WO2023244000A1 - Composé et élément électroluminescent organique le comprenant - Google Patents

Composé et élément électroluminescent organique le comprenant Download PDF

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WO2023244000A1
WO2023244000A1 PCT/KR2023/008159 KR2023008159W WO2023244000A1 WO 2023244000 A1 WO2023244000 A1 WO 2023244000A1 KR 2023008159 W KR2023008159 W KR 2023008159W WO 2023244000 A1 WO2023244000 A1 WO 2023244000A1
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문현진
김민준
김주호
이성재
홍성길
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주식회사 엘지화학
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    • C07D209/56—Ring systems containing three or more rings
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    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
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    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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    • 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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Definitions

  • This specification relates to compounds and organic light-emitting devices containing 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.
  • Organic light-emitting devices can be broadly divided into two types according to their operating principles as follows. First, excitons are formed in the organic layer by photons flowing into the device from an external light source, these excitons are separated into electrons and holes, and these electrons and holes are transferred to different electrodes and used as current sources (voltage sources). It is a type of light emitting device. The second type is a light-emitting device that applies voltage or current to two or more electrodes to inject holes and/or electrons into the organic semiconductor material layer forming the interface with the electrodes, and operates by the injected electrons and holes.
  • organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials.
  • Organic light-emitting devices that utilize the organic light-emitting phenomenon usually have a structure including an anode, a cathode, and an organic material layer between them.
  • the organic material layer is often composed of a multi-layer structure composed of different materials to increase the efficiency and stability of the organic light-emitting device. For example, it consists of 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. You can lose.
  • this organic light-emitting device when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic material layer. When the injected holes and electrons meet, an exciton is formed, and this exciton is When it falls back to the ground state, it glows.
  • These organic light-emitting devices are known to have characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast.
  • Materials used as organic layers in organic light-emitting devices can 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 function.
  • charge transport materials such as hole injection materials, hole transport materials, electron suppression materials, electron transport materials, and electron injection materials, depending on their function.
  • color of the light there are blue, green, and red light emitting materials, as well as yellow and orange light emitting materials needed to achieve better natural colors.
  • a host/dopant system can be used as a luminescent material.
  • the principle is that when a small amount of dopant, which has a smaller energy band gap and higher luminous efficiency than the host that mainly constitutes the light-emitting layer, is mixed into the light-emitting layer, excitons generated in the host are transported to the dopant, producing highly efficient light.
  • the wavelength of the host moves to the wavelength of the dopant, light of the desired wavelength can be obtained depending on the type of dopant used.
  • the materials that make up the organic layer within the device such as hole injection material, hole transport material, light-emitting material, electron suppressor material, electron transport material, and electron injection material, must be stable and efficient materials. As this is supported by , the development of new materials continues to be required.
  • An exemplary embodiment of the present specification provides a compound of Formula 1 below.
  • L is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
  • Ar1 is hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • a first electrode a second electrode provided opposite the first electrode; and an organic light emitting device including one or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the above-mentioned compounds.
  • the compound of the present invention can be used as a material for the organic layer of an organic light-emitting device.
  • an organic light emitting device including the compound of the present invention an organic light emitting device with high efficiency, low voltage, and long lifespan characteristics can be obtained, and the compound of the present invention can be used as a hole injection layer, hole transport layer, or electron block of the organic light emitting device.
  • an organic light emitting device with low voltage, high efficiency, and long lifespan characteristics can be manufactured.
  • the compound of Formula 1 has a structure in which carbazole is substituted in the meta or ortho position on the benzene ring, and the conjugation is broken compared to substances containing a para structure or a meta + meta structure. Therefore, the band gap is large, so it is relatively easy to control the HOMO and LUMO values depending on the type of substituent. In addition, it has less steric hindrance than the ortho+ortho structure and has appropriate hole mobility.
  • the driving voltage of the organic electronic device can be lowered and the lifespan can be further improved.
  • FIG. 1 and 2 show examples of organic light-emitting devices according to the present invention.
  • substitution means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent.
  • the position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and if two or more substituents are substituted. , two or more substituents may be the same or different from each other.
  • substituted or unsubstituted refers to deuterium; halogen group; Cyano group (-CN); silyl group; boron group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; and substituted or unsubstituted heterocyclic groups, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituents.
  • a substituent group in which two or more substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are connected.
  • halogen groups include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).
