Organic electroluminescent device and polycyclic compound for organic electroluminescent device

Abstract

The present application relates to an organic electroluminescent device, including a first electrode, a second electrode, and an emission layer between the first electrode and the second electrode, wherein the emission layer contains a polycyclic compound represented by the following formula 1 and exhibits high emission efficiency: Formula 1

Description

[0001] Cross - reference to related applications

[0002] This application claims priority and the benefit of Korean Patent Application No. 10 - 2019 - 0092407, filed on Jul. 30, 2019, the entire content of which is incorporated herein by reference. Technical field

[0003] One or more aspects of embodiments of the present disclosure relate to an organic electroluminescent device and a polycyclic compound used therein, and more particularly, to a polycyclic compound used as a light - emitting material and an organic electroluminescent device including the polycyclic compound. Background art

[0004] Recently, the development of organic electroluminescent display devices as image display devices has been actively carried out. Different from liquid crystal display devices, organic electroluminescent display devices are self - emissive display devices, in which holes and electrons injected from a first electrode and a second electrode are recombined in an emission layer, and a light - emitting material containing an organic compound in the emission layer emits light to achieve image display.

[0005] In the application of organic electroluminescent devices to display devices, a reduction in the driving voltage of the organic electroluminescent device, as well as an increase in emission efficiency and lifespan, are required (or desired), and the development of materials for organic electroluminescent devices capable of stably achieving these characteristics is constantly being sought.

[0006] In particular, recently, in order to realize an organic electroluminescent device with high efficiency, technologies based on phosphorescent emission (which uses the energy in the triplet state) or delayed fluorescence emission (which uses the phenomenon of singlet exciton generation through triplet exciton collision (triplet - triplet annihilation, TTA)) are being developed, and the development of materials for thermally activated delayed fluorescence (TADF) using the delayed fluorescence phenomenon is being carried out. Summary of the invention

[0007] One or more aspects of embodiments of the present disclosure relate to an organic electroluminescent device that exhibits excellent (suitable) emission efficiency.

[0008] The present disclosure also provides a polycyclic compound, which is a material for an organic electroluminescent device having high - efficiency properties.

[0009] Embodiments of the present disclosure provide a polycyclic compound represented by the following formula 1:

[0010] Formula 1

[0011]

[0012] In Formula 1, Ar1 to Ar4 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, R a to R f are each independently a hydrogen atom, a deuterium atom, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, a substituted or unsubstituted oxy group, or a substituted or unsubstituted thio group. "a", "c", "d", and "f" are each independently an integer from 0 to 4, and "b" and "e" are each independently an integer from 0 to 3.

[0013] In embodiments where Ring A1 and Ring A2 are linked via L, L can be O, S, BR p 、NR q 、(P═O)R s 、(P═S)R t 、(C═O), a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.

[0014] In embodiments where Ring A3 and Ring A4 are linked via L, L can be a direct bond, O, S, BR p 、NR q 、(P═O)R s 、(P═S)R t 、(C═O), a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms, provided that L is not a phenylene group substituted with a carbazole group.

[0015] In embodiments where Ring H1 and Ring H2 are linked via L, L connects Ar1 and Ar3 to each other, and L can be a direct bond, O, S, BR p 、NR q 、(P═O)R s 、(P═S)R t 、(C═O), a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms, and

[0016] R p 、R q 、R s and R tEach independently may be a hydrogen atom, a deuterium atom, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, a substituted or unsubstituted oxy group, or a substituted or unsubstituted thio group.

[0017] In an embodiment, Ar1 to Ar4 may each independently be a substituted or unsubstituted phenyl group.

[0018] In an embodiment, Formula 1 may be represented by any one of the following Formulas 1-1 to 1-3:

[0019] Formula 1-1

[0020]

[0021] Formula 1-2

[0022]

[0023] Formula 1-3

[0024]

[0025] In Formulas 1-1 to 1-3, Ar1 to Ar4, R a to R f ,"a" to "f", and L are the same as defined in Formula 1.

[0026] In an embodiment, Formula 1 may be represented by the following Formula 2:

[0027] Formula 2

[0028]

[0029] In Formula 2, R g , R h , R i and R j may each independently be a hydrogen atom, a deuterium atom, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, a substituted or unsubstituted oxy group, or a substituted or unsubstituted thio group, "g", "h", "i", and "j" may each independently be an integer from 0 to 5, and L, R a to R f and "a" to "f" are the same as defined in Formula 1.

[0030] In Formula 1, L may be a direct bond or may be represented by any one of the following Formulas L1 to L9:

[0031]

[0032] In Formulas L1 to L9, R m may be a hydrogen atom, a deuterium atom, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted oxy group, or a substituted or unsubstituted thio group, provided that R in Formula L1 m is not a substituted or unsubstituted carbazole group.

[0033] In an embodiment, Formula 1-1 may be represented by any one of the following Formulas 1-1A to 1-1O:

[0034]

[0035]

[0036] In Formulas 1-1A to 1-1O, R1 to R 22 and R1' to R 21 ' may each independently be a hydrogen atom, a deuterium atom, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted oxy group, or a substituted or unsubstituted thio group.

[0037] In an embodiment, Formula 1-2 may be represented by any one of the following Formulas 1-2A to 1-2E:

[0038]

[0039] In Formulas 1-2A to 1-2E, R1 to R 22 and R1' to R 21 ' may each independently be a hydrogen atom, a deuterium atom, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted oxy group, or a substituted or unsubstituted thio group, provided that R in Formula 1-2B 22 is not a substituted or unsubstituted carbazole group.

[0040] In an embodiment, Formula 1-3 may be represented by any one of the following Formulas 1-3A to 1-3F:

[0041]

[0042] In Formulas 1-3A to 1-3F, R1 to R 22 and R1' to R 21 ' may each independently be a hydrogen atom, a deuterium atom, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted oxy group, or a substituted or unsubstituted thio group.

[0043] In an embodiment, the polycyclic compound represented by Formula 1 may be a blue dopant that emits blue light having a central wavelength of about 470 nm or less than 470 nm.

[0044] In an embodiment of the present disclosure, an organic electroluminescent device is provided. The organic electroluminescent device includes a first electrode; a second electrode on the first electrode; and an emission layer between the first electrode and the second electrode and containing the polycyclic compound of the embodiment. Each of the first electrode and the second electrode independently contains: one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, In, Sn, and Zn; a compound selected from two or more of them; a mixture selected from two or more of them; and oxides of the foregoing substances.

[0045] In an embodiment, the emission layer may be intended to emit delayed fluorescence.

[0046] In an embodiment, the emission layer may contain a host and a dopant, and the dopant may include the polycyclic compound.

[0047] In an embodiment, the emission layer may emit light having a central wavelength of about 430 nm to about 470 nm. BRIEF DESCRIPTION OF THE DRAWINGS

[0048] The drawings are included to provide a further understanding of the present disclosure and are incorporated into and constitute a part of this specification. The drawings illustrate exemplary embodiments of the present disclosure and, together with the description, are used to explain the principles of the present disclosure. In the drawings:

[0049] Figure 1 is a cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present disclosure;

[0050] Figure 2is a cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present disclosure;

[0051] Figure 3 is a cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present disclosure; and

[0052] Figure 4 is a cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present disclosure. Detailed Description

[0053] The present disclosure may have various modifications and may be implemented in different forms, and exemplary embodiments will be explained in more detail with reference to the accompanying drawings. However, the present disclosure may be implemented in different forms and should not be construed as being limited to the embodiments set forth herein. On the contrary, all modifications, equivalents, and alternatives included within the spirit and technical scope of the present disclosure should be included in the present disclosure.

[0054] It should 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, directly connected to, or directly coupled to the other element (without any intervening third element), or there may be one or more intervening third elements.

[0055] The same reference numerals refer to the same elements throughout. In addition, in the drawings, the thickness, ratio, and / or dimensions of the constituent elements may be enlarged for effective explanation of the technical content.

[0056] The term "and / or" includes one or more combinations that can be defined by the related elements. Expressions such as "at least one (kind) of...", "one (kind) of...", and "selected from..." when preceding a list of elements modify the entire list of elements, rather than individual elements in the list. In addition, when describing embodiments of the present disclosure, the use of "may" means "one or more embodiments of the present disclosure".

[0057] It should be understood that although terms such as first, second, etc. may be used herein to describe various elements, these elements should not be limited by these terms. These terms are only used to distinguish one element from another. Thus, without departing from the teachings of the present disclosure, a first element may be referred to as a second element. Similarly, a second element may be referred to as a first element. As used herein, the singular form is also intended to include the plural form unless the context clearly indicates otherwise.

[0058] In addition, the terms "below", "beneath", "above", and "on" are used to explain the relationship of elements shown in the drawings. The terms are relative concepts and are interpreted based on the directions shown in the drawings.

[0059] 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 this invention belongs. It should be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that conforms to their meaning in the context of the relevant art and should not be interpreted in an idealized or overly formal sense unless expressly so defined herein.

[0060] It should be further understood that the terms "comprises" and / or "comprising", when used in this specification, specify the presence of the stated features, integers, steps, operations, elements, components, or combinations thereof, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.

[0061] Hereinafter, an organic electroluminescent device according to an embodiment of the present disclosure will be explained with reference to the drawings.

[0062] Figures 1 to 4 is a cross-sectional view schematically showing an organic electroluminescent device according to an embodiment of the present disclosure. Referring to Figures 1 to 4 , in an organic electroluminescent device 10 according to an embodiment, a first electrode EL1 and a second electrode EL2 are relatively positioned, and an emission layer EML may be disposed between the first electrode EL1 and the second electrode EL2.

[0063] In some embodiments, in addition to the emission layer EML, the organic electroluminescent device 10 of the embodiment further includes a plurality of functional groups (functional layers) between the first electrode EL1 and the second electrode EL2. The plurality of functional groups (functional layers) may include a hole transport region HTR and an electron transport region ETR. For example, 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 laminated one by one. In some embodiments, the organic electroluminescent device 10 may include a cover layer CPL on the second electrode EL2.

