Organic electroluminescent device and polycyclic compound for organic electroluminescent device

Abstract

Provided are an organic electroluminescent device and a polycyclic compound for use in the organic electroluminescent device. The organic electroluminescent device includes: a first electrode; an organic layer disposed on the first electrode; and a second electrode disposed on the organic layer, wherein the organic layer includes a polycyclic compound represented by Formula 1. The organic electroluminescent device can have high emission efficiency. The groups in Formula 1 are the same as defined in the specification.

Description

[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2020-0020252, filed on February 19, 2020, which is hereby incorporated by reference herein in its entirety. Technical Field

[0002] The present disclosure relates to an organic electroluminescent device and a polycyclic compound for an organic electroluminescent device. Background Art

[0003] Recently, organic electroluminescent display devices have been actively developed as image display devices. Unlike liquid crystal display devices, organic electroluminescent display 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, and a light-emitting material including an organic compound in the emissive layer emits light to display an image.

[0004] When organic electroluminescent devices are applied to display apparatuses, it is desired (eg, required) that the driving voltage of the organic electroluminescent devices be reduced and the emission efficiency and lifetime be increased, and the development of materials for organic electroluminescent devices that can stably obtain these characteristics is being continuously pursued.

[0005] Specifically, recently, in order to realize organic electroluminescent devices with high efficiency, technologies regarding phosphorescence emission (which uses triplet energy) or delayed fluorescence emission (which uses a phenomenon of generating singlet excitons by collision of triplet excitons (triplet-triplet annihilation, TTA)) are being developed, and thermally activated delayed fluorescence (TADF) materials using the delayed fluorescence phenomenon are being developed. Summary of the Invention

[0006] One or more aspects of embodiments of the present disclosure relate to an organic electroluminescent device exhibiting long life and high efficiency, and a polycyclic compound used in the organic electroluminescent device.

[0007] One or more aspects of the embodiments of the present disclosure also relate to an organic electroluminescent device including a thermally activated delayed fluorescent material and a polycyclic compound used as the thermally activated delayed fluorescent material.

[0008] According to an embodiment of the present disclosure, an organic electroluminescent device includes: a first electrode; an organic layer located on the first electrode; and a second electrode located on the organic layer, wherein the organic layer includes a polycyclic compound represented by the following Formula 1:

[0009] Formula 1

[0010]

[0011] In Formula 1, X1 to X4 may each independently be NR9, O or S; R1 to R8 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms; R9 may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms. wherein the ring A is a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and optionally (or "optionally"), R9 combines with an adjacent group to form a ring; "a" to "f" may each independently be an integer from 0 to 4; "m" and "n" may each independently be 0 or 1; the dotted line may represent a bond or a non-bond (for example, there is no bond between the groups on each side of the dotted line); and ring A may be represented by any one selected from the following formula 2-1 to formula 2-3:

[0012]

[0013]

[0014] In Formula 2-1 to Formula 2-3, "*" may represent a position for condensation (eg, a binding site with an adjacent atom); X5 and X6 may each independently be CR 30 R 31 NR 32 , O or S; R 30 to R 32 R and R are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms; and R 20 to R 29 Each of them may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, wherein, when ring A is represented by Formula 2-1 or Formula 2-2, at least one selected from "m" and "n" may be 1.

[0015] In an embodiment, the organic layer may include: a hole transport region on the first electrode; an emission layer on the hole transport region; and an electron transport region on the emission layer.

[0016] In an embodiment, the emission layer may include a polycyclic compound and may emit delayed fluorescence.

[0017] In an embodiment, the emission layer may be a delayed fluorescence emission layer including a host and a dopant, and the dopant may be a polycyclic compound.

[0018] In an embodiment, the emissive layer may be a thermally activated delayed fluorescent emissive layer that emits blue light.

[0019] In an embodiment, the electron transport region may include an electron transport layer on the emission layer and an electron injection layer on the electron transport layer, and the electron transport layer or the electron injection layer may include a polycyclic compound.

[0020] In an embodiment, Formula 2-2 may be expressed by any one selected from Formula 3-1 to Formula 3-4 below:

[0021]

[0022]

[0023] In Formulae 3-1 to 3-4, "*" may represent a position for condensation (eg, a binding site with an adjacent atom); R 30 、R 31 and R 33 "j" may be an integer of 0 to 5 and each independently be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms.

[0024] In an embodiment, Formula 2-3 may be expressed by any one selected from Formula 4-1 to Formula 4-3 below:

[0025]

[0026] In Formulae 4-1 to 4-3, "*" may represent a position for condensation (eg, a binding site with an adjacent atom); R 34 It may be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms; and “k” may be an integer of 0 to 5.

[0027] In an embodiment, the polycyclic compound represented by Formula 1 may be represented by the following Formula 5-1 or Formula 5-2:

[0028] Formula 5-1

[0029]

[0030] Formula 5-2

[0031]

[0032] In Formula 5-1 and Formula 5-2, X1 to X4, R1 to R8, R 20 、R 21 and “a” to “f” are the same as defined in Formula 1 and Formula 2-1, respectively.

[0033] In an embodiment, the polycyclic compound represented by Formula 1 may be represented by the following Formula 6-1 or Formula 6-2:

[0034] Formula 6-1

[0035]

[0036] Formula 6-2

[0037]

[0038] In formula 6-1 and formula 6-2, X1 to X5, R1 to R8, R 22 to R 25 and “a” to “f” are the same as defined in Formula 1 and Formula 2-2, respectively.

[0039] In an embodiment, the polycyclic compound represented by Formula 1 may be represented by any one selected from the following Formulas 7-1 to 7-3:

[0040] Formula 7-1

[0041]

[0042] Formula 7-2

[0043]

[0044] Formula 7-3

[0045]

[0046] In formula 7-1 to formula 7-3, X1 to X4, X6, R1 to R8, R 26 to R 29 and "a" to "f" are the same as defined in Formula 1 and Formulas 2-3, respectively.

[0047] In an embodiment, X1 to X4 may each independently be NR 11 or O, and R 11 The aromatic group may be a substituted or unsubstituted aromatic group having 6 to 30 ring carbon atoms.

[0048] In an embodiment, X1 and X4 may be the same, and X2 and X3 may be the same.

[0049] In an embodiment, the polycyclic compound represented by Formula 1 may be any one selected from compounds represented by Compound Group 1 to Compound Group 3 (to be described in more detail below).

[0050] In another embodiment of the present disclosure, a polycyclic compound represented by Formula 1 is provided. BRIEF DESCRIPTION OF THE DRAWINGS

[0051] The accompanying drawings are included to provide a further understanding of the present disclosure and are incorporated in and constitute a part of this specification. The accompanying drawings illustrate exemplary embodiments of the present disclosure and, together with the description, serve to explain the principles of the present disclosure. In the drawings:

[0052] Figure 1 is a cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present disclosure;

[0053] Figure 2 is a cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present disclosure;

[0054] Figure 3 is a cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present disclosure;

[0055] Figure 4 is a cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present disclosure; and

[0056] Figure 5 is a cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present disclosure. DETAILED DESCRIPTION

[0057] The subject matter of the present disclosure may have various modifications and may be implemented in different forms, and example embodiments will be explained in more detail with reference to the accompanying drawings. However, the subject matter of the present disclosure may be implemented in different forms and should not be interpreted as being limited to the embodiments set forth herein. On the contrary, all modifications, equivalents, and replacements within the spirit and technical scope of the present disclosure should be included in the present disclosure.

[0058] It will be understood that when an element (or region, layer, component, etc.) is referred to as being "on," "connected to" or "coupled to" another element, it can be directly on, connected to or coupled to the other element, or a third intervening element may be present.

[0059] The same reference numerals refer to the same elements throughout. In addition, in the drawings, in order to effectively explain the technical content, the thickness, proportion and size of the constituent elements are exaggerated.

[0060] The term "and / or" includes one or more combinations that may be defined by the relevant elements (components).

[0061] It will be understood that although the terms first, second, etc. can be used here to describe various elements, these elements should not be limited by these terms. These terms are only used to distinguish one element from another element. Therefore, without departing from the teachings of the present disclosure, the first element can be named as the second element. Similarly, the second element can be named as the first element. As used herein, unless the context clearly indicates otherwise, the singular form is also intended to include the plural form.

[0062] In addition, the terms "below," "under," "on," and "over" are used to explain the relationship of elements shown in the drawings. The terms are relative concepts and are explained based on the directions shown in the drawings.

[0063] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which the present invention belongs. It will also be understood that terms (such as those defined in common dictionaries) should be interpreted as having a meaning consistent with their meaning in the context of the relevant art and will not be interpreted in an ideal or overly formal sense unless expressly defined as such herein.

