WO2020106028A1 - Composé polycyclique et dispositif électroluminescent organique le comprenant - Google Patents

Composé polycyclique et dispositif électroluminescent organique le comprenant

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WO2020106028A1
WO2020106028A1 PCT/KR2019/015866 KR2019015866W WO2020106028A1 WO 2020106028 A1 WO2020106028 A1 WO 2020106028A1 KR 2019015866 W KR2019015866 W KR 2019015866W WO 2020106028 A1 WO2020106028 A1 WO 2020106028A1
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carbon atoms
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Korean (ko)
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금수정
홍완표
김경희
서상덕
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주식회사 엘지화학
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Priority to CN201980063764.6A priority Critical patent/CN112771030B/zh
Publication of WO2020106028A1 publication Critical patent/WO2020106028A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
    • C07D319/24—[b,e]-condensed with two six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
    • C07D327/06—Six-membered rings
    • C07D327/08—[b,e]-condensed with two six-membered carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
    • C07D339/08—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D411/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D497/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D497/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D497/04—Ortho-condensed systems
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants

Definitions

  • the present specification relates to a compound and an organic light emitting device including the same.
  • the organic light emitting device is a light emitting device 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 divided into two types according to the operation principle. First, excitons are formed in the organic layer by photons introduced into the device from an external light source, and the excitons are separated into electrons and holes, and the electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). It is a light emitting device of the form.
  • the second is a light emitting device in which holes or / or electrons are injected into the organic semiconductor material layer forming an interface with the electrode by applying voltage or current to two or more electrodes, and operated by the injected electrons and holes.
  • the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween.
  • the organic material layer is often composed of a multi-layered structure composed of different materials, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron suppression layer, an electron transport layer, an electron injection layer, etc. Can lose.
  • Materials used as the organic material layer in the organic light emitting device may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron suppressing materials, electron transport materials, and electron injection materials, depending on their function.
  • the light emitting materials include blue, green, and red light emitting materials, and yellow and orange light emitting materials necessary for realizing a better natural color depending on the light emitting color.
  • a host / dopant system may be used as a light emitting material to increase color purity and increase light emission efficiency through energy transfer.
  • the principle is that when a small amount of a dopant having a smaller energy band gap and higher luminous efficiency is mixed with the luminescent layer than the host mainly constituting the luminescent layer, exciton generated from the host is transported as a dopant to produce light with high efficiency. At this time, since the wavelength of the host moves to the wavelength of the dopant, light of a desired wavelength can be obtained according to the type of the dopant used.
  • materials constituting an organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron suppressing material, an electron transport material, an electron injection material, are stable and efficient materials It is supported by, and the development of new materials is still required.
  • One embodiment of the present specification provides a compound represented by the following Chemical Formula 1.
  • One of X1 and X2 is O or S, and the other is O, S or CRR ',
  • R1, R2, R and R ' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group, or combines with an adjacent group to form a substituted or unsubstituted ring,
  • R3 to R6 are represented by the following Chemical Formula 2, and the rest are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • Cy1 and Cy2 are the same as or different from each other, and each independently a substituted or unsubstituted ring,
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group, or combine with each other to form a substituted or unsubstituted heteroring,
  • the present invention is a first electrode; A second electrode provided opposite to the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, and at least one layer of the organic material layer includes the above-described compound.
  • the compounds described herein can be used as a material for the organic material layer of the organic light emitting device.
  • the organic light emitting device including the compound according to an exemplary embodiment of the present specification, it is possible to obtain an organic light emitting device having excellent light emission efficiency, low driving voltage, high efficiency and long life.
  • 1 to 3 show an example of an organic light emitting device according to an exemplary embodiment of the present specification.
  • One of X1 and X2 is O or S, and the other is O, S or CRR ',
  • R1, R2, R and R ' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group, or combines with an adjacent group to form a substituted or unsubstituted ring,
  • R3 to R6 are represented by the following Chemical Formula 2, and the rest are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • Cy1 and Cy2 are the same as or different from each other, and each independently a substituted or unsubstituted ring,
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group, or combine with each other to form a substituted or unsubstituted heteroring,
  • substitution means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where the substituent is substitutable, and when two or more are substituted , 2 or more substituents may be the same or different from each other.
  • substituted or unsubstituted in this specification is deuterium (-D); Halogen group; Cyano group (-CN); Nitro group; Hydroxy group; Silyl group; Boron group; Alkyl groups; Alkoxy groups; Cycloalkyl group; Aryl group; Amine group; And 1 or 2 or more substituents selected from the group consisting of heterocyclic groups, or substituted with two or more substituents among the above-exemplified substituents, or having no substituents.
  • a substituent having two or more substituents may be a terphenyl group. That is, the terphenyl group may be an aryl group, or may be interpreted as a substituent to which three phenyl groups are connected.
  • examples of the halogen group include fluorine (-F), chlorine (-Cl), bromine (-Br) or iodine (-I).
  • the silyl group may be represented by the formula of -SiY a Y b Y c , wherein Y a , Y b and Y c are each hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or it may be a substituted or unsubstituted aryl group.
  • the silyl group is specifically trimethylsilyl group, triethylsilyl group, tert-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, dimethylphenylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. There is, but is not limited to this.
  • the boron group may be represented by the formula -BY d Y e , wherein Y d and Y e are each hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or it may be a substituted or unsubstituted aryl group.
  • the boron group may include, but is not limited to, trimethyl boron group, triethyl boron group, tert-butyl dimethyl boron group, triphenyl boron group, phenyl boron group, and the like.
  • the alkyl group may be straight chain or branched chain, and carbon number is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms.
  • alkyl group examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, n-pentyl group, hexyl group, n -Hexyl group, heptyl group, n-heptyl group, octyl group, n-octyl group, and the like, but is not limited to these.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 60. According to one embodiment, the carbon number of the alkoxy group is 1 to 30. According to another exemplary embodiment, the alkoxy group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkoxy group has 1 to 10 carbon atoms. Specific examples of the alkoxy group include, but are not limited to, methoxy group, ethoxy group, propoxy group, butoxy group, and the like.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, and the like, but is not limited thereto.