  • the silyl group may be represented by the formula -SiY1Y2Y3, where Y1, Y2, and Y3 are each hydrogen; Substituted or unsubstituted alkyl group; Or, it may be a substituted or unsubstituted aryl group.
  • the silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. No.
  • the boron group may be represented by the chemical formula -BY4Y5, where Y4 and Y5 are each hydrogen; Substituted or unsubstituted alkyl group; Or, it may be a substituted or unsubstituted aryl group.
  • the boron group specifically includes, but is not limited to, dimethyl boron group, diethyl boron group, t-butylmethyl boron group, diphenyl boron group, and phenyl boron group.
  • the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the carbon number of the alkyl group is 1 to 30. According to another embodiment, the carbon number of the alkyl group is 1 to 20. According to another embodiment, the carbon number of the alkyl group is 1 to 10. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, and octyl groups.
  • the arylalkyl group refers to an alkyl group substituted with an aryl group.
  • the number of carbon atoms is not particularly limited, but according to one embodiment, the carbon number of the alkyl group is 1 to 30, and the carbon number of the aryl group substituted by the alkyl group is 6 to 30.
  • the amine group is -NH 2 ; Alkylamine group; N-alkylarylamine group; Arylamine group; N-arylheteroarylamine group; It may be selected from the group consisting of N-alkylheteroarylamine group and heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • amine groups include methylamine groups; dimethylamine group; ethylamine group; diethylamine group; phenylamine group; Naphthylamine group; Biphenylamine group; Anthracenylamine group; 9-methylanthracenylamine group; Diphenylamine group; Ditolylamine group; N-phenyltolylamine group; Triphenylamine group; N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenylterphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group, etc.
  • N-alkylarylamine group refers to an amine group in which the N of the amine group is substituted with an alkyl group and an aryl group.
  • N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted at the N of the amine group.
  • N-alkylheteroarylamine group refers to an amine group in which the N of the amine group is substituted with an alkyl group and a heteroaryl group.
  • alkyl groups in the alkylamine group, N-arylalkylamine group, alkylthioxy group, alkylsulfoxy group, and N-alkylheteroarylamine group are the same as examples of the alkyl groups described above.
  • the alkylthioxy group includes methylthioxy group; ethylthioxy group; tert-butylthioxy group; hexylthioxy group; Octylthioxy groups, etc.
  • examples of alkylsulfoxy groups include mesyl; ethyl sulfoxy group; Propyl alcohol oxygen group; Butyl sulfoxy group, etc., but is not limited thereto.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specifically, it includes cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, etc., but is 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.
  • the aryl group has 6 to 30 carbon atoms.
  • the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a monocyclic aryl group, such as a phenyl group, biphenyl group, or terphenyl 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, etc., but is not limited thereto.
  • the heteroaryl group is a cyclic 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 it is preferably 2 to 60 carbon atoms. According to one embodiment, the carbon number of the heterocyclic group is 2 to 30.
  • heterocyclic groups include pyridine group, pyrrole group, pyrimidine group, pyridazinyl group, furan group, thiophene group, imidazole group, pyrazole group, dibenzofuran group, dibenzothiophene group, carbazole group, etc. However, it is not limited to these.
  • the meaning of “adjacent” in “joining with adjacent groups to form a ring” is the same as described above, and the “ring” refers to a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocycle.
  • the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and, except for the non-monovalent ones, the cycloalkyl group, the aryl group, and combinations thereof.
  • hydrocarbon ring is benzene, cyclohexane, adamantane, bicyclo[2.2.1]heptane, bicyclo[2.2.1]octane, tetrahydronaphthalene, tetrahydroanthracene, 1,2, These include, but are not limited to, 3,4-tetrahydro-1,4-methanonaphthalene and 1,2,3,4-tetrahydro-1,4-ethanonaphthalene.
  • the arylene group is the same as defined for the aryl group above, except that it is a divalent group.
  • heteroarylene group is the same as defined for the heteroaryl group above, except that it is a divalent group.
  • L 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.
  • L is a direct bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms.
  • L is a direct bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 15 carbon atoms.
  • L is a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
  • L is a direct bond, or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.
  • L is a direct bond, or a substituted or unsubstituted arylene group having 6 to 15 carbon atoms.
  • L is a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent terphenyl group, or a substituted or unsubstituted divalent Naphthyl group, substituted or unsubstituted divalent pyrene group, substituted or unsubstituted divalent anthracene group, substituted or unsubstituted divalent phenanthrene group, substituted or unsubstituted divalent triphenylene group, substituted or unsubstituted It is a divalent fluorene group, or a substituted or unsubstituted divalent fluoranthene group.
