Organic electroluminescence device and polycyclic compound for organic electroluminescence device

Abstract

To provide an organic electroluminescence device having a long life-time and high efficiency, and a polycyclic compound used therefor.SOLUTION: An organic electroluminescence device includes a first electrode, a hole transport layer on the first electrode, an emission layer on the hole transport layer, an electron transport layer on the emission layer, and a second electrode on the electron transport layer, wherein the emission layer includes a polycyclic compound represented by Formula 1, thereby exhibiting high emission efficiency. In Formula 1, at least one selected from Ring A and Ring B is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring. Z is BAr2, POAr3, PSAr4, SiAr5Ar6, or GeAr7Ar8.SELECTED DRAWING: Figure 1

Description

[Technical field]

[0001] The present invention relates to an organic electroluminescent device and a polycyclic compound used therein. [Background technology]

[0002] Recently, organic electroluminescence displays (OLEDs) have been actively developed as image display devices. Unlike liquid crystal displays, OLEDs are so-called self-luminous displays that realize display by recombining holes and electrons injected from a first electrode and a second electrode in a light-emitting layer to cause a light-emitting material containing an organic compound in the light-emitting layer to emit light.

[0003] In order to apply organic electroluminescent devices to display devices, there is a demand for lower driving voltages, higher luminous efficiency, and longer life for the organic electroluminescent devices, and there is a continuous demand for the development of materials for organic electroluminescent devices that can stably achieve these demands.

[0004] In particular, in order to realize highly efficient organic electroluminescent devices, technologies related to phosphorescence emission that utilizes the energy of triplet states and delayed fluorescence emission that utilizes the phenomenon in which singlet excitons are generated by the collision of triplet excitons (TTA) have been developed recently, and development of thermally activated delayed fluorescence (TADF) materials that utilize the delayed fluorescence phenomenon is also progressing. Summary of the Invention [Problem to be solved by the invention]

[0005] An object of the present invention is to provide an organic electroluminescent device having a long life and high efficiency, and a polycyclic compound used therein.

[0006] Another object of the present invention is to provide an organic electroluminescent device comprising a thermally activated delayed fluorescent luminescent material and a polycyclic compound used as the thermally activated delayed fluorescent luminescent material. [Means for solving the problem]

[0007] According to one embodiment of the present invention, there is provided an organic electroluminescent device comprising a first electrode, a hole transport layer provided on the first electrode, a light emitting layer provided on the hole transport layer, an electron transport layer provided on the light emitting layer, and a second electrode provided on the electron transport layer, wherein the light emitting layer comprises a polycyclic compound represented by Chemical Formula 1 below. [ka] In Chemical Formula 1, ring A and ring B are each independently a substituted or unsubstituted aryl ring having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl ring having 2 to 30 ring carbon atoms, at least one of ring A and ring B is a substituted or unsubstituted heteroaryl ring having 2 to 30 ring carbon atoms, and Z is BAr 2 ,POAr 3 , P.S.Ar 4 , SiAr 5 Ar 6 , or GeAr 7 Ar 8 and Ar 1 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, 2 ~Ar 8 each independently represents a substituted or unsubstituted amino group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted aralkyl group having from 7 to 30 ring carbon atoms, a substituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, which may be bonded to an adjacent group to form a ring.

[0008] At least one of ring A and ring B in Chemical Formula 1 is represented by Chemical Formula 2 below. [ka] In Chemical Formula 2, X and Y are each independently a single bond, O, S, SO, or SO 2 , Se, NR 3 , P.R. 4 , POR 5 , P.S.R. 6 , SiR 7 R 8 , G.E.R. 9 R 10 , or B.R. 11 X and Y are not single bonds at the same time, and R 1 ~R 11 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted germyl group, a substituted or unsubstituted amino 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 boryl group, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having from 7 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, and may be bonded to an adjacent group to form a ring.

[0009] The light-emitting layer is an organic electroluminescent element that emits delayed fluorescence.

[0010] The light-emitting layer is a delayed fluorescent light-emitting layer containing a host and a dopant, and the dopant is an organic electroluminescent device containing the polycyclic compound.

[0011] The light-emitting layer is an organic electroluminescent device that is a thermally activated delayed fluorescent light-emitting layer that emits blue light.

[0012] Chemical Formula 1 is represented by Chemical Formula 3 below. [ka] In formula 3, Z' is BAr 2 ,POAr 3 , P.S.Ar 4 , SiAr 5 Ar 6 , or GeAr 7 Ar 8 and ring L is 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 ring A, ring B, and Z are as defined in formula 1.

[0013] In Chemical Formula 3, Z and Z' are the same as each other.

[0014] Chemical Formula 1 is represented by Chemical Formula 4 below. [ka] In chemical formula 4, W is B, PO, PS, SiAr 5 , or GeAr 7 ring M is 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; Ar 1 ' is a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having from 7 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, and 1 , Ar 5 , and Ar 7 is as defined in Chemical Formula 1.

[0015] In formula 1, Z is BAr 2 It is.

[0016] In Chemical Formula 1, Z is represented by Chemical Formula 5 below. [ka] In Chemical Formula 5, V 1 ~V 5 are each independently CR 12 or N and R 12 represents 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 boryl group, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having from 7 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, which may be bonded to an adjacent group to form a ring.

[0017] V in Chemical Formula 5 1 ~V 5 are each independently CR 12 and R 12 is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 2 to 10 carbon atoms.

[0018] At least one of ring A and ring B in chemical formula 1 is a substituted or unsubstituted pyrrolidone. The substituents are selected from the group consisting of aryl, substituted or unsubstituted thiophene, substituted or unsubstituted oxazine, and substituted or unsubstituted furan.

[0019] Chemical Formula 1 is represented by Chemical Formula 6 below. [ka] In Chemical Formula 6, A 1represents 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 boryl group, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having from 7 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, which may be bonded to adjacent groups to form a ring; n is an integer of from 0 to 5; X and Y each independently represent a single bond, O, S, SO, SO 2 , Se, NR 3 , P.R. 4 , POR 5 , P.S.R. 6 , SiR 7 R 8 , G.E.R. 9 R 10 , or B.R. 11 and R 1 ~R 11 each independently represents 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 boryl group, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having from 7 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, which may be bonded to an adjacent group to form a ring; Ar 1 is as defined in Chemical Formula 1.

[0020] The polycyclic compound represented by Chemical Formula 1 is any one of the compounds shown in the first compound group below. [Compound group 1] [ka] JPEG2024170578000009.jpg210148 JPEG2024170578000010.jpg90151

[0021] According to one embodiment of the present invention, there is provided a polycyclic compound represented by Chemical Formula 1. [Brief description of the drawings]

[0022] [Figure 1] 1 is a cross-sectional view illustrating an organic electroluminescent device according to an embodiment of the present invention. [Diagram 2] 1 is a cross-sectional view illustrating an organic electroluminescent device according to an embodiment of the present invention. [Diagram 3] 1 is a cross-sectional view illustrating an organic electroluminescent device according to an embodiment of the present invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0023] Since the present invention can be modified in various ways and can have various forms, specific embodiments are illustrated in the drawings and described in detail in the text, but it is not intended to limit the present invention to the specific disclosed forms, and it should be understood that the present invention includes all modifications, equivalents, and alternatives falling within the spirit and technical scope of the present invention.

