Organic light-emitting device

Abstract

The present disclosure relates to a tandem-type organic light-emitting device comprising a plurality of light-emitting layers and, more particularly, to a tandem-type organic light-emitting device that exhibits low driving voltage, high efficiency, and long lifetime through a combination of an N-type charge generation layer and adjacent layers thereof.

Description

organic light-emitting diode

[0001] The present invention relates to a tandem type organic light emitting device including a plurality of light emitting layers.

[0002] The technology of organic light emitting devices (OLEDs), one of the currently widely used flat panel display devices, is developing rapidly.

[0003] In general, an organic light-emitting device has an organic thin film layer including a light-emitting layer formed between an anode (hole injection electrode) and a cathode (electron injection electrode), and has a principle of emitting light when holes injected from the anode and electrons injected from the cathode pair up in the light-emitting layer and then disappear.

[0004] More specifically, the organic light-emitting device is configured to include an organic thin film layer formed between an anode and a cathode, and the organic thin film layer may be configured to include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer sequentially laminated on the anode, and holes injected from the anode and electrons injected from the cathode combine in the light-emitting layer to form excitons, which enter an unstable energy state (excited state) and then return to a stable ground state to emit light.

[0005] In the development of organic light-emitting devices, high efficiency, long lifespan, color purity, color stability according to changes in current and voltage, and ease of device manufacturing are important, so research and development are in progress according to each method. The structure of organic light-emitting devices can be broadly divided into a single-layer light-emitting structure with one light-emitting layer and a multilayer light-emitting structure with two or more light-emitting layers. Among these, a tandem structure of a multilayer light-emitting structure that stacks two or more light-emitting layers is mainly adopted for organic light-emitting devices with long lifespan.

[0006] Meanwhile, an organic light-emitting device with a tandem structure such as this is provided with a charge generation layer (CGL) between the light-emitting layers to double the current efficiency generated in the light-emitting layer and to facilitate charge distribution. This charge generation layer is a layer that generates charges, that is, electrons and holes, and performs the role of preventing an increase in the driving voltage by doubling the current efficiency generated in the light-emitting layer and facilitating charge distribution. This charge generation layer is generally composed of a P-type charge generation layer and an N-type charge generation layer.

[0007] In such a charge generation layer, if the charge transport does not occur smoothly due to the difference in energy level or current leakage occurs, the amount of electrons transported to the other light-emitting layer decreases, which not only causes the driving voltage to gradually increase but also has a negative impact on the lifespan, etc. Therefore, as the development of tandem devices with high performance such as low voltage, high efficiency, and long lifespan is increasingly demanded, the development of charge generation layers to match this is also necessary. Furthermore, since the combination of the charge generation layer and its adjacent layers has a significant effect on the device performance, finding the optimal combination is also important.

[0008] The purpose of the present invention is to reduce the driving voltage and improve the efficiency and lifespan of a tandem organic light-emitting device comprising a plurality of light-emitting layers by optimizing the combination of compounds included in adjacent layers. The above and additional tasks are described in detail below.

[0009] In order to solve the above problems, the present invention,

[0010] First electrode and second electrode;

[0011] A plurality of light-emitting layers positioned between the first electrode and the second electrode; and

[0012] A charge generation layer is included, each of which is positioned at least one between two adjacent light-emitting layers;

[0013] In a tandem organic light-emitting device, at least one of the charge generation layers includes an N-type charge generation layer,

[0014] At least one of the above N-type charge generation layers comprises a first compound represented by the following chemical formula 1,

[0015] At least one of the organic layers of the electron transport region adjacent to the N-type charge generation layer includes a second compound represented by the following chemical formula 2:

[0016] <Chemical Formula 1>

[0017]

[0018] In the above chemical formula 1,

[0019] R1 and R2 are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted sulfide group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, and a substituted or unsubstituted fused ring group, or adjacent ones may or may not combine with each other to form a substituted or unsubstituted ring,

[0020] However, either one of the above R1 and either one of the R2 is a bonding position that is connected to each other by a single bond,

[0021] <Chemical Formula 2>

[0022]

[0023] In the above chemical formula 2,

[0024] X is O or S,

[0025] R10 is each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted sulfide group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, and a substituted or unsubstituted fused ring group, or adjacent ones may or may not combine with each other to form a substituted or unsubstituted ring,

[0026] However, the above chemical formula 2 includes a substituted or unsubstituted triazine group.

[0027] The present invention relates to a tandem organic light-emitting device comprising a plurality of light-emitting layers, wherein the performance of the organic light-emitting device, such as low voltage, high efficiency, and long life, can be improved through optimization of the combination of compounds included in the organic layer of the N-type charge-generation layer and the adjacent electron-transport region. Furthermore, further improved performance can be realized through additional combination with the P-type charge-generation layer. The above effects and additional effects are described in detail below.

[0028] FIG. 1 is a schematic cross-sectional view of a tandem organic light-emitting device according to an embodiment of the present invention.

[0029] FIG. 2 is a schematic cross-sectional view of a tandem organic light-emitting device according to another embodiment of the present invention.

[0030] ** Explanation of symbols **

[0031] 1000, 2000: Tandem organic light-emitting diode

[0032] 100: First electrode

[0033] 200: Second electrode

[0034] 300: Emissive layer

[0035] 310: First light-emitting layer

[0036] 320: Second light-emitting layer

[0037] 400: Charge generation layer

[0038] 410: N-type charge generation layer

[0039] 420: P-type charge generation layer

[0040] 510: Hole injection layer

[0041] 520,530: Hole transport layer

[0042] 610,640: Hole-blocking layer (hole-blocking layer or hole-blocking layer)

[0043] 620: Electron injection layer

[0044] 630,650: Electron transport layer

[0045] In describing the present invention, if it is determined that a detailed description of a related known configuration or function may obscure the gist of the present invention, the detailed description will be omitted.

[0046] In this specification, when it is said that a part “includes” a certain component, this does not mean that other components are excluded, but rather that other components may be included, unless otherwise specifically stated.

[0047] In this specification, when it is said that a member is located 'on' another member, this includes not only cases where a member is in contact with another member, but also cases where another member exists between the two members.

[0048] When describing components of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used. These terms are only intended to distinguish the components from other components, and the nature, order, or sequence of the components are not limited by the terms. When it is described that a component is "connected," "coupled," or "connected" to another component, it should be understood that the component may be directly connected or connected to the other component, but another component may also be "connected," "coupled," or "connected" between each component.

[0049] In this specification, examples of substituents are described below, but are not limited thereto.

[0050] As used herein, the term "substitution" refers to the replacement of a hydrogen atom bonded to a carbon atom of a compound with another substituent. The position of substitution is not particularly limited as long as it is a position where substitution is possible, and when substitution is made with two or more substituents, the substituents may be the same or different.

[0051] In this specification, the term 'substituted or unsubstituted' means that it is substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, nitro, nitrile, alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, alkoxy, sulfide, aryloxy, heteroaryloxy, thio, amine, silyl, phosphine oxide, aryl, and heteroaryl groups, or is substituted with a substituent in which two or more substituents selected from the above group are connected, or has no substituents, and the selected substituents may or may not form a ring by combining with each other. An example of a substituent in which two or more substituents are connected is a biphenyl group. That is, a biphenyl group may correspond to an aryl group and at the same time correspond to a substituent having two phenyl groups connected, and at the same time correspond to an aryl group having one phenyl group substituted.

[0052] In the present specification, the alkyl group may be a straight or branched chain having 1 to 60 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, Examples thereof include, but are not limited to, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl. Specifically, the alkyl group may have 1 to 30 carbon atoms, and more specifically, 1 to 20 carbon atoms.

[0053] In the present specification, the alkenyl group may be a straight or branched chain having 2 to 60 carbon atoms, and specific examples thereof include, but are not limited to, a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 3-methyl-1-butenyl group, a 1,3-butadienyl group, an allyl group, a 1-phenylvinyl-1-yl group, a 2-phenylvinyl-1-yl group, a 2,2-diphenylvinyl-1-yl group, a 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, a 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, a stilbenyl group, and a styrenyl group. Specifically, the number of carbon atoms in the alkenyl group may be 2 to 30, and more specifically, 2 to 20.

[0054] In the present specification, the alkynyl group may be a straight or branched chain having 2 to 60 carbon atoms. Specifically, the alkynyl group may have 2 to 30 carbon atoms, and more specifically, 2 to 20 carbon atoms.

[0055] In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain having 1 to 60 carbon atoms, and specific examples thereof include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. Specifically, the alkoxy group may have 1 to 30 carbon atoms, and more specifically, 1 to 20 carbon atoms.

[0056] In the present specification, the cycloalkyl group may be monocyclic or polycyclic having 3 to 60 carbon atoms, and specific examples thereof include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl. Specifically, the cycloalkyl group may have 3 to 30 carbon atoms, and more specifically, 3 to 20 carbon atoms.

[0057] In the present specification, a heterocycloalkyl group is a group that contains at least one non-carbon atom, i.e., a heteroatom, and specifically, may be a cycloalkyl group that contains at least one heteroatom selected from the group consisting of O, N, S, Se, etc., and may be a monocyclic or polycyclic group having 2 to 60 carbon atoms. Specifically, the heterocycloalkyl group may have 2 to 30 carbon atoms, and more specifically, may have 2 to 20 carbon atoms.

[0058] In the present specification, a sulfide group includes S and may have 1 to 60 carbon atoms. Specific examples include, but are not limited to, an alkyl sulfide group such as a dimethyl sulfide group, an aryl sulfide group such as diphenyl sulfide, and a heteroaryl sulfide group substituted with a heteroaryl group. Specifically, the sulfide group may have 1 to 30 carbon atoms, and more specifically, 1 to 20 carbon atoms.

[0059] In the present specification, the aryloxy group may be a substituent that contains O, and the O atom may be directly connected as a radical, and may have 6 to 60 carbon atoms. Specific examples include phenoxy groups, naphthoxy groups, biphenoxy groups, etc., which are oxy groups substituted with aryl groups, but are not limited thereto. The heteroaryloxy group is an oxy group substituted with heteroaryl groups, and may have 2 to 60 carbon atoms. Specifically, the aryloxy group may have 6 to 30 carbon atoms, and more specifically, may have 6 to 20 carbon atoms.

[0060] In the present specification, the thio group includes S and may have 1 to 60 carbon atoms. Specific examples include, but are not limited to, alkylthio groups such as methylthio, ethylthio, butylthio, pentylthio, and hexylthio, arylthio groups such as phenylthio, and naphthylthio, and heteroarylthio groups substituted with heteroaryl groups. Specifically, the thio group may have 1 to 30 carbon atoms, and more specifically, 1 to 20 carbon atoms.

[0061] In the present specification, the silyl group may be a substituent containing Si, and the Si atom may be directly connected as a radical, and may have 1 to 60 carbon atoms. Specific examples thereof include, but are not limited to, alkylsilyl groups such as trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, and propyldimethylsilyl groups, arylsilyl groups such as triphenylsilyl, diphenylsilyl, and phenylsilyl groups, and heteroarylsilyl groups substituted with heteroaryl groups. Specifically, the silyl group may have 1 to 30 carbon atoms, and more specifically, 1 to 20 carbon atoms.

[0062] In the present specification, the phosphine oxide group includes P=O and may have 1 to 60 carbon atoms. Specific examples include, but are not limited to, an alkylphosphine oxide group such as a dimethylphosphine oxide group, an arylphosphine oxide group such as a diphenylphosphine oxide group and a dinaphthylphosphine oxide group, and a heteroarylphosphine oxide group substituted with a heteroaryl group. Specifically, the phosphine oxide group may have 1 to 30 carbon atoms, and more specifically, 1 to 20 carbon atoms.

[0063] In the present specification, the aryl group may be monocyclic or polycyclic having 6 to 60 carbon atoms. In the case of a monocyclic aryl group, specific examples thereof include a phenyl group, but are not limited thereto. In the case of a polycyclic aryl group, specific examples thereof include a biphenyl group, a terphenyl group, a naphthyl group, anthracenyl group, a phenanthrenyl group, a triphenylenyl group, a pyrenyl group, a fluorenyl group, and the like, but are not limited thereto. Specifically, the aryl group may have 6 to 50 carbon atoms, and more specifically, 6 to 30 carbon atoms.

[0064] In the present specification, a heteroaryl group includes at least one non-carbon atom, i.e., a heteroatom, and may specifically include at least one heteroatom selected from the group consisting of O, N, S, and Se, and may be a monocyclic or polycyclic group having 2 to 60 carbon atoms. Specific examples include a thiophenyl group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridinyl group, a bipyridinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrazinyl group, a quinolinyl group, a quinazolyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, a pyridoindolyl group, a benzothienopyrimidyl group, an indenocarbazolyl group, an isoquinolinyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophenyl group, Examples thereof include, but are not limited to, a dibenzothiophenyl group, a benzofuranyl group, a phenanthridinyl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group. Specifically, the heteroaryl group may have 2 to 50 carbon atoms, and more specifically, 2 to 30 carbon atoms.

[0065] In the present specification, the amine group may be selected from the group consisting of -NH2, an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group.

[0066] In this specification, an arylene group refers to a divalent aryl group having two bonding positions to an aryl group, and a heteroarylene group also refers to a divalent heteroaryl group having two bonding positions to a heteroaryl group. The descriptions of the aryl group and heteroaryl group described above can be applied to these groups, except that they are each divalent groups.

[0067] In the present specification, the fused ring group includes a fused ring group in which an aryl group and a cycloalkyl group are fused, a fused ring group in which a heteroaryl group and a cycloalkyl group are fused, a fused ring group in which an aryl group and a heterocycloalkyl group are fused, or a fused ring group in which a heteroaryl group and a heterocycloalkyl group are fused. According to one embodiment, the tetralin group represented by the structural formula below may correspond to one of the fused ring groups in which an aryl group and a cycloalkyl group are fused, and benzo-1,4-dioxane may correspond to one of the fused ring groups in which an aryl group and a heterocycloalkyl group are fused.

[0068]

[0069] In the chemical formula or structural formula in this specification, * or indicates the binding position.

[0070] In this specification, identical symbols within a chemical formula or structural formula may be the same or different.

[0071] In this specification, when a range such as "C2~C50", "0 to 7", etc. is described, even if there is no special description, it can be reduced to various ranges within the described range and is considered to be described in this specification. For example, C2~C50 is considered to describe various reduction ranges such as C2~C50, C5~C50, C6~C30, C6~C20, C6~C15, C6~C10, C12~C30 together with C2~C50. Therefore, the description of numerical ranges in this specification may be reduced or corrected in the future.

[0072] Throughout this specification, the term interaction with a dopant may mean coordination of an organic compound with a dopant including an alkali metal, an alkaline earth metal, a rare earth metal, a lanthanum metal, etc. within an N-type charge generation layer, and in one embodiment, may include a case where an organic compound and a dopant combine to form a gap state.

[0073] Meanwhile, the various embodiments of the present invention may be combined with any other embodiments unless explicitly stated otherwise. Hereinafter, embodiments of the present invention and the resulting effects will be described.

[0074] The present invention relates to a tandem organic light-emitting device, which may refer to an organic light-emitting diode and a panel including the organic light-emitting diode, or may refer to an electronic device including the panel and a circuit. Here, for example, the electronic device may include a display device, a lighting device, a solar cell, a portable or mobile terminal (e.g., a smart phone, a tablet, a PDA, an electronic dictionary, a PMP, etc.), a navigation terminal, a game machine, various TVs, various computer monitors, etc., and is not limited thereto, and may be any type of device as long as it includes the above-described component(s).