[0064] It will also be understood that when the terms “comprises” and / or “includes” and variations thereof are used in this specification, it indicates the presence of the stated features, numbers, steps, operations, elements, parts or combinations thereof, but does not preclude the presence or addition of one or more other features, numbers, steps, operations, elements, parts or combinations thereof.

[0065] Hereinafter, an organic electroluminescent device according to an embodiment of the present disclosure will be explained with reference to the accompanying drawings.

[0066] Figures 1 to 5 1 and 2 are cross-sectional views schematically illustrating an organic electroluminescent device according to an exemplary embodiment of the present disclosure. Figures 1 to 5 In the organic electroluminescent device 10 of the embodiment, the first electrode EL1 and the second electrode EL2 are disposed opposite to each other, and the organic layer OL may be disposed between the first electrode EL1 and the second electrode EL2.

[0067] At the same time, refer to Figures 2 to 5, the organic layer OL of the embodiment may include a plurality of functional layers. The plurality of functional layers may include a hole transport region HTR, an emission layer EML, and an electron transport region ETR. That is, the organic electroluminescent device 10 of the embodiment may include a first electrode EL1, a hole transport region HTR, an emission layer EML, an electron transport region ETR, and a second electrode EL2 stacked in the stated order. In addition, the organic electroluminescent device 10 of the embodiment may include a cap layer CPL (see FIG. 1 ) provided on the second electrode EL2. Figure 5 ).

[0068] The organic electroluminescent device 10 of the embodiment may include a polycyclic compound of the embodiment, which will be explained later, in the organic layer OL disposed between the first electrode EL1 and the second electrode EL2. When the organic layer OL includes an emission layer EML, the emission layer EML may include the polycyclic compound of the embodiment. However, the embodiments of the present disclosure are not limited thereto, but the organic electroluminescent device 10 of the embodiment may include a polycyclic compound of the embodiment, which will be explained later, in the hole transport region HTR or the electron transport region ETR, which are multiple functional layers other than the emission layer EML disposed between the first electrode EL1 and the second electrode EL2, or may include a polycyclic compound of the embodiment, which will be explained later, in the cap layer CPL disposed on the second electrode EL2.

[0069] When with Figure 2 When compared, Figure 3 1 shows a cross-sectional view of an organic electroluminescent device 10 of an embodiment, wherein the hole transport region HTR includes a hole injection layer HIL and a hole transport layer HTL, and the electron transport region ETR includes an electron injection layer EIL and an electron transport layer ETL. Figure 2 When compared, Figure 4 The cross-sectional view of the organic electroluminescent device 10 of the embodiment is shown, wherein the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL and an electron blocking layer EBL, and the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL and a hole blocking layer HBL. Figure 3 When compared, Figure 5 A cross-sectional view of an organic electroluminescent device 10 of an embodiment including a cap layer CPL disposed on the second electrode EL2 is shown.

[0070] The first electrode EL1 is conductive. The first electrode EL1 can be formed using a metal alloy or a conductive compound. The first electrode EL1 can be a pixel electrode or an anode. The first electrode EL1 can be a transmissive electrode, a transflective electrode, or a reflective electrode. When the first electrode EL1 is a transmissive electrode, the first electrode EL1 can be formed using a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), and / or indium tin zinc oxide (ITZO). When the first electrode EL1 is a transflective electrode or a reflective electrode, the first electrode EL1 can include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, compounds thereof, or mixtures thereof (e.g., a mixture of Ag and Mg). In one embodiment, the first electrode EL1 can have a structure including multiple layers, including a reflective layer or a transflective layer formed using 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, the embodiments of the present disclosure are not limited thereto. The thickness of the first electrode EL1 may be about 100 Å. to about For example, about to about

[0071] The organic layer OL is provided on the first electrode EL1. The organic layer OL may have a single layer formed using a single material, a single layer formed using multiple different materials, or a multilayer structure including multiple layers formed using multiple different materials. For example, the organic layer OL may have a single layer structure of an emission layer EML or a multilayer structure including a hole transport region HTR, an emission layer EML, and an electron transport region ETR (e.g., consisting of a hole transport region HTR, an emission layer EML, and an electron transport region ETR).

[0072] The organic layer OL of the organic electroluminescent device 10 of the embodiment includes the polycyclic compound of the embodiment of the present disclosure. If the organic layer OL has a multilayer structure including multiple layers, any layer selected from the multiple layers may include the polycyclic compound of the embodiment. For example, the organic layer OL may include a hole transport region HTR provided on the first electrode EL1, an emission layer EML provided on the hole transport region HTR, and an electron transport region ETR provided on the emission layer EML, and the emission layer EML or the electron transport region ETR may include the polycyclic compound of the embodiment of the present disclosure.

[0073] In the specification, the term "substituted or unsubstituted" refers to (for example, partially) being unsubstituted or substituted with at least one substituent selected from the group consisting of a deuterium atom, a halogen atom, a cyano group, a nitro group, an amino group (or 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. In addition, 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.

[0074] In the specification, the term "forming a ring by combining with an adjacent group" may refer to forming a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle (e.g., a heterocyclic ring) by combining 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 combining with an adjacent group may be a monocyclic ring or a polycyclic ring. In addition, the ring formed by combining with an adjacent group may combine with another ring to form a spiro structure.

[0075] In the specification, the term "adjacent group" may refer to a substituent that replaces an atom directly bonded 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 closest to the corresponding substituent. For example, in 1,2-dimethylbenzene, the two methyl groups may be interpreted as "adjacent groups" to each other, and in 1,1-diethylcyclopentane, the two ethyl groups may be interpreted as "adjacent groups" to each other.

[0076] In the specification, the halogen atom may be a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0077] In the specification, boryl includes alkylboryl and arylboryl. Boryl can refer to an alkyl or aryl group defined below that is bound to a boron atom. Non-limiting examples of boryl include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, diphenylboryl, phenylboryl, etc.

[0078] In the specification, an alkyl group (e.g., an alkyl group) may be a linear, branched, or cycloalkyl group. The carbon number of the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Non-limiting examples of alkyl groups 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.

[0079] In the specification, alkenyl refers to a hydrocarbon group including one or more carbon-carbon double bonds in the middle or at the end of an alkyl group of 2 or more carbon atoms. The alkenyl group can be straight chain or branched. The carbon number is not particularly limited, but can be 2 to 30, 2 to 20, or 2 to 10. Non-limiting examples of alkenyl include vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienylaryl, styryl, styrylvinyl, etc.

[0080] In the specification, alkynyl refers to a hydrocarbon group including one or more carbon-carbon triple bonds in the middle or at the end of an alkyl group of 2 or more carbon atoms. The alkynyl group may be straight chain or branched. The carbon number is not particularly limited, but may be 2 to 30, 2 to 20, or 2 to 10. Non-limiting examples of alkynyl groups include ethynyl, propynyl, etc.

[0081] In the specification, the hydrocarbon ring group may be an optional functional group or substituent derived from an aliphatic hydrocarbon ring or an optional functional group or substituent derived from an aromatic hydrocarbon ring. The carbon number of the hydrocarbon ring group for forming the ring may be 5 to 60, 5 to 30, or 5 to 20.

[0082] In the specification, an aryl group refers to a 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 carbon atoms in the aryl group used to form the ring may be 6 to 30, 6 to 20, or 6 to 15. Non-limiting examples of aryl groups may include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, pentaphenyl, hexaphenyl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, Ji et al.

[0083] In the specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure. Non-limiting examples of substituted fluorenyl groups are as follows (for example, shown below). However, the embodiments of the present disclosure are not limited thereto.

[0084]

[0085] In the specification, a heterocyclic group refers to an optional functional group or substituent derived from a ring including one or more heteroatoms selected from B, O, N, P, Si, and S (e.g., as ring-forming heteroatoms other than carbon atoms). Heterocyclic groups include aliphatic heterocyclic groups and aromatic heterocyclic groups. Aromatic heterocyclic groups may be heteroaryl groups. Aliphatic heterocyclic rings and aromatic heterocyclic rings may be monocyclic or polycyclic.

[0086] In the specification, the heterocyclic group may include one or more of B, O, N, P, Si and S as heteroatoms (e.g., as ring-forming heteroatoms other than carbon atoms). When the heterocyclic group includes two or more heteroatoms, the two or more heteroatoms may be the same or different. The heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and may include a heteroaryl group. The carbon number of the ring for forming the heterocyclic group may be 2 to 30, 2 to 20 or 2 to 10.

