Organic electroluminescent devices and polycyclic compounds for use in organic electroluminescent devices

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, wherein the emission layer comprises a polycyclic compound represented by Formula 1, thereby exhibiting high emission efficiency: Formula 1, wherein at least one of n1 to n6 is 1.

Description

[0001] Cross-references to related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2020-0064093, filed on May 28, 2020, 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 use in organic electroluminescent devices. Background Technology

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

[0005] In applications of organic electroluminescent devices to displays, there is a need (or expectation) for lower driving voltages and increased emission efficiency and / or lifetime of organic electroluminescent devices, and there is a ongoing need (or expectation) for the development of materials for organic electroluminescent devices that can reliably achieve the aforementioned needs.

[0006] In particular, recently, in order to realize highly efficient organic electroluminescent devices, techniques for phosphorescence emission (which uses energy in the triplet state) and / or delayed fluorescence emission (which uses the phenomenon of singlet exciton generation through collision of triplet excitons (triplet-triplet annihilation, TTA)) are being developed, and materials for thermally activated delayed fluorescence (TADF) using the delayed fluorescence phenomenon 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 the embodiments of this disclosure also relate to organic electroluminescent devices comprising materials that emit thermally activated delayed fluorescence and polycyclic compounds used as thermally activated delayed fluorescence materials.

[0009] In one or more embodiments, a polycyclic compound represented by Formula 1 is provided:

[0010] Formula 1

[0011]

[0012] In Equation 1, Y1 and Y2 can each be independently B, N, P=O or P=S; X1 to X 12 Each can be independently a BAr1, O, S, NAr2, or a direct bond; Ar1 ​​and Ar2 can each be independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation; Y3 and R1 to R 12 Each of the following groups may be independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, 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 forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, and / or may be bonded to one or more adjacent groups to form one or more rings; "a" to "f" may each be independently an integer from 0 to 4, "j" and "k" may each be independently an integer from 0 to 3; "g" to "i" and "l" may each be independently an integer from 0 to 2; and n1 to n6 may each be independently 0 or 1, wherein at least one of n1 to n6 is 1.

[0013] In one or more implementations, Y1 and Y2 can be the same.

[0014] In one or more embodiments, Equation 1 can be represented by the following Equation 2:

[0015] Formula 2

[0016]

[0017] In Equation 2, Y 31 It can be CA or N; A can be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, 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 forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring; "j′" and "k′" can each be an integer from 0 to 2 independently; and Y1, Y2, X1 to X 12 R1 to R 12 The "a" to "i", "l" and n1 to n6 are the same as those defined in Equation 1.

[0018] In one or more embodiments, Equation 1 can be represented by the following Equation 3:

[0019] Formula 3

[0020]

[0021] In Equation 3, Y 32 It can be CA1A2 or NA3; A1 to A3 can each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, 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 forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring; "j′" can be an integer from 0 to 2; and Y1, Y2, X1 to X 12 R1 to R 12 The "a" to "i", "k", "l" and n1 to n6 are the same as those defined in Equation 1.

[0022] In one or more embodiments, Equation 1 can be represented by the following Equation 4:

[0023] Formula 4

[0024]

[0025] In Equation 4, "q" and "r" can each be an integer from 0 to 5 independently; "p" and "s" can each be an integer from 0 to 4 independently; and Y1 to Y3, X1 to X4, R1, R2, R7 to R 12 “a”, “b”, “g”, “h”, n1 and n2 are the same as those defined in Equation 1.

[0026] In one or more embodiments, Equation 2 can be represented by the following Equation 5:

[0027] Formula 5

[0028]

[0029] In Equation 5, "p" to "s" can each be an integer from 0 to 4 independently; and Y1, Y2, Y... 31 X1 to X4, R1, R2, R7 to R 12 “a”, “b”, “g” and “h” are the same as those defined in Equation 2.

[0030] In one or more embodiments, Equation 2 can be represented by the following Equation 6:

[0031] Formula 6

[0032]

[0033] In Equation 6, "p" to "t" can each be an integer from 0 to 4 independently; and Y1, Y2, Y... 31 X1, X2, R1, R7 to R 12 The "a" and "g" are the same as those defined in Equation 2.

[0034] In one or more embodiments, the compound represented by Formula 1 may be at least one of the compounds represented in Compound Group 1.

[0035] In one or more embodiments of this disclosure, an organic electroluminescent device is provided, comprising: a first electrode; a hole transport region disposed (e.g., provided) 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 first electrode and the second electrode each independently comprise at least one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, In, Zn, Sn, compounds thereof, mixtures thereof, and oxides thereof, and the emission layer comprises the polycyclic compound of one or more embodiments.

[0036] In one or more embodiments, the emitting layer can emit delayed fluorescence.

[0037] In one or more embodiments, 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.

[0038] In one or more embodiments, the emitting layer may be a thermally activated delayed fluorescence emitting layer that emits blue light. Attached Figure Description

[0039] 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:

[0040] Figure 1 This is a schematic illustration of a cross-sectional view of an organic electroluminescent device according to one or more embodiments of the present disclosure;

[0041] Figure 2 This is a schematic illustration of a cross-sectional view of an organic electroluminescent device according to one or more embodiments of the present disclosure;

[0042] Figure 3 This schematically illustrates a cross-sectional view of an organic electroluminescent device according to one or more embodiments of the present disclosure; and

[0043] Figure 4 This is a schematic cross-sectional view illustrating one or more embodiments of an organic electroluminescent device according to the present disclosure. Detailed Implementation

[0044] This disclosure may have various modifications and may be implemented in different forms, and exemplary embodiments will be explained in more 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 in this disclosure.

[0045] It should be understood that when a component (or area, layer, part, etc.) is referred to as being “on”, “connected to”, or “linked to” another component, it can be directly on, directly connected to, or directly linked to another component (without any intermediate component in between), or there can be one or more third intermediate components.

[0046] The same reference numerals refer to the same elements throughout. Furthermore, in the accompanying drawings, the thickness, scale, and dimensions of the constituent elements are enlarged for effective explanation of the technical content. The term "and / or" includes one or more combinations that can be defined by related elements. Expressions such as "at least one of...", "one of...", and "selected from" modify the entire column of elements when preceding a column of elements, but 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".

[0047] 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. Therefore, without departing from the teachings of this disclosure, a first element may be referred to as a second element. Similarly, a second element may be referred to as a first element. As used herein, the singular form is intended to also include the plural form unless the context clearly indicates otherwise.

[0048] Furthermore, the terms "below," "under," "above," and "above" are used to explain the relationship between the elements shown in the accompanying drawings. These terms are relative concepts and are interpreted based on the directions shown in the drawings.

[0049] 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 be further understood that terms (e.g., those defined in commonly used 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, unless expressly defined herein.

[0050] It should be further understood that the terms “comprises” and / or “comprising”, when used in this specification, specify the presence of a designated feature, number, step, operation, element, component, or combination thereof, but do not exclude the presence or addition of one or more other features, numbers, steps, operations, elements, components, or combinations thereof.

[0051] In the following, an organic electroluminescent device according to one or more embodiments of the present disclosure will be explained with reference to the accompanying drawings.

[0052] Figures 1 to 4 This is a schematic cross-sectional view of an organic electroluminescent device according to an exemplary embodiment of the present disclosure. Reference Figures 1 to 4 In an organic electroluminescent device 10 according to one or more embodiments, a first electrode EL1 and a second electrode EL2 are disposed opposite to each other, and an emission layer EML may be disposed between the first electrode EL1 and the second electrode EL2.

