Organic electroluminescence device and polycyclic compound for organic electroluminescence device

Abstract

This application relates to an organic electroluminescent device, comprising: a first electrode, a hole transport region disposed on the first electrode, an emission layer disposed on the hole transport region, an electron transport region disposed on the emission layer, and a second electrode disposed on the electron transport region. The emission layer may contain a polycyclic compound represented by Formula 1, thereby exhibiting high luminous efficiency: [Formula 1]

Description

[0001] Cross-reference to related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2019-0164049, filed on December 10, 2019, the entire contents of which are incorporated herein by reference. Technical Field

[0003] One or more aspects of the embodiments of this disclosure relate to organic electroluminescent devices and polycyclic compounds for said organic electroluminescent devices. Background Technology

[0004] Organic light-emitting displays (OLEDs) are currently being developed as image display devices. Unlike liquid crystal displays (LCDs), OLEDs are so-called self-emissive display devices, in which holes and electrons injected from a first electrode and a second electrode recombine in an emitting layer, and thus the luminescent material in the emitting layer, which includes organic compounds, emits light to achieve the display.

[0005] In applications of organic electroluminescent devices to display devices, there is a demand for organic electroluminescent devices with low driving voltage, high luminous efficiency and / or long lifespan, and there is a demand for new materials that can reliably obtain such properties for organic electroluminescent devices.

[0006] In recent years, in order to realize efficient organic electroluminescent devices, materials utilizing triplet energy phosphorescence emission, delayed fluorescence triplet-triplet annihilation (TTA) (where singlet excitons are generated through collisions of triplet excitons) and / or thermally activated delayed fluorescence (TADF) are being developed. Summary of the Invention

[0007] One or more aspects of the embodiments of this disclosure relate to organic electroluminescent devices having long lifespan and high efficiency, and polycyclic compounds used therein.

[0008] One or more aspects of embodiments of this disclosure relate to organic electroluminescent devices comprising thermally activated delayed fluorescence emission materials, and polycyclic compounds used as thermally activated delayed fluorescence emission materials.

[0009] One or more exemplary embodiments of this disclosure provide an organic electroluminescent device, comprising: a first electrode; a hole transport region disposed on the first electrode; an emission layer disposed on the hole transport region; an electron transport region disposed on the emission layer; and a second electrode disposed on the electron transport region, wherein the emission layer comprises a polycyclic compound represented by Formula 1:

[0010] [Formula 1]

[0011]

[0012] In Formula 1, Ar1 and Ar2 can each be independently 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; Ar3 and Ar4 can each be independently 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 / or bonded to adjacent groups to form a ring; R1 to R4 can each be independently a hydrogen atom, a deuterium 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 cyclic carbon atoms, or a substituted or unsubstituted alkyl group having 2 to 30 cyclic carbon atoms. The heteroaryl group with one cyclic carbon atom, where a and b can each be an integer from 0 to 3 independently, and X1 and X2 can each be a hydrogen atom, a deuterium atom, a cyano group, a carbonyl group, 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and at least one of X1 and X2 can be a cyano group, a carbonyl group, a substituted amine group, a substituted or unsubstituted heteroaryl group containing N having 2 to 30 cyclic carbon atoms, or an aryl group having 6 to 30 cyclic carbon atoms as a substituent of a cyano group, a carbonyl group, or an amine group.

[0013] In an implementation, the emission layer may be designed to emit delayed fluorescence.

[0014] In an embodiment, the emission layer may be a delayed fluorescence emission layer comprising a first compound and a second compound, and the first compound may include the polycyclic compound.

[0015] In one implementation, the emitting layer may be a delayed fluorescence emitting layer that emits blue light.

[0016] In the embodiments, X1 may be a cyano group, a carbonyl group, a substituted amine group, a substituted or unsubstituted heteroaryl group containing N and having 2 to 30 cyclic carbon atoms, or an aryl group having 6 to 30 cyclic carbon atoms as a substituent, and X2 may be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0017] In the embodiments, X1 and X2 may each be independently a cyano group, a carbonyl group, a substituted amine group, a substituted or unsubstituted heteroaryl group containing N and having 2 to 30 cyclic carbon atoms, or an aryl group having 6 to 30 cyclic carbon atoms as a substituent of a cyano group, a carbonyl group or an amine group.

[0018] In the implementation scheme, at least one of X1 and X2 can be represented by any one of 1-1 to 1-4:

[0019]

[0020] In 1-2 to 1-4, R6 and R9 can each be independently 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; R7 and R8 can each be independently 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 / or can be bonded to adjacent groups to form a ring; d can be an integer from 0 to 4; and X3 can be represented by any of 1-1 to 1-3.

[0021] In the implementation scheme, equation 1 can be represented by equation 2-1 or equation 2-2:

[0022] [Equation 2-1]

[0023]

[0024] [Equation 2-2]

[0025]

[0026] In Equations 2-1 and 2-2, X2, R1 to R4, Ar1 to Ar4, and a and b can each be independently the same as those defined in Equation 1.

[0027] In the implementation scheme, equation 1 can be represented by equation 3-1 or equation 3-2:

[0028] [Equation 3-1]

[0029]

[0030] [Equation 3-2]

[0031]

[0032] In equations 3-1 and 3-2, R 21 R 22 R 31 and R 32Each of these can be a hydrogen atom, a deuterium 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. e to h can each be an integer from 0 to 4. The dashed line can refer to an optional bond. X2, R1 to R4, Ar1 to Ar4, and a and b can each be the same as defined in Formula 1.

[0033] In the implementation scheme, equation 1 can be represented by equation 4-1 or equation 4-2:

[0034] [Equation 4-1]

[0035]

[0036] [Equation 4-2]

[0037]

[0038] In Formulas 4-1 and 4-2, X3 and X4 can each independently be a cyano group, a carbonyl group, a substituted amine group, a substituted or unsubstituted heteroaryl group containing N and having 2 to 30 cyclic carbon atoms, R9 and R9' can each independently be a hydrogen atom, a deuterium 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, d and d' can each independently be an integer from 0 to 4, and X2, R1 to R4, Ar1 to Ar4, and a and b can each independently be the same as defined in Formula 1.

[0039] In the implementation scheme, Ar1 and Ar2 can each be independently represented by Equation 5:

[0040] [Formula 5]

[0041]

[0042] In Formula 5, Y1 to Y5 can each be independently CA (e.g., a carbon atom substituted by A) or N, and A can be a hydrogen atom, a deuterium atom, or an alkyl group having 1 to 20 carbon atoms.

[0043] In the implementation plan, equation 1 can be represented by equation 6:

[0044] [Formula 6]

[0045]

[0046] In Equation 6, R10 and R 11 Each of these can be a hydrogen atom, a deuterium 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. j and k can each be an integer from 0 to 4. The dashed line can refer to an optional bond. R1 to R4, X1 and X2, Ar1, Ar2, and a and b can each be the same as defined in Formula 1.

[0047] In the implementation scheme, the compound represented by Formula 1 can be any one of the compounds represented by Compound Group 1.

[0048] One or more exemplary embodiments of this disclosure provide polycyclic compounds represented by Formula 1. Attached Figure Description

[0049] The accompanying drawings are included to provide a further understanding of this disclosure, and are incorporated in and form part of this specification. The drawings illustrate exemplary embodiments of this disclosure and, together with the description, serve to explain the principles of this disclosure. In the drawings:

[0050] Figure 1 This is a schematic cross-sectional view illustrating an organic electroluminescent device according to an embodiment of the present disclosure;

[0051] Figure 2 This is a schematic cross-sectional view illustrating an organic electroluminescent device according to an embodiment of the present disclosure.