[0087] In the specification, the aliphatic heterocyclic group may include one or more selected from B, O, N, P, Si, and S as heteroatoms (e.g., as ring-forming heteroatoms other than carbon atoms). The number of carbon atoms in the ring forming the aliphatic heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10. Non-limiting examples of the aliphatic heterocyclic group may include an oxirane group, an oxirane group, a pyrrolidinyl group, a piperidinyl group, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, a thiocyclopentanyl group, a tetrahydropyranyl group, a 1,4-dioxanyl group, and the like.

[0088] In the specification, the heteroaryl group may be a heteroaryl group including one or more heteroatoms selected from B, O, N, P, Si and S as heteroatoms (e.g., as ring-forming heteroatoms other than carbon atoms). When the heteroaryl group includes two or more heteroatoms, the two or more heteroatoms may be the same or different. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. The number of carbon atoms in the ring forming the heteroaryl group may be 2 to 30, 2 to 20, or 2 to 10. Non-limiting examples of heteroaryl groups can include thienyl, furanyl, 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, dibenzothirolyl, dibenzofuranyl, and the like.

[0089] In the specification, the carbon number of the amino group is not particularly limited, but can be 1 to 30. The amino group can include an alkylamino group, an arylamino group, or a heteroarylamino group. Non-limiting examples of the amino group include a methylamino group, a dimethylamino group, a phenylamino group, a diphenylamino group, a naphthylamino group, a 9-methyl-anthrylamino group, a triphenylamino group, and the like.

[0090] In the specification, the mercapto group may include an alkylthio group and an arylthio group.

[0091] In the specification, the alkoxy group may have a straight chain, a branched chain or a cyclic chain. The carbon number of the alkoxy group is not particularly limited, but may be, for example, 1 to 20 or 1 to 10. Non-limiting examples of the alkoxy group include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, benzyloxy, etc.

[0092] The polycyclic compound according to an embodiment of the present disclosure is represented by the following Formula 1:

[0093] Formula 1

[0094]

[0095] In Formula 1, X1 to X4 are each independently NR9, O or S.

[0096] In Formula 1, R1 to R8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms.

[0097] In Formula 1, R9 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and optionally, R9 combines with an adjacent group to form a ring.

[0098] In Formula 1, "a" is an integer of 0 to 4. Meanwhile, when "a" is 2 or greater, a plurality of R2 groups may be the same or different.

[0099] In Formula 1, "b" is an integer of 0 to 4. Meanwhile, when "b" is 2 or greater, a plurality of R3 groups may be the same or different.

[0100] In Formula 1, "c" is an integer of 0 to 4. Meanwhile, when "c" is 2 or greater, a plurality of R4 groups may be the same or different.

[0101] In Formula 1, "d" is an integer of 0 to 4. Meanwhile, when "d" is 2 or greater, a plurality of R5 groups may be the same or different.

[0102] In Formula 1, "e" is an integer of 0 to 4. Meanwhile, when "e" is 2 or greater, a plurality of R6 groups may be the same or different.

[0103] In Formula 1, "f" is an integer of 0 to 4. Meanwhile, when "f" is 2 or greater, a plurality of R7 groups may be the same or different.

[0104] In Formula 1, "m" and "n" are each independently 0 or 1, and a dotted line represents a bond or non-bond (e.g., there is no bond between the groups on each side of the dotted line). For example, when "m" is 0, in (B) m The surrounding dotted lines represent non-bonds (absence of bonds), and when "m" is 1, in (B) m The surrounding dotted lines represent bonds. When "n" is 0, in (B) n The surrounding dashed lines represent non-bonds, and when "n" is 1, in (B) n The surrounding dotted line represents a bond. The term "bond" as used herein refers to a state in which a single bond is formed between a carbon atom and a boron (B) atom connected (e.g., connected by a dotted line) as in the following Formula 1-1, and the term "non-bond" as used herein refers to a state in which a single bond is formed between carbon and hydrogen without B as in the following Formula 1-2:

[0105]

[0106] In Formula 1, Ring A is an aryl group or a heteroaryl group having (e.g., satisfying) aromaticity. In one embodiment, in Formula 1, Ring A is a non-aromatic condensed polycyclic group or a non-aromatic condensed heteropolycyclic group. In one embodiment, in Formula 1, Ring A is represented by any one selected from the following Formulas 2-1 to 2-3:

[0107]

[0108]

[0109] In Formula 2-1 to Formula 2-3, "*" represents a position for condensation in Formula 1 (for example, a bonding site with an adjacent atom).

[0110] In formula 2-1 to formula 2-3, X5 and X6 are independently CR 30 R 31 NR 32 , O or S.

[0111] In formula 2-1 to formula 2-3, R 30 to R 32 Each is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms.

[0112] In formula 2-1 to formula 2-3, R 20 to R 29 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms.

[0113] When ring A is represented by Formula 2-1 or Formula 2-2, at least one selected from "m" and "n" is 1. In an embodiment, when ring A is represented by Formula 2-1 or Formula 2-2, "m" in Formula 1 may be 1 and "n" may be 0, or "m" in Formula 1 may be 0 and "n" may be 1.

[0114] In an embodiment, when Ring A of Formula 1 is represented by Formula 2-1 or Formula 2-2, "m" and "n" in Formula 1 may both be 1.

[0115] In an embodiment, when ring A is represented by Formula 2-3, "m" and "n" may both be 0, or at least one selected from "m" and "n" may be 1. In an embodiment, when ring A is represented by Formula 2-3, "m" and "n" in Formula 1 may both be 1.

[0116] In an embodiment, X1 to X4 in Formula 1 may each independently be NR 11 or O, and R 11 The aromatic group may be a substituted or unsubstituted aromatic group having 6 to 30 ring carbon atoms.

[0117] In an embodiment, X1 and X4 in Formula 1 may be the same, and X2 and X3 in Formula 1 may be the same.

[0118] In an embodiment, Formula 2-2 may be expressed by any one selected from the following Formulas 3-1 to 3-4:

[0119]

[0120]

[0121] In Formula 3-1 to Formula 3-4, "*" represents a position for condensation (for example, a bonding site with an adjacent atom).

[0122] In formula 3-1, R 30 and R 31 Each of them may independently be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms.

[0123] In formula 3-2, R 33 It may be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, and "j" may be an integer from 0 to 5. Meanwhile, when "j" is 2 or more, multiple R 33 The groups are the same or different.

[0124] In an embodiment, Formula 2-3 may be expressed by any one selected from Formula 4-1 to Formula 4-3 below:

[0125]

[0126] In Formula 4-1 to Formula 4-3, "*" represents a position for condensation (for example, a bonding site with an adjacent atom).

[0127] In formula 4-3, R 34 is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms.

[0128] In Formula 4-3, "k" is an integer from 0 to 5. Meanwhile, when "k" is 2 or more, a plurality of R34 The groups are the same or different.

[0129] In an embodiment, Ring A of Formula 1 may be represented by Formula 2-1. In this case, the polycyclic compound represented by Formula 1 may be represented by Formula 5-1 or Formula 5-2 below:

[0130] Formula 5-1

[0131]

[0132] Formula 5-2

[0133]

[0134] In Formula 5-1 and Formula 5-2, X1 to X4, R1 to R8, R 20 、R 21 and “a” to “f” are the same as those defined in conjunction with Formula 1 and Formula 2-1, respectively.

[0135] In an embodiment, Ring A of Formula 1 may be represented by Formula 2-2. In this case, the polycyclic compound represented by Formula 1 may be represented by Formula 6-1 or Formula 6-2 below:

[0136] Formula 6-1

[0137]

[0138] Formula 6-2

[0139]

[0140] In formula 6-1 and formula 6-2, X1 to X5, R1 to R8, R 22 to R 25 and “a” to “f” are the same as those defined in conjunction with Formula 1 and Formula 2-2, respectively.

[0141] In an embodiment, Ring A of Formula 1 may be represented by Formula 2-3. In this case, the polycyclic compound represented by Formula 1 may be represented by any one selected from the following Formulas 7-1 to 7-3:

[0142] Formula 7-1

[0143]

[0144] Formula 7-2

[0145]

[0146] Formula 7-3

[0147]

[0148] In formula 7-1 to formula 7-3, X1 to X4, X6, R1 to R8, R 26 to R 29 and “a” to “f” are the same as defined in conjunction with Formula 1 and Formulas 2-3, respectively.

