Organic compound and organic electroluminescent device using the same

Abstract

The present invention relates to a novel compound having excellent carrier transport ability, light emitting ability, and thermal stability, and to an organic electroluminescence device having improved properties such as light emitting efficiency, driving voltage, and lifespan by incorporating the compound in one or more organic layers.

Description

[Technical Field]

[0001] The present invention relates to a novel organic light-emitting compound and an organic electroluminescence device using the same, and more particularly to a compound having excellent electron transport ability, and an organic electroluminescence device having improved properties such as luminous efficiency, driving voltage, and lifespan by incorporating the compound in one or more organic material layers. [Background technology]

[0002] When a voltage is applied between two electrodes in an organic electroluminescence device, holes are injected into the organic layer from the positive electrode and electrons are injected into the organic layer from the negative electrode. The injected holes and electrons combine to form excitons, which emit light when they return to the ground state. The materials used in the organic layer can be classified according to their function into light-emitting materials, hole-injecting materials, hole-transporting materials, electron-transporting materials, electron-injecting materials, etc.

[0003] Depending on the emitted color, luminescent materials are divided into blue, green, and red luminescent materials, and yellow and orange luminescent materials for achieving more natural colors. In addition, a host / dopant system can be used as the luminescent material to improve color purity and luminous efficiency through energy transfer.

[0004] Dopant materials are divided into fluorescent dopants that use organic materials and phosphorescent dopants that use metal complex compounds containing heavy atoms such as Ir and Pt. In this regard, the development of phosphorescent materials can theoretically improve luminous efficiency by up to four times compared to fluorescence, so much research is being conducted not only on phosphorescent dopants but also on phosphorescent host materials.

[0005] Currently, NPB, BCP, and Alq3 are widely known as materials for hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, while anthracene derivatives have been reported as materials for light-emitting layers. In particular, metal complex compounds containing Ir, such as Firpic, Ir(ppy)3, and (acac)Ir(btp)2, which have the advantage of improving efficiency, are used as blue, green, and red phosphorescent dopants, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.

[0006] However, although conventional organic layer materials are advantageous in terms of light-emitting properties, they have low glass transition temperatures and very poor thermal stability, which means that the lifespan of organic electroluminescent devices is not satisfactory. Therefore, there is a demand for the development of organic layer materials with excellent performance. Summary of the Invention [Problem to be solved by the invention]

[0007] The present invention has as its technical object the provision of a novel compound that has excellent heat resistance, carrier transport ability, light-emitting ability, and the like and can be used as an organic layer material for an organic electroluminescence device, specifically as an electron transport layer, an electron transport auxiliary layer, or a light-emitting layer.

[0008] Another technical object of the present invention is to provide an organic electroluminescence device that contains the novel compound and thereby has a low driving voltage, high luminous efficiency, and an improved lifespan.

[0009] Other objects and advantages of the present invention will be more clearly set forth in the detailed description of the invention and claims that follow. [Means for solving the problem]

[0010] To achieve the above object, the present invention provides a compound represented by the following Chemical Formula 1:

[0011] [ka]

[0012] In the above Chemical Formula 1, X1 to X3 are the same or different and each independently represent C(R5) or N, provided that at least two of X1 to X3 represent N; Y1 and Y2 are the same or different and each independently represents O, S, or NR 11 and wherein Y1 and Y2 are selected from the group consisting of: Ar1 and Ar2 are the same or different and each independently represent C1 to C 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 atoms, C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C3-C 40 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron groups, C6-C 60 Arylphosphine groups, C6-C 60 arylphosphine oxide groups, and C6-C 60 or which may be joined to any adjacent group to form a fused ring; R1 to R5 and R 11 are the same or different and each independently represent hydrogen, deuterium (D), halogen, cyano group, nitro group, C1 to C 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 atoms, C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C3-C 40 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron groups, C6-C 60 Arylphosphine groups, C6-C 60 arylphosphine oxide groups, and C6-C 60 or which may be joined to any adjacent group to form a fused ring; o, p, and q are each independently an integer of 0 to 4, and r is an integer of 0 to 3; The Ar1 to Ar2, R1 to R5, and R 11 The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, and arylamine group each independently include deuterium (D), halogen, cyano group, nitro group, C1 to C6 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 atoms, C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C1-C 40 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron groups, C6-C 60Arylphosphine groups, C6-C 60 arylphosphine oxide groups, and C6-C 60 In this case, when there are a plurality of the substituents, they may be the same or different.

[0013] The present invention also provides an organic electroluminescence device comprising a positive electrode, a negative electrode, and one or more organic layers interposed between the positive electrode and the negative electrode, wherein at least one of the one or more organic layers comprises a compound represented by Chemical Formula 1.

[0014] The organic layer containing the compound represented by Chemical Formula 1 may be selected from the group consisting of an emitting layer, an emitting auxiliary layer, a hole injection layer, a hole transport layer, an electron injection layer, a life improvement layer, an electron transport layer, and an electron transport auxiliary layer. In this case, the compound represented by Chemical Formula 1 may be included as a phosphorescent host material in the emitting layer, a material in the electron transport layer, and a material in the electron transport auxiliary layer. [Effects of the Invention]

[0015] According to one embodiment of the present invention, the compound represented by Chemical Formula 1 has excellent electron transporting ability, light emitting ability, heat resistance, etc., and can be used as an organic layer material for an organic electroluminescence device.

[0016] In particular, when the compound represented by Chemical Formula 1 of the present invention is used as an electron transport layer or electron transport auxiliary layer material, it can exhibit higher thermal stability, lower driving voltage, higher mobility, higher current efficiency, and longer life properties than conventional host materials or electron transport materials.

[0017] As a result, an organic electroluminescent device comprising the compound of Formula 1 can be significantly improved in terms of excellent light-emitting performance, low driving voltage, long life, and high efficiency, and can therefore be effectively applied to full-color display panels, etc.

[0018] The effects of the present invention are not limited to the above-mentioned examples, and various other effects are included in this specification. DETAILED DESCRIPTION OF THE INVENTION

[0019] The present invention will be described in detail below.

[0020] <New organic compounds> The present invention provides novel compounds, such as polycyclic spiro compounds, which are excellent in thermal stability, carrier transport ability, and light-emitting ability.

[0021] The compound represented by Chemical Formula 1 has a polycyclic spiro bond core containing at least two heteroatoms (e.g., S-S / O-S / S-NR' / NR'-NR'' / O-NR'), and an electron-withdrawing group (EWG) with excellent electron transport ability is directly bonded to the core structure to form a basic skeleton.

[0022] Specifically, the compound of Chemical Formula 1 has an electron-donating effect due to the unshared electron pair of the heteroatom (O or S) contained in the polycyclic spiro core structure. Therefore, when such a compound is applied to an organic light-emitting device, the luminous efficiency of the device can be improved, and the durability and stability of the device can be improved, thereby efficiently extending the life of the device.

[0023] Furthermore, to improve the electron transfer rate, the introduction of triazine or pyrimidine, an azine-based functional group with strong electron-withdrawing group (EWG), can provide physicochemical properties that are more suitable for electron injection and electron transport. When the compound of Formula 1 is used as a material for the electron transport layer or electron transport auxiliary layer, it can easily accommodate electrons from the anode and smoothly transfer electrons to the light-emitting layer, thereby reducing the driving voltage of the device and achieving high efficiency and long life.

[0024] In particular, when an EWG (e.g., an azine group) is substituted on a ring such as N in the polycyclic spiro core structure, the EWG effect is stronger due to the effect of the N atom, which has a lower electronegativity than O, so the driving voltage of the device can be reduced and high efficiency can be achieved. Also, when an EWG is substituted on a ring other than N or S in the polycyclic spiro core structure, NR 11 has a bulkier structure than O atoms, and S also has a larger orbital region than O atoms, so it is a structure that can relatively lower the packing density during device fabrication. Due to the above-mentioned effect, mobility is reduced, which allows the construction of a stable, long-life device.

