WO2023085860A1 - Composé et dispositif électroluminescent organique le comprenant - Google Patents

Composé et dispositif électroluminescent organique le comprenant Download PDF

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WO2023085860A1
WO2023085860A1 PCT/KR2022/017781 KR2022017781W WO2023085860A1 WO 2023085860 A1 WO2023085860 A1 WO 2023085860A1 KR 2022017781 W KR2022017781 W KR 2022017781W WO 2023085860 A1 WO2023085860 A1 WO 2023085860A1
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substituted
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aryl group
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김민준
윤준
이성재
홍성길
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주식회사 엘지화학
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Priority to CN202280029544.3A priority Critical patent/CN117177978A/zh
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    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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    • H10K50/00—Organic light-emitting devices
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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Definitions

  • the present specification relates to a compound and an organic light emitting device including the same.
  • an organic light emitting device is a light emitting device using an organic semiconductor material, and requires exchange of holes and/or electrons between an electrode and an organic semiconductor material.
  • the organic light emitting device can be roughly divided into two types according to the operation principle as follows. First, excitons are formed in the organic material layer by photons introduced into the device from an external light source, and these excitons are separated into electrons and holes, and these electrons and holes are transferred to different electrodes and used as a current source (voltage source) It is a light emitting device of the form.
  • the second is a type of light emitting device that injects holes and/or electrons into the organic semiconductor material layer forming the interface with the electrodes by applying voltage or current to two or more electrodes and operates by the injected electrons and holes.
  • the organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often composed of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron suppression 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, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and when the injected holes and electrons meet, excitons are formed. When it falls back to the ground state, it glows.
  • Such an organic light emitting device is known to have characteristics such as self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, and high contrast.
  • Materials used as the organic 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 suppression materials, electron transport materials, and electron injection materials, depending on their functions.
  • Light-emitting materials include blue, green, and red light-emitting materials according to light-emitting colors, and yellow and orange light-emitting materials required to realize better natural colors.
  • a host/dopant system may be used as a light emitting material.
  • the principle is that when a small amount of a dopant having a smaller energy band gap and higher luminous efficiency than the host constituting the light emitting layer is mixed in the light emitting layer in a small amount, excitons generated in the host are transported to the dopant to emit light with high efficiency.
  • the wavelength of the host moves to the wavelength range of the dopant, light of a desired wavelength can be obtained according to the type of dopant used.
  • materials constituting the organic material layer in the device such as hole injection materials, hole transport materials, light emitting materials, electron suppression materials, electron transport materials, electron injection materials, etc. are stable and efficient materials. Supported by this, the development of new materials is continuously required.
  • An exemplary embodiment of the present specification provides a compound represented by Formula 1 below.
  • X1 to X8 and X11 to X18 are the same as or different from each other, and are each independently N or CR,
  • one of X1 to X8 is N;
  • one of X11 to X18 is N;
  • R are the same as or different from each other and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aryl group,
  • Y1 and Y2 are the same as or different from each other and are each independently O or S,
  • L1 to L3 are the same as or different from each other and each independently represent a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
  • Ar1 is a substituted or unsubstituted aliphatic hydrocarbon ring group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; or two or more of these are condensed ring groups.
  • the first electrode a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layers includes the aforementioned compound.
  • the compound of the present invention can be used as a material for an organic material layer of an organic light emitting device.
  • an organic light emitting device including the compound of the present invention an organic light emitting device having high efficiency, low voltage and long lifespan characteristics can be obtained, and when the compound of the present invention is included in the light emitting layer of the organic light emitting device, a high color gamut can be obtained. It is possible to manufacture an organic light emitting device having
  • FIG 1 and 2 show an example of an organic light emitting device according to the present invention.
  • substitution means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position to be substituted is not limited as long as the hydrogen atom is substituted, that is, a position where the substituent is substituted, and when two or more are substituted , Two or more substituents may be the same as or different from each other.
  • substituted or unsubstituted means deuterium; halogen group; Cyano group (-CN); silyl group; boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or is substituted with a substituent in which two or more substituents from among the above exemplified substituents are connected, or does not have any substituents.
  • a substituent in which two or more 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 silyl group may be represented by a chemical formula of -SiY1Y2Y3, wherein Y1, Y2 and Y3 are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group.
  • the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like, but is not limited thereto. don't
  • the boron group may be represented by a chemical formula of -BY4Y5, wherein Y4 and Y5 are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group.
  • the boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, but is not limited thereto.
  • the alkyl group may be straight or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 10.
  • alkyl group examples include, but are not limited to, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group.
  • the amine group is -NH 2 ; Alkylamine group; N-alkyl arylamine group; Arylamine group; N-arylheteroarylamine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • the amine group include a methylamine group; dimethylamine group; ethylamine group; diethylamine group; phenylamine group; naphthylamine group; Biphenylamine group; an anthracenylamine group; 9-methylanthracenylamine group; diphenylamine group; ditolylamine group; N-phenyltolylamine group; triphenylamine group; N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenyl naphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenylterphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group and the
  • 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 refers to an amine group in which N of the amine group is substituted with an aryl group and a heteroaryl group.
  • the N-alkylheteroarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and a heteroaryl group.
  • alkyl group of an alkylamine group, an N-arylalkylamine group, an alkylthioxy group, an alkylsulfoxy group, and an N-alkylheteroarylamine group is the same as the above-mentioned alkyl group.
  • the alkylthioxy group includes a methylthioxyl group; Ethylthioxy group; tert-butyl thioxy group; Hexylthioxy group; and octylthioxy group
  • the alkyl sulfoxy group includes mesyl; ethyl sulfoxy group; propyl sulfoxy group; Butyl sulfoxy group and the like, but is not limited thereto.