[0053] In one or more embodiments, in addition to the emitter layer EML, the organic electroluminescent device 10 of one or more embodiments further includes multiple functional layers between the first electrode EL1 and the second electrode EL2. The multiple functional layers may include a hole transport region HTR and an electron transport region ETR. For example, the organic electroluminescent device 10 of one or more embodiments 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 one or more embodiments, the organic electroluminescent device 10 of one or more embodiments may include a capping layer CPL disposed on the second electrode EL2.

[0054] One or more embodiments of the organic electroluminescent device 10 include one or more polycyclic compounds of the embodiments described below in the emitter layer EML disposed between the first electrode EL1 and the second electrode EL2. However, embodiments of the present disclosure are not limited thereto, and in addition to the emitter layer EML, one or more embodiments of the organic electroluminescent device 10 may include one or more polycyclic compounds of the embodiments in the hole transport region HTR and / or electron transport region ETR included in a plurality of functional layers disposed between the first electrode EL1 and the second electrode EL2, or may include one or more polycyclic compounds of the embodiments in the capping layer CPL disposed on the second electrode EL2.

[0055] At the same time, when with Figure 1 In comparison, Figure 2 A cross-sectional view of an organic electroluminescent device 10 according to one or more embodiments 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. In one or more embodiments, when with Figure 1 In comparison, Figure 3 A cross-sectional view of an organic electroluminescent device 10 is shown, comprising one or more embodiments, 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 compared with... Figure 2 In comparison, Figure 4 A cross-sectional view of an organic electroluminescent device 10, comprising one or more embodiments, is shown, including a capping layer CPL disposed on a second electrode EL2.

[0056] The first electrode EL1 is conductive. The first electrode EL1 can be formed using a metal alloy or any suitable conductive compound. The first electrode EL1 can be a pixel electrode or an anode. The first electrode EL1 can be a transmissive electrode, a semi-transmissive reflective electrode, or a reflective electrode. If the first electrode EL1 is a transmissive electrode, it can be formed using a transparent metal oxide (e.g., indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), and / or indium tin zinc oxide (ITZO)). If the first electrode EL1 is a semi-transmissive reflective electrode or a reflective electrode, it can contain Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, their compounds, or mixtures thereof (e.g., a mixture of Ag and Mg). Furthermore, the first electrode EL1 can have a structure comprising multiple layers, including a reflective or semi-transmissive reflective layer formed using any of the above 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 to approximately For example, about to approximately

[0057] The hole transport region HTR is provided on the first electrode EL1. The hole transport region HTR may include at least one of the following: hole injection layer HIL, hole transport layer HTL, hole buffer layer, and electron blocking layer EBL.

[0058] The hole transport region (HTR) can have a single layer (e.g., a single-layer structure) formed using a single material (e.g., composed of a single material), a single layer formed using multiple different materials, or a multilayer structure including multiple layers formed using multiple different materials.

[0059] 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 using a hole injection material and a hole transport material. In one or more embodiments, the hole transport region HTR can have a single-layer structure formed using a variety of different materials, or a structure of 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 stacked from the first electrode EL1, but is not limited thereto.

[0060] Hole transport regions (HTRs) can be formed using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and laser-induced thermal imaging (LITI).

[0061] 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″-tris{(N-2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA), poly(3,4-ethylenedioxythiophene) / poly(4-phenylethyl) 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] and / or dipyrazino[2,3-f:2′,3′-h]quinoxaline-2,3,6,7,10,11-hexacarboxynitrile (HAT-CN).

[0062] Hole transport layers (HTLs) can contain suitable materials, such as carbazole derivatives (e.g., N-phenylcarbazole and / or polyvinylcarbazole), fluorene-based derivatives, N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine (TPD), triphenylamine-based 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.

[0063] The electron blocking layer (EBL) may contain, for example, carbazole derivatives (e.g., N-phenylcarbazole and / or polyvinylcarbazole), fluorene-based derivatives, N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine (TPD), triphenylamine-based derivatives (e.g., 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA)), N,N′-bis(naphthyl-1-yl)-N,N′-diphenyl-benzidine (NPB), 4,4′-cyclohexylenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4′-bis[N,N′-(3-tolyl)amino-3,3′-dimethylbiphenyl] (HMTPD), mCP, etc.

[0064] 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... to approximately For example, the thickness of the electron blocking layer EBL can be approximately to approximately Satisfactory (or suitable) hole transport properties can be achieved without a significant increase in driving voltage when the thicknesses of the hole transport region HTR, hole injection layer HIL, hole transport layer HTL, and electron blocking layer EBL each independently satisfy the ranges described above.

[0065] 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 uniformly or non-uniformly dispersed in the hole transport region (HTR). The charge-generating material may be, for example, a p-doper. The p-doper may be, but is not limited to, a quinone derivative, a metal oxide, or a cyano-containing compound. For example, non-limiting examples of p-dopers may include quinone derivatives (e.g., tetracyanoquinone dimethyl ether (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7′,8,8′-tetracyanoquinone dimethyl ether (F4-TCNQ)) and metal oxides (e.g., tungsten oxide and / or molybdenum oxide).

[0066] 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 based on the wavelength of light emitted from the emitter layer (EML) and can increase the light emission efficiency. Any of the materials that can be included in the hole transport region (HTR) can be used as the material included in the hole buffer layer. The electron blocking layer (EBL) is a layer that prevents or reduces electron injection from the electron transport region (ETR) to the hole transport region (HTR).

[0067] The emitter layer EML is 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.

[0068] The emitting layer (EML) can emit one of the following colors of light: red, green, blue, white, yellow, and cyan. The EML can contain fluorescent or phosphorescent materials.

[0069] In one or more embodiments, the emitting layer EML may be a fluorescent emitting layer. For example, a portion of the light emitted from the emitting layer EML may be thermally activated delayed fluorescence (TADF). In one or more embodiments, the emitting layer EML may include a light-emitting component that emits (e.g., is intended to emit) thermally activated delayed fluorescence, and in one or more embodiments, the emitting layer EML may be a thermally activated delayed fluorescence emitting layer that emits (e.g., is intended to emit) blue light.

[0070] The emitting layer EML of one or more embodiments of the organic electroluminescent device 10 comprises a polycyclic compound according to one or more embodiments of the present disclosure.

[0071] In the description, the term "substituted or unsubstituted" corresponds to an unsubstituted group or a group substituted by at least one substituent selected from the group consisting of deuterium, halogen, cyano, nitro, amino, silyl, oxy, thio, sulfinyl, sulfonyl, carbonyl, boron, phosphine oxide, phosphine sulfide, alkyl, alkenyl, alkoxy, aryl, and heterocyclic groups. In one or more embodiments, each of the exemplified substituents may be substituted or unsubstituted. For example, a biphenyl group may be interpreted as an aryl group or a phenyl group substituted with a phenyl group.

[0072] In the description, the term "forming a ring via bonding with an adjacent group" can mean forming a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle via bonding with an adjacent group. Hydrocarbon rings include aliphatic hydrocarbon rings and aromatic hydrocarbon rings. Heterocycles include aliphatic heterocycles and aromatic heterocycles. The ring formed by bonding with an adjacent group can be a monocyclic ring or a polycyclic ring. In one or more embodiments, the ring formed by bonding with an adjacent group can bond with another ring to form a spirostructure.

[0073] In the description, the term "adjacent group" can refer to a pair of substituent groups in which the first substituent is connected to an atom directly attached to another atom substituted by the second substituent; a pair of substituent groups attached to the same atom; or a pair of substituent groups in which the first substituent is spatially located at the position closest to the second substituent. 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.

