Organic electroluminescence device and polycyclic compound for organic electroluminescence device

Abstract

The present disclosure provides an organic electroluminescence device and a polycyclic compound for an organic electroluminescence device. The organic electroluminescence device of an embodiment of the present disclosure includes a first electrode, a hole transport region on the first electrode, an emission layer on the hole transport region, an electron transport region on the emission layer, and a second electrode on the electron transport region, wherein the emission layer can include a polycyclic compound represented by Formula 1, thereby exhibiting high luminous efficiency: Formula 1 wherein at least one selected from R1 to R3 is represented by Formula 2: Formula 2

Description

[0001] Cross-references to related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2019-0142844, filed on November 8, 2019, the entire contents of which are incorporated herein by reference. Technical Field

[0003] This disclosure relates herein to organic electroluminescent devices and polycyclic compounds for use in organic electroluminescent devices. Background Technology

[0004] Recently, there has been active development of organic electroluminescent displays (OLEDs) as image display devices. Unlike liquid crystal displays (LCDs), OLEDs are self-emissive display devices in which holes and electrons injected from the first and second electrodes recombine in the emitting layer, thereby emitting light by a light-emitting material containing organic compounds to display an image.

[0005] When applying organic electroluminescent devices to display devices, there is a requirement (or expectation) for organic electroluminescent devices with low driving voltage, high luminous efficiency and long lifespan, and there is an ongoing need to develop materials for organic electroluminescent devices that can reliably achieve these characteristics.

[0006] In recent years, in particular in order to achieve high-efficiency organic electroluminescent devices, technologies are being developed for phosphorescence emission using triplet energy or for delayed fluorescence using triplet-triplet annihilation (TTA) in which singlet excitons are generated through collisions of triplet excitons. Furthermore, thermally activated delayed fluorescence (TADF) materials using the delayed fluorescence phenomenon are being developed. Summary of the Invention

[0007] One or more aspects of the embodiments of this disclosure provide an organic electroluminescent device having a long lifespan and high efficiency, and a polycyclic compound used therein.

[0008] One or more aspects of the embodiments of this disclosure also provide an organic electroluminescent device comprising a thermally activated delayed fluorescence emission material and a polycyclic compound used as a thermally activated delayed fluorescence emission material.

[0009] Embodiments of this disclosure provide an organic electroluminescent device comprising: a first electrode; a hole transport region on the first electrode; an emission layer on the hole transport region; an electron transport region on the emission layer; and a second electrode on the electron transport region, wherein the first electrode and the second electrode each independently comprise: at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, In, Sn, and Zn, or a compound selected from two or more of them, a mixture selected from two or more of them, or an oxide thereof, wherein the emission layer comprises a polycyclic compound represented by the following formula 1:

[0010] Formula 1

[0011]

[0012] In Formula 1 above, Z1 and Z2 can each independently be NAr1, O, or S, provided that Z1 and Z2 are not simultaneously O; Ar1 ​​can be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and Ar1 can be attached to an adjacent group to form a ring; R1 to R3 can each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and any R1 to R3 can be attached to an adjacent group to form a ring; a and b can each independently be an integer selected from 0 to 4; c can be an integer selected from 0 to 3; and at least one selected from R1 to R3 can be represented by Formula 2 below:

[0013] Formula 2

[0014]

[0015] In Formula 2 above, R4 to R8 may each be independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and any R4 to R8 may be attached to an adjacent group to form a ring; d, e, and g may each be independently an integer selected from 0 to 4; and f and h may each be independently an integer selected from 0 to 5.

[0016] In one embodiment, the emitting layer may emit delayed fluorescence. The emitting layer may be a delayed fluorescence emitting layer comprising a first compound and a second compound, and the first compound may include a polycyclic compound. The emitting layer may be a thermally delayed fluorescence emitting layer that emits light having a maximum emission wavelength of about 440 nm to about 470 nm.

[0017] Equation 1 can be expressed by Equation 3 below:

[0018] Formula 3

[0019]

[0020] In Formula 3 above, Y1 to Y5 may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and at least one selected from Y1 to Y5 may be represented by Formula 2 above; R1 to R3 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and any R1 to R3 may be attached to an adjacent group to form a ring; i to k may each independently be an integer selected from 0 to 2; and Z1 and Z2 may be the same as defined in Formula 1.

[0021] Z1 and Z2 above can each be NAr1 or O independently.

[0022] In the implementation, equation 3 can be represented by the following equation 4:

[0023] Formula 4

[0024]

[0025] In Formula 4 above, Ar2 can be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and Ar2 can be attached to an adjacent group to form a ring, and Z1, Y1 to Y5, R1 to R3 and i to k can be the same as defined in Formula 3.

[0026] Each of Y1 to Y5 above can be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted arylamine group having 6 to 30 cyclic carbon atoms, a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted carbazole group, and at least one selected from Y1 to Y5 above can be represented by Formula 2 above.

[0027] In the implementation, equation 3 above can be represented by equation 5 or equation 6 below:

[0028] Formula 5

[0029]

[0030] Formula 6

[0031]

[0032] In Formulas 5 and 6 above, Y1 to Y5 may each be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and Z1, Z2, R1 to R8 and d to k may be the same as those defined in Formulas 2 and 3.

[0033] Equation 3 can be represented by Equation 7 below:

[0034] Formula 7

[0035]

[0036] In Formula 7 above, Y1, Y2, Y4 and Y5 may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and Z1, Z2, R1 to R8 and d to k may be the same as those defined in Formulas 2 and 3.

[0037] Equation 3 above can be represented by Equation 8 or Equation 9 below:

[0038] Formula 8

[0039]

[0040] Formula 9

[0041]

[0042] In Formulas 8 and 9 above, Y1 to Y5 can each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and Z1, Z2, R1 to R8 and d to k can be the same as those defined in Formulas 2 and 3.

[0043] Ar1 above can be represented by the following equation 10:

[0044] Formula 10

[0045]

[0046] In Formula 10 above, Y can be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; and m can be an integer selected from 0 to 5.

[0047] Embodiments of this disclosure provide polycyclic compounds represented by Formula 1 above. Attached Figure Description

[0048] The accompanying drawings are included to provide a further understanding of this disclosure, and are incorporated in and constitute a part of this specification. The drawings illustrate exemplary embodiments of the present disclosure and, together with the description, serve to explain the principles of the disclosure. In the drawings:

[0049] Figure 1 A cross-sectional view of an organic electroluminescent device according to an embodiment of the present disclosure is shown for illustrative purposes.

[0050] Figure 2 A cross-sectional view of an organic electroluminescent device according to an embodiment of the present disclosure is shown for illustrative purposes.

[0051] Figure 3 A cross-sectional view of an organic electroluminescent device according to an embodiment of the present disclosure is shown schematically; and

[0052] Figure 4 A cross-sectional view of an organic electroluminescent device according to an embodiment of the present disclosure is shown for illustrative purposes. Detailed Implementation

[0053] This disclosure may be modified and may be embodied in various forms, and exemplary embodiments will be explained in more detail with reference to the accompanying drawings. However, this disclosure may be embodied in various forms and should not be construed as limited to the embodiments set forth herein. Rather, all modifications, equivalents, and substitutions that are included within the spirit and scope of this disclosure should be included herein.

[0054] In the description, it should be understood that when an element or layer is referred to as being “on”, “connected to” or “attached to” another element or layer, it may be directly on, directly connected to or directly attached to the other element or layer (without any intermediate elements between them), or there may be intermediate elements or layers.

[0055] The same reference numerals refer to the same elements throughout the drawings. Furthermore, for the effective description of the technical content, the thickness, scale, and dimensions of the elements are enlarged in the drawings.