[0052] Figure 3 This schematically illustrates a cross-sectional view of an organic electroluminescent device according to an embodiment of the present disclosure; and

[0053] Figure 4 This is a schematic cross-sectional view illustrating an organic electroluminescent device according to an embodiment of the present disclosure. Detailed Implementation

[0054] This disclosure may have various modifications and may be implemented in different forms, and exemplary embodiments will be explained in detail with reference to the accompanying drawings. However, this disclosure may be implemented in different forms and should not be construed as being limited to the embodiments set forth herein. Rather, all modifications, equivalents, and substitutions included within the spirit and scope of this disclosure should be included within this disclosure.

[0055] In the description, it should be understood that when a component or layer is referred to as being "on," "connected to," or "attached to" another component or layer, it can be directly on, directly connected to, or directly attached to the other component or layer, or there can be an intermediate component or layer. When a component is referred to as being "directly on," "directly connected to," or "directly attached to" another component, there is no intermediate component.

[0056] The same numbers throughout refer to the same components, and their repeated descriptions are not required. In the accompanying drawings, the thickness, scale, and dimensions of the components may be enlarged to effectively describe the technical content.

[0057] The term “and / or” includes any and all combinations of one or more of the related listed items. As used herein, the singular forms “a,” “an,” and “the” are intended to also include the plural forms unless the context clearly indicates otherwise.

[0058] As used herein, expressions such as “at least one of…”, “one of…”, and “selected from” modify the entire column of elements when preceding a column of elements, and do not modify any individual element in that column. Furthermore, the use of “may” when describing embodiments of this disclosure means “one or more embodiments of this disclosure”.

[0059] 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. Singular terms may include plural forms unless the context clearly indicates otherwise.

[0060] Furthermore, terms such as "below," "down," "above," and "up" 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 drawings.

[0061] 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 meaning consistent with their meaning in the context of the relevant field, unless explicitly defined herein, and should not be interpreted in an ideal or overly formal sense.

[0062] It should be understood that the terms “includes,” “including,” “comprises,” “comprising,” and / or “have” are intended to specify the presence of a designated feature, integer, step, operation, element, component, or combination thereof in the disclosure, but do not exclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.

[0063] In the following description, an organic electroluminescent device according to an embodiment of the present disclosure and the compounds contained therein will be described with reference to the accompanying drawings.

[0064] Figures 1 to 4 This is a schematic cross-sectional view illustrating an organic electroluminescent device according to an embodiment of the present disclosure. Reference Figures 1 to 4 In each organic electroluminescent device 10, the first electrode EL1 and the second electrode EL2 are arranged to face each other, and the emission layer EML can be disposed between the first electrode EL1 and the second electrode EL2.

[0065] In addition to the emitter layer EML, each organic electroluminescent device 10 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, each organic electroluminescent device 10 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 may include a capping layer CPL disposed on the second electrode EL2.

[0066] The organic electroluminescent device 10 of the embodiment may contain a polycyclic compound, which will be described later, in the emitter layer EML disposed between the first electrode EL1 and the second electrode EL2. However, the embodiment is not limited to this, and the organic electroluminescent device 10 of the embodiment may contain the compound according to the embodiment not only in the emitter layer EML, but also in the hole transport region HTR and / or the electron transport region ETR (which are among the multiple functional layers disposed between the first electrode EL1 and the second electrode EL2), and / or in the capping layer CPL disposed on the second electrode EL2.

[0067] and Figure 1 compared to, 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 compared to, 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 compared to, Figure 4 A cross-sectional view of an organic electroluminescent device 10 according to an embodiment is shown, the organic electroluminescent device 10 including a capping layer CPL disposed on a second electrode EL2.

[0068] The first electrode EL1 may be conductive. The first electrode EL1 may be formed of a metal alloy and / or a conductive compound. The first electrode EL1 may be a pixel electrode and / or a positive electrode (e.g., an anode). The first electrode EL1 may be a transmissive electrode, a semi-transmissive reflective electrode, or a reflective electrode. When the first electrode EL1 is a transmissive electrode, it may contain a transparent metal oxide (e.g., 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 semi-transmissive reflective electrode or a reflective electrode, it may contain silver (Ag), magnesium (Mg), copper (Cu), aluminum (Al), platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), neodymium (Nd), iridium (Ir), chromium (Cr), lithium (Li), calcium (Ca), LiF / Ca, LiF / Al, molybdenum (Mo), titanium (Ti), indium (In), tin (Sn), zinc (Zn), their compounds, mixtures thereof (e.g., a mixture of Ag and Mg), or oxides thereof.

[0069] In some embodiments, the first electrode EL1 may have a multilayer structure, including a reflective or semi-transparent reflective layer formed of the materials described above, and a transparent conductive 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

[0070] A hole transport region HTR is provided on the first electrode EL1. The hole transport region HTR may include at least one of a hole injection layer HIL, a hole transport layer HTL, a hole buffer layer, and an electron blocking layer.

[0071] The hole transport region (HTR) can have a single layer made of a single material, a single layer made of multiple different materials, or a multilayer structure including multiple layers made of multiple different materials.

[0072] For example, the hole transport region HTR can have a single-layer structure of a hole injection layer HIL or a hole transport layer HTL, or it can have a single-layer structure formed of a hole injection material and a hole transport material. In some embodiments, the hole transport region HTR can 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 sequentially from the first electrode EL1, but the embodiments are not limited thereto.

[0073] Hole transport regions (HTRs) can be formed using any suitable method (e.g., vacuum deposition, spin coating, tape casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and / or laser-induced thermal imaging (LITI) method).

[0074] The hole injection layer (HIL) may contain, for example, phthalocyanine compounds (e.g., 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”-tri{N-(2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA), poly(3,4-ethylenedioxythiophene) / poly(4- Poly(4-styrene sulfonate) (PEDOT / PSS), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), polyaniline / camphor sulfonic acid (PANI / CSA), polyaniline / poly(4-styrene sulfonate) (PANI / PSS), N,N'-di(naphthyl-1-yl)-N,N'-diphenyl-benzidine (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-hexacarbonyl nitrile (HAT-CN), etc.

[0075] Hole transport layer (HTL) can contain any suitable material. For example, HTL can further contain carbazole derivatives (e.g., N-phenylcarbazole and / or polyvinylcarbazole), fluorene 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)), N,N'-bis(naphthyl-1-yl)-N,N'-diphenyl-benzidine (NPD), 4,4'-cyclohexylenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), 1,3-bis(N-carbazolyl)benzene (mCP), etc.

[0076] The electron blocking layer (EBL) may contain, for example, carbazole derivatives (e.g., N-phenylcarbazole and / or polyvinylcarbazole), fluorene 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)), N,N'-bis(naphthyl-1-yl)-N,N'-diphenyl-benzidine (NPD), 4,4'-cyclohexylenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), mCP, etc.

[0077] The hole transport region (HTR) can have approximately to approximately The thickness, for example, approximately 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... to approximately For example, the thickness of the electron blocking layer EBL can be approximately to approximately When the thicknesses of the hole transport region (HTR), hole injection layer (HIL), hole transport layer (HTL), and electron blocking layer (EBL) meet the ranges described above, satisfactory hole transport properties can be achieved without a significant increase in driving voltage.