  • 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 number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. Specifically, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but are not limited thereto.
  • 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 number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl 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, triphenylene group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
  • the heteroaryl group is a ring group containing one or more of N, O, P, S, Si, and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms. According to one embodiment, the carbon number of the heterocyclic group is 2 to 30.
  • the heterocyclic group include a pyridine group, a pyrrole group, a pyrimidine group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, and the like. However, it is not limited to these.
  • the arylene group is the same as defined in the above aryl group except that it is a divalent group.
  • heteroarylene group is the same as defined in the above heteroaryl group, except that it is a divalent group.
  • Chemical Formula 1 is any one of Chemical Formulas 1-A to 1-G.
  • X1 to X18, L3, Y1, Y2 and Ar1 are as defined in Formula 1 above.
  • Chemical Formula 1 is any one of Chemical Formulas 1-1 to 1-16.
  • X1 to X18, L1 to L3, Y1, Y2 and Ar1 are as defined in Formula 1 above.
  • Chemical Formula 1 is any one of the following Chemical Formulas 2-1 to 2-3.
  • X1 to X18, L1 to L3, and Ar1 are as defined in Formula 1 above.
  • Chemical Formula 1 is any one of Chemical Formulas 2-A to 2-C.
  • Chemical Formula 1 is any one of the following Chemical Formulas 2-4 to 2-7.
  • Chemical Formula 1 is any one of Chemical Formulas 2-8 to 2-11.
  • Chemical Formula 1 is any one of Chemical Formulas 2-12 to 2-15.
  • X1 to X18, L1 to L3, and Ar1 are as defined in Formula 1 above.
  • Chemical Formula 1 is any one of the following Chemical Formulas 2-16 to 2-19.
  • X1 to X18, L1 to L3, and Ar1 are as defined in Formula 1 above.
  • X1 is N and the others are CH.
  • X2 is N and the others are CH.
  • X3 is N and the others are CH.
  • X4 is N and the others are CH.
  • X5 is N and the others are CH.
  • X6 is N and the others are CH.
  • X7 is N and the others are CH.
  • X8 is N and the others are CH.
  • X11 is N and the others are CH.
  • X12 is N and the others are CH.
  • X13 is N and the others are CH.
  • X14 is N and the others are CH.
  • X15 is N and the others are CH.
  • X16 is N and the others are CH.
  • X17 is N and the others are CH.
  • X18 is N and the others are CH.
  • Y1 and Y2 are O.
  • Y1 and Y2 are S.
  • Y1 is S and Y2 is O.
  • Y1 is O and Y2 is S.
  • R is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aryl group.
  • R is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, or a substituted or unsubstituted carbon atom having 6 to 10 carbon atoms. It is an aryl group of 30.
  • R is hydrogen; heavy hydrogen; An alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with heavy hydrogen; an alkoxy group having 1 to 10 carbon atoms unsubstituted or substituted with heavy hydrogen; Or an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen.
  • R is hydrogen, heavy hydrogen, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms.
  • R is hydrogen or deuterium.
  • L1 to L3 are the same as or different from each other, and each independently represents a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted 3 to 30 carbon atoms. It is a heteroarylene group.
  • L1 to L3 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted 3 to 20 carbon atoms. It is a heteroarylene group.
  • L1 to L3 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted 3 to 15 carbon atoms. It is a heteroarylene group.
  • L1 to L3 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, or a substituted or unsubstituted divalent naphthyl group.
  • L1 to L3 are the same as or different from each other, and are each independently a phenylene group substituted or unsubstituted with deuterium, a divalent biphenyl group substituted or unsubstituted with deuterium, a substituted or unsubstituted deuterium group, It is an unsubstituted divalent naphthyl group, a divalent fluorene group substituted or unsubstituted with deuterium, a divalent anthracene group substituted or unsubstituted with deuterium, or a divalent phenanthrene group substituted or unsubstituted with deuterium.
  • L1 to L3 are the same as or different from each other, and are each independently a phenylene group substituted or unsubstituted with deuterium, a divalent biphenyl group substituted or unsubstituted with deuterium, or a deuterium substituted or an unsubstituted divalent naphthyl group.
  • L1 to L3 are the same as or different from each other, and each independently represents a phenylene group, a divalent biphenyl group, or a divalent naphthyl group.
  • L1 and L2 are the same as each other, and are a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms.
  • L1 and L2 are the same as each other, and a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent naphthyl group, or a substituted or unsubstituted divalent naphthyl group A divalent fluorene group, a substituted or unsubstituted divalent anthracene group, or a substituted or unsubstituted divalent phenanthrene group.
  • L1 and L2 are the same, and a phenylene group substituted or unsubstituted with deuterium, a divalent biphenyl group substituted or unsubstituted with deuterium, a divalent naphthyl group substituted or unsubstituted with deuterium , A divalent fluorene group substituted or unsubstituted with deuterium, a divalent anthracene group substituted or unsubstituted with deuterium, or a divalent phenanthrene group substituted or unsubstituted with deuterium.
  • L1 and L2 are the same as each other, and are a phenylene group substituted or unsubstituted with deuterium, a divalent biphenyl group substituted or unsubstituted with deuterium, or a divalent naphth substituted or unsubstituted with deuterium. It is a til group.
  • L1 and L2 are different from each other and are a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms.
  • L1 and L2 are different from each other, and are a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent naphthyl group, or a substituted or unsubstituted divalent naphthyl group.
  • L1 and L2 are different from each other, and are a phenylene group substituted or unsubstituted with deuterium, a divalent biphenyl group substituted or unsubstituted with deuterium, and a divalent naphthyl group substituted or unsubstituted with deuterium.
