WO2023244000A1 - Compound and organic light-emitting element comprising same - Google Patents

Compound and organic light-emitting element comprising same Download PDF

Info

Publication number
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
Authority
WO
WIPO (PCT)
Prior art keywords
group
substituted
unsubstituted
layer
carbon atoms
Prior art date
Application number
PCT/KR2023/008159
Other languages
French (fr)
Korean (ko)
Inventor
문현진
김민준
김주호
이성재
홍성길
Original Assignee
주식회사 엘지화학
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Publication of WO2023244000A1 publication Critical patent/WO2023244000A1/en

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
    • H10K50/181—Electron blocking layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

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.

Landscapes

  • 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

The present specification relates to a compound represented by chemical formula 1, and an organic light-emitting element comprising same.

Description

화합물 및 이를 포함하는 유기 발광 소자Compounds and organic light-emitting devices containing them
본 출원은 2022년 06월 15일 한국특허청에 제출된 한국 특허 출원 제10-2022-0072898호의 출원일의 이익을 주장하며, 그 내용 전부는 본 명세서에 포함된다.This application claims the benefit of the filing date of Korean Patent Application No. 10-2022-0072898 filed with the Korea Intellectual Property Office on June 15, 2022, the entire contents of which are included in this specification.
본 명세서는 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다. This specification relates to compounds and organic light-emitting devices containing the same.
본 명세서에서, 유기 발광 소자란 유기 반도체 물질을 이용한 발광 소자로서, 전극과 유기 반도체 물질 사이에서의 정공 및/또는 전자의 교류를 필요로 한다. 유기 발광 소자는 동작 원리에 따라 하기와 같이 크게 두 가지로 나눌 수 있다. 첫째는 외부의 광원으로부터 소자로 유입된 광자에 의하여 유기물층에서 엑시톤(exiton)이 형성되고, 이 엑시톤이 전자와 정공으로 분리되고, 이 전자와 정공이 각각 다른 전극으로 전달되어 전류원(전압원)으로 사용되는 형태의 발광 소자이다. 둘째는 2개 이상의 전극에 전압 또는 전류를 가하여 전극과 계면을 이루는 유기 반도체 물질층에 정공 및/또는 전자를 주입하고, 주입된 전자와 정공에 의하여 작동하는 형태의 발광 소자이다.In this specification, 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.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자억제층, 전자수송층, 전자주입층 등으로 이루어 질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. 이러한 유기 발광 소자는 자발광, 고휘도, 고효율, 낮은 구동 전압, 넓은 시야각, 높은 콘트라스트 등의 특성을 갖는 것으로 알려져 있다.In general, organic 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. Here, 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. In the structure of 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.
유기 발광 소자에서 유기물층으로 사용되는 재료는 기능에 따라, 발광 재료와 전하 수송 재료, 예컨대 정공 주입 재료, 정공 수송 재료, 전자 억제 물질, 전자 수송 재료, 전자 주입 재료 등으로 분류될 수 있다. 발광 재료는 발광색에 따라 청색, 녹색, 적색 발광 재료와 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 재료가 있다.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. Depending on the 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.
또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 재료로서 호스트/도펀트 계를 사용할 수 있다. 그 원리는 발광층을 주로 구성하는 호스트보다 에너지 대역 간극이 작고 발광 효율이 우수한 도펀트를 발광층에 소량 혼합하면, 호스트에서 발생한 엑시톤이 도펀트로 수송되어 효율이 높은 빛을 내는 것이다. 이 때 호스트의 파장이 도펀트의 파장대로 이동하므로, 이용하는 도펀트의 종류에 따라 원하는 파장의 빛을 얻을 수 있다.Additionally, in order to increase color purity and increase luminous efficiency through energy transfer, 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. At this time, since 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.
전술한 유기 발광 소자가 갖는 우수한 특징들을 충분히 발휘하기 위해서는 소자 내 유기물층을 이루는 물질, 예컨대 정공 주입 물질, 정공 수송 물질, 발광 물질, 전자 억제 물질, 전자 수송 물질, 전자 주입 물질 등이 안정하고 효율적인 재료에 의하여 뒷받침되므로 새로운 재료의 개발이 계속 요구되고 있다.In order to fully demonstrate the excellent characteristics of the above-described organic light-emitting device, 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.
본 명세서에는 화합물 및 이를 포함하는 유기 발광 소자가 기재된다. Disclosed herein are compounds and organic light-emitting devices containing the same.
본 명세서의 일 실시상태는 하기 화학식 1의 화합물을 제공한다.An exemplary embodiment of the present specification provides a compound of Formula 1 below.
[화학식 1][Formula 1]
Figure PCTKR2023008159-appb-img-000001
Figure PCTKR2023008159-appb-img-000001
상기 화학식 1에 있어서,In Formula 1,
L은 직접결합, 치환 또는 비치환된 아릴렌기, 또는 치환 또는 비치환된 헤테로아릴렌기이고,L is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
Ar1은 수소, 중수소, 할로겐기, 니트릴기, 치환 또는 비치환된 알킬기, 치환 또는 비치환되는 아릴기, 또는 치환 또는 비치환된 헤테로아릴기이다.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.
또한, 본 발명의 일 실시상태에 따르면, 제1 전극; 상기 제1 전극과 대향하여 구비되는 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비되는 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상이 전술한 화합물을 포함하는 유기 발광 소자를 제공한다.Additionally, according to an exemplary embodiment of the present invention, 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.
본 발명의 화합물은 유기 발광 소자의 유기물층의 재료로서 사용될 수 있다. 본 발명의 화합물을 포함하여 유기 발광 소자를 제조하는 경우, 고효율, 저전압 및 장수명 특성을 갖는 유기 발광 소자를 얻을 수 있으며, 본 발명의 화합물을 유기 발광 소자의 정공주입층, 정공수송층, 또는 전자저지층에 포함하는 경우, 낮은 전압, 높은 효율, 및 장수명의 특성을 가지는 유기 발광 소자를 제조할 수 있다.The compound of the present invention can be used as a material for the organic layer of an organic light-emitting device. When manufacturing 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. When included in the layer, an organic light emitting device with low voltage, high efficiency, and long lifespan characteristics can be manufactured.
상기 화학식 1의 화합물은 벤젠고리에 카바졸이 메타(meta)나 오쏘(ortho) 위치로 치환되는 구조로써, 파라(para) 구조가 포함되거나 메타+메타 구조인 물질들보다 컨쥬게이션이 끊어져 있는 상태이므로 밴드갭이 커서 치환기의 종류에 따라 HOMO 및 LUMO 값을 상대적으로 조절하기 쉬운 구조이다. 또한 오쏘+오쏘 구조보다 입체 장애가 적어 적절한 홀 이동도를 가지고 있다.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.
따라서, 상기 화학식 1로 표시되는 화합물들을 합성하여 정공주입층, 정공수송층 또는 전자차단층에 소자평가를 진행하였을 때, 유기 전자 소자의 구동전압을 낮추고, 수명을 보다 향상시킬 수 있다.Therefore, when the compounds represented by Formula 1 are synthesized and device evaluation is performed on the hole injection layer, hole transport layer, or electron blocking layer, the driving voltage of the organic electronic device can be lowered and the lifespan can be further improved.
도 1 및 도 2는 본 발명에 따른 유기 발광 소자의 예를 도시한 것이다.1 and 2 show examples of organic light-emitting devices according to the present invention.
[부호의 설명][Explanation of symbols]
1: 기판1: substrate
2: 제1 전극2: first electrode
3: 유기물층3: Organic layer
4: 제2전극4: Second electrode
5: 정공주입층5: Hole injection layer
6: 정공수송층6: Hole transport layer
7: 전자억제층7: Electron suppression layer
8: 발광층8: Light-emitting layer
9: 정공저지층9: Hole blocking layer
10: 전자주입 및 수송층10: Electron injection and transport layer
이하 본 명세서에 대하여 더욱 상세히 설명한다. Hereinafter, this specification will be described in more detail.
본 명세서에 있어서, 어떤 부분이 어떤 구성요소를 "포함" 한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성 요소를 더 포함할 수 있는 것을 의미한다.In this specification, when a part “includes” a certain component, this means that it may further include other components rather than excluding other components, unless specifically stated to the contrary.
본 명세서에 있어서, 어떤 부재가 다른 부재 "상에" 위치하고 있다고 할 때, 이는 어떤 부재가 다른 부재에 접해 있는 경우뿐 아니라 두 부재 사이에 또 다른 부재가 존재하는 경우도 포함한다.In this specification, when a member is said to be located “on” another member, this includes not only the case where a member is in contact with another member, but also the case where another member exists between the two members.
상기 "치환" 이라는 용어는 화합물의 탄소 원자에 결합된 수소 원자가 다른 치환기로 바뀌는 것을 의미하며, 치환되는 위치는 수소 원자가 치환되는 위치 즉, 치환기가 치환 가능한 위치라면 한정하지 않으며, 2 이상 치환되는 경우, 2 이상의 치환기는 서로 동일하거나 상이할 수 있다.The term "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.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 시아노기(-CN); 실릴기; 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되었거나 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 바이페닐기일 수 있다. 즉, 바이페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 도 있다.As used herein, the term “substituted or unsubstituted” 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. For example, “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.
상기 치환기들의 예시들은 하기에서 설명하나, 이에 한정되는 것은 아니다. Examples of the above substituents are described below, but are not limited thereto.
본 명세서에 있어서, 할로겐기의 예로는 불소(F), 염소(Cl), 브롬(Br) 또는 요오드(I)가 있다.In this specification, examples of halogen groups include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).
본 명세서에 있어서, 실릴기는 -SiY1Y2Y3의 화학식으로 표시될 수 있고, 상기 Y1, Y2 및 Y3는 각각 수소; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기일 수 있다. 상기 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다. In the present specification, 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.
본 명세서에 있어서, 붕소기는 -BY4Y5의 화학식으로 표시될 수 있고, 상기 Y4 및Y5는 각각 수소; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기일 수 있다. 상기 붕소기는 구체적으로 디메틸붕소기, 디에틸붕소기, t-부틸메틸붕소기, 디페닐붕소기, 페닐붕소기 등이 있으나 이에 한정되지 않는다.In the present specification, 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.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 60인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 30이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 알킬기의 구체적인 예로는 메틸기, 에틸기, 프로필기, 이소프로필기, 부틸기, 이소부틸기, tert-부틸기, 펜틸기, 헥실기, 헵틸기, 옥틸기 등이 있으나, 이들에 한정되지 않는다.In the present specification, 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.
본 명세서에 있어서, 상기 아릴알킬기는 아릴기로 치환된 알킬기를 말한다. 탄소수는 특별히 한정하지 않으나, 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 30이고, 알킬기에 치환된 아릴기의 탄소수는 6 내지 30이다. In the present specification, 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.
본 명세서에 있어서, 아민기는 -NH2; 알킬아민기; N-알킬아릴아민기; 아릴아민기; N-아릴헤테로아릴아민기; N-알킬헤테로아릴아민기 및 헤테로아릴아민기로 이루어진 군으로부터 선택될 수 있으며, 탄소수는 특별히 한정되지 않으나, 1 내지 30인 것이 바람직하다. 아민기의 구체적인 예로는 메틸아민기; 디메틸아민기; 에틸아민기; 디에틸아민기; 페닐아민기; 나프틸아민기; 바이페닐아민기; 안트라세닐아민기; 9-메틸안트라세닐아민기; 디페닐아민기; 디톨릴아민기; N-페닐톨릴아민기; 트리페닐아민기; N-페닐바이페닐아민기; N-페닐나프틸아민기; N-바이페닐나프틸아민기; N-나프틸플루오레닐아민기; N-페닐페난트레닐아민기; N-바이페닐페난트레닐아민기; N-페닐플루오레닐아민기; N-페닐터페닐아민기; N-페난트레닐플루오레닐아민기; N-바이페닐플루오레닐아민기 등이 있으나, 이에 한정되는 것은 아니다.In this specification, the amine group is -NH 2 ; 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. Specific examples of 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., but is not limited thereto.
본 명세서에 있어서, N-알킬아릴아민기는 아민기의 N에 알킬기 및 아릴기가 치환된 아민기를 의미한다.In the present specification, 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.
본 명세서에 있어서, N-아릴헤테로아릴아민기는 아민기의 N에 아릴기 및 헤테로아릴기가 치환된 아민기를 의미한다.In the present specification, 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.
본 명세서에 있어서, N-알킬헤테로아릴아민기는 아민기의 N에 알킬기 및 헤테로아릴기가 치환된 아민기를 의미한다.In the present specification, 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.
본 명세서에 있어서, 알킬아민기, N-아릴알킬아민기, 알킬티옥시기, 알킬술폭시기, N-알킬헤테로아릴아민기 중의 알킬기는 전술한 알킬기의 예시와 같다. 구체적으로 알킬티옥시기로는 메틸티옥시기; 에틸티옥시기; tert－부틸티옥시기; 헥실티옥시기; 옥틸티옥시기 등이 있고, 알킬술폭시기로는 메실; 에틸술폭시기; 프로필술폭시기; 부틸술폭시기 등이 있으나, 이에 한정되는 것은 아니다.In this specification, the 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. Specifically, the alkylthioxy group includes methylthioxy group; ethylthioxy group; tert-butylthioxy group; hexylthioxy group; Octylthioxy groups, etc., and examples of alkylsulfoxy groups include mesyl; ethyl sulfoxy group; Propyl alcohol oxygen group; Butyl sulfoxy group, etc., but is not limited thereto.
본 명세서에 있어서, 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 일 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 시클로프로필기, 시클로부틸기, 시클로펜틸기, 시클로헥실기, 시클로헵틸기, 시클로옥틸기 등이 있으나, 이에 한정되지 않는다. In the present specification, 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.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며, 단환식 아릴기 또는 다환식 아릴기일 수 있다. In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group.
일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 30이다. According to one embodiment, the aryl group has 6 to 30 carbon atoms.
일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 20이다. According to one embodiment, the aryl group has 6 to 20 carbon atoms.
상기 아릴기가 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트레닐기, 파이레닐기, 페릴레닐기, 트리페닐렌기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.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.
본 명세서에 있어서, 헤테로아릴기는 이종원자로 N, O, P, S, Si 및 Se 중 1개 이상을 포함하는 고리기로서, 탄소수는 특별히 한정되지 않으나 탄소수 2 내지 60인 것이 바람직하다. 일 실시상태에 따르면, 상기 헤테로고리기의 탄소수는 2 내지 30이다. 헤테로고리기의 예로는 피리딘기, 피롤기, 피리미딘기, 피리다지닐기, 퓨란기, 티오펜기, 이미다졸기, 피라졸기, 디벤조퓨란기, 디벤조티오펜기, 카바졸기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, 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. Examples of 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.
본 명세서에 있어서, "인접한 기와 서로 결합하여 고리를 형성"에서 "인접한"의 의미는 전술한 바와 동일하며, 상기 "고리"는 치환 또는 비치환된 탄화수소고리; 또는 치환 또는 비치환된 헤테로고리를 의미한다.In the present specification, 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.
