Organic electroluminescent device

Abstract

Provided is an organic electroluminescent device having high luminous efficiency, the organic electroluminescent device including a first electrode, a second electrode facing the first electrode, and an emission layer disposed between the first electrode and the second electrode. The emission layer includes a polycyclic compound represented by Formula 1: [Formula 1]

Description

[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2020-0019642 filed on February 18, 2020, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0002] The disclosure relates to organic electroluminescent devices and polycyclic compounds used therein. Background Art

[0003] Recently, development of organic electroluminescent displays (ELDs) as image display devices has been actively underway. These devices are so-called self-luminous display devices, in which holes and electrons injected from a first electrode and a second electrode recombine in an emissive layer to generate excitons. These generated excitons then return to a ground state to emit light, thereby achieving display.

[0004] In applying organic electroluminescent devices to display apparatuses, there is a continuous demand for obtaining good color reproducibility by improving the luminous efficiency of the organic electroluminescent devices and for the development of materials for organic electroluminescent devices capable of stably obtaining such characteristics.

[0005] In recent years, in particular, in order to realize high-efficiency organic electroluminescent devices, technologies regarding phosphorescent emission utilizing triplet energy or delayed fluorescence emission utilizing triplet-triplet annihilation (TTA) (in which singlet excitons are generated by collision of triplet excitons) and thermally activated delayed fluorescence (TADF) materials utilizing the delayed fluorescence emission phenomenon have continued to develop. Summary of the Invention

[0006] Disclosed is an organic electroluminescent device having excellent luminous efficiency.

[0007] The disclosure also provides a polycyclic compound as a material for an organic electroluminescent device, the polycyclic compound having high color purity characteristics and high efficiency characteristics.

[0008] Embodiments of the inventive concept provide an organic electroluminescent device according to an embodiment, which may include a first electrode, a second electrode facing the first electrode, and an emission layer disposed between the first electrode and the second electrode. The first electrode and the second electrode may each independently include at least one material selected from the group consisting of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, compounds thereof, and mixtures thereof. The emission layer may include a polycyclic compound represented by Formula 1:

[0009] [Formula 1]

[0010]

[0011] In Formula 1, X1 may be NAr2, O or S, Y1 to Y8 may each independently be CM1 or a carbon atom bonded to a group represented by Formula 2, each M1 may independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, optionally, each M1 may independently bond with an adjacent group to form a ring, Ar1 and Ar2 may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 3 wherein R1 to R5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms; optionally, R1 to R5 can each independently combine with an adjacent group to form a ring; a, b, c and d can each independently be an integer from 0 to 2; at least one group represented by Formula 2 can be bonded to at least one pair of substituents selected from the group consisting of Y1 and Y2, Y3 and Y4, Y5 and Y6, and Y7 and Y8:

[0012] [Formula 2]

[0013]

[0014] In Formula 2, each X2 and each X3 can independently be NAr3, O or S, each Ar3 can independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, each R6 and each R7 can independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, optionally, each R6 and each R7 can independently combine with an adjacent group to form a ring, each e can independently be an integer from 0 to 3, each f can independently be an integer from 0 to 4, and * represents the binding position with the adjacent atom.

[0015] In an embodiment, the polycyclic compound represented by Formula 1 may be represented by one of Formulas 1-1a to 1-1c:

[0016] [Formula 1-1a]

[0017]

[0018] [Formula 1-1b]

[0019]

[0020] [Formula 1-1c]

[0021]

[0022] In Formulae 1-1a to 1-1c, Y1 to Y8, Ar1, Ar2, a, b, c, d, and R1 to R5 may be the same as defined in Formula 1.

[0023] In an embodiment, the polycyclic compound represented by Formula 1 may be represented by Formula 3-1 or Formula 3-2:

[0024] [Formula 3-1]

[0025]

[0026] [Formula 3-2]

[0027]

[0028] In formula 3-1 and formula 3-2, X 21 、X 22 、X 31 and X 32 Each of Ar4 and Ar5 may be independently NAr4, O or S, each Ar4 may be independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, R 61 、R 62 、R 71 and R 72 can be independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 61 、R 62 、R 71 and R 72 Each of the above groups may independently combine with an adjacent group to form a ring, a1 and d2 may each independently be an integer from 0 to 2, a2, d1, b1 and c1 may each independently be an integer from 0 to 4, e1 and e2 may each independently be an integer from 0 to 3, f1 and f2 may each independently be an integer from 0 to 4, and X1, Ar1 and R1 to R5 may be the same as defined in Formula 1.

[0029] In an embodiment, the polycyclic compound represented by Formula 1 can be represented by one of Formulae 4-1a to 4-1d:

[0030] [Formula 4-1a]

[0031]

[0032] [Formula 4-1b]

[0033]

[0034] [Formula 4-1c]

[0035]

[0036] [Formula 4-1d]

[0037]

[0038] In Formulae 4-1a to 4-1d, X 21 , X 22 , X 31 , and X 32 may each independently be NAr4, O, or S, each Ar4may independently be a substituted or unsubstituted aryl having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroaryl having 2 to 30 ring-forming carbon atoms, R 61 , R 62 , R 71 , and R 72 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and optionally, R 61 , R 62 , R 71 , and R 72 may each independently be combined with an adjacent group to form a ring, a1, b2, c2, and d2may each independently be an integer of 0 to 2, a2, b1, c1, and d1may each independently be an integer of 0 to 4, e1and e2may each independently be an integer of 0 to 3, f1and f2may each independently be an integer of 0 to 4, and X1, Ar1, and R1to R5may be the same as defined in Formula 1.

[0039] In an embodiment, the polycyclic compound represented by Formula 4-1a can have a linearly symmetric structure with respect to an imaginary line passing through the central nitrogen atom and R5.

[0040] In an embodiment, the polycyclic compound represented by Formula 4-1d may have a linear symmetrical structure with respect to an imaginary line passing through the central nitrogen atom and R5.

[0041] In an embodiment, the polycyclic compound represented by Formula 1 may be represented by one of Formulas 4-2a to 4-2d:

[0042] [Formula 4-2a]

[0043]

[0044] [Formula 4-2b]

[0045]

[0046] [Formula 4-2c]

[0047]

[0048] [Formula 4-2d]

[0049]

[0050] In Formula 4-2a to Formula 4-2d, X 21 、X 22 、X 31 and X 32 Each of Ar4 and Ar5 may be independently NAr4, O or S, each Ar4 may be independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, R 61 、R 62 、R 71 and R 72 can be independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 61 、R 62 、R 71 and R 72 Each may independently combine with an adjacent group to form a ring, e1 and e2 may each independently be an integer from 0 to 3, f1 and f2 may each independently be an integer from 0 to 4, and X1 and Ar1 may be the same as defined in Formula 1.

[0051] In an embodiment, the polycyclic compound represented by Formula 1 may be represented by Formula 5-1 or Formula 5-2:

[0052] [Formula 5-1]

[0053]

[0054] [Formula 5-2]

[0055]

[0056] In Formula 5-1 and Formula 5-2 above, each of X1, X2, X3, Ar1, R6, R7, e, and f can be independently the same as defined in Formula 1 and Formula 2.

[0057] In an embodiment, Ar1 and Ar2 can each be independently a substituted or unsubstituted phenyl.

[0058] In an embodiment, R6 and R7 can each be independently an unsubstituted methyl, an unsubstituted isopropyl, an unsubstituted tert-butyl, a substituted or unsubstituted diphenylamine group, or an unsubstituted phenyl.

[0059] In an embodiment, the emission layer can emit delayed fluorescence.

[0060] In an embodiment, the emission layer can emit light in a blue wavelength range.

[0061] In an embodiment, the emission layer can include a first compound and a second compound, and the first compound can include the polycyclic compound.

