Organic electroluminescent device

Abstract

The present disclosure relates to an organic electroluminescent device. The organic electroluminescent device of the embodiments includes a first electrode, a second electrode, and a plurality of functional layers disposed between the first electrode and the second electrode, wherein at least one of the plurality of functional layers includes a polycyclic compound represented by Formula 1, thereby showing excellent luminous efficiency in a short wavelength region. Formula 1

Description

[0001] Cross-references to related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2019-0174228, filed on December 24, 2019, the entire contents of which are incorporated herein by reference. Technical Field

[0003] One or more aspects of embodiments of this disclosure relate to organic electroluminescent devices and polycyclic compounds used therein, for example, to polycyclic compounds used as luminescent materials and organic electroluminescent devices comprising such polycyclic compounds. 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 displays, in which holes and electrons injected from the first and second electrodes recombine in the emitting layer, thereby causing the emitting layer, which contains luminescent materials of organic compounds, to emit light for display purposes.

[0005] When applying organic electroluminescent devices to display devices, there is a need for organic electroluminescent devices with low driving voltage, improved emission efficiency and long lifespan, and new materials for organic electroluminescent devices that can stably achieve these characteristics are needed.

[0006] Recently, in order to realize highly 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 embodiments of this disclosure relate to organic electroluminescent devices that exhibit excellent emission efficiency in the short wavelength region.

[0008] One or more aspects of embodiments of this disclosure relate to polycyclic compounds as materials for organic electroluminescent devices having high color purity and long lifespan characteristics.

[0009] One or more exemplary embodiments of this disclosure provide polycyclic compounds represented by Formula 1:

[0010] Formula 1

[0011]

[0012] In Formula 1, A1 to A5 may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted oxygen group, a substituted or unsubstituted thio group, a substituted or unsubstituted thiocarbonyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms for cyclization, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms for cyclization, and / or may be combined with adjacent groups to form a fused heterocycle. At least one of A1 to A5 or the fused heterocycle may be or include an electron acceptor, and "Du" may be represented by Formula 2.

[0013] Formula 2

[0014]

[0015] In Equation 2, R1 to R 22 At least one of them may be cyano, fluoro, or trifluoromethyl, and the remainder may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted oxygen group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms for cyclization, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms for cyclization, and "-*" may indicate a connecting position.

[0016] In the implementation, equation 1 can be represented by any one of equations 1-A to 1-D:

[0017] Formula 1-A

[0018]

[0019] Formula 1-B

[0020]

[0021] Formula 1-C

[0022]

[0023] Formula 1-D

[0024]

[0025] In Equation 1-A, at least one of X1 to X5 can be N, and the rest can each be CR. a In Equations 1-C and 1-D, Y1 to Y3 can each be independently represented as O, S, and NR. e C (=S) or C (=O). In equations 1-A and 1-B, A 11 To A 14Each of the following can be 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 carbon atoms for cyclization, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms for cyclization. In formulas 1-A to 1-D, R a To R e Each of the following can be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aliphatic cyclogroup with 6 to 30 carbon atoms for cyclization, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms for cyclization, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms for cyclization, and “Du” can be the same as defined in Formula 2.

[0026] In the implementation, Equation 1 can be represented by any one of Equations 1-1 to 1-23. In Equations 1-1 to 1-23, "Du" can be the same as that defined in Equation 2.

[0027]

[0028] In an embodiment, the electron acceptor may be a substituted or unsubstituted heterocycle having at least one nitrogen atom as a cyclic atom, or a substituted or unsubstituted boron group.

[0029] In embodiments, the fused heterocycle may be a substituted or unsubstituted heterocycle having a boron atom as a cyclizing atom.

[0030] In embodiments, the electron-accepting group may include cyano, fluorine, carbonyl, or sulfonyl groups.

[0031] In Equation 2, R1 to R 22 At least one of them may be cyano, fluoro, or trifluoromethyl, and the rest may each be a hydrogen atom.

[0032] In Equation 2, the selections are from R1 to R... 22 At least two of them can be cyano, fluoro, or trifluoromethyl, and the rest can each be a hydrogen atom.

[0033] In an embodiment, the polycyclic compound represented by Formula 1 can be a material that emits thermally activated delayed fluorescence.

[0034] In an embodiment, the polycyclic compound represented by Formula 1 can be a material that emits blue light with a maximum emission wavelength of about 470 nanometers or less.

[0035] One or more exemplary embodiments of this disclosure provide an organic electroluminescent device comprising a first electrode; a second electrode on the first electrode; and a plurality of functional layers disposed between the first electrode and the second electrode; wherein at least one of the plurality of functional layers comprises a polycyclic compound. The first electrode and the second electrode may each independently comprise at least one selected from 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, molybdenum (Mo), titanium (Ti), indium (In), tin (Sn), and zinc (Zn), two or more compounds thereof, mixtures of two or more thereof, or oxides 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.

[0036] In an implementation, the multiple functional layers may include a hole transport region; an emission layer on the hole transport region; and an electron transport region on the emission layer, wherein the emission layer may include a polycyclic compound represented by Formula 1.

[0037] In one implementation, the emitting layer may emit delayed fluorescence.

[0038] In one implementation, the emitting layer can emit light with a maximum emission wavelength of about 470 nanometers or less. Attached Figure Description

[0039] The accompanying drawings are included to provide a further understanding of this disclosure, and are incorporated in and form 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:

[0040] Figure 1 A cross-sectional view illustrating an organic electroluminescent device according to an embodiment of the present disclosure;

[0041] Figure 2 A cross-sectional view illustrating an organic electroluminescent device according to an embodiment of the present disclosure;

[0042] Figure 3 A cross-sectional view of an organic electroluminescent device according to an embodiment of the present disclosure is shown for illustrative purposes; and

[0043] Figure 4 A cross-sectional view illustrating an organic electroluminescent device according to an embodiment of the present disclosure. Detailed Implementation

[0044] This disclosure may have various modifications and may be embodied in different forms, and exemplary embodiments will be explained in more detail with reference to the accompanying drawings. However, this disclosure may be embodied in different forms and should not be construed as 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 herein.

[0045] It should be understood that when a component (or area, layer, part, etc.) is referred to as being "on" another component, "connected to" or "attached to" another component, it may be directly on, directly connected to or directly attached to the other component, or there may be intermediate components. When a component is referred to as being "directly on" another component, "directly connected to" or "directly attached to" another component, there are no intermediate components.

[0046] The same reference numerals refer to the same elements throughout the drawings, and their repeated descriptions may be omitted. Furthermore, in the drawings, to effectively explain the technical content, the thickness, scale, and dimensions of the constituent elements may be enlarged.

[0047] The term “and / or” includes any and all combinations of one or more of the associated listed items. Unless the context clearly indicates otherwise, the singular forms “a,” “an,” and “the” as used herein are also intended to include the plural forms.

[0048] As used herein, expressions such as "at least one…", "a…", and "selected from…" modify the entire list of elements without modifying any individual element within that list when preceding a list of elements. Furthermore, the use of "may" in describing embodiments of this disclosure refers to "one or more embodiments of this disclosure".

[0049] It should be understood that although the terms first, second, etc., are 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. Therefore, without departing from the teachings of the invention, a first element may be referred to as a second element. Similarly, a second element may be referred to as a first element. Unless the context clearly indicates otherwise, the singular forms used herein are intended to include the plural forms as well.

[0050] Additionally, terms such as "below," "under," "above," and "above" are used to explain the relationships between the elements shown in the accompanying drawings. These terms are relative concepts and are used based on the orientation shown in the drawings.

