Organic electroluminescent device and polycyclic compound for organic electroluminescent device

Abstract

An organic electroluminescent device and a polycyclic compound for the organic electroluminescent device are provided. 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 1: #imgabs0# wherein in Formula 1, at least one selected from Ring A and Ring B is a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and Ar 1 and Z are the same as described in the specification.

Description

[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2019-0003819, filed on January 11, 2019, which is hereby incorporated by reference herein in its entirety. Technical Field

[0002] The present disclosure herein relates to organic electroluminescent devices and polycyclic compounds for use therein. Background Art

[0003] Recently, the development of organic electroluminescent display devices as image display devices has been actively carried out. Unlike liquid crystal display devices, organic electroluminescent display devices are self-luminous display devices in which holes and electrons injected from the first electrode and the second electrode are recombined in the emission layer and the light-emitting material (which is an organic compound included in the emission layer) emits light to realize the display of images.

[0004] When an organic electroluminescent device is applied to a display apparatus, the organic electroluminescent device is required to have a low driving voltage, high luminous efficiency, and a long life, and 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, a technology for emitting phosphorescence using triplet energy or emitting delayed fluorescence using triplet-triplet annihilation (TTA) (which is a phenomenon in which singlet excitons are generated due to the collision of triplet excitons) has 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 the embodiments of the present disclosure relate to an organic electroluminescent device having a long lifetime 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 fluorescent emission material and a polycyclic compound used as the thermally activated delayed fluorescent emission material.

[0008] An embodiment of the inventive concept provides an organic electroluminescent device, comprising: 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 1:

[0009] Formula 1

[0010]

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

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

[0013] Formula 2

[0014]

[0015] In Formula 2: X and Y can be 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 cannot both be direct links at the same time; and R 1 To R 11may 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, wherein R 1 To R 11 One or more selected from among 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 fluorescent emission layer configured to emit blue light.

[0019] Formula 1 can be expressed by Formula 3:

[0020] Formula 3

[0021]

[0022] In formula 3: Z' can 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 can be expressed by Formula 4:

[0025] Formula 4

[0026]

[0027] In formula 4: Z can 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 It may be the same as defined in Formula 1.

[0028] In Formula 1, Z can be BAr 2 .

[0029] Z can be expressed by Equation 5:

[0030] Formula 5

[0031]

[0032] In Formula 5, V 1 To V 5 Can be independently CR 12 or N; R 12 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 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 R 12 It may combine with an adjacent group to form a ring, and * indicates a binding site with the adjacent atom.

[0033] In Formula 5, V 1 To V 5 Can be independently CR 12 , where R 12 It 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 substituted or unsubstituted pyrrole, substituted or unsubstituted thiophene, substituted or unsubstituted oxazine, or substituted or unsubstituted furan.

[0035] Formula 1 can be expressed 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 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 A 1 can combine with adjacent groups to form a ring; n is an integer from 0 to 5; 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 ; 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, wherein R 1 To R 11 One or more selected from among may combine with an adjacent group to form a ring; and Ar 1 It may be the same as defined in Formula 1.

[0039] The polycyclic compound represented by Formula 1 may be selected from 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 accompanying drawings are included to provide a further understanding of the inventive concept and are incorporated in and constitute a part of this specification. The accompanying drawings illustrate example embodiments of the inventive concept and together with the description serve 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 illustrating an organic electroluminescent device according to an embodiment of the inventive concept; and

[0044] Figure 3 is a cross-sectional view schematically illustrating an organic electroluminescent 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 the 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 being limited to the embodiments set forth herein. On the contrary, all modifications, equivalents, and substitutes included in the spirit and technical scope of the inventive concept should be included in the inventive concept.

[0046] The same reference numerals always represent the same elements. In the accompanying drawings, for the clarity of illustration, the size of the structure is exaggerated. It will be understood that, although the terms first, second, etc. can be used to describe various elements here, these elements should not be limited by these terms. These terms are only used to distinguish one element from another element. Therefore, without departing from the teachings of the present invention, the first element can be named as the second element. Similarly, the second element can be named as the first element. As used herein, unless the context clearly indicates otherwise, the singular form is also intended to include the plural form.

