Organic compound and organic light-emitting device comprising same

Abstract

An n-type charge generation layer formed by comprising a compound represented by chemical formula 1, according to the present invention, facilitates hole and electron transport in multiple light-emitting stacks, thus allowing an organic light-emitting device comprising the n-type charge generation layer to achieve low driving voltage, high efficiency, and long lifetime.

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] 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.

[0003] 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.

[0004] 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.

[0005] 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.

[0006] 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.

[0007] Therefore, research on the components included in the above intermediate layer is being actively conducted.

[0008] [Prior Art Literature]

[0009] (Prior patent document 1) CN 111410655

[0010] (Prior patent document 2) KR 20160018332

[0011] (Prior patent document 3) KR 20250021017

[0012] The purpose of the present invention is to provide a novel organic compound and an organic light-emitting device comprising the same.

[0013] In addition to the above-mentioned tasks, embodiments according to the present invention can be used to achieve other tasks not specifically mentioned.

[0014] 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.

[0015] 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.

[0016] In order to solve the above problem, according to one embodiment of the present invention, an organic compound having a novel structure represented by the following chemical formula 1 can be provided, and the definition of the following chemical formula 1 is the same as that described in the present specification and claims.

[0017] [Chemical Formula 1]

[0018]

[0019] According to another embodiment of the present invention, an organic light-emitting device may be provided, which may include a first electrode; a second electrode facing the first electrode; and an organic layer disposed between the first electrode and the second electrode; wherein the organic layer may include one selected from the group consisting of a hole injection layer, a hole transport layer, a hole transport assisting layer, a light-emitting layer (dopant and host), an electron transport assisting layer, an electron transport layer, a charge generation layer, an electron injection layer, and combinations thereof, and at least one of the organic layers includes an organic compound represented by the chemical formula 1.

[0020] According to another embodiment of the present invention, an organic light-emitting device may be provided, comprising: an anode; a cathode facing the anode; and N light-emitting stacks between the anode and the cathode, wherein N is an integer of 2 or greater, and N-1 n-type charge generation layers are disposed between different light-emitting stacks of the N light-emitting stacks, and at least one of the n-type charge generation layers includes a compound represented by the chemical formula 1 of the present invention.

[0021] An organic light-emitting device including an n-type charge generation layer organic compound represented by the chemical formula 1 of the present invention can secure characteristics such as low driving voltage, high efficiency, long life, and stability.

[0022] In addition, the organic compound represented by the chemical formula 1 of the present invention prevents diffusion of an alkali metal into a surrounding layer through coordination with a metal component, and facilitates hole and electron movement in a plurality of light-emitting stacks, so that an organic light-emitting device including the charge generation layer can secure the characteristics of low driving voltage, high efficiency, and long life.

[0023] 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.

[0024] The above effects and additional effects are described in detail below.

[0025] FIG. 1 schematically illustrates an organic light-emitting device having a tandem structure including two light-emitting stacks having n-type charge generation layers arranged thereon according to one embodiment of the present invention.

[0026] FIG. 2 schematically illustrates an organic light-emitting device having a tandem structure including three light-emitting stacks having n-type charge generation layers arranged thereon according to one embodiment of the present invention.

[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 described as “including,” “having,” “consisting of,” “arranged,” or “equipped,” other parts may be added unless “only” is used. When a component is described as 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 the component, but also that other components may be interposed between the component and any component disposed on (or below) the component.

[0032] The term “metal component” used herein refers to a metal element component and a derivative thereof that can be used in a constituent layer of an organic light-emitting device. For example, the metal element component may include, but is not limited to, alkali metals such as lithium (Li), sodium (Na), potassium (K), and cesium (Cs); alkaline earth metals such as magnesium (Mg), strontium (Sr), barium (Ba), and radium (Ra); lanthanide metals such as ytterbium (Yb), and combinations thereof. For example, as a derivative of the metal element component, an alkali metal halide-based material such as NaF, LiF, CsF, BaF2, MgF2, or an alkaline earth metal halide-based material, and / or an organometallic material such as Liq, lithium benzoate, and sodium stearate can be used, but is not limited thereto.

[0033] The term “halogen group” as used herein includes fluorine, chlorine, bromine and iodine.

[0034] 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 10 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.

[0035] The term “cycloalkyl group” as used herein refers to a cyclic alkyl radical. Unless otherwise specified, a cycloalkyl group contains 3 to 10 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.

[0036] 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 10 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.

[0037] The term “cycloalkenyl group” as used herein refers to a cyclic alkenyl radical. Unless otherwise specified, a cycloalkenyl group contains 3 to 10 carbon atoms, and further, the cycloalkenyl group may be optionally substituted.

[0038] 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, and may include, but is not limited to, ethynyl, 2-propanyl, and the like. Additionally, an alkynyl group may be optionally substituted.

[0039] 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.

[0040] The terms “aralkyl group” or “arylalkyl group” 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.

[0041] 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 carbon atoms 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, phenanthrenyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, and the like. In addition, an aryl group may be optionally substituted.

[0042] The terms “heteroaryl group” or “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 1 to 30 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, triazinyl, a polycyclic ring such as phenoxathinyl, indolizinyl, indolyl, purinyl, quinolyl, isoquinolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, carbazolyl, phenylcarbazolyl, 9-phenylcarbazolyl, and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 3-pyridinyl, It may include, but is not limited to, 4-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, etc. Additionally, the heteroaryl group may be optionally substituted.

[0043] 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.

[0044] The term “carbon ring” used in this specification may be used as a term that includes 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.

[0045] 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.

[0046] The terms “alkylamino group,” “arylalkylamino group,” “arylamino group,” and “heteroarylamino group” used in this specification 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 additionally, the alkylamino group, arylalkylamino group, arylamino group, and heteroarylamino group may be optionally substituted.

[0047] 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 additionally, the alkylsilyl group, arylsilyl group, alkoxy group, aryloxy group, alkylthio group, and arylthio group may be optionally substituted.

[0048] 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.

[0049] The term “substitution” as used herein means that a hydrogen (H) atom bonded to a carbon atom of the organic 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.