[0075]

[0076] The present invention will be described in detail below.

[0077] The tandem organic light-emitting device of the present invention comprises a first electrode and a second electrode, a plurality of light-emitting layers positioned between the first electrode and the second electrode, and a charge generation layer positioned at at least one location between two adjacent light-emitting layers, wherein when at least one of the charge generation layers includes an N-type charge generation layer and a P-type charge generation layer, at least one of the N-type charge generation layers includes a pyridine-quinoline-based first compound, and at least one of the organic material layers of an electron transport region adjacent to the N-type charge generation layer includes a spirofluorenexanthene-triazine-based second compound.

[0078] FIG. 1 is a schematic cross-sectional view showing a tandem organic light-emitting device according to an embodiment of the present invention, and illustrates a 2-stack tandem organic light-emitting device having two light-emitting layers. However, the present invention is not limited thereto, and may be a tandem organic light-emitting device having a 3-stack structure having three light-emitting layers, a 4-stack structure having four light-emitting layers, or n or more light-emitting layers. In the case of a 2-stack structure having two light-emitting layers, there may be one charge generation layer, in the case of a 3-stack structure having three light-emitting layers, there may be two charge generation layers, and in the case of an n-stack structure having n light-emitting layers, there may be n-1 charge generation layers. In addition, when each of the n-1 charge generation layers includes an N-type charge generation layer, any one layer of the n-1 N-type charge generation layers may include the first compound, any two layers may include the first compound, and all of the n-1 layers may include the first compound.

[0079] As illustrated in FIG. 1, a tandem organic light-emitting device (1000) according to an embodiment of the present invention includes a first electrode (100), a second electrode (200), a plurality of light-emitting layers (300) positioned between the first electrode (100) and the second electrode (200), and a charge generation layer (400) positioned at at least one location between two adjacent light-emitting layers (310, 320), and at least one of the charge generation layers (400) may include an N-type charge generation layer (410) and a P-type charge generation layer (420). At this time, as illustrated in FIG. 1, the N-type charge generation layer (410) may be positioned closer to the first electrode (100), and the P-type charge generation layer (420) may be positioned closer to the second electrode (200).

[0080] The above first electrode (100) may be an anode that supplies holes, may be made of a material having a relatively large work function value, and may be made of a TCO such as ITO, IZO, ITZO, SnO, ZnO, ICO, and AZO according to one embodiment, but is not limited thereto and known materials may be applied.

[0081] The second electrode (200) may be a cathode that supplies electrons and is located on the front side of the display area, and may be made of a conductive material having a relatively small work function value. In one embodiment, the second electrode may be made of a material having good reflective properties, such as aluminum (Al), magnesium (Mg), calcium (Ca), silver (Ag), or an alloy or combination thereof, but is not limited thereto and known materials may be applied.

[0082] The above-described light-emitting layer (300) is a layer (EML) that emits light by the recombination of transferred electrons and holes, and may be formed of a material that can emit light in the visible light range by transporting and combining electrons and holes, respectively. A material with good quantum efficiency for fluorescence or phosphorescence may be preferred. Specifically, the light-emitting layer may include a host and a dopant, and may have a form in which the dopant is doped into the host. Known materials may be applied to the host and the dopant, respectively.

[0083] The above charge generation layer (400) is a layer (charge generation layer, CGL) located between each light-emitting layer in order to supply positive and negative charges to each light-emitting layer in a tandem structure, and may be configured to include an N-type charge generation layer (410, N-CGL) and a P-type charge generation layer (420, P-CGL), and may further include additional layers as needed. The N-type charge generation layer (410) serves to supply electrons to the light-emitting layer, and the P-type charge generation layer serves to supply holes to the light-emitting layer.

[0084] Meanwhile, a hole transport region that transports holes may exist in each of the plurality of light-emitting layers, and this hole transport region may be configured to include one or more organic layers. According to one embodiment, the hole transport region may be configured to include one or more of a hole injection layer (HIL) that injects holes, a hole transport layer (HTL) that transports holes, a layer that simultaneously injects and transports holes, and an electron blocking layer (EBL) that blocks electron transport, and may further include additional layers as needed.

[0085] Additionally, an electron transport region that transports electrons to each of the plurality of light-emitting layers may also exist, and this electron transport region may also be configured to include one or more organic layers. According to one embodiment, the electron transport region may be configured to include one or more of an electron injection layer (EIL) that injects electrons, an electron transport layer (ETL) that transports electrons, a layer that simultaneously injects and transports electrons, and a hole blocking layer (HBL, hole blocking layer or hole blocking layer) that blocks hole transport, and may further include additional layers as needed.

[0086] Specifically, in the case of a tandem organic light-emitting device having two light-emitting layers as shown in FIG. 1, it may be configured to include a first hole transport region that transports holes to a first light-emitting layer (310), a first electron transport region that transports electrons to the first light-emitting layer (310), a second hole transport region that transports holes to a second light-emitting layer (320), and a second electron transport region that transports electrons to the second light-emitting layer (320).

[0087] The above first hole transport region is located between the first electrode (100) and the first light-emitting layer (310) and may include a hole injection layer (510) that injects holes and a hole transport layer (520) that transports the injected holes, but is not necessarily limited thereto.

[0088] The above first electron transport region is located between the N-type charge generation layer (410) and the first light-emitting layer (310) and may be configured to include a hole-blocking layer (610) that transports electrons and blocks the movement of holes, but is not necessarily limited thereto. The hole-blocking layer (610) may also be an electron transport layer that transports electrons. That is, the first electron transport region may be configured only with the hole-blocking layer or only with the electron transport layer, but is not limited thereto and may be configured to include both the electron transport layer and the hole-blocking layer. Fig. 2 is a schematic cross-sectional view showing a tandem organic light-emitting device (2000) in which the first electron transport region includes a hole-blocking layer (610) and an electron transport layer (650). In other words, the electron transport region adjacent to the N-type charge generation layer (410) may be configured to include one or more organic layers selected from a hole-blocking layer and an electron transport layer, and the organic layer in direct contact with the N-type charge generation layer (410) may be a hole-blocking layer (610) as in FIG. 1, or an electron transport layer (650) as in FIG. 2, and is not limited thereto, and may be a layer that simultaneously injects and transports electrons.

[0089] The above second hole transport region is located between the P-type charge generation layer (420) and the second light-emitting layer (320) and may be configured to include a hole transport layer (530) that transports holes, but is not necessarily limited thereto.

[0090] The second electron transport region is located between the second electrode (200) and the second light-emitting layer (320) and may include an electron injection layer (620) that injects electrons and an electron transport layer (630) that transports the injected electrons, but is not necessarily limited thereto.

[0091] The tandem organic light-emitting device of the present invention may further include various known layers on the inner and / or outer sides of both electrodes in addition to the layers described above.

[0092] The present invention is characterized in that, in the above-described tandem organic light-emitting device, at least one of the N-type charge generation layers comprises a pyridine-quinoline-based first compound, and at the same time, at least one of the organic layers of an electron transport region adjacent to the N-type charge generation layer comprises a spirofluorenxanthene-triazine-based second compound. Specifically, the organic layer of the electron transport region adjacent to the N-type charge generation layer may be configured to include at least one of an electron transport layer and a hole blocking layer, and one, two, or both of these may include the second compound. According to one embodiment, the organic layer of the electron transport region in direct contact with the N-type charge generation layer may include the second compound, and in this case, the organic layer may be an electron transport layer or a hole blocking layer. Furthermore, according to one embodiment, when there is an electron transport layer positioned on the N-type charge generation layer and a hole blocking layer positioned on the electron transport layer, both the electron transport layer and the hole blocking layer may include the second compound.

[0093]

[0094] Below, the first pyridine-quinoline compound included in the N-type charge generation layer is described in detail.

[0095] The above first compound can be represented by the following chemical formula 1.

[0096] <Chemical Formula 1>

[0097]

[0098] In the above chemical formula 1,

[0099] R1 and R2 are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted sulfide group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, and a substituted or unsubstituted fused ring group, or adjacent ones may or may not combine with each other to form a substituted or unsubstituted ring, provided that any one of the R1 and any one of the R2 are connected to each other by a single bond. It becomes a connecting bonding position. The above R1 and R2 may be the same or different, and the R1s and R2s may also be the same or different.

[0100] Specifically, R1 and R2 are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a substituted or unsubstituted C1~C30 alkyl group, a substituted or unsubstituted C1~C30 alkenyl group, a substituted or unsubstituted C1~C30 alkynyl group, a substituted or unsubstituted C3~C30 cycloalkyl group, a substituted or unsubstituted C1~C30 heterocycloalkyl group, a substituted or unsubstituted C1~C30 alkoxy group, a substituted or unsubstituted C1~C30 sulfide group, a substituted or unsubstituted C6~C50 aryl group, a substituted or unsubstituted C2~C50 heteroaryl group, a substituted or unsubstituted C6~C30 aryloxy group, a substituted or unsubstituted C2~C30 heteroaryloxy group, a substituted or unsubstituted C1~C30 thio group, substituted Or it may be selected from the group consisting of an unsubstituted C1~C30 amine group, a substituted or unsubstituted C1~C30 silyl group, a substituted or unsubstituted C1~C30 phosphine oxide group and a substituted or unsubstituted C3~C30 fused ring group, and when substituted, the substituent is deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a substituted or unsubstituted C1~C10 alkyl group, a substituted or unsubstituted C1~C10 alkenyl group, a substituted or unsubstituted C1~C10 alkynyl group, a substituted or unsubstituted C3~C10 cycloalkyl group, a substituted or unsubstituted C1~C10 heterocycloalkyl group, a substituted or unsubstituted C1~C10 alkoxy group, a substituted or unsubstituted C1~C10 sulfide group, a substituted or unsubstituted C6~C20 aryl group, a substituted or unsubstituted It may be at least one selected from a C2~C20 heteroaryl group, a substituted or unsubstituted C6~C20 aryloxy group, a substituted or unsubstituted C2~C20 heteroaryloxy group, a substituted or unsubstituted C1~C20 thio group, a substituted or unsubstituted C1~C20 amine group, a substituted or unsubstituted C1~C20 silyl group, a substituted or unsubstituted C1~C20 phosphine oxide group, and a substituted or unsubstituted C3~C20 fused ring group.

[0101]

[0102] According to one embodiment of the present invention, the chemical formula 1 may be represented by the following chemical formula 1-1.

[0103] <Chemical Formula 1-1>

[0104]

[0105] In the above chemical formula 1-1,

[0106] R1 and R2 are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a substituted or unsubstituted C1~C30 alkyl group, a substituted or unsubstituted C6~C50 aryl group, or a substituted or unsubstituted C2~C50 heteroaryl group, and when substituted, the substituent may be at least one selected from deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a substituted or unsubstituted C1~C10 alkyl group, a substituted or unsubstituted C6~C20 aryl group, and a substituted or unsubstituted C2~C20 heteroaryl group, provided that at least one of R1 and R2 may not be hydrogen.

[0107] Specifically, the chemical formula 1-1 above can be represented by the following chemical formula 1-2 or 1-3. The following chemical formula 1-2 represents the case where R2 in the above chemical formula 1-1 is not hydrogen, and the following chemical formula 1-3 represents the case where R1 in the above chemical formula 1-1 is not hydrogen.

[0108] <Chemical Formula 1-2>

[0109]

[0110] <Chemical Formula 1-3>

[0111]

[0112] In the above chemical formulas 1-2 and 1-3,

[0113] R1 and R2 are the same as defined in the above chemical formula 1-1,

[0114] L1 is each independently a substituted or unsubstituted C6~C20 arylene group or a substituted or unsubstituted C2~C20 heteroarylene group,

[0115] Ar1 is each independently a substituted or unsubstituted C6~C30 aryl group or a substituted or unsubstituted C2~C30 heteroaryl group,

[0116] When substituted, the substituent may be at least one selected from among deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a substituted or unsubstituted C1~C10 alkyl group, a substituted or unsubstituted C6~C20 aryl group, and a substituted or unsubstituted C2~C20 heteroaryl group.

[0117] n can be an integer from 0 to 4, each independently.

[0118] More specifically, the above chemical formula 1-2 may be any one of the following chemical formulas 1-2-1 to 1-2-3. In this way, the pyridine group may be bonded to a position immediately next to the nitrogen (N) of the quinoline group.

[0119] <Chemical Formula 1-2-1>

[0120]

[0121] <Chemical Formula 1-2-2>

[0122]

[0123] <Chemical Formula 1-2-3>

[0124]

[0125] In the above chemical formulas 1-2-1 to 1-2-3,

[0126] R1, L1, Ar1 and n may be the same as defined in the above chemical formula 1-2.

[0127] More specifically, the chemical formula 1-2 may be any one of the following chemical formulas 1-2-1A to 1-2-1D.

[0128] <Chemical Formula 1-2-1A> <Chemical Formula 1-2-1B>

[0129]

[0130] <Chemical Formula 1-2-1C> <Chemical Formula 1-2-1D>

[0131]

[0132] In the above chemical formulas 1-2-1A to 1-2-1D,

[0133] R1, L1, Ar1 and n may be the same as defined in the above chemical formula 1-2.

[0134] More specifically, the chemical formula 1-2 may be any one of the following chemical formulas 1-2-2A to 1-2-2D.

[0135] <Chemical Formula 1-2-2A> <Chemical Formula 1-2-2B>

[0136]

[0137] <Chemical Formula 1-2-2C> <Chemical Formula 1-2-2D>

[0138]

[0139] In the above chemical formulas 1-2-2A to 1-2-2D,

[0140] R1, L1, Ar1 and n may be the same as defined in the above chemical formula 1-2.

[0141] More specifically, the chemical formula 1-2 may be any one of the following chemical formulas 1-2-3A to 1-2-3D.

[0142] <Chemical Formula 1-2-3A> <Chemical Formula 1-2-3B>

[0143]

[0144]

[0145] <Chemical Formula 1-2-3C> <Chemical Formula 1-2-3D>

[0146]

[0147] In the above chemical formulas 1-2-3A to 1-2-3D,

[0148] R1, L1, Ar1 and n may be the same as defined in the above chemical formula 1-2.

[0149] And the above chemical formula 1-3 can also be any one of the following chemical formulas 1-3-1 to 1-3-3. In this way, the pyridine group can be bonded to the position right next to the nitrogen (N) of the quinoline group.

[0150] <Chemical Formula 1-3-1>

[0151]

[0152] <Chemical Formula 1-3-2>

[0153]

[0154] <Chemical Formula 1-3-3>

[0155]

[0156] In the above chemical formulas 1-3-1 to 1-3-3,

[0157] R2, L1, Ar1 and n may be the same as defined in the above chemical formula 1-3.

[0158] More specifically, the above chemical formula 1-3 may be the following chemical formula 1-3-1A or 1-3-1B.

[0159] <Chemical Formula 1-3-1A> <Chemical Formula 1-3-1B>

[0160]

[0161] In the above chemical formula 1-3-1A or 1-3-1B,

[0162] R2, L1, Ar1 and n may be the same as defined in the above chemical formula 1-3.

[0163] More specifically, the above chemical formula 1-3 may be any one of the following chemical formulas 1-3-2A to 1-3-2D.

[0164] <Chemical Formula 1-3-2A> <Chemical Formula 1-3-2B>

[0165]

[0166] <Chemical Formula 1-3-2C> <Chemical Formula 1-3-2D>

[0167]

[0168] In the above chemical formulas 1-3-2A to 1-3-2D,

[0169] R2, L1, Ar1 and n may be the same as defined in the above chemical formula 1-3.