[0047] In this specification, it is understood that the terms "comprising", "including" and / or "having" are intended to indicate that a specific feature, number, step, operation, element, part or combination thereof may be present, but do not exclude the possibility of 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 be an intermediate part. Conversely, 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 of", "one of", and "selected from" are followed (or preceded) by a list of elements, they modify the entire list of elements, not the 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] In the following, reference will be made to Figures 1 to 3An organic electroluminescent device according to an embodiment of the inventive concept is explained.

[0050] Reference Figures 1 to 3 , the organic electroluminescent device 10 according to 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 , which 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 electroluminescent device 10 may include a polycyclic compound of an embodiment of the present disclosure in the emission layer EML.

[0052] and Figure 1 compared to, Figure 2 1 shows a cross-sectional view of an organic electroluminescent device 10 according to an embodiment, wherein the hole transport region HTR includes a hole injection layer HIL and a hole transport layer HTL, and the electron transport region ETR includes an electron injection layer EIL and an electron transport layer ETL. Figure 1 compared to, Figure 3 A cross-sectional view of an organic electroluminescent device 10 according to an embodiment is shown, wherein the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL and an electron blocking layer EBL, and the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL and a hole blocking layer HBL.

[0053] In the organic electroluminescent 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 may be a transmissive electrode, a transflective electrode or a reflective electrode. When the first electrode EL1 is a transmissive electrode, the first electrode EL1 may 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 transflective electrode or a reflective electrode, the first electrode EL1 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / 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 may have a structure including a plurality of layers, the plurality of layers including: a reflective layer or a transflective 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 may have a multilayer structure of ITO / Ag / ITO.

[0055] The hole transport region HTR may be disposed on the first electrode EL1. The hole transport region HTR may 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 may have a structure of 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.

[0057] For example, the hole transport region HTR may have a structure of a single layer as the hole injection layer HIL or the hole transport layer HTL, or may 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 may have a structure of a single layer formed of a plurality of different materials, or may have 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 sequentially stacked from the first electrode EL1, but the embodiment is not limited thereto.

[0058] The hole transport region HTR may 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 polyetherketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium tetrakis(pentafluorophenyl)borate (PPBI), N,N'-diphenyl-N,N'-bis[4-(di-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine (DNTPD), phthalocyanine compounds (such as copper phthalocyanine), 4,4',4"-tris(3-methyl-phenyl-phenylamino)-triphenylamine (m-MTDATA), N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPB), N,N'-bis(1-naphthyl)-N,N'-diphenyl-2,2'-dimethylbenzidine (DNTPD), The invention also includes the following embodiments, wherein the present invention comprises 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-hexanitrile (HAT-CN), etc., but the embodiments of the present invention 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-methylphenylamino)phenyl]cyclohexane (TAPC), a carbazole derivative (such as N-phenylcarbazole or polyvinylcarbazole), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4,4',4"-tri(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, which may be disposed between the hole transport layer HTL and the emission layer EML. The electron blocking layer EBL may be used to prevent or reduce electron injection from the electron transport region ETR to 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(naphthalene-l-yl)-N,N'-diphenyl-benzidine (NPB), 4,4'-cyclohexylene-bis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), 1,3-di(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 approximately To about For example, approximately 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 appropriate) hole transport performance may be achieved without significantly increasing driving voltage.

[0064] In addition to the described materials, the hole transport region HTR may further include a charge generating material to improve conductivity. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region HTR. The charge generating material may be, for example, a p-dopant. The p-dopant may be selected from quinone derivatives, metal oxides, and cyano-containing compounds, but the embodiments of the present disclosure are not limited thereto. Non-limiting examples of p-dopants 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 luminous efficiency by compensating for an optical resonance distance according to the wavelength of light emitted from the emission layer EML. Any material included in the hole transport region HTR may also be used as a 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, approximately To about The emission layer EML may have a structure of 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 thermally activated delayed fluorescence of blue light.