  • the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, etc., as a monocyclic aryl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., but is not limited thereto. no.
  • the fluorenyl group may be substituted, and two substituents may combine with each other to form a spiro structure.
  • Spirofluorenyl groups such as, (9,9-dimethylfluorenyl group), and And a substituted fluorenyl group such as (9,9-diphenylfluorenyl group).
  • a substituted fluorenyl group such as (9,9-diphenylfluorenyl group
  • the heterocyclic group is a hetero atom and is a ring group containing at least one of N, O, S, and Se, and carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms. According to one embodiment, the heterocyclic group has 2 to 30 carbon atoms.
  • heterocyclic group examples include pyridine group, pyrrole group, pyrimidine group, quinoline group, pyridazinyl group, furan group, thiophene group, imidazole group, pyrazole group, dibenzofuran group, dibenzothiophene group , Carbazole group, benzocarbazole group, naphthobenzofuran group, benzonaphthothiophene group, indenocarbazole group, and the like, but is not limited thereto.
  • the amine group may be represented by the formula -NY f Y g , wherein Y f and Y g are each hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or it may be a substituted or unsubstituted heteroaryl group.
  • the amine group is specifically a dimethylamine group; Diphenylamine group; Dicyclohexylamine group, and the like, but is not limited to these.
  • heterocyclic group may be applied, except that the heteroaryl group is aromatic.
  • adjacent A group may mean a substituent substituted on an atom directly connected to an atom in which the substituent is substituted, a substituent located closest in conformation to the substituent, or another substituent substituted on the atom in which the substituent is substituted.
  • two substituents substituted in the ortho position on the benzene ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" to each other.
  • ring is 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 examples of the cycloalkyl group or aryl group, except for the divalent group.
  • the description of the aryl group may be applied, except that the aromatic hydrocarbon ring is divalent.
  • the heterocyclic group may be applied to the description of the heterocyclic group, except that it is divalent.
  • the description of the aryl group described above may be applied, except that the arylene group is a divalent group.
  • heteroaryl group described above may be applied, except that the heteroarylene group is a divalent group.
  • one of the X1 and X2 is O or S, the other is O, S or CRR '.
  • any one of X1 and X2 is O or S, and the other is O or S.
  • X1 and X2 are O or S.
  • X1 and X2 are each O.
  • X1 and X2 are each S.
  • one of X1 and X2 is O, and the other is S.
  • one of X1 and X2 is O, and the other is CRR '.
  • one of X1 and X2 is S and the other is CRR '.
  • R and R ' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • R and R ' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
  • R and R ' are the same as 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 30 carbon atoms.
  • R and R ' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or it is a C1-C20 alkyl group.
  • R and R ' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; Or a substituted or unsubstituted ethyl group.
  • R and R ' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Or an ethyl group.
  • R and R ' are each a methyl group.
  • Cy1 and Cy2 are the same as or different from each other, and each independently a substituted or unsubstituted ring having 6 to 60 carbon atoms.
  • Cy1 and Cy2 are the same as or different from each other, and each independently a substituted or unsubstituted ring having 6 to 30 carbon atoms.
  • Cy1 and Cy2 are the same or different from each other, and each independently is a substituted or unsubstituted 1 to 3 ring ring.
  • Cy1 and Cy2 are the same as or different from each other, and each independently a substituted or unsubstituted 1 to 3 ring of 6 to 60 carbon atoms.
  • Cy2 is substituted or unsubstituted benzene.
  • Cy2 is benzene.
  • Cy1 is a substituted or unsubstituted aromatic hydrocarbon ring; Or an aromatic heterocycle containing O or S as a substituted or unsubstituted hetero element.
  • Cy1 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms; Or it is an aromatic heterocycle containing O or S as a hetero atom having 2 to 30 carbon atoms.
  • Cy1 is substituted or unsubstituted benzene; Substituted or unsubstituted indene; Substituted or unsubstituted benzofuran; Or substituted or unsubstituted benzothiophene.
  • Cy1 is benzene; Indene; Benzofuran; Or benzothiophene.
  • the formula 1 is represented by any one of the following formulas 1-1 to 1-4.
  • R1 to R6, Cy2, X1 and X2 are the same as defined in Formula 1,
  • X3 to X6 are the same as or different from each other, and each independently O, S or CR “R '",
  • R21 to R36, R "and R '" are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group, or combines with an adjacent group to form a substituted or unsubstituted ring.
  • X3 to X6 are the same as or different from each other, and each independently O or S.
  • the R "and R '" are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • R "and R '" are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
  • R "and R '" are the same as 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 30 carbon atoms.
  • R "and R '" are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or it is a C1-C20 alkyl group.
  • R "and R '" are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; Or a substituted or unsubstituted ethyl group.
  • R "and R '" are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Or an ethyl group.
  • R21 to R36 are the same as or different from each other, and each independently hydrogen or deuterium.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or combine with each other to form a substituted or unsubstituted ring.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring.
  • R1 and R2 are the same as 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 30 carbon atoms, or combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 20 carbon atoms; Or an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with deuterium or an alkyl group having 1 to 20 carbon atoms, or combined with each other to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms. .
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 10 carbon atoms; Or an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, or combined with each other to form fluorene unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; Or a substituted or unsubstituted phenyl group, or combine with each other to form a substituted or unsubstituted fluorene.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Or it is a phenyl group unsubstituted or substituted with a methyl group, or combines with each other to form fluorene unsubstituted or substituted with a t-butyl group.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Phenyl group; Or a tolyl group, or combine with each other to form fluorene unsubstituted or substituted with t-butyl group.
  • At least one of the R3 to R6 is represented by the following formula (2), the rest are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group, or combine with each other to form a substituted or unsubstituted heteroring,
  • R3 to R6 are represented by Formula 2, and the rest are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • two of R3 to R6 are represented by Formula 2, and the other two are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • two of R3 to R6 are represented by Chemical Formula 2, and the other two are each independently hydrogen or deuterium.
