 비치환된 디벤조퓨란기; 나프토벤조퓨란기; 아릴기로 치환 또는 비치환된 디벤조티오펜기; 알킬기, 또는 아릴기로 치환 또는 비치환된 카바졸기; 알킬기, 또는 아릴기로 치환 또는 비치환된 플루오렌기; 아릴기로 치환 또는 비치환된 티오펜기; 아릴기로 치환 또는 비치환된 퓨란기; 벤조티오펜기; 벤조퓨란기; 알킬기, 또는 아릴기로 치환 또는 비치환된 벤조카바졸기; 알킬기, 또는 아릴기로 치환 또는 비치환된 벤조플루오렌기; 인돌카바졸기; 피리딜기; 아릴기로 치환 또는 비치환된 이소퀴놀릴기; 퀴놀릴기; 아릴기로 치환 또는 비치환된 퀴나졸릴기; 아릴기로 치환 또는 비치환된 트리아진기; 아릴기로 치환 또는 비치환된 벤즈이미다졸기; 아릴기로 치환 또는 비치환된 벤조옥사졸기; 아릴기로 치환 또는 비치환된 벤조티아졸기; 알킬기, 또는 아릴기로 치환 또는 비치환된 다이하이드로아크리딘기; 알킬기, 또는 아릴기로 치환 또는 비치환된 크산텐기; 또는 알킬기, 또는 아릴기로 치환 또는 비치환된 디벤조실롤기이다.According to another embodiment, 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; A benzocarbazole group substituted or unsubstituted with an alkyl group or an aryl group; A benzofluorene group substituted or unsubstituted with an alkyl group or an aryl group; Indolecarbazole group; A pyridyl group; An isoquinolyl group substituted or unsubstituted with an aryl group; Quinolyl group; A quinazolyl group substituted or unsubstituted with an aryl group; A triazine group substituted or unsubstituted with an aryl group; A benzimidazole group substituted or unsubstituted with an aryl group; A benzoxazole group substituted or unsubstituted with an aryl group; A benzothiazole group substituted or unsubstituted with an aryl group; An alkyl group, or a dihydroacridine group substituted or unsubstituted with an aryl group; A xanthene group substituted or unsubstituted with an alkyl group or an aryl group; Or a dibenzosilyl group substituted or unsubstituted with an alkyl group or an aryl group.
또 하나의 일 실시상태에 있어서, 상기 Ar9 내지 Ar11은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 페닐기; 바이페닐기; 페닐기로 치환 또는 비치환된 나프틸기; 페난트렌기; 안트라센기; 트리페닐렌기; 페닐기로 치환 또는 비치환된 디벤조퓨란기; 나프토벤조퓨란기; 페닐기로 치환 또는 비치환된 디벤조티오펜기; 메틸기, 에틸기, 또는 페닐기로 치환 또는 비치환된 카바졸기; 메틸기, 또는 페닐기로 치환 또는 비치환된 플루오렌기; 페닐기로 치환 또는 비치환된 티오펜기; 페닐기로 치환 또는 비치환된 퓨란기; 벤조티오펜기; 벤조퓨란기; 메틸기, 또는 페닐기로 치환 또는 비치환된 벤조카바졸기; 메틸기, 또는 페닐기로 치환 또는 비치환된 벤조플루오렌기; 인돌카바졸기; 페닐기 또는 나프틸기로 치환 또는 비치환된 피리딜기; 페닐기로 치환 또는 비치환된 이소퀴놀릴기; 퀴놀릴기; 페닐기로 치환 또는 비치환된 퀴나졸릴기; 페닐기로 치환 또는 비치환된 트리아진기; 페닐기로 치환 또는 비치환된 벤즈이미다졸기; 페닐기로 치환 또는 비치환된 벤조옥사졸기; 페닐기로 치환 또는 비치환된 벤조티아졸기; 메틸기, 또는 페닐기로 치환 또는 비치환된 다이하이드로아크리딘기; 메틸기, 또는 페닐기로 치환 또는 비치환된 크산텐기; 또는 메틸기, 또는 페닐기로 치환 또는 비치환된 디벤조실롤기이다.In another embodiment, 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 phenyl group; Benzothiophene group; Benzofuran group; A methyl group, or a benzocarbazole group substituted or unsubstituted with a phenyl group; A methyl group, or a benzofluorene group substituted or unsubstituted with a phenyl group; Indolecarbazole group; A pyridyl group substituted or unsubstituted with a phenyl group or a naphthyl group; An isoquinolyl group substituted or unsubstituted with a phenyl group; Quinolyl group; A quinazolyl group substituted or unsubstituted with a phenyl group; A triazine group substituted or unsubstituted with a phenyl group; A benzimidazole group substituted or unsubstituted with a phenyl group; A benzoxazole group substituted or unsubstituted with a phenyl group; A benzothiazole group substituted or unsubstituted with a phenyl group; A methyl group, or a dihydroacridine group substituted or unsubstituted with a phenyl group; A methyl group, or a xanthylene group substituted or unsubstituted with a phenyl group; Or a dibenzosilyl group substituted or unsubstituted with a methyl group or a phenyl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar9 내지 Ar11은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 또는 하기 구조들 중 선택될 수 있다.In one embodiment of the present specification, Ar9 to Ar11 are the same or different from each other and each independently hydrogen; Or one of the following structures.
Figure PCTKR2018013380-appb-I000053
Figure PCTKR2018013380-appb-I000053
Figure PCTKR2018013380-appb-I000054
Figure PCTKR2018013380-appb-I000054
Figure PCTKR2018013380-appb-I000055
Figure PCTKR2018013380-appb-I000055
본 발명의 유기 발광 소자는 전술한 화학식 1로 표시되는 화합물을 이용하여 한 층 이상의 유기물층을 형성하는 것을 제외하고는, 통상의 유기 발광 소자의 제조방법 및 재료에 의하여 제조될 수 있다.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).
상기 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥 코팅, 잉크젯 프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.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. Here, 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.
본 발명의 유기 발광 소자의 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 발명의 유기 발광 소자는 유기물층으로서 정공 주입층, 정공 수송층, 발광층, 전자 수송층, 전자 주입층 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 invention may have a single layer structure, but may have 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 injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as an organic material layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers.
본 발명의 유기 발광 소자에서, 상기 유기물층은 전자수송층 또는 전자주입층을 포함할 수 있고, 상기 전자수송층 또는 전자주입층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.In the organic light emitting device of the present invention, 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).
본 발명의 유기 발광 소자에서, 상기 유기물층은 정공주입층 또는 정공수송층을 포함할 수 있고, 상기 정공주입층 또는 정공수송층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.In the organic light emitting device of the present invention, 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).
또 하나의 실시 상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층이 상기 화학식 1로 표시되는 화합물을 포함한다. In another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by the general formula (1).
또 하나의 실시 상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 발광층의 도펀트로서 포함할 수 있다. According to another embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer may include the compound represented by Formula 1 as a dopant in the light emitting layer.
또 하나의 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 화학식 1로 표시되는 화합물을 발광층의 도펀트로서 포함하고, 형광 호스트 또는 인광 호스트를 포함하며, 다른 유기화합물, 금속 또는 금속화합물을 도펀트로 포함할 수 있다.In another embodiment, 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.
또 하나의 예로서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 화학식 1로 표시되는 화합물을 발광층의 도펀트로서 포함하고, 형광 호스트 또는 인광 호스트를 포함하며, 이리듐계(Ir) 도펀트와 함께 사용할 수 있다.As another example, the organic layer may include a light emitting layer, and 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.
