Organic electroluminescent device and polycyclic compound for the same

Abstract

Provided are an organic electroluminescent device and a polycyclic compound for the organic electroluminescent device. The organic electroluminescent device includes a first electrode, a hole transport region on the first electrode, an emission layer on the hole transport region, an electron transport region on the emission layer, and a second electrode on the electron transport region, in which the emission layer includes a polycyclic compound represented by Formula 4: # imgabs0 # wherein in Formula 4, R1 represents a hydrogen atom, R2 represents a hydrogen atom, and R3 represents a hydrogen atom; the variables are the same as described in the specification.

Description

[0001] This application is a divisional application of the patent application 202010012614.7, titled "Organic Electroluminescent Device and Polycyclic Compound for Organic Electroluminescent Device", filed on January 7, 2020. Technical Field

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

[0003] Recently, the development of organic electroluminescent display devices as image display devices has been actively carried out. Different from liquid crystal display devices, an organic electroluminescent display device is a self-luminous display device 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 (which is an organic compound included in the emission layer) emits light to realize the display of an image.

[0004] When applying an organic electroluminescent device to a display device, it is required that the organic electroluminescent device has a low driving voltage, a high luminous efficiency, and a long lifespan. Therefore, there is a continuous need for the development of materials for an organic electroluminescent device that can stably (appropriately) achieve the above requirements.

[0005] For example, in order to realize an organic electroluminescent device with high efficiency, in recent years, techniques using triplet energy emission phosphorescence or using triplet-triplet annihilation (TTA, which is a phenomenon of generating singlet excitons due to the collision of triplet excitons) to emit delayed fluorescence have been developed, and the development of thermally activated delayed fluorescence (TADF) materials using the delayed fluorescence phenomenon has been actively carried out. Summary of the Invention

[0006] One or more aspects of embodiments of the present disclosure relate to an organic electroluminescent device having a long lifespan and high efficiency and a polycyclic compound for the organic electroluminescent device.

[0007] Embodiments of the present disclosure also relate to an organic electroluminescent device including a thermally activated delayed fluorescence emitting material and a polycyclic compound used as a thermally activated delayed fluorescence emitting material.

[0008] Embodiments of the inventive concept provide an organic electroluminescent device including: a first electrode; a hole transport region located on the first electrode; an emission layer located on the hole transport region; an electron transport region located on the emission layer; and a second electrode located on the electron transport region, wherein the emission layer includes a polycyclic compound represented by Formula 1:

[0009] Formula 1

[0010]

[0011] In Formula 1: Ring A and Ring B can each independently be a substituted or unsubstituted aryl having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms, and at least one selected from Ring A and Ring B can be a substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms; Z can be BAr 2 , POAr 3 , PSAr 4 , SiAr 5 Ar 6 or GeAr 7 Ar 8 ; Ar 1 can be a substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms; Ar 2 to Ar 8 can each independently be a substituted or unsubstituted amino group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms, wherein one or more selected from Ar 2 to Ar 8 can combine with adjacent groups to form a ring.

[0012] At least one selected from Ring A and Ring B in Formula 1 can be represented by Formula 2:

[0013] Formula 2

[0014]

[0015] In Formula 2: X and Y can each independently be a direct bond, O, S, SO, SO 2 , Se, NR 3 , PR 4 , POR 5 , PSR 6 , SiR 7 R 8 , GeR 9 R 10 or BR 11 , provided that X and Y cannot both be direct bonds at the same time; and R 1 to R 11Each of them may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a phosphine oxide group, a phosphine sulfide group, a silyl group, a carbonyl group, a boron group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, wherein one or more selected from R 1 to R 11 may combine with an adjacent group to form a ring.

[0016] The emission layer may be configured to emit delayed fluorescence.

[0017] The emission layer may be a delayed fluorescence emission layer including a host and a dopant, wherein the dopant may be a polycyclic compound of Formula 1.

[0018] The emission layer may be a thermally activated delayed fluorescence emission layer configured to emit blue light.

[0019] Formula 1 may be represented by Formula 3:

[0020] Formula 3

[0021]

[0022] In Formula 3: Z′ may be BAr 2 , POAr 3 , PSAr 4 , SiAr 5 Ar 6 or GeAr 7 Ar 8 ; ring L may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms; and ring A, ring B, and Z may be the same as defined in Formula 1.

[0023] In Formula 3, Z and Z' may be the same.

[0024] Formula 1 may be represented by Formula 4:

[0025] Formula 4

[0026]

[0027] In Formula 4: Z may be B, PO, PS, SiAr 5 or GeAr 7 ; ring M may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms; Ar1 ' may be a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms; and ring A, ring B, Ar 1 , Ar 5 and Ar 7 may be the same as defined in formula 1.

[0028] In formula 1, Z may be BAr 2 .

[0029] Z may be represented by formula 5:

[0030] Formula 5

[0031]

[0032] In formula 5, V 1 to V 5 may each independently be CR 12 or N; R 12 may be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted oxy group, a substituted or unsubstituted mercapto group, a substituted or unsubstituted amino group, a phosphinyl group, a phosphinothioyl group, a silyl group, a carbonyl group, a boron group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, wherein R 12 may combine with an adjacent group to form a ring, and * represents the bonding position with an adjacent atom.

[0033] In formula 5, V 1 to V 5 may each independently be CR 12 , wherein R 12 may be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 2 to 10 carbon atoms.

[0034] In formula 1, at least one selected from ring A and ring B may be a substituted or unsubstituted pyrrole, a substituted or unsubstituted thiophene, a substituted or unsubstituted oxazine, or a substituted or unsubstituted furan.

[0035] Formula 1 may be represented by formula 6:

[0036] Formula 6

[0037]

[0038] In formula 6: A1 It may be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted oxy group, a substituted or unsubstituted mercapto group, a substituted or unsubstituted amino group, a phosphine oxide group, a phosphine sulfide group, a silyl group, a carbonyl group, a boron group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, wherein, A 1 may combine with an adjacent group to form a ring; n is an integer from 0 to 5; X and Y may each independently be a direct bond, O, S, SO 2 , Se, NR 3 , PR 4 , POR 5 , PSR 6 , SiR 7 R 8 , GeR 9 R 10 or BR 11 ; R 1 to R 11 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted oxy group, a substituted or unsubstituted mercapto group, a substituted or unsubstituted amino group, a phosphine oxide group, a phosphine sulfide group, a silyl group, a carbonyl group, a boron group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, wherein, one or more selected from R 1 to R 11 may combine with an adjacent group to form a ring; and Ar 1 may be the same as defined in Formula 1.

[0039] The polycyclic compound represented by Formula 1 may be selected from the compounds collectively referred to as Compound Group 1.

[0040] One or more embodiments of the inventive concept provide a polycyclic compound represented by Formula 1. BRIEF DESCRIPTION OF THE DRAWINGS

[0041] The drawings are included to provide a further understanding of the inventive concept and are incorporated into and constitute a part of this specification. The drawings illustrate exemplary embodiments of the inventive concept and, together with the description, are used to explain the principles of the inventive concept. In the drawings:

[0042] Figure 1 is a cross-sectional view schematically showing an organic electroluminescent device according to an embodiment of the inventive concept;

[0043] Figure 2 is a cross-sectional view schematically showing an organic light-emitting device according to an embodiment of the inventive concept; and

[0044] Figure 3 is a cross-sectional view schematically showing an organic light-emitting device according to an embodiment of the inventive concept. Detailed Description

[0045] The inventive concept 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 inventive concept may be implemented in different forms and should not be construed as limited to the embodiments set forth herein. On the contrary, all modifications, equivalents, and alternatives included within the spirit and technical scope of the inventive concept should be included in the inventive concept.