  • R4 and R6 are represented by Chemical Formula 2, and R3 and R5 are each independently hydrogen or deuterium.
  • two substituents represented by the formula (2) are the same as each other.
  • L1 and L2 are the same as or different from each other, and 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.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; An arylene group having 6 to 30 carbon atoms; Or a heteroarylene group having 2 to 30 carbon atoms.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylene group; Naphthylene group; A divalent fluorenyl group; A divalent carbazolyl group; Divalent dibenzofuranyl group; Or a divalent dibenzothiophenyl group.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; Or an arylene group having 6 to 20 carbon atoms.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a phenylene group.
  • L1 and L2 are each a direct bond.
  • Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with each other to form a substituted or unsubstituted heteroring.
  • Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or combine with each other to form a substituted or unsubstituted heteroring.
  • Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a heterocyclic group containing O, S or N as a substituted or unsubstituted hetero atom having 2 to 30 carbon atoms, or combine with each other to form a hetero ring containing O, S or N as a substituted or unsubstituted hetero element.
  • Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A deuterium, cyano group, halogen group, substituted or unsubstituted silyl group, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of alkyl groups having 1 to 20 carbon atoms; Or substituted with one or more substituents selected from the group consisting of deuterium, cyano group, halogen group, substituted or unsubstituted silyl group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms and substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • heterocyclic group containing O, S or N as an unsubstituted hetero atom having 2 to 30 carbon atoms, or combined with each other, deuterium, cyano group, halogen group, substituted or unsubstituted silyl group, substituted or unsubstituted carbon number 1
  • Heterocycle containing O, S or N is formed by a hetero atom substituted or unsubstituted with one or more substituents selected from the group consisting of an alkyl group of 20 to 20 and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted with at least one substituent selected from the group consisting of deuterium, cyano group, halogen group, trialkylsilyl group having 3 to 60 carbon atoms, and alkyl group having 1 to 20 carbon atoms.
  • Heterocycle containing O, S or N is formed by a hetero atom substituted or unsubstituted with one or more substituents selected from the group consisting of groups.
  • Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group having 6 to 20 carbon atoms; Or a heterocyclic group having 2 to 20 carbon atoms, and Ar1 and Ar2 are deuterium, cyano group, halogen group, trialkylsilyl group having 3 to 30 carbon atoms, alkyl group having 1 to 10 carbon atoms, 1 to 10 carbon atoms substituted with deuterium.
  • It may include at least one substituent selected from the group consisting of an alkyl group, an alkyl group having 1 to 10 carbon atoms substituted with a halogen group, an aryl group having 6 to 30 carbon atoms and an aryl group having 6 to 30 carbon atoms substituted with deuterium.
  • Ar1 and Ar2 are each a phenyl group, and combine with each other to form carbazole, and the carbazole is deuterium, cyano group, halogen group, trialkylsilyl group having 3 to 30 carbon atoms, carbon number 1 Selected from the group consisting of an alkyl group of 10 to 10, an alkyl group of 1 to 10 carbon atoms substituted with deuterium, an alkyl group of 1 to 10 carbon atoms substituted with a halogen group, an aryl group of 6 to 30 carbon atoms and an aryl group of 6 to 30 carbon atoms substituted with deuterium. It may contain one or more substituents.
  • Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted dibenzothiophenyl group; Or a substituted or unsubstituted carbazole group, or combine with each other to form a substituted or unsubstituted carbazole.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Naphthyl group; 9,9-dimethylfluorenyl group; Dibenzofuranyl group; Dibenzothiophenyl group; Or a carbazolyl group, wherein Ar1 and Ar2 are deuterium, cyano groups, halogen groups, trialkylsilyl groups having 1 to 30 carbon atoms, alkyl groups having 1 to 10 carbon atoms, alkyl groups having 1 to 10 carbon atoms substituted with deuterium, and halogen groups It may include one or more substituents selected from the group consisting of an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms and an aryl group having 6 to 30 carbon atoms substituted with deuterium.
  • Ar1 and Ar2 are each a phenyl group, and combine with each other to form carbazole, and the carbazole is deuterium, cyano group, halogen group, trialkylsilyl group having 3 to 30 carbon atoms, carbon number 1 Selected from the group consisting of an alkyl group of 10 to 10, an alkyl group of 1 to 10 carbon atoms substituted with deuterium, an alkyl group of 1 to 10 carbon atoms substituted with a halogen group, an aryl group of 6 to 30 carbon atoms and an aryl group of 6 to 30 carbon atoms substituted with deuterium. It may contain one or more substituents.
  • Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substitute with one or more substituents selected from the group consisting of deuterium, cyano group, halogen group, trimethylsilyl group, alkyl group having 1 to 10 carbon atoms, alkyl group having 1 to 10 carbon atoms substituted with deuterium, and alkyl group having 1 to 10 carbon atoms substituted with halogen group Or an unsubstituted phenyl group; Substitute with one or more substituents selected from the group consisting of deuterium, cyano group, halogen group, trimethylsilyl group, alkyl group having 1 to 10 carbon atoms, alkyl group having 1 to 10 carbon atoms substituted with deuterium, and alkyl group having 1 to 10 carbon atoms substituted with halogen group Or an unsubstituted biphenyl group; Substitute with one or more substituents selected from the group consisting of deuterium
  • the formula 1 is represented by the following formula 2-1.
  • R1, R2, Cy1, Cy2, X1 and X2 are the same as defined in Formula 1,
  • R101 and R102 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group,
  • L11 to L14 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar11 to Ar14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups of Ar11 to Ar14 combine with each other to form a substituted or unsubstituted heteroring.
  • Chemical Formula 2-1 is represented by Chemical Formula 2-2 below.
  • Cy1, Cy2, X1, X2, R1, R2, R101, R102, L11 to L14, Ar11 to Ar14 are as defined in Chemical Formula 2-1.
  • the -N (-L11-Ar11) (-L12-Ar12) and -N (-L14-Ar13) (-L14-Ar14) are the same as each other.
  • the formula 2-1 is represented by any one of the following formulas 2-1-1 to 2-1-4.
