Organic compound and organic light-emitting device comprising same

Abstract

The present invention is to provide an organic light-emitting device comprising a novel organic compound as an electron transport layer material. The organic light-emitting device comprising the compound represented by chemical formula 1 of the present invention as an electron transport layer material exhibits excellent characteristics such as driving voltage, external quantum efficiency (EQE), and long lifespan.

Description

Organic compounds and organic light-emitting devices containing the same

[0001] The present invention relates to an organic compound and an organic light-emitting device comprising the same.

[0002]

[0003] Organic light-emitting diodes (OLEDs) have a simpler structure than other flat panel displays such as liquid crystal displays (LCDs), plasma display panels (PDPs), and field emission displays (FEDs), and have various advantages in manufacturing processes. They also have high brightness and excellent viewing angle characteristics, a fast response speed, and low driving voltage. Therefore, they are being actively developed and commercialized for use as light sources for flat panel displays such as wall-mounted TVs, backlights for displays, lighting, and billboards.

[0004] Organic light-emitting diodes (OLEDs) consist of an intermediate layer sandwiched between two electrodes. These devices utilize the principle that electrons and holes are injected from the two electrodes into the light-emitting layer, whereby excitons are generated by the combination of electrons and holes, and light is emitted when the generated excitons drop from the excited state to the ground state.

[0005] An organic light-emitting device may include at least one light-emitting layer. Typically, an organic light-emitting device having multiple light-emitting layers includes light-emitting layers that emit light having different peak wavelengths, thereby enabling a specific color to be realized through a combination of light having different peak wavelengths.

[0006] These organic light-emitting devices can be divided into top-emitting and bottom-emitting devices. Top-emitting devices use a reflective cathode to emit light generated in the light-emitting layer toward a translucent anode. Conversely, bottom-emitting devices use a reflective anode to emit light generated in the light-emitting layer and reflected by the anode toward a transparent cathode toward the driving thin-film transistor.

[0007] Meanwhile, the biggest challenges facing organic light-emitting diodes (OLEDs) are their lifespan and efficiency. As displays become larger, these efficiency and lifespan issues become increasingly crucial. The properties of the components contained in the intermediate layer, which consists of a single or multiple layers containing a light-emitting layer between the anode and cathode, in an OLED device affect the device's operating voltage, luminous efficiency, and brightness. These characteristics, in turn, significantly impact the device's lifespan.

[0008] Therefore, research on the components included in the above intermediate layer is being actively conducted.

[0009] [Prior Art Literature]

[0010] KR 10-2048688 B1

[0011] JP 5194596 B2

[0012]

[0013] The purpose of the present invention is to provide a novel organic compound and an organic light-emitting device comprising the same.

[0014] In addition to the above-mentioned tasks, embodiments according to the present invention can be used to achieve other tasks not specifically mentioned.

[0015] The present invention is not limited to the purposes mentioned above, and other purposes and advantages of the present invention that are not mentioned can be understood by the following description and will be more clearly understood by the embodiments of the present invention.

[0016] In addition, it will be readily apparent that the objects and advantages of the present invention can be realized by the means and combinations thereof set forth in the claims.

[0017]

[0018] In order to solve the above problem, according to one embodiment of the present invention, an organic light-emitting device can be provided, including a first electrode; a second electrode facing the first electrode; and one or more intermediate layers disposed between the first electrode and the second electrode, wherein the intermediate layer includes an electron transport layer, and the electron transport layer includes an organic compound represented by the following chemical formula 1.

[0019] The definition of the following chemical formula 1 is the same as that described in the present specification and claims.

[0020]

[0021]

[0022] The organic light-emitting device of the present invention can improve the driving voltage, efficiency, and lifespan characteristics of the organic light-emitting device by including the organic compound represented by the chemical formula 1 of the present invention in the electron transport layer.

[0023] In addition, the organic light-emitting device of the present invention can excellently implement the color coordinates targeted by the light-emitting layer even when combined with a light-emitting layer of any color by including the organic compound represented by the chemical formula 1 of the present invention in the electron transport layer.

[0024] The effects of this specification are not limited to the effects mentioned above, and other effects not mentioned will be clearly understood by those skilled in the art from the description below.

[0025] The above effects and additional effects are described in detail below.

[0026]

[0027] The above-described purposes, features and advantages are described in detail below, so that a person having ordinary knowledge in the technical field to which the present invention pertains can easily implement the technical idea of ​​the present invention.

[0028] In describing this specification, if it is determined that a detailed description of a related known technology may unnecessarily obscure the gist of this specification, the detailed description is omitted.

[0029] In this specification, when a component is used as "includes," "has," "consists of," "arranges," or "provides," other parts may be added unless "only" is used. When a component is expressed in the singular, it includes the plural unless otherwise explicitly stated.

[0030] In interpreting the components in this specification, even if there is no separate explicit description, it is interpreted to include the range of error.

[0031] In this specification, the phrase "any component is disposed "on (or below)" a component or "on (or below)" a component may mean not only that any component is disposed in contact with the upper surface (or lower surface) of said component, but also that other components may be interposed between said component and any component disposed on (or below) said component.

[0032] The term "halogen group" as used herein includes fluorine, chlorine, bromine and iodine.

[0033] The term "alkyl group" as used herein refers to both straight-chain alkyl radicals and branched-chain alkyl radicals. Unless specifically defined, an alkyl group contains 1 to 30 carbon atoms and may include, but is not limited to, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, pentyl, isoamyl, hexyl, and the like. Additionally, an alkyl group may be optionally substituted.

[0034] The term "cycloalkyl group" as used herein refers to a cyclic alkyl radical. Unless otherwise specified, a cycloalkyl group contains 3 to 20 carbon atoms and may include, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantyl, and the like. Additionally, a cycloalkyl group may be optionally substituted.

[0035] The term "alkenyl group" as used herein refers to both straight-chain alkenyl radicals and branched-chain alkenyl radicals having at least one carbon-carbon double bond. Unless otherwise specified, an alkenyl group contains 2 to 30 carbon atoms and may include, but is not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like. Additionally, an alkenyl group may be optionally substituted.

[0036] The term "cycloalkenyl group" as used herein refers to a cyclic alkenyl radical. Unless otherwise specified, a cycloalkenyl group contains 3 to 20 carbon atoms, and further, the cycloalkenyl group may be optionally substituted.

[0037] The term "alkynyl group" as used herein refers to both straight-chain alkynyl radicals and branched-chain alkynyl radicals having at least one carbon-carbon triple bond. Unless otherwise specified, an alkynyl group contains 2 to 30 carbon atoms. It may include, but is not limited to, ethynyl, 2-propynyl, and the like. Additionally, an alkynyl group may be optionally substituted.

[0038] The term "cycloalkynyl group" as used herein refers to a cyclic alkynyl radical. Unless otherwise specified, a cycloalkynyl group contains 3 to 20 carbon atoms, and further, the cycloalkynyl group may be optionally substituted.

[0039] The terms “aralkyl group” or “arylalkyl group” as used herein are used interchangeably and mean an alkyl group having an aromatic group as a substituent, and further, the aralkyl group (arylalkyl group) may be optionally substituted.

[0040] The terms "aryl group" or "aromatic group" as used herein are used interchangeably, and an aryl group includes both a single ring group and a polycyclic ring group. A polycyclic ring may include a "fused ring" which is two or more rings in which two carbons are common to two adjacent rings. It may also include a form in which two or more rings are simply attached to each other or fused. Unless otherwise specified, an aryl group contains 6 to 30 carbon atoms and may include, but is not limited to, phenyl, naphthyl, anthracenyl, phenanthryl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirofluorenyl, and the like. In addition, an aryl group may be optionally substituted.

[0041] The terms "heteroaryl group" and "heteroaromatic group" as used herein are used interchangeably, and heteroaryl groups include both monocyclic and polycyclic groups. Polycyclic rings may include "fused rings," which are two or more rings in which two carbons or heteroatoms are common to two adjacent rings. Furthermore, they may also include forms in which two or more rings are simply attached to each other or fused together. Unless otherwise specified, a heteroaryl group contains 5 to 60 carbon atoms, wherein at least one carbon in the ring is substituted with a heteroatom such as oxygen (O), nitrogen (N), sulfur (S), or selenium (Se), and includes a 6-membered monocyclic ring such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; a polycyclic ring such as phenoxathinyl, indolizinyl, indolyl, purinyl, quinolyl, isoquinolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, phenylcarbazolyl, 9-phenylcarbazolyl, and carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, and 2-pyrimidinyl. may include, but is not limited to. Additionally, the heteroaryl group may be optionally substituted.