[0056] The term "and / or" includes all combinations of one or more of the related configurations that can be defined. For example, expressions such as "at least one...", "a...", and "selected from..." modify the entire column of elements without modifying any individual element in that column when preceding a column of elements. Furthermore, when describing embodiments of this disclosure, the word "may" refers to "one or more embodiments of this disclosure".

[0057] It should be understood that although the terms “first,” “second,” etc., may be used herein to describe various elements, these elements should not be limited by these terms. These terms are used only to distinguish one element from another. For example, without departing from the scope of exemplary embodiments of this disclosure, a first element may be referred to as a second element, and similarly, a second element may be referred to as a first element. Unless the context clearly indicates otherwise, singular terms may include plural forms.

[0058] Additionally, terms such as "below," "down," "above," and "upper" are used to describe the relationships of the configurations shown in the accompanying drawings. These terms are used as relative concepts and are described with reference to the directions indicated in the accompanying drawings.

[0059] Unless otherwise defined, all terms used herein (including technical and scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. It should also be understood that terms defined in common dictionaries should be interpreted as having the same meaning as in the context of the prior art, and are expressly defined herein unless interpreted in an ideal or overly formal sense.

[0060] It should be understood that the terms “comprising,” “including,” or “having” are intended to indicate the presence of the stated features, integers, steps, operations, elements, components, or combinations thereof in this disclosure, but do not exclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.

[0061] Hereinafter, organic electroluminescent devices according to embodiments of the present disclosure and compounds included therein will be described with reference to the accompanying drawings.

[0062] Figures 1 to 4 A cross-sectional view of an organic electroluminescent device according to an embodiment of the present disclosure is shown for illustrative purposes. See also Figures 1 to 4 In the organic electroluminescent device 10 according to the embodiment, the first electrode EL1 and the second electrode EL2 are arranged to face each other, and the emission layer EML is provided between the first electrode EL1 and the second electrode EL2.

[0063] Furthermore, in addition to the emitter layer EML, the organic electroluminescent device 10 of the embodiment may further include multiple functional layers between the first electrode EL1 and the second electrode EL2. The multiple functional layers may include a hole transport region HTR and an electron transport region ETR. For example, the organic electroluminescent device 10 according to the embodiment may include a first electrode EL1, a hole transport region HTR, an emitter layer EML, an electron transport region ETR, and a second electrode EL2 stacked sequentially. In some embodiments, the organic electroluminescent device 10 of the embodiment may include a capping layer CPL on the second electrode EL2.

[0064] The organic electroluminescent device 10 of the embodiment includes a polycyclic compound, which will be described in more detail later, in the emission layer EML between the first electrode EL1 and the second electrode EL2. However, the embodiment is not limited to this, and the organic electroluminescent device 10 may include the polycyclic compound not only in the emission layer EML, but also in the hole transport region HTR or electron transport region ETR of the plurality of functional layers constituting the first electrode EL1 and the second electrode EL2, or in the capping layer CPL provided on the second electrode EL2.

[0065] At the same time, with Figure 1 Compare, Figure 2 A cross-sectional view of an organic electroluminescent device 10 according to an embodiment is shown, wherein the hole transport region HTR includes a hole injection layer HIL and a hole transport layer HTL, and the electron transport region ETR includes an electron injection layer EIL and an electron transport layer ETL. Figure 1 Compare, Figure 3 A cross-sectional view of an organic electroluminescent device 10 according to an embodiment is shown, wherein the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL, and an electron blocking layer EBL, and the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL, and a hole blocking layer HBL. Figure 2 Compare, Figure 4 A cross-sectional view of an organic electroluminescent device 10, showing an embodiment in which a capping layer CPL is included on the second electrode EL2.

[0066] The first electrode EL1 is conductive. The first electrode EL1 may be formed of a metal alloy or any suitable conductive compound. The first electrode EL1 may be a pixel electrode and / or a positive electrode. The first electrode EL1 may be a transmissive electrode, a transmissive-reflective electrode, or a reflective electrode. When the first electrode EL1 is a transmissive electrode, it may comprise a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), and / or indium tin zinc oxide (ITZO). When the first electrode EL1 is a transmissive or reflective electrode, the first electrode EL1 may include at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, In, Sn, and Zn, or a compound thereof, a mixture thereof (e.g., a mixture of Ag and Mg), or an oxide thereof, wherein "oxide thereof" means one selected from oxides, oxides of compounds, and oxides of mixtures of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, In, Sn, and Zn. In some embodiments, the first electrode EL1 may have a multilayer structure including a reflective or transmissive layer and a transmissive layer formed of ITO, IZO, ZnO, ITZO, etc. For example, the first electrode EL1 may have a three-layer structure of ITO / Ag / ITO, but is not limited thereto. The thickness of the first electrode EL1 may be approximately to approximately For example, about to approximately

[0067] The hole transport region HTR is provided on the first electrode EL1. The hole transport region HTR may include at least one of the hole injection layer HIL, the hole transport layer HTL, the hole buffer layer, and the electron blocking layer.

[0068] The hole transport region (HTR) can have a single layer formed of a single material, a single layer formed of multiple different materials, or a multilayer structure including multiple layers formed of multiple different materials.

[0069] For example, the hole transport region HTR may have a single-layer structure of a hole injection layer HIL or a hole transport layer HTL, and may have a single-layer structure formed of a hole injection material and a hole transport material. In some embodiments, the hole transport region HTR may have a single-layer structure formed of a variety of different materials, or a structure in which hole injection layer HIL / hole transport layer HTL, hole injection layer HIL / hole transport layer HTL / hole buffer layer, hole injection layer HIL / hole buffer layer, hole transport layer HTL / hole buffer layer, or hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL are stacked in the order stated from the first electrode EL1, but the embodiments are not limited thereto.

[0070] Hole transport regions (HTRs) can be formed using one or more suitable methods, such as vacuum deposition, spin coating, casting, Langmuir-Brookett (LB) method, inkjet printing, laser printing and / or laser-induced thermal imaging (LITI).

[0071] Hole injection layer HIL may include, for example, phthalocyanine compounds (such as copper phthalocyanine); N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine (DNTPD), 4,4',4”-[tris(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), 4,4',4”-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4”-tris{N-(2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), polyaniline / camphor sulfonic acid (PANI / CSA), polyaniline / poly(4-styrene sulfonate) (PANI / PSS), N,N'-di(naphthyl-l-yl)-N,N'-diphenyl-benzidine (NPB), 2,2'-dimethyl-N,N'-di-[(1-naphthyl)-N,N'-diphenyl]-1,1'-biphenyl-4,4'-diamine (α-NPD), triphenylamine-containing polyether ketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium tetra(pentafluorophenyl)borate, dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexaonitrile (HAT-CN), etc.

[0072] The hole transport layer (HTL) may further include suitable materials such as, for example, carbazole derivatives (e.g., N-phenylcarbazole and / or polyvinylcarbazole), fluorine derivatives, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), triphenylamine derivatives (e.g., 4,4',4”-tris(N-carbazolyl)triphenylamine (TCTA)), and N,N'-bis(naphthyl-1-yl)-N,N'-diphenyl-benzidine (NPB). ), 2,2'-dimethyl-N,N'-di-[(1-naphthyl)-N,N'-diphenyl]-1,1'-biphenyl-4,4'-diamine (α-NPD), 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline] (TAPC), 3,3'-dimethyl-N4,N4,N4',N4'-tetra-m-tolyl-[1,1'-biphenyl]-4,4'-diamine (HMTPD), 1,3-bis(N-carbazolyl)benzene (mCP), etc.