[0050] The above substituents may each independently be selected from the group consisting of deuterium, a cyano group, a nitro group, a halogen group, a hydroxy group, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a heteroalkyl group having 2 to 30 carbon atoms, an aralkyl group having 6 to 30 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a heteroarylalkyl group having 3 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, and an aryloxy group having 6 to 30 carbon atoms.

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

[0052] Unless otherwise specified, the units used in this specification are based on weight (wt). For example, if “%” is stated, it is interpreted as weight percent (wt%).

[0053] Hereinafter, the organic compound according to the present invention and the organic light-emitting device including the same will be described in detail.

[0054] The organic compound of the present invention can be expressed by the following chemical formula 1.

[0055] [Chemical Formula 1]

[0056]

[0057] Here,

[0058] X is oxygen (O) or sulfur (S),

[0059] n1 is an integer from 0 to 3,

[0060] n2, n3 and n4 are integers from 0 to 2,

[0061] n5 is an integer from 0 to 4,

[0062] L1 is selected from the group consisting of 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, and a substituted or unsubstituted heteroarylalkylene group having 6 to 60 carbon atoms,

[0063] Ar is selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 17 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] R1, R2, R3, R4 and R5 are the same or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, 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 are bonded to adjacent groups to form a substituted or unsubstituted can form unsubstituted rings,

[0065] L1, Ar, R1, R2, The substituents of R3, R4 and R5 are each independently selected from the group consisting of deuterium, a cyano group, a nitro group, a halogen group, a hydroxy group, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a heteroalkyl group having 2 to 30 carbon atoms, an aralkyl group having 6 to 30 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 60 carbon atoms, a heteroarylalkyl group having 3 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms and an aryloxy group having 6 to 30 carbon atoms. There are more than one type, and when substituted with multiple substituents, they are the same or different from each other, and can combine with adjacent groups to form a substituted or unsubstituted ring.

[0066] According to one embodiment of the present invention, in the organic compound represented by the above chemical formula 1, L1 may be a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 60 carbon atoms. For example, L1 may be, but is not limited to, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a dibenzofuranyl group, a diphenzothiophenyl group, a phenyl group substituted with a deuterium or deuterium-substituted alkyl, a biphenyl group substituted with a deuterium or deuterium-substituted alkyl, a naphthyl group substituted with a deuterium or deuterium-substituted alkyl, an anthracenyl group substituted with a deuterium or deuterium-substituted alkyl, a phenanthrenyl group substituted with a deuterium or deuterium-substituted alkyl, a dibenzofuranyl group substituted with a deuterium or deuterium-substituted alkyl, a diphenzothiophenyl group substituted with a deuterium or deuterium-substituted alkyl, or a combination thereof.

[0067] According to one embodiment of the present invention, in the organic compound represented by the above chemical formula 1, L1 may be a substituted or unsubstituted arylene group having 6 to 30 carbon atoms. In this case, unlike a heteroarylene group, the influence of deviating from a preferred HOMO energy level or LUMO energy level can be minimized. For example, L1 may be a phenyl group, a naphthyl group, an anthracenyl group, a phenyl group substituted with a deuterium or deuterium-substituted alkyl, a naphthyl group substituted with a deuterium or deuterium-substituted alkyl, or an anthracenyl group substituted with a deuterium or deuterium-substituted alkyl.

[0068] L1 is selected from the group consisting of 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 1 to 30 carbon atoms, and a substituted or unsubstituted heteroarylalkylene group having 6 to 60 carbon atoms,

[0069] Ar is selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 17 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 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,

[0070] R1, R2, R3, R4 and R5 are the same or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, 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 1 to 30 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 are bonded to adjacent groups to form a substituted or unsubstituted can form unsubstituted rings,

[0071] L1, Ar, R1, R2, The substituents of R3, R4 and R5 are each independently selected from the group consisting of deuterium, a cyano group, a nitro group, a halogen group, a hydroxy group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a heteroalkyl group having 2 to 30 carbon atoms, an aralkyl group having 6 to 30 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 1 to 30 carbon atoms, a heteroarylalkyl group having 3 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms and an aryloxy group having 6 to 30 carbon atoms. There are more than one type, and when substituted with multiple substituents, they are the same or different from each other, and can combine with adjacent groups to form a substituted or unsubstituted ring.

[0072] According to one embodiment of the present invention, in the organic compound represented by the above chemical formula 1, L1 may be a substituted or unsubstituted arylene group having 6 to 30, 6 to 17, 6 to 14, or 6 to 12 carbon atoms, or a substituted or unsubstituted heteroarylene group having 1 to 30, 1 to 10, 4 to 10, 5 to 10, or 9 to 10 carbon atoms. For example, L1 may be, but is not limited to, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a dibenzofuranyl group, a diphenzothiophenyl group, a phenyl group substituted with a deuterium or deuterium-substituted alkyl, a biphenyl group substituted with a deuterium or deuterium-substituted alkyl, a naphthyl group substituted with a deuterium or deuterium-substituted alkyl, an anthracenyl group substituted with a deuterium or deuterium-substituted alkyl, a phenanthrenyl group substituted with a deuterium or deuterium-substituted alkyl, a dibenzofuranyl group substituted with a deuterium or deuterium-substituted alkyl, a diphenzothiophenyl group substituted with a deuterium or deuterium-substituted alkyl, or a combination thereof.

[0073] According to one embodiment of the present invention, in the organic compound represented by the above chemical formula 1, L1 may be a substituted or unsubstituted arylene group having 6 to 30, 6 to 17, 6 to 14 or 6 to 12 carbon atoms. In this case, unlike a heteroarylene group, the influence of deviating from a preferred HOMO energy level or LUMO energy level can be minimized. For example, L1 may be a phenyl group, a naphthyl group, an anthracenyl group, a phenyl group substituted with a deuterium or deuterium-substituted alkyl, a naphthyl group substituted with a deuterium or deuterium-substituted alkyl, or an anthracenyl group substituted with a deuterium or deuterium-substituted alkyl.

[0074] According to one embodiment of the present invention, in the organic compound represented by the above chemical formula 1, when L1 is a phenyl group, a naphthyl group, or anthracenyl group, it can have characteristics as a compound suitable for an n-type charge generation layer, and when L1 is a phenyl group or a naphthyl group, it can have characteristics as a compound having a HOMO-LUMO energy level more suitable for an n-type charge generation layer.