[0051] Unless otherwise specified, 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 invention pertains. It should be further understood that, unless expressly defined herein, terms (e.g., those defined in common dictionaries) should be interpreted as having a meaning consistent with their meaning in the context of the relevant field and should not be interpreted in an idealized or overly formal sense.

[0052] It should be further understood that when the terms “includes,” “including,” “comprises,” “comprising,” and / or “have” are used in this specification, they specify the presence of the described features, numbers, steps, operations, elements, parts, or combinations thereof, but do not exclude the presence or addition of one or more other features, numbers, steps, operations, elements, parts, or combinations thereof.

[0053] The organic electroluminescent device according to embodiments of the present disclosure will be explained below with reference to the accompanying drawings.

[0054] Figures 1 to 4 This is a schematic cross-sectional view of an organic electroluminescent device according to an embodiment of the present disclosure. 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 disposed opposite to each other, and an emission layer EML can be disposed (inserted) between the first electrode EL1 and the second electrode EL2.

[0055] In some embodiments, in addition to the emitter layer EML, the organic electroluminescent device 10 may further include multiple functional layers between the first electrode EL1 and the second electrode EL2. These multiple functional layers may include a hole transport region HTR and / or an electron transport region ETR. For example, the 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 one after the other. In some embodiments, the organic electroluminescent device 10 may include a capping layer CPL disposed on the second electrode EL2.

[0056] The organic electroluminescent device 10 of the embodiments may include the polycyclic compound of the embodiments (explained later) in the emitter layer EML disposed between the first electrode EL1 and the second electrode EL2. However, the embodiments of this disclosure are not limited thereto. In addition to the emitter layer EML, the organic electroluminescent device 10 of the embodiments may also include the polycyclic compound of the embodiments in the hole transport region HTR or the electron transport region ETR (which are disposed in multiple functional layers between the first electrode EL1 and the second electrode EL2) (explained later). For example, the organic electroluminescent device 10 of the embodiments may include the polycyclic compound of the embodiments in at least one of the multiple functional layers.

[0057] and Figure 1 Compare, Figure 2 A cross-sectional view of the 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 the organic electroluminescent device 10 of the 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. When combined with... Figure 2 When comparing, Figure 4 A cross-sectional view of an organic electroluminescent device 10 according to an embodiment is shown, which includes a capping layer CPL disposed on a second electrode EL2.

[0058] The first electrode EL1 may be conductive. The first electrode EL1 may be formed using a metal alloy and / or a conductive compound. The first electrode EL1 may be an anode. The first electrode EL1 may be a pixel 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 be formed using 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-reflective electrode or a reflective electrode, it may include 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, molybdenum (Mo), titanium (Ti), their compounds, or mixtures thereof (e.g., a mixture of Ag and Mg). In some embodiments, the first electrode EL1 may have a structure comprising multiple layers, including a reflective or transmissive layer formed using the aforementioned materials and a transmissive conductive layer formed using ITO, IZO, ZnO, and / or ITZO. For example, the first electrode EL1 may include a three-layer structure of ITO / Ag / ITO. However, embodiments of this disclosure are not limited thereto. The thickness of the first electrode EL1 may be approximately [missing information]. to approximately For example, about to approximately

[0059] The 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 EBL. The thickness of the hole transport region HTR may be approximately [missing information]. to approximately

[0060] The hole transport region (HTR) may have a single layer formed using a single material, a single layer formed using multiple different materials, or a multilayer structure comprising multiple layers formed using multiple different materials.

[0061] 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, or it may have a single-layer structure formed using a hole injection material and a hole transport material (e.g., together). In some embodiments, the hole transport region HTR may have a single-layer structure formed using 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 on the first electrode EL1, but there are no limitations.

[0062] Hole transport regions (HTRs) can be formed using any suitable method, such as vacuum deposition, spin coating, casting, Langmuir-Brookett (LB) method, inkjet printing, laser printing, and / or laser-induced thermal imaging (LITI).

[0063] 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]-phenyl-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-phenylene) Poly(phenylene 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 (NPB), triphenylamine-containing polyether ketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium [tetra(pentafluorophenyl)borate] and / or dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexaonitrile (HAT-CN).

[0064] The hole transport layer (HTL) may further include, for example, carbazole derivatives (such as N-phenylcarbazole and / or polyvinylcarbazole), fluorenyl 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'-bis(naphthyl-1-yl)-N,N'-diphenyl-benzidine (NPB), 4,4'-cyclohexylbis[N,N-bis(4-methyl)phenyl]aniline (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), 1,3-bis(N-carbazolyl)benzene (mCP), etc.

[0065] 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) meet the above ranges, satisfactory hole transport performance can be achieved without a significant increase in driving voltage.

[0066] 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 substantially uniformly or non-uniformly dispersed in the hole transport region (HTR). The charge-generating material may be, for example, a p-dopant. The p-dopant may be at least one of quinone derivatives, metal oxides, and cyano-containing compounds, but is not limited thereto. Non-limiting examples of p-dops 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).

[0067] 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 optical resonant distance of the wavelength of light emitted from the emitter layer (EML), and can thereby increase the light emission efficiency of the device. Materials that may 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 electrons injected from the electron transport region (ETR) into the hole transport region (HTR).

[0068] The emitter layer EML can be provided on the hole transport region (HTR). The emitter layer EML may have, for example, approximately to approximately or about to approximately The thickness of the emitter layer (EML) is as follows. The EML can be a single layer formed using a single material, a single layer formed using multiple different materials, or a multilayer structure with multiple layers formed using multiple different materials.

[0069] In the organic electroluminescent device 10 of the embodiment, the emission layer EML may include the polycyclic compound of the embodiment.

[0070] The polycyclic compound according to the embodiments can be represented by Formula 1, where "Du" in Formula 1 can be represented by Formula 2. In the polycyclic compound according to the embodiments represented by Formula 1, "Du" corresponds to an electron donor, and the remaining portion of Formula 1 includes the substituents A1 to A5. It may include electron acceptors.

[0071] Formula 1

[0072]

[0073] Formula 2

[0074]

[0075] In Formula 1, A1 to A5 may each be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted oxygen group, a substituted or unsubstituted thio group, a substituted or unsubstituted thiocarbonyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms for cyclization, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms for cyclization, and / or may be combined with adjacent groups to form a fused heterocycle.

[0076] At least one of A1 to A5, or a fused heterocycle formed by combining one or more of A1 to A5 with an adjacent group, may be an electron acceptor. At least one of A1 to A5, or a fused heterocycle formed by combining one or more of A1 to A5 with an adjacent group, may include an electron acceptor group.

[0077] For example, at least one of A1 to A5 may include a cyano, fluorine, carbonyl, or sulfonyl group as a substituent. In some embodiments, the fused heterocycle formed by combining at least one of A1 to A5 with an adjacent group may include a cyano, fluorine, carbonyl, or sulfonyl group as a substituent. In embodiments, the cyano, fluorine, carbonyl, or sulfonyl group may be an electron-accepting group.

[0078] At least one of A1 to A5 may be a substituted or unsubstituted heterocycle comprising at least one nitrogen atom as a cyclizing atom, or a substituted or unsubstituted boron group. For example, at least one of A1 to A5 may be a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, or a substituted or unsubstituted triazineyl. In some embodiments, at least one of A1 to A5 may be a substituted or unsubstituted phenyl-substituted boron group. In some embodiments, the substituted or unsubstituted heterocycle comprising at least one nitrogen atom as a cyclizing atom and / or the substituted or unsubstituted boron group may each be an electron acceptor.

