Organic electroluminescent device and polycyclic compound for organic electroluminescent device

Abstract

To provide an organic electroluminescent element with high efficiency and a polycyclic compound used for the same.SOLUTION: An organic electroluminescent element includes a first electrode EL1, an organic layer OL, and a second electrode EL2, and the organic layer OL includes a polycyclic compound expressed by Chemical Formula 1 (Chemical Formula 1).SELECTED DRAWING: Figure 1

Description

[Technical field]

[0001] The present invention relates to an organic electroluminescent device and a polycyclic compound for an organic electroluminescent device. [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 and higher luminous efficiency of the organic electroluminescent devices, and there is a continuous demand for the development of materials for organic electroluminescent devices that can stably achieve these goals.

[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 underway. Summary of the Invention [Problem to be solved by the invention]

[0005] An object of the present invention is to provide a highly efficient organic electroluminescent device 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] In one embodiment, there is provided an organic electroluminescent device comprising a first electrode, an organic layer disposed on the first electrode, and a second electrode disposed on the organic layer, the organic layer comprising a polycyclic compound represented by Chemical Formula 1:

[0008] [ka] ...(chemical formula 1) In the above Chemical Formula 1, X 1 ~X 4 are each independently NR 9 , O, or S, and R 1 ~R 8 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having from 1 to 20 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; R 9 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having from 1 to 20 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, or is bonded to an adjacent group to form a ring, a to f each independently represent an integer of from 0 to 4, m and n each independently represent 0 or 1, a dotted line represents a bond or non-bond, and ring A is represented by any one of the following chemical formulas 2-1 to 2-3.

[0009] [ka] (Chemical formula 2-1) JPEG0007633036000003.jpg5875(Chemical formula 2-2) JPEG0007633036000004.jpg5977 (chemical formula 2-3) In the above Chemical Formula 2-1 to Chemical Formula 2-3, the mark "*" indicates the position of condensation, and X 5 and X 6 are each independently CR 30 R 31 , N.R. 32 , O, or S, and R 30 ~R 32 each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having from 1 to 20 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; R 20 ~R 29 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having from 1 to 20 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, with the proviso that when the ring A is represented by the chemical formula 2-1 or 2-2, at least one of the m and n is 1.

[0010] The organic layer includes a hole transport region disposed over the first electrode, an emissive layer disposed over the hole transport region, and an electron transport region disposed over the emissive layer.

[0011] The light-emitting layer contains the polycyclic compound and emits delayed fluorescence.

[0012] The light-emitting layer is a delayed fluorescent light-emitting layer containing a host and a dopant, and the dopant is the polycyclic compound.

[0013] The light-emitting layer is a thermally activated delayed fluorescent light-emitting layer that emits blue light.

[0014] The electron transport region includes an electron transport layer disposed on the light emitting layer and an electron injection layer disposed on the electron transport layer, and the electron transport layer or the electron injection layer includes the polycyclic compound.

[0015] The above-mentioned Chemical Formula 2-2 is represented by any one of the following Chemical Formulas 3-1 to 3-4. [ka] (Chemical formula 3-1) JPEG0007633036000006.jpg7471(Chemical formula 3-2) JPEG0007633036000007.jpg3571 (chemical formula 3-3) JPEG0007633036000008.jpg3571(Chemical formula 3-4) In the above Chemical Formula 3-1 to Chemical Formula 3-4, the mark "*" indicates the position of condensation, and R 30 , R 31 , and R 33 each independently represents a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and j is an integer of 0 to 5.

[0016] The above-mentioned Chemical Formula 2-3 is represented by any one of the following Chemical Formulas 4-1 to 4-3. [ka] (Chemical formula 4-1) JPEG0007633036000010.jpg4678 (chemical formula 4-2) JPEG0007633036000011.jpg8077 (chemical formula 4-3) In the above Chemical Formula 4-1 to Chemical Formula 4-3, the mark "*" indicates the position of condensation, and R 34 represents a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and k is an integer of 0 to 5.

[0017] The above-mentioned Chemical Formula 1 is represented by the following Chemical Formula 5-1 or 5-2. [ka] ...(chemical formula 5-1) TIFF0007633036000013.tif62160 ...(chemical formula 5-2) In the above Chemical Formula 5-1 and Chemical Formula 5-2, X 1 ~X 4 , R 1 ~R 8 , R 20 , R 21 , a to f are as defined in Chemical Formula 1 and Chemical Formula 2-1.

[0018] The above-mentioned Chemical Formula 1 is represented by the following Chemical Formula 6-1 or 6-2. [ka] ...(chemical formula 6-1) TIFF0007633036000015.tif59156 ...(chemical formula 6-2) In the above Chemical Formula 6-1 and Chemical Formula 6-2, X 1 ~X 5 , R 1 ~R 8 , R 22 ~R 25 , a to f are as defined in Chemical Formula 1 and Chemical Formula 2-2.

[0019] The above Chemical Formula 1 is represented by any one of the following Chemical Formulas 7-1 to 7-3. [ka] ...(chemical formula 7-1) TIFF0007633036000017.tif55159 ...(chemical formula 7-2) TIFF0007633036000018.tif56161 ...(chemical formula 7-3) In the above Chemical Formula 7-1 and Chemical Formula 7-3, X 1 ~X 4 , X 6 , R 1 ~R 8 , R 26 ~R 29 , a to f are as defined in Chemical Formula 1 and Chemical Formula 2-3.

[0020] X 1 ~X 4 are each independently NR 11 or O, 11 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[0021] X 1 and X 4 are the same as each other, and the X 2 and X 3 are equivalent to each other.

[0022] The compound represented by Chemical Formula 1 is any one of the compounds shown in the following first to third compound groups.

[0023] In another embodiment, a polycyclic compound represented by Formula 1 is provided. Effect of the Invention

[0024] The organic electroluminescent device according to an embodiment of the present invention can achieve high efficiency.

[0025] The polycyclic compound according to an embodiment of the present invention can improve the efficiency of an organic electroluminescent device. [Brief description of the drawings]

[0026] [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. [Figure 4] 1 is a cross-sectional view illustrating an organic electroluminescent device according to an embodiment of the present invention. [Diagram 5] 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

[0027] 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 included within the spirit and technical scope of the present invention.

[0028] As used herein, when a component (or region, layer, portion, etc.) is referred to as being "on" or "coupled" to another component, it means that it may be directly disposed, coupled, or connected to the other component, or that a third component may be disposed therebetween.

[0029] The same reference numerals refer to the same components. Also, in the drawings, thicknesses, proportions and dimensions of the components are exaggerated for the purpose of effectively explaining the technical contents.

[0030] "And / or" includes all combinations of one or more of the associated construct.

[0031] Terms such as first and second are used to describe various components, but the components are not limited to the terms. The terms are used only to distinguish one structural element from another. For example, a first component may be named a second component, and similarly, a second component may be named a first component, without departing from the scope of the present invention. A singular expression includes a plural expression unless the context clearly indicates otherwise.

[0032] In addition, terms such as "under", "below", "up" and "above" are used to describe the relationship between components shown in the drawings. The terms are relative concepts and are described based on the directions shown in the drawings.

[0033] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which the present invention belongs. Furthermore, terms such as those defined in commonly used dictionaries should be interpreted to have a meaning consistent with the meaning in the context of the relevant art, and are expressly defined herein, unless interpreted in an idealized or overly formal sense.

[0034] It should be understood that the terms "comprise" or "have" specify the presence of any feature, numeral, step, operation, component, part, or combination thereof described hereinabove in the specification, but do not preclude the presence or additional possibility of one or more other features, numerals, steps, operations, components, parts, or combinations thereof.

[0035] On the other hand, 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, an oxy group, a thio group, a sulfinyl group, a sulfonyl group, a carbonyl group, a boron group, a phosphine oxide group, a phosphine sulfide group, an alkyl group, an alkenyl group, an alkoxy group, a hydrocarbon ring group, an aryl group, and a heterocyclic group. In addition, each of the substituents exemplified above may be substituted or unsubstituted. For example, a biphenyl group may be interpreted as an aryl group, or as a phenyl group substituted with a phenyl group.

[0036] In this specification, "adjacent groups bond together to form a ring" means adjacent groups bond together to form a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle. Hydrocarbon rings include aliphatic hydrocarbon rings and aromatic hydrocarbon rings. Heterocyclic groups include aliphatic heterocyclic groups and aromatic heterocyclic groups. The ring formed by bonding adjacent groups together is a monocycle or polycycle. In addition, the ring formed by bonding together may be linked to another ring to form a spiro structure.