[0170] More specifically, the chemical formula 1-3 may be any one of the following chemical formulas 1-3-3A to 1-3-3D.

[0171] <Chemical Formula 1-3-3A> <Chemical Formula 1-3-3B>

[0172]

[0173] <Chemical Formula 1-3-3C> <Chemical Formula 1-3-3D>

[0174]

[0175] In the above chemical formulas 1-3-3A to 1-3-3D,

[0176] R2, L1, Ar1 and n may be the same as defined in the above chemical formula 1-3.

[0177] Meanwhile, in the chemical formulas mentioned above, R1 and R2 are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a substituted or unsubstituted methyl group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted anthracene group, a substituted or unsubstituted chrysene group, a substituted or unsubstituted benzophenanthrene group, a substituted or unsubstituted benzoanthracene group, a substituted or unsubstituted pyrene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted diphenylfluorene group, a substituted or unsubstituted dimethylfluorene group, a substituted or unsubstituted spirobifluorene group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted benzophenanthrene group, a substituted or unsubstituted benzoanthracene group, a substituted or unsubstituted pyrimidine ... An unsubstituted pyrazine group, a substituted or unsubstituted pyridazine group, a substituted or unsubstituted trizine group, a substituted or unsubstituted quinoline group, a substituted or unsubstituted isoquinoline group, a substituted or unsubstituted quinoxaline group, a substituted or unsubstituted phthalazine group, a substituted or unsubstituted cinnoline group, a substituted or unsubstituted 1,5-naphthyridine group, a substituted or unsubstituted 1,6-naphthyridine group, a substituted or unsubstituted 1,7-naphthyridine group, a substituted or unsubstituted 1,8-naphthyridine group, a substituted or unsubstituted 2,5-naphthyridine group, a substituted or unsubstituted 2,6-naphthyridine group, a substituted or unsubstituted 2,7-naphthyridine group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted It may be a benzoxazole group, a substituted or unsubstituted benzothiazole group, or a substituted or unsubstituted benzimidazole group, and when substituted, the substituent may be at least one selected from among deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a substituted or unsubstituted C1~C10 alkyl group, a substituted or unsubstituted C6~C20 aryl group, and a substituted or unsubstituted C2~C20 heteroaryl group.In one embodiment, it may be at least one of a deuterium group, a cyano group, a methyl group, a t-butyl group, a phenyl group, a naphthyl group, a biphenyl group, a pyridine group, a quinoline group, and an isoquinoline group, but is not particularly limited thereto.

[0178] In addition, in the chemical formulas mentioned above, L1 is each independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted chrysenylene group, a substituted or unsubstituted benzophenanthrenylene group, a substituted or unsubstituted benzoanthracenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted diphenylfluorenylene group, a substituted or unsubstituted dimethylfluorenylene group, a substituted or unsubstituted spirobifluorenylene group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted pyrimidinylene group, a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted pyridazinylene group, a substituted or unsubstituted pyridazinylene group, a substituted or unsubstituted trizinylene group, a substituted or unsubstituted quinolinylene group, A substituted or unsubstituted isoquinolinylene group, a substituted or unsubstituted quinazolilene group, a substituted or unsubstituted quinoxalylene group, a substituted or unsubstituted phthalazinylene group, a substituted or unsubstituted cinnolinylene group, a substituted or unsubstituted 1,5-naphthyridinylene group, a substituted or unsubstituted 1,6-naphthyridinylene group, a substituted or unsubstituted 1,7-naphthyridinylene group, a substituted or unsubstituted 1,8-naphthyridinylene group, a substituted or unsubstituted 2,5-naphthyridinylene group, a substituted or unsubstituted 2,6-naphthyridinylene group, a substituted or unsubstituted 2,7-naphthyridinylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted benzoxazolilene group, a substituted or unsubstituted It may be a benzothiazolylene group or a substituted or unsubstituted benzoimidazolilene group, and when substituted, the substituent may be at least one selected from among deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a substituted or unsubstituted C1~C10 alkyl group, a substituted or unsubstituted C6~C20 aryl group, and a substituted or unsubstituted C2~C20 heteroaryl group, and according to one embodiment, deuterium, a cyano group, a methyl group, a t-butyl group, a phenyl group, a naphthyl group, a biphenyl group, a pyridine group,It may be one or more of a quinoline group and an isoquinoline group, but is not particularly limited thereto.

[0179] Also, in the chemical formulas described above, n can be an integer from 0 to 3, and specifically, can be 0, 1, or 2. When n is 2 or more, multiple L1s can be the same or different from each other.

[0180] Meanwhile, in the chemical formulas mentioned above, Ar1 is each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted anthracene group, a substituted or unsubstituted chrysene group, a substituted or unsubstituted benzophenanthrene group, a substituted or unsubstituted benzoanthracene group, a substituted or unsubstituted pyrene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted diphenylfluorene group, a substituted or unsubstituted dimethylfluorene group, a substituted or unsubstituted spirobifluorene group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted pyrazine group, a substituted or unsubstituted pyridazine group, a substituted or unsubstituted trizine group, a substituted or unsubstituted quinoline group, a substituted or unsubstituted Isoquinoline group, substituted or unsubstituted quinazoline group, substituted or unsubstituted quinoxaline group, substituted or unsubstituted phthalazine group, substituted or unsubstituted cinnoline group, substituted or unsubstituted 1,5-naphthyridine group, substituted or unsubstituted 1,6-naphthyridine group, substituted or unsubstituted 1,7-naphthyridine group, substituted or unsubstituted 1,8-naphthyridine group, substituted or unsubstituted 2,5-naphthyridine group, substituted or unsubstituted 2,6-naphthyridine group, substituted or unsubstituted 2,7-naphthyridine group, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted benzoxazole group, substituted or unsubstituted benzothiazole group, substituted or unsubstituted benzimidazole group, substituted or unsubstituted It may be a 1,10-phenanthroline group, a substituted or unsubstituted benzoquinoline group, or a substituted or unsubstituted 4,5-diazaspirobifluorene group, and when substituted, the substituent may be at least one selected from among deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a substituted or unsubstituted C1~C10 alkyl group, a substituted or unsubstituted C6~C20 aryl group, and a substituted or unsubstituted C2~C20 heteroaryl group.Adjacent substituents may or may not combine with each other to form a substituted or unsubstituted ring.

[0181] According to one embodiment, the Ar1 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted trizine group, a substituted or unsubstituted quinoline group, a substituted or unsubstituted isoquinoline group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted 1,10-phenanthroline group, a substituted or unsubstituted 4,5-diazaspirobifluorene group, or a substituted or unsubstituted spirobifluorene group, and when substituted, the substituent is as described above, and according to one embodiment, one of deuterium, a halogen group, a cyano group, a methyl group, a t-butyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrene group, a pyridine group, a quinoline group, and an isoquinoline group. It may be composed of the above, but is not particularly limited thereto. Meanwhile, among the substituents that can be substituted for Ar1, adjacent ones can combine with each other to form a substituted or unsubstituted ring, and specifically, can form benzene or naphthyl. In one embodiment, when Ar1 is a dibenzofuran group in which two adjacent substituents are substituted, and the two adjacent substituents combine with each other to form a benzene ring, Ar1 can consequently be a naphthobenzofuran group.

[0182] According to one embodiment of the present invention, Ar1 may be independently one of the structural formulae Ar1-1 to Ar1-17 below, and in terms of a structure that allows for smoother coordination with an N-type dopant such as Li or Yb, it may be preferable to be one of the structural formulae Ar1-1, which is a substituted or unsubstituted 1,10-phenanthroline group, and the structural formulae Ar1-14 to Ar1-17, which are substituted or unsubstituted 4,5-diazaspirobifluorene groups.

[0183] [Ar1-1]

[0184]

[0185] [Ar1-2] [Ar1-3] [Ar1-4] [Ar1-5] [Ar1-6] [Ar1-7]

[0186]

[0187] [Ar1-8] [Ar1-9] [Ar1-10]

[0188]

[0189] [Ar1-11] [Ar1-12] [Ar1-13]

[0190]

[0191] [Ar1-14] [Ar1-15] [Ar1-16] [Ar1-17]

[0192]

[0193] In the above structural formulas Ar1-1 to Ar1-17,

[0194] R3 and R4 are each independently selected from hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a substituted or unsubstituted C1~C10 alkyl group, a substituted or unsubstituted C6~C20 aryl group, and a substituted or unsubstituted C2~C20 heteroaryl group, and * indicates a position bonded to L1. According to one embodiment, R3 may be independently composed of one or more selected from hydrogen, deuterium, a halogen group, a cyano group, a methyl group, a t-butyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrene group, a pyridine group, a quinoline group, and an isoquinoline group, but is not particularly limited thereto. Preferably, R3 may not be hydrogen, but may be a phenyl group in terms of structural stability and thermal stability. Additionally, according to one embodiment, R4 may independently be composed of one or more of a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrene group, a pyridine group, a quinoline group, and an isoquinoline group, but is not limited thereto.

[0195] Specifically, the above structural formula Ar1-1 may be the following structural formula Ar1-1-1.

[0196] [Ar1-1-1]

[0197]

[0198] In the above structural formula Ar1-1-1, R3 has the same definition as in the above structural formula Ar1-1.

[0199] According to one embodiment of the present invention, Ar1 may independently be any one of the following structural formulas.

[0200]

[0201]

[0202] According to one embodiment of the present invention, the first compound may be any one of compounds 1-1 to 1-588 below. The compounds below are merely examples and are not limiting.

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228] The first compound described so far is a compound with pyridine-quinoline as its main core, and when applied to an N-type charge-generation layer, it effectively improves the performance of the organic light-emitting device, such as the driving voltage, efficiency, and lifespan. Specifically, the unshared electron pairs of nitrogens (N) included in the first compound smoothly interact with dopants such as Li and Yb, thereby preventing the problem of the dopants from moving to the adjacent P-type charge-generation layer, thereby preventing a decrease in the efficiency and lifespan of the organic light-emitting device. In particular, the pyridine group is a strong electron-withdrawing group, and due to the strong electron-withdrawing effect, electron movement is increased, thereby further increasing the efficiency of the device. In addition, it is possible to improve the electron injection and transfer characteristics into the layer of the adjacent electron transport region, thereby reducing the driving voltage. Therefore, the tandem organic light-emitting device of the present invention, which includes the first compound as a host material of the N-type charge-generation layer, can realize low voltage, high efficiency, and long lifespan.

[0229] Meanwhile, the N-type charge generation layer of the tandem organic light-emitting device of the present invention may include an N-type dopant together with the first compound. Specifically, the N-type dopant may be a material containing a metal element, and specifically may include at least one of a metal, a metal compound, and an organic complex of a metal. Here, the metal element may be specifically one or more selected from lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), ytterbium (Yb), samarium (Sm), tin (Sn), copper (Cu), titanium (Ti), cadmium (Cd), mercury (Hg), lead (Pb), bismuth (Bi), zinc (Zn), iron (Fe), cobalt (Co), nickel (Ni), indium (In), gallium (Ga), thorium (Th), uranium (U), silver (Ag), aluminum (Al), gold (Au), molybdenum (Mo), niobium (Nb), palladium (Pd), platinum (Pt), and europium (Eu). According to one embodiment, the metal element may be an alkali metal such as lithium, an alkaline earth metal such as calcium, strontium, or a lanthanide metal such as ytterbium. Such an N-type dopant may be included in the form of being doped into the first compound, and at this time, the doping amount may be 0.1 to 20 wt% based on the weight of the first compound, and specifically, may be 0.5 to 15 wt%, but is not limited thereto and may vary depending on the type of the metal element.

[0230] Hereinafter, a second spirofluorene xanthene-triazine compound included in at least one organic layer of an electron transport region adjacent to an N-type charge generation layer is specifically described.

[0231] The above second compound can be represented by the following chemical formula 2.

[0232] <Chemical Formula 2>

[0233]

[0234] In the above chemical formula 2,

[0235] X is O or S,

[0236] R10 is each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted sulfide group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, and a substituted or unsubstituted fused ring group, or adjacent ones may or may not combine with each other to form a substituted or unsubstituted ring,

[0237] However, the above chemical formula 2 includes a substituted or unsubstituted triazine group. The R10s may be the same or different.

[0238] Specifically, R10 is each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a substituted or unsubstituted C1~C30 alkyl group, a substituted or unsubstituted C1~C30 alkenyl group, a substituted or unsubstituted C1~C30 alkynyl group, a substituted or unsubstituted C3~C30 cycloalkyl group, a substituted or unsubstituted C1~C30 heterocycloalkyl group, a substituted or unsubstituted C1~C30 alkoxy group, a substituted or unsubstituted C1~C30 sulfide group, a substituted or unsubstituted C6~C50 aryl group, a substituted or unsubstituted C2~C50 heteroaryl group, a substituted or unsubstituted C6~C30 aryloxy group, a substituted or unsubstituted C2~C30 heteroaryloxy group, a substituted or unsubstituted C1~C30 thio group, a substituted or It may be selected from the group consisting of an unsubstituted C1~C30 amine group, a substituted or unsubstituted C1~C30 silyl group, a substituted or unsubstituted C1~C30 phosphine oxide group, and a substituted or unsubstituted C3~C30 fused ring group, and when substituted, the substituent is deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a substituted or unsubstituted C1~C10 alkyl group, a substituted or unsubstituted C1~C10 alkenyl group, a substituted or unsubstituted C1~C10 alkynyl group, a substituted or unsubstituted C3~C10 cycloalkyl group, a substituted or unsubstituted C1~C10 heterocycloalkyl group, a substituted or unsubstituted C1~C10 alkoxy group, a substituted or unsubstituted C1~C10 sulfide group, a substituted or unsubstituted C6~C20 aryl group, a substituted or unsubstituted It may be at least one selected from a C2~C20 heteroaryl group, a substituted or unsubstituted C6~C20 aryloxy group, a substituted or unsubstituted C2~C20 heteroaryloxy group, a substituted or unsubstituted C1~C20 thio group, a substituted or unsubstituted C1~C20 amine group, a substituted or unsubstituted C1~C20 silyl group, a substituted or unsubstituted C1~C20 phosphine oxide group, and a substituted or unsubstituted C3~C20 fused ring group.

[0239] Adjacent R10s may combine with each other to form a substituted or unsubstituted ring, specifically benzene or naphthyl, and when the formed ring is substituted, the substituent may be the same as the definition of R10 above.

[0240] Specifically, the above chemical formula 2 may include a substituent represented by the following structural formula A.

[0241] [Structural formula A]

[0242]

[0243] In the above structural formula A,

[0244] Ar2 and Ar3 are each independently a substituted or unsubstituted C1~C30 alkyl group, a substituted or unsubstituted C1~C30 alkenyl group, a substituted or unsubstituted C1~C30 alkynyl group, a substituted or unsubstituted C3~C30 cycloalkyl group, a substituted or unsubstituted C1~C30 heterocycloalkyl group, a substituted or unsubstituted C1~C30 alkoxy group, a substituted or unsubstituted C1~C30 sulfide group, a substituted or unsubstituted C6~C50 aryl group, a substituted or unsubstituted C2~C50 heteroaryl group, a substituted or unsubstituted C6~C30 aryloxy group, a substituted or unsubstituted C2~C30 heteroaryloxy group, a substituted or unsubstituted C1~C30 thio group, a substituted or unsubstituted C1~C30 amine group, a substituted or unsubstituted It can be selected from the group consisting of a C1~C30 silyl group, a substituted or unsubstituted C1~C30 phosphine oxide group, and a substituted or unsubstituted C3~C30 fused ring group,

[0245] L2 may be independently a substituted or unsubstituted C6~C30 arylene group, a substituted or unsubstituted C2~C30 heteroarylene group, or a substituted or unsubstituted C2~C30 fused ring group,

[0246] m can be an integer from 0 to 4.