[0149] In an embodiment, the polycyclic compound represented by Formula 1 may be any one selected from the compounds represented in the following Compound Group 1, but the embodiments of the present disclosure are not limited thereto:

[0150] Compound Group 1

[0151]

[0152]

[0153]

[0154] In an embodiment, the polycyclic compound represented by Formula 1 may be any one selected from the compounds represented in the following Compound Group 2, but the embodiments of the present disclosure are not limited thereto:

[0155] Compound Group 2

[0156]

[0157]

[0158]

[0159]

[0160] In an embodiment, the polycyclic compound represented by Formula 1 may be any one selected from the compounds represented in the following Compound Group 3, but the embodiments of the present disclosure are not limited thereto:

[0161] Compound Group 3

[0162]

[0163]

[0164] The aforementioned polycyclic compound can be used in the organic electroluminescent device 10 of the embodiment and can improve the efficiency and life of the organic electroluminescent device 10. In one embodiment, the polycyclic compound can be used in the organic layer OL of the organic electroluminescent device 10 of the embodiment and can improve the emission efficiency, electron transport characteristics and life of the organic electroluminescent device 10.

[0165] The organic layer OL may include one selected from two or more polycyclic compounds represented by Formula 1. For example, the organic layer OL may include at least one selected from the compounds represented by the aforementioned compound groups 1 to 3. In one embodiment, the organic layer OL may include one or more different polycyclic compounds each represented by Formula 1.

[0166] Refer again Figures 2 to 5 , the organic layer OL may include a hole transport region HTR, an emission layer EML, and an electron transport region ETR.

[0167] The hole transport region HTR is disposed on the first electrode EL1 , and may include a hole injection layer HIL, a hole transport layer HTL, a hole buffer layer, and / or an electron blocking layer EBL.

[0168] The hole transport region HTR may have a single layer formed using a single material, a single layer formed using a plurality of different materials, or a multilayer structure including a plurality of layers formed using different materials.

[0169] For example, the hole transport region HTR may have a single-layer structure of the hole injection layer HIL or the hole transport layer HTL, or may have a single-layer structure formed using a hole injection material and a hole transport material. In one embodiment, the hole transport region HTR may have a single-layer structure formed using a plurality of different materials, or a structure of a hole injection layer HIL / hole transport layer HTL, a hole injection layer HIL / hole transport layer HTL / hole buffer layer, a hole injection layer HIL / hole buffer layer, a hole transport layer HTL / hole buffer layer, or a hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL stacked from the first electrode EL1. However, the embodiments of the present disclosure are not limited thereto.

[0170] The hole transport region HTR may be formed using various suitable 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 / or a laser induced thermal imaging (LITI) method.

[0171] 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-phenylene)sulfonylene glycol)sulfonyl chloride (PTTA), and poly(ethylenedioxythiophene). sulfonate) (PEDOT / PSS), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), N,N′-di(naphthalen-1-yl)-N,N′-diphenyl-benzidine (NPD), triphenylamine-containing polyetherketone (TPAPEK), 4-isopropyl-4′-methyldiphenyliodonium tetrakis(pentafluorophenyl)borate and / or dipyrazino[2,3-f:2′,3′-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN).

[0172] The hole transport layer HTL may include commonly used materials (e.g., materials known in the art). For example, it may also include carbazole derivatives (such as N-phenylcarbazole and / or 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 (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), and the like.

[0173] The electron blocking layer EBL may include, for example, carbazole derivatives (such as N-phenylcarbazole and / or 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 (NPD), 4,4′-cyclohexylenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (HMTPD) and / or mCP.

[0174] The thickness of the hole transport region HTR may be about to about For example, about to about The thickness of the hole injection layer HIL can be, for example, about to about And the thickness of the hole transport layer HTL can be about to about For example, the thickness of the electron blocking layer EBL may be about to about When the thicknesses of the hole transport region HTR, the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL all satisfy the above ranges, satisfactory hole transport characteristics can be achieved without significantly increasing driving voltage.

[0175] In addition to the above materials, the hole transport region HTR may further include a charge generating material to increase conductivity. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region HTR. The charge generating material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano compound. For example, non-limiting examples of p-dopants may include quinone derivatives (such as tetracyanoquinodimethane (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ)), metal oxides (such as tungsten oxide and / or molybdenum oxide), and the like.

[0176] 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 resonance distance according to the wavelength of light emitted from the emission layer EML to increase luminous efficiency. The material 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 substantially prevents electrons from being injected from the electron transport region ETR into the hole transport region HTR.

[0177] The emission layer EML is provided on the hole transport region HTR. The emission layer EML may have, for example, an area of ​​about to about or about to about The emission layer EML may have a single layer formed using a single material, a single layer formed using a plurality of different materials, or a multilayer structure including a plurality of layers formed using a plurality of different materials.

[0178] The emission layer EML may emit one selected from red light, green light, blue light, white light, yellow light, and cyan light, and may include a fluorescent emission material or a phosphorescent emission material.

[0179] In an embodiment, the emission layer EML may be a fluorescent emission layer. For example, the light emitted from the emission layer EML may be partially emitted due to thermally activated delayed fluorescence (TADF). That is, a portion of the light emitted from the emission layer EML may be emitted due to thermally activated delayed fluorescence (TADF). In an embodiment, the emission layer EML may include a luminescent component that emits thermally activated delayed fluorescence. In an embodiment, the emission layer EML may be a blue light emitting layer that emits thermally activated delayed fluorescence.

[0180] The emission layer EML of the organic electroluminescent device 10 of the embodiment may include a polycyclic compound according to an embodiment of the present disclosure. In one embodiment, the polycyclic compound may be used in the emission layer EML of the organic electroluminescent device 10 of the embodiment and may improve the emission efficiency and lifespan of the organic electroluminescent device 10.

[0181] The emission layer EML may include one or two or more polycyclic compounds represented by Formula 1. For example, the emission layer EML may include at least one compound selected from the compounds represented by Compound Group 1 to Compound Group 3. In one embodiment, the emission layer EML may include one or more different polycyclic compounds each represented by Formula 1.

[0182] In an embodiment, the emission layer EML may include a host and a dopant, the host may be a host for emitting delayed fluorescence, and the dopant may be a dopant for emitting delayed fluorescence. Meanwhile, the polycyclic compound of the embodiment represented by Formula 1 may be included as a dopant material of the emission layer EML. For example, the polycyclic compound of the embodiment represented by Formula 1 may be used as a TADF dopant.

[0183] In one embodiment, the organic electroluminescent device 10 of the embodiment may include multiple emission layers. The multiple emission layers may be stacked in sequence to provide, for example, an organic electroluminescent device 10 that can emit white light. The organic electroluminescent device 10 including multiple emission layers may be an organic electroluminescent device having a tandem structure. When the organic electroluminescent device 10 includes multiple emission layers, at least one emission layer may include a polycyclic compound according to the present disclosure.

[0184] The emission layer EML may further include a dopant, and the dopant may use a suitable (e.g., known) material. For example, the dopant may be selected from 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 / or N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalene-2-yl)vinyl)phenyl)-N-phenylaniline (N-BD AVBi)), 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 and / or 1,6-bis(N,N-diphenylamino)pyrene), and 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi). However, the embodiments of the present disclosure are not limited thereto.

[0185] The emission layer EML may also include commonly used materials (e.g., materials known in the art). For example, the emission layer EML may include tris(8-hydroxyquinoline)aluminum (Alq3), bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 4,4′-bis(N-carbazole-9-yl)biphenyl (CBP), 1,3-bis(N-carbazole-9-yl)benzene (mCP), 2,8-bis(diphenylphosphoryl)dibenzo[b,d]furan (PPF), 4,4′,4″-tris(carbazole-9-yl)-triphenylamine (TCTA), poly(N-vinylcarbazole) (PVK), 9,10-di(naphthalene-2-yl)anthracene (ADN), 2-tert-butyl-9,10-di(naphthalene-2-yl)anthracene. At least one selected from among (TBADN), distyryl arylene (DSA), 4,4′-bis(9-carbazolyl)-2,2′-diphenyl-biphenyl (CDBP), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH-2), hexaphenylcyclotrisiloxane (DPSiO3), octaphenylcyclotetrasiloxane (DPSiO4), and 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi) is used as the host material. However, the embodiments of the present disclosure are not limited thereto.

[0186] When the emission layer EML emits red light, the emission layer EML may further include, for example, a fluorescent material including tris(dibenzoylmethane)phenanthroline europium (PBD:Eu(DBM)3(Phen)) or perylene. When the emission layer EML emits red light, the dopant included in the emission layer EML may be selected from, for example, a metal complex or an organic metal complex (such as bis(1-phenylisoquinolinolato)iridium acetylacetonate (PIQIr(acac)), bis(1-phenylquinolinolato)iridium acetylacetonate (PQIr(acac)), tris(1-phenylquinolinolato)iridium (PQIr) and / or platinum octaethylporphyrin (PtOEP)), rubrene and its derivatives, and 4-dicyanomethylidene-2-(p-dimethylaminophenyl)-6-methyl-4H-pyran (DCM) and its derivatives.