[0037] In the present specification, the term "adjacent group" refers to a substituent substituted on an atom directly connected 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 that is sterically 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-diethylcyclopentane are interpreted as "adjacent groups" to each other.

[0038] In this specification, examples of halogen atoms include a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0039] In this specification, the boron group includes an alkyl boron group and an aryl boron group. The boron group means a boron atom bonded to the alkyl or aryl group defined above. Examples of the boron group include, but are not limited to, a trimethyl boron group, a triethyl boron group, a t-butyl dimethyl boron group, a triphenyl boron group, a diphenyl boron group, and a phenyl boron group.

[0040] 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, ada Mantyl, 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 Examples of such alkyl groups include, but are not limited to, n-heptadecyl, n-octadecyl, n-nonadecyl, n-icosyl, 2-ethylicosyl, 2-butylicosyl, 2-hexylicosyl, 2-octylicosyl, n-henicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, and n-triacontyl groups.

[0041] In this specification, an alkenyl group refers to a hydrocarbon group containing one or more carbon double bonds in the middle or at the end of an alkyl group having two or more carbon atoms. The alkenyl group is linear or branched. The number of carbon atoms is not particularly limited, but is 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups include, but are not limited to, vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienylaryl, styrenyl, and styrylvinyl groups.

[0042] In this specification, an alkynyl group refers to a hydrocarbon group containing one or more carbon triple bonds in the middle or at the end of an alkyl group having two or more carbon atoms. The alkynyl group is linear or branched. The number of carbon atoms is not particularly limited, but is 2 to 30, 2 to 20, or 2 to 10. Specific examples of the alkynyl group include, but are not limited to, an ethynyl group and a propynyl group.

[0043] In the present specification, the term "hydrocarbon ring group" refers to any functional group or substituent derived from an aliphatic hydrocarbon ring, or any functional group or substituent derived from an aromatic hydrocarbon ring. The number of ring carbon atoms in the hydrocarbon ring group is 5 to 60, 5 to 30, or 5 to 20.

[0044] In this specification, the aryl group means any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group is a monocyclic aryl group or a polycyclic aryl group. The number of ring carbon atoms of the aryl group is 6 to 30, 6 to 20, or 6 to 15. 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.

[0045] In this specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. Examples of fluorenyl groups that may be substituted include, but are not limited to, the following:

[0046] [ka] JPEG0007633036000020.jpg3941 JPEG0007633036000021.jpg3256 JPEG0007633036000022.jpg3539

[0047] In this specification, a heterocyclic group refers to any functional group or substituent derived from a ring containing one or more of B, O, N, P, Si, and S as heteroatoms. Heterocyclic groups include aliphatic heterocyclic groups and aromatic heterocyclic groups. Aromatic heterocyclic groups are heteroaryl groups. The aliphatic heterocycles and aromatic heterocycles are monocyclic or polycyclic.

[0048] In this specification, the heterocyclic group includes one or more of B, O, N, P, Si, and S as a heteroatom. If the heterocyclic group includes two or more heteroatoms, the two or more heteroatoms may be the same or different. The heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and is a concept including a heteroaryl group. The number of ring carbon atoms of the heterocyclic group is 2 to 30, 2 to 20, or 2 to 10.

[0049] In this specification, an aliphatic heterocyclic group contains one or more heteroatoms selected from B, O, N, P, Si, and S. The number of ring carbon atoms in the aliphatic heterocyclic group is 2 to 30, 2 to 20, or 2 to 10. Examples of the aliphatic heterocyclic group include, but are not limited to, an oxirane group, a thiirane group, a pyrrolidine group, a piperidine group, a tetrahydrofuran group, a tetrahydrothiophene group, a thiane group, a tetrahydropyran group, and a 1,4-dioxane group.

[0050] In this specification, the heteroaryl group includes one or more of B, O, N, P, Si, and S as a heteroatom. If the heteroaryl group includes two or more heteroatoms, the two or more heteroatoms may be the same or different. The heteroaryl group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The number of ring carbon atoms of the heteroaryl group is 2 to 30, 2 to 20, or 2 to 10. Examples of the heteroaryl group include a thiophenyl group, a furanyl group, a pyrrolyl group, an imidazolyl group, a triazolyl group, a pyridinyl group, a bipyridinyl group, a pyrimidinyl group, a triazinyl group, a triazolyl group, an acridyl group, a pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxanyl 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-arylcarbazolyl group. , N-heteroarylcarbazolyl groups, N-alkylcarbazolyl groups, benzoxazolyl groups, benzimidazolyl groups, benzothiazolyl groups, benzocarbazolyl groups, benzothiophenyl groups, dibenzothiophenyl groups, thienothiophenyl groups, benzofuranyl groups, phenanthrolinyl groups, thiazolyl groups, isoxazolyl groups, oxazolyl groups, oxadiazolyl groups, thiadiazolyl groups, phenothiazinyl groups, dibenzosilolyl groups, and dibenzofuran groups.

[0051] 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.

[0052] In this specification, the number of carbon atoms of the amino group is not particularly limited, but is from 1 to 30. The amino group includes an alkylamino group, an arylamino group, or a heteroarylamino group. Examples of the amino group include, but are not limited to, a methylamino group, a dimethylamino group, a phenylamino group, a diphenylamino group, a naphthylamino group, a 9-methyl-anthracenylamino group, and a triphenylamino group.

[0053] As used herein, thiol groups include alkylthio and arylthio groups.

[0054] In this specification, the alkoxy group is linear, branched, or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but may be, for example, 1 to 20 or 1 to 10. Examples of oxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, benzyloxy, etc.

[0055] Hereinafter, an organic electroluminescent device according to an embodiment of the present invention and an embodiment of a compound contained therein will be described with reference to the drawings.

[0056] 1 to 5 are cross-sectional views each showing a schematic configuration of an organic electroluminescent device according to an embodiment of the present invention. Referring to Fig. 1 to 5, in an organic electroluminescent device 10 according to an embodiment, a first electrode EL1 and a second electrode EL2 are disposed facing each other, and an organic layer OL is disposed between the first electrode EL1 and the second electrode EL2.

[0057] 2 to 5, the organic layer OL according to an embodiment includes a plurality of functional layers. The plurality of functional layers include a hole transport region HTR, an emission layer EML, and an electron transport region ETR. That is, the 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. The organic electroluminescent device 10 according to an embodiment of the present invention further includes a capping layer CPL disposed on the second electrode EL2.

[0058] In an embodiment of the organic light emitting device 10, an organic layer OL disposed between a first electrode EL1 and a second electrode EL2 includes a polycyclic compound according to an embodiment of the present invention described below. If the organic layer OL includes an emission layer EML, the emission layer EML includes a polycyclic compound according to an embodiment of the present invention. However, the embodiment is not limited thereto. In an embodiment of the organic light emitting device 10, in addition to the emission layer EML, a hole transport region HTR or an electron transport region ETR, which are a plurality of functional layers disposed between the first electrode EL1 and the second electrode EL2, may include a polycyclic compound according to an embodiment of the present invention described below, or a capping layer CPL disposed on the second electrode EL2 may include a polycyclic compound according to an embodiment of the present invention described below.

[0059] Meanwhile, Fig. 3 shows 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. 2. Fig. 4 shows 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. 2. Fig. 5 shows a cross-sectional view of an organic electroluminescent device 10 according to an embodiment in which a capping layer CPL is disposed on the second electrode EL2, in comparison with Fig. 3.

[0060] 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 a pixel electrode or a positive electrode. 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 includes a transparent metal oxide, such as 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 (e.g., a mixture of Ag and Mg). Or, it is a multi-layer structure including a reflective film or semi-transparent film made of the above-mentioned material, and a transparent conductive film made of ITO, IZO, ZnO, ITZO, etc. For example, the first electrode EL1 may have a triple-layer structure of ITO / Ag / ITO, but is not limited thereto. The thickness of the first electrode EL1 may be about 100 nm to about 1000 nm, for example, about 100 nm to about 300 nm.

[0061] The organic layer OL is disposed on the first electrode EL1. The organic layer OL has a multi-layer structure having a single layer made of a single material, a single layer made of multiple different materials, or a multiple layer made of multiple different materials. For example, the organic layer OL may have a single layer structure of an emitting layer EML, or a multi-layer structure of a hole transport region HTR, an emitting layer EML, and an electron transport region ETR, but the embodiment is not limited thereto.