[0074] In the description, examples of halogen atoms may include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0075] In the description, alkyl groups can be abaxial alkyl groups or cyclic alkyl groups, unless otherwise classified. The number of carbon atoms in an alkyl group can be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of alkyl groups may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl. Undecyl, dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, hexadecyl, nonadecanyl, triadecyl, tridecyl, tridecyl, pentadecyl, hexadecyl, heptadecanyl, hexadecyl, nonadecanyl, triadecyl, etc., but not limited thereto. Examples of cyclic alkyl groups may include cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, cyclooctyl, etc., but not limited thereto.

[0076] In the description, an alkenyl group can refer to a hydrocarbon group containing one or more carbon double bonds at the middle and / or any end of an alkyl group having two or more carbon atoms. The alkenyl group can be a straight-chain group or a branched group. The number of carbon atoms is not particularly limited, but can be 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups include, but are not limited to, vinyl groups, 1-butenyl groups, 1-pentenyl groups, 1,3-butadienylaryl groups, styryl groups, styrylvinyl groups, etc.

[0077] In this description, an alkynyl group refers to a hydrocarbon group containing one or more carbon triple bonds at the middle and / or any end of an alkyl group having two or more carbon atoms. The alkynyl group can be a straight-chain group or a branched-chain group. The number of carbon atoms is not particularly limited, but can be 2 to 30, 2 to 20, or 2 to 10. Examples of alkynyl groups include, but are not limited to, ethynyl groups, propynyl groups, etc.

[0078] In the description, the hydrocarbon ring group can be a functional group or substituent derived from an aliphatic hydrocarbon ring, or a functional group or substituent derived from an aromatic hydrocarbon ring. The number of carbons in the hydrocarbon ring group used to form the ring can be 5 to 60, 5 to 30, or 5 to 20.

[0079] In this description, an aryl group can refer to a functional group or substituent derived from an aromatic hydrocarbon ring. An aryl group can be a monocyclic or polycyclic aryl group. The number of carbons in the aryl group used to form the ring can be 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups can include phenyl, naphthyl, fluorenyl, anthraceneyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, hexaphenyl, benzo[a]phenanthryl, pyrene, benzo[a]fluoranyl, anthraceneyl, etc. Basic, but not restricted.

[0080] In this description, a heterocyclic group can refer to a functional group or substituent derived from a ring containing one or more of B, O, N, P, Si, and S as heteroatoms. Heterocyclic groups include aliphatic heterocyclic groups and aromatic heterocyclic groups. Aromatic heterocyclic groups can be heteroaryl groups. Aliphatic and aromatic heterocycles can each be monocyclic or polycyclic independently.

[0081] In the description, the heterocyclic group may contain one or more of B, O, N, P, Si, and S as heteroatoms. If the heterocyclic group contains 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 has the concept of including a heteroaryl group. The number of carbons in the heterocyclic group for forming the ring may be 2 to 30, 2 to 20, or 2 to 10.

[0082] In the description, the aliphatic heterocyclic group may contain one or more of B, O, N, P, Si, and S as heteroatoms. The number of carbon atoms in the aliphatic heterocyclic group used to form the ring may be 2 to 30, 2 to 20, or 2 to 10. Examples of aliphatic heterocyclic groups may be oxetane propane groups, thiohexane propane groups, pyrrolidinyl groups, piperidine groups, tetrahydrofuran groups, tetrahydrothiophene groups, thiane groups, tetrahydropyran groups, 1,4-dioxane groups, etc., but are not limited thereto.

[0083] In the description, the heteroaryl group may contain one or more of B, O, N, P, Si, and S as heteroatoms (e.g., 1 to 5 or 1 to 3 heteroatoms). If the heteroaryl group contains two or more heteroatoms, the two or more heteroatoms may be the same or different. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. The number of carbons in the heteroaryl group for forming the ring may be 2 to 30, 2 to 20, or 2 to 10. Examples of heteroaryl groups may include those derived from the following groups: thiophene, furan, pyrrole, imidazole, 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, thiazole, isoxazole, oxazole, oxadiazole, thiadiazole, phenothiazine, dibenzothiophene, dibenzofuran, etc., but are not limited thereto.

[0084] In the description, the number of carbon atoms in the amine group is not particularly limited, but can be from 1 to 30. The amine group can include alkylamine groups, arylamine groups, or heteroarylamine groups. Examples of amine groups include, but are not limited to, methylamine groups, dimethylamine groups, phenylamine groups, diphenylamine groups, naphthylamine groups, 9-methyl-anthraylamine groups, etc.

[0085] In the description, the thio group may include alkyl thio groups and aryl thio groups.

[0086] In the description, "atoms used to form a ring" can refer to ring-forming atoms.

[0087] In the description, "direct bond" can refer to a chemical bond, such as a single bond.

[0088] The polycyclic compound according to one or more embodiments of this disclosure is represented by the following formula 1:

[0089] Formula 1

[0090]

[0091] In Equation 1, Y1 and Y2 are each independently B, N, P=O or P=S.

[0092] In Equation 1, X1 to X 12 Each is independently a BAr1, O, S, NAr2 or a direct bond; and Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring.

[0093] In Equation 1, Y3 and R1 to R 12 Each of the following is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, 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 forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, and / or bonded to each adjacent group to form a ring.

[0094] In Equation 1, "a" to "f" are each an independent integer from 0 to 4. Furthermore, if "a" is 2 or greater than 2, multiple R1 groups are the same or different; if "b" is 2 or greater than 2, multiple R2 groups are the same or different; if "c" is 2 or greater than 2, multiple R3 groups are the same or different; if "d" is 2 or greater than 2, multiple R4 groups are the same or different; if "e" is 2 or greater than 2, multiple R5 groups are the same or different; and if "f" is 2 or greater than 2, multiple R6 groups are the same or different.

[0095] In Equation 1, "j" and "k" are each independent integers from 0 to 3. Also, if "j" is 2 or greater than 2, multiple R... 10 The groups are the same or different, and if "k" is 2 or greater than 2, multiple R groups are allowed. 11 The functional groups may be the same or different.

[0096] In Equation 1, "g" through "i" and "l" are each independently an integer from 0 to 2. Furthermore, if "g" is 2, multiple R7 groups are identical or different; if "h" is 2, multiple R8 groups are identical or different; if "i" is 2, multiple R9 groups are identical or different; and if "l" is 2, multiple R... 12 The functional groups are the same or different.

[0097] In Equation 1, n1 to n6 are each independently 0 or 1, where at least one of them is 1.

[0098] In one or more embodiments, Equation 1 can be represented by the following Equation 2:

[0099] Formula 2

[0100]

[0101] In Equation 2, Y 31It is CA or N, and A can be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, 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 forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring.

[0102] In Equation 2, "j′" and "k′" are each an independent integer from 0 to 2. Also, if "j′" is 2, multiple R... 10 The groups are the same or different, and if "k′" is 2, multiple R 11 The functional groups are the same or different.

[0103] In Equation 2, Y1, Y2, X1 to X 12 R1 to R 12 The "a" to "i", "l" and n1 to n6 are the same as those defined in Equation 1.

[0104] In one or more embodiments, Equation 2 can be represented by the following Equation 5:

[0105] Formula 5

[0106]

[0107] In Equation 5, "p" to "s" are each an independent integer from 0 to 4. Furthermore, if "p" is 2 or greater than 2, the multiple R9 groups are identical or different; if "q" is 2 or greater than 2, the multiple R9 groups are... 10 Whether the groups are the same or different, if "r" is 2 or greater, multiple Rs 11 The groups are the same or different, and if "s" is 2 or greater than 2, multiple Rs 12 The functional groups are the same or different.

