Organic light-emitting devices

Abstract

The present specification provides an organic light-emitting device including a first organic layer and a second organic layer.

Description

Technical Field

[0001] This specification relates to organic light emitting devices.

[0002] This application claims the priority of Korean Patent Application No. 10-2018-0147239 filed with the Korean Intellectual Property Office on November 26, 2018, the entire contents of which are incorporated herein by reference. Background Art

[0003] Generally speaking, the phenomenon of organic light emitting refers to the phenomenon of converting electrical energy into light energy using organic substances. An organic light emitting device using the phenomenon of organic light emitting generally has a structure including an anode and a cathode and an organic layer located between them. Here, in order to improve the efficiency and stability of the organic light emitting device, the organic layer is mostly formed by a multilayer structure composed of different substances, for example, it can be formed by a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. For the structure of such an organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when the excitons re-transition to the ground state, light is emitted.

[0004] There is a continuous demand for the development of new materials for organic light-emitting devices as described above. Summary of the invention

[0005] Technical issues

[0006] The present specification provides an organic light emitting device including a compound represented by Chemical Formula 1 in a first organic layer and a compound represented by Chemical Formula 2 in a second organic layer, thereby providing an organic light emitting device having low driving voltage, high efficiency, excellent lifespan characteristics, or high color purity.

[0007] Solution to the problem

[0008] The present specification provides an organic light-emitting device, comprising: an anode, a cathode, a first organic layer and a second organic layer provided between the anode and the cathode,

[0009] The first organic layer includes a compound represented by the following chemical formula 1:

[0010] The second organic layer includes a compound represented by the following Chemical Formula 2.

[0011] [Chemical formula 1]

[0012]

[0013] In the above chemical formula 1,

[0014] X is B; P=O; or P=S,

[0015] Z1 to Z3 are the same or different from each other, and are each independently a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring,

[0016] A1 is N(R101) or O, A2 is N(R102) or O,

[0017] R101 and R102 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent substituents are combined with each other to form a substituted or unsubstituted ring,

[0018] [Chemical formula 2]

[0019]

[0020] In the above chemical formula 2,

[0021] Y is O or S,

[0022] R21 to R24 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are represented by the following chemical formula 3, or adjacent substituents are combined with each other to form a substituted or unsubstituted ring,

[0023] At least one of R21 to R24 is represented by the following Chemical Formula 3,

[0024] r21 to r24 are the same or different from each other and are each independently an integer from 0 to 4. When r21 is 2 or more, R21 is the same or different from each other. When r22 is 2 or more, R22 is the same or different from each other. When r23 is 2 or more, R23 is the same or different from each other. When r24 is 2 or more, R24 is the same or different from each other.

[0025] [Chemical formula 3]

[0026]

[0027] In the above chemical formula 3,

[0028] X1 is N or C(R31), X2 is N or C(R32), X3 is N or C(R33), at least one of X1 to X3 is N,

[0029] R31, R32 and R33 are the same or different from each other and are independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or combine with Ar1 or Ar2 to form a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring,

[0030] Ar1 and Ar2 are the same or different from each other, and are each independently an aryl group substituted or unsubstituted by R41, or a heterocyclic group substituted or unsubstituted by R42, or are combined with R31, R32 or R33 to form a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring,

[0031] R41 and R42 are the same as or different from each other, and are each independently selected from deuterium, a halogen group, a nitrile group, an alkyl group, a halogenated alkyl group, an alkoxy group, a silyl group, an aryl group, and a heterocyclic group, or are a group formed by connecting two or more substituents,

[0032] L is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group,

[0033] m is an integer from 0 to 4. When m is 2 or more, L are the same or different from each other.

[0034] * is a site that binds to Chemical Formula 2.

[0035] Effects of the Invention

[0036] The organic light emitting device according to one embodiment of the present specification includes the compound of Chemical Formula 1 and the compound of Chemical Formula 2, and thus has excellent characteristics of long life, high efficiency, and low driving voltage. BRIEF DESCRIPTION OF THE DRAWINGS

[0037] Figures 1 to 4 An example of the organic light emitting device of the present invention is illustrated.

[0038] [Explanation of symbols]

[0039] 0: substrate

[0040] 1: Cathode

[0041] 2: Electron transport layer

[0042] 3: Hole transport layer

[0043] 4: Anode

[0044] 5: Organic layer

[0045] 6: Organic layer

[0046] 7: Hole blocking layer or electron regulation layer

[0047] 11: Luminous layer 1

[0048] 12: Luminous layer 2

[0049] 13: Luminous layer 3

[0050] 101: Luminous Layer

[0051] 201: First organic layer

[0052] 202: Second organic layer DETAILED DESCRIPTION

[0053] The present specification will be described in more detail below. However, the following description relates to one embodiment of the present invention, and all possible substitutions within the scope of equivalents are included.

[0054] First, some terms used in this specification are clarified.

[0055] In the present specification, when a part is indicated to “include / comprise” a certain component, unless there is a particular description to the contrary, it means that other components may be further included, rather than excluding other components.

[0056] In this specification, Cn means that the number of carbon atoms is n.

[0057] In this specification, Cn1-Cn2 means that the number of carbon atoms is n1 to n2.

[0058] In the present specification, examples of substituents are described below, but are not limited thereto.

[0059] The term "substituted" mentioned above means that the hydrogen atom bonded to the carbon atom of the compound is replaced by another substituent. The substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted. When there are more than two substitutions, the two or more substituents may be the same or different from each other.

[0060] In this specification, the term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium; halogen group; nitrile group; alkyl group; haloalkyl group; alkoxy group; haloalkoxy group; cycloalkyl group; silyl group; alkenyl group; amine group; arylamine group; aryl group; and heterocyclic groups containing one or more N, O, S, Se and Si atoms, or substituted by a substituent formed by connecting two or more substituents among the substituents exemplified above, or having no substituents. For example, "a substituent formed by connecting two or more substituents" can be a biphenyl group. That is, the biphenyl group can be an aryl group, and can also be interpreted as a substituent formed by connecting two phenyl groups.

[0061] In this specification, two or more substituents are linked together, which means that the hydrogen of any substituent is replaced by another substituent. For example, isopropyl and phenyl can be linked together to form substituent.

[0062] In this specification, three substituents connected include not only (substituent 1)-(substituent 2)-(substituent 3) connected continuously, but also (substituent 2) and (substituent 3) connected to (substituent 1). For example, two phenyl groups and an isopropyl group can be connected to form The same description as above also applies to the case where 4 or more substituents are connected.

[0063] In this manual, * or It indicates a site that bonds to other substituents or bonding parts.

[0064] In one embodiment of the present specification, "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, a halogen group; a nitrile group; a C1-C20 alkyl group; a C1-C20 haloalkyl group; a C1-C20 alkoxy group; a C1-C20 haloalkoxy group; a C3-C20 cycloalkyl group; a C1-C50 silyl group; a C2-C20 alkenyl group; an amine group; a C6-C50 arylamine group; a C6-C30 aryl group; and a C2-C30 heterocyclic group containing one or more of N, O, S, Se and Si atoms, or substituted by a substituent formed by connecting two or more substituents, or having no substituents.

[0065] In one embodiment of the present specification, "substituted or unsubstituted" means substituted with one substituent selected from deuterium, C1-C10 alkyl, C6-C30 aryl and C2-C30 heterocyclic group, or a substituent formed by connecting two or more substituents, or having no substituent.

[0066] In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.

[0067] In the present specification, the alkyl group may be a linear or branched group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30, 1 to 20, 1 to 10, or 1 to 5. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 4-methylhexyl, and 5-methylhexyl.

[0068] In this specification, a haloalkyl group may be straight chain or branched chain, and refers to a hydrogen atom of the alkyl group being replaced by one or more halogen groups. The number of carbon atoms is not particularly limited, but is preferably 1 to 30, 1 to 20, 1 to 10, or 1 to 5. The haloalkyl group may be applied to the above description of the alkyl group. Specific examples of haloalkyl groups include fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, dibromomethyl, tribromomethyl, etc., but are not limited thereto.

[0069] In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, and more preferably a cycloalkyl group having 3 to 30, 3 to 15, or 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0070] In this specification, alkoxy is a group to which an alkyl group is connected on an oxygen atom, and therefore can be straight chain, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30, 1 to 20, 1 to 10 or 1 to 5. Specifically, it can be methoxy, ethoxy, n-propoxy, isopropoxy, isopropyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc., but is not limited thereto.

[0071] In the present specification, the alkenyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30, 2 to 20, 2 to 10, or 2 to 5. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthalene-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl, etc., but are not limited thereto.

[0072] In the present specification, the silyl group can be represented by the chemical formula -SiRaRbRc, wherein Ra, Rb and Rc can each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The silyl group specifically includes trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl and the like, but is not limited thereto.

[0073] In the present specification, the amine group can be represented by the chemical formula of -NRfRg, and the above Rf and Rg can each be hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group. The above amine group can be selected from alkylamine, arylalkylamine, arylamine, arylheteroarylamine, alkylheteroarylamine, and heteroarylamine, and more specifically, can be dimethylamine, diphenylamine, etc., but are not limited thereto.

[0074] In the present specification, an aryl group refers to a univalent aromatic hydrocarbon or a univalent group of an aromatic hydrocarbon derivative. In the present specification, an aromatic hydrocarbon refers to a compound containing a planar ring with completely conjugated π electrons, and a group derived from an aromatic hydrocarbon refers to a structure in which an aromatic hydrocarbon or a cyclic aliphatic hydrocarbon is condensed in an aromatic hydrocarbon. In addition, in the present specification, an aryl group includes a univalent group formed by connecting two or more aromatic hydrocarbons or aromatic hydrocarbon derivatives to each other. The aryl group is not particularly limited, but is preferably an aryl group having 6 to 50, 6 to 30, 6 to 25, 6 to 20, 6 to 18, or 6 to 13 carbon atoms, and the above aryl group may be monocyclic or polycyclic. Specifically, as a monocyclic aryl group, it may be phenyl, biphenyl, terphenyl, etc., but it is not limited thereto. Specifically, as a polycyclic aryl group, there are naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, yl, fluorenyl, etc., but are not limited to these.

[0075] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0076] In this specification, when it is indicated that the fluorenyl group may be substituted, the substituted fluorenyl group includes all compounds in which the substituents of the five-membered ring of fluorene are spiro-bonded to each other to form an aromatic hydrocarbon ring. The above-mentioned substituted fluorenyl group includes 9,9'-spirobifluorene, spiro[cyclopentane-1,9'-fluorene], spiro[benzo[c]fluorene-7,9-fluorene], etc., but is not limited thereto.

[0077] In this specification, heteroaryl refers to a monovalent aromatic heterocyclic group. Here, heteroaryl refers to a monovalent group of an aromatic ring or an aromatic ring derivative, and is a group containing one or more of N, O, S and Si as heteroatoms in the ring. The above-mentioned aromatic ring derivatives include all structures in which an aromatic ring or an aliphatic ring is fused in an aromatic ring. In addition, in this specification, heteroaryl includes a monovalent group formed by connecting an aromatic ring containing two or more heteroatoms or a derivative of an aromatic ring containing a heteroatom. The number of carbon atoms of the above-mentioned heteroaryl is preferably 2 to 50, 2 to 30, 2 to 20, 2 to 18, or 2 to 13.

[0078] Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, triazolyl, pyridinyl, bipyridinyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pteridinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, pyridoindolyl, indenopyrimidine (5H-indenopyrimidine), carbazolyl, benzo[1-(4-nitro-2-yl)pyrimidine, 1-nitro-1-nitro-1-carbazolyl ... oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, phenanthroline, isothiophene oxazolyl, and thiadiazolyl, but are not limited thereto.

[0079] In the present specification, an arylene group refers to a group having two bonding positions on an aryl group, that is, a divalent group. The above description of the aryl group is applicable to these groups except that they are each a divalent group.

[0080] In the present specification, a heteroarylene group refers to a group having two bonding positions on a heteroaryl group, that is, a divalent group. The above description of the heteroaryl group is applicable to these groups except that they are each a divalent group.

[0081] In this specification, "adjacent" groups may refer to substituents substituted on atoms directly connected to the atom substituted by the substituent, substituents closest to the substituent in stereostructure, or other substituents substituted on the atom substituted by the substituent. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring can be interpreted as "adjacent" groups to each other.

[0082] In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, "ring" means a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.

[0083] In the present specification, the hydrocarbon ring may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from the examples of the above-mentioned cycloalkyl or aryl groups except that the above-mentioned monovalent group is not present. Examples of condensed rings of aromatic and aliphatic groups include, but are not limited to, 1,2,3,4-tetrahydronaphthalene and 2,3-dihydro-1H-indene.

[0084] In the present specification, the aromatic ring may be monocyclic or polycyclic, and may be selected from the examples of the above-mentioned aryl groups except that it is not monovalent.

[0085] In the present specification, the heterocyclic ring contains one or more non-carbon atoms, i.e., heteroatoms. Specifically, the heteroatoms may contain one or more atoms selected from O, N, S, Si, etc. The heterocyclic ring may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from the examples of the above-mentioned heteroaryl groups except that it is not monovalent.

[0086] In Chemical Formulae 1 and 2 of the present specification, even when a substituent to be substituted is not explicitly indicated, substitution with deuterium is included.

[0087] Next, an organic light-emitting device and a compound including the same according to one embodiment of the present specification will be described.

[0088] The present specification provides an organic light-emitting device, which includes: an anode, a cathode, a first organic layer and a second organic layer between the anode and the cathode, the first organic layer contains a compound represented by the chemical formula 1, and the second organic layer contains a compound represented by the chemical formula 2.

[0089] The compound represented by the above chemical formula 1 according to one embodiment includes boron (B) and two nitrogen atoms at the center. Since the boron compound is introduced, the orbital overlap between HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) is minimized, thereby maintaining a wide band gap while having a high triplet energy. Therefore, high efficiency of the device can be expected.

[0090] The compound represented by the above chemical formula 2 has a structure in which a heterocyclic ring containing one or more N is connected to a spirocyclic ring containing O or S. Due to the above spirocyclic ring containing O or S, steric hindrance is generated in the compound. The above steric hindrance prevents crystallization and improves thermal stability during film formation, so that the layer can be stably formed even at a high evaporation temperature. In one embodiment, when the compound represented by chemical formula 2 is used for an organic layer, due to the high thermal stability and processability, the effect of improving the life of the device can be expected. In addition, a heterocyclic ring containing one or more N is used as a substituent, so that high efficiency of the device can be expected.