[0062] The organic layer OL of the organic electroluminescent device 10 according to an embodiment includes a polycyclic compound according to an embodiment of the present invention. If the organic layer OL has a multi-layer structure having a plurality of layers, any one of the layers includes a polycyclic compound according to an embodiment of the present invention. For example, the organic layer OL may include a hole transport region HTR disposed on the first electrode EL1, an emitting layer EML disposed on the hole transport region HTR, and an electron transport region ETR disposed on the emitting layer EML, and the emitting layer EML or the electron transport region ETR may include a polycyclic compound according to an embodiment of the present invention.

[0063] The polycyclic compound according to an embodiment of the present invention is represented by the following Chemical Formula 1.

[0064] [ka] ...(chemical formula 1) In Chemical Formula 1, X 1 ~X 4 are each independently NR 9 , O or S.

[0065] In Chemical Formula 1, R 1 ~R 8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having from 1 to 20 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.

[0066] In Chemical Formula 1, R 9 The terminal group is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having from 1 to 20 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, or is bonded to an adjacent group to form a ring.

[0067] In Chemical Formula 1, a is an integer of 0 to 4, and if a is 2 or more, a plurality of R 2 are the same or different from each other.

[0068] In Chemical Formula 1, b is an integer of 0 to 4, and if b is 2 or more, then multiple R 3 are the same or different from each other.

[0069] In formula 1, c is an integer of 0 to 4, and if c is 2 or more, then multiple R 4 are the same or different from each other.

[0070] In Chemical Formula 1, d is an integer of 0 to 4, and if d is 2 or more, then multiple R 5 are the same or different from each other.

[0071] In Chemical Formula 1, e is an integer of 0 to 4, and if e is 2 or more, then multiple R 6 are the same or different from each other.

[0072] In Chemical Formula 1, f is an integer of 0 to 4, and if f is 2 or more, then multiple R 7 are the same or different from each other.

[0073] In Chemical Formula 1, m and n are each independently 0 or 1, and the dotted line represents a bond or no bond. For example, when m is 0, (B) m The dotted lines around the periphery indicate non-bonding. If m is 1, then (B) m The dotted lines around the periphery represent bonds. If n is 0, then (B) n The dotted lines around the edge indicate non-bonding. If n is 1, then (B) n The dotted lines around the carbon atom represent bonds. A bond means that a single bond is formed between B and the carbon atom connected by the dotted line as in 1-1 below, and a non-bond means that there is no B and the carbon atom forms a single bond with hydrogen as in 1-2 below.

[0074] [ka] (1-1) JPEG0007633036000025.jpg6891...(1-2) In Chemical Formula 1, Ring A is an aryl group or a heteroaryl group satisfying aromaticity. More specifically, in Chemical Formula 1, Ring A is represented by any one of the following Chemical Formulas 2-1 to 2-3.

[0075] [ka] ...(chemical formula 2-1) JPEG0007633036000027.jpg5773...(Chemical formula 2-2) JPEG0007633036000028.jpg5977...(Chemical formula 2-3) In Chemical Formulae 2-1 to 2-3, the mark "*" indicates the position of condensation in Chemical Formula 1.

[0076] In Chemical Formula 2-1 to Chemical Formula 2-3, Chemical Formula X 5 and X 6 are each independently CR 30 R 31 , N.R. 32 , O, or S.

[0077] In Chemical Formula 2-1 to Chemical Formula 2-3, R 30 ~R 32 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having from 1 to 20 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.

[0078] In Chemical Formula 2-1 to Chemical Formula 2-3, R 20 ~R 29are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having from 1 to 20 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.

[0079] However, when the ring A is represented by the formula 2-1 or 2-2, at least one of m and n is 1. In one embodiment, when the ring A of the formula 1 is represented by the formula 2-1 or 2-2, m of the formula 1 may be 1 and n may be 0, or m of the formula 1 may be 0 and n may be 1.

[0080] In one embodiment, when ring A in Chemical Formula 1 is represented by Chemical Formula 2-1 or 2-2, m and n in Chemical Formula 1 may be 1, respectively.

[0081] In one embodiment, when ring A of Chemical Formula 1 is represented by Chemical Formula 2-3, m and n may each be 0, or at least one of m and n may be 1. In one embodiment, when ring A of Chemical Formula 1 is represented by Chemical Formula 2-3, m and n of Chemical Formula 1 may each be 1.

[0082] In one embodiment, the X in Formula 1 1 ~X 4 are each independently NR 11 , or O and R 11 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[0083] In one embodiment, X in Formula 1 1 and X 4 are the same as each other, and X in chemical formula 1 2 and X 3 are equivalent to each other.

[0084] In one embodiment, Chemical Formula 2-2 is represented by any one of Chemical Formulas 3-1 to 3-4 below.

[0085] [ka] ...(chemical formula 3-1) JPEG0007633036000030.jpg7470...(Chemical formula 3-2) JPEG0007633036000031.jpg3570...(Chemical formula 3-3) JPEG0007633036000032.jpg3570...(Chemical formula 3-4) In Chemical Formulae 3-1 to 3-4, the mark "*" indicates the position of condensation.

[0086] In Chemical Formula 3-1, R 30 and R 31 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0087] In Chemical Formula 3-2, R 33 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and j is an integer of 0 to 5. On the other hand, if j is 2 or more, multiple R 33 are the same or different from each other.

[0088] In one embodiment, Chemical Formula 2-3 is represented by any one of the following Chemical Formulas 4-1 to 4-3.

[0089] [ka] ...(Chemical formula 4-1) JPEG0007633036000034.jpg4678...(Chemical formula 4-2) JPEG0007633036000035.jpg8077...(Chemical formula 4-3) In Chemical Formulae 4-1 to 4-3, the mark "*" indicates the position of condensation.

[0090] In Chemistry 4-3, R 34 is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0091] In Chemical Formula 4-3, k is an integer of 0 to 5. If k is 2 or more, multiple R 34 are the same or different from each other.

[0092] In one embodiment, ring A of formula 1 is represented by formula 2-1. In this case, formula 1 is represented by formula 5-1 or formula 5-2. [ka] ...(chemical formula 5-1) JPEG0007633036000037.jpg49127...(Chemical formula 5-2) In Chemical Formula 5-1 and Chemical Formula 5-2, X 1 ~X 4 , R 1 ~R 8 , R 20 , R 21 , a to f are as defined in Chemical Formula 1 and Chemical Formula 2-1.

[0093] In one embodiment, ring A of formula 1 is represented by formula 2-2. In this case, formula 1 is represented by formula 6-1 or formula 6-2. [ka] ...(chemical formula 6-1) JPEG0007633036000039.jpg50128...(Chemical formula 6-2) In Chemical Formula 6-1 and Chemical Formula 6-2, X 1 ~X 5 , R 1 ~R 8 , R 22 ~R 25 , a to f are as defined in Chemical Formula 1 and Chemical Formula 2-2.

[0094] In one embodiment, ring A in Chemical Formula 1 is represented by Chemical Formula 2-3. In this case, in one embodiment, Chemical Formula 1 is represented by any one of the following Chemical Formulas 7-1 to 7-3.

[0095] [ka] ...(chemical formula 7-1) JPEG0007633036000041.jpg51152...(Chemical formula 7-2) JPEG0007633036000042.jpg51143...(Chemical formula 7-3) In Chemical Formula 7-1 and Chemical Formula 7-3, X 1 ~X 4 , X 6 , R 1 ~R 8 , R 26 ~R 29 , a to f are as defined in Chemical Formula 1 and Chemical Formula 2-3.

[0096] In one embodiment, the polycyclic compound represented by Chemical Formula 1 is any one selected from the compounds shown in the following first compound group, but is not limited thereto. [First compound group] [ka] JPEG0007633036000044.jpg143128 JPEG0007633036000045.jpg141123

[0097] In one embodiment, the polycyclic compound represented by Chemical Formula 1 is any one selected from the compounds shown in the following second compound group, but is not limited thereto. [Second compound group] [ka] JPEG0007633036000047.jpg125143 JPEG0007633036000048.jpg128145 JPEG0007633036000049.jpg130146

[0098] In one embodiment, the polycyclic compound represented by Chemical Formula 1 is any one selected from the compounds shown in the following third compound group, but is not limited thereto. [Third compound group] [ka] JPEG0007633036000051.jpg141140

[0099] The above-mentioned polycyclic compound is used in the organic electroluminescent device 10 of the embodiment to improve the efficiency of the organic electroluminescent device. In particular, the above-mentioned polycyclic compound is used in the organic layer OL of the organic electroluminescent device 10 of the embodiment to improve the luminous efficiency and electron transport property of the organic electroluminescent device.