[0078] In addition to the materials described above, the hole transport region (HTR) may further contain a charge-generating material to increase conductivity. The charge-generating material may be substantially 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 a quinone derivative, a metal oxide, or a cyano-containing compound, but is not limited thereto. Non-limiting examples of p-dopers include, but are not limited to, quinone derivatives (e.g., tetracyanoquinone dimethyl ether (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinone dimethyl ether (F4-TCNQ)), metal oxides (e.g., tungsten oxide and / or molybdenum oxide), etc.

[0079] 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 based on the wavelength of light emitted from the emitter layer (EML) and can increase the light emission efficiency. Materials that can be included in the hole transport region (HTR) may also be included in the hole buffer layer. The electron blocking layer (EBL) can prevent or reduce electron injection from the electron transport region (ETR) into the hole transport region (HTR).

[0080] An 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 made of a single material, a single layer made of multiple different materials, or a multilayer structure with multiple layers made of multiple different materials.

[0081] The emitting layer can be designed to emit one of the following colors of light: red, green, blue, white, yellow, and cyan. The emitting layer EML can contain fluorescent emitting materials and / or phosphorescent emitting materials.

[0082] In an embodiment, the emitting layer EML can be a fluorescent emitting layer. For example, some of the light emitted from the emitting layer EML can be caused by thermally activated delayed fluorescence (TADF). For example, the emitting layer EML can include a light-emitting component for emitting thermally activated delayed fluorescence, and in an embodiment, the emitting layer EML can be an emitting layer for emitting thermally activated delayed fluorescence that emits blue light.

[0083] The emitting layer EML of the organic electroluminescent device 10 of the embodiment comprises a polycyclic compound according to the embodiments of the present disclosure.

[0084] In the description, the term "substituted or unsubstituted" means unsubstituted or substituted by at least one substituent selected from the group consisting of deuterium, halogen, cyano, nitro, amino, silyl, oxy, thio, sulfinyl, sulfonyl, carbonyl, boron, phosphine oxide, phosphine sulfide, alkyl, alkenyl, alkoxy, aliphatic cyclic, aryl, and heterocyclic groups. In some embodiments, each of these substituents may be further substituted or unsubstituted. For example, a biphenyl group may be interpreted as a so-called aryl group, or as a phenyl group substituted with a phenyl group.

[0085] In the description, the term "bonded to an adjacent group to form a ring" can refer to the state of bonding to an adjacent group to form a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring. The hydrocarbon ring can be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The ring formed by bonding to an adjacent group can be a monocyclic or polycyclic ring. In some embodiments, the ring formed by bonding to each other can be further linked to another ring to form a spirocyclic structure.

[0086] In the description, the term "adjacent group" can refer to a substituent on the same atom or point, a substituent on an atom directly connected to the base atom or point, or a substituent spatially positioned (e.g., within an intramolecular bonding distance) to the corresponding 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.

[0087] In the description, examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms.

[0088] In the description, the alkyl group can be a straight-chain, branched, or cyclic alkyl group. The number of carbon atoms in the alkyl group can be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Non-limiting examples of alkyl groups include methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, sec-butyl groups, tert-butyl groups, isobutyl groups, 2-ethylbutyl groups, 3,3-dimethylbutyl groups, n-pentyl groups, isopentyl groups, neopentyl groups, tert-pentyl groups, cyclopentyl groups, 1-methylpentyl groups, 3-methylpentyl groups, 2-ethylpentyl groups, 4-methyl-2-pentyl groups, n-hexyl groups, 1-methylhexyl groups, 2-ethyl... Hexyl group, 2-butylhexyl group, cyclohexyl group, 4-methylcyclohexyl group, 4-tert-butylcyclohexyl group, n-heptyl group, 1-methylheptyl group, 2,2-dimethylheptyl group, 2-ethylheptyl group, 2-butylheptyl group, n-octyl group, tert-octyl group, 2-ethyloctyl group, 2-butyloctyl group, 2-hexyloctyl group, 3,7-dimethyloctyl group, cyclooctyl group, n-nonyl group, n-decyl group, adamantyl group, 2-ethyl Decyl group, 2-butyldecyl group, 2-hexyldecyl group, 2-octyldecyl group, n-undecyl group, n-dodecyl group, 2-ethyldodecyl group, 2-butyldodecyl group, 2-hexyldodecyl group, 2-octyldodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecanyl group, n-hexadecyl group, 2-ethylhexadecyl group, 2-butylhexadecyl group, 2-hexylhexadecyl group, 2-octylhexadecyl group, n-heptadecyl group, n-octadecyl group, n-octadecyl group, n-heptadecyl group, n-octadecyl group, n-hexa ...

[0089] In this description, the term "aryl group" can refer to any functional group or substituent derived from an aromatic hydrocarbon ring. An aryl group can be a monocyclic or polycyclic aryl group. The number of cyclic carbon atoms in the aryl group can be 6 to 30, 6 to 20, or 6 to 15. Non-limiting examples of aryl groups include phenyl, naphthyl, fluorenyl, anthraceneyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, hexaphenyl, benzo[a]phenanthryl, pyrene, benzo[a]fluoranyl, and anthraceneyl. Base, etc.

[0090] In the description, the heteroaryl group may contain at least one of boron (B), oxygen (O), nitrogen (N), phosphorus (P), silicon (Si), and sulfur (S) as a heteroatom. When the 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 group or a polycyclic heteroaryl group. The number of cyclic carbon atoms in the heteroaryl group may be 2 to 30, 2 to 20, or 2 to 10, and the number of cyclic heteroatoms may be 1 to 5, 1 to 3, for example, 1, 2, or 3. Non-limiting examples of heteroaryl groups include those derived from: thiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, triazole, pyridine, bipyridine, pyrimidine, triazine, acridine, pyridazine, pyrazine, quinoline, quinazoline, quinoxaline, phenoxazine, phthalazine, pyridopyrimidine, pyridopyrazine, pyrazinopyrazine, isoquinoline, indole, carbazole, N-arylcarbazole, N-heteroarylcarbazole, N-alkylcarbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophene, dibenzothiophene, thienothiophene, benzofuran, phenanthroline, isoxazole, thiadiazole, phenothiazine, dibenzothiophene, dibenzofuran, etc.

[0091] The number of carbon atoms in the amine group is not specifically limited in the description, but can be from 1 to 30. The amine group can be an alkylamine group, an arylamine group, or a heteroarylamine group. Non-limiting examples of amine groups include methylamine groups, dimethylamine groups, phenylamine groups, diphenylamine groups, naphthylamine groups, 9-methyl-anthraylamine groups, triphenylamine groups, etc.

[0092] In the description, "-*" refers to a connection point.

[0093] The polycyclic compound according to the embodiments of this disclosure can be represented by Formula 1:

[0094] [Formula 1]

[0095]

[0096] In Formula 1, Ar1 and Ar2 can each be independently 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.

[0097] In Formula 1, Ar3 and Ar4 can each be independently 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 / or can be bonded to adjacent groups to form a ring.

[0098] In Formula 1, R1 to R4 can each be independently a hydrogen atom, a deuterium 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0099] In Equation 1, a and b can each be an integer from 0 to 3 independently. When a is 2 or greater than 2, multiple R1s can be the same or different from each other, and when b is 2 or greater than 2, multiple R2s can be the same or different from each other.

[0100] In Formula 1, X1 and X2 can each independently be a hydrogen atom, a deuterium atom, a cyano group, a carbonyl group, 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0101] However, in some embodiments, at least one of X1 and X2 is a cyano group, a carbonyl group, a substituted amine group, a substituted or unsubstituted heteroaryl group containing N and having 2 to 30 cyclic carbon atoms, or an aryl group having 6 to 30 cyclic carbon atoms as a substituent of a cyano group, a carbonyl group or an amine group.