[0091] As for the compound represented by the above chemical formula 2, it is not a symmetrical structure (that is, a structure in which R21 and R22, or R23 and R24 simultaneously include the structure of chemical formula 3). That is, the structure of the above chemical formula 3 is asymmetrically included. At this time, due to the asymmetric structure of chemical formula 2, the dipole moment of the molecule is improved. Therefore, when the compound represented by chemical formula 2 is included in an organic layer (for example, an electron transport layer) between the cathode and the light-emitting layer, the electron injection rate into the light-emitting layer is increased, thereby reducing the driving voltage of the organic light-emitting device. In addition, due to the asymmetric structure, the crystallinity in the solution state decreases, so that when the organic layer is formed, an economic effect can be expected in terms of time and / or cost.

[0092] The dipole moment value of the compound represented by Chemical Formula 2 according to one embodiment of the present specification is 0.6 debye or more. The dipole moment value may be attributed to structural characteristics.

[0093] In this specification, the dipole moment is a physical quantity indicating the degree of polarity and can be calculated using the following mathematical formula 1.

[0094] [Mathematical formula 1]

[0095]

[0096] ρ(r0): molecular density

[0097] V: Volume

[0098] ■r:the point of observation

[0099] ■d 3 r0: per unit volume (an elementary volume)

[0100] In the above mathematical formula 1, the value of the dipole moment can be obtained by calculating the molecular density. For example, the molecular density can be calculated by using a method called Hirshfeld Charge Analysis to obtain the charge and dipole of each atom and then calculating it according to the following formula.

[0101] Weight Function

[0102]

[0103] ■ α (r α ): spherical average ground state atomic density

[0104] (spherically averaged ground-state atomic density)

[0105] ■∑ β ρ β (r β ): promolcule density

[0106] Deformation Density

[0107]

[0108] ρ(r): molecular density

[0109] ■ α (r α ): located at coordinate R α The density of free atoms α at

[0110] (density of the free atom α located at coordinates R α )

[0111] Atomic Charge

[0112] q(α)=-∫ρ d (r)W α (r)d 3 r

[0113] ■Wα (r): weight function

[0114] As described above, the compound of Chemical Formula 2 is a material with excellent electron injection effect due to its asymmetric structure. Therefore, it is preferred to maintain the hole-electron balance in the light-emitting layer. The LUMO energy of the compound represented by Chemical Formula 1 is high (i.e., the absolute value is small). When the compound of Chemical Formula 1 is used as a dopant for the light-emitting layer, most of the electrons transferred from the compound of Chemical Formula 2 are transferred to the main body of the light-emitting layer without being transferred to the compound of Chemical Formula 1, thereby improving stability. Therefore, the organic light-emitting device containing the compound of Chemical Formula 1 and the compound of Chemical Formula 2 has excellent efficiency and lifespan.

[0115] In one embodiment of the present specification, the above-mentioned X is B; P=O; or P=S.

[0116] In one embodiment of the present specification, the above-mentioned X is B.

[0117] In one embodiment of the present specification, the above Z1 to Z3 are the same as or different from each other, and are each independently a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.

[0118] In one embodiment of the present specification, the above Z1 to Z3 are the same as or different from each other, and are each independently a substituted or unsubstituted C6-C20 hydrocarbon ring, or a substituted or unsubstituted C2-C20 heterocycle.

[0119] In one embodiment of the present specification, the above Z1 to Z3 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic to tricyclic hydrocarbon ring, or a substituted or unsubstituted monocyclic to tricyclic heterocyclic ring.

[0120] In one embodiment of the present specification, the above-mentioned Z1 to Z3 are the same as or different from each other, and are each independently a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted carbazole ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted dibenzothiophene ring, or a substituted or unsubstituted dibenzoselenophene ring.

[0121] In one embodiment of the present specification, the above Z1 to Z3 are the same as or different from each other, and are each independently a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted carbazole ring, a substituted or unsubstituted dibenzofuran ring, or a substituted or unsubstituted dibenzothiophene ring.

[0122] In one embodiment of the present specification, the above-mentioned Z1 is a hydrocarbon ring which may be substituted by R1, or a heterocyclic ring which may be substituted by R1.

[0123] In one embodiment of the present specification, the above-mentioned Z2 is a hydrocarbon ring which may be substituted by R2, or a heterocyclic ring which may be substituted by R2.

[0124] In one embodiment of the present specification, the above-mentioned Z3 is a hydrocarbon ring which may be substituted by R3, or a heterocyclic ring which may be substituted by R3.

[0125] In one embodiment of the present specification, Z1 is a benzene ring substituted or unsubstituted by R1, a naphthalene ring substituted or unsubstituted by R1, a carbazole ring substituted or unsubstituted by R1, a dibenzofuran ring substituted or unsubstituted by R1, or a dibenzothiophene ring substituted or unsubstituted by R1.

[0126] In one embodiment of the present specification, the above-mentioned Z2 is a benzene ring substituted or unsubstituted by R2, a naphthalene ring substituted or unsubstituted by R2, a carbazole ring substituted or unsubstituted by R2, a dibenzofuran ring substituted or unsubstituted by R2, or a dibenzothiophene ring substituted or unsubstituted by R2.

[0127] In one embodiment of the present specification, the above Z3 is a benzene ring which may be substituted by R3.

[0128] In one embodiment of the present specification, at least one of Z1 and Z2 is a substituted or unsubstituted aromatic hydrocarbon ring, preferably a substituted or unsubstituted benzene ring.

[0129] In one embodiment of the present specification, Z1 is an aromatic hydrocarbon ring which may be substituted by R1, and Z2 is an aromatic hydrocarbon ring which may be substituted by R2.

[0130] In one embodiment of the present specification, Z1 is a hydrocarbon ring which may be substituted by R1, and Z2 is an aromatic heterocyclic ring which may be substituted by R2.

[0131] In one embodiment of the present specification, the above-mentioned R1 to R3 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent substituents are combined with each other to form a substituted or unsubstituted ring.

[0132] In one embodiment of the present specification, the above-mentioned R1 to R3 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C1-C10 haloalkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C30 silyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C1-C10 amine group, a substituted or unsubstituted C6-C60 arylamine group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, or adjacent substituents are combined with each other to form a substituted or unsubstituted ring.

[0133] In one embodiment of the present specification, the above-mentioned R1 to R3 are the same as or different from each other, and are each independently a substituent selected from hydrogen, deuterium, a halogen group, a nitrile group, a C1-C10 alkyl group, a C1-C10 alkoxy group, a C1-C10 amine group, a C6-C60 arylamine group, a C6-C30 aryl group, and a C2-C30 heterocyclic group, or a substituent formed by connecting two or more substituents.

[0134] In one embodiment of the present specification, the above-mentioned R1 to R3 are the same as or different from each other, and are each independently hydrogen, deuterium, a C1-C10 alkyl group, a C6-C60 arylamine group which is substituted or unsubstituted with a C1-C10 alkyl group or a C6-C60 arylamine group, a C6-C30 aryl group, or a C2-C30 heterocyclic group.

[0135] In one embodiment of the present specification, the above R1 to R3 are the same or different from each other, and are independently hydrogen, deuterium, C1-C6 alkyl, C6-C60 arylamine substituted or unsubstituted by C1-C10 alkyl, C6-C30 aryl, or C2-C30 heterocyclic group. In another embodiment, the heterocyclic group of the above R1 to R3 is an N-containing heterocyclic group, specifically a carbazolyl group.

[0136] In one embodiment of the present specification, the above R1 to R3 are the same as or different from each other, and are each independently a methyl group; an ethyl group; a tert-butyl group; a phenyl group; a biphenyl group; a diphenylamine group which is substituted or unsubstituted with a diphenylamine group, a ditolylamine group or a bis(tert-butyl)phenyl)amine group; or a carbazole group.

[0137] In one embodiment of the present specification, two adjacent R1s are bonded to each other to form a substituted or unsubstituted monocyclic or bicyclic aromatic hydrocarbon ring.

[0138] In one embodiment of the present specification, two adjacent R2s are bonded to each other to form a substituted or unsubstituted monocyclic or bicyclic aromatic hydrocarbon ring.

[0139] In one embodiment of the present specification, two adjacent R1s are bonded to each other to form a benzene ring which may be substituted with a C1-C10 alkyl group.

[0140] In one embodiment of the present specification, two adjacent R2s are bonded to each other to form a benzene ring which is substituted or unsubstituted with a C1-C10 alkyl group.

[0141] In one embodiment of the present specification, R3 is a substituent selected from hydrogen, deuterium, a C1-C10 alkyl group, a C6-C60 arylamine group, and a C2-C30 heterocyclic group, or a substituent formed by connecting two or more substituents.

[0142] In one embodiment of the present specification, R3 is hydrogen, deuterium, a C1-C10 alkyl group, a C6-C60 arylamine group which may be substituted with a C1-C10 alkyl group, or a C2-C30 heterocyclic group.

[0143] In one embodiment of the present specification, R3 is hydrogen, deuterium, a C1-C10 alkyl group, a C6-C60 arylamine group, or a C2-C30 heterocyclic group.

[0144] In one embodiment of the present specification, R3 is hydrogen, deuterium, methyl, ethyl, tert-butyl, diphenylamino which may be substituted with tert-butyl, or carbazolyl.

[0145] In one embodiment of the present specification, the above R3 is hydrogen, deuterium, methyl, diphenylamino or carbazolyl.

[0146] In one embodiment of the present specification, the above-mentioned R1 and R2 are the same as or different from each other, and are each independently a substituent selected from hydrogen, deuterium, a C1-C10 alkyl group, a C6-C60 arylamine group, a C6-C30 aryl group, and a C2-C30 heterocyclic group, or a substituent formed by connecting two or more substituents.

[0147] In one embodiment of the present specification, the above R1 and R2 are the same or different from each other, and are independently hydrogen, deuterium, C1-C10 alkyl, C6-C60 arylamine substituted or unsubstituted by C1-C10 alkyl or C6-C60 arylamine, C6-C30 aryl, or C2-C30 heterocyclic group. In another embodiment, the heterocyclic group of R1 and R3 is an N-containing heterocyclic group, specifically a carbazolyl group.

[0148] In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are independently hydrogen, deuterium, or a C1-C10 alkyl group.

[0149] In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, or a C1-C6 alkyl group.

[0150] In one embodiment of the present specification, R1 and R2 are the same as or different from each other and are independently methyl, ethyl, tert-butyl, phenyl, biphenyl, or diphenylamino which may be substituted with diphenylamino, methyl or tert-butyl.

[0151] In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently a methyl group, an ethyl group or a tert-butyl group.

[0152] In one embodiment of the present specification, the above-mentioned A1 is N(R101) or O.

[0153] In one embodiment of the present specification, the above-mentioned A2 is N(R102) or O.

[0154] In one embodiment of the present specification, the above-mentioned A1 is N(R101).

[0155] In one embodiment of the present specification, the above-mentioned A2 is N(R102).

[0156] In one embodiment of the present specification, the above-mentioned A1 is O.

[0157] In one embodiment of the present specification, the above-mentioned A2 is O.

[0158] In one embodiment of the present specification, R101 and R102 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0159] In one embodiment of the present specification, R101 and R102 are the same as or different from each other, and are each independently a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C30 aryl group.

[0160] In one embodiment of the present specification, R101 and R102 are the same as or different from each other, and are each independently a C1-C10 alkyl group, or a C6-C30 aryl group which may be substituted with a C1-C10 alkyl group.

[0161] In one embodiment of the present specification, X is B, A1 is N(R101), A2 is N(R102), R101 and R102 are the same as or different from each other, and are each independently a C1-C10 alkyl group, or a C6-C30 aryl group which may be substituted or unsubstituted by a C1-C10 alkyl group.

[0162] In one embodiment of the present specification, R101 and R102 are the same as or different from each other and are each independently a methyl group, a tert-butyl group, a phenyl group which may be substituted by a methyl group or a tert-butyl group, or a biphenyl group which may be substituted by a tert-butyl group.

[0163] In one embodiment of the present specification, the above Chemical Formula 1 may be represented by any one of the following Chemical Formulas 101 to 108.

[0164] [Chemical Formula 101]

[0165]

[0166] [Chemical formula 102]

[0167]

[0168] [Chemical formula 103]

[0169]

[0170] [Chemical formula 104]

[0171]

[0172] [Chemical formula 105]

[0173]

[0174] [Chemical formula 106]

[0175]

[0176] [Chemical formula 107]

[0177]

[0178] [Chemical formula 108]

[0179]

[0180] In the above Chemical Formulas 101 to 108,

[0181] X, A1 and A2 are defined as in Chemical Formula 1.

[0182] Q is O, S, Se, N(R51) or C(R52)(R53),

[0183] R11 to R20 and R51 to R53 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent substituents are combined with each other to form a substituted or unsubstituted ring,

[0184] r11 and r12 are integers from 0 to 4. When r11 and r12 are 2 or more, R11 and R12 are the same as or different from each other.

[0185] r13 is an integer from 0 to 3. When r13 is 2 or more, R13 are the same or different from each other.

[0186] r14 to r20 are integers of 0 to 6, and when r14 to r20 are 2 or more, R14 to R20 are the same as or different from each other.

[0187] In one embodiment of the present specification, the definition of R1 can be applied to R11. In another embodiment, the definition of R2 can be applied to R12, R14 to R20. In another embodiment, the definition of R3 can be applied to R13.

[0188] In one embodiment of the present specification, the above-mentioned Q is O, S or N(R51).

[0189] In one embodiment of the present specification, the above-mentioned Q is O or S.

[0190] In one embodiment of the present specification, the above R51 is a substituted or unsubstituted C6-C30 aryl group.

[0191] In one embodiment of the present specification, the above R51 is a C6-C20 aryl group.

[0192] In one embodiment of the present specification, the above-mentioned R51 is a phenyl group.

[0193] In one embodiment of the present specification, R52 and R53 are the same as or different from each other, and are each independently a methyl group or a phenyl group.