[0064] The organic electroluminescent device 10 of the embodiment may include the polycyclic compound of the embodiment, which will be explained in more detail later, in the emission layer EML between the first electrode EL1 and the second electrode EL2. However, the embodiment of the present disclosure is not limited thereto, and the organic electroluminescent device 10 of the embodiment may include the polycyclic compound of the embodiment in the hole transport region HTR and / or the electron transport region ETR, where the hole transport region HTR and / or the electron transport region ETR are multiple functional groups (functional layers) between the first electrode EL1 and the second electrode EL2.

[0065] Meanwhile, when compared with Figure 1 compared to Figure 2 shows a cross-sectional view of the organic electroluminescent device 10 of the embodiment, where 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. When compared with Figure 1 compared to Figure 3 shows a cross-sectional view of the organic electroluminescent device 10 of the embodiment, where the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL, and an electron blocking layer EBL; and the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL, and a hole blocking layer HBL. When compared with Figure 2 compared to Figure 4 shows a cross-sectional view of the organic electroluminescent device 10 of the embodiment, which includes a cover layer CPL on the second electrode EL2.

[0066] The first electrode EL1 has conductivity. The first electrode EL1 can be formed using a metal alloy or a suitable conductive compound. The first electrode EL1 can be an anode. The first electrode EL1 can be a pixel electrode. The first electrode EL1 can be a transmissive electrode, a transflective electrode, or a reflective electrode. If 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)). If 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, their compounds, or a mixture thereof (e.g., a mixture of Ag and Mg). Additionally, the first electrode EL1 can have a structure including multiple layers, the multiple layers including a reflective layer and / or a transflective layer formed using any of the above materials, and a transmissive conductive layer formed using ITO, IZO, ZnO, and / or ITZO. For example, the first electrode EL1 can 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 can be about to about For example, about to about

[0067] A hole transport region HTR is provided on the first electrode EL1. The hole transport region HTR can include at least one selected from a hole injection layer HIL, a hole transport layer HTL, a hole buffer layer, and an electron blocking layer EBL. The thickness of the hole transport region HTR can be about to about

[0068] The hole transport region HTR can 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.

[0069] For example, the hole transport region HTR can have a structure of a single layer of a hole injection layer HIL or a hole transport layer HTL, or can have a structure of a single layer formed using a hole injection material and a hole transport material. In some embodiments, the hole transport region HTR can have a structure of a single layer formed using multiple 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 laminated from the first electrode EL1, but is not limited thereto.

[0070] One or more suitable methods (e.g., vacuum deposition method, spin coating method, casting method, Langmuir-Blodgett (LB) method, inkjet printing method, laser printing method, and / or laser-induced thermal imaging (LITI) method) can be used to form the hole transport region HTR.

[0071] The hole injection layer HIL can include, for example, phthalocyanine compounds (e.g., copper phthalocyanine), N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-phenyl-4,4'-diamine (DNTPD), 4,4',4''-[tris(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4''-tris{N-(2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (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 (NPB), triphenylamine-containing polyether ketone (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).

[0072] The hole transport layer HTL can include, for example, carbazole derivatives (e.g., N-phenylcarbazole and / or polyvinylcarbazole), fluorene-based derivatives, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), triphenylamine-based derivatives (e.g., 4,4',4''-tris(N-carbazolyl)triphenylamine (TCTA)), N,N'-di(1-naphthyl)-N,N'-diphenyl-benzidine (NPB), 4,4'-cyclohexylidenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), 1,3-bis(N-carbazolyl)benzene (mCP), etc.

[0073] The thickness of the hole transport region HTR can 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 can be about to about When the thicknesses of the hole transport region HTR, hole injection layer HIL, hole transport layer HTL, and electron blocking layer EBL satisfy any of the ranges described above, satisfactory (suitable) hole transport properties can be achieved without a significant increase in the driving voltage.

[0074] In addition to the materials described above, the hole transport region HTR can further include a charge generation material to increase conductivity. The charge generation material can be uniformly or non-uniformly dispersed in the hole transport region HTR. The charge generation material can be, for example, a p-dopant. The p-dopant can be one selected from quinone derivatives, metal oxides, and compounds containing a cyano group, but is not limited thereto. Non-limiting examples of the p-dopant can include quinone derivatives (such as tetracyanoquinodimethane (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7’,8,8’-tetracyanoquinodimethane (F4-TCNQ)) and metal oxides (such as tungsten oxide and / or molybdenum oxide), but are not limited thereto.

[0075] As described above, in addition to the hole injection layer HIL and the hole transport layer HTL, the hole transport region HTR can further include at least one selected from a hole buffer layer and an electron blocking layer EBL. The hole buffer layer can compensate for the optical resonance distance according to the wavelength of the light emitted from the emission layer EML and can increase the light emission efficiency. The materials that can be included in the hole transport region HTR can be used as the materials included in the hole buffer layer. The electron blocking layer EBL is a layer that functions to prevent or reduce the injection of electrons from the electron transport region ETR to the hole transport region HTR.

[0076] An emission layer EML is provided on the hole transport region HTR. The emission layer EML can have, for example, a thickness of about to about or about to about The emission layer EML can have a single layer formed of a single material, a single layer formed of multiple different materials, or a multilayer structure having multiple layers formed of multiple different materials.

[0077] In the organic electroluminescent device 10 of the embodiment, the emission layer EML can include the polycyclic compound of the embodiment.

[0078] In the present description, the term "substituted or unsubstituted" corresponds to an unsubstituted group or a group 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, a silyl group, an oxy group, a thio 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 (e.g., a heterocycle). In addition, each of the exemplified substituents may itself 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.

[0079] In the description, the term "forming a ring by bonding to an adjacent group" may refer to forming a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle by the bonding of one group to an adjacent group. The hydrocarbon ring includes an aliphatic hydrocarbon ring and an aromatic hydrocarbon ring. The heterocycle includes an aliphatic heterocycle and an aromatic heterocycle. The ring formed by bonding to an adjacent group may be a monocyclic or polycyclic ring. In some embodiments, the ring formed by bonding to an adjacent group may be bonded to another ring to form a spiro structure.

[0080] In the description, the term "adjacent group" may refer to: a pair of substituent groups in which a first substituent is connected to an atom directly connected to another atom substituted with a second substituent; a pair of substituent groups connected to the same atom; or a pair of substituent groups in which a first substituent is spatially located at the position closest to a second 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.

[0081] In the description, the halogen atom may be a fluorine atom, a chlorine atom, a bromine atom, and / or an iodine atom.

[0082] In the description, the alkyl group can be a straight-chain, branched-chain or cyclic alkyl group. The number of carbon atoms in the alkyl group can be 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6. Examples of the alkyl group can 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-butyl octyl, 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-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, etc., but are not limited thereto.

[0083] In the description, the hydrocarbon ring can refer to an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring having 5 to 60, 5 to 30 or 5 to 20 carbon atoms for forming the ring. The hydrocarbon ring can be a functional group or a substituent derived from an aliphatic hydrocarbon ring, or a functional group or a substituent derived from an aromatic hydrocarbon ring. The number of carbon atoms in the hydrocarbon ring for forming the ring can be 5 to 60, 5 to 30 or 5 to 20.

[0084] In the description, the aryl group can refer to a functional group or a substituent derived from an aromatic hydrocarbon ring. The aryl group can be a monocyclic aryl group or a polycyclic aryl group. The number of carbon atoms in the aryl group for forming the ring can be 6 to 30, 6 to 20 or 6 to 15. Examples of the aryl group can include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, quaterphenyl, quinquephenyl, sexiphenyl, benzo[a]pyrenyl, pyrenyl, benzo[a]fluoranthenyl, yl, etc., but are not limited thereto.

[0085] In the description, a heterocyclic group (heterocycle) may refer to a functional group or substituent derived from a ring containing one or more heteroatoms selected from B, O, N, P, Si, and S. Heterocyclic groups include aliphatic heterocyclic groups and aromatic heterocyclic groups. The aromatic heterocyclic group may be a heteroaryl group. The aliphatic heterocycle and the aromatic heterocycle may each independently be monocyclic or polycyclic.

[0086] In the description, a heterocycle may contain one or more selected from B, O, N, P, Si, and S as heteroatoms. If the heterocycle contains two or more heteroatoms, the two or more heteroatoms may be the same or different. The heterocycle may be a monocyclic heterocycle or a polycyclic heterocycle and has a concept including heteroaryl. The number of carbon atoms for forming the ring of the heterocycle (e.g., heteroaryl) may be 2 to 30, 2 to 20, or 2 to 10.

[0087] In the description, an aliphatic heterocyclic group may contain one or more selected from B, O, N, P, Si, and S as heteroatoms. The number of carbon atoms for forming the ring of the aliphatic heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10. Examples of the aliphatic heterocyclic group may include an oxiranyl group, a thiiranyl group, a pyrrolidinyl group, a piperidine group, a tetrahydrofuran group, a tetrahydrothiophene group, a thiacyclohexyl group, a tetrahydropyran group, a 1,4-dioxanyl group, etc., but are not limited thereto.

[0088] In the description, a heteroaryl group may contain one or more of B, O, N, P, Si, and S as heteroatoms. If the heteroaryl group contains two or more heteroatoms, the two or more heteroatoms may be the same or different. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. The number of carbon atoms for forming the ring of the heteroaryl group may be 2 to 30, 2 to 20, or 2 to 10. Examples of the heteroaryl group may include groups derived from the following: thiophene, furan, pyrrole, imidazole, triazole, pyridine, bipyridine, pyrimidine, triazine, acridine, pyridazine, pyrazine, quinoline, quinazoline, quinoxaline, phenoxazine, phthalazine, pyridopyrimidine, pyridopyrazine, pyrazinopyrazine, isoquinoline, indole, carbazole, N-arylcarbazole, N-heteroarylcarbazole, N-alkylcarbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophene, dibenzothiophene, thienothiophene, benzofuran, phenanthroline, thiazole, isoxazole, oxazole, oxadiazole, thiadiazole, phenothiazine, dibenzosilole, dibenzofuran, etc., but are not limited thereto.

[0089] In the description, a thio group may include an alkylthio group and an arylthio group.

