Compound and organic light-emitting device comprising same

Abstract

The present specification relates to a compound of chemical formula 1 and an organic light-emitting device comprising same. Efficiency, driving voltage, and stability can be improved through the balancing of holes and electrons of the organic light-emitting device by the chemical structure of the compound of chemical formula 1.

Description

Compound and organic light-emitting device containing the same

[0001] This application claims the benefit of Korean Patent Application No. 10-2024-0006838, filed with the Korean Intellectual Property Office on January 16, 2024, the entire contents of which are incorporated herein by reference.

[0002] The present specification relates to a compound and an organic light-emitting device comprising the same.

[0003] In this specification, an organic light-emitting device is a light-emitting device using an organic semiconductor material, and requires the exchange of holes and / or electrons between an electrode and the organic semiconductor material. Organic light-emitting devices can be broadly divided into two types according to their operating principles. First, a light-emitting device is a type in which excitons are formed in an organic layer by photons that enter 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 a current source (voltage source). Second, a light-emitting device is a type in which holes and / or electrons are injected into an organic semiconductor material layer forming an interface with the electrodes by applying voltage or current to two or more electrodes, and is operated by the injected electrons and holes.

[0004] In general, organic light emitting diodes (OLEDs) are devices that utilize the organic light emitting phenomenon, typically comprising an anode and a cathode, with an organic layer between them. These organic layers are often multilayered, composed of different materials, to enhance the efficiency and stability of the device. For example, they may include a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in this device, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode. Excitons form when the injected holes and electrons meet, and light is emitted when these excitons fall back to their ground state. These devices are known to exhibit characteristics such as self-luminescence, high brightness, high efficiency, low operating voltage, wide viewing angle, and high contrast.

[0005] Materials used as organic layers in organic light-emitting devices can be classified according to their function into light-emitting materials and charge-transport materials, such as hole-injecting materials, hole-transporting materials, electron-blocking materials, electron-transporting materials, and electron-injecting materials. Light-emitting materials include blue, green, and red light-emitting materials according to their emission color, as well as yellow and orange light-emitting materials required to realize better natural colors.

[0006] Furthermore, a host / dopant system can be used as a light-emitting material to enhance color purity and luminescence efficiency through energy transfer. This principle is achieved by mixing a small amount of a dopant with a smaller energy band gap and superior luminescence efficiency than the host, which primarily constitutes the light-emitting layer, into the light-emitting layer. This allows excitons generated in the host to be transported to the dopant, resulting in high-efficiency light emission. Since the wavelength of the host shifts to that of the dopant, light of a desired wavelength can be obtained depending on the type of dopant used.

[0007] In order to fully demonstrate the excellent characteristics of the aforementioned organic light-emitting device, the materials forming the organic layer within the device, such as hole injection materials, hole transport materials, luminescent materials, electron blocking materials, electron transport materials, and electron injection materials, must be supported by stable and efficient materials, and therefore, the development of new materials is continuously required.

[0008] The present specification describes compounds and organic light-emitting devices comprising the same.

[0009] One embodiment of the present disclosure provides a compound of the following chemical formula 1.

[0010] [Chemical Formula 1]

[0011]

[0012] In the above chemical formula 1,

[0013] X is O or S,

[0014] L1 and L2 are the same or different from each other, and each independently represents a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0015] Ar1 and Ar2 are the same or different, and each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted bicyclic heteroaryl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted ring group condensed therewith,

[0016] R1 to R4 are the same or different and are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0017] R5 is hydrogen or deuterium,

[0018] a is an integer from 1 to 4,

[0019] b is 1 or 2,

[0020] d is an integer from 1 to 3,

[0021] c is an integer from 1 to 5,

[0022] If a to d are each 2 or more, the substituents in the parentheses are the same or different,

[0023] r and q are integers from 1 to 10,

[0024] If r or q is 2 or more, the substituents in parentheses are the same or different.

[0025] In addition, according to one embodiment of the present invention, an organic light-emitting device is provided, including a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers includes the above-described compound.

[0026] The compound of the present invention can be used as a material for an organic layer of an organic light-emitting device. In particular, when used in a hole injection layer, hole transport layer, or electron blocking layer, it exhibits characteristics of low voltage, high efficiency, and / or long life.

[0027] Figures 1 and 2 illustrate examples of organic light-emitting devices according to the present invention.

[0028] [Explanation of symbols]

[0029] 1: Substrate

[0030] 2: First electrode

[0031] 3: Organic layer

[0032] 4: Second electrode

[0033] 5: Hole injection layer

[0034] 6: Hole transport layer

[0035] 7: Electron suppression layer

[0036] 8: Emissive layer

[0037] 9: Hole-suppressing layer

[0038] 10: Electron injection and transport layer

[0039] The following describes this specification in more detail.

[0040] The present specification relates to a compound of chemical formula 1 and an organic light-emitting device comprising the same, and can improve efficiency, operating voltage, and stability through the balance of holes and electrons in an organic light-emitting device according to the chemical structure of chemical formula 1.

[0041] The compound of the present invention has a substituted or unsubstituted biphenyl group positioned between dibenzofuran or dibenzothiophene and an amine group. This allows the hole transport properties of the compound to be controlled, thereby controlling the hole and electron balance of the device.

[0042] Additionally, the HOMO and LUMO energy levels of the compound can be adjusted by substituents connected to the amine group, thereby controlling the energy barrier with the organic layer.

[0043] In this specification, when a part is said to "include" a certain component, this does not mean that it excludes other components, but rather that it may include other components, unless otherwise specifically stated.

[0044] In this specification, when it is said that a member is located “on” another member, this includes not only cases where the member is in contact with the other member, but also cases where another member exists between the two members.

[0045] The term "substitution" above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of substitution is not limited as long as it is a position where the hydrogen atom is replaced, i.e., a position where the substituent can be replaced, and when two or more are substituted, the two or more substituents may be the same or different from each other.

[0046] The term "substituted or unsubstituted" as used herein means substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a nitrile group (-CN); a silyl group; a boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; and a substituted or unsubstituted heteroaryl group, or substituted with a substituent in which two or more substituents among the above-mentioned substituents are linked, or has no substituents. For example, "a substituent linked with two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent in which two phenyl groups are linked.

[0047] Examples of the above substituents are described below, but are not limited thereto.

[0048] In this specification, examples of halogen groups include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

[0049] In the present specification, a silyl group may be represented by the chemical formula -SiY1Y2Y3, wherein Y1, Y2, and Y3 may each be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

[0050] In the present specification, the boron group may be represented by the chemical formula -BY4Y5, wherein Y4 and Y5 may each be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. The boron group specifically includes, but is not limited to, a dimethyl boron group, a diethyl boron group, a t-butylmethyl boron group, a diphenyl boron group, a phenyl boron group, etc.

[0051] In the present specification, the alkyl group may be linear or branched, and the carbon number is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include, but are not limited to, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and the like.

[0052] In this 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 alkyl group has 1 to 30 carbon atoms, and the aryl group substituted with the alkyl group has 6 to 30 carbon atoms.

[0053] In the present specification, the amine group may be selected from the group consisting of -NH2; an alkylamine group; an N-alkylarylamine group; an arylamine group; an N-arylheteroarylamine group; an N-alkylheteroarylamine group and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group; a dimethylamine group; an ethylamine group; a diethylamine group; a phenylamine group; a naphthylamine group; a biphenylamine group; anthracenylamine group; a 9-methylanthracenylamine group; a diphenylamine group; a ditolylamine group; an N-phenyltolylamine group; a triphenylamine group; an N-phenylbiphenylamine group; an N-phenylnaphthylamine group; an N-biphenylnaphthylamine group; an N-naphthylfluorenylamine group; an N-phenylphenanthrenylamine group; an N-biphenylphenanthrenylamine group; an N-phenylfluorenylamine group; N-phenylterphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group, etc., but are not limited thereto.

[0054] In this specification, an N-alkylarylamine group means an amine group in which an alkyl group and an aryl group are substituted for N of the amine group.

[0055] In this specification, an N-arylheteroarylamine group means an amine group in which an aryl group and a heteroaryl group are substituted for N of the amine group.

[0056] In this specification, an N-alkylheteroarylamine group means an amine group in which an alkyl group and a heteroaryl group are substituted for N of the amine group.

[0057] In the present specification, the alkyl group among the alkylamine group, N-arylalkylamine group, alkylthioxy group, alkylsulfoxy group, and N-alkylheteroarylamine group is the same as the examples of the alkyl group described above. Specifically, the alkylthioxy group includes a methylthioxy group; an ethylthioxy group; a tert-butylthioxy group; a hexylthioxy group; an octylthioxy group, etc., and the alkylsulfoxy group includes, but is not limited to, a mesyl group; an ethylsulfoxy group; a propylsulfoxy group; a butylsulfoxy group, etc.