[0102] In some implementations, in Formula 1, any hydrogen atom can be replaced by a deuterium atom.

[0103] In the embodiments, X1 in Formula 1 may be a cyano group, a carbonyl group, a substituted amine group, a substituted or unsubstituted heteroaryl group containing N and having 2 to 30 cyclic carbon atoms, or an aryl group having 6 to 30 cyclic carbon atoms as a substituent of a cyano group, a carbonyl group or an amine group, and X2 may be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0104] In the embodiments, X1 and X2 may each be independently a cyano group, a carbonyl group, a substituted amine group, a substituted or unsubstituted heteroaryl group containing N and having 2 to 30 cyclic carbon atoms, or an aryl group having 6 to 30 cyclic carbon atoms as a substituent of a cyano group, a carbonyl group or an amine group.

[0105] In the implementation scheme, at least one of X1 and X2 in Equation 1 can be represented by one of 1-1 to 1-4:

[0106]

[0107] In 1-2, R6 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.

[0108] In 1-3, R7 and R8 can each be independently 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 / or can be bonded to adjacent groups to form a ring.

[0109] In 1-4, R9 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.

[0110] In 1-4, d can be an integer from 0 to 4, and when d is 2 or greater than 2, multiple R9s can be the same or different from each other.

[0111] In 1-4, X3 can be represented by any of the methods from 1-1 to 1-3.

[0112] In the implementation scheme, equation 1 can be represented by equation 2-1 or equation 2-2:

[0113] [Equation 2-1]

[0114]

[0115] [Equation 2-2]

[0116]

[0117] In Equations 2-1 and 2-2, X2, R1 to R4, Ar1 to Ar4, and a and b can each be independently the same as those defined in Equation 1.

[0118] In the implementation scheme, equation 1 can be represented by equation 3-1 or equation 3-2:

[0119] [Equation 3-1]

[0120]

[0121] In Equation 3-1, R 21 and R 22 Each of the following can be independently a hydrogen atom, a deuterium 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0122] In Equation 3-1, e can be an integer from 0 to 4, and when e is 2 or greater than 2, multiple R 21 They can be the same as or different from each other.

[0123] In Equation 3-1, f can be an integer from 0 to 4, and when f is 2 or greater than 2, multiple R 22 They can be the same as or different from each other.

[0124] In Equation 3-1, X2, R1 to R4, Ar1 to Ar4, and a and b can each be independently the same as those defined in Equation 1.

[0125] [Equation 3-2]

[0126]

[0127] In Equation 3-2, R 21 R 22 R 31 and R 32 Each of the following can be independently a hydrogen atom, a deuterium 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0128] In Equation 3-2, e can be an integer from 0 to 4, and when e is 2 or greater than 2, multiple R 21 They can be the same as or different from each other.

[0129] In Equation 3-2, f can be an integer from 0 to 4, and when f is 2 or greater than 2, multiple R 22 They can be the same as or different from each other.

[0130] In Equation 3-2, g can be an integer from 0 to 4, and when g is 2 or greater than 2, multiple R 31 They can be the same as or different from each other.

[0131] In Equation 3-2, h can be an integer from 0 to 4, and when h is 2 or greater than 2, multiple R 32 They can be the same as or different from each other.

[0132] In Equation 3-2, R1 to R4, Ar1 to Ar4, and a and b can each be independently the same as those defined in Equation 1.

[0133] In Formulas 3-1 and 3-2, the dashed lines represent optional bonds (e.g., the relationship between the two groups at the ends of the dashed lines can be bonded or unbonded). "Bonded" means that carbon atoms are bonded to each other to form a single bond, and "unbonded" means that carbon atoms are not bonded to each other and each carbon atom is bonded to a hydrogen atom.

[0134] In the implementation scheme, equation 1 can be represented by equation 4-1 or equation 4-2:

[0135] [Equation 4-1]

[0136]

[0137] In Formula 4-1, X3 can be a cyano group, a carbonyl group, a substituted amine group, or a substituted or unsubstituted heteroaryl group containing N and having 2 to 30 cyclic carbon atoms.

[0138] In Formula 4-1, R9 can be a hydrogen atom, a deuterium 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0139] In Equation 4-1, d can be an integer from 0 to 4, and when d is 2 or greater than 2, multiple R9s can be the same or different from each other.

[0140] In Equation 4-1, X2, R1 to R4, Ar1 to Ar4, and a and b can each be independently the same as those defined in Equation 1.

[0141] [Equation 4-2]

[0142]

[0143] In Formula 4-2, X3 and X4 can each be independently a cyano group, a carbonyl group, a substituted amine group, or a substituted or unsubstituted heteroaryl group containing N and having 2 to 30 cyclic carbon atoms.

[0144] In Formula 4-2, R9 and R9' can each independently be a hydrogen atom, a deuterium 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0145] In Equation 4-2, d and d' can each be an integer from 0 to 4 independently, and when d is 2 or greater than 2, multiple R9s can be the same or different from each other, and when d' is 2 or greater than 2, multiple R9's can be the same or different from each other.

[0146] In Equation 4-2, R1 to R4, Ar1 to Ar4, and a and b can each be independently the same as those defined in Equation 1.

[0147] In the implementation scheme, Ar1 and Ar2 can each be independently represented by Equation 5:

[0148] [Formula 5]

[0149]

[0150] In Equation 5, Y1 to Y5 can each be independently CA (e.g., carbon atoms substituted by A) or N.

[0151] In Formula 5, A can be a hydrogen atom, a deuterium atom, or an alkyl group having 1 to 20 carbon atoms.

[0152] In the implementation plan, equation 1 can be represented by equation 6:

[0153] [Formula 6]

[0154]

[0155] In Equation 6, R 10 and R 11 Each of the following can be independently a hydrogen atom, a deuterium 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0156] In Equation 6, j can be an integer from 0 to 4, and when j is 2 or greater than 2, multiple R 10 They are the same or different from each other.

[0157] In Equation 6, k can be an integer from 0 to 4, and when k is 2 or greater than 2, multiple R 11 They can be the same as or different from each other.

[0158] In Equation 6, the dashed line represents an optional key, as described above.

[0159] In Equation 6, R1 to R4, X1, X2, Ar1, Ar2, and a and b can each be independently the same as those defined in Equation 1.

[0160] In the embodiments, the polycyclic compound represented by Formula 1 can be any of the compounds selected from Group 1 of compounds. However, this disclosure is not limited thereto.

[0161] [Compound Group 1]

[0162]

[0163]

[0164]

[0165] In the implementation scheme, the compounds represented by compound group 1 may each independently have one or more hydrogen atoms substituted by deuterium atoms.

[0166] The polycyclic compounds described above can be used in the organic electroluminescent device 10 of the embodiment to improve the efficiency and / or lifespan of the organic electroluminescent device. For example, the polycyclic compounds described above can be used in the emitting layer EML of the organic electroluminescent device 10 of the embodiment to improve the luminous efficiency and / or lifespan of the organic electroluminescent device.

[0167] 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 compound.

[0168] In some embodiments, the host can be a host for delayed fluorescence emission, and the dopant can be a dopant for delayed fluorescence emission. In some embodiments, the polycyclic compound represented by Formula 1 can be included as a dopant material in the emission layer EML. For example, the polycyclic compound of the embodiment represented by Formula 1 can be used as a TADF dopant.