[0046] Like reference numerals always denote like elements. In the drawings, the dimensions of structures are exaggerated for clarity of illustration. It will 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 invention, a first element may be named a second element. Similarly, a second element may be named a first element. As used herein, unless the context clearly indicates otherwise, the singular form is also intended to include the plural form.

[0047] In this specification, it should be understood that the terms "comprising," "including," and / or "having" are intended to indicate that there may be a specific feature, number, step, operation, element, part, or combination thereof, but do not preclude the presence or addition of one or more other specific features, numbers, steps, operations, elements, parts, or combinations thereof. It will also be understood that when a part such as a layer, film, region, plate, etc. is referred to as being "on" another part, the part may be "directly on" the other part, or there may also be an intermediate part. In contrast, when a part such as a layer, film, region, plate, etc. is referred to as being "directly on" another part, there may be no intermediate part.

[0048] When expressions such as "at least one (kind / er) of...," "one (kind / er) of...," and "selected from... (or selected from among...)" are used after (or before) a list of elements, they modify the entire list of elements, rather than individual elements in the list. In addition, when describing embodiments of the present invention, the use of "may" refers to "one or more embodiments of the present invention."

[0049] Hereinafter, reference will be made to Figures 1 to 3To explain an organic light-emitting device according to an embodiment of the inventive concept.

[0050] Referring to Figures 1 to 3 , an organic light-emitting device 10 according to an 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 that are sequentially stacked.

[0051] The first electrode EL1 and the second electrode EL2 may be disposed (e.g., arranged or positioned) to face each other, and a plurality of organic layers may be disposed between the first electrode EL1 and the second electrode EL2. The plurality of organic layers may include a hole transport region HTR, an emission layer EML, and an electron transport region ETR. The organic light-emitting device 10 may include a polycyclic compound of an embodiment of the present disclosure in the emission layer EML.

[0052] Compared with Figure 1 ,, Figure 2 shows a cross-sectional view of an organic light-emitting device 10 according to an embodiment, in which the hole transport region HTR includes a hole injection layer HIL and a hole transport layer HTL, and the electron transport region ETR includes an electron injection layer EIL and an electron transport layer ETL. In addition, compared with Figure 1 ,, Figure 3 shows a cross-sectional view of an organic light-emitting device 10 according to an embodiment, in which the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL, and an electron blocking layer EBL, and the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL, and a hole blocking layer HBL.

[0053] In the organic light-emitting device 10 of one or more embodiments, the first electrode EL1 may have conductivity. The first electrode EL1 may be formed of a metal alloy or a conductive compound. The first electrode EL1 may be an anode.

[0054] The first electrode EL1 can be a transmissive electrode, a transmissive-reflective electrode, or a reflective electrode. When the first electrode EL1 is a transmissive electrode, the first electrode EL1 can be formed of a transparent metal oxide such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc. When the first electrode EL1 is a transmissive-reflective 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, or a compound or mixture thereof (e.g., a mixture of Ag and Mg). In one or more embodiments, the first electrode EL1 can have a structure including multiple layers, the multiple layers including: a reflective layer or a transmissive-reflective layer formed of any of the described materials; and a transparent conductive layer formed of ITO, IZO, ZnO, ITZO, etc. For example, the first electrode EL1 can have a multilayer structure of ITO / Ag / ITO.

[0055] The hole transport region HTR can be disposed 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.

[0056] The hole transport region HTR can have a structure: 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.

[0057] For example, the hole transport region HTR can have a structure of a single layer as the hole injection layer HIL or the hole transport layer HTL, or can have a structure of a single layer formed of a hole injection material and a hole transport material. In one or more embodiments, the hole transport region HTR can have a structure of a single layer formed of multiple different materials, or can have a structure of hole injection layer HIL / hole transport layer HTL, hole injection layer HIL / hole transport layer HTL / hole buffer layer, hole injection layer HIL / hole buffer layer, hole transport layer HTL / hole buffer layer, or hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL sequentially stacked from the first electrode EL1, but the embodiments are not limited thereto.

[0058] The hole transport region HTR can be formed by using one or more suitable methods such as a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Blodgett (LB) method, an inkjet printing method, a laser printing method, and / or a laser-induced thermal imaging (LITI) method.

[0059] The hole injection layer HIL of the organic electroluminescent device 10 of one or more embodiments may include any suitable hole injection material, for example, triphenylamine-containing polyether ketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium tetrakis(pentafluorophenyl)borate (PPBI), N,N'-diphenyl-N,N'-bis[4-(di-m-tolylamino)phenyl]-biphenyl-4,4'-diamine (DNTPD), phthalocyanine compounds such as copper phthalocyanine, 4,4',4''-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPB), N,N'-bis(1-naphthyl)-N,N'-diphenyl-2,2'-dimethyl-biphenyl-4,4'-diamine (α-NPD), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4''-tris(N,N-2-naphthylphenylamino)triphenylamine (2-TNATA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN), etc., but the embodiments of the present disclosure are not limited thereto.

[0060] The hole transport layer HTL of the organic electroluminescent device 10 of one or more embodiments may include any suitable hole transport material, for example, 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC), carbazole derivatives such as N-phenylcarbazole or polyvinylcarbazole, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4,4',4''-tris(N-carbazolyl)triphenylamine (TCTA), N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPB), N,N'-bis(1-naphthyl)-N,N'-diphenyl-2,2'-dimethyl-biphenyl-4,4'-diamine (α-NPD), etc., but the embodiments of the present disclosure are not limited thereto.

[0061] The hole transport region HTR may further include an electron blocking layer EBL, and the electron blocking layer EBL may be disposed between the hole transport layer HTL and the emission layer EML. The electron blocking layer EBL can be used to prevent or reduce the injection of electrons from the electron transport region ETR into the hole transport region HTR.

[0062] The electron blocking layer EBL may include any suitable electron blocking material, for example, carbazole derivatives (such as N-phenylcarbazole and / or polyvinylcarbazole), fluorene derivatives, triphenylamine derivatives (such as 4,4’,4”-tris(N-carbazolyl)triphenylamine (TCTA)), N,N’-bis(3-methylphenyl)-N,N’-diphenyl-(1,1’-biphenyl)-4,4’-diamine (TPD), N,N'-di(naphthalen-1-yl)-N,N'-diphenyl-benzidine (NPB), 4,4’-cyclohexylidene-bis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4’-bis[N,N’-(3-tolyl)amino]-3,3’-dimethylbiphenyl (HMTPD), 1,3-bis(carbazol-9-yl)benzene (mCP), etc. The electron blocking layer EBL may also include a polycyclic compound according to an embodiment of the inventive concept as described herein.

[0063] The thickness of the hole transport region HTR may be about to about For example, about to about The thickness of the hole injection layer HIL may be, for example, about to about The thickness of the hole transport layer HTL may be about to about For example, the thickness of the electron blocking layer EBL may be about to about When the thicknesses of the hole transport region HTR, the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL satisfy any of the described ranges, satisfactory (or suitable) hole transport performance can be achieved without significantly increasing the driving voltage.

[0064] In addition to the described materials, the hole transport region HTR may further include a charge generation material to improve conductivity. The charge generation material may be uniformly or non-uniformly dispersed in the hole transport region HTR. The charge generation material may be, for example, a p-dopant. The p-dopant may be selected from quinone derivatives, metal oxides, and cyanide-containing compounds, but the embodiments of the present disclosure are not limited thereto. Non-limiting examples of the p-dopant may be, for example, quinone derivatives (such as tetracyanoquinodimethane (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ)), metal oxides (such as tungsten oxide and / or molybdenum oxide), etc., but the embodiments of the present disclosure are not limited thereto.