[0194] In one embodiment of the present specification, the above-mentioned R11 to R20 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0195] In one embodiment of the present specification, the above-mentioned R11 to R20 are the same as or different from each other, and are each independently hydrogen, deuterium, a C1-C10 alkyl group, a C6-C60 arylamine group which is substituted or unsubstituted by a C1-C10 alkyl group or a C6-C60 arylamine group, a C6-C30 aryl group, or a C2-C30 heterocyclic group.

[0196] In one embodiment of the present specification, the above R11 to R20 are the same or different from each other, and are independently hydrogen, deuterium, C1-C6 alkyl, C6-C60 arylamine substituted or unsubstituted by C1-C10 alkyl, C6-C30 aryl, or C2-C30 heterocyclic group. In another embodiment, the above heterocyclic group of R11 to R20 is an N-containing heterocyclic group, specifically a carbazolyl group.

[0197] In one embodiment of the present specification, the above R11 to R20 are the same as or different from each other, and are each independently a methyl group; an ethyl group; a tert-butyl group; a phenyl group; a biphenyl group; a diphenylamine group which is substituted or unsubstituted with a diphenylamine group, a ditolylamine group or a bis(tert-butyl)phenyl)amine group; or a carbazole group.

[0198] In one embodiment of the present specification, R13 is a substituent selected from hydrogen, deuterium, a C1-C10 alkyl group, a C6-C60 arylamine group, and a C2-C30 heterocyclic group, or a substituent formed by connecting two or more substituents.

[0199] In one embodiment of the present specification, R13 is hydrogen, deuterium, a C1-C10 alkyl group, a C6-C60 arylamine group which may be substituted with a C1-C10 alkyl group, or a C2-C30 heterocyclic group.

[0200] In one embodiment of the present specification, R13 is hydrogen, deuterium, a C1-C10 alkyl group, a C6-C60 arylamine group, or a C2-C30 heterocyclic group.

[0201] In one embodiment of the present specification, R13 is hydrogen, deuterium, methyl, ethyl, tert-butyl, diphenylamino which may be substituted with tert-butyl, or carbazolyl.

[0202] In one embodiment of the present specification, R13 is hydrogen, deuterium, methyl, diphenylamino or carbazolyl.

[0203] In one embodiment of the present specification, the above R11, R12, R14 to R20 are the same as or different from each other, and are each independently a substituent selected from hydrogen, deuterium, a C1-C10 alkyl group, a C6-C60 arylamine group, a C6-C30 aryl group, and a C2-C30 heterocyclic group, or a substituent formed by connecting two or more substituents.

[0204] In one embodiment of the present specification, the above R11, R12, R14 to R20 are the same or different from each other, and are independently hydrogen, deuterium, C1-C10 alkyl, C6-C60 arylamine substituted or unsubstituted by C1-C10 alkyl or C6-C60 arylamine, C6-C30 aryl, or C2-C30 heterocyclic group. In another embodiment, the above heterocyclic group of R11, R12, R14 to R20 is an N-containing heterocyclic group, specifically a carbazolyl group.

[0205] In one embodiment of the present specification, the above R11, R12, R14 to R20 are the same as or different from each other, and are each independently hydrogen, deuterium or a C1-C10 alkyl group.

[0206] In one embodiment of the present specification, the above R11, R12, R14 to R20 are the same as or different from each other, and are each independently hydrogen, deuterium or a C1-C6 alkyl group.

[0207] In one embodiment of the present specification, the above R11, R12, R14 to R20 are the same as or different from each other, and are independently methyl; ethyl; tert-butyl; phenyl; biphenyl; or diphenylamino which may be substituted by diphenylamino, methyl or tert-butyl.

[0208] In one embodiment of the present specification, the above R11, R12, R14 to R20 are the same as or different from each other, and are each independently a methyl group, an ethyl group or a tert-butyl group.

[0209] In one embodiment of the present specification, the compound represented by the above Chemical Formula 1 is any one selected from the following compounds.

[0210]

[0211]

[0212] In one embodiment of the present specification, the above-mentioned Y is O or S.

[0213] In one embodiment of the present specification, the above-mentioned Y is O.

[0214] In one embodiment of the present specification, the above-mentioned Y is S.

[0215] In one embodiment of the present specification, the above R21 to R24 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are represented by the above Chemical Formula 3, or adjacent substituents are combined with each other to form a substituted or unsubstituted ring, and at least one of R21 to R24 is represented by the above Chemical Formula 3.

[0216] In one embodiment of the present specification, the R21 is represented by the above Chemical Formula 3.

[0217] In one embodiment of the present specification, the R22 is represented by the above Chemical Formula 3.

[0218] In one embodiment of the present specification, the R23 is represented by the above Chemical Formula 3.

[0219] In one embodiment of the present specification, the R24 is represented by the above Chemical Formula 3.

[0220] In one embodiment of the present specification, the above R21 to R24 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C6-C30 heterocyclic group, or are represented by the above Chemical Formula 3, or adjacent substituents are combined with each other to form a substituted or unsubstituted C3-C30 ring.

[0221] In one embodiment of the present specification, the above R21 to R24 are the same as or different from each other, and are independently hydrogen, deuterium, a C1-C10 alkyl group, or a C6-C30 aryl group substituted or unsubstituted by a C1-C10 alkyl group, or are represented by the above Chemical Formula 3, or adjacent substituents are combined with each other to form a benzene ring.

[0222] In one embodiment of the present specification, the above R21 to R24 are the same as or different from each other, and are each independently hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, phenyl substituted or unsubstituted with methyl or tert-butyl, biphenyl, or naphthyl, or are represented by the above Chemical Formula 3, or adjacent substituents are combined with each other to form a benzene ring.

[0223] In one embodiment of the present specification, one or more of the above R21 to R24 are represented by the above Chemical Formula 3, and the rest are the same or different from each other and are independently hydrogen, deuterium, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C6-C30 heterocyclic group, or two adjacent R21, two adjacent R22, two adjacent R23, or two adjacent R24 are combined with each other to form a substituted or unsubstituted C3-C30 ring.

[0224] In one embodiment of the present specification, one or two of the above R21 to R24 are represented by the above Chemical Formula 3, and the rest are the same as or different from each other and are independently hydrogen, deuterium, a C1-C10 alkyl group, or a C6-C30 aryl group substituted or unsubstituted by a C1-C10 alkyl group, or two adjacent R21s, two adjacent R22s, two adjacent R23s, or two adjacent R24s are combined with each other to form a benzene ring.

[0225] In one embodiment of the present specification, one or two of the above R21 to R24 are represented by the above Chemical Formula 3, and the rest are the same or different from each other and are independently hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, phenyl substituted or unsubstituted with methyl or tert-butyl, biphenyl or naphthyl, or two adjacent R21, two adjacent R22, two adjacent R23, or two adjacent R24 are combined with each other to form a benzene ring.

[0226] In one embodiment of the present specification, one or two of the above R21 to R24 are represented by the above Chemical Formula 3, and the rest are the same or different from each other and are independently hydrogen, deuterium, or a phenyl group which is substituted or unsubstituted with a methyl group, or two of the adjacent R21s or two of the adjacent R22s are combined with each other to form a benzene ring.

[0227] In one embodiment of the present specification, two adjacent R21's are bonded to each other to form a substituted or unsubstituted benzene ring.

[0228] In one embodiment of the present specification, two adjacent R22's are bonded to each other to form a substituted or unsubstituted benzene ring.

[0229] In one embodiment of the present specification, two adjacent R21's are bonded to each other to form a benzene ring.

[0230] In one embodiment of the present specification, two adjacent R22 are bonded to each other to form a benzene ring.

[0231] In one embodiment of the present specification, the above-mentioned r21 to r24 are the same or different from each other, and each independently represents an integer from 0 to 4. When r21 is 2 or more, R21 is the same or different from each other, when r22 is 2 or more, R22 is the same or different from each other, when r23 is 2 or more, R23 is the same or different from each other, and when r24 is 2 or more, R24 is the same or different from each other.

[0232] In one embodiment of the present specification, r21 to r24 are the same as or different from each other, and are each independently 0 to 2.

[0233] In one embodiment of the present specification, the above-mentioned X1 is N or C(R31).

[0234] In one embodiment of the present specification, the above-mentioned X2 is N or C(R32).

[0235] In one embodiment of the present specification, the above-mentioned X3 is N or C(R33).

[0236] In one embodiment of the present specification, at least one of X1 to X3 is N.

[0237] In one embodiment of the present specification, two or more of the above X1 to X3 are N.

[0238] In one embodiment of the present specification, all of X1 to X3 are N.

[0239] In one embodiment of the present specification, X1 is N, X2 is N, and X3 is C(R33). In another embodiment, R33 is combined with Ar2 to form a benzene ring.

[0240] In one embodiment of the present specification, X1 is N, X2 is C(R32), and X3 is N. In another embodiment, R33 is combined with Ar2 to form a benzene ring.

[0241] In one embodiment of the present specification, the above R31, R32 and R33 are the same as or different from each other, and are independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are combined with Ar1 or Ar2 to form a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.

[0242] In one embodiment of the present specification, the above R31, R32 and R33 are the same or different from each other, and are independently hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C2-C30 heterocyclic group, or combine with Ar1 or Ar2 to form a substituted or unsubstituted C6-C30 aromatic hydrocarbon ring, or a substituted or unsubstituted C2-C30 heterocyclic ring. In another embodiment, "substituted or unsubstituted" means substituted by a substituent selected from deuterium, C1-C10 alkyl, C6-C30 aryl and C2-C30 heteroaryl, or a substituent formed by connecting two or more substituents, or having no substituent.

[0243] In one embodiment of the present specification, the above R31, R32 and R33 are the same or different from each other, and are independently hydrogen, deuterium, substituted or unsubstituted monocyclic to tetracyclic aryl, or substituted or unsubstituted monocyclic to tetracyclic heterocyclic group, or combined with Ar1 or Ar2 to form a substituted or unsubstituted monocyclic to tetracyclic aromatic hydrocarbon ring, or a substituted or unsubstituted monocyclic to tetracyclic heterocyclic ring. In another embodiment, "substituted or unsubstituted" refers to being substituted by a substituent selected from deuterium, C1-C10 alkyl, C6-C30 aryl and C2-C30 heteroaryl, or a substituent formed by connecting two or more substituents, or having no substituent.

[0244] In one embodiment of the present specification, the above-mentioned R31, R32 and R33 are the same as or different from each other, and are independently hydrogen, deuterium, phenyl, biphenyl, naphthyl, carbazolyl, phenylcarbazolyl or benzocarbazolyl, or are combined with Ar1 or Ar2 to form a benzene ring substituted or unsubstituted by a C6-C30 aromatic group or a C2-C30 heterocyclic group.

[0245] In one embodiment of the present specification, each of R31, R32 and R33 is hydrogen or deuterium.

[0246] In one embodiment of the present specification, R31, R32 and R33 are hydrogen.

[0247] In one embodiment of the specification, the above R31 is combined with Ar1 to form a substituted or unsubstituted ring, a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.

[0248] In one embodiment of the present specification, the above R32 is combined with Ar1 to form a substituted or unsubstituted ring, a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.

[0249] In one embodiment of the present specification, the above R32 is combined with Ar2 to form a substituted or unsubstituted ring, a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.

[0250] In one embodiment of the present specification, the above R33 is combined with Ar2 to form a substituted or unsubstituted ring, a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.

[0251] In one embodiment of the present specification, the above R31 is bonded to Ar1 to form a benzene ring which may be substituted by R41.

[0252] In one embodiment of the present specification, the above R32 is bonded to Ar1 to form a benzene ring which may be substituted by R41.

[0253] In one embodiment of the present specification, the above R32 is bonded to Ar2 to form a benzene ring which may be substituted by R41.

[0254] In one embodiment of the present specification, the above R33 is bonded to Ar2 to form a benzene ring which may be substituted by R41.

[0255] In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are combined with R31, R32 or R33 to form a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.

[0256] In one embodiment of the present specification, the above-mentioned Ar1 and Ar2 are the same as or different from each other, and are each independently a C6-C30 aryl group substituted or unsubstituted by a substituent selected from the group consisting of deuterium, cyano, C1-C10 alkyl, C6-C30 aryl and C2-C20 heterocyclic group, or a substituent formed by connecting two or more substituents selected from the above group; or a C6-C30 heterocyclic group substituted or unsubstituted by a substituent selected from the group consisting of deuterium, cyano, C1-C10 alkyl, C6-C30 aryl and C2-C20 heterocyclic group, or a substituent formed by connecting two or more substituents selected from the above group.

[0257] In one embodiment of the present specification, the above-mentioned Ar1 and Ar2 are the same as or different from each other, and are each independently a C6-C30 aryl group substituted or unsubstituted by a substituent selected from the group consisting of deuterium, cyano, C6-C30 aryl and C2-C20 heterocyclic group, or a substituent formed by connecting two or more substituents selected from the above group; or a C6-C30 heterocyclic group substituted or unsubstituted by a substituent selected from the group consisting of deuterium, C6-C30 aryl and C2-C20 heterocyclic group, or a substituent formed by connecting two or more substituents selected from the above group.

[0258] In one embodiment of the present specification, the above-mentioned Ar1 and Ar2 are the same as or different from each other, and are each independently a C6-C20 aromatic group substituted or unsubstituted by a substituent selected from the group consisting of deuterium, cyano, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl and carbazole, or a substituent formed by connecting two or more substituents selected from the above group.

[0259] In one embodiment of the present specification, the above-mentioned Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group substituted or unsubstituted by R41, or a heterocyclic group substituted or unsubstituted by R42, or are combined with R31, R32 or R33 to form an aromatic hydrocarbon ring substituted or unsubstituted by R41, or a heterocyclic ring substituted or unsubstituted by R42.

[0260] In one embodiment of the present specification, the above-mentioned Ar1 and Ar2 are the same as or different from each other, and are each independently a C6-C30 aryl group substituted or unsubstituted by R41, or a C2-C30 heterocyclic group substituted or unsubstituted by R42, or are combined with R31, R32 or R33 to form a C6-C30 aromatic hydrocarbon ring substituted or unsubstituted by R41, or a C2-C30 heterocyclic ring substituted or unsubstituted by R42.

[0261] In one embodiment of the present specification, the above-mentioned Ar1 and Ar2 are the same as or different from each other, and are each independently a C6-C20 aryl group substituted or unsubstituted by R41, or a C2-C20 heterocyclic group substituted or unsubstituted by R42, or are combined with R31, R32 or R33 to form a C6-C20 aromatic hydrocarbon ring substituted or unsubstituted by R41, or a C2-C20 heterocyclic ring substituted or unsubstituted by R42.