[0075] According to one embodiment of the present invention, in the organic compound represented by the above chemical formula 1, Ar may be a substituted or unsubstituted aryl group having 6 to 17, 6 to 14, or 6 to 12 carbon atoms, or a substituted or unsubstituted heteroaryl group having 1 to 30, 1 to 10, 4 to 10, 5 to 10, or 9 to 10 carbon atoms. In this case, since it can have a high glass transition temperature (Tg) even with a low molecular weight, the deposition temperature can be lowered, and thus the thermal stability of the compound can be improved during the deposition process and operation of the organic light-emitting device after manufacturing the device. For example, Ar is a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a carbazolyl group, a pyridinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a benzoxyzolyl group, a benzothiazolyl group, a benzoimidazolyl group, a phenanthroline group, a phenyl group substituted with a deuterium or deuterium-substituted alkyl, a biphenyl group substituted with a deuterium or deuterium-substituted alkyl, a naphthyl group substituted with a deuterium or deuterium-substituted alkyl, an anthracenyl group substituted with a deuterium or deuterium-substituted alkyl, a phenanthrenyl group substituted with a deuterium or deuterium-substituted alkyl, a pyrenyl group substituted with a deuterium or deuterium-substituted alkyl, a It may be, but is not limited to, a carbazolyl group, a pyridinyl group substituted with a deuterium or deuterium-substituted alkyl, a dibenzofuranyl group substituted with a deuterium or deuterium-substituted alkyl, a dibenzothiophenyl group substituted with a deuterium or deuterium-substituted alkyl, a pyrimidinyl group substituted with a deuterium or deuterium-substituted alkyl, a quinolinyl group substituted with a deuterium or deuterium-substituted alkyl, an isoquinolinyl group substituted with a deuterium or deuterium-substituted alkyl, a benzoxyzolyl group substituted with a deuterium or deuterium-substituted alkyl, a benzothiazolyl group substituted with a deuterium or deuterium-substituted alkyl, a benzoimidazolyl group substituted with a deuterium or deuterium-substituted alkyl, a phenanthroline group substituted with a deuterium or deuterium-substituted alkyl, or a combination thereof.

[0076] According to one embodiment of the present invention, in the organic compound represented by the above chemical formula 1, Ar may be a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a 2-pyridinyl group, a 3-pyridinyl group, a 4-pyridinyl group, a 2-pyrimidinyl group, a 4-pyrimidinyl group, a 4-pyrimidinyl group, a quinolinyl group, or an isoquinolinyl group.

[0077] According to one embodiment of the present invention, in the organic compound represented by the above chemical formula 1, Ar may be bonded to positions 1 to 8 of the following chemical formula A. In addition, Ar and L1 of the above chemical formula 1 may be bonded to one benzene of the following chemical formula A. When L1 of the above chemical formula 1 is bonded to position 4 of the following chemical formula A, Ar may be bonded to one of positions 1 to 3; when L1 of the above chemical formula 1 is bonded to position 3 of the following chemical formula A, Ar may be bonded to one of positions 1, 2, and 4; when L1 of the above chemical formula 1 is bonded to position 2 of the following chemical formula A, Ar may be bonded to one of positions 1, 3, and 4; when L1 of the above chemical formula 1 is bonded to position 1 of the following chemical formula A, Ar may be bonded to one of positions 2 to 4.

[0078] [Chemical Formula A]

[0079]

[0080] According to one embodiment of the present invention, in the organic compound represented by the above chemical formula 1, R1 may be hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a combination thereof, but is not limited thereto.

[0081] According to one embodiment of the present invention, in the organic compound represented by the above chemical formula 1, R1 may be selected from hydrogen (H), deuterium (D), a methyl group substituted with deuterium (CD3), an unsubstituted phenyl group (Ph), or a combination thereof, and when selected in this manner, the structural stability and thermal stability of the organic compound represented by the chemical formula 1 are excellent.

[0082] According to one embodiment of the present invention, in the organic compound represented by the above chemical formula 1, R1 may be bonded to position 2 or 9 in the following chemical formula B. In addition, when R1 of the above chemical formula 1 is bonded to position 2 of the following chemical formula B, L1 of the above chemical formula 1 is bonded to position 9, and when R1 of the above chemical formula 1 is bonded to position 9 of the following chemical formula B, L1 of the above chemical formula 1 may be bonded to position 2.

[0083] [Chemical Formula B]

[0084]

[0085] According to one embodiment of the present invention, the organic compound represented by the chemical formula 1 of the present invention includes a phenanthroline moiety represented by the chemical formula B. Phenanthroline includes nitrogen (N) having a sp2 hybrid orbital that is relatively rich in electrons, and this nitrogen binds to an alkali metal or alkaline earth metal, which is a dopant of an n-type charge generation layer, to form a gap state. By the formed gap state, electrons can be smoothly transferred from the n-type charge generation layer to the electron transport layer, and the alkali metal or alkaline earth metal can not diffuse into the p-type charge generation layer, so that the lifespan can be improved.

[0086] According to one embodiment of the present invention, the linker (L1) of the organic compound represented by the chemical formula 1 of the present invention acts as a passage for allowing the abundant electrons of the core to reach Ar through conjugation control, and controls the HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital). This is because the Ar group acts as an important factor in exhibiting electron transfer characteristics. The Ar group has a large electron affinity, so it lowers the LUMO energy level, and as a result, the energy gap becomes smaller, which can facilitate electron transfer.

[0087] According to one embodiment of the present invention, Ar of the organic compound represented by Chemical Formula 1 of the present invention can easily control the electron transport capability by improving the pi (π)-electron density and controlling the LUMO energy. Therefore, by making electron injection smoother, electron injection into the electron transport layer increases, thereby having the effect of achieving a balance with the large amount of holes injected from the anode. When Ar is an aryl group having 6 to 17 carbon atoms, it has a non-bulky structure (e.g., a phenyl group, a biphenyl group, a naphthyl group, anthracenyl group, a phenanthrenyl group), and can easily form a plate-like structure than a bulky aryl group (e.g., a triphenylene group), thereby increasing electron mobility. When Ar is a heteroaryl group having 1 to 30 carbon atoms, it has a large electron affinity, thereby lowering the LUMO energy level and narrowing the energy gap, and thus has excellent electron transport capability, making it more suitable as an n-type charge generation layer material.