[0108] In Equation 5, Y1, Y2, Y 31 X1 to X4, R1, R2, R7 to R 12 “a”, “b”, “g” and “h” are the same as those defined in Equation 2.

[0109] In one or more embodiments, Equation 2 can be represented by the following Equation 6:

[0110] Formula 6

[0111]

[0112] In Equation 6, "p" to "t" are each an independent integer from 0 to 4. Furthermore, if "p" is 2 or greater than 2, multiple R9 groups are identical or different; if "q" is 2 or greater than 2, multiple R9 groups are... 10 Whether the groups are the same or different, if "r" is 2 or greater, multiple Rs 11 Whether the groups are the same or different, if "s" is 2 or greater than 2, multiple R 12 The groups are the same or different, and if "t" is 2 or greater than 2, multiple R8 groups are the same or different.

[0113] In Equation 6, Y1, Y2, Y... 31 X1, X2, R1, R7 to R 12 The "a" and "g" are the same as those defined in Equation 2.

[0114] In one or more embodiments, Equation 1 can be represented by the following Equation 3:

[0115] Formula 3

[0116]

[0117] In Equation 3, Y 32 It is CA1A2 or NA3, and A1 to A3 can each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, 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 forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring.

[0118] In Equation 3, "j′" is an integer from 0 to 2. Also, if "j′" is 2, multiple R... 10 The functional groups are the same or different.

[0119] In Equation 3, Y1, Y2, X1 to X 12 R1 to R 12 The "a" to "i", "k", "l" and n1 to n6 are the same as those defined in Equation 1.

[0120] In one or more embodiments, Equation 1 can be represented by the following Equation 4:

[0121] Formula 4

[0122]

[0123] In Equation 4, "q" and "r" are each an independent integer from 0 to 5. Also, if "q" is 2 or greater than 2, multiple R... 10The groups are the same or different, and if "r" is 2 or greater than 2, there are multiple Rs. 11 The functional groups are the same or different.

[0124] In Equation 4, "p" and "s" are each an independent integer from 0 to 4. Furthermore, if "p" is 2 or greater than 2, the multiple R9 groups are identical or different, and if "s" is 2 or greater than 2, the multiple R9 groups are... 12 The functional groups are the same or different.

[0125] In Equation 4, Y1 to Y3, X1 to X4, R1, R2, R7 to R 12 “a”, “b”, “g”, “h”, n1 and n2 are the same as those defined in Equation 1.

[0126] In one or more implementations, Y1 and Y2 can be the same.

[0127] In one or more implementations, Y1 and Y2 can each be B independently.

[0128] In one or more embodiments, Y3 may be a substituted or unsubstituted amino group, and / or bonded to R. 10 and R 11 At least one of them can form a ring.

[0129] In one or more embodiments, X1 to X4 may not all be direct keys at the same time, and at least one of n1 and n2 may be 1.

[0130] In one or more embodiments, the polycyclic compound represented by Formula 1 may be at least one of the compounds represented in Group 1 of the following compounds, but one or more embodiments of this disclosure are not limited thereto:

[0131] Compound group 1

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142] In one or more embodiments, in the compounds represented in group 1, at least one hydrogen atom may be independently replaced by a deuterium atom.

[0143] Polycyclic compounds can be used in one or more embodiments of the organic electroluminescent device 10 to improve the efficiency and lifetime of the organic electroluminescent device. For example, polycyclic compounds can be used in the emission layer EML of one or more embodiments of the organic electroluminescent device 10 to improve the emission efficiency and lifetime of the organic electroluminescent device.

[0144] In one or more embodiments, the emission layer EML may be a delayed fluorescence emission layer comprising a first compound and a second compound, and the polycyclic compound of one or more embodiments 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.

[0145] In one or more embodiments, the host may be a host for emitting delayed fluorescence, and the dopant may be a dopant for emitting delayed fluorescence. In one or more embodiments, a polycyclic compound of one or more embodiments represented by Formula 1 may be included as a dopant material for the emission layer EML. For example, a polycyclic compound of one or more embodiments represented by Formula 1 may be used as a TADF dopant.

[0146] In one or more embodiments, the organic electroluminescent device 10 of one or more embodiments may include multiple emission layers. The multiple emission layers may be stacked sequentially. For example, the organic electroluminescent device 10 including multiple emission layers may emit white light. The organic electroluminescent device including multiple emission layers may be an organic electroluminescent device having a tandem structure. If the organic electroluminescent device 10 includes multiple emission layers, at least one emission layer EML may contain a polycyclic compound as described above according to this disclosure.

[0147] The emitter layer (EML) may further contain dopant materials, and the dopant can be any suitable material. For example, styrene derivatives (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4′-[(di-p-tolylamino)styrene]stilbene (DPAVB) and / or N-(4-((E)-2-(6-((E)-4-(diphenylamino)styrene)naphth-2-yl)vinyl)phenyl)-N-phenylaniline (N-BDAVBi) At least one of the following can be used as a dopant: perylene and / or its derivatives (e.g., 2,5,8,11-tetratert-butylperylene (TBP)), 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 / or 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi)).

[0148] The emitter layer EML can further contain other suitable host materials. For example, the emitter layer EML can contain tris(8-hydroxyquinoline)aluminum (Alq3), bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 4,4'-bis(N-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 the following: stilbene arylene (DSA), 4,4'-bis(9-carbazolyl)-2,2'-dimethylbiphenyl (CDBP), 2-methyl-9,10-bis(naphthyl-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), but is not limited thereto.

[0149] In cases where the emitting layer EML is intended to emit red light, the emitting layer EML may further comprise, for example, a fluorescent material, including tris(dibenzoylmethane)phenanthroline europium (PBD:Eu(DBM)3(Phen)) and / or perylene. In cases where the emitting layer EML is intended to emit red light, the dopant contained in the emitting layer EML may be selected from, 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 / or octaethylporphyrin platinum (PtOEP)), rubrene and its derivatives, and 4-dicyanomethylene-2-(p-dimethylaminostyryl)-6-methyl-4H-pyran (DCM) and its derivatives.

[0150] In cases where the emitting layer EML is intended to emit green light, the emitting layer EML may further comprise, for example, a fluorescent material, including tris(8-hydroxyquinoline)aluminum (Alq3). In cases where the emitting layer EML is intended to emit green light, the dopant contained in the emitting layer EML may be selected from, for example, metal complexes or organometallic complexes (e.g., planar tris(2-phenylpyridine)iridium (Ir(ppy)3)) and coumarins and their derivatives.

[0151] In cases where the emitting layer EML is intended to emit blue light, the emitting layer EML may further comprise a fluorescent material, said fluorescent material comprising at least 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). In cases where the emitting layer EML is intended to emit blue light, the dopant contained in the emitting layer EML may be selected, for example, from metal complexes or organometallic complexes (e.g., (4,6-F₂ppy)₂Irpic) and perylene and its derivatives.

[0152] In such Figures 1 to 4 In one or more embodiments of the organic electroluminescent device 10 shown, an electron transport region (ETR) is provided on an emitter layer (EML). The electron transport region (ETR) may include at least one of an electron blocking layer (HBL), an electron transport layer (ETL), and an electron injection layer (EIL). However, embodiments of this disclosure are not limited thereto.

[0153] The electron transport region (ETR) can have a single layer (e.g., a single-layer structure) formed using a single material (e.g., composed of a single material), a single layer formed using multiple different materials, or a multilayer structure having multiple layers formed using multiple different materials.