[0024] In the drawings, like reference numerals are used for like elements. In the accompanying drawings, the dimensions of the structures are exaggerated to make the present invention clearer. Terms such as first and second are used to describe various elements, but elements are not limited to the terms. Terms are used only to distinguish one structural element from another. For example, the first element may be referred to as the second element, and similarly, the second element may be referred to as the first element, without departing from the scope of the present invention. A singular expression includes a plural expression unless the context clearly indicates otherwise.

[0025] In this application, the terms "comprise" or "have" are intended to indicate the presence of a feature, number, step, operation, component, part, or combination thereof described in the specification above, and should be understood as not precluding the presence or additional possibility of one or more other features, numbers, steps, operations, components, parts, or combinations thereof. In addition, when a layer, film, region, plate, or other part is described as being "on" another part, this includes not only the case where it is "directly on" the other part, but also the case where there is another part between them.

[0026] In this specification, -* denotes the position of attachment.

[0027] In this specification, "substituted or unsubstituted" means that the group is substituted or unsubstituted with one or more substituents selected from the group consisting of a deuterium atom, a halogen atom, a cyano group, a nitro group, an amino group, a silyl group, a boryl group, a phosphine oxide group, a phosphine sulfide group, a germyl group, an alkyl group, an aryl group, and a heterocyclic group. Each of the substituents exemplified above may be substituted or unsubstituted. For example, a biphenylyl group may be interpreted as an aryl group, or as a phenyl group substituted with a phenyl group.

[0028] In this specification, "bonding with adjacent groups to form a ring" means bonding with adjacent groups to form a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted hetero ring. The hydrocarbon ring includes an aliphatic hydrocarbon ring and an aromatic hydrocarbon ring. The hetero ring includes an aliphatic hetero ring and an aromatic hetero ring. The hydrocarbon ring and the hetero ring are monocyclic and polycyclic. In addition, the ring formed by bonding with adjacent groups may be linked to another ring to form a spiro structure.

[0029] In this specification, "adjacent groups" refers to a substituent substituted on an atom directly bonded to the atom on which the corresponding substituent is substituted, another substituent substituted on an atom on which the corresponding substituent is substituted, or a substituent structurally most adjacent to the corresponding substituent. For example, two methyl groups in 1,2-dimethylbenzene are interpreted as "adjacent groups" to each other, and two ethyl groups in 1,1-diethylcyclopentene are interpreted as "adjacent groups" to each other.

[0030] In this specification, examples of halogen atoms include a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0031] In this specification, an alkyl group is linear, branched, or cyclic. The number of carbon atoms in an alkyl group is 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, s-butyl, t-butyl, i-butyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, i-pentyl, neopentyl, t-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylbutyl ... Hexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-t-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, t-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl n-butyldecyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl , n-heptadecyl group, n-octadecyl group, n-nonadecyl group, n-icosyl group, 2-ethylicosyl group, 2-butylicosyl group, 2-hexylicosyl group, 2-octylicosyl group, n-henicosyl group, n-docosyl group, n-tricosyl group, n-tetracosyl group, n-pentacosyl group, n-hexacosyl group, n-heptacosyl group, n-octacosyl group, n-nonacosyl group, and n-triacontyl group, but are not limited to these.

[0032] As used herein, an aryl group refers to any functional group or substituent derived from an aromatic hydrocarbon ring. An aryl group may be a monocyclic aryl group or a polycyclic aryl group. The number of ring carbon atoms of the aryl group is 6 or more and 30 or less, 6 or more and 20 or less, or 6 or more and 15 or less. Examples of the aryl group include, but are not limited to, a phenyl group, a naphthyl group, a fluorenyl group, an anthracenyl group, a phenanthryl group, a biphenylyl group, a terphenylyl group, a quaterphenylyl group, a quinquephenylyl group, a sexiphenylyl group, a triphenylenyl group, a pyrenyl group, a benzofluoranthenyl group, and a chrysenyl group.

[0033] In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. Examples of the fluorenyl group that may be substituted include, but are not limited to, the following: [ka]

[0034] In this specification, the heteroaryl group is a heteroaryl group containing one or more of O, N, P, Si, and S as a heteroatom. The number of ring carbon atoms of the heteroaryl group is 2 to 30, or 2 to 20. The heteroaryl group is a monocyclic heteroaryl group or a polycyclic heteroaryl group. The polycyclic heteroaryl group may have, for example, a two-ring or three-ring structure. Examples of the heteroaryl group include a thiophenyl group, a furanyl 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 pyrimidyl group, a triazinyl group, a triazolyl group, an acridinyl group, a pyridazinyl group, a quinolinyl group, a quinazolyl 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, and an N-allyl group. Examples of such alkyl groups include, but are not limited to, a carbazolyl group, an N-heteroarylcarbazolyl group, an N-alkylcarbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophenyl group, a dibenzothiophenyl group, a thienothiophenyl group, a benzofuranyl group, a phenanthrolinyl group, a thiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, a dibenzosilolyl group, and a dibenzofuranyl group.

[0035] In this specification, the silyl group includes an alkylsilyl group and an arylsilyl group. Examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like.

[0036] In this specification, the number of carbon atoms of the amino group is not particularly limited, but may be 1 or more and 30 or less. The amino group includes an alkylamino group and an arylamino group. Examples of the amino group include, but are not limited to, a methylamino group, a dimethylamino group, a phenylamino group, a naphthylamino group, a 9-methyl-anthracenylamino group, and a triphenylamino group.

[0037] As used herein, the phosphine oxide group is defined as a group consisting of, for example, a small number of alkyl and aryl groups. The phosphine sulfide group may be substituted with at least one of an alkyl group and an aryl group. Examples of the phosphine oxide group include, but are not limited to, a phenylphosphine oxide group and a diphenylphosphine oxide group. In the present specification, the phosphine sulfide group may be substituted with at least one of an alkyl group and an aryl group. Examples of the phosphine sulfide group include, but are not limited to, a phenylphosphine sulfide group and a diphenylphosphine sulfide group.

[0038] In the present specification, the boryl group may be substituted with at least one of an alkyl group and an aryl group. Examples of the boryl group include, but are not limited to, a phenylboryl group and a diphenylboryl group.

[0039] In the present specification, the germyl group may be substituted with at least one of an alkyl group and an aryl group, for example. Examples of the germyl group include, but are not limited to, a phenylgermyl group and a diphenylgermyl group.

[0040] Hereinafter, an organic electroluminescence device according to one embodiment of the present invention will be described with reference to FIGS.

[0041] 1 to 3, an organic electroluminescent device 10 according to an embodiment of the present invention includes 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.

[0042] The first electrode EL1 and the second electrode EL2 are disposed opposite to each other, and a plurality of organic layers are disposed between the first electrode EL1 and the second electrode EL2. The plurality of organic layers include a hole transport region HTR, an emission layer EML, and an electron transport region ETR. In the organic electroluminescent device 10 according to an embodiment, the emission layer EML includes a polycyclic compound according to an embodiment.

[0043] Meanwhile, Fig. 2 is a cross-sectional view of an organic electroluminescent 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 comparison with Fig. 1. Fig. 3 is a cross-sectional view of an organic electroluminescent 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, in comparison with Fig. 1.

[0044] In the organic electroluminescent device 10 according to the embodiment, the first electrode EL1 has electrical conductivity. The first electrode EL1 is made of a metal alloy or a conductive compound. The first electrode EL1 is an anode.