본 명세서의 일 실시상태에 있어서, 상기 유기 발광 소자는 상기 발광층이 상기 화학식 1로 표시되는 화합물을 도펀트로서 포함하는 녹색 유기 발광 소자이다.In one embodiment of the present invention, 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.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 상기 발광층이 상기 화학식 1로 표시되는 화합물을 도펀트로서 포함하는 적색 유기 발광 소자이다.According to one embodiment of the present invention, 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.
또 하나의 일 실시상태에 있어서, 상기 유기 발광 소자는 상기 발광층이 상기 화학식 1로 표시되는 화합물을 도펀트로서 포함하는 청색 유기 발광 소자이다.In another embodiment, 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.
또 하나의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 화학식 1로 표시되는 화합물을 발광층의 호스트로서 포함할 수 있다.According to another embodiment, 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.
또 하나의 예로서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 화학식 1로 표시되는 화합물을 발광층의 호스트로서 포함하고, 도펀트를 포함할 수 있다.As another example, 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, and may include a dopant.
본 명세서의 일 실시상태에 있어서, 상기 제1 전극은 양극이고, 제2 전극은 음극이다.In one embodiment of the present invention, the first electrode is an anode and the second electrode is a cathode.
또 하나의 일 실시상태에 따르면, 상기 제1 전극은 음극이고, 제2 전극은 양극이다.According to another embodiment, the first electrode is a cathode and the second electrode is a cathode.
본 발명의 유기 발광 소자의 구조는 도 1 및 도 2에 나타낸 것과 같은 구조를 가질 수 있으나, 이에만 한정되는 것은 아니다.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.
도 1에는 기판(1) 위에 양극(2), 발광층(3) 및 음극(4)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화합물은 상기 발광층(3)에 포함될 수 있다.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. In FIG. In such a structure, the compound may be included in the light emitting layer (3).
도 2에는 기판(1) 위에 양극(2), 정공 주입층(5), 정공 수송층(6), 발광층(7), 전자 수송층(8) 및 음극(4)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화합물은 상기 정공 주입층(5), 정공 수송층(6), 발광층(7) 또는 전자 수송층(8)에 포함될 수 있다.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. In such a structure, 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.
예컨대, 본 발명에 따른 유기 발광 소자는 스퍼터링(sputtering)이나 전자빔 증발(e-beam evaporation)과 같은 PVD(physical vapor deposition) 방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공 주입층, 정공 수송층, 발광층 및 전자 수송층을 포함하는 유기물층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수도 있다.For example, the organic light emitting device according to the present invention 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, To form an anode, 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. In addition to such a method, 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.
상기 유기물층은 정공 주입층, 정공 수송층, 발광층 및 전자 수송층 등을 포함하는 다층 구조일 수도 있으나, 이에 한정되지 않고 단층 구조일 수 있다. 또한, 상기 유기물층은 다양한 고분자 소재를 사용하여 증착법이 아닌 용매 공정(solvent process), 예컨대 스핀 코팅, 딥 코팅, 닥터 블레이딩, 스크린 프린팅, 잉크젯 프린팅 또는 열 전사법 등의 방법에 의하여 더 적은 수의 층으로 제조할 수 있다.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.
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 preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of 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.
상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 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.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.
상기 정공 주입 물질로는 낮은 전압에서 양극으로부터 정공을 잘 주입 받을 수 있는 물질로서, 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(porphyrine), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴헥사아자트리페닐렌 계열의 유기물, 퀴나크리돈(quinacridone) 계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.As 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. Specific examples of 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.
상기 정공 수송 물질로는 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다.As 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.
상기 발광층은 적색, 녹색 또는 청색을 발광할 수 있으며, 인광 물질 또는 형광 물질로 이루어질 수 있다. 상기 발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 구체적인 예로는 8-히드록시-퀴놀린 알루미늄 착물(Alq3); 카르바졸 계열 화합물; 이량체화 스티릴(dimerized styryl) 화합물; BAlq; 10-히드록시벤조 퀴놀린-금속 화합물; 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물; 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자; 스피로(spiro) 화합물; 폴리플루오렌, 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다.The light emitting 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.
발광층의 호스트 재료로는 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.Examples of the host material of the light emitting layer include a condensed aromatic ring derivative or a heterocyclic compound. Specific examples of 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.
상기 도펀트 재료로는 방향족 아민 유도체, 스트릴아민 화합물, 붕소 착체, 플루오란텐 화합물, 금속 착체 등이 있다. 구체적으로 방향족 아민 유도체로는 치환 또는 비치환된 아릴아미노기를 갖는 축합 방향족환 유도체로서, 아릴아미노기를 갖는 피렌, 안트라센, 크리센, 페리플란텐 등이 있으며, 스티릴아민 화합물로는 치환 또는 비치환된 아릴아민에 적어도 1개의 아릴비닐기가 치환되어 있는 화합물로, 아릴기, 실릴기, 알킬기, 시클로알킬기 및 아릴아미노기로 이루어진 군에서 1 또는 2 이상 선택되는 치환기가 치환 또는 비치환된다. 구체적으로 스티릴아민, 스티릴디아민, 스티릴트리아민, 스티릴테트라아민 등이 있으나, 이에 한정되지 않는다. 또한, 금속 착체로는 이리듐 착체, 백금 착체 등이 있으나, 이에 한정되지 않는다.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. Examples of the styrylamine compound 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. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.
상기 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 Al 착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다.As 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.
상기 전자 주입 물질로는 전자를 수송하는 능력을 갖고, 음극으로부터의 전자주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며, 발광층에서 생성된 여기자의 정공 주입층에의 이동을 방지하고, 또한, 박막형성능력이 우수한 화합물이 바람직하다. 구체적으로는 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 함질소 5원환 유도체 등이 있으나, 이에 한정되지 않는다. The electron 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.
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- 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.
상기 정공차단층은 정공의 음극 도달을 저지하는 층으로, 일반적으로 정공주입층과 동일한 조건으로 형성될 수 있다. 구체적으로 옥사디아졸 유도체나 트리아졸 유도체, 페난트롤린 유도체, BCP, 알루미늄 착물 (aluminum complex) 등이 있으나, 이에 한정되지 않는다.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.
본 발명에 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 invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.
<합성예><Synthesis Example>
합성예 1.Synthesis Example 1
합성예 1. <중간체 1-1>의 합성Synthesis Example 1. Synthesis of <Intermediate 1-1>
하기 반응식 1에 따라 중간체 1-1을 합성하였다.Intermediate 1-1 was synthesized according to Reaction Scheme 1 below.