[0058] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. In one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. In another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. In another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, examples thereof include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

[0059] In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The monocyclic aryl group may be, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, etc. The polycyclic aryl group may be, but is not limited to, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenylene group, a chrysenyl group, a fluorenyl group, etc.

[0060] In this specification, the arylene group is as defined in the above aryl group, except that it is a divalent group.

[0061] In the present specification, a heteroaryl group is a ring group containing at least one of N, O, P, S, Si, and Se as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. Examples of the heterocyclic group include, but are not limited to, a pyridine group, a pyrrole group, a pyrimidine group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, and the like.

[0062] In this specification, the heteroarylene group is as defined in the heteroaryl group above, except that it is divalent.

[0063] In this specification, the meaning of “adjacent” in “forming a ring by bonding with adjacent groups” is the same as described above, and the “ring” means a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle.

[0064] 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 may be selected from examples of a cycloalkyl group, an aryl group, and a combination thereof, except for the non-monovalent ones, and the hydrocarbon ring may include, but is not limited to, benzene, cyclohexane, adamantane, bicyclo[2.2.1]heptane, bicyclo[2.2.1]octane, tetrahydronaphthalene, tetrahydroanthracene, 1,2,3,4-tetrahydro-1,4-methanonaphthalene, and 1,2,3,4-tetrahydro-1,4-ethanonaphthalene.

[0065] As used herein, the term "fused ring" refers to a ring-shaped structure in an organic compound in which two or more rings share two or more atoms. For example, an example of a fused ring of aliphatic and aromatic hydrocarbon rings is tetrahydronaphthalene.

[0066] Unless otherwise defined herein, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of embodiments of the present 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, this specification, including definitions, will control unless a specific passage is cited. Furthermore, the materials, methods, and examples are illustrative only and not intended to be limiting.

[0067] In this specification, the chemical formula 1 is any one of the chemical formulas 1-1 to 1-3 below.

[0068] [Chemical Formula 1-1]

[0069]

[0070] [Chemical Formula 1-2]

[0071]

[0072] [Chemical Formula 1-3]

[0073]

[0074] In the above chemical formulas 1-1 to 1-3, X, L1, L2, R1, R3, R4, Ar1, Ar2, a to d, r and q are as defined in the above chemical formula 1,

[0075] R2' is hydrogen or deuterium,

[0076] b' is an integer from 1 to 3, and when b' is 2 or greater, R2' are equal to or different from each other.

[0077] In this specification, the chemical formula 1 is any one of the chemical formulas 1-4 to 1-6 below.

[0078] [Chemical Formula 1-4]

[0079]

[0080] [Chemical Formula 1-5]

[0081]

[0082] [Chemical Formula 1-6]

[0083]

[0084] In the above chemical formulas 1-4 to 1-6, L1, L2, R1, R3, R4, Ar1, Ar2, a to d, r and q are as defined in the above chemical formula 1,

[0085] R2' is hydrogen or deuterium,

[0086] b' is an integer from 1 to 3, and when b' is 2 or greater, R2' are equal to or different from each other.

[0087] In this specification, the chemical formula 1 is any one of the chemical formulas 1-7 to 1-9 below.

[0088] [Chemical Formula 1-7]

[0089]

[0090] [Chemical Formula 1-8]

[0091]

[0092] [Chemical Formula 1-9]

[0093]

[0094] In the above chemical formulas 1-7 to 1-9, L1, L2, R1, R3, R4, Ar1, Ar2, a to d, r and q are as defined in the above chemical formula 1,

[0095] R2' is hydrogen or deuterium,

[0096] b' is an integer from 1 to 3, and when b' is 2 or greater, R2' are equal to or different from each other.

[0097] In this specification, X is O.

[0098] In this specification, X is S.

[0099] In the present specification, L1 and L2 are the same as or different from each other, and each independently represents a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.

[0100] In the present specification, L1 and L2 are the same as or different from each other, and each independently represents a direct bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0101] In the present specification, L1 and L2 are the same as or different from each other, and each independently represents a direct bond or an arylene group having 6 to 30 carbon atoms.

[0102] In the present specification, L1 and L2 are the same as or different from each other, and each independently represents a direct bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

[0103] In the present specification, L1 and L2 are the same as or different from each other, and each independently represents a direct bond or an arylene group having 6 to 20 carbon atoms.

[0104] In the present specification, L1 and L2 are the same as or different from each other, and each independently represents a direct bond or a substituted or unsubstituted arylene group having 6 to 15 carbon atoms.

[0105] In the present specification, L1 and L2 are the same as or different from each other, and each independently represents a direct bond or an arylene group having 6 to 15 carbon atoms.

[0106] In the present specification, L1 and L2 are the same as or different from each other, and each independently represents a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent naphthyl group, a substituted or unsubstituted divalent terphenyl group, a substituted or unsubstituted divalent anthracene group, or a substituted or unsubstituted divalent phenanthrene group.

[0107] In the present specification, L1 and L2 are the same as or different from each other, and each independently represents a direct bond, a phenylene group, a divalent biphenyl group, a divalent naphthyl group, a divalent terphenyl group, a divalent anthracene group, or a divalent phenanthrene group.

[0108] In this specification, L1 and L2 are equal to each other.

[0109] In this specification, L1 and L2 are different from each other.

[0110] In this specification, L1 and L2 are direct bonds.

[0111] In this specification, L1 and L2 are phenylene groups.

[0112] In this specification, L1 and L2 are divalent biphenyl groups.

[0113] In this specification, L1 and L2 are divalent anthracene groups.

[0114] In this specification, L1 and L2 are divalent phenanthrene groups.

[0115] In this specification, the L1 is a direct bond.

[0116] In this specification, L1 is a phenylene group.

[0117] In this specification, L1 is a divalent biphenyl group.

[0118] In this specification, L1 is a divalent anthracene group.

[0119] In this specification, L1 is a divalent phenanthrene group.

[0120] In this specification, the L2 is a direct bond.

[0121] In this specification, L2 is a phenylene group.

[0122] In this specification, L2 is a divalent biphenyl group.

[0123] In this specification, L2 is a divalent anthracene group.

[0124] In this specification, L2 is a divalent phenanthrene group.

[0125] In the present specification, R1 to R4 are the same as or different from each other, and each independently represents hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0126] In the present specification, R1 to R4 are the same as or different from each other, and each independently represents hydrogen, deuterium, a nitrile group, a halogen 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 unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0127] In the present specification, R1 to R4 are the same as or different from each other, and each independently represents hydrogen, deuterium, a nitrile group, a halogen 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 unsubstituted heteroaryl group having 3 to 20 carbon atoms.

[0128] In the present specification, R1 to R4 are the same as or different from each other, and are each independently hydrogen, deuterium, a nitrile group, a halogen group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.

[0129] In the present specification, R1 to R4 are the same as or different from each other, and are each independently hydrogen, deuterium, a nitrile group, a halogen group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms.

[0130] In the present specification, R1 and R4 are the same or different from each other, and are each independently hydrogen or deuterium.

[0131] In this specification, R5 is hydrogen.

[0132] In this specification, R5 is deuterium.

[0133] In this specification, R2' is hydrogen.

[0134] In this specification, R2' is deuterium.

[0135] In the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted bicyclic heteroaryl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted ring group in which these are condensed.

[0136] In the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or tricyclic aryl group, a substituted or unsubstituted bicyclic heteroaryl group, a substituted or unsubstituted monocyclic or tricyclic cycloalkyl group, or a substituted or unsubstituted ring group in which these are condensed.

[0137] In the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted bicyclic heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted ring group in which these are condensed.

[0138] In the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted bicyclic heteroaryl group having 3 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, or a substituted or unsubstituted ring group in which these are condensed.

[0139] In the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents an aryl group unsubstituted or substituted with a deuterium, a halogen group, a nitrile group, an alkyl group, or an aryl group; a bicyclic heteroaryl group unsubstituted or substituted with a deuterium, a halogen group, a nitrile group, an alkyl group, or an aryl group; a cycloalkyl group unsubstituted or substituted with a deuterium, a halogen group, a nitrile group, an alkyl group, or an aryl group; or a substituted or unsubstituted ring group in which these are condensed.

[0140] In the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a monocyclic or tricyclic aryl group substituted or unsubstituted with deuterium, a halogen group, a nitrile group, an alkyl group, or an aryl group; a bicyclic heteroaryl group substituted or unsubstituted with deuterium, a halogen group, a nitrile group, an alkyl group, or an aryl group; a monocyclic or tricyclic cycloalkyl group substituted or unsubstituted with deuterium, a halogen group, a nitrile group, an alkyl group, or an aryl group; or a substituted or unsubstituted ring group formed by condensation of these.