[0065] In addition to the hole injection layer HIL and the hole transport layer HTL, the hole transport region HTR may further include at least one selected from a hole buffer layer and an electron blocking layer EBL. The hole buffer layer may improve the light emission efficiency by compensating for the optical resonance distance according to the wavelength of the light emitted from the emission layer EML. Any of the materials included in the materials of the hole transport region HTR may also be used as the material included in the hole buffer layer.

[0066] The emission layer EML may be disposed on the hole transport region HTR. The emission layer EML may have, for example, a thickness of about to about . The emission layer EML may have a structure: 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.

[0067] The emission layer EML may emit one selected from red light, green light, blue light, white light, yellow light, and cyan light. The emission layer EML may include a fluorescent emission material and / or a phosphorescent emission material.

[0068] In one or more embodiments, the emission layer EML may be a fluorescent emission layer. For example, some of the light emitted from the emission layer EML may be emitted by thermally activated delayed fluorescence (TADF). For example, the emission layer EML may include an emission component (or component) that emits thermally activated delayed fluorescence, and in one or more embodiments, the emission layer EML may be an emission layer that emits blue thermally activated delayed fluorescence.

[0069] In this specification, ─* may refer to a connection site.

[0070] In this specification, the term "substituted or unsubstituted" may refer to a group that is unsubstituted or substituted with at least one substituent selected from a deuterium atom, a halogen atom, a cyano group, a silyl group, an oxy group, a thio group, an amino group, an alkyl group, an alkoxy group, a hydrocarbon ring group, an aryl group, and a heterocyclic group. In addition, each of the substituents listed above may itself be substituted or unsubstituted. For example, a biphenyl group may be an aryl group or a phenyl group substituted with a phenyl group.

[0071] In this specification, the expression "forming a ring by binding to an adjacent group" may refer to forming a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring by binding to an adjacent group. The hydrocarbon ring includes an aliphatic hydrocarbon ring and an aromatic hydrocarbon ring. The heterocyclic ring (or heterocyclic group) includes an aliphatic heterocyclic ring and an aromatic heterocyclic ring. The ring formed by binding to an adjacent group may be a monocyclic ring or a polycyclic ring. In addition, the ring formed by binding may bind to another ring to form a spiro structure.

[0072] In the present specification, the term "adjacent groups" may refer to a pair of substituents in which a first substituent is attached to an atom directly connected to another atom substituted with a second substituent, a pair of substituents attached to the same atom (where the pair of substituents may be different from each other), or a pair of substituents in which the first substituent is spatially located closest to the second substituent. For example, in 1,2-dimethylbenzene, the two methyl groups may be "adjacent groups" to each other, and in 1,1-diethylcyclopentane, the two ethyl groups may be "adjacent groups" to each other.

[0073] In the present specification, "ring-forming atoms (atoms for forming a ring)" may refer to atoms that form a ring.

[0074] In the present specification, a halogen atom may be, for example, a fluorine atom, a chlorine atom, a bromine atom, and / or an iodine atom.

[0075] In the present specification, an alkyl group may have a straight-chain form, a branched-chain form, or a cyclic form. The number of carbon atoms in the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of the alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyl octyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyl decyl, 2-butyl decyl, 2-hexyldecyl, 2-octyl decyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyl dodecyl, 2-hexyldodecyl, 2-octyl dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butyl hexadecyl, 2-hexyl hexadecyl, 2-octyl hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyl eicosyl, 2-hexyl eicosyl, 2-octyl eicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, etc., but the embodiments of the present disclosure are not limited thereto. In the present specification, iPr may represent isopropyl.

[0076] In this specification, an aryl group may refer to an aromatic hydrocarbon ring functional group or substituent. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. The number of ring-forming carbon atoms in the aryl group may be from 6 to 30, from 6 to 20, or from 6 to 15. Examples of the aryl group may include a phenyl group, a naphthyl group, a fluorenyl group, an anthracenyl group, a phenanthryl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a quinquephenyl group, a sexiphenyl group, a benzo[9,10]phenanthryl group, a pyrenyl group, a benzofluoranthenyl group, groups, etc., but the embodiments of the present disclosure are not limited thereto. In this specification, Ph may represent a phenyl group.

[0077] In this specification, the fluorenyl group may be substituted, and two substituents may optionally combine with each other to form a spiro structure. Examples of the substituted fluorenyl group are as follows, but the embodiments of the present disclosure are not limited thereto:

[0078]

[0079] In this specification, a heteroaryl group may be a cyclic aromatic group including one or more of O, N, P, Si, S, Se, Ge, and B as ring-forming heteroatoms. The number of ring-forming carbon atoms in the heteroaryl group may be from 2 to 30 or from 2 to 20. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. The polycyclic heteroaryl group may have, for example, a bicyclic structure or a tricyclic structure. Examples of the heteroaryl group may include a thienyl group, a furyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidinyl group, a triazinyl group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxazinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolinyl group, an indolyl group, a carbazolyl group, an N-arylcarbazolyl group, an N-heteroarylcarbazolyl group, an N-alkylcarbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothienyl group, a dibenzothienyl group, a thienothienyl group, a benzofuryl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a dibenzothiophenylene group, a dibenzofuryl group, etc., but the embodiments of the present disclosure are not limited thereto.

[0080] In this specification, a silyl group includes an alkylsilyl group and an arylsilyl group. Examples of the silyl group may include a trimethylsilyl group, a triethylsilyl group, a tert-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, etc., but the embodiments of the present disclosure are not limited thereto.

[0081] In the present specification, the number of carbon atoms of the amino group is not particularly limited, but may be from 1 to 30. The amino group may include an alkylamino group and an arylamino group. Examples of the amino group may include methylamino, dimethylamino, phenylamino, naphthylamino, 9-methyl-anthrylamino, diphenylamino, etc., but the embodiments of the present disclosure are not limited thereto.

[0082] In one or more embodiments, the emission layer EML may include a polycyclic compound represented by Formula 1:

[0083] Formula 1

[0084]

[0085] In Formula 1, Ring A and Ring B may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

[0086] In Formula 1, at least one selected from Ring A and Ring B may be a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. On the contrary, when neither Ring A nor Ring B is a heteroaryl group, the molecular stability is reduced, resulting in deterioration of the luminous efficiency and / or lifetime of the organic electroluminescent device in which the polycyclic compound is used.

[0087] In Formula 1, Z may be BAr 2 , POAr 3 , PSAr 4 , SiAr 5 Ar 6 or GeAr 7 Ar 8 .

[0088] In Formula 1, Ar 1 may be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

[0089] In Formula 1, Ar 2 to Ar 8 may each independently be a substituted or unsubstituted amino group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and one or more selected from Ar 2 to Ar 8 may combine with an adjacent group to form a ring. In other words, one or more selected from Ar 2to Ar 8 One or more selected from the group consisting of optionally (or "optionally") combine with adjacent groups to form a ring.

[0090] In one or more embodiments, at least one selected from ring A and ring B in Formula 1 may be represented by Formula 2:

[0091] Formula 2

[0092]

[0093] In Formula 2, X and Y may each independently be a direct bond, O, S, SO, SO 2 , Se, NR 3 , PR 4 , POR 5 , PSR 6 , SiR 7 R 8 , GeR 9 R 10 or BR 11 .

[0094] In Formula 2, R 1 to R 11 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a phosphine oxide group, a phosphine sulfide group, a silyl group, a carbonyl group, a boron group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and one or more selected from R 1 to R 11 may combine with adjacent groups to form a ring.