본 명세서에 있어서, 탄화수소고리는 방향족 탄화수소고리, 지방족 탄화수소고리, 또는 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리일 수 있으며, 상기 1가가 아닌 것을 제외하고 상기 시클로알킬기, 아릴기, 및 이들의 조합의 예시 중에서 선택될 수 있으며, 상기 탄화수소고리는 벤젠, 시클로헥산, 아다만탄, 바이시클로[2.2.1]헵탄, 바이시클로[2.2.1]옥탄, 테트라하이드로나프탈렌, 테트라하이드로안트라센, 1,2,3,4-테트라하이드로-1,4-메타노나프탈렌, 및 1,2,3,4-테트라하이드로-1,4-에타노나프탈렌 등이 있으나, 이에만 한정되는 것은 아니다.In the present specification, 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. It can be selected from examples, and the 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.
본 명세서에서 달리 정의되지 않는 한, 본 명세서에서 사용되는 모든 기술적 및 과학적 용어는 본 발명이 속하는 기술 분야의 당업자에 의해 통상적으로 이해되는 바와 동일한 의미를 갖는다. 본 명세서에서 설명되는 것과 유사하거나 등가인 방법 및 재료가 본 발명의 실시 형태의 실시 또는 시험에서 사용될 수 있지만, 적합한 방법 및 재료가 후술된다. 본 명세서에서 언급되는 모든 간행물, 특허 출원, 특허 및 다른 참고 문헌은 전체적으로 본 명세서에 참고로 포함되며, 상충되는 경우 특정 어구(passage)가 언급되지 않으면, 정의를 비롯한 본 명세서가 우선할 것이다. 게다가, 재료, 방법, 및 실시예는 단지 예시적인 것이며 제한하고자 하는 것은 아니다.Unless otherwise defined herein, all technical and scientific terms used herein have the same meaning as commonly understood by a person skilled in the art to which the present invention pertains. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of embodiments of the invention, suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety, and in case of conflict, the present specification, including definitions, will control unless a specific passage is mentioned. Moreover, the materials, methods, and examples are illustrative only and are not intended to be limiting.
본 명세서에 있어서, 아릴렌기는 2가기인 것을 제외하고, 상기 아릴기에서 정의한 바와 같다.In the present specification, the arylene group is the same as defined for the aryl group above, except that it is a divalent group.
본 명세서에 있어서, 헤테로아릴렌기는 2가기인 것을 제외하고, 상기 헤테로아릴기에서 정의한 바와 같다.In the present specification, the heteroarylene group is the same as defined for the heteroaryl group above, except that it is a divalent group.
본 명세서의 일 실시상태에 따르면, 상기 L은 직접결합, 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기, 또는 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 L은 직접결합, 치환 또는 비치환된 탄소수 6 내지 20의 아릴렌기, 또는 치환 또는 비치환된 탄소수 3 내지 20의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 L은 직접결합, 치환 또는 비치환된 탄소수 6 내지 15의 아릴렌기, 또는 치환 또는 비치환된 탄소수 3 내지 15의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 L은 직접결합, 또는 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기이다.According to an exemplary embodiment of the present specification, L is a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L은 직접결합, 또는 치환 또는 비치환된 탄소수 6 내지 20의 아릴렌기이다.According to an exemplary embodiment of the present specification, L is a direct bond, or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L은 직접결합, 또는 치환 또는 비치환된 탄소수 6 내지 15의 아릴렌기이다.According to an exemplary embodiment of the present specification, L is a direct bond, or a substituted or unsubstituted arylene group having 6 to 15 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L은 직접결합, 치환 또는 비치환된 페닐렌기, 치환 또는 비치환된 2가의 비페닐기, 치환 또는 비치환된 2가의 터페닐기, 치환 또는 비치환된 2가의 나프틸기, 치환 또는 비치환된 2가의 파이렌기, 치환 또는 비치환된 2가의 안트라센기, 치환 또는 비치환된 2가의 페난트렌기, 치환 또는 비치환된 2가의 트리페닐렌기, 치환 또는 비치환된 2가의 플루오렌기, 또는 치환 또는 비치환된 2가의 플루오란텐기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 L은 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기이다.According to an exemplary embodiment of the present specification, L is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L은 치환 또는 비치환된 탄소수 6 내지 20의 아릴렌기이다.According to an exemplary embodiment of the present specification, L is a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L은 치환 또는 비치환된 탄소수 6 내지 15의 아릴렌기이다.According to an exemplary embodiment of the present specification, L is a substituted or unsubstituted arylene group having 6 to 15 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L은 치환 또는 비치환된 페닐렌기, 치환 또는 비치환된 2가의 비페닐기, 치환 또는 비치환된 2가의 터페닐기, 치환 또는 비치환된 2가의 나프틸기, 치환 또는 비치환된 2가의 파이렌기, 치환 또는 비치환된 2가의 안트라센기, 치환 또는 비치환된 2가의 페난트렌기, 치환 또는 비치환된 2가의 트리페닐렌기, 치환 또는 비치환된 2가의 플루오렌기, 또는 치환 또는 비치환된 2가의 플루오란텐기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 L은 치환 또는 비치환된 페닐렌기, 치환 또는 비치환된 2가의 비페닐기, 치환 또는 비치환된 2가의 터페닐기, 또는 치환 또는 비치환된 2가의 나프틸기이다. According to an exemplary embodiment of the present specification, 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. am.
본 명세서의 일 실시상태에 따르면, 상기 L은 치환 또는 비치환된 페닐렌기, 치환 또는 비치환된 2가의 비페닐기, 또는 치환 또는 비치환된 2가의 나프틸기이다. According to an exemplary embodiment of the present specification, L is a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, or a substituted or unsubstituted divalent naphthyl group.
본 명세서의 일 실시상태에 따르면, 상기 L은 직접결합, 또는 페닐렌기이다.According to an exemplary embodiment of the present specification, L is a direct bond or a phenylene group.
본 명세서의 일 실시상태에 따르면, 상기 L은 치환 또는 비치환된 2가의 비페닐기, 또는 치환 또는 비치환된 2가의 나프틸기이다. According to an exemplary embodiment of the present specification, L is a substituted or unsubstituted divalent biphenyl group, or a substituted or unsubstituted divalent naphthyl group.
본 명세서의 일 실시상태에 따르면, 상기 L은 직접결합이다. According to an exemplary embodiment of the present specification, L is a direct bond.
본 명세서의 일 실시상태에 따르면, 상기 L은 페닐렌기이다.According to an exemplary embodiment of the present specification, L is a phenylene group.
본 명세서의 일 실시상태에 따르면, 상기 L은 2가의 비페닐기이다.According to an exemplary embodiment of the present specification, L is a divalent biphenyl group.
본 명세서의 일 실시상태에 따르면, 상기 L은 2가의 나프틸기이다.According to an exemplary embodiment of the present specification, L is a divalent naphthyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 1-1 내지 화학식 1-4 중 어느 하나이다.According to an exemplary embodiment of the present specification, Formula 1 is any one of the following Formulas 1-1 to 1-4.
[화학식 1-1][Formula 1-1]
Figure PCTKR2023008159-appb-img-000002
Figure PCTKR2023008159-appb-img-000002
[화학식 1-2][Formula 1-2]
Figure PCTKR2023008159-appb-img-000003
Figure PCTKR2023008159-appb-img-000003
[화학식 1-3][Formula 1-3]
Figure PCTKR2023008159-appb-img-000004
Figure PCTKR2023008159-appb-img-000004
[화학식 1-4][Formula 1-4]
Figure PCTKR2023008159-appb-img-000005
Figure PCTKR2023008159-appb-img-000005
상기 화학식 1-1 내지 1-4에 있어서, Ar은 상기 화학식 1에서 정의한 것과 같고, In Formulas 1-1 to 1-4, Ar is as defined in Formula 1,
a는 0 내지 3의 정수이고, a is an integer from 0 to 3,
b는 1 내지 3의 정수이다. b is an integer from 1 to 3.
본 명세서의 일 실시상태에 따르면, 상기 Ar은 수소, 중수소, 할로겐기, 니트릴기, 치환 또는 비치환된 알킬기, 치환 또는 비치환되는 아릴기, 또는 치환 또는 비치환된 헤테로아릴기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 Ar은 수소, 중수소, 할로겐기, 니트릴기, 치환 또는 비치환된 탄소수 1 내지 10의 알킬기, 치환 또는 비치환되는 탄소수 6 내지 30의 아릴기, 또는 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 Ar은 수소, 중수소, 할로겐기, 니트릴기, 치환 또는 비치환된 탄소수 1 내지 10의 알킬기, 치환 또는 비치환되는 탄소수 6 내지 20의 아릴기, 또는 치환 또는 비치환된 탄소수 3 내지 20의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 Ar은 수소, 중수소, 할로겐기, 니트릴기, 치환 또는 비치환된 탄소수 1 내지 10의 알킬기, 치환 또는 비치환되는 탄소수 6 내지 15의 아릴기, 또는 치환 또는 비치환된 탄소수 3 내지 15의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 Ar은 수소, 중수소, 할로겐기, 니트릴기, 탄소수 1 내지 10의 알킬기, 탄소수 6 내지 30의 아릴기, 또는 탄소수 3 내지 30의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 Ar은 수소, 중수소, 할로겐기, 니트릴기, 탄소수 1 내지 10의 알킬기, 탄소수 6 내지 20의 아릴기, 또는 탄소수 3 내지 20의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 Ar은 수소, 중수소, 할로겐기, 니트릴기, 탄소수 1 내지 10의 알킬기, 탄소수 6 내지 15의 아릴기, 또는 탄소수 3 내지 15의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 Ar은 수소, 중수소, 할로겐기, 니트릴기, 탄소수 1 내지 10의 알킬기, 탄소수 6 내지 30의 단환 또는 다환의 아릴기, 또는 탄소수 3 내지 30의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 Ar은 수소, 중수소, 할로겐기, 니트릴기, 탄소수 1 내지 10의 알킬기, 탄소수 6 내지 20의 단환 또는 다환의 아릴기, 또는 탄소수 3 내지 20의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 Ar은 수소, 중수소, 할로겐기, 니트릴기, 탄소수 1 내지 10의 알킬기, 탄소수 10 내지 30의 다환의 아릴기, 또는 탄소수 3 내지 30의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 Ar은 수소, 중수소, 할로겐기, 니트릴기, 탄소수 1 내지 10의 알킬기, 탄소수 10 내지 20의 다환의 아릴기, 또는 탄소수 3 내지 20의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 Ar은 치환 또는 비치환된 페닐기; 치환 또는 비치환된 비페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 안트라세닐기; 치환 또는 비치환된 페난트릴기; 치환 또는 비치환된 파이레닐기; 치환 또는 비치환된 페릴레닐기; 치환 또는 비치환된 크라이세닐기; 치환 또는 비치환된 플루오레닐기; 또는 치환 또는 비치환된 나프틸기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 Ar은 치환 또는 비치환된 페닐기, 치환 또는 비치환된 비페닐기, 치환 또는 비치환된 나프틸기, 치환 또는 비치환된 페난트렌기, 치환 또는 비치환된 디벤조퓨란기, 또는 치환 또는 비치환된 디벤조티오펜기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 Ar은 아릴기로 치환 또는 비치환된 페닐기, 아릴기로 치환 또는 비치환된 비페닐기, 아릴기로 치환 또는 비치환된 나프틸기, 아릴기로 치환 또는 비치환된 페난트렌기, 아릴기로 치환 또는 비치환된 디벤조퓨란기, 또는 아릴기로 치환 또는 비치환된 디벤조티오펜기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 Ar은 탄소수 6 내지 30의 아릴기로 치환 또는 비치환된 페닐기, 탄소수 6 내지 30의 아릴기로 치환 또는 비치환된 비페닐기, 탄소수 6 내지 30의 아릴기로 치환 또는 비치환된 나프틸기, 탄소수 6 내지 30의 아릴기로 치환 또는 비치환된 페난트렌기, 탄소수 6 내지 30의 아릴기로 치환 또는 비치환된 디벤조퓨란기, 또는 탄소수 6 내지 30의 아릴기로 치환 또는 비치환된 디벤조티오펜기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 Ar은 탄소수 6 내지 20의 아릴기로 치환 또는 비치환된 페닐기, 탄소수 6 내지 20의 아릴기로 치환 또는 비치환된 비페닐기, 탄소수 6 내지 20의 아릴기로 치환 또는 비치환된 나프틸기, 탄소수 6 내지 20의 아릴기로 치환 또는 비치환된 페난트렌기, 탄소수 6 내지 20의 아릴기로 치환 또는 비치환된 디벤조퓨란기, 또는 탄소수 6 내지 20의 아릴기로 치환 또는 비치환된 디벤조티오펜기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 Ar은 페닐기, 비페닐기, 페닐기로 치환 또는 비치환된 나프틸기, 페난트렌기, 디벤조퓨란기, 또는 디벤조티오펜기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 구조식 중 어느 하나이다. According to an exemplary embodiment of the present specification, Formula 1 is one of the following structural formulas.
Figure PCTKR2023008159-appb-img-000006
Figure PCTKR2023008159-appb-img-000006
Figure PCTKR2023008159-appb-img-000007
Figure PCTKR2023008159-appb-img-000007
상기 화학식 1의 화합물의 치환기는 당 기술분야에 알려져 있는 방법에 의하여 결합될 수 있으며, 치환기의 종류, 위치 또는 개수는 당 기술분야에 알려져 있는 기술에 따라 변경될 수 있다.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.
또한, 상기와 같은 구조의 코어 구조에 다양한 치환기를 도입함으로써 도입된 치환기의 고유 특성을 갖는 화합물을 합성할 수 있다. 예컨대, 유기 발광 소자 제조시 사용되는 정공 주입층 물질, 정공 수송용 물질, 발광층 물질 및 전자 수송층 물질에 주로 사용되는 치환기를 상기 코어 구조에 도입함으로써 각 유기물층에서 요구하는 조건들을 충족시키는 물질을 합성할 수 있다.In addition, by introducing various substituents into the core structure of the above structure, it is possible to synthesize compounds having the unique properties of the introduced substituents. For example, by introducing substituents mainly used in hole injection layer materials, hole transport materials, light emitting layer materials, and electron transport layer materials used in the manufacture of organic light-emitting devices into the core structure, a material that satisfies the conditions required for each organic material layer can be synthesized. You can.
또한, 본 발명에 따른 유기 발광 소자는 제1 전극; 상기 제1 전극과 대향하여 구비되는 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비되는 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 전술한 화합물을 포함하는 것을 특징으로 한다.Additionally, the organic light emitting device according to the present invention 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.
본 발명의 유기 발광 소자는 전술한 화합물을 이용하여 한 층 이상의 유기물층을 형성하는 것을 제외하고는, 통상의 유기 발광 소자의 제조방법 및 재료에 의하여 제조될 수 있다.The organic light emitting device of the present invention can be manufactured 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.
상기 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥 코팅, 잉크젯 프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.The compound may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution application method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.
본 발명의 유기 발광 소자의 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 발명의 유기 발광 소자는 유기물층으로서 정공주입층, 정공수송층, 정공주입 및 정공수송을 동시에 하는 층, 발광층, 전자수송층, 전자주입층 등을 포함하는 구조를 가질 수 있다. 그러나, 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기물층 또는 더 많은 수의 유기물층을 포함할 수 있다.The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole 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. However, the structure of the organic light emitting device is not limited to this and may include fewer or more organic material layers.
본 발명의 유기 발광 소자에서, 상기 유기물층은 전자수송층, 전자주입층 및 전자주입과 전자수송을 동시에 하는 층 중 1층 이상을 포함할 수 있고, 상기 층들 중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.In the organic light emitting device of the present invention, 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.
또 하나의 유기 발광 소자에서, 상기 유기물층은 전자수송층 또는 전자주입층을 포함할 수 있고, 상기 전자수송층 또는 전자주입층이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.In another organic light emitting device, 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.
본 발명의 유기 발광 소자에서, 상기 유기물층은 정공주입층, 정공수송층 및 정공주입과 정공수송을 동시에 하는 층 중 1층 이상을 포함할 수 있고, 상기 층들 중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.In the organic light emitting device of the present invention, 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.