[0141] In the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with a deuterium, a halogen group, a nitrile group, an alkyl group, or an aryl group; a bicyclic heteroaryl group having 3 to 30 carbon atoms substituted or unsubstituted with a deuterium, a halogen group, a nitrile group, an alkyl group, or an aryl group; a cycloalkyl group having 3 to 30 carbon atoms substituted or unsubstituted with a deuterium, a halogen group, a nitrile group, an alkyl group, or an aryl group; or a substituted or unsubstituted ring group in which these are condensed.

[0142] In the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with a deuterium, a halogen group, a nitrile group, an alkyl group, or an aryl group; a bicyclic heteroaryl group having 3 to 20 carbon atoms substituted or unsubstituted with a deuterium, a halogen group, a nitrile group, an alkyl group, or an aryl group; a cycloalkyl group having 3 to 20 carbon atoms substituted or unsubstituted with a deuterium, a halogen group, a nitrile group, an alkyl group, or an aryl group; or a substituted or unsubstituted ring group in which these are condensed.

[0143] In the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a phenyl group, a biphenyl group, a terphenyl group, an anthracene group, a naphthyl group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a fluorene group substituted with an aryl group, a fluorene group unsubstituted or substituted with an alkyl group, an adamantyl group, or a tetrahydronaphthalene group unsubstituted or substituted with an alkyl group.

[0144] In this specification, Ar1 and Ar2 are the same.

[0145] In this specification, Ar1 and Ar2 are different from each other.

[0146] In the present specification, at least one of Ar1 and Ar2 is an aryl group having 10 to 30 carbon atoms.

[0147] In the present specification, at least one of Ar1 and Ar2 is an aryl group having 10 to 30 carbon atoms, which is unsubstituted or substituted with one or more substituents selected from deuterium, a halogen group, a nitrile group, an alkyl group, and an aryl group.

[0148] In the present specification, at least one of Ar1 and Ar2 is an aryl group having 10 to 30 carbon atoms, which is unsubstituted or substituted with one or more substituents selected from deuterium, a halogen group, a nitrile group, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 30 carbon atoms.

[0149] In the present specification, at least one of Ar1 and Ar2 is an anthracene group, a naphthyl group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a fluorene group substituted with an aryl group, or a fluorene group substituted or unsubstituted with an alkyl group.

[0150] In the present specification, at least one of Ar1 and Ar2 is an anthracene group, a naphthyl group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a fluorene group substituted with a phenyl group, or a fluorene group substituted or unsubstituted with a methyl group.

[0151] In this specification, the chemical formula 1 is any one of the compounds below.

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212] .

[0213] In the above compound, n is the number of deuterium atoms substituted in the compound in parentheses, n is an integer greater than or equal to 0, and the maximum value is the number of substitutable positions in the compound in parentheses.

[0214] The substituent of the compound of the above chemical formula 1 can be combined by a method known in the art, and the type, position or number of the substituent can be changed according to a technique known in the art.

[0215] In addition, by introducing various substituents into the core structure as described above, compounds having the unique properties of the introduced substituents can be synthesized. 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 satisfying the conditions required for each organic layer can be synthesized.

[0216] In addition, an organic light-emitting device according to the present invention is an organic light-emitting device comprising a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, characterized in that one or more of the organic layers includes the compound described above.

[0217] The organic light-emitting device of the present invention can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the above-described compound.

[0218] The above compound can be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution coating method refers to, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc.

[0219] The organic layer of the organic light-emitting device of the present invention may be formed as a single layer structure, but may also be formed as a multilayer structure in which two or more organic layers are laminated. 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 injects holes and transports holes, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as the organic layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers or a larger number of organic layers.

[0220] In the organic light-emitting device of the present invention, the organic layer includes at least one layer among an electron transport layer, an electron injection layer, and a layer that simultaneously injects and transports electrons, and at least one layer among the layers includes the compound of the chemical formula 1.

[0221] In another organic light-emitting device, the organic layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes a compound of the above chemical formula 1.

[0222] In the organic light-emitting device of the present invention, the organic layer includes at least one layer among a hole injection layer, a hole transport layer, and a layer that simultaneously injects holes and transports holes, and at least one layer among the layers includes the compound of the chemical formula 1.

[0223] In the organic light-emitting device of the present invention, the organic layer includes an electron blocking layer, and the electron blocking layer includes a compound of the chemical formula 1.

[0224] In another organic light-emitting device, the organic layer includes a hole injection layer or a hole transport layer, and the hole transport layer or the hole injection layer includes the compound of the chemical formula 1.

[0225] In the organic light-emitting device of the present invention, the organic layer includes a hole injection layer, a hole transport layer, or an electron suppression layer, and the hole injection layer, the hole transport layer, or the electron suppression layer includes the compound.

[0226] In one embodiment of the present specification, the first electrode is an anode and the second electrode is a cathode.

[0227] According to another embodiment, the first electrode is a cathode and the second electrode is an anode.

[0228] (1) Anode / hole transport layer / light emitting layer / cathode

[0229] (2) Anode / hole injection layer / hole transport layer / light-emitting layer / cathode

[0230] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0231] (4) Anode / hole transport layer / light emitting layer / electron transport layer / cathode

[0232] (5) Anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0233] (6) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode

[0234] (7) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0235] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / cathode

[0236] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0237] (10) Anode / hole transport layer / electron suppression layer / light emitting layer / electron transport layer / cathode

[0238] (11) Anode / hole transport layer / electron suppression layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0239] (12) Anode / hole injection layer / hole transport layer / electron suppression layer / light emitting layer / electron transport layer / cathode

[0240] (13) Anode / hole injection layer / hole transport layer / electron suppression layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0241] (14) Anode / hole transport layer / light emitting layer / hole suppression layer / electron transport layer / cathode

[0242] (15) Anode / hole transport layer / light emitting layer / hole suppression layer / electron transport layer / electron injection layer / cathode

[0243] (16) Anode / hole injection layer / hole transport layer / light emitting layer / hole suppression layer / electron transport layer / cathode

[0244] (17) Anode / hole injection layer / hole transport layer / light emitting layer / hole suppression layer / electron transport layer / electron injection layer / cathode

[0245] (18) Anode / hole injection layer / hole transport layer / electron suppression layer / light-emitting layer / hole blocking layer / electron injection and transport layer / cathode

[0246] The structure of the organic light-emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.

[0247] Figure 1 illustrates the structure of an organic light-emitting device in which a first electrode (2), an organic layer (3), and a second electrode (4) are sequentially laminated on a substrate (1). In such a structure, the compound of the chemical formula 1 may be included in the organic layer (3).

[0248] FIG. 2 illustrates the structure of an organic light-emitting device in which a first electrode (2), a hole injection layer (5), a hole transport layer (6), an electron suppression layer (7), a light-emitting layer (8), a hole suppression layer (9), an electron injection and transport layer (10), and a second electrode (4) are sequentially laminated on a substrate (1). In this structure, the compound of the chemical formula 1 may be included in the hole injection layer (5), the hole transport layer (6), or the electron suppression layer (7).

[0249] For example, the organic light-emitting device according to the present invention can be manufactured by forming an anode by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, and then forming an organic layer including at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a layer that simultaneously transports and injects holes, a light-emitting layer, an electron transport layer, an electron injection layer, and a layer that simultaneously transports and injects electrons, 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 manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0250] The above organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. In addition, the above organic layer may be manufactured with a smaller number of layers using various polymer materials by a solvent process other than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer.

[0251] The above anode is an electrode that injects holes, and as the anode material, a material having a high work function is generally preferred so that holes can be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline.

[0252] The above 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 the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayered materials such as LiF / Al or LiO2 / Al.

[0253] The above hole injection layer is a layer that facilitates 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, and it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include, but are not limited to, metal porphyrine, oligothiophene, arylamine-based organic compounds, hexanitrilehexaazatriphenylene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinone, and conductive polymers such as polyaniline and polythiophene. The thickness of the hole injection layer may be 1 to 150 nm. If the thickness of the above hole injection layer is 1 nm or more, there is an advantage of being able to prevent the hole injection characteristics from being deteriorated, and if it is 150 nm or less, there is an advantage of being able to prevent the driving voltage from being increased to improve the movement of holes due to the thickness of the hole injection layer being too thick.

[0254] According to one embodiment of the present specification, the hole injection layer includes, but is not limited to, a compound represented by the following chemical formula HI-1.