[0090] In the description, the oxy group may include an alkoxy group and an aryloxy group. The alkoxy group may be a straight-chain, branched-chain, or cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but may be, for example, 1 to 20 or 1 to 10. Examples of the oxy group may include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, benzyloxy, and the like. However, the embodiments of the present disclosure are not limited thereto.

[0091] In the description, the direct bond may refer to a single bond.

[0092] Meanwhile, in the description, refers to the connection position.

[0093] In the description, the "atom for forming a ring" may refer to a ring-forming atom.

[0094] The emission layer EML of the organic electroluminescent device 10 of the embodiment may include a polycyclic compound of the embodiment represented by the following formula 1:

[0095] Formula 1

[0096]

[0097] In Formula 1, Ar1 to Ar4 may be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring. In Formula 1, R a to R f may each independently be a hydrogen atom, a deuterium atom, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted oxy group, or a substituted or unsubstituted thio group. In Formula 1, "a", "c", "d", and "f" may each independently be an integer from 0 to 4, and "b" and "e" may each independently be an integer from 0 to 3.

[0098] The polycyclic compound of the embodiment represented by Formula 1 may have a combined structure of two polycyclic aromatic groups connected to each other by a linker L. In the embodiment, the polycyclic aromatic group may include a core portion represented by the following formula 1A:

[0099] Formula 1A

[0100]

[0101] The two polycyclic aromatic groups linked by L can be symmetric with respect to L. L can be linked to any one of the three rings constituting the azaborine moiety in the core part of the polycyclic aromatic group that can be represented by Formula 1A (as represented by in Formula 1A).

[0102] In Formula 1, in embodiments where each of "a" to "f" is an integer of 2 or greater than 2, multiple ones of R a to R f can be the same or at least one of them can be different from the rest.

[0103] In the polycyclic compound of the embodiment represented by Formula 1, in embodiments where ring A1 and ring A2 are linked via L, L can be O, S, BR p , NR q , (P═O)R s , (P═S)R t , (C═O), a substituted or unsubstituted arylene group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms for forming a ring.

[0104] In Formula 1, in embodiments where ring A3 and ring A4 are linked via L, L can be a direct bond, O, S, BR p , NR q , (P═O)R s , (P═S)R t , (C═O), a substituted or unsubstituted arylene group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms for forming a ring. Meanwhile, in embodiments where ring A3 and ring A4 are linked via L, the case where L is a phenylene group substituted with a substituted or unsubstituted carbazole group is excluded.

[0105] In Formula 1, in embodiments where ring H1 and ring H2 are linked via L, L connects Ar1 and Ar3 to each other, and L can be a direct bond, O, S, BR p , NR q , (P═O)R s , (P═S)R t , (C═O), a substituted or unsubstituted arylene group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms for forming a ring.

[0106] In cases where L is BR p , NR q , (P═O)Rs or (P = S)R t In the embodiments where p R q R s R t and R can each independently be a hydrogen atom, a deuterium atom, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted oxy group, or a substituted or unsubstituted thio group.

[0107] In the polycyclic compound of the embodiment represented by Formula 1, Ar1 to Ar4 can each independently be a substituted or unsubstituted benzene ring (for example, a substituted or unsubstituted phenyl group). In the substituted benzene ring (phenyl group), the benzene ring can be substituted with at least one selected from a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring.

[0108] In Formula 1, L can be a direct bond or can be represented by any one of Formulas L1 to L9. The direct bond can be a single bond. In Formula 1, in the embodiments where ring A1 and ring A2 are connected via L, L can be represented by any one of Formulas L1 to L9, excluding the case where L is a direct bond. In the polycyclic compound represented by Formula 1, in the embodiments where ring A3 and ring A4 are connected via L, or in the embodiments where ring H1 and ring H2 are connected via L, L can be a direct bond or can be represented by any one of the following Formulas L1 to L9.

[0109]

[0110] In Formulas L1 to L9, R m can be a hydrogen atom, a deuterium atom, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted oxy group, or a substituted or unsubstituted thio group. If L is represented by Formula L1, the case where R m is a substituted or unsubstituted carbazole group can be excluded.

[0111] Formula 1 can be represented by the following Formula 2:

[0112] Formula 2

[0113]

[0114] In Formula 2, Rg , R h , R i and R j may each independently be a hydrogen atom, a deuterium atom, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, a substituted or unsubstituted oxy group, or a substituted or unsubstituted thio group, and "g", "h", "i", and "j" may each independently be an integer from 0 to 5.

[0115] In Formula 2, in embodiments where each of "g" to "j" is an integer of 2 or greater than 2, R g to R j among a plurality of them may be the same or at least one of them may be different from the rest.

[0116] In Formula 2, the same explanations (descriptions) as those provided for L, R a to R f and "a" to "f" can be applied.

[0117] Formula 1 may be represented by any one of the following Formulas 1-1 to 1-3:

[0118] Formula 1-1

[0119]

[0120] Formula 1-2

[0121]

[0122] Formula 1-3

[0123]

[0124] In Formulas 1-1 to 1-3, the same explanations (descriptions) as those provided for Ar1 to Ar4, R a to R f , "a" to "f", and L can be applied.

[0125] The polycyclic compound of the embodiment represented by Formula 1-1 may be represented by any one of the following Formulas 1-1A to 1-1O:

[0126]

[0127]

[0128] In Formulas 1-1A to 1-1O, R1 to R 22 and R1' to R21 ' may each independently be a hydrogen atom, a deuterium atom, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, a substituted or unsubstituted oxy group, or a substituted or unsubstituted thio group. For example, R1 to R 22 and R1' to R 21 ' may each independently be a hydrogen atom, a methyl group, an isopropyl group, a tert-butyl group, a phenyl group, etc., but the embodiments of the present disclosure are not limited thereto.

[0129] Formula 1-1A can be represented by the following Formula 1-1A'.

[0130] Formula 1-1A'

[0131]

[0132] According to the combinations of substituents shown in Table 1 below, the polycyclic compounds represented by Formula 1-1A' can be represented by Compounds 1-1A-1 to 1-1A-9. In Table 1, H represents a hydrogen atom, Me represents a methyl group, iPr represents an isopropyl group, tBu represents a tert-butyl group, and Ph represents a phenyl group.

[0133] Table 1

[0134] Compound number <![CDATA[R b > <![CDATA[R c > <![CDATA[R h > <![CDATA[R m > <![CDATA[R e > <![CDATA[R f > <![CDATA[R j > 1-1A-1 H H H H H H H 1-1A-2 H Me Me H H Me Me 1-1A-3 H iPr iPr H H iPr iPr 1-1A-4 H tBu tBu H H tBu tBu 1-1A-5 H Ph Ph H H Ph Ph 1-1A-6 Me Me Me H Me Me Me 1-1A-7 Me iPr iPr H Me iPr iPr 1-1A-8 Me tBu tBu H Me tBu tBu 1-1A-9 Me Ph Ph H Me Ph Ph

[0135] Formula 1-1B can be represented by the following Formula 1-1B'.

[0136] Formula 1-1B'

[0137]

[0138] According to the combinations of substituents shown in Table 2 below, the polycyclic compounds represented by Formula 1-1B' can be represented by Compounds 1-1B-1 to 1-1B-9. In Table 2, H represents a hydrogen atom, Me represents a methyl group, iPr represents an isopropyl group, tBu represents a tert-butyl group, and Ph represents a phenyl group.

[0139] Table 2

[0140] Compound number <![CDATA[R b > <![CDATA[R c > <![CDATA[R h > <![CDATA[R m > <![CDATA[R e > <![CDATA[R f > <![CDATA[R j > 1-1B-1 H H H H H H H 1-1B-2 H Me Me H H Me Me 1-1B-3 H iPr iPr H H iPr iPr 1-1B-4 H tBu tBu H H tBu tBu 1-1B-5 H Ph Ph H H Ph Ph 1-1B-6 Me Me Me H Me Me Me 1-1B-7 Me iPr iPr H Me iPr iPr 1-1B-8 Me tBu tBu H Me tBu tBu 1-1B-9 Me Ph Ph H Me Ph Ph

[0141] Formula 1-1C can be represented by the following Formula 1-1C'.

[0142] Formula 1-1C'

[0143]

[0144] According to the combinations of substituents shown in Table 3 below, the polycyclic compounds represented by Formula 1-1C’ can be represented by Compounds 1-1C-1 to 1-1C-10. In Table 3, H represents a hydrogen atom, Me represents a methyl group, iPr represents an isopropyl group, tBu represents a tert-butyl group, and Ph represents a phenyl group.

[0145] Table 3

[0146] Compound number <![CDATA[R b > <![CDATA[R c > <![CDATA[R h > <![CDATA[R m > <![CDATA[R e > <![CDATA[R f > <![CDATA[R j > 1-1C-1 H H H H H H H 1-1C-2 H Me Me H H Me Me 1-1C-3 H H H Me H H H 1-1C-4 H iPr iPr H H iPr iPr 1-1C-5 H tBu tBu H H tBu tBu 1-1C-6 H Ph Ph H H Ph Ph 1-1C-7 Me Me Me H Me Me Me 1-1C-8 Me iPr iPr H Me iPr iPr 1-1C-9 Me tBu tBu H Me tBu tBu 1-1C-10 Me Ph Ph H Me Ph Ph

[0147] Formula 1-1D can be represented by the following Formula 1-1D’.

[0148] Formula 1-1D’

[0149]

[0150] According to the combinations of substituents shown in Table 4 below, the polycyclic compounds represented by Formula 1-1D’ can be represented by Compounds 1-1D-1 to 1-1D-10. In Table 4, H represents a hydrogen atom, Me represents a methyl group, iPr represents an isopropyl group, tBu represents a tert-butyl group, and Ph represents a phenyl group.

[0151] Table 4

[0152] Compound number <![CDATA[R b > <![CDATA[R c > <![CDATA[R h > <![CDATA[R m > <![CDATA[R e > <![CDATA[R f > <![CDATA[R j > 1-1D-1 H H H H H H H 1-1D-2 H Me Me H H Me Me 1-1D-3 H H H Me H H H 1-1D-4 H iPr iPr H H iPr iPr 1-1D-5 H tBu tBu H H tBu tBu 1-1D-6 H Ph Ph H H Ph Ph 1-1D-7 Me Me Me H Me Me Me 1-1D-8 Me iPr iPr H Me iPr iPr 1-1D-9 Me tBu tBu H Me tBu tBu 1-1D-10 Me Ph Ph H Me Ph Ph

[0153] Formula 1-1E can be represented by the following Formula 1-1E’.