  • R1, R2, Cy2, X1, X2, L11 to L14, Ar11 to Ar14, R101 and R102 are as defined in Chemical Formula 2-1,
  • X7 to X10 are the same as or different from each other, and each independently O, S or CRaRb,
  • R41 to R56, Ra and Rb are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group, or combines with an adjacent group to form a substituted or unsubstituted ring.
  • X7 to X10 are the same as or different from each other, and each independently O or S.
  • the Ra and Rb are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • Ra and Rb are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
  • Ra and Rb are the same as 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 30 carbon atoms.
  • Ra and Rb are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or it is a C1-C20 alkyl group.
  • Ra and Rb are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; Or a substituted or unsubstituted ethyl group.
  • Ra and Rb are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Or an ethyl group.
  • the R41 to R56 are the same as or different from each other, and each independently hydrogen or deuterium.
  • the R101 and R102 are the same as or different from each other, and each independently hydrogen or deuterium.
  • L11 to L14 are the same as or different from each other, and 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.
  • the L11 to L14 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.
  • L11 to L14 are the same as or different from each other, and each independently a direct bond; An arylene group having 6 to 30 carbon atoms; Or a heteroarylene group having 2 to 30 carbon atoms.
  • L11 to L14 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylene group; Naphthylene group; A divalent fluorenyl group; A divalent carbazolyl group; Divalent dibenzofuranyl group; Or a divalent dibenzothiophenyl group.
  • L11 to L14 are the same as or different from each other, and each independently a direct bond; Or an arylene group having 6 to 20 carbon atoms.
  • L11 to L14 are the same as or different from each other, and each independently a direct bond; Or a phenylene group.
  • L11 to L14 are each a direct bond.
  • the Ar11 To Ar14 are the same as or different from each other, each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups of Ar11 to Ar14 combine with each other to form a substituted or unsubstituted heteroring.
  • Ar11 to Ar14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or adjacent groups of Ar11 to Ar14 combine with each other to form a substituted or unsubstituted heterocycle having 2 to 60 carbon atoms.
  • Ar11 to Ar14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a heterocyclic group containing O, S, or N as a substituted or unsubstituted hetero atom having 2 to 30 carbon atoms, or adjacent groups among Ar11 to Ar14 combine with each other to form a substituted or unsubstituted heterocycle having 4 to 30 carbon atoms. .
  • Ar11 to Ar14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A deuterium, cyano group, halogen group, substituted or unsubstituted silyl group, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of alkyl groups having 1 to 20 carbon atoms; Or substituted with one or more substituents selected from the group consisting of deuterium, cyano group, halogen group, substituted or unsubstituted silyl group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms and substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • heterocyclic group containing O, S or N as an unsubstituted hetero atom having 2 to 30 carbon atoms, or combined with each other, deuterium, cyano group, halogen group, substituted or unsubstituted silyl group, substituted or unsubstituted carbon number 1
  • Heterocycle containing O, S or N is formed by a hetero atom substituted or unsubstituted with one or more substituents selected from the group consisting of an alkyl group of 20 to 20 and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • Ar11 to Ar14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted with at least one substituent selected from the group consisting of deuterium, cyano group, halogen group, trialkylsilyl group having 3 to 60 carbon atoms, and alkyl group having 1 to 20 carbon atoms.
  • Heterocycle containing O, S or N is formed by a hetero atom substituted or unsubstituted with one or more substituents selected from the group consisting of groups.
  • Ar11 to Ar14 are the same as or different from each other, and each independently an aryl group having 6 to 20 carbon atoms; Or a heterocyclic group having 2 to 20 carbon atoms, and Ar1 and Ar2 are deuterium, cyano group, halogen group, trialkylsilyl group having 3 to 30 carbon atoms, alkyl group having 1 to 10 carbon atoms, 1 to 10 carbon atoms substituted with deuterium. It may include one or more substituents selected from the group consisting of an alkyl group, an alkyl group having 1 to 10 carbon atoms substituted with a halogen group, an aryl group having 6 to 30 carbon atoms and an aryl group substituted with deuterium.
  • Ar11 and Ar12 are each a phenyl group, and combine with each other to form carbazole, and the carbazole is deuterium, cyano group, halogen group, trialkylsilyl group having 3 to 30 carbon atoms, carbon number 1 It includes at least one substituent selected from the group consisting of an alkyl group of 10 to 10, an alkyl group of 1 to 10 carbon atoms substituted with deuterium, an alkyl group of 1 to 10 carbon atoms substituted with a halogen group, an aryl group of 6 to 30 carbon atoms and an aryl group substituted with deuterium. can do.
  • Ar13 and Ar14 are each a phenyl group, and combine with each other to form carbazole, and the carbazole is deuterium, cyano group, halogen group, trialkylsilyl group having 3 to 30 carbon atoms, carbon number 1 It includes at least one substituent selected from the group consisting of an alkyl group of 10 to 10, an alkyl group of 1 to 10 carbon atoms substituted with deuterium, an alkyl group of 1 to 10 carbon atoms substituted with a halogen group, an aryl group of 6 to 30 carbon atoms and an aryl group substituted with deuterium. can do.
  • Ar11 to Ar14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted fluorenyl group; Or a substituted or unsubstituted dibenzofuranyl group, or adjacent groups of Ar11 to Ar14 combine with each other to form a substituted or unsubstituted carbazole.
  • Ar11 to Ar14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substitute with one or more substituents selected from the group consisting of deuterium, cyano group, halogen group, trimethylsilyl group, alkyl group having 1 to 10 carbon atoms, alkyl group having 1 to 10 carbon atoms substituted with deuterium, and alkyl group having 1 to 10 carbon atoms substituted with halogen group Or an unsubstituted phenyl group; Substitute with one or more substituents selected from the group consisting of deuterium, cyano group, halogen group, trimethylsilyl group, alkyl group having 1 to 10 carbon atoms, alkyl group having 1 to 10 carbon atoms substituted with deuterium, and alkyl group having 1 to 10 carbon atoms substituted with halogen group Or an unsubstituted biphenyl group; Substitute with one or more substituents selected from the group consisting of deuterium
  • the formula 1 is represented by the following formula 1-5 or 1-6.