[0095] Formula 2 represents an embodiment in which one selected from ring A and ring B in Formula 1 is a heteroaryl ring (heteroaryl group), and excludes the case where X and Y in Formula 2 are both direct bonds at the same time.

[0096] In one or more embodiments, Ar in Formula 1 1 may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and Ar 1 may combine with adjacent groups to form a ring.

[0097] In one or more embodiments, when Ar in Formula 1 1When it is an aryl or heteroaryl that binds to an adjacent group to form a ring, Formula 1 can be represented by Formula 3:

[0098] Formula 3

[0099]

[0100] In Formula 3, Z′ can be BAr 2 , POAr 3 , PSAr 4 , SiAr 5 Ar 6 or GeAr 7 Ar 8 .

[0101] In Formula 3, ring L can be a substituted or unsubstituted aryl having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroaryl having 2 to 30 ring-forming carbon atoms.

[0102] In Formula 3, ring A, ring B and Z can be the same as those defined in Formula 1.

[0103] In one or more embodiments, Z and Z' in Formula 3 can be the same as each other.

[0104] In one or more embodiments, Ar 2 to Ar 8 in Formula 1 can each independently be a substituted or unsubstituted aryl having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted aralkyl having 7 to 30 carbon atoms or a substituted or unsubstituted heteroaryl having 2 to 30 ring-forming carbon atoms, and one or more selected from Ar 2 to Ar 8 can bind to an adjacent group to form a ring.

[0105] In one or more embodiments, when Ar 2 to Ar 8 in Formula 1 are each independently an aryl or heteroaryl that binds to an adjacent group to form a ring, Formula 1 can be represented by Formula 4:

[0106] Formula 4

[0107]

[0108] In Formula 4, Z can be B, PO, PS, SiAr 5 or GeAr 7 .

[0109] In Formula 4, ring M can be a substituted or unsubstituted aryl having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroaryl having 2 to 30 ring-forming carbon atoms.

[0110] In Formula 4, Ar 1 ' can be a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0111] In Formula 4, Ring A, Ring B, Ar 1 , Ar 5 and Ar 7 can be the same as defined in Formula 1.

[0112] In one or more embodiments, Z in Formula 1 can be BAr 2 .

[0113] In one or more embodiments, when Z in Formula 1 is BAr 2 , Z can be represented by Formula 5:

[0114] Formula 5

[0115]

[0116] In Formula 5, V 1 to V 5 can each independently be CR 12 or N. At least one selected from V 1 to V 5 can be CR 12 .

[0117] In Formula 5, R 12 can be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a phosphine oxide group, a phosphine sulfide group, a silyl group, a carbonyl group, a boron group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. One or more R 12 can combine with adjacent groups to form a ring, and * represents the bonding position to an adjacent atom.

[0118] In one or more embodiments, V 1 to V 5 in Formula 5 can each independently be CR 12 , where R 12 can be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 2 to 10 carbon atoms.

[0119] In one or more embodiments, at least one selected from Ring A and Ring B in Formula 1 may be a substituted or unsubstituted pyrrole, a substituted or unsubstituted thiophene, a substituted or unsubstituted oxazine, or a substituted or unsubstituted furan.

[0120] In one or more embodiments, Formula 1 may be represented by Formula 6:

[0121] Formula 6

[0122]

[0123] In Formula 6, A 1 may be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a phosphinyl group, a phosphinothioyl group, a silyl group, a carbonyl group, a boron group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and one or more A 1 may combine with adjacent groups to form a ring.

[0124] In Formula 6, n may be an integer from 0 to 5. When n is 2 or greater, multiple A 1 may be the same as or different from each other.

[0125] In Formula 6, X and Y may each independently be a direct bond, O, S, SO, 2 Se, NR 3 PR 4 POR 5 PSR 6 SiR 7 R 8 GeR 9 R 10 or BR 11 .

[0126] In Formula 6, R 1 to R 11 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a phosphinyl group, a phosphinothioyl group, a silyl group, a carbonyl group, a boron group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and from R 1 to R 11One or more selected from the following may combine with adjacent groups to form a ring.

[0127] In Formula 6, Ar 1 may be the same as defined in Formula 1.

[0128] The polycyclic compound of this embodiment represented by Formula 1 may be a delayed fluorescence emission material. The polycyclic compound of this embodiment may be a thermally activated delayed fluorescence material.

[0129] For example, the polycyclic compound represented by Formula 1 may have a small difference between the singlet energy level (S1) and the triplet energy level (T1), and thus be used as a thermally activated delayed fluorescence material. The polycyclic compound represented by Formula 1 in the embodiment may be represented by any one selected from the compounds in Compound Group 1:

[0130] Compound Group 1

[0131]

[0132]

[0133] The described polycyclic compound represented by Formula 1 can be used in the organic electroluminescent device 10 of one or more embodiments to improve the luminous efficiency and / or lifespan of the organic electroluminescent device 10. For example, the described polycyclic compound represented by Formula 1 can be used in the emission layer EML of the organic electroluminescent device 10 to improve the luminous efficiency and / or lifespan of the organic electroluminescent device 10.

[0134] In one or more embodiments, the emission layer EML may include a host and a dopant. The host can be used for delayed fluorescence emission, and the dopant can be used for delayed fluorescence emission. The polycyclic compound represented by Formula 1 can be included as a dopant material in the emission layer EML. For example, the polycyclic compound represented by Formula 1 can be used as a TADF dopant.

[0135] In one or more embodiments, the emission layer EML may include any suitable host material, for example, tris(8-hydroxyquinoline) aluminum (Alq 3) 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), 2-tert-butyl-9,10-bis(naphthalen-2-yl)anthracene (TBADN), distyrylarylene compound (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 (DPSiO 3 ) octaphenylcyclotetrasiloxane (DPSiO 4 ) 2,8-bis(diphenylphosphoryl)dibenzofuran (PPF), etc. However, the embodiments of the present disclosure are not limited thereto, and any suitable delayed fluorescence emitting host material may be included (including) in addition to the described host materials.

[0136] In addition, the emission layer EML of the organic electroluminescent device 10 of this embodiment may include any suitable dopant material, for example, styryl derivatives (such as 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 (such as 2,5,8,11-tetra-tert-butylperylene (TBP)), pyrene and / or its derivatives (such as 1,1'-dipyrene, 1,4-dipyrenylbenzene and / or 1,4-bis(N,N-diphenylamino)pyrene), etc.

[0137] Referring again to Figures 1 to 3 , in the organic electroluminescent device 10 of the embodiment, the electron transport region ETR may be disposed on the emission layer EML. The electron transport region ETR may include at least one selected from the hole blocking layer HBL, the electron transport layer ETL, and the electron injection layer EIL, but the embodiments of the present disclosure are not limited thereto.

[0138] The electron transport region ETR may have a structure: 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.

[0139] For example, the electron transport region ETR may have a structure of a single layer as an electron injection layer EIL or an electron transport layer ETL, or may have a structure of a single layer formed of an electron injection material and an electron transport material. In one or more embodiments, the electron transport region ETR may have a structure of a single layer formed of a plurality of different materials, or may have 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 sequentially stacked from the emission layer EML. However, the embodiments of the present disclosure are not limited thereto. The thickness of the electron transport region ETR may be, for example, about to about

[0140] One or more suitable methods (such as a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Blodgett (LB) method, an inkjet printing method, a laser printing method, and / or a laser-induced thermal imaging (LITI) method) may be used to form the electron transport region ETR.

[0141] When the electron transport region ETR includes an electron transport layer ETL, the electron transport region ETR may include, for example, tris(8-hydroxyquinoline)aluminum (Alq 3 )), 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-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-ol)aluminum (BAlq), bis(benzoquinoline-10-hydroxy)beryllium (Bebq 2 )), and / or 9,10-di(naphthalen-2-yl)anthracene (ADN). However, the embodiments of the present disclosure are not limited thereto.