[0025] In addition, the compound represented by Formula 1 of the present invention has steric hindrance due to the spiro-type structure, which prevents crystallization during film formation and maintains high thermal stability, providing stability at high deposition temperatures. Furthermore, the spiro-type core structure provides excellent electrochemical stability, a high glass transition temperature (Tg), and excellent carrier transport ability. Therefore, improved efficiency, low driving voltage, and improved lifespan characteristics can be achieved in organic light-emitting devices.

[0026] As described above, when the compound represented by Chemical Formula 1 of the present invention is used as an organic layer material of an organic electroluminescent device, preferably as an emitting layer material (blue, green, and / or red phosphorescent host material), an electron transport layer / injection layer material, a hole transport layer / injection layer material, an emitting auxiliary layer material, or a lifetime improvement layer material, the performance and lifetime characteristics of the organic electroluminescent device can be significantly improved. In particular, when the compound of the present invention is used as an electron transport layer or electron transport auxiliary layer material, significant performance improvements can be expected in terms of device efficiency, driving voltage, and lifetime characteristics. As a result, such an organic electroluminescent device can maximize the performance of a full-color organic light-emitting panel.

[0027] The compound represented by Chemical Formula 1 according to the present invention has a polycyclic spirobixanthene group containing at least two heteroatoms (SS / OS / S-NR' / NR'-NR'' / O-NR') as a core structure, and a nitrogen-containing heteroaromatic ring (e.g., azine, X1-X3-containing ring) having electron-withdrawing group (EWG) properties with excellent electron transport ability is directly bonded to the core structure to form a basic skeleton structure.

[0028] The polycyclic spiro core structure includes at least two heteroatoms (e.g., Y1-Y2 containing rings). According to one embodiment of such a polycyclic spiro core structure, Y1 and Y2 are the same or different and each independently represent O, S, and NR 11 and wherein Y1 and Y2 are selected from the group consisting of: with the proviso that the case where Y1 and Y2 are simultaneously O is excluded. Specifically, it is preferred that Y1 and Y2 are different from each other.

[0029] where R 11 is hydrogen, deuterium (D), halogen, cyano group, nitro group, C1-C 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 atoms, C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C3-C 40 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron groups, C6-C 60 Arylphosphine groups, C6-C 60 arylphosphine oxide groups, and C6-C 60 or which may be combined with any adjacent group to form a fused ring. 11 If there are multiple R11 may be the same or different. 11 are hydrogen, deuterium (D), C1 to C 40 Alkyl groups of C6 to C 60 and heteroaryl groups having 5 to 60 ring atoms.

[0030] According to one embodiment, the polycyclic spirocore (e.g., Y1-Y2 containing ring) structure may be further embodied in any one of the following structural formulae, including, but not limited to:

[0031] [ka]

[0032] In the above formula, * means a linking site to Chemical Formula 1; R 11 are hydrogen, deuterium (D), C1 to C 40 Alkyl groups of C6 to C 60 and heteroaryl groups having 5 to 60 ring atoms, R1 to R4, o, p, q, and r are each defined as in Chemical Formula 1.

[0033] The polycyclic spiro core (for example, the ring containing Y1 and Y2) may be substituted with various substituents, each of which may be R1 to R4. R1 to R4 may be the same or different and each independently represent hydrogen, deuterium (D), halogen, cyano, nitro, C1 to C2, or the like. 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 atoms, C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C3-C40 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron groups, C6-C 60 Arylphosphine groups, C6-C 60 arylphosphine oxide groups, and C6-C 60 or which may be combined with any adjacent group to form a fused ring. 11 When there are a plurality of R1 to R4, the plurality of R1 to R4 may be the same or different from each other. Specifically, R1 to R4 may be the same or different from each other and each independently represent hydrogen, deuterium (D), a cyano group, C1 to C 40 Alkyl groups of C6 to C 60 and heteroaryl groups having 5 to 60 ring atoms, or are preferably fused rings formed by bonding these with adjacent groups.

[0034] Here, o, p, and q are each independently an integer of 0 to 4, and r may be an integer of 0 to 3. When o is 0, R1 is hydrogen, and when o is 1 to 3, R1 may have the above-mentioned substituents excluding hydrogen. p, q, and r are similarly applicable.

[0035] In Chemical Formula 1 according to the present invention, a nitrogen-containing heteroaromatic ring (e.g., azine, ring containing X1 to X3) having excellent electron transport ability and EWG properties is directly linked to one phenyl ring of the polycyclic spiro core structure (e.g., ring containing Y1 to Y2).

[0036] The nitrogen-containing heterocycle (e.g., a ring containing X1 to X3) is a monocyclic or polycyclic nitrogen-containing heteroaryl group containing at least two nitrogen atoms. According to one embodiment of the nitrogen-containing heteroaromatic ring, X1 to X3 are the same or different and each independently represent C(R5) or N, provided that at least two of X1 to X3 contain N. Specifically, they contain 2 to 3 N. By including a heterocycle containing 2 to 3 nitrogen atoms, the ring exhibits better electron absorption properties and is advantageous for electron injection and transport.

[0037] where R5 is hydrogen, deuterium (D), C1 to C 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 atoms, C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C3-C 40 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron groups, C6-C 60 Arylphosphanyl groups, C6-C 60 Monoarylphosphinyl groups, C6-C 60 Diarylphosphinyl groups, C6-C 60 Arylamine groups, C5-C 60 and heteroarylamine groups having 5 to 60 ring atoms, or these may be bonded to any adjacent group to form a condensed ring. In this case, when there are multiple R5, the multiple R5 may be the same or different from each other. Specifically, R5 is selected from the group consisting of hydrogen, deuterium (D), C1 to C 40 Alkyl groups of C6 to C 60 and heteroaryl groups having 5 to 60 ring atoms.

[0038] According to one specific example, the nitrogen-containing heterocycle (e.g., X1-X3-containing ring) may be further embodied as any one selected from the following structural formulae, but is not limited thereto:

[0039] [ka]

[0040] In the above formula, * means a linking site to Chemical Formula 1; W is O or S; Ar1 and Ar2 are defined as in Chemical Formula 1.

[0041] The nitrogen-containing heterocycle (for example, a ring containing X1 to X3) may be substituted with various substituents, such as Ar1 and Ar2. Ar1 and Ar2 may be the same or different and each independently represent a C1 to C 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 atoms, C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C3-C 40 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron groups, C6-C 60 Arylphosphine groups, C6-C 60 arylphosphine oxide groups, and C6-C 60 or these may be bonded to any adjacent group to form a fused ring. Specifically, Ar1 and Ar2 are each independently selected from the group consisting of C6 to C 60or a heteroaryl group having 5 to 60 ring atoms.

[0042] According to one embodiment, Ar1 and Ar2 may be the same or different and may each independently be embodied as any one of the following structural formulae, but are not limited thereto:

[0043] [ka]

[0044] [ka]

[0045] In the above formula, * denotes a linking site to the above-mentioned Chemical Formula 1. Although not shown in the above-mentioned structural formula, the compound may be substituted with at least one substituent known in the art (for example, the same as the defined portion of R5).

[0046] In the above-mentioned Chemical Formula 1, Ar1 to Ar2, R1 to R5, and R 11 The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, and arylamine group each independently include deuterium (D), halogen, cyano group, nitro group, C1 to C6 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 atoms, C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C1-C 40Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron groups, C6-C 60 Arylphosphine groups, C6-C 60 arylphosphine oxide groups, and C6-C 60 In this case, when there are a plurality of the substituents, they may be the same or different.

[0047] According to one embodiment of the present invention, the compound represented by Chemical Formula 1 may be further embodied as any one of the following Chemical Formulas 2 to 9, depending on the type of heteroatom introduced into the polycyclic spiro core structure, but is not limited thereto.