본 발명의 유기 발광 소자에서, 상기 유기물층은 정공주입층, 또는 정공수송층을 포함할 수 있고, 상기 정공주입층 또는 정공수송층이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.In the organic light emitting device of the present invention, the organic material layer may include a hole 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.
본 발명의 유기 발광 소자에서, 상기 유기물층은 전자억제층을 포함하고, 상기 전자억제층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. In the organic light emitting device of the present invention, the organic material layer includes an electron blocking layer, and the electron blocking layer may include a compound represented by Formula 1 above.
본 발명의 유기 발광 소자에서, 상기 유기물층은 정공수송층 또는 전자억제층을 포함하고, 상기 정공수송층 또는 전자억제층은 상기 화합물을 포함할 수 있다.In the organic light emitting device of the present invention, 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.
본 발명의 유기 발광 소자에서, 상기 유기물층은 정공주입층, 정공수송층, 정공주입과 정공수송을 동시에 하는 층, 및 전자 억제층 중 1층 이상을 포함할 수 있고, 상기 층들 중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.In the organic light emitting device of the present invention, 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.
또 하나의 유기 발광 소자에서, 상기 유기물층은 정공주입층 또는 정공수송층을 포함할 수 있고, 상기 정공수송층 또는 정공주입층이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.In another organic light emitting device, 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.
본 발명의 유기 발광 소자에서, 상기 정공수송층과 발광층 사이에 추가의 전자억제층을 포함할 수 있다. In the organic light emitting device of the present invention, an additional electron blocking layer may be included between the hole transport layer and the light emitting layer.
본 발명의 유기 발광 소자에서, 상기 정공수송층과 전자억제층은 서로 접할 수 있고, 상기 전자억제층은 상기 화학식 1의 화합물을 포함한다. In the organic light emitting device of the present invention, 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.
본 발명의 유기 발광 소자에서, 상기 발광층과 전자억제층은 서로 접할 수 있고, 상기 전자억제층은 상기 화학식 1의 화합물을 포함한다. In the organic light emitting device of the present invention, 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.
본 발명의 유기 발광 소자에서, 상기 전자억제층과 양극 사이에 정공주입층 또는 정공수송층이 추가로 구비될 수 있다. In the organic light emitting device of the present invention, a hole injection layer or a hole transport layer may be additionally provided between the electron blocking layer and the anode.
본 발명의 유기 발광 소자에서, 상기 정공수송층과 전자억제층은 서로 접한다.In the organic light emitting device of the present invention, the hole transport layer and the electron blocking layer are in contact with each other.
본 명세서의 일 실시상태에 있어서, 상기 제1 전극은 양극이고, 제2 전극은 음극이다.In one embodiment of the present specification, the first electrode is an anode and the second electrode is a cathode.
또 하나의 일 실시상태에 따르면, 상기 제1 전극은 음극이고, 제2 전극은 양극이다.According to another exemplary embodiment, the first electrode is a cathode and the second electrode is an anode.
(1) 양극/정공수송층/발광층/음극(1) Anode/hole transport layer/light emitting layer/cathode
(2) 양극/정공주입층/정공수송층/발광층/음극(2) Anode/hole injection layer/hole transport layer/light emitting layer/cathode
(3) 양극/정공주입층/정공버퍼층/정공수송층/발광층/음극(3) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/cathode
(4) 양극/정공수송층/발광층/전자수송층/음극(4) Anode/hole transport layer/light emitting layer/electron transport layer/cathode
(5) 양극/정공수송층/발광층/전자수송층/전자주입층/음극(5) Anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(6) 양극/정공주입층/정공수송층/발광층/전자수송층/음극(6) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode
(7) 양극/정공주입층/정공수송층/발광층/전자수송층/전자주입층/음극(7) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(8) 양극/정공주입층/정공버퍼층/정공수송층/발광층/전자수송층/음극(8) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/cathode
(9) 양극/정공주입층/정공버퍼층/정공수송층/발광층/전자수송층/전자주입층 /음극(9) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(10) 양극/ 정공수송층/전자억제층/발광층/전자수송층/음극(10) Anode/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/cathode
(11) 양극/ 정공수송층/전자억제층/발광층/전자수송층/전자주입층/음극(11) Anode/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/electron injection layer/cathode
(12) 양극/정공주입층/정공수송층/전자억제층/발광층/전자수송층/음극(12) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/cathode
(13)양극/정공주입층/정공수송층/전자억제층/발광층/전자수송층/전자주입 층/음극(13) Anode/hole injection layer/hole transport layer/electron suppression layer/light-emitting layer/electron transport layer/electron injection layer/cathode
(14) 양극/정공수송층/발광층/정공억제층/전자수송층/음극(14) Anode/hole transport layer/light emitting layer/hole suppression layer/electron transport layer/cathode
(15) 양극/정공수송층/발광층/ 정공억제층/전자수송층/전자주입층/음극(15) Anode/hole transport layer/light emitting layer/hole suppression layer/electron transport layer/electron injection layer/cathode
(16) 양극/정공주입층/정공수송층/발광층/정공억제층/전자수송층/음극(16) Anode/hole injection layer/hole transport layer/light emitting layer/hole suppression layer/electron transport layer/cathode
(17)양극/정공주입층/정공수송층/발광층/정공억제층/전자수송층/전자주입 층/음극(17) Anode/hole injection layer/hole transport layer/light-emitting layer/hole suppression layer/electron transport layer/electron injection layer/cathode
(18)양극/정공주입층/정공수송층/전자억제층/발광층/정공저지층/전자주입및 수송층/음극(18) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/hole blocking layer/electron injection and transport layer/cathode
본 발명의 유기 발광 소자의 구조는 도 1 또는 도 2에 나타낸 것과 같은 구조를 가질 수 있으나, 이에만 한정되는 것은 아니다.The structure of the organic light emitting device of the present invention may have the same structure as shown in Figure 1 or Figure 2, but is not limited thereto.
도 1에는 기판(1) 위에 제1 전극(2), 유기물층(3) 및 제2 전극(4)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 유기물층(3)에 포함될 수 있다.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. In this structure, the compound represented by Formula 1 may be included in the organic layer 3.
도 2에는 기판(1) 위에 제1 전극(2), 정공주입층(5), 정공수송층(6), 전자억제층(7), 발광층(8), 정공저지층(9), 전자주입 및 수송층(10) 및 제2 전극(4)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 정공수송층(6) 또는 전자억제층(7)에 포함될 수 있다.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. In this structure, the compound represented by Formula 1 may be included in the hole transport layer 6 or the electron suppression layer 7.
예컨대, 본 발명에 따른 유기 발광 소자는 스퍼터링(sputtering)이나 전자빔 증발(e-beam evaporation)과 같은 PVD(physical vapor deposition) 방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공주입층, 정공수송층, 정공수송 및 정공주입을 동시에 하는 층, 발광층, 전자수송층, 전자주입층, 및 전자수송 및 전자주입을 동시에하는 층으로 이루어진 군으로부터 선택된 1층 이상을 포함하는 유기물층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수도 있다.For example, the organic light emitting device according to the present invention 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. 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. In addition to this method, 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.
상기 유기물층은 정공주입층, 정공수송층, 발광층 및 전자수송층 등을 포함하는 다층 구조일 수도 있으나, 이에 한정되지 않고 단층 구조일 수 있다. 또한, 상기 유기물층은 다양한 고분자 소재를 사용하여 증착법이 아닌 용매 공정(solvent process), 예컨대 스핀 코팅, 딥 코팅, 닥터 블레이딩, 스크린 프린팅, 잉크젯 프린팅 또는 열 전사법 등의 방법에 의하여 더 적은 수의 층으로 제조할 수 있다.The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, but is not limited to this and may have a single-layer structure. In addition, 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.
상기 양극은 정공을 주입하는 전극으로, 양극 물질로는 통상 유기물층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 본 발명에서 사용될 수 있는 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO, Indium Tin Oxide), 인듐아연 산화물(IZO, Indium Zinc Oxide)과 같은 금속 산화물; ZnO : Al 또는 SnO2 : Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.The anode is an electrode that injects holes, and the anode material is generally preferably a material with a large work function to facilitate hole injection into the organic layer. Specific examples of 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.
상기 음극은 전자를 주입하는 전극으로, 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다.The cathode is an electrode that injects electrons, and 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.
상기 정공주입층은 양극으로부터 발광층으로 정공의 주입을 원활하게 하는 역할을 하는 층이며, 정공 주입 물질로는 낮은 전압에서 양극으로부터 정공을 잘 주입 받을 수 있는 물질로서, 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린(porphyrine), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴헥사아자트리페닐렌 계열의 유기물, 퀴나크리돈(quinacridone) 계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다. 정공주입층의 두께는 1 내지 150nm일 수 있다. 상기 정공주입층의 두께가 1nm 이상이면, 정공 주입 특성이 저하되는 것을 방지할 수 있는 이점이 있고, 150nm 이하이면, 정공주입층의 두께가 너무 두꺼워 정공의 이동을 향상시키기 위해 구동전압이 상승되는것을 방지할 수 있는 이점이 있다.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) of the hole injection material It is preferable that the molecular orbital is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrilehexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. organic substances, anthraquinone, polyaniline, and polythiophene series conductive polymers, etc., but are not limited to these. 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.
본 명세서의 일 실시상태에 따르면, 상기 정공주입층은 하기 화학식 HI-1 로 표시되는 화합물을 포함하나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the hole injection layer includes, but is not limited to, a compound represented by the following formula HI-1.
[화학식 HI-1][Formula HI-1]
Figure PCTKR2023008159-appb-img-000008
Figure PCTKR2023008159-appb-img-000008
상기 화학식 HI-1에 있어서,In the formula HI-1,
L301 내지 L303은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,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 내지 R303는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 헤테로아릴기; 및 이들의 조합으로 이루어진 군에서 선택되는 어느 하나이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성한다.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.
본 명세서의 일 실시상태에 따르면, 상기 R301 내지 R303는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환된 헤테로아릴기; 및 이들의 조합으로 이루어진 군에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 R301 내지 R303는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 카바졸기; 치환 또는 비치환된 페닐기; 바이페닐기; 또는 메틸기로 치환 또는 비치환된 플루오렌기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 L301 내지 L303은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 아릴렌기; 또는 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 L301 내지 L303은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 페닐렌이다.According to an exemplary embodiment of the present specification, L301 to L303 are the same or different from each other and are each independently directly bonded; Or it is phenylene.
본 명세서의 일 실시상태에 따르면, 상기 화학식 HI-1은 하기 화합물로 표시된다.According to an exemplary embodiment of the present specification, the formula HI-1 is represented by the following compound.
Figure PCTKR2023008159-appb-img-000009
Figure PCTKR2023008159-appb-img-000009
상기 정공수송층은 정공의 수송을 원활하게 하는 역할을 할 수 있다. 정공 수송 물질로는 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다. 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.
정공주입층과 정공수송층 사이에 추가로 정공버퍼층이 구비될 있으며, 당 기술분야에 알려져 있는 정공주입 또는 수송재료를 포함할 수 있다.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.
본 명세서의 일 실시상태에 따르면, 상기 정공수송층은 상기 화학식 1 이외의 다른 재료를 포함하는 경우, 하기 화학식 HT-2로 표시되는 화합물을 포함하나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, 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.
[화학식 HT-2][Formula HT-2]
Figure PCTKR2023008159-appb-img-000010
Figure PCTKR2023008159-appb-img-000010
상기 화학식 HT-2에 있어서,In the formula HT-2,
R403 내지 R406는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 헤테로아릴기; 및 이들의 조합으로 이루어진 군에서 선택되는 어느 하나이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하고,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,
L403는 치환 또는 비치환된 아릴렌기, 또는 치환 또는 비치환된 헤테로아릴렌기이고,L403 is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
l403은 1 내지 3의 정수이고, l403이 2 이상이면, L403은 서로 같거나 상이하다.l403 is an integer from 1 to 3, and if l403 is 2 or more, L403 is the same or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 R403 내지 R406는 서로 같거나 상이하고, 각가 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 헤테로아릴기; 및 이들의 조합으로 이루어진 군에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 R403 내지 R406는 서로 같거나 상이하고, 각가 독립적으로 탄소수 6 내지 30의 아릴기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 R403 내지 R406는 서로 같거나 상이하고, 각가 독립적으로 페닐기, 비페닐기, 또는 나프틸기이다According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 R403 내지 R406는 서로 같거나 상이하고, 각가 독립적으로 페닐기이다. According to an exemplary embodiment of the present specification, R403 to R406 are the same as or different from each other, and each independently represents a phenyl group.
본 명세서의 일 실시상태에 따르면, 상기 L403은 탄소수 6 내지 30의 아릴렌기, 또는 아릴렌기로 치환된 탄소수 3 내지 30의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 L403은 페닐렌기, 2가의 비페닐기, 또는 아릴기로 치환 또는 비치환된 2가의 카바졸기이다.According to an exemplary embodiment of the present specification, L403 is a divalent carbazole group unsubstituted or substituted with a phenylene group, a divalent biphenyl group, or an aryl group.