[0154] 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 a single-layer structure formed using an electron injection material and an electron transport material. In some embodiments, the ETR can have a single-layer structure containing multiple different materials, or a structure of an electron transport layer (ETL) / electron injection layer (EIL) or a hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) stacked from the emitter layer (EML), but is not limited thereto. The thickness of the ETR can be, for example, approximately [missing information - likely a number]. to approximately

[0155] The electron transport region (ETR) can be formed using one or more suitable methods (e.g., vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing and / or laser-induced thermal imaging (LITI) method).

[0156] If the electron transport region (ETR) includes an electron transport layer (ETL), the ETL may contain anthracene-based compounds. The ETL 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), 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, but not limited thereto. The thickness of the electron transport layer (ETL) can be approximately to approximately Or it could be, for example, about to approximately If the thickness of the electron transport layer (ETL) meets the range described above, satisfactory (or suitable) electron transport properties can be obtained without a significant increase in driving voltage.

[0157] If the electron transport region (ETR) includes an electron injection layer (EIL), the EIL may comprise a metal halide (e.g., LiF, NaCl, CsF, RbCl and / or RbI), a lanthanide (e.g., Yb), a metal oxide (e.g., Li₂O and / or BaO), and / or lithium hydroxyquinoline (LiQ). However, embodiments of this disclosure are not limited thereto. The EIL may also 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 greater. For example, the insulating organometallic salt may be selected from metal acetates, metal benzoates, metal acetoacetates, metal acetylacetonates, and metal stearates. The thickness of the EIL may be approximately... to approximately For example, about to approximately If the thickness of the electron injection layer (EIL) meets the range described above, satisfactory (or suitable) electron injection properties can be obtained without a significant increase in driving voltage.

[0158] The electron transport region (ETR) may include a hole blocking layer (HBL) as described above. The hole blocking layer (HBL) may contain at least one of, for example, 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). However, embodiments of this disclosure are not limited thereto.

[0159] 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 semi-transmissive reflective electrode, or a reflective electrode. If the second electrode EL2 is a transmission electrode, the second electrode EL2 can contain a transparent metal oxide, such as ITO, IZO, ZnO, ITZO, etc.

[0160] If 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, compounds containing them, or mixtures thereof (e.g., a mixture of Ag and Mg). In one or more embodiments, the second electrode EL2 may have a multilayer structure, the multilayer structure including a reflective or semi-transparent reflective layer formed using any of the materials described above, and a transparent conductive layer formed using ITO, IZO, ZnO, ITZO, etc.

[0161] 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.

[0162] refer to Figure 4 One or more embodiments of the organic electroluminescent device 10 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.

[0163] An organic electroluminescent device 10 according to one or more embodiments of the present disclosure is characterized by comprising a polycyclic compound represented by Formula 1 and exhibiting high efficiency and long lifetime. In one or more embodiments, the organic electroluminescent device 10 of one or more embodiments can exhibit high efficiency and long lifetime characteristics in the deep blue wavelength region.

[0164] The present disclosure will be explained in detail below with reference to implementation schemes and comparative implementation schemes. The following implementation schemes are merely examples to aid in understanding the present disclosure, and the scope of the present disclosure is not limited thereto.

[0165] Example

[0166] Synthesis of polycyclic compounds

[0167] The methods for synthesizing polycyclic compounds explained below are merely embodiments (e.g., examples), and the methods for synthesizing polycyclic compounds according to one or more embodiments of this disclosure are not limited thereto.

[0168] 1. Synthesis of Compound 1

[0169]

[0170] (1) Under an Ar atmosphere, 1,3-dibromo-5-chlorobenzene (100.0 g), diphenylamine (125.2 g), bis(dibenzylacetone)palladium(O) (Pd(dba)2, 4.2 g), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos, 3.1 g), and sodium tert-butoxide (NaOtBu, 72.0 g) were added to a 1,000 mL three-necked flask and dissolved in toluene (1,000 mL). The resulting mixture was then heated and refluxed for approximately 2 hours. After the temperature was restored to room temperature, water was added, and the reaction product was extracted with CH2Cl2. The organic layer was collected and dried over MgSO4, and the solvent was removed by vacuum distillation. The crude product obtained was separated by silica gel column chromatography to obtain 148 g (90% yield) of intermediate A. The mass number of intermediate A, measured by fast atom bombardment-mass spectrometry (FAB-MS), is 446.

[0171] (2) Under an Ar atmosphere, intermediate A (70.0 g), aniline (21.8 g), Pd(dba)₂ (0.9 g), SPhos (0.64 g), and NaOtBu (22.6 g) were placed in a 1,000 mL three-necked flask and dissolved in toluene (500 mL). The resulting mixture was then heated and refluxed for approximately 1 hour. After the temperature was restored to room temperature, water was added, and the reaction product was extracted with CH₂Cl₂. The organic layer was collected and dried over MgSO₄, and the solvent was removed by vacuum distillation. Ethanol was added to the crude product thus obtained, and the mixture was washed to obtain 74.2 g (94% yield) of intermediate B. The mass number of intermediate B, as measured by FAB-MS, was 503.

[0172] (3) The aziroboron heterocyclohexadiene derivative C was synthesized with reference to non-patent literature (Adv. Funct. Mater. 2018, 28, 1802031), the entire contents of which are incorporated herein by reference.

[0173] (4) Under an Ar atmosphere, intermediates B (20.0 g), C (21.4 g), Pd(dba)₂ (0.22 g), SPhos (0.16 g), and NaOtBu (3.8 g) were placed in a 1,000 mL three-necked flask and dissolved in toluene (300 mL). The resulting mixture was then heated and refluxed for approximately 3 hours. Water was added to the mixture, and the reaction product was extracted with CH₂Cl₂. The organic layer was collected and dried over MgSO₄, and the solvent was removed by vacuum distillation. The crude product obtained was separated by silica gel column chromatography to obtain 33.8 g (89% yield) of intermediate D. The mass number of intermediate D, measured by FAB-MS, was 956.

[0174] (5) Under an Ar atmosphere, intermediate D (32.0 g) was placed in a 500 mL three-necked flask, dissolved in 1,2,4-trichlorobenzene (200 mL), and cooled to approximately 0 °C in an ice bath. Boron triiodide (BI3, 40 g) and triphenylborane (BPh3, 9.7 g) were added, and the mixture was heated to approximately 200 °C and stirred for approximately 12 hours. The resulting product was cooled to approximately 0 °C in an ice bath, and N,N-diisopropylethylamine (50 mL) was added. After the temperature was restored to room temperature, the reaction solution was filtered using silica gel, and the solvent in the filtrate was removed by vacuum distillation. The crude product thus obtained was recrystallized in toluene to obtain 1.98 g (6% yield) of compound 1. The mass number of compound 1, as measured by FAB-MS, was 982.

[0175] 2. Synthesis of Compound 2

[0176]

[0177] (1) Oxaborone derivative E was synthesized with reference to non-patent literature (Chem. Commun. 2015, 51, 9443-9446), the entire contents of which are incorporated herein by reference.

[0178] (2) Under an Ar atmosphere, intermediates B (20.0 g), E (18.3 g), Pd(dba)₂ (0.22 g), SPhos (0.16 g), and NaOtBu (3.8 g) were placed in a 1,000 mL three-necked flask and dissolved in toluene (250 mL). The resulting mixture was then heated and refluxed for approximately 3 hours. After the temperature was restored to room temperature, water was added, and the reaction product was extracted with CH₂Cl₂. The organic layer was collected and dried over MgSO₄, and the solvent was removed by vacuum distillation. The crude product obtained was separated by silica gel column chromatography to obtain 32.2 g (92% yield) of intermediate F. The mass number of intermediate F, measured by FAB-MS, was 883.