[0048] [ka]

[0049] [ka]

[0050] [ka]

[0051] [ka]

[0052] [ka]

[0053] [ka]

[0054] [ka]

[0055] [ka]

[0056] In the above formula, X1~X3, Ar1~Ar2, R1~R4, R 11 , o, p, q, and r are defined as in Chemical Formula 1, respectively.

[0057] According to another embodiment of the present invention, the compound represented by Chemical Formula 1 may be further embodied as any one of the following Chemical Formulas 10 to 20 depending on the type of nitrogen-containing heterocycle (e.g., X1 to X3-containing ring), but is not limited thereto.

[0058] [ka]

[0059] [ka]

[0060] [ka]

[0061] [ka]

[0062] [ka]

[0063] [ka]

[0064] [ka]

[0065] [ka]

[0066] [ka]

[0067] [ka]

[0068] [ka]

[0069] In the above formula, W is O or S; Y1 to Y2, Ar1 to Ar2, R1 to R4, o, p, q, and r are each defined as in Chemical Formula 1.

[0070] According to another embodiment of the present invention, the compound represented by Chemical Formula 1 may be further embodied as any one of the following Chemical Formulas 21 to 28, depending on the bonding position of the axially bonded ring formed in the polycyclic spiro core, but is not limited thereto.

[0071] [ka]

[0072] [ka]

[0073] [ka]

[0074] [ka]

[0075] [ka]

[0076] [ka]

[0077] [ka]

[0078] [ka]

[0079] In the above formula, Ring A may be a typical hydrocarbon ring or a hydrocarbon ring containing one or more heteroatoms as known in the art, which may be fused, bridged, or spirocyclically bonded to another adjacent ring (e.g., core structure). For example, ring A may be selected from the group consisting of a monocyclic or polycyclic alicyclic ring, a monocyclic or polycyclic heteroalicyclic ring, a monocyclic or polycyclic aromatic ring, or a monocyclic or polycyclic heteroaromatic ring. Specifically, ring A may be a C6-C 18 or a heteroaromatic ring having 5 to 18 ring atoms.

[0080] X1 to X3, Y1 to Y2, Ar1 to Ar2, R1 to R4, o, p, q, and r are each defined as in Chemical Formula 1.

[0081] According to yet another embodiment of the present invention, the compound represented by Chemical Formula 1 may be further embodied as any one of the following Chemical Formulas 29 to 31 depending on the bonding position of the nitrogen-containing heterocycle, but is not limited thereto.

[0082] [ka]

[0083] [ka]

[0084] [ka]

[0085] In the above formula, X1 to X3, Y1 to Y2, Ar1 to Ar2, R1 to R4, o, p, q, and r are each defined as in claim 1.

[0086] The compound represented by Chemical Formula 1 according to the present invention described above may be further embodied as any one of the following compounds 1 to 120. However, the compound represented by Chemical Formula 1 according to the present invention is not limited to the following examples.

[0087] [ka]

[0088] [ka]

[0089] [ka]

[0090] [ka]

[0091] [ka]

[0092] [ka]

[0093] [ka]

[0094] [ka]

[0095] In the present invention, the "number of ring atoms" refers to the number of ring atoms constituting the cyclic structure, and the ring atom may refer to carbon or a heteroatom selected from the group consisting of N, O, S, and Se. For example, the number of ring atoms in pyridine is 6, including 5 C atoms and 1 N atoms constituting the pyridine ring.

[0096] In the present invention, "alkyl" means a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, etc.

[0097] In the present invention, "alkenyl" means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and one or more carbon-carbon double bonds. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, and 2-butenyl.

[0098] In the present invention, "alkynyl" means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and one or more carbon-carbon triple bonds. Examples thereof include, but are not limited to, ethynyl and 2-propynyl.

[0099] In the present invention, the term "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms, which is a single ring or a combination of two or more rings. It may also include a form in which two or more rings are pendant or fused to each other. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, etc.

[0100] In the present invention, the term "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 ring atoms. In this case, one or more carbon atoms, preferably 1 to 3 carbon atoms, in the ring are substituted with a heteroatom such as N, O, S, or Se. In addition, the term may include a form in which two or more rings are pendant or fused to each other, and may further include a form in which two or more rings are fused to an aryl group. Examples of such heteroaryls include, but are not limited to, 6-membered monocyclic rings such as pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.

[0101] In the present invention, "aryloxy" refers to a monovalent substituent represented by RO-, where R means an aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.

[0102] In the present invention, "alkyloxy" refers to a monovalent substituent represented by R'O-, where R' is an alkyl having 1 to 40 carbon atoms and may have a linear, branched, or cyclic structure. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.

[0103] In the present invention, the term "arylamine" refers to an amine substituted with an aryl having 6 to 40 carbon atoms.

[0104] In the present invention, the term "cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.

[0105] In the present invention, "heterocycloalkyl" refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 ring atoms, in which one or more carbon atoms, preferably 1 to 3 carbon atoms in the ring, are substituted with a heteroatom such as N, O, S, or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine.

[0106] In the present invention, "alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 40 carbon atoms.

[0107] In the present invention, the term "fused ring" means a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, a fused heteroaromatic ring, or a combination thereof.

[0108] <Electron transport layer material> The present invention provides an electron transport layer comprising the compound represented by Chemical Formula 1.

[0109] The electron transport layer (ETL) serves to transport electrons injected from the negative electrode to an adjacent layer, specifically, the light-emitting layer.

[0110] The compound represented by Chemical Formula 1 may be used alone as an electron transport layer (ETL) material or may be used in combination with electron transport layer materials known in the art, but is preferably used alone.

[0111] Electron transport layer materials that can be used with the compound of Formula 1 include conventional electron transport materials known in the art. Examples of usable electron transport materials include, but are not limited to, oxazole-based compounds, isoxazole-based compounds, triazole-based compounds, isothiazole-based compounds, oxadiazole-based compounds, thiadiazole-based compounds, perylene-based compounds, aluminum complexes (e.g., Alq3 (tris(8-quinolinolato)-aluminum), BAlq, SAlq, Almq3), and gallium complexes (e.g., Gaq'2OPiv, Gaq'2OAc, and 2(Gaq'2)). These may be used alone or in combination.

[0112] In the present invention, when the compound of Chemical Formula 1 and the electron transport layer material are used in combination, the mixing ratio thereof is not particularly limited and can be appropriately adjusted within a range known in the art.

[0113] <Electron transport auxiliary layer material> The present invention also provides an electron transporting auxiliary layer comprising the compound represented by Chemical Formula 1.

[0114] The electron transport layer is disposed between the light emitting layer and the electron transport layer and serves to prevent excitons or holes generated in the light emitting layer from diffusing into the electron transport layer.

[0115] The compound represented by Chemical Formula 1 may be used alone as the electron transport auxiliary layer material, or may be used in combination with an electron transport layer material known in the art, but is preferably used alone.

[0116] Materials for the electron transporting auxiliary layer that can be mixed with the compound of Formula 1 include conventional electron transporting materials known in the art, such as oxadiazole derivatives, triazole derivatives, pentane derivatives (e.g., BCP), and nitrogen-containing heterocyclic derivatives.

[0117] In the present invention, when the compound of Chemical Formula 1 and the electron transport auxiliary layer material are used in combination, the mixing ratio thereof is not particularly limited and can be appropriately adjusted within a range known in the art.

[0118] <Organic electroluminescence element> Another aspect of the present invention relates to an organic electroluminescence device (organic EL device) containing the compound represented by Chemical Formula 1 according to the present invention.

[0119] Specifically, the present invention relates to an organic electroluminescence device including a positive electrode (anode), a negative electrode (cathode), and one or more organic material layers interposed between the positive electrode and the negative electrode, wherein at least one of the one or more organic material layers includes a compound represented by Chemical Formula 1. In this case, the compound may be used alone or in combination of two or more kinds.