[0045] The first electrode EL1 is a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. If the first electrode EL1 is a transmissive electrode, the first electrode EL1 is made of a transparent metal oxide, for example, ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO (indium tin zinc oxide), etc. If the first electrode EL1 is a semi-transmissive electrode or a reflective electrode, the first electrode EL1 includes 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 (for example, an alloy of Ag and Mg). In addition, the first electrode EL1 may have a multi-layer structure including a reflective film or semi-transmissive film formed of the exemplified material, and a transparent conductive film formed of ITO, IZO, ZnO, ITZO, etc. For example, the first electrode EL1 may include a multi-layer structure of ITO / Ag / ITO.

[0046] The hole transport region HTR is provided on the first electrode EL1 and includes at least one of a hole injection layer HIL, a hole transport layer HTL, a hole buffer layer, and an electron blocking layer EBL.

[0047] The hole transport region HTR may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multi-layer structure having a plurality of layers made of a plurality of different materials.

[0048] For example, the hole transport region HTR may have a single layer structure of a hole injection layer HIL or a hole transport layer HTL, or a single structure formed of a hole injection material and a hole transport material. The hole transport region HTR may have a single layer structure having 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, which are stacked in order from the first electrode EL1, but is not limited thereto.

[0049] The hole transport region HTR can be formed using various methods such as a vacuum deposition method, a spin coating method, a Langmuir-Blodgett (LB) method, an inkjet printing method, a laser printing method, a laser induced thermal imaging (LITI) method, and the like.

[0050] The hole injection layer HIL of the organic electroluminescent device 10 according to an embodiment includes a known hole injection material. For example, the hole injection layer HIL may include a triphenylamine-containing polyether ketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium tetrakis(pentafluorophenyl)borate (PPBI), N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-phenyl-4,4'-diamine (DNTPD), a phthalocyanine compound 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-4,4'-diamine (α-NPD), 4, These may include, but are not limited to, 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), or HAT-CN (dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile).

[0051] The hole transport layer HTL of the organic electroluminescent device 10 according to an embodiment includes a known hole transport material. For example, the hole transport layer HTL may include carbazole derivatives such as 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC), N-phenylcarbazole, polyvinylcarbazole, etc., 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-4,4'-diamine (α-NPD), etc. However, the hole transport layer HTL is not limited thereto.

[0052] On the other hand, the hole transport region HTR may further include an electron blocking layer EBL. is disposed between the hole transport layer HTL and the light emitting layer EML. The electron blocking layer EBL is a layer that serves to prevent the injection of electrons from the electron transport region ETR to the hole transport region HTR.

[0053] The electron blocking layer (EBL) comprises common materials known in the art. The electron blocking layer EBL may include, for example, a carbazole derivative such as N-phenylcarbazole or polyvinylcarbazole, a fluorene derivative, a triphenylamine derivative such as TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine) or TCTA (4,4',4"-tris(N-carbazolyl)triphenylamine), NPB (N,N'-di(naphthalen-1-yl)-N,N'-diphenyl-benzidine), TAPC (4,4'-cyclohexylidenebis[N,N-bis(4-methylphenyl)benzenamine]), HMTPD (4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl), or mCP. As described above, the hole blocking layer EBL may include a polycyclic compound according to one embodiment of the present invention.

[0054] The thickness of the hole transport region HTR may be about 10 nm to about 1000 nm, for example, about 10 nm to about 500 nm. The thickness of the hole injection layer HIL may be, for example, about 3 nm to about 100 nm, and the thickness of the hole transport layer HTL may be about 3 nm to about 100 nm. For example, the thickness of the electron blocking layer EBL may be about 1 nm to about 100 nm. If the thicknesses of the hole transport region HTR, the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL satisfy the above-mentioned ranges, sufficient hole transport properties can be obtained without a substantial increase in driving voltage.

[0055] In addition to the above-mentioned materials, the hole transport region HTR may further include a charge generating material to improve conductivity. The charge generating material is uniformly or non-uniformly dispersed in the hole transport region HTR. The charge generating material is, for example, a p-dopant. The p-dopant may be any one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. For example, non-limiting examples of the p-dopant include quinone derivatives such as TCNQ (tetracyanoquinodimethane) and F4-TCNQ (2,3,5,6-tetrafluoro-tetracyanoquinodimethane), metal oxides such as tungsten oxide and molybdenum oxide, etc., but are not limited thereto.

[0056] As described above, the hole transport region HTR may further include at least one of a hole buffer layer and an electron blocking layer EBL in addition to the hole injection layer HIL and the hole transport layer HTL. The hole buffer layer compensates for the resonance distance according to the wavelength of light emitted from the emission layer EML to increase light emission efficiency. The material contained in the hole buffer layer is a material that can be contained in the hole transport region HTR.

[0057] The light-emitting layer EML is provided on the hole transport region HTR. The thickness of the light-emitting layer EML may be, for example, 10 nm to 60 nm. The light-emitting layer EML has a multilayer structure having a single layer made of a single material, a single layer made of multiple different materials, or multiple layers made of multiple different materials.

[0058] The light-emitting layer EML emits one of red, green, blue, white, yellow, and cyan light. The light-emitting layer EML includes a fluorescent or phosphorescent light-emitting material.

[0059] In one embodiment, the emitting layer EML is a fluorescent emitting layer. For example, a portion of the light emitted from the emitting layer EML is thermally activated delayed fluorescence. Specifically, the emitting layer EML includes a light-emitting component that emits thermally activated delayed fluorescence, and in one embodiment, the emitting layer EML is a light-emitting layer that emits blue light and emits thermally activated delayed fluorescence.

[0060] In one embodiment, the emissive layer EML comprises a polycyclic compound represented by Chemical Formula 1. [ka]

[0061] In Chemical Formula 1, ring A and ring B are each independently a substituted or unsubstituted aryl ring having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl ring having 2 to 30 ring carbon atoms.

[0062] Meanwhile, in Chemical Formula 1, at least one of Ring A and Ring B is a substituted or unsubstituted heteroaryl ring having 2 to 30 ring carbon atoms. If neither Ring A nor Ring B is a heteroaryl ring, the molecular stability may be reduced, and the luminous efficiency or lifetime may be reduced when applied to an organic electroluminescent device.

[0063] In formula 1, Z is BAr 2 ,POAr 3 , P.S.Ar 4 , SiAr 5 Ar 6 , or GeAr 7 Ar 8 It is.

[0064] In Chemical Formula 1, Ar 1 represents a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having from 7 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms.

[0065] In Chemical Formula 1, Ar 2 ~Ar 8 each independently represents a substituted or unsubstituted amino group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having from 7 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, which may be bonded to an adjacent group to form a ring.

[0066] In one embodiment, at least one of ring A and ring B in Chemical Formula 1 is represented by Chemical Formula 2 below. [ka]

[0067] In Chemical Formula 2, X and Y are each independently a single bond, O, S, SO, or SO 2 , Se, NR 3 , P.R. 4 , POR 5 , P.S.R. 6 , SiR 7 R 8 , G.E.R. 9 R 10 , or B.R. 11 It is.

[0068] In Chemical Formula 2, R 1 ~R 11 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted germyl group, a substituted or unsubstituted amino 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, R is a boryl group, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having from 7 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms. 1 ~R 11 may be bonded to adjacent groups to form a ring.