[0179] (3) Under an Ar atmosphere, intermediate F (32.0 g) was placed in a 1,000 mL three-necked flask, dissolved in 1,2,4-trichlorobenzene (200 mL), and cooled to approximately 0 °C. Boron triiodide (BI3, 40 g) and triphenylborane (BPh3, 9.7 g) were added, and the mixture was heated to approximately 195 °C and stirred for approximately 17 hours. The resulting product was cooled to approximately 0 °C, and N,N-diisopropylethylamine (50 mL) was added. After the temperature was restored to room temperature, the reaction solution was filtered using silica gel, and the solvent in the filtrate was removed by vacuum distillation. The crude product thus obtained was recrystallized in toluene to obtain 1.51 g (5% yield) of compound 2. The mass number of compound 2, as measured by FAB-MS, was 899.

[0180] 3. Synthesis of Compound 3

[0181]

[0182] (1) Thiaborinine derivative G was synthesized by referring to non-patent literature (Adv. Funct. Mater. 2018, 28, 1802031).

[0183] (2) Under an Ar atmosphere, intermediate B (20.0 g), thiaborone derivative G (19.0 g), Pd(dba)2 (0.22 g), SPhos (0.16 g), and NaOtBu (3.8 g) were placed in a 1,000 mL three-necked flask and dissolved in toluene (250 mL). The resulting mixture was then heated and refluxed for approximately 3 hours. Water was added, and the reaction product was extracted with CH2Cl2. The organic layer was collected and dried over MgSO4, and the solvent was removed by vacuum distillation. The crude product obtained was separated by silica gel column chromatography to obtain 30.6 g (86% yield) of intermediate H. The mass number of intermediate H, measured by FAB-MS, was 899.

[0184] (3) Under an Ar atmosphere, intermediate H (30.0 g) was placed in a 1,000 mL three-necked flask, dissolved in 1,2,4-trichlorobenzene (200 mL), and cooled to approximately 0 °C in an ice bath. Boron triiodide (BI3, 40 g) and triphenylborane (BPh3, 9.7 g) were added, and the mixture was heated to approximately 200 °C and stirred for approximately 10 hours. The resulting product was cooled to approximately 0 °C in an ice bath, and N,N-diisopropylethylamine (50 mL) was added. After the temperature was restored to room temperature, the reaction solution was filtered using silica gel, and the solvent in the filtrate was removed by vacuum distillation. The crude product thus obtained was separated by recrystallization in toluene and recrystallization in 1,2-dichlorobenzene (ODCB) to obtain 1.07 g (3% yield) of compound 3. The mass number of compound 3, as measured by FAB-MS, was 923.

[0185] 4. Synthesis of Compound 41

[0186]

[0187] (1) Under an Ar atmosphere, intermediate B (30.0 g), 3-bromo-10-phenylphenoxazine (20.2 g), Pd(dba)₂ (0.34 g), SPhos (0.24 g), and NaOtBu (5.72 g) were placed in a 1,000 mL three-necked flask and dissolved in toluene (250 mL). The resulting mixture was then heated and refluxed for approximately 3 hours. Water was added to the mixture, and the reaction product was extracted with CH₂Cl₂. The organic layer was collected and dried over MgSO₄, and the solvent was removed by vacuum distillation. The crude product obtained was separated by silica gel column chromatography to obtain 34.8 g (77% yield) of intermediate J. The mass number of intermediate J, as measured by FAB-MS, was 760.

[0188] (2) Under an Ar atmosphere, intermediate J (30.0 g) was placed in a 1,000 mL three-necked flask, dissolved in 1,2,4-trichlorobenzene (200 mL), and cooled to approximately 0 °C in an ice bath. Boron triiodide (BI3, 40 g) and triphenylborane (BPh3, 9.7 g) were added, and the mixture was heated to approximately 200 °C and stirred for approximately 18 hours. The resulting product was cooled to approximately 0 °C in an ice bath, and N,N-diisopropylethylamine (50 mL) was added. After the temperature was restored to room temperature, the reaction solution was filtered using silica gel, and the solvent in the filtrate was removed by vacuum distillation. The crude product thus obtained was separated by recrystallization in toluene and recrystallization in ODCB to obtain 1.99 g (yield 12%) of compound 41. The mass number of compound 41, as measured by FAB-MS, was 776.

[0189] 5. Synthesis of Compound 52

[0190]

[0191] (1) Under an Ar atmosphere, 2-bromo-10-phenylphenoxazine (60.0 g), aniline (16.5 g), Pd(dba)₂ (1.0 g), SPhos (0.72 g), and NaOtBu (17.0 g) were placed in a 2,000 mL three-necked flask and dissolved in toluene (600 mL). The resulting mixture was then heated and refluxed for approximately 2 hours. Water was added to the mixture, and the reaction product was extracted with CH₂Cl₂. The organic layer was collected and dried over MgSO₄, and the solvent was removed by vacuum distillation. The crude product obtained was separated by silica gel column chromatography to obtain 46.6 g (75% yield) of intermediate K. The mass number of intermediate K, as measured by FAB-MS, was 350.

[0192] (2) Under an Ar atmosphere, 1,3,5-tribromobenzene (100.0 g), diphenylamine (52.6 g), Pd(dba)2 (1.8 g), bis(diphenylphosphino)ferrocene (dppf, 3.5 g), and NaOtBu (30.6 g) were placed in a 2,000 mL three-necked flask and dissolved in toluene (600 mL). The resulting mixture was then heated and refluxed for approximately 3 hours. Water was added to the mixture, and the reaction product was extracted with CH2Cl2. The organic layer was collected and dried over MgSO4, and the solvent was removed by vacuum distillation. The crude product obtained was separated by silica gel column chromatography to obtain 51.2 g (80% yield) of intermediate L. The mass number of intermediate L, measured by FAB-MS, was 403.

[0193] (3) Under an Ar atmosphere, intermediate L (20.0 g), intermediate K (34.8 g), Pd(dba)2 (0.28 g), SPhos (0.20 g), and NaOtBu (9.60 g) were placed in a 1,000 mL three-necked flask and dissolved in toluene (250 mL). The resulting mixture was then heated and refluxed for approximately 3 hours. Water was added, and the reaction product was extracted with CH2Cl2. The organic layer was collected and dried over MgSO4, and the solvent was removed by vacuum distillation. The crude product obtained was separated by silica gel column chromatography to obtain 31.8 g (68% yield) of intermediate M. The mass number of intermediate M, measured by FAB-MS, was 942.

[0194] (4) Under an Ar atmosphere, intermediate M (30.0 g) was placed in a 300 mL three-necked flask, dissolved in 1,2,4-trichlorobenzene (220 mL), and cooled to approximately 0 °C in an ice bath. Boron triiodide (BI3, 40 g) and triphenylborane (BPh3, 9.7 g) were added, and the mixture was heated to approximately 190 °C for approximately 12 hours. The resulting product was cooled to approximately 0 °C in an ice bath, and N,N-diisopropylethylamine (50 mL) was added. After the temperature was restored to room temperature, the reaction solution was filtered using silica gel, and the solvent in the filtrate was removed by vacuum distillation. The crude product obtained was separated by recrystallization in toluene and recrystallization in ODCB to obtain 1.49 g (5% yield) of compound 52. The mass number of compound 52, as measured by FAB-MS, was 965.

[0195] 6. Synthesis of Compound 55

[0196]

[0197] (1) Under an Ar atmosphere, 2-bromodibenzo-p-dioxin (60.0 g), aniline (21.2 g), Pd(dba)₂ (1.3 g), SPhos (0.92 g), and NaOtBu (22.0 g) were placed in a 2,000 mL three-necked flask and dissolved in toluene (1,000 mL). The resulting mixture was then heated and refluxed for approximately 4 hours. Water was added to the mixture, and the reaction product was extracted with CH₂Cl₂. The organic layer was collected and dried over MgSO₄, and the solvent was removed by vacuum distillation. The crude product obtained was separated by silica gel column chromatography to obtain 43.8 g (70% yield) of intermediate N. The mass number of intermediate N, as measured by FAB-MS, was 275.