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

[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 deuterium atoms, halogen atoms, cyano groups, silyl groups, oxy groups, sulfenyl groups, amino groups, alkyl groups, alkoxy groups, hydrocarbon ring groups, aryl groups and heterocyclic groups. 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 combining with an adjacent group" may refer to forming a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle by combining with an adjacent group. The hydrocarbon ring includes an aliphatic hydrocarbon ring and an aromatic hydrocarbon ring. The heterocycle (or heterocyclic group) includes an aliphatic heterocycle and an aromatic heterocycle. The ring formed by combining with an adjacent group may be a monocyclic ring or a polycyclic ring. In addition, the ring formed by combining may be combined with 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 connected to an atom directly connected to another atom substituted with a second substituent, a pair of substituents connected to the same atom (wherein the pair of substituents may be different from each other), or a pair of substituents in which a first substituent is spatially located closest to a second substituent. For example, in 1,2-dimethylbenzene, two methyl groups may be "adjacent groups" to each other, and in 1,1-diethylcyclopentane, 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 forming a ring.

[0074] In the present specification, the 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, the alkyl group may have a linear form, a branched form or a cyclic form. The carbon number of the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6. Examples of the alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyl Decyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, etc., but the embodiments of the present disclosure are not limited thereto. In the present specification, iPr may represent an isopropyl group.

[0076] In the present specification, an aryl group may refer to an aromatic hydrocarbon ring functional group or a substituent. An 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 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups may include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, pentaphenyl, hexaphenyl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, In the present specification, Ph may represent a phenyl group.

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

[0078]

[0079] In the present specification, the heteroaryl group may be a cyclic aromatic group including one or more of O, N, P, Si, S, Se, Ge and B as a ring-forming heteroatom. The number of ring-forming carbon atoms in the heteroaryl group may be 2 to 30 or 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 heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, N-arylcarbazolyl, N-heteroarylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothiphenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, dibenzosilyl, dibenzofuranyl, and the like, but embodiments of the present disclosure are not limited thereto.

[0080] In the present 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 carbon number of the amino group is not particularly limited, but can be 1 to 30. The amino group can include an alkylamino group and an arylamino group. Examples of the amino group can include a methylamino group, a dimethylamino group, a phenylamino group, a naphthylamino group, a 9-methyl-anthrylamino group, a diphenylamino group, 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 carbon atoms. In contrast, when neither Ring A nor Ring B is a heteroaryl group, molecular stability may be reduced, thereby deteriorating the luminous efficiency and / or life of an organic electroluminescent device in which the polycyclic compound is used.

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

[0088] In formula 1, Ar 1 It may be 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.

[0089] In formula 1, Ar 2 To Ar 8 and Ar may be 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 from Ar 2 To Ar 8 One or more selected from among Ar may combine with an adjacent group to form a ring. 2To Ar 8 One or more selected groups are optionally (or "optionally") combined 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 can be 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 .

[0094] In formula 2, R 1 To R 11 and R 2 and R 3 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 R 1 To R 11 One or more selected from among may combine with an adjacent group 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 heteroaromatic ring (heteroaryl group), and excludes the case in which both X and Y in Formula 2 are 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 Can combine with adjacent groups to form a ring.

[0097] In one or more embodiments, when Ar in Formula 1 1When it is an aryl group or a heteroaryl group that combines with 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 may 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.

[0102] In Formula 3, Ring A, Ring B and Z may be the same as defined in Formula 1.

[0103] In one or more embodiments, Z and Z' in Formula 3 may be identical to each other.

[0104] In one or more embodiments, Ar in Formula 1 2 To Ar 8 may be each independently 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 from Ar 2 To Ar 8 One or more selected from among may combine with an adjacent group to form a ring.