[0187] When the emission layer EML emits green light, the emission layer EML may further include, for example, a fluorescent material including tris(8-hydroxyquinoline)aluminum (Alq3). When the emission layer EML emits green light, the dopant included in the emission layer EML may be selected from, for example, a metal complex or an organometallic complex (such as f-tris(2-phenylpyridine)iridium (Ir(ppy)3)) and coumarin and its derivatives.

[0188] When the emission layer EML emits blue light, the emission layer EML may further include a fluorescent material, wherein the fluorescent material includes any one selected from the group consisting of spiro-DPVBi, spiro-6P, distyryl benzene (DSB), distyryl arylene (DSA), polyfluorene (PFO) polymers, and poly(p-phenylene vinylene) (PPV) polymers. When the emission layer EML emits blue light, the dopant included in the emission layer EML may be selected from, for example, metal complexes or organometallic complexes (such as (4,6-F2ppy)2Irpic) and perylene and its derivatives.

[0189] The electron transport region ETR is disposed 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 the present disclosure is not limited thereto.

[0190] The electron transport region ETR may have a single layer formed using a single material, a single layer formed using a plurality of different materials, or a multilayer structure including a plurality of layers formed using a plurality of different materials.

[0191] For example, the electron transport region ETR may have a single layer structure of an electron injection layer EIL or an electron transport layer ETL, or a single layer structure formed using an electron injection material and an electron transport material. In addition, the electron transport region ETR may have a single layer structure including a plurality of 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 emission layer EML. However, the embodiments of the present disclosure are not limited thereto. The thickness of the electron transport region ETR may be, for example, about to about

[0192] The electron transport region ETR of the organic electroluminescent device 10 of the embodiment may include the polycyclic compound according to the embodiment of the present disclosure. For example, the electron transport region ETR may include the polycyclic compound represented by Formula 1.

[0193] When the electron transport region ETR has a multilayer structure including a plurality of layers, any one of the plurality of layers may include the polycyclic compound represented by Formula 1. For example, the electron transport region ETR may include an electron transport layer ETL disposed on the emission layer EML and an electron injection layer EIL disposed on the electron transport layer ETL, and the electron transport layer ETL or the electron injection layer EIL may include the polycyclic compound according to an embodiment of the present disclosure.

[0194] The electron transport region ETR may include one or two or more polycyclic compounds represented by Formula 1. For example, the electron transport region ETR may include at least one compound selected from the compounds represented in the aforementioned compound groups 1 to 3. In one embodiment, the electron transport region ETR may include one or more different polycyclic compounds each represented by Formula 1.

[0195] The electron transport region ETR may be formed using various suitable 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 / or a laser induced thermal imaging (LITI) method.

[0196] In addition to the polycyclic compound, the electron transport region ETR may also include a suitable (e.g., known) material. When the electron transport region ETR includes an electron transport layer ETL, the electron transport layer ETL may include an anthracene compound. The electron transport layer ETL 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, bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 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-hydroxyquinolinol-N1,O8)-(1,1′-biphenyl-4-hydroxy)aluminum (BAlq), bis(benzoquinolinol-10-hydroxy)beryllium (Bebq2), 9,10-di(naphthalene-2-yl)anthracene (ADN), or a mixture thereof. However, the embodiments of the present disclosure are not limited thereto. The thickness of the electron transport layer ETL may be about 100 Å. to about and can be, for example, about to about When the thickness of the electron transport layer ETL satisfies the above range, satisfactory electron transport characteristics may be obtained without significantly increasing driving voltage.

[0197] When the electron transport region ETR includes an electron injection layer EIL, the electron transport region ETR may include a metal halide (such as LiF, NaCl, CsF, RbCl and / or RbI), a lanthanide metal (such as Yb), a metal oxide (such as Li2O and / or BaO) and / or lithium hydroxyquinoline (LiQ). However, the embodiments of the present disclosure are not limited thereto. The electron injection layer EIL may also be formed using a mixed material of an electron injection 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 and / or a metal stearate. The thickness of the electron injection layer EIL may be about 1000 nm. to about or about to about When the thickness of the electron injection layer EIL satisfies the above range, satisfactory electron injection characteristics can be obtained without significantly increasing driving voltage.

[0198] The electron transport region ETR may include the hole blocking layer HBL as described above. The hole blocking layer HBL may include, for example, at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) and 4,7-diphenyl-1,10-phenanthroline (Bphen). However, the present disclosure is not limited thereto.

[0199] 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. When the second electrode EL2 is a transmissive electrode, the second electrode EL2 may include a transparent metal oxide, such as ITO, IZO, ZnO, ITZO, or the like.

[0200] When the second electrode EL2 is a transmissive electrode or a transflective electrode, the second electrode EL2 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, a compound thereof, or a mixture thereof (e.g., a mixture of Ag and Mg). The second electrode EL2 may have a multilayer structure including a reflective layer or a transflective layer formed using the above materials and a transparent conductive layer formed using ITO, IZO, ZnO, ITZO, or the like.

[0201] In one embodiment, the second electrode EL2 may be connected to the auxiliary electrode. When the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.

[0202] At the same time, refer to Figure 4 , 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, for example, 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), and the like.

[0203] The organic electroluminescent device 10 according to an embodiment of the present disclosure includes the polycyclic compound represented by Formula 1 and can exhibit suitable (e.g., excellent) emission efficiency and long life. In addition, the organic electroluminescent device 10 of the embodiment can exhibit high efficiency and long life characteristics in the blue wavelength region.

[0204] Hereinafter, the polycyclic compound according to the embodiment and the organic electroluminescent device according to the embodiment of the present disclosure will be specifically explained with reference to Examples and Comparative Examples. The following examples are merely illustrations for helping to understand the present disclosure, and the scope of the present disclosure is not limited thereto.

[0205] Example

[0206] Synthesis of polycyclic compounds

[0207] The synthesis method of the polycyclic compound explained below is merely an exemplary embodiment, and the synthesis method of the polycyclic compound according to an embodiment of the present disclosure is not limited thereto.

[0208] 1. Synthesis of Compounds 1-9

[0209]

[0210] (1) Synthesis of intermediate 1-9a

[0211] 3,5-bis(diphenylamino)phenol (1 eq.), 1-bromo-3-fluorobenzene (1.1 eq.), and potassium carbonate (2 eq.) were added to DMF, and then stirred at about 160° C. for about 24 hours under a nitrogen atmosphere. After cooling, the reaction solution was washed three times with ethyl acetate and water, and the organic layer obtained was dried over anhydrous MgSO4 and dried under reduced pressure. Intermediate 1-9a was obtained by column chromatography (yield: 80%).

[0212] (2) Synthesis of intermediate 1-9b

[0213] Intermediate 1-9a (1 eq.), N1,N1,N3,N3,N5-pentaphenylbenzene-1,3,5-triamine (1.1 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.1 eq.), and sodium tert-butoxide (3 eq.) were dissolved in toluene and then stirred at about 100° C. for about 12 hours under a nitrogen atmosphere. After cooling, the reaction solution was washed three times with ethyl acetate and water, and the organic layer obtained was dried over anhydrous MgSO4 and dried under reduced pressure. Intermediate 1-9b was obtained by column chromatography (yield: 75%).

[0214] (3) Synthesis of intermediate 1-9c

[0215] Intermediate 1-9c (1 eq.) was dissolved in o-dichlorobenzene, the flask was cooled to about 0°C under a nitrogen atmosphere, and BBr3 (4 eq.) was slowly injected therein. After the addition was complete, the temperature was raised to about 160°C and stirred for about 24 hours. After cooling, triethylamine was slowly added dropwise to the flask until heating was stopped to complete the reaction, and hexane was added thereto for precipitation. A solid component was obtained by filtration. The solid component thus obtained was separated by column chromatography and further separated by recrystallization with MC / Hex to obtain Intermediate 1-9c (yield: 15%).

[0216] (4) Synthesis of Compounds 1-9

[0217] Intermediate 1-9c (1 eq.) was dissolved in o-dichlorobenzene, the flask was cooled to about 1.5 ℃ under a nitrogen atmosphere, and BI3 (2.5 eq.) was slowly injected therein. After the addition was completed, the temperature was raised to about 160 ℃ and stirred for about 6 hours. After cooling, triethylamine was slowly added dropwise to the flask until heating was stopped to complete the reaction, and hexane was added thereto for precipitation. A solid component was filtered and obtained. The solid component thus obtained was separated by silica filtration and further separated by recrystallization with MC / Hex to obtain compound 1-9 (yield: 10%).