[0079] Furthermore, the fused heterocycle formed by combining one of A1 to A5 with an adjacent group may be a substituted or unsubstituted heterocycle including a boron atom as a cyclizing atom, and in embodiments, the fused heterocycle may be or include an electron acceptor.

[0080] In this description, the term "substituted or unsubstituted" refers to an unsubstituted state, or a state substituted by at least one substituent selected from the group consisting of: deuterium, halogen, cyano, nitro, amino, silyl, oxy, thio, sulfinyl, sulfonyl, carbonyl, boron, phosphonyl oxide, phosphonyl sulfide, alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl, aryl, and heterocyclic groups. Each of the above substituents may be unsubstituted or further substituted. For example, biphenyl can be interpreted as aryl or phenyl substituted with phenyl.

[0081] In this description, the term "forming a ring by bonding with an adjacent group" can refer to the formation of a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle. The hydrocarbon ring may be or include aliphatic or aromatic hydrocarbon rings. The heterocycle may be or include aliphatic or aromatic heterocycles. The ring formed by bonding with an adjacent group can be monocyclic or polycyclic. Furthermore, the ring formed by bonding with an adjacent group can bond with another ring to form a spirostructure.

[0082] In this description, the term "adjacent group" may refer to a substituent on the same atom or point, a substituent directly attached to an atom of the base atom or point, or a substituent spatially positioned relative to the corresponding substituent (e.g., within an intramolecular bonding distance). For example, in 1,2-dimethylbenzene, the two methyl groups can be interpreted as "adjacent groups" to each other, and in 1,1-diethylcyclopentane, the two ethyl groups can be interpreted as "adjacent groups" to each other.

[0083] In this description, the alkyl group may be straight-chain, branched, or cyclic. The number of carbon atoms in the alkyl group may 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, 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-butyl 2-Hexyldecyl, 2-Octylide, n-Undecyl, n-Dodecyl, 2-Ethyldodecyl, 2-Butyldodecyl, 2-Hexyldodecyl, 2-Octylide, n-Tridecyl, n-Tetradecyl, n-Pentadedecyl, n-Hexadecyl, 2-Ethylhexadecyl, 2-Butylhexadecyl, 2-Hexylhexadecyl, 2-Octylide, n-Heptadedecyl, n-Octadedecyl, n-Nondecyl, n-Eicosyl, 2-Ethyleicosyl, 2-Butyleicosyl, 2-Hexyleicosyl, 2-Octylide, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, etc.

[0084] In this description, the term "hydrocycloyl group" may refer to any optional functional group or substituent derived from an aliphatic hydrocarbon ring. The hydrocycloyl group may be a saturated hydrocycloyl group with 5 to 20 carbon atoms for cyclization.

[0085] In this description, the term "aryl" may refer to any optional functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be monocyclic or polycyclic. The number of carbons in the aryl group used for ring formation may be 6 to 30, 6 to 20, or 6 to 15. Non-limiting examples of aryl groups include phenyl, naphthyl, fluorenyl, anthracene, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, hexaphenyl, triphenylene, pyrene, benzofluoranthracene, 1,2-benzophenanthryl, etc.

[0086] In this description, the heterocyclic group may include one or more of boron (B), oxygen (O), nitrogen (N), phosphorus (P), silicon (Si), and sulfur (S) as heteroatoms. When the heterocyclic group includes two or more heteroatoms, the two or more heteroatoms may be the same or different. The heterocyclic group may be a monocyclic or polycyclic heterocyclic group, and in some embodiments may be a heteroaryl group. The number of carbons in the heterocyclic group for cyclization may be 2 to 30, 2 to 20, or 2 to 10.

[0087] In this description, a heteroaryl group may include one or more of B, O, N, P, Si, and S as heteroatoms. When a heteroaryl group includes two or more heteroatoms, the two or more heteroatoms may be the same or different. The heteroaryl group may be a monocyclic heteroaryl or a polycyclic heteroaryl. The number of carbons in the heteroaryl group for cyclization may be 2 to 30, 2 to 20, or 2 to 10. Non-limiting examples of heteroaryl groups include thienyl, furanyl, pyrrolyl, imidazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazolopyrazinyl, isoquinolinyl, indolyl, carbazoleyl, N-arylcarbazoleyl, N-heteroarylcarbazoleyl, N-alkylcarbazoleyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazoleyl, benzothiaphenyl, dibenzothiaphenyl, thienothiaphenyl, benzofuranyl, phenanthrololinyl, thiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, thiadiazolyl, phenthiazolyl, dibenzothiazolyl, dibenzofuranyl, etc.

[0088] In this description, the oxygen group may be an alkoxy or an aryloxy group. An alkoxy group may include a straight alkyl chain, a branched alkyl chain, or a cycloalkyl chain. The number of carbon atoms in the alkoxy group is not specifically limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the aryloxy group for cyclization is not specifically limited, but may be, for example, 6 to 30, 6 to 20, or 6 to 15. Non-limiting examples of oxygen groups include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentoxy, hexoxy, octoxy, nonoxy, decoxy, benzyloxy, etc. However, embodiments of this disclosure are not limited thereto.

[0089] In this description, the thio group can be alkathio or arylthio. The number of carbons in the alkathio group is not specifically limited, but can be, for example, 1 to 20 or 1 to 10. The number of carbons in the arylthio group is not specifically limited, but can be, for example, 6 to 30, 6 to 20 or 6 to 15. For example, the alkyl group in the alkathio group can be the same as the alkyl group described above, and the aryl group in the arylthio group can be the same as the aryl group described above.

[0090] In this description, the boron group may be alkoboryl or arylboryl. Non-limiting examples of the boron group include dimethylboryl, diethylboryl, tert-butylmethylboryl, diphenylboryl, phenylboryl, etc. For example, the alkyl group in the alkoboryl group may be the same as the alkyl group described above, and the aryl group in the arylboryl group may be the same as the aryl group described above.

[0091] In this description, "-*" indicates a connection point.

[0092] In the polycyclic compounds according to the embodiments, Formula 1 can be represented by any one of Formula 1-A to Formula 1-D:

[0093] Formula 1-A

[0094]

[0095] Formula 1-B

[0096]

[0097] Formula 1-C

[0098]

[0099] Formula 1-D

[0100]

[0101] In Equation 1-A, at least one of X1 to X5 can be N, and the rest can each be CR. a For example, in compounds represented by formulas 1-A, one of X1 to X5 can be N, and the others can be CR. a In some embodiments, two or three of X1 to X5 in the compounds represented by formulas 1-A may be N, and the others may be CR. a .

[0102] In Equation 1-A, R a It can be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aliphatic cyclogroup having 6 to 30 carbon atoms for cyclization, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for cyclization, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for cyclization. For example, R a It can be a hydrogen atom, methyl, tert-butyl, cyclohexyl, adamantyl, phenyl, or pyridyl. However, the embodiments disclosed herein are not limited thereto.

[0103] In Equation 1-B, R b and R cEach of these groups can independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aliphatic cyclogroup with 6 to 30 carbon atoms for cyclization, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms for cyclization, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms for cyclization. For example, R b and R c Each of the phenyl groups can be an unsubstituted phenyl or an alkyl-substituted phenyl group. However, the embodiments disclosed herein are not limited thereto.

[0104] In equations 1-A and 1-B, A 11 To A 14 Each of the following can be 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 carbon atoms for cyclization, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms for cyclization. A 11 To A 14 Each of these atoms can be a hydrogen atom or a methyl group independently. However, the embodiments disclosed herein are not limited thereto.