[0142] When the electron transport region ETR includes an electron transport layer ETL, the thickness of the electron transport layer ETL may be about to about For example, about to about When the thickness of the electron transport layer (ETL) satisfies the described range, satisfactory (or appropriate) electron transport performance can be achieved without significantly increasing the driving voltage.

[0143] When the electron transport region (ETR) includes an electron injection layer (EIL), the electron transport region (ETR) may include, for example, metal halides (such as LiF, NaCl, CsF, RbCl, RbI, and / or KI), lanthanide metals (such as Yb), metal oxides (such as Li 2 O, BaO), and / or lithium quinolate (LiQ), etc., but the embodiments of the present disclosure are not limited thereto. The electron injection layer (EIL) may also be formed of a mixture of an electron transport material and an insulating organometallic salt. The organometallic salt may be a material having a band gap of about 4 eV or more. In one or more embodiments, the organometallic salt may include, for example, metal acetates, metal benzoates, metal acetoacetates, metal acetylacetonates, and / or metal stearates.

[0144] When the electron transport region (ETR) includes an electron injection layer (EIL), the thickness of the electron injection layer (EIL) may be about to about or about to about When the thickness of the electron injection layer (EIL) satisfies the described range, satisfactory (or appropriate) electron injection performance can be achieved without significantly increasing the driving voltage.

[0145] The electron transport region (ETR) may include a hole blocking layer (HBL) as described above. The hole blocking layer (HBL) may include at least one selected from, for example, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) and 4,7-diphenyl-1,10-phenanthroline (Bphen), but the embodiments of the present disclosure are not limited thereto.

[0146] The second electrode (EL2) may be disposed on the electron transport region (ETR). The second electrode (EL2) may have conductivity. The second electrode (EL2) may be formed of a metal alloy and / or a conductive compound. The second electrode (EL2) may be a cathode. The second electrode (EL2) may be a transmissive electrode, a transmissive-reflective electrode, or a reflective electrode. When the second electrode (EL2) is a transmissive electrode, the second electrode (EL2) may be formed of a transparent metal oxide such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc.

[0147] When the second electrode EL2 is a transmissive reflective electrode or a reflective electrode, the second electrode EL2 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, or a compound or mixture thereof (e.g., a mixture of Ag and Mg). In one or more embodiments, the second electrode EL2 may have a structure with multiple layers, the multiple layers including: a reflective layer or a transmissive reflective layer formed of any of the described materials; and a transparent conductive layer formed of ITO, IZO, ZnO, ITZO, etc.

[0148] In one or more embodiments, the second electrode EL2 may be connected to an auxiliary electrode. When the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.

[0149] In the organic electroluminescent device 10, when voltages are applied to the first electrode EL1 and the second electrode EL2, respectively, holes injected from the first electrode EL1 may move to the emission layer EML through the hole transport region HTR, and electrons injected from the second electrode EL2 may move to the emission layer EML through the electron transport region ETR. Electrons and holes may recombine in the emission layer EML to generate excitons, and the excitons may emit light when the excitons fall back from the excited state to the ground state.

[0150] When the organic electroluminescent device 10 is a top emission type (e.g., a top emission organic electroluminescent device), the first electrode EL1 may be a reflective electrode, and the second electrode EL2 may be a transmissive electrode or a transmissive reflective electrode. When the organic electroluminescent device 10 is a bottom emission type (e.g., a bottom emission organic electroluminescent device), the first electrode EL1 may be a transmissive electrode or a transmissive reflective electrode, and the second electrode EL2 may be a reflective electrode.

[0151] The organic electroluminescent device 10 according to one or more embodiments of the inventive concept may exhibit improved luminous efficiency and lifetime characteristics when using the polycyclic compound of the present embodiment described as an emission layer material.

[0152] Embodiments of the inventive concept provide a polycyclic compound represented by Formula 1:

[0153] Formula 1

[0154]

[0155] In Formula 1, Ring A and Ring B may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

[0156] In Formula 1, at least one selected from Ring A and Ring B may be a substituted or unsubstituted heteroaryl having 2 to 30 ring-forming carbon atoms. On the contrary, when neither Ring A nor Ring B is a heteroaryl, the molecular stability is reduced, so that when the polycyclic compound is applied to an organic electroluminescent device, the luminous efficiency and / or lifespan deteriorate.

[0157] In Formula 1, Z may be BAr 2 , POAr 3 , PSAr 4 , SiAr 5 Ar 6 or GeAr 7 Ar 8 .

[0158] In Formula 1, Ar 1 may be a substituted or unsubstituted aryl having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 30 ring-forming carbon atoms.

[0159] In Formula 1, Ar 2 to Ar 8 may each independently be a substituted or unsubstituted amino group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and one or more selected from Ar 2 to Ar 8 may combine with adjacent groups to form a ring.

[0160] In one or more embodiments, at least one selected from Ring A and Ring B in Formula 1 may be represented by Formula 2:

[0161] Formula 2

[0162]

[0163] In Formula 2, X and Y may each independently be a direct bond, O, S, SO, SO 2 , Se, NR 3 , PR 4 , POR 5 , PSR 6 , SiR 7 R 8 , GeR 9 R 10 or BR 11 .

[0164] In Formula 2, R 1 to R 11 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a phosphine oxide group, a phosphine sulfide group, a silyl group, a carbonyl group, a boron group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and one or more selected from R 1 to R 11 may combine with adjacent groups to form a ring.

[0165] Formula 2 represents an embodiment in which one selected from Ring A and Ring B in Formula 1 is a heteroaryl group, and excludes the case where X and Y in Formula 2 are both direct bonds at the same time.

[0166] The description of the polycyclic compound provided in the organic electroluminescent device of this embodiment can be similarly applied to the polycyclic compound represented by Formula 1 of this embodiment.

[0167] The polycyclic compound according to the embodiment may be any one selected from the compounds collectively referred to as Compound Group 1.

[0168] Hereinafter, the inventive concept will be explained in more detail with reference to exemplary and comparative examples. However, the following embodiments are merely examples intended to facilitate the understanding of the inventive concept, and the scope of the inventive concept is not limited thereto.

[0169] Synthesis Example

[0170] The polycyclic compound according to the embodiment of the inventive concept can be synthesized, for example, according to the following examples. However, the synthesis method of the polycyclic compound according to the embodiment of the inventive concept is not limited thereto.

[0171] 1. Synthesis of Compound 8

[0172] The polycyclic compound 8 according to the embodiment of the inventive concept can be synthesized, for example, in the following manner:

[0173]

[0174] Synthesis of Intermediate Compound A

[0175] Under an Ar atmosphere, 9.63 g (20 mmol) of N 1 -(2,3-dichlorophenyl)-N 1 ,N 3 ,N 3-Triphenyl-1,3-benzenediamine, 2.0 mL (22 mmol) of aniline, 0.71 g (1.0 mmol) of dichloro-bis[di-tert-butyl-(4-dimethylaminophenyl)phosphine]palladium(II) ((Amphos)PdCl 2 ) and 2.11 g (22 mmol) of NaOtBu were added to a 300 mL three-necked flask, and the mixture was stirred at 120 °C for 1 hour in 100 mL of xylene solvent. After air cooling, water was added thereto to separate the organic layer, and the solvent was distilled off. The obtained crude product was purified by column chromatography (silica gel) to obtain 7.40 g of Compound A as a white solid (yield 69%). The molecular weight of Compound A measured by fast atom bombardment mass spectrometry (FAB-MS) was 537.