[0198] (2) Under an Ar atmosphere, intermediate N (40.0 g), intermediate L (29.2 g), Pd(dba)₂ (0.82 g), SPhos (0.60 g), and NaOtBu (14.0 g) were placed in a 2,000 mL three-necked flask and dissolved in toluene (550 mL). The resulting mixture was then heated and refluxed for approximately 3 hours. Water was added, and the reaction product was extracted with CH₂Cl₂. The organic layer was collected and dried over MgSO₄, and the solvent was removed by vacuum distillation. The crude product obtained was separated by silica gel column chromatography to obtain 37.4 g (65% yield) of intermediate O. The mass number of intermediate O, measured by FAB-MS, was 791.

[0199] (3) Under an Ar atmosphere, intermediate O (30.0 g) was placed in a 1,000 mL three-necked flask, dissolved in 1,2,4-trichlorobenzene (250 mL), and cooled to approximately 0 °C in an ice bath. Boron triiodide (BI3, 40 g) and triphenylborane (BPh3, 9.7 g) were added, and the mixture was heated to approximately 200 °C and stirred for approximately 15 hours. The resulting product was cooled to approximately 0 °C in an ice bath, and N,N-diisopropylethylamine (50 mL) was added. After the temperature was restored to room temperature, the reaction solution was filtered using silica gel, and the solvent in the filtrate was removed by vacuum distillation. The crude product thus obtained was separated by recrystallization in toluene and recrystallization in ODCB to obtain 2.73 g (9% yield) of compound 55. The mass number of compound 55, as measured by FAB-MS, was 815.

[0200] 7. Synthesis of Compound 67

[0201]

[0202] (1) Under an Ar atmosphere, 100.0 g of 2-bromo-9-phenylcarbazole, 29.0 g of aniline, 1.8 g of Pd(dba)2, 1.28 g of SPhos, and 29.9 g of NaOtBu were placed in a 2,000 mL three-necked flask and dissolved in 90 mL of toluene. The resulting mixture was then heated and refluxed for about 4 hours. Water was added to the mixture, and the reaction product was extracted with CH2Cl2. The organic layer was collected and dried over MgSO4, and the solvent was removed by vacuum distillation. The crude product obtained was separated by silica gel column chromatography to obtain 70.6 g (68% yield) of intermediate P. The mass number of intermediate P, as measured by FAB-MS, was 334.

[0203] (2) Under an Ar atmosphere, intermediate P (40.0 g), intermediate L (24.2 g), Pd(dba)₂ (0.68 g), dppf (1.3 g), and NaOtBu (12.1 g) were placed in a 2,000 mL three-necked flask and dissolved in toluene (450 mL). The resulting mixture was then heated and refluxed for approximately 3 hours. Water was added to the mixture, and the reaction product was extracted with CH₂Cl₂. The organic layer was collected and dried over MgSO₄, and the solvent was removed by vacuum distillation. The crude product obtained was separated by silica gel column chromatography to obtain 40.8 g (52% yield) of intermediate Q. The mass number of intermediate Q, measured by FAB-MS, was 656.

[0204] (3) Under an Ar atmosphere, intermediates Q (38.0 g), K (20.2 g), Pd(dba)₂ (0.32 g), SPhos (0.24 g), and NaOtBu (5.56 g) were placed in a 1,000 mL three-necked flask and dissolved in toluene (300 mL). The resulting mixture was then heated and refluxed for approximately 2 hours. Water was added, and the reaction product was extracted with CH₂Cl₂. The organic layer was collected and dried over MgSO₄, and the solvent was removed by vacuum distillation. The crude product obtained was separated by silica gel column chromatography to obtain 34.8 g (65% yield) of intermediate R. The mass number of intermediate R, measured by FAB-MS, was 926.

[0205] (4) Under an Ar atmosphere, intermediate R (30.0 g) was placed in a 1,000 mL three-necked flask, dissolved in 1,2,4-trichlorobenzene (300 mL), and cooled to approximately 0 °C in an ice bath. Boron triiodide (BI3, 40 g) and triphenylborane (BPh3, 9.7 g) were added, and the mixture was heated to approximately 200 °C and stirred for approximately 18 hours. The resulting product was cooled to approximately 0 °C in an ice bath, and N,N-diisopropylethylamine (50 mL) was added. After the temperature was restored to room temperature, the reaction solution was filtered using silica gel, and the solvent in the filtrate was removed by vacuum distillation. The crude product thus obtained was separated by recrystallization in toluene and recrystallization in ODCB to obtain 2.12 g (7% yield) of compound 67. The mass number of compound 67, as measured by FAB-MS, was 949.

[0206] Manufacturing of organic electroluminescent devices

[0207] The organic electroluminescent devices of Examples 1 to 7 were manufactured using the above-described compounds as materials for the emitting layer.

[0208] Example compounds

[0209]

[0210] The organic electroluminescent devices of Comparative Examples 1 to 7 were manufactured using the following comparative compounds as materials for the emitter layer.

[0211] Comparison of compounds

[0212]

[0213] The organic electroluminescent devices of the embodiments and comparative examples were manufactured by the following methods.

[0214] On the glass substrate, there will be approximately The ITO layer was patterned to a thickness of [thickness value], washed with ultrapure water, and treated with UV ozone for approximately 10 minutes. Then, HAT-CN was deposited to a thickness of [thickness value]. The thickness of α-NPD is deposited to approximately [amount missing]. The thickness, and the mCP is deposited to approximately The thickness is increased to form a hole transport region.

[0215] Then, the example compound or comparative compound and mCBP are co-deposited at a weight ratio of 1:99 to form a compound with approximately A layer of thickness is formed to create an emission layer.

[0216] 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].

[0217] In this embodiment, a vacuum deposition apparatus is used to form a hole transport region, an emitter layer, an electron transport region, and a second electrode.

[0218] Evaluation of the properties of organic electroluminescent devices

[0219] To evaluate the properties of the organic electroluminescent devices according to the embodiments and comparative examples, the maximum emission wavelength (nm), the maximum external quantum yield (%), and the emission at approximately 1,000 cd / m² were measured. 2 The external quantum efficiency (%) at a given brightness was measured using the C9920-11 brightness distribution characteristic measurement system from Hamamatsu Photonics Co.

[0220] Table 1

[0221]

[0222] Referring to the results in Table 1, it can be confirmed that, compared to the comparative examples, the external quantum efficiency is improved when the emitter layer contains a polycyclic compound according to one or more embodiments. The example compounds, compared to the comparative compounds, include structures in which the heterocycle is further fused to one of the phenyl rings of the core structure. Without being bound by any particular theory, it is believed that in the example compounds, increased molecular conjugation leads to increased emission intensity, and therefore, improved external quantum efficiency if applied to a device.

[0223] It was confirmed that the efficiency of the apparatus in the examples was improved compared to most comparative examples. Without being bound by any particular theory, it is believed that in the heterocycles of the example compounds, nitrogen or oxygen is positioned at the para site relative to boron, effectively (or appropriately) generating push-pull electrons, and thus, due to resonance effects, the structure becomes relatively prone to generating reverse intersystemic crossovers.