[0073] Electron blocking layer (EBL) may include, for example, carbazole derivatives (such as N-phenylcarbazole and / or polyvinylcarbazole), fluorine derivatives, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), triphenylamine derivatives (such as 4,4',4”-tris(N-carbazolyl)triphenylamine (TCTA)), N,N'-di(naphthyl-1-yl)-N,N'-di Phenylacetidine (NPB), 2,2'-dimethyl-N,N'-di-[(1-naphthyl)-N,N'-diphenyl]-1,1'-biphenyl-4,4'-diamine (α-NPD), 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), mCP, etc.

[0074] The thickness of the hole transport region (HTR) can be approximately to approximately For example, about to approximately The thickness of the hole injection layer (HIL) can be, for example, approximately to approximately Furthermore, the thickness of the hole transport layer (HTL) can be approximately [missing information]. to approximately For example, the thickness of the electron blocking layer (EBL) can be approximately [missing information]. to approximately When the thicknesses of the hole transport region HTR, hole injection layer HIL, hole transport layer HTL, and electron blocking layer EBL each independently satisfy the above ranges, satisfactory (or appropriate) hole transport properties can be achieved without a significant increase in driving voltage.

[0075] In addition to the materials described above, the hole transport region (HTR) may further include a charge-generating material to increase conductivity. The charge-generating material may be uniformly or non-uniformly dispersed in the hole transport region (HTR). The charge-generating material may be, for example, a p-doper. The p-doper may be, but is not limited to, a quinone derivative, a metal oxide, or a cyano-containing compound. Non-limiting examples of p-dopers may include quinone derivatives (such as tetracyanoquinone dimethyl (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethyl (F4-TCNQ)) and metal oxides (such as tungsten oxide and / or molybdenum oxide), etc.

[0076] As described above, in addition to the hole injection layer (HIL) and the hole transport layer (HTL), the hole transport region (HTR) may further include at least one of a hole buffer layer and an electron blocking layer (EBL). The hole buffer layer can compensate for the resonant distance according to the wavelength of light emitted from the emitter layer (EML) and can increase the light emission efficiency. Materials that may be included in the hole transport region (HTR) can be used as materials that may be included in the hole buffer layer. The electron blocking layer (EBL) is a layer used to prevent or reduce the injection of electrons from the electron transport region (ETR) into the hole transport region (HTR).

[0077] The emitter layer EML is provided on the hole transport region HTR. The thickness of the emitter layer EML can be, for example, approximately to approximately Or about to approximately The emitter layer (EML) can have a single layer formed of a single material, a single layer formed of multiple different materials, or a multilayer structure with multiple layers formed of multiple different materials.

[0078] The emitting layer (EML) can emit one of the following colors of light: red, green, blue, white, yellow, and cyan. The EML may include fluorescent or phosphorescent emitting materials.

[0079] In an embodiment, the emitting layer EML may be a fluorescent emitting layer. For example, some light emitted from the emitting layer EML may be caused by thermally activated delayed fluorescence (TADF). The emitting layer EML may include a luminescent component that emits thermally activated delayed fluorescence, and in an embodiment, the emitting layer EML may be an emitting layer that emits thermally activated delayed fluorescence (emitting blue light). In an embodiment, the emitting layer EML may emit light having a maximum emission wavelength of about 440 nm to about 470 nm.

[0080] The emitting layer EML of the organic electroluminescent device 10 of the embodiment includes a polycyclic compound according to an embodiment of the present disclosure.

[0081] In the description, the term "substituted or unsubstituted" may refer to an unsubstituted group or a group substituted by at least one substituent selected from the group consisting of: deuterium, halogen, cyano, nitro, amino, silyl, oxy, mercapto, sulfinyl, sulfonyl, carbonyl, boron, phosphonyl oxide, phosphonyl sulfide, alkyl, alkenyl, alkoxy, cycloalkyl, aryl, and heterocyclic groups. Furthermore, each of the substituents listed above may be substituted or unsubstituted. For example, biphenyl may be described as aryl or a phenyl group substituted with a phenyl group.

[0082] In the description, the term "attached to an adjacent group to form a ring" indicates that a group is attached to an adjacent group to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle. Hydrocarbon rings include aliphatic hydrocarbon rings and aromatic hydrocarbon rings. Heterocycles include aliphatic heterocycles and aromatic heterocycles. Rings formed by attaching to adjacent groups can each be independently monocyclic or polycyclic. Additionally, rings formed by linking to each other can be attached to another ring to form a spirostructure.

[0083] In the description, the term "adjacent group" may refer to a pair of substituents in which the first substituent is attached to an atom that is directly attached to another atom substituted by the second substituent; a pair of substituents attached to the same atom; or a pair of substituents in which the first substituent is located spatially closest to the second substituent. For example, the two methyl groups in 1,2-dimethylbenzene can be interpreted as "adjacent groups" to each other, and the two ethyl groups in 1,1-diethylcyclopentane can be interpreted as "adjacent groups" to each other.

[0084] In the description, examples of halogen atoms may include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0085] In the description, the alkyl group may be a straight-chain alkyl group, a branched alkyl group, or a cycloalkyl group. The number of carbons in the alkyl group is 1 to 50, 1 to 30, 1 to 20, 1 to 10, 1 to 8, or 1 to 6. Examples of alkyl groups may include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2- Butyldecyl, 2-hexyldecyl, 2-octyldecyl, undecyl, dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, hexadecyl, hexadecyl, nonadecanyl, triadecyl, etc.

[0086] In the description, alkenyl can refer to a hydrocarbon group comprising at least one carbon-carbon double bond at the middle and / or any end of an alkyl group having two or more carbon atoms. Alkenyl groups can be straight-chain or branched. Although there is no specific limitation on the number of carbon atoms, it can be 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups include, but are not limited to, vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienylaryl, styryl, styrylvinyl, etc.

[0087] In the description, alkynyl can refer to a hydrocarbon group comprising at least one carbon-carbon triple bond at the middle and / or any end of an alkyl group having two or more carbon atoms. The alkynyl group can be straight-chain or branched. Although there is no specific limitation on the number of carbon atoms, it can be 2 to 30, 2 to 20, or 2 to 10. Specific examples of alkynyl groups may include, but are not limited to, ethynyl, propynyl, etc.

[0088] In the description, the cycloalkyl group can be any functional group or substituent derived from an aliphatic hydrocarbon ring, or any functional group or substituent derived from an aromatic hydrocarbon ring. The number of cyclic carbon atoms in the cycloalkyl group can be 5 to 60, 5 to 30, or 5 to 20.

[0089] In this description, aryl can refer to any functional group or substituent derived from an aromatic hydrocarbon ring. Aryl can be monocyclic or polycyclic. The number of cyclic carbon atoms in the aryl group can be 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracene, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, hexaphenyl, triphenylene, pyrene, benzofluoranthracene, 1,2-benzophenanthryl, etc.

[0090] In this description, a heterocyclic group can refer to any functional group or substituent derived from a ring containing at least one of B, O, N, P, Si, and S as a cyclic heteroatom. Heterocyclic groups include aliphatic heterocyclic groups and aromatic heterocyclic groups. Aromatic heterocyclic groups can be heteroaryl. Aliphatic heterocycles (aliphatic heterocyclic groups) and aromatic heterocycles (aromatic heterocyclic groups) can each be monocyclic or polycyclic independently.

[0091] In the description, the heterocyclic group may include at least one of B, O, N, P, Si, and S as a cyclic heteroatom. When the heterocyclic group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heterocyclic group may be a monocyclic or polycyclic heterocyclic group, and may include heteroaryl groups. The number of cyclic carbon atoms in the heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10.