[0176] Synthesis of Intermediate Compound B

[0177] Under an Ar atmosphere, 7.37 g (13.7 mmol) of Compound A, 4.08 g (15.0 mmol) of 2-bromo-1-phenyl-1H-indole, 0.13 g (0.14 mmol) of Pd 2 (dba) 3 , 0.26 g (0.55 mmol) of 2-dicyclohexylphosphino-2',6'-diisopropoxy-1,1'-biphenyl (Ruphos) and 1.44 g (15.0 mmol) of NaOtBu were added to a 200 mL three-necked flask, and the mixture was stirred at 100 °C for 3 hours in 70 mL of toluene solvent. After air cooling, water was added thereto to separate the organic layer, and the solvent was distilled off. The obtained crude product was purified by column chromatography (silica gel) to obtain 6.79 g of Compound B as a white solid (yield 68%). The molecular weight of Compound B measured by FAB-MS was 728.

[0178] Synthesis of Compound 8

[0179] Under an Ar atmosphere, 50 mL of a dehydrated tert-butylbenzene solution of Compound B (6.78 g (9.3 mmol)) was added to a 300 mL three-necked flask and stirred at -78 °C, and then 19.5 mL (37 mmol) of a 1.9 M pentane solution of tert-butyllithium (t-BuLi) was added dropwise thereto. After the addition was complete, the temperature was raised to 60 °C and the mixture was stirred for 2 hours, and then the components having a boiling point lower than that of tert-butylbenzene were distilled off under reduced pressure. The resulting mixture was cooled to -30 °C, and 1.8 mL (19 mmol) of BBr 3After the addition was completed, the temperature was raised to room temperature, and the mixture was stirred for 2 hours. Thereafter, the mixture was cooled again to 0 °C, and 1.7 mL (9.8 mmol) of N,N-diisopropylethylamine was added dropwise thereto. After the addition was completed, the temperature was raised to room temperature, and the mixture was stirred for 1 hour. Then, the temperature was raised to 120 °C, and the mixture was heated and stirred for 8 hours. The obtained reaction solution was cooled to room temperature, and toluene and an aqueous solution of NaOAc cooled in an ice bath were added to separate the solution. Subsequently, the solution was purified by short column chromatography (silica gel) and recrystallized with a toluene / hexane solvent to obtain 5.09 g of compound 8 as a yellow solid (yield 78%).

[0180] Compound 8 was confirmed by FAB-MS and NMR. The molecular weight of compound 8 measured by FAB-MS was 702, and by 1 1H-NMR (CDCl 3 ) the chemical shift values δ of compound 8 were: 8.43 (1H), 7.94 (1H), 7.69 - 7.48 (6H), 7.37 - 7.22 (11H), 7.10 - 6.98 (12H), and 6.86 - 6.81 (4H).

[0181] 2. Synthesis of Compound 10

[0182] The polycyclic compound 10 according to an embodiment of the inventive concept can be synthesized, for example, according to the following manner:

[0183]

[0184] Synthesis of Intermediate Compound C

[0185] Under an Ar atmosphere, 6.28 g (20 mmol) of 2,3-dichlorophenyl-diphenylamine, 2.0 mL (22 mmol) of aniline, 0.71 g (1.0 mmol) of (Amphos)PdCl 2 and 2.11 g (22 mmol) of NaOtBu were added to a 300 mL three-necked flask, and the mixture was stirred at 120 °C for 1 hour in 100 mL of xylene solvent. After air cooling, water was added thereto to separate the organic layer, and the solvent was distilled off. The obtained crude product was purified by column chromatography (silica gel) to obtain 6.00 g of compound C as a white solid (yield 81%). The molecular weight of compound C measured by FAB-MS was 370.

[0186] Synthesis of Intermediate Compound D

[0187] Under an Ar atmosphere, 5.97 g (16.1 mmol) of compound C, 4.38 g (17.7 mmol) of 3-bromo-6-chloro-benzo[b]thiophene, 0.15 g (0.16 mmol) of Pd 2 (dba) 3 , 0.30 g (0.64 mmol) of Ruphos and 1.70 g (17.7 mmol) of NaOtBu were added to a 200 mL three-necked flask, and in 80 mL of toluene solvent, the mixture was stirred at 100 °C for 3 hours. After air cooling, water was added thereto to separate the organic layer, and the solvent was distilled off. The obtained crude product was purified by column chromatography (silica gel) to obtain 5.27 g of compound D as a white solid (yield 61%). The molecular weight of compound D measured by FAB-MS was 536.

[0188] Synthesis of intermediate compound E

[0189] Under an Ar atmosphere, 5.26 g (9.8 mmol) of compound D, 1.66 g (9.8 mmol) of diphenylamine, 0.18 g (0.20 mmol) of Pd 2 (dba) 3 , 0.36 g (0.78 mmol) of Ruphos and 1.04 g (10.8 mmol) of NaOtBu were added to a 200 mL three-necked flask, and in 50 mL of toluene solvent, the mixture was stirred at 110 °C for 8 hours. After air cooling, water was added thereto to separate the organic layer, and the solvent was distilled off. The obtained crude product was purified by column chromatography (silica gel) to obtain 5.05 g of compound E as a white solid (yield 77%). The molecular weight of compound E measured by FAB-MS was 669.

[0190] Synthesis of compound 10

[0191] Under an Ar atmosphere, 40 mL of a dehydrated tert-butylbenzene solution of compound E (5.03 g (7.5 mmol)) was added to a 300 mL three-necked flask and stirred at -78 °C, then 15.8 mL (30 mmol) of a 1.9 M t-BuLi pentane solution was added dropwise thereto. After the addition was completed, the temperature was raised to 60 °C and the mixture was stirred for 2 hours. Thereafter, the components having a boiling point lower than that of tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -30 °C, and 1.4 mL (15 mmol) of BBr 3After the addition was complete, the temperature was raised to room temperature, and the mixture was stirred for 2 hours. Thereafter, the mixture was cooled again to 0 °C, and 1.4 mL (8.0 mmol) of N,N-diisopropylethylamine was added dropwise thereto. After the addition was complete, the temperature was raised to room temperature, and the mixture was stirred for 1 hour. Then, the temperature was raised to 120 °C, and the mixture was heated and stirred for 8 hours. The resulting reaction solution was cooled to room temperature, and toluene and an aqueous NaOAc solution cooled in an ice bath were added to separate the solution. Subsequently, the solution was purified by flash column chromatography (silica gel) and recrystallized with a toluene / hexane solvent to obtain 4.00 g of compound 10 as a yellow solid (yield 83%).

[0192] Compound 10 was confirmed by FAB-MS and NMR. The molecular weight of compound 10 measured by FAB-MS was 643, and the chemical shift value δ of compound 10 measured by 1 1H-NMR (CDCl 3 ) was: 8.01 (1H), 7.77 (1H), 7.71 (1H), 7.43 (1H), 7.31 - 7.16 (11H), 7.10 - 6.98 (13H), and 6.86 - 6.82 (2H).

[0193] 3. Synthesis of Compound 11

[0194] The polycyclic compound 11 according to an embodiment of the inventive concept can be synthesized, for example, in the following manner:

[0195]

[0196] Synthesis of Intermediate Compound F

[0197] Under an Ar atmosphere, 100 mL of a dehydrated THF solution of 6-chloro-1-phenyl-1H-indole (4.55 g (20 mmol)) was added to a 500 mL three-necked flask and stirred at -78 °C. Then, 13 mL (21 mmol) of a 1.6 M n-BuLi hexane solution was added dropwise thereto (added drop by drop) and stirred for 2 hours. 20 mL of a dehydrated THF solution of 5.33 g (21 mmol) of iodine was added dropwise thereto and stirred at -78 °C for 2 hours, and then stirred at room temperature for 3 hours. After the reaction, the mixture was washed with water. The obtained organic phase was concentrated to obtain a viscous material. The obtained crude product was purified by column chromatography (silica gel) to obtain 6.00 g of compound F as a white solid (yield 85%). The molecular weight of compound F measured by FAB-MS was 353.