[0262] In one embodiment of the present specification, the above-mentioned Ar1 and Ar2 are the same as or different from each other, and are independently a monocyclic to pentacyclic aromatic group substituted or unsubstituted by R41, or a monocyclic to pentacyclic heterocyclic group substituted or unsubstituted by R42, or are combined with R31, R32 or R33 to form a monocyclic to pentacyclic aromatic hydrocarbon ring substituted or unsubstituted by R41; or a monocyclic to pentacyclic heterocyclic ring substituted or unsubstituted by R42.

[0263] In one embodiment of the present specification, the above-mentioned Ar1 and Ar2 are the same as or different from each other, and are each independently a monocyclic to tetracyclic aromatic group substituted or unsubstituted by R41, or a monocyclic to tetracyclic heterocyclic group substituted or unsubstituted by R42, or are combined with R31, R32 or R33 to form a monocyclic to tetracyclic aromatic hydrocarbon ring substituted or unsubstituted by R41; or a monocyclic to tetracyclic heterocyclic ring substituted or unsubstituted by R42.

[0264] In one embodiment of the present specification, the above-mentioned Ar1 and Ar2 are the same as or different from each other, and are each independently a monocyclic to tricyclic aromatic group substituted or unsubstituted by R41, or a monocyclic to tricyclic heterocyclic group substituted or unsubstituted by R42, or are combined with R31, R32 or R33 to form a monocyclic to tricyclic aromatic hydrocarbon ring substituted or unsubstituted by R41; or a monocyclic to tricyclic heterocyclic ring substituted or unsubstituted by R42.

[0265] In one embodiment of the present specification, the above-mentioned Ar1 and Ar2 are the same as or different from each other, and are each independently phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluoranthene, phenanthracene, anthracene, fluorenyl or dimethylfluorenyl, and the above-mentioned substituents are substituted by R41 or unsubstituted.

[0266] In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a monocyclic to pentacyclic heterocyclic group containing N, O, S or Si which may be substituted or unsubstituted by R42.

[0267] In one embodiment of the present specification, Ar1 and Ar2 are the same or different from each other and are independently carbazolyl, phenylcarbazolyl, benzocarbazolyl, indenylcarbazolyl, dibenzothiophenyl, dibenzofuran, dibenzosilole, phenoxy R42 is substituted or unsubstituted by R42.

[0268] In one embodiment of the present specification, Ar1 and R31 are combined to form a substituted or unsubstituted ring, a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.

[0269] In one embodiment of the present specification, Ar1 and R32 are combined to form a substituted or unsubstituted ring, a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.

[0270] In one embodiment of the present specification, Ar2 and R32 are combined to form a substituted or unsubstituted ring, a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.

[0271] In one embodiment of the present specification, Ar2 and R33 are combined to form a substituted or unsubstituted ring, a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.

[0272] In one embodiment of the present specification, Ar1 and R31 are bonded to form a benzene ring which may be substituted by R41.

[0273] In one embodiment of the present specification, the above-mentioned Ar1 and R32 are bonded to form a benzene ring which may be substituted by R41.

[0274] In one embodiment of the present specification, the above-mentioned Ar2 and R32 are bonded to form a benzene ring which may be substituted by R41.

[0275] In one embodiment of the present specification, the above-mentioned Ar2 and R33 are bonded to form a benzene ring which may be substituted by R41.

[0276] In one embodiment of the present specification, the above R41 and R42 are the same as or different from each other, and are each independently selected from deuterium, a halogen group, a nitrile group, an alkyl group, a halogenated alkyl group, an alkoxy group, a silyl group, an aryl group and a heterocyclic group, or are a group formed by connecting two or more substituents.

[0277] In one embodiment of the present specification, the above-mentioned R41 and R42 are the same as or different from each other, and are each independently selected from deuterium, a halogen group, a nitrile group, a C1-C20 alkyl group, a C1-C20 haloalkyl group, a C1-C20 alkoxy group, a C1-C50 silyl group, a C6-C50 aryl group, and a C2-C50 heterocyclic group, or are a group formed by connecting two or more substituents.

[0278] In one embodiment of the present specification, the above-mentioned R41 and R42 are the same as or different from each other, and are each independently selected from deuterium, a halogen group, a nitrile group, a C1-C10 alkyl group, a C1-C10 haloalkyl group, a C1-C10 alkoxy group, a C1-C30 silyl group, a C6-C30 aryl group, and a C2-C30 heterocyclic group, or are a group formed by connecting two or more substituents.

[0279] In one embodiment of the present specification, the above-mentioned R41 and R42 are the same as or different from each other, and are each independently selected from deuterium, a halogen group, a nitrile group, a C1-C5 alkyl group, a C1-C5 haloalkyl group, a C1-C5 alkoxy group, a C1-C20 silyl group, a C6-C20 aryl group, and a C2-C20 heterocyclic group, or are a group formed by connecting two or more substituents.

[0280] In one embodiment of the present specification, the above R41 and R42 are the same as or different from each other, and are each independently selected from deuterium, a halogen group, a nitrile group, a C1-C20 alkyl group, a C1-C20 haloalkyl group, a C1-C20 alkoxy group, a C1-C50 silyl group, a monocyclic to pentacyclic aryl group, and a monocyclic to pentacyclic heterocyclic group, or are a group formed by connecting two or more substituents.

[0281] In one embodiment of the present specification, the above-mentioned R41 and R42 are the same as or different from each other, and are each independently selected from deuterium, a halogen group, a nitrile group, a C1-C10 alkyl group, a C1-C10 haloalkyl group, a C1-C10 alkoxy group, a C1-C30 silyl group, a monocyclic to tetracyclic aromatic group, and a monocyclic to tetracyclic heterocyclic group, or are a group formed by connecting two or more substituents.

[0282] In one embodiment of the present specification, the above-mentioned R41 and R42 are the same as or different from each other, and are each independently selected from deuterium, a halogen group, a nitrile group, a C1-C5 alkyl group, a C1-C5 haloalkyl group, a C1-C5 alkoxy group, a C1-C20 silyl group, a monocyclic to tricyclic aromatic group, and a monocyclic to tricyclic heterocyclic group, or are a group formed by connecting two or more substituents.

[0283] In one embodiment of the present specification, R41 and R42 are the same or different from each other and are independently selected from deuterium, nitrile, methyl, ethyl, propyl, isopropyl, n-butyl, tert-butyl, trifluoromethyl, methoxy, ethoxy, trimethylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluoranthene, phenanthracene, anthracene, fluorenyl, dimethylfluorenyl, carbazolyl, phenylcarbazolyl, benzocarbazolyl, indenocarbazolyl, dibenzothiophenyl, dibenzofuranyl, dibenzosilole, phenanthroline, The invention can be any one of the following substituents: oxazinyl, phenothiazinyl, phenazinyl, acridinyl, dihydrophenazinyl, dihydroacridinyl, pyridinyl, pyrimidinyl, quinolyl, isoquinolyl, quinazolinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrimidoindolyl and pyridoindolyl, or a group in which two or more substituents are connected.

[0284] In one embodiment of the present specification, the above-mentioned L is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group.

[0285] In one embodiment of the present specification, the above-mentioned L is a direct bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C2-C30 divalent heterocyclic group.

[0286] In one embodiment of the present specification, L is a direct bond, a C6-C30 arylene group, or a C2-C30 divalent heterocyclic group. The arylene group or divalent heterocyclic group may be substituted or unsubstituted with a substituent selected from a nitrile group, a C1-C10 alkyl group, a C6-C30 aryl group, and a C2-C30 heterocyclic group, or a substituent formed by connecting two or more substituents.

[0287] In one embodiment of the present specification, L is a direct bond, a monocyclic to pentacyclic arylene group, or a monocyclic to pentacyclic divalent heterocyclic group. The arylene group or divalent heterocyclic group is substituted or unsubstituted with a substituent selected from a nitrile group, a C1-C10 alkyl group, a C6-C30 aryl group, and a C2-C30 heterocyclic group, or a substituent formed by connecting two or more substituents.

[0288] In one embodiment of the present specification, L is a direct bond, a monocyclic to tetracyclic arylene group, or a monocyclic to tetracyclic divalent heterocyclic group. The arylene group or divalent heterocyclic group is substituted or unsubstituted with a substituent selected from a nitrile group, a C1-C10 alkyl group, a C6-C30 aryl group, and a C2-C30 heterocyclic group, or a substituent formed by connecting two or more substituents.

[0289] In one embodiment of the present specification, L is a direct bond, a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, an anthrylene group, a divalent phenanthryl group, a divalent triphenylene group, a divalent fluoranthene group, a divalent phenanthrenyl group, a divalent fluorenyl group, a divalent fluorenyl group, a divalent dimethylfluorenyl group, a divalent carbazolyl group, a divalent phenylcarbazolyl group, a divalent benzocarbazolyl group, a divalent indenocarbazolyl group, a divalent dibenzothiophenyl group, a divalent dibenzofuranyl group, a divalent dibenzosilyl group, a divalent phenanthrenyl group The connecting group (L) is substituted or unsubstituted with one substituent selected from the group consisting of a nitrile group, a C1-C10 alkyl group, a C6-C30 aryl group, and a C2-C30 heterocyclic group, or a substituent formed by connecting two or more substituents.

[0290] In one embodiment of the present specification, the above-mentioned L is a direct bond, a C6-C30 arylene group, or a C2-C30 divalent heterocyclic group.

[0291] In one embodiment of the present specification, the above-mentioned L is a direct bond, a C6-C30 arylene group, or a C2-C30 divalent N-containing heterocyclic group.

[0292] In one embodiment of the present specification, L is a direct bond, a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, a divalent dibenzothiophenyl group, a divalent dibenzofuranyl group, a divalent pyridyl group, a divalent pyrimidyl group, a divalent quinolyl group, or a divalent isoquinolyl group.

[0293] In one embodiment of the present specification, the above-mentioned L is a direct bond, a phenylene group, a divalent pyridyl group, or a divalent dibenzothiophenyl group.

[0294] In one embodiment of the present specification, the above-mentioned L is a direct bond, a phenylene group, a biphenylene group, or a naphthylene group.

[0295] In one embodiment of the present specification, the above-mentioned L is a direct bond.

[0296] In one embodiment of the present specification, the m is an integer of 0 to 2.

[0297] In one embodiment of the present specification, the above m is 0 or 1.

[0298] In one embodiment of the present specification, the above m is 0.

[0299] In one embodiment of the present specification, the r21 is an integer from 0 to 2.

[0300] In one embodiment of the present specification, the above r22 is an integer from 0 to 2.

[0301] In one embodiment of the present specification, the above r23 is an integer from 0 to 2.

[0302] In one embodiment of the present specification, the above r24 is an integer from 0 to 2.

[0303] In one embodiment of the present specification, the above r21 is 1.

[0304] In one embodiment of the present specification, the above r22 is 1.

[0305] In one embodiment of the present specification, the above r23 is 1.

[0306] In one embodiment of the present specification, the above r24 is 1.

[0307] In one embodiment of the present specification, the above Chemical Formula 3 is represented by any one of the following Chemical Formulas 301 to 303.

[0308] [Chemical formula 301]

[0309]

[0310] [Chemical formula 302]

[0311]

[0312] [Chemical formula 303]

[0313]

[0314] In the above chemical formulas 301 to 303,

[0315] The definitions of L, m, Ar1 and Ar2 are the same as those in Chemical Formula 3,

[0316] At least one of X1 to X3 is N, and the others are CH or CD,

[0317] R30 is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

[0318] r30 is an integer of 0 to 4, and when r30 is 2 or more, R30 are the same as or different from each other.

[0319] In one embodiment of the present specification, in the above chemical formula 301, X1 is N or C(R31), X2 is N or C(R32), X3 is N or C(R33), one or more of X1 to X3 is N, R31, R32 and R33 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0320] In one embodiment of the present specification, in the above Chemical Formula 301, R31, R32, and R33 are hydrogen.

[0321] In one embodiment of the present specification, R30 is hydrogen, deuterium, a substituted or unsubstituted C1-10 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group.

[0322] In one embodiment of the present specification, the above R30 is hydrogen, methyl, phenyl or benzocarbazolyl.

[0323] In one embodiment of the present specification, the above R30 is hydrogen.

[0324] In one embodiment of the present specification, the above Chemical Formula 2 is represented by any one of the following Chemical Formulas 201 to 204.

[0325] [Chemical formula 201]

[0326]

[0327] [Chemical formula 202]

[0328]

[0329] [Chemical formula 203]

[0330]

[0331] [Chemical formula 204]

[0332]

[0333] In the above chemical formulas 201 to 204,

[0334] X1 to X3, L, m, Ar1, Ar2, R21 to R24, r21 to r24 and Y are defined as in Chemical Formula 2,

[0335] X4 is N or C (R34), X5 is N or C (R35), X6 is N or C (R36), at least one of X4 to X6 is N,

[0336] R34, R35 and R36 are the same or different from each other, and are independently hydrogen or deuterium, or are combined with Ar3 or Ar4 to form a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring,

[0337] Ar3 and Ar4 are the same or different from each other, and are each independently an aryl group substituted or unsubstituted by R43, or a heterocyclic group substituted or unsubstituted by R44, or are combined with R34, R35 or R36 to form a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring,

[0338] R43 and R44 are the same as or different from each other, and are each independently selected from deuterium, a halogen group, a nitrile group, an alkyl group, a halogenated alkyl group, an alkoxy group, a silyl group, an aryl group, and a heterocyclic group, or are a group formed by connecting two or more substituents,

[0339] L11 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group,

[0340] m11 is an integer of 0 to 4. When m11 is 2 or more, L11 are the same as or different from each other.

[0341] In one embodiment of the present specification, the above chemical formulas 201 to 204 It can be represented by any one of the above Chemical Formulas 301 to 303.

[0342] In one embodiment of the present specification, the above description about L can be applied to the above L11.

[0343] In one embodiment of the present specification, the above description about m can be applied to the above m11.

[0344] In one embodiment of the present specification, the above description about X1 to X3 can be applied to X4 to X6.

[0345] In one embodiment of the present specification, the above description about Ar1 and Ar2 can be applied to Ar3 and Ar4.