[0105] In one or more embodiments, when Ar in Formula 1 2 To Ar 8 When all are independently an aryl group or a heteroaryl group that combines with 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, the ring M may 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.

[0110] In formula 4, Ar 1 ' 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.

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

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

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

[0114] Formula 5

[0115]

[0116] In Formula 5, V 1 To V 5 Can be independently CR 12 or N. From V 1 To V 5 At least one of the selected 12 .

[0117] In Formula 5, R 12 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 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 It may combine with an adjacent group to form a ring, and * indicates a binding site with the adjacent atom.

[0118] In one or more embodiments, V in Formula 5 1 To V 5 Can be independently CR 12 , where R 12 It may 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 substituted or unsubstituted pyrrole, substituted or unsubstituted thiophene, substituted or unsubstituted oxazine, or substituted or unsubstituted furan.

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

[0121] Formula 6

[0122]

[0123] In formula 6, A 1 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 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 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, a plurality of A 1 May be the same as or different from each other.

[0125] In Formula 6, X and Y can be 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 .

[0126] In formula 6, R 1 To R 11 and R 2 and R 3 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 R 1 To R 11One or more selected from among may combine with an adjacent group to form a ring.

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

[0128] The polycyclic compound of the present embodiment represented by Formula 1 may be a delayed fluorescence emitting material. The polycyclic compound of the present 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), thereby being used as a thermally activated delayed fluorescent material. The polycyclic compound represented by Formula 1 of the embodiment may be represented by any one selected from the compounds in Compound Group 1:

[0130] Compound Group 1

[0131]

[0132]

[0133] The polycyclic compound represented by Formula 1 described above can be used in the organic electroluminescent device 10 of one or more embodiments to improve the luminous efficiency and / or life of the organic electroluminescent device 10. For example, the polycyclic compound represented by Formula 1 described above can be used in the emission layer EML of the organic electroluminescent device 10 to improve the luminous efficiency and / or life 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 may be used to delay fluorescence emission, and the dopant may be used to delay fluorescence emission. The emission layer EML may contain (include) a polycyclic compound represented by Formula 1 as a dopant material. For example, the polycyclic compound represented by Formula 1 may 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-di(naphthalene-2-yl)anthracene (ADN), 4,4',4"-tri(carbazol-9-yl)-triphenylamine (TCTA), 1,3,5-tri(N-phenylbenzimidazol-2-yl)benzene (TPBi), 2-tert-butyl-9,10-di(naphthalene-2-yl)anthracene (TBADN), distyrylarylene Compounds (distyrylarylene, DSA), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), 2-methyl-9,10-bis(naphthalene-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 in addition to the described host materials, any suitable delayed fluorescent emission host material may be included.

[0136] In addition, the emission layer EML of the organic electroluminescent device 10 of the present 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)naphthalene-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] Refer again 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 embodiment of the present disclosure is not limited thereto.

[0138] The electron transport region ETR may have a structure of 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, but the embodiments of the present disclosure are not limited thereto. The thickness of the electron transport region ETR may be, for example, about 1000 Å. To about

[0140] The electron transport region ETR may be formed 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.

[0141] When the electron transport region ETR includes the electron transport layer ETL, the electron transport region ETR may include, for example, tris(8-hydroxyquinoline)aluminum (Alq 3 ), 1,3,5-tris[(3-pyridyl)-phenyl-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bp hen), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (tBu-PBD), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), bis(benzoquinoline-10-hydroxy)beryllium (Bebq 2 ) and / or 9,10-di(naphthalene-2-yl)anthracene (ADN), but the embodiments of the present disclosure are not limited thereto.

[0142] When the electron transport region ETR includes the electron transport layer ETL, the thickness of the electron transport layer ETL may be about 100 Å. To about For example, approximately To about When the thickness of the electron transport layer ETL satisfies the described range, satisfactory (or appropriate) electron transport performance may be achieved without significantly increasing driving voltage.