[0105] In Equations 1-C and 1-D, Y1 to Y3 can each be independently represented as O, S, and NR. e C (=S) or C (=O). In Equation 1-C, Y1 and Y2 can be the same or different. R e It can be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aliphatic cyclogroup having 6 to 30 carbon atoms for cyclization, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for cyclization, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for cyclization. For example, R e It can be a substituted or unsubstituted phenyl group. However, the embodiments disclosed herein are not limited thereto.

[0106] Furthermore, in Equation 1-D, R d It can be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aliphatic cyclogroup having 6 to 30 carbon atoms for cyclization, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for cyclization, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for cyclization. For example, R d It can be a substituted or unsubstituted phenyl group. However, the embodiments disclosed herein are not limited thereto.

[0107] In the polycyclic compound according to the embodiments, "Du" can be represented by Formula 2. In Formula 2, R1 to R 22At least one of them may be cyano, fluoro, or trifluoromethyl, and the remainder may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, an substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, an substituted or unsubstituted aryl group with 6 to 30 carbon atoms for cyclization, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms for cyclization.

[0108] In Equation 2, the selections are from R1 to R... 22 Any one of them may be cyano, fluoro, or trifluoromethyl, and the remainder may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted oxygen group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for cyclization, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for cyclization. For example, selected from R1 to R 22 Any one of them can be cyano, fluoro, or trifluoromethyl, and the rest can each be a hydrogen atom.

[0109] In some embodiments, in Equation 2, R1 to R... 22 Two of them can each independently be cyano, fluoro, or trifluoromethyl, and the remaining can each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted oxygen group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for cyclization, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for cyclization. For example, selected from R1 to R 22 Two of them can each be independently a cyano, fluoro, or trifluoromethyl group, and the remaining ones can each be hydrogen atoms. In some embodiments, the group selected is R1 to R2. 22 The two groups can be the same and are selected from cyano, fluoro, and trifluoromethyl groups, and in some embodiments, are selected from R1 to R2. 22 The two groups can be different from each other and are selected from cyano, fluoro, and trifluoromethyl.

[0110] In some embodiments, in Equation 2, R1 to R... 22 The three groups can each independently be cyano, fluoro, or trifluoromethyl, and the remaining group can each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted oxygen group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for cyclization, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for cyclization. For example, selected from R1 to R... 22The three groups can each be independently cyano, fluoro, or trifluoromethyl, and the remaining groups can each be hydrogen atoms. In some embodiments, the group selected is R1 to R2. 22 The three groups can be the same and are selected from cyano, fluoro, and trifluoromethyl. In some embodiments, at least one of the three groups can be different from the other two and can be selected from cyano, fluoro, and trifluoromethyl.

[0111] Formula 2 can be represented by any one of compounds (A)-1 to (A)-18. Compounds (A)-1 to (A)-18 correspond to those selected from R1 to R7, R... 10 To R 16 and R 19 To R 22 Examples of compounds in which one is a cyano group and the others are each hydrogen atoms. For example, compound (A)-1 corresponds to a compound in which R1 in formula 2 is a cyano group and R2 to R... 22 The case where each atom is hydrogen. The compound represented by the case where R5 is substituted with a cyano group is the same as the case where R9 is substituted with a cyano group (e.g., due to molecular symmetry). Similarly, the case where R6 is substituted with a cyano group is the same as the case where R8 is substituted with a cyano group; where R... 15 The case of substitution by cyano group and R in it 17 The same applies when cyano is substituted; and where R 14 The case of substitution by cyano group and R in it 18 The same applies to compounds substituted with cyano groups. Therefore, these cases are not described separately as separate compounds.

[0112]

[0113] Formula 2 can be represented by any one of compounds (B)-1 to (B)-18. Compounds (B)-1 to (B)-18 correspond to those selected from R1 to R7, R... 10 To R 16 and R 19 To R 22 Examples of compounds in which one is a fluorine group and the others are each hydrogen atoms. For example, compound (B)-1 corresponds to a compound in which R1 in formula 2 is a fluorine group and R2 to R... 22 The case where each is a hydrogen atom. As described in the example compound containing a cyano substituent, the compound represented by the case where R5 is substituted with a fluorine group is the same as the case where R9 is substituted with a fluorine group, and so on. Because R6 and R8, R 15 and R 17 R 14 and R 18 They are also equivalent due to the symmetry described above, so they are not described separately as other compounds.

[0114]

[0115] Formula 2 can be represented by any one of compounds (C)-1 to (C)-18. Compounds (C)-1 to (C)-18 correspond to those selected from R1 to R7, R... 10 To R 16 and R 19 To R 22 Examples of compounds in which one is trifluoromethyl and the others are hydrogen atoms. For example, compound (C)-1 corresponds to a compound in which R1 in formula 2 is trifluoromethyl and R2 to R... 22 The case where each is a hydrogen atom. As described in the example compound containing a cyano substituent, the compound represented by the case where R5 is substituted with a trifluoromethyl group is the same as the case where R9 is substituted with a trifluoromethyl group. Because R6 and R8, R 15 and R 17 R 14 and R 18 They are also equivalent due to the symmetry described above, so they are not described separately as other compounds.

[0116]

[0117] Formula 2 can be represented by any one of compounds (D)-1 to (D)-152. Compounds (D)-1 to (D)-152 correspond to those selected from R1 to R7, R... 10 To R 16 and R 19 To R 22 Examples of compounds in which two or three are cyano groups and the others are each hydrogen atoms. For example, compound (D)-1 corresponds to a compound in which R1 and R2 in formula 2 are cyano groups and R3 to R4 are hydrogen atoms. 22 In the case where each atom is hydrogen. Furthermore, compound (D)-44 corresponds to R3 and R... 16 It is a cyano group and R1, R2, R4 to R 15 R 17 To R 22 The case where each atom is a hydrogen atom.

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127] Formula 2 can be represented by any one of compounds (E)-1 to (E)-152. Compounds (E)-1 to (E)-152 correspond to those selected from R1 to R7, R... 10 To R 16 and R 19 To R 22 Examples of compounds in which two or three are fluorine groups and the others are hydrogen atoms. For example, compound (E)-1 corresponds to a compound in which R1 and R2 in formula 2 are fluorine groups and R3 to R... 22 In the case where each atom is hydrogen. Furthermore, compound (E)-44 corresponds to R3 and R... 16 It is fluorine-based and R1, R2, R4 to R 15 R 17 To R 22 The case where each atom is a hydrogen atom.

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137] Formula 2 can be represented by any one of compounds (F)-1 to (F)-302. Compounds (F)-1 to (F)-302 correspond to those selected from R1 to R7, R... 10 To R 16 and R 19 To R 22Examples of compounds in which two or three are independently cyano or fluorine groups. For example, compounds selected from R1 to R7, R... 10 To R 16 and R 19 To R 22 One of the two groups can be a cyano group, the other a fluorine group, and the remaining substituents can be hydrogen atoms. In some embodiments, the substituents are selected from R1 to R7, R... 10 To R 16 and R 19 To R 22 One of the three groups can be a cyano group, the other two can be fluorine groups, and the remaining substituents can be hydrogen atoms. In some embodiments, the substituents are selected from R1 to R7, R... 10 To R 16 and R 19 To R 22 Any one of the three groups can be fluorine, the other two can be cyano, and the remaining substituents can be hydrogen atoms. The compound represented by R5 being substituted with one cyano or one fluorine group is the same as the compound represented by R9 being substituted with one cyano or one fluorine group. Because R6 and R8, R... 15 and R 17 R 14 and R 18 They can also be described as described above, so they are not described separately as other compounds.