  • L1 and L2 are different from each other, and are a phenylene group substituted or unsubstituted with deuterium, a divalent biphenyl group substituted or unsubstituted with deuterium, or a divalent naphth substituted or unsubstituted with deuterium. It is a til group.
  • L3 is a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms.
  • L3 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent naphthyl group, or a substituted or unsubstituted divalent fluorene group.
  • L3 is a phenylene group substituted or unsubstituted with deuterium, a divalent biphenyl group substituted or unsubstituted with deuterium, a divalent naphthyl group substituted or unsubstituted with deuterium, a substituted or unsubstituted deuterium It is an unsubstituted divalent fluorene group, a divalent anthracene group substituted or unsubstituted with deuterium, or a divalent phenanthrene group substituted or unsubstituted with deuterium.
  • L3 is a phenylene group substituted or unsubstituted with deuterium, a divalent biphenyl group substituted or unsubstituted with deuterium, or a divalent naphthyl group substituted or unsubstituted with deuterium.
  • Ar1 is a substituted or unsubstituted aliphatic hydrocarbon ring group having 3 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; or a condensed ring thereof.
  • Ar1 is a substituted or unsubstituted aliphatic hydrocarbon ring group having 3 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms; or a condensed ring thereof.
  • Ar1 is an aliphatic hydrocarbon ring group having 3 to 30 carbon atoms unsubstituted or substituted with deuterium; an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen; A heteroaryl group having 3 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen; or a condensed ring thereof.
  • Ar1 is an aliphatic hydrocarbon ring group having 3 to 30 carbon atoms unsubstituted or substituted with an aryl group; an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an aryl group; a heteroaryl group having 3 to 30 carbon atoms unsubstituted or substituted with an aryl group; or a condensed ring thereof.
  • Ar1 is an aliphatic hydrocarbon ring group having 3 to 20 carbon atoms unsubstituted or substituted with an aryl group; an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with an aryl group; a heteroaryl group having 3 to 20 carbon atoms unsubstituted or substituted with an aryl group; or a condensed ring thereof.
  • Ar1 is an aliphatic hydrocarbon ring group having 3 to 20 carbon atoms unsubstituted or substituted with an aryl group substituted or unsubstituted with deuterium; an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with an aryl group substituted or unsubstituted with heavy hydrogen; a heteroaryl group having 3 to 20 carbon atoms unsubstituted or substituted with an aryl group unsubstituted or substituted with heavy hydrogen; or a condensed ring thereof.
  • Ar1 is an aliphatic hydrocarbon ring group having 3 to 20 carbon atoms; an aryl group having 6 to 20 carbon atoms; a heteroaryl group having 3 to 20 carbon atoms; or a condensed ring thereof.
  • Ar1 is an aliphatic hydrocarbon ring group having 3 to 30 carbon atoms unsubstituted or substituted with an alkyl group or an aryl group; an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group, an aryl group, or a heteroaryl group; a heteroaryl group having 3 to 30 carbon atoms unsubstituted or substituted with an alkyl group, an aryl group, or a heteroaryl group; or a condensed ring thereof.
  • Ar1 is an aliphatic hydrocarbon ring group having 3 to 20 carbon atoms unsubstituted or substituted with an alkyl group or an aryl group; an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with an alkyl group, an aryl group, or a heteroaryl group; a heteroaryl group having 3 to 20 carbon atoms unsubstituted or substituted with an alkyl group, an aryl group, or a heteroaryl group; or a condensed ring thereof.
  • Ar1 is an aliphatic hydrocarbon ring group having 3 to 30 carbon atoms unsubstituted or substituted with deuterium, an alkyl group or an aryl group; an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen, an alkyl group, an aryl group, or a heteroaryl group; a heteroaryl group having 3 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen, an alkyl group, an aryl group, or a heteroaryl group; or a condensed ring thereof.
  • Ar1 is an adamantyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; A spiroadamanthene fluorene group unsubstituted or substituted with deuterium, an alkyl group or an aryl group; A fluorene group unsubstituted or substituted with heavy hydrogen, an alkyl group or an aryl group; A cyclopentyl group unsubstituted or substituted with a deuterium, an alkyl group or an aryl group; A cyclohexyl group unsubstituted or substituted with heavy hydrogen, an alkyl group or an aryl group; A phenyl group unsubstituted or substituted with heavy hydrogen, an alkyl group, an aryl group, or a heteroaryl group; Biphenyl group unsubstituted or substituted with heavy hydrogen, an alkyl group, an aryl group, or a heteroaryl
  • Ar1 is an adamantyl group unsubstituted or substituted with an alkyl group or an aryl group; A spiroadamanthene fluorene group unsubstituted or substituted with an alkyl group or an aryl group; A fluorene group unsubstituted or substituted with an alkyl group or an aryl group; a cyclopentyl group unsubstituted or substituted with an alkyl group or an aryl group; A cyclohexyl group unsubstituted or substituted with an alkyl group or an aryl group; a phenyl group unsubstituted or substituted with an alkyl group, an aryl group, or a heteroaryl group; a biphenyl group unsubstituted or substituted with an alkyl group, an aryl group, or a heteroaryl group; A terphenyl group unsubstituted or substituted with an alkyl