본 명세서의 일 실시상태에 따르면, 상기 L403은 페닐렌기, 또는 페닐기로 치환된 2가의 카바졸기이다.According to an exemplary embodiment of the present specification, L403 is a phenylene group or a divalent carbazole group substituted with a phenyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 HT-2는 하기 화합물이다.According to an exemplary embodiment of the present specification, the formula HT-2 is the following compound.
Figure PCTKR2023008159-appb-img-000011
Figure PCTKR2023008159-appb-img-000011
정공수송층과 발광층 사이에 전자억제층이 구비될 수 있다. 상기 전자억제층은 전술한 스피로 화합물 또는 당 기술분야에 알려져 있는 재료가 사용될 수 있다.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.
본 명세서의 일 실시상태에 따르면, 상기 전자억제층은 상기 화학식 1 이외의 다른 재료를 포함하는 경우, 하기 화학식 EB-1로 표시되는 화합물을 포함하나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, 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.
[화학식 EB-1][Formula EB-1]
Figure PCTKR2023008159-appb-img-000012
Figure PCTKR2023008159-appb-img-000012
상기 화학식 EB-1에 있어서,In the formula EB-1,
R318 내지 R320는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 헤테로아릴기; 및 이들의 조합으로 이루어진 군에서 선택되는 어느 하나이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하고,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,
r318은 1 내지 5의 정수이며, 상기 r318이 2 이상인 경우, 2 이상의 상기 R318은 서로 같거나 상이하며,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,
r319는 1 내지 5의 정수이고, 상기 r319가 2 이상인 경우, 2 이상의 상기 R319는 서로 같거나 상이하다.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.
본 명세서의 일 실시상태에 따르면, 상기 R318은 치환 또는 비치환된 아릴기; 치환 또는 비치환된 헤테로아릴기; 및 이들의 조합으로 이루어진 군에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present specification, R318 is a substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of combinations thereof.
본 명세서의 일 실시상태에 따르면, 상기 R318은 카바졸기; 페닐기; 바이페닐기; 또는 트리페닐렌이다.According to an exemplary embodiment of the present specification, R318 is a carbazole group; phenyl group; Biphenyl group; Or triphenylene.
본 명세서의 일 실시상태에 따르면, 상기 R318은 트리페닐렌이다.According to an exemplary embodiment of the present specification, R318 is triphenylene.
본 명세서의 일 실시상태에 따르면, 상기 R319 및 R320은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이거나, 인접한 기와 서로 결합하여 알킬기로 치환된 방향족탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 R319 및 R320은 서로 같거나 상이하고, 각각 독립적으로 페닐기이거나, 인접한 기와 서로 결합하여 메틸기로 치환된 인덴을 형성한다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 R319 및 R320은 페닐기이다.According to an exemplary embodiment of the present specification, R319 and R320 are phenyl groups.
본 명세서의 일 실시상태에 따르면, 상기 화학식 EB-1은 하기 화합물로 표시된다.According to an exemplary embodiment of the present specification, the formula EB-1 is represented by the following compound.
Figure PCTKR2023008159-appb-img-000013
Figure PCTKR2023008159-appb-img-000013
상기 발광층은 적색, 녹색 또는 청색을 발광할 수 있으며, 인광 물질 또는 형광 물질로 이루어질 수 있다. 상기 발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 구체적인 예로는 8-히드록시-퀴놀린 알루미늄 착물(Alq3); 카르바졸 계열 화합물; 이량체화 스티릴(dimerized styryl) 화합물; BAlq; 10-히드록시벤조 퀴놀린-금속 화합물; 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물; 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자; 스피로(spiro) 화합물; 폴리플루오렌, 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다.The light-emitting layer may emit red, green, or blue light and may be 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.
발광층의 호스트 재료로는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. 구체적으로 축합 방향족환 유도체로는 안트라센 유도체, 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고, 헤테로환 함유 화합물로는 카바졸 유도체, 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이에 한정되지 않는다.Host materials for the light-emitting layer include condensed aromatic ring derivatives or heterocycle-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type compounds. These include, but are not limited to, furan compounds and pyrimidine derivatives.
본 명세서의 일 실시상태에 따르면, 상기 호스트는 하기 화학식 H-1로 표시되는 화합물을 포함하나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the host includes, but is not limited to, a compound represented by the following formula H-1.
[화학식 H-1][Formula H-1]
Figure PCTKR2023008159-appb-img-000014
Figure PCTKR2023008159-appb-img-000014
상기 화학식 H-1에 있어서,In the above formula H-1,
L20 및 L21은 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 2가의 헤테로고리기이고,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 및 Ar21은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,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,
R201은 수소; 중수소; 할로겐기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,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,
r201은 1 내지 8의 정수이며, 상기 r201이 2 이상인 경우, 2 이상의 R201은 서로 같거나 상이하다.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.
본 명세서의 일 실시상태에 있어서, 상기 L20 및 L21은 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기; 또는 탄소수 2 내지 30의 단환 또는 다환의 2가의 헤테로고리기이다.In an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 있어서, 상기 L20 및 L21은 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 중수소로 치환 또는 비치환된 페닐렌기; 중수소로 치환 또는 비치환된 바이페닐릴렌기; 중수소로 치환 또는 비치환된 나프틸렌기; 2가의 디벤조퓨란기; 또는 2가의 디벤조티오펜기이다.In an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar20 및 Ar21은 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리기다.In an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar20 및 Ar21은 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 20의 단환 내지 4환의 아릴기; 또는 치환 또는 비치환된 탄소수 6 내지 20의 단환 내지 4환의 헤테로고리기다.In an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar20 및 Ar21은 서로 동일하거나 상이하고, 각각 독립적으로 중수소, 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 페닐기; 중수소, 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 바이페닐기; 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 나프틸기; 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 티오펜기; 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 디벤조퓨란기; 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 나프토벤조퓨란기; 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 디벤조티오펜기; 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 나프토벤조티오펜기이다.In an exemplary embodiment of the present specification, 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 to 20 carbon atoms; Dibenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or it is a naphthobenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 Ar20 및 Ar21은 서로 동일하거나 상이하고, 각각 독립적으로 중수소로 치환 또는 비치환된 페닐기; 중수소로 치환 또는 비치환된 바이페닐기; 터페닐기; 중수소로 치환 또는 비치환된 나프틸기; 페닐기로 치환 또는 비치환된 티오펜기; 페난트렌기; 디벤조퓨란기; 나프토벤조퓨란기; 디벤조티오펜기; 또는 나프토벤조티오펜기이다.In an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 있어서, 상기 Ar20 및 Ar21은 나프틸기이다.In one embodiment of the present specification, Ar20 and Ar21 are naphthyl groups.
본 명세서의 일 실시상태에 있어서, 상기 Ar20 및 Ar21은 서로 동일하거나 상이하고, 각각 독립적으로 1-나프틸기, 또는 2-나프틸기이다.In an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 R201은 수소이다.According to an exemplary embodiment of the present specification, R201 is hydrogen.
본 명세서의 일 실시상태에 따르면, 상기 화학식 H-1은 하기 화합물로 표시된다.According to an exemplary embodiment of the present specification, the formula H-1 is represented by the following compound.
Figure PCTKR2023008159-appb-img-000015
Figure PCTKR2023008159-appb-img-000015
발광층이 적색 발광을 하는 경우, 발광 도펀트로는 PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum)와 같은 인광 물질이나, Alq3(tris(8-hydroxyquinolino)aluminum)와 같은 형광 물질이 사용될 수 있으나, 이에만 한정된 것은 아니다. 발광층이 녹색 발광을 하는 경우, 발광 도펀트로는 Ir(ppy)3(fac tris(2-phenylpyridine)iridium)와 같은 인광물질이나, Alq3(tris(8-hydroxyquinolino)aluminum)와 같은 형광 물질이 사용될 수 있으나, 이에만 한정된 것은 아니다. 발광층이 청색 발광을 하는 경우, 발광 도펀트로는 (4,6-F2ppy)2Irpic와 같은 인광 물질이나, spiro-DPVBi, spiro-6P, 디스틸벤젠(DSB), 디스트릴아릴렌(DSA), PFO계 고분자, PPV계 고분자와 같은 형광 물질이 사용될 수 있으나, 이에만 한정된 것은 아니다.When the light-emitting layer emits red light, 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. If the light-emitting layer emits green light, 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. However, it is not limited to this. If the light-emitting layer emits blue light, 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.
본 명세서의 일 실시상태에 따르면, 상기 도펀트는 하기 화학식 D-1로 표시되는 화합물을 포함하나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the dopant includes, but is not limited to, a compound represented by the following formula D-1.
[화학식 D-1][Formula D-1]
Figure PCTKR2023008159-appb-img-000016
Figure PCTKR2023008159-appb-img-000016
상기 화학식 D-1에 있어서,In Formula D-1,
T1 내지 T6은 서로 같거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,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 및 t6은 각각 1 내지 4의 정수이며,t5 and t6 are each integers from 1 to 4,
상기 t5가 2 이상인 경우, 상기 2 이상의 T5는 서로 같거나 상이하고,When t5 is 2 or more, the 2 or more T5 are the same or different from each other,
상기 t6가 2 이상인 경우, 상기 2 이상의 T6는 서로 같거나 상이하다.When the t6 is 2 or more, the 2 or more T6s are the same or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 T1 내지 T6은 서로 같거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 T1 내지 T6은 서로 같거나 상이하고, 각각 독립적으로 수소; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 니트릴기, 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 T1 내지 T6은 서로 같거나 상이하고, 각각 독립적으로 수소; 메틸기로 치환된 페닐기; 또는 터부틸기로 치환된 디벤조퓨란기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 화학식 D-1는 하기 화합물로 표시된다.According to an exemplary embodiment of the present specification, Formula D-1 is represented by the following compound.
Figure PCTKR2023008159-appb-img-000017
Figure PCTKR2023008159-appb-img-000017
전자수송층과 발광층 사이에 정공억제층이 구비될 수 있으며, 당 기술분야에 알려져 있는 재료가 사용될 수 있다.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.
상기 전자수송층은 전자의 수송을 원활하게 하는 역할을 할 수 있다. 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 Al 착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다. 전자수송층의 두께는 1 내지 50nm일 수 있다. 전자수송층의 두께가 1nm 이상이면, 전자 수송 특성이 저하되는 것을 방지할 수 있는 이점이 있고, 50nm 이하이면, 전자수송층의 두께가 너무 두꺼워 전자의 이동을 향상시키기 위해 구동전압이 상승되는 것을 방지할 수 있는 이점이 있다.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. If 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.
상기 전자주입층은 전자의 주입을 원활하게 하는 역할을 할 수 있다. 전자 주입 물질로는 전자를 수송하는 능력을 갖고, 음극으로부터의 전자주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며, 발광층에서 생성된 여기자의 정공 주입층에의 이동을 방지하고, 또한, 박막형성능력이 우수한 화합물이 바람직하다. 구체적으로는 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 함질소 5원환 유도체 등이 있으나, 이에 한정되지 않는다. The electron 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. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, metals. These include, but are not limited to, complex compounds and nitrogen-containing five-membered ring derivatives.
본 명세서의 일 실시상태에 따르면, 상기 전자주입 및 수송층은 하기 화학식 ET-1의 화합물을 포함하나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the electron injection and transport layer includes, but is not limited to, a compound of the following formula ET-1.
[화학식 ET-1][Formula ET-1]
Figure PCTKR2023008159-appb-img-000018
Figure PCTKR2023008159-appb-img-000018
상기 화학식 ET-1에 있어서,In the formula ET-1,
Z11 내지 Z13 중 적어도 하나는 N이고, 나머지는 CH이고,At least one of Z11 to Z13 is N, the others are CH,
L601는 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L601 is directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar601 내지 Ar603은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,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,
l601은 1 내지 5의 정수이며, 상기 l601이 2 이상인 경우, 상기 2 이상의 L601은 서로 같거나 상이하다.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.
본 명세서의 일 실시상태에 따르면, 상기 L601은 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기이다.According to an exemplary embodiment of the present specification, L601 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L601은 페닐렌기; 바이페닐릴렌기; 또는 나프틸렌기이다.According to an exemplary embodiment of the present specification, L601 is a phenylene group; Biphenylylene group; Or it is a naphthylene group.
본 명세서의 일 실시상태에 따르면, 상기 Ar601 및 Ar602는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 Ar601 및 Ar602는 페닐기이다.According to an exemplary embodiment of the present specification, Ar601 and Ar602 are phenyl groups.
본 명세서의 일 실시상태에 따르면, 상기 Ar603은 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar603 is a heteroaryl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar603은 페닐기로 치환 또는 비치환된 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar603 is a heteroaryl group substituted or unsubstituted with a phenyl group.
본 명세서의 일 실시상태에 따르면, 상기 Ar603은 페닐기로 치환 또는 비치환된 트리아진기이다.According to an exemplary embodiment of the present specification, Ar603 is a triazine group substituted or unsubstituted by a phenyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 ET-1은 하기 화합물로 표시된다.According to an exemplary embodiment of the present specification, the formula ET-1 is represented by the following compound.