[0169] In some embodiments, the organic electroluminescent device 10 of the embodiment may include multiple emission layers. The multiple emission layers may be stacked and provided sequentially, and for example, the organic electroluminescent device 10 including multiple emission layers may be designed to emit white light. The organic electroluminescent device including multiple emission layers may be an organic electroluminescent device having a tandem structure. When the organic electroluminescent device 10 includes multiple emission layers, at least one emission layer EML may contain a polycyclic compound according to embodiments of the present disclosure.

[0170] The emitter layer (EML) may further contain dopants, and any suitable material can be used as a dopant. For example, styrene derivatives (e.g., 1,4-bis[2-(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)), perylene, and... At least one of the following can be used as a dopant: pyrene and / or its derivatives (e.g., 2,5,8,11-tetratert-butylperylene (TBPe)), pyrene and / or its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenebenzene, 1,4-bis(N,N-diphenylamino)pyrene, 1,6-bis(N,N-diphenylamino)pyrene), and 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi). However, the embodiments are not limited thereto.

[0171] The emitter layer EML can further contain any suitable material as the host material. For example, the emitter layer EML can contain tris(8-hydroxyquinoline)aluminum (Alq3), bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 4,4'-bis(carbazole-9-yl)biphenyl (CBP), 1,3-bis(carbazole-9-yl)benzene (mCP), 2,8-bis(diphenylphosphino)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 (TBADN). The main material may be at least one of stilbene arylene (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), without limitation.

[0172] When the emitting layer EML is intended to emit red light, the emitting layer EML may further contain, for example, a fluorescent material, including tris(dibenzoylmethane)phenanthroline europium (PBD:Eu(DBM)3(Phen)) or perylene. When the emitting layer EML is intended to emit red light, the dopants contained in the emitting layer EML may be, for example, metal complexes or organometallic complexes (e.g., iridium bis(1-phenylisoquinoline)acetylacetonate (PIQIr(acac)), iridium bis(1-phenylquinoline)acetylacetonate (PQIr(acac)), tris(1-phenylquinoline)iridium (PQIr) and octaethylporphyrin platinum (PtOEP)), rubrene and / or its derivatives, and / or 4-dicyanomethylene-2-(p-dimethylaminostyryl)-6-methyl-4H-pyran (DCM) and / or its derivatives).

[0173] When the emitting layer EML is intended to emit green light, the emitting layer EML may further include, for example, a fluorescent material, such as tris(8-hydroxyquinoline)aluminum (Alq3). When the emitting layer EML is intended to emit green light, the dopants included in the emitting layer EML may be selected, for example, from metal complexes, organometallic complexes (e.g., planar-tris(2-phenylpyridine)iridium (Ir(ppy)3)), coumarins and their derivatives.

[0174] When the emitting layer EML is intended to emit blue light, the emitting layer EML may further comprise, for example, a fluorescent material, including any one selected from the group consisting of spiro-DPVBi, spiro-6P, stilbene-phenylene (DSB), stilbene-arylene (DSA), polyfluorene-based polymers (PFO), and poly(p-phenylenevinylene) (PPV)-based polymers. When the emitting layer EML is intended to emit blue light, the dopant contained in the emitting layer EML may be selected from, for example, metal complexes, organometallic complexes (e.g., (4,6-F₂ppy)₂Irpic), and perylene and / or its derivatives.

[0175] exist Figures 1 to 4 In the organic electroluminescent device 10 of the illustrated 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.

[0176] The electronic transport region (ETR) can have a single layer made of a single material, a single layer made of multiple different materials, or a multi-layer structure including multiple layers made of multiple different materials.

[0177] For example, the electron transport region (ETR) can have a single-layer structure of an electron injection layer (EIL) or an electron transport layer (ETL), or it can have a single-layer structure formed of an electron injection material and an electron transport material. In some embodiments, the electron transport region (ETR) can have a single-layer structure formed of a variety of different materials, or it can have a structure in which an electron transport layer (ETL) / electron injection layer (EIL) or a hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) are stacked sequentially from the emitter layer (EML), but is not limited thereto. The thickness of the electron transport region (ETR) can be, for example, approximately [missing information - likely a number]. to approximately

[0178] The electron transport region (ETR) can be formed using any suitable method (e.g., vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, laser-induced thermal imaging (LITI) method, etc.).

[0179] When the electron transport region (ETR) includes an electron transport layer (ETL), the ETR may contain an anthracene-based compound. However, embodiments are not limited to this, and the electron transport region may contain, 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-(diphenylphosphino)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-quinoline-N1,O8)-(1,1'-biphenyl-4-oxoline)aluminum (BAlq), bis(benzoquinoline-10-oxoline)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 range described above, satisfactory electron transport characteristics can be obtained without a significant increase in driving voltage.

[0180] When the electron transport region (ETR) includes an electron injection layer (EIL), the ETR can be formed using metal halides (e.g., LiF, NaCl, CsF, RbCl and / or RbI), lanthanides (e.g., Yb), metal oxides (e.g., Li₂O and / or BaO), or lithium quinoline (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. The organometallic salt can include, for example, metal acetates, metal benzoates, metal acetoacetates, metal acetylacetonates, and / or metal stearates. The thickness of the EIL can be approximately... to approximately or about to approximately When the thickness of the electron injection layer (EIL) meets the range described above, satisfactory electron injection properties can be obtained without a significant increase in driving voltage.

[0181] 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-(diphenylphosphino)phenyl] ether oxide (DPEPO), and 4,7-diphenyl-1,10-phenanthroline (Bphen).

[0182] A second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 can be a common electrode or a negative electrode (e.g., a cathode). The second electrode EL2 can be a transmission electrode, a semi-transmissive reflective electrode, or a reflective 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.).

[0183] When the second electrode EL2 is a semi-transparent reflective electrode or a reflective electrode, the second electrode EL2 may contain Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, In, Sn, Zn, their compounds, mixtures thereof (e.g., a mixture of Ag and Mg) or their oxides.

[0184] In some embodiments, the second electrode EL2 may have a multilayer structure, which includes a reflective or semi-transparent reflective layer formed of the materials described above, and a transparent conductive layer formed of ITO, IZO, ZnO, ITZO, etc.

[0185] In some implementations, the second electrode EL2 can be connected to an auxiliary electrode. When the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 can be reduced.

[0186] refer to 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 contain, 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.

[0187] The organic electroluminescent device 10 according to the embodiments of this disclosure may contain a polycyclic compound represented by Formula 1 as described above, thereby obtaining excellent luminous efficiency and / or 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.

[0188] 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. The illustrative examples are provided for understanding the present disclosure only, and the scope of the disclosure is not limited thereto.

[0189] [Example]

[0190] (Synthesis of polycyclic compounds)

[0191] In the following description, methods for synthesizing polycyclic compounds are provided as examples, but the methods for synthesizing according to embodiments of this disclosure are not limited to the following examples.

[0192] 1. Synthesis of Compound 2

[0193] (Synthesis of intermediate A)

[0194]

[0195] Under an Ar atmosphere, 1-bromo-2,3,5-trichlorobenzene (440.0 g, 154 mmol), diphenylamine (26.0 g, 154 mmol), Pd(dba)₂ (2.65 g, 4.61 mmol), tri-tert-butylphosphonium tetrafluoroborate (1.78 g, 6.15 mmol), t-BuONa (34.7 g, 34.7 mmol), and toluene (500 mL) were added to a three-necked round-bottom flask and stirred at 90 °C for 5 hours. After cooling to room temperature, 500 mL of water was added, and the resulting mixture was subjected to liquid-liquid separation to concentrate the organic layer. This was purified by column chromatography to obtain intermediate A (40.5 g, 75.6% yield).