[0218] 2. Synthesis of Compounds 1-10

[0219]

[0220] (1) Synthesis of intermediate 1-10a

[0221] N1,N1,N3,N3,N5-pentaphenylbenzene-1,3,5-triamine (2.2 eq.), 1,3-dibromobenzene (1 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.1 eq.), and sodium tert-butoxide (3 eq.) were dissolved in toluene and then stirred at about 100° C. for about 12 hours under a nitrogen atmosphere. After cooling, the reaction solution was washed three times with ethyl acetate and water, and the organic layer obtained was dried over anhydrous MgSO4 and dried under reduced pressure. Intermediate 1-10a was obtained by column chromatography (yield: 65%).

[0222] (2) Synthesis of intermediate 1-10b

[0223] Intermediate 1-10a (1 eq.) was dissolved in o-dichlorobenzene, the flask was cooled to about 0°C under a nitrogen atmosphere, and BBr3 (4 eq.) was slowly injected therein. After the addition was complete, the temperature was raised to about 160°C and stirred for about 24 hours. After cooling, triethylamine was slowly added dropwise to the flask until heating was stopped to complete the reaction, and hexane was added thereto for precipitation. Filtering was performed to obtain a solid component. The solid component thus obtained was separated by column chromatography and further separated by recrystallization with MC / Hex to obtain Intermediate 1-10b (yield: 15%).

[0224] (3) Synthesis of Compounds 1-10

[0225] Intermediate 1-10b (1 eq.) was dissolved in o-dichlorobenzene, the flask was cooled to about 0°C under a nitrogen atmosphere, and BI3 (2.5 eq.) was slowly injected therein. After the addition was completed, the temperature was raised to about 160°C and stirred for about 6 hours. After cooling, triethylamine was slowly added dropwise to the flask until heating was stopped to complete the reaction, and hexane was added thereto for precipitation. A solid component was filtered and obtained. The solid component thus obtained was separated by silica filtration and further separated by recrystallization with MC / Hex to obtain compound 1-10 (yield: 10%).

[0226] 3. Synthesis of Compound 2-2

[0227]

[0228] (1) Synthesis of intermediate 2-2a

[0229] 2,7-Dibromo-9-phenyl-9H-carbazole (1 eq.), 3,5-bis(diphenylamino)phenol (2.5 eq.), and potassium carbonate (5 eq.) were added to DMSO, followed by stirring at approximately 180°C for approximately 24 hours under a nitrogen atmosphere. After cooling, the reaction solution was washed five times with ethyl acetate and water, and the resulting organic layer was dried over anhydrous MgSO4 and dried under reduced pressure. Intermediate 2-2a was obtained by column chromatography (yield: 50%).

[0230] (2) Synthesis of intermediate 2-2b

[0231] Intermediate 2-2a (1 eq.) was dissolved in o-dichlorobenzene, the flask was cooled to about 0°C under a nitrogen atmosphere, and BBr3 (4 eq.) was slowly injected therein. After the addition was completed, the temperature was raised to about 160°C and stirred for about 24 hours. After cooling, triethylamine was slowly added dropwise to the flask until heating was stopped to complete the reaction, and hexane was added thereto for precipitation. A solid component was obtained by filtration. The solid component thus obtained was separated by column chromatography and further separated by recrystallization with MC / Hex to obtain intermediate 2-2b (yield: 15%).

[0232] (3) Synthesis of Compound 2-2

[0233] Intermediate 2-2b (1 eq.) was dissolved in o-dichlorobenzene, the flask was cooled to about 0°C under a nitrogen atmosphere, and BI3 (2.5 eq.) was slowly injected therein. After the addition was completed, the temperature was raised to about 160°C and stirred for about 6 hours. After cooling, triethylamine was slowly added dropwise to the flask until heating was stopped to complete the reaction, and hexane was added thereto for precipitation. A solid component was filtered and obtained. The solid component thus obtained was separated by silica filtration and further separated by recrystallization with MC / Hex to obtain compound 2-2 (yield: 10%).

[0234] 4. Synthesis of Compound 2-3

[0235]

[0236] (1) Synthesis of intermediate 2-3a

[0237] 1,3-Dibromo-5-phenoxybenzene (1 eq.), diphenylamine (1 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.01 eq.), tri-tert-butylphosphine (0.05 eq.), and sodium tert-butoxide (3 eq.) were dissolved in toluene and stirred at about 90° C. for about 2 hours under a nitrogen atmosphere. After cooling, the reaction solution was washed three times with ethyl acetate and water, and the organic layer thus obtained was dried over anhydrous MgSO 4 and dried under reduced pressure. Intermediate 2-3a was obtained by column chromatography (yield: 65%).

[0238] (2) Synthesis of intermediate 2-3b

[0239] Intermediate 2-3a (1 eq.), aniline (1.1 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.01 eq.), tri-tert-butylphosphine (0.05 eq.) and sodium tert-butoxide (3 eq.) were dissolved in toluene and stirred at about 90° C. for about 2 hours under a nitrogen atmosphere. After cooling, the reaction solution was washed three times with ethyl acetate and water, and the organic layer thus obtained was dried over anhydrous MgSO 4 and dried under reduced pressure. Intermediate 2-3b was obtained by column chromatography (yield: 75%).

[0240] (3) Synthesis of intermediate 2-3c

[0241] Intermediate 2-3b (2.1 eq.), 2,7-dibromo-9-phenyl-9H-carbazole (1 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.1 eq.) and sodium tert-butoxide (3 eq.) were dissolved in toluene and stirred at about 100° C. for about 24 hours under a nitrogen atmosphere. After cooling, the reaction solution was washed three times with ethyl acetate and water, and the organic layer obtained was dried over anhydrous MgSO 4 and dried under reduced pressure. Intermediate 2-3c was obtained by column chromatography (yield: 65%).

[0242] (4) Synthesis of intermediate 2-3d

[0243] Intermediate 2-3c (1 eq.) was dissolved in o-dichlorobenzene, the flask was cooled to about 0°C under a nitrogen atmosphere, and BBr3 (4 eq.) was slowly injected therein. After the addition was completed, the temperature was raised to about 160°C and stirred for about 24 hours. After cooling, triethylamine was slowly added dropwise to the flask until heating was stopped to complete the reaction, and hexane was added thereto for precipitation. A solid component was filtered to obtain the solid component. The solid component thus obtained was separated by column chromatography and further separated by recrystallization with MC / Hex to obtain intermediate 2-3d (yield: 15%).

[0244] (5) Synthesis of Compound 2-3

[0245] Intermediate 2-3d (1 eq.) was dissolved in o-dichlorobenzene, the flask was cooled to about 0°C under a nitrogen atmosphere, and BI3 (2.5 eq.) was slowly injected therein. After the addition was completed, the temperature was raised to about 160°C and stirred for about 6 hours. After cooling, triethylamine was slowly added dropwise to the flask until heating was stopped to complete the reaction, and hexane was added thereto for precipitation. A solid component was filtered and obtained. The solid component thus obtained was separated by silica filtration and further separated by recrystallization with MC / Hex to obtain compound 2-3 (yield: 10%).

[0246] 5. Synthesis of Compound 2-13

[0247]

[0248] (1) Synthesis of intermediate 2-13a

[0249] N1,N1,N3,N3,N5-pentaphenylbenzene-1,3,5-triamine (2.2 eq.), 3,7-dibromodibenzo[b,d]furan (1 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.1 eq.), and sodium tert-butoxide (3 eq.) were dissolved in toluene and then stirred at about 100° C. for about 12 hours under a nitrogen atmosphere. After cooling, the reaction solution was washed three times with ethyl acetate and water, and the organic layer obtained was dried over anhydrous MgSO4 and dried under reduced pressure. Intermediate 2-13a was obtained by column chromatography (yield: 65%).

[0250] (2) Synthesis of intermediate 2-13b

[0251] Intermediate 2-13a (1 eq.) was dissolved in o-dichlorobenzene, the flask was cooled to about 0°C under a nitrogen atmosphere, and BBr3 (4 eq.) was slowly injected therein. After the addition was complete, the temperature was raised to about 160°C and stirred for about 24 hours. After cooling, triethylamine was slowly added dropwise to the flask until heating was stopped to complete the reaction, and hexane was added thereto for precipitation. A solid component was obtained by filtration. The solid component thus obtained was separated by column chromatography and further separated by recrystallization with MC / Hex to obtain intermediate 2-13b (yield: 15%).

[0252] (3) Synthesis of Compound 2-13

[0253] Intermediate 2-13b (1 eq.) was dissolved in o-dichlorobenzene, the flask was cooled to about 0°C under a nitrogen atmosphere, and BI3 (2.5 eq.) was slowly injected therein. After the addition was completed, the temperature was raised to about 160°C and stirred for about 6 hours. After cooling, triethylamine was slowly added dropwise to the flask until heating was stopped to complete the reaction, and hexane was added thereto for precipitation. A solid component was filtered and obtained. The solid component thus obtained was separated by silica filtration and further separated by recrystallization with MC / Hex to obtain compound 2-13 (yield: 10%).