[0069] Either ring A or ring B in Chemical Formula 1 is a heteroaryl ring, and X and Y in Chemical Formula 2 are not simultaneously single bonds.

[0070] In one embodiment, the Ar 1 represents a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, which may be bonded to an adjacent group to form a ring.

[0071] In one embodiment, the Ar 1 has a substituent that bonds with one of the ring-forming atoms of ring B in Chemical Formula 1 to form a fused ring, Chemical Formula 1 may be represented by Chemical Formula 3 below. [ka]

[0072] In formula 3, Z' is Ar in formula 1. 1 Z' corresponds to one of the substituents of BAr 2 ,POAr 3 , P.S.Ar 4 , SiAr 5 Ar 6 , or GeAr 7 Ar 8 It is.

[0073] In Chemical Formula 3, ring L is Ar in Chemical Formula 1. 1Each ring L is independently a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms.

[0074] In Chemical Formula 3, ring A, ring B, and Z are as defined in Chemical Formula 1.

[0075] In one embodiment, Z and Z′ in Formula 3 may be the same as each other.

[0076] Ar in formula 1 2 ~Ar 8 each independently represents a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having from 7 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, and may be bonded to an adjacent group to form a ring.

[0077] In one embodiment, the Ar 2 , Ar 3 , Ar 4 , Ar 5 and Ar 6 or Ar 7 and Ar 8 Either of Ar 1 When the ring B in Chemical Formula 1 is substituted with an amino group having a substituent, and the amino group is bonded to one of the ring-forming atoms of Ring B in Chemical Formula 1 to form a fused ring, Chemical Formula 1 may be represented by the following Chemical Formula 4. [ka]

[0078] W in Chemical Formula 4 corresponds to Z in Chemical Formula 1 in which ring M is substituted. W is B, PO, PS, SiAr 5 , or GeAr 7 It is.

[0079] In formula 4, ring M is Ar 2 , Ar 3 , Ar 4, Ar 6 or Ar 8 and each independently represents a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms.

[0080] In formula 4, Ar 1 ' is a substituent of an amino group substituted on ring M, and Ar 1 ' is a substituted or unsubstituted alkyl group having from 1 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having from 7 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms.

[0081] In Chemical Formula 4, ring A, ring B, Ar 1 , Ar 5 , and Ar 7 is as defined in Chemical Formula 1.

[0082] In one embodiment, Z in Formula 1 is BAr 2 It is.

[0083] Z in Chemical Formula 1 is BAr 2 When this is the case, Z may be represented by the following formula 5: [ka]

[0084] In Chemical Formula 5, V 1 ~V 5 are each independently CR 12 or N. On the other hand, V 1 ~V 5 At least one of the following is CR 12 It is.

[0085] In Chemical Formula 5, R 12each independently represents 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 boryl group, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having from 7 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, and may be bonded to an adjacent group to form a ring.

[0086] In one embodiment, V of Formula 5 1 ~V 5 are each independently CR 12 and R 12 is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 2 to 10 carbon atoms.

[0087] In one embodiment, at least one of ring A and ring B in Chemical Formula 1 is a substituted or unsubstituted pyrrole, a substituted or unsubstituted thiophene, a substituted or unsubstituted oxazine, or a substituted or unsubstituted furan.

[0088] In one embodiment, Chemical Formula 1 is represented by Chemical Formula 6 below. [ka]

[0089] In Chemical Formula 6, A 1represents 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 boryl group, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having from 7 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, and may be bonded to an adjacent group to form a ring.

[0090] In Chemical Formula 6, n is an integer of 0 to 5. On the other hand, if n is 2 or more, a plurality of A 1 may be the same as or different from each other.

[0091] In Chemical Formula 6, X and Y are each independently a single bond, O, S, SO, or SO 2 , Se, NR 3 , P.R. 4 , POR 5 , P.S.R. 6 , SiR 7 R 8 , G.E.R. 9 R 10 , or B.R. 11 It is.

[0092] In Chemical Formula 6, R 1 ~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 boryl group, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having from 7 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms. 1 ~R 11 may be bonded to an adjacent group to form a ring.

[0093] In formula 6, Ar 1 is as defined in Chemical Formula 1.

[0094] The polycyclic compound according to one embodiment represented by Chemical Formula 1 is a delayed fluorescent light-emitting material. This polycyclic compound is a thermally activated delayed fluorescent light-emitting material.

[0095] For example, the polycyclic compound represented by Chemical Formula 1 has a small difference between the singlet energy level S1 and the triplet energy level T1, and may be used as a thermally activated delayed fluorescent material. In detail, the polycyclic compound according to one embodiment represented by Chemical Formula 1 may be represented by any one of the compounds shown in the following first compound group. In the following compound group 1, iPr represents an isopropyl group, and Ph represents a phenyl group.

[0096] [First compound group] [ka] JPEG2024170578000019.jpg194149 JPEG2024170578000020.jpg90151

[0097] The polycyclic compound represented by Chemical Formula 1 described above is used in the organic electroluminescent device 10 according to an embodiment to improve the efficiency and lifetime of the organic electroluminescent device. In particular, the polycyclic compound represented by Chemical Formula 1 described above is used in the emission layer EML of the organic electroluminescent device 10 according to an embodiment to improve the luminous efficiency and lifetime of the organic electroluminescent device.

[0098] In one embodiment, the emission layer EML includes a host and a dopant, the host is a delayed fluorescent host, and the dopant is a delayed fluorescent dopant. Meanwhile, the polycyclic compound according to one embodiment represented by Chemical Formula 1 is included as a dopant material in the emission layer EML. For example, the polycyclic compound according to one embodiment represented by Chemical Formula 1 may be used as a TADF dopant.

[0099] On the other hand, the emitting layer EML contains a known host material. For example, in one embodiment, the emitting layer EML contains Alq 3 (tris(8-hydroxyquinolino)aluminum), CBP (4,4'-bis(N-carbazolyl)-1,1'-biphenyl), PVK (poly(n-vinylcarbazole), ADN (9,10-di(naphthalen-2-yl)anthracene), TCTA (4,4',4"-tris(carbazol-9-yl)-triphenylamine), TPBi (1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene), TBADN (3-tert-butyl-9 ,10-Di(naphth-2-yl)anthracene), DSA (Distyrylarylene), CDBP (4,4'-Bis(9-carbazolyl)-2,2'-dimethyl-biphenyl), MADN (2-Methyl-9,10-bis(naphthalen-2-yl)anthracene), DPEPO (Bis[2-(diphenylphosphino)phenyl]ether oxide), CP1 (Hexaphenylcyclotriphosphazene), UGH2 (1,4-Bis(triphenylsilyl)benzene), DPSiO 3 (Hexaphenylcyclotrisiloxane), DPSiO 4 (octaphenylcyclotetrasiloxane), or PPF (2,8-bis(diphenylphosphoryl)diphenylfuran). However, the host materials are not limited to these, and may include other known delayed fluorescent light host materials in addition to the host materials listed.

[0100] Meanwhile, in the organic electroluminescent device 10 according to an embodiment, the emission layer EML may further include a known dopant material. The emission layer MEL may further include a styryl derivative (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzV) as a dopant. B), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2-yl)vinyl)phenyl)-N-phenylbenzenamine (N-BDAVBi), perylene and its derivatives (e.g., 2,5,8,11-tetra-t-butylperylene (TBP)), pyrene and its derivatives (e.g., 1,1-dipyrene, 1,4-dipyrenylbenzene, 1,4-bis(N,N-diphenylamino)pyrene), and the like.