[0062] In an embodiment, the polycyclic compound represented by Formula 1 can be selected from one of the compounds represented by Compound Group 1:

[0063] [Compound Group 1]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073] BRIEF DESCRIPTION OF DRAWINGS

[0074] The accompanying drawings are included to provide a further understanding of the inventive concept and are incorporated into and constitute a part of this specification. The accompanying drawings illustrate embodiments of the inventive concept and, together with the description, serve to explain the principles of the inventive concept. In the drawings:

[0075] Figure 1 is a schematic cross-sectional view illustrating an organic electroluminescent device according to an embodiment of the inventive concept;

[0076] Figure 2 is a schematic cross-sectional view illustrating an organic electroluminescent device according to an embodiment of the inventive concept;

[0077] Figure 3 is a schematic cross-sectional view illustrating an organic electroluminescent device according to an embodiment of the inventive concept; and

[0078] Figure 4 is a schematic cross-sectional view illustrating an organic electroluminescent device according to an embodiment of the inventive concept. DETAILED DESCRIPTION

[0079] The inventive concept can be modified in many alternative forms and therefore specific embodiments will be depicted in the drawings and described in detail. However, it should be understood that this is not intended to limit the inventive concept to the particular form disclosed, but is intended to cover all modifications, equivalents and alternatives falling within the spirit and scope of the invention.

[0080] In the disclosure, when an element (or region, layer, part, etc.) is referred to as being "on," "connected to" or "coupled to" another element, this means that the element can be directly disposed on, directly connected / coupled to the other element, or a third element can be disposed therebetween.

[0081] The same reference numerals denote the same elements. In the accompanying drawings, the thickness, proportion, and size of elements may be exaggerated in order to effectively describe the technical content.

[0082] As used herein, the term "and / or" includes any and all combinations of one or more of the relevant listed items. For example, "A and / or B" may be understood to mean "A, B, or A and B". The terms "and" and "or" may be used in the sense of conjunctions or antonyms of conjunctions and may be understood to be equivalent to "and / or". Throughout this disclosure, the expression "at least one of A, B, and C" may mean only A, only B, only C, both A and B, both A and C, both B and C, all of A, B, and C, or variations thereof.

[0083] For purposes of its meaning and interpretation, the term "at least one of" is intended to include the meaning of "at least one selected from the group consisting of." For example, "at least one of A and B" can be understood to mean "A, B, or A and B." When the term "at least one of" follows a list of elements, it modifies the entire list and does not modify the individual elements in the list.

[0084] It will 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 only used to distinguish one element from another. For example, a first element may be referred to as a second element, and similarly, a second element may be referred to as a first element, without departing from the scope of the exemplary embodiments of the inventive concept. Unless the context clearly indicates otherwise, terms in the singular may include plural forms.

[0085] Terms such as “below,” “lower,” “above,” and “upper” are used to describe the relationship of the configurations shown in the drawings. The terms are used as relative concepts and are described with reference to directions indicated in the drawings.

[0086] As used herein, the terms "about" or "approximately" are inclusive of the stated value and mean within an acceptable range of deviation from the particular value as determined by one of ordinary skill in the art, taking into account the measurements in question and errors associated with measurement of the particular quantity (e.g., limitations of the measurement system). For example, "about" can mean within one or more standard deviations, or within ±20%, ±10%, ±5% of the stated value.

[0087] 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 the inventive concept belongs. It will also be understood that terms defined in common dictionaries should be interpreted as having a meaning consistent with their meaning in the context of the relevant art, and they will not be interpreted in an ideal or overly formal sense unless expressly defined herein.

[0088] It should be understood that the terms "comprises," "has," and / or "includes" and variations thereof are intended to indicate the presence of stated features, integers, steps, operations, elements, components, or combinations thereof in the disclosure, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.

[0089] Hereinafter, an organic electroluminescent device according to an embodiment of the inventive concept and a polycyclic compound of an embodiment included therein will be described with reference to the accompanying drawings.

[0090] Figures 1 to 4 is a schematic cross-sectional view illustrating an organic electroluminescent device according to an embodiment of the inventive concept. Referring to Figures 1 to 4 In the organic electroluminescent device 10 according to the embodiment, a first electrode EL1 and a second electrode EL2 are disposed to face each other, and an emission layer EML can be disposed between the first electrode EL1 and the second electrode EL2.

[0091] Further, the organic electroluminescent device 10 of the embodiment includes an organic layer between the first electrode EL1 and the second electrode EL2, in addition to the emission layer EML. The organic layer can include a hole transport region HTR and an electron transport region ETR. For example, the organic electroluminescent device 10 according to the embodiment can include a first electrode EL1, a hole transport region HTR, an emission layer EML, an electron transport region ETR, and a second electrode EL2, which are sequentially stacked. The organic electroluminescent device 10 of the embodiment can further include a cap layer CPL disposed on the second electrode EL2.

[0092] The organic electroluminescent device 10 of the embodiment can include a polycyclic compound of the embodiment, which will be described later, in the organic layer disposed between the first electrode EL1 and the second electrode EL2. For example, the polycyclic compound of the embodiment, which will be described later, can be included in the emission layer EML. However, the embodiment is not limited thereto, and the organic electroluminescent device 10 of the embodiment can include the polycyclic compound according to the embodiment, which will be described later, not only in the emission layer EML but also in the hole transport region HTR or the electron transport region ETR, which can be a partial organic layer disposed between the first electrode EL1 and the second electrode EL2.

[0093] In comparison with the related art Figure 1 , Figure 2 is a schematic cross-sectional view illustrating the organic electroluminescent device 10 of the embodiment, in which 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 comparison with the related art Figure 1 , Figure 3 is a schematic cross-sectional view illustrating the organic electroluminescent device 10 of the embodiment, in which 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. In comparison with the related art Figure 2 , Figure 4 is a schematic cross-sectional view illustrating the organic electroluminescent device 10 of the embodiment, which includes a cap layer CPL disposed on the second electrode EL2.

[0094] The first electrode EL1 has electrical conductivity. The first electrode EL1 may be formed of a metal alloy 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 transflective electrode, or a reflective electrode. When the first electrode EL1 is a transmissive electrode, the first electrode EL1 may include a transparent metal oxide such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), and indium tin zinc oxide (ITZO). When the first electrode EL1 is a transflective electrode or a reflective electrode, the first electrode EL1 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, compounds thereof, or mixtures thereof (e.g., a mixture of Ag and Mg).

[0095] The first electrode EL1 may have a multilayer structure including a reflective film or a transflective film formed of the above materials and a transparent conductive film formed of indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc. For example, the first electrode EL1 may have a three-layer structure of ITO / Ag / ITO, but is not limited thereto. The thickness of the first electrode EL1 may be about 1000 nm. to approximately For example, the thickness of the first electrode EL1 can be about to approximately within the range.

[0096] The hole transport region HTR is disposed 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, for example, about 1000 Å. to approximately within the range.

[0097] The hole transport region HTR may have a single layer formed of a single material, a single layer formed of different materials, or a multilayer structure including a plurality of layers formed of different materials.

[0098] 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 may have a single-layer structure formed of a hole injection material and a hole transport material. The hole transport region HTR may have a single-layer structure formed of different materials, or may have a structure in which a hole injection layer HIL / hole transport layer HTL, a hole injection layer HIL / hole transport layer HTL / hole buffer layer (not shown), a hole injection layer HIL / hole buffer layer (not shown), a hole transport layer HTL / hole buffer layer, or a hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL are sequentially stacked from the first electrode EL1, but the embodiment is not limited thereto.

[0099] The hole transport region HTR may be formed using various methods such as a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Blodgett (LB) method, an inkjet printing method, a laser printing method, and a laser induced thermal imaging (LITI) method.

[0100] The hole injection layer HIL may include, for example, a phthalocyanine compound (such as copper phthalocyanine), N,N'-diphenyl-N,N'-bis[4-(di-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine (DNTPD), 4,4',4"-[tris(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tris{N-(2-naphthyl)-N-phenylamino)-triphenylamine (2-TNATA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) The products include polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine (NPB), triphenylamine-containing polyetherketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium tetrakis(pentafluorophenyl)borate, dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexanitrile (HAT-CN), etc.

[0101] The hole transport layer HTL may include, for example, carbazole derivatives (such as N-phenylcarbazole and polyvinylcarbazole), fluorene derivatives, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), triphenylamine derivatives (such as 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA)), N,N'-di(naphthalene-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), 1,3-bis(N-carbazolyl)benzene (mCP), and the like.

[0102] The thickness of the hole transport region HTR can be about to approximately For example, the thickness of the hole transport region HTR can be about to approximately The thickness of the hole injection layer HIL can be, for example, about to approximately and the thickness of the hole transport layer HTL can be in the range of about to approximately For example, the thickness of the electron blocking layer EBL can be about to approximately If the thicknesses of the hole transport region HTR, the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL satisfy the above ranges, satisfactory hole transport performance may be achieved without significantly increasing the driving voltage.