Figure PCTKR2023008159-appb-img-000019
Figure PCTKR2023008159-appb-img-000019
본 명세서의 일 실시상태에 따르면, 상기 전자주입 및 수송층은 상기 화학식 ET-1의 화합물과 금속착체를 포함한다. According to an exemplary embodiment of the present specification, the electron injection and transport layer includes a compound of the formula ET-1 and a metal complex.
상기 금속 착체 화합물로서는 8-하이드록시퀴놀리나토 리튬, 비스(8-하이드록시퀴놀리나토)아연, 비스(8-하이드록시퀴놀리나토)구리, 비스(8-하이드록시퀴놀리나토)망간, 트리스(8-하이드록시퀴놀리나토)알루미늄, 트리스(2-메틸-8-하이드록시퀴놀리나토)알루미늄, 트리스(8-하이드록시퀴놀리나토)갈륨, 비스(10-하이드록시벤조[h]퀴놀리나토)베릴륨, 비스(10-하이드록시벤조[h]퀴놀리나토)아연, 비스(2-메틸-8-퀴놀리나토)클로로갈륨, 비스(2-메틸-8-퀴놀리나토)(o-크레졸라토)갈륨, 비스(2-메틸-8-퀴놀리나토)(1-나프톨라토)알루미늄, 비스(2-메틸-8-퀴놀리나토)(2-나프톨라토)갈륨 등이 있으나, 이에 한정되지 않는다.Examples of the metal complex 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.
상기 정공차단층은 정공의 음극 도달을 저지하는 층으로, 일반적으로 전자주입층과 동일한 조건으로 형성될 수 있다. 구체적으로 옥사디아졸 유도체나 트리아졸 유도체, 페난트롤린 유도체, BCP, 알루미늄 착물 (aluminum complex) 등이 있으나, 이에 한정되지 않는다.The hole blocking layer 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.
본 명세서의 일 실시상태에 따르면, 상기 정공차단층은 하기 화학식 HB-1의 화합물을 포함하나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the hole blocking layer includes, but is not limited to, a compound of the following formula HB-1.
[화학식 HB-1][Formula HB-1]
Figure PCTKR2023008159-appb-img-000020
Figure PCTKR2023008159-appb-img-000020
상기 화학식 HB-1에 있어서,In the formula HB-1,
Z101 내지 Z103 중 적어도 하나는 N이고, 나머지는 CH이고,At least one of Z101 to Z103 is N, the others are CH,
L61는 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L61 is directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar61 내지 Ar63은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.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.
본 명세서의 일 실시상태에 따르면, 상기 L61은 직접결합, 또는 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기이다.According to an exemplary embodiment of the present specification, L61 is a direct bond, or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L61은 직접결합; 페닐렌기; 바이페닐릴렌기; 또는 나프틸렌기이다.According to an exemplary embodiment of the present specification, L61 is a direct bond; phenylene group; Biphenylylene group; Or it is a naphthylene group.
본 명세서의 일 실시상태에 따르면, 상기 Ar61 및 Ar62는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 Ar61 및 Ar62는 비페닐기이다.According to an exemplary embodiment of the present specification, Ar61 and Ar62 are biphenyl groups.
본 명세서의 일 실시상태에 따르면, 상기 Ar63은 탄소수 6 내지 30의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, Ar63 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar63은 스피로비플루오렌이다.According to an exemplary embodiment of the present specification, Ar63 is spirobifluorene.
본 명세서의 일 실시상태에 따르면, 상기 화학식 HB-1은 하기 화합물로 표시된다. According to an exemplary embodiment of the present specification, the formula HB-1 is represented by the following compound.
Figure PCTKR2023008159-appb-img-000021
Figure PCTKR2023008159-appb-img-000021
본 발명에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light emitting device according to the present invention may be a front emitting type, a back emitting type, or a double-sided emitting type depending on the material used.
본 발명의 유기 발광 소자는 전술한 화합물을 이용하여 한 층 이상의 유기물층을 형성하는 것을 제외하고는, 통상의 유기 발광 소자의 제조방법 및 재료에 의하여 제조될 수 있다.The organic light emitting device of the present invention can be manufactured 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.
상기 화학식 1의 화합물의 제조방법 및 이들을 이용한 유기 발광 소자의 제조는 이하의 실시예에서 구체적으로 설명한다. 그러나, 하기 실시예는 본 발명을 예시하기 위한 것이며, 본 발명의 범위가 이들에 의하여 한정되는 것은 아니다.The method for producing the compound of Formula 1 and the production of organic light-emitting devices using the same will be described in detail in the examples below. However, the following examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.
하기 반응식에 있어서, 치환기의 종류 및 개수는 당업자가 공지된 출발물질을 적절히 선택함에 따라 다양한 종류의 중간체를 합성할 수 있다. 반응 종류 및 반응 조건은 당기술분야에 알려져 있는 것들이 이용될 수 있다. In the following reaction formula, various types of intermediates can be synthesized by appropriately selecting starting materials known to those skilled in the art regarding the type and number of substituents. Reaction types and reaction conditions known in the art can be used.
제조예 1Manufacturing Example 1
Figure PCTKR2023008159-appb-img-000022
Figure PCTKR2023008159-appb-img-000022
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 A(30g, 75.32mmol), 및 화합물 B(25.69g, 76.82mmol)을 toluene 300 mL에 완전히 녹인 후 NaOtBu(10.13g, 105.45mmol)을 첨가하고, [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.27g, 0.37mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 여과하여 염기를 제거한 후 톨루엔을 감압농축 시키고 에틸아세테이트 240 mL으로 재결정하여 화합물 C (30.93g, 수율:63%)를 제조하였다.Compound A (30 g, 75.32 mmol) and Compound B (25.69 g, 76.82 mmol) were completely dissolved in 300 mL of toluene in a 500 mL round bottom flask under a nitrogen atmosphere, then NaOtBu (10.13 g, 105.45 mmol) was added, [1 ,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.27g, 0.37mmol) was added and heated and stirred for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, toluene was concentrated under reduced pressure and recrystallized with 240 mL of ethyl acetate to prepare Compound C (30.93 g, yield: 63%).
MS[M+H]+= 652MS[M+H] + = 652
제조예 2Production example 2
Figure PCTKR2023008159-appb-img-000023
Figure PCTKR2023008159-appb-img-000023
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 C(15g, 23.01mmol), 및 화합물D(3.61g, 23.01mmol)을 톨루엔 220 mL에 완전히 녹인 후 NaOtBu(3.09g, 32.21mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.06g, 0.11mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 여과하여 염기를 제거한 후 톨루엔을 감압농축 시키고 에틸아세테이트 240 mL으로 재결정하여 화합물 1 (14.07g, 수율:84%)를 제조하였다.Compound C (15 g, 23.01 mmol) and Compound D (3.61 g, 23.01 mmol) were completely dissolved in 220 mL of toluene in a 500 mL round bottom flask under a nitrogen atmosphere, then NaOtBu (3.09 g, 32.21 mmol) was added, and Bis ( After adding tri- tert -butylphosphine) palladium(0) (0.06g, 0.11mmol), it was heated and stirred for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, toluene was concentrated under reduced pressure and recrystallized with 240 mL of ethyl acetate to prepare Compound 1 (14.07g, yield: 84%).
MS[M+H]+= 728MS[M+H] + = 728
제조예 3Production example 3
Figure PCTKR2023008159-appb-img-000024
Figure PCTKR2023008159-appb-img-000024
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 C(15g, 23.01mmol), 및 화합물 E(5.36g, 23.01mmol)을 톨루엔 220 mL에 완전히 녹인 후 NaOtBu(3.09g, 32.21mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.06g, 0.11mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 여과하여 염기를 제거한 후 톨루엔을 감압농축 시키고 에틸아세테이트 240 mL으로 재결정하여 화합물 2 (17.21g, 수율:93%)를 제조하였다.Compound C (15 g, 23.01 mmol) and Compound E (5.36 g, 23.01 mmol) were completely dissolved in 220 mL of toluene in a 500 mL round bottom flask under a nitrogen atmosphere, then NaOtBu (3.09 g, 32.21 mmol) was added, and Bis ( After adding tri- tert -butylphosphine) palladium(0) (0.06g, 0.11mmol), it was heated and stirred for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, toluene was concentrated under reduced pressure and recrystallized with 240 mL of ethyl acetate to prepare Compound 2 (17.21 g, yield: 93%).
MS[M+H]+= 804MS[M+H] + = 804
제조예 4Production example 4
Figure PCTKR2023008159-appb-img-000025
Figure PCTKR2023008159-appb-img-000025
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 C(15g, 23.01mmol), 및 화합물 F(7.11g, 23.01mmol)을 톨루엔 220 mL에 완전히 녹인 후 NaOtBu(3.09g, 32.21mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.06g, 0.11mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 여과하여 염기를 제거한 후 톨루엔을 감압농축 시키고 에틸아세테이트 240 mL으로 재결정하여 화합물 3 (19.04g, 수율:94%)를 제조하였다.Compound C (15 g, 23.01 mmol) and Compound F (7.11 g, 23.01 mmol) were completely dissolved in 220 mL of toluene in a 500 mL round bottom flask under a nitrogen atmosphere, then NaOtBu (3.09 g, 32.21 mmol) was added, and Bis ( After adding tri- tert -butylphosphine) palladium(0) (0.06g, 0.11mmol), it was heated and stirred for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, toluene was concentrated under reduced pressure and recrystallized with 240 mL of ethyl acetate to prepare Compound 3 (19.04 g, yield: 94%).
MS[M+H]+= 880MS[M+H] + = 880
제조예 5Production example 5
Figure PCTKR2023008159-appb-img-000026
Figure PCTKR2023008159-appb-img-000026
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 C(15g, 23.01mmol), 및 화합물 G(6.51g, 23.01mmol)을 톨루엔 220 mL에 완전히 녹인 후 NaOtBu(3.09g, 32.21mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.06g, 0.11mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 여과하여 염기를 제거한 후 톨루엔을 감압농축 시키고 에틸아세테이트 240 mL으로 재결정하여 화합물 4 (17.49g, 수율:89%)를 제조하였다.Compound C (15 g, 23.01 mmol) and Compound G (6.51 g, 23.01 mmol) were completely dissolved in 220 mL of toluene in a 500 mL round bottom flask under a nitrogen atmosphere, then NaOtBu (3.09 g, 32.21 mmol) was added, and Bis ( After adding tri- tert -butylphosphine) palladium(0) (0.06g, 0.11mmol), it was heated and stirred for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, toluene was concentrated under reduced pressure and recrystallized with 240 mL of ethyl acetate to prepare Compound 4 (17.49 g, yield: 89%).
MS[M+H]+= 854MS[M+H] + = 854
제조예 6Production example 6
Figure PCTKR2023008159-appb-img-000027
Figure PCTKR2023008159-appb-img-000027
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 C(15g, 23.01mmol), 및 화합물 H(7.67g, 23.01mmol)을 톨루엔 220 mL에 완전히 녹인 후 NaOtBu(3.09g, 32.21mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.06g, 0.11mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 여과하여 염기를 제거한 후 톨루엔을 감압농축 시키고 에틸아세테이트 240 mL으로 재결정하여 화합물 5 (18.93g, 수율:91%)를 제조하였다.Compound C (15 g, 23.01 mmol) and Compound H (7.67 g, 23.01 mmol) were completely dissolved in 220 mL of toluene in a 500 mL round bottom flask under a nitrogen atmosphere, then NaOtBu (3.09 g, 32.21 mmol) was added, and Bis ( After adding tri- tert -butylphosphine) palladium(0) (0.06g, 0.11mmol), it was heated and stirred for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, toluene was concentrated under reduced pressure and recrystallized with 240 mL of ethyl acetate to prepare Compound 5 (18.93 g, yield: 91%).
MS[M+H]+= 904MS[M+H] + = 904
제조예 7Production example 7
Figure PCTKR2023008159-appb-img-000028
Figure PCTKR2023008159-appb-img-000028
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 C(15g, 23.01mmol), 및 화합물 I(6.28g, 23.01mmol)을 톨루엔 220 mL에 완전히 녹인 후 NaOtBu(3.09g, 32.21mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.06g, 0.11mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 여과하여 염기를 제거한 후 톨루엔을 감압농축 시키고 에틸아세테이트 240 mL으로 재결정하여 화합물 6 (15.73g, 수율:81%)를 제조하였다.Compound C (15 g, 23.01 mmol) and Compound I (6.28 g, 23.01 mmol) were completely dissolved in 220 mL of toluene in a 500 mL round bottom flask under a nitrogen atmosphere, then NaOtBu (3.09 g, 32.21 mmol) was added, and Bis ( After adding tri- tert -butylphosphine) palladium(0) (0.06g, 0.11mmol), it was heated and stirred for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, toluene was concentrated under reduced pressure and recrystallized with 240 mL of ethyl acetate to prepare Compound 6 (15.73 g, yield: 81%).
MS[M+H]+= 844MS[M+H] + = 844
제조예 8 Production example 8
Figure PCTKR2023008159-appb-img-000029
Figure PCTKR2023008159-appb-img-000029
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 C(15g, 23.01mmol), 및 화합물 J(4.76g, 23.01mmol)을 톨루엔 220 mL에 완전히 녹인 후 NaOtBu(3.09g, 32.21mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.06g, 0.11mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 여과하여 염기를 제거한 후 톨루엔을 감압농축 시키고 에틸아세테이트 240 mL으로 재결정하여 화합물 7 (14.14g, 수율:79%)를 제조하였다.Compound C (15 g, 23.01 mmol) and Compound J (4.76 g, 23.01 mmol) were completely dissolved in 220 mL of toluene in a 500 mL round bottom flask under a nitrogen atmosphere, then NaOtBu (3.09 g, 32.21 mmol) was added, and Bis ( After adding tri-tert-butylphosphine) palladium(0) (0.06g, 0.11mmol), it was heated and stirred for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, toluene was concentrated under reduced pressure and recrystallized with 240 mL of ethyl acetate to prepare Compound 7 (14.14 g, yield: 79%).
MS[M+H]+= 778MS[M+H]+= 778
실시예 1-1Example 1-1