[0100] The organic layer OL contains one or more polycyclic compounds represented by Chemical Formula 1. For example, the organic layer OL may contain at least one compound selected from the compounds shown in the first to third compound groups described above.

[0101] 2 to 5, the organic layer OL includes a hole-transporting region HTR, an emitting layer EML, and an electron-transporting region ETR.

[0102] The hole transport region HTR is disposed 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 (not shown), and an electron blocking layer EBL.

[0103] The hole transport region HTR may have a single layer of a single material, a single layer of a plurality of different materials, or a multi-layer structure having a plurality of layers of a plurality of different materials.

[0104] 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 layer structure of a hole injection material and a hole transport material. The hole transport region HTR may have a single layer structure of a plurality of different materials, or a structure of a hole injection layer HIL / hole transport layer HTL, a hole injection layer HIL / hole transport layer HTL / hole buffer layer (not shown), a hole injection layer HIL / hole buffer layer (not shown), 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 the embodiment is not limited thereto.

[0105] The hole transport region HTR 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).

[0106] The hole injection layer HTL may be, for example, a phthalocyanine compound such as copper phthalocyanine, DNTPD (N,N'-diphenyl-N,N'-bis-[4-phenyl-m-tolylamino)-phenyl]-biphenyl-4,4'-diamine), m-MTDATA (4,4',4"-[tris(3-methylphenyl)phenylamino)triphenylamine), TDATA (4,4',4"-tris(N,N-diphenylamino)triphenylamine), 2-TNATA (4,4',4"-tris{N,-(2-naphthyl)-N-phenylamino}-triphenylamine), PEDOT / PSS (poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonyl)sulfonyl) polyaniline / poly(4-styrenesulfonate)), NPD (N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine), polyether ketone with triphenylamine (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium tetrakis(pentafluorophenyl)borate, HAT-CN (dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile), and the like.

[0107] The hole transport layer HTL includes common materials known in the art. For example, it may include carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, fluorene derivatives, triphenylamine derivatives such as TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine), TCTA (4,4',4"-tris(N-carbazolyl)triphenylamine), NPD (N,N'-di(naphthalen-1-yl)-N,N'-diphenyl-benzidine), TAPC (4,4'-cyclohexylidenebis[N,N-bis(4-methylphenyl)benzeneamine]), HMTPD (4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl), mCP (1,3-bis(N-carbazolyl)benzene), etc.

[0108] 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), TCTA (4,4',4"-tris(N-carbazolyl)triphenylamine), NPD (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.

[0109] The thickness of the hole transport region HTR may be about 5 nm to about 1,500 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, a satisfactory level of hole transport properties can be obtained without a substantial increase in driving voltage.

[0110] In addition to the above-mentioned materials, the hole transport region HTR further includes 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 one of, but is not limited to, a quinone derivative, a metal oxide, and a cyano group-containing compound. For example, non-limiting examples of the p-dopant include, but are not limited to, a quinone derivative such as TCNQ (tetracyanoquinodimethane) and F4-TCNQ (2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane), a metal oxide such as tungsten oxide and molybdenum oxide, and the like.

[0111] As described above, the hole transport region HTR includes at least one of a hole buffer layer (not shown) and an electron blocking layer EBL in addition to the hole transport layer HTL and the hole injection layer HIL. The hole buffer layer (not shown) compensates for the resonance distance according to the wavelength of light emitted from the emission layer EML to increase light emission efficiency. The material included in the hole buffer layer (not shown) is a material that can be included in the hole transport region HTR. 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.

[0112] The light-emitting layer EML is disposed on the hole-transporting region HTR. The light-emitting layer EML has a thickness of, for example, about 10 nm to about 100 nm, or about 10 nm to about 30 nm. The light-emitting layer EML has a multilayer structure having a single layer made of a single material, a single layer made of a plurality of different materials, or a plurality of layers made of a plurality of different materials.

[0113] 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.

[0114] In one embodiment, the emitting layer EML is a fluorescent emitting layer. For example, a part of the light emitted from the emitting layer EML may be due to thermally activated delayed fluorescence (TADF). In particular, the emitting layer EML includes a light-emitting component that emits thermally activated delayed fluorescence, and in one embodiment, the emitting layer EML may be a thermally activated delayed fluorescence emitting layer that emits blue light.

[0115] The emission layer EML of the organic electroluminescent device 10 according to an embodiment includes a polycyclic compound according to an embodiment of the present invention. In particular, the above-mentioned polycyclic compound is used in the emission layer EML of the organic electroluminescent device 10 according to an embodiment to improve the luminous efficiency of the organic electroluminescent device.

[0116] The emitting layer EML may contain one or more polycyclic compounds represented by Chemical Formula 1. For example, the emitting layer EML may contain at least one compound selected from the compounds shown in the above-mentioned first to third compound groups.

[0117] 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 of one embodiment represented by Chemical Formula 1 is included as a dopant material of the emission layer EML. For example, the polycyclic compound of one embodiment represented by Chemical Formula 1 may be used as a TADF dopant.

[0118] Meanwhile, although not shown, the organic electroluminescent device 10 of an embodiment may include a plurality of light-emitting layers. The plurality of light-emitting layers are provided by being sequentially stacked, and for example, the organic electroluminescent device 10 including the plurality of light-emitting layers may emit white light. The organic electroluminescent device 10 including the plurality of light-emitting layers is an organic electroluminescent device having a tandem structure. If the organic electroluminescent device 10 includes a plurality of light-emitting layers, at least one of the light-emitting layers EML includes the polycyclic compound according to the present invention as described above.

[0119] The light-emitting layer EML may further include a dopant, and known materials are used as the dopant. For example, styryl derivatives (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4"-[(di-p-tolylamino)styryl]stilbene (DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2-yl)vinyl)phenyl)-N-phenylbenzenamine (N-BDAVBi), perylene and its derivatives (e.g., 2,5,8,8,11-tetra-t At least one of 1,1-tetra-t-butylperylene (TBPe), pyrene and its derivatives (e.g., 1,1-dipyrene, 1,4-dipyrenylbenzene, 1-4-bis(N,N-diphenylamino)pyrene, 1,6-bis(N,N-diphenylamino)pyrene), 2,5,8,11-tetra-t-butylperylene (TBP), and TPBi (1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene) may be used as a dopant, but is not limited thereto.

[0120] The light-emitting layer EML may further include a common material known in the art as a host material. For example, the light-emitting layer EML may include Alq 3(tris(8-hydroxyquinolino)aluminum), DPEPO (bis-[2-(diphenylphosphino)phenyl]ether oxide), CBP (4,4'-bis(N-carbazol-9-yl)biphenyl), mCP (1,3-bis(carbazol-9-yl)benzene), PPF (2,8-bis(diphenylphosphoryl)dibenzo[b,d]furan), TCTA (4,4',4"-tris(carbazol-9-yl)-triphenylamine), PVK (poly(N-vinylcarbazole) , ADN (9,10-di(naphthalen-2-yl)anthracene), 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), CP1 (hexaphenylcyclotriphosphazene), UGH-2 (1,4-bis(triphenylsilyl)benzene), DPSiO 3 (Hexaphenylcyclotrisiloxane), DPSiO 4 (octaphenylcyclotetrasiloxane), PPF (2,8-bis(diphenylphosphoryl)dibenzofuran), and TPBi (1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene).

[0121] When the emitting layer EML emits red light, the emitting layer EML is, for example, PBD:Eu(DBM) 3The light-emitting layer EML further includes a fluorescent material including (Phen) (tris(dibenzoylmethanato)phenanthroline europium) or perylene. When the light-emitting layer EML emits red light, the dopant included in the light-emitting layer EML is selected from, for example, metal complexes such as PIQIr(acac) (bis(1-phenylisoquinoline)acetylacetonate iridium), PQIr(acac) (bis(1-phenylquinoline)acetylacetonate iridium), PQIr (tris(1-phenylquinoline)iridium), and PtOEP (octaethylporphyrin platinum), or organometallic complexes, rubrene and its derivatives, and 4-dicyanomethylene-2-(p-dimethylaminostyryl)-6-methyl-4H-pyran (DCM) and its derivatives.

[0122] When the emitting layer EML emits green light, the emitting layer EML is, for example, Alq 3 When the light emitting layer emits green light, the dopant contained in the light emitting layer EML is, for example, Ir(ppy). 3 (fac-tris(2-phenylpyridine)iridium), or organometallic complexes, and coumarin and its derivatives.