[0103] In addition to the above materials, the hole transport region HTR may further include a charge generating material to improve 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-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano-containing compound, but is not limited thereto. For example, non-limiting examples of p-dopants may include quinone derivatives (such as tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ)), metal oxides (such as tungsten oxide and molybdenum oxide), etc., but are not limited thereto.

[0104] 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 (not shown) and an electron blocking layer EBL. The hole buffer layer (not shown) may compensate for the optical resonance distance according to the wavelength of light emitted from the emission layer EML to improve luminous efficiency. The material that may be included in the hole transport region HTR may be used as the material that may be included in the hole buffer layer. The electron blocking layer EBL is a layer for preventing electrons from being injected from the electron transport region ETR into the hole transport region HTR.

[0105] The emission layer EML may be disposed on the hole transport region HTR. The thickness of the emission layer EML may be, for example, about to approximately For example, the thickness of the emission layer EML can be about to approximately The emission layer EML may have a single layer formed of a single material, a single layer formed of different materials, or a multilayer structure having a plurality of layers formed of different materials.

[0106] In the specification, the term "substituted or unsubstituted" may mean that it is unsubstituted or substituted with at least one substituent selected from the group consisting of a deuterium atom, a halogen atom, a cyano group, a nitro group, an amine group, a silyl group, an oxy group, a sulfenyl group, a sulfinyl group, a sulfonyl group, a carbonyl group, a boron group, a phosphine oxide group, a phosphine sulfide group, an alkyl group, an alkenyl group, an alkoxy group, a hydrocarbon ring group, an aryl group, and a heterocyclic group. Each of the above 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.

[0107] In the specification, the term "bonding to an adjacent group to form a ring" may mean that it is bonded to an adjacent group to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring. Hydrocarbon rings include aliphatic hydrocarbon rings and aromatic hydrocarbon rings. Heterocyclic rings include aliphatic heterocyclic rings and aromatic heterocyclic rings. Hydrocarbon rings and heterocyclic rings may be monocyclic or polycyclic. The ring formed by bonding to each other may be connected to another ring to form a spiro structure.

[0108] In the specification, the term "bonded to adjacent groups to form a ring" may mean that two adjacent rings are bonded to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.

[0109] In the specification, the term "adjacent group" may refer to a substituent that replaces an atom directly connected to an atom substituted with a corresponding substituent, another substituent that replaces an atom substituted with a corresponding substituent, or a substituent that is spatially located closest to the corresponding substituent. For example, the two methyl groups in 1,2-dimethylbenzene can be interpreted as "adjacent groups" to each other, and the two ethyl groups in 1,1-diethylcyclopentane can be interpreted as "adjacent groups" to each other.

[0110] In the specification, examples of the halogen atom may include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0111] In the specification, the alkyl group may be linear, branched, or cyclic. The number of carbon atoms in the alkyl group is 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of the alkyl group 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, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-Hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, etc., but are not limited thereto.

[0112] In the specification, the hydrocarbon ring may represent any functional group or substituent derived from an aliphatic hydrocarbon ring. The number of ring-forming carbon atoms in the hydrocarbon ring may be 5 to 20.

[0113] In the specification, an aryl group refers to any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. The number of ring carbon atoms in the aryl group may be 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups may include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, pentaphenyl, hexaphenyl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, etc., but not limited thereto.

[0114] In the specification, a heterocyclic group refers to any functional group or substituent derived from a ring containing at least one of B, O, N, P, Si, and S as a heteroatom. Heterocyclic groups include aliphatic heterocyclic groups and aromatic heterocyclic groups. Aromatic heterocyclic groups may be heteroaryl groups. Aliphatic heterocyclic groups and aromatic heterocyclic groups may be monocyclic or polycyclic.

[0115] When the heterocyclic group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and conceptually may include a heteroaryl group. The number of ring carbon atoms in the heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10.

[0116] The number of ring carbon atoms in the aliphatic heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10. Examples of the aliphatic heterocyclic group include, but are not limited to, oxiranyl, thioethanethiol, pyrrolidinyl, piperidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, thianyl, tetrahydropyranyl, 1,4-dioxanyl, and the like.

[0117] When the heteroaryl group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. The number of ring carbon atoms in the heteroaryl group may be 2 to 30, 2 to 20, or 2 to 10. Examples of heteroaryl groups may include, but are not limited to, thienyl, furyl, pyrrolyl, imidazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, N-arylcarbazolyl, N-heteroarylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothiphenyl, benzofuranyl, phenanthrolinyl, thiazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, phenothiazinyl, dibenzothiaryl, dibenzofuranyl, and the like.

[0118] In the specification, the number of carbon atoms in the amine group is not particularly limited, but can be 1 to 30. The amine group can include an alkyl amine group and an aryl amine group. Examples of the amine group include a methyl amine group, a dimethyl amine group, a phenyl amine group, a diphenyl amine group, a naphthyl amine group, a 9-methyl-anthryl amine group, and the like, but are not limited thereto.

[0119] In the specification, the aryl group in the aryl amine group is the same as the examples of the aryl group described above.

[0120] In the specification, the direct bond can mean a single bond.

[0121] In the specification, “-*” means a position of connection, and * means a bonding site to an adjacent atom.

[0122] The emission layer EML of the organic electroluminescent device 10 of the embodiment can include the polycyclic compound of the embodiment represented by the following Formula 1.

[0123] [Formula 1]

[0124]

[0125] In Formula 1, X1may be NAr2, O, or S.

[0126] In Formula 1, Y1to Y8may each independently be CM1or a carbon atom bonded to a group represented by Formula 2. Each M1may independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and each M1may independently be bonded to an adjacent group to form a ring, if desired.

[0127] For example, M1may be a hydrogen atom or a deuterium atom. However, the embodiment is not limited thereto.

[0128] In Formula 1, Ar1and Ar2may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. For example, Ar1and Ar2may each independently be a substituted or unsubstituted phenyl group. For example, Ar1and Ar2may each independently be an unsubstituted phenyl group or a phenyl group substituted with deuterium.

[0129] In Formula 1, R1 to R5 can be independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. Alternatively, R1 to R5 can be independently combined with adjacent groups to form a ring. For example, R1 to R4 can be independently a hydrogen atom or a deuterium atom. For example, R5 can be a hydrogen atom. However, embodiments are not limited thereto.

[0130] In Formula 1, a, b, c, and d may each independently be an integer from 0 to 2. For example, a, b, c, and d may each be 0.

[0131] At least one group represented by Formula 2 may be bonded to at least one pair of substituents, wherein the at least one pair of substituents may be selected from the group consisting of Y1 and Y2, Y3 and Y4, Y5 and Y6, and Y7 and Y8. For example, one or two groups represented by the following Formula 2 may be bonded to the polycyclic compound represented by Formula 1. However, the embodiment is not limited thereto.

[0132] [Formula 2]

[0133]

[0134] In Formula 2, each X2 and each X3 can independently be NAr3, O, or S.

[0135] In Formula 2, each Ar3 can independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, Ar3 can be an unsubstituted phenyl group or a phenyl group substituted with deuterium.

[0136] In Formula 2, each R6 and each R7 can independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 ring carbon atoms, optionally, each R6 and each R7 can independently combine with adjacent groups to form a ring. For example, each R6 and each R7 can independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted alkyl group with 1 to 5 carbon atoms. For example, each R6 and each R7 can independently be an unsubstituted methyl group, an unsubstituted isopropyl group, an unsubstituted tert-butyl group, a substituted or unsubstituted biphenylamine group, or an unsubstituted phenyl group.

[0137] In Formula 2, each e may be an integer from 0 to 3. For example, e may be 0 or 1.

[0138] In Formula 2, each f may be an integer from 0 to 4. For example, f may be 0 or 1.

[0139] In an embodiment, the polycyclic compound represented by Formula 1 may be represented by one of Formulas 1-1a to 1-1c:

[0140] [Formula 1-1a]

[0141]

[0142] [Formula 1-1 b]

[0143]

[0144] [Formula 1-1 c]

[0145]

[0146] The cases where X1 in Formula 1 is NAr2, O, and S are respectively reflected in Formulas 1-1a to 1-1c.

[0147] In Formulae 1-1a to 1-1c, the same descriptions as those mentioned above in Formula 1 may apply to Y1 to Y8, Ar1, Ar2, a, b, c, d, and R1 to R5.