[0346] According to one embodiment of the present specification, the above Chemical Formula 2 is represented by any one of the following Chemical Formulas 211 to 218.

[0347] [Chemical formula 211]

[0348]

[0349] [Chemical formula 212]

[0350]

[0351] [Chemical formula 213]

[0352]

[0353] [Chemical formula 214]

[0354]

[0355] [Chemical formula 215]

[0356]

[0357] [Chemical formula 216]

[0358]

[0359] [Chemical formula 217]

[0360]

[0361] [Chemical formula 218]

[0362]

[0363] In the above chemical formulas 211 to 218,

[0364] Definitions of X1 to X3, L, m, Ar1, Ar2, R21 to R24, r21 to r24, and Y are the same as those in Chemical Formula 2.

[0365] According to one embodiment of the present specification, the above Chemical Formula 2 is represented by any one of the following Chemical Formulas 401 to 403.

[0366] [Chemical Formula 401]

[0367]

[0368] [Chemical formula 402]

[0369]

[0370] [Chemical formula 403]

[0371]

[0372] In the above chemical formulas 401 to 403,

[0373] X1 to X3, L, m, Ar1, Ar2, R21, R22, R24, r21, r22, r24 and Y are defined as in Chemical Formula 2,

[0374] R25 and R26 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group,

[0375] r25 and r26 are the same or different from each other and are each independently an integer of 0 to 6. When r25 is 2 or more, R25 is the same or different from each other, and when r26 is 2 or more, R26 is the same or different from each other.

[0376] In one embodiment of the present specification, the above description about R21 and R22 can be applied to R25 and R26.

[0377] According to one embodiment of the present specification, the compound represented by the above Chemical Formula 2 is any one selected from the following compounds.

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396]

[0397]

[0398]

[0399]

[0400]

[0401]

[0402]

[0403]

[0404]

[0405]

[0406]

[0407]

[0408]

[0409]

[0410]

[0411]

[0412]

[0413]

[0414]

[0415]

[0416]

[0417]

[0418]

[0419]

[0420]

[0421]

[0422]

[0423]

[0424]

[0425]

[0426]

[0427]

[0428]

[0429]

[0430]

[0431]

[0432]

[0433]

[0434]

[0435]

[0436]

[0437]

[0438] The present specification provides an organic light-emitting device, which includes: an anode, a cathode, a first organic layer and a second organic layer between the anode and the cathode, the first organic layer contains a compound represented by the chemical formula 1, and the second organic layer contains a compound represented by the chemical formula 2.

[0439] The organic light-emitting device according to the present specification may include an additional organic layer in addition to the first organic layer and the second organic layer.

[0440] In the present specification, when it is mentioned that a certain member is located “on” another member, it includes not only a case where the certain member is in contact with the other member but also a case where other members are present between the two members.

[0441] In this specification, the above-mentioned "layer" is interchangeable with the "film" mainly used in this technical field, and refers to a coating covering the target area. The size of the above-mentioned "layer" is not limited, and the sizes of each "layer" can be the same or different. In one embodiment, the size of the "layer" can be equal to the size of the entire device, can be equivalent to the size of a specific functional area, or can be as small as a sub-pixel.

[0442] In this specification, a specific substance A is contained in layer B, which means that i) more than one substance A is contained in one layer of layer B, and ii) layer B is composed of more than one layer and substance A is contained in more than one layer of the multiple layers of layer B.

[0443] In this specification, the specific substance A is contained in the C layer or the D layer, which means i) contained in one or more layers of one or more C layers, or ii) contained in one or more layers of one or more D layers, or iii) contained in one or more layers of one or more C layers and one or more layers of one or more D layers, respectively.

[0444] The organic layer of the organic light-emitting device of the present specification may be formed by a single-layer structure, or may be formed by a multi-layer structure in which two or more organic layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, etc. However, the structure of the organic light-emitting device is not limited thereto, and may include more or less organic layers.

[0445] In one embodiment of the present specification, the compound represented by the above Chemical Formula 1 is included in the first organic layer.

[0446] In one embodiment of the present specification, the first organic layer includes a hole injection layer, a hole transport layer, a hole regulation layer, an electron blocking layer, a layer that simultaneously transports and injects holes, or a light-emitting layer.

[0447] In one embodiment of the present specification, the first organic layer is a light-emitting layer.

[0448] In one embodiment of the present specification, the light-emitting layer includes the compound represented by the above Chemical Formula 1 as a dopant of the light-emitting layer.

[0449] In one embodiment of the present specification, the compound represented by the above chemical formula 1 contains 0.01 parts by weight or more and less than 20 parts by weight relative to 100 parts by weight of the total weight of the first organic layer. More preferably, the compound contains 1 part by weight or more and 10 parts by weight or less relative to 100 parts by weight of the total weight of the first organic layer.

[0450] In one embodiment of the present specification, the light-emitting layer includes the compound represented by the above Chemical Formula 1, and the light-emitting layer including the compound represented by the above Chemical Formula 1 emits blue light.

[0451] In another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound as a dopant of the light-emitting layer, and may further include a host.

[0452] In one embodiment of the present specification, the first organic layer is a light-emitting layer, and further comprises an anthracene derivative in addition to the compound represented by the chemical formula 1. Specifically, the compound is included as a dopant of the light-emitting layer, and the anthracene derivative is included as a host of the light-emitting layer.

[0453] In one embodiment of the present specification, the anthracene derivative is a compound represented by the following chemical formula H01 or H02,

[0454] [Chemical formula H01]

[0455]

[0456] [Chemical formula H02]

[0457]

[0458] In the above chemical formulas H01 and H02,

[0459] D refers to deuterium, k1 is an integer from 0 to 8, k2 is an integer from 0 to 7,

[0460] L21 to L23 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0461] Ar21 to Ar23 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0462] In one embodiment of the present specification, L21 to L23 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms and containing N, O or S.

[0463] In one embodiment of the present specification, L21 to L23 are the same as or different from each other, and are each independently a direct bond, a phenylene group, a biphenylene group, or a naphthylene group, and each of L21 to L23 may contain one or more deuterium groups.

[0464] In one embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0465] In one embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0466] In one embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and are each independently phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, dibenzofuranyl, naphthobenzofuranyl, dibenzothienyl, or naphthobenzothienyl, and Ar21 to Ar23 may each contain one or more deuterium.

[0467] In one embodiment of the present specification, Ar21 and Ar22 are different from each other.

[0468] In one embodiment of the present specification, Ar21 is a substituted or unsubstituted aryl group, and Ar22 is a substituted or unsubstituted aryl group.

[0469] In one embodiment of the present specification, Ar21 is a substituted or unsubstituted aryl group, and Ar22 is a substituted or unsubstituted heteroaryl group.

[0470] In one embodiment of the present specification, Ar21 is an aryl group which may be substituted by deuterium, and Ar22 is an aryl group which may be substituted by deuterium.

[0471] In one embodiment of the present specification, Ar21 is an aryl group which may be substituted by deuterium, and Ar22 is a heteroaryl group which may be substituted by deuterium.

[0472] In one embodiment of the present specification, Ar23 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0473] In one embodiment of the present specification, Ar23 is an aryl group having 6 to 20 carbon atoms which may be substituted with deuterium.

[0474] In one embodiment of the present specification, Ar23 is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, or a phenanthryl group.

[0475] In one embodiment of the present specification, the anthracene derivative is any one selected from the following compounds.

[0476]

[0477]

[0478]

[0479] The organic layer (specifically, the light-emitting layer) may contain one or more of the compound represented by the chemical formula H. Specifically, the first host represented by the chemical formula H and the second host represented by the chemical formula H may be contained in the organic layer.

[0480] The weight ratio of the first host represented by the above Chemical Formula H to the second host represented by the above Chemical Formula H is 95:5 to 5:95, more preferably 30:70 to 70:30.

[0481] In another embodiment, the first body and the second body are different from each other.

[0482] In another embodiment, Ar21 and Ar22 of the first entity represented by the above chemical formula H are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Ar21 of the second entity represented by the above chemical formula H is a substituted or unsubstituted aryl group, and Ar22 is a substituted or unsubstituted heteroaryl group.

[0483] In one embodiment of the present specification, the organic light-emitting device further includes one or more light-emitting layers in addition to the light-emitting layer including the compound represented by the chemical formula 1. The one or more light-emitting layers may each include the fluorescent dopant or the phosphorescent dopant.

[0484] According to one embodiment of the present specification, the organic light-emitting device includes two or more light-emitting layers, one of the two or more light-emitting layers includes a fluorescent dopant, and the other includes a phosphorescent dopant.

[0485] According to one embodiment of the present invention, a light-emitting layer including the compound represented by the above Chemical Formula 1 is included, and the maximum light-emitting peak of the light-emitting layer is in the range of 400 nm to 500 nm.

[0486] In one embodiment of the present specification, the organic light-emitting device includes two or more light-emitting layers.

[0487] In one embodiment of the present specification, the maximum emission peaks of the respective light-emitting layers are different from each other. Specifically, the organic light-emitting device further includes one or more light-emitting layers that exhibit a maximum emission peak in a wavelength range different from the wavelength range in which the light-emitting layer including one or more compounds represented by the above chemical formula 1 exhibits a maximum emission peak.

[0488] The maximum emission peak of the light-emitting layer including the compound represented by the above Chemical Formula 1 is in the range of 400nm to 500nm, and the maximum emission peak of another light-emitting layer may be in the range of 510nm to 580nm, or 610nm to 680nm.

[0489] In one embodiment of the present specification, a light-emitting layer other than the light-emitting layer containing one or more compounds represented by the above Chemical Formula 1 contains a phosphorescent dopant. Specifically, one or more light-emitting layers showing a maximum light-emitting peak in a wavelength range different from the wavelength range showing the maximum light-emitting peak of the light-emitting layer containing one or more compounds represented by the above Chemical Formula 1 contain a phosphorescent dopant.

[0490] In one embodiment of the present specification, one light-emitting layer is blue, and the other light-emitting layer may include a blue, red or green light-emitting compound known in the art.

[0491] According to one embodiment of the present invention, the organic light-emitting device comprises two or more light-emitting layers, one light-emitting layer comprises a fluorescent dopant, and the other light-emitting layer comprises a phosphorescent dopant.

[0492] When the organic light-emitting device of the present invention includes two or more light-emitting layers, the two or more light-emitting layers may be stacked in sequence in the vertical direction or in parallel in the horizontal direction.

[0493] In one embodiment of the present specification, the organic light-emitting device includes three or more light-emitting layers. In one embodiment, the three or more light-emitting layers are stacked in sequence, and the three or more light-emitting layers can all show a maximum light-emitting peak in the same wavelength range. In this case, the maximum light-emitting peak is in the blue region of 400nm to 500nm.

[0494] In one embodiment of the present specification, the compound represented by the above Chemical Formula 2 is included in the second organic layer.

[0495] In one embodiment of the present specification, the compound represented by the above Chemical Formula 2 is included in a hole blocking layer, an electron regulating layer, an electron transport layer, an electron injection layer, or a layer that simultaneously transports and injects electrons.

[0496] In one embodiment of the present specification, the second organic layer is included in a hole blocking layer, an electron regulating layer, an electron transporting layer, an electron injecting layer, or a layer that simultaneously transports and injects electrons.

[0497] In one embodiment of the present specification, the second organic layer includes an electron transport layer or a layer that simultaneously transports and injects electrons.

[0498] In one embodiment of the present specification, the first organic substance layer and the second organic substance layer are provided in contact with each other.

[0499] In one embodiment of the present specification, a first organic layer is provided between the anode and the cathode. In another embodiment, the second organic layer is provided between the first organic layer and the cathode.

[0500] In one embodiment of the present specification, the second organic layer is provided in contact with a cathode.

[0501] In one embodiment of the present specification, an electron transport region is further included between the second organic layer and the first organic layer.

[0502] In one embodiment of the present specification, the second organic layer is provided in contact with the light-emitting layer, and more specifically, in contact with the surface of the cathode facing the light-emitting layer.

[0503] In one embodiment of the present specification, the second organic layer further includes, in addition to the compound represented by Chemical Formula 2, one or more n-type dopants selected from alkali metals and alkaline earth metals.

[0504] When an organic alkali metal compound or an organic alkaline earth metal compound is used as an n-type dopant, the stability of holes in the light-emitting layer can be ensured, thereby increasing the life of the organic light-emitting device. In addition, the electron mobility of the electron transport layer and the ratio of the organic alkali metal compound or the organic alkaline earth metal compound are adjusted to maximize the balance between holes and electrons in the light-emitting layer, thereby increasing the luminous efficiency.

[0505] In the present specification, as the n-type dopant for the second organic layer, LiQ is more preferred. The second organic layer may include the heterocyclic compound of Chemical Formula 2 and the n-type dopant in a weight ratio of 1:9 to 9:1. Preferably, the heterocyclic compound of Chemical Formula 2 and the n-type dopant may be included in a ratio of 2:8 to 8:2, and more preferably, in a ratio of 3:7 to 7:3.

[0506] In one embodiment of the present specification, the cathode is a multilayer structure of metal or metal alloy.

[0507] In one embodiment, the organic light-emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate.

[0508] In one embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode. In another embodiment, the first electrode is a cathode, and the second electrode is an anode.

[0509] In one embodiment of the present specification, the organic light-emitting device may be an organic light-emitting device of a normal structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

[0510] In one embodiment of the present specification, the organic light emitting device may be an organic light emitting device of a reverse structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0511] Figures 1 to 4 The stacked structure of the organic light emitting device of the present invention is illustrated.

[0512] Figure 1 An organic light-emitting device is shown in which a substrate 0, a cathode 1, a second organic layer 202, a first organic layer 201, and an anode 4 are sequentially stacked in a vertical direction. In one embodiment of the present specification, the compound represented by the above chemical formula 1 is contained in the first organic layer 201, and the compound represented by the above chemical formula 2 is contained in the second organic layer 202.

[0513] Figures 2 to 4 The laminated structure of the organic light-emitting device of the present invention is shown, each of which includes two or more light-emitting layers.

[0514] Figure 2 An organic light-emitting device is shown in which a substrate 0, a cathode 1, an electron transport layer 2, a hole blocking layer or electron regulating layer 7, a light-emitting layer 1 (11), an organic layer 5, a light-emitting layer 2 (12), a hole transport layer 3, and an anode 4 are sequentially stacked in a vertical direction. In one embodiment of the present specification, the compound represented by the above chemical formula 1 is contained in the organic layer 5 or the hole transport layer 3. In one embodiment, the compound represented by the above chemical formula 2 is contained in the electron transport layer 2, the hole blocking layer or electron regulating layer 7, or the organic layer 5.