ITO(indium tin oxide)가 1,000Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀러포어사(Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 수송시켰다.A glass substrate coated with a thin film of ITO (indium tin oxide) with a thickness of 1,000 Å was placed in distilled water with a detergent dissolved in it and washed ultrasonically. At this time, 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. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, it was ultrasonic washed with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned for 5 minutes using oxygen plasma and then transported to a vacuum evaporator.
이렇게 준비된 양극인 ITO 투명 전극 위에 하기 화합물 HI1 및 하기 화합물 HI2의 화합물을 98:2(몰비)의 비가 되도록 100Å의 두께로 열 진공 증착하여 정공주입층을 형성하였다. 상기 정공주입층 위에 하기 화학식 HT1으로 표시되는 화합물(1150Å)을 진공 증착하여 정공수송층을 형성하였다. 이어서, 상기 정공수송층 위에 막 두께 50Å으로 화합물 1을 진공 증착하여 전자억제층을 형성하였다. 이어서, 상기 전자억제층 위에 막 두께 200Å으로 하기 화학식 BH로 표시되는 화합물 및 하기 화학식 BD로 표시되는 화합물을 25:1의 중량비로 진공증착하여 발광층을 형성하였다. 상기 발광층 위에 막 두께 50Å으로 하기 화학식 HB1으로 표시되는 화합물을 진공 증착하여 정공저지층을 형성하였다. 이어서, 상기 정공저지층 위에 하기 화학식 ET1으로 표시되는 화합물과 하기 화학식 LiQ로 표시되는 화합물을 1:1의 중량비로 진공증착하여 310Å의 두께로 전자 주입 및 수송층을 형성하였다. 상기 전자 주입 및 수송층 위에 순차적으로 12Å두께로 리튬플로라이드(LiF)와 1,000Å 두께로 알루미늄을 증착하여 음극을 형성하였다. On the ITO transparent electrode, which is the anode prepared in this way, the compounds of the following compound HI1 and the following compound HI2 were thermally vacuum deposited to a thickness of 100 Å 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 Å) represented by the following chemical formula HT1 on the hole injection layer. Next, Compound 1 was vacuum deposited to a film thickness of 50 Å on the hole transport layer to form an electron blocking layer. Subsequently, 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 Å 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 Å on the light emitting layer. Next, 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 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1,000 Å on the electron injection and transport layer.
Figure PCTKR2023008159-appb-img-000030
Figure PCTKR2023008159-appb-img-000030
상기의 과정에서 유기물의 증착속도는 0.4~0.7Å/sec를 유지하였고, 음극의 리튬플로라이드는 0.3Å/sec, 알루미늄은 2Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 2X10-7 ~ 5X10-6 torr를 유지하여, 유기 발광 소자를 제작하였다.In the above process, the deposition rate of organic matter was maintained at 0.4~0.7Å/sec, the deposition rate of lithium fluoride of the cathode was maintained at 0.3Å/sec, and the deposition rate of aluminum was maintained at 2Å/sec, and the vacuum degree during deposition was 2X10 -7 ~ An organic light emitting device was manufactured by maintaining 5X10 -6 torr.
실시예 1-2 내지 실시예 1-7Example 1-2 to Example 1-7
화합물 1 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는, 상기 실시예 1-1과 동일한 방법으로 유기 발광 소자를 제조하였다. 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.
비교예 1-1 내지 1-7Comparative Examples 1-1 to 1-7
화합물 1 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는, 상기 실시예 1-1과 동일한 방법으로 유기 발광 소자를 제조하였다. 하기 표 1에서 사용한 EB2 내지 EB8 의 화합물은 하기와 같다.
Figure PCTKR2023008159-appb-img-000031
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.
Figure PCTKR2023008159-appb-img-000031
Figure PCTKR2023008159-appb-img-000032
Figure PCTKR2023008159-appb-img-000032
실험예 1Experimental Example 1
상기 실시예 및 비교예에서 제조한 유기 발광 소자에 전류를 인가하였을 때, 전압, 효율, 색좌표 및 수명을 측정하고 그 결과를 하기 표 1에 나타내었다. T95은 휘도가 초기 휘도(1600 nit)에서 95%로 감소되는데 소요되는 시간을 의미한다.When current was applied to the organic light-emitting devices manufactured in the examples and comparative examples, the voltage, efficiency, color coordinate, and lifespan were measured, and the results are shown in Table 1 below. T95 refers to the time it takes for the luminance to decrease from the initial luminance (1600 nit) to 95%.
화합물
(전자억제층)compound
(electron suppression layer) 		전압
(V@10mA
/cm2)Voltage
(V@10mA
/cm 2 ) 		효율
(cd/A@10mA
/cm2)efficiency
(cd/A@10mA
/cm 2 ) 		색좌표
(x,y)Color coordinates
(x,y) 		T95
(hr)T95
(hr)
실시예 1-1Example 1-1 화합물 1 Compound 1 3.463.46 6.396.39 (0.143, 0.046)(0.143, 0.046) 212212
실시예 1-2Example 1-2 화합물 2 compound 2 3.473.47 6.436.43 (0.144, 0.046)(0.144, 0.046) 221221
실시예 1-3Example 1-3 화합물 3 Compound 3 3.543.54 6.466.46 (0.144, 0.045)(0.144, 0.045) 225225
실시예 1-4Example 1-4 화합물 4 Compound 4 3.523.52 6.516.51 (0.143, 0.046)(0.143, 0.046) 217217
실시예 1-5Examples 1-5 화합물 5 Compound 5 3.593.59 6.536.53 (0.143, 0.046)(0.143, 0.046) 216216
실시예 1-6Example 1-6 화합물 6 Compound 6 3.413.41 6.316.31 (0.144, 0.045)(0.144, 0.045) 205205
실시예 1-7Example 1-7 화합물 7 Compound 7 3.433.43 6.476.47 (0.145, 0.045)(0.145, 0.045) 210210
비교예 1-1Comparative Example 1-1 EB2EB2 3.823.82 6.226.22 (0.144, 0.045)(0.144, 0.045) 191191
비교예 1-2Comparative Example 1-2 EB3EB3 3.623.62 6.176.17 (0.143, 0.046)(0.143, 0.046) 178178
비교예 1-3Comparative Example 1-3 EB4EB4 3.813.81 6.206.20 (0.144, 0.046)(0.144, 0.046) 188188
비교예 1-4Comparative Example 1-4 EB5EB5 3.843.84 5.875.87 (0.143, 0.046)(0.143, 0.046) 174174
비교예 1-5Comparative Example 1-5 EB6EB6 3.603.60 6.286.28 (0.144, 0.046)(0.144, 0.046) 173173
비교예 1-6Comparative Example 1-6 EB7EB7 3.513.51 6.256.25 (0.144, 0.045)(0.144, 0.045) 171171
비교예 1-7Comparative Example 1-7 EB8EB8 3.723.72 5.965.96 (0.143, 0.045)(0.143, 0.045) 187187
상기 표 1에 나타난 바와 같이, 본 발명의 화합물을 전자억제층으로 사용한 유기 발광 소자는, 유기 발광 소자의 효율, 구동 전압 및 안정성 면에서 우수한 특성을 나타내었다.As shown in Table 1, 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.
특히, 화합물 EB2와 EB5를 사용한 비교예 1-1 및 1-4와 실시예 1-1 내지 1-7을 비교하면, 아민와 카바졸 사이의 비페닐 연결기와 카바졸의 결합위치에 따른 효과의 차이를 알 수 있다. In particular, when comparing Comparative Examples 1-1 and 1-4 using compounds EB2 and EB5 and Examples 1-1 to 1-7, the difference in effect depending on the binding position of the biphenyl linkage group between amine and carbazole and carbazole can be seen.
실시예 1-1 내지 1-7과 같이, 비페닐 연결기와 카바졸이 하나는 오쏘결합이고, 하나는 메타결합인 경우, 둘다 오쏘 결합인 비교예 1-1 보다 저전압, 고효율, 장수명의 특성을 보인다. As in Examples 1-1 to 1-7, when one of the biphenyl linking groups and the carbazole is an ortho bond and one is a meta bond, it has the characteristics of low voltage, high efficiency, and long life compared to Comparative Example 1-1, where both are ortho bonds. see.
비페닐 연결기과 카바졸이 파라결합을 한 화합물 EB-5를 사용한 비교예 1-5과 비교하면, 실시예 1-1 내지 1-7의 전압, 효율, 수명이 더 개선된 것을 확인할 수 있다. Compared with Comparative Example 1-5 using compound EB-5 in which a biphenyl linking group and carbazole are para-bonded, it can be seen that the voltage, efficiency, and lifespan of Examples 1-1 to 1-7 are further improved.
화합물 EB3 및 EB4의 경우, 아민에 하나의 카바졸만 결합하고 있다. 이들을 사용한 비교예 1-2 및 1-3과 비교할 경우, 실시예 1-1 내지 1-7의 전압, 효율, 수명이 개선된 것을 확인할 수 있다. In the case of compounds EB3 and EB4, only one carbazole is bound to the amine. When compared with Comparative Examples 1-2 and 1-3 using these, it can be seen that the voltage, efficiency, and lifespan of Examples 1-1 to 1-7 are improved.
화합물 EB6 내지 EB8은 아민에 결합된 비페닐 연결기에 카바졸기가 각각 오쏘-파라, 메타-파라, 메타-메타의 치환위치를 가진다. 화학식 1의 경우, 오쏘-메타의 치환위치를 가지고 있다. In compounds EB6 to EB8, 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.
화합물 EB6 내지 EB8을 사용한 비교예 1-5 내지 1-7은 실시예 1-1 내지 1-7과 비교하여, 전압과 효율도 떨어지만, 수명의 차이는 전압이나 효율의 차이보다 더 크다.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.
상기 표 1의 결과와 같이, 본 발명에 따른 화합물은 전자 차단 능력이 우수하여 유기 발광 소자에 적용 가능함을 확인할 수 있었다.As shown in Table 1 above, it was confirmed that the compound according to the present invention has excellent electron blocking ability and can be applied to organic light-emitting devices.
실시예 2-1 내지 실시예 2-7Example 2-1 to Example 2-7
화합물1 대신 EB1의 화합물을 사용하고, HT1 대신 하기 표 2에 기재된 화합물을 사용하는 것을 제외하고는, 상기 실시예 1-1과 동일한 방법으로 유기 발광 소자를 제조하였다. 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.
비교예 2-1 내지 2-7Comparative Examples 2-1 to 2-7
제조예 1의 화합물 대신 하기 표 2에 기재된 화합물을 사용하는 것을 제외하고는, 상기 실시예 1-1과 동일한 방법으로 유기 발광 소자를 제조하였다. 하기 표 2에서 사용한 HT2 내지 HT8의 화합물은 하기와 같다. 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.
Figure PCTKR2023008159-appb-img-000033
Figure PCTKR2023008159-appb-img-000033
Figure PCTKR2023008159-appb-img-000034
Figure PCTKR2023008159-appb-img-000034
실험예 2Experimental Example 2
상기 실시예 및 비교예에서 제조한 유기 발광 소자에 전류를 인가하였을 때, 전압, 효율, 색좌표 및 수명을 측정하고 그 결과를 하기 표 2에 나타내었다. T95은 휘도가 초기 휘도(1600 nit)에서 95%로 감소되는데 소요되는 시간을 의미한다.When current was applied to the organic light emitting devices manufactured in the above examples and comparative examples, the voltage, efficiency, color coordinate, and lifespan were measured, and the results are shown in Table 2 below. T95 refers to the time it takes for the luminance to decrease from the initial luminance (1600 nit) to 95%.
화합물
(정공수송층)compound
(Hole transport layer) 		전압
(V@10mA
/cm2)Voltage
(V@10mA
/cm 2 ) 		효율
(cd/A@10mA
/cm2)efficiency
(cd/A@10mA
/cm 2 ) 		색좌표
(x,y)Color coordinates
(x,y) 		T95
(hr)T95
(hr)
실시예 2-1Example 2-1 화합물 1 Compound 1 3.743.74 6.456.45 (0.143, 0.046)(0.143, 0.046) 202202
실시예 2-2Example 2-2 화합물 2 compound 2 3.723.72 6.566.56 (0.143, 0.045)(0.143, 0.045) 212212
실시예 2-3Example 2-3 화합물 3 Compound 3 3.783.78 6.556.55 (0.144, 0.046)(0.144, 0.046) 210210
실시예 2-4Example 2-4 화합물 4 Compound 4 3.773.77 6.716.71 (0.143, 0.046)(0.143, 0.046) 199199
실시예 2-5Example 2-5 화합물 5 Compound 5 3.693.69 6.636.63 (0.143, 0.045)(0.143, 0.045) 201201
실시예 2-6Example 2-6 화합물 6 Compound 6 3.583.58 6.426.42 (0.144, 0.045)(0.144, 0.045) 194194
실시예 2-7Example 2-7 화합물 7 Compound 7 3.543.54 6.506.50 (0.144, 0.046)(0.144, 0.046) 203203
비교예 2-1Comparative Example 2-1 HT2HT2 3.913.91 5.725.72 (0.144, 0.045)(0.144, 0.045) 172172
비교예 2-2Comparative Example 2-2 HT3HT3 3.843.84 6.216.21 (0.143, 0.046)(0.143, 0.046) 175175
비교예 2-3Comparative Example 2-3 HT4HT4 3.973.97 6.136.13 (0.143, 0.046)(0.143, 0.046) 171171
비교예 2-4Comparative Example 2-4 HT5HT5 3.923.92 5.895.89 (0.144, 0.045)(0.144, 0.045) 169169
비교예 2-5Comparative Example 2-5 HT6HT6 3.753.75 6.336.33 (0.143, 0.046)(0.143, 0.046) 186186
비교예 2-6Comparative Example 2-6 HT7HT7 3.663.66 5.965.96 (0.145, 0.045)(0.145, 0.045) 175175
비교예 2-7Comparative Example 2-7 HT8HT8 3.783.78 5.765.76 (0.144, 0.046)(0.144, 0.046) 178178
상기 표 2에 나타난 바와 같이, 본 발명의 화합물을 정공수송층으로 사용한 유기 발광 소자는, 유기 발광 소자의 효율, 구동 전압 및 안정성 면에서 우수한 특성을 나타내었다.As shown in Table 2, 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.
앞서 표 1과 같이 전자억제층에 사용한 경우뿐 아니라, 동일 물질을 정공수송층에 사용하였을 때에도, 비교예 2-1 내지 2-4보다 실시예 2-1 내지 2-7이 저전압, 고효율, 장수명의 특성을 가지는 것을 확인할 수 있다.Not only when used in the electron suppressing layer as shown in Table 1, but also when the same material was used in the hole transport layer, 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.
실시예 2-1 내지 2-7과 같이, 비페닐 연결기와 카바졸이 하나는 오쏘결합이고, 하나는 메타결합인 경우, 둘다 오쏘 결합인 비교예 2-1 보다 저전압, 고효율, 장수명의 특성을 보인다. As in Examples 2-1 to 2-7, when one of the biphenyl linking groups and the carbazole is an ortho bond and one is a meta bond, the characteristics of low voltage, high efficiency, and long life are achieved compared to Comparative Example 2-1, where both are ortho bonds. see.
비페닐 연결기과 카바졸이 파라결합을 한 화합물 HT5를 사용한 비교예 2-5과 비교하면, 실시예 2-1 내지 2-7의 전압, 효율, 수명이 더 개선된 것을 확인할 수 있다. Compared with Comparative Example 2-5 using compound HT5 in which a biphenyl linking group and carbazole are para-bonded, it can be seen that the voltage, efficiency, and lifespan of Examples 2-1 to 2-7 are further improved.
화합물 HT3 및 HT4의 경우, 아민에 하나의 카바졸만 결합하고 있다. 이들을 사용한 비교예 2-2 및 2-3과 비교할 경우, 실시예 2-1 내지 2-7의 전압, 효율, 수명이 개선된 것을 확인할 수 있다. In the case of compounds HT3 and HT4, only one carbazole is bound to the amine. When compared with Comparative Examples 2-2 and 2-3 using these, it can be seen that the voltage, efficiency, and lifespan of Examples 2-1 to 2-7 are improved.
화합물 EB6 내지 EB8은 아민에 결합된 비페닐 연결기에 카바졸기가 각각 오쏘-파라, 메타-파라, 메타-메타의 치환위치를 가진다. 화학식 1의 경우, 오쏘-메타의 치환위치를 가지고 있다. In compounds EB6 to EB8, 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.
화합물 EB6 내지 EB8을 사용한 비교예 2-5 내지 2-7은 실시예 2-1 내지 2-6과 비교하여, 전압과 효율도 떨어지만, 수명의 차이는 전압이나 효율의 차이보다 더 크다.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.
상기 표 2의 결과와 같이, 본 발명에 따른 화합물은 정공 수송 능력이 우수하여 유기 발광 소자에 적용 가능함을 확인할 수 있었다.As shown in Table 2 above, it was confirmed that the compound according to the present invention has excellent hole transport ability and can be applied to organic light-emitting devices.
이상을 통해 본 발명의 바람직한 실시예(전자억제층, 정공수송층)에 대하여 설명하였지만, 본 발명은 이에 한정되는 것이 아니고 특허청구범위와 발명의 상세한 설명의 범위 안에서 여러 가지로 변형하여 실시하는 것이 가능하고 이 또한 발명의 범주에 속한다.Although the preferred embodiments (electron blocking layer, hole transport layer) of the present invention have been described above, the present invention is not limited thereto and can be implemented with various modifications within the scope of the claims and detailed description of the invention. And this also falls under the category of invention.