[0143] When the electron transport region ETR includes the electron injection layer EIL, the electron transport region ETR may include, for example, a metal halide (such as LiF, NaCl, CsF, RbCl, RbI and / or KI), a lanthanide metal (such as Yb), a metal oxide (such as Li 2 The electron injection layer EIL may be a mixture of an electron transport material and an insulating organic metal salt. The organic metal salt may be a material having an energy band gap of about 4 eV or greater. In one or more embodiments, the organic metal salt may include, for example, a metal acetate, a metal benzoate, a metal acetoacetate, a metal acetylacetonate and / or a metal stearate.

[0144] When the electron transport region ETR includes the electron injection layer EIL, the thickness of the electron injection layer EIL may be about 100 Å. To about or approximately To about When the thickness of the electron injection layer EIL satisfies the described range, satisfactory (or appropriate) electron injection performance may be achieved without significantly increasing 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, for example, at least one selected from 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 electrical 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 transflective 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 transflective electrode or a reflective electrode, the second electrode EL2 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / 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 be a structure having a plurality of layers, the plurality of layers including: a reflective layer or a transflective 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 the 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. The electrons and holes may be recombined in the emission layer EML to generate excitons, and the excitons may emit light when the excitons fall back from an excited state to a 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 transflective 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 transflective 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 lifespan characteristics using the described polycyclic compound of the present embodiment 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 group having 2 to 30 ring carbon atoms. In contrast, when neither Ring A nor Ring B is a heteroaryl group, molecular stability may be reduced, thereby deteriorating luminous efficiency and / or life when the polycyclic compound is applied to an organic electroluminescent device.

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

[0158] In formula 1, Ar 1 It may be 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.

[0159] In formula 1, Ar 2 To Ar 8 and Ar may be 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 from Ar 2 To Ar 8 One or more selected from among may combine with an adjacent group 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 can be 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 .

[0164] In formula 2, R 1 To R 11 and R 2 and R 3 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 R 1 To R 11 One or more selected from among may combine with an adjacent group 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 in which X and Y in Formula 2 are both direct bonds at the same time.

[0166] The description of the polycyclic compound provided above in conjunction with 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 compounds collectively referred to as Compound Group 1.

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

[0169] Synthesis Example

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

[0171] 1. Synthesis of Compound 8

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

[0173]

[0174] Synthesis of intermediate compound A

[0175] Under Ar atmosphere, 9.63 g (20 mmol) of N 1 -(2,3-Dichlorophenyl)-N 1 ,N 3 ,N 3-triphenyl-1,3-phenylenediamine, 2.0 mL (22 mmol) of aniline, 0.71 g (1.0 mmol) of dichlorobis[di-tert-butyl-(4-dimethylaminophenyl)phosphine]palladium(II) ((Amphos)PdCl 2 ) and 2.11g (22mmol) of NaOtBu were added to a 300mL three-necked flask, and in 100mL of xylene solvent, the mixture was stirred at 120°C for 1 hour. 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 7.40g of compound A (yield of 69%) as a white solid. 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 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 , 0.26g (0.55mmol) of 2-dicyclohexylphosphine-2', 6'-diisopropoxy-1,1'-biphenyl (Ruphos) and 1.44g (15.0mmol) of NaOtBu were added to a 200mL three-necked flask, and in 70mL 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 6.79g of compound B (yield 68%) as a white solid. The molecular weight of compound B measured by FAB-MS is 728.