[0042] The term "heterocyclic group" used herein means a group in which at least one of the carbon atoms constituting an aryl group, a cycloalkyl group, a cycloalkenyl group, a cycloalkynyl group, an arylalkyl group, an arylamino group, etc. is substituted with a heteroatom such as oxygen (O), nitrogen (N), or sulfur (S), and with reference to the above definition, includes a heteroaryl group, a heterocycloalkyl group, a heterocycloalkenyl group, a heterocycloalkynyl group, a heteroarylalkyl group, a heteroarylamino group, etc., and further, the heterocycle may be optionally substituted.

[0043] The term "carbon ring" used in this specification may be used as a term including all alicyclic ring groups such as "cycloalkyl group," "cycloalkenyl group," and "cycloalkynyl group" and aromatic ring groups such as "aryl group (aromatic group)", unless there is a special limitation.

[0044] The terms “heteroalkyl group,” “heteroalkenyl group,” “heteroalkynyl group,” and “heteroarylalkyl group” used herein mean a group in which at least one of the carbon atoms constituting the group is substituted with a heteroatom such as oxygen (O), nitrogen (N), or sulfur (S), and further, the heteroalkyl group, heteroalkenyl group, heteroalkynyl group, and heteroarylalkyl group may be optionally substituted.

[0045] The terms “alkylamino group,” “arylalkylamino group,” “arylamino group,” and “heteroarylamino group” used herein mean an amino group (or amine group) substituted with the alkyl group, arylalkyl group, aryl group, or heteroaryl group, and include all primary, secondary, and tertiary amino groups (or amine groups), and further, the alkylamino group, arylalkylamino group, arylamino group, and heteroarylamino group may be optionally substituted.

[0046] The terms “alkylsilyl group,” “arylsilyl group,” “alkoxy group,” “aryloxy group,” “alkylthio group,” and “arylthio group” used in this specification mean that the silyl group, oxy group, and thio group are substituted with the alkyl group and aryl group, respectively, and further, the alkylsilyl group, arylsilyl group, alkoxy group, aryloxy group, alkylthio group, and arylthio group may be optionally substituted.

[0047] The terms "arylene group", "arylalkylene group", "heteroarylene group", and "heteroarylalkylene group" as used herein mean that each of the aryl group, arylalkyl group, heteroaryl group, and heteroarylalkyl group is a divalent substituent that further includes one substitution. Additionally, the arylene group, arylalkylene group, heteroarylene group, and heteroarylalkylene group may be optionally substituted.

[0048] The term "substitution" as used herein means that a hydrogen (H) atom bonded to a carbon atom of the compound of the present invention is replaced with a substituent other than hydrogen, and when there are multiple substituents, each substituent may be the same or different from each other.

[0049] Unless specifically limited in this specification, the position to be substituted is not limited as long as it is a position where a hydrogen atom is substituted, i.e., a position where a substituent can be substituted, and when two or more substituents exist, the substituents may be the same or different from each other.

[0050] The substituent defined herein is a deuterium, a cyano group, a trifluoromethyl group, a nitro group, a halogen group, a hydroxy group, a trimethylsilyl group (TMS), an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, a cycloalkenyl group having 3 to 20 carbon atoms, an alkynyl group having 2 to 30 carbon atoms, a cycloalkynyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, a heteroaryl group having 5 to 60 carbon atoms, a heteroarylalkyl group having 6 to 60 carbon atoms, an amine group, an alkylamino group having 1 to 30 carbon atoms, an arylalkylamino group having 7 to 30 carbon atoms, an arylamino group having 6 to 30 carbon atoms, a carbon 5 At least one selected from the group consisting of a heteroarylamino group having 1 to 60 carbon atoms, a silyl group, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkylthio group having 1 to 30 carbon atoms, and an arylthio group having 6 to 30 carbon atoms may be selected.

[0051] Each target and substituent defined in this specification may be the same or different unless otherwise specified.

[0052] Hereinafter, the organic compound according to the present invention and the organic light-emitting device including the same will be described in detail.

[0053] The organic light-emitting device of the present invention may include a first electrode; a second electrode facing the first electrode; and one or more intermediate layers disposed between the first electrode and the second electrode, wherein the intermediate layer includes an electron transport layer.

[0054] Here, the electron transport layer includes a compound represented by the following chemical formula 1.

[0055]

[0056] Here,

[0057] X is oxygen (O) or sulfur (S),

[0058] Y1, Y2 and Y3 are nitrogen (N) or CR4,

[0059] At least two of Y1, Y2 and Y3 are nitrogen (N),

[0060] n1, n2 and n3 are integers from 0 to 4,

[0061] L1 and L2 are the same or different from each other, and are each independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkylene group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 60 carbon atoms, a substituted or unsubstituted azaarylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylalkylene group having 6 to 60 carbon atoms,

[0062] Ar1 and Ar2 are the same or different from each other, and are each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroarylalkyl group having 6 to 60 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 5 to 60 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and can combine with adjacent groups to form a substituted or unsubstituted ring.

[0063] R1, R2, R3, R4 are selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroarylalkyl group having 6 to 60 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 5 to 60 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and can combine with adjacent groups to form a substituted or unsubstituted ring,

[0064] The substituents of L1, L2, Ar1, Ar2, R1, R2, R3, and R4 are each independently selected from the group consisting of deuterium, cyano, trifluoromethyl, nitro, halogen, hydroxy, trimethylsilyl (TMS), an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, a cycloalkenyl group having 3 to 20 carbon atoms, an alkynyl group having 2 to 30 carbon atoms, a cycloalkynyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, a heteroaryl group having 5 to 60 carbon atoms, a heteroarylalkyl group having 6 to 60 carbon atoms, an amine group, an alkylamino group having 1 to 30 carbon atoms, and a At least one selected from the group consisting of an arylalkylamino group, an arylamino group having 6 to 30 carbon atoms, a heteroarylamino group having 5 to 60 carbon atoms, a silyl group, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkylthio group having 1 to 30 carbon atoms, and an arylthio group having 6 to 30 carbon atoms, and when substituted with multiple substituents, they may be the same as or different from each other, and may combine with adjacent groups to form a substituted or unsubstituted ring.

[0065] According to one embodiment of the present invention, L1 and L2 are the same as or different from each other, and can each independently be a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted azaarylene group having 6 to 30 carbon atoms.

[0066] According to one embodiment of the present invention, “azarylene group” means that at least one of the carbon atoms of the arylene group is substituted with a nitrogen (N) atom, and may include, but is not limited to, pyridinyl, pyrimidinyl, pyridazinyl, etc.

[0067] According to one embodiment of the present invention, L1 and L2 are the same as or different from each other, and can each independently be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridinyl group, or a substituted or unsubstituted pyrimidinyl group.

[0068] According to one embodiment of the present invention, L1 and L2 are the same as or different from each other, and can each independently be a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 60 carbon atoms.

[0069] According to one embodiment of the present invention, L1 and L2 are the same as or different from each other, and may each independently be a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms. For example, it may be a single bond or a substituted or unsubstituted phenylene group.

[0070] According to one embodiment of the present invention, Ar1 and Ar2 are the same as or different from each other, and can each be independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms. For example, they can be selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group.

[0071] According to one embodiment of the present invention, Ar1 and Ar2 are the same as or different from each other, and can each independently be selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms. For example, they can be selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenyl group.

[0072] According to one embodiment of the present invention, Ar2 may be a substituted or unsubstituted aryl group having 6 to 15 carbon atoms. For example, it may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0073] According to one embodiment of the present invention, at least two of Y1, Y2, and Y3 are nitrogen (N). For example, Y1, Y2 may be nitrogen (N), Y1, Y3 may be nitrogen (N), Y2, Y3 may be nitrogen (N), and one of Y1, Y2, and Y3 that is not nitrogen (N) may be CR4, and a pyrimidine may be expressed by the selection of Y1 to Y3.