[0247] When substituted, the substituent is a deuterium, halogen group, cyano group, nitro group, nitrile group, substituted or unsubstituted C1~C10 alkyl group, substituted or unsubstituted C1~C10 alkenyl group, substituted or unsubstituted C1~C10 alkynyl group, substituted or unsubstituted C3~C10 cycloalkyl group, substituted or unsubstituted C1~C10 heterocycloalkyl group, substituted or unsubstituted C1~C10 alkoxy group, substituted or unsubstituted C1~C10 sulfide group, substituted or unsubstituted C6~C20 aryl group, substituted or unsubstituted C2~C20 heteroaryl group, substituted or unsubstituted C6~C20 aryloxy group, substituted or unsubstituted C2~C20 heteroaryloxy group, substituted or unsubstituted C1~C20 thio group, substituted or unsubstituted It may be at least one selected from a C1~C20 amine group, a substituted or unsubstituted C1~C20 silyl group, a substituted or unsubstituted C1~C20 phosphine oxide group, and a substituted or unsubstituted C3~C20 fused ring group.

[0248] According to one embodiment of the present invention, the chemical formula 2 may be one of the following chemical formulas 2-1 to 2-5.

[0249] <Chemical Formula 2-1> <Chemical Formula 2-2>

[0250]

[0251] <Chemical Formula 2-3> <Chemical Formula 2-4>

[0252]

[0253] <Chemical Formula 2-5>

[0254]

[0255] In the above chemical formulas 2-1 to 2-5,

[0256] X and R10 are the same as defined in the above chemical formula 2, but one of R10 in each chemical formula is the above structural formula A.

[0257] Specifically, the above chemical formula 2 may be the following chemical formula 2-1-1 or 2-1-2.

[0258] <Chemical Formula 2-1-1> <Chemical Formula 2-1-2>

[0259]

[0260] In the above chemical formulas 2-1-1 and 2-1-2,

[0261] X and R10 may be the same as defined in the above chemical formula 2, and Ar2, Ar3, L2 and m may be the same as defined in the above structural formula A.

[0262] More specifically, the above chemical formula 2 may be any one of the following chemical formulas 2-1-1A to 2-1-1D and 2-1-2A to 2-1-2D.

[0263] <Chemical Formula 2-1-1A> <Chemical Formula 2-1-1B>

[0264]

[0265] <Chemical Formula 2-1-1C> <Chemical Formula 2-1-1D>

[0266]

[0267] <Chemical Formula 2-1-2A> <Chemical Formula 2-1-2B>

[0268]

[0269] <Chemical Formula 2-1-2C> <Chemical Formula 2-1-2D>

[0270]

[0271] In the above chemical formulas 2-1-1A to 2-1-1D and 2-1-2A to 2-1-2D,

[0272] X and R10 may be the same as defined in the above chemical formula 2, and Ar2, Ar3, L2 and m may be the same as defined in the above structural formula A.

[0273] Meanwhile, in the chemical formulas mentioned above, R10 is each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a substituted or unsubstituted C1~C20 alkyl group, a substituted or unsubstituted C1~C20 cycloalkyl group, a substituted or unsubstituted C1~C20 heterocycloalkyl group, a substituted or unsubstituted C1~C20 alkoxy group, a substituted or unsubstituted C1~C20 sulfide group, a substituted or unsubstituted C6~C30 aryl group, a substituted or unsubstituted C2~C30 heteroaryl group, a substituted or unsubstituted C6~C20 aryloxy group, a substituted or unsubstituted C2~C20 heteroaryloxy group, a substituted or unsubstituted C1~C20 thio group, a substituted or unsubstituted C1~C20 silyl group, a substituted or unsubstituted C1~C20 It may be selected from the group consisting of a phosphine oxide group and a substituted or unsubstituted C3~C20 fused ring group, and when substituted, the substituent may be at least one selected from deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a methyl group, a t-butyl group, a methoxy group, -OCF3, -CF3, a trimethylsilyl group (TMS), a triphenylsilyl group, a phenyl group, a naphthyl group, a biphenyl group, a pyridine group, a quinoline group, and an isoquinoline group, but is not particularly limited thereto.

[0274] According to one embodiment, R10 is each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a substituted or unsubstituted methyl group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted methoxy group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted anthracene group, a substituted or unsubstituted chrysene group, a substituted or unsubstituted benzophenanthrene group, a substituted or unsubstituted benzoanthracene group, a substituted or unsubstituted pyrene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted diphenylfluorene group, a substituted or unsubstituted dimethylfluorene group, a substituted or unsubstituted spirobifluorene group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted Pyrimidine group, substituted or unsubstituted pyrazine group, substituted or unsubstituted pyridazine group, substituted or unsubstituted trizine group, substituted or unsubstituted quinoline group, substituted or unsubstituted isoquinoline group, substituted or unsubstituted quinazoline group, substituted or unsubstituted quinoxaline group, substituted or unsubstituted phthalazine group, substituted or unsubstituted cinnoline group, substituted or unsubstituted 1,5-naphthyridine group, substituted or unsubstituted 1,6-naphthyridine group, substituted or unsubstituted 1,7-naphthyridine group, substituted or unsubstituted 1,8-naphthyridine group, substituted or unsubstituted 2,5-naphthyridine group, substituted or unsubstituted 2,6-naphthyridine group, substituted or unsubstituted 2,7-naphthyridine group, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted It may be a dibenzothiophene group, a substituted or unsubstituted benzoxazole group, a substituted or unsubstituted benzothiazole group, or a substituted or unsubstituted benzimidazole group, and when substituted, the substituent is deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a methyl group, a t-butyl group, a methoxy group, -OCF3, -CF3, a trimethylsilyl group (TMS), a triphenylsilyl group, a phenyl group, a naphthyl group, a biphenyl group, a pyridine group,It may be at least one selected from a quinoline group and an isoquinoline group, but is not particularly limited thereto. According to a specific embodiment, R10 may be hydrogen; -F; -CF3; -OCF3; -CN; a phenyl group unsubstituted or substituted with at least one selected from -F, -CF3, -OCF3 and -CN; or a naphthyl group unsubstituted or substituted with at least one selected from -F, -CF3, -OCF3 and -CN.

[0275] Meanwhile, in the chemical formulas mentioned above, L2 is each independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted chrysenylene group, a substituted or unsubstituted benzophenanthrenylene group, a substituted or unsubstituted benzoanthracenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted diphenylfluorenylene group, a substituted or unsubstituted dimethylfluorenylene group, a substituted or unsubstituted spirobifluorenylene group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted pyrimidinylene group, a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted pyridazinylene group, a substituted or unsubstituted pyridazinylene group, a substituted or unsubstituted trizinylene group, a substituted or unsubstituted quinolinylene group, A substituted or unsubstituted isoquinolinylene group, a substituted or unsubstituted quinazolilene group, a substituted or unsubstituted quinoxalylene group, a substituted or unsubstituted phthalazinylene group, a substituted or unsubstituted cinnolinylene group, a substituted or unsubstituted 1,5-naphthyridinylene group, a substituted or unsubstituted 1,6-naphthyridinylene group, a substituted or unsubstituted 1,7-naphthyridinylene group, a substituted or unsubstituted 1,8-naphthyridinylene group, a substituted or unsubstituted 2,5-naphthyridinylene group, a substituted or unsubstituted 2,6-naphthyridinylene group, a substituted or unsubstituted 2,7-naphthyridinylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted benzofuranylene group, a substituted or unsubstituted A benzothiophenylene group, a substituted or unsubstituted furanylene group, a substituted or unsubstituted thiophenylene group, a substituted or unsubstituted benzoxazolyllene group, a substituted or unsubstituted benzothiazolylene group, a substituted or unsubstituted benzoimidazolyllene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted phenoxazinylene group, a substituted or unsubstituted phenothiazinylene group, a substituted or unsubstituted phenoxathynylene group, a substituted or unsubstituted phenazinylene group, a substituted or unsubstituted dibenzosiloylene group,It may be a substituted or unsubstituted indenocarbazolilene group or a substituted or unsubstituted benzocarbazolilene group, and when substituted, the substituent may be at least one selected from among deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a substituted or unsubstituted C1~C10 alkyl group, a substituted or unsubstituted C1~C10 alkoxy group, a substituted or unsubstituted C1~C20 silyl group, a substituted or unsubstituted C6~C20 aryl group, and a substituted or unsubstituted C2~C20 heteroaryl group, and according to one embodiment, deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a methyl group, a t-butyl group, a methoxy group, -OCF3, -CF3, a trimethylsilyl group (TMS), a triphenylsilyl group, a phenyl group, a naphthyl group, a biphenyl group, a pyridine group, a quinoline group, and It may be one or more selected from the isoquinoline group, but is not particularly limited thereto.

[0276] Meanwhile, in the chemical formulas described above, m can be an integer from 0 to 3, and specifically, can be 0, 1, or 2. When m is 2 or greater, multiple L2s can be the same or different from each other.

[0277] Meanwhile, in the chemical formulas described above, Ar2 and Ar3 may each independently be a substituted or unsubstituted C6~C30 aryl group, a substituted or unsubstituted C2~C30 heteroaryl group, a substituted or unsubstituted C1~C30 silyl group, or a substituted or unsubstituted C3~C30 fused ring group, and Ar2 and Ar3 may be the same or different.

[0278] Specifically, Ar2 and Ar3 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted anthracene group, a substituted or unsubstituted chrysene group, a substituted or unsubstituted benzophenanthrene group, a substituted or unsubstituted benzoanthracene group, a substituted or unsubstituted pyrene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted diphenylfluorene group, a substituted or unsubstituted dimethylfluorene group, a substituted or unsubstituted spirobifluorene group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted pyrazine group, a substituted or unsubstituted pyridazine group, a substituted or unsubstituted trizine group, a substituted or unsubstituted quinoline group, a substituted or unsubstituted isoquinoline group, A substituted or unsubstituted quinazoline group, a substituted or unsubstituted quinoxaline group, a substituted or unsubstituted phthalazine group, a substituted or unsubstituted cinnoline group, a substituted or unsubstituted 1,5-naphthyridine group, a substituted or unsubstituted 1,6-naphthyridine group, a substituted or unsubstituted 1,7-naphthyridine group, a substituted or unsubstituted 1,8-naphthyridine group, a substituted or unsubstituted 2,5-naphthyridine group, a substituted or unsubstituted 2,6-naphthyridine group, a substituted or unsubstituted 2,7-naphthyridine group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted benzofuran group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted furan group, a substituted or unsubstituted thiophene group, a substituted or unsubstituted benzoxazole group, a substituted or An unsubstituted benzothiazole group, a substituted or unsubstituted benzimidazole group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted benzocarbazole group, a substituted or unsubstituted phenoxazine group, a substituted or unsubstituted phenothiazine, a substituted or unsubstituted phenoxathine group, a substituted or unsubstituted phenazine group, a substituted or unsubstituted acridine group, a substituted or unsubstituted tetraphenylsilyl group,It may be a combination of at least one selected from a substituted or unsubstituted dimethylsilole group and a substituted or unsubstituted cyclopentabenzofuran group, and when substituted, the substituent may be at least one selected from a deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a substituted or unsubstituted C1~C10 alkyl group, a substituted or unsubstituted C1~C10 alkoxy group, a substituted or unsubstituted C6~C30 aryl group and a substituted or unsubstituted C2~C30 heteroaryl group, and according to one embodiment, a deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a methyl group, a t-butyl group, a methoxy group, -OCF3, -CF3, a trimethylsilyl group (TMS), a triphenylsilyl group, a tetraphenylsilyl group, a phenyl group, a naphthyl group, a biphenyl group, a pyridine group, a quinoline group and an isoquinoline group. There may be one or more of the following, but is not particularly limited to them:

[0279] According to one embodiment of the present invention, the second compound may include one or more substituents selected from -F, -CF3, -OCF3, and -CN, and specifically may include one or more -CN. More specifically, 1) at least one of R10 may include -CN, 2) the linker L2 may include -CN, or 3) at least one of Ar2 and Ar3 may include -CN.

[0280] According to one embodiment of the present invention, the second compound may be any one of compounds 2-1 to 2-828 below. The compounds below are merely examples and are not limiting.

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328] The second compound described so far is a compound with spirofluorenxanthene-triazine as its main core, which has excellent electron transport capability and can prevent excessive movement of holes. Therefore, when applied to organic layers in the electron transport region, such as electron transport layers and hole blocking layers, it lowers the operating voltage of organic light-emitting devices and effectively improves efficiency and lifespan.

[0329] The tandem organic light-emitting device of the present invention uses the first compound described above as an N-type charge generation layer host material, and at the same time, the second compound described above is applied to one or more of the electron transport layer and the hole blocking layer, which are organic layers adjacent to the N-type charge generation layer, thereby further reducing the driving voltage and more effectively improving the efficiency and lifespan. When the N-type charge generation layer including the first compound and the organic layer of the electron transport region including the second compound are formed, the energy barrier between the two layers is optimized, thereby improving the electron injection and transfer characteristics, and as a result, the charge balance of the light-emitting layer in the stack is optimized, thereby enabling improved performance such as efficiency and lifespan.

[0330] Meanwhile, in the tandem organic light-emitting device of the present invention, the P-type charge generation layer adjacent to the N-type charge generation layer including the first compound may include a third amine compound.

[0331] Specifically, the third compound can be represented by the following chemical formula 3.

[0332] <Chemical Formula 3>

[0333]

[0334] In the above chemical formula 3,

[0335] L3 to L5 may each independently be a substituted or unsubstituted C6~C30 arylene group, a substituted or unsubstituted C2~C30 heteroarylene group, or a substituted or unsubstituted C2~C30 fused ring group,

[0336] Ar4 to Ar6 are each independently a substituted or unsubstituted C1~C30 alkyl group, a substituted or unsubstituted C1~C30 alkenyl group, a substituted or unsubstituted C1~C30 alkynyl group, a substituted or unsubstituted C3~C30 cycloalkyl group, a substituted or unsubstituted C1~C30 heterocycloalkyl group, a substituted or unsubstituted C1~C30 alkoxy group, a substituted or unsubstituted C1~C30 sulfide group, a substituted or unsubstituted C6~C50 aryl group, a substituted or unsubstituted C2~C50 heteroaryl group, a substituted or unsubstituted C6~C30 aryloxy group, a substituted or unsubstituted C2~C30 heteroaryloxy group, a substituted or unsubstituted C1~C30 thio group, a substituted or unsubstituted C1~C30 amine group, a substituted or unsubstituted It can be selected from the group consisting of a C1~C30 silyl group, a substituted or unsubstituted C1~C30 phosphine oxide group, and a substituted or unsubstituted C3~C30 fused ring group,

[0337] o to q can each independently be an integer from 0 to 4.

[0338] According to one embodiment of the present invention, Ar4 to Ar6 may not all be amine groups.

[0339] According to one embodiment of the present invention, one, two, or all three of Ar4 to Ar6 may be a substituted or unsubstituted carbazole group, a substituted or unsubstituted dimethylfluorene group, a substituted or unsubstituted diphenylfluorene group, or a substituted or unsubstituted spirobifluorene group, and when two or more substituents are substituted, adjacent substituents may or may not combine with each other to form a ring.