[0092] In the description, the aliphatic heterocyclic group may include at least one of B, O, N, P, Si, and S as a cyclic heteroatom. The number of cyclic carbon atoms in the aliphatic heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10. Examples of aliphatic heterocyclic groups include, but are not limited to, ethylene oxide, cyclothioalkyl, pyrrolidinyl, piperidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, thioalkyl, tetrahydropyranyl, 1,4-dioxane, etc.

[0093] In the description, a heteroaryl group may include at least one of B, O, N, P, Si, and S as a cyclic heteroatom. When a heteroaryl group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heteroaryl group may be a monocyclic heteroaryl or a polycyclic heteroaryl. The number of cyclic carbon atoms in the heteroaryl group may be 2 to 30, 2 to 20, or 2 to 10. Examples of heteroaryl groups may include, but are not limited to, thiophene, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinel, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phenothiazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazole, N-arylcarbazole, N-heteroarylcarbazole, N-alkylcarbazole, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiaphene, thiophene-thiaphene, benzofuranyl, phenanthrolyl, isoxazolyl, thiadiazolyl, phenothiazolyl, phenothiazinyl, dibenzothiophene, dibenzofuranyl, etc.

[0094] In the description, the number of carbon atoms in the amino group is not particularly limited, but can be from 1 to 30. The amino group can include alkylamino, arylamino, or heteroarylamino. Examples of amino groups include, but are not limited to, methylamino, dimethylamino, aniline, diphenylamino, naphthylamino, 9-methyl-anthraylamino, triphenylamino, etc.

[0095] In the description, the thio group may include alkylthio and arylthio.

[0096] In the description, the alkoxy group (oxy group) can be straight-chain, branched, or cyclic. There is no particular limitation on the number of carbon atoms in the alkoxy group, but it can be, for example, 1 to 20 or 1 to 10. Examples of alkoxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentoxy, hexoxy, octoxy, nonoxy, decoxy, benzyloxy, etc.

[0097] Additionally, in the description, "-*" indicates the location to be connected (e.g., binding site).

[0098] The polycyclic compounds according to embodiments of this disclosure are represented by the following formula 1:

[0099] Formula 1

[0100]

[0101] In Equation 1, Z1 and Z2 can each be NAr1, O, or S independently. However, Z1 and Z2 cannot both be O at the same time.

[0102] In Formula 1, Ar1 can be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and Ar1 can be attached to an adjacent group to form a ring.

[0103] In Formula 1, R1 to R3 may each be independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and any R1 to R3 may be attached to an adjacent group to form a ring.

[0104] In Equation 1, a and b can each be an integer selected from 0 to 4 independently. At the same time, when a is an integer of 2 or greater, multiple R1s are the same or different from each other, and when b is an integer of 2 or greater, multiple R2s are the same or different from each other.

[0105] In Equation 1, c can be an integer selected from 0 to 3. Also, when c is an integer of 2 or greater, multiple R3s may be the same or different from each other.

[0106] In Equation 1, at least one selected from R1 to R3 is represented by Equation 2 below:

[0107] Formula 2

[0108]

[0109] In Formula 2, R4 to R8 may each be independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and any R4 to R8 may be attached to an adjacent group to form a ring.

[0110] In Equation 2, d, e, and g can each be an integer selected from 0 to 4 independently. At the same time, when d is an integer of 2 or greater, multiple R4s are the same or different from each other; when e is an integer of 2 or greater, multiple R5s are the same or different from each other; and when g is an integer of 2 or greater, multiple R7s are the same or different from each other.

[0111] In Equation 2, f and h can each be an integer selected from 0 to 5 independently. At the same time, when f is an integer of 2 or greater, multiple R6s are the same or different from each other, and when h is an integer of 2 or greater, multiple R8s are the same or different from each other.

[0112] In an implementation, Equation 2 can be connected to a specific location of Equation 1. In this case, Equation 1 can be represented by the following Equation 3:

[0113] Formula 3

[0114]

[0115] In Formula 3, Y1 to Y5 may each be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and at least one selected from Y1 to Y5 may be represented by Formula 2.

[0116] In Formula 3, R1 to R3 may each be independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and any R1 to R3 may be attached to an adjacent group to form a ring.

[0117] In Equation 3, i to k can each be an integer selected from 0 to 2 independently. At the same time, when i is 2, multiple R1s are the same or different from each other; when j is 2, multiple R2s are the same or different from each other; and when k is 2, multiple R3s are the same or different from each other.

[0118] In Equation 3, Z1 and Z2 are the same as those defined in Equation 1.

[0119] In the implementation, Z1 and Z2 in Equations 1 and 3 can each be NAr1 or O independently.

[0120] In this implementation, Z2 can be NAr1. In this case, equation 3 can be represented by the following equation 4:

[0121] Formula 4

[0122]

[0123] In Formula 4, Ar2 can be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and Ar2 can be attached to an adjacent group to form a ring.

[0124] In Equation 4, Z1, Y1 to Y5, R1 to R3, and i to k are the same as those defined in Equation 3.

[0125] In the implementation, any one of Y1 to Y5 selected from Equations 3 and 4 can be represented by Equation 2.

[0126] In this implementation, Y1 in Equation 3 can be represented by Equation 2. In this case, Equation 3 can be represented by the following Equation 5:

[0127] Formula 5

[0128]

[0129] In Formula 5, Y2 to Y5 can each be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0130] In Equation 5, Z1, Z2, R1 to R8 and d to k are the same as those defined in Equations 2 and 3.

[0131] In this implementation, Y2 in Equation 3 can be represented by Equation 2. In this case, Equation 3 can be represented by the following Equation 6:

[0132] Formula 6

[0133]

[0134] In Formula 6, Y1, Y3 to Y5 can each be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0135] In Equation 6, Z1, Z2, R1 to R8 and d to k are the same as those defined in Equations 2 and 3.

[0136] In this implementation, Y3 in Equation 3 can be represented by Equation 2. In this case, Equation 3 can be represented by the following Equation 7:

[0137] Formula 7

[0138]

[0139] In Formula 7, Y1, Y2, Y4 and Y5 may each be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0140] In Equation 7, Z1, Z2, R1 to R8 and d to k are the same as those defined in Equations 2 and 3.

[0141] In this implementation, Y4 in Equation 3 can be represented by Equation 2. In this case, Equation 3 can be represented by Equation 8 below:

[0142] Formula 8

[0143]

[0144] In Formula 8, Y1 to Y3 and Y5 can each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0145] In Equation 8, Z1, Z2, R1 to R8 and d to k are the same as those defined in Equations 2 and 3.

[0146] In this implementation, Y5 in Equation 3 can be represented by Equation 2. In this case, Equation 3 can be represented by the following Equation 9:

[0147] Formula 9

[0148]

[0149] In Formula 9, Y1 to Y4 can each be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0150] In Equation 9, Z1, Z2, R1 to R8 and d to k are the same as those defined in Equations 2 and 3.

[0151] In the embodiments, Y1 to Y5 in Formulas 3 to 9 may each be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted arylamine group having 6 to 30 cyclic carbon atoms, a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted carbazole group.

[0152] In the implementation, Ar1 in Equations 1, 3, and 5 to 9 can be represented by the following Equation 10:

[0153] Formula 10

[0154]

[0155] In Formula 10, Y can be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0156] In Equation 10, m is an integer selected from 0 to 5, and when m is an integer of 2 or greater, multiple Ys are either the same or different from each other.

[0157] In the implementation, Ar1 and / or Ar2 (in Equation 4) can be represented by Equation 10.

[0158] In embodiments, the polycyclic compound represented by Formula 1 may be any one of the compounds represented by group 1 below. However, this disclosure is not limited thereto:

[0159] Compound group 1

[0160] The polycyclic compounds represented by Formulas 1 to 9 can be used in the organic electroluminescent device 10 of the embodiments to improve the efficiency and lifespan of the organic electroluminescent device. For example, the polycyclic compounds can be used in the emission layer EML of the organic electroluminescent device 10 of the embodiments to improve the luminous efficiency and lifespan of the organic electroluminescent device.