[0254] 6. Synthesis of Compound 3-1

[0255]

[0256] (1) Synthesis of intermediate 3-1a

[0257] 4-Fluoro-2-((3-fluorophenyl)amino)benzoic acid (1 eq.) was added to CH 3 CN at a concentration of about 0.44 M. After heating to about 90° C., phosphorus (V) oxychloride (2.2 eq.) was slowly added over about 1 hour. After the addition was completed, the reaction solution was stirred at about 90° C. for about 2 hours. After cooling, H 2 O (70 eq.) was added thereto, followed by stirring at about 100° C. for about 3 hours. After cooling, the reaction solution was washed three times with ethyl acetate and water, and the organic layer thus obtained was dried over anhydrous MgSO 4 and dried under reduced pressure. Intermediate 3-1a was obtained by column chromatography (yield: 30%).

[0258] (2) Synthesis of intermediate 3-1b

[0259] Intermediate 3-1a (1 eq.), bromobenzene (1.1 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.01 eq.), tri-tert-butylphosphine (0.05 eq.) and sodium tert-butoxide (3 eq.) were dissolved in toluene and stirred at about 90° C. for about 2 hours under a nitrogen atmosphere. After cooling, the reaction solution was washed three times with ethyl acetate and water, and the organic layer obtained was dried over anhydrous MgSO 4 and dried under reduced pressure. Intermediate 3-1b was obtained by column chromatography (yield: 65%).

[0260] (3) Synthesis of Intermediate 3-1c

[0261] 5-Iodobenzene-1,3-diol (1 eq.), fluorobenzene (1.1 eq.), and potassium carbonate (2 eq.) were added to DMSO, followed by stirring at approximately 160°C for approximately 12 hours under a nitrogen atmosphere. After cooling, the reaction solution was washed five times with ethyl acetate and water, and the resulting organic layer was dried over anhydrous MgSO4 and dried under reduced pressure. Intermediate 3-1c was obtained by column chromatography (yield: 50%).

[0262] (4) Synthesis of intermediate 3-1d

[0263] Intermediate 3-1c (1 eq.), bis((2-trimethylsilyl)phenyl)amine (2.2 eq.), cuprous iodide (0.05 eq.), potassium hydroxide (5 eq.) and 1,10-phenanthroline (0.05 eq.) were added to xylene, and then stirred at about 110° C. for about 24 hours under a nitrogen atmosphere. After cooling, the reaction solution was washed five times with ethyl acetate and water, and the organic layer thus obtained was dried over anhydrous MgSO 4 and dried under reduced pressure. Intermediate 3-1d was obtained by column chromatography (yield: 50%).

[0264] (5) Synthesis of intermediate 3-1e

[0265] Intermediate 3-1b (1 eq.), Intermediate 3-1d (2.2 eq.) and cesium carbonate (5 eq.) were dissolved in DMSO and then stirred at about 160° C. for about 24 hours under a nitrogen atmosphere. After cooling, the reaction solution was washed five times with ethyl acetate and water, and the organic layer obtained was dried over anhydrous MgSO4 and dried under reduced pressure. Intermediate 3-1e was obtained by column chromatography (yield: 35%).

[0266] (6) Synthesis of Compound 3-1

[0267] BBr3 (5 eq.) was dissolved in o-dichlorobenzene, the flask was cooled to about 0°C under a nitrogen atmosphere, and the intermediate 3-1e (1 eq.) dissolved in o-dichlorobenzene was slowly added over about one hour. After the addition was completed, stirring was performed at room temperature for about 2 hours, and the reaction solution was cooled to about 0°C. Then, diisopropylethylamine (15 eq.) was added thereto. After the addition, the temperature was raised to about 160°C and stirring was performed for about 24 hours. After the reaction was completed, hexane was added thereto for precipitation. Filter and obtain a solid component. The solid component thus obtained was separated by column chromatography, and further separated by recrystallization with MC / Hex to obtain 3-1 (yield: 15%).

[0268] 7. Synthesis of Compound 3-2

[0269]

[0270] (1) Synthesis of intermediate 3-2a

[0271] 2,2′,4,4′-Tetrahydroxybenzophenone was heated at about 220° C. for about 6 hours using a sand bath, and Intermediate 3-2a was obtained by column chromatography (yield: 85%).

[0272] (2) Synthesis of intermediate 3-2b

[0273] Intermediate 3-2a (1 eq.), 1-fluoro-3-iodo-5-phenoxybenzene (2.2 eq.), and cesium carbonate (5 eq.) were dissolved in DMSO and then stirred at about 160° C. for about 24 hours under a nitrogen atmosphere. After cooling, the reaction solution was washed five times with ethyl acetate and water, and the organic layer obtained was dried over anhydrous MgSO4 and dried under reduced pressure. Intermediate 3-2b was obtained by column chromatography (yield: 35%).

[0274] (3) Synthesis of intermediate 3-2c

[0275] Intermediate 3-2b (1 eq.), bis((2-trimethylsilyl)phenyl)amine (2.2 eq.), cuprous iodide (0.05 eq.), potassium hydroxide (5 eq.) and 1,10-phenanthroline (0.05 eq.) were added to xylene, and then stirred at about 110° C. for about 24 hours under a nitrogen atmosphere. After cooling, the reaction solution was washed five times with ethyl acetate and water, and the organic layer thus obtained was dried over anhydrous MgSO 4 and dried under reduced pressure. Intermediate 3-2c was obtained by column chromatography (yield: 55%).

[0276] (4) Synthesis of Compound 3-2

[0277] BBr3 (5 eq.) was dissolved in o-dichlorobenzene, the flask was cooled to about 0°C under a nitrogen atmosphere, and the intermediate 3-2c (1 eq.) dissolved in o-dichlorobenzene was slowly added over about one hour. After the addition was completed, stirring was performed at room temperature for about 2 hours, and the reaction solution was cooled to about 0°C. Then, diisopropylethylamine (15 eq.) was added thereto. After the addition, the temperature was raised to about 160°C and stirring was performed for about 24 hours. After the reaction was completed, hexane was added thereto for precipitation. Filter and obtain a solid component. The solid component thus obtained was separated by column chromatography, and further separated by recrystallization with MC / Hex to obtain compound 3-2 (yield: 15%).

[0278] 8. Synthesis of Compound 3-4

[0279]

[0280] (1) Synthesis of intermediate 3-4a

[0281] 3-Bromo-5-(diphenylamino)phenol (1 eq.), bis((2-trimethylsilyl)phenyl)amine (1.1 eq.), cuprous iodide (0.05 eq.), potassium hydroxide (5 eq.) and 1,10-phenanthroline (0.05 eq.) were added to xylene, and then stirred at about 110° C. for about 24 hours under a nitrogen atmosphere. After cooling, the reaction solution was washed five times with ethyl acetate and water, and the organic layer thus obtained was dried over anhydrous MgSO 4 and dried under reduced pressure. Intermediate 3-4a was obtained by column chromatography (yield: 55%).

[0282] (2) Synthesis of intermediate 3-4b

[0283] Intermediate 3-4a (2.2 eq.), 3,6-difluoro-10-phenylacridin-9(10H)-one (1 eq.), and cesium carbonate (5 eq.) were dissolved in DMSO and then stirred at approximately 160°C under a nitrogen atmosphere for approximately 24 hours. After cooling, the reaction solution was washed five times with ethyl acetate and water, and the resulting organic layer was dried over anhydrous MgSO4 and dried under reduced pressure. Intermediate 3-4b was obtained by column chromatography (yield: 35%).

[0284] (3) Synthesis of Compound 3-4

[0285] BBr3 (5 eq.) was dissolved in o-dichlorobenzene, the flask was cooled to about 0°C under a nitrogen atmosphere, and the intermediate 3-4b (1 eq.) dissolved in o-dichlorobenzene was slowly added over about an hour. After the addition was completed, stirring was performed at room temperature for about 2 hours, and the reaction solution was cooled to about 0°C. Then, diisopropylethylamine (15 eq.) was added thereto. After the addition, the temperature was raised to about 160°C and stirring was performed for about 24 hours. After the reaction was completed, hexane was added thereto for precipitation. Filter and obtain a solid component. The solid component thus obtained was separated by column chromatography, and further separated by recrystallization with MC / Hex to obtain compound 3-4 (yield: 15%).

[0286] Example compounds

[0287]

[0288]

[0289] An organic electroluminescent device of a comparative example was manufactured by using the comparative compound as a material for an emission layer.