[0196] (Synthesis of intermediate B)

[0197]

[0198] In an Ar atmosphere, intermediate A (39.0 g, 112 mmol), 4,4'-dimethyldiphenylamine (44.1 g, 224 mmol), Pd(dba)2 (1.93 g, 3.36 mmol), tri-tert-butylphosphonium tetrafluoroborate (1.30 g, 4.47 mmol), t-BuONa (25.0 g, 2.33 mmol), and toluene (500 mL) were added to a three-necked round-bottom flask and stirred at 120 °C for 5 hours. After cooling to room temperature, 500 mL of water was added, and the resulting mixture was subjected to liquid-liquid separation to concentrate the organic layer. The concentrated organic layer was purified by column chromatography to obtain intermediate B (51.4 g, yield 68.6%).

[0199] (Synthesis of intermediate C)

[0200]

[0201] In an Ar atmosphere, intermediate B (26.8 g, 40 mmol) was added to a three-necked round-bottom flask and dissolved in 333 mL of tert-butylbenzene. While cooling to -30 °C, 50 mL of a 1.6 M tert-butyllithium pentane solution was added. After the addition was complete, the mixture was heated to 60 °C and stirred for 2 hours, and then the components with boiling points lower than tert-butylbenzene were removed by distillation. The mixture was cooled again to -30 °C, 20 g of boron tribromide was added, and the mixture was heated to room temperature and stirred for 1 hour. The mixture was then cooled again in an ice bath, and 11 mL of N,N-diisopropylethylamine was added. The mixture was then heated to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, and liquid separation was performed by adding 200 mL of water and 500 mL of dichloromethane to obtain the organic layer. The organic layer was passed through a column packed with silica gel, and the effluent was then concentrated and recrystallized with toluene to obtain intermediate C (comparative compound X-3, 3.40 g, yield 13.2%).

[0202] (Synthesis of intermediate D)

[0203]

[0204] In an Ar atmosphere, intermediate C (3.00 g, 4.7 mmol), benzyltrimethylammonium tribromide (1.91 g, 4.9 mmol), and 200 mL of ethyl acetate were added to a three-necked round-bottom flask. The mixture was stirred at room temperature for 7 hours, and then heated to 50 °C and stirred for 7 hours. After cooling to room temperature, the reaction solution was concentrated. The concentrated reaction solution was subjected to liquid separation by adding 100 mL of water and 300 mL of dichloromethane to concentrate the organic layer, thereby obtaining intermediate D (2.79 g, yield 82.8%).

[0205] (Synthesis of Compound 2)

[0206]

[0207] In an Ar atmosphere, intermediate D (2.50 g, 3.5 mmol), carbazole (0.87 g, 5.2 mmol), Pd(dba)2 (0.10 g, 0.17 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.07 g, 0.24 mmol), t-BuONa (0.78 g, 8.1 mmol), and toluene (50 mL) were added to a three-necked round-bottom flask and stirred at 90 °C for 5 hours. After cooling to room temperature, the resulting mixture was subjected to liquid separation by adding 100 mL of water and 300 mL of dichloromethane to obtain an organic layer. The obtained organic layer was passed through a column packed with silica gel. The effluent was concentrated and recrystallized from toluene to obtain compound 2 (2.12 g, yield 75.8%). The molecular weight of compound 2 was 809, as determined by FAB MS. Sublimation purification was performed (350 °C, 9 × 10⁻⁶). -5 Pa) and conduct device evaluation.

[0208] 2. Synthesis of Compound 5

[0209] (Synthesis of intermediate E)

[0210]

[0211] In an Ar atmosphere, 1,3,5-tribromobenzene (25.0 g, 79.4 mmol), diphenylamine (53.8 g, 318 mmol), Pd(dba)₂ (1.37 g, 2.38 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.92 g, 3.17 mmol), t-BuONa (26.7 g, 278 mmol), and toluene (200 mL) were added to a three-necked round-bottom flask and stirred at 90 °C for 5 hours. After cooling to room temperature, the resulting mixture was liquid-separated by adding 200 mL of water to concentrate the organic layer. The concentrated organic layer was recrystallized from toluene to obtain intermediate E (41.1 g, 89.3% yield).

[0212] (Synthesis of intermediate F)

[0213]

[0214] In an Ar atmosphere, intermediate E (20.0 g, 34.5 mmol), boron tribromide (25.0 g, 100 mmol), and o-dichlorobenzene (200 mL) were added to a three-necked round-bottom flask and stirred at 180 °C for 9 hours. After cooling to room temperature, 50 mL of N,N-diisopropylethylamine was added. The resulting mixture was subjected to liquid separation by adding 100 mL of water and 300 mL of dichloromethane to concentrate the organic layer, and recrystallized from toluene to obtain intermediate F (6.41 g, 31.6% yield).

[0215] (Synthesis of intermediate G)

[0216]

[0217] In an Ar atmosphere, intermediate F (5.0 g, 8.51 mmol), benzyltrimethylammonium tribromide (9.96 g, 25.5 mmol), and ethyl acetate (300 mL) were added to a three-necked round-bottom flask. After stirring at room temperature for 7 hours, the mixture was refluxed for 7 hours. After cooling to room temperature, the reaction solution was concentrated. The concentrated reaction solution was subjected to liquid separation by adding 100 mL of water and 300 mL of dichloromethane to concentrate the organic layer, and recrystallized from toluene to obtain intermediate G (2.10 g, 33.1% yield).

[0218] (Synthesis of compound 5)

[0219]

[0220] In an Ar atmosphere, intermediate G (2.00 g, 2.68 mmol), carbazole (1.35 g, 8.07 mmol), Pd(dba)2 (0.11 g, 0.19 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.06 g, 0.21 mmol), t-BuONa (0.77 g, 8.01 mmol), and toluene (100 mL) were added to a three-necked round-bottom flask and stirred at 90 °C for 15 hours. After cooling to room temperature, the resulting mixture was separated by adding 100 mL of water and 200 mL of dichloromethane to obtain an organic layer. The obtained organic layer was passed through a column packed with silica gel. The effluent was concentrated and recrystallized from toluene to obtain compound 5 (1.50 g, 60.9% yield). The molecular weight of compound 5 was 918, as measured by FAB-MS. Sublimation purification was performed (380 °C, 9 × 10⁻⁶). -5 Pa) and conduct device evaluation.

[0221] 3. Synthesis of Compound 26

[0222] (Synthesis of intermediate H)

[0223]

[0224] Under an Ar atmosphere, 1,3-dibromo-2-chloro-5-fluorobenzene (20.0 g, 69.4 mmol), carbazole (23.2 g, 139 mmol), cesium carbonate (45.2 g, 139 mmol), and NMP (150 mL) were added to a three-necked round-bottom flask, and the mixture was stirred at 180 °C for 15 hours. After cooling to room temperature, the resulting mixture was liquid-liquid separated by adding 300 mL of water and 200 mL of toluene to concentrate the organic layer. The concentrated organic layer was purified by column chromatography to obtain intermediate H (12.1 g, 40.0% yield).