[0154] Formula 1-1E’

[0155]

[0156] According to the combinations of substituents shown in Table 5 below, the polycyclic compounds represented by Formula 1-1E’ can be represented by Compounds 1-1E-1 to 1-1E-10. In Table 5, H represents a hydrogen atom, Me represents a methyl group, iPr represents an isopropyl group, tBu represents a tert-butyl group, and Ph represents a phenyl group.

[0157] Table 5

[0158] Compound number <![CDATA[R b > <![CDATA[R c > <![CDATA[R h > <![CDATA[R m > <![CDATA[R e > <![CDATA[R f > <![CDATA[R j > 1-1E-1 H H H H H H H 1-1E-2 H Me Me H H Me Me 1-1E-3 H H H Me H H H 1-1E-4 H iPr iPr H H iPr iPr 1-1E-5 H tBu tBu H H tBu tBu 1-1E-6 H Ph Ph H H Ph Ph 1-1E-7 Me Me Me H Me Me Me 1-1E-8 Me iPr iPr H Me iPr iPr 1-1E-9 Me tBu tBu H Me tBu tBu 1-1E-10 Me Ph Ph H Me Ph Ph

[0159] Formula 1-1F can be represented by the following Formula 1-1F’.

[0160] Formula 1-1F’

[0161]

[0162] According to the combinations of substituents shown in Table 6 below, the polycyclic compounds represented by Formula 1-1F’ can be represented by Compounds 1-1F-1 to Compound 1-1F-9. In Table 6, H represents a hydrogen atom, Me represents a methyl group, iPr represents an isopropyl group, tBu represents a tert-butyl group, and Ph represents a phenyl group.

[0163] Table 6

[0164] Compound number <![CDATA[R b > <![CDATA[R c > <![CDATA[R h > <![CDATA[R m > <![CDATA[R e > <![CDATA[R f > <![CDATA[R j > 1-1F-1 H H H H H H H 1-1F-2 H Me Me H H Me Me 1-1F-3 H H H Me H H H 1-1F-4 H iPr iPr H H iPr iPr 1-1F-5 H tBu tBu H H tBu tBu 1-1F-6 H Ph Ph H H Ph Ph 1-1F-7 Me Me Me H Me Me Me 1-1F-8 Me iPr iPr H Me iPr iPr 1-1F-9 Me tBu tBu H Me tBu tBu

[0165] Formula 1-1G can be represented by the following Formula 1-1G’.

[0166] Formula 1-1G’

[0167]

[0168] According to the combinations of substituents shown in Table 7 below, the polycyclic compounds represented by Formula 1-1G’ can be represented by Compounds 1-1G-1 to Compound 1-1G-10. In Table 7, H represents a hydrogen atom, Me represents a methyl group, iPr represents an isopropyl group, tBu represents a tert-butyl group, and Ph represents a phenyl group.

[0169] Table 7

[0170] Compound number <![CDATA[R c > <![CDATA[R g > <![CDATA[R h > <![CDATA[R m > <![CDATA[R f > <![CDATA[R i > <![CDATA[R j > 1-1G-1 H H H H H H H 1-1G-2 Me H Me H Me H Me 1-1G-3 H H H Me H H H 1-1G-4 iPr H iPr H iPr H iPr 1-1G-5 tBu H tBu H tBu H tBu 1-1G-6 Ph H Ph H Ph H Ph 1-1G-7 Me Me Me H Me Me Me 1-1G-8 iPr Me iPr H iPr Me iPr 1-1G-9 tBu Me tBu H tBu Me tBu 1-1G-10 Ph Me Ph H Ph Me Ph

[0171] Formula 1-1H can be represented by the following Formula 1-1H’.

[0172] Formula 1-1H’

[0173]

[0174] According to the combinations of substituents shown in Table 8 below, the polycyclic compounds represented by Formula 1-1H’ can be represented by Compounds 1-1H-1 to Compound 1-1H-10. In Table 8, H represents a hydrogen atom, Me represents a methyl group, iPr represents an isopropyl group, tBu represents a tert-butyl group, and Ph represents a phenyl group.

[0175] Table 8

[0176] Compound number <![CDATA[R c > <![CDATA[R g > <![CDATA[R h > <![CDATA[R m > <![CDATA[R f > <![CDATA[R i > <![CDATA[R j > 1-1H-1 H H H H H H H 1-1H-2 Me H Me H Me H Me 1-1H-3 H H H Me H H H 1-1H-4 iPr H iPr H iPr H iPr 1-1H-5 tBu H tBu H tBu H tBu 1-1H-6 Ph H Ph H Ph H Ph 1-1H-7 Me Me Me H Me Me Me 1-1H-8 iPr Me iPr H iPr Me iPr 1-1H-9 tBu Me tBu H tBu Me tBu 1-1H-10 Ph Me [[ID=336 H ​ ​ ​

[0177] The polycyclic compounds of the embodiments represented by Formula 1-2 can be represented by any one of the following Formulas 1-2A to 1-2E.

[0178]

[0179] In Formulas 1-2A to 1-2E, R1 to R 22 and R1’ to R21 ' may each independently be a hydrogen atom, a deuterium atom, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted oxy group, or a substituted or unsubstituted thio group. For example, R1 to R 22 and R1' to R 21 ' may each independently be a hydrogen atom, a methyl group, an isopropyl group, a tert-butyl group, a phenyl group, etc., but the embodiments of the present disclosure are not limited thereto. However, embodiments in which R 22 in Formula 1-2B is a substituted or unsubstituted carbazole group are excluded.

[0180] Formula 1-2A can be represented by the following Formula 1-2A'.

[0181] Formula 1-2A'

[0182]

[0183] According to the combinations of substituents shown in Table 9 below, the polycyclic compounds represented by Formula 1-2A' can be represented by Compounds 1-2A-1 to Compounds 1-2A-5. In Table 9, H represents a hydrogen atom, Me represents a methyl group, iPr represents an isopropyl group, tBu represents a tert-butyl group, and Ph represents a phenyl group.

[0184] Table 9

[0185] ​ <![CDATA[R c > <![CDATA[R g > <![CDATA[R h > <![CDATA[R f > <![CDATA[R i > <![CDATA[R j > 1-2A-1 H H H H H H 1-2A-2 ​ H ​ ​ H ​ 1-2A-3 ​ H ​ ​ H ​ 1-2A-4 ​ H ​ ​ H ​ 1-2A-5 ​ H ​ ​ H ​

[0186] Formula 1-2B can be represented by the following Formula 1-2B'.

[0187] Formula 1-2B'

[0188]

[0189] According to the combinations of substituents shown in Table 10 below, the polycyclic compounds represented by Formula 1-2B' can be represented by Compounds 1-2B-1 to Compounds 1-2B-5. In Table 10, H represents a hydrogen atom, Me represents a methyl group, iPr represents an isopropyl group, tBu represents a tert-butyl group, and Ph represents a phenyl group.

[0190] Table 10

[0191] ​ <![CDATA[R c > <![CDATA[R g > <![CDATA[R h > <![CDATA[R m > <![CDATA[R f > <![CDATA[R i > <![CDATA[R j > 1-2B-1 H H H H H H H 1-2B-2 ​ H ​ H ​ H ​ 1-2B-3 ​ H ​ H ​ H ​ 1-2B-4 ​ H ​ H ​ H ​ 1-2B-5 ​ H ​ H ​ H ​

[0192] Formula 1-2C can be represented by the following Formula 1-2C'.

[0193] Formula 1-2C'

[0194]

[0195] According to the combinations of substituents shown in Table 11 below, the polycyclic compounds represented by Formula 1-2C’ can be represented by Compounds 1-2C-1 to 1-2C-9. In Table 11, H represents a hydrogen atom, Me represents a methyl group, iPr represents an isopropyl group, tBu represents a tert-butyl group, and Ph represents a phenyl group.

[0196] Table 11

[0197]

[0198]

[0199] Formula 1-2D can be represented by the following Formula 1-2D’.

[0200] Formula 1-2D’

[0201]

[0202] According to the combinations of substituents shown in Table 12 below, the polycyclic compounds represented by Formula 1-2D’ can be represented by Compounds 1-2D-1 to 1-2D-10. In Table 12, H represents a hydrogen atom, Me represents a methyl group, iPr represents an isopropyl group, tBu represents a tert-butyl group, and Ph represents a phenyl group.

[0203] Table 12

[0204] ​ <![CDATA[R c > <![CDATA[R g > <![CDATA[R h > <![CDATA[R m > <![CDATA[R f > <![CDATA[R i > <![CDATA[R j > 1-2D-1 H H H H H H H 1-2D-2 ​ H ​ H ​ H ​ 1-2D-3 H H H ​ H H H 1-2D-4 ​ H ​ H ​ H ​ 1-2D-5 ​ H ​ H ​ H ​ 1-2D-6 ​ H ​ H ​ H ​ 1-2D-7 ​ ​ ​ H ​ ​ ​ 1-2D-8 ​ ​ ​ H ​ ​ iPr 1-2D-9 tBu Me tBu H tBu Me tBu 1-2D-10 Ph Me Ph H Ph Me Ph

[0205] Formula 1-2E can be represented by the following Formula 1-2E’.

[0206] Formula 1-2E’

[0207]

[0208] According to the combinations of substituents shown in Table 13 below, the polycyclic compounds represented by Formula 1-2E’ can be represented by Compounds 1-2E-1 to 1-2E-10. In Table 13, H represents a hydrogen atom, Me represents a methyl group, iPr represents an isopropyl group, tBu represents a tert-butyl group, and Ph represents a phenyl group.