[반응식 1][Reaction Scheme 1]
Figure PCTKR2018013380-appb-I000056
Figure PCTKR2018013380-appb-I000056
질소 분위기 하에서 1-클로로-3-플루오로디벤조[b,d]퓨란[1-chloro-3-fluorodibenzo[b,d]furan] (25.0g, 0.113mol )과 아닐린 (11.6g, 0.125mol), 비스(트리-tert-부틸포스핀)팔라듐(0) [Bis(tri-tert-butylphosphine)palladium(0)] (1.2g, 2.27mmol ), NaOtBu (27.g, 0.283mol) 및 크실렌 200mL가 들어간 플라스크를 12시간 동안 가열 교반하였다. 반응액을 실온까지 냉각한 후, 물과 다이클로로메테인을 가하여 추출 및 세척하였다. 유기층을 회수하여 추출 용매를 제거한 후 실리카겔 컬럼 크로마토그래피 (전개액: 다이클로로메테인 / 노르말헥산 = 1/1(부피비))로 정제하여, 흰색의 중간체 1-1을 18.0g, 55% 수율 (HPLC[High-performance liquid chromatography] 99% 순도)로 얻었다. MS:[M+H]+= 278Fluorodibenzo [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. The organic layer was recovered, and the solvent was removed, and the residue was purified by silica gel column chromatography (developing solution: dichloromethane / n-hexane = 1/1 (volume ratio)) to obtain 18.0 g of white intermediate 1-1 at a yield of 55% HPLC [High-performance liquid chromatography] 99% purity). MS: [M + H] &lt; + &gt; = 278
합성예 2. <중간체 1-2>의 합성Synthesis Example 2. Synthesis of <Intermediate 1-2>
하기 반응식 2에 따라 중간체 1-2를 합성하였다.Intermediate 1-2 was synthesized according to Reaction Scheme 2 below.
[반응식 2][Reaction Scheme 2]
Figure PCTKR2018013380-appb-I000057
Figure PCTKR2018013380-appb-I000057
상기 합성예 1에서 1-클로로-3-플루오로디벤조[b,d]퓨란 [1-chloro-3-fluorodibenzo[b,d]furan]을 1-클로로-3-메톡시디벤조[b,d]퓨란 [1-chloro-3-methoxydibenzo[b,d]furan]으로 변경하는 것을 제외하고 거의 유사한 방법으로 합성을 진행하여 흰색 분말 형태의 중간체 1-2를 22.5g, 67% 수율로 얻었다. MS:[M+H]+= 290B-d] furan was obtained in the same manner as in Synthesis Example 1, except that 1-chloro-3-fluorodibenzo [b, Synthesis was carried out in almost the same manner as in Example 1 except that the compound was changed to furan [1-chloro-3-methoxydibenzo [b, d] furan] to obtain 22.5 g of intermediate 1-2 in the form of a white powder in 67% yield. MS: [M + H] &lt; + &gt; = 290
합성예 3. <중간체 2>의 합성Synthesis Example 3. Synthesis of <Intermediate 2>
하기 반응식 3에 따라 중간체 2를 합성하였다.Intermediate 2 was synthesized according to Scheme 3 below.
[반응식 3][Reaction Scheme 3]
Figure PCTKR2018013380-appb-I000058
Figure PCTKR2018013380-appb-I000058
질소분위기 하에서 중간체 1-1(18.0g, 0.065mol), 소듐 tert-부톡사이드[sodium tert-butoxide] (15.0g, 0.162mol), 디클로로비스[디-tert-부틸(p-디메틸아미노페닐)포스피노]팔라듐(II) {dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II)} (1.38g, 1.95mmol) 그리고 1-브로모-2,3-디클로로벤젠 [1-bromo-2,3-dichlorobenzene] (14.7g, 0.065mol)을 o-크실렌 150ml에 녹인 후 6시간 환류 시켰다. 반응 혼합물을 식힌 후, 에틸아세테이트와 증류수를 첨가하여 층분리한 후 유기층을 회수하였다. 이후 유기층을 증류수로 2회 세척한 후 용매를 제거하여 갈색의 고형분을 얻었다. 컬럼 크로마토그래피를 이용하여 (전개액: 에틸아세테이트/노르말헥산 = 1/5 (부피비)) 순수한 분말 형태인 중간체 2를 14g, 51%의 수율로 얻었다. MS:[M+H]+= 422(18.0 g, 0.065 mol), sodium tert-butoxide (15.0 g, 0.162 mol), dichlorobis [di-tert-butyl (p-dimethylaminophenyl) (1.38 g, 1.95 mmol) and 1-bromo-2,3-dichlorobenzene (1-bromo- 2,3-dichlorobenzene] (14.7 g, 0.065 mol) was dissolved in 150 ml of o-xylene and refluxed for 6 hours. After the reaction mixture was cooled, ethyl acetate and distilled water were added thereto to separate the layers, and the organic layer was recovered. The organic layer was washed twice with distilled water, and then the solvent was removed to obtain a brown solid. 14 g of Intermediate 2 in the form of pure powder was obtained in a yield of 51% using column chromatography (eluent: ethyl acetate / n-hexane = 1/5 (volume ratio)). MS: [M + H] &lt; + &gt; = 422
합성예 4. <중간체 3>의 합성Synthesis Example 4. Synthesis of <Intermediate 3>
하기 반응식 4에 따라 중간체 3을 합성하였다.Intermediate 3 was synthesized according to Scheme 4 below.
[반응식 4][Reaction Scheme 4]
Figure PCTKR2018013380-appb-I000059
Figure PCTKR2018013380-appb-I000059
질소분위기 하에서 중간체 2 (21.0g, 0.050mol), 중간체 1-2 (15.8g, 0.055mol), 소듐 tert-부톡사이드 [sodium tert-butoxide] (12.0g, 0.124mol), 그리고 디클로로비스[디-tert-부틸(p-디메틸아미노페닐)포스피노]팔라듐(II) {dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II)} (1.06g, 1.49mmol)을 o-크실렌 100mL에 녹인 후 12시간 환류 및 교반 시켰다. 반응 혼합물을 식힌 후, 에틸아세테트와 증류수를 첨가하여 층분리한 후 유기층을 회수하였다. 이후 유기층을 증류수로 2회 세척한 후 용매를 제거하여 갈색의 고형분을 얻었다. 컬럼 크로마토그래피를 이용하여 (전개액: 에틸아세테이트/노르말헥산 = 1/3 (부피비)) 순수한 분말 형태인 중간체 3을 61%의 수율로 얻었다. MS:[M+H]+= 675Intermediate 2 (21.0 g, 0.050 mol), Intermediate 1-2 (15.8 g, 0.055 mol), sodium tert-butoxide (12.0 g, 0.124 mol) and dichlorobis [di- (p-dimethylaminophenyl) phosphino] palladium (II)} (1.06 g, 1.49 mmol) was dissolved in 100 mL of o-xylene, After dissolving, the mixture was refluxed for 12 hours and stirred. After the reaction mixture was cooled, ethylacetate and distilled water were added thereto to separate the layers, and the organic layer was recovered. The organic layer was washed twice with distilled water, and then the solvent was removed to obtain a brown solid. Intermediate 3 in the form of a pure powder was obtained in a yield of 61% using column chromatography (eluent: ethyl acetate / n-hexane = 1/3 (volume ratio)). MS: [M + H] &lt; + &gt; = 675
합성예 5. <중간체 4>의 합성Synthesis Example 5. Synthesis of <Intermediate 4>
하기 반응식 5에 따라 중간체 4를 합성하였다.Intermediate 4 was synthesized according to Reaction Scheme 5 below.