[0088] According to one embodiment of the present invention, the organic compound represented by the chemical formula 1 of the present invention is characterized in that L1 and Ar are bonded to one benzene based on the chemical formula A, and in the case of a compound at the para position, it may be a structure in which L1 is connected to position 1 of the chemical formula A and Ar is connected to position 4; or L1 is connected to position 4 and Ar is connected to position 1; and in the case of a compound at the meta position, it may be a structure in which L1 is connected to position 1 of the chemical formula A and Ar is connected to position 3; or L1 is connected to position 2 and Ar is connected to position 4; or L1 is connected to position 3 and Ar is connected to position 1; or L1 is connected to position 4 and Ar is connected to position 2; and in the case of a compound at the ortho position, it may be a structure in which L1 is connected to position 1 of the chemical formula A and Ar is connected to position 2; or L1 is connected to position 2 and Ar is connected to position 3; or L1 is connected to position 4; or L1 is connected to position 2 and Ar is connected to position 1; It can be a structure in which L1 is connected to position 3 and Ar is connected to position 2; or L1 is connected to position 4 and Ar is connected to position 3. For example, in chemical formula A, if L1 is connected to position 1 and Ar is connected to position 3; L1 is connected to position 2 and Ar is connected to position 4; L1 is connected to position 3 and Ar is connected to position 1; or L1 is connected to position 4 and Ar is connected to position 2, a plate-like structure is formed, inducing stacking between molecules, and thus increasing electron mobility, which can result in better electron transfer capability.

[0089] According to one embodiment of the present invention, the organic compound of the chemical formula 1 can be expressed by the following chemical formulas 2 to 4.

[0090] In the following chemical formulas 2 to 4,

[0091] n6, n7, n 8, n9 and n 10 is an integer from 0 to 4,

[0092] R6, R7, R8, R9 and R 10is 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 1 to 30 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,

[0093] R6, R7, R8, R9 and R 10 The substituents of are each independently at least one selected from the group consisting of deuterium, a cyano group, a nitro group, a halogen group, a hydroxy group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a heteroalkyl group having 2 to 30 carbon atoms, an aralkyl group having 6 to 30 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 1 to 30 carbon atoms, a heteroarylalkyl group having 3 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, and an aryloxy group having 6 to 30 carbon atoms, and a plurality of When substituted with a substituent, they are the same or different from each other, and can combine with adjacent groups to form a substituted or unsubstituted ring.

[0094] X, n1, n2, n3, n4 and n5 are as defined in the above chemical formula 1,

[0095] Ar, R1, R 2,R3, R4 and R5 and their substituents are as defined in the above chemical formula 1.

[0096] According to one embodiment of the present invention, in the organic compounds represented by the following chemical formulas 2 to 4, R6, R7, R8, R9 and R 10 can be hydrogen or deuterium.

[0097]

[0098]

[0099] 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 2-12, 3-1 to 3-12, and 4-1 to 4-4, but is not limited thereto.

[0100] According to one embodiment of the present invention, the chemical formula 2 can be expressed by the following chemical formulas 2-1 to 2-12, the chemical formula 3 can be expressed by the following chemical formulas 3-1 to 3-12, and the chemical formula 4 can be expressed by the following chemical formulas 4-1 to 4-4, but is not limited thereto.

[0101] In the following chemical formulas 2-1 to 2-12, 3-1 to 3-12 and 4-1 to 4-4,

[0102] X, n1, n2, n3, n4 and n5 are as defined in the above chemical formula 1,

[0103] Ar, R1, R 2, R3, R4 and R5 and their substituents are as defined in the above chemical formula 1,

[0104] n6, n7, n8, n9 and n 10 is as defined in the above chemical formulas 2 to 4,

[0105] R6, R7, R8, R9 and R 10 And their substituents are as defined in the above chemical formulas 2 to 4.

[0106] According to one embodiment of the present invention, based on L1 of the above chemical formula 1, the chemical formulas A and B can form an ortho-position bond, for example, it can be chemical formulas 2-9 to 2-12 below. In addition, based on L1, the chemical formulas A and B can form a meta-position bond, for example, it can be chemical formulas 2-5 to 2-8 and 3-5 to 3-8 below. In addition, based on L1, the chemical formulas A and B can form a para-position bond, for example, it can be chemical formulas 2-1 to 2-4 and 3-1 to 3-4 below.

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121] According to one embodiment of the present invention, Ar of the above chemical formula 1 may be selected from compounds of M1 to M16 below. * means a part in which the following partial compound is bonded to the above chemical formula A by a single bond.

[0122]

[0123]

[0124]

[0125] According to one embodiment of the present invention, the organic compound represented by Chemical Formula 1, specifically, the organic compound represented by Chemical Formula 2-1 to 2-12, Chemical Formula 3-1 to 3-12 or Chemical Formula 4-1 to 4-4 may be selected from the group consisting of compounds shown in Table 1 below, but is not limited thereto. In Table 1 below, n1 is 1, R1 is bonded to position 2 of Chemical Formula B, and n2 to n 10 If this is 0 or 1, R2 to R 10 is hydrogen. In addition, among the items in Table 1 below, the Ar bonding position indicates that Ar is single-bonded at one of positions 1 to 4 of the chemical formula A.

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142] According to one embodiment of the present invention, the compound described in Table 1 can be expressed as follows.

[0143]

[0144]

[0145]

[0146]

[0147]

[0148] The organic light-emitting device of the present invention may be an organic light-emitting device having a tandem structure.

[0149] The 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 anodes and cathodes opposed to each other on a substrate and a light-emitting layer laminated between the anodes and cathodes to emit 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.

[0150] In the case of an organic light-emitting device having a tandem structure according to an embodiment of the present invention, N emitting stacks are included, and N-1 charge generation layers (charge generation layers (CGLs) or charge generation layers) are arranged between different emitting stacks, so that the device 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 more, and for example, N can be one of 2, 3, 4, and 5. According to an embodiment of the present invention, the n-type charge generation layer of the organic light-emitting device including a plurality of emitting stacks can include an organic compound represented by Chemical Formula 1. For example, when N is 2, it may include one n-type charge generation layer and one p-type charge generation layer, and when N is 3, it may include two n-type charge generation layers and two p-type charge generation layers.