[0340] According to one embodiment of the present invention, the chemical formula 3 may be one of the following chemical formulas 3-1 to 3-4.

[0341] <Chemical Formula 3-1>

[0342]

[0343] <Chemical Formula 3-2>

[0344]

[0345] <Chemical Formula 3-3>

[0346]

[0347] <Chemical Formula 3-4>

[0348]

[0349] In the above chemical formulas 3-1 to 3-4, Ar4, Ar6, L3 to L5 and o to q may be the same as defined in the above chemical formula 3,

[0350] R20 to R23 are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a substituted or unsubstituted C1~C10 alkyl group, a substituted or unsubstituted C1~C10 alkenyl group, a substituted or unsubstituted C1~C10 alkynyl group, a substituted or unsubstituted C3~C10 cycloalkyl group, a substituted or unsubstituted C1~C10 heterocycloalkyl group, a substituted or unsubstituted C1~C10 alkoxy group, a substituted or unsubstituted C1~C10 sulfide group, a substituted or unsubstituted C6~C20 aryl group, a substituted or unsubstituted C2~C20 heteroaryl group, a substituted or unsubstituted C6~C20 aryloxy group, a substituted or unsubstituted C2~C20 heteroaryloxy group, a substituted or unsubstituted C1~C20 thio group, It may be at least one selected from a substituted or unsubstituted C1~C20 silyl group, a substituted or unsubstituted C1~C20 phosphine oxide group, and a substituted or unsubstituted C3~C20 fused ring group, and adjacent ones may or may not be combined with each other to form a ring.

[0351] r can be an integer from 0 to 4, each independently.

[0352] Specifically, the chemical formula 3 may be one of the chemical formulas 3-5 to 3-10 below.

[0353] <Chemical Formula 3-5>

[0354]

[0355] <Chemical Formula 3-6>

[0356]

[0357] <Chemical Formula 3-7>

[0358]

[0359] <Chemical Formula 3-8>

[0360]

[0361] <Chemical Formula 3-9>

[0362]

[0363] <Chemical Formula 3-10>

[0364]

[0365] In the above chemical formulas 3-5 to 3-10, Ar4, L3 to L5 and o to q may have the same definitions as in the above chemical formula 3, and R20 to R23 and r may also have the same definitions as described above.

[0366] Meanwhile, in the chemical formulas mentioned above, Ar4 to Ar6 may each independently be selected from the group consisting of a substituted or unsubstituted C3~C30 cycloalkyl group, a substituted or unsubstituted C1~C30 heterocycloalkyl group, a substituted or unsubstituted C6~C50 aryl group, a substituted or unsubstituted C2~C50 heteroaryl group, a substituted or unsubstituted C1~C30 silyl group and a substituted or unsubstituted C3~C30 fused ring group, and when substituted, the substituent may be deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a substituted or unsubstituted C1~C10 alkyl group, a substituted or unsubstituted C1~C10 alkenyl group, a substituted or unsubstituted C1~C10 alkynyl group, a substituted or unsubstituted C3~C10 cycloalkyl group, a substituted or unsubstituted C1~C10 heterocycloalkyl group, a substituted or unsubstituted C1~C10 It may be at least one selected from an unsubstituted C1~C10 alkoxy group, a substituted or unsubstituted C1~C10 sulfide group, a substituted or unsubstituted C6~C20 aryl group, a substituted or unsubstituted C2~C20 heteroaryl group, a substituted or unsubstituted C6~C20 aryloxy group, a substituted or unsubstituted C2~C20 heteroaryloxy group, a substituted or unsubstituted C1~C20 thio group, a substituted or unsubstituted C1~C20 silyl group, a substituted or unsubstituted C1~C20 phosphine oxide group, and a substituted or unsubstituted C3~C20 fused ring group.

[0367] According to one embodiment, Ar4 to Ar6 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted anthracene group, a substituted or unsubstituted chrysene group, a substituted or unsubstituted benzophenanthrene group, a substituted or unsubstituted benzoanthracene group, a substituted or unsubstituted pyrene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted diphenylfluorene group, a substituted or unsubstituted dimethylfluorene group, a substituted or unsubstituted spirobifluorene group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted pyrazine group, a substituted or unsubstituted pyridazine group, a substituted or unsubstituted trizine group, a substituted or unsubstituted quinoline group, a substituted or unsubstituted Isoquinoline group, substituted or unsubstituted quinazoline group, substituted or unsubstituted quinoxaline group, substituted or unsubstituted phthalazine group, substituted or unsubstituted cinnoline group, substituted or unsubstituted 1,5-naphthyridine group, substituted or unsubstituted 1,6-naphthyridine group, substituted or unsubstituted 1,7-naphthyridine group, substituted or unsubstituted 1,8-naphthyridine group, substituted or unsubstituted 2,5-naphthyridine group, substituted or unsubstituted 2,6-naphthyridine group, substituted or unsubstituted 2,7-naphthyridine group, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted benzofuran group, substituted or unsubstituted benzothiophene group, substituted or unsubstituted furan group, substituted or unsubstituted thiophene group, substituted or unsubstituted A benzoxazole group, a substituted or unsubstituted benzothiazole group, a substituted or unsubstituted benzimidazole group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted benzocarbazole group, a substituted or unsubstituted phenoxazine group, a substituted or unsubstituted phenothiazine, a substituted or unsubstituted phenoxathine group, a substituted or unsubstituted phenazine group, a substituted or unsubstituted acridine group, a substituted or unsubstituted tetraphenylsilyl group,It may be a substituted or unsubstituted dimethylsilole group, a substituted or unsubstituted cyclopentabenzofuran group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted norbornene group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted tetralin group, a substituted or unsubstituted benzo-1,4-dioxane group, and when substituted, the substituent may be at least one selected from among deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a methyl group, a t-butyl group, a methoxy group, an adamantyl group, a norbornene group, a cyclohexyl group, a tetralin group, a benzo-1,4-dioxane group, -OCF3, -CF3, a trimethylsilyl group (TMS), a triphenylsilyl group, a tetraphenylsilyl group, a phenyl group, a naphthyl group, a biphenyl group, a pyridine group, a quinoline group, and an isoquinoline group, but in particular, It is not limited. According to a specific embodiment, in the chemical formulas 3-5 to 3-8, Ar4 may each independently be a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group.

[0368] Meanwhile, in the chemical formulas mentioned above, R20 is each independently deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a substituted or unsubstituted C1~C10 alkyl group, a substituted or unsubstituted C1~C10 alkenyl group, a substituted or unsubstituted C1~C10 alkynyl group, a substituted or unsubstituted C3~C10 cycloalkyl group, a substituted or unsubstituted C1~C10 heterocycloalkyl group, a substituted or unsubstituted C1~C10 alkoxy group, a substituted or unsubstituted C1~C10 sulfide group, a substituted or unsubstituted C6~C20 aryl group, a substituted or unsubstituted C2~C20 heteroaryl group, a substituted or unsubstituted C6~C20 aryloxy group, a substituted or unsubstituted C2~C20 heteroaryloxy group, a substituted or unsubstituted C1~C20 thio group, It may be a substituted or unsubstituted C1~C20 silyl group, a substituted or unsubstituted C1~C20 phosphine oxide group, or a substituted or unsubstituted C3~C20 fused ring group, and according to one embodiment, it may be at least one selected from deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a methyl group, a t-butyl group, a methoxy group, an adamantyl group, a norbornene group, a cyclohexyl group, a tetraline group, a benzo-1,4-dioxane group, -OCF3, -CF3, a trimethylsilyl group (TMS), a triphenylsilyl group, a tetraphenylsilyl group, a phenyl group, a naphthyl group, a biphenyl group, a pyridine group, a quinoline group, and an isoquinoline group, but is not particularly limited thereto. These R20s may be the same or different.

[0369] Meanwhile, in the chemical formulas described above, R21 may independently be a substituted or unsubstituted C6~C20 aryl group or a substituted or unsubstituted C2~C20 heteroaryl group, and specifically may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted biphenyl group, but is not particularly limited thereto.

[0370] In the chemical formulas described above, R22 and R23 can each independently be a substituted or unsubstituted C1~C10 alkyl group, a substituted or unsubstituted C6~C20 aryl group, or a substituted or unsubstituted C2~C20 heteroaryl group, and R22s can be combined with each other to form a substituted or unsubstituted ring. According to a specific embodiment, R22 and R23 can each independently be a substituted or unsubstituted methyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group. In addition, R22s can be combined with each other to form a substituted or unsubstituted ring, and specifically, can form a substituted or unsubstituted fluorene ring, a substituted or unsubstituted adamantyl ring, etc., and when substituted, the substituent can be the same as the definition of R20 described above. R22s or R23s can be the same or different. In one embodiment, when R22 is bonded to each other to form a substituted or unsubstituted fluorene ring, the structure may be as follows. In the structural formula below, * indicates a position bonded to L3, L4, or L5.

[0371]

[0372] Meanwhile, in the chemical formulas described above, L4 to L6 may each independently be a substituted or unsubstituted C6~C20 arylene group or a substituted or unsubstituted C2~C20 heteroarylene group, and when substituted, the substituent may be at least one selected from deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a methyl group, a t-butyl group, a methoxy group, an adamantyl group, a norbornene group, a cyclohexyl group, a tetraline group, a benzo-1,4-dioxane group, -OCF3, -CF3, a trimethylsilyl group (TMS), a triphenylsilyl group, a tetraphenylsilyl group, a phenyl group, a naphthyl group, a biphenyl group, a pyridine group, a quinoline group, and an isoquinoline group, but is not particularly limited thereto. According to a specific embodiment, L4 to L6 may each independently be a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group.

[0373] Meanwhile, in the chemical formulas described above, o to r can each independently be an integer from 0 to 3, and specifically, can be 0, 1, or 2. When o, p, q, or r is 2 or more, multiple L3s, L4s, L5s, or R20s can be the same or different from each other.

[0374] According to one embodiment of the present invention, the third compound may be one of the chemical formulae 3-7 to 3-10, and in this way, two or all three of Ar4 to Ar6 may be substituted or unsubstituted fluorene groups, and specifically, may be a substituted or unsubstituted dimethylfluorene group, a substituted or unsubstituted diphenylfluorene group, or a substituted or unsubstituted spirobifluorene group.

[0375] According to one embodiment of the present invention, the third compound may be any one of compounds 3-1 to 3-112 below. The compounds below are merely examples and are not limiting.

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382] Meanwhile, the P-type charge generation layer of the tandem organic light-emitting device of the present invention may include a P-type dopant together with a third compound. The P-type dopant may be a radialene compound containing one or more, two or more, three or more, or four or more cyano groups, and may be included in a form doped into the third compound. According to a specific embodiment, the P-type dopant may be HAT-CN, TCNQ, NDP-9, F4-TCNQ, etc., but is not particularly limited thereto.

[0383] Hereinafter, the present invention will be described in more detail with synthetic examples, practical examples, and experimental examples. However, the following contents do not limit the scope of the present invention.

[0384] Synthesis of compounds

[0385] Synthesis Example 1. Synthesis of the first compound

[0386] Synthesis Example 1-1. Synthesis of Compound 1-3

[0387]

[0388] 2-(4-bromonaphthalen-1-yl)-1,10-phenanthroline (15.0 g, 38.93 mmol), 2-(pyridin-2-yl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (14.2 g, 42.83 mmol), potassium carbonate (16.1 g, 116.80 mmol), and tetrakis(triphenylphophine)palladium (2.2 g, 1.95 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 150 mL of 1,4-dioxane and 75 mL of water. After the reaction was complete, the mixture was cooled to room temperature, EtOH was added, the solid was filtered, and washed with EtOH and water. The solid was dissolved in dichlorobenzene, and then filtered under reduced pressure through silica gel and Celite to obtain the filtrate. The obtained filtrate was concentrated under reduced pressure and recrystallized in dichlorobenzene to obtain compound 1-3 (13.4 g, 67.4%).

[0389]

[0390] Synthetic Example 1-2. Synthesis of Compound 1-165

[0391]

[0392] 2-(4-bromophenyl)-1,10-phenanthroline (15.0 g, 44.75 mmol), 2-(pyridin-2-yl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (16.4 g, 49.22 mmol), potassium carbonate (18.6 g, 134.25 mmol), and tetrakis(triphenylphophine)palladium (2.6 g, 2.24 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 150 mL of 1,4-dioxane and 75 mL of water. After the reaction was completed, the mixture was cooled to room temperature, EtOH was added, the solid was filtered, and washed with EtOH and water. The solid was dissolved in dichlorobenzene, and then filtered under reduced pressure through silica gel and Celite to obtain the filtrate. The obtained filtrate was concentrated under reduced pressure and recrystallized from dichlorobenzene to obtain compound 1-165 (15.2 g, 73.8%).

[0393]

[0394] Synthetic Example 1-3. Synthesis of Compound 1-167

[0395] Synthesis of intermediate 1-1

[0396]

[0397] 2-chloro-9-phenyl-1,10-phenanthroline (15.0 g, 51.59 mmol), 2-(4-bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (16.1 g, 56.75 mmol), potassium carbonate (21.4 g, 154.77 mmol), and tetrakis(triphenylphophine)palladium (3.0 g, 2.58 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 150 mL of 1,4-dioxane and 75 mL of water. After the reaction was complete, the mixture was cooled to room temperature, EtOH was added, the solid was filtered, and washed with EtOH and water. The solid was dissolved in toluene, and then filtered under reduced pressure through silica gel and Celite to obtain a filtrate. The obtained filtrate was concentrated under reduced pressure and then recrystallized in toluene to obtain intermediate 1-1 (14.9 g, 70.2%).

[0398] Synthesis of compound 1-167

[0399]

[0400] Intermediate 1-1 (14.5 g, 35.25 mmol) and 2-(pyridin-2-yl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (12.9 g, 38.78 mmol), potassium carbonate (14.6 g, 105.76 mmol), and tetrakis(triphenylphophine)palladium (2.0 g, 1.76 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 145 mL of 1,4-dioxane and 70 mL of water. After the reaction was completed, the mixture was cooled to room temperature, EtOH was added, the solid was filtered, and washed with EtOH and water. The solid was dissolved in dichlorobenzene, and then filtered under reduced pressure through silica gel and Celite to obtain a filtrate. The obtained filtrate was concentrated under reduced pressure and recrystallized in dichlorobenzene to obtain compound 1-167 (13.1 g, 69.2%).

[0401]

[0402] Synthetic Example 1-4. Synthesis of Compound 1-172

[0403] Synthesis of intermediates 1-2

[0404]

[0405] 1-(6-bromopyridin-2-yl)ethan-1-one (20.0 g, 99.98 mmol), phenylboronic acid (13.4 g, 109.98 mmol), potassium carbonate (41.5 g, 299.94 mmol), and tetrakis(triphenylphophine)palladium (5.8 g, 5.00 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 200 mL of 1,4-dioxane and 100 mL of water. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was extracted with ethyl acetate and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was purified by column chromatography to obtain intermediate 1-2 (17.2 g, 87.2%).

[0406] Synthesis of intermediates 1-3

[0407]

[0408] Intermediate 1-2 (17.0 g, 89.19 mmol), 2-amino-6-bromonicotinaldehyde (22.5 g, 112.05 mmol), and 120 mL of toluene were added to a round-bottomed flask. Potassium hydroxide (14.5 g, 258.57 mmol) dissolved in 85 mL of ethanol was added dropwise, and the mixture was stirred at 80°C overnight. After the reaction was completed, the mixture was cooled to room temperature, methanol was added, filtered, and the solid was washed with methyl. The solid was dissolved in toluene, and the filtrate was filtered through silica gel and Celite under reduced pressure to obtain a filtrate. The filtrate was concentrated under reduced pressure and recrystallized from toluene to obtain intermediate 1-3 (15.3 g, 49.1%).