[반응식 5][Reaction Scheme 5]
Figure PCTKR2018013380-appb-I000060
Figure PCTKR2018013380-appb-I000060
아르곤분위기 하에서, 중간체 3 (1.0 당량)을 tert-뷰틸벤젠에 녹인 용액에 tert-뷰틸리튬 펜탄 용액 (2.0 당량)을 천천히 주입하였으며,. 이때 온도는 -10℃가 유지되도록 하였다. 이 후, 60℃까지 승온하여 2시간 동안 교반한 후, -50℃까지 냉각하고 삼브롬화 붕소 (2.0 당량)를 천천히 첨가하고, 첨가가 완료된 후 서서히 온도를 실온까지 상승시킨 다음, 다시 0℃로 냉각하고 N,N-디이소프로필에틸아민 (2.0 당량)을 가하였다. 이후 증류관과 냉각관을 설치하여 승온하면서 저비점 용매를 제거하면서 온도를 상승시켜 120℃까지 올린 후 3시간동안 교반하였다. 반응 종료 후 반응액을 실온까지 냉각시키고, 차가운 아세트산 나트륨 수용액 가하여 교반시킨다. 반응 혼합물에 에틸아세테이트를 가한 후 유기층을 분리하여 용매를 제거하고, 톨루엔/노르말헥산을 이용하여 재결정으로 정제하였다. 건조 후 중간체 4를 27% 수율로 얻었다. MS:[M+H]+= 635Tert-butyllithium pentane solution (2.0 eq.) Was slowly poured into a solution of Intermediate 3 (1.0 eq.) In tert-butylbenzene under argon atmosphere. At this time, the temperature was kept at -10 ° C. Thereafter, the mixture was heated to 60 DEG C and stirred for 2 hours. Then, the mixture was cooled to -50 DEG C and boron tribromide (2.0 equivalents) was added slowly. After the addition was completed, the temperature was gradually raised to room temperature, Cooled and N, N-diisopropylethylamine (2.0 eq.) Was added. Thereafter, a distillation tube and a cooling tube were installed, the temperature was raised while removing the low-boiling solvent while raising the temperature, and the temperature was raised to 120 ° C, followed by stirring for 3 hours. After completion of the reaction, the reaction solution is cooled to room temperature, and a cold aqueous sodium acetate solution is added thereto. Ethyl acetate was added to the reaction mixture, the organic layer was separated, the solvent was removed, and the residue was purified by recrystallization using toluene / n-hexane. After drying, Intermediate 4 was obtained in 27% yield. MS: [M + H] &lt; + &gt; = 635
합성예Synthetic example 6. <화합물  6. Compound 1>의1> 합성 synthesis
하기 반응식 6에 따라 화합물 1을 합성하였다. Compound 1 was synthesized according to Scheme 6 below.
[반응식 6][Reaction Scheme 6]
Figure PCTKR2018013380-appb-I000061
Figure PCTKR2018013380-appb-I000061
중간체 4 (1.0 당량)를 디메틸포름아마이드[DMF]에 녹인 후 2,6-디-tert-부틸피리딘 [2,6-Di-tert-butylpyridine] (1.3 당량) 첨가하고 100℃에서 12시간 가열 교반하였다. 반응물을 1 몰 농도의 염산 수용액에 첨가한 후 침전물을 여과하였다. 다시 여과물을 재결정(톨루엔)으로 정제하여 순수한 화합물 1을 89%의 수율로 얻었다. MS:[M+H]+= 6152,6-Di-tert-butylpyridine (1.3 eq.) Was added to the solution, and the mixture was stirred at 100 ° C for 12 hours. Respectively. The reaction product was added to a 1 molar hydrochloric acid aqueous solution, and the precipitate was filtered. The filtrate was further purified by recrystallization (toluene) to obtain pure Compound 1 in a yield of 89%. MS: [M + H] &lt; + &gt; = 615
합성예 7. <중간체 6>의 합성Synthesis Example 7 Synthesis of Intermediate 6
Figure PCTKR2018013380-appb-I000062
Figure PCTKR2018013380-appb-I000062
질소분위기 하에서 중간체 5 (13.2g, 0.055mol), 중간체 1-2 (15.8g, 0.055mol), 소듐 tert-부톡사이드 [sodium tert-butoxide] (10.6g, 0.11mol) 그리고 비스(트리-tert-부틸포스핀)팔라듐(0) [Bis(tri-tert-butylphosphine)palladium(0)](0.28g, 0.55mmol)을 톨루엔 200mL에 녹인 후 12시간 환류 및 교반 시켰다. 반응 혼합물을 식힌 후, 에틸아세테이트와 증류수를 첨가하여 층분리한 후 유기층을 회수하였다. 이후 유기층을 증류수로 2회 세척한 후 용매를 제거한 다음 클로로포름과 헥산을 이용하여 재결정을 하였다. 순수한 분말 형태인 중간체 6를 76%의 수율로 얻었다. MS:[M+H]+= 448Intermediate 5 (13.2 g, 0.055 mol), Intermediate 1-2 (15.8 g, 0.055 mol), sodium tert-butoxide (10.6 g, 0.11 mol) and bis- Butylphosphine palladium (0) (0.28 g, 0.55 mmol) was dissolved in 200 mL of toluene, and the mixture was refluxed and stirred for 12 hours. After the reaction mixture was cooled, ethyl acetate and distilled water were added thereto to separate the layers, and the organic layer was recovered. Then, the organic layer was washed twice with distilled water, and then the solvent was removed, followed by recrystallization using chloroform and hexane. Intermediate 6 in pure powder form was obtained in 76% yield. MS: [M + H] &lt; + &gt; = 448
합성예 8. <중간체 7>의 합성Synthesis Example 8. Synthesis of Intermediate 7
Figure PCTKR2018013380-appb-I000063
Figure PCTKR2018013380-appb-I000063
질소분위기 하에서 중간체 6 (23.8g, 0.053mol), 중간체 1-1 (17.5g, 0.063mol), 소듐 tert-부톡사이드 [sodium tert-butoxide] (10.6g, 0.11mol) 그리고 비스(트리-tert-부틸포스핀)팔라듐(0) [Bis(tri-tert-butylphosphine)palladium(0)](0.27g, 0.53mmol)을 o-자일렌 [o-xylene] 200mL에 녹인 후 12시간 환류 및 교반 시켰다. 반응 혼합물을 식힌 후, 에틸아세테트와 증류수를 첨가하여 층분리한 후 유기층을 회수하였다. 이후 유기층을 증류수로 2회 세척한 후 용매를 제거한 다음 클로로포름과 헥산을 이용하여 재결정을 하였다. 순수한 분말 형태인 중간체 7을 68%의 수율로 얻었다. MS:[M+H]+= 689Intermediate 6 (23.8 g, 0.053 mol), Intermediate 1-1 (17.5 g, 0.063 mol), sodium tert-butoxide (10.6 g, 0.11 mol) and bis- Butylphosphine palladium (0) (0.27 g, 0.53 mmol) was dissolved in 200 mL of o-xylene and refluxed and stirred for 12 hours. After the reaction mixture was cooled, ethylacetate and distilled water were added thereto to separate the layers, and the organic layer was recovered. Then, the organic layer was washed twice with distilled water, and then the solvent was removed, followed by recrystallization using chloroform and hexane. Intermediate 7 in the form of a pure powder was obtained in a yield of 68%. MS: [M + H] &lt; + &gt; = 689
합성예 9. <중간체 8>의 합성Synthesis Example 9. Synthesis of <Intermediate 8>
Figure PCTKR2018013380-appb-I000064
Figure PCTKR2018013380-appb-I000064
상기 합성예 5와 같은 방법으로 중간체 8을 21% 수율로 얻었다. MS:[M+H]+= 649Intermediate 8 was obtained in a yield of 21% in the same manner as in Synthesis Example 5. MS: [M + H] &lt; + &gt; = 649
합성예 10. <화합물 2>의 합성Synthesis Example 10 Synthesis of <Compound 2>