[0120] The one or more organic material layers may be one or more of a hole injection layer, a hole transport layer, an emitting layer, an emitting auxiliary layer, a lifetime improving layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one of the organic material layers contains the compound represented by Chemical Formula 1. Specifically, the organic material layer containing the compound of Chemical Formula 1 may be an emitting layer, an emitting auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and / or a lifetime improving layer, and more specifically, it is preferably an electron transport layer or an electron transport auxiliary layer.

[0121] The light-emitting layer of the organic electroluminescent device according to the present invention contains a host material and a dopant material, and in this case, the host material may contain the compound of Chemical Formula 1. Furthermore, the light-emitting layer of the present invention may contain, as a host, a compound known in the art in addition to the compound of Chemical Formula 1.

[0122] When the compound represented by Chemical Formula 1 is contained as an emission layer material of an organic electroluminescent device, preferably as a blue, green, or red phosphorescent host material, the binding strength between holes and electrons in the emission layer is increased, thereby improving the efficiency (light-emitting efficiency and power efficiency), lifespan, brightness, driving voltage, etc. of the organic electroluminescent device. Specifically, the compound represented by Chemical Formula 1 is preferably contained in the organic electroluminescent device as a green and / or red phosphorescent host, fluorescent host, or dopant material. In particular, the compound represented by Chemical Formula 1 of the present invention is preferably an exciplex N-type host material for green phosphorescence in an emission layer with high efficiency.

[0123] The structure of the organic electroluminescent device of the present invention is not particularly limited, and may include a structure in which a substrate, a positive electrode, a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, and a negative electrode are sequentially stacked. In this case, one or more of the hole injection layer, hole transport layer, light-emitting auxiliary layer, light-emitting layer, electron transport layer, and electron injection layer may contain the compound represented by Chemical Formula 1. Preferably, the light-emitting layer, more preferably the phosphorescent host, may contain the compound represented by Chemical Formula 1. In addition, an electron injection layer may be further stacked on the electron transport layer.

[0124] The organic electroluminescent element of the present invention may have a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic layer.

[0125] The organic electroluminescence device of the present invention can be manufactured by forming organic layers and electrodes using materials and methods known in the art, except that at least one of the organic layers contains the compound represented by Chemical Formula 1.

[0126] The organic layer may be formed by a vacuum deposition method or a solution coating method, such as, but not limited to, spin coating, deep coating, doctor blading, inkjet printing, or thermal transfer.

[0127] The substrate used in manufacturing the organic electroluminescence device of the present invention is not particularly limited, and examples thereof include, but are not limited to, silicon wafers, quartz, glass plates, metal plates, plastic films, and sheets.

[0128] The positive electrode material may be any positive electrode material known in the art, without limitation, including, but not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO:Sb; conductive polymers such as polythiopene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiopene] (PEDT), polypyrrole, or polyaniline; and carbon black.

[0129] The negative electrode material may be any negative electrode material known in the art, including, but not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; and multilayer structures such as LiF / Al or LiO / Al.

[0130] The hole injection layer, hole transport layer, electron injection layer, and electron transport layer are not particularly limited, and ordinary materials known in the art can be used without any restrictions. [Example]

[0131] The present invention will be described in detail below with reference to examples. However, the following examples are merely illustrative of the present invention and are not intended to limit the scope of the present invention.

[0132] [Preparation Examples 1-9 Core Synthesis] The polycyclic spiro-based core structure according to the present invention can be prepared according to the following reaction scheme 1. However, the present invention is not limited thereto and can be prepared according to any conventional reaction method known in the art.

[0133] [ka]

[0134] In the above reaction scheme, Hal 1 in compound (A) may be a common halogen element known in the art, specifically Br or I. Hal 2 in compound (B) may be a common halogen element, specifically Cl, Br, or I.

[0135] In the core structure, Y1 to Y2, R1 to R4, o, p, q, and r are each defined as in Chemical Formula 1.

[0136] [Preparation example 1] <Step 1> Synthesis of 2-chlorospiro[thioxanthene-9,9'-xanthene] [ka]

[0137] Under a nitrogen atmosphere, 1-bromo-2-phenoxybenzene (50 g, 200.7 mmol) as compound (A) in Reaction Scheme 1 was dissolved in 670 mL of THF. While stirring at -78°C, 1.6 M n-BuLi solution (134 mL, 220.8 mmol) was added dropwise and the mixture was stirred for 1 hour. 2-Chloro-9H-thioxanthen-9-one (54.4 g, 220.8 mmol) as compound (B) in Reaction Scheme 1 was dissolved in 220 mL of THF and added dropwise. After stirring for 30 minutes, the mixture was warmed to room temperature and stirred for 2 hours. After confirming the disappearance of the raw materials, the solvent was concentrated under reduced pressure, and 115 mL of AcOH and 115 mL of HCl were added. The mixture was heated and stirred at 70°C for 1 hour. After cooling to room temperature, the reaction solution was extracted with dichloromethane, MgSO4 was added to remove moisture, and the mixture was filtered. After filtration, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 2-chlorospiro[thioxanthene]-9,9'-xanthene (45.0 g, yield 56.2%). Mass: [(M+H) + ]:399 <Step 2> Synthesis of Core 1 [ka]

[0138] 2-Chlorospiro[thioxanthene-9,9'-xanthene] (45.0 g, 112.8 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (37.2 g, 146.6 mmol), Pd(dppf)Cl2 (2.5 g, 6.7 mmol), KOAc (65.3 g, 665.4 mmol), and Xphos (6.3 g, 13.3 mmol) were added to 750 mL of 1,4-dioxane and heated under reflux for 12 hours. After the reaction was complete, the mixture was extracted with dichloromethane, and the water was removed by adding MgSO4. The mixture was then filtered. After filtration, the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane, followed by solidification using methanol. The solid was filtered, washed with methanol, and dried in an oven to give Core 1 (45.2 g, 81.7% yield). Mass: [(M+H) + ]:491 [Preparation example 2] <Step 1> Synthesis of 4'-chlorospiro[thioxanthene-9,9'-xanthene] [ka]

[0139] In Step 1 of [Preparation Example 1], 4'-chlorospiro[thioxanthene-9,9'-xanthene] (42.0 g, yield 55.84%) was obtained in the same manner as in Step 1 of [Preparation Example 1] using (2-bromophenyl)(phenyl)sulfane (50 g, 188.6 mmol), 4-chloro-9H-xanthen-9-one (47.8 g, 207.4 mmol), n-BuLi 1.6 M solution (129 ml, 207.4 mmol), THF 830 ml, AcOH 108 ml, and HCl 108 ml. Mass: [(M+H) + ]:399 <Step 2> Core2 synthesis [ka]

[0140] Core 2 (39.5 g, yield 76.5%) was obtained by the same procedure as in <Step 2> of [Preparation Example 1], except that 4'-chlorospiro[thioxanthene-9,9'-xanthene] (42.0 g, 105.3 mmol) was used instead of 2-chlorospiro[thioxanthene-9,9'-xanthene] as the reactant in <Step 2> of [Preparation Example 1]. Mass: [(M+H) + ]:491

[0141] [Preparation Example 3] Step 1: Synthesis of 3-chloro-10-phenyl-10H-spiro[acridine-9,9'-xanthene] [ka]

[0142] In Step 1 of [Preparative Example 1], 1-bromo-2-phenoxybenzene (50 g, 200.7 mmol), 3-chloro-10-phenylacridin-9(10H)-one (67.5 g, 220.8 mmol), n-BuLi 1.6 M solution (138 ml, 220.8 mmol), THF 1000 ml, AcOH 115 ml, and HCl 115 ml were used to obtain 3-chloro-10-phenyl-10H-spiro[acridine-9,9'-xanthene] (48.1 g, yield 52.3%) in the same manner as in Step 1 of [Preparative Example 1]. Mass: [(M+H) + ]:458

[0143] <Step 2> Core3 synthesis [ka]