[0148] In an embodiment, the polycyclic compound represented by Formula 1 may be represented by one of Formulas 1-2a to 1-2c:

[0149] [Formula 1-2a]

[0150]

[0151] [Formula 1-2b]

[0152]

[0153] [Formula 1-2c]

[0154]

[0155] The case where R1 to R5 in the polycyclic compound represented by Formula 1 are hydrogen atoms or deuterium atoms is reflected in Formulas 1-2a to 1-2c.

[0156] In Formulae 1-2a to 1-2c, positions at which the group represented by Formula 2 is bonded to the polycyclic compound represented by Formula 1 are represented by Y1 to Y6.

[0157] In Formulae 1-2a to 1-2c, the same description as mentioned in Formula 1 above may apply to X1, Y1 to Y8, and Ar1.

[0158] In embodiments, the polycyclic compound represented by Formula 1 can be represented by Formula 3-1 or Formula 3-2:

[0159] [Formula 3-1]

[0160]

[0161] [Formula 3-2]

[0162]

[0163] The position at which the group represented by Formula 2 is bound to the polycyclic compound represented by Formula 1 is embodied in Formula 3-1 and Formula 3-2.

[0164] The case in which the group represented by Formula 2 is bound to Y1 and Y2 in Formula 1 is embodied in Formula 3-1. The case in which the group represented by Formula 2 is bound to Y7 and Y8 in Formula 1 is embodied in Formula 3-2.

[0165] In Formula 3-1 and Formula 3-2, X 21 , X 22 , X 31 , and X 32 may each independently be NAr4, O, or S. For example, X 21 , X 22 , X 31 , and X 32 may each independently be NAr4or O.

[0166] In Formula 3-1 and Formula 3-2, each Ar4may independently be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. For example, Ar4may be an unsubstituted phenyl group. Embodiments are not limited thereto, however.

[0167] In Formula 3-1 and Formula 3-2, R 61 , R 62 , R 71 , and R 72 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. Optionally, R 61 , R 62 , R 71 , and R 72 may each independently be bound to an adjacent group to form a ring. For example, R 61 , R 62 , R 71 , and R 72Each of them may independently be a hydrogen atom, a methyl group or an unsubstituted biphenylamine group. However, the embodiment is not limited thereto.

[0168] In Formula 3-1 and Formula 3-2, a1 and d2 may each independently be an integer from 0 to 2. a2, d1, b1, and c1 may each independently be an integer from 0 to 4. e1 and e2 may each independently be an integer from 0 to 3. f1 and f2 may each independently be an integer from 0 to 4. For example, a1, a2, b1, c1, d1, d2, e1, e2, f1, and f2 may each be 0.

[0169] The same description as mentioned in the above Formula 1 may apply to X1, Ar1, and R1 to R5.

[0170] In an embodiment, the polycyclic compound represented by Formula 1 may be represented by one of Formulas 4-1a to 4-1d:

[0171] [Formula 4-1a]

[0172]

[0173] [Formula 4-1b]

[0174]

[0175] [Formula 4-1c]

[0176]

[0177] [Formula 4-1d]

[0178]

[0179] The positions at which two groups represented by Formula 2 are bonded to the polycyclic compound represented by Formula 1 are shown in Formulas 4-1a to 4-1d.

[0180] In Formulas 4-1a to 4-1d, X 21 、X 22 、X 31 and X 32 and R5 may each independently be NAr4, O, or S. In an embodiment, the polycyclic compound represented by Formula 4-1a may have a linear symmetrical structure with respect to an imaginary line passing through the central nitrogen atom and R5. For example, in the polycyclic compound represented by Formula 4-1a, X1=NAr1, X 21 =X 22 , X 31 =X 32 , R1=R4,R2=R3,R 61 =R 62 , R 71 =R 72, a1=d2, b1=c1, e1=e2, f1=f2. However, the embodiment is not limited thereto.

[0181] In an embodiment, the polycyclic compound represented by Formula 4-1d may have a linear symmetrical structure with respect to an imaginary line passing through the central nitrogen atom and R5. For example, in the polycyclic compound represented by Formula 4-1d, X1=NAr1, X 21 =X 22 , X 31 =X 32 , R1=R4,R2=R3,R 61 =R 62 , R 71 =R 72 , a2=d1, b2=c2, e1=e2, f1=f2. However, the embodiment is not limited thereto.

[0182] In Formulae 4-1a to 4-1d, each Ar4 can independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, Ar4 can be an unsubstituted phenyl group or a phenyl group substituted with deuterium.

[0183] In Formula 4-1a to Formula 4-1d, R 61 、R 62 、R 71 and R 72 can be independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 61 、R 62 、R 71 and R 72 Each of them can independently combine with an adjacent group to form a ring. For example, R 61 、R 62 、R 71 and R 72 Each of R and R is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms. 61 、R 62 、R 71 and R 72 Each of them may independently be an unsubstituted methyl group, an unsubstituted isopropyl group, an unsubstituted tert-butyl group, a substituted or unsubstituted biphenylamino group, or an unsubstituted phenyl group.

[0184] In Formulae 4-1a to 4-1d, a1, b2, c2, and d2 can each independently be an integer of 0 to 2. a2, b1, c1, and d1 can each independently be an integer of 0 to 4. e1 and e2 can each independently be an integer of 0 to 3. f1 and f2 can each independently be an integer of 0 to 4. For example, a1, a2, b1, b2, c1, c2, d1, d2, e1, e2, f1, and f2 can each be 0.

[0185] The same description as mentioned in Formula 1 above can be applied to X1, Ar1, and R1 to R5.

[0186] In an embodiment, the polycyclic compound represented by Formula 1 can be represented by one of Formulae 4-2a to 4-2d:

[0187] [Formula 4-2a]

[0188]

[0189] [Formula 4-2b]

[0190]

[0191] [Formula 4-2c]

[0192]

[0193] [Formula 4-2d]

[0194]

[0195] In Formulae 4-2a to 4-2d, the case where R1 to R5 in Formulae 4-1a to 4-1d are each a hydrogen atom is embodied in Formulae 4-2a to 4-2d.

[0196] In Formulae 4-2a to 4-2d, the same description as mentioned in Formula 1, Formula 2, and Formulae 4-1a to 4-1d above can be applied to X1, X 21 , X 22 , X 31 , X 32 , R 61 , R 62 , R 71 , R 72 , Ar1, e1, e2, f1, and f2.

[0197] In an embodiment, the polycyclic compound represented by Formula 1 can be represented by Formula 5-1 or Formula 5-2.

[0198] [Formula 5-1]

[0199]

[0200] [Formula 5-2]

[0201]

[0202] The cases in which Formula 4-2a and Formula 4-2d have a partially symmetrical structure are embodied in Formula 5-1 and Formula 5-2, respectively. In Formula 5-1 and Formula 5-2, X1may be NAr1in embodiments. However, embodiments are not limited thereto, and in embodiments, X1may be O or S. For example, X1may be O.

[0203] In Formula 5-1 and Formula 5-2, the same descriptions as mentioned in the descriptions of Formula 1 and Formula 2 above can be applied to X1, X2, X3, Ar1, R6, R7, e, and f.

[0204] The polycyclic compound of embodiments includes fused aromatic rings formed around a boron atom and a nitrogen atom, and thus has a polyharmonic molecular skeleton, and can minimize changes in the molecular skeleton even in an excited state.

[0205] Accordingly, the organic electroluminescent device 10 of embodiments includes the polycyclic compound of embodiments in an emission layer EML, and thus can have high light-emitting efficiency.

[0206] In embodiments, the polycyclic compound represented by Formula 1 can be one selected from among the compounds represented by Compound Group 1. Compound Group 1 includes Compound 1 to Compound 99:

[0207] [Compound Group 1]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217] The polycyclic compound of the embodiment can be used as a blue light emitting material. For example, the polycyclic compound of the embodiment can be used as a light emitting material that emits blue light having a central emission wavelength in a wavelength range of less than or equal to about 470 nm. For example, the polycyclic compound of the embodiment can be a light emitting material having a central emission wavelength in a wavelength range of about 430 nm to about 470 nm. The polycyclic compound of the embodiment represented by Formula 1 can be a blue thermally activated delayed fluorescence dopant.