  • Ar1 is an adamantyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; A spiroadamanthene fluorene group unsubstituted or substituted with deuterium, an alkyl group or an aryl group; A fluorene group unsubstituted or substituted with heavy hydrogen, an alkyl group or an aryl group; A cyclopentyl group unsubstituted or substituted with a deuterium, an alkyl group or an aryl group; A cyclohexyl group unsubstituted or substituted with heavy hydrogen, an alkyl group or an aryl group; A phenyl group unsubstituted or substituted with deuterium or an aryl group; a biphenyl group unsubstituted or substituted with an aryl group; A terphenyl group unsubstituted or substituted with deuterium, an alkyl group
  • Ar1 is an adamantyl group unsubstituted or substituted with an alkyl group or an aryl group; A spiroadamanthene fluorene group unsubstituted or substituted with an alkyl group or an aryl group; A fluorene group unsubstituted or substituted with an alkyl group or an aryl group; a cyclopentyl group unsubstituted or substituted with an alkyl group or an aryl group; A cyclohexyl group unsubstituted or substituted with an alkyl group or an aryl group; A phenyl group unsubstituted or substituted with an aryl group; a biphenyl group unsubstituted or substituted with an aryl group; A terphenyl group unsubstituted or substituted with an aryl group; A naphthyl group unsubstituted or substituted with an aryl group;
  • Ar1 is an adamantyl group unsubstituted or substituted with an aryl group; A spiroadamanthenefluorene group unsubstituted or substituted with an aryl group; A fluorene group unsubstituted or substituted with an alkyl group or an aryl group; A cyclopentyl group unsubstituted or substituted with an aryl group; A cyclohexyl group unsubstituted or substituted with an aryl group; A phenyl group unsubstituted or substituted with an aryl group; a biphenyl group unsubstituted or substituted with an aryl group; A terphenyl group unsubstituted or substituted with an aryl group; A naphthyl group unsubstituted or substituted with an aryl group; an anthracene group unsubstituted or substituted with an aryl group;
  • Ar1 is an adamantyl group; Spiroadamanthene fluorene group; a fluorene group unsubstituted or substituted with a methyl group or a phenyl group; A cyclopentyl group unsubstituted or substituted with a phenyl group; a cyclohexyl group unsubstituted or substituted with a phenyl group or a naphthyl group; A phenyl group unsubstituted or substituted with a phenyl group or a naphthyl group; a biphenyl group unsubstituted or substituted with a phenyl group or a naphthyl group; A terphenyl group unsubstituted or substituted with a phenyl group or a naphthyl group; a naphthyl group unsubstituted or substituted with a phenyl group
  • Ar1 is a substituted or unsubstituted aliphatic hydrocarbon ring group having 3 to 30 carbon atoms; A substituted or unsubstituted aryl group having 10 to 30 carbon atoms; A substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; or a condensed ring thereof.
  • Ar1 is a substituted or unsubstituted aliphatic hydrocarbon ring group having 3 to 20 carbon atoms; A substituted or unsubstituted aryl group having 10 to 20 carbon atoms; A substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms; or a condensed ring thereof.
  • Ar1 is an aliphatic hydrocarbon ring group having 3 to 30 carbon atoms unsubstituted or substituted with deuterium; an aryl group having 10 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen; A heteroaryl group having 3 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen; or a condensed ring thereof.
  • Ar1 is an aliphatic hydrocarbon ring group having 3 to 30 carbon atoms unsubstituted or substituted with an aryl group; an aryl group having 10 to 30 carbon atoms unsubstituted or substituted with an aryl group; a heteroaryl group having 3 to 30 carbon atoms unsubstituted or substituted with an aryl group; or a condensed ring thereof.
  • Ar1 is an aliphatic hydrocarbon ring group having 3 to 20 carbon atoms unsubstituted or substituted with an aryl group; an aryl group having 10 to 20 carbon atoms unsubstituted or substituted with an aryl group; a heteroaryl group having 3 to 20 carbon atoms unsubstituted or substituted with an aryl group; or a condensed ring thereof.
  • Ar1 is an aliphatic hydrocarbon ring group having 3 to 20 carbon atoms unsubstituted or substituted with an aryl group substituted or unsubstituted with deuterium; an aryl group having 10 to 20 carbon atoms unsubstituted or substituted with an aryl group substituted or unsubstituted with heavy hydrogen; a heteroaryl group having 3 to 20 carbon atoms unsubstituted or substituted with an aryl group unsubstituted or substituted with heavy hydrogen; or a condensed ring thereof.
  • Ar1 is an aliphatic hydrocarbon ring group having 3 to 20 carbon atoms; an aryl group having 10 to 20 carbon atoms; a heteroaryl group having 3 to 20 carbon atoms; or a condensed ring thereof.
  • Ar1 is an aliphatic hydrocarbon ring group having 3 to 30 carbon atoms unsubstituted or substituted with an alkyl group or an aryl group; an aryl group having 10 to 30 carbon atoms unsubstituted or substituted with an alkyl group, an aryl group, or a heteroaryl group; a heteroaryl group having 3 to 30 carbon atoms unsubstituted or substituted with an alkyl group, an aryl group, or a heteroaryl group; or a condensed ring thereof.
  • Ar1 is an aliphatic hydrocarbon ring group having 3 to 20 carbon atoms unsubstituted or substituted with an alkyl group or an aryl group; an aryl group having 10 to 20 carbon atoms unsubstituted or substituted with an alkyl group, an aryl group, or a heteroaryl group; a heteroaryl group having 3 to 20 carbon atoms unsubstituted or substituted with an alkyl group, an aryl group, or a heteroaryl group; or a condensed ring thereof.
  • Ar1 is an aliphatic hydrocarbon ring group having 3 to 30 carbon atoms unsubstituted or substituted with deuterium, an alkyl group or an aryl group; an aryl group having 10 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen, an alkyl group, an aryl group, or a heteroaryl group; a heteroaryl group having 3 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen, an alkyl group, an aryl group, or a heteroaryl group; or a condensed ring thereof.