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154] Formula 2 can be represented by any one of compounds (G)-1 to (G)-302. Compounds (G)-1 to (G)-302 correspond to those selected from R1 to R7, R... 10 To R 16 and R 19 To R 22 Examples of compounds in which two or three are independently cyano or trifluoromethyl. For example, compounds selected from R1 to R7, R 10 To R 16 and R 19 To R 22 One of the two groups can be a cyano group, the other can be a trifluoromethyl group, and the remaining substituents can be hydrogen atoms. In some embodiments, the substituents are selected from R1 to R7, R... 10 To R 16 and R 19 To R 22 One of the three groups can be a cyano group, the other two can be trifluoromethyl groups, and the remaining substituents can be hydrogen atoms. In some embodiments, the substituents are selected from R1 to R7, R... 10 To R 16 and R 19 To R 22 Any one of the three can be trifluoromethyl, the other two can be cyano, and the remaining substituents can be hydrogen atoms. The compound represented by R5 being substituted with one cyano or one trifluoromethyl group is the same as the compound represented by R9 being substituted with one cyano or one trifluoromethyl group. Because R6 and R8, R... 15 and R 17 R 14 and R 18 They are also equivalent due to the symmetry described above, so they are not described separately as other compounds.

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169] Formula 2 can be represented by any one of compounds (H)-1 to (H)-302. Compounds (H)-1 to (H)-302 correspond to those selected from R1 to R7, R... 10 To R 16 and R 19 To R 22 Examples of compounds in which two or three are independently fluorinated or trifluoromethyl groups. For example, compounds selected from R1 to R7, R... 10 To R 16 and R 19 To R 22 One of the two groups can be a fluorine group, the other can be a trifluoromethyl group, and the remaining substituents can be hydrogen atoms. In some embodiments, the substituents are selected from R1 to R7, R... 10 To R 16 and R 19 To R 22 One of the three groups can be a fluorine group, the other two can be trifluoromethyl groups, and the remaining substituents can be hydrogen atoms. In some embodiments, the substituents are selected from R1 to R7, R... 10 To R 16 and R 19 To R 22 Any one of the three can be trifluoromethyl, the other two can be fluorine, and the remaining substituents can be hydrogen atoms. The compound represented by R5 being substituted with one fluorine or one trifluoromethyl group is the same as the compound represented by R9 being substituted with one fluorine or one trifluoromethyl group. Because R6 and R8, R... 15 and R 17 R 14 and R 18 They are also equivalent due to the symmetry described above, so they are not described separately as other compounds.

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192] The electron donor “Du” of the polycyclic compound represented by Formula 2 can be represented by any one of the compounds (A)-1 to (A)-18, (B)-1 to (B)-18, (C)-1 to (C)-18, (D)-1 to (D)-152, (E)-1 to (E)-152, (F)-1 to (F)-302, (G)-1 to (G)-302 and (H)-1 to (H)-302.

[0193] In the polycyclic compounds of the embodiments, the electron donor indicated by "Du" includes at least one electron-accepting group as a substituent, and the electron donor is weakened compared to cases where no electron-accepting group is present, so that the polycyclic compounds of the embodiments can emit light in a relatively short wavelength region. For example, the electron donor "Du" of the polycyclic compounds of the embodiments includes diindronecarbazole (where the three carbazole groups are fused) and includes at least one electron-accepting group (such as cyano, fluoro, and / or trifluoromethyl). Therefore, the polycyclic compounds of the embodiments can emit light in the wavelength region of 470 nm or smaller and exhibit excellent luminous efficiency characteristics.

[0194] Equation 1 can be represented by any one of Equations 1-1 to 1-23. In Equations 1-1 to 1-23, “Du” is represented by Equation 2. Furthermore, in Equations 1-1 to 1-23, “Du” can be represented by any one of (A)-1 to (A)-18, (B)-1 to (B)-18, (C)-1 to (C)-18, (D)-1 to (D)-152, (E)-1 to (E)-152, (F)-1 to (F)-302, (G)-1 to (G)-302, and (H)-1 to (H)-302.

[0195]

[0196] The polycyclic compounds of the embodiments have a D (donor)-A (acceptor) molecular structure. Due to the large torsion angle between the electron donor and acceptor of the diindencarbazole, the polycyclic compounds of the embodiments can be used as thermally activated delayed fluorescence (TADF) materials. Furthermore, because of the introduction of electron-acceptor substituents on the electron donor, the degree of electron supply is relatively low; therefore, the polycyclic compounds of the embodiments can be used as luminescent materials to emit light in the blue wavelength region.

[0197] The polycyclic compound in the embodiments may be any of the compounds represented in compound group 1. The organic electroluminescent device 10 of the embodiments may include at least one polycyclic compound represented in compound group 1 in the emitting layer EML.

[0198] Compound group 1

[0199]

[0200]

[0201] The polycyclic compounds of the embodiments can be used as blue emitting materials. For example, the polycyclic compounds according to the embodiments can be used as luminescent materials to emit a maximum emission wavelength (λ) in the wavelength region of about 470 nm or smaller. max Blue light. For example, the polycyclic compound of the embodiments may be a luminescent material having a maximum emission wavelength in the wavelength region of about 430 nm to about 470 nm. The polycyclic compound of the embodiments represented by Formula 1 may be a blue thermally activated delayed fluorescence dopant. However, the embodiments of this disclosure are not limited thereto.

[0202] In the organic electroluminescent device 10 of the embodiment, when the emitting layer EML comprises the polycyclic compound of the embodiment, the emitting layer EML can emit delayed fluorescence. For example, the emitting layer EML can emit thermally activated delayed fluorescence (TADF).

[0203] In some embodiments, the organic electroluminescent device 10 of the embodiment may include a plurality of emission layers EML. The plurality of emission layers EML may be stacked one after another and provided. For example, the organic electroluminescent device 10 including a plurality of emission layers EML may emit white light. The organic electroluminescent device 10 including a plurality of emission layers EML may be an organic electroluminescent device having a series structure. When the organic electroluminescent device 10 includes a plurality of emission layers EML, at least one emission layer EML may include a polycyclic compound of the embodiment.

[0204] In embodiments, the emission layer EML includes a host and a dopant, and may include a polycyclic compound as a dopant. For example, in the organic electroluminescent device 10 of an embodiment, the emission layer EML may include a host to emit delayed fluorescence and a dopant to emit delayed fluorescence, and may include a polycyclic compound as a dopant to emit delayed fluorescence. The emission layer EML may include at least one of the polycyclic compounds represented in compound group 1 as a thermally activated delayed fluorescence dopant.

[0205] In some embodiments, the emitter layer EML may further comprise any suitable host material and the aforementioned polycyclic compound.

[0206] For example, in an embodiment, the emitter layer EML may include, as a host material, tris(8-hydroxyquinoline)aluminum (Alq3), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), poly(N-vinylcarbazole) (PVK), 9,10-bis(naphthyl-2-yl)anthracene (ADN), 4,4',4”-tris(carbazolyl-9-yl)-triphenylamine (TCTA), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBi), 3-tert-butyl-9,10-bis(naphthyl-2-yl)anthracene (TBADN), stilbene aromatic hydrocarbon (DSA), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), 2-methyl Examples of suitable host materials include 9,10-bis(naphthyl-2-yl)anthracene (MADN), bis[2-(diphenylphosphine)phenyl]ether oxide (DPEPO), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH2), hexaphenylcyclotrisiloxane (DPSiO3), octaphenylcyclotetrasiloxane (DPSiO4), 2,8-bis(diphenylphospho)dibenzo[b,d]furan (PPF), 3,3'-bis(N-carbazolyl)-1,1'-biphenyl (mCBP), and 1,3-bis(N-carbazolyl)benzene (mCP). However, embodiments of this disclosure are not limited thereto. Any suitable host material other than the host materials described above may be included to emit delayed fluorescence.