[0515] Figure 3 An organic light-emitting device is shown in which a substrate 0, a cathode 1, an electron transport layer 2, a hole blocking layer or electron regulating layer 7, a light-emitting layer 1 (11), an organic layer 5, a light-emitting layer 2 (12), an organic layer 6, a light-emitting layer 3 (13), a hole transport layer 3 and an anode 4 are sequentially stacked in a vertical direction. In one embodiment of the present specification, the compound represented by the above chemical formula 1 is contained in the organic layer 5, the organic layer 6 or the hole transport layer 3.

[0516] Figure 4An organic light-emitting device is shown in which a substrate 0, a cathode 1, an electron transport layer 2, a hole blocking layer or electron regulating layer 7, a light-emitting layer 101, a hole transport layer 3 and an anode 4 are stacked in this order, and the light-emitting layer 1 (11) and the light-emitting layer 2 (12) of the light-emitting layer 101 are stacked in parallel in the horizontal direction. In one embodiment of the present specification, the compound represented by the above chemical formula 1 is contained in the hole transport layer 3. In one embodiment, the compound represented by the above chemical formula 2 is contained in the electron transport layer 2 or the hole blocking layer or electron regulating layer 7.

[0517] In one embodiment, the compound represented by the chemical formula 2 is contained in the electron transport layer 2, the hole blocking layer or the electron regulating layer 7, the organic layer 5 or the organic layer 6. In one embodiment of the present invention, the light emitting layer 1 (11), the light emitting layer 2 (12) and the light emitting layer 3 (13) emit the same color. In one embodiment, the light emitting layer 1 (11), the light emitting layer 2 (12) and the light emitting layer 3 (13) emit blue light.

[0518] picture Figure 2 and Figure 3 When a plurality of light-emitting layers are stacked, the organic layer provided between the plurality of light-emitting layers may be an intermediate layer. The intermediate layer is also generally referred to as an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron attracting layer, a connecting layer, an intermediate insulating layer, and may be composed of known materials as long as it has the function of supplying electrons to the adjacent layer on the anode side and supplying holes to the adjacent layer on the cathode side. In one embodiment of the present invention, the organic layer 5 located between the light-emitting layer 1 and the light-emitting layer 2 is a charge generation layer or an intermediate insulating layer. In one embodiment of the present invention, the organic layer 6 located between the light-emitting layer 2 and the light-emitting layer 3 is a charge generation layer or an intermediate insulating layer.

[0519] However, the structure of the organic light-emitting device according to one embodiment of the present specification is not limited to Figures 1 to 4 , which can be any of the following structures.

[0520] (1) Anode / hole transport layer / light-emitting layer / cathode

[0521] (2) Anode / hole injection layer / hole transport layer / light-emitting layer / cathode

[0522] (3) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode

[0523] (4) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0524] (5) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / cathode

[0525] (6) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0526] (7) Anode / hole transport layer / hole regulation layer / light-emitting layer / electron transport layer / cathode

[0527] (8) Anode / hole transport layer / hole regulation layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0528] (9) Anode / hole injection layer / hole transport layer / hole regulation layer / light-emitting layer / electron transport layer / cathode

[0529] (10) Anode / hole injection layer / hole transport layer / hole regulation layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0530] (11) Anode / hole transport layer / light-emitting layer / electron regulation layer / electron transport layer / cathode

[0531] (12) Anode / hole transport layer / light-emitting layer / electron regulation layer / electron transport layer / electron injection layer / cathode

[0532] (13) Anode / hole injection layer / hole transport layer / light-emitting layer / electron regulation layer / electron transport layer / cathode

[0533] (14) Anode / hole injection layer / hole transport layer / light-emitting layer 1 / intermediate layer / light-emitting layer 2 / electron transport layer / electron injection layer / cathode

[0534] (15) Anode / hole injection layer / hole transport layer / light-emitting layer 1 / intermediate layer / light-emitting layer 2 / intermediate layer / light-emitting layer 3 / electron transport layer / electron injection layer / cathode

[0535] In one embodiment of the present invention, the first organic layer is a light-emitting layer, a light-emitting layer 1, a light-emitting layer 2 or a light-emitting layer 3.

[0536] When the organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0537] The organic layer of the organic light-emitting device may be formed by various methods.

[0538] In one embodiment, a metal or a conductive metal oxide or an alloy thereof can be evaporated on a substrate to form an anode, and after an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer is formed on the anode, a substance that can be used as a cathode is evaporated on the organic layer, thereby manufacturing an organic light-emitting device.

[0539] In another embodiment, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (International Patent Application Publication No. 2003 / 012890). However, the manufacturing method is not limited thereto.

[0540] The respective organic layers may be formed by any conventional deposition techniques, such as vapor deposition, liquid deposition (continuous and discontinuous techniques), and thermal transfer. Continuous deposition techniques include, but are not limited to, spin coating, gravure coating, curtain coating, dip coating, slot-die coating, spray coating, and continuous nozzle coating. Discontinuous deposition techniques include, but are not limited to, ink jet printing, gravure printing, and screen printing.

[0541] In one embodiment of the present specification, the first organic layer and the second organic layer may be formed by a physical vapor deposition method (PVD) such as evaporation, sputtering or electron beam evaporation.

[0542] According to another embodiment, the first organic layer and the second organic layer may be formed as an organic layer by solution coating, which may include spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roller coating, etc., but is not limited thereto.

[0543] In one embodiment of the present specification, other layers in the organic light-emitting device can be produced using any known substances as long as they are useful for the respective layers. Preferred substances suitable for the organic layer are exemplified below, but the present invention is not limited thereto.

[0544] As the above-mentioned anode material, in order to enable holes to be smoothly injected into the organic layer, a material with a large work function is preferably used. For example, there are metals such as vanadium, chromium, copper, zinc, gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, etc., but are not limited thereto.

[0545] In order to facilitate the injection of electrons into the organic layer, the cathode material is preferably a material with a small work function, such as metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al, etc., but not limited thereto.

[0546] The above-mentioned light-emitting layer may include a host material and a dopant material. The host material includes an aromatic fused ring derivative or a heterocyclic compound. Specifically, as an aromatic fused ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., as heterocyclic compounds, there are dibenzofuran derivatives, ladder furan compounds, etc. Pyrimidine derivatives, etc., but are not limited to these.

[0547] As the dopant material, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are aromatic fused ring derivatives having substituted or unsubstituted arylamine groups, such as pyrene, anthracene, In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine group, and is substituted or unsubstituted with one or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamine groups. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but not limited thereto. In addition, as metal complexes, there are iridium complexes, platinum complexes, etc., but not limited thereto.

[0548] The hole injection layer is a layer that receives holes from the electrode. The hole injection material is preferably a material that has the ability to transport holes, has the effect of receiving holes from the anode, and has an excellent hole injection effect on the light-emitting layer or the light-emitting material. Moreover, it is preferably a material that has an excellent ability to prevent the excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material. Moreover, it is preferably a material with excellent thin film forming ability. In addition, 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. As specific examples of hole injection materials, there are metal porphyrins, oligothiophenes, and arylamine organics; hexanitrile hexaazatriphenylene organics; quinacridone organics; perylene organics; conductive polymers such as anthraquinone, polyaniline, and polythiophene, but are not limited to these.

[0549] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer, and a material with a large hole mobility is suitable. As specific examples, there are arylamine organic substances, conductive polymers, and block copolymers having both conjugated and non-conjugated parts, but it is not limited to these.

[0550] The electron transport layer is a layer that receives electrons from the electron injection layer and transfers the electrons to the light-emitting layer. The electron transport material is a material that can well receive electrons from the cathode and transfer them to the light-emitting layer, and is suitable for materials with high electron mobility. As specific examples, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited to this. The electron transport layer can be used together with any desired cathode material as used in the prior art. In particular, a suitable cathode material is a common material having a low work function and accompanied by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium and samarium, etc., in each case accompanied by an aluminum layer or a silver layer.

[0551] The electron injection layer is a layer that receives electrons from the electrode. The electron injection material is preferably a material that has excellent electron transport capability, has an effect of receiving electrons from the cathode, and has an excellent electron injection effect on the light-emitting layer or the light-emitting material. In addition, it is preferably a material that prevents the excitons generated in the light-emitting layer from migrating to the hole injection layer and has excellent thin film forming capability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and derivatives thereof, metal coordination compounds, and nitrogen-containing five-membered ring derivatives.

[0552] Examples of the metal coordination compounds include, but are not limited to, 8-hydroxyquinoline lithium, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, tris(8-hydroxyquinoline) aluminum, tris(2-methyl-8-hydroxyquinoline) aluminum, tris(8-hydroxyquinoline) gallium, bis(10-hydroxybenzo[h]quinoline) beryllium, bis(10-hydroxybenzo[h]quinoline) zinc, bis(2-methyl-8-quinoline) gallium chloride, bis(2-methyl-8-quinoline)(o-cresol) gallium, bis(2-methyl-8-quinoline)(1-naphthol) aluminum, and bis(2-methyl-8-quinoline)(2-naphthol) gallium.

[0553] The electron blocking layer is a layer that prevents the electrons injected from the electron injection layer from entering the hole injection layer through the light-emitting layer to improve the life and efficiency of the device. Known materials can be used without restriction, and can be formed between the light-emitting layer and the hole injection layer, or between the light-emitting layer and the layer that simultaneously performs hole injection and hole transport.

[0554] The hole blocking layer is a layer that prevents holes from reaching the cathode and can usually be formed using the same conditions as the electron injection layer. Examples of the compound include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and aluminum complexes.

[0555] The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a bi-directional emission type according to the materials used.

[0556] Modes for Carrying Out the Invention

[0557] Below, in order to specifically describe this specification, examples are given and described in detail. However, the embodiments according to this specification can be deformed into various different forms, and it should not be interpreted that the scope of this application is limited to the embodiments described in detail below. The embodiments of this application are provided to more completely describe this specification to those skilled in the art.

[0558] Preparation Example 1-1: Preparation of Compound D1

[0559]

[0560] A flask containing 1-bromo-2,3-dichlorobenzene (22.6 g), intermediate D1-A (21.4 g), Pd(PtBu3)2 (1.02 g), NaOtBu (38.4 g) and toluene (800 ml) was heated at 110°C and stirred for 30 minutes. The reaction solution was cooled to room temperature, NH4Cl saturated solution (sat.aq.) and toluene were added and separated, and the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (methyl tert-butyl ether / hexane) to obtain intermediate D1-B (12.4 g). The mass spectrometry of the obtained solid showed that [M+H] + A peak was confirmed at 323.

[0561]

[0562] Under an argon atmosphere, at 0°C, a 1.7M tert-butyllithium pentane solution (9.2ml) was added to a flask containing intermediate D1-B (4.8g) and tert-butylbenzene (160ml). After the addition was completed, the temperature was raised to 70°C and stirred for 4 hours to distill off the pentane. The mixture was cooled to -40°C, boron tribromide (1.6ml) was added, the temperature was raised to room temperature and stirred for 4 hours. Then, the mixture was cooled to 0°C again, N,N-diisopropylethylamine (6.6ml) was added, stirred at room temperature, and then stirred at 80°C for 4 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added and separated, and the solvent was distilled off under reduced pressure. Acetonitrile was added to obtain D1 (2.3g). The mass spectrometry results of the obtained solid showed that [M+H] + A peak was confirmed at Δ=297.

[0563] Preparation Example 1-2: Preparation of Compound D2

[0564]

[0565] A flask containing 3-bromo-4,5-dichlorophenol (24.2 g), intermediate D2-A (33.8 g), Pd(PtBu3)2 (1.02 g), NaOtBu (38.4 g) and toluene (800 ml) was heated at 110°C and stirred for 30 minutes. The reaction solution was cooled to room temperature, NH4Cl saturated solution (sat.aq.) and toluene were added and separated, and the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (methyl tert-butyl ether / hexane) to obtain intermediate D2-B (39.4 g). The mass spectrometry of the obtained solid showed that [M+H] + A peak was confirmed at =463.

[0566]

[0567] Under an argon atmosphere, at 0°C, a 1.7M tert-butyllithium pentane solution (9.2ml) was added to a flask containing intermediate D2-B (6.9g) and tert-butylbenzene (160ml). After the addition was completed, the temperature was raised to 70°C and stirred for 4 hours to distill off the pentane. The mixture was cooled to -40°C, boron tribromide (1.6ml) was added, the temperature was raised to room temperature and stirred for 4 hours. Then, the mixture was cooled to 0°C again, N,N-diisopropylethylamine (6.6ml) was added, stirred at room temperature, and stirred at 80°C for 4 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added and separated, and the solvent was distilled off under reduced pressure. Acetonitrile was added to obtain intermediate D2-C (3.2g). The mass spectrometry results of the obtained solid showed that [M+H] + A peak was confirmed at =437.

[0568]

[0569] Intermediate D2-C (2.8 g), nonafluorobutane-1-sulfonyl fluoride (2.2 g) and potassium carbonate (1.5 g) were dissolved in acetonitrile (40 ml), heated to 50° C. and stirred for 4 hours. After cooling to room temperature, distilled water was added to remove potassium carbonate, thereby obtaining intermediate D2-D (4.3 g).

[0570]

[0571] A flask containing intermediate D2-D (10.7 g), intermediate B-5 (2.5 g), Pd(PtBu3)2 (0.10 g), NaOtBu (3.0 g) and toluene (100 ml) was heated at 110°C and stirred for 30 minutes. The reaction solution was cooled to room temperature, NH4Cl saturated solution (sat.aq.) and toluene were added and separated, and the solvent was distilled off under reduced pressure. Purification was performed using silica gel column chromatography (developing solution: hexane / ethyl acetate = 50% / 50% (volume ratio)) to obtain D2 (6.2 g). The mass spectrometry of the obtained solid showed that [M+H] + A peak was confirmed at 588.