[0101] 1 to 3, in an organic electroluminescent device 10 according to an embodiment, an electron transport region ETR is provided on an emission layer EML. The electron transport region ETR includes at least one of an electron blocking layer, an electron transport layer ETL, and an electron injection layer EIL, but is not limited thereto.

[0102] The electron transport region ETR has a single layer made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials.

[0103] For example, the electron transport region ETR may have a single layer structure of an electron injection layer EIL or an electron transport layer ETL, or may have a single layer structure made of an electron injection material and an electron transport material. The electron transport region ETR may have a single layer structure made 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 stacked in order from the first electrode EL1, but is not limited thereto. The thickness of the electron transport region ETR may be, for example, about 10 nm to about 150 nm.

[0104] The electron transport region ETR can be formed using various methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and laser induced thermal imaging (LITI).

[0105] When the electron transport region ETR includes an electron transport layer ETL, for example, the electron transport region ETR is 3 (Tris(8-hydroxyquinolinato)aluminum), 1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene, 2,4,6-tris(3'-pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzoimidazolyl-1-ylphenyl)-9,10-dinaphthylanthracene, TPBi(1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene), BCP(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bph en (4,7-diphenyl-1,10-phenanthroline), TAZ (3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole), NTAZ (4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole), tBu-PBD (2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole), BAlq (bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-biphenyl-4-olato)aluminum), Bebq 2 (beryllium bis(benzoquinolin-10-olato), ADN (9,10-di(naphthalen-2-yl)anthracene), and mixtures thereof.

[0106] When the electron transport region ETR includes the electron transport layer ETL, the thickness of the electron transport layer ETL may be about 10 nm to about 100 nm, for example, about 15 nm to about 50 nm. When the thickness of the electron transport layer HTL satisfies the above-mentioned range, sufficient electron transport properties can be obtained without a substantial increase in driving voltage.

[0107] When the electron transport region ETR includes an electron injection layer EIL, the electron transport region ETR may be, for example, LiF, LiQ (lithium quinolinate), Li 2Lanthanum group metals such as O, BaO, NaCl, CsF, and Yb, or metal halides such as RbCl, RbI, and KI may be used, but are not limited thereto. The electron injection layer EIL may also be made of a material in which an electron transport material and an insulating organo metal salt are mixed. Organic metal salts have an energy band gap of about 4 eV. Specifically, for example, the organic metal salt includes metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate, or metal stearate.

[0108] When the electron transport region ETR includes the electron injection layer ETL, the thickness of the electron injection layer ETL is about 0.1 nm to about 10 nm, or about 0.3 nm to about 9 nm. When the thickness of the electron injection layer EIL satisfies the above-mentioned range, sufficient electron injection characteristics can be obtained without a substantial increase in driving voltage.

[0109] The electron transport region ETR includes the hole blocking layer HBL as described above. The hole blocking layer HBL may include, for example, at least one of BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline) and Bphen (4,7-diphenyl-1,10-phenanthroline), but is not limited thereto.

[0110] The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 has electrical conductivity. The second electrode EL2 is made of a metal alloy or a conductive compound. The second electrode layer EL2 is a cathode. The second electrode EL2 may be a transmissive electrode, a semi-transmissive electrode, or a is a reflective electrode. If the second electrode EL2 is a transmissive electrode, the second electrode EL2 is made of a transparent metal oxide, for example, ITO, IZO, ZnO, ITZO, or the like.

[0111] If the second electrode EL2 is a semi-transmissive electrode or a reflective electrode, the second electrode EL2 contains 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 addition, the second electrode EL2 may have a multi-layer structure including a reflective film or semi-transmissive film formed of the above-mentioned materials, and a transparent conductive film formed of ITO, IZO, ZnO, ITZO, or the like.

[0112] Although not shown, the second electrode EL2 is connected to an auxiliary electrode When the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 can be reduced.

[0113] In the organic electroluminescent device 10, when a voltage is applied to the first electrode EL1 and the second electrode EL2, holes injected from the first electrode EL1 are transported through the hole transport region HTR. Electrons injected from the second electrode EL2 move to the emission layer EML via the electron transport region ETR. Electrons and holes recombine in the emission layer EML to generate excitons, and emit light when the excitons fall from the excited state to the ground state.

[0114] If the organic electroluminescent device 10 is a front emission type, the first electrode EL1 is a reflective electrode, and the second electrode EL2 is a transmissive electrode or a semi-transmissive electrode. If the organic electroluminescent device 10 is a back emission type, the first electrode EL1 is a transmissive electrode or a semi-transmissive electrode, and the second electrode EL2 is a reflective electrode.

[0115] The organic electroluminescent device 10 according to the embodiment of the present invention uses the above-mentioned polycyclic compound as a light-emitting layer material. When used as an organic light emitting diode, it shows improved luminous efficiency and life characteristics.

[0116] According to one embodiment of the present invention, there is provided a polycyclic compound represented by the following Chemical Formula 1: [ka]

[0117] In Chemical Formula 1, ring A and ring B are each independently a substituted or unsubstituted aryl ring having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl ring having 2 to 30 ring carbon atoms.

[0118] Meanwhile, in Chemical Formula 1, at least one of Ring A and Ring B is a substituted or unsubstituted heteroaryl ring having 2 to 30 ring carbon atoms. If neither Ring A nor Ring B is a heteroaryl ring, the molecular stability may be reduced, and the luminous efficiency or lifetime may be reduced when applied to an organic electroluminescent device.

[0119] In formula 1, Z is BAr 2 ,POAr 3 , P.S.Ar 4 , SiAr 5 Ar 6 , or GeAr 7 Ar 8 It is.

[0120] In Chemical Formula 1, Ar 1 represents a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having from 7 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms.

[0121] In Chemical Formula 1, Ar 2 ~Ar 8 each independently represents a substituted or unsubstituted amino group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having from 7 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, which may be bonded to an adjacent group to form a ring.

[0122] In one embodiment, at least one of ring A and ring B in Chemical Formula 1 is represented by Chemical Formula 2 below. [ka]

[0123] In the following formula 2, X and Y are each independently a single bond, O, S, SO, SO 2 , Se, NR 3 , P.R. 4 , POR 5 , P.S.R. 6 , SiR 7 R 8 , G.E.R. 9 R 10 , or B.R. 11 It is.

[0124] In Chemical Formula 2, R 1 ~R 2 each independently represents 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, R is an alkyl group, a boryl group, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having from 7 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms. 3 ~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 boryl group, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having from 7 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms. 1 ~R 11 may be bonded to an adjacent group to form a ring.

[0125] Either ring A or ring B in Chemical Formula 1 is a heteroaryl ring, and X and Y in Chemical Formula 2 are not simultaneously single bonds.

[0126] The polycyclic compound represented by Chemical Formula 1 according to an embodiment of the present invention may be the same as that described above with respect to the polycyclic compound in the organic electroluminescent device according to the embodiment of the present invention.