Figure PCTKR2018013380-appb-I000065
Figure PCTKR2018013380-appb-I000065
상기 합성예 6과 같은 방법으로 화합물 2를 63% 수율로 얻었다. MS:[M+H]+= 629 Compound 2 was obtained in a yield of 63% in the same manner as in Synthesis Example 6. MS: [M + H] &lt; + &gt; = 629
합성예 11. <중간체 9>의 합성Synthesis Example 11 Synthesis of Intermediate 9
Figure PCTKR2018013380-appb-I000066
Figure PCTKR2018013380-appb-I000066
질소분위기 하에서 화합물 2(5g, 8mmol)를 테트라하이드로퓨란(THF) 140mL에 녹인 후 0℃로 냉각시킨다. N-브로모숙신이미드 [N-bromosuccinimide](2.8g, 16mmol)를 N,N-디메틸포름아미드 [N,N-dimethylformamide] 20mL에 녹인 후, 화합물 2가 있는 반응용액에 30분동안 0℃에서 천천히 적가하였다. 이후 상온에서 1시간 교반해 주었고, 소듐 티오황산염 [Sodium thiosulfate] 포화용액을 첨가하여 층분리한 후 유기층을 회수하였다. 이후 유기층을 브라인용액으로 2회 세척한 후 용매를 제거한 다음 헥산을 이용하여 재결정을 하였다. 순수한 분말 형태인 중간체 9를 81%의 수율로 얻었다. MS:[M+H]+= 785Compound 2 (5 g, 8 mmol) was dissolved in 140 mL of tetrahydrofuran (THF) under a nitrogen atmosphere, followed by cooling to 0 占 폚. After dissolving N-bromosuccinimide (2.8 g, 16 mmol) in 20 mL of N, N-dimethylformamide, the reaction solution containing Compound 2 was stirred at 0 ° C Lt; / RTI &gt; Then, the mixture was stirred at room temperature for 1 hour, and a saturated solution of sodium thiosulfate was added to separate the layers, and the organic layer was recovered. Then, the organic layer was washed twice with brine solution, the solvent was removed, and recrystallization was performed using hexane. Intermediate 9, in the form of a pure powder, was obtained in a yield of 81%. MS: [M + H] &lt; + &gt; = 785
합성예 12. <화합물 3>의 합성Synthesis Example 12 Synthesis of <Compound 3>
Figure PCTKR2018013380-appb-I000067
Figure PCTKR2018013380-appb-I000067
질소분위기 하에서 중간체 9 (4.8g, 6.1mmol), 페닐보론산 [phenylboronic acid] (1.6g, 13.4mmol), 제삼인삼칼륨[potassium phosphate tribasic] (3.9g, 18.3mmol) 그리고 비스(트리-tert-부틸포스핀)팔라듐(0) [Bis(tri-tert-butylphosphine)palladium(0)](30mg, 0.06mmol)을 1,4-다이옥산 [1,4-dioxane] 30mL/증류수 10mL에 녹인 후 6시간 환류 및 교반 시켰다. 반응 혼합물을 식힌 후, 암모늄클로라이드와 증류수를 첨가하여 층분리한 후 유기층을 회수하였다. 이후 유기층을 증류수로 2회 세척한 후 용매를 제거한 다음 톨루엔과 헥산을 이용하여 재결정을 하였다. 순수한 분말 형태인 화합물 3을 74%의 수율로 얻었다. MS:[M+H]+= 781(4.8 g, 6.1 mmol), phenylboronic acid (1.6 g, 13.4 mmol), potassium phosphate tribasic (3.9 g, 18.3 mmol) and bis (tri- Butylphosphine palladium (0) (30 mg, 0.06 mmol) was dissolved in 10 mL of 1, 4-dioxane [1, 4-dioxane] Lt; / RTI &gt; and stirred. After the reaction mixture was cooled, ammonium chloride and distilled water were added to separate the layers, and the organic layer was recovered. Then, the organic layer was washed twice with distilled water, the solvent was removed, and recrystallization was performed using toluene and hexane. Compound 3 in pure powder form was obtained in a yield of 74%. MS: [M + H] &lt; + &gt; = 781
합성예 13. <중간체 12>의 합성Synthesis Example 13 Synthesis of <Intermediate 12>
Figure PCTKR2018013380-appb-I000068
Figure PCTKR2018013380-appb-I000068
질소분위기 하에서 중간체 11 (18g, 0.052mol), 중간체 10 (34.6g, 0.109mol), 소듐 tert-부톡사이드 [sodium tert-butoxide] (22.5g, 0.234mol) 그리고 비스(트리-tert-부틸포스핀)팔라듐(0) [Bis(tri-tert-butylphosphine)palladium(0)](0.27g, 0.52mmol)을 o-자일렌 [o-xylene] 200mL에 녹인 후 12시간 환류 및 교반 시켰다. 반응 혼합물을 식힌 후, 에틸아세테트와 암모늄클로라이드 포화수용액을 첨가하여 층분리한 후 유기층을 회수하였다. 이후 유기층을 증류수로 2회 세척한 후 용매를 제거한 다음 클로로포름과 헥산을 이용하여 재결정을 하였다. 순수한 분말 형태인 중간체 12를 64%의 수율로 얻었다. MS:[M+H]+= 819(34 g, 0.109 mol), sodium tert-butoxide (22.5 g, 0.234 mol) and bis (tri-tert-butylphosphine) (0.27 g, 0.52 mmol) of bis (tri-tert-butylphosphine) palladium (0) was dissolved in 200 mL of o-xylene and refluxed and stirred for 12 hours. After the reaction mixture was cooled, a saturated aqueous solution of ethyl acetate and ammonium chloride was added to separate the layers, and the organic layer was recovered. Then, the organic layer was washed twice with distilled water, and then the solvent was removed, followed by recrystallization using chloroform and hexane. Intermediate 12 in the form of a pure powder was obtained in a yield of 64%. MS: [M + H] &lt; + &gt; = 819
합성예 14. <중간체 13>의 합성Synthesis Example 14. Synthesis of Intermediate 13
Figure PCTKR2018013380-appb-I000069
Figure PCTKR2018013380-appb-I000069
상기 합성예 5와 같은 방법으로 중간체 13을 23% 수율로 얻었다. MS:[M+H]+= 765Intermediate 13 was obtained in a yield of 23% in the same manner as in Synthesis Example 5. MS: [M + H] &lt; + &gt; = 765
합성예 15. <화합물 4>의 합성Synthesis Example 15. Synthesis of <Compound 4>
Figure PCTKR2018013380-appb-I000070
Figure PCTKR2018013380-appb-I000070
질소분위기 하에서 중간체 13 (5.5g, 7.2mmol)와 p-톨루엔 술폰산 수화물 [p-toluenesulfonic acid monohydrate] (2.74g, 14.4mmol)을 o-자일렌 [o-xylene] 50mL에 녹인 후, 딘-스타크(Dean-Stark) 초자를 이용하여 24시간 환류 및 교반하였다. 상온으로 냉각 후 다량의 톨루엔과 탄화수소나트륨[sodium hydrogen carbonate] 포화 수용액을 첨가하여 층분리한 후 유기층을 회수하였다. 이후 유기층을 증류수로 2회 세척한 후 용매를 제거한 다음 톨루엔과 헥산을 이용하여 재결정을 하였다. 순수한 분말 형태인 화합물 4를 80%의 수율로 얻었다. MS:[M+H]+= 747Toluene sulfonic acid monohydrate] (2.74 g, 14.4 mmol) was dissolved in 50 mL of o-xylene [o-xylene] under nitrogen atmosphere, 0.0 &gt; (Dean-Stark) &lt; / RTI &gt; After cooling to room temperature, a large amount of toluene and a saturated aqueous solution of sodium hydrogen carbonate were added to separate the layers, and the organic layer was recovered. Then, the organic layer was washed twice with distilled water, the solvent was removed, and recrystallization was performed using toluene and hexane. Compound 4 in pure powder form was obtained in a yield of 80%. MS: [M + H] &lt; + &gt; = 747
<실시예><Examples>
실시예 1.Example 1.