[0198] Synthesis of Intermediate Compound G

[0199] Under an Ar atmosphere, 5.98 g (16.9 mmol) of compound F, 4.78 g (16.9 mmol) of 2-bromo-5-chloro-N-phenyl-aniline, 0.16 g (0.17 mmol) of Pd 2 (dba) 3 , 0.25 g (0.34 mmol) of dppf and 1.79 g (18.6 mmol) of NaOtBu were added to a 300 mL three-necked flask, and the mixture was stirred at 80 °C for 6 hours in 85 mL of toluene solvent. After air cooling, water was added thereto to separate the organic layer, and the solvent was distilled off. The obtained crude product was purified by column chromatography (silica gel) to obtain 4.96 g of compound G as a white solid (yield 58%). The molecular weight of compound G measured by FAB-MS was 506.

[0200] Synthesis of intermediate compound H

[0201] Under an Ar atmosphere, 100 mL of a dehydrated THF solution of compound G (4.93 g (9.7 mmol)) was added to a 500 mL three-necked flask and stirred at -78 °C. Then, 12.5 mL (20 mmol) of a 1.6 M n-BuLi hexane solution was added dropwise thereto and stirred for 2 hours. After that, 1.0 mL (10 mmol) of BBr 3 was added dropwise thereto and stirred at -78 °C for 1 hour, and then stirred at room temperature for 3 hours. The mixture was cooled to 0 °C, and then 10 mL (10 mmol) of a 1.0 M THF solution of 2,4,6-triisopropylphenylmagnesium bromide was added dropwise thereto and stirred at 0 °C for 2 hours and stirred at room temperature for 3 hours. After the reaction, the mixture was washed with water. The obtained organic phase was concentrated to obtain a viscous material. The obtained crude product was purified by column chromatography (silica gel) to obtain 4.36 g of compound H as a yellow solid (yield 70%). The molecular weight of compound H measured by FAB-MS was 640.

[0202] Synthesis of compound 11

[0203] Under an Ar atmosphere, 4.35 g (6.8 mmol) of compound H, 2.30 g (13.6 mmol) of diphenylamine, 0.31 g (0.34 mmol) of Pd 2 (dba) 3, 0.63 g (1.36 mmol) of Ruphos and 1.44 g (15.0 mmol) of NaOtBu were added to a 200 mL three-necked flask, and the mixture was stirred at 110 °C for 8 hours in 70 mL of toluene solvent. After air cooling, water was added thereto to separate the organic layer, and the solvent was distilled off. The obtained crude product was purified by column chromatography (silica gel) to obtain 3.20 g of compound 11 as a yellow solid (yield: 52%).

[0204] Compound 11 was confirmed by FAB-MS and NMR. The molecular weight of compound 11 measured by FAB-MS was 906, and by 1 1H-NMR (CDCl 3 ) the chemical shift value δ of compound 11 was: 8.39 (1H), 7.69 - 7.56 (5H), 7.31 - 7.22 (12H), 7.10 - 6.98 (15H), 6.86 - 6.81 (2H), 6.40 (1H), 2.90 - 2.85 (3H), and 1.22 - 1.16 (18H).

[0205] 4. Synthesis of Compound 12

[0206] The polycyclic compound 12 according to an embodiment of the inventive concept can be synthesized, for example, in the following manner:

[0207]

[0208] Synthesis of Intermediate Compound I

[0209] Under an Ar atmosphere, 9.86 g (50 mmol) of 4,4'-dimethyl diphenylamine (p,p′-ditolylamine), 10.65 g (50 mmol) of 2-bromo-benzo[b]thiophene, 0.46 g (0.50 mmol) of Pd 2 (dba) 3 , 0.93 g (2.0 mmol) of Ruphos and 5.29 g (55 mmol) of NaOtBu were added to a 500 mL three-necked flask, and the mixture was stirred at 100 °C for 2 hours in 250 mL of toluene solvent. After air cooling, water was added thereto to separate the organic layer, and the solvent was distilled off. The obtained crude product was purified by column chromatography (silica gel) to obtain 15.15 g of compound I as a white solid (yield: 92%). The molecular weight of compound I measured by FAB-MS was 329.

[0210] Synthesis of Intermediate Compound K

[0211] 15.13 g (46 mmol) of Compound I and 25.45 g (143 mmol) of N-bromosuccinimide (NBS) were added to a 1000 mL round-bottom flask, and 30 mL of acetic acid was added thereto. The mixture was stirred at 0 °C in 300 mL of chloroform solvent for 2 hours. After air cooling, an aqueous solution of sodium thiosulfate was added to separate the organic layer, and the solvent was distilled off. The obtained crude product was purified by column chromatography (silica gel) to obtain 23.16 g of Compound K as a white solid (yield 89%). The molecular weight of Compound K measured by FAB-MS was 562.

[0212] Synthesis of Compound 12

[0213] Under an Ar atmosphere, 160 mL of a dehydrated tert-butylbenzene solution of Compound K (23.13 g (40.9 mmol)) was added to a 1000 mL three-necked flask and stirred at -78 °C. Then, 129 mL (245 mmol) of a 1.9 M solution of t-BuLi in pentane was added dropwise thereto. After the addition was complete, the temperature was raised to room temperature and the mixture was stirred for 2 hours. Thereafter, the mixture was cooled to -30 °C, and 7.8 mL (82 mmol) of BBr 3 . After the addition was complete, the temperature was raised to room temperature and the mixture was stirred for 2 hours. Thereafter, the mixture was cooled to 0 °C again, and 14.9 mL (82 mmol) of 1,2,2,6,6-pentamethylpiperidine was added dropwise thereto. After the addition was complete, the temperature was raised to room temperature and the mixture was stirred for 1 hour. Then, the temperature was raised to 160 °C and the mixture was heated and stirred for 10 hours. The reaction solution was cooled to 0 °C, and 164 mL (164 mmol) of a 1.0 M solution of 2,4,6-trimethylphenylmagnesium bromide in THF was added dropwise thereto, and the mixture was stirred at 0 °C for 2 hours and at room temperature for 3 hours. After the reaction, a phosphate buffer solution (pH 6) and toluene were added to separate the solution. Subsequently, the solution was purified by column chromatography (silica gel) and recrystallized with a toluene / hexane solvent to obtain 4.55 g of Compound 12 as a yellow solid (yield 19%).

[0214] Compound 12 was confirmed by FAB-MS and NMR. The molecular weight of Compound 12 measured by FAB-MS was 585. By 1 H-NMR (CDCl 3)The measured chemical shift values δ of Compound 12 are as follows: 8.05 (1H), 7.93 (1H), 7.51 - 7.40 (2H), 7.19 - 7.11 (5H), 6.99 - 6.95 (4H), 2.38 - 2.31 (18H), and 2.20 - 2.16 (6H).