[0127] The polycyclic compound according to one embodiment is any one selected from the compounds listed in the first compound group described above. EXAMPLES

[0128] The present invention will be described in more detail with reference to the following specific examples and comparative examples. The following examples are merely illustrative for the purpose of aiding understanding of the present invention, and the scope of the present invention is not limited thereto.

[0129] (Synthesis example) The polycyclic compound according to one embodiment of the present invention is synthesized, for example, as follows: However, the method for synthesizing the polycyclic compound according to one embodiment of the present invention is not limited to the following.

[0130] 1. Synthesis of Compound 8 Compound 8, which is a polycyclic compound according to one embodiment of the present invention, is synthesized, for example, by the following reaction. [ka]

[0131] (Synthesis of intermediate compound A) In an Ar atmosphere, add N 1 -(2,3-dichlorophenyl)-N 1 ,N 2 ,N 3 - 9.63 g (20 mmol) of triphenyl-1,3-benzenediamine, 2.0 mL (22 mmol) of aniline, (Amphos)PdCl 20.71 g (1.0 mmol) of 1H2O3 and 2.11 g (22 mmol) of NaOtBu were added and stirred in 100 mL of xylene solvent at 120°C for 1 hour. After cooling in air, water was added to separate the organic layer, and the solvent was removed. The resulting crude product was purified by column chromatography (silica gel), yielding 7.40 g (69% yield) of compound A as a white solid. The molecular weight of compound A was 537.

[0132] (Synthesis of intermediate compound B) In an Ar atmosphere, 7.37 g (13.7 mol) of compound A, 4.08 g (15.0 mmol) of 2-bromo-1-phenyl-1H-indole, and Pd 2 (dba) 3 0.13g (0.14mmol), 0.26g (0.55mmol) of Ruphos (2-dicyclohexylphosphino-2',6'-diisopropoxybiphenyl), and 1.44g (15.0mmol) of NaOtBu were added, and the mixture was stirred at 100°C for 3 hours in 70mL of toluene solvent. After cooling in air, water was added to separate the organic layer, and the solvent was removed. The obtained crude product was purified by column chromatography (silica gel), and 6.79g (yield 68%) of compound B was obtained as a white solid. The molecular weight of compound B measured by FAB-MS measurement was 728.

[0133] (Synthesis of compound 8) In an Ar atmosphere, 50 mL of a dehydrated t-butylbenzene solution of 6.78 g (9.3 mmol) of compound B was added to a 300 mL three-neck flask and stirred at -78°C. 19.5 mL (37 mmol) of a 1.9 M pentane solution of t-BuLi was added dropwise to the flask. After the dropwise addition was completed, the temperature was raised to 60°C and the mixture was stirred for 2 hours, after which components with a boiling point lower than that of t-butylbenzene were removed under reduced pressure. The mixture was cooled to -30°C and stirred with BBr. 3After the dropwise addition, the temperature was raised to room temperature and stirred for 2 hours. After that, it was further cooled to 0°C, and 1.7mL (9.8mmol) of N,N-diisopropylethylamine was dropped. After the dropwise addition, the temperature was raised to room temperature and stirred for 1 hour, and then the temperature was raised to 120°C and heated and stirred for 8 hours. The reaction solution was cooled to room temperature, and an aqueous NaOAc solution cooled in an ice bath and toluene were added to separate the liquids. Next, the product was purified by short column chromatography (silica gel), and then recrystallized with a toluene / hexane solvent to obtain 5.09g (78% yield) of yellow solid compound 8.

[0134] Compound 8 was identified by FAB-MS and NMR. The molecular weight of compound 8 measured by FAB-MS was 702. 1 H-NMR (CDCl 3 ) measurement The measured 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).

[0135] 2. Synthesis of Compound 10 Compound 10, which is a polycyclic compound according to one embodiment of the present invention, can be synthesized, for example, by the following reaction. [ka]

[0136] (Synthesis of intermediate compound C) In an Ar atmosphere, 6.28 g (20 mmol) of 2,3-dichloro-N,N-diphenyl-1,3-benzenediamine and 2.0 mL (2 2mmol), (Amphos)PdCl 20.71 g (1.0 mmol) of and 2.11 g (22 mmol) of NaOtBu were added, and the mixture was stirred in 100 mL of xylene solvent at 120°C for 1 hour. After cooling in air, water was added to separate the organic layer, and the solvent was removed. The resulting crude product was purified by column chromatography (silica gel), and 6.00 g (81% yield) of compound C was obtained as a white solid. The molecular weight of compound C measured by FAB-MS was 370.

[0137] (Synthesis of intermediate compound D) In an Ar atmosphere, 5.97 g (16.1 mol) of compound C and 4.38 g (17.7 mmol) of 3-bromo-6-chloro-benzo[b]thiophene were placed in a 200 mL three-neck flask. , Pd 2 (dba) 3 0.15g (0.16mmol), 0.30g (0.64mmol) of Ruphos, and 1.70g (17.7mmol) of NaOtBu were added and stirred in 80mL of toluene solvent at 100°C for 3 hours. After cooling in air, water was added to separate the organic layer and the solvent was removed. The obtained crude product was purified by column chromatography (silica gel), and 5.27g (yield 61%) of compound D was obtained as a white solid. The molecular weight of compound D measured by FAB-MS measurement was 536.

[0138] (Synthesis of intermediate compound E) In an Ar atmosphere, 5.26 g (9.8 mol) of compound D, 1.66 g (9.8 mmol) of diphenylamine, and Pd 2 (dba) 3 0.18 g (0.20 mmol) of toluene, 0.36 g (0.78 mmol) of Ruphos, and 1.04 g (10.8 mmol) of NaOtBu were added and stirred in 50 mL of toluene solvent at 110°C for 8 hours. After cooling in air, water was added to separate the organic layer, and the solvent was removed. The resulting crude product was purified by column chromatography (silica gel), and 5.05 g (yield 777%) of compound E was obtained as a white solid. The molecular weight of compound E measured by FAB-MS was 669. I did.

[0139] (Synthesis of compound 10) In an Ar atmosphere, 40 mL of a dehydrated t-butylbenzene solution of 5.03 g (7.5 mmol) of compound E was added to a 300 mL three-neck flask and stirred at -78°C. 15.8 mL (30 mmol) of a 1.9 M pentane solution of t-BuLi was added dropwise to the flask. After the dropwise addition was completed, the temperature was raised to 60°C and the mixture was stirred for 2 hours, after which components with a boiling point lower than that of t-butylbenzene were removed under reduced pressure. The mixture was cooled to -30°C and stirred with BBr. 3 After the dropwise addition, the temperature was raised to room temperature and stirred for 2 hours. After that, it was further cooled to 0°C, and 1.4mL (8.0mmol) of N,N-diisopropylethylamine was dropped. After the dropwise addition, the temperature was raised to room temperature and stirred for 1 hour, and then the temperature was raised to 120°C and heated and stirred for 8 hours. The reaction solution was cooled to room temperature, and an aqueous NaOAc solution cooled in an ice bath and toluene were added to separate the liquids. Next, the product was purified by short column chromatography (silica gel), and then recrystallized with a toluene / hexane solvent to obtain 4.00g (yield 83%) of yellow solid compound 10.

[0140] Compound 10 was identified by FAB-MS and NMR. The molecular weight of compound 10 measured by FAB-MS was 643. 1 H-NMR (CDCl 3 ) measurement The chemical shift values ​​δ of compound 10 measured by FT-IR spectrophotometer 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).