[0572] Preparation Example 1-3: Preparation of Compound D3

[0573]

[0574] A flask containing 3-bromo-4,5-dichlorophenol (24.2 g), intermediate D3-A (56.2 g), Pd(PtBu3)2 (1.02 g), NaOtBu (38.4 g) and toluene (800 ml) was heated at 110°C and stirred for 30 minutes. The reaction solution was cooled to room temperature, NH4Cl saturated solution (sat.aq.) and toluene were added and separated, and the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (methyl tert-butyl ether / hexane) to obtain intermediate D3-B (47.2 g). The mass spectrometry of the obtained solid showed that [M+H] + A peak was confirmed at 687.

[0575]

[0576] Under an argon atmosphere, at 0°C, a 1.7M tert-butyllithium pentane solution (9.2ml) was added to a flask containing intermediate D3-B (10.2g) and tert-butylbenzene (160ml). After the addition was completed, the temperature was raised to 70°C and stirred for 4 hours to distill off the pentane. The mixture was cooled to -40°C, boron tribromide (1.6ml) was added, the temperature was raised to room temperature and stirred for 4 hours. Then, the mixture was cooled to 0°C again, N,N-diisopropylethylamine (6.6ml) was added, stirred at room temperature, and stirred at 80°C for 4 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added and separated, and the solvent was distilled off under reduced pressure. Acetonitrile was added to obtain intermediate D3-C (4.9g). The mass spectrometry results of the obtained solid showed that [M+H] + A peak was confirmed at =661.

[0577]

[0578] Intermediate D3-C (4.2 g), nonafluorobutane-1-sulfonyl fluoride (2.2 g) and potassium carbonate (1.5 g) were dissolved in acetonitrile (40 ml), heated to 50° C. and stirred for 4 hours. After cooling to room temperature, distilled water was added to remove potassium carbonate, thereby obtaining intermediate D3-D (5.8 g).

[0579]

[0580] A flask containing intermediate D3-D (14.0 g), intermediate C-5 (2.5 g), Pd(PtBu3)2 (0.10 g), NaOtBu (3.0 g) and toluene (100 ml) was heated at 110°C and stirred for 30 minutes. The reaction solution was cooled to room temperature, NH4Cl saturated solution (sat.aq.) and toluene were added and separated, and the solvent was distilled off under reduced pressure. Purification was performed by silica gel column chromatography (developing solution: hexane / ethyl acetate = 50% / 50% (volume ratio)) to obtain D3 (7.7 g). The mass spectrometry of the obtained solid showed that [M+H] + A peak was confirmed at Δ=810.

[0581] Preparation Example 1-4: Preparation of Compound D4

[0582]

[0583] A flask containing 1-bromo-2,3-dichloro-5-methylbenzene (24.0 g), intermediate D4-A (28.8 g), Pd(PtBu3)2 (0.51 g), NaOtBu (19.2 g) and toluene (400 ml) was heated at 110°C and stirred for 30 minutes. The reaction solution was cooled to room temperature, NH4Cl saturated solution (sat.aq.) and toluene were added and separated, and the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (methyl tert-butyl ether / hexane) to obtain intermediate D4-B (33.0 g). The mass spectrometry of the obtained solid showed that [M+H] + A peak was confirmed at 440.

[0584]

[0585] A flask containing intermediate D4-B (19.3 g), intermediate D4-C (18.1 g), Pd(PtBu3)2 (0.22 g), NaOtBu (8.42 g) and toluene (400 ml) was heated at 110°C and stirred for 30 minutes. The reaction solution was cooled to room temperature, NH4Cl saturated solution (sat.aq.) and toluene were added and separated, and the solvent was distilled off under reduced pressure. Purification was performed using silica gel column chromatography (developing solution: hexane / ethyl acetate = 50% / 50% (volume ratio)) to obtain intermediate D4-D (18.0 g). The mass spectrometry of the obtained solid showed that [M+H] + A peak was confirmed at 817.

[0586]

[0587] Under an argon atmosphere, at 0°C, a 1.7M tert-butyllithium pentane solution (9.2ml) was added to a flask containing intermediate D4-D (12.2g) and tert-butylbenzene (160ml). After the addition was completed, the temperature was raised to 70°C and stirred for 4 hours to distill off the pentane. The mixture was cooled to -40°C, boron tribromide (1.6ml) was added, the temperature was raised to room temperature and stirred for 4 hours. Then, the mixture was cooled to 0°C again, N,N-diisopropylethylamine (6.6ml) was added, stirred at room temperature, and then stirred at 80°C for 4 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added and separated, and the solvent was distilled off under reduced pressure. Acetonitrile was added to obtain D4 (6.4g). The mass spectrometry results of the obtained solid showed that [M+H] + A peak was confirmed at 791.

[0588] Preparation Example 1-5: Preparation of Compound D5

[0589]

[0590] A flask containing 1-bromo-2,3-dichloro-5-methylbenzene (24.0 g), intermediate D5-A (56.4 g), Pd(PtBu3)2 (1.02 g), NaOtBu (38.4 g) and toluene (800 ml) was heated at 110°C and stirred for 30 minutes. The reaction solution was cooled to room temperature, NH4Cl saturated solution (sat.aq.) and toluene were added and separated, and the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (methyl tert-butyl ether / hexane) to obtain intermediate D5-B (99.8 g). The mass spectrometry of the obtained solid showed that [M+H] + A peak was confirmed at ΔH = 685.

[0591]

[0592] Under an argon atmosphere, at 0°C, a 1.7M tert-butyllithium pentane solution (9.2ml) was added to a flask containing intermediate D5-B (10.2g) and tert-butylbenzene (160ml). After the addition was completed, the temperature was raised to 70°C and stirred for 4 hours to distill off the pentane. The mixture was cooled to -40°C, boron tribromide (1.6ml) was added, the temperature was raised to room temperature and stirred for 4 hours. Then, the mixture was cooled to 0°C again, N,N-diisopropylethylamine (6.6ml) was added, stirred at room temperature, and stirred at 80°C for 4 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added and separated, and the solvent was distilled off under reduced pressure. Acetonitrile was added to obtain D5 (5.2g). The mass spectrometry results of the obtained solid showed that [M+H] + A peak was confirmed at 659.

[0593] Preparation Example 1-6: Preparation of Compound D6

[0594]

[0595] A flask containing 1-bromo-2,3-dichloro-5-methylbenzene (24.0 g), intermediate D6-A (17.3 g), Pd(PtBu3)2 (0.51 g), NaOtBu (19.2 g) and toluene (400 ml) was heated at 110°C and stirred for 30 minutes. The reaction solution was cooled to room temperature, NH4Cl saturated solution (sat.aq.) and toluene were added and separated, and the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (methyl tert-butyl ether / hexane) to obtain intermediate D6-B (24.6 g). The mass spectrometry of the obtained solid showed that [M+H] + A peak was confirmed at 328.

[0596]

[0597] A flask containing intermediate D6-B (14.4 g), intermediate D6-C (14.7 g), Pd(PtBu3)2 (0.22 g), NaOtBu (8.42 g) and toluene (400 ml) was heated at 110°C and stirred for 30 minutes. The reaction solution was cooled to room temperature, NH4Cl saturated solution (sat.aq.) and toluene were added and separated, and the solvent was distilled off under reduced pressure. Purification was performed using silica gel column chromatography (developing solution: hexane / ethyl acetate = 50% / 50% (volume ratio)) to obtain intermediate D6-D (14.0 g). The mass spectrometry of the obtained solid showed that [M+H] + A peak was confirmed at 627.

[0598]

[0599] Under an argon atmosphere, at 0°C, a 1.7M tert-butyllithium pentane solution (9.2ml) was added to a flask containing intermediate D6-D (9.4g) and tert-butylbenzene (160ml). After the addition was completed, the temperature was raised to 70°C and stirred for 4 hours to distill off the pentane. The mixture was cooled to -40°C, boron tribromide (1.6ml) was added, the temperature was raised to room temperature and stirred for 4 hours. Then, the mixture was cooled to 0°C again, N,N-diisopropylethylamine (6.6ml) was added, stirred at room temperature, and then stirred at 80°C for 4 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added and separated, and the solvent was distilled off under reduced pressure. Acetonitrile was added to obtain D6 (4.4g). The mass spectrometry results of the obtained solid showed that [M+H] + A peak was confirmed at =601.

[0600] Preparation Example 1-7: Preparation of Compound D7

[0601]

[0602] A flask containing 1-bromo-2,3-dichloro-5-methylbenzene (22.6 g), intermediate D7-A (28.8 g), Pd(PtBu3)2 (0.51 g), NaOtBu (19.2 g) and toluene (400 ml) was heated at 110°C and stirred for 30 minutes. The reaction solution was cooled to room temperature, NH4Cl saturated solution (sat.aq.) and toluene were added and separated, and the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (methyl tert-butyl ether / hexane) to obtain intermediate D7-B (30.1 g). The mass spectrometry of the obtained solid showed that [M+H] + A peak was confirmed at =426.

[0603]

[0604] A flask containing intermediate D7-B (18.7 g), intermediate D7-C (15.4 g), Pd(PtBu3)2 (0.22 g), NaOtBu (8.42 g) and toluene (400 ml) was heated at 110°C and stirred for 30 minutes. The reaction solution was cooled to room temperature, NH4Cl saturated solution (sat.aq.) and toluene were added and separated, and the solvent was distilled off under reduced pressure. Purification was performed using silica gel column chromatography (developing solution: hexane / ethyl acetate = 50% / 50% (volume ratio)) to obtain intermediate D7-D (15.5 g). The mass spectrometry of the obtained solid showed that [M+H] + A peak was confirmed at 741.

[0605]

[0606] Under an argon atmosphere, at 0°C, a 1.7M tert-butyllithium pentane solution (9.2ml) was added to a flask containing intermediate D7-D (11.1g) and tert-butylbenzene (160ml). After the addition was completed, the temperature was raised to 70°C and stirred for 4 hours to distill off the pentane. The mixture was cooled to -40°C, boron tribromide (1.6ml) was added, the temperature was raised to room temperature and stirred for 4 hours. Then, the mixture was cooled to 0°C again, N,N-diisopropylethylamine (6.6ml) was added, stirred at room temperature, and then stirred at 80°C for 4 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added and separated, and the solvent was distilled off under reduced pressure. Acetonitrile was added to obtain D7 (5.2g). The mass spectrometry results of the obtained solid showed that [M+H] + A peak was confirmed at 715.

[0607] Preparation Example 1-8: Preparation of Compound D8

[0608]

[0609] A flask containing 1-bromo-2,3-dichlorobenzene (22.6 g), intermediate D8-A (16.9 g), Pd(PtBu3)2 (0.51 g), NaOtBu (19.2 g) and toluene (400 ml) was heated at 110°C and stirred for 30 minutes. The reaction solution was cooled to room temperature, NH4Cl saturated solution (sat.aq.) and toluene were added and separated, and the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (methyl tert-butyl ether / hexane) to obtain intermediate D8-B (25.5 g). The mass spectrometry of the obtained solid showed that [M+H] + A peak was confirmed at 315.

[0610]

[0611] A flask containing intermediate D8-B (20.0 g), intermediate D8-C (13.9 g), Pd(PtBu3)2 (0.33 g), NaOtBu (12.23 g) and toluene (400 ml) was heated at 110°C and stirred for 30 minutes. The reaction solution was cooled to room temperature, NH4Cl saturated solution (sat.aq.) and toluene were added and separated, and the solvent was distilled off under reduced pressure. Purification was performed using silica gel column chromatography (developing solution: hexane / ethyl acetate = 50% / 50% (volume ratio)) to obtain intermediate D8-D (9.8 g). The mass spectrometry of the obtained solid showed that [M+H] + A peak was confirmed at 497.

[0612]

[0613] Under an argon atmosphere, at 0°C, a 1.7M tert-butyllithium pentane solution (9.2ml) was added to a flask containing intermediate D8-D (7.4g) and tert-butylbenzene (160ml). After the addition was completed, the temperature was raised to 70°C and stirred for 4 hours to distill off the pentane. The mixture was cooled to -40°C, boron tribromide (1.6ml) was added, the temperature was raised to room temperature and stirred for 4 hours. Then, the mixture was cooled to 0°C again, N,N-diisopropylethylamine (6.6ml) was added, stirred at room temperature, and then stirred at 80°C for 4 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added and separated, and the solvent was distilled off under reduced pressure. Acetonitrile was added to obtain D8 (2.2g). The mass spectrometry results of the obtained solid showed that [M+H] + A peak was confirmed at =471.

[0614] Preparation Example 2-1: Preparation of Compound E1

[0615]

[0616] Under a nitrogen atmosphere, E1-A (20 g, 43.6 mmol) and E1-B (10.5 g, 43.6 mmol) were added to 400 ml of tetrahydrofuran, stirred and refluxed. Then, potassium carbonate (18.1 g, 130.9 mmol) was dissolved in 18 ml of water and added, and tetrakis(triphenylphosphine)palladium (1.5 g, 1.3 mmol) was added after sufficient stirring. After reacting for 3 hours, the mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was put into 20 times 468 mL of chloroform and dissolved, and the organic layer was separated after washing with water twice. Anhydrous magnesium sulfate was added and stirred, and then the filtrate was filtered and distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound E1 (13.1 g, 56%, MS: [M+H] + =537).

[0617] Preparation Example 2-2: Preparation of Compound E2

[0618]

[0619] The above-mentioned E2 compound was produced by the same method as the production method of Production Example 2-1 except that each starting material was used as in the above-mentioned reaction formula.

[0620] MS:[M+H] + =614

[0621] Preparation Example 2-3: Preparation of Compound E3

[0622]

[0623] The above-mentioned E3 compound was produced by the same method as the production method of Production Example 2-1 except that each starting material was used as in the above-mentioned reaction formula.

[0624] MS:[M+H] + =639

[0625] Preparation Example 2-4: Preparation of Compound E4

[0626]

[0627] The above-mentioned compound E4 was produced by the same method as the production method of Production Example 2-1 except that each starting material was used as in the above-mentioned reaction formula.

[0628] MS:[M+H] + =716

[0629] Preparation Example 2-5: Preparation of Compound E5

[0630]

[0631] The above-mentioned compound E5 was produced by the same method as the production method of Production Example 2-1 except that each starting material was used as in the above-mentioned reaction formula.

[0632] MS:[M+H] + =640

[0633] Preparation Example 2-6: Preparation of Compound E6

[0634]

[0635] The above-mentioned compound E6 was produced by the same method as the production method of Production Example 2-1 except that each starting material was used as in the above-mentioned reaction formula.