[0207] In the organic electroluminescent device 10 of the embodiment, the emission layer EML may further include any suitable dopant material. In the embodiment, the emission layer EML may include 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 N-(4-((E)-2-(6-((E)-4-(diphenylamino)styrene)naphth-2-yl)vinyl)phenyl)-N-phenylaniline (N-BDAVBi)), perylene and its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)), pyrene and its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenebenzene, 1,4-bis(N,N-diphenylamino)pyrene), etc.) as dopant.

[0208] like Figures 1 to 4 As shown, in the organic electroluminescent device 10 of this embodiment, the electron transport region (ETR) is provided on the emitter layer (EML). The electron transport region (ETR) may include at least one of the hole blocking layer (HBL), the electron transport layer (ETL), and the electron injection layer (EIL). However, embodiments of this disclosure are not limited thereto.

[0209] The electronic transport region (ETR) can have a single layer formed using a single material, a single layer formed using multiple different materials, or a multilayer structure with multiple layers formed using multiple different materials.

[0210] 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), or a single-layer structure formed using an electron injection material and an electron transport material. In some embodiments, the ETR may have a single-layer structure containing multiple different materials, or a structure stacked from the emitter layer (EML) of an electron transport layer (ETL) / electron injection layer (EIL), or a hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL). However, there are no limitations. The thickness of the ETR may be, for example, approximately [missing information - likely a number]. to approximately

[0211] 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 and / or laser-induced thermal imaging (LITI).

[0212] When the electron transport region (ETR) includes an electron transport layer (ETL), the ETL may include anthracene compounds. 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, 2-(4-(N-phenylbenzimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), and 3-(4-biphenyl)-4-phenyl 5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphth-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(naphth-2-yl)anthracene (ADN), 1,3-bis[3,5-bis(pyridin-3-yl)phenyl]benzene (BmPyPhB), or mixtures thereof, but without limitation. The thickness of the electron transport layer ETL can be approximately to approximately And it can be, for example, about to approximately When the thickness of the electron transport layer (ETL) meets the above range, satisfactory electron transport performance can be obtained without a significant increase in driving voltage.

[0213] When the electron transport region (ETR) includes an electron injection layer (EIL), the ETR may include metal halides (such as LiF, NaCl, CsF, RbCl, and / or RbI), lanthanides (such as ytterbium (Yb)), metal oxides (such as Li₂O and / or BaO), or lithium 8-hydroxyquinoline (LiQ). However, embodiments of this disclosure are not limited thereto. The electron injection layer (EIL) may be formed using a mixture of an electron injection material and an insulating organometallic salt. The insulating organometallic salt may be a material having a band gap of about 4 eV or higher. The insulating organometallic salt may include, for example, one or more metal acetates, metal benzoates, metal acetoacetates, metal acetylacetonates, and / or metal stearates. The thickness of the electron injection layer (EIL) may be approximately [missing information]. to approximately or about to approximately When the thickness of the electron injection layer (EIL) meets the range described above, satisfactory electron injection performance can be obtained without a significant increase in driving voltage.

[0214] The electron transport region (ETR) may include a hole blocking layer (HBL) as described above. The hole blocking layer (HBL) may include, for example, at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) and 4,7-diphenyl-1,10-phenanthroline (Bphen). However, embodiments of this disclosure are not limited thereto.

[0215] The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 can be a common electrode and / or a cathode. 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 include a transparent metal oxide, such as ITO, IZO, ZnO, ITZO, etc.

[0216] When the second electrode EL2 is a transmissive or reflective electrode, the second electrode EL2 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, their compounds, or mixtures thereof (e.g., a mixture of Ag and Mg). The second electrode EL2 may have a multilayer structure, including a reflective or transmissive layer formed using the above-mentioned materials and a transparent conductive layer formed using ITO, IZO, ZnO, ITZO, etc.

[0217] In some embodiments, 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.

[0218] On the second electrode EL2 of the organic electroluminescent device 10 of the embodiment, a capping layer CPL may be further disposed. The capping layer CPL may include, for example, N,N′-diphenyl-N,N′-bis(1-naphthyl)-1,1′-biphenyl-4,4′-diamine (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.

[0219] The organic electroluminescent device 10 according to embodiments of the present disclosure may include a polycyclic compound of the embodiments in at least one functional layer disposed between a first electrode EL1 and a second electrode EL2. For example, the organic electroluminescent device 10 according to embodiments of the present disclosure includes the polycyclic compound of the embodiments in the emission layer EML, thereby exhibiting excellent emission efficiency in the blue light emission wavelength region. In some embodiments, the polycyclic compound of the embodiments can be used as a thermally activated delayed fluorescence emission material, and the emission layer EML can exhibit high emission efficiency performance via thermally activated delayed fluorescence emission by including the polycyclic compound of the embodiments.

[0220] In some embodiments, the polycyclic compound may be included in an organic layer other than the emitting layer EML as a material for the organic electroluminescent device 10. For example, the organic electroluminescent device 10 according to embodiments of the present disclosure may include a polycyclic compound in at least one functional layer disposed between the first electrode EL1 and the second electrode EL2 or in a capping layer CPL disposed on the second electrode EL2.

[0221] The following description, with reference to and comparative embodiments, will explain in more detail the polycyclic compounds according to the embodiments and the organic electroluminescent devices according to the embodiments of this disclosure. The following embodiments are merely illustrative and are not intended to aid in understanding this disclosure; their scope is not limited thereto.

[0222] Example

[0223] 1. Polycyclic compounds synthesized according to the embodiments

[0224] Synthesize compounds 1, 3, 4 and 5

[0225] [Reaction 1-1]

[0226]

[0227] Compound A (synthesized by the method for Sub 1-1 described in patent document WO2018131877, the entire contents of which are incorporated herein by reference) (20.0 g, 47.5 mmol), 4-bromobenzonitrile (9.50 g, 52.2 mmol), bis(dibenzylacetone)palladium(O) (Pd2(dba)3, 0.87 g, 0.95 mmol), tri-tert-butylphosphonium tetrafluoroborate (P(t-Bu)3HBF4, 1.10 g, 3.80 mmol), and sodium tert-butoxide (NaOtBu, 6.85 g, 71.3 mmol) were added to toluene (1.2 L), and the mixture was heated and stirred at 80 °C for 2 hours. Water was then added, and the mixture was separated by diatomaceous earth filtration, followed by concentration of the organic layer. The product was purified by silica gel column chromatography to obtain intermediate 1 (21.0 g, 85% yield). The molecular weight, measured by FAB-MS, was m / z = 523 (M). + +1).

[0228] [Reaction 1-2]

[0229]

[0230] The additional reaction using intermediate 1 was carried out under substantially the same conditions as described above, and compounds 1, 3, 4, and 5 were synthesized. The yields and weights of the synthesized compounds are described in the synthetic schemes disclosed in reactions 1-2 above.