[0151] In the present invention, the light-emitting stack refers to a unit structure including an organic layer including an electron transport layer (ETL) and a hole transport layer (HTL), and an organic emitting layer (EML) disposed between the electron transport layer and the hole transport layer. The organic layer may further include an electron injection layer (EIL), a hole injection layer (HIL), an electron transport auxiliary layer, and a hole transport auxiliary layer, and other organic layers may be further included depending on the structure or design of the organic light-emitting device.

[0152] Hereinafter, various embodiments of the present invention will be described with reference to the attached drawings.

[0153] FIG. 1 is a drawing showing the structure of an organic light-emitting device according to one embodiment of the present invention. As illustrated in FIG. 1, the organic light-emitting device (100) of the present invention includes an anode (100A) and a cathode (100B) facing each other, and an intermediate layer (100C) positioned between the anode (100A) and the cathode (100B). The intermediate layer (100C) includes a first light-emitting stack (810) positioned between the anode (100A) and the cathode (100B) and including a first light-emitting layer (410); a second light-emitting stack (820) positioned between the first light-emitting stack (810) and the cathode (100B) and including a second light-emitting layer (420); and a charge generation layer (700) positioned between the first and second light-emitting stacks (810 and 820). The first light-emitting stack (810) includes a hole injection layer (200), a first hole transport layer (310), a first light-emitting layer (410), and a first electron transport layer (510), and the second light-emitting stack (820) includes a second hole transport layer (320), a second light-emitting layer (420), a second electron transport layer (520), and an electron injection layer (600).

[0154] The above anode (100A) may include, but is not limited to, a material such as indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO) that is transparent, has a relatively large work function value, and has excellent conductivity.

[0155] The above cathode (100B) 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 cathode that allows light to pass through may be formed using indium tin oxide (ITO) or indium zinc oxide (IZO), but is not limited thereto. In order to prevent external moisture, etc. from penetrating into the organic light-emitting device, a capping layer (CPL) and / or a protective film (protecting layer or encapsulation layer or seal cap) formed on the upper portion of the cathode of the organic light-emitting device may be further included.

[0156] The above hole transport layer (310, 320) must be formed of a material having excellent hole transport properties. For example, it may include a phthalocyanine derivative, a porphyrin derivative, a triarylamine derivative, or an indolocarbazole derivative. 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., but are not limited thereto.

[0157] Although not shown in Fig. 1, in order to increase the efficiency of the light-emitting layer, an electron transport auxiliary layer or a hole transport auxiliary layer may be additionally included in contact with the light-emitting layer.

[0158] The above light-emitting layer (410, 420) may be formed by being doped with a dopant to improve the luminous efficiency of the host and the device, and the light-emitting layer (410, 420) may emit light in blue, green, or red, but is not limited thereto, and may be combined with light-emitting layers of various colors and color coordinates used in organic light-emitting devices. For example, the CIEx coordinate of the blue light-emitting layer may have a range of 0.01 to 0.15, and the CIEy coordinate may have a range of 0.03 to 0.07, and the CIEx coordinate of the green light-emitting layer may have a range of 0.19 to 0.32, and the CIEy coordinate may have a range of 0.65 to 0.76.

[0159] The light-emitting layer dopant material and the light-emitting layer host material can be selected according to the selected color of the light-emitting layer (410, 420) included in the organic light-emitting device of the present invention. For example, when the total weight of the light-emitting layer host is 100 wt%, the doping concentration of the light-emitting layer dopant can be adjusted within the range of 1 to 20 wt%, and is not limited thereto, but may be, for example, 3 to 15 wt%, for example, 5 to 10 wt%, for example, 3 to 8 wt%, for example, 2 to 7 wt%, but is not limited thereto.

[0160] For example, the dopant of the light-emitting layer (410, 420) is a general material used in the present technical field, such as N1,N1,N6,N6-tetrakis(4-(1-silyl)phenyl)pyrene-1,6-diamine, iridium metal complex (e.g., Ir(ppy)3), 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 (2,12-Di-tert-butyl-5,9-bis(4-(tert-butyl)phenyl)-7-(3,5-di-tert-butylphenyl)-5,9-dihydro5,9-diaza-13b-boranaphtho[3,2,1-de]anthracene, t-DABNA-dtB, etc., but are not limited thereto.

[0161] The electron transport layer (510, 520) and electron injection layer (600) can stably supply electrons to the light-emitting layer through smooth electron transport. The materials of the electron transport layer (510, 520) and electron injection layer (600) require high electron mobility. For example, each independently 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, naphthyridine derivatives, aldazine derivatives, Examples thereof include carbazole derivatives, indole derivatives, phosphine oxide derivatives, bistyryl 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 compounds can be used alone, but they can also be mixed with other materials. For example, they can include, but are not limited to, substances 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.

[0162] The charge generation layer (700) is arranged between the first light-emitting stack (810) and the second light-emitting stack (820), and supplies charges to the first light-emitting stack and the second light-emitting stack. In addition, the charge generation layer plays a role in controlling charge balance in the first light-emitting stack and the second light-emitting stack, and may be composed of multiple layers by including an n-type charge generation layer (n-CGL) (700A) and a p-type charge generation layer (p-CGL) (700B), but is not limited thereto, and may be composed of a single layer.

[0163] The above n-type charge generation layer (700A) injects electrons into the first light-emitting stack (810). According to one embodiment of the present invention, the n-type charge generation layer may be formed of a single component of an n-type host material. According to another embodiment of the present invention, the n-type charge generation layer may be formed by adding an n-type dopant material to an n-type host material. The n-type host material may include an organic compound represented by Chemical Formula 1 according to the present invention, and thus, the organic light-emitting device according to the present invention may secure the characteristics of low driving voltage, high efficiency, and long lifespan.

[0164] When the n-type charge generation layer (700A) of the present invention is formed by including the n-type dopant material, the n-type dopant material may be an alkali metal or alkaline earth metal compound for electron injection or electron transport. For example, it includes, but is not limited to, alkali metals such as lithium (Li), sodium (Na), potassium (K), cesium (Cs), and / or alkaline earth metals such as magnesium (Mg), strontium (Sr), barium (Ba), and radium (Ra).