[0074] According to one embodiment of the present invention, the compound represented by the above chemical formula 1 is characterized in that, based on the following chemical formula a (X is oxygen (O) or sulfur (S)), a substituted or unsubstituted pyrimidine and a substituted or unsubstituted carbazole are connected to one benzene (1 to 4 or 6 to 9), and an energy level suitable for an electron transport layer can be adjusted by the pyrimidine, and an electron transport ability can be easily controlled by the carbazole. At this time, when the pyrimidine and the carbazole are connected to each other in the ortho position, they are suitable as an electron transport layer material, and when connected in the meta or para position, they can be more suitable as an electron transport layer material.

[0075]

[0076] According to one embodiment of the present invention, the organic compound of the chemical formula 1 may be expressed by the following chemical formulas 2 to 5, but is not limited thereto.

[0077]

[0078]

[0079] In the above chemical formulas 2 to 5, X, Y1 to Y3, n1 to n3, L1, L2, Ar1, Ar2, R1 to R4 and its substituents are as defined in the above chemical formula 1.

[0080] According to one embodiment of the present invention, the organic compound of the chemical formula 1 may be expressed by the following chemical formulas 2-1 to 2-3, 3-1 to 3-3, 4-1 to 4-3, and 5-1 to 5-3, but is not limited thereto.

[0081] According to one embodiment of the present invention, the chemical formula 2 can be expressed by the following chemical formulas 2-1 to 2-3, the chemical formula 3 can be expressed by the following chemical formulas 3-1 to 3-3, the chemical formula 4 can be expressed by the following chemical formulas 4-1 to 4-3, and the chemical formula 5 can be expressed by the following chemical formulas 5-1 to 5-3, but is not limited thereto.

[0082]

[0083]

[0084]

[0085]

[0086] In the above chemical formulas 2-1 to 2-3, 3-1 to 3-3, 4-1 to 4-3 and 5-1 to 5-3, X, Y1 to Y3, n1 to n3, L1, L2, Ar1, Ar2, R1 to R4 and its substituents are as defined in the above chemical formula 1.

[0087] The above chemical formulas 2-1 to 2-3, 3-1 to 3-3, 4-1 to 4-3 and 5-1 to 5-3 are characterized in that a substituted or unsubstituted pyrimidine and a substituted or unsubstituted carbazole are connected to one benzene (1 to 4 or 6 to 9) based on the following chemical formula a (X is oxygen (O) or sulfur (S)). The pyrimidine and carbazole are suitable as an electron transport layer material when connected to each other in the ortho position, and may be more suitable as an electron transport layer material when connected to the meta or para position. For example, a compound at the meta or para position can be explained with reference to the position of chemical formula a. In the case of a compound at the meta position, a carbazole is connected to position 1 of chemical formula a, a pyrimidine is connected to position 3; a carbazole is connected to position 2, and a pyrimidine is connected to position 4; It can be a structure in which carbazole is connected at position 3 and pyrimidine is connected at position 1; or carbazole is connected at position 4 and pyrimidine is connected at position 2. In the case of compounds in the para position, it can be a structure in which carbazole is connected at position 1 and pyrimidine is connected at position 3 in chemical formula a; or carbazole is connected at position 2 and pyrimidine is connected at position 4; or carbazole is connected at position 3 and pyrimidine is connected at position 1; or carbazole is connected at position 4 and pyrimidine is connected at position 2.

[0088]

[0089] According to one embodiment of the present invention, L1 and L2 of the above chemical formula 1 may be selected from a single bond or compounds of A1 to A6 below. In the partial compounds below, * indicates a part in which the partial compound is bonded by a single bond.

[0090]

[0091] According to one embodiment of the present invention, Ar1 and Ar2 of the above chemical formula 1 may be selected from compounds B1 to B22 below. In the partial compounds below, * indicates a part in which the partial compound is bonded by a single bond.

[0092]

[0093]

[0094] According to one embodiment of the present invention, the chemical formula 2-1 may be selected from the group consisting of compounds shown in Table 1 below, but is not limited thereto. In Table 1 below, Y1 and Y2 are nitrogen (N), Y3 is carbon (CR4), and R1 to R4 are hydrogen. In addition, "-" means a single bond.

[0095] [Table 1]

[0096]

[0097]

[0098]

[0099]

[0100] According to one embodiment of the present invention, the chemical formula 2-2 may be selected from the group consisting of compounds shown in Table 2 below, but is not limited thereto. In Table 2 below, Y1 and Y2 are nitrogen (N), Y3 is carbon (CR4), and R1 to R4 are hydrogen. In addition, "-" means a single bond.

[0101] [Table 2]

[0102]

[0103]

[0104]

[0105]

[0106] According to one embodiment of the present invention, the chemical formula 2-3 may be selected from the group consisting of compounds shown in Table 3 below, but is not limited thereto. In Table 3 below, Y1 and Y2 are nitrogen (N), Y3 is carbon (CR4), and R1 to R4 are hydrogen. In addition, "-" means a single bond.

[0107] [Table 3]

[0108]

[0109]

[0110]

[0111]

[0112] According to one embodiment of the present invention, the chemical formula 3-1 may be selected from the group consisting of compounds shown in Table 4 below, but is not limited thereto. In Table 4 below, Y1 and Y2 are nitrogen (N), Y3 is carbon (CR4), and R1 to R4 are hydrogen. In addition, "-" means a single bond.

[0113] [Table 4]

[0114]

[0115]

[0116]

[0117]

[0118] According to one embodiment of the present invention, the chemical formula 3-2 may be selected from the group consisting of compounds shown in Table 5 below, but is not limited thereto. In Table 5 below, Y1 and Y2 are nitrogen (N), Y3 is carbon (CR4), and R1 to R4 are hydrogen. In addition, "-" means a single bond.

[0119] [Table 5]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125] According to one embodiment of the present invention, the chemical formula 3-3 may be selected from the group consisting of compounds shown in Table 6 below, but is not limited thereto. In Table 6 below, Y1 and Y2 are nitrogen (N), Y3 is carbon (CR4), and R1 to R4 are hydrogen. In addition, "-" means a single bond.

[0126] [Table 6]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132] According to one embodiment of the present invention, the chemical formula 4-1 may be selected from the group consisting of compounds shown in Table 7 below, but is not limited thereto. In Table 7 below, Y1 and Y2 are nitrogen (N), Y3 is carbon (CR4), and R1 to R4 are hydrogen. In addition, "-" means a single bond.

[0133] [Table 7]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139] According to one embodiment of the present invention, the chemical formula 4-2 may be selected from the group consisting of compounds shown in Table 8 below, but is not limited thereto. In Table 8 below, Y1 and Y2 are nitrogen (N), Y3 is carbon (CR4), and R1 to R4 are hydrogen. In addition, "-" means a single bond.

[0140] [Table 8]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146] According to one embodiment of the present invention, the chemical formula 4-3 may be selected from the group consisting of compounds shown in Table 9 below, but is not limited thereto. In Table 9 below, Y1 and Y2 are nitrogen (N), Y3 is carbon (CR4), and R1 to R4 are hydrogen. In addition, "-" means a single bond.

[0147] [Table 9]

[0148]

[0149]

[0150]

[0151]

[0152] According to one embodiment of the present invention, the chemical formula 5-1 may be selected from the group consisting of compounds shown in Table 10 below, but is not limited thereto. In Table 10 below, Y1 and Y2 are nitrogen (N), Y3 is carbon (CR4), and R1 to R4 are hydrogen. In addition, "-" means a single bond.

[0153] [Table 10]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159] According to one embodiment of the present invention, the chemical formula 5-2 may be selected from the group consisting of compounds shown in Table 11 below, but is not limited thereto. In Table 11 below, Y1 and Y2 are nitrogen (N), Y3 is carbon (CR4), and R1 to R4 are hydrogen. In addition, "-" means a single bond.

[0160] [Table 11]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176] According to one embodiment of the present invention, the chemical formula 5-3 may be selected from the group consisting of compounds shown in Table 12 below, but is not limited thereto. In Table 12 below, Y1 and Y2 are nitrogen (N), Y3 is carbon (CR4), and R1 to R4 are hydrogen. In addition, "-" means a single bond.