[0144] Core 3 (35.5 g, yield 61.5%) was obtained by the same procedure as in Step 2 of [Preparation Example 1], except that 3-chloro-10-phenyl-10H-spiro[acridine-9,9'-xanthene] (48.1 g, 105.0 mmol) was used instead of 2-chlorospiro[thioxanthene-9,9'-xanthene] as the reactant in Step 2 of [Preparation Example 1]. Mass: [(M+H) + ]:550

[0145] [Preparation Example 4] Step 1: Synthesis of 2'-chloro-10-phenyl-10H-spiro[acridine-9,9'-thioxanthene] [ka]

[0146] In Step 1 of [Preparation Example 1], 2-bromo-N,N-diphenylaniline (50 g, 154.2 mmol), 2-chloro-9H-thioxanthen-9-one (41.8 g, 169.6 mmol), n-BuLi 1.6 M solution (106 ml, 169.6 mmol), THF 700 ml, AcOH 89 ml, and HCl 89 ml were used to obtain 2'-chloro-10-phenyl-10H-spiro[acridine-9,9'-thioxanthene] (37.8 g, yield 51.7%) in the same manner as in Step 1 of [Preparation Example 1]. Mass: [(M+H) + ]:474

[0147] <Step 2> Core 4 synthesis [ka]

[0148] Core 4 (35.5 g, yield 78.7%) was obtained by the same procedure as in Step 2 of [Preparation Example 1], except that 2'-chloro-10-phenyl-10H-spiro[acridine-9,9'-thioxanthene] (37.8 g, 79.8 mmol) was used instead of 2-chlorospiro[thioxanthene-9,9'-xanthene] as the reactant in Step 2 of [Preparation Example 1]. Mass: [(M+H) + ]:566

[0149] [Preparation Example 5] Step 1: Synthesis of 2-chloro-10-phenyl-10H-spiro[acridine-9,9'-xanthene] [ka]

[0150] In Step 1 of [Preparative Example 1], 2-chloro-10-phenyl-10H-spiro[acridine-9,9'-xanthene] (60.0 g, yield 65.3%) was obtained in the same manner as in Step 1 of [Preparative Example 1] using 1-bromo-2-phenoxybenzene (50 g, 200.7 mmol), 2-chloro-10-phenylacridin-9(10H)-one (67.5 g, 220.8 mmol), n-BuLi 1.6 M solution (138 ml, 220.8 mmol), THF 900 ml, AcOH 114 ml, and HCl 114 ml. Mass: [(M+H) + ]:458 <Step 2> Core5 synthesis [ka]

[0151] Core 5 (48.8 g, yield 67.8%) was obtained by the same procedure as in Step 2 of [Preparation Example 1], except that 2-chloro-10-phenyl-10H-spiro[acridine-9,9'-xanthene] (60.0 g, 131.0 mmol) was used instead of 2-chlorospiro[thioxanthene-9,9'-xanthene] as the reactant in Step 2 of [Preparation Example 1]. Mass: [(M+H) + ]:550

[0152] [Preparation Example 6] Step 1: Synthesis of 4'-chlorospiro[benzo[b]xanthene-12,9'-thioxanthene] [ka]

[0153] In Step 1 of [Preparation Example 1], 2-bromo-3-phenoxynaphthalene (30 g, 100.3 mmol), 4-chloro-9H-thioxanthen-9-one (27.2 g, 110.3 mmol), n-BuLi 1.6 M solution (68.9 ml, 110.3 mmol), THF 450 ml, AcOH 58 ml, and HCl 58 ml were used to obtain 4'-chlorospiro[benzo[b]xanthene-12,9'-thioxanthene] (24.6 g, yield 54.64%) in the same manner as in Step 1 of [Preparation Example 1]. Mass: [(M+H) + ]:449

[0154] <Step 2> Core6 synthesis [ka]

[0155] Core 6 (20.0 g, yield 67.5%) was obtained by the same procedure as in Step 2 of [Preparation Example 1], except that 4'-chlorospiro[benzo[b]xanthene-12,9'-thioxanthene] (24.6 g, 54.8 mmol) was used instead of 2-chlorospiro[thioxanthene-9,9'-xanthene] as the reactant in Step 2 of [Preparation Example 1]. Mass: [(M+H) + ]:540

[0156] [Preparation Example 7] <Step 1> Synthesis of 2-bromospiro[thioxanthene-9,9'-xanthene]-7-carbonitrile [ka]

[0157] In Step 1 of [Preparative Example 1], 2-bromospiro[thioxanthene-9,9'-xanthene]-7-carbonitrile (26.2 g, yield 46.4%) was obtained in the same manner as in Step 1 of [Preparative Example 1] using 1-bromo-2-phenoxybenzene (30 g, 120.4 mmol), 7-bromo-9-oxo-9H-thioxanthene-2-carbonitrile (41.8 g, 132.5 mmol), n-BuLi 1.6 M solution (83 ml, 132.5 mmol), THF 550 ml, AcOH 69 ml, and HCl 69 ml. Mass: [(M+H) + ]:469

[0158] <Step 2> Synthesis of Core7 [ka]

[0159] 2-Bromospiro[thioxanthene-9,9'-xanthene]-7-carbonitrile (26.2 g, 55.9 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (18.5 g, 72.7 mmol), Pd(dppf)Cl2 (1.2 g, 1.7 mmol), and KOAc (16.5 g, 168 mmol) were added to 200 mL of 1,4-dioxane and heated under reflux for 12 hours. After the reaction was complete, the mixture was extracted with dichloromethane, and MgSO4 was added to remove water and then filtered. After filtration, the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane, followed by solidification using methanol. The solid was filtered, washed with methanol, and dried in an oven to give Core 7 (20.5 g, 71.1% yield). Mass: [(M+H) + ]:515

[0160] [Preparation Example 8] Step 1: Synthesis of 4'-chloro-10-phenyl-10H-spiro[acridine-9,9'-thioxanthene] [ka]

[0161] In Step 1 of [Preparation Example 1], 2-bromo-N,N-diphenylaniline (30 g, 92.5 mmol), 4-chloro-9H-thioxanthen-9-one (25.1 g, 101.8 mmol), n-BuLi 1.6 M solution (63 ml, 101.8 mmol), THF 410 ml, AcOH 53 ml, and HCl 53 ml were used to obtain 4'-chloro-10-phenyl-10H-spiro[acridine-9,9'-thioxanthene] (25.5 g, yield 58.1%) in the same manner as in Step 1 of [Preparation Example 1]. Mass: [(M+H) + ]:474

[0162] <Step 2> Core8 synthesis [ka]

[0163] Core 8 (19.9 g, yield 65.4%) was obtained by the same procedure as in Step 2 of [Preparation Example 1], except that 4'-chloro-10-phenyl-10H-spiro[acridine-9,9'-thioxanthene] (25.5 g, 53.8 mmol) was used instead of 2-chlorospiro[thioxanthene-9,9'-xanthene] as the reactant in Step 2 of [Preparation Example 1]. Mass: [(M+H) + ]:565

[0164] [Preparation Example 9] Step 1: Synthesis of 4-bromo-10-phenyl-10H-spiro[acridine-9,9'-thioxanthene] [ka]

[0165] In Step 1 of [Preparation Example 1], 4-bromo-10-phenyl-10H-spiro[acridine-9,9'-thioxanthene] (44.5 g, yield 59.2%) was obtained in the same manner as in Step 1 of [Preparation Example 1] using (2-bromophenyl)(phenyl)sulfane (50 g, 188.6 mmol), 4-bromo-10-phenylacridin-9(10H)-one (72.6 g, 207.4 mmol), n-BuLi 1.6 M solution (129 ml, 207.4 mmol), THF 830 ml, AcOH 108 ml, and HCl 108 ml. Mass: [(M+H) + ]:399

[0166] <Step 2> Synthesis of Core9 [ka]

[0167] Core 9 (38.0 g, yield 60.2%) was obtained by the same procedure as in Step 2 of Preparative Example 7, except that 4-bromo-10-phenyl-10H-spiro[acridine-9,9'-thioxanthene] (44.5 g, 111.5 mmol) was used instead of 2-bromospiro[thioxanthene-9,9'-xanthene]-7-carbonitrile as the reactant in Step 2 of Preparative Example 7. Mass: [(M+H) + ]:566