[0209] Table 13

[0210] Compound number <![CDATA[R a > <![CDATA[R c > <![CDATA[R h > <![CDATA[R m > <![CDATA[R d > <![CDATA[R f > <![CDATA[R j > 1-2E-1 H H H H H H H 1-2E-2 H Me Me H H Me Me 1-2E-3 H H H Me H H H 1-2E-4 H iPr iPr H H iPr iPr 1-2E-5 H tBu tBu H H tBu tBu 1-2E-6 H Ph Ph H H Ph Ph 1-2E-7 Me Me Me H Me Me Me 1-2E-8 Me iPr iPr H Me iPr iPr 1-2E-9 Me tBu tBu H Me tBu tBu 1-2E-10 Me Ph Ph H Me Ph Ph

[0211] The polycyclic compounds of the embodiments represented by Formulae 1-3 can be represented by any one of Formulae 1-3A to 1-3F below:

[0212]

[0213]

[0214] In Formulae 1-3A to 1-3F, R1 to R 22 and R1' to R 21 ' can each independently be a hydrogen atom, a deuterium atom, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted oxy group, or a substituted or unsubstituted thio group. For example, R1 to R 22 and R1' to R 21 ' can each independently be a hydrogen atom, a methyl group, an isopropyl group, a tert-butyl group, a phenyl group, etc., but the embodiments of the present disclosure are not limited thereto.

[0215] Formula 1-3A can be represented by the following Formula 1-3A'.

[0216] Formula 1-3A'

[0217]

[0218] According to the combinations of substituents shown in Table 14 below, the polycyclic compounds represented by Formula 1-3A' can be represented by Compounds 1-3A-1 to 1-3A-9. In Table 14, H represents a hydrogen atom, Me represents a methyl group, iPr represents an isopropyl group, tBu represents a tert-butyl group, and Ph represents a phenyl group.

[0219] Table 14

[0220]

[0221]

[0222] Formula 1-3B can be represented by the following Formula 1-3B'.

[0223] Formula 1-3B'

[0224]

[0225] According to the combinations of substituents shown in Table 15 below, the polycyclic compounds represented by Formula 1-3B’ can be represented by Compounds 1-3B-1 to Compounds 1-3B-9. In Table 15, H represents a hydrogen atom, Me represents a methyl group, iPr represents an isopropyl group, tBu represents a tert-butyl group, and Ph represents a phenyl group.

[0226] Table 15

[0227] Compound number <![CDATA[R b > <![CDATA[R c > <![CDATA[R h > <![CDATA[R e > <![CDATA[R f > <![CDATA[R j > 1-3B-1 H H H H H H 1-3B-2 H Me Me H Me Me 1-3B-3 H iPr iPr H iPr iPr 1-3B-4 H tBu tBu H tBu tBu 1-3B-5 H Ph Ph H Ph Ph 1-3B-6 Me Me Me Me Me Me 1-3B-7 Me iPr iPr Me iPr iPr 1-3B-8 Me tBu tBu Me tBu tBu 1-3B-9 Me Ph Ph Me Ph Ph

[0228] Formula 1-3C can be represented by the following Formula 1-3C’.

[0229] Formula 1-3C’

[0230]

[0231] According to the combinations of substituents shown in Table 16 below, the polycyclic compounds represented by Formula 1-3C’ can be represented by Compounds 1-3C-1 to Compounds 1-3C-9. In Table 16, H represents a hydrogen atom, Me represents a methyl group, iPr represents an isopropyl group, tBu represents a tert-butyl group, and Ph represents a phenyl group.

[0232] Table 16

[0233] Compound number <![CDATA[R b > <![CDATA[R c > <![CDATA[R h > <![CDATA[R m > <![CDATA[R e > <![CDATA[R f > <![CDATA[R j > 1-3C-1 H H H H H H H 1-3C-2 H Me Me H H Me Me 1-3C-3 H iPr iPr H H iPr iPr 1-3C-4 H tBu tBu H H tBu tBu 1-3C-5 H Ph Ph H H Ph Ph 1-3C-6 Me Me Me H Me Me Me 1-3C-7 Me iPr iPr H Me iPr iPr 1-3C-8 Me tBu tBu H Me tBu tBu 1-3C-9 Me Ph Ph H Me Ph Ph

[0234] Formula 1-3D can be represented by the following Formula 1-3D’.

[0235] Formula 1-3D’

[0236]

[0237] According to the combinations of substituents shown in Table 17 below, the polycyclic compounds represented by Formula 1-3D’ can be represented by Compounds 1-3D-1 to Compounds 1-3D-10. In Table 17, H represents a hydrogen atom, Me represents a methyl group, iPr represents an isopropyl group, tBu represents a tert-butyl group, and Ph represents a phenyl group.

[0238] Table 17

[0239]

[0240]

[0241] Formula 1-3E can be represented by the following Formula 1-3E’.

[0242] Formula 1-3E’

[0243]

[0244] According to the combinations of substituents shown in Table 18 below, the polycyclic compounds represented by Formula 1-3E’ can be represented by Compounds 1-3E-1 to Compounds 1-3E-10. In Table 18, H represents a hydrogen atom, Me represents a methyl group, iPr represents an isopropyl group, tBu represents a tert-butyl group, and Ph represents a phenyl group.

[0245] Table 18

[0246] Compound number <![CDATA[R b > <![CDATA[R c > <![CDATA[R h > <![CDATA[R m > <![CDATA[R e > <![CDATA[R f > <![CDATA[R j > 1-3E-1 H H H H H H H 1-3E-2 H Me Me H H Me Me 1-3E-3 H H H Me H H H 1-3E-4 H iPr iPr H H iPr iPr 1-3E-5 H tBu tBu H H tBu tBu 1-3E-6 H Ph Ph H H Ph Ph 1-3E-7 Me Me Me H Me Me Me 1-3E-8 Me iPr iPr H Me iPr iPr 1-3E-9 Me tBu tBu H Me tBu tBu 1-3E-10 Me Ph Ph H Me Ph Ph

[0247] Formula 1-3F can be represented by the following Formula 1-3F’.

[0248] Formula 1-3F’

[0249]

[0250] According to the combinations of substituents shown in Table 19 below, the polycyclic compounds represented by Formula 1-3F’ can be represented by Compounds 1-3F-1 to Compounds 1-3F-10. In Table 19, H represents a hydrogen atom, Me represents a methyl group, iPr represents an isopropyl group, tBu represents a tert-butyl group, and Ph represents a phenyl group.

[0251] Table 19

[0252] Compound number <![CDATA[R a > <![CDATA[R c > <![CDATA[R h > <![CDATA[R m > <![CDATA[R d > <![CDATA[R f > <![CDATA[R j > 1-3F-1 H H H H H H H 1-3F-2 H Me Me H H Me Me 1-3F-3 H H H Me H H H 1-3F-4 H iPr iPr H H iPr iPr 1-3F-5 H tBu tBu H H tBu tBu 1-3F-6 H Ph Ph H H Ph Ph 1-3F-7 Me Me Me H Me Me Me 1-3F-8 Me iPr iPr H Me iPr iPr 1-3F-9 Me tBu tBu H Me tBu tBu 1-3F-10 Me Ph Ph H Me Ph Ph

[0253] The polycyclic compounds of the embodiments may be any one of the compounds represented by Formula 1-1 to Formula 1-3. The organic electroluminescent device 10 of the embodiments may include at least one polycyclic compound selected from 1-1A-1 to 1-1A-9, 1-1B-1 to 1-1B-9, 1-1C-1 to 1-1C-10, 1-1D-1 to 1-1D-10, 1-1E-1 to 1-1E-10, 1-1F-1 to 1-1F-9, 1-1G-1 to 1-1G-10, 1-1H-1 to 1-1H-10, 1-2A-1 to 1-2A-5, 1-2B-1 to 1-2B-5, 1-2C-1 to 1-2C-9, 1-2D-1 to 1-2D-10, 1-2E-1 to 1-2E-10, 1-3A-1 to 1-3A-9, 1-3B-1 to 1-3B-9, 1-3C-1 to 1-3C-9, 1-3D-1 to 1-3D-10, 1-3E-1 to 1-3E-10, and 1-3F-1 to 1-3F-10 in the emission layer EML. The polycyclic compounds of the embodiments may be materials for emitting thermally activated delayed fluorescence. The polycyclic compounds of the embodiments have a structure in which two polycyclic aromatic groups are bonded via a linker, and may emit light with a narrow full width at half maximum (FWHM) in the deep blue wavelength region, and may exhibit high efficiency properties when compared with compounds having a structure including one polycyclic aromatic group not connected via a linker.

[0254] The polycyclic compound of the embodiment represented by Formula 1 may be a luminescent material having an emission center wavelength (λ 最大 ) in a wavelength region of about 470 nm or less than 470 nm. For example, the polycyclic compound of the embodiment represented by Formula 1 may be a luminescent material having an emission center wavelength in a wavelength region of about 430 nm to about 490 nm. The polycyclic compound of the embodiment represented by Formula 1 may be a blue thermally activated delayed fluorescence dopant.

[0255] In the organic electroluminescent device 10 of the embodiments, the emission layer EML may emit delayed fluorescence. For example, the emission layer EML may emit thermally activated delayed fluorescence (TADF).

[0256] In some embodiments, the organic electroluminescent device 10 of the embodiments may include a plurality of emission layers. The plurality of emission layers may be laminated one by one. For example, the organic electroluminescent device 10 including a plurality of emission layers may emit white light. The organic electroluminescent device including a plurality of emission layers may be an organic electroluminescent device having a tandem structure. If the organic electroluminescent device 10 includes a plurality of emission layers, at least one emission layer EML may include the polycyclic compound of the embodiments.

[0257] In an embodiment, the emission layer EML includes a host and a dopant, and may include a polycyclic compound of the embodiment as a dopant. For example, in the organic electroluminescent device 10 of the embodiment, the emission layer EML may include a host for emitting delayed fluorescence and a dopant for emitting delayed fluorescence, and may include a polycyclic compound as a dopant for emitting delayed fluorescence. The emission layer EML may include at least one of the polycyclic compounds of the present embodiment as a thermally activated delayed fluorescence dopant.

[0258] In an embodiment, the emission layer EML may be a delayed fluorescence emission layer, and the emission layer EML may include any suitable host material and the polycyclic compound described above. For example, in an embodiment, the polycyclic compound may be used as a TADF dopant.