  • L is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
  • L is a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.
  • L is a substituted or unsubstituted arylene group having 6 to 15 carbon atoms.
  • L is a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent terphenyl group, a substituted or unsubstituted divalent naphthyl group, Substituted or unsubstituted divalent pyrene group, substituted or unsubstituted divalent anthracene group, substituted or unsubstituted divalent phenanthrene group, substituted or unsubstituted divalent triphenylene group, substituted or unsubstituted divalent flu It is an orene group, or a substituted or unsubstituted divalent fluoranthene group.
  • L is a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent terphenyl group, or a substituted or unsubstituted divalent naphthyl group.
  • L is a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, or a substituted or unsubstituted divalent naphthyl group.
  • L is a direct bond or a phenylene group.
  • L is a substituted or unsubstituted divalent biphenyl group, or a substituted or unsubstituted divalent naphthyl group.
  • L is a direct bond
  • L is a phenylene group.
  • L is a divalent biphenyl group.
  • L is a divalent naphthyl group.
  • Formula 1 is any one of the following Formulas 1-1 to 1-4.
  • a is an integer from 0 to 3
  • b is an integer from 1 to 3.
  • Ar is hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • Ar is hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or It is an unsubstituted heteroaryl group having 3 to 30 carbon atoms.
  • Ar is hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or It is an unsubstituted heteroaryl group having 3 to 20 carbon atoms.
  • Ar is hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, or a substituted or It is an unsubstituted heteroaryl group having 3 to 15 carbon atoms.
  • Ar is hydrogen, deuterium, a halogen group, a nitrile group, an alkyl group with 1 to 10 carbon atoms, an aryl group with 6 to 30 carbon atoms, or a heteroaryl group with 3 to 30 carbon atoms.
  • Ar is hydrogen, deuterium, a halogen group, a nitrile group, an alkyl group with 1 to 10 carbon atoms, an aryl group with 6 to 20 carbon atoms, or a heteroaryl group with 3 to 20 carbon atoms.
  • Ar is hydrogen, deuterium, a halogen group, a nitrile group, an alkyl group with 1 to 10 carbon atoms, an aryl group with 6 to 15 carbon atoms, or a heteroaryl group with 3 to 15 carbon atoms.
  • Ar is hydrogen, deuterium, a halogen group, a nitrile group, an alkyl group having 1 to 10 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms. am.
  • Ar is hydrogen, deuterium, a halogen group, a nitrile group, an alkyl group having 1 to 10 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms. am.
  • Ar is hydrogen, deuterium, a halogen group, a nitrile group, an alkyl group having 1 to 10 carbon atoms, a polycyclic aryl group having 10 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.
  • Ar is hydrogen, deuterium, a halogen group, a nitrile group, an alkyl group with 1 to 10 carbon atoms, a polycyclic aryl group with 10 to 20 carbon atoms, or a heteroaryl group with 3 to 20 carbon atoms.
  • Ar is a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted anthracenyl group; Substituted or unsubstituted phenanthryl group; Substituted or unsubstituted pyrenyl group; Substituted or unsubstituted perylenyl group; Substituted or unsubstituted chrysenyl group; Substituted or unsubstituted fluorenyl group; Or a substituted or unsubstituted naphthyl group.
  • Ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrene group, or a substituted or unsubstituted diphenyl group. It is a benzofuran group, or a substituted or unsubstituted dibenzothiophene group.
  • Ar is a phenyl group substituted or unsubstituted with an aryl group, a biphenyl group substituted or unsubstituted with an aryl group, a naphthyl group substituted or unsubstituted with an aryl group, or a phenant group substituted or unsubstituted with an aryl group. It is a dibenzofuran group substituted or unsubstituted with a lene group, an aryl group, or a dibenzothiophene group substituted or unsubstituted with an aryl group.
  • Ar is a phenyl group substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms, a biphenyl group substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or An unsubstituted naphthyl group, a phenanthrene group substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms, a dibenzofuran group substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms, or substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms. It is a ringed dibenzothiophene group.
  • Ar is a phenyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms, a biphenyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or An unsubstituted naphthyl group, a phenanthrene group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms, a dibenzofuran group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms, or substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms. It is a ringed dibenzothiophene group.
  • Ar is a phenyl group, a biphenyl group, a naphthyl group substituted or unsubstituted by a phenyl group, a phenanthrene group, a dibenzofuran group, or a dibenzothiophene group.