[0409] Synthesis of intermediates 1-4

[0410]

[0411] Intermediate 1-3 (15.0 g, 41.52 mmol), bis(pinacolato)diboron (12.7 g, 49.83 mmol), potassium acetate (12.2 g, 124.57 mmol), and [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1.0 g, 1.25 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 225 mL of 1,4-dioxane. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was extracted with ethyl acetate and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was dissolved in dichloromethane, filtered through silica gel and Celite under reduced pressure, and concentrated under reduced pressure to obtain intermediate 1-4 (14.7 g, 86.7%).

[0412] Synthesis of compound 1-172

[0413]

[0414] 2-(4-bromophenyl)-1,10-phenanthroline (10.0 g, 29.83 mmol), intermediate 1-4 (13.4 g, 32.82 mmol), potassium carbonate (12.4 g, 89.50 mmol), and tetrakis(triphenylphophine)palladium (1.7 g, 1.49 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 100 mL of 1,4-dioxane and 50 mL of water. After the reaction was completed, the mixture was cooled to room temperature, EtOH was added, the solid was filtered, and washed with EtOH and water. The solid was dissolved in dichlorobenzene, and the filtrate was filtered through silica gel and Celite under reduced pressure to obtain a filtrate. The obtained filtrate was concentrated under reduced pressure, and recrystallized from dichlorobenzene to obtain compound 1-172 (10.8 g, 67.5%).

[0415]

[0416] Synthetic Example 1-5. Synthesis of Compound 1-482

[0417] Synthesis of intermediates 1-5

[0418]

[0419] 2-Bromo-7-chloroquinoline (15.0 g, 61.86 mmol), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (14.0 g, 68.04 mmol), potassium carbonate (25.6 g, 185.57 mmol), and tetrakis(triphenylphophine)palladium (3.6 g, 3.09 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 150 mL of 1,4-dioxane and 75 mL of water. After the reaction was completed, the mixture was cooled to room temperature, EtOH was added, the solid was filtered, and washed with EtOH and water. The solid was dissolved in toluene, and then filtered under reduced pressure through silica gel and Celite to obtain the filtrate. The obtained filtrate was concentrated under reduced pressure and then recrystallized in toluene to obtain intermediate 1-5 (13.3 g, 89.3%).

[0420] Synthesis of intermediates 1-6

[0421]

[0422] 2-(4-chlorophenyl)-9-phenyl-1,10-phenanthroline (15.0 g, 40.89 mmol), bis(pinacolato)diboron (12.5 g, 49.07 mmol), potassium acetate (12.0 g, 122.67 mmol), and [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1.0 g, 1.23 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 225 mL of 1,4-dioxane. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was extracted with ethyl acetate and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was dissolved in dichloromethane, filtered under reduced pressure through silica gel and celite, and concentrated under reduced pressure to obtain intermediate 1-6 (14.2 g, 75.8%).

[0423] Synthesis of compound 1-482

[0424]

[0425] Intermediate 1-6 (14.0 g, 30.54 mmol), intermediate 1-5 (8.1 g, 33.60 mmol), potassium carbonate (12.7 g, 91.63 mmol), and tetrakis(triphenylphophine)palladium (1.8 g, 1.53 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 140 mL of 1,4-dioxane and 70 mL of water. After the reaction was completed, the mixture was cooled to room temperature, EtOH was added, the solid was filtered, and washed with EtOH and water. The solid was dissolved in dichlorobenzene, and the filtrate was filtered through silica gel and Celite under reduced pressure to obtain a filtrate. The obtained filtrate was concentrated under reduced pressure, and recrystallized from dichlorobenzene to obtain compound 1-482 (12.3 g, 75.0%).

[0426]

[0427] Synthetic Example 1-6. Synthesis of Compound 1-523

[0428] Synthesis of intermediates 1-7

[0429]

[0430] 7-Bromo-2-chloroquinoline (15.0 g, 61.86 mmol), 2-(4-chlorophenyl)-9-phenyl-1,10-phenanthroline (14.0 g, 68.04 mmol), potassium carbonate (25.6 g, 185.57 mmol), and tetrakis(triphenylphophine)palladium (3.6 g, 3.09 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 150 mL of 1,4-dioxane and 75 mL of water. After the reaction was completed, the mixture was cooled to room temperature, EtOH was added, the solid was filtered, and washed with EtOH and water. The solid was dissolved in toluene, and the filtrate was filtered through silica gel and Celite under reduced pressure to obtain a filtrate. The obtained filtrate was concentrated under reduced pressure, and recrystallized from toluene to obtain intermediate 1-7 (13.3 g, 89.3%).

[0431] Synthesis of compound 1-523

[0432]

[0433] Intermediate 1-6 (14.0 g, 30.54 mmol) and intermediate 1-7 (8.1 g, 33.60 mmol), potassium carbonate (12.7 g, 91.63 mmol), and tetrakis(triphenylphophine)palladium (1.8 g, 1.53 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 140 mL of 1,4-dioxane and 70 mL of water. After the reaction was completed, the mixture was cooled to room temperature, EtOH was added, the solid was filtered, and washed with EtOH and water. The solid was dissolved in dichlorobenzene, and the filtrate was filtered through silica gel and Celite under reduced pressure to obtain a filtrate. The obtained filtrate was concentrated under reduced pressure, and recrystallized from dichlorobenzene to obtain compound 1-523 (12.3 g, 75.0%).

[0434]

[0435] Synthetic Example 1-7. Synthesis of Compound 1-543

[0436] Synthesis of intermediates 1-8

[0437]

[0438] 2-Bromo-9-phenyl-1,10-phenanthroline (15.0 g, 44.75 mmol), (4-bromonaphthalen-1-yl)boronic acid (12.3 g, 49.22 mmol), potassium carbonate (18.6 g, 134.25 mmol), and tetrakis(triphenylphophine)palladium (2.6 g, 2.24 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 150 mL of 1,4-dioxane and 75 mL of water. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was extracted with ethyl acetate and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was purified by column chromatography to obtain intermediate 1-8 (12.7 g, 61.5%).

[0439] Synthesis of intermediates 1-9

[0440]

[0441] Intermediate 1-8 (12.5 g, 27.09 mmol), bis(pinacolato)diboron (8.3 g, 32.51 mmol), potassium acetate (8.0 g, 81.28 mmol), [1,11'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.7 g, 0.81 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 190 mL of 1,4-dioxane. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was extracted with ethyl acetate and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was dissolved in dichloromethane, filtered through silica gel and Celite under reduced pressure, and concentrated under reduced pressure to obtain intermediate 1-9 (12.0 g, 87.1%).

[0442] Synthesis of intermediates 1-10

[0443]

[0444] 2-Bromo-8-chloroquinoline (15.0 g, 61.86 mmol), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (14.0 g, 68.04 mmol), potassium carbonate (25.6 g, 185.57 mmol), and tetrakis(triphenylphophine)palladium (3.6 g, 3.09 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 150 mL of 1,4-dioxane and 75 mL of water. After the reaction was complete, the mixture was cooled to room temperature, EtOH was added, the solid was filtered, and washed with EtOH and water. The solid was dissolved in toluene, and then filtered under reduced pressure through silica gel and Celite to obtain the filtrate. The obtained filtrate was concentrated under reduced pressure and recrystallized in toluene to obtain intermediate 1-10 (11.4 g, 76.6%).

[0445] Synthesis of compound 1-543

[0446]

[0447] Intermediate 1-9 (11.5 g, 22.62 mmol), intermediate (6.0 g, 24.88 mmol), potassium carbonate (9.4 g, 67.86 mmol), and tetrakis(triphenylphophine)palladium (1.3 g, 1.13 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 115 mL of 1,4-dioxane and 60 mL of water. After the reaction was completed, the mixture was cooled to room temperature, EtOH was added, the solid was filtered, and washed with EtOH and water. The solid was dissolved in dichlorobenzene, and the filtrate was filtered through silica gel and Celite under reduced pressure to obtain a filtrate. The obtained filtrate was concentrated under reduced pressure, and recrystallized from dichlorobenzene to obtain compound 1-543 (8.5 g, 64.1%).

[0448]

[0449] Synthetic Example 1-8. Synthesis of Compound 1-560

[0450] Synthesis of intermediates 1-11

[0451]

[0452] 2-Bromo-5-chloroquinoline (15.0 g, 61.86 mmol), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (14.0 g, 68.04 mmol), potassium carbonate (25.6 g, 185.57 mmol), and tetrakis(triphenylphophine)palladium (3.6 g, 3.09 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 150 mL of 1,4-dioxane and 75 mL of water. After the reaction was completed, the mixture was cooled to room temperature, EtOH was added, the solid was filtered, and washed with EtOH and water. The solid was dissolved in toluene, and then filtered under reduced pressure through silica gel and Celite to obtain the filtrate. The obtained filtrate was concentrated under reduced pressure and recrystallized in toluene to obtain intermediate 1-11 (12.7 g, 85.3%).

[0453] Synthesis of compound 1-560

[0454]

[0455] Intermediate 1-6 (12.5 g, 27.27 mmol), intermediate 1-11 (7.2 g, 30.00 mmol), potassium carbonate (11.3 g, 81.81 mmol), and tetrakis(triphenylphophine)palladium (1.6 g, 1.36 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 125 mL of 1,4-dioxane and 65 mL of water. After the reaction was completed, the mixture was cooled to room temperature, EtOH was added, the solid was filtered, and washed with EtOH and water. The solid was dissolved in dichlorobenzene, and the filtrate was filtered through silica gel and Celite under reduced pressure to obtain a filtrate. The obtained filtrate was concentrated under reduced pressure, and recrystallized from dichlorobenzene to obtain compound 1-560 (11.2 g, 76.5%).

[0456]

[0457] Synthetic Example 1-9. Synthesis of Compound 1-574

[0458] Synthesis of intermediates 1-12

[0459]

[0460] 2'-Bromospiro[cyclopenta[2,1-b:3,4-b']dipyridine-5,9'-fluorene] (15.0 g, 37.76 mmol), bis(pinacolato)diboron (11.5 g, 45.31 mmol), potassium acetate (11.1 g, 113.27 mmol), and [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.9 g, 1.13 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 225 mL of 1,4-dioxane. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was extracted with ethyl acetate and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was dissolved in dichloromethane, filtered under reduced pressure through silica gel and celite, and concentrated under reduced pressure to obtain intermediate 1-12 (13.5 g, 80.5%).

[0461] Synthesis of compound 1-574

[0462]

[0463] Intermediate 1-12 (13.0 g, 29.26 mmol), 6-chloro-2-(pyridin-2-yl)quinoline (7.7 g, 32.18 mmol), potassium carbonate (12.1 g, 87.77 mmol), and tetrakis(triphenylphophine)palladium (1.7 g, 1.46 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 130 mL of 1,4-dioxane and 65 mL of water. After the reaction was completed, the mixture was cooled to room temperature, EtOH was added, the solid was filtered, and washed with EtOH and water. The solid was dissolved in dichlorobenzene, and the filtrate was filtered through silica gel and Celite under reduced pressure to obtain a filtrate. The obtained filtrate was concentrated under reduced pressure, and recrystallized from dichlorobenzene to obtain compound 1-574 (10.8 g, 70.6%).

[0464]

[0465] Synthetic Example 1-10. Synthesis of Compound 1-583

[0466]

[0467] 2-Bromospiro[cyclopenta[2,1-b:3,4-b']dipyridine-5,9'-fluorene] (15.0 g, 37.73 mmol), 2-(pyridin-2-yl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (13.8 g, 41.50 mmol), potassium carbonate (15.6 g, 113.18 mmol), and tetrakis(triphenylphophine)palladium (2.2 g, 1.89 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 150 mL of 1,4-dioxane and 75 mL of water. After the reaction was completed, the mixture was cooled to room temperature, EtOH was added, the solid was filtered, and washed with EtOH and water. After dissolving the solid in dichlorobenzene, the filtrate was filtered under reduced pressure through silica gel and celite to obtain a filtrate. The obtained filtrate was concentrated under reduced pressure and recrystallized from dichlorobenzene to obtain compound 1-583 (12.0 g, 60.9%).

[0468]

[0469] Synthesis Example 2. Synthesis of the second compound

[0470] Synthesis Example 2-1. Synthesis of Compound 2-58

[0471]

[0472] In a 1 L round-bottom flask, completely dissolve 3'-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (15.0 g, 30.7 mmol), 4,4,5,5,-tetramethyl-2-(spiro[fluorene-9,9'-xanthen]-2'-yl)-1,3,2-dioxaborolane (14.8 g, 32.2 mmol), and tetrakis(triphenylphophine)palladium (1.8 g, 1.5 mmol) in 300 mL of 1,4-dioxane. Add potassium carbonate (12.7 g, 92.0 mmol) dissolved in 150 mL of H2O, and reflux and stir for 8 hours. After the reaction is complete, cool to room temperature and concentrate under reduced pressure to obtain a filtrate. The obtained filtrate is extracted with dichloromethane and water. The organic layer is dehydrated with MgSO4, concentrated under reduced pressure, and the obtained filtrate is recrystallized to obtain compound 2-58 (18.3 g, 81%).

[0473]

[0474] Synthetic Example 2-2. Synthesis of Compound 2-284

[0475]

[0476] In a 1 L round-bottom flask, completely dissolve 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (12.0 g, 30.9 mmol), 4,4,5,5-tetramethyl-2-(spiro[fluorene-9,9'-xanthen]-2'-yl)-1,3,2-dioxaborolane (14.9 g, 32.5 mmol), and tetrakis(triphenylphophine)palladium (1.8 g, 1.5 mmol) in 310 mL of 1,4-dioxane. Add potassium carbonate (12.8 g, 92.7 mmol) dissolved in 150 mL of H2O, and stir under reflux for 8 hours. When the reaction is complete, cool to room temperature and concentrate under reduced pressure to obtain a filtrate. Extract the obtained filtrate using dichloromethane and water. The organic layer is dehydrated with MgSO4, concentrated under reduced pressure, and the resulting filtrate is recrystallized to obtain compound 2-284 (14.8 g, 75%).

[0477]

[0478] Synthesis Example 2-3. Synthesis of Compound 2-334

[0479]

[0480] In a 500 mL round-bottomed flask, completely dissolve 2,4-di([1,1'-biphenyl]-4-yl)-6-(2-bromophenyl)-1,3,5-triazine (10.0 g, 18.5 mmol), 4,4,5,5-tetramethyl-2-(spiro[fluorene-9,9'-xanthen]-2'-yl)-1,3,2-dioxaborolane (8.9 g, 19.4 mmol), and tetrakis(triphenylphophine)palladium (1.1 g, 0.9 mmol) in 180 mL of 1,4-dioxane. Add potassium carbonate (7.7 g, 55.5 mmol) dissolved in 90 mL of H2O, and stir under reflux for 8 hours. When the reaction is complete, cool to room temperature and concentrate under reduced pressure to obtain a filtrate. The obtained filtrate is extracted using dichloromethane and water. The organic layer is dehydrated with MgSO4, concentrated under reduced pressure, and the obtained filtrate is recrystallized to obtain compound 2-334 (10.6 g, 72%).