ITO(indium tin oxide)가 1300Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이 때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀리포어사(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, 이소프로필알콜, 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 thin glass substrate coated with ITO (indium tin oxide) having a thickness of 1300 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, Fischer Co. product was used as a detergent, and 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.
상기와 같이 준비된 ITO 투명 전극 위에 하기 화합물 [HI-A]를 600Å의 두께로 진공증착하여 정공 주입층을 형성하였다. 상기 정공 주입층 위에 하기 화합물 [HAT-CN] (50Å) 및 하기 화합물 [HT-A] (600Å)를 순차적으로 진공 증착하여 정공 수송층을 형성하였다.The following compound [HI-A] was vacuum deposited on the ITO transparent electrode prepared above to a thickness of 600 Å to form a hole injection layer. The following compound [HAT-CN] (50 Å) and the following compound [HT-A] (600 Å) were sequentially vacuum-deposited on the hole injection layer to form a hole transport layer.
이어서, 상기 정공 수송층 위에 막 두께 200Å으로 하기 화합물 [BH]와 [BD]를 25:1의 중량비로 진공증착하여 발광층을 형성하였다.Subsequently, the following compounds [BH] and [BD] were vacuum deposited on the hole transport layer at a weight ratio of 25: 1 at a thickness of 200 ANGSTROM to form a light emitting layer.
이렇게 준비된 다음 호스트로 [BH-A]와 화합물 1을 25:1의 중량비로 200Å두께로 진공증착하여 발광층을 형성하였다. 그 다음에 [ET-A] 와 Liq를 1:1 비율로 300Å을 증착하였고, 이 위에 순차적으로 10Å 두께로 리튬 플루라이드(LiF)와 1,000Å 두께로 알루미늄을 증착하여 음극을 형성하여, 유기 발광 소자를 제조하였다.Then, [BH-A] and Compound 1 were vacuum-deposited to a thickness of 200 Å 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.
상기의 과정에서 유기물의 증착속도는 0.4 ~ 0.9 Å/sec를 유지하였고, 음극의 리튬플루오라이드는 0.3 Å/sec, 알루미늄은 2 Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 1 × 10-7 내지 5 × 10-8 torr를 유지하여, 유기 발광 소자를 제작하였다.The deposition rate of the organic material was maintained at 0.4 to 0.9 Å / sec, the lithium fluoride at the cathode was maintained at a deposition rate of 0.3 Å / sec, and the deposition rate of aluminum was maintained at 2 Å / sec. by keeping the -7 to 5 × 10 -8 torr, an organic light emitting device was produced.
Figure PCTKR2018013380-appb-I000071
Figure PCTKR2018013380-appb-I000071
Figure PCTKR2018013380-appb-I000072
Figure PCTKR2018013380-appb-I000072
실시예 2.Example 2.
상기 실시예 1에서, 화합물 1 대신 화합물 3을 사용하고, 호스트 [BH-A] 대신 [BH-B]를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다.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].
실시예 3.Example 3.
상기 실시예 1에서, 화합물 1 대신 화합물 3을 사용하고, 호스트 [BH-A] 대신 [BH-C]를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다.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].
실시예 4.Example 4.
상기 실시예 1에서, 화합물 1 대신 화합물 3을 사용하고, 호스트 [BH-A]에 호스트 [BH-B]를 더 포함([BH-A]와 [BH-B])의 중량비: 1:1)한 것을 제외하고는, 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다.In 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. [
실시예 5.Example 5.
상기 실시예 1에서 화합물 1 대신 화합물 3를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다.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.
실시예 6.Example 6.
상기 실시예 1에서 화합물 1 대신 화합물 4를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다.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.
<비교예><Comparative Example>
비교예 1.Comparative Example 1
상기 실시예 1에서 화합물 1 대신 [BD-A]를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다.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.
비교예 2.Comparative Example 2
상기 실시예 1에서 화합물 1 대신 [BD-B]를 사용하고, 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다.An organic luminescent device was prepared in the same manner as in Example 1 except that [BD-B] was used in place of the compound 1 in Example 1. [
비교예 3.Comparative Example 3
상기 실시예 1에서 화합물 1 대신 [BD-C]를 사용하고, 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다.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.
전술한 방법으로 제조한 유기 발광 소자를 10 mA/cm2 의 전류밀도에서 구동전압과 발광 효율을 측정하였고, 20 mA/cm2 의 전류밀도에서 초기 휘도 대비 90%가 되는 시간(T90)을 측정하였다. 그 결과를 하기 표 1에 나타내었다.The driving voltage and the luminous efficiency were measured at a current density of 10 mA / cm &lt; 2 &gt; at the current density of 20 mA / cm &lt; 2 &gt; and the time (T 90 ) Respectively. The results are shown in Table 1 below.
번호number 호스트Host 도펀트Dopant 전압(V)Voltage (V) 효율(Cd/A)Efficiency (Cd / A) 색좌표(x,y)The color coordinates (x, y) 수명(hr)Life (hr)
at 10mA/cm2 at 10 mA / cm 2 at 10mA/cm2 at 10 mA / cm 2 T90 at 20mA/cm2 T 90 at 20 mA / cm 2
실시예 1Example 1 BH-ABH-A 화합물 1Compound 1 3.553.55 4.94.9 (0.13, 0.05)(0.13, 0.05) 160160
실시예 2Example 2 BH-BBH-B 화합물 3Compound 3 3.403.40 5.405.40 (0.13, 0.05)(0.13, 0.05) 230230
실시예 3Example 3 BH-CBH-C 화합물 3Compound 3 3.723.72 5.305.30 (0.13, 0.06)(0.13, 0.06) 210210
실시예 4Example 4 BH-A + BH-BBH-A + BH-B 화합물 3Compound 3 3.403.40 5.405.40 (0.13, 0.06)(0.13, 0.06) 230230
실시예 5Example 5 BH-ABH-A 화합물 3Compound 3 3.473.47 5.455.45 (0.13, 0.06)(0.13, 0.06) 215215
실시예 6Example 6 BH-ABH-A 화합물 4Compound 4 3.503.50 5.475.47 (0.13, 0.06)(0.13, 0.06) 240240
비교예 1Comparative Example 1 BH-ABH-A BD-ABD-A 3.653.65 4.94.9 (0.13, 0.12)(0.13, 0.12) 200200
비교예 2Comparative Example 2 BH-ABH-A BD-BBD-B 3.603.60 5.335.33 (0.13, 0.05)(0.13, 0.05) 115115
비교예 3Comparative Example 3 BH-ABH-A BD-CBD-C 3.433.43 3.783.78 (0.12, 0.04)(0.12, 0.04) 110110
상기 표 1의 결과로부터, 본 발명에 따른 화학식 1로 표시되는 화합물은 청색 유기 발광 소자에서 각각 높은 발광효율과 장수명의 특징을 가지는 것을 확인 할 수 있다. 구체적으로 본원 실시예 1 내지 6이, 보론계 화합물이나 본원 화학식 1과 구조가 상이한 화합물을 사용한 비교예 2 및 3보다 소자의 수명 특성이 매우 우수함을 확인할 수 있다. From the results of Table 1, it can be seen that the compound represented by Formula 1 according to the present invention has high luminescence efficiency and long lifetime characteristics in the blue organic light emitting device. Specifically, it can be confirmed that Examples 1 to 6 of the present invention have much better lifetime characteristics than the boron-based compounds and Comparative Examples 2 and 3 using a compound having a different structure from that of the present invention.