  • Ar1 is a fluorene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; adamantyl group unsubstituted or substituted with heavy hydrogen, an alkyl group or an aryl group; A spiroadamanthene fluorene group unsubstituted or substituted with deuterium, an alkyl group or an aryl group; A cyclopentyl group unsubstituted or substituted with a deuterium, an alkyl group or an aryl group; A cyclohexyl group unsubstituted or substituted with heavy hydrogen, an alkyl group or an aryl group; Biphenyl group unsubstituted or substituted with heavy hydrogen, an alkyl group, an aryl group, or a heteroaryl group; A terphenyl group unsubstituted or substituted with heavy hydrogen, an alkyl group, an aryl group;
  • Ar1 is a fluorene group unsubstituted or substituted with an alkyl group or an aryl group; adamantyl group unsubstituted or substituted with an alkyl group or an aryl group; A spiroadamanthene fluorene group unsubstituted or substituted with an alkyl group or an aryl group; a cyclopentyl group unsubstituted or substituted with an alkyl group or an aryl group; A cyclohexyl group unsubstituted or substituted with an alkyl group or an aryl group; a biphenyl group unsubstituted or substituted with an alkyl group, an aryl group, or a heteroaryl group; A terphenyl group unsubstituted or substituted with an alkyl group, an aryl group, or a heteroaryl group; a naphthyl group unsubsti
  • Ar1 is a fluorene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; adamantyl group unsubstituted or substituted with deuterium or an alkyl group; Spiroadamanthene fluorene group unsubstituted or substituted with deuterium or an alkyl group; A cyclopentyl group unsubstituted or substituted with a deuterium, an alkyl group or an aryl group; A cyclohexyl group unsubstituted or substituted with heavy hydrogen, an alkyl group or an aryl group; a biphenyl group unsubstituted or substituted with an aryl group; A terphenyl group unsubstituted or substituted with heavy hydrogen or an aryl group; A naphthyl group unsubstituted or substituted with deuterium or an aryl group; An
  • Ar1 is a fluorene group unsubstituted or substituted with an alkyl group or an aryl group; adamantyl group unsubstituted or substituted with an alkyl group or an aryl group; A spiroadamanthene fluorene group unsubstituted or substituted with an alkyl group or an aryl group; a cyclopentyl group unsubstituted or substituted with an alkyl group or an aryl group; A cyclohexyl group unsubstituted or substituted with an alkyl group or an aryl group; substituted or unsubstituted with an aryl group; a biphenyl group unsubstituted or substituted with an aryl group; A terphenyl group unsubstituted or substituted with an aryl group; A naphthyl group unsubstituted or substituted with an aryl group;
  • Ar1 is a fluorene group unsubstituted or substituted with an alkyl group or an aryl group; adamantyl group; Spiroadamanthene fluorene group; A cyclopentyl group unsubstituted or substituted with an aryl group; A cyclohexyl group unsubstituted or substituted with an aryl group; a biphenyl group unsubstituted or substituted with an aryl group; A terphenyl group unsubstituted or substituted with an aryl group; A naphthyl group unsubstituted or substituted with an aryl group; an anthracene group unsubstituted or substituted with an aryl group; A phenanthrene group unsubstituted or substituted with an aryl group; A triphenylene group unsubstituted or substituted with an aryl group; A pyren
  • Ar1 is an adamantyl group; Spiroadamanthene fluorene group; a fluorene group unsubstituted or substituted with a methyl group or a phenyl group; A cyclopentyl group unsubstituted or substituted with a phenyl group; a cyclohexyl group unsubstituted or substituted with a phenyl group or a naphthyl group; a biphenyl group unsubstituted or substituted with a phenyl group or a naphthyl group; A terphenyl group unsubstituted or substituted with a phenyl group or a naphthyl group; a naphthyl group unsubstituted or substituted with a phenyl group or a naphthyl group; an anthracene group unsubstituted or substituted with a phen
  • Formula 1 is one of the following structural formulas.
  • Substituents of the compound of Formula 1 may be combined by a method known in the art, and the type, position or number of substituents may be changed according to techniques known in the art.
  • the organic light emitting device includes a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layers contains the aforementioned compound.
  • the organic light emitting device of the present invention may be manufactured by conventional organic light emitting device manufacturing methods and materials, except for forming one or more organic material layers using the above compounds.
  • 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 coating method means spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.
  • the organic material layer of the organic light emitting device of the present invention may have a single-layer structure, or 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 may have a structure including a hole injection layer, a hole transport layer, a hole injection and hole transport layer simultaneously, a light emitting layer, an electron transport layer, an electron injection layer, and the like as organic material layers.
  • the structure of the organic light emitting diode is not limited thereto and may include a smaller number of organic material layers or a larger number of organic material layers.
  • the organic material layer may include at least one of an electron transport layer, an electron injection layer, and a layer that simultaneously injects and transports electrons, and at least one of the layers is represented by Chemical Formula 1. compounds may be included.
  • 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 compound represented by Chemical Formula 1.
  • the organic material layer may include at least one of a hole injection layer, a hole transport layer, and a layer that simultaneously injects and transports holes, and at least one of the layers is represented by Chemical Formula 1. compounds may be included.
  • the organic material layer may include a hole injection layer or a hole transport layer, and the hole transport layer or hole injection layer may include the compound represented by Chemical Formula 1.
  • the first electrode is an anode and the second electrode is a cathode.
  • the first electrode is a cathode
  • the second electrode is an anode
  • the structure of the organic light emitting device of the present invention may have a structure shown in FIGS. 1 and 2, but is not limited thereto.