[0123] When the emitting layer EML emits blue light, the emitting layer EML further includes a fluorescent material including any one selected from the group consisting of spiro-DPVBi, spiro-6P, DSB (distyryl-benzene), DSA (distyryl-arylene), PFO (polyfluorene)-based polymers, and PPV (poly(p-phenylenevinylene)-based polymers. When the emitting layer EML emits blue light, the dopant included in the emitting layer EML is, for example, (4,6-F2ppy). 2 The compound is selected from metal complexes such as Irpic, or organometallic complexes, and perylene and its derivatives.

[0124] The electron transport region ETR is disposed on the light emitting layer EML and includes at least one of a hole blocking layer HBL, an electron transport layer ETL, and an electron injection layer EIL, but the embodiment is not limited thereto.

[0125] 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.

[0126] 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 light emitting layer EML, but is not limited thereto. The thickness of the electron transport region ETR may be, for example, about 100 nm to about 150 nm.

[0127] In one embodiment, the electron transport region ETR of the organic electroluminescent device 10 includes a polycyclic compound according to one embodiment of the present invention. For example, the electron transport region ETR may include a polycyclic compound represented by Chemical Formula 1.

[0128] When the electron transport region ETR has a multi-layer structure having a plurality of layers, any one of the plurality of layers contains the polycyclic compound represented by Chemical Formula 1. For example, the electron transport region ETR may include an electron transport layer ETL disposed on the light emitting layer EML, and an electron injection layer EIL disposed on the electron transport layer ETL, and the electron transport layer ETL or the electron injection layer EIL may contain the polycyclic compound according to an embodiment of the present invention.

[0129] The electron transport region ETR includes one or more polycyclic compounds represented by Chemical Formula 1. For example, the electron transport region ETR may include at least one selected from the compounds shown in the first to third compound groups described above.

[0130] The electron transport region ETR can be formed using various methods such as vacuum deposition, spin coating, casting, LB method, inkjet printing, laser printing, laser thermal transfer (LITI), and the like.

[0131] The electron transport region ETR further includes a known substance other than the polycyclic compound. If the electron transport region ETR includes an electron transport layer ETL, the electron transport region ETR includes an anthracene-based compound. However, the electron transport region is not limited thereto. For example, the electron transport region may include Alq 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, DPEPO (bis[2-(diphenylphosphino)phenyl]phenyl ether oxide), 2-(4-(N-phenylbenzoimidazolyl-1-ylphenyl)-9,10-dinaphthylanthracene, TPBi (1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl), BCP (2,9-dimethyl-4,7-diphenyl nyl-1,10-phenanthroline), Bphen (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(benzoquinoline-10-olate), ADN (9,10-di(naphthalene-2-yl)anthracene), or a mixture thereof. The thickness of the electron transport layer ETL is 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, a satisfactory level of electron transport properties can be obtained without a substantial increase in driving voltage.

[0132] If the electron transport region ETR includes an electron injection layer EIL, the electron transport region ETR may be a metal halide such as LiF, NaCl, CsF, RbCl, or RbI, a lanthanum group metal such as Yb, or Li 2 Metal oxides such as O, BaO, or LiQ (lithium quinolate) 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. The organo metal salt is a material having an energy band gap of about 4 eV or more. In detail, for example, the organo metal salt includes metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate, or metal stearate. The thickness of the electron injection layer EIL is about 0.1 nm to about 10 nm, or about 0.3 nm to about 9 nm. If the thickness of the electron injection layer EIL satisfies the above-mentioned range, a satisfactory level of electron injection characteristics can be obtained without a substantial increase in driving voltage.

[0133] The electron transport region ETR includes the hole blocking layer HBL as described above. The hole blocking layer HBL may include at least one of, for example, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), DPEPO (bis[2-(diphenylphosphino)phenyl]phenyl ether oxide), and Bphen (4,7-diphenyl-1,10-phenanthroline), but is not limited thereto.

[0134] The second electrode EL2 is disposed on the electron transport region ETR. The second electrode EL2 is a common electrode or a negative electrode. The second electrode EL2 is a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. If the second electrode EL2 is a transmissive electrode, the second electrode EL2 is made of a transparent metal oxide, such as ITO, IZO, ZnO, ITZO, etc.

[0135] 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 containing these (e.g., a mixture of Ag and Mg), or has a multi-layer structure including a reflective film or semi-transmissive film made of the above material and a transparent conductive film made of ITO, IZO, ZnO, ITZO, or the like.

[0136] Although not shown, the second electrode EL2 is connected to an auxiliary electrode, If the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 can be reduced.

[0137] 4, the organic electroluminescent device 10 according to an embodiment further includes a capping layer CPL on the second electrode EL2. The capping layer CPL may be, for example, α-NPD, NPB, TPD, m-MTDATA, Alq 3 , CuPc, TPD15 (N4,N4,N4',N4'-tetra(biphenyl-4-yl)biphenyl-4,4'-diamine), TCTA (4,4',4"-tris(carbazolesol-9-yl)triphenylamine), and the like.

[0138] As described above, the organic electroluminescent device 10 according to an embodiment of the present invention exhibits excellent luminous efficiency characteristics by including the polycyclic compound represented by Chemical Formula 1. In addition, the organic electroluminescent device 10 according to an embodiment of the present invention exhibits high efficiency characteristics in the blue wavelength region.

[0139] Hereinafter, a compound according to an embodiment of the present invention and an organic electroluminescent device according to an embodiment of the present invention will be described in detail with reference to embodiments and comparative examples. The following embodiments are merely examples for aiding in understanding the present invention, and the scope of the present invention is not limited thereto. EXAMPLES

[0140] (Synthesis of polycyclic compounds) The synthesis method of the polycyclic compound described below is merely an example, and the synthesis method of the polycyclic compound according to the embodiment of the present invention is not limited to the following example.

[0141] 1. Synthesis of Compounds 1-9 [ka]

[0142] (1) Synthesis of intermediate 1-9a 3,5-Bis(diphenylamino)phenol (1 eq.), 1-bromo-3-fluorobenzene (1.1 eq.), and potassium carbonate (2 eq.) were added to DMF, and the mixture was stirred at 160°C for 24 hours under a nitrogen atmosphere. After cooling, the mixture was washed three times with ethyl acetate and water, and the resulting organic layer was diluted with MgSO 4 After drying at 40°C, the mixture was dried under reduced pressure. Intermediate 1-9a was obtained by column chromatography (yield: 80%).

[0143] (2) Synthesis of intermediate 1-9b Intermediate 1-9a (1 eq.), N1,N1,N3,N3,N5-pentaphenylbenzene-1,3,5-triamine (1.1 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.1 eq.), and sodium t-butoxide (3 eq.) were dissolved in toluene, and the mixture was stirred at 100°C for 12 hours under a nitrogen atmosphere. After cooling, the mixture was washed three times with ethyl acetate and water, and the resulting organic layer was diluted with MgSO 4 After drying at 40°C, the mixture was dried under reduced pressure. Intermediate 1-9b was obtained by column chromatography (yield: 75%).

[0144] (3) Synthesis of intermediate 1-9c After dissolving intermediate 1-9c (1 eq.) in orthodichlorobenzene, the flask was cooled to 0°C under a nitrogen atmosphere and then cooled with BBr 3(4 eq.) was gradually added. After the dropwise addition was completed, the temperature was raised to 160°C and the mixture was stirred for 24 hours. After cooling, triethylamine was gradually added dropwise to the flask until the heat generation ceased, and the reaction was terminated. After that, hexane was added to precipitate the solid matter, and the solid matter was obtained by filtration. The obtained solid matter was purified by column chromatography, and then further purified by MC / Hex recrystallization to obtain intermediate 1-9c. (Yield: 15%)

[0145] (4) Synthesis of Compounds 1-9 After dissolving intermediate 1-9c (1 eq) in orthodichlorobenzene, the flask was cooled to 0°C under nitrogen and then cooled with BI 3 (2.5eq) was gradually added. After the dropwise addition was completed, the temperature was raised to 160 degrees Celsius and the mixture was stirred for 6 hours. After cooling, triethylamine was gradually added dropwise to the flask until the heat generation ceased, and the reaction was terminated. After that, hexane was added to precipitate the solid matter, and the solid matter was obtained by filtration. The obtained solid matter was purified by silica filtration, and then further purified by MC / Hex recrystallization to obtain compound 1-9. (Yield: 10%)

[0146] 2. Synthesis of Compounds 1-10 [ka]

[0147] (1) Synthesis of intermediate 1-10a N1,N1,N3,N3,N5-Pentaphenylbenzene-1,3,5-triamine (2.2 eq.), 1,3-dibromobenzene (1 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.1 eq.), and sodium t-butoxide (3 eq.) were dissolved in toluene, and the mixture was stirred at 100°C for 12 hours under a nitrogen atmosphere. After cooling, the mixture was washed three times with ethyl acetate and water, and the resulting organic layer was diluted with MgSO 4 After drying at 40° C., the mixture was dried under reduced pressure. Intermediate 1-10a was obtained by column chromatography (yield: 65%).