[0141] 3. Synthesis of Compound 11 Compound 11, which is a polycyclic compound according to one embodiment of the present invention, can be synthesized, for example, by the following reaction. [ka]

[0142] (Synthesis of intermediate compound F) Under Ar atmosphere, 100 mL of a dehydrated THF solution of 4.55 g (20 mmol) of 6-chloro-1-phenyl-1H-indole was added to a 500 mL three-neck flask and stirred at -78 ° C. Here, 13 mL (21 mmol) of a 1.6 M hexane solution of n-BuLi was dropped and stirred for 2 hours. 20 mL of a dehydrated THF solution of 5.33 g (21 mmol) of iodine was dropped to this, and stirred at -78 ° C for 2 hours, and then stirred at room temperature for 3 hours. After the reaction, this mixture was washed with water. The obtained organic phase was concentrated to obtain a viscous substance. The obtained crude product was purified by column chromatography (silica gel), and 6.00 g (yield 85%) of a white solid compound F was obtained. The molecular weight of compound F measured by FAB-MS measurement was 353.

[0143] (Synthesis of intermediate compound G) In an Ar atmosphere, 5.98 g (16.9 mol) of compound F and 4.78 g (16.9 mm) of 2-bromo-5-chloro-N-phenyl-benzenamine were placed in a 300 mL three-neck flask. ol), Pd 2 (dba) 3 0.16g (0.17mmol), 0.25g (0.34mmol) of dppf, and 1.79g (18.6mmol) of NaOtBu were added and stirred in 85mL of toluene solvent at 80°C for 6 hours. After cooling in air, water was added to separate the organic layer and the solvent was removed. The obtained crude product was purified by column chromatography (silica gel), and 4.96g (yield 58%) of compound G was obtained as a white solid. The molecular weight of compound G measured by FAB-MS measurement was 506.

[0144] (Synthesis of intermediate compound H) In an Ar atmosphere, 100 mL of a dehydrated THF solution of 4.93 g (9.7 mmol) of compound G was added to a 500 mL three-neck flask and stirred at -78°C. 12.5 mL (20 mmol) of a 1.6 M hexane solution of n-BuLi was added dropwise to the flask and stirred for 2 hours, after which BBr 31.0mL (10mmol) of was added dropwise, stirred at -78°C for 1 hour, and stirred at room temperature for 3 hours. After cooling to 0°C, 10mL (10mmol) of 1.0M 2,4,6-triisopropylphenylmagnesium bromide in THF was added dropwise, stirred at 0°C for 2 hours, and then stirred at room temperature for 3 hours. After the reaction, the mixture was washed with water. The organic phase obtained was concentrated to obtain a viscous substance. The obtained crude product was purified by column chromatography (silica gel), and 4.36g (yield 70%) of compound H was obtained as a yellow solid. The molecular weight of compound H measured by FAB-MS was 640.

[0145] (Synthesis of Compound 11) In an Ar atmosphere, 4.35 g (6.8 mol) of compound H, 2.30 g (13.6 mmol) of diphenylamine, and Pd 2 (dba) 3 0.31 g (0.34 mmol) of toluene, 0.63 g (1.36 mmol) of Ruphos, and 1.44 g (15.0 mmol) of NaOtBu were added, and the mixture was stirred in 70 mL of toluene at 110°C for 8 hours. After cooling in air, water was added to separate the organic layer, and the solvent was removed. The resulting crude product was After purification by column chromatography (silica gel), 3.20 g (52% yield) of compound 11 was obtained as a yellow solid.

[0146] Compound 11 was identified by FAB-MS and NMR. The molecular weight of compound 11 measured by FAB-MS was 906. 1 H-NMR (CDCl 3 ) measurement The chemical shift values ​​δ of compound 11 measured by FT-IR spectrophotometer 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).

[0147] 4. Synthesis of Compound 12 Compound 12, which is a polycyclic compound according to one embodiment of the present invention, is synthesized, for example, by the following reaction. [ka]

[0148] (Synthesis of intermediate compound I) In a 500 mL three-neck flask, 9.86 g (50 mol) of p,p'-ditolylamine, 10.65 g (50 mmol) of 2-bromobenzo[b]thiophene, and Pd 2 (dba) 3 0.46g (0.50mmol), 0.93g (2.0mmol) of Ruphos, and 5.29g (55mmol) of NaOtBu were added and stirred in 250mL of toluene solvent at 100°C for 2 hours. After cooling in air, water was added to separate the organic layer, and the solvent was removed. The obtained crude product was purified by column chromatography (silica gel), and 15.15g (92% yield) of white solid compound I was obtained. The molecular weight of compound I measured by FAB-MS measurement was 329.

[0149] (Synthesis of intermediate compound K) In a 1000mL round bottom flask, 15.13g (46mmol) of compound I, 25.45g (143mmol) of N-bromosuccinimide, and 30mL of acetic acid were added, and the mixture was stirred in 30mL of chloroform solvent at 0°C for 2 hours. After cooling in air, an aqueous sodium thiosulfate solution was added to separate the organic layer, and the solvent was removed. After purification by column chromatography (silica gel), 23.16g (89% yield) of white solid compound K was obtained. The molecular weight of compound K measured by FAB-MS measurement was 562.

[0150] (Synthesis of compound 12) In an Ar atmosphere, 160 mL of a dehydrated t-butylbenzene solution of 23.13 g (40.9 mmol) of compound A was added to a 1000 mL three-neck flask and stirred at -78°C. 129 mL (245 mmol) of a 1.9 M pentane solution of t-BuLi was added dropwise to the flask. After the dropwise addition was completed, the temperature was raised to room temperature and stirred for 2 hours. Then, the flask was cooled to -30°C and BBr 3 After the dropwise addition, the temperature was raised to room temperature and stirred for 1 hour. After that, it was further cooled to 0°C, and 14.9 mL (82 mmol) of 1,2,2,6,6-pentamethylpiperidine was added dropwise. After the dropwise addition, the temperature was raised to room temperature and stirred for 1 hour. After stirring for 1 hour, 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 164mL (164mmol) of 1.0M 2,4,6-triisopropylphenylmagnesium bromide in THF was added dropwise, and the mixture was stirred at 0°C for 2 hours, and then stirred at room temperature for 3 hours. After the reaction, phosphate buffer (pH 6) and toluene were added and the mixture was separated. Next, the mixture was purified by column chromatography (silica gel) and then recrystallized with a toluene / hexane solvent to obtain 4.55g (yield 19%) of yellow solid compound 12.

[0151] 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 in the measurement were 8.05 (1H), 7.93 (1H), 7.57-7.40 (2H), 7.19-7.11 (5H), 6.99-6.95 (4H), 2.38-2.31 (18H), and 2.20-2.16 (6H).

[0152] (Example of element creation) The polycyclic compounds 8, 10, 11, and 12 described above were used as materials for the light-emitting layer to fabricate organic electroluminescent devices of Examples 1 to 4. The compounds used in the light-emitting layer in Examples 1 to 4 and Comparative Examples 1 to 4 are shown below. [Example Compounds] [ka]

[0153] The organic electroluminescent devices of Comparative Examples 1 to 4 were produced using the following Comparative Example compounds R-1 to R-4 as materials for the light-emitting layer. [Comparative Example Compound] [ka]

[0154] For the organic electroluminescence devices of Examples 1 to 4 and Comparative Examples 1 to 4, ITO was patterned on a glass substrate to a thickness of 150 nm, then washed with ultrapure water and subjected to UV ozone treatment for 10 minutes. Next, HAT-CN was evaporated to a thickness of 10 nm, α-NPD was evaporated to a thickness of 80 nm, and mCP was evaporated to a thickness of 5 nm to form a hole transport region.