Claims (11)

  1. 하기 화학식 1의 화합물: Compound of formula 1:
    [화학식 1][Formula 1]
    Figure PCTKR2023008159-appb-img-000035
    Figure PCTKR2023008159-appb-img-000035
    상기 화학식 1에 있어서,In Formula 1,
    L은 직접결합, 치환 또는 비치환된 아릴렌기, 또는 치환 또는 비치환된 헤테로아릴렌기이고,L is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
    Ar은 수소, 중수소, 할로겐기, 니트릴기, 치환 또는 비치환된 알킬기, 치환 또는 비치환되는 아릴기, 또는 치환 또는 비치환된 헤테로아릴기이다.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.
  2. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 1-1 내지 화학식 1-4 중 어느 하나인 것인 화합물: The method according to claim 1, wherein the formula 1 is any one of the following formulas 1-1 to 1-4:
    [화학식 1-1][Formula 1-1]
    Figure PCTKR2023008159-appb-img-000036
    Figure PCTKR2023008159-appb-img-000036
    [화학식 1-2][Formula 1-2]
    Figure PCTKR2023008159-appb-img-000037
    Figure PCTKR2023008159-appb-img-000037
    [화학식 1-3][Formula 1-3]
    Figure PCTKR2023008159-appb-img-000038
    Figure PCTKR2023008159-appb-img-000038
    [화학식 1-4][Formula 1-4]
    Figure PCTKR2023008159-appb-img-000039
    Figure PCTKR2023008159-appb-img-000039
    상기 화학식 1-1 내지 1-4에 있어서, Ar은 상기 화학식 1에서 정의한 것과 같고, In Formulas 1-1 to 1-4, Ar is as defined in Formula 1,
    a는 0 내지 3의 정수이고, a is an integer from 0 to 3,
    b는 1 내지 3의 정수이다. b is an integer from 1 to 3.
  3. 청구항 1에 있어서, 상기 L은 직접결합, 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기, 또는 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴렌기인 것인 화합물.The compound according to claim 1, wherein 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.
  4. 청구항 1에 있어서, 상기 L은 직접결합, 또는 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기인 것인 화합물.The compound according to claim 1, wherein L is a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
  5. 청구항 1에 있어서, 상기 L은 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기인 것인 화합물.The compound according to claim 1, wherein L is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
  6. 청구항 1에 있어서, 상기 L은 직접결합인 것인 화합물.The compound according to claim 1, wherein L is a direct bond.
  7. 청구항 1에 있어서, 상기 Ar은 치환 또는 비치환되는 탄소수 6 내지 30의 아릴기, 또는 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기인 것인 화합물.The compound according to claim 1, wherein Ar 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.
  8. 청구항 1에 있어서, 상기 화학식 1은 하기 구조식 중 어느 하나인 것인 화합물: The compound according to claim 1, wherein Formula 1 is one of the following structural formulas:
    Figure PCTKR2023008159-appb-img-000040
    Figure PCTKR2023008159-appb-img-000040
    Figure PCTKR2023008159-appb-img-000041
    Figure PCTKR2023008159-appb-img-000041
  9. 제1 전극; 상기 제1 전극과 대향하여 구비되는 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비되는 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상이 청구항 1 내지 8 중 어느 한 항에 따른 화합물을 포함하는 유기 발광 소자.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 includes the compound according to any one of claims 1 to 8. .
  10. 청구항 9에 있어서, 상기 유기물층은 정공주입층 또는 정공수송층을 포함하고, 상기 정공주입층 또는 정공수송층은 상기 화합물을 포함하는 유기 발광 소자.The organic light-emitting device of claim 9, wherein the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound.
  11. 청구항 9에 있어서, 상기 유기물층은 전자억제층을 포함하고, 상기 전자억제층은 상기 화합물을 포함하는 유기 발광 소자.The organic light emitting device of claim 9, wherein the organic material layer includes an electron blocking layer, and the electron blocking layer includes the compound.
PCT/KR2023/008159 2022-06-15 2023-06-14 Compound and organic light-emitting element comprising same WO2023244000A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2022-0072898 2022-06-15
KR20220072898 2022-06-15