[0148] (2) Synthesis of intermediate 1-10b Intermediate 1-10a (1 eq.) was dissolved in orthodichlorobenzene, and the flask was cooled to 0°C under a nitrogen atmosphere and then cooled with BBr 3 (4 eq.) was gradually added. After the dropwise addition was completed, the temperature was raised to 160 degrees Celsius and the mixture was stirred for 24 hours. After cooling, triethylamine was gradually added dropwise to the flask until the heat generation ceased, and the reaction was terminated. After that, hexane was added to precipitate the solid matter, and the solid matter was obtained by filtration. The obtained solid matter was purified by column chromatography, and then further purified by MC / Hex recrystallization to obtain intermediate 1-10b. (Yield: 15%)

[0149] (3) Synthesis of Compounds 1-10 After dissolving intermediate 1-10b (1 eq) in orthodichlorobenzene, the flask was cooled to 0°C under nitrogen and then cooled with BI 3 (2.5eq) was gradually added. After the dropwise addition was completed, the temperature was raised to 160 degrees Celsius and the mixture was stirred for 6 hours. After cooling, triethylamine was gradually added dropwise to the flask until the heat generation ceased, and the reaction was terminated. After that, hexane was added to precipitate the mixture, and the solid matter was obtained by filtration. The obtained solid matter was purified by silica filtration, and then further purified by MC / Hex recrystallization to obtain compound 1-10. (Yield: 10%)

[0150] 3. Synthesis of Compound 2-2 [ka]

[0151] (1) Synthesis of intermediate 2-2a 2,7-Dibromo-9-phenyl-9H-carbazole (1 eq.), 3,5-bis(diphenylamino)phenol (2.5 eq.), and potassium carbonate (5 eq.) were added to DSMO, and the mixture was stirred at 180°C for 24 hours under a nitrogen atmosphere. After cooling, the mixture was washed five times with ethyl acetate and water, and the resulting organic layer was diluted with MgSO 4 After drying at 40° C., the mixture was dried under reduced pressure. Intermediate 2-2a was obtained by column chromatography (yield: 50%).

[0152] (2) Synthesis of intermediate 2-2b Intermediate 2-2a (1 eq.) was dissolved in orthodichlorobenzene, and the flask was cooled to 0°C under a nitrogen atmosphere and then cooled with BBr 3 (4 eq.) was gradually added. After the dropwise addition was completed, the temperature was raised to 160 degrees Celsius and the mixture was stirred for 24 hours. After cooling, triethylamine was gradually added dropwise to the flask until the heat generation ceased. After the reaction was terminated, hexane was added to precipitate the product, and the solid matter was filtered to obtain it. The obtained solid matter was purified by column chromatography, and then further purified by MC / Hex recrystallization to obtain compound 2-2b. (Yield: 15%)

[0153] (3) Synthesis of Compound 2-2 After dissolving intermediate 2-2b (1 eq) in orthodichlorobenzene, the flask was cooled to 0°C under a nitrogen atmosphere and then cooled with BI 3 (2.5eq) was gradually added. After the dropwise addition was completed, the temperature was raised to 160 degrees Celsius and the mixture was stirred for 6 hours. After cooling, triethylamine was gradually added dropwise to the flask until the heat generation ceased. After the reaction was terminated, hexane was added to precipitate the mixture, and the solid matter was filtered to obtain it. The obtained solid matter was purified by silica filtration, and then further purified by MC / Hex recrystallization to obtain compound 2-2. (Yield: 10%)

[0154] 4. Synthesis of Compound 2-3 [ka]

[0155] (1) Synthesis of intermediate 2-3a 1,3-Dibromo-5-phenoxybenzene (1 eq.), diphenylamine (1 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.01 eq.), tri-tert-butylphosphine (0.05 eq.), and sodium t-butoxide (3 eq.) were dissolved in toluene, and the mixture was stirred at 90°C for 2 hours under a nitrogen atmosphere. After cooling, the mixture was washed three times with ethyl acetate and water, and the resulting organic layer was diluted with MgSO 4 After drying at 40°C, the mixture was dried under reduced pressure. Intermediate 2-3a was obtained by column chromatography (yield: 65%).

[0156] (2) Synthesis of intermediate 2-3b Intermediate 2-3a (1 eq.), aniline (1.1 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.01 eq.), tri-tert-butylphosphine (0.05 eq.), and sodium t-butoxide (3 eq.) were dissolved in toluene, and the mixture was stirred at 90°C for 2 hours under a nitrogen atmosphere. After cooling, the mixture was washed three times with ethyl acetate and water, and the resulting organic layer was diluted with MgSO 4 After drying at 40°C, the mixture was dried under reduced pressure. Intermediate 2-3b was obtained by column chromatography (yield: 75%).

[0157] (3) Synthesis of intermediate 2-3c Intermediate 2-3b (2.1 eq.), 2,7-dibromo-9-phenyl-9H-carbazole (1 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.1 eq.), and sodium t-butoxide (3 eq.) were dissolved in toluene, and the mixture was stirred at 100°C for 24 hours under a nitrogen atmosphere. After cooling, the mixture was washed three times with ethyl acetate and water, and the resulting organic layer was diluted with MgSO 4 After drying at 40°C, the mixture was dried under reduced pressure. Intermediate 2-3c was obtained by column chromatography (yield: 65%).

[0158] (4) Synthesis of intermediate 2-3d After dissolving intermediate 2-3c (1 eq.) in orthodichlorobenzene, the flask was cooled to 0°C under a nitrogen atmosphere and then cooled with BBr 3 (4 eq.) was gradually added. After the dropwise addition was completed, the temperature was raised to 160 degrees Celsius and the mixture was stirred for 24 hours. After cooling, triethylamine was gradually added dropwise to the flask until the heat generation ceased, and the reaction was terminated. After that, hexane was added to precipitate the solid matter, and the solid matter was obtained by filtration. The obtained solid matter was purified by column chromatography, and then further purified by MC / Hex recrystallization to obtain intermediate 2-3b. (Yield: 15%)

[0159] (5) Synthesis of compound 2-3 After dissolving intermediate 2-3b (1 eq) in orthodichlorobenzene, the flask was cooled to 0°C under nitrogen atmosphere and then cooled with BI 3(2.5eq) was gradually added. After the dropwise addition, the temperature was raised to 160 degrees Celsius and the mixture was stirred for 6 hours. After cooling, triethylamine was gradually added dropwise to the flask until the heat generation ceased. After the reaction was terminated, hexane was added to precipitate the mixture, and the solid matter was filtered to obtain it. The obtained solid matter was purified by silica filtration, and then further purified by MC / Hex recrystallization to obtain compound 2-3. (Yield: 10%)

[0160] 5. Synthesis of Compounds 2-13 [ka]

[0161] (1) Synthesis of intermediate 2-13a N1,N1,N3,N3,N5-Pentaphenylbenzene-1,3,5-triamine (2.2 eq.), 3,3-dibromodibenzo[b,d]furan (1 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.1 eq.), and sodium t-butoxide (3 eq.) were dissolved in toluene, and the mixture was stirred at 100°C for 12 hours under a nitrogen atmosphere. After cooling, the mixture was washed three times with ethyl acetate and water, and the resulting organic layer was diluted with MgSO 4 After drying at 40° C., the mixture was dried under reduced pressure. Intermediate 2-13a was obtained by column chromatography (yield: 65%).