  • Formula 1 is one of the following structural formulas.
  • Substituents of the compound of Formula 1 may be combined by methods 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 opposite the first electrode; And an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer contains the above-described compound.
  • the organic light emitting device of the present invention can be manufactured using conventional organic light emitting device manufacturing methods and materials, except that one or more organic material layers are formed using the above-described compounds.
  • the compound may be formed into 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 refers to 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 layer that simultaneously performs hole injection and hole transport, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer.
  • 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 one or more of an electron transport layer, an electron injection layer, and a layer that performs both electron injection and electron transport, and one or more of the layers is represented by the formula (1) It may contain compounds.
  • the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include the compound represented by Formula 1.
  • the organic material layer may include one or more layers among a hole injection layer, a hole transport layer, and a layer that performs both hole injection and hole transport, and one or more of the layers is represented by the formula (1) It may contain compounds.
  • 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 compound represented by Formula 1 above.
  • the organic material layer includes an electron blocking layer, and the electron blocking layer may include a compound represented by Formula 1 above.
  • the organic material layer includes a hole transport layer or an electron blocking layer, and the hole transport layer or the electron blocking layer may include the compound.
  • the organic layer may include one or more of a hole injection layer, a hole transport layer, a layer that simultaneously performs hole injection and hole transport, and an electron suppression layer, and one or more of the layers may be It may include a compound represented by Formula 1.
  • the organic material layer may include a hole injection layer or a hole transport layer, and the hole transport layer or the hole injection layer may include the compound represented by Formula 1.
  • an additional electron blocking layer may be included between the hole transport layer and the light emitting layer.
  • the hole transport layer and the electron blocking layer may be in contact with each other, and the electron blocking layer includes the compound of Formula 1 above.
  • the light emitting layer and the electron blocking layer may be in contact with each other, and the electron blocking layer includes the compound of Formula 1 above.
  • a hole injection layer or a hole transport layer may be additionally provided between the electron blocking layer and the anode.
  • the hole transport layer and the electron blocking layer are in contact with each other.
  • the first electrode is an anode and the second electrode is a cathode.
  • the first electrode is a cathode and the second electrode is an anode.
  • the structure of the organic light emitting device of the present invention may have the same structure as shown in Figure 1 or Figure 2, but is not limited thereto.
  • Figure 1 illustrates the structure of an organic light-emitting device in which a first electrode 2, an organic material layer 3, and a second electrode 4 are sequentially stacked on a substrate 1.
  • the compound represented by Formula 1 may be included in the organic layer 3.
  • FIG. 2 shows a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 8, a hole blocking layer 9, an electron injection layer and
  • the structure of an organic light emitting device in which the transport layer 10 and the second electrode 4 are sequentially stacked is illustrated.
  • the compound represented by Formula 1 may be included in the hole transport layer 6 or the electron suppression layer 7.
  • the organic light emitting device deposits a metal, a conductive metal oxide, or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation.
  • PVD physical vapor deposition
  • An anode is formed by depositing a layer on which a hole injection layer, a hole transport layer, a layer that simultaneously performs hole transport and hole injection, a light emitting layer, an electron transport layer, an electron injection layer, and a layer that performs both electron transport and electron injection are selected from the group consisting of It can be manufactured by forming an organic material layer containing one or more selected layers and then depositing a material that can be used as a cathode thereon.
  • an organic light-emitting device can also be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, but is not limited to this and may have a single-layer structure.
  • the organic material layer uses a variety of polymer materials to form a smaller number of layers by using a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be manufactured in layers.
  • the anode is an electrode that injects holes
  • the anode material is generally preferably a material with a large work function to facilitate hole injection into the organic layer.
  • anode materials 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); 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 are included, but are not limited to these.
  • the cathode is an electrode that injects electrons
  • the cathode material is preferably a material with a low work function to facilitate electron injection into the organic layer.
  • Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof;
  • There are multi-layer structure materials such as LiF/Al or LiO 2 /Al, but they are not limited to these.
  • the hole injection layer is a layer that serves to facilitate the injection of holes from the anode to the light emitting layer, and the hole injection material is a material that can well inject holes from the anode at a low voltage.
  • HOMO highest occupied
  • the molecular orbital is between the work function of the anode material and the HOMO of the surrounding organic layer.
  • hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrilehexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances.
  • the thickness of the hole injection layer may be 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 characteristics from deteriorating, and if it is 150 nm or less, the thickness of the hole injection layer is so thick that the driving voltage is increased to improve the movement of holes. There is an advantage to preventing this.