[0225] (Synthesis of intermediate I)

[0226]

[0227] In an Ar atmosphere, intermediate H (10.0 g, 23.0 mmol), diphenylamine (7.77 g, 45.9 mmol), Pd(dba)₂ (0.53 g, 0.92 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.33 g, 1.14 mmol), t-BuONa (5.52 g, 57.4 mmol), and toluene (50 mL) were added to a three-necked round-bottom flask, and the mixture was stirred at 70 °C for 7 hours. After cooling to room temperature, the resulting mixture was liquid-liquid separated by adding 100 mL of water to concentrate the organic layer. The concentrated organic layer was recrystallized from toluene to obtain intermediate I (12.8 g, 91.1% yield).

[0228] (Synthesis of intermediate J)

[0229]

[0230] In an Ar atmosphere, intermediate I (10.0 g, 40 mmol) was added to a three-necked round-bottom flask and dissolved in 80 mL of tert-butylbenzene. While cooling to -30 °C, 20 mL of a 1.6 M tert-butyllithium pentane solution was added. After the addition was complete, the mixture was heated to 60 °C and stirred for 2 hours, and then the components with boiling points lower than tert-butylbenzene were removed by distillation. The mixture was cooled again to -30 °C, 8 g of boron tribromide was added, and the mixture was heated to room temperature and stirred for 1 hour. The mixture was then cooled again in an ice bath, and 5.7 mL of N,N-diisopropylethylamine was added. The mixture was then heated to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, and liquid separation was performed by adding 100 mL of water and 300 mL of dichloromethane to obtain the organic layer. The organic layer was passed through a column packed with silica gel, and the effluent was then concentrated and recrystallized with toluene to obtain intermediate J (1.34 g, yield 14.0%).

[0231] (Synthesis of intermediate K)

[0232]

[0233] In an Ar atmosphere, intermediate J (1.20 g, 2.05 mmol), benzyltrimethylammonium tribromide (2.40 g, 6.15 mmol), and ethyl acetate (100 mL) were added to a three-necked round-bottom flask. After stirring at room temperature for 7 hours, the mixture was refluxed for 7 hours. After cooling to room temperature, the reaction solution was concentrated. The concentrated reaction solution was subjected to liquid separation by adding 100 mL of water and 300 mL of dichloromethane to concentrate the organic layer, and recrystallized from toluene to obtain intermediate K (0.54 g, 35.5% yield).

[0234] (Synthesis of compound 26)

[0235]

[0236] In an Ar atmosphere, intermediate K (0.50 g, 0.67 mmol), carbazole (0.34 g, 2.0 mmol), Pd(dba)₂ (0.030 g, 0.052 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.016 g, 0.055 mmol), t-BuONa (0.19 g, 2.0 mmol), and toluene (30 mL) were added to a three-necked round-bottom flask and stirred at 90 °C for 15 hours. After cooling to room temperature, the resulting mixture was subjected to liquid separation by adding 50 mL of water and 100 mL of dichloromethane to obtain an organic layer. The obtained organic layer was passed through a column packed with silica gel. The effluent was concentrated and recrystallized from toluene to obtain compound 26 (0.51 g, 82.8% yield). The molecular weight of compound 26 was 916, as measured by FAB MS. Sublimation purification was performed (380 °C, 9 × 10⁻⁶). -5 Pa) and conduct device evaluation.

[0237] 4. Synthesis of Compound 36

[0238] (Synthesis of compound 36)

[0239]

[0240] In an Ar atmosphere, intermediate G (1.00 g, 1.34 mmol), 9-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaneborane-2-yl)phenyl]-9H-carbazole (1.49 g, 4.04 mmol), Pd(dba)2 (0.054 g, 0.094 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.031 g, 0.11 mmol), t-BuONa (0.39 g, 4.1 mmol), and toluene (80 mL) were added to a three-necked round-bottom flask and stirred at 90 °C for 15 hours. After cooling to room temperature, the resulting mixture was subjected to liquid separation by adding 100 mL of water and 200 mL of dichloromethane to obtain an organic layer. The obtained organic layer was passed through a column packed with silica gel. The effluent was concentrated and recrystallized from toluene to obtain compound 36 (0.73 g, 50.8% yield). The molecular weight of compound 36 is 1070, as measured by FAB MS. It was purified by sublimation (420℃, 9 × 10⁻⁶). -5 Pa) and conduct device evaluation.

[0241] (Manufacturing of organic electroluminescent devices)

[0242] The organic electroluminescent devices of Examples 1 to 4 were manufactured using the compounds of the embodiments described above as their respective emitter layer materials.

[0243] [Example Compounds]

[0244]

[0245] Organic electroluminescent devices of Comparative Examples 1 to 8 were manufactured using comparative example compounds X-1 to X-8 as their respective emitter layer materials.

[0246] [Comparative Compounds]

[0247]

[0248] The organic electroluminescent devices of the embodiments and comparative examples were manufactured by the following methods.

[0249] Will have about A layer of ITO of a certain thickness was patterned on a glass substrate, washed with ultrapure water, and treated with UV ozone for approximately 10 minutes. Then, HAT-CN was deposited onto... The thickness of α-NPD was deposited to... The thickness, and the mCP was deposited to The thickness is increased to form a hole transport region.

[0250] Next, the polycyclic compound of the example or the comparative compound and mCBP (3,3'-bis(N-carbazole)-1,1'-biphenyl) were co-deposited at a ratio of 10:90 to form a compound having approximately The thickness of the emission layer.

[0251] Formed on the emitter layer using TPBi Thick layers, formed with LiF A thick layer is formed, thus creating an electron transport region. Next, an area approximately [missing information] is formed using aluminum (Al). The second electrode has a thickness of [missing information].

[0252] In the embodiments, a hole transport region, an emitter layer, an electron transport region, and a second electrode are each formed using a vacuum deposition apparatus.

[0253] (Evaluation of the characteristics of organic electroluminescent devices)

[0254] To evaluate the characteristics of the organic electroluminescent devices according to the embodiments and comparative examples, luminance distribution characteristics were measured at 1000 cd / m² using a C9920-11 luminance distribution characteristics measurement device from Hamamatsu Photonics, Inc. 2 Maximum external quantum yield (%) and external quantum efficiency (%) at brightness.

[0255] [Table 1]

[0256]

[0257] Referring to the results in Table 1, it is confirmed that when the emitter layer contains a polycyclic compound according to the embodiments, the external quantum efficiency of the device is improved compared to the comparative examples.

[0258] The compound in the examples contains an amine group at a set or predetermined position and is not bound by the correctness of any theory or explanation. It is believed that the thermal stability of the polycyclic compound is improved by introducing substituents that can improve the molecular durability at the X1 and / or X2 positions. Therefore, the external quantum efficiency of the device containing the compound is improved.

[0259] The organic electroluminescent device of the embodiment can achieve high luminous efficiency by using a polycyclic compound represented by Formula 1 as the emitting layer material.

[0260] The organic electroluminescent device according to the embodiments of this disclosure can achieve high efficiency and long service life.

[0261] The polycyclic compounds according to embodiments of this disclosure can improve the efficiency and / or lifespan (lifetime) of organic electroluminescent devices.

[0262] As used herein, the terms “substantially,” “about,” and similar terms are used as terms of approximation rather than as terms of degree, and are intended to explain the inherent biases in measurements or calculations that would be recognized by one of ordinary skill in the art.

[0263] Any numerical ranges listed herein are intended to include all subranges of the same numerical precision falling 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 (and inclusive), i.e., a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as 2.4 to 7.6. Any maximum numerical limit listed herein is intended to include all lower numerical limits falling within it, and any minimum numerical limit listed in this specification is intended to include all higher numerical limits falling within it. Therefore, the applicant reserves the right to amend this specification (including the claims) to expressly list any subranges falling within the scope expressly listed herein.