[0177] [Table 12]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183] According to one embodiment of the present invention, the compounds described in Tables 1 to 12 can be expressed as follows.

[0184]

[0185]

[0186]

[0187]

[0188]

[0189] The organic light-emitting device of the present invention comprises a first electrode; a second electrode facing the first electrode; and one or more intermediate layers disposed between the first electrode and the second electrode; wherein the intermediate layer comprises an electron transport layer, and the electron transport layer may comprise a compound represented by the chemical formula 1.

[0190] The above organic light-emitting device may further include at least one selected from the group consisting of a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an emitting layer (EML), an electron transport auxiliary layer, and an electron injection layer (EIL) as an intermediate layer.

[0191] For example, an organic light-emitting device may have a structure in which a first electrode, a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an emission layer (EML), an electron transport layer (ETL), an electron injection layer (EIL), and a second electrode are sequentially stacked.

[0192] An organic light-emitting device according to an embodiment of the present invention may include an electron transport layer comprising a compound represented by Chemical Formula 1. For example, when an organic compound represented by Chemical Formula 1 is used as an electron transport layer material, it may have an energy level suitable for an electron transport layer that transfers electrons from an electron injection layer to a light-emitting layer.

[0193] An organic light-emitting device according to one embodiment of the present invention can excellently implement a target color coordinate even when an electron transport layer including an organic compound represented by the above chemical formula 1 is combined with a light-emitting layer of any color.

[0194] The first electrode may be an anode, and the first electrode may include a material such as indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO) that is transparent and has excellent conductivity.

[0195] The second electrode may be a cathode, and the second electrode may include materials such as lithium (Li), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag). In addition, in the case of a top-emitting organic light-emitting device, a transparent second electrode through which light can pass may be formed using indium tin oxide (ITO) or indium zinc oxide (IZO).

[0196] A capping layer (CPL) may be formed on the surface of the second electrode. The capping layer may be formed of, for example, a material such as N4,N4'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD).

[0197] Additionally, a protective film (encapsulation layer or protecting layer) may be additionally disposed on the capping layer to protect the organic light-emitting element from moisture, oxygen, etc. This protective film may be formed of a curable adhesive composition containing an inorganic moisture absorbent.

[0198] The above hole injection layer or hole transport layer compound is not particularly limited, and any compound that is typically used as a hole injection layer or hole transport layer compound may be used. Non-limiting examples of the hole injection layer or hole transport layer compound may include phthalocyanine derivatives, porphyrin derivatives, triarylamine derivatives, indolocarbazole derivatives, and the like. For example, 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN), copper phthalocyanine (CuPc), 4,4',4"-tris(3-methylphenylamino)triphenylamine (m-MTDATA), 4,4',4"-tris(3-methylphenylamino)phenoxybenzene (m-MTDAPB), 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), 4,4',4"-tris(N-(2-naphthyl)-N-phenylamino)-triphenylamine (2-TNATA), N4,N4,N4',N4'-Tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine (N4,N4,N4',N4'-Tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, bis(N-(1-naphthyl-n-phenyl))benzidine (α-NPD), N,N'-di(naphthalen-1-yl)-N,N'-biphenyl-benzidine (NPB), N,N'-biphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), etc.

[0199] The compound included in the light-emitting layer is not particularly limited, and any compound that is typically used as a light-emitting layer compound may be used. A single light-emitting compound or a light-emitting host compound may be used.

[0200] The luminescent compound of the above-mentioned luminescent layer may include, but is not limited to, a compound capable of causing luminescence through phosphorescence, fluorescence, thermally activated delayed fluorescence, i.e., TADF (also referred to as E-type delayed fluorescence), triplet-triplet annihilation, or a combination of these processes. The luminescent compound may be selected from a variety of materials depending on the desired luminescent color. Non-limiting examples of luminescent compounds include condensed ring derivatives such as phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopyrene, dibenzopyrene, rubrene, and chrysene, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, bistyryl derivatives, bistyrylarylene derivatives, diazindacene derivatives, furan derivatives, benzofuran derivatives, isobenzofuran derivatives, dibenzofuran derivatives, coumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethine derivatives, cyanine derivatives, oxobenzoanthracene derivatives, xanthenes Examples thereof include derivatives, rhodamine derivatives, fluorescein derivatives, pyrylium derivatives, carbostyril derivatives, acridine derivatives, oxazine derivatives, phenylene oxide derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furopyridine derivatives, 1,2,5-thiadiazolopyrene derivatives, pyrromethene derivatives, perinone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, violantrone derivatives, phenazine derivatives, acridone derivatives, deazaflavin derivatives, fluorene derivatives, benzofluorene derivatives, aromatic boron derivatives, aromatic nitrogen boron derivatives, and metal complexes (complexes of metals such as Ir, Pt, Au, Eu, Ru, Re, Ag, and Cu and heteroaromatic ring ligands, etc.).For example, N1,N1,N6,N6-tetrakis(4-(1-silyl)phenyl)pyrene-1,6-diamine, 2,12-di-tert-butyl-5,9-bis(4-(tert-butyl)phenyl)-7-(3,5-di-tert-butylphenyl)-5,9-dihydro-5,9-diaza-13b-boranaphtho[3,2,1-de]anthracene (t-DABNA-dtB), Platinumoctaethylporphyrin (PtOEP), Ir(ppy)3, Ir(ppy)2(acac), Ir(mppy)3, Ir(PPy)2(m-bppy), BtpIr(acac), Ir(btp)2(acac), Ir(2-phq)3, Hex-Ir(phq)3, Ir(fbi)2(acac), fac-Tris(2-(3-p-xylyl)phenyl)pyridine iridium(III), Eu(dbm)3(Phen), Ir(piq)3, Ir(piq)2(acac), Ir(Fliq)2(acac), Ir(Flq)2(acac), Ru(dtb-bpy)3·2(PF6), Ir(BT)2(acac), Ir(DMP)3, Ir(Mphq)3IR(phq)2tpy, fac-Ir(ppy)2Pc, Ir(dp)PQ2, Ir(Dpm)(Piq)2, Hex-Ir(piq)2(acac), Hex-Ir(piq)3, Includes Ir(dmpq)3, Ir(dmpq)2(acac), FPQIrpic, FIrpic, etc.

[0201] As the host compound of the light-emitting layer, a luminescent host, a hole-transporting host, an electron-transporting host, or a combination thereof can be used. Non-limiting examples of luminescent host compounds include condensed ring derivatives such as anthracene or pyrene, bisstyryl derivatives such as bisstyrylanthracene derivatives or distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, benzofluorene derivatives, N-phenylcarbazole derivatives, carbazonitrile derivatives, and the like. Non-limiting examples of hole-transporting host materials include carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, triarylamine derivatives, indolocarbazole derivatives, and benzoxazinophenoxazine derivatives. Non-limiting examples of electron-transporting host materials include pyridine derivatives, triazine derivatives, phosphine oxide derivatives, benzofuropyridine derivatives, and dibenzoxacillin derivatives. For example, it includes 9,10-bis(2-naphthyl)anthracene (ADN), tris(8-hydroxyquinolinato)aluminum (Alq3), BAlq (8-hydroxyquinoline beryllium salt), DPVBi (4,4'-bis(2,2-biphenylethenyl)-1,1'-biphenyl) series, spiro-DPVBi (spiro-4,4'-bis(2,2-biphenylethenyl)-1,1'-biphenyl), LiPBO (2-(2-benzooxazolyl)-phenol lithium salt), bis(biphenylvinyl)benzene, aluminum-quinoline metal complexes, imidazole, thiazole, and oxazole metal complexes, etc.