  • R1, R2, Cy1, Cy2, X1 and X2 are the same as defined in Formula 1,
  • R103 to R108 and Ar101 to Ar104 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group,
  • n1 and n2 are each an integer of 0 to 8, and when n1 and n2 are each 2 or more, the substituents in 2 or more parentheses are the same or different from each other.
  • the R103 to R108 are the same as or different from each other, and each independently hydrogen or deuterium.
  • the R107 and R108 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 10 carbon atoms; Or an aryl group having 6 to 30 carbon atoms.
  • the R107 and R108 are the same as or different from each other, and each independently hydrogen; Or deuterium.
  • Ar101 to Ar104 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • Ar101 to Ar104 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • Ar101 to Ar104 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a heterocyclic group containing O, S or N as a substituted or unsubstituted hetero atom having 2 to 30 carbon atoms.
  • Ar101 to Ar104 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A deuterium, cyano group, halogen group, substituted or unsubstituted silyl group, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of alkyl groups having 1 to 20 carbon atoms; Or substituted with one or more substituents selected from the group consisting of deuterium, cyano group, halogen group, substituted or unsubstituted silyl group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms and substituted or unsubstituted aryl group having 6 to 30 carbon atoms. Or a heterocyclic group containing O, S or N as an unsubstituted hetero atom having 2 to 30 carbon atoms.
  • Ar101 to Ar104 are the same as or different from each other, and each independently an aryl group having 6 to 20 carbon atoms; Or a heterocyclic group having 2 to 20 carbon atoms, wherein Ar101 to Ar104 are deuterium, cyano group, halogen group, trialkylsilyl group having 3 to 30 carbon atoms, alkyl group having 1 to 10 carbon atoms, 1 to 10 carbon atoms substituted with deuterium It may include at least one substituent selected from the group consisting of an alkyl group, an alkyl group having 1 to 10 carbon atoms substituted with a halogen group, an aryl group having 6 to 30 carbon atoms and an aryl group having 6 to 30 carbon atoms substituted with deuterium.
  • Ar101 to Ar104 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted dibenzothiophenyl group; Or a substituted or unsubstituted carbazolyl group.
  • Ar101 to Ar104 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Naphthyl group; 9,9-dimethylfluorenyl group; Dibenzofuranyl group; Dibenzothiophenyl group; Or a carbazolyl group, wherein Ar101 to A104 are deuterium, cyano groups, halogen groups, trialkylsilyl groups having 1 to 30 carbon atoms, alkyl groups having 1 to 10 carbon atoms, alkyl groups having 1 to 10 carbon atoms substituted with deuterium, and halogen groups It may include one or more substituents selected from the group consisting of an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms and an aryl group having 6 to 30 carbon atoms substituted with deuterium.
  • Ar101 to Ar104 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substitute with one or more substituents selected from the group consisting of deuterium, cyano group, halogen group, trimethylsilyl group, alkyl group having 1 to 10 carbon atoms, alkyl group having 1 to 10 carbon atoms substituted with deuterium, and alkyl group having 1 to 10 carbon atoms substituted with halogen group Or an unsubstituted phenyl group; Substitute with one or more substituents selected from the group consisting of deuterium, cyano group, halogen group, trimethylsilyl group, alkyl group having 1 to 10 carbon atoms, alkyl group having 1 to 10 carbon atoms substituted with deuterium, and alkyl group having 1 to 10 carbon atoms substituted with halogen group Or an unsubstituted biphenyl group; Substitute with one or more substituents selected from the group consisting of deuterium
  • the formula 1 may be represented by any one of the following compounds.
  • the compound of Formula 1 may be prepared as in Scheme 1 below.
  • Reaction Scheme 1 below describes the synthesis process of some compounds corresponding to Formula 1 herein, but various compounds corresponding to Formula 1 herein can be synthesized using the same synthesis process as in Reaction Scheme 1 below, and the substituents are in the art. It can be combined by a known method, the type, position and number of substituents can be changed according to techniques known in the art.
  • Intermediate 3 was synthesized by Suzuki coupling reaction of Intermediate 1 (IM-1) and Intermediate 2 (IM-2), and Intermediate 3 (IM) was prepared using a Grignard reagent.
  • Intermediate 4 (IM-4) containing tertiary alcohol can be obtained from the ester of -3).
  • the final compound can be obtained by Buckwald amination in Intermediate 5 (IM-5) obtained by a ring-closing reaction using concentrated sulfuric acid in Intermediate 4 (IM-4).
  • intermediate 3 may be made of a ketone by an intramolecular condensation reaction using concentrated sulfuric acid, and intermediate 6 (IM-6) by a subsequent bromination reaction. Subsequently, a nucleation reaction is performed on the ketone using aryl lithium, and then intermediate 7 (IM-7) is obtained by reaction with sulfuric acid.
  • the final compound can be obtained by a Buchwald amination reaction using various arylamines.
  • compounds having various energy band gaps may be synthesized by introducing various substituents to the core structure of Chemical Formula 1 above.
  • the HOMO and LUMO energy levels of the compound can be adjusted by introducing various substituents to the core structure having the above structure.
  • the organic light emitting device includes a first electrode; A second electrode provided opposite to the first electrode; And at least one layer of an organic material provided between the first electrode and the second electrode, and at least one layer of the organic material layer includes a compound represented by Chemical Formula 1 described above.
  • the organic light emitting device of the present specification may be manufactured by a conventional method and a method of manufacturing an organic light emitting device, except that one or more organic material layers are formed using the compound represented by Chemical Formula 1 above.
  • the compound may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • the solution application method means spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.
  • the organic material layer of the organic light emitting device of the present specification may have a single layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention is a hole injection layer, a hole transport layer, a layer simultaneously performing hole transport and hole injection as an organic material layer, an electron suppressing layer, a light emitting layer, an electron transport layer and an electron injection layer, a layer simultaneously performing electron transport and electron injection It may have a structure including a.
  • the structure of the organic light emitting device is not limited to this, and may include fewer or more organic material layers.