  • the hole injection layer includes, but is not limited to, a compound represented by the following formula HI-1.
  • L301 to L303 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • R301 to R303 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; and combinations thereof, or is combined with adjacent groups to form a substituted or unsubstituted ring.
  • R301 to R303 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of combinations thereof.
  • R301 to R303 are the same as or different from each other, and are each independently a substituted or unsubstituted carbazole group; Substituted or unsubstituted phenyl group; Biphenyl group; Or it is a fluorene group substituted or unsubstituted with a methyl group.
  • L301 to L303 are the same or different from each other and are each independently directly bonded; Arylene group; Or it is a heteroarylene group.
  • L301 to L303 are the same or different from each other and are each independently directly bonded; Or it is phenylene.
  • the formula HI-1 is represented by the following compound.
  • the hole transport layer may play a role in facilitating the transport of holes.
  • the hole transport material is a material that can transport holes from the anode or hole injection layer and transfer them to the light emitting layer, and a material with high mobility for holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions, but are not limited to these.
  • An additional hole buffer layer may be provided between the hole injection layer and the hole transport layer, and may include hole injection or transport materials known in the art.
  • the hole transport layer when the hole transport layer includes a material other than Chemical Formula 1, it includes a compound represented by the following Chemical Formula HT-2, but is not limited thereto.
  • R403 to R406 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted amine group; Substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of combinations thereof, or by combining with 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 if l403 is 2 or more, L403 is the same 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; Substituted or unsubstituted amine group; 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 divalent carbazole group unsubstituted or substituted with a phenylene group, a divalent biphenyl group, or an aryl group.
  • L403 is a phenylene group or a divalent carbazole group substituted with a phenyl group.
  • the formula HT-2 is the following compound.
  • An electron blocking layer may be provided between the hole transport layer and the light emitting layer.
  • the electron suppressing layer may be made of the spiro compound described above or a material known in the art.
  • the electron blocking layer when the electron blocking layer includes a material other than Formula 1, it includes a compound represented by the following Formula EB-1, but is not limited thereto.
  • R318 to R320 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of combinations thereof, or by combining with adjacent groups to form a substituted or unsubstituted ring,
  • r318 is an integer from 1 to 5, and when r318 is 2 or more, 2 or more of R318 are the same or different from each other,
  • r319 is an integer of 1 to 5, and when r319 is 2 or more, 2 or more R319s are the same or different from each other.
  • R318 is a substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of combinations thereof.
  • R318 is a carbazole group; phenyl group; Biphenyl group; Or triphenylene.
  • R318 is triphenylene
  • R319 and R320 are the same or different from each other and are each independently a substituted or unsubstituted aryl group, or are combined with adjacent groups to form an aromatic hydrocarbon ring substituted with an alkyl group.
  • R319 and R320 are the same or different from each other and are each independently a phenyl group, or are combined with adjacent groups to form an indene substituted with a methyl group.
  • R319 and R320 are phenyl groups.
  • the formula EB-1 is represented by the following compound.
  • 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 range by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV) series polymer; Spiro compounds; Polyfluorene, rubrene, etc., but are not limited to these.
  • Alq 3 8-hydroxy-quinoline aluminum complex
  • Carbazole-based compounds dimerized styryl compounds
  • BAlq 10-hydroxybenzoquinoline-metal compound
  • Compounds of the benzoxazole, benzthiazole and benzimidazole series Compounds of the benzoxazole, benzthiazole and benzimidazole series
  • Poly(p-phenylenevinylene) (PPV) series polymer Poly(p-phenylenevinylene) (PPV) series polymer
  • Host materials for the light-emitting layer include condensed aromatic ring derivatives or heterocycle-containing compounds.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type compounds. These include, but are not limited to, furan compounds and pyrimidine derivatives.
  • the host includes, but is not limited to, a compound represented by the following formula H-1.
  • L20 and L21 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
  • Ar20 and Ar21 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • R201 is hydrogen; heavy hydrogen; halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • r201 is an integer from 1 to 8, and when r201 is 2 or more, 2 or more R201 are the same or different from each other.
  • L20 and L21 are the same or different from each other and are each independently directly bonded; A monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; Or it is a monocyclic or polycyclic divalent heterocyclic group having 2 to 30 carbon atoms.