[0162] (2) Synthesis of intermediate 2-13b Intermediate 2-13a (1 eq.) was dissolved in orthodichlorobenzene, and the flask was cooled to 0°C under a nitrogen atmosphere and then cooled with BBr 3 (4 eq.) was gradually added. After the dropwise addition was completed, the temperature was raised to 160°C and the mixture was stirred for 24 hours. After cooling, triethylamine was gradually added dropwise to the flask until the heat generation ceased, and the reaction was terminated. After that, hexane was added to precipitate the solid matter, and the solid matter was obtained by filtration. The obtained solid matter was purified by column chromatography, and then further purified by MC / Hex recrystallization to obtain intermediate 2-13b. (Yield: 15%)

[0163] (3) Synthesis of Compound 2-13 After dissolving intermediate 2-13b (1 eq) in orthodichlorobenzene, the flask was cooled to 0°C under a nitrogen atmosphere and then cooled with BI 3 (2.5eq) was gradually added. After the dropwise addition was completed, the temperature was raised to 160 degrees Celsius and the mixture was stirred for 6 hours. After cooling, triethylamine was gradually added dropwise to the flask until the heat generation ceased. After the reaction was terminated, hexane was added to precipitate the mixture, and the solid matter was filtered to obtain it. The obtained solid matter was purified by silica filtration, and then further purified by MC / Hex recrystallization to obtain compound 2-13. (Yield: 10%)

[0164] 6. Synthesis of Compound 3-1 [ka]

[0165] (1) Synthesis of intermediate 3-1a 4-Fluoro-2-((3-fluorophenyl)amino)benzoic acid (1 eq.) in CH 3 After adding 0.44M in CN and heating to 90°C, phosphorus(V) oxychloride (2.2 eq.) was added slowly over 1 hour. After addition was complete, the mixture was stirred at 90°C for 2 hours. After cooling, H 2 O (70 eq.) was added and stirred at 100°C for 3 hours. After cooling, the mixture was washed three times with ethyl acetate and water, and the resulting organic layer was diluted with MgSO 4 After drying at 40°C, the mixture was dried under reduced pressure. Intermediate 3-1a was obtained by column chromatography (yield: 30%).

[0166] (2) Synthesis of intermediate 3-1b Intermediate 3-1a (1 eq.), bromobenzene (1.1 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.01 eq.), tri-tert-butylphosphine (0.05 eq.), and sodium t-butoxide (3 eq.) were dissolved in toluene, and the mixture was stirred at 90°C for 2 hours under a nitrogen atmosphere. After cooling, the mixture was washed three times with ethyl acetate and water, and the resulting organic layer was diluted with MgSO 4 After drying at 40° C., the mixture was dried under reduced pressure. Intermediate 3-1b was obtained by column chromatography (yield: 65%).

[0167] (3) Synthesis of intermediate 3-1c 5-Iodobenzene-1,3-diol (1 eq.), fluorobenzene (1.1 eq.), and potassium carbonate (2 eq.) were dissolved in DMSO, and the mixture was stirred at 160°C for 12 hours under a nitrogen atmosphere. After cooling, the mixture was washed five times with ethyl acetate and water, and the resulting organic layer was diluted with MgSO 4 After drying at 40° C., the mixture was dried under reduced pressure. Intermediate 3-1c was obtained by column chromatography (yield: 50%).

[0168] (4) Synthesis of intermediate 3-1d Intermediate 3-1c (1 eq.), bis(2-(trimethylsilyl)phenyl)amine (2.2 eq.), copper iodide (0.05 eq.), potassium hydroxide (5 eq.), and 1,10-phenanthroline (0.05 eq.) were added to xylene, and the mixture was stirred at 110°C for 24 hours under a nitrogen atmosphere. After cooling, the mixture was washed five times with ethyl acetate and water, and the resulting organic layer was extracted with MgSO 4 After drying at 40°C, the mixture was dried under reduced pressure. Intermediate 3-1d was obtained by column chromatography (yield: 50%).

[0169] (5) Synthesis of intermediate 3-1e Intermediate 3-1b (1 eq.), intermediate 3-1d (2.2 eq.), and cesium carbonate (5 eq.) were dissolved in DMSO, and the mixture was stirred at 160°C for 24 hours under a nitrogen atmosphere. After cooling, the mixture was washed five times with ethyl acetate and water, and the resulting organic layer was diluted with MgSO 4 After drying at 40° C., the mixture was dried under reduced pressure. Intermediate 3-1e was obtained by column chromatography (yield: 35%).

[0170] (6) Synthesis of Compound 3-1 BBr 3(5 eq.) was dissolved in orthodichlorobenzene, and the flask was cooled to 0 degrees Celsius under a nitrogen atmosphere, and intermediate 3-1e (1 eq.) dissolved in orthodichlorobenzene was slowly added over a period of 1 hour. After the addition, the mixture was stirred at room temperature for 2 hours, cooled to 0 degrees Celsius, and diisopropylethylamine (15 eq.) was added. After the addition, the temperature was raised to 160 degrees Celsius and stirred for 24 hours. After the reaction was completed, hexane was added to precipitate, and the solid was filtered to obtain it. The obtained solid was purified by column chromatography and further purified by MC / Hex recrystallization to obtain compound 3-1. (Yield: 15%)

[0171] 7. Synthesis of Compound 3-2 [ka]

[0172] (1) Synthesis of intermediate 3-2a 2,2',4,4'-Tetrahydroxybenzophenone was heated at 220 degrees Celsius for 6 hours using a sand bath, and then intermediate 3-2a was obtained by column chromatography (yield: 85%).

[0173] (2) Synthesis of intermediate 3-2b Intermediate 3-2a (1 eq.), 1-fluoro-3-iodo-5-phenoxybenzene (2.2 eq.), and cesium carbonate (5 eq.) were dissolved in DMSO, and the mixture was stirred at 160°C for 24 hours under a nitrogen atmosphere. After cooling, the mixture was washed five times with ethyl acetate and water, and the resulting organic layer was diluted with MgSO 4 After drying at 40° C., the mixture was dried under reduced pressure. Intermediate 3-2b was obtained by column chromatography (yield: 35%).

[0174] (3) Synthesis of intermediate 3-2c Intermediate 3-2b (1 eq.), bis(2-(trimethylsilyl)phenyl)amine (2.2 eq.), copper iodide (0.05 eq.), potassium hydroxide (5 eq.), and 1,10-phenanthroline (0.05 eq.) were added to xylene, and the mixture was stirred at 110°C for 24 hours under a nitrogen atmosphere. After cooling, the mixture was washed five times with ethyl acetate and water, and the resulting organic layer was extracted with MgSO4 After drying at 40° C., the mixture was dried under reduced pressure. Intermediate 3-2c was obtained by column chromatography (yield: 55%).

[0175] (4) Synthesis of compound 3-2 BBr 3 (5 eq.) was dissolved in orthodichlorobenzene, and the flask was cooled to 0 degrees Celsius under nitrogen atmosphere, and intermediate 3-2c (1 eq.) dissolved in orthodichlorobenzene was slowly added over 1 hour. After the addition, the mixture was stirred at room temperature for 2 hours, cooled to 0 degrees Celsius, and diisopropylethylamine (15 eq.) was added dropwise. After the addition, the temperature was raised to 160 degrees Celsius and stirred for 24 hours. After the reaction was completed, hexane was added to precipitate, and the solid was filtered to obtain it. The obtained solid was purified by column chromatography and further purified by MC / Hex recrystallization to obtain compound 3-2. (Yield: 15%)

[0176] 8. Synthesis of Compound 3-4 [ka]

[0177] (1) Synthesis of intermediate 3-4a 3-Bromo-5-(diphenylamino)phenol (1 eq.), bis(2-(trimethylsilyl)phenyl)amine (1.1 eq.), copper iodide (0.05 eq.), potassium hydroxide (5 eq.), and 1,10-phenanthroline (0.05 eq.) were added to xylene, and the mixture was stirred at 110°C for 24 hours under a nitrogen atmosphere. After cooling, the mixture was washed five times with ethyl acetate and water, and the resulting organic layer was extracted with MgSO 4 After drying at 40°C, the mixture was dried under reduced pressure. Intermediate 3-4a was obtained by column chromatography (yield: 55%).

[0178] (2) Synthesis of intermediate 3-4b Intermediate 3-4a (2.2 eq.), 3,6-difluoro-10-phenylacridin-9(10H)-one (1 eq.), and cesium carbonate (5 eq.) were dissolved in DMSO, and the mixture was stirred at 160°C for 24 hours under a nitrogen atmosphere. After cooling, the mixture was washed five times with ethyl acetate and water, and the resulting organic layer was diluted with MgSO 4 After drying at 40°C, the mixture was dried under reduced pressure. Intermediate 3-4b was obtained by column chromatography (yield: 35%).