[0218] The polycyclic compound of the embodiment includes fused aromatic rings formed around a boron atom and a nitrogen atom, and thus can have a polyharmonic molecular skeleton. Accordingly, the polycyclic compound can be provided in a form in which the aromatic rings are bound to each other to maintain a stable molecular structure. The organic electroluminescent device 10 of the embodiment includes the polycyclic compound of the above-described embodiment in the emission layer, and thus can have excellent luminous efficiency.

[0219] In the organic electroluminescent device 10 of the embodiment, the emission layer EML can emit delayed fluorescence. For example, the emission layer EML can emit thermally activated delayed fluorescence (TADF).

[0220] Although not shown in the drawings, the organic electroluminescent device 10 of the embodiment can include a plurality of emission layers. The plurality of emission layers can be sequentially stacked and disposed, for example, the organic electroluminescent device 10 including a plurality of emission layers can emit white light. The organic electroluminescent device 10 including a plurality of emission layers can be an organic electroluminescent device having a tandem structure. When the organic electroluminescent device 10 includes a plurality of emission layers, at least one emission layer can include the polycyclic compound of the above-described embodiment.

[0221] The emission layer EML can include a first compound and a second compound different from the first compound, and the first compound can include the polycyclic compound of the embodiment. For example, the emission layer EML can include a host and a dopant, and can include the polycyclic compound of the above-described embodiment as a dopant. The second compound can be a host. For example, in the organic electroluminescent device 10 of the embodiment, the emission layer EML can include a host for delayed fluorescence emission and a dopant for delayed fluorescence emission, and can include the polycyclic compound of the above-described embodiment as a dopant for delayed fluorescence emission. The emission layer EML can include at least one of the polycyclic compounds represented by the above-described Compound Group 1 as a thermally activated delayed fluorescence dopant.

[0222] In the embodiment, the emission layer EML can be a delayed fluorescence emission layer, and the emission layer EML can include a known host material and the polycyclic compound of the above-described embodiment. For example, in the embodiment, the polycyclic compound can be used as a TADF dopant.

[0223] The polycyclic compound of the embodiment may be a thermally activated delayed fluorescent host or a phosphorescent host. The emission layer EML including the polycyclic compound of the embodiment may be a phosphorescent emission layer or a thermally activated delayed fluorescent emission layer. For example, the emission layer EML may be a thermally activated delayed fluorescent emission layer.

[0224] The emission layer EML may include one or two or more polycyclic compounds of the above-mentioned compound group 1.

[0225] In the organic electroluminescent device 10 of the embodiment, the emission layer EML may include a known host material. For example, the emission layer EML may include at least one of bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-bis(carbazol-9-yl)benzene (mCP), tris(4-carbazol-9-ylphenyl)amine (TCTA), and 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi) as a host material. However, the embodiment is not limited thereto. For example, tris(8-hydroxyquinoline)aluminum (Alq3), poly(N-vinylcarbazole) (PVK), 9,10-di(naphthalene-2-yl)anthracene (ADN), 2-tert-butyl-9,10-di(naphthalene-2-yl)anthracene (TBADN), distyrylarylene (DSA), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH2), hexaphenylcyclotrisiloxane (DPSiO3), octaphenylcyclotetrasiloxane (DPSiO4), etc. can be used as the main material.

[0226] In the organic electroluminescent device 10 of the embodiment, the emission layer EML may include anthracene derivatives, pyrene derivatives, fluoranthene derivatives, Derivatives, dihydrobenzanthracene derivatives or benzo[9,10]phenanthrene derivatives. For example, the emission layer EML may include anthracene derivatives or pyrene derivatives.

[0227] The emission layer EML may include an anthracene derivative represented by Formula G below.

[0228] [Formula G]

[0229]

[0230] In formula G, R 31 to R 40may be independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 31 to R 40 Can each independently combine with an adjacent group to form a ring. 31 to R 40 Each may independently combine with an adjacent group to form a saturated hydrocarbon ring or an unsaturated hydrocarbon ring.

[0231] In Formula G, p and q may each independently be an integer from 0 to 5.

[0232] Formula G can be represented by one of Compound G-1 to Compound G-16:

[0233]

[0234] In an embodiment, the emission layer EML may further include a known dopant material. In an embodiment, the emission layer EML may further include styryl derivatives (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB), and N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalene-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-dipyrenylbenzene, 1,4-bis(N,N-diphenylamino)pyrene), etc. as dopants.

[0235] exist Figures 1 to 4 In the organic electroluminescent device 10 of the embodiment shown in FIG, the electron transport region ETR is provided on the emission layer EML. The electron transport region ETR may include at least one of a hole blocking layer HBL, an electron transport layer ETL, and an electron injection layer EIL, but embodiments of the inventive concept are not limited thereto.

[0236] The electron transport region ETR may have a single layer formed of a single material, a single layer formed of different materials, or a multilayer structure including a plurality of layers formed of different materials.

[0237] 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 may have a single-layer structure formed of an electron injection material and an electron transport material. The electron transport region ETR may have a single-layer structure formed of different materials, or may have a structure in which an electron transport layer ETL / electron injection layer EIL or a hole blocking layer HBL / electron transport layer ETL / electron injection layer EIL are sequentially stacked from the emission layer EML, but is not limited thereto. The thickness of the electron transport region ETR may be, for example, about 1000 nm. to approximately within the range.

[0238] The electron transport region ETR may be formed using various methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, laser induced thermal imaging (LITI), etc.

[0239] When the electron transport region ETR includes the electron transport layer ETL, the electron transport region ETR may include an anthracene compound. However, embodiments of the inventive concept are not limited thereto, and the electron transport region ETR may include, for example, tris(8-hydroxyquinoline)aluminum (Alq3), 1,3,5-tris[(3-pyridyl)-phenyl-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-benzo[d]imidazol-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-(naphthalene-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-hydroxyquinolinolato-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), bis(benzoquinolinolato-10-hydroxy)beryllium (Bebq2), 9,10-di(naphthalene-2-yl)anthracene (ADN), 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB), or a mixture thereof. The thickness of the electron transport layer ETL can be about 500 nm. to approximately For example, the thickness of the electron transport layer ETL can be about to approximately If the thickness of the electron transport layer ETL satisfies the above range, satisfactory electron transport performance may be obtained without significantly increasing the driving voltage.

[0240] When the electron transport region ETR includes an electron injection layer EIL, the electron transport region ETR may be a metal halide (such as LiF, NaCl, CsF, RbCl, RbI, and CuI), a lanthanide metal (such as Yb), a metal oxide (such as Li2O and BaO), or 8-hydroxyquinoline lithium (LiQ), but is not limited thereto. The electron injection layer EIL may also be formed of a mixed material of an electron transport material and an insulating organic metal salt. The organic metal salt may be a material having an energy band gap of about 4 eV or greater. The organic metal salt may include, for example, a metal acetate, a metal benzoate, a metal acetoacetate, a metal acetylacetonate, or a metal stearate. The thickness of the electron injection layer EIL may be about 1000 nm. to approximately For example, the thickness of the electron injection layer EIL can be about to approximately If the thickness of the electron injection layer EIL satisfies the above range, satisfactory electron injection performance can be obtained without significantly increasing the driving voltage.

[0241] As described above, the electron transport region ETR may include a hole blocking layer HBL. 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), but is not limited thereto.

[0242] The second electrode EL2 is disposed on the electron transport region ETR. The second electrode EL2 may be a common electrode or a cathode. The second electrode EL2 may be a transmissive electrode, a transflective electrode, or a reflective electrode. If the second electrode EL2 is a transmissive electrode, the second electrode EL2 may include a transparent metal oxide such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO).

[0243] If the second electrode EL2 is a transflective electrode or a reflective electrode, the second electrode EL2 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, compounds thereof, or mixtures thereof (e.g., a mixture of Ag and Mg). The second electrode EL2 may have a multilayer structure including a reflective film or a transflective film formed of the above materials and a transparent conductive film formed of indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), or the like.

[0244] Although not shown, the second electrode EL2 may be connected to the auxiliary electrode. If the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.

[0245] A capping layer CPL may be further provided on the second electrode EL2 of the organic electroluminescent device 10 of the embodiment. The capping layer CPL may include a multi-layer or a single layer.