[0290] Comparative compounds

[0291]

[0292] The organic electroluminescent device of the example and the organic electroluminescent device of the comparative example were respectively manufactured by the methods described below.

[0293] On a glass substrate, there will be approximately The ITO was patterned with a thickness of , washed with ultrapure water and treated with UV-ozone for about 30 minutes. Then, NPD was vacuum deposited to a thickness of about to form a hole injection layer, and TATA was vacuum deposited to a thickness of about The hole transport layer is formed by vacuum depositing the compound CzSi to a thickness of about thickness.

[0294] Then, the polycyclic compound of the example or the comparative compound was co-deposited with mCP at a ratio of 1:99 to form a The thickness of the emission layer.

[0295] On the emission layer, TSPO1 is used to form a A layer with a thickness of about 1000 nm was formed as an electron transport layer, and TPBi was used as an electron injection layer compound to form a layer with a thickness of about 1000 nm. On the electron transport layer, alkali metal halide LiF is deposited to a thickness of about The thickness of the electron injection layer was 1000 nm, and Al was vacuum deposited to a thickness of about 1000 nm. A thickness of 1000 nm was used to form a LiF / Al electrode, thereby manufacturing an organic electroluminescent device.

[0296] (Evaluation of Performance of Organic Electroluminescent Devices)

[0297] In order to evaluate the performance of the organic electroluminescent devices of Examples and Comparative Examples, the luminance of the organic electroluminescent devices was measured at a luminance of about 1,000 cd / m 2 Maximum emission wavelength (nm) and external quantum efficiency (e.g., emission efficiency) (%) under .

[0298] Table 1

[0299]

[0300] Referring to the results of Table 1, it can be confirmed that when the polycyclic compound according to the embodiment is included in the emission layer, external quantum efficiency is improved when compared with the comparative example.

[0301] Since the polycyclic compound according to the embodiment has a wide plate-like skeleton, the multiple resonance effect can be further activated, and a high-level orientation ratio of the transition dipole moment of the dopant can be achieved in the host matrix of the emission layer. Therefore, ΔE can be further reduced. ST (For example, it represents the difference between the lowest singlet excitation energy level (S1 level) and the lowest triplet excitation energy level (T1 level)), and the emission efficiency can be improved.

[0302] The organic electroluminescent device according to the embodiment of the present disclosure can achieve high efficiency and long lifespan.

[0303] The polycyclic compound according to an embodiment of the present disclosure may improve the lifespan and efficiency of an organic electroluminescent device.

[0304] When describing embodiments of the present invention, the use of “may” refers to “one or more embodiments of the present invention.” Additionally, the term “exemplary” is intended to indicate an example or illustration.

[0305] As used herein, the terms "substantially", "approximately" and similar terms are used as approximate terms rather than as terms of degree, and are intended to explain the inherent deviations of measured or calculated values ​​that will be recognized by those of ordinary skill in the art. In addition, any numerical range stated herein is intended to include all subranges of the same numerical precision contained within the stated range. For example, the range of "1.0 to 10.0" is intended to include all subranges between the stated minimum value 1.0 and the stated maximum value 10.0 (and including the stated minimum value 1.0 and the stated maximum value 10.0), that is, 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 stated herein is intended to include all smaller numerical limits contained therein, and any minimum numerical limit stated in this specification is intended to include all larger numerical limits contained therein. Therefore, the applicant reserves the right to amend this specification (including claims) to explicitly state any subrange contained within the range explicitly stated herein. All such ranges are intended to be inherently described in this specification, such that amendment to expressly recite any such sub-ranges would be satisfactory.

[0306] Although exemplary embodiments of the present invention have been described, it is understood that the present invention is not limited to these exemplary embodiments, but various suitable changes and modifications can be made by one skilled in the art within the spirit and scope of the present invention as claimed and its equivalents.

Claims

1. An organic electroluminescent device, comprising: a first electrode; an organic layer, located on the first electrode; as well as a second electrode, located on the organic layer; Wherein, the organic layer includes a polycyclic compound represented by the following Formula 1: Formula 1 In formula 1, X1 to X4 are independently NR9, O or S, R1 to R8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, 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, R9 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and optionally, R9 combines with an adjacent group to form a ring, a to f are each independently an integer from 0 to 4, m and n are independently 0 or 1, Dashed lines represent bonds or nonbonds, and Ring A is represented by any one selected from the following Formula 2-1 to Formula 2-3: Among them, in formula 2-1 to formula 2-3, * indicates the binding site with the adjacent atom, X5 and X6 are independently CR 30 R 31 NR 32 , O or S, R 30 to R 32 are independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms, and R 20 to R 29 are independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms, and When ring A is represented by Formula 2-1 or Formula 2-2, at least one selected from m and n is 1.

2. The organic electroluminescent device according to claim 1, wherein The organic layer comprises: a hole transport region, located on the first electrode; an emission layer located on the hole transport region; and The electron transport region is located on the emission layer.

3. The organic electroluminescent device according to claim 2, wherein: The emission layer includes the polycyclic compound and emits delayed fluorescence.

4. The organic electroluminescent device according to claim 3, wherein The emission layer is a delayed fluorescent emission layer including a host and a dopant, and The dopant is the polycyclic compound.

5. The organic electroluminescent device according to claim 3, wherein The emission layer is a thermally activated delayed fluorescent emission layer to emit blue light. The organic electroluminescent device according to claim 2 , wherein: The electron transport region includes: an electron transport layer located on the emission layer; and an electron injection layer located on the electron transport layer, and Wherein, the electron transport layer or the electron injection layer includes the polycyclic compound.

7. The organic electroluminescent device according to claim 1, wherein Formula 2-2 is expressed by any one selected from the following Formulas 3-1 to 3-4: and Among them, in formula 3-1 to formula 3-4, * indicates the binding site with the adjacent atom, R 30 、R 31 and R 33 are independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, and j is an integer from 0 to 5.

8. The organic electroluminescent device according to claim 1, wherein Formula 2-3 is expressed by any one selected from the following Formulas 4-1 to 4-3: Formula 4-3 and Among them, in formula 4-1 to formula 4-3, * indicates the binding site with the adjacent atom, R 34 is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, and k is an integer from 0 to 5.

9. The organic electroluminescent device according to claim 1, wherein The polycyclic compound represented by Formula 1 is represented by the following Formula 5-1 or Formula 5-2: Formula 5-1 Formula 5-2 and Among them, in formula 5-1 and formula 5-2, X1 to X4, R1 to R8, R 20 、R 21 and a to f are the same as those defined in combination with Formula 1 and Formula 2-1, respectively.

10. The organic electroluminescent device according to claim 1, wherein The polycyclic compound represented by Formula 1 is represented by the following Formula 6-1 or Formula 6-2: Formula 6-1 Formula 6-2 and Among them, in formula 6-1 and formula 6-2, X1 to X5, R1 to R8, R 22 to R 25 and a to f are the same as those defined in combination with Formula 1 and Formula 2-2, respectively. The organic electroluminescent device according to claim 1 , wherein: The polycyclic compound represented by Formula 1 is represented by any one selected from the following Formulas 7-1 to 7-3: Formula 7-1 Formula 7-2 Formula 7-3 and Among them, in formula 7-1 to formula 7-3, X1 to X4, X6, R1 to R8, R 26 to R 29 and a to f are the same as those defined in Formula 1 and Formula 2-3, respectively.

12. The organic electroluminescent device according to claim 1, wherein: X1 to X4 are independently NR 11 or O; and R 11 It is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

13. The organic electroluminescent device according to claim 1, wherein: X1 and X4 are identical; and X2 and X3 are the same.

14. The organic electroluminescent device according to claim 1, wherein The polycyclic compound represented by Formula 1 is any one selected from the compounds represented by the following Compound Group 1 to Compound Group 3: Compound Group 1 Compound Group 2 Compound Group 3 15. A polycyclic compound, said polycyclic compound being represented by the following formula 1: Formula 1 in, In formula 1, X1 to X4 are independently NR9, O or S, R1 to R8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, 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, R9 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and optionally, R9 combines with an adjacent group to form a ring, a to f are each independently an integer from 0 to 4, m and n are independently 0 or 1, Dashed lines represent bonds or nonbonds, and Ring A is represented by any one selected from the following Formula 2-1 to Formula 2-3: Among them, in formula 2-1 to formula 2-3, * indicates the binding site with the adjacent atom, X5 and X6 are independently CR 30 R 31 NR 32 , O or S, R 30 to R 32 are independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms, and R 20 to R 29 are independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms, and When ring A is represented by Formula 2-1 or Formula 2-2, at least one selected from m and n is 1.

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