[0179] (3) Synthesis of compound 3-4 BBr 3 (5 eq.) was dissolved in orthodichlorobenzene, and the flask was cooled to 0 degrees Celsius under nitrogen atmosphere, and intermediate 3-4b (1 eq.) dissolved in orthodichlorobenzene was slowly added over 1 hour. After the addition, the mixture was stirred at room temperature for 2 hours, cooled to 0 degrees Celsius, and diisopropylethylamine (15 eq.) was added dropwise. After the addition, the temperature was raised to 160 degrees Celsius and stirred for 24 hours. After the reaction was completed, hexane was added to precipitate, and the solid was filtered to obtain it. The obtained solid was purified by column chromatography and further purified by MC / Hex recrystallization to obtain compound 3-4. (Yield: 15%)

[0180] [Example Compounds] [ka] JPEG0007633036000061.jpg73125 Comparative organic electroluminescent devices were produced using the following comparative compounds as light-emitting layer materials.

[0181] [Comparative Example Compound] [ka] The organic electroluminescent devices of the examples and comparative examples were produced in the following manner.

[0182] After patterning ITO to a thickness of 120 nm on a glass substrate, it was washed with ultrapure water and subjected to UV ozone treatment for 30 minutes. Then, NPD was vacuum-deposited to a thickness of 30 nm as a hole injection layer, and TATA was vacuum-deposited to a thickness of 20 nm as a hole transport layer. The compound CzSi was vacuum-deposited to a thickness of 10 nm on top of the hole transport layer.

[0183] Next, when forming a light-emitting layer, the polycyclic compound of one example or the compound of the comparative example and mCP were co-deposited in a ratio of 1:99 to form a layer having a thickness of 20 nm.

[0184] After forming TSP01 to a thickness of 20 nm on the light-emitting layer, TPBI was deposited to a thickness of 30 nm as an electron injection layer compound. LiF, an alkali metal halide, was deposited to a thickness of 1 nm on top of the electron transport layer as an electron injection layer, and Al was vacuum-deposited to a thickness of 300 nm to form a LiF / Al electrode, thereby producing an organic electroluminescent device.

[0185] (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 the brightness of 1000 cd / m 2 The external quantum efficiency (%) was measured.

[0186] [Table 1] Referring to the results in Table 1, it can be seen that when the polycyclic compound according to one embodiment is included in the light emitting layer, the external quantum efficiency is improved compared to the comparative example.

[0187] The polycyclic compound according to one embodiment has a wide plate-like skeleton, which further activates the multiple resonance effect and provides a high horizontal alignment rate of the transition dipole moment of the dopant in the host matrix of the light-emitting layer. ST can be further reduced, thereby improving the luminous efficiency. [Explanation of symbols]

[0188] 10: Organic electroluminescent element EL1: First electrode EL2: 2nd electrode OL: Organic phase HTR: Hole transport region EML: Emitting layer ETR: Electron transport region

Claims

1. A first electrode; an organic layer disposed over the first electrode; a second electrode disposed over the organic layer; The organic layer is an organic electroluminescent device including a polycyclic compound represented by the following Chemical Formula 1: 【Chemistry 1】 ...(chemical formula 1) In the above Chemical Formula 1, X １ ~X ４ are each independently NR ９ , O, or S; R １ ~R ８ each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having from 1 to 20 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, R ９ is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having from 1 to 20 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, or is bonded to an adjacent group to form a ring, a to f each independently represents an integer of 0 to 4, m and n each independently represent 0 or 1; Dotted lines indicate bonds or non-bonds. Ring A is represented by any one of the following chemical formulas 2-1 to 2-3: 【Chemistry 2】 ...(Chemical formula 2-1) 【change】 ...(Chemical formula 2-2) 【change】 ...(Chemical formula 2-3) In the above Chemical Formula 2-1 to Chemical Formula 2-3, The "*" mark indicates the position to be condensed. X ５ and X ６ are each independently CR ３０ R ３１ , N.R. ３２ , O, or S; R ３０ ~R ３２ each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having from 1 to 20 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, R ２０ ~R ２９ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having from 1 to 20 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; provided that when the ring A is represented by the formula 2-1 or 2-2, at least one of m and n is 1.

2. The organic layer is 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; The organic electroluminescent device according to claim 1 .

3. The light-emitting layer contains the polycyclic compound and emits delayed fluorescence. The organic electroluminescent device according to claim 2 .

4. The light-emitting layer is a delayed fluorescent light-emitting layer containing a host and a dopant, The dopant is the polycyclic compound. The organic electroluminescent device according to claim 3 .

5. The light-emitting layer is a thermally activated delayed fluorescent light-emitting layer that emits blue light. The organic electroluminescent device according to claim 3.

6. 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; The organic electroluminescent device according to claim 2 , wherein the electron transport layer or the electron injection layer contains the polycyclic compound.

7. The formula 2-2 is represented by any one of the following formulas 3-1 to 3-4: The organic electroluminescent device according to claim 1: 【Chemistry 3】 ...(Chemical formula 3-1) 【change】 ...(Chemical formula 3-2) 【change】 ...(Chemical formula 3-3) 【change】 ...(Chemical formula 3-4) In the above Chemical Formula 3-1 to Chemical Formula 3-4, The "*" mark indicates the position to be condensed. R ３０ , R ３１ , and R ３３ each independently represents a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, j is an integer of 0 to 5.

8. The organic electroluminescent device according to claim 1, wherein the formula 2-3 is represented by any one of the following formulas 4-1 to 4-3: 【Chemistry 4】 ...(Chemical formula 4-1) 【change】 ...(Chemical formula 4-2) 【change】 ...(Chemical formula 4-3) In the above Chemical Formula 4-1 to Chemical Formula 4-3, The "*" mark indicates the position to be condensed. R ３４ is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, k is an integer of 0 or more and 5 or less.

9. The organic electroluminescent device according to claim 1, wherein the formula 1 is represented by the following formula 5-1 or 5-2: 【Chemistry 5】 ...(Chemical formula 5-1) 【change】 ...(Chemical formula 5-2) In the above Chemical Formula 5-1 and Chemical Formula 5-2, X １ ~X ４ , R １ ~R ８ , R ２０ , R ２１ , a to f are as defined in Chemical Formula 1 and Chemical Formula 2-1.

10. The organic electroluminescent device according to claim 1, wherein the formula 1 is represented by the following formula 6-1 or 6-2: 【Chemistry 6】 ...(Chemical formula 6-1) 【change】 ...(Chemical formula 6-2) In the above Chemical Formula 6-1 and Chemical Formula 6-2, X １ ~X ５ , R １ ~R ８ , R ２２ ~R ２５ , a to f are as defined in Chemical Formula 1 and Chemical Formula 2-2.

11. The organic electroluminescent device according to claim 1, wherein the formula 1 is represented by any one of the following formulas 7-1 to 7-3: 【Chemistry 7】 ...(Chemical formula 7-1) 【change】 ...(Chemical formula 7-2) 【change】 ...(Chemical formula 7-3) In the above Chemical Formula 7-1 to Chemical Formula 7-3, X １ ~X ４ , X ６ , R １ ~R ８ , R ２６ ~R ２９ , a to f are as defined in Chemical Formula 1 and Chemical Formula 2-3.

12. The X １ ~X ４ are each independently NR １１ , or 0, The R １１ 2. The organic electroluminescent device according to claim 1, wherein is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

13. The X １ and X ４ are the same as each other, The X ２ and X ３ The organic electroluminescent device according to claim 1 , wherein

14. The organic electroluminescent device according to claim 1, wherein the compound represented by Chemical Formula 1 is any one of the compounds represented by the following first to third compound groups: [First compound group] 【Chemistry 8】 【change】 【change】 [Second compound group] 【Chemistry 9】 【change】 【change】 【change】 [Third compound group] 【Chemistry 10】 【change】 。

15. A polycyclic compound represented by the following chemical formula 1: 【Chemistry 10】 ...(chemical formula 1) In the above Chemical Formula 1, X １ ~X ４ are each independently NR ９ , O, or S; R １ ~R ８ each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having from 1 to 20 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, R ９ is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having from 1 to 20 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, or is bonded to an adjacent group to form a ring, a to f each independently represents an integer of 0 to 4, m and n each independently represent 0 or 1; Dotted lines indicate bonds or non-bonds. Ring A is represented by any one of the following chemical formulas 2-1 to 2-3: 【Chemistry 10】 ...(Chemical formula 2-1) 【change】 ...(Chemical formula 2-2) 【change】 ...(Chemical formula 2-3) In the above Chemical Formula 2-1 to Chemical Formula 2-3, The "*" mark indicates the position to be condensed. X ５ and X ６ are each independently CR ３０ R ３１ , N.R. ３２ , O, or S; R ３０ ~R ３２ each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having from 1 to 20 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, R ２０ ~R ２９ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having from 1 to 20 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; provided that when the ring A is represented by the formula 2-1 or 2-2, at least one of m and n is 1.

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