[0246] In an embodiment, the cap layer CPL may be an organic layer or an inorganic layer. For example, when the cap layer CPL includes an inorganic material, the inorganic material may include an alkali metal compound (such as LiF), an alkaline earth metal compound (such as MgF2, SiON, SiN X 、SiO y )wait.

[0247] For example, when the cap layer CPL includes an organic material, the organic material may include α-NPD, NPB, TPD, m-MTDATA, Alq3, CuPc, N4,N4,N4',N4'-tetrakis(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15), 4,4',4"-tris(carbazol-9-yl)triphenylamine (TCTA), etc., or may include epoxy resin or acrylate such as methacrylate. However, the embodiment is not limited thereto, and the cap layer CPL may also include the following compounds P1 to P5.

[0248]

[0249]

[0250] The organic electroluminescent device 10 according to an embodiment of the inventive concept may include the polycyclic compound of the above embodiment in the emission layer EML disposed between the first electrode EL1 and the second electrode EL2 to achieve excellent luminous efficiency. The polycyclic compound according to the embodiment may be a thermally activated delayed fluorescence dopant, and the emission layer EML may include the polycyclic compound of the embodiment to emit thermally activated delayed fluorescence, thereby achieving good luminous efficiency.

[0251] The polycyclic compound of the above-described embodiment may be included in an organic layer other than the emission layer EML as a material for the organic electroluminescent device 10. For example, the organic electroluminescent device 10 according to an embodiment of the inventive concept may include the above-described polycyclic compound in at least one functional layer disposed between the first electrode EL1 and the second electrode EL2 or in a cap layer CPL disposed on the second electrode EL2.

[0252] The polycyclic compounds of the above embodiments may have a multi-resonance molecular skeleton with aromatic rings fused around B, N, O, and S. Therefore, the polycyclic compounds according to the embodiments can maintain a stable molecular structure and exhibit a high lowest triplet excitation energy level, and thus can be used as delayed fluorescence luminescent materials. The organic electroluminescent devices of the embodiments including the polycyclic compounds of the embodiments in the emission layer can exhibit high luminous efficiency.

[0253] Hereinafter, the polycyclic compound according to the embodiment of the inventive concept and the organic electroluminescent device of the embodiment will be described in detail with reference to examples and comparative examples. The examples shown below are only shown for understanding the inventive concept, and the scope of the inventive concept is not limited thereto.

[0254] [Example Compounds]

[0255]

[0256] [Comparative Example Compounds]

[0257]

[0258] 1. Synthesis Example

[0259] The polycyclic compound according to the embodiment can be synthesized, for example, in the following manner. However, the process of synthesizing the polycyclic compound to be described below is provided as an example, and thus the process of synthesizing the polycyclic compound according to the embodiment of the inventive concept is not limited to the following example.

[0260] 1-1. Synthesis of Compound 2

[0261]

[0262]

[0263] A. Synthesis of Compound A

[0264] 1,3,5-tribromobenzene (25.0 g, 79 mmol), diphenylamine (11.2 g, 66 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 1.51 g, 1.7 mmol), 2-dicyclohexylphosphine-2',6'-diisopropoxybiphenyl (Ruphos, 1.3 g, 2.8 mmol) and sodium tert-butoxide ( t BuONa, 7.6 g, 79 mmol) was added to toluene (400 mL) and heated at 80° C. for 5 hours. After cooling, toluene and water were added and separated. The organic layer was concentrated, purified by column chromatography (silica gel), concentrated, filtered, and washed with hexane to obtain compound A (18.1 g, yield: 68%).

[0265] B. Synthesis of Compound B

[0266] 3-Phenoxy-N-phenylaniline (15.0 g, 57 mmol), 1-bromo-3-iodobenzene (17.9 g, 63 mmol), palladium (II) acetate (Pd (OAc) 2, 28 mg, 1.3 mmol), 4,5-bis (diphenylphosphine) -9,9-dimethylxanthene (Xantphos, 1.46 g, 2.5 mmol) and t BuONa (6.60 g, 69 mmol) was added to toluene (400 mL) and heated at 80° C. for 5 hours. After cooling, toluene and water were added and separated. The organic layer was concentrated, purified by column chromatography (silica gel), concentrated, filtered, and washed with hexane to obtain compound B (16.7 g, yield: 70%).

[0267] C. Synthesis of Compound C

[0268] Compound B (16.0 g, 38 mmol), aniline (3.60 g, 38 mmol), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 1.10 g, 2 mmol), tri-tert-butylphosphine tetrafluoroborate (PtBu3 . HBF4, 0.42 g, 2.3 mmol) and t BuONa (4.43 g, 46 mmol) was added to toluene (400 mL) and heated at 80° C. for 5 hours. After cooling, toluene and water were added and separated. The organic layer was concentrated, purified by column chromatography (silica gel), concentrated, filtered, and washed with hexane to obtain compound C (12.4 g, yield: 75%).

[0269] D. Synthesis of Compound D

[0270] Compound D (13.2 g, yield 88%) was obtained in the same manner as in the synthesis of Compound C using Compound C (12.3 g, 27 mmol) and Compound A (5.50 g, 13.6 mmol).

[0271] E. Synthesis of Compound 2

[0272] Compound D (13.2 g, 12 mmol) was added to 1,2-dichlorobenzene (ODCB, 127 mL), BBr3 (12.0 g) was added, and the mixture was heated at 150 ° C for 20 hours. After cooling, triethylamine (TEA, 36 g, 0.36 mol) was added, toluene was added to dissolve, water was added and separated, and the organic layer was concentrated and purified by column chromatography (silica gel) to obtain compound 2 (2.90 g, yield: 22%). Sublimation purification (410 ° C, 3.7 × 10 -3After that, the device was evaluated. FAB-MS showed m / z=1130 (M + +1)

[0273] 1-2. Synthesis of Compound 4

[0274]

[0275] A. Synthesis of Compound E

[0276] 3-(Diphenylamino)phenol (10.0 g, 57 mmol), 1-bromo-3-fluorobenzene (19.4 g, 74 mmol) and CsCO (37.2 g, 0.11 mol) were added to 1-methyl-2-pyrrolidone (NMP, 100 mL) and stirred at 150° C. for 20 hours. Water and toluene were added and separated. The organic layer was concentrated, purified by column chromatography (silica gel), concentrated, filtered, and washed with hexane to obtain compound E (16.7 g, yield: 70%).

[0277] B. Synthesis of Compound F

[0278] In the same manner as in the synthesis of Compound 2, Compound F (10.4 g, yield: 65%) was obtained from Compound E (16.0 g, 38.4 mmol).

[0279] C. Synthesis of Compound G

[0280] In the same manner as in the synthesis of Compound C, Compound G (12.8 g, yield: 78%) was obtained from Compound F (16.0 g, 37.7 mmol) and aniline (3.5 g, 38 mmol).

[0281] D. Synthesis of Compound H

[0282] In the same manner as in the synthesis of Compound D, Compound H (14.1 g, yield: 74%) was obtained from Compound G (15.5 g, 36 mmol) and Compound A (7.5 g, 17 mmol).

[0283] E. Synthesis of Compound 4

[0284] In the same manner as the synthesis of compound 2, compound 4 (2.60 g, yield: 20%) was obtained from compound H (13.0 g, 12 mmol). Sublimation purification (415° C., 3.8×10 -3 After that, the device was evaluated. FAB-MS showed m / z=1130 (M + +1)

[0285] 1-3. Synthesis of Compound 6

[0286]

[0287] A. Synthesis of Compound I

[0288] Under the same conditions as those for the synthesis of Compound E, Compound I (13.6 g, yield: 77%) was synthesized from 3-phenoxyphenol (13.8 g, 74 mmol) and 1-bromo-3-fluorobenzene (10.0 g, 57 mmol).

[0289] B. Synthesis of Compound J

[0290] In the same manner as in the synthesis of Compound 2, Compound J (11.5 g, yield: 87%) was synthesized from Compound I (13.2 g, 39 mmol).

[0291] C. Synthesis of Compound K

[0292] In the same manner as in the synthesis of Compound C, Compound K (10.5 g, yield: 92%) was obtained from Compound J (11.0 g, 32 mmol) and aniline (2.90 g, 32 mmol).

[0293] D. Synthesis of Compound L

[0294] In the same manner as in the synthesis of Compound D, Compound L (11.2 g, yield: 85%) was obtained from Compound K (10.3 g, 29 mmol) and Compound A (5.5 g, 14 mmol).