[0231] Synthetic compound 2

[0232] [Reaction 2-1]

[0233]

[0234] Compound B (5.00 g, 14.5 mmol), 4-bromobenzonitrile (5.81 g, 31.9 mmol), bis(dibenzylacetone)palladium(O) (Pd2(dba)3, 0.27 g, 0.29 mmol), tri-tert-butylphosphonium tetrafluoroborate (P(t-Bu)3HBF4, 0.34 g, 1.16 mmol), and sodium tert-butoxide (NaOtBu, 2.09 g, 21.8 mmol) were added to toluene (200 mL), and the mixture was heated and stirred at 80 °C for 2 hours. Water was then added, and the mixture was separated by diatomaceous earth filtration, followed by concentration of the organic layer. Purification by silica gel column chromatography yielded intermediate 2 (5.56 g, 70% yield). The molecular weight, measured by FAB-MS, was m / z = 548 (M). + +1). Compound B was purchased from Tokyo Chemical Industry Co., Ltd. and used in the synthesis.

[0235] [Reaction 2-2]

[0236]

[0237] Another reaction was carried out under substantially the same conditions as described above to provide compound 2 (5.11 g, 89% yield). The molecular weight, as measured by FAB-MS, was m / z = 855 (M). + +1).

[0238] Synthesized compounds 6, 8, 9 and 10

[0239] [Reaction 3-1]

[0240]

[0241] Compound A (20.0 g, 47.5 mmol), 1-fluoro-4-iodobenzene (11.6 g, 52.2 mmol), bis(dibenzylacetone)palladium(0) (Pd2(dba)3, 0.87 g, 0.95 mmol), tri-tert-butylphosphonium tetrafluoroborate (P(t-Bu)3HBF4, 1.10 g, 3.80 mmol), and sodium tert-butoxide (NaOtBu, 6.85 g, 71.3 mmol) were added to toluene (1.2 L), and the mixture was heated and stirred at 80 °C for 2 hours. Water was then added, and the mixture was separated by diatomaceous earth filtration. The organic layer was then concentrated and purified by silica gel column chromatography to obtain intermediate 3 (20.1 g, 82% yield). The molecular weight, measured by FAB-MS, was m / z = 517 (M). + +1).

[0242] [Reaction 3-2]

[0243]

[0244] The reactions were carried out under substantially the same conditions as described above to provide compounds 6, 8, 9, and 10. The yields and weights of the synthesized compounds are described in the synthetic scheme disclosed in reaction 3-2.

[0245] Synthetic compound 7

[0246] [Reaction 4-1]

[0247]

[0248] Compound B (5.00 g, 14.5 mmol), 1-fluoro-4-iodobenzene (7.08 g, 31.9 mmol), bis(dibenzylacetone)palladium(0) (Pd2(dba)3, 0.87 g, 0.95 mmol), tri-tert-butylphosphonium tetrafluoroborate (P(t-Bu)3HBF4, 1.10 g, 3.80 mmol), and sodium tert-butoxide (NaOtBu, 6.85 g, 71.3 mmol) were added to toluene (1.2 L), and the mixture was heated and stirred at 80 °C for 2 hours. Water was then added, and the mixture was separated by diatomaceous earth filtration. The organic layer was then concentrated and purified by silica gel column chromatography to obtain intermediate 4 (6.18 g, 80% yield). The molecular weight, measured by FAB-MS, was m / z = 534 (M). + +1).

[0249] [Reaction 4-2]

[0250]

[0251] Another reaction was carried out under substantially the same conditions as described above to provide compound 7 (5.12 g, 79% yield). The molecular weight, as measured by FAB-MS, was m / z = 841 (M). + +1).

[0252] Synthesized compounds 12, 13, 14 and 15

[0253] [Reaction 5-1]

[0254]

[0255] Compound A (20.0 g, 47.5 mmol), 1-iodo-4-(trifluoromethyl)benzene (14.2 g, 52.2 mmol), bis(dibenzylideneacetone)palladium(0) (Pd2(dba)3, 0.87 g, 0.95 mmol), tri-tert-butylphosphonium tetrafluoroborate (P(t-Bu)3HBF4, 1.10 g, 3.80 mmol), and sodium tert-butoxide (NaOtBu, 6.85 g, 71.3 mmol) were added to toluene (1.2 L), and the mixture was heated and stirred at 80 °C for 2 hours. Water was then added, and the mixture was separated by diatomaceous earth filtration. The organic layer was then concentrated and purified by silica gel column chromatography to obtain intermediate 5 (20.1 g, 78% yield). The molecular weight, measured by FAB-MS, was m / z = 566 (M). + +1).

[0256] Reaction 5-2

[0257]

[0258] The subsequent reactions were carried out under substantially the same conditions as described above to provide compounds 12, 13, 14, and 15. The yields and weights of the synthesized compounds are described in the synthetic scheme disclosed in reaction 5-2 above.

[0259] Synthetic compound 11

[0260] [Reaction 6-1]

[0261]

[0262] Compound B (5.00 g, 14.5 mmol), 1-iodo-4-(trifluoromethyl)benzene (8.67 g, 31.9 mmol), bis(dibenzylideneacetone)palladium(0) (Pd2(dba)3, 0.87 g, 0.95 mmol), tri-tert-butylphosphonium tetrafluoroborate (P(t-Bu)3HBF4, 1.10 g, 3.80 mmol), and sodium tert-butoxide (NaOtBu, 6.85 g, 71.3 mmol) were added to toluene (1.2 L), and the mixture was heated and stirred at 80 °C for 2 hours. Water was then added, and the mixture was separated by diatomaceous earth filtration. The organic layer was then concentrated and purified by silica gel column chromatography to obtain intermediate 6 (6.88 g, 80% yield). The molecular weight, measured by FAB-MS, was m / z = 634 (M). + +1).

[0263] [Reaction 6-2]

[0264]

[0265] Another reaction was carried out under substantially the same conditions as described above to provide compound 11 (6.12 g, yield 81%). The molecular weight, as measured by FAB-MS, was m / z = 942 (M). + +1).

[0266] 2. Evaluation of polycyclic compounds

[0267] The luminescence properties of the polycyclic compounds of the examples and the comparative compounds of the comparative examples were evaluated. The compounds of the examples and the comparative compounds of the comparative examples used in evaluating the luminescence properties are as follows.

[0268] (Compounds in the Examples)

[0269]

[0270]

[0271] (Comparative compounds for comparative examples)

[0272]

[0273] Evaluate the luminescent properties of compounds

[0274] A 5.0 mM toluene solution was prepared for use with the compounds in the examples and the comparative compounds in the comparative examples, and the luminescence properties were evaluated using a JASCOV-670 spectrometer. Emission spectra were measured at room temperature (e.g., approximately 298 K) and 77 K. Table 1 shows the maximum emission wavelength λ in the emission spectra measured at room temperature. max The full width at half maximum (FWHM) of the emission spectrum was measured. Furthermore, the photoluminescence quantum yield (PLQY) of a 5.0 mM toluene solution was measured using a HAMAMATSU Quantaurus-QY instrument.

[0275] Table 1

[0276]

[0277]

[0278] Referring to the results in Table 1, it can be seen that the polycyclic compounds 1 to 15 of the Examples each exhibit a maximum emission wavelength of 470 nm or less, thus emitting deep blue light. In contrast, the comparative compounds X-1 to X-6 emit light with relatively longer wavelengths compared to the Example compounds. From the evaluation of the luminescence properties of the compounds shown in Table 1, it can be seen that the polycyclic compounds of the Examples of the present invention emit light in the short wavelength region of 470 nm or less and exhibit good quantum efficiency performance.

[0279] 3. Manufacturing and evaluating organic electroluminescent devices

[0280] Manufacturing organic electroluminescent devices

[0281] On the glass substrate, there will be approximately The ITO layer was patterned to a thickness of approximately [thickness value] and rinsed with ultrapure water, ultrasonically cleaned, exposed to UV for approximately 30 minutes, and treated with ozone to form the first electrode. Then, HAT-CN was deposited to approximately [thickness value value]. The thickness of α-NPD is deposited to approximately [amount missing]. And deposit mCP to approximately The thickness is increased to form a hole transport region.