  • the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or electron injection layer may include the aforementioned compound.
  • the organic material layer may include a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer may include the above-described compound.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the above-described compound.
  • the organic material layer includes a light emitting layer
  • the light emitting layer may include the above-described compound as a dopant in the light emitting layer.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes the above-described compound as a dopant in the light emitting layer, and may further include a host.
  • the organic light emitting diode includes a light emitting layer, and the light emitting layer further includes a compound represented by the following Chemical Formula H in addition to the compound represented by the Chemical Formula 1. Specifically, the above-mentioned compound is included as a dopant in the light-emitting layer, and the compound represented by the following formula (H) is included as a host in the light-emitting layer.
  • L21 to L23 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • R21 to R27 are the same as 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 silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • Ar21 to Ar23 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • a 0 or 1.
  • a position of -L23-Ar23 is connected to hydrogen or deuterium.
  • L21 to L23 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.
  • L21 to L23 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms containing N, O, or S.
  • L21 to L23 are the same as or different from each other, and each independently a direct bond; Deuterium, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms or an arylene group having 6 to 30 carbon atoms unsubstituted or substituted with a heteroaryl group having 2 to 30 carbon atoms; Or a heteroarylene group having 2 to 30 carbon atoms unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms.
  • L21 to L23 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted divalent dibenzofuran group; Or a substituted or unsubstituted divalent dibenzothiophene group.
  • L21 to L23 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylene group; Or a naphthylene group, L21 to L23 may each contain one or more deuterium.
  • L21 is a direct bond.
  • L22 is a direct bond; Or a phenylene group.
  • L23 is a direct bond.
  • L1 may include deuterium. Specifically, L1 contains 1 or more deuterium.
  • L2 may include deuterium. Specifically, L2 contains one or more deuterium.
  • L3 may include deuterium. Specifically, L3 contains one or more deuterium.
  • Ar21 to Ar23 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • Ar21 to Ar23 are the same as or different from each other, and each independently substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • Ar21 to Ar23 are the same as or different from each other, and each independently substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.
  • Ar21 to Ar23 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted phenanthryl group; A substituted or unsubstituted phenylene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted benzofluorenyl group; A substituted or unsubstituted furan group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstit
  • Ar21 to Ar23 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthryl group; Dibenzofuran group; Naphthobenzofuran group; Dibenzothiophene group; Or a naphthobenzothiophene group, Ar21 to Ar23 may each contain one or more deuterium.
  • Ar21 and Ar22 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthryl group; Dibenzofuran group; Naphthobenzofuran group; Dibenzothiophene group; Or a naphthobenzothiophene group.
  • Ar21 and Ar22 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; 1-naphthyl group; 2-naphthyl group; Or dibenzofuran group.
  • Ar23 is a phenyl group; Biphenyl group; It is a naphthyl group.
  • Ar23 is a naphthyl group.
  • Ar1 may include deuterium. Specifically, Ar1 contains one or more deuterium.
  • Ar2 may include deuterium. Specifically, Ar2 contains one or more deuterium.
  • Ar3 may include deuterium. Specifically, Ar3 contains one or more deuterium.
  • Ar21 and Ar22 are different from each other.
  • Ar21 is a substituted or unsubstituted aryl group
  • Ar22 is a substituted or unsubstituted aryl group
  • Ar21 is a substituted or unsubstituted aryl group
  • Ar22 is a substituted or unsubstituted heteroaryl group.
  • Ar21 is an aryl group unsubstituted or substituted with deuterium
  • Ar22 is an aryl group unsubstituted or substituted with deuterium
  • Ar21 is an aryl group unsubstituted or substituted with deuterium
  • Ar22 is a heteroaryl group unsubstituted or substituted with deuterium.
  • R21 to R27 are the same as 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 silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • R201 to R207 are the same as or different from each other, and each independently hydrogen or deuterium.
  • R201 to R207 are hydrogen.
  • R201 to R207 are deuterium.
  • Chemical Formula H is represented by the following Chemical Formula H01 or H02.
  • L21 to L23 and Ar21 to Ar23 are the same as defined in Formula H, D means deuterium, k1 is an integer from 0 to 8, and k2 is an integer from 0 to 7.
  • the compound represented by Chemical Formula H is any one selected from the following compounds.
  • the content of the dopant is 1 part by weight to 20 parts by weight based on 100 parts by weight of the host, preferably 1 part by weight to 5 parts by weight It can contain.
  • the driving voltage of the manufactured organic light emitting device is low and the luminous efficiency is high.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes the above-described compound as a dopant in the light emitting layer, a fluorescent host or a phosphorescent host, and other organic compounds, metals or metal compounds as dopants It can contain.
  • the compound represented by Chemical Formula H may be included as one type in the organic material layer (specifically, the light emitting layer), or may be included as two or more types. Specifically, the first host represented by Chemical Formula H and the second host represented by Chemical Formula H may be included in the organic material layer.
  • the weight ratio of the first host represented by Chemical Formula H and the second host represented by Chemical Formula H is 95: 5 to 5:95, more preferably 30:70 to 70:30.
  • the first host and the second host are different from each other.
  • Ar21 and Ar22 of the first host represented by Chemical Formula H are the same or different from each other, and each independently an substituted or unsubstituted aryl group;
  • Ar21 of the second host represented by Formula H is a substituted or unsubstituted aryl group, and Ar22 is a substituted or unsubstituted heteroaryl group.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes the above-described compound as a dopant in the light emitting layer, a fluorescent host or a phosphorescent host, and can be used with an iridium-based (Ir) dopant.
  • the organic material layer includes a light emitting layer
  • the light emitting layer may include the above-described compound as a host of the light emitting layer.
  • the organic material layer may include a light emitting layer
  • the light emitting layer may include the above-described compound as a host of the light emitting layer, and may further include a dopant.
  • the organic material layer includes an electron suppression layer, and the electron suppression layer may include the above-described compound.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is an anode
  • the organic light emitting device may have, for example, a stacked structure as described below, but is not limited thereto.