[0295] E. Synthesis of Compound 6

[0296] In the same manner as the synthesis of compound 2, compound 6 (2.0 g, yield: 18%) was obtained from compound L (11.0 g, 11 mmol). Sublimation purification (390° C., 3.5×10 -3 After that, the device was evaluated. FAB-MS showed m / z = 980 (M + +1)

[0297] 1-4. Synthesis of Compound 28

[0298]

[0299] A. Synthesis of Compound M

[0300] In the same manner as in the synthesis of Compound A, Compound M (17.7 g, yield: 79%) was synthesized from 1,3-dibromo-5-fluorobenzene (20.0 g, 79 mmol) and diphenylamine (11.1 g, 66 mmol).

[0301] B. Synthesis of Compound N

[0302] In the same manner as in the synthesis of Compound C, Compound N (15.1 g, yield: 85%) was synthesized from Compound M (17.2 g, 50 mmol) and aniline (4.7 g, 50 mmol).

[0303] C. Synthesis of Compound O

[0304] N1-(3-bromophenyl)-N1,N3,N3-triphenylbenzene-1,3-diamine (18.5 g, 38 mmol), compound N (14.7 g, 41 mmol), Pd(dba)2 (1.08 g, 1.88 mmol), PtBu3·HBF4 (0.41 g, 2.2 mmol) and t BuONa (4.34 g, 46 mmol) was added to toluene (400 mL) and heated at 80° C. for 5 hours. After cooling, toluene and water were added and separated. The organic layer was concentrated, purified by column chromatography (silica gel), concentrated, filtered, and washed with hexane to obtain compound O (24.8 g, yield: 86%).

[0305] D. Synthesis of Compound P

[0306] Under the same conditions as those for the synthesis of Compound E, Compound P (20.2 g, yield: 70%) was synthesized from 3-bromophenol (16.3 g, 94 mmol) and Compound O (24.0 g, 31 mmol).

[0307] E. Synthesis of Compound Q

[0308] In the same manner as in the synthesis of Compound 2, Compound Q (7.0 g, yield: 35%) was synthesized from Compound P (20.0 g, 22 mmol).

[0309] F. Synthesis of Compound R

[0310] In the same manner as in the synthesis of Compound O, Compound R (7.1 g, yield: 86%) was synthesized from Compound Q (6.5 g, 7 mmol) and N1,N1,N3-triphenylbenzene-1,3-diamine (2.55 g, 8 mmol).

[0311] G. Synthesis of Compound 28

[0312] In the same manner as the synthesis of compound 2, compound R (7.0 g, 6 mmol) was used to obtain compound 28 (2.24 g, yield: 33%). Sublimation purification (410° C., 3.3×10 -3After that, the device was evaluated. FAB-MS showed m / z=1205 (M + +1)

[0313] 1-5. Synthesis of Compound 30

[0314]

[0315] A. Synthesis of Compound T

[0316] In the same manner as in the synthesis of Compound O, Compound T (19.9 g, yield: 80%) was synthesized from Compound B (15.0 g, 36 mmol) and Compound N (14.0 g, 40 mmol).

[0317] B. Synthesis of Compound U

[0318] Under the same conditions as those for the synthesis of Compound E, Compound U (16.3 g, yield: 75%) was synthesized from Compound T (19.0 g, 28 mmol) and 3-bromophenol (14.3 g, 83 mmol).

[0319] C. Synthesis of Compound V

[0320] In the same manner as in the synthesis of Compound 2, Compound V (6.4 g, yield: 40%) was synthesized from Compound U (16.0 g, 19 mmol).

[0321] D. Synthesis of Compound W

[0322] In the same manner as in the synthesis of Compound O, Compound W (6.7 g, yield: 92%) was obtained from Compound V (6.0 g, 7 mmol) and 3-phenoxy-N-phenylaniline (2.60 g, 8 mmol).

[0323] E. Synthesis of Compound 30

[0324] In the same manner as the synthesis of compound 2, compound 30 (1.26 g, yield: 21%) was obtained from compound W (6.0 g, 6 mmol). Sublimation purification (410° C., 3.2×10 -3 After that, the device was evaluated. FAB-MS showed m / z=1055 (M + +1).

[0325] 1-6. Synthesis of Compound 56

[0326]

[0327] A. Synthesis of Compound X

[0328] Compound J (10.0 g, 29 mmol), N1,N1,N3,N3-tetraphenylbenzene-1,3,5-triamine (6.1 g, 14 mmol), Pd(dba)2(0.82 g, 1.43 mmol), PtBu3·HBF4(0.31 g, 1.7 mmol) and t BuONa (3.3 g, 34 mmol) was added to toluene (200 mL) and heated at 80°C for 5 hours. After cooling, toluene and water were added and separated. The organic layer was concentrated, purified by column chromatography (silica gel), concentrated, filtered, and washed with hexane to obtain Compound X (11.0 g, yield: 80%).

[0329] B, Synthesis of Compound 56

[0330] Compound 56 (1.3 g, yield: 12%) was obtained in the same manner as the synthesis of Compound 2, using Compound X (10.8 g, 11 mmol). Sublimation purification (400°C, 3.8 x 10 -3 Pa) was performed, and device evaluation was performed. FAB-MS showed m / z = 980 (M + +1).

[0331] 2, Evaluation of Energy Level of Compound

[0332] The luminescent properties of the polycyclic compound of Example and the organic electroluminescent device of Example including the polycyclic compound of Example in the emission layer were evaluated in the following manner. The method of manufacturing the organic electroluminescent device for evaluation is described below.

[0333] The organic electroluminescent devices of Example 1 to Example 6 were manufactured using the above-described Compound 2, Compound 4, Compound 6, Compound 28, Compound 30, and Compound 56 as a dopant material for an emission layer. Comparative Example 1 to Comparative Example 3 are organic electroluminescent devices manufactured using Comparative Example Compound X1 to Comparative Example Compound X3, respectively, as a dopant material for an emission layer.

[0334] (MANUFACTURE OF ORGANIC ELECTROLUMINESCENT DEVICE)

[0335] On a glass substrate, ITO was patterned to a thickness of about 1500 A, washed with ultrapure water, cleaned with ultrasonic waves, irradiated with UV for 30 minutes, and then subjected to ozone treatment. Thereafter, HAT-CN was deposited to a thickness of about 10 A, α-NPD was deposited to a thickness of about 200 A, and mCP was deposited to a thickness of about 100 A to form a hole transport region.

[0336] ​​​​When forming each emission layer, the polycyclic compound of the embodiment or the comparative example compound and the host material are co-deposited at a weight ratio of 1:99 to form a The emission layers formed by co-deposition in Examples 1 to 6 were deposited by mixing Compound 2, Compound 4, Compound 6, Compound 28, Compound 30, and Compound 56 with a host material, respectively. In Comparative Examples 1 to 3, Comparative Example Compounds X1 to X3 were each mixed with a host material and deposited. When forming the emission layer, mCP was used as the host material.

[0337] Then, on the emission layer, sequentially, TPBi is formed with A layer of thickness of LiF is formed having A layer with a thickness of 1000 nm is formed to form an electron transport region. The thickness of the second electrode is .

[0338] In an example, the hole transport region, the emission layer, the electron transport region, and the second electrode are formed using a vacuum deposition apparatus.

[0339] [Functional compounds]

[0340]

[0341] (Evaluation of organic electroluminescent device characteristics)

[0342] Table 1 shows the evaluation results of the organic electroluminescent devices of Examples 1 to 6 and Comparative Examples 1 to 3. Table 1 shows the maximum emission wavelengths (λ max ), EQE max and EQE max1000nit In the characteristic evaluation results of the examples and comparative examples shown in Table 1, the maximum emission wavelength (λ max ) represents the wavelength showing the maximum value in the emission spectrum, EQE max (External quantum efficiency) represents the maximum value of external quantum efficiency, EQE max1000nit Indicates 1000cd / m 2 The maximum value of the external quantum efficiency.

[0343] [Table 2]

[0344]

[0345] Referring to the results in Table 1, it can be confirmed that the organic electroluminescent devices of Examples 1 to 6 emit light in a blue wavelength range of about 460 nm to about 470 nm. The organic electroluminescent devices of Examples 1 to 6 show excellent external quantum efficiency: EQEmax Values ​​of 20% or greater, EQE max1000nit The value is 18.9% or more. It can be seen that the organic electroluminescent devices of Examples 1 to 6 including the polycyclic compounds according to the embodiment have improved luminous efficiency.