[0161] In an embodiment, the emission layer EML may be a delayed fluorescence emission layer comprising a first compound and a second compound, and the polycyclic compound of the embodiment represented by Formula 1 may be included in the first compound of the emission layer EML. For example, the first compound may be a dopant, and the second compound may be the host. The host may be a host for delayed fluorescence emission, and the dopant may be a dopant for delayed fluorescence emission. For example, the polycyclic compound of the embodiment represented by Formula 1 may be used as a TADF dopant.

[0162] In some embodiments, the organic electroluminescent device 10 of the embodiment may include multiple emitting layers. The multiple emitting layers may be stacked sequentially; for example, the organic electroluminescent device 10 including multiple emitting layers may emit white light. The organic electroluminescent device 10 including multiple emitting layers may be an organic electroluminescent device having a series structure. When the organic electroluminescent device 10 includes multiple emitting layers, at least one emitting layer EML may include a polycyclic compound according to the present disclosure as described above.

[0163] The emitter layer (EML) may further include dopants, and any suitable material can be used as a dopant. For example, styrene derivatives (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4”-[(di-p-tolylamino)styrene]stilbene (DPAVB) and / or N-(4-((E)-2-(6-((E)-4-(diphenylamino)styrene)naphth-2-yl)vinyl)phenyl)-N-phenylaniline (N-BDAVBi) At least one of the following can be used as a dopant: perylene or its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)), pyrene or its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenebenzene, 1,4-bis(N,N-diphenylamino)pyrene and / or 1,6-bis(N,N-diphenylamino)pyrene) and 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBi), but the dopant is not limited thereto.

[0164] The emitter layer EML may further include a suitable host material. For example, the emitter layer EML may include, but is not limited to, tris(8-hydroxyquinoline)aluminum (Alq3), bis[2-(diphenylphosphine)phenyl]ether oxide (DPEPO), 4,4'-bis(carbazole-9-yl)biphenyl (CBP), 1,3-bis(carbazole-9-yl)benzene (mCP), 2,8-bis(diphenylphospho)dibenzo[b,d]furan (PPF), 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), poly(N-vinylcarbazole) (PVK), 9,10-bis(naphthyl-2-yl)anthracene (ADN), and 3-tert-butyl-9,10-bis(naphthyl-2-yl)anthracene (TB). At least one of the following is used as the host material: ADN, stilbene aromatic hydrocarbon (DSA), 4,4'-bis(9-carbazolyl)-2,2'-dimethylbiphenyl (CDBP), 2-methyl-9,10-bis(naphth-2-yl)anthracene (MADN), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH-2), hexaphenylcyclotrisiloxane (DPSiO3), octaphenylcyclotetrasiloxane (DPSiO4), 2,8-bis(diphenylphospho)dibenzofuran (PPF), and 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi).

[0165] When the emitting layer EML emits red light, the emitting layer EML may further include, for example, a fluorescent material comprising, tris(dibenzoylmethyl)phenanthroline europium (PBD:Eu(DBM)3(Phen)) and / or perylene. When the emitting layer EML emits red light, the dopants included in the emitting layer EML may be, for example, metal complexes (such as bis(1-phenylisoquinoline) iridium acetylacetonate (PIQIr(acac)), bis(1-phenylquinoline) iridium acetylacetonate (PQIr(acac)), tris(1-phenylquinoline) iridium (PQIr) and / or octaethylporphyrin platinum (PtOEP)), organometallic complexes, rubrene and / or its derivatives and / or 4-dicyanomethylene-2-(p-dimethylaminostyryl)-6-methyl-4H-pyran (DCM) and / or its derivatives).

[0166] When the emitting layer EML emits green light, the emitting layer EML may further include, for example, a fluorescent material comprising, tris(8-hydroxyquinoline)aluminum (Alq3). When the emitting layer EML emits green light, the dopants included in the emitting layer EML may be selected, for example, from metal complexes (such as planar-tris(2-phenylpyridine)iridium (Ir(ppy)3)), organometallic complexes, coumarins and their derivatives.

[0167] When the emitting layer EML emits blue light, the emitting layer EML may further include, for example, a fluorescent material, comprising any one selected from the group consisting of: spiro-DPVBi, spiro-6P, stilbene (DSB), stilbene aromatics (DSA), and polyfluorene (PFO) polymers and poly(p-phenylenevinylene) (PPV) polymers. When the emitting layer EML emits blue light, the dopants included in the emitting layer EML may be selected, for example, from metal complexes (such as (4,6-F₂ppy)₂Irpic), organometallic complexes, perylene, and their derivatives.

[0168] exist Figures 1 to 4 In the organic electroluminescent device 10 shown in the embodiment, an electron transport region (ETR) is provided on the emitter layer (EML). The electron transport region (ETR) may include at least one of a hole blocking layer (HBL), an electron transport layer (ETL), and an electron injection layer (EIL), but the embodiment is not limited thereto.

[0169] The electron transport region (ETR) can have a single layer formed of a single material, a single layer formed of multiple different materials, or a multilayer structure comprising multiple layers formed of multiple different materials.

[0170] For example, the electron transport region (ETR) may have a single-layer structure of an electron injection layer (EIL) or an electron transport layer (ETL), and may have a single-layer structure formed of an electron injection material and an electron transport material. In some embodiments, the electron transport region (ETR) may have a single-layer structure formed of a variety of different materials, or may have a structure in which electron transport layer (ETL) / electron injection layer (EIL) and / or hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) are stacked in the stated order starting from the emitter layer (EML), but is not limited thereto. The thickness of the electron transport region (ETR) may be, for example, approximately to approximately

[0171] The electron transport region (ETR) can be formed using one or more suitable methods, such as vacuum deposition, spin coating, casting, Langmuir-Brookett (LB) method, inkjet printing, laser printing, laser-induced thermal imaging (LITI), etc.

[0172] When the electron transport region (ETR) includes an electron transport layer (ETL), the ETL may include anthracene compounds. However, this disclosure is not limited thereto, and the ETL may include, for example, tris(8-hydroxyquinoline)aluminum (Alq3), 1,3,5-tris[(3-pyridyl)-benzene-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, bis[2-(diphenylphosphine)phenyl]ether oxide (DPEPO), 2-(4-(N-phenylbenzimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), and 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP). 4,7-Diphenyl-1,10-phenanthroline (Bphen), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthyl-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (tBu-PBD), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), bis(benzoquinoline-10-hydroxy)beryllium (Bebq2), 9,10-bis(naphthyl-2-yl)anthracene (ADN), or mixtures thereof. The thickness of the electron transport layer (ETL) can be approximately to approximately For example, about to approximately When the thickness of the electron transport layer (ETL) meets the above range, satisfactory (or appropriate) electron transport characteristics can be obtained without a significant increase in the driving voltage.

[0173] If the electron transport region (ETR) includes an electron injection layer (EIL), the ETR can be formed using metal halides (such as LiF, NaCl, CsF, RbCl, and / or RbI), lanthanides (such as Yb), metal oxides (such as Li₂O and / or BaO), and / or lithium 8-hydroxyquinoline (LiQ), but this disclosure is not limited thereto. The EIL can also be formed from a mixture of an electron injection material and an insulating organometallic salt. The organometallic salt can be a material having a band gap of about 4 eV or greater. For example, the organometallic salt can include metal acetates, metal benzoates, metal acetoacetates, metal acetylacetonates, and / or metal stearates. The thickness of the EIL can be approximately [missing information - likely a value]. to approximately Or about to approximately When the thickness of the electron injection layer (EIL) meets any of the above-mentioned ranges, satisfactory (or appropriate) electron injection properties can be obtained without a significant increase in the driving voltage.