[0202] The electron injection layer or electron transport auxiliary layer compound is not particularly limited, and any compound that is typically used as an electron injection layer or electron transport auxiliary layer compound may be used. Non-limiting examples of electron injection layer or electron transport auxiliary layer compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives, thiophene derivatives, triazole derivatives, thiadiazole derivatives, metal complexes of oxine derivatives, quinolinol-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives, imidazopyridine derivatives, borane derivatives, benzoimidazole derivatives, benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives, Examples thereof include naphthyridine derivatives, aldazine derivatives, carbazole derivatives, indole derivatives, phosphine oxide derivatives, bisstyryl derivatives, quinolinol-based metal complexes, hydroxyazole-based metal complexes, azomethine-based metal complexes, tropolone-based metal complexes, flavonol-based metal complexes, benzoquinoline-based metal complexes, and metal salts. These materials can be used alone, but they can also be mixed with other materials. For example, they can include materials such as 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, tris(8-hydroxyquinolinato)aluminum (Alq3), LiF, Liq, Li2O, BaO, NaCl, and CsF.

[0203] According to one embodiment of the present invention, the organic light-emitting device of the present invention may be a tandem organic light-emitting device having a tandem structure.

[0204] In the present invention, the light-emitting stack refers to a unit structure including an intermediate layer including an electron transport layer (ETL) and a hole transport layer (HTL), and an organic light-emitting layer (EML) disposed between the electron transport layer and the hole transport layer. The intermediate layer may further include an electron injection layer (EIL), a hole injection layer (HIL), an electron transport auxiliary layer, and an electron blocking layer (EBL), and other intermediate layers may be further included depending on the structure or design of the organic light-emitting device.

[0205] The organic light-emitting device (tandem organic light-emitting device) having a tandem structure of the present invention may include a plurality of light-emitting stacks (or light-emitting sections) including first electrodes and second electrodes facing each other on a substrate and a light-emitting layer that is laminated between the first electrode and the second electrode and emits light of a specific wavelength range. The plurality of light-emitting stacks may be applied to emit the same color or different colors. In addition, one light-emitting stack may include one or more light-emitting layers, and when there are two or more light-emitting layers, they may emit the same or different colors.

[0206] The tandem organic light-emitting device includes a first electrode; one or more intermediate layers disposed between the first electrode and the second electrode; wherein the intermediate layers are electron transport layers and N light-emitting stacks, wherein N is an integer of 2 or greater; N-1 n-type charge generation layers and N-1 p-type charge generation layers are disposed between different light-emitting stacks; and the electron transport layers may include a compound represented by the chemical formula 1.

[0207] The above intermediate layer may further include at least one selected from the group consisting of a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an emitting layer (EML), an electron transport auxiliary layer, and an electron injection layer (EIL).

[0208] According to one embodiment of the present invention, the tandem organic light-emitting device includes N emitting stacks, and N-1 charge generation layers (CGLs) are disposed between different emitting stacks, and can be formed in a structure connected by the charge generation layers, and the N-1 charge generation layers (CGLs) can include N-1 n-type charge generation layers (n-CGLs) and N-1 p-type charge generation layers (p-CGLs). In this case, N is an integer of 2 or greater, and for example, N can be one of 2, 3, 4, and 5. For example, when N is 2, it can include one n-type charge generation layer and one p-type charge generation layer, and when N is 3, it can include two n-type charge generation layers and two p-type charge generation layers.

[0209] According to one embodiment of the present invention, the tandem organic light-emitting device includes first and second electrodes facing each other, and an intermediate layer positioned between the first electrode and the second electrode. The intermediate layer includes a first light-emitting stack positioned between the first electrode and the second electrode and including a first light-emitting layer; a second light-emitting stack positioned between the first light-emitting stack and the second electrode and including a second light-emitting layer; and a first charge generation layer positioned between the first light-emitting stack and the second light-emitting stack. The first light-emitting stack includes a hole injection layer, a first hole transport layer, an electron blocking layer, a first light-emitting layer, and a first electron transport layer, and the second light-emitting stack includes a second hole transport layer, a second light-emitting layer, a second electron transport layer, and an electron injection layer.

[0210] According to one embodiment of the present invention, the tandem organic light-emitting device includes a first electrode and a second electrode facing each other, and an intermediate layer positioned between the first electrode and the second electrode. The intermediate layer includes a first light-emitting stack positioned between the first electrode and the second electrode and including a first light-emitting layer; a second light-emitting stack including a second light-emitting layer; a third light-emitting stack including a third light-emitting layer; a first charge generation layer positioned between the first light-emitting stack and the second light-emitting stack; and a second charge generation layer positioned between the second light-emitting stack and the third light-emitting stack. The first charge generation layer and the second charge generation layer may include a first n-type charge generation layer and a second n-type charge generation layer, and a first p-type charge generation layer and a second p-type charge generation layer, respectively. The first n-type charge generation layer and the second n-type charge generation layer may be the same as or different from each other. The first light-emitting stack includes a hole injection layer, a first hole transport layer, an electron blocking layer, a first light-emitting layer, and a first electron transport layer, the second light-emitting stack includes a second hole transport layer, a second light-emitting layer, and a second electron transport layer, and the third light-emitting stack includes a third hole transport layer, a third light-emitting layer, a third electron transport layer, and an electron injection layer.

[0211] The above hole injection layer, first hole transport layer, second hole transport layer, third hole transport layer, electron blocking layer, first light-emitting layer, second light-emitting layer, third light-emitting layer, and electron injection layer can be used in the same manner as the hole transport layer, electron blocking layer, light-emitting layer, and electron injection layer materials mentioned above.

[0212] The above n-type charge generation layer may be formed by a single component of an amphoteric compound that can be used as an n-type host, and may be formed by doping, for example, a dopant for electron injection or electron transport, such as an alkali metal or alkaline earth metal compound, in addition to the n-type host. Metal components that can be used as dopants for electron injection or electron transport include, but are not limited to, alkali metals such as lithium (Li), sodium (Na), potassium (K), and cesium (Cs), and / or alkaline earth metals such as magnesium (Mg), strontium (Sr), barium (Ba), and radium (Ra). For example, the dopant may be added in a proportion of about 1 to 30 wt% based on the amphoteric compound used as an n-type host, but is not limited thereto.

[0213] The above p-type charge generation layer may include a p-type dopant material and a p-type host material. The p-type charge generation layer is disposed on the n-type charge generation layer and has a structure in contact with the n-type charge generation layer. The p-type dopant material may be made of an organic material such as a metal oxide, F4-TCNQ (tetrafluoro-tetracyanoquinodimethane), HAT-CN (Hexaazatriphenylene-hexacarbonitrile), hexaazatriphenylene derivatives, or a metal material such as V2O5, MoOx, WO3, etc., but is not limited thereto. The p-type host material may be formed of a material capable of transporting holes, for example, a material including at least one of NPD (N,N'-bis(naphthalen-1-yl)-N,N'-bis(phenyl)-2,2'-dimethylbenzidine), TPD (N,N'-bis-(3-methylphenyl)-N,N'-bis-(phenyl)-benzidine), and MTDATA (4,4',4 Tris(N-3-methylphenyl-N-phenyl-amino)-triphenylamine), but is not limited thereto.

[0214] According to one embodiment of the present invention, at least one electron transport layer in the tandem organic light-emitting device may include a compound represented by the chemical formula 1 of the present invention alone or as a mixture of two types.

[0215] One of the two types of mixtures above may be a compound represented by the chemical formula 1 of the present invention, and the other type may be any compound that is commonly used as an electron injection layer or electron transport layer compound. Non-limiting examples of electron injection layer or electron transport layer compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives, thiophene derivatives, triazole derivatives, thiadiazole derivatives, metal complexes of oxine derivatives, quinolinol-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives, imidazopyridine derivatives, borane derivatives, benzoimidazole derivatives, benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives, Examples thereof include naphthyridine derivatives, aldazine derivatives, carbazole derivatives, indole derivatives, phosphine oxide derivatives, bisstyryl derivatives, quinolinol-based metal complexes, hydroxyazole-based metal complexes, azomethine-based metal complexes, tropolone-based metal complexes, flavonol-based metal complexes, benzoquinoline-based metal complexes, and metal salts. These materials can be used alone, but they can also be mixed with other materials.For example, 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 1-(4-(10-([1,1'-biphenyl]-4-yl)anthracen-9-yl)phenyl)-2-ethyl-1H-benzo[d]imidazole, tris(8-hydroxyquinolinato)aluminum (Alq3), LiF, Liq, Li2O, BaO, It may contain materials such as NaCl and CsF.