[0168] [Synthesis Examples 1 to 19] [Synthesis Example 1] Synthesis of Inv6 [ka]

[0169] 2-Chloro-4-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-6-phenyl-1,3,5-triazine (15.0 g, 30.1 mmol), Core 6 (17.9 g, 33.1 mmol) from [Preparation Example 6], Pd(Pph3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.5 g, 90.2 mmol) were added to 120 ml of toluene, 30 ml of EtOH, and 30 ml of HO and heated under reflux for 4 hours. After the reaction was complete, the mixture was extracted with dichloromethane, added with MgSO4, and filtered. The solvent in the filtered organic layer was removed, followed by column chromatography using dichloromethane and hexane, followed by recrystallization with toluene and acetone to obtain Inv6 (28.2 g, 84.8% yield). Mass: [(M+H) + ]:878

[0170] [Synthesis Example 2] Synthesis of Inv7 [ka]

[0171] 3'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (15.0 g, 40.7 mmol), 4,4,5,5-tetramethyl-2-(3'-phenylspiro[thioxanthene-9,9'-xanthene]-4-yl)-1,3,2-dioxaborolane (25.3 g, 44.7 mmol), Pd(Pph3)4 (1.4 g, 1.2 mmol), and K2CO3 (16.9 g, 122.0 mmol) were added to 160 ml of toluene, 40 ml of EtOH, and 40 ml of H2O, and the mixture was heated under reflux for 4 hours. After the reaction was complete, the mixture was extracted with dichloromethane, added with MgSO4, and filtered. After removing the solvent from the filtered organic layer, the residue was subjected to column chromatography using dichloromethane and hexane, and then recrystallized from toluene and acetone to obtain Inv7 (19.87 g, yield 62.9%). Mass: [(M+H) + ]:773

[0172] [Synthesis Example 3] Synthesis of Inv8 [ka]

[0173] 4'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-carbonitrile (15.0 g, 40.7 mmol), 4,4,5,5-tetramethyl-2-(spiro[benzo[c]xanthene-7,9'-thioxanthene]-9-yl)-1,3,2-dioxaborolane (24.2 g, 44.7 mmol), Pd(Pph3)4 (1.4 g, 1.2 mmol), and K2CO3 (16.9 g, 122.0 mmol) were added to 160 ml of toluene, 40 ml of EtOH, and 40 ml of HO, and the mixture was heated under reflux for 4 hours. After the reaction was complete, the mixture was extracted with dichloromethane, added with MgSO4, and filtered. After removing the solvent from the filtered organic layer, the residue was subjected to column chromatography using dichloromethane and hexane, and then recrystallized from toluene and acetone to obtain Inv8 (21.0 g, yield 69.1%). Mass: [(M+H) + ]:747

[0174] [Synthesis Example 4] Synthesis of Inv13 [ka]

[0175] 3'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (15.0 g, 40.7 mmol), 10-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-thioxanthene] (25.3 g, 44.7 mmol), Pd(Pph3)4 (1.4 g, 1.2 mmol), and K2CO3 (16.9 g, 122.0 mmol) were added to 160 ml of toluene, 40 ml of EtOH, and 40 ml of HO, and the mixture was heated under reflux for 4 hours. After the reaction was complete, the mixture was extracted with dichloromethane, added with MgSO4, and filtered. After removing the solvent from the filtered organic layer, the residue was subjected to column chromatography using dichloromethane and hexane, and then recrystallized from toluene and acetone to obtain Inv13 (18.1 g, yield 57.7%). Mass: [(M+H) + ]:772

[0176] [Synthesis Example 5] Synthesis of Inv29 [ka]

[0177] 3'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (15.0 g, 40.8 mmol), Core 3 (17.9 g, 33.1 mmol) from [Preparation Example 3], Pd(Pph3)4 (1.4 g, 1.2 mmol), and K2CO3 (16.9 g, 122.3 mmol) were added to 160 ml of toluene, 40 ml of EtOH, and 40 ml of HO and heated under reflux for 4 hours. After the reaction was complete, the mixture was extracted with dichloromethane, added with MgSO4, and filtered. After removing the solvent from the filtered organic layer, the mixture was subjected to column chromatography using dichloromethane and hexane, followed by recrystallization with toluene and acetone to obtain Inv29 (24.6 g, 79.9% yield). Mass: [(M+H) + ]:755

[0178] [Synthesis Example 6] Synthesis of Inv40 [ka]

[0179] 3'-(6-chloro-2-phenylpyrimidin-4-yl)-[1,1'-biphenyl]-4-carbonitrile (15.0 g, 35.7 mmol), Core 1 (19.3 g, 39.3 mmol) from [Preparation Example 1], Pd(Pph3)4 (1.2 g, 1.07 mmol), and K2CO3 (14.8 g, 107.2 mmol) were added to 120 ml of toluene, 30 ml of EtOH, and 30 ml of HO and heated under reflux for 4 hours. After the reaction was complete, the mixture was extracted with dichloromethane, added with MgSO4, and filtered. After removing the solvent from the filtered organic layer, the mixture was subjected to column chromatography using dichloromethane and hexane, followed by recrystallization with toluene and acetone to obtain Inv40 (19.5 g, 72.9% yield). Mass: [(M+H) + ]:748

[0180] [Synthesis Example 7] Synthesis of Inv41 [ka]

[0181] Inv41 (15.8 g, 63.5% yield) was obtained by the same procedure as in Synthesis Example 3, except that 2-chloro-4-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-6-phenyl-1,3,5-triazine (15.0 g, 30.06 mmol) was used instead of 3'-(6-chloro-2-phenylpyrimidin-4-yl)-[1,1'-biphenyl]-4-carbonitrile. Mass: [(M+H) + ]:827

[0182] [Synthesis Example 8] Synthesis of Inv44 [ka]

[0183] 2-(4-Chlorophenyl)-4,6-diphenyl-1,3,5-triazine (8.0 g, 23.3 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[thioxanthene-9,9'-xanthene]-4-yl)-1,3,5-triazine (18.5 g, 25.6 mmol), Pd(OAc) (0.2 g, 0.7 mmol), XPhos (1.1 g, 2.33 mmol), and CsCO (22.7 g, 69.8 mmol) were added to 100 ml of toluene, 25 ml of EtOH, and 25 ml of HO, and the mixture was heated under reflux for 4 hours. After completion of the reaction, the mixture was extracted with dichloromethane, added with MgSO, and filtered. After removing the solvent from the filtered organic layer, the residue was subjected to column chromatography using dichloromethane and hexane, and then recrystallized from toluene and acetone to obtain Inv44 (16.5 g, yield 78.5%). Mass: [(M+H) + ]:903

[0184] [Synthesis Example 9] Synthesis of Inv46 [ka]

[0185] 2-Chloro-4-phenyl-6-(3-(pyridin-3-yl)phenyl)-1,3,5-triazine (15.0 g, 43.5 mmol), Core 8 (27.1 g, 47.8 mmol) from [Preparation Example 8], Pd(Pph3)4 (1.5 g, 1.3 mmol), and K2CO3 (18.0 g, 130.5 mmol) were added to 160 ml of toluene, 40 ml of EtOH, and 40 ml of HO and heated under reflux for 4 hours. After the reaction was complete, the mixture was extracted with dichloromethane, added with MgSO4, and filtered. The solvent in the filtered organic layer was removed, followed by column chromatography using dichloromethane and hexane, followed by recrystallization with toluene and acetone to obtain Inv46 (28.0 g, 86.1% yield). Mass: [(M+H) +]:748

[0186] [Synthesis Example 10] Synthesis of Inv54 [ka]