  • L20 and L21 are the same or different from each other and are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium; A biphenylylene group substituted or unsubstituted with deuterium; Naphthylene group substituted or unsubstituted with deuterium; divalent dibenzofuran group; Or it is a divalent dibenzothiophene group.
  • Ar20 and Ar21 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
  • Ar20 and Ar21 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted monocyclic to 4-ring heterocyclic group having 6 to 20 carbon atoms.
  • Ar20 and Ar21 are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A biphenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Naphthyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A thiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Dibenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Naphthobenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6
  • Ar20 and Ar21 are the same as or different from each other, and are each independently a phenyl group substituted or unsubstituted with deuterium; Biphenyl group substituted or unsubstituted with deuterium; Terphenyl group; Naphthyl group substituted or unsubstituted with deuterium; A thiophene group substituted or unsubstituted with a phenyl group; phenanthrene group; Dibenzofuran group; Naphthobenzofuran group; Dibenzothiophene group; Or it is a naphthobenzothiophene group.
  • Ar20 and Ar21 are naphthyl groups.
  • Ar20 and Ar21 are the same as or different from each other, and each independently represents a 1-naphthyl group or a 2-naphthyl group.
  • R201 is hydrogen
  • the formula H-1 is represented by the following compound.
  • the light-emitting dopants include PIQIr(acac)(bis(1-phenylsoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), and PQIr(tris(1-phenylquinoline)iridium).
  • phosphorescent materials such as PtOEP (octaethylporphyrin platinum), or fluorescent materials such as Alq 3 (tris(8-hydroxyquinolino)aluminum) may be used, but are not limited to these.
  • a phosphor 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 phosphor such as Ir(ppy) 3 (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum)
  • Alq3 tris(8-hydroxyquinolino)aluminum
  • the light-emitting dopant may be a phosphorescent material such as (4,6-F2ppy) 2 Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), Fluorescent materials such as PFO-based polymers and PPV-based polymers may be used, but are not limited to these.
  • the dopant includes, but is not limited to, a compound represented by the following formula D-1.
  • T1 to T6 are the same or different from each other, and are each independently hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • t5 and t6 are each integers from 1 to 4,
  • t5 is 2 or more, the 2 or more T5 are the same or different from each other,
  • the 2 or more T6s are the same or different from each other.
  • T1 to T6 are the same as or different from each other, and are each independently hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • T1 to T6 are the same as or different from each other, and are each independently hydrogen; A straight or branched alkyl group having 1 to 30 carbon atoms; a nitrile group, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Or it is a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms that is substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms.
  • T1 to T6 are the same as or different from each other, and are each independently hydrogen; A phenyl group substituted with a methyl group; Or it is a dibenzofuran group substituted with a terbutyl group.
  • Formula D-1 is represented by the following compound.
  • a hole blocking layer may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used.
  • the electron transport layer may play a role in facilitating the transport of electrons.
  • the electron transport material is a material that can easily inject electrons from the cathode and transfer them to the light-emitting layer, and a material with high mobility for electrons is suitable. Specific examples include Al complex of 8-hydroxyquinoline; Complex containing Alq 3 ; organic radical compounds; Hydroxyflavone-metal complexes, etc., but are not limited to these.
  • the thickness of the electron transport layer may be 1 to 50 nm.
  • the thickness of the electron transport layer is 1 nm or more, there is an advantage in preventing the electron transport characteristics from deteriorating, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the driving voltage from increasing to improve the movement of electrons. There are benefits to this.
  • the electron injection layer may serve to facilitate injection of electrons.
  • the electron injection material has the ability to transport electrons, has an excellent electron injection 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 has an excellent electron injection effect from the cathode to the light emitting layer or light emitting material. , Compounds with excellent thin film forming ability are preferred.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, metals.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, metals.
  • fluorenone anthraquinodimethane
  • diphenoquinone diphenoquinone
  • thiopyran dioxide oxazole
  • oxadiazole triazole
  • imidazole imidazole
  • perylenetetracarboxylic acid
  • the electron injection and transport layer includes, but is not limited to, a compound of the following formula ET-1.
  • At least one of Z11 to Z13 is N, the others are CH,
  • L601 is directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar601 to Ar603 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • l601 is an integer from 1 to 5, and when l601 is 2 or more, the 2 or more L601s are the same or different from each other.
  • L601 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
  • L601 is a phenylene group; Biphenylylene group; Or it is a naphthylene group.
  • Ar601 and Ar602 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • Ar601 and Ar602 are phenyl groups.