[0155] Next, when forming the light-emitting layer, the polycyclic compound of one embodiment of the present invention or the comparative compound and DPEPO were co-deposited in a ratio of 20:80 to form a layer having a thickness of 20 nm. Next, a layer having a thickness of 10 nm was formed using DPEPO. That is, in the light-emitting layer formed by co-deposition, in Examples 1 to 4, compounds 8, 10, 11, and 12 were mixed with DPEPO and deposited, respectively, and in Comparative Examples 1 to 4, comparative compounds R-1, R-2, R-3, and R-4 were mixed with DPEPO and deposited.

[0156] A 30 nm thick layer of TPBi was formed on the light-emitting layer, followed by a 0.5 nm thick layer of LiF to form the electron transport region, and then a 100 nm thick second electrode was formed of aluminum (Al).

[0157] In the examples, the hole transport region, the light emitting layer, the electron transport region, and the second electrode were formed using a vacuum deposition apparatus.

[0158] (Evaluation of the characteristics of organic electroluminescent devices) In order to evaluate the characteristics of the organic electroluminescent devices according to the examples and comparative examples, the maximum emission wavelength (nm) and external quantum yield (%) were measured. The measurements were performed using a Hamamatsu Photonics C9920-11 brightness distribution characteristic measuring device. The lifetime was measured at an initial brightness of 100 cd / m 2 The half-life of the luminance from 10 mA / cm is shown. 2 means the value at [Table 1]

[0159] Referring to Table 1, it can be seen that the organic electroluminescent devices of Examples 1 to 4, in which the polycyclic compound according to one embodiment of the present invention is used as a dopant material in the light-emitting layer, exhibit higher external quantum efficiency than those of Comparative Examples 1 to 4. It can also be seen that the organic electroluminescent devices of Examples 1 to 4, in which the polycyclic compound according to one embodiment of the present invention is used as a dopant material in the light-emitting layer, achieve a longer life than those of Comparative Examples 1 to 4.

[0160] Referring to the results in Table 1, it can be seen that the example compounds can be used as highly efficient and long-life thermally activated delayed fluorescent materials.

[0161] In the case of the organic electroluminescent device according to one embodiment of the present invention, the polycyclic compound according to the above-mentioned embodiment is contained in the light emitting layer, thereby exhibiting high light emitting efficiency.

[0162] Compared with the Examples, the Comparative Example compounds R-1 to R-4 do not contain a stable heteroaryl ring in the core molecule, and therefore the organic electroluminescent devices of Comparative Examples 1 to 4 exhibit lower external quantum efficiency and shorter device life than the Examples.

[0163] Although the present invention has been described above with reference to preferred embodiments thereof, it will be understood by those skilled in the art or those having ordinary knowledge in the art that various modifications and variations of the present invention can be made without departing from the spirit and technical scope of the present invention as set forth in the claims below.

[0164] Therefore, the technical scope of the present invention should be determined not by the contents described in the detailed description of the specification, but by the claims. [Explanation of symbols]

[0165] 10: Organic electroluminescent element EL1: First electrode EL2: second electrode HTR: hole transport region EML: Light-emitting layer ETR: Electron transport region

Claims

1. A polycyclic compound represented by the following chemical formula 4. 【Chemistry 1】 (In the above Chemical Formula 4, Ar １ and Ar １ each ' is independently a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having from 7 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, Ring A and ring B are each independently a substituted or unsubstituted aryl ring having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl ring having from 2 to 30 ring carbon atoms, and at least one of ring A and ring B is represented by chemical formula 2: 【Chemistry 2】 ring M is a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, W is B, PO, PS, SiAr ５ , or GeAr ７ and Ar ５ and Ar ７ each independently represents a substituted or unsubstituted amino group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted aryl group having from 6 to 30 ring carbon atoms, a substituted aralkyl group having from 7 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, In Chemical Formula 2, X and Y each independently represent a single bond, O, S, SO, or SO ２ , Se, N.R. ３ , P.R. ４ , P.O.R. ５ , P.S.R. ６ , SiR ７ R ８ , GeR ９ R １０ , or B.R. １１ X and Y are not simultaneously single bonds, R １ and R ２ 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 boryl group, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms; when ring A is represented by chemical formula 2, R １ and R ２ are bonded to form a ring, R ３ ~R １１ each independently represents 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 boryl group, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having from 7 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, The R １ ~R １１ may be bonded to an adjacent group to form a ring or may not be bonded to an adjacent group, * indicates the bond position.)

2. The polycyclic compound according to claim 1 , wherein W is B.

3. A polycyclic compound represented by the following chemical formula 4. 【Chemistry 3】 (In Chemical Formula 4, Ar １ and Ar １ each ' is independently a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having from 7 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, ring A and ring B are each independently a substituted or unsubstituted aryl ring having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl ring having from 2 to 30 ring carbon atoms, and at least one of ring A and ring B is a substituted or unsubstituted pyrrole, a substituted or unsubstituted thiophene, a substituted or unsubstituted oxazine, or a substituted or unsubstituted furan; ring M is a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, W is for BAr ２ , POAr ３ , P.S.Ar ４ , SiAr ５ Ar ６ , or GeAr ７ Ar ８ and Ar ２ ~Ar ８ are each independently a substituted or unsubstituted amino group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, a substituted aralkyl group having from 7 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms.

4. A first electrode; a hole transport region disposed over the first electrode; a light-emitting layer disposed over the hole transport region; an electron transport region disposed over the light emitting layer; a second electrode disposed over the electron transport region; The light-emitting layer comprises the polycyclic compound according to claim 1 .

5. The organic electroluminescent device according to claim 4 , wherein the light-emitting layer emits delayed fluorescence.

6. The organic electroluminescent device according to claim 4 , wherein the light-emitting layer is a thermally activated delayed fluorescent light-emitting layer.

7. The organic electroluminescent device according to claim 4 , wherein the light-emitting layer emits blue light.

8. 5. The organic electroluminescent device according to claim 4, wherein the first electrode and the second electrode each independently include 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, In, Sn, and Zn, a compound including a plurality of elements selected from the group consisting of these elements, a mixture including a plurality of elements selected from the group consisting of these elements, or one or more oxides selected from the group consisting of these elements.

9. The hole transport region is a hole injection layer disposed over the first electrode; a hole transport layer disposed on the hole injection layer; Including, The thickness of the hole injection layer is about 3 nm to about 100 nm; The organic electroluminescent device of claim 4, wherein the hole transport layer has a thickness of about 1 nm to about 100 nm.

10. The electron transport region is an electron transport layer disposed over the light emitting layer; an electron injection layer disposed on the electron transport layer; Including, the thickness of the electron transport layer is from about 10 nm to about 100 nm; The organic electroluminescent device according to claim 4, wherein the electron injection layer has a thickness of about 0.1 nm to about 10 nm.

11. The organic electroluminescent device according to claim 4, wherein the light-emitting layer has a thickness of about 10 nm to about 60 nm.

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