[0216] According to one embodiment of the present invention, a mixture including a compound represented by the chemical formula 1 of the present invention may be used in the second electron transport layer or the third electron transport layer.

[0217] Meanwhile, conventional tandem organic light-emitting devices mainly use alkali metal complexes such as LiF and Liq as doping materials to improve the efficiency of the electron transport layer. However, the compound represented by the chemical formula 1 of the present invention can be used together with organic compounds known as conventional electron injection layer or electron transport layer materials in addition to alkali metal complexes. For example, 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole or 1-(4-(10-([1,1'-biphenyl]-4-yl)anthracen-9-yl)phenyl)-2-ethyl-1H-benzo[d]imidazole can be used as a doping material (or mixed material). Conventional alkali metal complexes have excellent electron injection capabilities, helping to improve the efficiency of electron transport layers. However, they are expensive. However, the compound of the present invention exhibits excellent electron injection and electron mobility, enabling the production of economical tandem organic light-emitting devices without the use of alkali metal complexes.

[0218] According to one embodiment of the present invention, when the compound of the present invention is applied as a mixture to the electron transport layer of a tandem organic light-emitting device, the mixing ratio of the compound represented by the chemical formula 1 of the present invention and the compound C (see compound C of Example 89 below) may be 0.5 to 2:1 by weight. When the compound of the present invention is included in an amount of less than 0.5 by weight, the driving voltage of the tandem organic light-emitting device may increase and the lifespan may be shortened. In addition, when it exceeds 2 by weight, its role cannot be sufficiently exerted relative to the added weight.

[0219] A tandem organic light-emitting device according to one embodiment of the present invention may include a tandem structure in which four or more light-emitting stacks and three or more charge-generating layers are arranged between a first electrode and a second electrode. In this case, at least one of the electron transport layers may include a compound represented by Chemical Formula 1 according to the present invention.

[0220] An organic light-emitting device according to one embodiment of the present invention may be a front-emitting device or a back-emitting device.

[0221] An organic light-emitting device according to one embodiment of the present invention can be used in a display device.

[0222] An organic light-emitting device according to one embodiment of the present invention can be applied to a transparent display device, a mobile display device, a flexible display device, etc., but is not limited thereto.

[0223]

[0224] Hereinafter, the synthesis methods of the above compounds are described using representative examples. However, the synthesis methods of the compounds of the present invention are not limited to the methods exemplified below, nor are the implementations of the present invention limited to the following examples and experimental examples.

[0225]

[0226] [Synthesis example]

[0227] As a representative example, a synthetic example for compound 7 is described, and the compounds described in Table 13 and the compounds of chemical formula 1 of the present invention can be synthesized similarly to the reaction of compound 7.

[0228] 1. Synthesis of compound 7

[0229] [Reaction Formula 1]

[0230]

[0231] Under a nitrogen stream, reactant 1 (14.7 mmol), reactant 2 (16.1 mmol), NaOH (44.1 mmol), Pd2(dba)3 (0.74 mmol), SPhos (2.94 mmol), and O-Xylene were added to a 500 mL flask, stirred, and refluxed. After completion of the reaction, the organic layer was extracted using ethyl acetate (EtOAc) and water. The extracted solution was treated with MgSO4 to remove residual moisture, concentrated under reduced pressure, and purified using column chromatography, followed by recrystallization to obtain the product (compound 7).

[0232] Representative synthesized compounds are shown in Table 13 below, and the specific compounds of the present invention and similar compounds can be synthesized through the above synthetic examples.

[0233] [Table 13]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239] [Experimental Example 1] Measurement and Results of Electron Transport Layer HOMO and LUMO Levels

[0240] The compound of the present invention has been confirmed to have effects through the following experiments, which are only representative examples and the experimental examples are not limited thereto.

[0241] The electron transport layer has an appropriate LUMO level between the electron transport auxiliary layer and the electron injection layer or between the emitting layer (if there is no electron transport auxiliary layer) and the electron injection layer, thereby allowing electrons to be transferred to the electron transport auxiliary layer or the emitting layer (if there is no electron transport auxiliary layer). To this end, it is preferable that the LUMO energy difference between the electron transport auxiliary layer or the emitting layer (if there is no electron transport auxiliary layer) be smaller than the LUMO energy difference between the electron injection layer and the electron transport auxiliary layer.

[0242] In order to confirm whether the compounds represented by the chemical formula 1 of the present invention are suitable as electron transport layer materials, HOMO and LUMO were calculated using Gaussian software (B3LYP DFT 6-31G(d) by Gaussian'16.0), and the results are shown in Table 14 below.

[0243] [Table 14]

[0244]

[0245]

[0246] [Example 1] Manufacturing of an organic light-emitting device (blue light-emitting layer)

[0247] The substrate on which the anode of the organic light-emitting device, ITO (100 nm), was laminated was patterned into cathode, anode, and insulating layers through a photolithography process, and then the surface was treated with UV-ozone and O2:N2 plasma for the purpose of increasing the work function of the anode (ITO) and cleaning it.

[0248] Next, a mixture of NDP-9 (2-(7-Dicyanomethylene-1,3,4,5,6,8,9,10-octafluoro-7H-pyren-2-ylidene)-malononitrile) and N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine (N4,N4,N4',N4'-Tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine) was deposited at a weight ratio of 3:97 to form a hole injection layer (HIL) on the anode to a thickness of 10 nm.

[0249] Next, on top of the hole injection layer, N4,N4,N4',N4'-Tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine (N4,N4,N4',N4'-Tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine) is vacuum-deposited to form a hole transport layer with a thickness of 100 nm, and on top of the hole transport layer (HTL), an electron blocking layer (EBL) is formed. N-Phenyl-N-(4-(spiro[benzo[d,e]anthracene-7,9'-fluorene]-2'-yl)phenyl)dibenzo[b,d]furan-4-amine was formed with a thickness of 15 nm.

[0250] 9,10-Bis(2-naphthyl)anthracene (ADN) was deposited as a host with a thickness of 25 nm on the electron blocking layer (EBL) and 2,12-Di-tert-butyl-5,9-bis(4-(tert-butyl)phenyl)-7-(3,5-di-tert-butylphenyl)-5,9-dihydro-5,9-diaza-13b-boranaphtho[3,2,1-de]anthracene was deposited as a dopant. t-DABNA-dtB) was doped at approximately 3 wt%.

[0251] Thereon, the compound 7 of the present invention and Liq were mixed in a weight ratio of 1:1 and deposited to a thickness of 25 nm as an electron transport layer (ETL), and on the electron transport layer, a mixture of ytterbium (Yb) and lithium fluoride (LiF) in a weight ratio of 2:1 was deposited to a thickness of 1 nm as an electron injection layer (EIL), and a mixture of magnesium (Mg) and silver (Ag) in a weight ratio of 1:9 was deposited to a thickness of 16 nm as a cathode. On the cathode, N4,N4'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD) was deposited to a thickness of 60 nm as a capping layer. An organic light-emitting device was manufactured by forming a protective film (encapsulation layer or protecting layer) to protect the organic light-emitting device from oxygen (O2) or moisture in the air by bonding a seal cap containing a desiccant with a UV-curable adhesive on the capping layer.

[0252]

[0253] [Examples 2 to 88] Manufacturing of organic light-emitting devices

[0254] An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound described in Table 15 below was used instead of compound 7 used as the electron transport layer material in Example 1.

[0255]

[0256] [Comparative Examples 1 to 7] Manufacturing of Organic Light-Emitting Devices

[0257] Organic light-emitting devices of Comparative Examples 1 to 7 were manufactured in the same manner as in Example 1, except that the material of Compound 7 used as the electron transport layer material of Example 1 was changed to Comparative Compounds A to G below.

[0258]

[0259]

[0260] [Experimental Example 2] Device Performance Analysis

[0261] For the organic light-emitting devices of Examples 1 to 88 and Comparative Examples 1 to 7, 10 mA / cm was measured using KONICA MINOLTA CS-2000. 2 The driving voltage (Op V) and efficiency (EQE) were measured by applying current, and 10 mA / cm was measured using McScience M6000. 2 The lifespan (LT95) was measured by determining the time it takes for the luminance to decrease from the initial luminance to 95% using constant current driving. The measurement results are shown in Table 15 below.