[0224] Comparative Examples 4 and 5 (using Comparative Compounds X-4 and X-5) have structures in which oxygen is bonded to boron, and Comparative Example 7 (using Comparative Compound X-7) includes a structure in which heterocyclic fusion occurs; however, these comparative examples exhibit lower device efficiency when compared to the examples. Without being bound by any particular theory, it is believed that the effects of the example compounds cannot be achieved simply by introducing oxygen into the aromatic ring bonded to boron or by forming a fused ring, but the choice and combination of positions are necessary for generating a resonance effect in the molecule.

[0225] One or more embodiments of the organic electroluminescent device use a polycyclic compound represented by Formula 1 and can achieve high emission efficiency.

[0226] Organic electroluminescent devices according to one or more embodiments of this disclosure can achieve high efficiency and long lifespan.

[0227] Polycyclic compounds according to one or more embodiments of this disclosure can improve the lifespan and efficiency of organic electroluminescent devices.

[0228] As used herein, the terms “use,” “using,” and “used” can be considered synonymous with the terms “utilize,” “utilizing,” and “utilized,” respectively.

[0229] Furthermore, the terms “basically,” “about,” and similar terms are used as terms of approximation rather than terms of degree, and are intended to explain the inherent biases in measurements or calculations that would be recognized by a person skilled in the art.

[0230] Furthermore, 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.

[0231] Although exemplary embodiments of this disclosure have been described, it should be understood that this disclosure is not intended to be limited to these exemplary embodiments, and various changes and modifications can be made by those skilled in the art within the spirit and scope of the claims and their equivalents.

Claims

1. An organic electroluminescent device, comprising: First electrode; Hole transport region on the first electrode; The emission layer on the hole transport region; The electron transmission region on the emission layer; as well as The second electrode on the electron transport region, The first electrode and the second electrode each independently comprise at least one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, Mo, Ti, In, Zn, Sn, and their compounds and mixtures; LiF; or a mixture of LiF with at least one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, Mo, Ti, In, Zn, Sn, and their compounds and mixtures, and The emitter layer comprises a polycyclic compound represented by Formula 1: Formula 1 ,as well as In Equation 1, Y1 and Y2 are each independently B, N, P=O or P=S. X1 to X 12 Each is independently a BAr1, O, S, NAr2 or a single bond; X1 and X2 are not simultaneously single bonds; X3 and X4 are not simultaneously single bonds; X5 and X6 are not simultaneously single bonds; X7 and X8 are not simultaneously single bonds; X9 and X... 10 Not both are single bonds, and X 11 and X 12 Not both are single keys, Ar1 and Ar2 are each independently an aryl group, either substituted or unsubstituted, having 6 to 30 carbon atoms for ring formation, or a heteroaryl group, either substituted or unsubstituted, having 2 to 30 carbon atoms for ring formation. Y3 and R1 to R 12 Each group is independently selected from hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted amino groups, substituted or unsubstituted oxygen groups, substituted or unsubstituted thio groups, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms for forming a ring, or substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms for forming a ring, and / or bonded to one or more adjacent groups to form one or more rings. "a" through "f" are each an independent integer from 0 to 4. "j" and "k" are each an independent integer from 0 to 3. "g" through "i" and "l" are each an independent integer from 0 to 2, and n1 to n6 are each independently 0 or 1, and at least one of n1 to n6 is 1.

2. The organic electroluminescent device of claim 1, wherein the emitting layer is designed to emit delayed fluorescence.

3. The organic electroluminescent device of claim 1, wherein the emission layer is a delayed fluorescence emission layer comprising a first compound and a second compound, and The first compound includes the polycyclic compound.

4. The organic electroluminescent device of claim 1, wherein the emitting layer is a thermally activated delayed fluorescence emitting layer that emits blue light.

5. The organic electroluminescent device as claimed in claim 1, wherein Y1 and Y2 are the same.

6. The organic electroluminescent device of claim 1, wherein Y1 and Y2 are each independently boron, and Y3 is a substituted or unsubstituted amino group, and / or bonded to R. 10 and R 11 At least one of them can form a ring.

7. The organic electroluminescent device as claimed in claim 1, wherein... At least one of n1 and n2 is 1.

8. The organic electroluminescent device as claimed in claim 1, wherein formula 1 is represented by the following formula 2: Formula 2 ,as well as In Equation 2, Y 31 Is it CA or N? A is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, 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 forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring. "j′" and "k′" are each an independent integer from 0 to 2, and Y1, Y2, X1 to X 12 R1 to R 12 The "a" to "i", "l" and n1 to n6 are the same as those defined in Equation 1.

9. The organic electroluminescent device as claimed in claim 1, wherein formula 1 is represented by the following formula 3: Formula 3 ,as well as In Equation 3, Y 32 Is it CA1A2 or NA3? A1 to A3 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, 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 forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring. "j′" is an integer between 0 and 2, and Y1, Y2, X1 to X 12 R1 to R 12 The "a" to "i", "k", "l" and n1 to n6 are the same as those defined in Equation 1.

10. The organic electroluminescent device as claimed in claim 1, wherein formula 1 is represented by the following formula 4: Formula 4 ,as well as In Equation 4, "q" and "r" are each an integer from 0 to 5. "p" and "s" are each an integer from 0 to 4, and Y1 to Y3, X1 to X4, R1, R2, R7 to R 12 The characters "a", "b", "g", "h", n1, and n2 are the same as those defined in Equation 1.

11. The organic electroluminescent device as claimed in claim 8, wherein formula 2 is represented by the following formula 5: Formula 5 ,as well as In Equation 5, "p" through "s" are each an independent integer from 0 to 4, and Y1, Y2, Y 31 X1 to X4, R1, R2, R7 to R 12 The "a", "b", "g" and "h" are the same as those defined in Equation 2.

12. The organic electroluminescent device as claimed in claim 8, wherein formula 2 is represented by the following formula 6: Formula 6 ,as well as In Equation 6, "p" to "t" are each an independent integer from 0 to 4, and Y1, Y2, Y 31 X1, X2, R1, R7 to R 12 The "a" and "g" are the same as those defined in Equation 2.

13. The organic electroluminescent device of claim 1, wherein the polycyclic compound represented by formula 1 is at least one of the compounds represented in group 1 of the following compounds: Compound group 1 Where iPr represents an isopropyl group, Ph represents a phenyl group, and Me represents a methyl group.

14. The organic electroluminescent device of claim 1, wherein the first electrode and the second electrode each independently comprise at least one of oxides of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, Mo, Ti, In, Zn, and Sn; or a mixture of LiF and at least one of oxides of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, Mo, Ti, In, Zn, and Sn.

15. Polycyclic compounds represented by the following formula 1: Formula 1 ， In Equation 1, Y1 and Y2 are each independently B, N, P=O or P=S. X1 to X 12 Each is independently a BAr1, O, S, NAr2 or a single bond; X1 and X2 are not simultaneously single bonds; X3 and X4 are not simultaneously single bonds; X5 and X6 are not simultaneously single bonds; X7 and X8 are not simultaneously single bonds; X9 and X... 10 Not both are single bonds, and X 11 and X 12 Not both are single keys, Ar1 and Ar2 are each independently an aryl group, either substituted or unsubstituted, having 6 to 30 carbon atoms for ring formation, or a heteroaryl group, either substituted or unsubstituted, having 2 to 30 carbon atoms for ring formation. Y3 and R1 to R 12 Each of the following is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, 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 forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, and / or bonded to one or more adjacent groups to form one or more rings. "a" through "f" are each an independent integer from 0 to 4. "j" and "k" are each an independent integer from 0 to 3. "g" through "i" and "l" are each an independent integer from 0 to 2, and n1 to n6 are each independently 0 or 1, and at least one of n1 to n6 is 1.

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