[0259] In an embodiment, the emission layer EML may include any suitable host material. For example, in an embodiment, the emission layer EML may include tris(8-hydroxyquinolinato)aluminum (Alq3), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), poly(N-vinylcarbazole) (PVK), 9,10-bis(naphthalen-2-yl)anthracene (ADN), 4,4',4''-tris(carbazol-9-yl)-triphenylamine (TCTA), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBi), 3-tert-butyl-9,10-bis(naphthalen-2-yl)anthracene (TBADN), stilbene-substituted arylide (DSA), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), bis[2-(diphenylphosphino)phenyl] ether oxide (DPEPO), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH2), hexaphenylcyclotrisiloxane (DPSiO3), octaphenylcyclotetrasiloxane (DPSiO4), 2,8-bis(diphenylphosphoryl)dibenzofuran (PPF), 3,3'-bis(N-carbazolyl)-1,1'-biphenyl (mCBP), 1,3-bis(N-carbazolyl)benzene (mCP), etc. as the host material. However, the embodiments of the present disclosure are not limited thereto. Any suitable host material for emitting delayed fluorescence other than the proposed host materials may be included.

[0260] In the organic electroluminescent device 10 of the embodiment, the emission layer EML may further include any suitable dopant material. In an embodiment, the emission layer EML may include a styryl derivative (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)naphthalen-2-yl)vinyl)phenyl)-N-phenylaniline (N-BDAVBi)), perylene and / or its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)), pyrene and / or its derivatives (e.g., 1,1-dipyrene, 1,4-dipyrenylbenzene, and / or 1,4-bis(N,N-diphenylamino)pyrene), etc.) as a dopant.

[0261] In the organic electroluminescent device 10 of the embodiment as shown in Figures 1 to 4 an electron transport region ETR is provided over the emission layer EML. The electron transport region ETR may include at least one selected from a hole blocking layer HBL, an electron transport layer ETL, and an electron injection layer EIL. However, the embodiments of the present disclosure are not limited thereto.

[0262] The electron transport region ETR may have a single layer formed of a single material, a single layer formed of a plurality of different materials, or a multilayer structure having a plurality of layers formed of a plurality of different materials.

[0263] 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 of an electron injection material and an electron transport material. In some embodiments, 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 laminated from the emission layer EML, but is not limited thereto. The thickness of the electron transport region ETR may be, for example, about to about

[0264] The electron transport region ETR may be formed using one or more suitable methods (e.g., vacuum deposition method, spin coating method, casting method, Langmuir-Blodgett (LB) method, inkjet printing method, laser printing method, and / or laser induced thermal imaging (LITI) method).

[0265] If the electron transport region (ETR) includes an electron transport layer (ETL), the ETR may include anthracene-based compounds. The ETR may include, for example, tris(8-hydroxyquinolinato)aluminum (Alq3), 1,3,5-tris[(3-pyridinyl)-phenyl-3-yl]benzene, 2,4,6-tris(3’-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), 3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (tBu-PBD), bis(2-methyl-8-quinolinato-N1,O8)-(1,1’-biphenyl-4-yl)aluminum (BAlq), bis(benzoquinolinato-10-yl)beryllium (Bebq2), 9,10-di(naphthalen-2-yl)anthracene (ADN), 1,3-bis[3,5-bis(pyridin-3-yl)phenyl]benzene (BmPyPhB), or mixtures thereof, without limitation. The thickness of the ETL may be from about to about and may be, for example, about to about If the thickness of the ETL meets the range described above, satisfactory (or suitable) electron transport properties can be obtained without a significant increase in driving voltage.

[0266] If the ETR includes an electron injection layer (EIL), the EIL may include metal halides (such as LiF, NaCl, CsF, RbCl, and / or RbI), lanthanide metals (such as Yb), metal oxides (such as Li2O and / or BaO), and / or lithium quinolate (LiQ). However, the embodiments of the present disclosure are not limited thereto. A mixture material of an electron transport material and an insulating organometallic salt may also be used to form the EIL. The organometallic salt may be a material having a band gap of about 4 eV or greater than 4 eV. For example, the organometallic salt may include, for example, metal acetates, metal benzoates, metal acetoacetates, metal acetylacetonates, and / or metal stearates. The thickness of the EIL may be from about to about For example, about to about If the thickness of the electron injection layer EIL satisfies the range described above, satisfactory (or suitable) electron injection properties can be obtained without a significant increase in the driving voltage.

[0267] The electron transport region ETR may include a hole blocking layer HBL. The hole blocking layer HBL may contain, 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 embodiments of the present disclosure are not limited thereto.

[0268] A second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 may be a common electrode and / or a cathode. The second electrode EL2 may be a transmissive electrode, a semi-transmissive reflective electrode, or a reflective electrode. If the second electrode EL2 is a transmissive electrode, the second electrode EL2 may contain a transparent metal oxide, for example, ITO, IZO, ZnO, ITZO, etc.

[0269] If the second electrode EL2 is a semi-transmissive reflective electrode or a reflective electrode, the second electrode EL2 may contain Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, their compounds, or their mixtures (for example, a mixture of Ag and Mg). The second electrode EL2 may have a multilayer structure including a reflective layer or a semi-transmissive reflective layer formed using any of the materials described above and a transparent conductive layer formed using ITO, IZO, ZnO, ITZO, etc.

[0270] In some embodiments, the second electrode EL2 may be connected to an auxiliary electrode. If the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 can be reduced.

[0271] On the second electrode EL2 of the organic electroluminescent device 10 of the embodiment, a cover layer CPL may be further placed. The cover layer CPL may contain, 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), etc.

[0272] The organic electroluminescent device 10 according to an embodiment of the present disclosure includes the polycyclic compound of the embodiment in an emission layer EML positioned between a first electrode EL1 and a second electrode EL2, thereby exhibiting excellent (suitable) emission efficiency and a narrow full width at half maximum in the emission wavelength region of blue light. In addition, the polycyclic compound according to the embodiment can emit thermally activated delayed fluorescence, and the emission layer EML can include the polycyclic compound of the embodiment to emit thermally activated delayed fluorescence and exhibit high emission efficiency properties.

[0273] The polycyclic compound of the embodiment can be included as a material for the organic electroluminescent device 10 in an organic layer other than the emission layer EML. For example, the organic electroluminescent device 10 according to an embodiment of the present disclosure can include the polycyclic compound in at least one functional layer between the first electrode EL1 and the second electrode EL2 or in an overcoat layer on the second electrode EL2.

[0274] The polycyclic compound of the embodiment has a combined structure in which two polycyclic aromatic groups are connected via a linker, can exhibit a high lowest triplet excitation energy level, and can be used as a material for emitting delayed fluorescence. In addition, the organic electroluminescent device of the embodiment including the polycyclic compound of the embodiment in the emission layer emits blue light with a narrow full width at half maximum and can exhibit high efficiency properties.

[0275] Hereinafter, the polycyclic compound according to the embodiment and the organic electroluminescent device of the embodiment of the present disclosure will be specifically explained with reference to the embodiments and comparative embodiments. The following embodiments are only examples for helping the understanding of the present disclosure, and the scope of the present disclosure is not limited thereto.

[0276] Examples

[0277] 1. Synthesis of the polycyclic compound of the embodiment

[0278] First, the synthesis method of the polycyclic compound according to one or more embodiments will be specifically explained with reference to the synthesis methods of reference compounds 1 to 10. However, the synthesis method of the polycyclic compound explained below is only an exemplary embodiment, and the synthesis method of the polycyclic compound of the present disclosure is not limited thereto.

[0279] The example compounds 1 to 10 provided as the following examples are as follows:

[0280]

[0281] (1) Synthesis of Compound 1

[0282] Compound 1 according to the embodiment can be synthesized through steps such as the following Reaction 1-1 and Reaction 1-2.

[0283] Synthesis of Intermediate 1

[0284] Intermediate 1 can be synthesized by the following Reaction 1-1.

[0285] Reaction 1-1

[0286]

[0287] Dissolve compound X1 (5,9-diphenyl-5,9-dihydro-5,9-diaza-13b-boraphenanthro[3,2,1-de]anthracene) (9.5 g, 22.6 mmol) in THF (300 ml), and add bromine (3.61 g, 22.6 mmol) thereto at about 40 °C, followed by stirring for about 10 hours. After completion of the reaction, the resulting product is concentrated, filtered, and separated by silica gel column chromatography (toluene:hexane = 2:3) to obtain Intermediate 1 (10.17 g, yield 90%).

[0288] Synthesis of Compound 1

[0289] Compound 1 can be synthesized by the following Reaction 1-2.

[0290] Reaction 1-2

[0291]

[0292] Add the thus obtained Intermediate 1 (5.0 g, 10.0 mmol) and 1,4-phenylenediboronic acid (0.83 g, 5.0 mmol) to toluene (100 ml), and add PdCl2(PPh3)2 (0.35 g, 0.5 mmol) and K3PO4 (6.4 g, 30.0 mmol) thereto, followed by heating at about 80 °C and stirring for about 6 hours. Thereafter, add water, and the resulting product is extracted with toluene and concentrated. The crude product is separated by silica gel column chromatography (toluene:hexane = 2:3) to obtain Compound 1 (4.0 g, yield 87%). The measured value of the molecular weight of Compound 1 measured by fast atom bombardment-mass spectrometry (FAB-MS) is m / z = 915 (M + +1).

[0293] (2) Synthesis of Compound 2

[0294] Compound 2 according to the embodiment can be synthesized, for example, by the following Reaction 2.

[0295] Reaction 2

[0296]

[0297] Intermediate 1 (5.0 g, 10.0 mmol) and 1,3-phenylenediboronic acid (0.83 g, 5.0 mmol) were added to toluene (100 ml), and PdCl2(PPh3)2 (0.35 g, 0.5 mmol) and K3PO4 (6.4 g, 30.0 mmol) were added thereto. Subsequently, it was heated at about 80 °C and stirred for about 6 hours. Thereafter, water was added, and the resulting product was extracted with toluene and concentrated. The product was separated by silica gel column chromatography (toluene:hexane = 2:3) to obtain Compound 2 (3.8 g, yield 83%). The measured value of the molecular weight of Compound 2 measured by FAB-MS was m / z = 915 (M + +1).

[0298] (3) Synthesis of Compound 3

[0299] Compound 3 according to the embodiment can be synthesized, for example, by the following Reaction 3.