[0215] Examples of device fabrication

[0216] The organic electroluminescent devices in Examples 1 to 4 were fabricated using the polycyclic compounds of Compound 8, Compound 10, Compound 11, and Compound 12 described above as the emitting layer materials. The compounds used in the emitting layers of Examples 1 to 4 are shown below:

[0217] [Compounds in the examples]

[0218]

[0219] The organic electroluminescent devices in Comparative Examples 1 to 4 were fabricated using the comparative compounds R-1 to R-4 shown below as the emitting layer materials:

[0220] [Compounds in the comparative examples]

[0221]

[0222] The organic electroluminescent devices in Examples 1 to 4 and Comparative Examples 1 to 4 were each independently formed by performing the following process: Patterning ITO with a thickness of and washing with ultrapure water, and treating with UV ozone for 10 minutes; thereafter, depositing HAT-CN to have a thickness of and depositing α-NPD to have a thickness of and depositing mCP to have a thickness of to form a hole transport region;

[0223] Next, by co-depositing each polycyclic compound or each comparative compound of this example and DPEPO at a ratio of 20:80 to form a layer with a thickness of to form an emitting layer; then, using DPEPO to form a layer with a thickness of Thus, in Examples 1 to 4, the emitting layers formed by co-deposition were deposited by mixing Compound 8, Compound 10, Compound 11, and Compound 12 with DPEPO respectively, and in Comparative Examples 1 to 4, the emitting layers formed by co-deposition were deposited by mixing Comparative Compound R-1, Comparative Compound R-2, Comparative Compound R-3, and Comparative Compound R-4 with DPEPO respectively;

[0224] A layer with a thickness is formed on the emission layer using TPBi, and a layer with a thickness is formed using LiF, thereby forming an electron transport region. Subsequently, a second electrode with a thickness is formed using aluminum (Al).

[0225] The hole transport region, emission layer, electron transport region, and second electrode are formed using a vacuum deposition device.

[0226] Performance evaluation of the organic electroluminescent device

[0227] The maximum emission wavelength (nm) and external quantum yield (%) are measured to evaluate the characteristics of the organic electroluminescent devices according to the examples and comparative examples. In the measurement, a luminance orientation characteristic measurement device of Hamamatsu Photonics C9920-11 is used as the measurement device. The lifetime represents the luminance half-life starting from the initial luminance of 100 cd / m 2 , and EQE (external quantum efficiency or external quantum yield) refers to the value at 10 mA / cm 2 .

[0228] Table 1

[0229]

[0230] Referring to Table 1, it can be found that, compared with the organic electroluminescent devices of Comparative Examples 1 to 4, the organic electroluminescent devices in Examples 1 to 4 in which the polycyclic compound of this embodiment is used as a dopant material in the emission layer exhibit high external quantum efficiency. It can also be found that, compared with the organic electroluminescent devices of Comparative Examples 1 to 4, the organic electroluminescent devices in Examples 1 to 4 in which the polycyclic compound of this embodiment is used as a dopant material in the emission layer exhibit long lifetimes.

[0231] Referring to the results in Table 1, it is believed that the compounds in the examples can be used as thermally activated delayed fluorescence materials with high efficiency and long lifetimes.

[0232] The organic electroluminescent device can exhibit high luminous efficiency by including the polycyclic compound of this embodiment.

[0233] Compared with the examples, it can be found that, because Comparative Compounds R-1 to R-4 do not contain suitable stable heteroaromatic rings (heteroaryl groups) in the core molecules, the organic electroluminescent devices of Comparative Examples 1 to 4 exhibit low external quantum efficiency and low device lifetimes.

[0234] As used herein, the term "use" and its variations can be considered to be synonymous with the term "utilize" and its variations, respectively.

[0235] 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 variations in measured or calculated values that would be recognized by a person of ordinary skill in the art.

[0236] 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, the range "1.0 to 10.0" is intended to include all sub-ranges between the recited minimum value of 1.0 and the recited maximum value of 10.0 (and including 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, by way of 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 amend this specification (including the claims) to expressly recite any sub-ranges that are subsumed within the ranges expressly recited herein.

[0237] While example embodiments of the invention have been described, it should be understood that the invention should not be limited to these example embodiments, but rather that various changes and modifications may be made by a person of ordinary skill in the art within the spirit and scope of the invention as defined by the claims and their equivalents.

[0238] Accordingly, the technical scope of the invention should not be limited to the content described in the detailed description of the specification, but rather should be defined by the claims and their equivalents.

Claims

1. An organic electroluminescent device, the organic electroluminescent device comprises: a first electrode; a hole transport region located on the first electrode; an emission layer located on the hole transport region; an electron transport region located on the emission layer; and a second electrode located on the electron transport region, wherein the emission layer comprises a polycyclic compound represented by Formula 4: Formula 4 In Formula 4, Z is B, PO, PS, SiAr 5 or GeAr 7 , ring M is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, Ar 1 ′ is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, ring B is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, Ar 1 is a substituted or unsubstituted aryl having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 30 ring-forming carbon atoms, Ar 5 and Ar 7 are each independently a substituted or unsubstituted amino group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and may optionally combine with adjacent groups to form a ring, ring A is represented by Formula 2: Formula 2 In Formula 2, X and Y are each independently a direct bond, O, S, SO, SO 2 , Se, NR 3 , PR 4 , POR 5 , PSR 6 , SiR 7 R 8 , GeR 9 R 10 or BR 11 , provided that X and Y are not both direct bonds at the same time, R 1 and R 2 combine to form a substituted aromatic hydrocarbon ring, R 3 to R 11 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a phosphine oxide group, a phosphine sulfide group, a silyl group, a carbonyl group, a boron group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, wherein one or more selected from R 1 to R 11 optionally combine with adjacent groups to form a ring, and -* indicates the connection position.

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

3. The organic electroluminescent device according to claim 1, wherein, the emission layer is a thermally activated delayed fluorescence emission layer.

4. The organic electroluminescent device according to claim 1, wherein, the emission layer is configured to emit blue light.

5. The organic electroluminescent device according to claim 1, wherein, Z is B.

6. The organic electroluminescent device according to claim 1, wherein, both the first electrode and the second electrode independently comprise at least one selected from the group consisting of: Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, compounds of two or more of them, mixtures of two or more of them, and transparent metal oxides.

7. The organic electroluminescent device according to claim 1, wherein, the hole transport region comprises: a hole injection layer located on the first electrode; and a hole transport layer located on the hole injection layer.

8. The organic electroluminescent device according to claim 7, wherein, The thickness of the hole injection layer is to And The thickness of the hole transport layer is to 9. The organic electroluminescent device according to claim 1, wherein, the electron transport region comprises: an electron transport layer located on the emission layer; and an electron injection layer located on the electron transport layer.

10. The organic electroluminescent device according to claim 9, wherein, The thickness of the electron transport layer is to and The thickness of the electron injection layer is to 11. The organic electroluminescent device according to claim 1, wherein, The thickness of the emission layer is to 12. The organic electroluminescent device according to claim 6, wherein, the transparent metal oxide comprises at least one selected from indium tin oxide, indium zinc oxide, zinc oxide, and indium tin zinc oxide.

13. A polycyclic compound represented by Formula 4: Formula 4 In Formula 4, Z is B, PO, PS, SiAr 5 or GeAr 7 , ring M is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, Ar 1 ′ is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, ring B is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, Ar 1 is a substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms, Ar 5 and Ar 7 are each independently a substituted or unsubstituted amino group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and may optionally combine with an adjacent group to form a ring, ring A is represented by Formula 2: Formula 2 In Formula 2, X and Y are each independently a direct bond, O, S, SO, SO 2 , Se, NR 3 , PR 4 , POR 5 , PSR 6 , SiR 7 R 8 , GeR 9 R 10 or BR 11 , provided that X and Y are not both direct bonds at the same time, R 1 and R 2 combine to form a substituted aromatic hydrocarbon ring, R 3 to R 11 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a phosphinyl group, a phosphinothioyl group, a silyl group, a carbonyl group, a boron group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, wherein, Selected from R 1 to R 11 One or more selected optionally combine with adjacent groups to form a ring, and -* indicates the connection position.

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