[0174] The electron transport region (ETR) may include a hole blocking layer (HBL) as described above. The hole blocking layer (HBL) may include, but is not limited to, at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), bis[2-(diphenylphosphine)phenyl] ether oxide (DPEPO), and 4,7-diphenyl-1,10-phenanthroline (Bphen).

[0175] The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 can be a common electrode and / or a negative electrode. The second electrode EL2 can be a transmission electrode, a transmission-reflection electrode, or a reflection electrode. When the second electrode EL2 is a transmission electrode, the second electrode EL2 can be formed of a transparent metal oxide (e.g., ITO, IZO, ZnO, ITZO, etc.).

[0176] When the second electrode EL2 is a transmissive or reflective electrode, the second electrode EL2 may include at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, In, Sn, and Zn, or compounds thereof, or mixtures thereof (e.g., a mixture of Ag and Mg), or oxides thereof. In some embodiments, the second electrode EL2 may have a multilayer structure including a reflective or transmissive layer formed of any of the above materials and a transparent conductive layer formed of ITO, IZO, ZnO, ITZO, etc.

[0177] In some implementations, the second electrode EL2 may be connected to an auxiliary electrode. When the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.

[0178] Also see Figure 4 The organic electroluminescent device 10 according to the embodiment may further include a capping layer CPL on the second electrode EL2. The capping layer CPL may include, for example, α-NPD, NPB, TPD, m-MTDATA, Alq3, CuPc, N4,N4,N4',N4'-tetra(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15), 4,4',4"-tris(carbazole-9-yl)triphenylamine (TCTA), etc.

[0179] The organic electroluminescent device 10 according to embodiments of the present disclosure may include a polycyclic compound represented by Formula 1 as described above, thereby achieving excellent luminous efficiency and long lifespan characteristics. Furthermore, the organic electroluminescent device 10 of the embodiments can achieve high efficiency and long lifespan characteristics in the blue wavelength region.

[0180] The compounds and organic electroluminescent devices according to embodiments of the present disclosure will be described in more detail below with reference to examples and comparative examples. However, the examples shown below are for illustrative purposes only and the scope of the disclosure is not limited thereto.

[0181] Example

[0182] Synthesis of polycyclic compounds

[0183] In the following description, methods for synthesizing polycyclic compounds are provided as examples, but the synthesis methods according to embodiments of this disclosure are not limited to the following examples.

[0184] 1. Synthesis of Compound 1

[0185]

[0186] Compound A (9.05 g, 22.6 mmol) (which can be synthesized by the method disclosed in Synthesis Example (9) (Compounds (1-401)) of patent document WO 2016 / 152544, which is incorporated herein by reference in its entirety) was dissolved in THF (300 ml), and Br2 (3.61 g, 22.6 mmol) was added to it at 40 °C, and the reaction mixture was stirred for 10 hours. After the reaction was complete, the reaction product was concentrated, filtered, and fractionated (silica gel, toluene:hexane = 2:3) to obtain compound B (10.17 g, 90% yield).

[0187] Compound B (10 g, 20 mmol), compound C (10.5 g, 21 mmol), bis(dibenzylacetone)palladium(O) (Pd(dba)2, 0.183 g, 0.20 mmol), tri-tert-butylphosphonium tetrafluoroborate (P(t-Bu)3HBF4, 72.2 mg, 0.40 mmol), and sodium tert-butoxide (NaOt-Bu, 3.27 g, 34.0 mmol) were added to 100 mL of toluene, and the mixture was heated and stirred at 80 °C for 2 hours. After the addition of water, the resulting mixture was subjected to diatomaceous earth filtration and liquid separation to concentrate the organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain compound 1 (15.3 g, 84% yield). The molecular weight of compound 1, as measured by fast atom bombardment mass spectrometry (FAB MS), was 916.

[0188] 2. Synthesis of Compound 4

[0189]

[0190] Compound E (12.0 g, 85% yield) was synthesized by substantially the same reaction as in the synthesis of compound B, except that compound D (which can be synthesized by the method disclosed in Synthesis Example (8) (compounds (1-447)) of patent document WO 2016 / 152544, which is incorporated herein by reference in its entirety) was used instead of compound A.

[0191] Compound 4 (5.0 g, 72% yield) was synthesized by essentially the same method as compound 1, except that compound E was used instead of compound B. The molecular weight of compound 4, as measured by FAB MS, was 1083.

[0192] 3. Synthesis of Compound 22

[0193] (Synthesis of compound G)

[0194]

[0195] 1,5-Dibromo-2,3-dichlorobenzene (15.0 g, 49.7 mmol), diphenylamine (17.7 g, 104 mmol), Pd(dba)₂ (286 mg, 0.5 mmol), P(t-Bu)₃HBF₄ (269 mg, 1.49 mmol), and NaOt-Bu (14.3 g, 149 mmol) were added to 110 mL of toluene, and the mixture was heated and stirred at 80 °C for 2 hours. After the addition of water, the resulting mixture was subjected to diatomaceous earth filtration and liquid separation to concentrate the organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain compound G (19.9 g, 83% yield).

[0196] (Synthesis of compound H)

[0197]

[0198] Compound G (10.0 g, 20.8 mmol), compound F (15.2 g, 22.9 mmol), Pd(dba)2 (119 mg, 0.21 mmol), P(t-Bu)3HBF4 (112 mg, 0.62 mmol), and NaOt-Bu (3.0 g, 31.1 mmol) were added to 50 mL of toluene, and the mixture was heated and stirred at 95 °C for 2 hours. After the addition of water, the resulting mixture was subjected to diatomaceous earth filtration and liquid separation to concentrate the organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain compound H (23.1 g, 75% yield).

[0199] (Synthesis of compound 22)

[0200]

[0201] Compound H (23.0 g, 20.7 mmol) was added to tert-butylbenzene (tBuPh, 120 mL) and cooled to -15 °C. Tert-butyllithium (tBuLi, 1.6 M, 25.9 mL, 41.5 mmol) was added dropwise, and the reaction mixture was stirred at 60 °C for 3 hours. The resulting mixture was cooled again to -15 °C, and BBr3 (5.19 g, 41.5 mmol) was added and stirred at room temperature for 1 hour, followed by ice cooling. N,N-diisopropylethylamine (iPr2NEt, 5.4 g, 41.5 mmol) was added, and the mixture was stirred at an internal temperature of 100 °C for 3 hours. The reaction solution was ice-cooled. The resulting mixture was subjected to diatomaceous earth filtration and liquid separation to concentrate the organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain compound 22 (5.6 g, 25% yield). The molecular weight of compound 22, as measured by FAB MS, was 1084.

[0202] 4. Synthesis of Compound 31

[0203] (Synthesis of Compound I)

[0204]

[0205] 1-Bromo-2,3-dichlorobenzene (15.0 g, 66.4 mmol), bis(4-tert-butylphenyl)amine (20.6 g, 73.0 mmol), Pd(dba)2 (382 mg, 0.66 mmol), P(t-Bu)3HBF4 (359 mg, 2.0 mmol), and NaOt-Bu (9.57 g, 99.6 mmol) were added to 150 mL of toluene, and the mixture was heated and stirred at 60 °C for 5 hours. After the addition of water, the resulting mixture was subjected to diatomaceous earth filtration and liquid separation to concentrate the organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain compound I (21.2 g, 75% yield).

[0206] (Synthesis of compound K)

[0207]

[0208] The synthesis of compound K was carried out by essentially the same method as the synthesis of compound H, except that compounds I and J were used instead of compounds G and F, respectively.