  • the structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 to 3, but 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 stacked on a substrate 1.
  • the compound may be included in the light emitting layer 3.
  • the anode 2 the hole injection layer 5, the hole transport layer 6, the light emitting layer 7, the layer 8 and the cathode 4 simultaneously performing electron injection and electron transport, sequentially on the substrate 1
  • the structure of the stacked organic light emitting device is illustrated.
  • the compound may be included in the hole injection layer 5, the hole transport layer 6, the light emitting layer 7, or the layer 8 simultaneously performing electron injection and electron transport.
  • the anode 2 the hole injection layer 5, the first hole transport layer 6a, the second hole transport layer 6b, the light emitting layer 7, the electron injection and electron transport layer simultaneously on the substrate 1
  • the structure of the organic light emitting device in which (8) and the cathode 4 are sequentially stacked is illustrated.
  • the compound is the hole injection layer (5), the first hole transport layer (6a), the second hole transport layer (6b), the light emitting layer (7) or a layer (8) for electron injection and electron transport simultaneously Can be included in
  • the organic light emitting device uses a metal vapor deposition (PVD) method, such as sputtering or e-beam evaporation, to have a metal or conductive metal oxide on the substrate or alloys thereof
  • PVD metal vapor deposition
  • an organic light emitting device may be made by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.
  • the organic material layer may be a multi-layer structure including a hole injection layer, a hole transport layer, a layer simultaneously performing hole injection and hole transport, an electron suppressing layer, a light emitting layer and an electron transport layer, an electron injection layer, an electron injection and electron transport layer, and the like. However, it is not limited thereto, and may be a single-layer structure.
  • the organic material layer may use a variety of polymer materials to reduce the number of solvent processes (e.g., spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer) rather than deposition. Can be prepared in layers.
  • the positive electrode is an electrode for injecting holes
  • a positive electrode material is preferably a material having a large work function to facilitate hole injection into an organic material layer.
  • Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
  • the cathode is an electrode for injecting electrons
  • the cathode material is preferably a material having a small work function to facilitate electron injection into an organic material layer.
  • 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;
  • There is a multilayer structure material such as LiF / Al or LiO 2 / Al, but is not limited thereto.
  • the hole injection layer is a layer that serves to smoothly inject holes from the anode to the light emitting layer.
  • a hole injection material can be well injected with holes from the anode, and HOMO (highest occupied) of the hole injection material It is preferable that the molecular orbital is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances.
  • the thickness of the hole injection layer may be 1 to 150 nm.
  • the thickness of the hole injection layer is 1 nm or more, there is an advantage of preventing the hole injection characteristics from being deteriorated. If it is 150 nm or less, the thickness of the hole injection layer is too thick, so that the driving voltage is increased to improve hole movement. There is an advantage that can be prevented.
  • the hole transport layer may serve to facilitate the transport of holes, and may be a single layer or a multi-layer structure of two or more layers.
  • a hole transport material a material capable of receiving holes from an anode or a hole injection layer and transporting holes to a light emitting layer is suitable as a material having high mobility for holes.
  • Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.
  • An electron suppressing layer may be provided between the hole transport layer and the light emitting layer.
  • the electron suppressing layer may be the above-described compound or a material known in the art.
  • the light emitting layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material.
  • a material capable of emitting light in the visible region by receiving and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, is preferably a material 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-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly (p-phenylenevinylene) (PPV) polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.
  • Alq 3 8-hydroxy-quinoline aluminum complex
  • Carbazole-based compounds Dimerized styryl compounds
  • BAlq 10-hydroxybenzo quinoline-metal compound
  • Benzoxazole, benzthiazole and benzimidazole compounds Benzoxazole, benzthiazole and benzimidazole compounds
  • Poly (p-phenylenevinylene) (PPV) polymers Spiro compounds
  • Polyfluorene, rubrene, and the like but are not limited to these.
  • the host material of the light emitting layer includes a condensed aromatic ring derivative or a heterocyclic compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc.
  • heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • PIQIr (acac) bis (1-phenylisoquinoline) acetylacetonateiridium
  • PQIr (acac) bis (1-phenylquinoline) acetylacetonate iridium
  • PQIr (tris (1-phenylquinoline) iridium are used as the emission dopant.
  • Phosphorescent materials such as octaethylporphyrin platinum (PtOEP), and fluorescent materials such as Alq 3 (tris (8-hydroxyquinolino) aluminum) may be used, but are not limited thereto.
  • a phosphorescent material such as Ir (ppy) 3 (fac tris (2-phenylpyridine) iridium) or a fluorescent material such as Alq3 (tris (8-hydroxyquinolino) aluminum) can be used as the light emitting dopant.
  • a fluorescent material such as Alq3 (tris (8-hydroxyquinolino) aluminum
  • a phosphorescent material such as (4,6-F2ppy) 2 Irpic is used as a light emitting dopant, but spiro-DPVBi, spiro-6P, distylbenzene (DSB), distriarylene (DSA), Fluorescent materials such as PFO-based polymers and PPV-based polymers may be used, but are not limited thereto.
  • a hole suppressing layer may be provided between the electron transporting layer and the light emitting layer, and the hole suppressing layer is a layer that prevents the cathode from reaching the hole, and may be generally formed under the same conditions as the hole injection layer.
  • the hole suppressing layer is a layer that prevents the cathode from reaching the hole, and may be generally formed under the same conditions as the hole injection layer.
  • oxadiazole derivatives triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, and the like, but are not limited thereto.
  • the electron transport layer may serve to facilitate the transport of electrons.
  • the electron transport material a material capable of receiving electrons well from the cathode and transferring them to the light emitting layer, a material having high mobility for electrons is suitable. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.
  • the thickness of the electron transport layer may be 1 to 50 nm. When the thickness of the electron transport layer is 1 nm or more, there is an advantage of preventing the electron transport properties from deteriorating, and when it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the driving voltage from rising to improve the movement of electrons. There is an advantage.
  • the electron injection layer may serve to facilitate injection of electrons.