  • Ar603 is a heteroaryl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • Ar603 is a heteroaryl group substituted or unsubstituted with a phenyl group.
  • Ar603 is a triazine group substituted or unsubstituted by a phenyl group.
  • the formula ET-1 is represented by the following compound.
  • the electron injection and transport layer includes a compound of the formula ET-1 and a metal complex.
  • metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, Tris(2-methyl-8-hydroxyquinolinato)aluminum, Tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato) aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato) gallium, etc. It is not limited to this.
  • the hole blocking layer is a layer that prevents holes from reaching the cathode, and can generally be formed under the same conditions as the electron injection layer. Specifically, it includes oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, etc., but is not limited thereto.
  • the hole blocking layer includes, but is not limited to, a compound of the following formula HB-1.
  • At least one of Z101 to Z103 is N, the others are CH,
  • L61 is directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar61 to Ar63 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • L61 is a direct bond, or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
  • L61 is a direct bond; phenylene group; Biphenylylene group; Or it is a naphthylene group.
  • Ar61 and Ar62 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • Ar61 and Ar62 are biphenyl groups.
  • Ar63 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • Ar63 is spirobifluorene.
  • the formula HB-1 is represented by the following compound.
  • the organic light emitting device may be a front emitting type, a back emitting type, or a double-sided emitting type depending on the material used.
  • the organic light emitting device of the present invention can be manufactured using conventional organic light emitting device manufacturing methods and materials, except that one or more organic material layers are formed using the above-described compounds.
  • a glass substrate coated with a thin film of ITO (indium tin oxide) with a thickness of 1,000 ⁇ was placed in distilled water with a detergent dissolved in it and washed ultrasonically.
  • a detergent manufactured by Fischer Co. was used, and distilled water filtered secondarily using a filter manufactured by Millipore Co. was used as distilled water.
  • ultrasonic cleaning was repeated twice with distilled water for 10 minutes.
  • the compounds of the following compound HI1 and the following compound HI2 were thermally vacuum deposited to a thickness of 100 ⁇ at a ratio of 98:2 (molar ratio) to form a hole injection layer.
  • a hole transport layer was formed by vacuum depositing a compound (1150 ⁇ ) represented by the following chemical formula HT1 on the hole injection layer.
  • Compound 1 was vacuum deposited to a film thickness of 50 ⁇ on the hole transport layer to form an electron blocking layer.
  • a compound represented by the following formula BH and a compound represented by the following formula BD were vacuum deposited on the electron blocking layer at a film thickness of 200 ⁇ at a weight ratio of 25:1 to form a light emitting layer.
  • a hole blocking layer was formed by vacuum depositing a compound represented by the following chemical formula HB1 with a film thickness of 50 ⁇ on the light emitting layer.
  • a compound represented by the following formula ET1 and a compound represented by the following formula LiQ were vacuum deposited on the hole blocking layer at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 310 ⁇ .
  • a cathode 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.
  • LiF lithium fluoride
  • the deposition rate of organic matter was maintained at 0.4 ⁇ 0.7 ⁇ /sec
  • the deposition rate of lithium fluoride of the cathode was maintained at 0.3 ⁇ /sec
  • the deposition rate of aluminum was maintained at 2 ⁇ /sec
  • the vacuum degree during deposition was 2X10 -7 ⁇
  • An organic light emitting device was manufactured by maintaining 5X10 -6 torr.
  • An organic light emitting device was manufactured in the same manner as Example 1-1, except that the compounds listed in Table 1 below were used instead of Compound 1.
  • An organic light emitting device was manufactured in the same manner as Example 1-1, except that the compounds listed in Table 1 below were used instead of Compound 1.
  • the compounds EB2 to EB8 used in Table 1 below are as follows.
  • T95 refers to the time it takes for the luminance to decrease from the initial luminance (1600 nit) to 95%.
  • Example 1-1 Compound 1 3.46 6.39 (0.143, 0.046) 212
  • Example 1-3 Compound 3 3.54 6.46 (0.144, 0.045) 225
  • Example 1-4 Compound 4 3.52 6.51 (0.143, 0.046) 217
  • Example 1-6 Compound 6 3.41 6.31 (0.144, 0.045) 205
  • Example 1-7 Compound 7 3.43 6.47 (0.145, 0.045) 210 Comparative Example 1-1 EB2 3.82 6.22 (0.144, 0.045) 191 Comparative Example 1-2 EB3 3.62 6.17 (0.143, 0.046) 178 Comparative Example 1-3 EB4 3.81 6.20 (0.144, 0.045)
  • the organic light-emitting device using the compound of the present invention as an electron blocking layer showed excellent characteristics in terms of efficiency, driving voltage, and stability of the organic light-emitting device.