[0264] Although this disclosure has been described with reference to exemplary embodiments thereof, it should be understood that this disclosure should not be limited to these exemplary embodiments, and various changes and modifications may be made by those skilled in the art without departing from the spirit and scope of this disclosure.

[0265] Therefore, the technical 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: any one selected from the group consisting of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, Mo, Ti, In, Sn, Zn, and compounds and mixtures thereof; LiF / Ca and / or LiF / Al; or a mixture of LiF / Ca and / or LiF / Al and any one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, Mo, Ti, In, Sn, Zn, and compounds and mixtures thereof, and wherein the emission layer comprises a polycyclic compound represented by Formula 1: [Formula 1] ， wherein, in Formula 1, Ar 1 and Ar 2 are each independently 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 Ar 3 and Ar 4 are each independently 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 / or are bonded to an adjacent group to form a ring, R 1 to R 4 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a and b are each independently an integer of 0 to 3, X 1 and X 2 are each independently a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted arylamine group with 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroarylamine group with 2 to 30 ring-forming carbon atoms, 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 at least one of X 1 and X 2 is a cyano group, a substituted or unsubstituted arylamine group with 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroarylamine group with 2 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group with 2 to 30 ring-forming carbon atoms including N, or an aryl group with 6 to 30 ring-forming carbon atoms having a cyano group, a substituted or unsubstituted arylamine group with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylamine group with 2 to 30 ring-forming carbon atoms as a substituent, wherein the "substituted or unsubstituted" means a state of being unsubstituted or substituted with at least one substituent selected from the group consisting of a deuterium atom, a halogen atom, a cyano group, a nitro group, and an alkyl group with 1 to 20 carbon atoms. 2.The organic electroluminescent device according to claim 1, wherein the emission layer is intended to emit 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 activated delayed fluorescence emission layer that emits blue light. 5.The organic electroluminescent device according to claim 1, wherein X 1 is a cyano group, a substituted or unsubstituted arylamine group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroarylamine group having 2 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms including N, or an aryl group having 6 to 30 ring-forming carbon atoms having a cyano group, a substituted or unsubstituted arylamine group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylamine group having 2 to 30 ring-forming carbon atoms as a substituent, and wherein X 2 is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. 6.The organic electroluminescent device according to claim 1, wherein X 1 and X 2 are each independently a cyano group, a substituted or unsubstituted arylamine group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroarylamine group having 2 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms including N, or an aryl group having 6 to 30 ring-forming carbon atoms having a cyano group, a substituted or unsubstituted arylamine group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylamine group having 2 to 30 ring-forming carbon atoms as a substituent. 7.The organic electroluminescent device according to claim 1, wherein at least one of X 1 and X 2 is represented by any one of 1-1, 1-3, and 1-4: in 1-3 and 1-4, R 9 is an aryl group having 6 to 30 ring-forming carbon atoms, or a heteroaryl group having 2 to 30 ring-forming carbon atoms, R 7 and R 8 are each independently an aryl group having 6 to 30 ring-forming carbon atoms, or a heteroaryl group having 2 to 30 ring-forming carbon atoms, and / or are bonded to an adjacent group to form a ring, d is 0, and X 3 is represented by 1-1 or 1-3. 8.The organic electroluminescent device according to claim 1, wherein formula 1 is represented by formula 2-1 or formula 2-2: [Formula 2-1] [Formula 2-2] in formula 2-1 and formula 2-2, X 2, R 1 to R 4, Ar 1 to Ar 4, a, and b are each independently the same as defined in formula 1. ， wherein 9.The organic electroluminescent device according to claim 1, wherein formula 1 is represented by formula 3-1 or formula 3-2: [Formula 3-1] [Formula 3-2] in formula 3-1 and formula 3-2, e to h are each independently an integer of 0 to 4, the dotted line is an optional bond, and X 2, R 1 to R 4, Ar 1 to Ar 4, a, and b are each independently the same as defined in formula 1. ​ ​ ​ ​ ​ ​ ​ ， wherein ​ ​ ​ ​ ​ ， wherein ​ R 21 , R 22 , R 31 , and R 32 are each independently a hydrogen atom, a deuterium atom, or an alkyl group having from 1 to 20 carbon atoms, ​ ​ X2, R1to R4, Ar1to Ar4, a, and b are each independently the same as defined in formula 1. 10.The organic electroluminescent device according to claim 1, wherein formula 1 is represented by formula 4-1 or formula 4-2: [Formula 4-1] [Formula 4-2] [Formula 4-1] [Formula 4-2] In formula 4-1 and formula 4-2, ， wherein, X3and X4are each independently a cyano group, a substituted or unsubstituted arylamine group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroarylamine group having 2 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group including N having 2 to 30 ring-forming carbon atoms, R9and R9’ are each independently a hydrogen atom, a deuterium atom, or an alkyl group having 1 to 20 carbon atoms, d and d’ are each independently an integer from 0 to 4, and X2, R1to R4, Ar1to Ar4, a, and b are each independently the same as defined in formula 1. 11.The organic electroluminescent device according to claim 1, wherein Ar1and Ar2are each independently represented by formula 5: [Formula 5] [Formula 5] In formula 5, ， wherein Y1to Y5are each independently CA or N, and A is a hydrogen atom, a deuterium atom, or an alkyl group having 1 to 20 carbon atoms. 12.The organic electroluminescent device according to claim 1, wherein formula 1 is represented by formula 6: [Formula 6] [Formula 6] In formula 6, ， wherein, j and k are each independently an integer from 0 to 4, R 10 and R 11 each independently is a hydrogen atom, a deuterium atom, or an alkyl group having 1 to 20 carbon atoms, a dotted line is an optional bond, and R1to R4, X1, X2, Ar1, Ar2, a, and b are each independently the same as defined in formula 1. 13.The organic electroluminescent device according to claim 1, wherein the compound represented by formula 1 is any one of the compounds represented by Compound Group 1: [Compound Group 1] [Compound Group 1] 14.The organic electroluminescent device according to claim 1, wherein the first electrode and the second electrode each independently comprise: any one selected from oxides of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, Mo, Ti, In, Sn, and Zn; or a mixture of LiF / Ca and / or LiF / Al with any one of oxides of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, Mo, Ti, In, Sn, and Zn. 。 15.A polycyclic compound represented by formula 1: [Formula 1] [Formula 1] In formula 1, ， wherein Ar1and Ar2are each independently 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 Ar3and Ar4are each independently 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 / or are bonded to an adjacent group to form a ring, R1to R4are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a and b are each independently an integer from 0 to 3, and X2, R1to R4, Ar1to Ar4, a, and b are each independently the same as defined in formula 1. X1and X2are each independently a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted arylamine group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroarylamine group having 2 to 30 ring-forming carbon atoms, 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 at least one of X1and X2is a cyano group, a substituted or unsubstituted arylamine group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroarylamine group having 2 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms including N, or an aryl group having 6 to 30 ring-forming carbon atoms having a cyano group, a substituted or unsubstituted arylamine group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylamine group having 2 to 30 ring-forming carbon atoms as a substituent, wherein the "substituted or unsubstituted" means a state of being unsubstituted or substituted with at least one substituent selected from the group consisting of a deuterium atom, a halogen atom, a cyano group, a nitro group, and an alkyl group having 1 to 20 carbon atoms.

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