[0262] [Table 15]

[0263]

[0264]

[0265] As confirmed in Table 15 above, it was confirmed that the organic light-emitting device including the compound represented by Chemical Formula 1 of the present invention as an electron transport layer material had a lower driving voltage, higher efficiency, and longer lifespan compared to Comparative Examples 1 to 7.

[0266]

[0267] [Example 89] Manufacturing of a tandem organic light-emitting device (1)

[0268] The substrate on which ITO (100 nm), the anode of the tandem organic light-emitting device, was laminated was patterned by dividing it into cathode and anode regions and an insulating layer through a photolithography process, and then the surface was treated with UV-ozone and O2:N2 plasma for the purpose of increasing the work function of the anode (ITO) and cleaning it.

[0269] Next, a hole injection layer (HIL) of 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN) was formed on the anode with a thickness of 10 nm. On the hole injection layer, N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine was vacuum-deposited to form a first hole transport layer (HTL 1) with a thickness of 90 nm.

[0270] An electron blocking layer (EBL) of 15 nm thick was formed on the first hole transport layer (HTL 1) using N-phenyl-N-(4-(spiro[benzo[d,e]anthracene-7,9'-fluorene]-2'-yl)phenyl)dibenzo[b,d]furan-4-amine.

[0271] On the electron blocking layer (EBL) above, 9,10-Bis(2-naphthyl)anthracene (ADN) as a host and 2,12-Di-tert-butyl-5,9-bis(4-(tert-butyl)phenyl)-7-(3,5-di-tert-butylphenyl)-5,9-dihydro-5,9-diaza-13b-boranaphtho[3,2,1-de]anthracene (t-DABNA-dtB) as a dopant were deposited. The first light-emitting layer (EML 1) was deposited to a thickness of 25 nm by doping with 3 wt% (host: dopant = 97:3 weight ratio).

[0272] Compound B was deposited on the first light-emitting layer to a thickness of 25 nm to form a first electron transport layer (ETL 1).

[0273] On the first electron transport layer (ETL 1), the following compound A and Li were mixed in a weight ratio of 98:2 to form a first n-type charge generation layer (n-CGL) with a thickness of 18.5 nm.

[0274] On the first n-type charge generation layer (n-CGL), N,N'-bis(naphthalen-1-yl)-N-N'-bis(phenyl)-2,2'-dimethylbenzidine (NPD) as a p-type host and HAT-CN as a dopant were co-deposited (host:dopant = 7:3 weight ratio) to form a first p-type charge generation layer (p-CGL) with a thickness of 8 nm.

[0275] A second hole transport layer (HTL 2) was formed by depositing N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine (N4,N4,N4',N4'-Tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine) to a thickness of 30 nm on the first p-type charge generation layer (p-CGL).

[0276] On the second hole transport layer, a second light-emitting layer (EML 2) was deposited with a thickness of 35 nm by doping 4,4'-N,N'-dicarbazole-biphenyl (CBP) as a host and Ir(ppy)3[tris(2-phenylpyridine)-iridium] as a dopant at 5 wt% (host: dopant = 95:5 weight ratio).

[0277] Compound 7 of the present invention and compound C were mixed in a weight ratio of 1:1 and deposited to a thickness of 30 nm on the second light-emitting layer (EML) to form a second electron transport layer (ETL 2).

[0278] Liq was deposited to a thickness of 1 nm as an electron injection layer (EIL) on the second electron transport layer (ETL 2). Aluminum (Al) was deposited to a thickness of 16 nm on the electron injection layer (EIL) to form a cathode.

[0279] A capping layer (CPL) was deposited on the cathode with a thickness of 60 nm using N4,N4'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD). A seal cap containing a desiccant was bonded to the capping layer (CPL) using a UV-curable adhesive to protect the tandem organic light-emitting diode from oxygen or moisture in the air.

[0280]

[0281]

[0282] [Examples 90 to 104] Manufacture of tandem organic light-emitting device (1)

[0283] Tandem organic light-emitting devices of Examples 90 to 104 were manufactured in the same manner as in Example 89, except that the compounds described in Table 16 below were used instead of Compound 7 used as the electron transport layer material in Example 1.

[0284]

[0285] [Comparative Examples 8 and 9] Manufacturing of Tandem Organic Light-Emitting Devices (1)

[0286] Tandem organic light-emitting devices of Comparative Examples 8 and 9 were manufactured in the same manner as in Example 89, except that the second electron transport layer material of Example 89 was changed as shown in Table 16 below.

[0287]

[0288] [Experimental Example 3] Device Performance Analysis

[0289] For the tandem organic light-emitting devices of Examples 89 to 104 and Comparative Examples 8 and 9, 10 mA / cm was applied using KONICA MINOLTA CS-2000. 2 The driving voltage (Op V) and efficiency (EQE) were measured by applying current, and 10 mA / cm was measured using McScience M6000. 2 The lifespan (LT95) was measured by determining the time it takes for the luminance to decrease from the initial luminance to 95% using constant current driving. The measurement results are shown in Table 16 below.

[0290] [Table 16]

[0291]

[0292] As confirmed in Table 16 above, when the compound represented by the chemical formula 1 of the present invention and compound C were mixed and included as a material of the second electron transport layer in a tandem organic light-emitting device, it was confirmed that the device had a lower driving voltage, higher efficiency, and longer lifespan compared to Comparative Examples 8 and 9.

[0293]

[0294] [Example 105] Manufacturing of a tandem organic light-emitting device (2)

[0295] The substrate on which ITO (100 nm), the anode of the tandem organic light-emitting device, was laminated was patterned by dividing it into cathode and anode regions and an insulating layer through a photolithography process, and then the surface was treated with UV-ozone and O2:N2 plasma for the purpose of increasing the work function of the anode (ITO) and cleaning it.

[0296] Next, a hole injection layer (HIL) of 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN) was formed on the anode with a thickness of 10 nm. A first hole transport layer (HTL 1) of 90 nm was formed on the hole injection layer by vacuum-depositing N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine.

[0297] An electron blocking layer (EBL) of 15 nm thick was formed on the first hole transport layer (HTL 1) using N-phenyl-N-(4-(spiro[benzo[d, e]anthracene-7,9'-fluorene]-2'-yl)phenyl)dibenzo[b,d]furan-4-amine.

[0298] On the electron blocking layer (EBL) above, 9,10-Bis(2-naphthyl)anthracene (ADN) as a host and 2,12-Di-tert-butyl-5,9-bis(4-(tert-butyl)phenyl)-7-(3,5-di-tert-butylphenyl)-5,9-dihydro-5,9-diaza-13b-boranaphtho[3,2,1-de]anthracene (t-DABNA-dtB) as a dopant were deposited. The first light-emitting layer (EML 1) was deposited to a thickness of 25 nm by doping with 3 wt% (host: dopant = 97:3 weight ratio).

[0299] Compound B was deposited on the first light-emitting layer to a thickness of 25 nm to form a first electron transport layer (ETL 1).

[0300] On the first electron transport layer (ETL 1), the following compound A and Li were mixed in a weight ratio of 98:2 to form a first n-type charge generation layer (n-CGL) with a thickness of 18.5 nm.

[0301] On the first n-type charge generation layer (n-CGL), N,N'-bis(naphthalen-1-yl)-N-N'-bis(phenyl)-2,2'-dimethylbenzidine (NPD) as a p-type host and HAT-CN as a dopant were co-deposited (host:dopant = 7:3 weight ratio) to form a first p-type charge generation layer (p-CGL) with a thickness of 80 nm.

[0302] A second hole transport layer (HTL 2) was formed by depositing N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine (N4,N4,N4',N4'-Tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine) to a thickness of 30 nm on the first p-type charge generation layer (p-CGL).

[0303] On the second hole transport layer, a second light-emitting layer (EML 2) was deposited with a thickness of 35 nm by doping 4,4'-N,N'-dicarbazole-biphenyl (CBP) as a host and Ir(ppy)3[tris(2-phenylpyridine)-iridium] as a dopant at 5 wt% (host: dopant = 95:5 weight ratio).