[0481]

[0482] Synthesis Example 2-4. Synthesis of Compound 2-393

[0483]

[0484] In a 1 L round-bottomed flask, completely dissolve 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (10.0 g, 25.8 mmol), 4,4,5,5-tetramethyl-2-(spiro[fluorene-9,9'-xanthen]-3'-yl)-1,3,2-dioxaborolane (12.4 g, 27.0 mmol), and tetrakis(triphenylphophine)palladium (1.5 g, 1.3 mmol) in 260 mL of 1,4-dioxane. Add potassium carbonate (10.7 g, 77.3 mmol) dissolved in 130 mL of H2O, and stir under reflux for 8 hours. When the reaction is complete, cool to room temperature and concentrate under reduced pressure to obtain a filtrate. Extract the obtained filtrate using dichloromethane and water. The organic layer is dehydrated with MgSO4, concentrated under reduced pressure, and the resulting filtrate is recrystallized to obtain compound 2-393 (13.1 g, 80%).

[0485]

[0486] Synthetic Example 2-5. Synthesis of Compound 2-515

[0487]

[0488] In a 500 mL round-bottomed flask, completely dissolve 2-chloro-4-phenyl-6-(3-triphenylsilyl)-1,3,5-triazine (10.0 g, 19.0 mmol), 4,4,5,5-tetramethyl-2-(spiro[fluorene-9,9'-xanthen]-3'-yl)-1,3,2-dioxaborolane (9.2 g, 20.0 mmol), and tetrakis(triphenylphophine)palladium (1.1 g, 1.0 mmol) in 190 mL of 1,4-dioxane. Add potassium carbonate (7.9 g, 57.0 mmol) dissolved in 90 mL of H2O, and stir under reflux for 8 hours. When the reaction is complete, cool to room temperature and concentrate under reduced pressure to obtain a filtrate. Extract the obtained filtrate using dichloromethane and water. The organic layer is dehydrated with MgSO4, concentrated under reduced pressure, and the resulting filtrate is recrystallized to obtain compound 2-515 (11.9 g, 76%).

[0489]

[0490] Synthetic Example 2-6. Synthesis of Compound 2-752

[0491]

[0492] In a 1 L round-bottomed flask, completely dissolve 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (13.0 g, 33.5 mmol), 7-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile (17.0 g, 35.2 mmol), and tetrakis(triphenylphophine)palladium (1.9 g, 1.7 mmol) in 330 mL of 1,4-dioxane. Add potassium carbonate (13.9 g, 57.0 mmol) dissolved in 160 mL of H2O, and stir under reflux for 8 hours. When the reaction is complete, cool to room temperature and concentrate under reduced pressure to obtain a filtrate. Extract the obtained filtrate using dichloromethane and water. The organic layer is dehydrated with MgSO4, concentrated under reduced pressure, and the resulting filtrate is recrystallized to obtain compound 2-752 (15.4 g, 69%).

[0493]

[0494] Synthetic Example 2-7. Synthesis of Compound 2-753

[0495]

[0496] In a 1 L round-bottom flask, completely dissolve 2-(4'-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (12.0 g, 25.8 mmol), 7-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile (13.1 g, 27.1 mmol), and tetrakis(triphenylphophine)palladium (1.5 g, 1.3 mmol) in 260 mL of 1,4-dioxane. Add potassium carbonate (10.7 g, 77.5 mmol) dissolved in 130 mL of H2O, and reflux and stir for 8 hours. When the reaction is complete, cool to room temperature and concentrate under reduced pressure to obtain a filtrate. Extract the obtained filtrate with dichloromethane and water. Remove moisture from the organic layer with MgSO4, concentrate under reduced pressure, and recrystallize the obtained filtrate to obtain compound 2-753 (12.7 g, 66%).

[0497]

[0498] Synthesis Example 3. Synthesis of the third compound

[0499] Synthesis Example 3-1. Synthesis of Compound 3-26

[0500]

[0501] In a 500 ml round bottom flask, N-([1,1'-biphenyl]-2-yl)-9,9-dimethyl-9H-fluoren-2-amine (15 g, 41.5 mmol) and 2-chloro-9-phenyl-9H-carbazole (12.7 g, 45.6 mmol), sodium tert butoxide (8.0 g, 83.0 mmol), and tri-tert-butylphosphine (0.5 g, 2.5 mmol) were mixed and dissolved in 200 ml of toluene. After that, Pd2(dba)3 (1.1 g, 1.2 mmol) was added and stirred under reflux for 12 hours under a nitrogen atmosphere. After completion of the reaction, the mixture was extracted with ethyl acetate and distilled water, the organic layer was dried over MgSO4, filtered, and the filtrate was concentrated under reduced pressure. The product was purified by column chromatography to obtain the target compound, compound 3-26 (18.8 g, 75.1%).

[0502]

[0503] Synthesis Example 3-2. Synthesis of Compound 3-29

[0504]

[0505] In a 500 ml round bottom flask, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (15 g, 41.5 mmol) and 2-chloro-9,9-diphenyl-9H-fluorene (16.1 g, 45.6 mmol), sodium tert butoxide (8.0 g, 83.0 mmol), and tri-tert-butylphosphine (0.5 g, 2.5 mmol) were mixed and dissolved in 200 ml of toluene. After that, Pd2(dba)3 (1.1 g, 1.2 mmol) was added and stirred under reflux for 10 hours under a nitrogen atmosphere. After completion of the reaction, the mixture was extracted with ethyl acetate and distilled water, the organic layer was dried over MgSO4, filtered, and the filtrate was concentrated under reduced pressure. The product was purified by column chromatography to obtain the target compound, compound 3-29 (19.1 g, 67.9%).

[0506]

[0507] Synthesis Example 3-3. Synthesis of Compound 3-56

[0508]

[0509] In a 500 ml round bottom flask, N-([1,1'-biphenyl]-2-yl)-9,9-dimethyl-9H-fluoren-2-amine (15 g, 41.5 mmol) and 9-(3-chlorophenyl)-9-phenyl-9H-fluorene (16.1 g, 45.6 mmol), sodium tert butoxide (8.0 g, 83.0 mmol), and tri-tert-butylphosphine (0.5 g, 2.5 mmol) were mixed and dissolved in 200 ml of toluene. Afterwards, Pd2(dba)3 (1.1 g, 1.2 mmol) was added and the mixture was refluxed and stirred for 12 hours under a nitrogen atmosphere. After completion of the reaction, the mixture was extracted with ethyl acetate and distilled water, the organic layer was dried over MgSO4, filtered, and the filtrate was concentrated under reduced pressure. The product was purified by column chromatography to obtain the target compound, compound 3-56 (20.4 g, 72.5%).

[0510]

[0511] Synthesis Example 3-4. Synthesis of Compound 3-60

[0512]

[0513] In a 500 ml round bottom flask, 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (15 g, 52.6 mmol) and 9-([1,1'-biphenyl]-4-yl)-2-chloro-9-phenyl-9H-fluorene (12.7 g, 57.8 mmol), sodium tert butoxide (8.0 g, 105.1 mmol), and tri-tert-butylphosphine (0.6 g, 3.2 mmol) were mixed and dissolved in 200 ml of toluene. After that, Pd2(dba)3 (1.4 g, 1.6 mmol) was added and the mixture was refluxed and stirred for 12 hours under a nitrogen atmosphere. After completion of the reaction, the mixture was extracted with ethyl acetate and distilled water, the organic layer was dried over MgSO4, filtered, and the filtrate was concentrated under reduced pressure. The product was purified by column chromatography to obtain the target compound, compound 3-60 (24.3 g, 68.2%).

[0514]

[0515] Synthesis Example 3-5. Synthesis of Compound 3-93

[0516]

[0517] In a 500 ml round bottom flask, N-(9,9-dimethyl-9H-fluoren-3-yl)-9,9-dimethyl-9H-fluoren-2-amine (15 g, 37.4 mmol) and 2-chloro-7-phenyl-9,9'-spirobi[fluorene] (17.5 g, 41.1 mmol), sodium tert butoxide (7.2 g, 74.7 mmol), and tri-tert-butylphosphine (0.5 g, 2.2 mmol) were mixed and dissolved in 200 ml of toluene. After that, Pd2(dba)3 (1.0 g, 1.1 mmol) was added and the mixture was refluxed and stirred for 14 hours under a nitrogen atmosphere. After completion of the reaction, the mixture was extracted with ethyl acetate and distilled water, the organic layer was dried over MgSO4, filtered, and the filtrate was concentrated under reduced pressure. The product was purified by column chromatography to obtain the target compound, compound 3-93 (23.6 g, 79.7%).

[0518]

[0519] Fabrication of tandem organic light-emitting devices

[0520] Comparative Example 1

[0521] After patterning the ITO substrate to have a light-emitting area of ​​2 mm × 2 mm, it was cleaned with isopropyl alcohol and UV ozone, respectively. This ITO substrate became the first electrode (anode). Thereafter, the cleaned ITO substrate was mounted on the substrate holder of a vacuum deposition device, and the pressure was adjusted to a vacuum of 1×10-7 torr. Afterwards, plasma treatment was performed for 3 minutes under a N2 atmosphere. First, the compound 3-26 was used as a host, and the NDP-9 material was used as a dopant, and the deposition was performed at a mass ratio of approximately 3% to form a first hole injection layer (first HIL) with a thickness of 5 nm. Then, the NPB material was vacuum-deposited to form a first hole transport layer (first HTL) with a thickness of 20 nm. Thereafter, the GH-1 material was used as a host, and the GD-1 material was used as a dopant, and the deposition was performed at a mass ratio of approximately 10% to form a green first light-emitting layer (first EML) with a thickness of 20 nm. And on this first light-emitting layer, compound 2-284 was vacuum-deposited to form a first hole-blocking layer (first HBL) with a thickness of 10 nm. Thereafter, comparative compound 2-1 was vacuum-deposited to form a first electron transport layer (first ETL) with a thickness of 10 nm. Next, compound 1-3 was co-deposited using a host and Yb as a dopant at a mass ratio of 1% to form a 10 nm thick N-type charge generation layer (N-CGL). Thereafter, compound 3-26 was co-deposited using a host and an NDP-9 material as a dopant at a mass ratio of approximately 5% to form a P-type charge generation layer (P-CGL). This P-type charge generation layer also functions as a second hole injection layer. Next, an NPB material was vacuum-deposited on the P-type charge generation layer to form a second hole transport layer (second HTL) with a thickness of 50 nm. Afterwards, the GH-1 material was used as a host and the GD-1 material was used as a dopant, and co-deposited at a mass ratio of approximately 10% to form a green second light-emitting layer (second EML) with a thickness of 20 nm.And on this second light-emitting layer, compound 2-284 was vacuum-deposited to form a second hole-blocking layer (second HBL) with a thickness of 5 nm. Then, a TmPyPb material was used as a host, and Liq was used as a dopant, and co-deposited to have a mass ratio of approximately 33% to form a second electron transport layer (second ETL) with a thickness of 20 nm. After that, a LiF material was vacuum-deposited to form an electron injection layer (EIL) with a thickness of 1 nm. And finally, Al was vacuum-deposited to a thickness of 100 nm to form a second electrode (cathode), thereby completing the fabrication of a tandem organic light-emitting device. Compounds 3-26, 2-284 and 1-3 used here are compounds synthesized in the previous synthesis example, and the structures of NDP-9, NPB, GH-1, GD-1, TmPyPb and Liq are shown in Table 1 below, respectively, and the structure of comparative compound 2-1 is shown in Table 2 below.

[0522]

[0523]

[0524] Comparative Examples 2 to 18

[0525] A tandem organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that the first electron transport layer material and the N-type charge generation layer host material were used as shown in Table 3 below.

[0526]

[0527] Examples 1 to 70

[0528] A tandem organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that the first electron transport layer material and the N-type charge generation layer host material were used as shown in Table 3 below.

[0529]

[0530] The driving voltage, current efficiency, and lifetime of the previously fabricated tandem organic light-emitting devices were measured at a driving current density of 10 mA / cm2. The results are shown in Table 3 below.

[0531] Classification 1 ETL Material N-CGL Host Material Operating Voltage (V) Current Efficiency (cd / A) Lifespan (T95) Comparison Example 1 Comparison Compound 2-1 Compound 1-36.77 119.03 142.24 Comparison Example 2 Comparison Compound 2-1 Compound 1-1656.84 117.15 144.55 Comparison Example 3 Comparison Compound 2-1 Compound 1-5836.86 117.60 150.54 Comparison Example 4 Comparison Compound 2-2 Compound 1-36.75 119.06 142.38 Comparison Example 5 Comparison Compound 2-2 Compound 1-1656.77 118.84 148.80 Comparison Example 6 Comparison Compound 2-2 Compound 1-5836.79119.13147.72Comparative Example 7Comparative Compound 2-3Compound 1-36.75116.28150.47Comparative Example 8Comparative Compound 2-3Compound 1-1656.79119.04144.58Comparative Example 9Comparative Compound 2-3Compound 1-5836.79117.69144.97Comparative Example 10Compound 2-58Comparative Compound 1-16.84114.05146.27Comparative Example 11Compound 2-284Comparative Compound 1-16.89118.83148.16Comparative Example 12Compound 2-752Comparative Compound 1-16.86117.79141.44Comparative Example 13 Compound 2-58 Comparison Compound 1-26.77 117.15 150.44 Comparison Example 14 Compound 2-28 4 Comparison Compound 1-26.78 118.96 144.40 Comparison Example 15 Compound 2-752 Comparison Compound 1-26.75 115.01 150.80 Comparison Example 16 Compound 2-58 Comparison Compound 1-36.79 115.79 149.44 Comparison Example 17 Compound 2-284 Comparison Compound 1-36.86 117.85 145.70 Comparison Example 18 Compound 2-752 Comparison Compound 1-36.79 117.79 150.62 Example 1 Compound 2-58 Compound 1-36.54125.48158.61 Example 2 Compound 2-284 Compound 1-36.58123.80157.42 Example 3 Compound 2-334 Compound 1-36.60124.79155.53 Example 4 Compound 2-393 Compound 1-36.57127.56157.82 Example 5 Compound 2-515 Compound 1-36.61122.86156.60 Example 6 Compound 2-752 Compound 1-36.55122.30151.36Example 7 Compound 2-753 Compound 1-36.54125.61153.92Example 8 Compound 2-58 Compound 1-1656.50124.38152.07Example 9 Compound 2-284 Compound 1-1656.51127.60155.03Example 10 Compound 2-334 Compound 1-1656.54125.26152.24Example 11 Compound 2-393 Compound 1-1656.53122.94157.91Example 12 Compound 2-515 Compound 1-1656.55 124.66 158.53 Example 13 Compound 2-752 Compound 1-1656.49 123.10 153.56 Example 14 Compound 2-753 Compound 1-1656.48 122.98 154.61 Example 15 Compound 2-58 Compound 1-1676.34 130.56 159.94 Example 16 Compound 2-284 Compound 1-1676.34 128.85 161.00 Example 17 Compound 2-334 Compound 1-1676.37 129.14 159.96 Example 18 Compound 2-393 Compound 1-1676.35 130.14 161.36 Example 19 Compound 2-515 Compound 1-1676.37 130.33 159.73 Example 20 Compound 2-752 Compound 1-1676.33 129.58 159.84 Example 21 Compound 2-753 Compound 1-1676.34 129.34 161.88 Example 22 Compound 2-58 Compound 1-1726.51 122.48 154.60 Example 23 Compound 2-284 Compound 1-1726.54 122.48 157.71 Example 24 Compound 2-334 Compound 1-1726.57 127.49 155.20 Example 25 Compound 2-393 Compound 1-1726.55 127.56 150.95 Example 26 Compound 2-515 Compound 1-1726.59 124.89 154.71 Example 27 Compound 2-752 Compound 1-1726.50 127.59 153.93 Example 28 Compound 2-753 Compound 1-1726.52 126.69 151.98 Example 29 Compound 2-58 Compound 1-48 26.37 123.84 154.12 Example 30 Compound 2-284 Compound 1-4826.38124.04154.09 Example 31 Compound 2-334 Compound 1-4826.41127.61154.61 Example 32 Compound 2-393 Compound 1-4826.35125.03156.84 Example 33 Compound 2-515 Compound 1-4826.39124.70158.44 Example 34 Compound 2-752 Compound 1-4826.36126.90157.48 Example 35 Compound 2-753 Compound 1-4826.36125.05157.11 Example 36 Compound 2-58 Compound 1-5236.39 125.19 155.43 Example 37 Compound 2-284 Compound 1-5236.39 126.40 155.02 Example 38 Compound 2-334 Compound 1-5236.43 124.75 156.78 Example 39 Compound 2-393 Compound 1-5236.40 126.50 155.31 Example 40 Compound 2-515 Compound 1-5236.43 126.73 157.84 Example 41 Compound 2-752 Compound 1-5236.39 127.25 158.04 Example 42 Compound 2-753 Compound 1-5236.40 124.03 154.36 Example 43 Compound 2-58 Compound 1-5436.45 123.75 153.64 Example 44 Compound 2-284 Compound 1-5436.46 125.05 157.95 Example 45 Compound 2-334 Compound 1-5436.48 124.25 157.45 Example 46 Compound 2-393 Compound 1-5436.46 124.79 156.80 Example 47 Compound 2-515 Compound 1-5436.48 124.04 154.09 Example 48 Compound 2-752 Compound 1-5436.45 125.25 158.50 Example 49 Compound 2-753 Compound 1-5436.46 127.13 153.61 Example 50 Compound 2-58 Compound 1-5606.41 123.95 154.19 Example 51 Compound 2-284 Compound 1-5606.42 124.15 155.64 Example 52 Compound 2-334 Compound 1-5606.45 124.99 158.29 Example 53 Compound 2-393 Compound 1-5606.43 128.11 153.56 Example 54 Compound 2-515 Compound 1-5606.44127.50154.74 Example 55 Compound 2-752 Compound 1-5606.41 124.18 154.52 Example 56 Compound 2-753 Compound 1-5606.42 126.58 157.79 Example 57 Compound 2-58 Compound 1-5746.66 120.10 153.48 Example 58 Compound 2-284 Compound 1-5746.68 121.33 154.46 Example 59 Compound 2-334 Compound 1-5746.71 119.80 154.55 Example 60 Compound 2-393 Compound 1-5746.71122.16151.64 Example 61 Compound 2-515 Compound 1-5746.70122.78150.89 Example 62 Compound 2-752 Compound 1-5746.67124.45151.23 Example 63 Compound 2-753 Compound 1-5746.67121.48151.68 Example 64 Compound 2-58 Compound 1-5836.63122.99152.58 Example 65 Compound 2-284 Compound 1-5836.66123.80151.61 Example 66 Compound 2-334 Compound 1-5836.67 122.15 150.88 Example 67 Compound 2-393 Compound 1-5836.68 122.23 155.64 Example 68 Compound 2-515 Compound 1-5836.65 119.79 154.26 Example 69 Compound 2-752 Compound 1-5836.63 119.89 151.09 Example 70 Compound 2-753 Compound 1-5836.63 123.76 150.82.