[0255] [Chemical formula HI-1]

[0256]

[0257] In the above chemical formula HI-1,

[0258] At least one of X'1 to X'6 is N, and the rest are CH,

[0259] R309 to R314 are the same or different, and each independently represent hydrogen; deuterium; a nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or combine with adjacent groups to form a substituted or unsubstituted ring.

[0260] According to one embodiment of the present specification, X'1 to X'6 are N.

[0261] According to one embodiment of the present specification, R309 to R314 are nitrile groups.

[0262] According to one embodiment of the present specification, the chemical formula HI-1 is represented by the following compound.

[0263]

[0264] The above-mentioned hole transport layer can play a role in facilitating hole transport. A hole transport material capable of transporting holes from the anode or hole injection layer and transferring them to the light-emitting layer, and a material with high hole mobility, is suitable. Specific examples include, but are not limited to, arylamine-based organic compounds, conductive polymers, and block copolymers with both conjugated and non-conjugated portions.

[0265] According to one embodiment of the present specification, the hole transport layer includes, but is not limited to, a compound represented by the following chemical formula HT-2.

[0266] [Chemical formula HT-2]

[0267]

[0268] In the above chemical formula HT-2,

[0269] R403 to R406 are the same or different, and each independently represent one selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted amine group; a substituted or unsubstituted heteroaryl group; and combinations thereof, or combine with adjacent groups to form a substituted or unsubstituted ring,

[0270] L403 is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0271] l403 is an integer from 1 to 3, and if l403 is 2 or greater, L403 are equal to or different from each other.

[0272] According to one embodiment of the present specification, R403 to R406 are the same as or different from each other, and are each independently one selected from the group consisting of a substituted or unsubstituted aryl group; a substituted or unsubstituted amine group; a substituted or unsubstituted heteroaryl group; and combinations thereof.

[0273] According to one 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.

[0274] According to one 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.

[0275] According to one embodiment of the present specification, R403 to R406 are the same as or different from each other, and each independently represents a phenyl group.

[0276] According to one embodiment of the present specification, the 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.

[0277] According to one embodiment of the present specification, the L403 is a divalent carbazole group substituted or unsubstituted with a phenylene group, a divalent biphenyl group, or an aryl group.

[0278] According to one embodiment of the present specification, the L403 is a divalent carbazole group substituted with a phenylene group or a naphthyl group.

[0279] According to one embodiment of the present specification, the chemical formula HT-2 is selected from the following compounds.

[0280]

[0281] An additional hole buffer layer may be provided between the hole injection layer and the hole transport layer, and includes a hole injection or transport material known in the art.

[0282] An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The electron blocking layer may be formed using the compound of the above chemical formula 1 or a material known in the art.

[0283] The above-mentioned light-emitting layer can emit red, green, or blue light, and can be made of a phosphorescent material or a fluorescent material. The above-mentioned light-emitting material is a material that can emit light in the visible light range by transporting holes and electrons from a hole transport layer and an electron transport layer, respectively, and combining them, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include, but are not limited to, 8-hydroxy-quinoline aluminum complex (Alq3); carbazole series compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; benzoxazole, benzthiazole, and benzimidazole series compounds; poly(p-phenylenevinylene) (PPV) series polymers; spiro compounds; polyfluorene, rubrene, etc.

[0284] Host materials for the light-emitting layer include condensed aromatic ring derivatives or heterocyclic compound-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compound-containing compounds include, but are not limited to, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc.

[0285] According to one embodiment of the present specification, the host includes, but is not limited to, a compound represented by the following chemical formula H-1.

[0286] [Chemical Formula H-1]

[0287]

[0288] In the above chemical formula H-1,

[0289] L20 and L21 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group,

[0290] Ar20 and Ar21 are the same or different, and each independently represent hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0291] R201 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0292] r201 is an integer from 1 to 8, and when r201 is 2 or more, 2 or more R201 are the same as or different from each other.

[0293] In one embodiment of the present specification, L20 and L21 are the same as or different from each other, and each independently represents a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a monocyclic or polycyclic divalent heterocyclic group having 2 to 30 carbon atoms.

[0294] In one embodiment of the present specification, L20 and L21 are the same as or different from each other, and each independently represent a direct bond; a phenylene group substituted or unsubstituted with deuterium; a biphenylylene group substituted or unsubstituted with deuterium; a naphthylene group substituted or unsubstituted with deuterium; a divalent dibenzofuran group; or a divalent dibenzothiophene group.

[0295] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

[0296] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic to tetracyclic heterocyclic group having 6 to 20 carbon atoms.

[0297] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represent a phenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl group unsubstituted or substituted 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; a dibenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzothiophene group unsubstituted or substituted 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.

[0298] In one 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; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group; a naphthyl group substituted or unsubstituted with deuterium; a thiophene group substituted or unsubstituted with a phenyl group; a phenanthrene group; a dibenzofuran group; a naphthobenzofuran group; a dibenzothiophene group; or a naphthobenzothiophene group.

[0299] In one embodiment of the present specification, Ar20 and Ar21 are naphthyl groups.

[0300] In one embodiment of the present specification, Ar20 and Ar21 are a 1-naphthyl group or a 2-naphthyl group.

[0301] According to one embodiment of the present specification, the R201 is hydrogen.

[0302] According to one embodiment of the present specification, the chemical formula H-1 is represented by the following compound.

[0303]

[0304] When the light-emitting layer emits red light, phosphorescent materials such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum), or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) can be used as light-emitting dopants, but are not limited thereto. When the light-emitting layer emits green light, phosphorescent materials such as Ir(ppy)3(fac tris(2-phenylpyridine)iridium), or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) can be used as light-emitting dopants, but are not limited thereto. When the light-emitting layer emits blue light, a phosphorescent material such as (4,6-F2ppy)2Irpic, or a fluorescent material such as spiro-DPVBi, spiro-6P, distilbenzene (DSB), distriarylene (DSA), PFO polymer, or PPV polymer can be used as a light-emitting dopant, but is not limited thereto.

[0305] According to one embodiment of the present specification, the dopant includes, but is not limited to, a compound represented by the following chemical formula D-1.

[0306] [Chemical Formula D-1]

[0307]

[0308] In the above chemical formula D-1,

[0309] T1 to T6 are the same or different and are each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0310] t5 and t6 are integers from 1 to 4, respectively.

[0311] If the above t5 is 2 or more, the two or more T5 are the same or different from each other,

[0312] When the above t6 is 2 or more, the two or more T6 are the same or different from each other.

[0313] According to one embodiment of the present specification, T1 to T6 are the same as or different from each other, and each independently represents hydrogen; a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0314] According to one embodiment of the present specification, T1 to T6 are the same as or different from each other, and each independently represent hydrogen; a straight-chain or branched-chain 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-chain alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0315] According to one embodiment of the present specification, T1 to T6 are the same as or different from each other, and are each independently a phenyl group; or a dibenzofuran group.

[0316] According to one embodiment of the present specification, the chemical formula D-1 is represented by the following compound.

[0317]

[0318] A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and a material known in the art may be used.

[0319] According to one embodiment of the present specification, the hole-suppressing layer includes a compound of the following chemical formula HB-1.

[0320] [Chemical formula HB-1]

[0321]

[0322] In the above chemical formula HB-1,

[0323] At least one of Z1 to Z3 is N, and the rest are CH,

[0324] L601 and L602 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0325] Ar601 to Ar603 are the same or different, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0326] According to one embodiment of the present specification, the L601 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0327] According to one embodiment of the present specification, L601 and L602 are the same as or different from each other, and are each independently a phenylene group; a biphenylylene group; or a divalent naphthylene group.

[0328] According to one embodiment of the present specification, Ar601 to Ar603 are the same as 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 a heteroaryl group having 3 to 30 carbon atoms.

[0329] According to one embodiment of the present specification, Ar601 to Ar603 are a phenyl group or a triphenylene group.

[0330] According to one embodiment of the present specification, the chemical formula HB-1 is represented by the following compound.

[0331]

[0332] The above electron transport layer can play a role in facilitating electron transport. As the electron transport material, a material that can easily receive electrons from the cathode and transfer them to the light-emitting layer, and a material with high electron mobility is suitable. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes. The thickness of the electron transport layer may be 1 to 50 nm. When the thickness of the electron transport layer is 1 nm or more, there is an advantage in that the electron transport characteristics can be prevented from being deteriorated, and when the thickness of the electron transport layer is 50 nm or less, there is an advantage in that the driving voltage can be prevented from increasing to improve electron movement due to the electron transport layer being too thick.