[0209] (Synthesis of compound 31)

[0210]

[0211] Compound 31 was synthesized using essentially the same method as compound 22, except that compound K was used instead of compound H. The molecular weight of compound 31, as measured by FAB MS, was 1084.

[0212] 5. Synthesis of Compound 37

[0213]

[0214] (Synthesis of compound L)

[0215] The synthesis of compound L was carried out by essentially the same method as the synthesis of compound 1, except that 5-bromo-1,2,3-trichlorobenzene was used instead of compound B.

[0216] (Synthesis of compound M)

[0217] The synthesis of compound M was carried out by essentially the same method as the synthesis of compound G, except that compound L was used instead of 1,5-dibromo-2,3-dichlorobenzene.

[0218] (Synthesis of compound 37)

[0219] Compound 37 was synthesized using essentially the same method as compound 22, except that compound M was used instead of compound H. The molecular weight of compound 37, as measured by FAB MS, was 916.

[0220] 6. Synthesis of Compound 43

[0221]

[0222] The synthesis of compound N was carried out by essentially the same method as that used for the synthesis of compound I, except that compound L was used instead of 1-dibromo-2,3-dichlorobenzene.

[0223] Compound 43 was synthesized using essentially the same method as compound 22, except that compound N was used instead of compound H. The molecular weight of compound 43, as measured by FAB MS, was 1141.

[0224] 7. Synthesis of Compound 49

[0225] (Synthesis of compound O)

[0226]

[0227] The synthesis of compound O was carried out by essentially the same method as that used in the synthesis of compound G, except that 1,3-dibromo-5-fluorobenzene was used instead of 1,5-dibromo-2,3-dichlorobenzene.

[0228] (Synthesis of compound P)

[0229]

[0230] Compound O (15.0 g, 34.8 mmol), phenol (6.6 g, 69.7 mmol), and K₂CO₃ (19.2 g, 139 mmol) were added to 1-methyl-2-pyrrolidone (NMP, 150 mL) and stirred at 150 °C for 24 hours. After adding water and toluene to the reaction solution, the reaction mixture was washed with water to concentrate the organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain compound P (12.0 g, 68% yield).

[0231] (Synthesis of compound Q)

[0232]

[0233] Compound P (11.5 g, 22.8 mmol) was added to 1,2-dichlorobenzene (ODCB, 100 mL), followed by BBr3 (25.6 g, 114 mmol), and the mixture was stirred at 180 °C for 10 hours. After the reaction mixture was ice-cooled, iPr2NEt (44.2 g, 342 mmol) was added. The reaction solution was added to acetonitrile (300 mL) and filtered. The crystals obtained by filtration were purified by silica gel column chromatography to obtain compound Q (9.3 g, 80% yield).

[0234] (Synthesis of compound R)

[0235]

[0236] The synthesis of compound R was carried out by essentially the same method as the synthesis of compound B, except that compound Q was used instead of compound A.

[0237] (Synthesis of compound 49)

[0238]

[0239] Compound 49 was synthesized using essentially the same method as compound 1, except that compound R was used instead of compound B. The molecular weight of compound 49, as measured by FAB MS, was 1009.

[0240] 8. Synthesis of Compound 63

[0241]

[0242] The synthesis of compound S was carried out by essentially the same method as that used for the synthesis of compound P, except that 4-bromophenol was used instead of phenol.

[0243] The synthesis of compound T was carried out by essentially the same method as the synthesis of compound Q, except that compound S was used instead of compound P.

[0244] Compound 63 was synthesized using essentially the same method as compound 1, except that compound T was used instead of compound B. The molecular weight of compound 63, as measured by FAB MS, was 1009.

[0245] 9. Synthesis of Compound 68

[0246] (Synthesis of compound U)

[0247]

[0248] 1,3-Dibromo-5-fluorobenzene (15.0 g, 59.1 mmol), diphenylamine (11.9 g, 70.9 mmol), Pd(dba)2 (849 mg, 0.5 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (Sphos, 1.01 g, 2.48 mmol), and NaOt-Bu (6.81 g, 70.9 mmol) were added to 150 mL of toluene, and the mixture was heated and stirred at 60 °C for 8 hours. After the addition of water, the resulting mixture was subjected to diatomaceous earth filtration and liquid separation to concentrate the organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain compound U (14.5 g, 72% yield).

[0249] (Synthesis of compound V)

[0250]

[0251] The synthesis of compound V was carried out by essentially the same method as the synthesis of compound 1, except that compound U was used instead of compound B, and N1,N1,N3-triphenylbenzene-1,3-diamine was used instead of compound C.

[0252] (Synthesis of compound W)

[0253]

[0254] The synthesis of compound W was carried out by essentially the same method as the synthesis of compound S, except that compound V was used instead of compound O.

[0255] (Synthesis of compound X)

[0256]

[0257] The synthesis of compound X was carried out by essentially the same method as the synthesis of compound Q, except that compound W was used instead of compound P.

[0258] (Synthesis of compound 68)

[0259]

[0260] Compound 68 was synthesized using essentially the same method as compound 1, except that compound X was used instead of compound B. The molecular weight of compound 68, as measured by FAB MS, was 1176.

[0261] 10. Synthesis of Compound 76

[0262]

[0263] The synthesis of compound Y was carried out by essentially the same method as the synthesis of compound 1, except that compound U was used instead of compound B.

[0264] The synthesis of compound Z was carried out by essentially the same method as the synthesis of compound P, except that compound Y was used instead of compound O.

[0265] Compound 76 was synthesized using essentially the same method as compound Q, except that compound Z was used instead of compound P. The molecular weight of compound 76, as measured by FAB MS, was 841.

[0266] Manufacturing of organic electroluminescent devices

[0267] The organic electroluminescent devices of Examples 1 to 10 were manufactured using the above-described compounds as emission layer materials.

[0268] Examples of compounds

[0269]

[0270] Organic electroluminescent devices of Comparative Examples 1 to 5 were manufactured using the comparative example compounds X1 to X5 shown below as emission layer materials.

[0271] Comparative compounds

[0272]

[0273] The organic electroluminescent devices of the embodiments and comparative examples were manufactured by the following method.

[0274] Will have about A layer of ITO of a certain thickness was patterned on a glass substrate, rinsed with ultrapure water, and treated with UV ozone for approximately 10 minutes. Subsequently, HAT-CN was deposited... The thickness of α-NPD will be deposited as The thickness, and deposit mCP as The thickness is increased to form a hole transport region.

[0275] Next, during the formation of the emission layer, a polycyclic compound (selected from the compounds of the examples and comparative examples) and mCBP (3,3'-bis(9H-carbazole-9-yl)biphenyl) were co-deposited at a ratio of 10:90 to form an emission layer with approximately A layer of thickness.

[0276] Formed on the emitter layer using TPBi Thick layers formed with LiF A thick layer is formed to create an electron transport region. Next, an area approximately [missing information] is formed using aluminum (Al). The second electrode has a thickness of [missing information].

[0277] In this embodiment, a vacuum deposition apparatus is used to form a hole transport region, an emitter layer, an electron transport region, and a second electrode.

[0278] Evaluation of the properties of organic electroluminescent devices

[0279] To evaluate the characteristics of the organic electroluminescent devices according to the embodiments and comparative examples, luminance light distribution characteristics measurement devices (C9920-11 from Hamamatsu Photonics) were used to measure at 1000 cd / m². 2 The maximum emission wavelength (nm), maximum external quantum yield (%), external quantum efficiency (%), and half-width (nm) at the brightness.

[0280] Table 1

[0281]

[0282] Referring to the results in Table 1, when the emitter layer includes a polycyclic compound according to this embodiment, it is confirmed that at least one of the maximum external quantum yield (%), external quantum efficiency (%), and half-width (nm) is improved compared with the comparative example.