[0532] As shown in the results of Table 3 above, compared to Comparative Examples 1 to 9 in which the first compound was used as the N-type charge generation layer host material but the second compound was not used as the first ETL material and Comparative Examples 10 to 18 in which the second compound was used as the first ETL material but the first compound was not used as the N-type charge generation layer host material, it can be confirmed that the driving voltage of the tandem organic light-emitting devices of Examples 1 to 70 according to the present invention is lower and the current efficiency and lifespan are improved. In this way, when the first pyridine-quinoline-based compound is used as the N-type charge generation layer host material and the second spirofluorene xanthene-triazine-based compound is used as the electron transport layer material adjacent to the N-type charge generation layer, the driving voltage is reduced and the efficiency and lifespan are effectively improved.

[0533]

[0534] Examples 71 to 78

[0535] A tandem organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that the first electron transport layer material, the N-type charge generation layer host material, and the P-type charge generation layer host material were used as shown in Table 4 below.

[0536]

[0537] The driving voltage, current efficiency, and lifetime of the previously fabricated tandem organic light-emitting devices were measured at a driving current density of 10 mA / cm2. The results are shown in Table 4 below.

[0538] Classification 1 ETL material N-CGL host material P-CGL host material Operating voltage (V) Current efficiency (cd / A) Lifespan (T95) Example 71 Compound 2-752 Compound 1-167 Compound 3-296.33 131.98 163.71 Example 72 Compound 2-753 Compound 1-167 Compound 3-296.32 132.23 164.01 Example 73 Compound 2-752 Compound 1-167 Compound 3-566.33 131.51 163.59 Example 74 Compound 2-753 Compound 1-167 Compound 3-566.30 131.59 163.42 Example 75 Compound 2-752 Compound 1-167 Compound 3-606.34 131.38 163.48 Example 76 Compound 2-753 Compound 1-167 Compound 3-606.31 132.14 162.94 Example 77 Compound 2-752 Compound 1-167 Compound 3-936.32 131.45 164.01 Example 78 Compound 2-753 Compound 1-167 Compound 3-936.31 132.36 163.46

[0539] Table 4 above shows the preliminary results of changing the third compound, which is the P-type charge generation layer host material, to compounds containing two or three or more fluorene groups, and it can be confirmed that the driving voltage, efficiency, and lifespan are further improved compared to the results of Examples 1 to 70. In this way, in tandem organic light-emitting devices, optimizing the combination of the N-type charge generation layer and the electron transport region layer, and further the combination with the P-type charge generation layer, is very important for improving the performance of the device.

[0540]

[0541] Although the present invention has been described above with reference to preferred embodiments thereof, it will be understood by those skilled in the art that various modifications and changes may be made to the present invention without departing from the technical spirit and scope of the present invention as set forth in the claims below.

Claims

1. First electrode and second electrode; A plurality of light-emitting layers positioned between the first electrode and the second electrode; and A charge generation layer is included, each of which is positioned at least one between two adjacent light-emitting layers; In a tandem organic light-emitting device, at least one of the charge generation layers includes an N-type charge generation layer, At least one of the above N-type charge generation layers comprises a first compound represented by the following chemical formula 1, A tandem organic light-emitting device, wherein at least one of the organic layers of the electron transport region adjacent to the N-type charge generation layer comprises a second compound represented by the following chemical formula 2: <Chemical Formula 1> In the above chemical formula 1, R1 and R2 are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted sulfide group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, and a substituted or unsubstituted fused ring group, or adjacent ones may or may not combine with each other to form a substituted or unsubstituted ring, However, either one of the above R1 and either one of the R2 is a bonding position that is connected to each other by a single bond, <Chemical Formula 2> In the above chemical formula 2, X is O or S, R10 is each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted sulfide group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, and a substituted or unsubstituted fused ring group, or adjacent ones may or may not combine with each other to form a substituted or unsubstituted ring, However, the above chemical formula 2 includes a substituted or unsubstituted triazine group.

2. In paragraph 1, The above chemical formula 1 is a tandem organic light-emitting device having the following chemical formula 1-1: <Chemical Formula 1-1> In the above chemical formula 1-1, R1 and R2 are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a substituted or unsubstituted C1~C30 alkyl group, a substituted or unsubstituted C6~C50 aryl group, or a substituted or unsubstituted C2~C50 heteroaryl group, and when substituted, the substituent is at least one selected from deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a substituted or unsubstituted C1~C10 alkyl group, a substituted or unsubstituted C6~C20 aryl group, and a substituted or unsubstituted C2~C20 heteroaryl group. However, at least one of the above R1 and R2 is not hydrogen.

3. In paragraph 2, The above chemical formula 1-1 is a tandem organic light-emitting device having the following chemical formula 1-2 or 1-3: <Chemical Formula 1-2> <Chemical Formula 1-3> In the above chemical formulas 1-2 and 1-3, R1 and R2 are the same as defined in the above chemical formula 1-1, L1 is each independently a substituted or unsubstituted C6~C20 arylene group or a substituted or unsubstituted C2~C20 heteroarylene group, Ar1 is a substituted or unsubstituted C6~C30 aryl group or a substituted or unsubstituted C2~C30 heteroaryl group, n is an integer from 0 to 4.

4. In paragraph 3, The above chemical formula 1-2 is any one of the following chemical formulas 1-2-1 to 1-2-3, The above chemical formula 1-3 is a tandem organic light-emitting device having any one of the following chemical formulas 1-3-1 to 1-3-3: <Chemical Formula 1-2-1> <Chemical Formula 1-2-2> <Chemical Formula 1-2-3> In the above chemical formulas 1-2-1 to 1-2-3, R1, L1, Ar1 and n are the same as defined in the above chemical formula 1-2, <Chemical Formula 1-3-1> <Chemical Formula 1-3-2> <Chemical Formula 1-3-3> In the above chemical formulas 1-3-1 to 1-3-3, R2, L1, Ar1 and n are the same as defined in the above chemical formula 1-3.

5. In paragraph 3, The above Ar1 is each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted anthracene group, a substituted or unsubstituted chrysene group, a substituted or unsubstituted benzophenanthrene group, a substituted or unsubstituted benzoanthracene group, a substituted or unsubstituted pyrene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted diphenylfluorene group, a substituted or unsubstituted dimethylfluorene group, a substituted or unsubstituted spirobifluorene group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted pyrazine group, a substituted or unsubstituted pyridazine group, a substituted or unsubstituted trizine group, a substituted or unsubstituted quinoline group, a substituted or unsubstituted isoquinoline group, a substituted or unsubstituted benzophenanthrene group, a substituted or unsubstituted benzoanthracene group, a substituted or unsubstituted pyrene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted diphenylfluorene group, a substituted or unsubstituted dimethylfluorene group, a substituted or unsubstituted spirobifluorene group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted pyrazine group, a substituted or unsubstituted pyridazine group, a substituted or unsubstituted trizine group, a substitute An unsubstituted quinazoline group, a substituted or unsubstituted quinoxaline group, a substituted or unsubstituted phthalazine group, a substituted or unsubstituted cinnoline group, a substituted or unsubstituted 1,5-naphthyridine group, a substituted or unsubstituted 1,6-naphthyridine group, a substituted or unsubstituted 1,7-naphthyridine group, a substituted or unsubstituted 1,8-naphthyridine group, a substituted or unsubstituted 2,5-naphthyridine group, a substituted or unsubstituted 2,6-naphthyridine group, a substituted or unsubstituted 2,7-naphthyridine group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted benzoxazole group, a substituted or unsubstituted benzothiazole group, a substituted or unsubstituted benzoimidazole group, a substituted or unsubstituted 1,10-phenanthroline group, a substituted or unsubstituted A tandem organic light-emitting device comprising a benzoquinoline group or a substituted or unsubstituted 4,5-diazaspirobifluorene group.

6. In paragraph 5, The above Ar1 is independently one of the following structural formulas Ar1-1 to Ar1-17, a tandem organic light emitting device: [Ar1-1] [Ar1-2] [Ar1-3] [Ar1-4] [Ar1-5] [Ar1-6] [Ar1-7] [Ar1-8] [Ar1-9] [Ar1-10] [Ar1-11] [Ar1-12] [Ar1-13] [Ar1-14] [Ar1-15] [Ar1-16] [Ar1-17] In the above structural formulas Ar1-1 to Ar1-17, R3 and R4 are each independently selected from hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a nitrile group, a substituted or unsubstituted C1~C10 alkyl group, a substituted or unsubstituted C6~C20 aryl group, and a substituted or unsubstituted C2~C20 heteroaryl group, * indicates the position where it is bound to L1.

7. In paragraph 1, The above first compound is any one of the following compounds 1-1 to 1-588, a tandem organic light-emitting device:

8. In paragraph 1, The above chemical formula 2 is a tandem organic light-emitting device including a substituent represented by the following structural formula A: [Structural formula A] In the above structural formula A, Ar2 and Ar3 are each independently a substituted or unsubstituted C1~C30 alkyl group, a substituted or unsubstituted C1~C30 alkenyl group, a substituted or unsubstituted C1~C30 alkynyl group, a substituted or unsubstituted C3~C30 cycloalkyl group, a substituted or unsubstituted C1~C30 heterocycloalkyl group, a substituted or unsubstituted C1~C30 alkoxy group, a substituted or unsubstituted C1~C30 sulfide group, a substituted or unsubstituted C6~C50 aryl group, a substituted or unsubstituted C2~C50 heteroaryl group, a substituted or unsubstituted C6~C30 aryloxy group, a substituted or unsubstituted C2~C30 heteroaryloxy group, a substituted or unsubstituted C1~C30 thio group, a substituted or unsubstituted C1~C30 amine group, a substituted or unsubstituted Selected from the group consisting of a C1~C30 silyl group, a substituted or unsubstituted C1~C30 phosphine oxide group, and a substituted or unsubstituted C3~C30 fused ring group, L2 is each independently a substituted or unsubstituted C6~C30 arylene group, a substituted or unsubstituted C2~C30 heteroarylene group, or a substituted or unsubstituted C2~C30 fused ring group, m is an integer from 0 to 4.

9. In paragraph 8, The above chemical formula 2 is a tandem organic light-emitting device, one of the following chemical formulas 2-1 to 2-5: <Chemical Formula 2-1> <Chemical Formula 2-2> <Chemical Formula 2-3> <Chemical Formula 2-4> <Chemical Formula 2-5> In the above chemical formulas 2-1 to 2-5, X and R10 are the same as defined in the above chemical formula 2, but one of R10 in each chemical formula is the above structural formula A.

10. In paragraph 9, The above chemical formula 2 is a tandem organic light-emitting device having the following chemical formula 2-1-1 or 2-1-2: <Chemical Formula 2-1-1> <Chemical Formula 2-1-2> In the above chemical formulas 2-1-1 and 2-1-2, X and R10 are the same as defined in the above chemical formula 2, and Ar2, Ar3, L2 and m are the same as defined in the above structural formula A.

11. In paragraph 1, The second compound is any one of the following compounds 2-1 to 2-828, a tandem organic light-emitting device:

12. In paragraph 1, The organic layer of the electron transport region includes at least one of an electron transport layer and a hole blocking layer, A tandem organic light-emitting device, wherein one or both of the electron transport layer and the hole blocking layer comprise the second compound.

13. In paragraph 1, The above N-type charge generation layer includes an N-type dopant, A tandem organic light-emitting device, wherein the N-type dopant comprises at least one selected from lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), ytterbium (Yb), samarium (Sm), tin (Sn), copper (Cu), titanium (Ti), cadmium (Cd), mercury (Hg), lead (Pb), bismuth (Bi), zinc (Zn), iron (Fe), cobalt (Co), nickel (Ni), indium (In), gallium (Ga), thorium (Th), uranium (U), silver (Ag), aluminum (Al), gold (Au), molybdenum (Mo), niobium (Nb), palladium (Pd), platinum (Pt), and europium (Eu).

14. In paragraph 1, It includes a P-type charge generation layer adjacent to the N-type charge generation layer, A tandem organic light-emitting device, wherein the P-type charge generation layer comprises an amine-based third compound.

15. In paragraph 14, The third compound is any one of the following compounds 3-1 to 3-112, a tandem organic light-emitting device:

16. An electronic device including the tandem organic light-emitting element of paragraph 1.

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