[0333] The above electron injection layer can play a role in facilitating electron injection. As the electron injection material, a compound having the ability to transport electrons, an electron injection effect from the cathode, an excellent electron injection effect for the light-emitting layer or light-emitting material, a compound that prevents the movement of excitons generated in the light-emitting layer to the hole injection layer, and an excellent thin film forming ability is preferable. Specifically, examples thereof include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

[0334] The electron injection and transport layer described above facilitates the injection and transport of electrons. Materials used in the electron injection and transport layers described above, or materials capable of effectively injecting electrons from the cathode and transporting them to the light-emitting layer, may be used.

[0335] According to one embodiment of the present specification, the electron injection and transport layer includes a compound of the following chemical formula EI-1.

[0336] [Chemical formula EI-1]

[0337]

[0338] In the above chemical formula EI-1,

[0339] At least one of Z11 to Z13 is N, and the rest are CH,

[0340] At least one of Z14 to Z16 is N, and the rest are CH,

[0341] L701 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0342] Ar701 to Ar704 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0343] l701 is an integer from 1 to 4, and when l701 is plural, L701 are equal to or different from each other.

[0344] According to one embodiment of the present specification, the L701 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0345] According to one embodiment of the present specification, the L701 is a phenylene group; a biphenylylene group; or a naphthylene group.

[0346] According to one embodiment of the present specification, the L701 is a phenylene group; or a naphthylene group.

[0347] According to one embodiment of the present specification, Ar701 to Ar704 are the same as 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 a heteroaryl group having 3 to 30 carbon atoms.

[0348] According to one embodiment of the present specification, Ar701 to Ar704 are phenyl groups.

[0349] According to one embodiment of the present specification, the chemical formula EI-1 is represented by the following compound.

[0350]

[0351] The above 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-naphtholato)aluminum, Bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc., but are not limited thereto.

[0352] The above hole blocking layer is a layer that blocks holes from reaching the cathode, and can generally be formed under the same conditions as the electron injection layer. Specifically, examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, and aluminum complexes.

[0353] The organic light-emitting device according to the present invention may be a front-emitting, back-emitting, or double-sided emitting type depending on the material used.

[0354] The organic light-emitting device of the present invention can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the above-described compound.

[0355] The method for preparing the compound of the above chemical formula 1 and the preparation of an organic light-emitting device using the compound are specifically described in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited by them.

[0356] In the following reaction scheme, the type and number of substituents can be appropriately selected by those skilled in the art from known starting materials, enabling the synthesis of various types of intermediates. The reaction types and reaction conditions known in the art can be utilized.

[0357] By appropriately combining the manufacturing formula and the intermediates described in the examples of this specification based on common technical knowledge, all of the compounds of the above chemical formula 1 described in this specification can be manufactured.

[0358] <Synthesis example>

[0359] Synthesis Example 1. Synthesis of Compound 1

[0360] Step 1) Synthesis of compound 1-A

[0361]

[0362] 1-Bromodibenzo[b,d]furan (20.0 g, 80.94 mmol) was completely dissolved in benzene-d6 (200 ml), and trifluoromethanesulfonic acid (3.6 ml, 40.47 mmol) was added and stirred for 25 minutes. After completion of the reaction, dichloromethane was added, the layers were separated, and the organic layer was obtained. It was dried over anhydrous magnesium sulfate (MgSO4) and filtered. The filtrate was concentrated under reduced pressure and recrystallized from ethyl acetate to obtain the compound 1-A (16.0 g, 77.79%).

[0363] Step 2) Synthesis of compound 1-B

[0364]

[0365] Compound 1-A (20.00 g, 78.70 mmol) and (5-chloro-[1,1'-biphenyl]-2-yl)boronic acid (19.21 g, 82.63 mmol) obtained in step 1 of the above Synthetic Example 1 were dissolved in tetrahydrofuran (200 ml), and then potassium carbonate (32.63 g, 236.10 mmol: water 100 ml) solution was added, followed by heating and stirring for 10 minutes. Bis(tri-tert-butylphosphine)palladium (0.12 g, 0.24 mmol) dissolved in tetrahydrofuran (20 ml) was added to the solution, followed by heating and stirring for 1 hour. After completion of the reaction and filtration, the layers were separated with toluene and water. After removal of the solvent, the compound 1-B (22.0 g, 77.25% yield) was obtained by recrystallization from ethyl acetate.

[0366] Step 3) Synthesis of compound 1

[0367]

[0368] To compound 1-B (20.0 g, 55.27 mmol), di([1,1'-biphenyl]-4-yl)amine (18.12 g, 56.37 mmol), and sodium tert-butoxide (7.44 g, 77.38 mmol) obtained in step 2 of the above Synthetic Example 1, toluene (200 ml) was added, and the mixture was heated and stirred for 10 minutes. Bis(tri-tert-butylphosphine)palladium (0.14 g, 0.27 mmol) dissolved in toluene (20 ml) was added to the mixture, and the mixture was heated and stirred for 1 hour. After completion of the reaction and filtration, the layers were separated with toluene and water. After removal of the solvent, the mixture was recrystallized from ethyl acetate to obtain compound 1 (28.0 g, 78.32% yield). (MS[M+H]+ = 647)

[0369] Synthesis Example 2. Synthesis of Compound 2

[0370]

[0371] Compound 2 (30.00 g, 77.89% yield) was obtained in the same manner as in step 3 of synthetic example 1 using compound 1-B (20.0 g, 55.27 mmol) and 4'-(naphthalen-1-yl)-N-phenyl-[1,1'-biphenyl]-4-amine (20.94 g, 56.37 mmol) obtained in step 2 of synthetic example 1. (MS[M+H]+ = 697)

[0372] Synthesis Example 3. Synthesis of Compound 3

[0373]

[0374] Compound 3 (32.50 g, 78.72% yield) was obtained in the same manner as in step 3 of synthetic example 1 using compound 1-B (20.0 g, 55.27 mmol) and N-(4-(phenanthren-9-yl)phenyl)-[1,1'-biphenyl]-4-amine (23.76 g, 56.37 mmol) obtained in step 2 of synthetic example 1. (MS[M+H]+ = 747)

[0375] Synthesis Example 4. Synthesis of Compound 4

[0376]

[0377] Compound 4 (29.50 g, 77.70% yield) was obtained in the same manner as in step 3 of Synthesis Example 1 using compound 1-B (20.0 g, 55.27 mmol) and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (20.38 g, 56.37 mmol) obtained in step 2 of Synthesis Example 1. (MS[M+H]+ = 687)

[0378] Synthesis Example 5. Synthesis of Compound 5

[0379] Step 1) Synthesis of compound 5-A

[0380]

[0381] Compound 5-A (16.0 g, 77.79%) was obtained using the same method as step 1 of Synthesis Example 1 using 2-bromodibenzo[b,d]furan (20.0 g, 80.94 mmol).

[0382] Step 2) Synthesis of compound 5-B

[0383]

[0384] Compound 5-B (22.0 g, 77.25% yield) was obtained using the compound 5-A (20.00 g, 78.70 mmol) obtained in step 1 of the above Synthesis Example 5 in the same manner as step 2 of the above Synthesis Example 1.

[0385] Step 3) Synthesis of compound 5

[0386]

[0387] Compound 5 (28.0 g, 78.32% yield) was obtained using the compound 5-B (20.0 g, 55.27 mmol) obtained in step 2 of the above Synthesis Example 5 in the same manner as step 3 of the above Synthesis Example 1. (MS[M+H]+ = 647)

[0388] Synthesis Example 6. Synthesis of Compound 6

[0389]

[0390] Compound 6 (30.00 g, 77.89% yield) was obtained in the same manner as in step 3 of synthesis example 1 using compound 5-B (20.0 g, 55.27 mmol) and 4'-(naphthalen-1-yl)-N-phenyl-[1,1'-biphenyl]-4-amine (20.94 g, 56.37 mmol) obtained in step 2 of synthesis example 5. (MS[M+H]+ = 697)

[0391] Synthesis Example 7. Synthesis of Compound 7

[0392]

[0393] Compound 7 (32.50 g, 78.72% yield) was obtained in the same manner as in step 3 of synthesis example 1 using compound 5-B (20.0 g, 55.27 mmol) and N-(4-(phenanthren-9-yl)phenyl)-[1,1'-biphenyl]-4-amine (23.76 g, 56.37 mmol) obtained in step 2 of synthesis example 5. (MS[M+H]+ = 747)

[0394] Synthesis Example 8. Synthesis of Compound 8

[0395]

[0396] Compound 8 (29.50 g, 77.70% yield) was obtained in the same manner as in step 3 of synthesis example 1 using compound 5-B (20.0 g, 55.27 mmol) and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (20.38 g, 56.37 mmol) obtained in step 2 of synthesis example 5. (MS[M+H]+ = 687)

[0397] Synthesis Example 9. Synthesis of Compound 9

[0398] Step 1) Synthesis of compound 9-A

[0399]

[0400] Compound 9-A (16.0 g, 77.79%) was obtained using the same method as step 1 of Synthesis Example 1 using 4-bromodibenzo[b,d]furan (20.0 g, 80.94 mmol).