  • the carbazole group on the biphenyl linkage bonded to the amine has substitution positions of ortho-para, meta-para, and meta-meta, respectively. In the case of Formula 1, it has an ortho-meta substitution position.
  • Comparative Examples 1-5 to 1-7 using compounds EB6 to EB8 have lower voltage and efficiency than Examples 1-1 to 1-7, but the difference in lifespan is greater than the difference in voltage or efficiency.
  • the compound according to the present invention has excellent electron blocking ability and can be applied to organic light-emitting devices.
  • An organic light-emitting device was manufactured in the same manner as Example 1-1, except that the compound EB1 was used instead of Compound 1, and the compound listed in Table 2 below was used instead of HT1.
  • An organic light-emitting device was manufactured in the same manner as Example 1-1, except that the compounds shown in Table 2 below were used instead of the compounds of Preparation Example 1.
  • the compounds HT2 to HT8 used in Table 2 below are as follows.
  • T95 refers to the time it takes for the luminance to decrease from the initial luminance (1600 nit) to 95%.
  • Example 2-1 Compound 1 3.74 6.45 (0.143, 0.046) 202
  • Example 2-3 Compound 3 3.78 6.55 (0.144, 0.046) 210
  • Example 2-4 Compound 4 3.77 6.71 (0.143, 0.046) 199
  • Example 2-5 Compound 5 3.69 6.63 (0.143, 0.045) 201
  • Example 2-6 Compound 6 3.58 6.42 (0.144, 0.045) 194
  • Example 2-7 Compound 7 3.54 6.50 (0.144, 0.046) 203 Comparative Example 2-1 HT2 3.91 5.72 (0.144, 0.045) 172 Comparative Example 2-2 HT3 3.84 6.21 (0.143, 0.046) 175 Comparative Example 2-3 HT4 3.97 6.13 (0.143, 0.046) 17
  • the organic light-emitting device using the compound of the present invention as a hole transport layer showed excellent characteristics in terms of efficiency, driving voltage, and stability of the organic light-emitting device.
  • Examples 2-1 to 2-7 showed lower voltage, higher efficiency, and longer life than Comparative Examples 2-1 to 2-4. It can be confirmed that it has characteristics.
  • the carbazole group on the biphenyl linkage bonded to the amine has substitution positions of ortho-para, meta-para, and meta-meta, respectively. In the case of Formula 1, it has an ortho-meta substitution position.
  • Comparative Examples 2-5 to 2-7 using compounds EB6 to EB8 are lower in voltage and efficiency than Examples 2-1 to 2-6, but the difference in life is larger than the difference in voltage or efficiency.
  • the compound according to the present invention has excellent hole transport ability and can be applied to organic light-emitting devices.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (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 représenté par la formule chimique 1, et un élément électroluminescent organique le comprenant.
PCT/KR2023/008159 2022-06-15 2023-06-14 Composé et élément électroluminescent organique le comprenant WO2023244000A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20170036641A (ko) * 2015-09-24 2017-04-03 주식회사 엘지화학 화합물 및 이를 포함하는 유기 전자 소자
KR20190088029A (ko) * 2018-01-17 2019-07-25 주식회사 엘지화학 유기 발광 소자
KR20200100299A (ko) * 2019-02-18 2020-08-26 주식회사 이엘엠 유기 전기 발광 조성물 및 이를 포함하는 유기 전기 발광 소자
CN111662225A (zh) * 2019-03-08 2020-09-15 江苏三月光电科技有限公司 一种含芘的有机化合物及其应用
KR20200144482A (ko) * 2019-06-18 2020-12-29 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자

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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
KR20170036641A (ko) * 2015-09-24 2017-04-03 주식회사 엘지화학 화합물 및 이를 포함하는 유기 전자 소자
KR20190088029A (ko) * 2018-01-17 2019-07-25 주식회사 엘지화학 유기 발광 소자
KR20200100299A (ko) * 2019-02-18 2020-08-26 주식회사 이엘엠 유기 전기 발광 조성물 및 이를 포함하는 유기 전기 발광 소자
CN111662225A (zh) * 2019-03-08 2020-09-15 江苏三月光电科技有限公司 一种含芘的有机化合物及其应用
KR20200144482A (ko) * 2019-06-18 2020-12-29 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자

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