[0187] 4'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (15.0 g, 40.7 mmol), Core 2 (21.9 g, 44.7 mmol) from [Preparation Example 2], Pd(Pph3)4 (1.4 g, 1.2 mmol), and K2CO3 (16.9 g, 122.0 mmol) were added to 160 ml of toluene, 40 ml of EtOH, and 40 ml of HO and heated under reflux for 4 hours. After the reaction was complete, the mixture was extracted with dichloromethane, added with MgSO4, and filtered. After removing the solvent from the filtered organic layer, the mixture was subjected to column chromatography using dichloromethane and hexane, followed by recrystallization with toluene and acetone to obtain Inv54 (22.5 g, 79.4% yield). Mass: [(M+H) + ]:697

[0188] [Synthesis Example 11] Synthesis of Inv56 [ka]

[0189] 4'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-carbonitrile (15.0 g, 40.7 mmol), Core 7 (23.1 g, 44.7 mmol) from [Preparation Example 7], Pd(Pph3)4 (1.4 g, 1.2 mmol), and K2CO3 (16.9 g, 122.0 mmol) were added to 160 ml of toluene, 40 ml of EtOH, and 40 ml of HO and heated under reflux for 4 hours. After the reaction was complete, the mixture was extracted with dichloromethane, added with MgSO4, and filtered. After removing the solvent from the filtered organic layer, it was subjected to column chromatography using dichloromethane and hexane, and then recrystallized from toluene and acetone to obtain Inv56 (23.2 g, 79.0% yield). Mass: [(M+H) + ]:722

[0190] [Synthesis Example 12] Synthesis of Inv63 [ka]

[0191] 2-Chloro-4-(9,9-diphenyl-9H-fluoren-2-yl)-6-phenyl-1,3,5-triazine (14.3 g, 28.2 mmol), Core 5 (17.0 g, 31.0 mmol) from [Preparation Example 5], Pd(Pph3)4 (1.0 g, 0.85 mmol), and K2CO3 (11.7 g, 84.6 mmol) were added to 120 ml of toluene, 30 ml of EtOH, and 30 ml of HO and heated under reflux for 4 hours. After the reaction was complete, the mixture was extracted with dichloromethane, added with MgSO4, and filtered. After removing the solvent from the filtered organic layer, it was subjected to column chromatography using dichloromethane and hexane, and then recrystallized from toluene and acetone to obtain Inv63 (21.0 g, 81.0% yield). Mass: [(M+H) + ]:920

[0192] [Synthesis Example 13] Synthesis of Inv78 [ka]

[0193] 2-([1,1'-biphenyl]-4-yl)-4-([1,1':2',1''-terphenyl]-3-yl)-6-chloro-1,3,5-triazine (10.0 g, 20.2 mmol), Core 4 (12.5 g, 22.2 mmol) from [Preparation Example 4], Pd(Pph3)4 (0.7 g, 0.6 mmol), and K2CO3 (8.4 g, 60.5 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of HO and heated under reflux for 4 hours. After the reaction was complete, the mixture was extracted with dichloromethane, added with MgSO4, and filtered. The solvent in the filtered organic layer was removed, followed by column chromatography using dichloromethane and hexane, followed by recrystallization with toluene and acetone to obtain Inv78 (14.2 g, 78.3% yield). Mass: [(M+H) + ]:899

[0194] [Synthesis Example 14] Synthesis of Inv86 [ka]

[0195] Inv86 (13.5 g, yield 68.9%) was obtained by the same procedure as in Synthesis Example 9, except that 2-([1,1'-biphenyl]-3-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (10.0 g, 23.8 mmol) was used instead of 2-([1,1'-biphenyl]-4-yl)-4-([1,1':2',1''-terphenyl]-3-yl)-6-chloro-1,3,5-triazine. Mass: [(M+H) + ]:823

[0196] [Synthesis Example 15] Synthesis of Inv97 [ka]

[0197] Inv97 (16.4 g, 86.4% yield) was obtained by the same procedure as in [Synthesis Example 9], except that 2'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile (10.0 g, 22.33 mmol) was used instead of 2-([1,1'-biphenyl]-4-yl)-4-([1,1':2',1''-terphenyl]-3-yl)-6-chloro-1,3,5-triazine. Mass: [(M+H) + ]:853

[0198] [Synthesis Example 16] Synthesis of Inv100 [ka]

[0199] 3-(4-chloro-6-(4-cyanophenyl)-1,3,5-triazin-2-yl)benzonitrile (15.0 g, 47.2 mmol), Core 9 (29.4 g, 51.9 mmol) from [Preparation Example 9], Pd(Pph3)4 (1.6 g, 1.4 mmol), and K2CO3 (19.6 g, 141.6 mmol) were added to 160 ml of toluene, 40 ml of EtOH, and 40 ml of HO and heated under reflux for 4 hours. After the reaction was complete, the mixture was extracted with dichloromethane, added with MgSO4, and filtered. After removing the solvent from the filtered organic layer, it was subjected to column chromatography using dichloromethane and hexane, and then recrystallized from toluene and acetone to obtain Inv100 (28.8 g, 84.6% yield). Mass: [(M+H) + ]:721

[0200] [Synthesis Example 17] Synthesis of Inv111 [ka]

[0201] Inv111 (19.8 g, 72.4% yield) was obtained by the same procedure as in [Synthesis Example 8], except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-(4-(naphthalen-1-yl)phenyl)-1,3,5-triazine (15.0 g, 31.9 mmol) was used instead of 2-(6-chloro-2-phenylpyrimidin-4-yl)-9,9-diphenyl-9H-fluorene-3-carbonitrile. Mass: [(M+H) + ]:858

[0202] [Synthesis Example 18] Synthesis of Inv113 [ka]

[0203] Inv113 (22.5 g, 71.7% yield) was obtained by the same procedure as in [Synthesis Example 16], except that 4'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-carbonitrile (15.0 g, 40.7 mmol) was used instead of 3-(4-chloro-6-(4-cyanophenyl)-1,3,5-triazin-2-yl)benzonitrile. Mass: [(M+H) + ]:772

[0204] [Synthesis Example 19] Synthesis of Inv115 [ka]

[0205] 3'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (15.0 g, 40.7 mmol), 10-phenyl-3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-xanthene] (24.6 g, 44.7 mmol), Pd(Pph3)4 (1.4 g, 1.2 mmol), and K2CO3 (16.9 g, 122.0 mmol) were added to 160 ml of toluene, 40 ml of EtOH, and 40 ml of HO, and the mixture was heated under reflux for 4 hours. After the reaction was complete, the mixture was extracted with dichloromethane, added with MgSO4, and filtered. After removing the solvent from the filtered organic layer, the residue was subjected to column chromatography using dichloromethane and hexane, and then recrystallized from toluene and acetone to obtain Inv115 (24.0 g, yield 78.0%). Mass: [(M+H) + ]:756

[0206] [Examples 1 to 19] Preparation of blue organic electroluminescence devices Each of the compounds synthesized above was purified to high purity by sublimation using a conventional method, and then blue organic electroluminescence devices were fabricated as follows.

[0207] First, a glass substrate coated with a 1200 Å thick indium tin oxide (ITO) thin film was ultrasonically cleaned in distilled water. After the distilled water cleaning, the substrate was ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a UV ozone cleaner (Powersonic 405, manufactured by HWASHIN TECH) and cleaned using UV for 5 minutes before being transferred to a vacuum deposition machine.

[0208] On the ITO transparent electrode prepared as described above, the following layers were stacked in the order of HT-1 + 2% HAT-CN (100 Å) / HT-1 (1400 Å) / HT-2 (50 Å) / BH + 2% BD (200 Å) / ET-2 (50 Å) / each of the Inv6 to Inv103 compounds: LiQ = 1:1 (300 Å) / LiF (10 Å) / Al (1000 Å) to prepare an organic electroluminescence device.