[0178] Synthesis of compound 8

[0179] Under 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 pentane solution of 1.9 M tert-butyl lithium (t-BuLi) was added dropwise (dropwise). After the addition was completed, the temperature was raised to 60°C, and the mixture was stirred for 2 hours, after which 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 was added dropwise thereto. 3. After the addition is completed, the temperature is raised to room temperature and the mixture is stirred for 2 hours. Afterwards, the mixture is cooled to 0°C again, and 1.7mL (9.8mmol) of N,N-diisopropylethylamine is added dropwise thereto. After the addition is completed, the temperature is raised to room temperature and the mixture is stirred for 1 hour, then, the temperature is raised to 120°C, and the mixture is heated and stirred for 8 hours. The obtained reaction solution is cooled to room temperature, and toluene and an aqueous NaOAc solution cooled in an ice bath are added to separate the solution. Subsequently, the solution is purified by short column chromatography (silica gel) and recrystallized with a toluene / hexane solvent to obtain 5.09g of compound 8 as a yellow solid (yield is 78%).

[0180] Compound 8 was confirmed by FAB-MS and NMR. The molecular weight of compound 8 measured by FAB-MS was 702. 1 H-NMR (CDCl 3 )The chemical shift values ​​δ of compound 8 measured by HPLC 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, in the following manner:

[0183]

[0184] Synthesis of intermediate compound C

[0185] Under 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 2.11g (22mmol) of NaOtBu was added into a 300mL three-necked flask, and in a 100mL xylene solvent, the mixture was stirred for 1 hour at 120°C. After air cooling, water was added thereto to separate the organic layer, and the solvent was distilled off. The crude product obtained was purified by column chromatography (silica gel), to obtain 6.00g of compound C (productive rate was 81%) as a white solid. The molecular weight of the compound C recorded by FAB-MS was 370.

[0186] Synthesis of intermediate compound D

[0187] Under 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 , 0.30g (0.64mmol) of Ruphos and 1.70g (17.7mmol) of NaOtBu are added in a 200mL three-necked flask, and in 80mL of toluene solvent, the mixture is stirred for 3 hours at 100°C. After air cooling, water is added thereto to separate the organic layer, and the solvent is distilled off. The crude product obtained is purified by column chromatography (silica gel), to obtain 5.27g of compound D (productive rate is 61%) as a white solid. The molecular weight of the compound D recorded by FAB-MS is 536.

[0188] Synthesis of intermediate compound E

[0189] Under 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 , 0.36g (0.78mmol) of Ruphos and 1.04g (10.8mmol) of NaOtBu were added into a 200mL three-necked flask, and in 50mL 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 5.05g of compound E (yield of 77%) as a white solid. The molecular weight of the compound E measured by FAB-MS is 669.

[0190] Synthesis of compound 10

[0191] Under 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, and then 15.8 mL (30 mmol) of a pentane solution of 1.9 M t-BuLi was added dropwise (dropwise). After the addition was completed, the temperature was raised to 60°C, and the mixture was stirred for 2 hours, after which 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 was added dropwise thereto. 3. After the addition is completed, the temperature is raised to room temperature and the mixture is stirred for 2 hours. Afterwards, the mixture is cooled to 0°C again, and 1.4mL (8.0mmol) of N,N-diisopropylethylamine is added dropwise thereto. After the addition is completed, the temperature is raised to room temperature and the mixture is stirred for 1 hour, then, the temperature is raised to 120°C, and the mixture is heated and stirred for 8 hours. The obtained reaction solution is cooled to room temperature, and toluene and an aqueous NaOAc solution cooled in an ice bath are added to separate the solution. Subsequently, the solution is purified by short column chromatography (silica gel) and recrystallized with a toluene / hexane solvent to obtain 4.00g of compound 10 as a yellow solid (yield is 83%).

[0192] Compound 10 was confirmed by FAB-MS and NMR. The molecular weight of compound 10 measured by FAB-MS was 643. 1 H-NMR (CDCl 3 )The chemical shift values ​​δ of compound 10 measured by HPLC were: 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 Ar atmosphere, 100mL of dehydrated THF solution of 6-chloro-1-phenyl-1H-indole (4.55g (20mmol)) was added to a 500mL three-necked flask and stirred at -78°C. Then, 13mL (21mmol) of a hexane solution of 1.6M n-BuLi was added dropwise thereto and stirred for 2 hours. 20mL of dehydrated THF solution of 5.33g (21mmol) of iodine was added dropwise thereto and stirred for 2 hours at -78°C, 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 6.00g of compound F (yield 85%) as a white solid. The molecular weight of compound F measured by FAB-MS is 353.