  • FIG. 1 illustrates a structure of an organic light emitting device in which an anode 2, an organic material layer 3, and a cathode 4 are sequentially stacked on a substrate 1.
  • the compound represented by Chemical Formula 1 may be included in the organic material layer 3.
  • the compound represented by Formula 1 may be included in the hole injection layer 5, the hole transport layer 6, or the electron blocking layer 7. Preferably, it may be included in the electron blocking layer (7).
  • the organic light emitting device uses a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form a metal or conductive metal oxide or an alloy thereof on a substrate. is deposited to form an anode, and from the group consisting of a hole injection layer, a hole transport layer, a hole transport and hole injection layer, a light emitting layer, an electron transport layer, an electron injection layer, and a layer that simultaneously transports and injects electrons thereon.
  • PVD physical vapor deposition
  • a hole injection layer a hole transport layer, a hole transport and hole injection layer
  • a light emitting layer an electron transport layer, an electron injection layer, and a layer that simultaneously transports and injects electrons thereon.
  • an organic material layer including one or more selected layers it can be prepared by depositing a material that can be used as a cathode thereon.
  • an organic light emitting device may be fabricated by sequentially depositing a cathode material, an organic
  • the organic material layer may have a multilayer 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 can be formed by a solvent process other than a deposition method using various polymer materials, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or a thermal transfer method. Can be made in layers.
  • the anode is an electrode for injecting holes, and a material having a high work function is preferable so that holes can be smoothly injected into the organic material layer.
  • the anode 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); combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
  • the cathode is an electrode for injecting electrons
  • the cathode material is a material having a small work function so as to facilitate electron injection into the 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 are multi-layered materials such as LiF/Al or LiO 2 /Al, but are not limited thereto.
  • the hole injection layer is a layer that serves to facilitate the injection of holes from the anode to the light emitting layer
  • the hole injection material is a material that can well inject holes from the anode at a low voltage
  • HOMO highest occupied molecular orbital
  • Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrilehexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene-based organic materials.
  • the hole injection layer may have a thickness of 1 to 150 nm. If the thickness of the hole injection layer is 1 nm or more, there is an advantage in preventing the hole injection characteristic from deteriorating, and if it is 150 nm or less, the thickness of the hole injection layer is too thick to increase the driving voltage to improve the movement of holes. There are advantages to avoiding this.
  • the hole injection layer includes a compound represented by Chemical Formula HI-1, but is not limited thereto.
  • R400 to R402 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 aryl group; A substituted or unsubstituted amine group; A substituted or unsubstituted heteroaryl group; And any one selected from the group consisting of combinations thereof, or bonded to adjacent groups to form a substituted or unsubstituted ring,
  • L402 is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.
  • L402 is a phenyl group.
  • R400 to R402 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; A substituted or unsubstituted heteroaryl group; And any one selected from the group consisting of combinations thereof.
  • R402 is a phenyl group substituted with a carbazole group or an arylamine group; A biphenyl group substituted with a carbazole group or an arylamine group; And any one selected from the group consisting of combinations thereof.
  • R400 and R401 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or combine with adjacent groups to form an aromatic hydrocarbon ring substituted with an alkyl group.
  • R400 and R401 are the same as or different from each other, and each independently represents an aryl group unsubstituted or substituted with an alkyl group.
  • R400 and R401 are the same as or different from each other, and each independently represents a phenyl group or a dimethylfluorene group.
  • Formula HI-1 is selected from the following compounds.
  • the hole injection layer includes a compound represented by Chemical Formula HI-2, but is not limited thereto.
  • X'1 to X'3 are the same as or different from each other, and are each independently hydrogen, deuterium, or a halogen group,
  • R309 to R314 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • x1' to x3' are each an integer of 1 to 4, and when they are 2 or more, the substituents in parentheses are the same as or different from each other.
  • X'1 to X'3 are halogen groups.
  • X'1 to X'3 are F or Cl.
  • X'1 to X'3 are F.
  • R309 to R314 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted amine group.
  • R309 to R314 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or nitrile.
  • R309 to R314 are nitrile groups.
  • Formula HI-2 is represented by the following compound.
  • the hole transport layer may play a role of facilitating hole transport.
  • a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and having high hole mobility is suitable. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated parts.
  • the hole transport layer includes a compound represented by Formula HT-2, but is not limited thereto.
  • R403 to R406 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 aryl group; A substituted or unsubstituted amine group; A substituted or unsubstituted heteroaryl group; And any one selected from the group consisting of combinations thereof, or bonded to adjacent groups to form a substituted or unsubstituted ring,
  • L403 is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group
  • l403 is an integer from 1 to 3, and when l403 is 2 or more, L403 is the same as or different from each other.
  • R403 to R406 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; A substituted or unsubstituted heteroaryl group; And any one selected from the group consisting of combinations thereof.
  • R403 to R406 are the same as or different from each other, and each independently represents an aryl group having 6 to 30 carbon atoms.
  • R403 to R406 are the same as or different from each other, and each independently represents a phenyl group, a biphenyl group, or a naphthyl group.
  • R403 to R406 are the same as or different from each other, and each independently represents a phenyl group.
  • L403 is an arylene group having 6 to 30 carbon atoms or a heteroarylene group having 3 to 30 carbon atoms substituted with an arylene group.
  • L403 is a phenylene group, a divalent biphenyl group, or a divalent carbazole group unsubstituted or substituted with an aryl group.
  • L403 is a divalent carbazole group substituted with a naphthyl group.
  • Formula HT-2 is selected from the following compounds.
  • a hole buffer layer may be additionally provided between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.
  • An electron blocking layer may be provided between the hole transport layer and the light emitting layer.