[0304] Compound B was deposited on the second light-emitting layer (EML) to a thickness of 30 nm to form a second electron transport layer (ETL 2).

[0305] A second n-type charge generation layer (n-CGL) was formed with a thickness of 18.5 nm by mixing the following chemicals A and Li in a weight ratio of 98:2 on the second electron transport layer (ETL 2).

[0306] A second p-type charge generation layer (p-CGL) was formed with a thickness of 8 nm by co-depositing N,N'-bis(naphthalen-1-yl)-N-N'-bis(phenyl)-2,2'-dimethylbenzidine (NPD) as a p-type host and HAT-CN as a dopant (host:dopant = 7:3 weight ratio) on the second n-type charge generation layer (n-CGL).

[0307] A third hole transport layer (HTL 3) was formed by depositing N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine (N4,N4,N4',N4'-Tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine) on the second type p-type charge generation layer (p-CGL) to a thickness of 30 nm.

[0308] On the third hole transport layer, a third light-emitting layer (EML 3) was deposited with a thickness of 35 nm by doping 4,4'-N,N'-dicarbazole-biphenyl (CBP) as a host and Ir(ppy)3[tris(2-phenylpyridine)-iridium] as a dopant at 5 wt% (host: dopant = 95:5 weight ratio).

[0309] The compound 7 of the present invention and the compound C were mixed in a weight ratio of 1:1 and deposited to a thickness of 30 nm on the third light-emitting layer (EML) to form a third electron transport layer (ETL 3).

[0310] Liq was deposited as an electron injection layer (EIL) with a thickness of 1 nm on the third electron transport layer (ETL 3).

[0311] A cathode of aluminum (Al) with a thickness of 16 nm was deposited on the electron injection layer (EIL).

[0312] A capping layer (CPL) was deposited on the cathode with a thickness of 60 nm using N4,N4'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD). A seal cap containing a desiccant was bonded to the capping layer (CPL) using a UV-curable adhesive to protect the tandem organic light-emitting diode from oxygen or moisture in the air.

[0313]

[0314]

[0315] [Examples 106 to 124] Manufacture of tandem organic light-emitting devices (2)

[0316] Tandem organic light-emitting devices of Examples 106 to 124 were manufactured in the same manner as in Example 106, except that the compounds described in Table 17 below were used instead of Compound 7 used as the third electron transport layer material in Example 105.

[0317]

[0318] [Comparative Examples 10 and 11] Manufacturing of Tandem Organic Light-Emitting Diodes (2)

[0319] Tandem organic light-emitting devices of Comparative Examples 10 and 11 were manufactured in the same manner as in Example 105, except that the third electron transport layer material of Example 105 was changed as shown in Table 17 below.

[0320]

[0321] [Experimental Example 4] Device Performance Analysis

[0322] For the tandem organic light emitting devices of Examples 105 to 124 and Comparative Examples 10 and 11, 10 mA / cm was applied using KONICA MINOLTA CS-2000. 2 The driving voltage (Op V) and efficiency (EQE) were measured by applying current, and 10 mA / cm was measured using McScience M6000. 2 The lifespan (LT95) was measured by determining the time it takes for the luminance to decrease from the initial luminance to 95% using constant current driving. The measurement results are shown in Table 17 below.

[0323] [Table 17]

[0324]

[0325] As confirmed in Table 17 above, when the compound represented by the chemical formula 1 of the present invention and compound C were mixed and included as materials for the third electron transport layer in a tandem organic light-emitting device, it was confirmed that the device had a lower operating voltage, higher efficiency, and longer lifespan compared to Comparative Examples 10 and 11.

[0326]

[0327] [Experimental Example 5] Performance Evaluation of Tandem Organic Light-Emitting Diodes According to the Compound Mixing Ratio of the Electron Transport Layer

[0328] In the organic light-emitting device of Example 105, the mixing ratio of the two electron transport layer materials included in the third electron transport layer was changed to manufacture the organic light-emitting devices of Examples 125 to 128 and Comparative Examples 12 to 14, and the performance of the tandem organic light-emitting device according to the weight ratio of the compound of the present invention was confirmed. The materials and their mixing ratios are as shown in Table 18 below, and the tandem organic light-emitting devices were each manufactured under the same conditions as Example 105 except for the mixing ratio.

[0329] The measurement methods for driving voltage, efficiency (EQE), and lifespan (LT95) were the same as in Experimental Example 4, and the results are shown in Table 18 below.

[0330] [Table 18]

[0331]

[0332] As confirmed in Table 18 above, when the compound represented by the chemical formula 1 of the present invention and compound C are mixed and included as materials for the third electron transport layer in a tandem organic light-emitting device, it was confirmed that the mixing ratio of compound C: compound 1 was preferably 1:0.5 to 2 by weight. When the compound of the present invention was included in an amount of less than 0.5 by weight (Comparative Examples 12 and 13), it was confirmed that the driving voltage of the tandem organic light-emitting device increased and the lifespan shortened. In addition, when the compound of the present invention exceeded 2 by weight (Comparative Example 14), it was confirmed that the efficiency and lifespan were lower than those of the tandem organic light-emitting devices of Examples 125 to 128. It is thought that the compound of the present invention affects electron mobility, and compound C affects electron injection, but it was determined that these roles were not sufficiently exerted as their mixing ratio changed.

[0333]

[0334] Although the embodiments of the present invention have been described in detail above, the scope of the present invention is not limited thereto, and various modifications and improvements made by those skilled in the art using the basic concept of the present invention defined in the following claims also fall within the scope of the present invention.

Claims

1. First electrode; a second electrode facing the first electrode; and comprising at least one intermediate layer disposed between the first electrode and the second electrode; The above intermediate layer includes an electron transport layer, An organic light-emitting device in which the electron transport layer comprises a compound represented by the following chemical formula 1. In the above chemical formula 1, X is oxygen (O) or sulfur (S), Y1, Y2 and Y3 are nitrogen (N) or CR4, At least two of Y1, Y2 and Y3 are nitrogen (N), n1, n2 and n3 are integers from 0 to 4, L1 and L2 are the same or different from each other, and are each independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 60 carbon atoms, Ar1 and Ar2 are the same or different from each other, and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, R1 to R4 are the same or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, When L1, L2, Ar1, Ar2, R1, R2, R3 and R4 are substituted, the substituents are each independently at least one selected from the group consisting of deuterium, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms and a heteroaryl group having 5 to 60 carbon atoms, and when there are multiple substituents, they are the same or different from each other.

2. In paragraph 1, The above chemical formula 1 is an organic light-emitting device which is a compound represented by the following chemical formulas 2 to 5. In the above chemical formulas 2 to 5, The above X, Y1 to Y3, n1 to n3, L1, L2, Ar1, Ar2 and R1 to R4 and its substituents are as defined in the above chemical formula 1.

3. In paragraph 1, The above chemical formula 1 is an organic light-emitting device which is a compound represented by the following chemical formulas 2-1 to 2-3, 3-1 to 3-3, 4-1 to 4-3 and 5-1 to 5-3. In the above chemical formulas 2-1 to 2-3, 3-1 to 3-3, 4-1 to 4-3 and 5-1 to 5-3, The above X, Y1 to Y3, n1 to n3, L1, L2, Ar1, Ar2 and R1 to R4 and its substituents are as defined in the above chemical formula 1.

4. In paragraph 1, An organic light-emitting device wherein the above L1 and L2 are the same or different and each independently represent a single bond or a substituted or unsubstituted arylene group having 6 to 10 carbon atoms.

5. In paragraph 1, An organic light-emitting device wherein the above L1 and L2 are the same or different from each other, and are each independently selected from a single bond or a substituted or unsubstituted phenylene group.

6. In paragraph 1, An organic light-emitting device wherein the above Ar1 and Ar2 are the same or different from each other and are each independently selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms.

7. In paragraph 1, An organic light-emitting device wherein the above Ar1 and Ar2 are the same or different and are each independently selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, and a substituted or unsubstituted dibenzofuranyl group.

8. In paragraph 1, An organic light-emitting device wherein the intermediate layer further comprises at least one selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport auxiliary layer, and an electron injection layer.

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