  • the electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, has an excellent electron injection effect on the light emitting layer or the light emitting material, prevents movement of excitons generated in the light emitting layer to the hole injection layer, and also , A compound having excellent thin film forming ability is preferred.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.
  • the organic light emitting device may be a front emission type, a back emission type, or a double-sided emission type depending on the material used.
  • intermediate A-1 (50.0 g, 0.167 mol) and intermediate A-2 (45.67 g, 0.20 mol), bis (tri-tert-butylphosphine) palladium (0) [Bis (tri-tert-butylphosphine) -palladium (0)] (0.85g, 1.67mmol), K 2 CO 3 (69.2g, 0.50mol) and a flask containing 550 mL of tetrahydrofuran (THF) was heated and stirred for 4 hours. After the reaction solution was cooled to room temperature, water and ethyl acetate were added, followed by extraction and washing. The organic layer was recovered to remove the extraction solvent, and then purified by recrystallization (chloroform / hexane) to obtain 50.4 g of Intermediate A-3.
  • intermediate A-4 (15.5 g, 0.038 mol) was dissolved in 30 mL acetic acid and 90 mL chloroform, and then a catalytic amount of the emulsified yellow phase was added, followed by stirring at 50 ° C for 4 hours.
  • the reaction solution was cooled to room temperature and filtered.
  • the filter cake was dissolved in toluene, neutralized with a saturated NaHCO 3 aqueous solution (saturated aq. NaHCO 3 ), and then extracted and washed.
  • the organic layer was recovered to remove the extraction solvent, and then purified by recrystallization (ethyl acetate / hexane) to obtain 12.0 g of Intermediate A-5.
  • the radiative transition probability (f) is a measure of fluorescence quantum efficiency and is calculated by the following equation. The greater the value of the radiation transition probability (f), the greater the luminous efficiency.
  • the radiative transition probability (f) of Comparative Examples 1 and 2 obtained a very small value compared to the compound BP-4 of Example 1, and as a result, the efficiency of the device containing compounds X-1 and X-2 would be very low. Can be expected
  • the emission wavelength can be predicted by the singlet energy value of Compound X-2, and since it is a very short wavelength compared to Compound BP-4, the efficiency of the device is expected to be very low when used as a blue light emitting dopant in the light emitting layer, so it is an appropriate blue light emitting dopant. Can not.
  • the luminous efficiency of the compound B-P-4 is higher than that of the compounds X-1 and X-2, and the efficiency of the blue light emitting device is also increased.
  • the measuring equipment used to measure the maximum emission wavelength is a JASCO FP-8600 fluorescence spectrophotometer.
  • the maximum emission wavelength can be obtained as follows.
  • a sample for measurement is prepared by dissolving the compound to be measured using toluene as a solvent at a concentration of 10 -5 M.
  • the sample solution is put in a quartz cell and degassing is performed using nitrogen gas (N 2 ) to remove oxygen in the solution, and then fluorescence intensity and maximum luminescence peak can be measured at room temperature (300K) using a measuring device.
  • N 2 nitrogen gas
  • fluorescence intensity and maximum luminescence peak can be measured at room temperature (300K) using a measuring device.
  • the x-axis is the wavelength ( ⁇ , unit: nm) and the y-axis is the emission intensity.
  • the maximum emission peak of Compound B-P-2 represented by Formula 1 is within 440 nm to 465 nm, but the compounds of Comparative Examples 3 to 5 (the structure without Cy1 in Formula 1) are outside the above range. Therefore, when the maximum emission peak of the compound represented by Formula 1 satisfies the range of 440 nm to 465 nm, it can be used as a blue light emitting dopant in the light emitting layer to increase the efficiency of the device.
  • a glass substrate coated with a thin film of indium tin oxide (ITO) at a thickness of 1300 ⁇ was put in distilled water in which detergent was dissolved and washed with ultrasonic waves.
  • ITO indium tin oxide
  • Fischer Co. was used as a detergent
  • distilled water filtered secondarily by a filter of Millipore Co. was used as distilled water.
  • ultrasonic cleaning was repeated twice with distilled water for 10 minutes.
  • ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying and then transported to a plasma cleaner.
  • the substrate was transferred to a vacuum evaporator.
  • the following compound HAT was thermally vacuum-deposited to a thickness of 50 Pa to form a hole injection layer. Thereafter, the following compound HT-A 800A was vacuum-deposited as a first hole transport layer, and subsequently the following compound HT-B 100B was deposited as a second hole transport layer.
  • the host BH-A and the dopant Compound A-P-3 were vacuum-deposited in a weight ratio of 96: 4 to form a 200-mm thick light emitting layer.
  • the deposition rate of the organic material was maintained at 0.4 to 1.0 ⁇ / sec
  • the lithium fluoride of the negative electrode was maintained at a deposition rate of 0.3 ⁇ / sec
  • the aluminum was maintained at a deposition rate of 2 ⁇ / sec. -7 to 5 x 10 -8 torr was maintained to produce an organic light emitting device.
  • An organic light-emitting device was manufactured in the same manner as in Example 3, except that the host and dopant compounds shown in Table 3 below were used as the light-emitting layer material in Example 3.
  • Example 3 the first host material, the second host material, and the dopant as the host material of the light emitting layer were vacuum deposited to a thickness of 200 Pa by using a weight ratio of 48: 48: 4.
  • an organic light emitting device was manufactured in the same manner as in Example 3, except that the host and dopant compounds shown in Table 4 below were used as the light emitting layer material.
  • the organic light emitting device of Examples 19 to 31 containing the compound of the present invention as a dopant in the light emitting layer has better light emission efficiency and lower driving voltage than the organic light emitting devices of Comparative Examples 9 to 12. And it was found. Specifically, as in Comparative Examples 3 and 4 described above, Compounds X-3 and X-4 of Comparative Examples do not have a Cy1 ring of Formula 1, and thus the luminous efficiency is poor.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un composé représenté par la formule chimique 1 et un dispositif électroluminescent organique le comprenant.
PCT/KR2019/015866 2018-11-19 2019-11-19 Composé polycyclique et dispositif électroluminescent organique le comprenant WO2020106028A1 (fr)

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