  • the electron blocking layer the aforementioned spiro compound or a material known in the art may be used.
  • the light emitting layer may emit red, green or blue light and may be made of a phosphorescent material or a fluorescent material.
  • the light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable.
  • 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, benzthiazole and benzimidazole series; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; Polyfluorene, rubrene, etc., 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, benzthiazole and benzimidazole series compounds of the benzoxazole, benzthiazole and benzimidazole series
  • PV poly(p-phenylenevinylene)-based polymers
  • spiro compounds Polyfluorene, rubrene, etc., but are not limited there
  • a host material for the light emitting layer includes a condensed aromatic ring derivative or a compound containing a hetero ring.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc.
  • heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.
  • the host includes a compound represented by Formula H-1 below, but is not limited thereto.
  • At least one of Xx to Xz is N, the others are the same or different from each other and are CH,
  • Ya and Yb are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group,
  • Ht is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group
  • ht is an integer of 1 to 4, and when ht is 2 or more, Ht is the same as or different from each other.
  • the Xx to Xz are N.
  • Ya and Yb are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
  • Ya and Yb are the same as or different from each other, and each independently represents an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 3 to 30 carbon atoms.
  • the Ya and Yb are phenyl groups.
  • Ht is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
  • Ht is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
  • Ht is a carbazole group.
  • Formula H-1 is the compound below, but is not limited thereto.
  • PIQIr (acac) bis (1-phenylisoquinoline) acetylacetonateiridium
  • PQIr (acac) bis (1-phenylquinoline) acetylacetonate iridium
  • PQIr (tris (1-phenylquinoline) iridium) are used as light emitting dopants.
  • a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a fluorescent material such as Alq 3 (tris(8-hydroxyquinolino)aluminum), but is 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) may be used as the light emitting dopant.
  • a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum)
  • Alq3 tris(8-hydroxyquinolino)aluminum
  • a phosphorescent material such as (4,6-F2ppy) 2 Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distryarylene (DSA), Fluorescent materials such as PFO-based polymers and PPV-based polymers may be used, but are not limited thereto.
  • a metal complex may be used as the dopant.
  • an iridium complex may be used as the dopant.
  • the iridium complex used for the dopant may have any one of the following structures, but is not limited thereto.
  • the electron transport layer may serve to facilitate electron transport.
  • the electron transport material a material capable of receiving electrons well from the cathode and transferring them to the light emitting layer, and a material having high electron mobility is suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes containing 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. If the thickness of the electron transport layer is 1 nm or more, there is an advantage in preventing deterioration of electron transport properties, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent an increase in driving voltage to improve electron movement. There are benefits to being able to
  • the electron injection layer may serve to smoothly inject electrons.
  • the electron injecting material has the ability to transport electrons, has an excellent electron injecting effect from the cathode, a light emitting layer or a light emitting material, prevents movement of excitons generated in the light emitting layer to the hole injection layer, and also , compounds having excellent thin film forming ability are preferred.
  • the electron injection and transport layer is a layer that facilitates electron injection and transport. Materials used in the electron injection layer and transport layer described above, or materials capable of receiving electrons from the cathode and transferring them to the light emitting layer may be used.
  • the electron injection and transport layer includes a compound represented by Formula EI-1.
  • At least one of Z11 to Z13 is N and the others are CH,
  • At least one of Z14 to Z16 is N and the others are CH,
  • L701 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar701 to Ar704 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,
  • 1701 is an integer of 1 to 4, and when 1701 is plural, L701 is the same as or different from each other.
  • L701 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
  • L701 is a phenylene group; a biphenylylene group; or a naphthylene group.
  • L701 is a phenylene group; or a naphthylene group.
  • Ar701 to Ar704 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms or a heteroaryl group having 3 to 30 carbon atoms. .
  • Ar701 to Ar704 are phenyl groups.
  • Formula HB-1 is represented by the following compound.
  • 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, and bis(2-methyl-8-quinolinato)(2-naphtolato)gallium. Not limited to this.
  • the hole blocking layer is a layer that blocks holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are not limited thereto.
  • the hole blocking layer includes a compound represented by Formula HB-1.
  • At least one of Z1 to Z3 is N and the others are CH,
  • L601 and L602 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar601 to Ar603 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.
  • L601 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
  • L601 and L602 are the same as or different from each other, and each independently a phenylene group; a biphenylylene group; or a naphthylene group.
  • Ar601 to Ar603 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms or a heteroaryl group having 3 to 30 carbon atoms. .
  • Ar601 to Ar603 are a phenyl group or a triphenylene group.
  • Formula HB-1 is represented by the following compound.
  • the organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a double side emission type depending on the material used.
  • the organic light emitting device of the present invention may be manufactured by conventional organic light emitting device manufacturing methods and materials, except for forming one or more organic material layers using the above compounds.
  • amine4 (15 g, 68.4 mmol), sub1-2 (38.3 g, 136.8 mmol), and sodium tert-butoxide (19.7 g, 205.2 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.7 g, 1.4 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure.
  • amine5 (15 g, 68.4 mmol), sub1-2 (38.3 g, 136.8 mmol), and sodium tert-butoxide (19.7 g, 205.2 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.7 g, 1.4 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure.
  • amine15 (15 g, 68.4 mmol), sub2-7 (27.9 g, 136.8 mmol), and sodium tert-butoxide (19.7 g, 205.2 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.7 g, 1.4 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure.
  • amine24 (15 g, 68.4 mmol), sub3-3 (27.9 g, 136.8 mmol), and sodium tert-butoxide (19.7 g, 205.2 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.7 g, 1.4 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure.