[0165] The n-type charge generation layer (700A) including the organic compound represented by the chemical formula 1 of the present invention has an excellent charge balance control, so that even if a small amount of dopant is added, it can sufficiently perform its role as an n-type charge generation layer. This allows for a reduced amount of dopant to be used, enabling economical manufacturing of the device. In addition, since the dopant has sufficient electrons, the amount of electrons remains the same even if doped in excess of 5 wt%. Therefore, even if the dopant is added in excess of 5 wt%, a better effect cannot be expected, and if it exceeds 10 wt%, leakage current and a short-circuit phenomenon of the organic light-emitting device may occur. Therefore, when the weight of the organic compound represented by the chemical formula 1 according to the present invention used as the n-type host is 100 wt%, the n-type dopant may be added in a ratio of about 0.1 to 10 wt%, for example, about 0.5 to 5 wt%. When the n-type dopant is added in the above ratio, the organic light-emitting device of the present invention can exhibit the best characteristics.

[0166] The above p-type charge generation layer (700B) injects holes into the second light-emitting stack (820). The 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(naphthalene-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.

[0167] FIG. 2 is a drawing showing the structure of an organic light-emitting device according to one embodiment of the present invention. As illustrated in FIG. 2, the organic light-emitting device of the present invention includes an anode (100A) and a cathode (100B) facing each other, and an intermediate layer (100C) positioned between the anode (100A) and the cathode (100B). The intermediate layer (100C) is positioned between the anode (100A) and the cathode (100B) and includes: a first light-emitting stack (810) including a first light-emitting layer (410); a second light-emitting stack (820) including a second light-emitting layer (420); a third light-emitting stack (830) including a third light-emitting layer (430); a first charge generation layer (710) positioned between the first light-emitting stack (810) and the second light-emitting stack (820); And a second charge generation layer (720) positioned between the second light-emitting stack (820) and the third light-emitting stack (830). The first charge generation layer (710) and the second charge generation layer (720) may include a first n-type charge generation layer (710A) and a second n-type charge generation layer (720A), and a first p-type charge generation layer (710B) and a second p-type charge generation layer (720B), respectively. The first n-type charge generation layer (710A) and the second n-type charge generation layer (720A) may be the same as or different from each other, and at least one may include an organic compound represented by Chemical Formula 1 according to the present invention. According to one embodiment of the present invention, both the first n-type charge generation layer and the second n-type charge generation layer may include an organic compound represented by Chemical Formula 1 according to the present invention.

[0168] According to one embodiment of the present invention, one of the first or second n-type charge generation layers may include an organic compound represented by the chemical formula 1 according to the present invention, and the other may use a compound disclosed in JP 4595346B2.

[0169] The first n-type charge generation layer (710A) and the second n-type charge generation layer (720A) and the first p-type charge generation layer (710B) and the second p-type charge generation layer (720B) of FIG. 2 can be applied in the same manner as the n-type charge generation layer (700A) and the p-type charge generation layer (700B) described in FIG. 1. For example, at least one of the first n-type charge generation layer (710A) and the second n-type charge generation layer (720A) can include an organic compound represented by the chemical formula 1 according to the present invention, and thereby, the organic light-emitting device can secure the characteristics of low driving voltage, high efficiency, and long life.

[0170] For example, if one of the first n-type charge generation layer (710A) and the second n-type charge generation layer (720A) includes an organic compound represented by the chemical formula 1 according to the present invention, it may be formed as a single component of an n-type host material, or may be formed by adding an n-type dopant material to the n-type host material. The description of the material type of the first n-type charge generation layer (710A) and the second n-type charge generation layer (720A) and the n-type host and n-type dopant may be equally applied to the description of the n-type charge generation layer (700A).

[0171] The types of compounds for forming the first p-type charge generation layer (710B) and the second p-type charge generation layer (720B) of FIG. 2 are the same as those described in relation to the p-type charge generation layer (700B) of FIG. 1, and the first p-type charge generation layer (710B) and the second p-type charge generation layer (720B) may be the same or different from each other.

[0172] The anode (100A), cathode (100B), hole injection layer (200), and electron injection layer (600) of FIG. 2 can be applied in the same manner as described in FIG. 1. The first hole transport layer (310), the second hole transport layer (320), and the third hole transport layer (330) of FIG. 2 can be applied in the same manner as or similarly to the hole transport layers (310, 320) of FIG. 1, and the compounds for forming the first hole transport layer (310), the second hole transport layer (320), and the third hole transport layer (330) can be the same or different from each other. The first light-emitting layer (410), the second light-emitting layer (420), and the third light-emitting layer (430) of FIG. 2 may be applied in the same or similar manner as described in relation to the light-emitting layers (410, 420) of FIG. 1, and the compounds for forming the first light-emitting layer (410), the second light-emitting layer (420), and the third light-emitting layer (430) may be the same or different from each other. The first electron transport layer (510), the second electron transport layer (520), and the third electron transport layer (530) of FIG. 2 may be applied in the same or similar manner as described in relation to the electron transport layers (510, 520) of FIG. 1, and the compounds for forming the first electron transport layer (510), the second electron transport layer (520), and the third electron transport layer (530) may be the same or different from each other.

[0173] Furthermore, although not shown in the drawing, an organic light-emitting device according to an embodiment of the present invention may include a tandem structure in which four or more light-emitting stacks and three or more charge-generation layers are arranged between an anode and a cathode. In this case, at least one of the n-type charge-generation layers may include an organic compound represented by Chemical Formula 1 according to the present invention.

[0174] Hereinafter, the synthesis method of the above compounds is described using representative examples. However, the synthesis method of the compounds of the present invention is not limited to the methods exemplified below.

[0175]

[0176] [Synthesis example]

[0177] 1. Synthesis of product 1

[0178] Product 1 can be synthesized as follows, but is not limited thereto.