[0636] MS:[M+H] + =746

[0637] Preparation Example 2-7: Preparation of Compound E7

[0638]

[0639] The above-mentioned compound E7 was produced by the same method as the production method of Production Example 2-1 except that each starting material was used as in the above-mentioned reaction formula.

[0640] MS:[M+H] + =729

[0641] Preparation Example 2-8: Preparation of Compound E8

[0642]

[0643] The above-mentioned E8 compound was produced by the same method as the production method of Production Example 2-1 except that each starting material was used as in the above-mentioned reaction formula.

[0644] MS:[M+H] + =795

[0645] Preparation Example 2-9: Preparation of Compound E9

[0646]

[0647] The above-mentioned E9 compound was produced by the same method as the production method of Production Example 2-1 except that each starting material was used as in the above-mentioned reaction formula.

[0648] MS:[M+H] + =763

[0649] Preparation Example 2-10: Preparation of Compound E10

[0650]

[0651] The above-mentioned E10 compound was produced by the same method as the production method of Production Example 2-1 except that each starting material was used as in the above-mentioned reaction formula.

[0652] MS:[M+H] + =808

[0653] Preparation Example 2-11: Preparation of Compound E11

[0654]

[0655] The E11 compound was produced by the same method as in Production Example 2-1 except that the starting materials were used as in the above reaction formula.

[0656] MS:[M+H] + =741

[0657] Preparation Example 2-12: Preparation of Compound E12

[0658]

[0659] The E12 compound was produced by the same method as in Production Example 2-1 except that the starting materials were used as in the above reaction formula.

[0660] MS:[M+H] + =679

[0661] Preparation Example 2-13: Preparation of Compound E13

[0662]

[0663] Under a nitrogen atmosphere, E13-A (20 g, 34.2 mmol) and E13-B (18.4 g, 68.4 mmol) were added to 400 ml of tetrahydrofuran, stirred and refluxed. Then, potassium carbonate (14.2 g, 102.7 mmol) was dissolved in 14 ml of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium (1.2 g, 1 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was added to 20 times 544 mL of chloroform and dissolved, the organic layer was separated after washing with water twice, anhydrous magnesium sulfate was added and stirred, and the filtrate was filtered and distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound E13 (18 g, 66%, MS: [M+H] + =795).

[0664] Experimental Example 1-1

[0665] ITO (indium tin oxide) is used The glass substrate coated with a film of a thickness of 10000 mm was placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent used a product of Fischer Co., and the distilled water used distilled water filtered twice by a filter manufactured by Millipore Co. After the ITO was washed for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was performed with a solvent of isopropanol, acetone and methanol and dried, and then transported to a plasma cleaning machine. In addition, after the above-mentioned substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

[0666] On the ITO transparent electrode prepared in this way, the following compound HI-A was applied as The hole injection layer was formed by thermal vacuum deposition of a thickness of 1000 nm. On the hole injection layer, the following compounds HAT were sequentially deposited in the following order: The first hole transport layer was formed by vacuum evaporation with a thickness of The second hole transport layer was formed by vacuum evaporation with a thickness of 1000 nm. On the hole transport layer, the following compound HT-B was deposited at a thickness of 1000 nm. On the electron blocking layer, the following compound BH and the previously prepared compound D1 were added at a weight ratio of 25:1 and The blue light-emitting layer was formed by vacuum evaporation with a thickness of 1000 nm. The following compound ET-A and lithium (Li) were deposited on the electron transport layer at a weight ratio of 100:1 and Aluminum is deposited on the electron injection layer in a vacuum evaporation process to form an electron injection layer. A cathode is formed by evaporation with a thickness of .

[0667]

[0668] In the above process, the evaporation rate of organic matter is maintained at 0.4 to Aluminum cathode maintenance The evaporation speed is 1×10 -7 Up to 5×10 -5 A support is provided to manufacture an organic light-emitting device.

[0669] Examples 1-2 to 1-104

[0670] In the above Example 1-1, an organic light-emitting device was manufactured by the same method as Example 1-1, except that the compounds shown in Table 1 below were used instead of Compound D1 and / or E1.

[0671]

[0672] Comparative Examples 1-1 to 1-21

[0673] In the above Example 1-1, an organic light-emitting device was manufactured by the same method as Example 1-1, except that the compounds shown in Table 1 below were used instead of Compound D1 and / or E1.

[0674]

[0675] For the organic light-emitting devices manufactured in the above-mentioned embodiments and comparative examples, at 10 mA / cm 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm 2 The time (T90) required for the luminance to reach 90% relative to the initial luminance was measured at a current density of . The above results are shown in Table 1 below.

[0676] [Table 1]

[0677]

[0678]

[0679]

[0680]

[0681]

[0682] As can be seen from Table 1 above, the organic light-emitting device containing all the compounds of Chemical Formulas 1 and 2 has the characteristics of high efficiency, low voltage and long life. Specifically, by comparing Examples 1-1 to 1-104 of the present invention with Comparative Examples 1-1 to 1-8, it can be seen that by including the compound of Chemical Formula 2 of the present invention, the device has low voltage and long life characteristics, and by comparing Examples 1-1 to 1-104 of the present invention with Comparative Examples 1-9 and 1-21, it can be seen that by including the compound of Chemical Formula 1 of the present invention, the device has high efficiency characteristics. Therefore, if the compound of Chemical Formula 1 having high efficiency characteristics is used together with the compound of Chemical Formula 2 having low voltage and long life characteristics, the characteristics lacking in the compound of Chemical Formula 1 and the compound of Chemical Formula 2 are mutually compensated, thereby realizing a more excellent device.

Claims

1. An organic light-emitting device, comprising: anode; cathode; and comprising a first organic layer and a second organic layer between the anode and the cathode, Wherein, the first organic layer comprises a compound represented by the following chemical formula 1; and The second organic layer includes a compound represented by the following chemical formula 202: Chemical formula 1 In the chemical formula 1, X is B, Z1 is a benzene ring substituted or unsubstituted by R1, Z2 is a benzene ring substituted or unsubstituted by R2, a naphthalene ring substituted or unsubstituted by R2, a dibenzofuran ring substituted or unsubstituted by R2, or a dibenzothiophene ring substituted or unsubstituted by R2, Z3 is a benzene ring substituted or unsubstituted by R3, R1 to R3 are the same as or different from each other, and are each independently hydrogen, deuterium, a C1-C10 alkyl group, a C6-C60 arylamine group substituted or unsubstituted by a C1-C10 alkyl group, a C6-C30 aryl group substituted or unsubstituted by a C1-C10 alkyl group, or a C2-C30 heterocyclic group, A1 is N(R101), A2 is N(R102), and R101 and R102 are the same as or different from each other, and are each independently hydrogen, deuterium, a C1-C10 alkyl group, or a C6-C30 aryl group which may be substituted or unsubstituted by a C1-C10 alkyl group, Chemical Formula 202 In the chemical formula 202, Y is O or S, R21, R22 and R24 are the same as or different from each other and are independently hydrogen, deuterium, a C1-C10 alkyl group, or a C6-C30 aryl group which is substituted or unsubstituted by a C1-C10 alkyl group, or adjacent substituents are combined to form a benzene ring, or R22 is represented by the following chemical formula 3, r21, r22 and r24 are the same or different from each other and are each independently an integer from 0 to 4. When r21 is 2 or more, R21 is the same or different from each other. When r22 is 2 or more, R22 is the same or different from each other. When r24 is 2 or more, R24 is the same or different from each other. [Chemical formula 3] In the chemical formula 202 and the chemical formula 3, Represented by any one of the following chemical formulas 301 to 303: Chemical Formula 301 Chemical Formula 302 Chemical Formula 303 In the chemical formulas 301 to 303, At least one of X1 to X3 is N, and the others are CH or CD, Ar1 and Ar2 are the same or different from each other, and are each independently a C6-C30 aryl group substituted or unsubstituted by R41, or a C2-C30 heterocyclic group substituted or unsubstituted by R42, R41 and R42 are the same as or different from each other, and are each independently one of the following substituents: deuterium, a halogen group, a nitrile group, a C1-C10 alkyl group, a C1-C20 haloalkyl group, a C1-C20 alkoxy group, a trimethylsilyl group, a triphenylsilyl group, a C6-C30 aryl group, and a C2-C30 heterocyclic group; or a group formed by connecting two or more of the above substituents, L is a direct bond, a C6-C30 arylene group which may be substituted by a C1-C10 alkyl group or an C2-C30 divalent heterocyclic group which may be substituted by a C1-C10 alkyl group or an m is an integer from 0 to 4. When m is 2 or more, L are the same or different from each other. R30 is hydrogen, deuterium, a C1-C10 alkyl group, or a C6-C30 aryl group which may be substituted with a C1-C10 alkyl group, and r30 is an integer of 0 to 4, and when r30 is 2 or more, R30 are the same as or different from each other.

2. The organic light emitting device according to claim 1, wherein: The chemical formula 202 is represented by the following chemical formula 203: Chemical Formula 203 In the chemical formula 203, X1 to X3, L, m, Ar1, Ar2, R21, R24, r21, r24 and Y are defined as in Chemical Formula 202, X4 is N or C (R34), X5 is N or C (R35), X6 is N or C (R36), at least one of X4 to X6 is N, R34, R35 and R36 are the same as or different from each other and are each independently hydrogen or deuterium, Ar3 and Ar4 are the same as or different from each other, and are each independently a C6-C30 aryl group substituted or unsubstituted by R43, or a C2-C30 heterocyclic group substituted or unsubstituted by R44, R43 and R44 are the same as or different from each other, and are each independently one of the following substituents: deuterium, a halogen group, a nitrile group, a C1-C10 alkyl group, a C1-C20 haloalkyl group, a C1-C20 alkoxy group, a trimethylsilyl group, a triphenylsilyl group, a C6-C30 aryl group, and a C2-C30 heterocyclic group; or a group formed by connecting two or more of the above substituents, L11 is a direct bond, a C6-C30 arylene group which may be substituted by a C1-C10 alkyl group or an C2-C30 divalent heterocyclic group which may be substituted by a C1-C10 alkyl group or an m11 is an integer of 0 to 4. When m11 is 2 or more, L11 are the same as or different from each other.

3. The organic light emitting device according to claim 1, wherein: The chemical formula 202 is represented by any one of the following chemical formulas 215 to 218: Chemical Formula 215 Chemical Formula 216 Chemical Formula 217 Chemical Formula 218 In the chemical formulas 215 to 218, The definitions of X1 to X3, L, m, Ar1, Ar2, R21, R22, R24, r21, r22, r24 and Y are the same as those in Chemical Formula 202.

4. The organic light emitting device according to claim 1, wherein: The chemical formula 202 is represented by any one of the following chemical formulas 401 to 403: Chemical Formula 401 Chemical Formula 402 Chemical Formula 403 In the chemical formulas 401 to 403, X1 to X3, L, m, Ar1, Ar2, R21, R22, R24, R21, R22, R24 and Y are defined as in Chemical Formula 202, R25 and R26 are the same as or different from each other, and are each independently hydrogen, deuterium, a C1-C10 alkyl group, or a C6-C30 aryl group, r25 and r26 are the same or different from each other and are each independently an integer of 0 to 6. When r25 is 2 or more, R25 is the same or different from each other, and when r26 is 2 or more, R26 is the same or different from each other.

5. The organic light emitting device according to claim 1, wherein: The chemical formula 1 is represented by any one of the following chemical formulas 101 to 108: Chemical Formula 101 Chemical Formula 102 Chemical Formula 103 Chemical Formula 104 Chemical Formula 105 Chemical formula 106 Chemical formula 107 Chemical formula 108 In the chemical formulas 101 to 108, X, A1 and A2 are defined as in Chemical Formula 1. Q is O or S, R11 to R20 are the same as or different from each other, and are each independently hydrogen, deuterium, a C1-C10 alkyl group, a C6-C60 arylamine group substituted or unsubstituted by a C1-C10 alkyl group, a C6-C30 aryl group substituted or unsubstituted by a C1-C10 alkyl group, or a C2-C30 heterocyclic group, r11 and r12 are integers from 0 to 4. When r11 and r12 are 2 or more, R11 and R12 are the same as or different from each other. r13 is an integer from 0 to 3. When r13 is 2 or more, R13 are the same or different from each other. r14 to r20 are integers of 0 to 6, and when r14 to r20 are 2 or more, R14 to R20 are the same as or different from each other.

6. The organic light emitting device according to claim 1, wherein: X is B, A1 is N(R101), A2 is N(R102), R101 and R102 are the same as or different from each other, and are each independently a C1-C10 alkyl group, or a C6-C30 aryl group which may be substituted with a C1-C10 alkyl group.

7. The organic light emitting device according to claim 1, wherein: The compound represented by the chemical formula 1 is any one selected from the following compounds:

8. The organic light emitting device according to claim 1, wherein: The compound represented by the chemical formula 202 is any one selected from the following compounds:

9. The organic light emitting device according to claim 1, wherein: The compound represented by the chemical formula 202 is any one selected from the following compounds:

10. The organic light emitting device according to claim 1, wherein: The compound represented by the chemical formula 202 is any one selected from the following compounds:

11. The organic light emitting device according to claim 1, wherein: The first organic layer is a light-emitting layer.

12. The organic light emitting device according to claim 1, wherein: The first organic layer is a light-emitting layer. The light-emitting layer includes a dopant substance. The dopant substance includes the compound represented by Chemical Formula 1.

13. The organic light emitting device according to claim 11, wherein: The organic light emitting device includes one or more light emitting layers in addition to the light emitting layer including the compound represented by Chemical Formula 1.

14. The organic light emitting device according to claim 11, wherein: The organic light emitting device further includes one or more light emitting layers that exhibit a maximum light emitting peak in a wavelength range different from a wavelength range of a maximum light emitting peak exhibited by the light emitting layer including the compound represented by Chemical Formula 1.

15. The organic light emitting device according to claim 11, wherein: The light emitting layer including the compound represented by the Chemical Formula 1 further includes a fluorescent dopant.

16. The organic light emitting device according to claim 14, wherein: The one or more light-emitting layers that exhibit a maximum light-emitting peak in a wavelength range different from a wavelength range of a maximum light-emitting peak exhibited by the light-emitting layer including the compound represented by Chemical Formula 1 include a phosphorescent dopant.

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