[0198] Synthesis of intermediate compound G

[0199] Under 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 , 0.25g (0.34mmol) of dppf and 1.79g (18.6mmol) of NaOtBu were added to a 300mL three-necked flask, and in 85mL of toluene solvent, the mixture was stirred at 80°C for 6 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 4.96g of compound G (yield 58%) as a white solid. The molecular weight of compound G measured by FAB-MS is 506.

[0200] Synthesis of intermediate compound H

[0201] Under 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 (dropwise) and stirred for 2 hours, after which 1.0 mL (10 mmol) of BBr was added dropwise. 3 , and stirred at -78 ° C for 1 hour, and then stirred at room temperature for 3 hours. The mixture was cooled to 0 ° C, after which 1.0M 2,4,6-triisopropylphenylmagnesium bromide THF solution 10mL (10mmol) 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 4.36g of compound H (yield 70%) as a yellow solid. The molecular weight of compound H measured by FAB-MS is 640.

[0202] Synthesis of compound 11

[0203] Under 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, 0.63g (1.36mmol) of Ruphos and 1.44g (15.0mmol) of NaOtBu were added into a 200mL three-necked flask, and in 70mL 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 3.20g of compound 11 (yield 52%) as a yellow solid.

[0204] Compound 11 was confirmed by FAB-MS and NMR. The molecular weight of compound 11 measured by FAB-MS was 906. 1 H-NMR (CDCl 3 )The chemical shift values ​​δ of compound 11 measured by HPLC were: 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 Ar atmosphere, 9.86 g (50 mmol) of 4,4'-dimethyldiphenylamine (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 , 0.93g (2.0mmol) of Ruphos and 5.29g (55mmol) of NaOtBu were added to a 500mL three-necked flask, and in 250mL of toluene solvent, the mixture was stirred at 100°C for 2 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 15.15g of compound I as a white solid (yield of 92%). The molecular weight of compound I measured by FAB-MS is 329.

[0210] Synthesis of intermediate compound K

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

[0212] Synthesis of compound 12

[0213] Under 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, and then 129 mL (245 mmol) of a pentane solution of 1.9 M t-BuLi was added dropwise (dropwise). After the addition was completed, 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 was added dropwise thereto. 3 . After the addition was completed, the temperature was raised to room temperature and the mixture was stirred for 2 hours. Afterwards, the mixture was cooled to 0 ° C again, and 14.9 mL (82 mmol) of 1,2,2,6,6-pentamethylpiperidine was added 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 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 THF solution of 1.0 M 2,4,6-trimethylphenylmagnesium bromide was added thereto, and stirred at 0 ° C for 2 hours, and stirred 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 (yield 19%) as a yellow solid.

[0214] Compound 12 was confirmed by FAB-MS and NMR. The molecular weight of compound 12 measured by FAB-MS was 585. 1 H-NMR (CDCl 3)The chemical shift values ​​δ of compound 12 measured were: 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] Example of device fabrication

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

[0217] [Compounds in the examples]

[0218]

[0219] Organic electroluminescent devices of Comparative Examples 1 to 4 were manufactured using Comparative Compounds R-1 to R-4 shown below as emission 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 are independently formed by performing the following process: forming a substrate having The ITO with a thickness of 1000 nm was patterned and washed with ultrapure water and treated with UV ozone for 10 min; thereafter, HAT-CN was deposited to have The thickness of α-NPD is 0.1, and α-NPD is deposited to have and depositing mCP to have a thickness of The thickness of the hole transport region is formed;

[0223] Next, the polycyclic compounds of the present example or the comparative compounds and DPEPO were co-deposited at a ratio of 20:80 to form Then, DPEPO is used to form a layer having a thickness of Therefore, in Examples 1 to 4, the emission 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 emission 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] TPBi is used to form a and using LiF to form a layer having a thickness of A layer with a thickness of 1000 nm was formed to form an electron transport region. Subsequently, aluminum (Al) was used to form a The thickness of the second electrode is .