또한, 본원 화학식 1로 표시되는 화합물 대신 파이렌계 화합물을 사용한 비교예 1은 색좌표에서 y의 값이 0.12를 나타내므로, 색순도가 매우 저하됨을 확인할 수 있다.Further, in Comparative Example 1 using a pyrene-based compound in place of the compound represented by the formula (1), the value of y in the color coordinate system was 0.12, so that it was confirmed that the color purity was greatly reduced.

Claims (16)

  1. 하기 화학식 1로 표시되는 화합물:A compound represented by the following formula (1):
    [화학식 1][Chemical Formula 1]
    Figure PCTKR2018013380-appb-I000073
    Figure PCTKR2018013380-appb-I000073
    상기 화학식 1에 있어서,In Formula 1,
    A1은 치환 또는 비치환된 방향족 탄화수소고리; 또는 치환 또는 비치환된 방향족 헤테로고리이며,A1 is a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle,
    W는 O, S, Se, NRa, PRb, C=O, CRcRd, SiReRf 또는 P(=O)Rg이고, W is O, S, Se, NRa, PRb, C = O, CRcRd, SiReRf or P (= O)
    X1은 N 또는 CR11이며, X2는 N 또는 CR12이고, X3는 N 또는 CR13이며, X1 is N or CR11, X2 is N or CR12, X3 is N or CR13,
    단, X2가 N인 경우 X3는 CR13이고, X3가 N인 경우 X2는 CR12이며,Provided that when X2 is N, X3 is CR13; when X3 is N, X2 is CR12;
    Ra 내지 Rg, R11 내지 R13, Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 알킬실릴기; 아릴실릴기; 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 알콕시아릴기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하며, 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 및 R2는 하기 화학식 2의 점선부와 연결되어 고리를 형성하고,R1 and R2 are connected to the dotted line of the formula (2) to form a ring,
    R3 및 R12; 또는 R3 및 R13은 하기 화학식 2의 점선부와 연결되어 고리를 형성하며,R3 and R12; Or R &lt; 3 &gt; and R &lt; 13 &gt; are connected to the dotted line of the formula (2)
    [화학식 2](2)
    Figure PCTKR2018013380-appb-I000074
    Figure PCTKR2018013380-appb-I000074
    상기 화학식 2에 있어서,In Formula 2,
    Y는 O, S, Se, NR21, PR22, C=O, CR23R24, SiR25R26 또는 P(=O)R27이고,Y is O, S, Se, NR21, PR22, C = O, CR23R24, SiR25R26 or P
    R21 내지 R27은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하며,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,
    A2는 치환 또는 비치환된 방향족 탄화수소고리; 또는 치환 또는 비치환된 방향족 헤테로고리이다.A2 is a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle.
  2. 청구항 1에 있어서,The method according to claim 1,
    상기 화학식 1은 하기 화학식 1-1 또는 화학식 1-2로 표시되는 것인 화합물:(1) is represented by the following general formula (1-1) or (1-2):
    [화학식 1-1][Formula 1-1]
    Figure PCTKR2018013380-appb-I000075
    Figure PCTKR2018013380-appb-I000075
    [화학식 1-2][Formula 1-2]
    Figure PCTKR2018013380-appb-I000076
    Figure PCTKR2018013380-appb-I000076
    상기 화학식 1-1 및 화학식 1-2에 있어서,In the above Formulas 1-1 and 1-2,
    W, X1, R1, R2, A1, Ar1 및 Ar2는 상기 화학식 1에서의 정의와 같고,W, X 1, R 1, R 2, A 1, Ar 1 and Ar 2 have the same definitions as in formula (1)
    X21 및 X31은 서로 같거나 상이하고, 각각 독립적으로 N 또는 CR41이며,X21 and X31 are the same or different and are each independently N or CR41,
    R41은 수소; 중수소; 할로겐기; 시아노기; 알킬실릴기; 아릴실릴기; 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 알콕시아릴기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하고,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 및 R4; 및 R3 및 R5는 상기 화학식 2의 점선부와 연결되어 고리를 형성한다.R3 and R4; And R &lt; 3 &gt; and R &lt; 5 &gt; are connected to the dotted line of formula (2) to form a ring.
  3. 청구항 1에 있어서,The method according to claim 1,
    상기 화학식 1은 하기 화학식 2-1 내지 화학식 2-7 중 어느 하나로 표시되는 것인 화합물:Wherein the compound represented by Formula 1 is represented by any one of the following Formulas 2-1 to 2-7:
    [화학식 2-1][Formula 2-1]
    Figure PCTKR2018013380-appb-I000077
    Figure PCTKR2018013380-appb-I000077
    [화학식 2-2][Formula 2-2]
    Figure PCTKR2018013380-appb-I000078
    Figure PCTKR2018013380-appb-I000078
    [화학식 2-3][Formula 2-3]
    Figure PCTKR2018013380-appb-I000079
    Figure PCTKR2018013380-appb-I000079
    [화학식 2-4][Chemical Formula 2-4]
    Figure PCTKR2018013380-appb-I000080
    Figure PCTKR2018013380-appb-I000080
    [화학식 2-5][Chemical Formula 2-5]
    Figure PCTKR2018013380-appb-I000081
    Figure PCTKR2018013380-appb-I000081
    [화학식 2-6][Chemical Formula 2-6]
    Figure PCTKR2018013380-appb-I000082
    Figure PCTKR2018013380-appb-I000082
    [화학식 2-7][Chemical Formula 2-7]
    Figure PCTKR2018013380-appb-I000083
    Figure PCTKR2018013380-appb-I000083
    상기 화학식 2-1 내지 화학식 2-7에 있어서,In Formulas 2-1 to 2-7,
    W, X1, X2, X3, A1, Ar1 및 Ar2는 상기 화학식 1에서의 정의와 같고,W, X 1, X 2, X 3, A 1, Ar 1 and Ar 2 have the same definitions as in the above formula (1)
    Y1 내지 Y14는 서로 같거나 상이하고, 각각 독립적으로 상기 화학식 2에서 Y의 정의와 같으며,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 내지 A34는 서로 같거나 상이하고, 각각 독립적으로 상기 화학식 2에서의 A2의 정의와 같다.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).
  4. 청구항 1에 있어서, The method according to claim 1,
    상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴기인 것인 화합물.Ar 1 and Ar 2 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.