[0401] Step 2) Synthesis of compound 9-B

[0402]

[0403] Compound 9-B (22.0 g, 77.25% yield) was obtained using the compound 9-A (20.00 g, 78.70 mmol) obtained in step 1 of the above Synthesis Example 9 in the same manner as step 2 of the above Synthesis Example 1.

[0404] Step 3) Synthesis of compound 9

[0405]

[0406] Compound 9 (28.0 g, 78.32% yield) was obtained using the compound 9-B (20.0 g, 55.27 mmol) obtained in step 2 of the above Synthesis Example 9 in the same manner as step 3 of the above Synthesis Example 1. (MS[M+H]+ = 647)

[0407] Synthesis Example 10. Synthesis of Compound 10

[0408]

[0409] Compound 10 (30.00 g, 77.89% yield) was obtained in the same manner as in step 3 of synthesis example 1 using compound 9-B (20.0 g, 55.27 mmol) and 4'-(naphthalen-1-yl)-N-phenyl-[1,1'-biphenyl]-4-amine (20.94 g, 56.37 mmol) obtained in step 2 of synthesis example 9. (MS[M+H]+ = 697)

[0410] Synthesis Example 11. Synthesis of Compound 11

[0411]

[0412] Compound 11 (32.50 g, 78.72% yield) was obtained in the same manner as in step 3 of synthesis example 1 using compound 9-B (20.0 g, 55.27 mmol) and N-(4-(phenanthren-9-yl)phenyl)-[1,1'-biphenyl]-4-amine (23.76 g, 56.37 mmol) obtained in step 2 of synthesis example 9. (MS[M+H]+ = 747)

[0413] Synthesis Example 12. Synthesis of Compound 12

[0414]

[0415] Compound 12 (29.50 g, 77.70% yield) was obtained in the same manner as in step 3 of synthesis example 1 using compound 9-B (20.0 g, 55.27 mmol) and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (20.38 g, 56.37 mmol) obtained in step 2 of synthesis example 9. (MS[M+H]+ = 687)

[0416] Synthesis Example 13. Synthesis of Compound 13

[0417] Step 1) Synthesis of compound 13-A

[0418]

[0419] Compound 13-A (16.0 g, 77.92%) was obtained using the same method as step 1 of Synthesis Example 1 using 1-bromodibenzo[b,d]thiophene (20.0 g, 76.00 mmol).

[0420] Step 2) Synthesis of compound 13-B

[0421]

[0422] Compound 13-B (22.0 g, 78.64% yield) was obtained using the compound 13-A (20.00 g, 74.02 mmol) obtained in step 1 of the above Synthesis Example 13 in the same manner as step 2 of the above Synthesis Example 1.

[0423] Step 3) Synthesis of compound 13

[0424]

[0425] Compound 13 (28.0 g, 79.82% yield) was obtained using the compound 13-B (20.0 g, 52.92 mmol) obtained in step 2 of the above Synthesis Example 13 in the same manner as step 3 of the above Synthesis Example 1. (MS[M+H]+ = 663)

[0426] Synthesis Example 14. Synthesis of Compound 14

[0427] Step 1) Synthesis of compound 14-A

[0428]

[0429] Compound 14-A (16.0 g, 77.92%) was obtained using the same method as step 1 of Synthesis Example 1 using 2-bromodibenzo[b,d]thiophene (20.0 g, 76.00 mmol).

[0430] Step 2) Synthesis of compound 14-B

[0431]

[0432] Compound 14-B (22.0 g, 78.64% yield) was obtained using the compound 14-A (20.00 g, 74.02 mmol) obtained in step 1 of the above Synthesis Example 14 in the same manner as step 2 of the above Synthesis Example 1.

[0433] Step 3) Synthesis of compound 14

[0434]

[0435] Compound 14 (28.0 g, 79.82% yield) was obtained using the compound 14-B (20.0 g, 52.92 mmol) obtained in step 2 of the above Synthesis Example 14 in the same manner as step 3 of the above Synthesis Example 1. (MS[M+H]+ = 663)

[0436] Synthesis Example 15. Synthesis of Compound 15

[0437] Step 1) Synthesis of compound 15-A

[0438]

[0439] Compound 15-A (16.0 g, 77.92%) was obtained using the same method as step 1 of Synthesis Example 1 using 4-bromodibenzo[b,d]thiophene (20.0 g, 76.00 mmol).

[0440] Step 2) Synthesis of compound 15-B

[0441]

[0442] Compound 15-B (22.0 g, 78.64% yield) was obtained using the compound 15-A (20.00 g, 74.02 mmol) obtained in step 1 of the above Synthesis Example 15 in the same manner as step 2 of the above Synthesis Example 1.

[0443] Step 3) Synthesis of compound 15

[0444]

[0445] Compound 15 (28.0 g, 79.82% yield) was obtained using the compound 15-B (20.0 g, 52.92 mmol) obtained in step 2 of the above Synthesis Example 15 in the same manner as step 3 of the above Synthesis Example 1. (MS[M+H]+ = 663)

[0446] Synthesis Example 16. Synthesis of Compound 16

[0447]

[0448] Compound 16 (16.0 g, 78.28% yield) was obtained using N,N-di([1,1'-biphenyl]-4-yl)-6-(dibenzo[b,d]-furan-1-yl)-[1,1'-biphenyl]-3-amine (20.0 g, 31.26 mmol) in the same manner as step 1 of Synthetic Example 1. (MS[M+H]+ = 654)

[0449] Synthesis Example 17. Synthesis of Compound 17

[0450]

[0451] Compound 17 (16.0 g, 78.40% yield) was obtained using the same method as step 1 of Synthetic Example 1 using 6-(dibenzo[b,d]-furan-1-yl)-N-(4'-(naphthalen-1-yl)-[1,1'-biphenyl]-4-yl)-N-phenyl-[1,1'-biphenyl]-3-amine (20.0 g, 28.99 mmol). (MS[M+H]+ = 704)

[0452] Synthesis Example 18. Synthesis of Compound 18

[0453]

[0454] Compound 18 (16.0 g, 78.40% yield) was obtained using N-([1.1'-biphenyl]-4-yl)-6-(dibenzo[b,d]-furan-1-yl)-N-(4-(phenanthren-9-yl)phenyl)-[1,1'-biphenyl]-3-amine (20.0 g, 27.03 mmol) in the same manner as in step 1 of Synthetic Example 1. (MS[M+H]+ = 755)

[0455] Synthesis Example 19. Synthesis of Compound 19

[0456]

[0457] Compound 19 (16.0 g, 78.60% yield) was obtained in the same manner as in step 1 of Synthetic Example 1 using N-([1.1'-biphenyl]-4-yl)-N-(6-(dibenzo[b,d]-furan-1-yl)-[1,1'-biphenyl]-3-yl)-9,9-dimethyl-9H-fluoren-2-amine (20.0 g, 29.42 mmol). (MS[M+H]+ = 692)

[0458] Synthesis Example 20. Synthesis of Compound 20

[0459]

[0460] Compound 20 (16.0 g, 78.28% yield) was obtained using N,N-di([1,1'-biphenyl]-4-yl)-6-(dibenzo[b,d]-furan-2-yl)-[1,1'-biphenyl]-3-amine (20.0 g, 31.26 mmol) in the same manner as step 1 of Synthetic Example 1. (MS[M+H]+ = 654)

[0461] Synthesis Example 21. Synthesis of Compound 21

[0462]

[0463] Compound 21 (16.0 g, 78.40% yield) was obtained using the same method as step 1 of Synthetic Example 1 using 6-(dibenzo[b,d]-furan-2-yl)-N-(4'-(naphthalen-1-yl)-[1,1'-biphenyl]-4-yl)-N-phenyl-[1,1'-biphenyl]-3-amine (20.0 g, 28.99 mmol). (MS[M+H]+ = 704)

[0464] Synthesis Example 22. Synthesis of Compound 22

[0465]

[0466] Compound 22 (16.0 g, 78.40% yield) was obtained using N-([1.1'-biphenyl]-4-yl)-6-(dibenzo[b,d]-furan-2-yl)-N-(4-(phenanthren-9-yl)phenyl)-[1,1'-biphenyl]-3-amine (20.0 g, 27.03 mmol) in the same manner as in step 1 of Synthetic Example 1. (MS[M+H]+ = 755)

[0467] Synthesis Example 23. Synthesis of Compound 23

[0468]