[0300] Reaction 3

[0301]

[0302] Intermediate 1 (4.0 g, 9.0 mmol) was added to THF (100 ml), and 1.6 M t BuLi (pentane solution, 11.2 ml, 17.9 mmol) was added dropwise thereto at about -30 °C. The temperature was raised to room temperature again, stirred for about 2 hours, the temperature was cooled to about -78 °C again, and a THF solution of PhBCl2 (20 ml) was added dropwise thereto. The temperature was raised to room temperature again, stirred for about 3 hours, and N,N-diisopropylethylamine (3.1 ml, 17.9 mmol) was added, followed by stirring overnight. Water and toluene were added to the reaction product and the liquid was separated. The organic layer was concentrated and separated by silica gel column chromatography (toluene:hexane = 1:1) to obtain Compound 3 (1.8 g, yield 48%). The measured value of the molecular weight of Compound 3 measured by FAB-MS was m / z = 927 (M + +1).

[0303] (4) Synthesis of Compound 4

[0304] Compound 4 according to the embodiment can be synthesized, for example, by the following Reaction 4.

[0305] Reaction 4

[0306]

[0307] Intermediate 1 (2.5 g, 5.0 mmol), aniline (0.23 g, 2.5 mmol), Pd2(dba)3 (91.7 mg, 0.1 mmol), P( t Bu)3HBF4 (36.1 mg, 0.2 mmol), t BuONa (1.13 g, 11.8 mmol) were added to toluene (50 ml), and then stirred at about 100 °C for about 8 hours. Then, water was added and the liquid layer was separated. The organic layer was separated and concentrated. The crude product was separated by silica gel column chromatography (toluene:hexane = 1:1) to obtain Compound 4 (1.86 g, yield 80%). The measured molecular weight of Compound 4 by FAB-MS was m / z = 930 (M + +1).

[0308] (5) Synthesis of Compound 5

[0309] Compound 5 according to the embodiment can be synthesized, for example, by the following Reaction 5.

[0310] Reaction 5

[0311]

[0312] At about 100 °C, Intermediate 1 (3.0 g, 6.0 mmol), Pd2(dba)3 (110 mg, 0.12 mmol), P( t Bu)3HBF4 (43.3 mg, 0.24 mmol), K3PO4·H2O (4.14 g, 18 mmol) were stirred for about 24 hours. Then, water was added and the liquid layer was separated. The organic layer was separated and concentrated. The crude product was separated by silica gel column chromatography (toluene:hexane = 1:1) to obtain Compound 5 (1.30 g, yield 51%). The measured molecular weight of Compound 5 by FAB-MS was m / z = 855 (M + +1).

[0313] (6) Synthesis of Compound 6

[0314] Compound 6 according to the embodiment can be synthesized, for example, by the following Reaction 6.

[0315] Reaction 6

[0316]

[0317] Intermediate 1 (5.0 g, 10 mmol), Na2S (3.9 g, 50 mmol), CuI (0.19 g, 1.0 mmol), and I2 (a small amount) were added to NMP (50 ml), and then stirred at about 200 °C for about 48 hours. Then, water was added, and the liquid layer was separated. The organic layer was separated and concentrated. The crude product was separated by silica gel column chromatography (toluene:hexane = 1:1) to obtain Compound 6 (1.30 g, yield 30%). The measured molecular weight of Compound 6 by FAB-MS was m / z = 871 (M + +1).

[0318] (7) Synthesis of Compound 7

[0319] Compound 7 according to the embodiment can be synthesized by, for example, the following Reaction 7.

[0320] Reaction 7

[0321]

[0322] Intermediate 1 (8.0 g, 16 mmol) was added to THF (100 ml), and 1.6 M t BuLi (pentane solution, 22.4 ml, 35.8 mmol) was added dropwise thereto at about -30 °C. The temperature was then raised to room temperature and stirred for about 2 hours, the temperature was cooled to about -78 °C again, and PhPOCl2 (3.5 g, 17.5 mmol) was added dropwise thereto, followed by stirring overnight. Water and toluene were added to the reaction solution and the liquid layer was separated. The organic layer was concentrated and separated by silica gel column chromatography (toluene:hexane = 1:1) to obtain Compound 7 (4.0 g, yield 52%). The measured molecular weight of Compound 7 by FAB-MS was m / z = 963 (M + +1).

[0323] (8) Synthesis of Compound 8

[0324] Compound 8 according to the embodiment can be synthesized by, for example, the following Reaction 8.

[0325] Reaction 8

[0326]

[0327] Compound 7 (3.0 g, 3.1 mmol) synthesized by Reaction 7 was added to 1,4-dioxane (50 ml), and Lawesson's reagent (1.89 g, 4.67 mmol) was added thereto. Subsequently, the mixture was heated and refluxed for about 60 hours. Water and toluene were added to the reaction solution, and the liquid layers were separated. The organic layer was concentrated and separated by silica gel column chromatography (toluene:hexane = 1:1) to obtain Compound 8 (1.1 g, yield 35%). The measured value of the molecular weight of Compound 8 measured by FAB-MS was m / z = 979 (M + +1).

[0328] (9) Synthesis of Compound 9

[0329] Compound 9 according to the embodiment can be synthesized, for example, by the following Reaction 9.

[0330] Reaction 9

[0331]

[0332] Intermediate 1 (8.0 g, 16 mmol) and Mg (0.39 g, 16 mmol) were added to THF, and the mixture was stirred at room temperature for about 1 hour. The reaction solution was added dropwise to a THF solution (100 ml) of 1,1'-carbonyldiimidazole (8.57 g, 52.9 mmol). After standing and cooling for about 12 hours, an aqueous NH4Cl solution was added to the reaction solution, extracted with ethyl acetate, and the organic layer was concentrated. The crude product was separated by silica gel column chromatography (toluene:hexane = 1:1) to obtain Compound 9 (1.1 g, yield 36%). The measured value of the molecular weight of Compound 9 measured by FAB-MS was m / z = 867 (M + +1).

[0333] (10) Synthesis of Compound 10

[0334] Compound 10 according to the embodiment can be synthesized, for example, by the following Reactions 10-1 to 10-3.

[0335] Synthesis of Intermediate 2

[0336] Intermediate 2 can be synthesized by the following Reaction 10-1:

[0337] Reaction 10-1

[0338]

[0339] 5-Bromo-1,2,3-trichlorobenzene and 1,3-phenylenediboronic acid (0.83 g, 5.0 mmol) were added to toluene (100 ml), and PdCl2(PPh3)2 (0.35 g, 0.5 mmol) and K3PO4 (6.4 g, 30.0 mmol) were added thereto. Subsequently, the mixture was heated at about 90 °C and stirred for about 6 hours. Thereafter, water was added, and the resulting product was extracted with toluene and concentrated. The crude product was separated by silica gel column chromatography (toluene:hexane = 2:3) to obtain Intermediate 2 (yield 70%).

[0340] Synthesis of Intermediate 3

[0341] Intermediate 3 can be synthesized by the following Reaction 10-2:

[0342] Reaction 10-2

[0343]

[0344] Intermediate 2 was mixed with diphenylamine, Pd2(dba)3, P(tBu)3, NaOtBu and toluene and stirred at about 90 °C. Thereafter, water was added, and the resulting product was extracted with toluene and concentrated. The crude product was separated by silica gel column chromatography (toluene:hexane = 2:3) to obtain Intermediate 3 (yield 75%).

[0345] Synthesis of Compound 10

[0346] Compound 3 can be synthesized by the following Reaction 10-3:

[0347] Reaction 10-3

[0348]

[0349] Under a nitrogen atmosphere, at about -30 °C, a 1.7 M solution of tert-butyllithium in pentane was added to a flask containing Intermediate 3 and tert-butylbenzene. After the dropwise addition was completed, the temperature was raised to about 60 °C and stirred for about 2 hours. The component having a boiling point lower than that of tert-butylbenzene was distilled off under reduced pressure. The temperature was cooled to about -30 °C, boron tribromide was added, the temperature was raised to room temperature and stirred for about 0.5 hour. Thereafter, the temperature was cooled to about 0 °C again, N,N-diisopropylethylamine was added, stirred at room temperature until the mixture cooled, and the temperature was raised to about 120 °C, then heated and stirred for about 3 hours. The reaction solution was cooled to room temperature, an aqueous solution of sodium acetate cooled in an ice bath was added thereto, and then heptane was added thereto, and the liquid layer was separated. Then, the crude product was separated by silica gel column chromatography (toluene:hexane = 2:3) to obtain Compound 10 (yield 13%). The measured value of the molecular weight of Compound 10 by FAB-MS was m / z = 915 (M+ +1).

[0350] In the synthesis examples described above, the synthesis of Compounds 1 to 10 and the synthesis of intermediate compounds were carried out with reference to the publicly disclosed patent document WO2016-152544, which is hereby incorporated by reference in its entirety.

[0351] 2. Evaluation of polycyclic compounds and fabrication and evaluation of organic electroluminescent devices

[0352] The fluorescence emission properties of the polycyclic compounds of the embodiments and the organic electroluminescent devices of the embodiments containing the polycyclic compounds of the embodiments in the emission layer were evaluated by the methods described below. The fabrication method of the organic electroluminescent devices for device evaluation is described below.

[0353] The organic electroluminescent devices of Examples 1 to 10 were fabricated using the polycyclic compounds of Compounds 1 to 10 as dopant materials for the emission layer, respectively. In addition, the organic electroluminescent devices of Comparative Examples were fabricated using Comparative Compounds X-1 to Comparative Compound X-6 as dopant materials for the emission layer, respectively.

[0354] The comparative compounds for the comparative examples are as follows:

[0355]

[0356] Evaluation of the luminescence properties of the compounds

[0357] A 5.0 mM toluene solution was prepared for each of the example compounds and comparative compounds, and the luminescence properties were evaluated using a JASCO V-670 spectrometer. The emission spectra were measured at room temperature and 77 K. In Table 20, the maximum emission wavelength λ 最大 in the emission spectrum measured at room temperature and the full width at half maximum (FWHM) in the emission spectrum are shown. In addition, the T1 level was calculated from the starting value of the emission spectrum at 77 K.