Publications (1)

Publication Number Publication Date
WO2023244000A1 true WO2023244000A1 (en) 2023-12-21

Family

ID=89191627

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2023/008159 WO2023244000A1 (en) 2022-06-15 2023-06-14 Compound and organic light-emitting element comprising same

Country Status (2)

Country Link
KR (1) KR20230173035A (en)
WO (1) WO2023244000A1 (en)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20170036641A (en) * 2015-09-24 2017-04-03 주식회사 엘지화학 Compound and organic electronic device comprising the same
KR20190088029A (en) * 2018-01-17 2019-07-25 주식회사 엘지화학 Organic light emitting device
KR20200100299A (en) * 2019-02-18 2020-08-26 주식회사 이엘엠 Organic Light Emitting Material and Organic Light Emitting Diode Having The Same
CN111662225A (en) * 2019-03-08 2020-09-15 江苏三月光电科技有限公司 Organic compound containing pyrene and application thereof
KR20200144482A (en) * 2019-06-18 2020-12-29 주식회사 엘지화학 Novel compound and organic light emitting device comprising the same

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BR112017016392B1 (en) 2015-03-25 2023-02-23 National Cancer Center THERAPEUTIC AGENT FOR BILIARY DUCT CANCER

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20170036641A (en) * 2015-09-24 2017-04-03 주식회사 엘지화학 Compound and organic electronic device comprising the same
KR20190088029A (en) * 2018-01-17 2019-07-25 주식회사 엘지화학 Organic light emitting device
KR20200100299A (en) * 2019-02-18 2020-08-26 주식회사 이엘엠 Organic Light Emitting Material and Organic Light Emitting Diode Having The Same
CN111662225A (en) * 2019-03-08 2020-09-15 江苏三月光电科技有限公司 Organic compound containing pyrene and application thereof
KR20200144482A (en) * 2019-06-18 2020-12-29 주식회사 엘지화학 Novel compound and organic light emitting device comprising the same

Also Published As

Publication number Publication date
KR20230173035A (en) 2023-12-26

Similar Documents

Publication Publication Date Title
WO2020145725A1 (en) Compound and organic light-emitting element comprising same
WO2019143151A1 (en) Organic light-emitting diode
WO2017119792A1 (en) Compound and organic electronic element comprising same
WO2020138963A1 (en) Compound and organic light emitting diode comprising same
WO2020091521A1 (en) Compound and organic light emitting device comprising same
WO2018182297A1 (en) Benzocarbazole-based compound and organic light-emitting device comprising same
WO2020159279A1 (en) Polycyclic compound and organic light-emitting element comprising same
WO2019164218A1 (en) Polycyclic compound and organic light emitting diode comprising same
WO2020167001A1 (en) Boron-containing compound, and organic light-emitting element comprising same
WO2022080927A1 (en) Compound and organic light-emitting device comprising same
WO2019194615A1 (en) Polycyclic compound and organic electronic device comprising same
WO2019172647A1 (en) Heterocyclic compound and organic light emitting device comprising same
WO2018070840A1 (en) Organic electroluminescent device
WO2017073931A1 (en) Spiro-type compound and organic light emitting element comprising same
WO2021029709A1 (en) Organic light-emitting device
WO2020130623A1 (en) Polycyclic compound and organic light-emitting device comprising same
WO2020153652A1 (en) Compound, and organic light emitting element including same
WO2020153653A1 (en) Compound and organic light-emitting diode comprising same
WO2023244000A1 (en) Compound and organic light-emitting element comprising same
WO2024101921A1 (en) Compound and organic light-emitting element comprising same
WO2023177176A1 (en) Compound and organic light-emitting element comprising same
WO2022177359A1 (en) Compound and organic light-emitting device comprising same
WO2022177358A1 (en) Compound and organic light-emitting device comprising same
WO2023136586A1 (en) Compound and organic light-emitting device comprising same
WO2024101948A1 (en) Compound and organic light-emitting element comprising same

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 23824214

Country of ref document: EP

Kind code of ref document: A1