[0469] Compound 23 (16.0 g, 78.60% yield) was obtained using N-([1.1'-biphenyl]-4-yl)-N-(6-(dibenzo[b,d]-furan-2-yl)-[1,1'-biphenyl]-3-yl)-9,9-dimethyl-9H-fluoren-2-amine (20.0 g, 29.42 mmol) in the same manner as in step 1 of Synthetic Example 1. (MS[M+H]+ = 692)

[0470] Synthesis Example 24. Synthesis of Compound 24

[0471]

[0472] Compound 24 (16.0 g, 78.28% yield) was obtained using N,N-di([1,1'-biphenyl]-4-yl)-6-(dibenzo[b,d]-furan-4-yl)-[1,1'-biphenyl]-3-amine (20.0 g, 31.26 mmol) in the same manner as step 1 of Synthetic Example 1. (MS[M+H]+ = 654)

[0473] Synthesis Example 25. Synthesis of Compound 25

[0474]

[0475] Compound 25 (16.0 g, 78.40% yield) was obtained using the same method as step 1 of Synthetic Example 1 using 6-(dibenzo[b,d]-furan-4-yl)-N-(4'-(naphthalen-1-yl)-[1,1'-biphenyl]-4-yl)-N-phenyl-[1,1'-biphenyl]-3-amine (20.0 g, 28.99 mmol). (MS[M+H]+ = 704)

[0476] Synthesis Example 26. Synthesis of Compound 26

[0477]

[0478] Compound 26 (16.0 g, 78.40% yield) was obtained using N-([1.1'-biphenyl]-4-yl)-6-(dibenzo[b,d]-furan-4-yl)-N-(4-(phenanthren-9-yl)phenyl)-[1,1'-biphenyl]-3-amine (20.0 g, 27.03 mmol) in the same manner as in step 1 of Synthetic Example 1. (MS[M+H]+ = 755)

[0479] Synthesis Example 27. Synthesis of Compound 27

[0480]

[0481] Compound 27 (16.0 g, 78.60% yield) was obtained in the same manner as in step 1 of Synthetic Example 1 using N-([1.1'-biphenyl]-4-yl)-N-(6-(dibenzo[b,d]-furan-4-yl)-[1,1'-biphenyl]-3-yl)-9,9-dimethyl-9H-fluoren-2-amine (20.0 g, 29.42 mmol). (MS[M+H]+ = 692)

[0482] Synthesis Example 28. Synthesis of Compound 28

[0483]

[0484] Compound 28 (16.0 g, 78.33% yield) was obtained using N,N-di([1,1'-biphenyl]-4-yl)-6-(dibenzo[b,d]-thiophene-1-yl)-[1,1'-biphenyl]-3-amine (20.0 g, 30.49 mmol) in the same manner as step 1 of Synthetic Example 1. (MS[M+H]+ = 670)

[0485] Synthesis Example 29. Synthesis of Compound 29

[0486]

[0487] Compound 29 (16.0 g, 78.33% yield) was obtained using N,N-di([1,1'-biphenyl]-4-yl)-6-(dibenzo[b,d]-thiophen-2-yl)-[1,1'-biphenyl]-3-amine (20.0 g, 30.49 mmol) in the same manner as step 1 of Synthetic Example 1. (MS[M+H]+ = 670)

[0488] Synthesis Example 30. Synthesis of Compound 30

[0489]

[0490] Compound 30 (16.0 g, 78.33% yield) was obtained using N,N-di([1,1'-biphenyl]-4-yl)-6-(dibenzo[b,d]-thiophene-4-yl)-[1,1'-biphenyl]-3-amine (20.0 g, 30.49 mmol) in the same manner as step 1 of Synthetic Example 1. (MS[M+H]+ = 670)

[0491] Experimental examples and comparative experimental examples>

[0492] Experimental Example 1-1

[0493] A glass substrate coated with a 1,400 Å thick ITO (Indium Tin Oxide) thin film was placed in distilled water containing detergent and ultrasonically cleaned. The detergent was a Fischer Co. product, and the distilled water was secondarily filtered through a Millipore Co. filter. After washing the ITO for 30 minutes, ultrasonically cleaned twice with distilled water for 10 minutes each. After washing with distilled water, ultrasonically cleaned with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using oxygen plasma and then transferred to a vacuum deposition machine.

[0494] On the ITO transparent electrode thus prepared, a hole injection layer was formed by thermal vacuum deposition of a compound represented by the following chemical formula HAT to a thickness of 100 Å. Thereon, a hole transport layer was formed by vacuum deposition of a compound represented by the following chemical formula HT1 to a thickness of 1150 Å, and then, as an electron blocking layer, compound 1 prepared in Synthesis Example 1 was thermal vacuum deposited to a thickness of 150 Å. Subsequently, a light-emitting layer was formed by vacuum depositing a compound represented by the following chemical formula BH and a compound represented by the following chemical formula BD at a weight ratio of 25:1 to a thickness of 200 Å. Subsequently, a hole blocking layer was formed by vacuum depositing a compound represented by the following chemical formula HB1 at a thickness of 50 Å. Subsequently, a layer performing both electron transport and electron injection was formed by thermal vacuum deposition of a compound represented by the following chemical formula ET1 and a compound represented by the following LiQ at a weight ratio of 1:1 to a thickness of 310 Å. An organic light-emitting device was manufactured by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1000 Å on the electron transport and electron injection layers to form a cathode.

[0495]

[0496] Experimental examples 1-2 to 1-30 and comparative experimental examples 1-1 to 1-5

[0497] Organic light-emitting devices of Experimental Examples 1-2 to 1-30 and Comparative Experimental Examples 1-1 to 1-5 were manufactured in the same manner as Experimental Example 1-1, except that the compounds described in Table 1 below were used instead of Compound 1 in Experimental Example 1-1. The organic light-emitting devices manufactured in the Experimental Examples and Comparative Experimental Examples were manufactured at 10 mA / cm 2 When a current of , voltage, efficiency, color coordinates, and lifespan were measured, and the results are shown in Table 1 below. Meanwhile, T95 refers to the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.

[0498] Electron suppression layer voltage (V @ 10 mA / cm 2)Efficiency (cd / A @ 10mA / cm 2)Color coordinate (x, y)Lifespan (T95, hr)Experimental example 1-1Compound 13.665.940.140, 0.043180Experimental example 1-2Compound 23.685.950.140, 0.043180Experimental example 1-3Compound 33.665.940.140, 0.043180Experimental example 1-4Compound 43.645.920.140, 0.043175Experimental example 1-5Compound 53.675.940.140, 0.043175Experimental example 1-6Compound 63.685.940.141, 0.043175Experimental example 1-7Compound 73.675.960.140, 0.044175Experimental Example 1-8 Compound 83.645.920.140, 0.043170Experimental Example 1-9 Compound 93.655.960.141, 0.043180Experimental Example 1-10 Compound 103.665.970.140, 0.043180Experimental Example 1-11 Compound 113.665.950.140, 0.043180Experimental Example 1-12 Compound 123.645.940.140, 0.044175Experimental Example 1-13 Compound 133.665.920.141, 0.044170Experimental Example 1-14 Compound 143.675.910.140, 0.044170Experimental example 1-15 Compound 153.665.920.141, 0.043170Experimental example 1-16 Compound 163.665.940.140, 0.043190Experimental example 1-17 Compound 173.685.950.140, 0.043190Experimental example 1-18 Compound 183.665.940.140, 0.043190Experimental example 1-19 Compound 193.645.920.140, 0.043185Experimental example 1-20 Compound 203.675.940.140, 0.043185 Experimental Example 1-21 Compound 213.685.940.141, 0.043185 Experimental Example 1-22 Compound 223.675.960.140, 0.044185 Experimental Example 1-23 Compound 233.645.920.140, 0.043180 Experimental Example 1-24 Compound 243.655.960.141, 0.043190 Experimental Example 1-25 Compound 253.665.970.140, 0.043190 Experimental Example 1-26 Compound 263.665.950.140, 0.043190 Experimental Example 1-27 Compound 273.645.940.140, 0.044185Experimental Example 1-28 Compound 283.665.920.141, 0.044180Experimental Example 1-29 Compound 293.675.910.140, 0.044180Experimental Example 1-30 Compound 303.665.920.141, 0.043180Comparative Experimental Example 1-1 EB14.055.000.145, 0.049100Comparative Experimental Example 1-2 EB24.104.950.145, 0.04990Comparative Experimental Example 1-3 EB34.005.120.144, 0.049110Comparative Experimental Example 1-4 EB43.905.560.144, 0.048145Comparison Experimental Example 1-5EB53.925.500.144, 0.048130.