[0358] Table 20

[0359] Compound <![CDATA[λ 最大 (nm)]]> FWHM (nm) <![CDATA[T1 level (eV)]]> Compound 1 466 24.8 2.57 Compound 2 465 25.8 2.58 Compound 3 438 22.3 2.74 Compound 4 458 26.7 2.56 Compound 5 465 26.8 2.57 Compound 6 464 26.6 2.58 Compound 7 447 35.5 2.75 Compound 8 453 38.6 2.73 Compound 9 466 33.6 2.63 Compound 10 463 29.0 2.63 Comparative compound X-1 459 28 2.58 Comparative compound X-2 467 28 2.56 Comparative compound X-3 464 25.7 2.58 Comparative compound X-4 468 35 2.53 Comparative compound X-5 432 43 2.72 Comparative compound X-6 445 46 2.68

[0360] Referring to the results in Table 20, the polycyclic compounds of the examples showed a maximum emission wavelength of about 470 nm or less than 470 nm, and from this result, it can be concluded that deep blue light is emitted. In addition, it was found that the polycyclic compounds of the examples showed similar emission wavelengths and T1 levels to Comparative Compounds X-1 and Comparative Compound X-2 having only one polycyclic aromatic group. The polycyclic compounds of the examples exhibited a T1 level of about 2.5 eV or greater than 2.5 eV, and by having a high T1 level, it is considered possible to emit thermally activated delayed fluorescence.

[0361] Manufacture of Organic Electroluminescent Device

[0362] On a glass substrate, ITO having a thickness of about is patterned and washed with ultrapure water, cleaned ultrasonically, exposed to UV for about 30 minutes, and treated with ozone. Then, HAT-CN is deposited to a thickness of about α-NPD is deposited to about and mCP is deposited to about in thickness to form a hole transport region.

[0363] Then, the polycyclic compound (or comparative compound) of the embodiment and mCBP are co-deposited at a ratio of 1:99 to form an emission layer to a thickness of about More specifically, an emission layer is formed by mixing and depositing one of Compounds 1 to 10 in Examples 1 to 10 or one of Comparative Compounds X-1 to X-6 in Comparative Examples 1 to 6 with mCBP, respectively.

[0364] Thereafter, on the emission layer, a layer having a thickness of about is formed using TPBi, and a layer having a thickness of about is formed using Liq to form an electron transport region. Then, a second electrode having a thickness of about is formed using aluminum (Al).

[0365] In the examples, a hole transport region, an emission layer, an electron transport region, and a second electrode are formed using a vacuum deposition apparatus.

[0366] Evaluation of Properties of Organic Electroluminescent Device

[0367] In Table 21, the evaluation results of the organic electroluminescent devices of Examples 1 to 10 and Comparative Examples 1 to 6 are shown. In Table 21, the maximum emission wavelength (λ 最大 ) and the external quantum efficiency (EQE 最大 , EQE 最大,1000nit ) of the thus-manufactured organic electroluminescent devices are compared and shown. Among the evaluation results of the properties of the examples and comparative examples shown in Table 21, the maximum emission wavelength (λ 最大 ) represents the wavelength showing the maximum value in the emission spectrum, EQE 最大 in the external quantum efficiency represents the maximum value of the external quantum yield, and EQE 最大,1000nit in the external quantum efficiency represents the yield at the point where the luminance is 1,000 cd / m 2 .

[0368] Table 21

[0369]

[0370]

[0371] Referring to the results in Table 21, it was confirmed that the organic electroluminescent devices of Examples 1 to 10 exhibited excellent maximum emission efficiency properties when compared with the organic electroluminescent devices of Comparative Examples 3 to 6.

[0372] The example compounds (Compound 1, Compound 2, and Compound 10) for Examples 1, 2, and 10 had a linking structure including two portions of the comparative compound X-1 for Comparative Example 1. Two portions in the example compounds were linked using an arylene group linker. It was found that Examples 1, 2, and 10 emitted light in a wavelength region similar to that of Comparative Example 1 and exhibited improved emission efficiency properties when compared with Comparative Example 1. Thus, it is believed that the example compounds of the present disclosure having a linking structure of two aromatic groups linked via a linker exhibit improved emission efficiency when compared with compounds having one aromatic group, without affecting the emission wavelength or full width at half maximum.

[0373] Meanwhile, when compared with the EQE 最大,1000nit values of Examples 1 to 10, the EQE 最大,1000nit values of Comparative Examples 1 to 6 were significantly lower. It is believed that the example compounds of the present disclosure exhibit excellent thermal stability and reliability properties when compared with comparative compounds X-3 to X-6 having two aromatic groups and comparative compounds containing only one aromatic group.

[0374] The comparative compound X-4 for Comparative Example 4 had a linking structure of two aromatic groups via a linker, but had a structure in which the phenylene group linker was replaced by a carbazole group, and it was confirmed that when compared with Example 10, it exhibited lower emission efficiency properties. It is believed that in comparative compound X-4, due to the rotation and / or vibration of the carbazole group substituted on the phenylene group, light cannot be emitted and the energy is dissipated to reduce the emission efficiency.

[0375] The polycyclic compounds of the embodiments have a linking structure in which two aromatic groups are linked via a linker, and when compared with the compound structure having one aromatic group, can exhibit improved emission efficiency properties while maintaining the emission wavelength properties and color purity properties of the aromatic groups. The organic electroluminescent devices of the embodiments contain the polycyclic compounds of the embodiments in the emission layer, thereby achieving a narrow full width at half maximum in the blue emission wavelength region and exhibiting excellent color properties and high emission efficiency properties.

[0376] The organic electroluminescent device of the embodiment can exhibit improved device characteristics with high efficiency in the blue wavelength region.

[0377] The polycyclic compound of the embodiment is included in the emission layer of the organic electroluminescent device and can contribute to increasing the efficiency of the organic electroluminescent device.

[0378] As used herein, the terms "use", "using", and "used" may be considered synonymous with the terms "utilize", "utilizing", and "utilized", respectively.

[0379] In addition, the terms "substantially", "about", and similar terms are used as approximate terms and not as terms of degree, and are intended to account for the inherent deviations in measured or calculated values that would be recognized by a person of ordinary skill in the art.

[0380] In addition, any numerical range recited herein is intended to include all sub-ranges of the same numerical precision subsumed within the recited range. For example, a range of "1.0 to 10.0" is intended to include all sub-ranges between (and including the end values) the recited minimum value of 1.0 and the recited maximum value of 10.0, that is, having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limitation recited herein is intended to include all lower numerical limitations subsumed therein, and any minimum numerical limitation recited in this specification is intended to include all higher numerical limitations subsumed therein. Accordingly, the applicant reserves the right to modify this specification (including the claims) to expressly recite any sub-ranges subsumed within the ranges expressly recited herein.

[0381] Although the exemplary embodiments of the present disclosure have been described, it should be understood that the present disclosure should not be limited by these exemplary embodiments, and various changes and modifications can be made by a person of ordinary skill in the art within the spirit and scope of the present disclosure as claimed by the claims and their equivalents.

Claims

1. An organic electroluminescent device, comprising: A first electrode; A second electrode on the first electrode; And An emission layer between the first electrode and the second electrode, the emission layer comprising a polycyclic compound represented by Formula 1, Wherein the first electrode and the second electrode each independently comprise: one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, In, Sn, and Zn; a compound selected from two or more of them; a mixture selected from two or more of them; and oxides of the foregoing substances: Formula 1 And wherein, in Formula 1, Ar1 to Ar4 are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, R a to R f each independently is a hydrogen atom, a deuterium atom, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, a substituted or unsubstituted oxy group, or a substituted or unsubstituted thio group, "a", "c", "d", and "f" are each independently an integer from 0 to 4, "b" and "e" are each independently an integer from 0 to 3, When ring A1 and ring A2 are connected via L, L is S, BR p , (P═O)R s , (P═S)R t , (C═O), or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms for forming a ring When rings A3 and A4 are connected via L, L is S, BR p , (P=O)R s , (P=S)R t , (C=O), or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms for forming a ring, When ring H1 and ring H2 are connected via L, L connects Ar1 and Ar3 to each other, and L is S, BR p , (P=O)R s , (P=S)R t , (C=O), or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms for forming a ring, and R p 、R q 、R s and R t each independently is a hydrogen atom, a deuterium atom, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, a substituted or unsubstituted oxy group, or a substituted or unsubstituted thio group.

2. The organic electroluminescent device according to claim 1, wherein Ar1 to Ar4 are each independently a substituted or unsubstituted phenyl group.

3. The organic electroluminescent device according to claim 1, wherein Formula 1 is represented by any one selected from Formula 1-1 to Formula 1-3: Formula 1-1 Formula 1-2 Formula 1-3 Among them, In Formula 1-1 to Formula 1-3, Ar1 to Ar4, R a to R f ,"a" to "f", and L are the same as defined in Formula 1.

4. The organic electroluminescent device according to claim 1, wherein Formula 1 is represented by Formula 2: Formula 2 Among them, In Formula 2, R g 、R h 、R i and R j each independently is a hydrogen atom, a deuterium atom, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, a substituted or unsubstituted oxy group, or a substituted or unsubstituted thio group, "g", "h", "i", and "j" are each independently an integer from 0 to 5, and L, R a to R f and "a" to "f" are the same as defined in Formula 1.

5. The organic electroluminescent device according to claim 1, wherein the emission layer is intended to emit delayed fluorescence.

6. The organic electroluminescent device according to claim 1, wherein The emission layer comprises a host and a dopant, and The dopant comprises the polycyclic compound.

7. The organic electroluminescent device according to claim 1, wherein the emission layer is intended to emit light having a central wavelength of 430 nm to 470 nm.

8. The organic electroluminescent device according to claim 3, wherein Formula 1-1 is represented by any one selected from Formula 1-1J, Formula 1-1L, Formula 1-1M to Formula 1-1O: Among them, In Formula 1-1J, Formula 1-1L, Formula 1-1M to Formula 1-1O, R1 to R 22 and R1' to R 21 ' are each independently a hydrogen atom, a deuterium atom, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted oxy group, or a substituted or unsubstituted thio group.

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