[0282] Then, the polycyclic compound or comparative compound of the embodiment is co-deposited with the host material at a ratio of 1:99 to form a structure having approximately An emission layer of a certain thickness. An emission layer formed by co-deposition is provided by mixing compounds 1 to 15 with mCBP and depositing the mixture in the apparatus of Examples 1 to 15, or by mixing comparative compounds X-1 to X-8 with mCBP and depositing the mixture in the apparatus of Comparative Examples 1 to 8.

[0283] Subsequently, on the emitter layer, TPBi is used to form approximately A layer of approximately [thickness] was formed using LiF. A layer of approximately [thickness value missing] is formed to create an electron transport region. Then, aluminum (Al) is used to form a layer with approximately [thickness value missing]. The second electrode has a thickness of [missing information].

[0284] The hole transport region, emitter layer, electron transport region, and second electrode are formed using vacuum deposition equipment.

[0285] Evaluation of the performance of organic electroluminescent devices

[0286] Table 2 shows the evaluation results of the organic electroluminescent devices of Examples 1 to 15 and Comparative Examples 1 to 8. In the evaluation results of the examples and comparative examples shown in Table 2, the maximum emission wavelength (λ) max The external quantum efficiency (EQE) indicates the wavelength representing the maximum value in the emission spectrum. max ) indicates the maximum value of the external quantum efficiency, and EQE max (1000 nits) indicates when the display shows 1000 cd / m³ 2 The external quantum efficiency at brightness.

[0287] Table 2

[0288]

[0289] Referring to the results in Table 2, it can be seen that, compared with the organic electroluminescent devices of Comparative Examples 1 to 8, the organic electroluminescent devices of Examples 1 to 15 emit short-wavelength deep blue light and exhibit high efficiency characteristics.

[0290] The polycyclic compounds of the examples each include at least one electron-accepting group (such as cyano, fluoro, and / or trifluoromethyl) substituted on the core of diindencarbazole, which acts as an electron donor, while the comparative compound does not include this. Without being limited by the correctness of any theory or explanation, it is believed that this enables the examples to exhibit fairly excellent luminous efficiency characteristics in the short wavelength region of 470 nm or smaller.

[0291] Compared to Comparative Examples 1 to 6, Examples 1 to 15 emitted light in the short wavelength region and exhibited improved luminous efficiency characteristics. For example, in the cases of Comparative Examples 4 and 5, diindronecarbazole was included as in the electron donors of the example compounds, but it was not substituted with an electron acceptor group, and thus the comparative compounds emitted light in the long wavelength region compared to the examples.

[0292] Comparative Examples 7 and 8 emit light in the short wavelength region of 470 nm or less, but exhibit reduced luminous efficiency compared to Examples 1 to 15.

[0293] Therefore, the organic electroluminescent device including the polycyclic compound of the embodiments can exhibit excellent luminous efficiency in the short wavelength region of 470 nm or less. The polycyclic compound of the embodiments includes a diindenzocarbazole core as an electron donor, which includes an electron accepting group (such as cyano, fluoro, and / or trifluoromethyl) as at least one substituent.

[0294] Furthermore, by having a structure having at least one substituent including an electron donor and an electron acceptor group (such as cyano, fluorine, and / or trifluoromethyl), the polycyclic compounds of the embodiments exhibit good quantum efficiency in the short wavelength region. The polycyclic compounds include a diindenzocarbazole core as an electron donor. The polycyclic compounds of the embodiments can be used as thermally activated delayed fluorescence materials.

[0295] Although exemplary embodiments of the invention have been described, it will be understood that the invention should not be limited to these exemplary embodiments, but rather that various changes and modifications can be made by those skilled in the art within the spirit and scope of this disclosure as set forth in the appended claims and their equivalents.

Claims

1. An organic electroluminescent device comprising: a first electrode; a second electrode on the first electrode; and a plurality of functional layers between the first electrode and the second electrode, wherein at least one of the plurality of functional layers comprises a polycyclic compound represented by Formula 1, and 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, a compound of two or more thereof, a mixture of two or more thereof, or an oxide thereof: Formula 1 wherein in Formula 1, A1to A5are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted thiocarbonyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for ring formation, and / or combine with an adjacent group to form a fused heterocycle, at least one of A1to A5or the fused heterocycle comprises an electron acceptor, and "Du" is represented by Formula 2: Formula 2 wherein in Formula 2, R1 to R 22 R5 to R9 and R 14 To R 18 At least one of them is cyano, fluoro, or trifluoromethyl, and the remainder is each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted oxygen group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms for cyclization, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms for cyclization. "-" means a linking position. 2.The organic electroluminescent device according to claim 1, wherein the plurality of functional layers comprise: a hole transport zone; an emission layer on the hole transport zone; and an electron transport zone on the emission layer, wherein the emission layer comprises the polycyclic compound represented by Formula 1. 3.The organic electroluminescent device according to claim 2, wherein the emission layer emits delayed fluorescence. 4.The organic electroluminescent device according to claim 2, wherein the emission layer emits light having a maximum emission wavelength of 470 nm or less. 5.The organic electroluminescent device according to claim 1, wherein Formula 1 is represented by any one of Formula 1-A to Formula 1-D: Formula 1-A Formula 1-B Formula 1-C Formula 1-D wherein in formula 1-A, at least one of X1to X5is N, and the rest are each CR a , In Formula 1-C and Formula 1-D, Y1to Y3are each independently O, S, NR e , C(=S), or C(=O). In Formulae 1-A and 1-B, A 11 to A 14 each independently is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for ring formation, In Formulae 1-A to 1-D, R a to R e each independently is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aliphatic cyclic group having 6 to 30 carbon atoms for ring formation, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for ring formation, and "Du" is the same as defined in Formula 2. 6.The organic electroluminescent device according to claim 1, wherein Formula 1 is represented by any one of Formula 1-1 to Formula 1-23: wherein in Formulae 1-1 to 1-23, "Du" is the same as defined in Formula 2. 7.The organic electroluminescent device according to claim 1, wherein the electron acceptor is a substituted or unsubstituted heterocycle having at least one nitrogen atom as a ring-forming atom, or a substituted or unsubstituted boron group. 8.The organic electroluminescent device according to claim 1, wherein the fused heterocycle is a substituted or unsubstituted heterocycle having a boron atom as a ring-forming atom.

9. The organic electroluminescence device according to claim 1, wherein in formula 2, at least one of R1 to R 22 is a cyano group, a fluoro group, or a trifluoromethyl group, and the rest are each a hydrogen atom.

10. The organic electroluminescence device according to claim 1, wherein in formula 2, at least two selected from R1 to R 22 are each a cyano group, a fluoro group, or a trifluoromethyl group, and the rest are each a hydrogen atom. 11.The organic electroluminescent device according to claim 1, wherein the polycyclic compound represented by Formula 1 is represented by at least one polycyclic compound in Compound Group 1: Compound Group 1 12. The organic electroluminescent device according to claim 1, wherein at least one of A1 to A5 or a fused heterocycle formed by combining one or more of A1 to A5 with an adjacent group comprises an electron-accepting group comprising a cyano group, a fluoro group, a carbonyl group, or a sulfonyl group.

13. The organic electroluminescent device according to claim 1, wherein the polycyclic compound represented by formula 1 is a material that emits blue light having a maximum emission wavelength of 470 nm or less.

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