[0179] [Reaction Formula 1]

[0180]

[0181] Under a nitrogen atmosphere, reactant 1 of P1 (22.1 mmol), reactant 2 of P1 (20.1 mmol), Pd(PPh3)4 (1.01 mmol), Cs2CO3 (60.3 mmol), 1,4-dioxane (200 mL), and H2O (40 mL) were added to a reaction flask and stirred and refluxed. After completion of the reaction, the mixture was concentrated and washed with water by stirring. The filtered solid was dried and recrystallized with toluene / hexane to obtain product 1 of P1.

[0182] The synthesis results of the product 1 of the above P1 are as shown in Table 2 below, and the product 1 was synthesized in the same manner as above, except that the reactants 1 and 2 of P1 were used instead of the reactants 1 and 2 of P2 to P16 in Table 2 below in the product synthesis method. In addition, the specific compounds of the present invention and similar compounds can be synthesized through the above synthesis examples.

[0183]

[0184]

[0185]

[0186]

[0187] [Experimental Example 1] Confirmation of HOMO and LUMO levels of the n-type charge generation layer

[0188] The charge generation layer serves as a cathode and an anode for each connected unit of a plurality of light-emitting stacks or tandem devices, and generates holes and electrons and injects them into the light-emitting layer of the tandem device structure. In the case of the n-type charge generation layer, it plays a role in transferring electrons to the electron transport layer at the interface by controlling the HOMO-LUMO level between the hole transport layer (or p-type charge generation layer) and the electron transport layer. For this purpose, it is preferable that the LUMO of the electron transport layer be similar to the HOMO level of the hole transport layer (or p-type charge generation layer).

[0189] In order to confirm whether the organic compound represented by the chemical formula 1 of the present invention is suitable as an n-type charge generation layer material, HOMO and LUMO were calculated using Gaussian software (B3LYP DFT 6-31G(d) by Gaussian'16.0), and the results are shown in Table 3 below.

[0190]

[0191] [Example 1] Manufacturing of organic light-emitting devices

[0192] The substrate on which ITO (100 nm), the anode of the organic light-emitting device, 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.

[0193] 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. 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.

[0194] 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 at 3 The first light-emitting layer (EML 1) was deposited to a thickness of 25 nm by doping with a weight % (host: dopant = 97:3, weight ratio).

[0195] A first electron transport layer (ETL 1) of 2-(4-(9,10-di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole) having a thickness of 25 nm was deposited on the first light-emitting layer.

[0196] On the first electron transport layer (ETL 1), an n-type charge generation layer (n-CGL) was formed with a thickness of 185 Å by mixing compound 1 as a host compound (n-type host) of the n-type charge generation layer and Li as a dopant compound (n-type dopant) of the n-type charge generation layer. At this time, when the weight of compound 1 as the n-type host was 100 wt%, the amount of Li as the mixed n-type dopant was 2 wt%.

[0197] A p-type charge generation layer (p-CGL) was formed with a thickness of 80 Å by co-depositing HAT-CN as a p-type dopant on the above n-type charge generation layer (n-CGL).

[0198] 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) on the p-type charge generation layer (p-CGL) to a thickness of 30 nm.

[0199] 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).

[0200] A second electron transport layer (ETL 2) was deposited on the second light-emitting layer (EML 2) with a thickness of 30 nm by mixing N-phenyl-N-(4-(10-phenylanthracen-9-yl)phenyl)pyridin-4-amine and Liq in a 1:1 ratio. LiQ was deposited on the second electron transport layer (ETL 2) with a thickness of 1 nm as an electron injection layer (EIL). Aluminum (Al) as the electron injection layer (EIL) was deposited as a cathode with a thickness of 16 nm. 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 organic light-emitting device from oxygen or moisture in the air.

[0201]

[0202] [Examples 2 to 112]

[0203] Organic light-emitting devices of Examples 2 to 112 were manufactured in the same manner as in Example 1, except that Compound 1 used as the n-type host material of the n-type charge generation layer of Example 1 was changed to that described in Table 3 below.

[0204]

[0205] [Comparative Examples 1 to 4]

[0206] Organic light-emitting devices of Comparative Examples 1 to 4 were manufactured in the same manner as in Example 1, except that Compound 1 used as the n-type host material of the n-type charge generation layer of Example 1 was changed to Comparative Compounds A to D below.

[0207]

[0208]

[0209] [Experimental Example 2] Performance Evaluation of Organic Light-Emitting Diodes

[0210] For the organic light-emitting devices of Examples 1 to 112 and Comparative Examples 1 to 4, 10 mA / cm was measured using KONICA MINOLTA CS-2000. 2 The efficiency (Cd / A) was measured by applying current, and 10mA / cm was measured using McScience M6000. 2 The lifespan (LT95) was measured by checking the time it takes for the luminance to decrease from the initial luminance to 95% by constant current driving.

[0211] The measurement results are shown in Table 4 below.

[0212]

[0213]

[0214]

[0215]

[0216] As shown in Table 4 above, the organic compound represented by Chemical Formula 1 of the present invention is characterized in that L1 and Ar are bonded to one benzene based on Chemical Formula A, and L1 and Ar are connected to each other in the para, meta, and ortho positions, thereby improving electron mobility, and it was confirmed that it is suitable as an n-type charge generation layer material compared to Comparison 1 to 3 without Ar.

[0217] In addition, the organic compound represented by the chemical formula 1 of the present invention has a structure in which, in the case of a compound at the para position, L1 is connected to position 1 of the chemical formula A and Ar is connected to position 4; or L1 is connected to position 4 and Ar is connected to position 1; in the case of a compound at the meta position, L1 is connected to position 1 of the chemical formula A and Ar is connected to position 3; or L1 is connected to position 2 and Ar is connected to position 4; or L1 is connected to position 3 and Ar is connected to position 1; or L1 is connected to position 4 and Ar is connected to position 2; and in the case of a compound at the ortho position, L1 is connected to position 1 of the chemical formula A and Ar is connected to position 2; or L1 is connected to position 2 and Ar is connected to position 3; or L1 is connected to position 4 and Ar is connected to position 3; or L1 is connected to position 2 and Ar is connected to position 1; or L1 is connected to position 3 and Ar is connected to position 2; or L1 is connected to position 3 and Ar is connected to position 2; or L1 is connected to position 3 and Ar is connected to position 2; or L1 is connected to position 1 and Ar is connected to position 1; or L1 is connected to position 3 and Ar is connected to position 2; It could be a structure where L1 is connected to number 4 and Ar is connected to number 3.