  • amine5 (15 g, 68.4 mmol), sub1-2 (19.1 g, 68.4 mmol), and sodium tert-butoxide (9.9 g, 102.6 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.7 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure.
  • compound 37_P-1 15 g, 29.3 mmol
  • sub1-1 8.2 g, 29.3 mmol
  • sodium tert-butoxide 4.2 g, 43.9 mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.1 g, 0.3 mmol
  • compound 52_P-1 15 g, 38.8 mmol
  • sub3-3 7.9 g, 38.8 mmol
  • sodium tert-butoxide 5.6 g, 58.2 mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.2 g, 0.4 mmol
  • compound 56_P-1 15 g, 38.8 mmol
  • sub4-4 7.9 g, 38.8 mmol
  • sodium tert-butoxide 5.6 g, 58.2 mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.2 g, 0.4 mmol
  • compound 57_P-1 15 g, 38.8 mmol
  • sub3-7 7.9 g, 38.8 mmol
  • sodium tert-butoxide 5.6 g, 58.2 mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.2 g, 0.4 mmol
  • compound 61_P-1 15 g, 38.8 mmol
  • sub4-4 7.9 g, 38.8 mmol
  • sodium tert-butoxide 5.6 g, 58.2 mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.2 g, 0.4 mmol
  • compound 65_P-1 15 g, 38.8 mmol
  • sub5-1 (10.9 g, 38.8 mmol)
  • sodium tert-butoxide 5.6 g, 58.2 mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.2 g, 0.4 mmol
  • a glass substrate coated with ITO (indium tin oxide) to a thickness of 1,000 ⁇ was put in distilled water in which detergent was dissolved and washed with ultrasonic waves.
  • a Fischer Co. product was used as the detergent
  • distilled water filtered through a second filter of a Millipore Co. product was used as the distilled water.
  • ultrasonic cleaning was performed for 10 minutes.
  • ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, dried, and transported to a plasma cleaner.
  • solvents such as isopropyl alcohol, acetone, and methanol
  • the following compound HI-1 was formed to a thickness of 1150 ⁇ as a hole injection layer on the prepared ITO transparent electrode, but the following compound A-1 was p-doped at a concentration of 1.5%.
  • the following HT-1 compound was vacuum deposited to form a hole transport layer having a thickness of 800 ⁇ .
  • an electron blocking layer was formed on the hole transport layer by vacuum depositing Compound 1 to a film thickness of 150 ⁇ .
  • the following RH-1 compound as a host and the following Dp-7 compound as a dopant were vacuum deposited at a weight ratio of 98:2 to form a red light emitting layer having a thickness of 400 ⁇ .
  • a hole blocking layer was formed on the light emitting layer by vacuum depositing the following HB-1 compound to a film thickness of 30 ⁇ . Subsequently, the following ET-1 compound and the following LiQ compound were vacuum deposited at a weight ratio of 2:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 300 ⁇ .
  • a negative electrode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 ⁇ and aluminum to a thickness of 1,000 ⁇ on the electron injection and transport layer.
  • the deposition rate of the organic material was maintained at 0.4 to 0.7 ⁇ /sec
  • the deposition rate of lithium fluoride on the negative electrode was 0.3 ⁇ /sec
  • the deposition rate of aluminum was 2 ⁇ /sec
  • the vacuum level during deposition was 2x10 -7 to Maintaining 5x10 -6 torr, an organic light emitting device was fabricated.
  • An organic light emitting device was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of Compound 1 in the organic light emitting device of Example 1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1, except that the compound shown in Table 1 was used instead of Compound 1 in the organic light emitting device of Example 1.
  • the lifetime T95 means the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.
  • the red organic light emitting device of Example 1 uses materials widely used in the prior art, and has a structure in which Dp-7 is used as a dopant for the red light emitting layer.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Organic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un composé de formule chimique 1 et un dispositif électroluminescent organique le comprenant.
PCT/KR2022/017781 2021-11-12 2022-11-11 Composé et dispositif électroluminescent organique le comprenant WO2023085860A1 (fr)

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KR20170005853A (ko) * 2014-05-14 2017-01-16 프레지던트 앤드 펠로우즈 오브 하바드 칼리지 유기 발광 다이오드 물질
KR20170030145A (ko) * 2015-09-08 2017-03-17 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20180073222A (ko) * 2016-12-22 2018-07-02 삼성전자주식회사 유기금속 화합물, 이를 포함한 유기 발광 소자 및 이를 포함한 진단용 조성물
CN110885338A (zh) * 2018-09-11 2020-03-17 江苏三月光电科技有限公司 一种以三芳胺为核心的有机化合物及其制备方法和其应用
KR102284600B1 (ko) * 2021-01-28 2021-08-02 (주)랩토 유기 금속 착물 및 이를 포함한 유기 전계발광 소자

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2712222C2 (ru) 2015-03-25 2020-01-27 Нэшнл Кэнсер Сентер Терапевтическое средство против рака желчных протоков

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20170005853A (ko) * 2014-05-14 2017-01-16 프레지던트 앤드 펠로우즈 오브 하바드 칼리지 유기 발광 다이오드 물질
KR20170030145A (ko) * 2015-09-08 2017-03-17 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20180073222A (ko) * 2016-12-22 2018-07-02 삼성전자주식회사 유기금속 화합물, 이를 포함한 유기 발광 소자 및 이를 포함한 진단용 조성물
CN110885338A (zh) * 2018-09-11 2020-03-17 江苏三月光电科技有限公司 一种以三芳胺为核心的有机化合物及其制备方法和其应用
KR102284600B1 (ko) * 2021-01-28 2021-08-02 (주)랩토 유기 금속 착물 및 이를 포함한 유기 전계발광 소자

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