  5. 청구항 1에 있어서, The method according to claim 1,
    상기 화학식 1로 표시되는 화합물은 하기 구조들 중 어느 하나로 표시되는 것인 화합물:Wherein the compound represented by Formula 1 is represented by any one of the following structures:
    Figure PCTKR2018013380-appb-I000084
    Figure PCTKR2018013380-appb-I000084
    Figure PCTKR2018013380-appb-I000085
    Figure PCTKR2018013380-appb-I000085
    Figure PCTKR2018013380-appb-I000086
    Figure PCTKR2018013380-appb-I000086
    Figure PCTKR2018013380-appb-I000087
    Figure PCTKR2018013380-appb-I000087
    Figure PCTKR2018013380-appb-I000088
    Figure PCTKR2018013380-appb-I000088
    Figure PCTKR2018013380-appb-I000089
    Figure PCTKR2018013380-appb-I000089
    Figure PCTKR2018013380-appb-I000090
    Figure PCTKR2018013380-appb-I000090
    Figure PCTKR2018013380-appb-I000091
    Figure PCTKR2018013380-appb-I000091
    Figure PCTKR2018013380-appb-I000092
    Figure PCTKR2018013380-appb-I000092
    Figure PCTKR2018013380-appb-I000093
    Figure PCTKR2018013380-appb-I000093
    Figure PCTKR2018013380-appb-I000094
    Figure PCTKR2018013380-appb-I000094
    Figure PCTKR2018013380-appb-I000095
    Figure PCTKR2018013380-appb-I000095
    Figure PCTKR2018013380-appb-I000096
    Figure PCTKR2018013380-appb-I000096
    Figure PCTKR2018013380-appb-I000097
    Figure PCTKR2018013380-appb-I000097
    Figure PCTKR2018013380-appb-I000098
    Figure PCTKR2018013380-appb-I000098
    Figure PCTKR2018013380-appb-I000099
    Figure PCTKR2018013380-appb-I000099
    Figure PCTKR2018013380-appb-I000100
    Figure PCTKR2018013380-appb-I000100
    Figure PCTKR2018013380-appb-I000101
    Figure PCTKR2018013380-appb-I000101
    Figure PCTKR2018013380-appb-I000102
    Figure PCTKR2018013380-appb-I000102
    Figure PCTKR2018013380-appb-I000103
    Figure PCTKR2018013380-appb-I000103
    Figure PCTKR2018013380-appb-I000104
    Figure PCTKR2018013380-appb-I000104
    Figure PCTKR2018013380-appb-I000105
    Figure PCTKR2018013380-appb-I000105
    Figure PCTKR2018013380-appb-I000106
    Figure PCTKR2018013380-appb-I000106
    Figure PCTKR2018013380-appb-I000107
    Figure PCTKR2018013380-appb-I000107
    Figure PCTKR2018013380-appb-I000108
    Figure PCTKR2018013380-appb-I000108
    Figure PCTKR2018013380-appb-I000109
    Figure PCTKR2018013380-appb-I000109
    Figure PCTKR2018013380-appb-I000110
    Figure PCTKR2018013380-appb-I000110
    Figure PCTKR2018013380-appb-I000111
    .
    Figure PCTKR2018013380-appb-I000111
    .
  6. 제1 전극; 상기 제1 전극과 대향하여 구비되는 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비되는 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상이 청구항 1 내지 5 중 어느 한 항에 따른 화합물을 포함하는 것인 유기 발광 소자.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 a compound according to any one of claims 1 to 5. The organic light- Light emitting element.
  7. 청구항 6에 있어서,The method of claim 6,
    상기 유기물층은 정공주입층 또는 정공수송층을 포함하고, 상기 정공주입층 또는 정공수송층은 상기 화합물을 포함하는 것인 유기 발광 소자.Wherein the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer comprises the compound.
  8. 청구항 6에 있어서,The method of claim 6,
    상기 유기물층은 전자수송층 또는 전자주입층을 포함하고, 상기 전자수송층 또는 전자주입층은 상기 화합물을 포함하는 것인 유기 발광 소자.Wherein the organic material layer includes an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer comprises the compound.
  9. 청구항 6에 있어서,The method of claim 6,
    상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화합물을 포함하는 것인 유기 발광 소자. Wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound.
  10. 청구항 6에 있어서, 상기 유기물층은 전자차단층 또는 정공차단층을 포함하고, 상기 전자차단층 또는 정공차단층은 상기 화합물을 포함하는 것인 유기 발광 소자.7. The organic light emitting device according to claim 6, wherein the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer comprises the compound.
  11. 청구항 6에 있어서,The method of claim 6,
    상기 유기물층은 발광층을 포함하고, 상기 발광층은 하기 화학식 1A로 표시되는 화합물을 포함하는 것인 유기 발광 소자:Wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises a compound represented by the following formula (1A):
    [화학식 1A]&Lt; EMI ID =
    Figure PCTKR2018013380-appb-I000112
    Figure PCTKR2018013380-appb-I000112
    상기 화학식 1A에 있어서,In the above formula (1A)
    L103 내지 L106은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,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 내지 Ar8은 서로 같거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,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,
    R101은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,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,
    p는 0 내지 6의 정수이며,p is an integer of 0 to 6,
    p가 2 이상인 경우 괄호 내의 치환기는 서로 같거나 상이하다.When p is 2 or more, the substituents in the parentheses are the same or different.
  12. 청구항 11에 있어서, The method of claim 11,
    상기 L103 내지 L106은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 하기 구조들 중 선택되는 것인 유기 발광 소자:L103 to L106 are the same or different and are each independently a direct bond; Or an organic electroluminescent element selected from the following structures:
    Figure PCTKR2018013380-appb-I000113
    .
    Figure PCTKR2018013380-appb-I000113
    .
  13. 청구항 11에 있어서,The method of claim 11,
    상기 Ar5 내지 Ar8는 서로 같거나 상이하고, 각각 독립적으로 수소; 또는 하기 구조들 중 선택되는 것인 유기 발광 소자: Ar5 to Ar8 are the same or different from each other and each independently hydrogen; Or an organic electroluminescent element selected from the following structures:
    Figure PCTKR2018013380-appb-I000114
    Figure PCTKR2018013380-appb-I000114
    Figure PCTKR2018013380-appb-I000115
    Figure PCTKR2018013380-appb-I000115
    Figure PCTKR2018013380-appb-I000116
    .
    Figure PCTKR2018013380-appb-I000116
    .
  14. 청구항 6에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 하기 화학식 1B로 표시되는 화합물을 포함하는 것인 유기 발광 소자:[7] The organic light emitting device of claim 6, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises a compound represented by the following Formula 1B:
    [화학식 1B]&Lt; RTI ID = 0.0 &
    Figure PCTKR2018013380-appb-I000117
    Figure PCTKR2018013380-appb-I000117
    상기 화학식 1B에 있어서,In the above formula (1B)
    L107 내지 L109는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,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 내지 Ar11은 서로 같거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,Ar9 to Ar11 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
    R102는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,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,
    q는 0 내지 7의 정수이며,q is an integer of 0 to 7,
    q가 2 이상인 경우 괄호 내의 치환기는 서로 같거나 상이하다. When q is 2 or more, the substituents in the parentheses are the same or different from each other.
  15. 청구항 14에 있어서, 15. The method of claim 14,
    상기 L107 내지 L109는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 하기 구조들 중 선택되는 것인 유기 발광 소자:L107 to L109 are the same or different and are each independently a direct bond; Or an organic electroluminescent element selected from the following structures:
    Figure PCTKR2018013380-appb-I000118
    .
    Figure PCTKR2018013380-appb-I000118
    .
  16. 청구항 14에 있어서,15. The method of claim 14,
    상기 Ar9 내지 Ar11은 서로 같거나 상이하고, 각각 독립적으로 수소; 또는 하기 구조들 중 선택되는 것인 유기 발광 소자:Ar9 to Ar11 are the same or different from each other, and each independently represents hydrogen; Or an organic electroluminescent element selected from the following structures:
    Figure PCTKR2018013380-appb-I000119
    Figure PCTKR2018013380-appb-I000119
    Figure PCTKR2018013380-appb-I000120
    Figure PCTKR2018013380-appb-I000120
    Figure PCTKR2018013380-appb-I000121
    .
    Figure PCTKR2018013380-appb-I000121
    .
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