[0499]

[0500] As shown in Table 1 above, the compound of the present invention has excellent electron blocking ability, and it was confirmed that an organic light-emitting device using the compound as an electron blocking layer exhibits remarkable effects in terms of driving voltage, efficiency, and lifespan.

[0501] Specifically, compounds EB1 to EB3 are compounds in which one of Ar1 and Ar2 is a tricyclic to hexacyclic heteroaryl group. Comparative experimental examples 1-1 to 1-3 using these in the electron blocking layer show that the driving voltage is high, the efficiency is low, and the lifespan is short compared to experimental examples 1-1 to 1-30.

[0502] Compounds EB4 and EB5 have a biphenyl linkage attached to the 3-position of dibenzofuran.

[0503] Compound 1 used in the experimental example of the present invention has a different substitution position of the biphenyl linkage group in dibenzofuran compared to compound EB4, and other substituent conditions are the same.

[0504] Compared with comparative examples 1-1 to 1-3, comparative examples 1-4 and 1-5 have a somewhat lower driving voltage, higher efficiency, and longer lifespan, but compared with experimental examples 1-1 to 1-30 of the present invention, the driving voltage is high, and the efficiency and lifespan are low.

[0505] In particular, when comparing Experimental Example 1-1 and Comparative Experimental Example 1-4, which have the same type of substituent but different substitution positions, it can be confirmed that Experimental Example 1-1 has superior effects in terms of voltage, efficiency, and lifespan.

[0506] Experimental examples 2-1 to 2-30 and comparative experimental examples 1-1, 2-1 to 2-3

[0507] Organic light-emitting devices of Experimental Examples 2-1 to 2-30 and Comparative Experimental Examples 2-1 to 2-3 were manufactured in the same manner as Experimental Example 1-1, except that the compound represented by the chemical formula EB1 was used as the electron blocking layer instead of the compound 1 in Experimental Example 1-1, and the compound described in Table 2 was used as the hole transport layer instead of the compound represented by the chemical formula HT1. The organic light-emitting devices manufactured in the Experimental Examples and Comparative Experimental Examples were manufactured at a current density of 10 mA / cm. 2 When a current of , voltage, efficiency, color coordinates, and lifespan were measured, and the results are shown in Table 2 below. Meanwhile, T95 refers to the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.

[0508] Hole transport layer voltage (V @ 10 mA / cm 2 )Efficiency (cd / A @ 10mA / cm 2)Color coordinate (x, y)Lifespan (T95, hr)Experimental example 2-1 Compound 13.615.870.140, 0.044180Experimental example 2-2 Compound 23.625.890.140, 0.043175Experimental example 2-3 Compound 33.615.870.140, 0.043180Experimental example 2-4 Compound 43.575.900.140, 0.043185Experimental example 2-5 Compound 53.625.880.140, 0.044175Experimental example 2-6 Compound 63.635.890.140, 0.043175Experimental example 2-7 Compound 73.625.870.140, 0.043180Experimental Example 2-8 Compound 83.585.910.141, 0.043180Experimental Example 2-9 Compound 93.615.880.140, 0.044180Experimental Example 2-10 Compound 103.635.890.140, 0.043180Experimental Example 2-11 Compound 113.615.890.140, 0.044175Experimental Example 2-12 Compound 123.585.900.140, 0.043180Experimental Example 2-13 Compound 133.605.880.140, 0.043170Experimental Example 2-14 Compound 143.585.880.140, 0.044170 Experimental Example 2-15 Compound 153.595.870.140, 0.043175 Experimental Example 2-16 Compound 163.615.870.140, 0.044190 Experimental Example 2-17 Compound 173.625.890.140, 0.043185 Experimental Example 2-18 Compound 183.615.870.140, 0.043190 Experimental Example 2-19 Compound 193.575.900.140, 0.043195 Experimental Example 2-20 Compound 203.625.880.140, 0.044185 Experimental Example 2-21 Compound 213.635.89 0.140, 0.043185 Experimental Example 2-22 Compound 223.625.87 0.140, 0.043190 Experimental Example 2-23 Compound 233.585.91 0.141, 0.043190 Experimental Example 2-24 Compound 243.615.88 0.140, 0.044190 Experimental Example 2-25 Compound 253.635.89 0.140, 0.043190 Experimental Example 2-26 Compound 263.615.89 0.140, 0.044185 Experimental Example 2-27 Compound 273.585.900.140, 0.043190Experimental Example 2-28 Compound 283.605.880.140, 0.043180Experimental Example 2-29 Compound 293.585.880.140, 0.044180Experimental Example 2-30 Compound 303.595.870.140, 0.043185Comparative Experimental Example 1-1HT14.055.000.145, 0.049100Comparative Experimental Example 2-1HT24.024.980.145, 0.04990Comparative Experimental Example 2-2HT33.985.000.144, 0.048110Comparative Experimental Example 2-3HT43.885.080.145, 0.048140.

[0509]

[0510] HT2 HT3 HT4

[0511] As shown in Table 2 above, the compound of the present invention has excellent hole transport capability, and it was confirmed that an organic light-emitting device using the compound as a hole transport layer exhibits remarkable effects in terms of driving voltage, efficiency, and lifespan.

[0512] Specifically, compounds HT2 to HT4 are those in which one of Ar1 and Ar2 in the above chemical formula 1 is a 3- to 6-ring heteroaryl group. Compared to comparative experimental examples 2-1 to 2-3 in which these were used in the hole transport layer, it can be confirmed that experimental examples 2-1 to 2-30 have lower driving voltage, higher efficiency, and longer lifespan.

Claims

1. A compound of the following chemical formula 1: In the above chemical formula 1, X is O or S, L1 and L2 are the same or different from each other, and each independently represents a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted bicyclic heteroaryl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted ring group in which these are condensed, R1 to R4 are the same or different and are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, R5 is hydrogen or deuterium, a is an integer from 1 to 4, b is 1 or 2, d is an integer from 1 to 3, c is an integer from 1 to 5, If a to d are 2 or more, the substituents in the parentheses are the same or different, r and q are integers from 1 to 10, If r or q is 2 or more, the substituents in parentheses are the same or different.

2. In claim 1, the chemical formula 1 is a compound which is any one of the chemical formulas 1-1 to 1-3 below: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] In the above chemical formulas 1-1 to 1-3, X, L1, L2, R1, R3, R4, Ar1, Ar2, a to d, r and q are as defined in the above chemical formula 1, R2' is hydrogen or deuterium, b' is an integer from 1 to 3, and when b' is 2 or greater, R2' are equal to or different from each other.

3. In claim 1, the chemical formula 1 is a compound which is any one of the chemical formulas 1-4 to 1-6 below: [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] In the above chemical formulas 1-4 to 1-6, L1, L2, R1, R3, R4, Ar1, Ar2, a to d, r and q are as defined in the above chemical formula 1, R2' is hydrogen or deuterium, b' is an integer from 1 to 3, and when b' is 2 or greater, R2' are equal to or different from each other.

4. In claim 1, the chemical formula 1 is a compound which is any one of the chemical formulas 1-7 to 1-9 below: [Chemical Formula 1-7] [Chemical Formula 1-8] [Chemical Formula 1-9] In the chemical formulas 1-7 to 1-9 above, L1, L2, R1, R3, R4, Ar1, Ar2, a to d, r and q are as defined in the chemical formula 1 above, R2' is hydrogen or deuterium, b' is an integer from 1 to 3, and when b' is 2 or greater, R2' are equal to or different from each other.

5. A compound according to claim 1, wherein L1 and L2 are the same as or different from each other, and each independently represents a direct bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

6. A compound according to claim 1, wherein R1 and R4 are the same or different and are each independently hydrogen or deuterium.

7. A compound according to claim 1, wherein Ar1 and Ar2 are the same.

8. A compound according to claim 1, wherein Ar1 and Ar2 are different from each other.

9. A compound according to claim 1, wherein at least one of Ar1 and Ar2 is an aryl group having 10 to 30 carbon atoms, which is unsubstituted or substituted with at least one substituent selected from deuterium, a halogen group, a nitrile group, an alkyl group, and an aryl group.

10. In claim 1, the compound having chemical formula 1 is any one of the following compounds: In the above compound, n is the number of deuterium substituted in the compound in parentheses, n is an integer greater than or equal to 0, and the maximum value is the number of substitutable positions in the compound in parentheses.

11. An organic light-emitting device comprising a first electrode; a second electrode provided opposite the first electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises a compound according to any one of claims 1 to 10.

12. An organic light-emitting device according to claim 10, wherein the organic layer comprises a hole injection layer, a hole transport layer or an electron suppression layer, and the hole injection layer, the hole transport layer or the electron suppression layer comprises the compound.

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