[0283] The polycyclic compounds of Examples 1 to 10 may exclude oxygen at at least one position of Z1 and Z2 in Formula 1, and may have PDA (planar donor-acceptor) emission by introducing a group represented by Formula 2 into a specific binding site. Therefore, it is believed that longer emission wavelengths can be prevented or reduced, and that an increase in half-width can be suppressed or reduced, thus achieving improved device efficiency.

[0284] Comparative Examples 1 to 4 include compounds in which oxygen is provided at both Z1 and Z2 positions in Formula 1, and indolecarbazole is a substituent. Therefore, it is believed that the compounds of Comparative Examples 1 to 4 have a relatively broad half-width and exhibit lower efficiency due to becoming CT (charge-transfer) emission.

[0285] Comparative Example 5 has compounds in which nitrogen is located at the Z1 and Z2 positions of Formula 1, but only includes diphenylamino groups as substituents. It is believed that Comparative Example 5 therefore exhibits particularly low luminescence efficiency.

[0286] By using a polycyclic compound represented by Formula 1 as the emitting layer material, the organic electroluminescent device of the embodiment can achieve high luminous efficiency in blue light, particularly in the wavelength region of 440 nm to 470 nm.

[0287] The organic electroluminescent device according to the embodiments of this disclosure can achieve high efficiency and long service life.

[0288] The polycyclic compounds according to embodiments of this disclosure can improve the efficiency and lifespan of organic electroluminescent devices.

[0289] As used herein, the terms “use,” “using,” and “used” can be considered synonymous with the terms “utilize,” “utilizing,” and “utilized,” respectively.

[0290] In addition, the terms “basically,” “about,” and similar terms are used as terms of approximation rather than terms of degree, and are intended to explain the inherent biases of measurements or calculations that would be recognized by a person skilled in the art.

[0291] Furthermore, any numerical ranges listed herein are intended to include all subranges with the same numerical precision within the listed range. For example, the range "1.0 to 10.0" is intended to include all subranges between the listed minimum value of 1.0 and the listed maximum value of 10.0 (inclusive), i.e., subranges with a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limit listed herein is intended to include all lower numerical limits included therein, and any minimum numerical limit listed in this specification is intended to include all higher numerical limits included therein. Therefore, the applicant reserves the right to modify this specification (including the claims) to explicitly list any subranges included within the scope explicitly listed herein.

[0292] Although this disclosure has been described with reference to exemplary embodiments thereof, it will be understood that this disclosure should not be limited to these embodiments, but that various changes and modifications may be made by those skilled in the art without departing from the spirit and scope of this disclosure.

[0293] Therefore, the scope of this disclosure is not intended to be limited to what is set forth in the detailed description of the specification, but is intended to be defined by the appended claims and their equivalents.

Claims

1. An organic electroluminescent device comprising: a first electrode; a hole transport zone on the first electrode; an emission layer on the hole transport zone; an electron transport zone on the emission layer; and a second electrode on the electron transport zone, wherein the first electrode and the second electrode each independently comprise one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, In, Sn, and Zn, or a compound selected from two or more of them, a mixture selected from two or more of them, or an oxide thereof, wherein the term “an oxide thereof” means one selected from an oxide of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, In, Sn, and Zn, an oxide of the compound, and an oxide of the mixture, and wherein the emission layer comprises a polycyclic compound represented by Formula 1: Formula 1 wherein, in Formula 1, Z 1 and Z 2 are each independently NAr 1 or O, provided that Z 1 and Z 2 are not simultaneously O, Ar 1 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and Ar 1 is optionally linked to an adjacent group to form a ring, R 1 to R 3 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and any of R 1 to R 3 are optionally linked to an adjacent group to form a ring, a and b are each independently an integer selected from 0 to 4, c is an integer selected from 0 to 3, and at least one selected from R 1 to R 3 is represented by Formula 2: Formula 2 wherein, in Formula 2, R 4 to R 8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and any of R 4 to R 8 are optionally linked to an adjacent group to form a ring, d, e, and g are each independently an integer selected from 0 to 4, and f and h are each independently an integer selected from 0 to 5. 2.The organic electroluminescent device according to claim 1, wherein the emission layer emits delayed fluorescence. 3.The organic electroluminescent device according to claim 1, wherein the emission layer is a delayed fluorescence emission layer comprising a first compound and a second compound, and the first compound comprises the polycyclic compound. 4.The organic electroluminescent device according to claim 1, wherein the emission layer is a thermally delayed fluorescence emission layer that emits light having a maximum emission wavelength of 440 nm to 470 nm. ​ 5. The organic electroluminescent device according to claim 1, wherein formula 1 is represented by formula 3: Formula 3 in formula 3, Y1to Y5are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 ring-forming carbon atoms, wherein, at least one selected from Y1to Y5is represented by formula 2, R1to R3are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 ring-forming carbon atoms, and any of R1to R3is optionally linked to an adjacent group to form a ring, i to k are each independently an integer selected from 0 to 2, and Z1and Z2are the same as defined in formula 1.

6. The organic electroluminescent device according to claim 5, wherein formula 3 is represented by formula 4: Formula 4 in formula 4, Ar2is a substituted or unsubstituted aryl group with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 ring-forming carbon atoms, and Ar2is optionally linked to an adjacent group to form a ring, and Z1, Y1to Y5, R1to R3, and i to k are the same as defined in formula 3.

7. The organic electroluminescent device according to claim 5, wherein Y1to Y5are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted arylamine group with 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted alkyl group with 1 to 8 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted carbazolyl group, and any of Y1to Y5selected from the above is represented by formula 2. wherein 8. The organic electroluminescent device according to claim 5, wherein formula 3 is represented by formula 5 or formula 6: Formula 5 Formula 6 in formula 5 and formula 6, Y1to Y5are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 ring-forming carbon atoms, and Z1, Z2, R1to R8, and d to k are the same as defined in formula 2 and formula 3.

9. The organic electroluminescent device according to claim 5, wherein formula 3 is represented by formula 7: Formula 7 in formula 7, Y1, Y2, Y4, and Y5are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 ring-forming carbon atoms, and Z1, Z2, R1to R8, and d to k are the same as defined in formula 2 and formula 3.

10. The organic electroluminescent device according to claim 5, wherein formula 3 is represented by formula 8 or formula 9: Formula 8 Formula 9 in formula 8 and formula 9, wherein ​ ​ ​ ​ ​ wherein ​ ​ ​ ​ ​ ​ wherein ​ Y1to Y5are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and Z1, Z2, R1to R8, and d to k are the same as defined in Formula 2 and Formula 3. 11.The organic electroluminescence device according to claim 1, wherein Ar1is represented by Formula 10: Formula 10 wherein In Formula 10, Y is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and m is an integer selected from 0 to 5. 12.The organic electroluminescence device according to claim 1, wherein the polycyclic compound represented by Formula 1 is any one selected from the group of compounds 1: Group of compounds 1 13.A polycyclic compound represented by Formula 1: Formula 1 wherein In Formula 1, Z1and Z2are each independently NAr1or O, provided that Z1and Z2are not simultaneously O, Ar1is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and Ar1is optionally connected to an adjacent group to form a ring, R1to R3are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and any of R1to R3is optionally connected to an adjacent group to form a ring, a and b are each independently an integer selected from 0 to 4, c is an integer selected from 0 to 3, and at least one selected from R1to R3is represented by Formula 2: Formula 2 In Formula 2, R4to R8are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and any of R4to R8is optionally connected to an adjacent group to form a ring, d, e, and g are each independently an integer selected from 0 to 4, and f and h are each independently an integer selected from 0 to 5.

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