[0218] Accordingly, when the organic compound represented by the chemical formula 1 of the present invention has a connection form as described above, that is, when Ar is an aryl group having 6 to 17 carbon atoms, stacking is induced by forming a plate-like structure rather than a bulky aryl group (e.g., triphenylene group, Comparative Example 4) in a non-bulky structure (e.g., phenyl group, biphenyl group, naphthyl group, anthracenyl group, phenanthrenyl group), and thus, electron mobility is increased, and it was confirmed that the organic light-emitting device including the organic compound represented by the chemical formula 1 of the present invention has a lower driving voltage, higher efficiency, and significantly increased lifespan than Comparative Examples 1 to 4. And, when Ar is a heteroaryl group having 1 to 30 carbon atoms, the electron affinity is high, so the LUMO energy level is lowered, the energy gap is reduced, and thus, it is possible to confirm that the organic light-emitting device including the organic compound represented by the chemical formula 1 of the present invention has a lower driving voltage, higher efficiency, and a significantly increased lifespan than Comparative Examples 1 to 4, as it has excellent electron transport ability.

[0219]

[0220] [Examples 113 to 121, Comparative Examples 5 to 10]

[0221] The n-type charge generation layer (n-CGL) of Example 1 includes an n-type charge generation layer compound and an alkali metal. An organic light-emitting device including compounds 708, 657, and 660 as an n-type charge generation layer compound and Li as an alkali metal was manufactured by changing the weight of the alkali metal relative to 100 wt% of the n-type charge generation layer compound, and the mixing ratio thereof was as shown in Table 5 below. Except for the mixing ratio thereof, each organic light-emitting device was manufactured under the same conditions as in Example 1.

[0222] [Experimental Example 3] Evaluation of device performance according to the amount of n-type dopant added.

[0223] Organic light-emitting devices of Examples 113 to 121 and Comparative Examples 5 to 10 were manufactured in the same manner as in Example 1, except that the amounts of Li, an n-type dopant added to Compound 708 used as an n-type host in the n-type charge generation layer of Example 51, Compound 657 used as an n-type host in the n-type charge generation layer of Example 48, and Compound 660 used as an n-type host in the n-type charge generation layer of Example 49, were changed as shown in Table 5 below. The amounts of the n-type dopant added in Table 5 below are based on the total weight of Compounds 708, 657, and 660 being 100 wt%.

[0224] As in Experimental Example 2 above, the driving voltage, efficiency (Cd / A), and lifespan (LT95) of the organic light-emitting devices of Examples 113 to 121 and Comparative Examples 5 to 10 were measured, respectively, and the measurement results are shown in Table 5 below.

[0225]

[0226] As confirmed in Table 5 above, when the n-type dopant Li is added in an amount of 0.5 to 5 wt% relative to 100 wt% of the n-type host (compounds 708, 657, 660), it can be confirmed that the organic light-emitting device exhibits excellent characteristics. The n-type dopant Li has sufficient electrons, and even when added in excess of 5 wt% to the n-type host compound, the total electron amount remains the same, so no further improvement effect could be expected. In addition, when the n-type dopant is added in excessive amounts, it can cause leakage current and short-circuiting in the organic light-emitting device, and rather, it results in increasing the voltage of the organic light-emitting device and reducing the efficiency and lifespan.

[0227] 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. An organic compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X is oxygen (O) or sulfur (S), n1 is an integer from 0 to 3, n2, n3 and n4 are integers from 0 to 2, n5 is an integer from 0 to 4, L1 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroarylene group having 1 to 30 carbon atoms, Ar is a substituted or unsubstituted aryl group having 6 to 17 carbon atoms or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, R1, R2, R3, R4 and R5 are the same or different from each other and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, L1, Up, R1, R2, R3, R4및 R5의 치환기는 각각 독립적으로 중수소, 탄소수 1 내지 10의 알킬기, 탄소수 6 내지 30의 아릴기 및 탄소수 1 내지 30의 헤테로아릴기로 이루어진 군으로부터 선택된 1종 이상이며, 복수 개의 치환기로 치환되는 경우 이들은 서로 동일하거나 상이하다.

2. In paragraph 1, The above chemical formula 1 is an organic compound represented by any one of the following chemical formulas 2 to 4: In the above chemical formulas 2 to 4, X, n1, n2, n3, n4 and n5 are as defined in the above chemical formula 1, Ar, R1, R 2, R3, R4 and R5 and their substituents are as defined in the above chemical formula 1, n6, n7, n 8, n9 and n 10 is an integer from 0 to 4, R6, R7, R8, R9 and R 10 is selected from the group consisting of hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, R6, R7, R8, R9 and R 10 The substituents are each independently at least one selected from the group consisting of deuterium, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 1 to 30 carbon atoms, and when substituted with multiple substituents, they are the same or different from each other.

3. In paragraph 1 or 2, The above chemical formula 1 is an organic compound represented by any one of the following chemical formulas 2-1 to 2-12, 3-1 to 3-12, and 4-1 to 4-4: In the chemical formulas 2-1 to 2-12, 3-1 to 3-12, and 4-1 to 4-4, X, n1, n2, n3, n4 and n5 are as defined in the above chemical formula 1, Ar, R1, R 2, R3, R4 and R5 and their substituents are as defined in the above chemical formula 1, n6, n7, n 8, n9 and n 10 is as defined in the above chemical formulas 2 to 4, R6, R7, R8, R9 and R 10 And its substituents are as defined in the above chemical formulas 2 to 4.

4. Bipolar; A cathode facing the anode; and N different light emitting stacks are included between the anode and cathode, wherein N is an integer greater than or equal to 2, N-1 n-type charge generation layers and N-1 p-type charge generation layers are arranged between the N different light-emitting stacks, An organic light-emitting device, wherein at least one of the n-type charge generation layers comprises a compound represented by the chemical formula 1 according to claim 1.

5. In paragraph 4, The above n-type charge generation layer is formed by adding an n-type dopant material to an n-type host material, An organic light-emitting device, wherein the n-type host material is a compound represented by the chemical formula 1.

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