[0346] In contrast, the organic electroluminescent devices of Comparative Examples 1 to 3 emitted blue light but had an EQE of 15.6% or less. max value and EQE of 13.2% or less max1000nit value, indicating low external quantum efficiency.

[0347] Comparative Example Compound X1 and Comparative Example Compound X2 have a multi-resonance structure in which an aromatic ring is linked to a boron atom and a nitrogen atom, but do not have a structure in which an aromatic ring is condensed.

[0348] Comparative Example Compound X3 includes multiple aromatic rings condensed with boron atoms and nitrogen atoms, and thus has the basic structure of Inventive Formula 1. However, it does not have a structure including a group represented by Inventive Formula 2.

[0349] In the polycyclic compound according to the embodiment of the inventive concept, multiple aromatic rings are fused around B and N, and the conjugated system can be extended. Therefore, the polycyclic compound of the embodiment has a stable molecular structure and a multi-resonant molecular skeleton and is included in the emission layer of the organic electroluminescent device, thereby exhibiting excellent luminous efficiency.

[0350] Organic electroluminescent devices according to embodiments of the inventive concept may achieve excellent luminous efficiency.

[0351] The polycyclic compound according to an embodiment of the inventive concept may be applied to an organic electroluminescent device to achieve excellent luminous efficiency.

[0352] Although the inventive concept has been described with reference to its preferred embodiments, it will be understood that the inventive concept should not be limited to these preferred embodiments, but that various changes and modifications may be made by those skilled in the art without departing from the spirit and scope of the inventive concept.

[0353] Therefore, the technical scope of the inventive concept is not intended to be limited to the contents set forth in the detailed description of the specification, but is intended to be defined by the appended claims.

Claims

1. An organic electroluminescent device, comprising: a first electrode; a second electrode facing the first electrode; as well as an emission layer, disposed between the first electrode and the second electrode, wherein the first electrode and the second electrode each independently comprise at least one material selected from the group consisting of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, compounds thereof, and mixtures thereof; Wherein, the emission layer includes a polycyclic compound represented by Formula 1: [Formula 1] In formula 1, X1 is NAr2, O or S, Y1 to Y8 are each independently CM1 or a carbon atom bonded to a group represented by Formula 2, Each M1 is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and optionally, each M1 is independently combined with an adjacent group to form a ring, Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, R1 to R5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and optionally, R1 to R5 are each independently combined with an adjacent group to form a ring, a, b, c and d are each independently an integer from 0 to 2, At least one group represented by Formula 2 is bonded to at least one pair of substituents selected from the group consisting of Y1 and Y2, Y3 and Y4, Y5 and Y6, and Y7 and Y8, [Formula 2] In formula 2, Each X2 and each X3 are independently NAr3, O or S, Each Ar3 is independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, Each R6 and each R7 are independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and optionally, each R6 and each R7 are independently combined with adjacent groups to form a ring, Each e is independently an integer from 0 to 3, Each f is independently an integer from 0 to 4, and * indicates the binding site with the adjacent atom.

2. The organic electroluminescent device according to claim 1, wherein The polycyclic compound represented by Formula 1 is represented by one of Formulas 1-1a to 1-1c: [Formula 1-1a] [Formula 1-1b] [Formula 1-1c] Among them, in Formula 1-1a to Formula 1-1c, Y1 to Y8, Ar1, Ar2, a, b, c, d, and R1 to R5 are the same as defined in Formula 1.

3. The organic electroluminescent device according to claim 1, wherein The polycyclic compound represented by Formula 1 is represented by one of Formulas 4-2a to 4-2d: [Formula 4-2a] [Formula 4-2b] [Formula 4-2c] [Formula 4-2d] Among them, in Formula 4-2a to Formula 4-2d, X 21 、X 22 、X 31 and X 32 are independently NAr4, O or S, Each Ar4 is independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, R 61 、R 62 、R 71 and R 72 are independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and optionally, R 61 、R 62 、R 71 and R 72 Each independently combines with an adjacent group to form a ring, e1 and e2 are each independently an integer from 0 to 3, f1 and f2 are each independently an integer from 0 to 4, and X1 and Ar1 are the same as defined in Formula 1.

4. The organic electroluminescent device according to claim 1, wherein The polycyclic compound represented by Formula 1 is represented by Formula 5-1 or Formula 5-2: [Formula 5-1] [Formula 5-2] Among them, in formula 5-1 and formula 5-2, Each of X1, X2, X3, Ar1, R6, R7, e and f is independently the same as defined in Formula 1 and Formula 2.

5. An organic electroluminescent device, comprising: a first electrode; a second electrode facing the first electrode; as well as an emission layer, disposed between the first electrode and the second electrode, wherein the first electrode and the second electrode each independently comprise at least one material selected from the group consisting of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, compounds thereof, and mixtures thereof; Wherein, the emission layer includes a polycyclic compound represented by Formula 3-1 or Formula 3-2: [Formula 3-1] [Formula 3-2] Among them, in formula 3-1 and formula 3-2, X1 is NAr2, O or S, Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, R1 to R5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and optionally, R1 to R5 are each independently combined with an adjacent group to form a ring, X 21 、X 22 、X 31 and X 32 are independently NAr4, O or S, Each Ar4 is independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, R 61 、R 62 、R 71 and R 72 are independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and optionally, R 61 、R 62 、R 71 and R 72 Each independently combines with an adjacent group to form a ring, a1 and d2 are each independently an integer from 0 to 2, a2, d1, b1 and c1 are each independently an integer from 0 to 4, e1 and e2 are each independently an integer from 0 to 3, f1 and f2 are each independently an integer from 0 to 4.

6. An organic electroluminescent device, comprising: a first electrode; a second electrode facing the first electrode; as well as an emission layer, disposed between the first electrode and the second electrode, wherein the first electrode and the second electrode each independently comprise at least one material selected from the group consisting of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, compounds thereof, and mixtures thereof; The emission layer includes a polycyclic compound represented by one of Formulas 4-1a to 4-1d: [Formula 4-1a] [Formula 4-1b] [Formula 4-1c] [Formula 4-1d] Among them, in Formula 4-1a to Formula 4-1d, X1 is NAr2, O or S, Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, R1 to R5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and optionally, R1 to R5 are each independently combined with an adjacent group to form a ring, X 21 、X 22 、X 31 and X 32 are independently NAr4, O or S, Each Ar4 is independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, R 61 、R 62 、R 71 and R 72 are independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and optionally, R 61 、R 62 、R 71 and R 72 Each independently combines with an adjacent group to form a ring, a1, b2, c2 and d2 are each independently an integer from 0 to 2, a2, b1, c1 and d1 are each independently an integer from 0 to 4, e1 and e2 are each independently an integer from 0 to 3, f1 and f2 are each independently an integer from 0 to 4.

7. The organic electroluminescent device according to claim 6, wherein: The polycyclic compound represented by Formula 4-1a has a linear symmetrical structure with respect to an imaginary line passing through the central nitrogen atom and R5.

8. The organic electroluminescent device according to claim 6, wherein: The polycyclic compound represented by Formula 4-1d has a linear symmetrical structure with respect to an imaginary line passing through the central nitrogen atom and R5.

9. The organic electroluminescent device according to claim 1, 5 or 6, wherein: Ar1 and Ar2 are each independently a substituted or unsubstituted phenyl group.

10. The organic electroluminescent device according to claim 1, 5 or 6, wherein: R6, R7, R 61 、R 62 、R 71 and R 72 are independently unsubstituted methyl, unsubstituted isopropyl, unsubstituted tert-butyl, substituted or unsubstituted biphenylamino or unsubstituted phenyl.

11. The organic electroluminescent device according to claim 1, 5 or 6, wherein: The emission layer emits delayed fluorescence.

12. The organic electroluminescent device according to claim 1, 5 or 6, wherein: The emission layer emits light in the blue wavelength range.

13. The organic electroluminescent device according to claim 1, 5 or 6, wherein: The emission layer includes a first compound and a second compound, and The first compound includes the polycyclic compound.

14. The organic electroluminescent device according to claim 1, 5 or 6, wherein: The polycyclic compound is selected from one of the compounds represented by compound group 1: [Compound Group 1] 。

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