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

[0226] Performance evaluation of organic electroluminescent devices

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

[0228] Table 1

[0229] category Dopant of the emission layer External quantum yield (%) <![CDATA[Lifetime LT 50 (h)]]> Example 1 Compound 8 15.3 19.4 Example 2 Compound 10 19.8 33.4 Example 3 Compound 11 16.3 10.8 Example 4 Compound 12 21.2 11.4 Comparative Example 1 Comparative Compound R-1 12.8 2.9 Comparative Example 2 Comparative Compound R-2 14.4 3.8 Comparison Example 3 Comparative Compound R-3 6.9 9.8 Comparison Example 4 Comparative Compound R-4 7.2 8.5

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

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

[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 the 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 life.

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

[0235] Additionally, the terms "substantially," "approximately," and similar terms are used as terms of approximation rather than terms of degree, and are intended to account for the inherent variations in measurements or calculations that would be recognized by those having ordinary skill in the art.

[0236] In addition, any numerical range stated herein is intended to include all subranges of the same numerical precision contained in the stated range. For example, the range "1.0 to 10.0" is intended to include all subranges between the stated minimum value 1.0 and the stated maximum value 10.0 (and including the stated minimum value 1.0 and the stated maximum value 10.0), that is, having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as 2.4 to 7.6. Any maximum numerical limit stated herein is intended to include all lower numerical limits contained therein, and any minimum numerical limit stated in this specification is intended to include all higher numerical limits contained therein. Therefore, the applicant reserves the right to modify this specification (including claims) to explicitly state any subrange contained in the scope explicitly stated herein.

[0237] Although example embodiments of the present invention have been described, it should be understood that the present invention should not be limited to those example embodiments, but various changes and modifications may be made by one skilled in the art within the spirit and scope of the present invention as defined by the claims and their equivalents.

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

Claims

1. A polycyclic compound, the polycyclic compound is represented by Formula 6: Formula 6 In formula 6, X and Y are independently a direct bond, O, S, or NR3, Ar1 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, A1 is 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, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, wherein one or more A1 optionally combine with adjacent groups to form a ring, R1 and R2 are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, and R1 and R2 are combined with adjacent groups to form an aromatic hydrocarbon ring, R3 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and n is an integer from 0 to 5, wherein at least one substituent among the substituted oxy group, the substituted thiol group, the substituted amino group, the substituted alkyl group having 1 to 10 carbon atoms, the substituted aryl group having 6 to 30 ring carbon atoms and the substituted aralkyl group having 7 to 30 carbon atoms is selected from a deuterium atom, a halogen atom, a cyano group, a silyl group, an oxy group, a thiol group, an amino group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 15 ring carbon atoms and a heterocyclic group having 2 to 20 ring carbon atoms.

2. A polycyclic compound, wherein The polycyclic compound is selected from the group consisting of compounds collectively referred to as Compound Group 1: Compound Group 1 3. An organic electroluminescent device, comprising: 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; as well as A second electrode is located on the electron transport region, wherein the first electrode and the second electrode each independently include at least one selected from the following: Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, a compound selected from two or more thereof, a mixture selected from two or more thereof, and a transparent metal oxide, and Wherein, the emission layer comprises the polycyclic compound according to any one of claims 1 and 2.

4. The organic electroluminescent device according to claim 3, wherein: The emission layer is configured to emit delayed fluorescence.

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

6. The organic electroluminescent device according to claim 3, wherein: The emission layer is a thermally activated delayed fluorescent emission layer configured to emit blue light.

7. The organic electroluminescent device according to claim 3, wherein: The transparent metal oxide includes at least one selected from indium tin oxide, indium zinc oxide, zinc oxide, and indium tin zinc oxide.

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