[0209] The structures of the compounds used here, HT-1, HAT-CN, HT-2, BH, BD, ET-1, ET-2, and LiQ, are as follows:

[0210] [ka]

[0211] [ka]

[0212] [ka]

[0213] [Comparative Examples 1 to 4] Preparation of blue organic electroluminescence devices Blue organic electroluminescence devices of Comparative Examples 1 to 4 were fabricated in the same manner as in Example 1, except that ET-1, ET-3, ET-4, and ET-5 were deposited to a thickness of 300 Å instead of Compound 1 as the electron transport layer material.

[0214] The structures of the ET-3, ET-4, and ET-5 used here are as follows:

[0215] [ka]

[0216] [Evaluation example 1] For each of the blue organic electroluminescence devices fabricated in Examples 1 to 19 and Comparative Examples 1 to 4, a current density of 10 mA / cm 2 Driving voltage, current efficiency, T 95 and the emission peak were measured, and the results are shown in Table 1 below.

[0217] [Table 1]

[0218] As shown in Table 1, the blue organic electroluminescent devices of Examples 1 to 19, which used the compounds according to the present invention as electron transport layer materials, exhibited superior performance in terms of driving voltage, emission peak, and current efficiency compared to the blue organic electroluminescent devices of Comparative Examples 1 to 4, which used conventional ET-1, ET-3, ET-4, and ET-5 as electron transport layer materials.

Claims

1. A compound represented by the following chemical formula 1: 【Chemistry 1】 In the above Chemical Formula 1, X １ ~X ３ are the same or different, and each independently represents C(R ５ ) or N, with the proviso that X １ ~X ３ at least two of are N, Y １ and Y ２ are the same or different from each other and each independently represent O, S, and NR １１ wherein Y is selected from the group consisting of １ and Y ２ is simultaneously O is excluded, Ar １ and Ar ２ are the same or different from each other, and each independently represents C １ ~C ４０ alkyl group of C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms, a heterocycloalkyl group having 3 to 40 ring atoms, C ６ ~C ６０ an aryl group having 5 to 60 ring atoms; a heteroaryl group having 5 to 60 ring atoms; １ ~C ４０ an alkyloxy group of C ６ ~C ６０ an aryloxy group of C ３ ~C ４０ an alkylsilyl group of C ６ ~C ６０ an arylsilyl group of C １ ~C ４０ alkylboron groups of C ６ ~C ６０ an arylboron group of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ an arylphosphine oxide group of the formula C ６ ~C ６０ or which may be joined to any adjacent group to form a fused ring; R １ ~R ５ and R １１ are the same or different and each independently represent hydrogen, deuterium (D), halogen, cyano group, nitro group, C １ ~C ４０ alkyl group of C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms, a heterocycloalkyl group having 3 to 40 ring atoms, C ６ ~C ６０ an aryl group having 5 to 60 ring atoms; a heteroaryl group having 5 to 60 ring atoms; １ ~C ４０ an alkyloxy group of C ６ ~C ６０ an aryloxy group of C ３ ~C ４０ an alkylsilyl group of C ６ ~C ６０ an arylsilyl group of C １ ~C ４０ alkylboron groups of C ６ ~C ６０ an arylboron group of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ an arylphosphine oxide group of the formula C ６ ~C ６０ or which may be joined to any adjacent group to form a fused ring; o, p, and q are each independently an integer of 0 to 4, and r is an integer of 0 to 3; The Ar １ ~Ar ２ , R １ ~R ５ , and R １１ The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, and arylamine group each independently represent a deuterium (D), a halogen, a cyano group, a nitro group, C １ ~C ４０ alkyl group of C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms, a heterocycloalkyl group having 3 to 40 ring atoms, C ６ ~C ６０ an aryl group having 5 to 60 ring atoms; a heteroaryl group having 5 to 60 ring atoms; １ ~C ４０ an alkyloxy group of C ６ ~C ６０ an aryloxy group of C １ ~C ４０ an alkylsilyl group of C ６ ~C ６０ an arylsilyl group of C １ ~C ４０ alkylboron groups of C ６ ~C ６０ an arylboron group of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ an arylphosphine oxide group of the formula C ６ ~C ６０ In this case, when there are a plurality of the substituents, they may be the same or different.

2. The Y １ and Y ２ The compound according to claim 1, wherein the ring-containing compound is any one selected from the following structural formulas: 【Chemistry 2】 In the above formula, * means a linking site to Chemical Formula 1; R １１ is hydrogen, deuterium (D), C １ ~C ４０ alkyl group of C ６ ~C ６０ and heteroaryl groups having 5 to 60 ring atoms, R １ ~R ４ , o, p, q, and r are defined as in claim 1, respectively.

3. Y １ and Y ２ The compound of claim 1 , wherein:

4. 2. The compound of claim 1, wherein the X-containing moiety is any one selected from the following structural formulas: 【Transformation 3】 In the above formula, * means a linking site to Chemical Formula 1; W is O or S; Ar １ and Ar ２ are defined as in claim 1.

5. Ar １ and Ar ２ are the same or different from each other, and each independently represents C ６ ~C ６０ and heteroaryl groups having 5 to 60 ring atoms.

6. Ar １ and Ar ２ are each independently any one selected from the following structural formulas: 【Chemistry 4】 【Transformation 5】 In the above formula, * indicates the linking site to Chemical Formula 1.

7. R １ ~R ４ are the same or different and each independently represent hydrogen, deuterium (D), a cyano group, C １ ~C ４０ alkyl group of C ６ ~C ６０ and heteroaryl groups having 5 to 60 ring atoms, or which are bonded to adjacent groups to form a fused ring.

8. The compound represented by Chemical Formula 1 is the compound according to claim 1, which is represented by any one of Chemical Formulas 2 to 9 below: 【Transformation 6】 【Transformation 7】 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 In the above formula, X １ ~X ３ , Ar １ ~Ar ２ , R １ ~R ４ , R １１ , o, p, q, and r are defined as in claim 1, respectively.

9. The compound represented by Chemical Formula 1 is the compound according to claim 1, which is represented by any one of Chemical Formulas 10 to 20 below: 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 [Chemistry 18] 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemistry 22】 【Chemistry 23】 【Chemistry 24】 In the above formula, W is O or S; Y １ ~Y ２ , Ar １ ~Ar ２ , R １ ~R ４ , o, p, q, and r are defined as in claim 1, respectively.

10. The compound represented by Chemical Formula 1 is the compound according to claim 1, which is represented by any one of Chemical Formulas 21 to 28 below: 【Chemistry 25】 【Chemistry 26】 【Chemistry 27】 【Chemistry 28】 【Chemistry 29】 【Transformation 30】 【Chemistry 31】 【Chemistry 32】 In the above formula, Ring A is a monocyclic or polycyclic alicyclic ring, a monocyclic or polycyclic heteroalicyclic ring, a monocyclic or polycyclic aromatic ring, or a monocyclic or polycyclic heteroaromatic ring; X １ ~X ３ , Y １ ~Y ２ , Ar １ ~Ar ２ , R １ ~R ４ , o, p, q, and r are defined as in claim 1, respectively.

11. The compound represented by Chemical Formula 1 is the compound according to claim 1, which is represented by any one of Chemical Formulas 29 to 31 below: 【Transformation 33】 【Transformation 34】 【Chemistry 35】 In the above formula, X １ ~X ３ , Y １ ~Y ２ , Ar １ ~Ar ２ , R １ ~R ４ , o, p, q, and r are defined as in claim 1, respectively.

12. The compound according to claim 1, wherein the compound represented by Chemical Formula 1 is represented by any one of Chemical Formulas 1 to 120 below. 【Transformation 36】 【Chemistry 37】 【Transformation 38】 【Chemistry 39】 【Chemistry 40】 【Chemistry 41】 【Chemistry 42】 【Chemistry 43】

13. The compound according to claim 1 , wherein the compound represented by Chemical Formula 1 is a material for a light-emitting layer, an electron-transporting layer, or an electron-transporting auxiliary layer.

14. An organic electroluminescence device comprising a positive electrode, a negative electrode, and one or more organic layers interposed between the positive electrode and the negative electrode, wherein at least one of the one or more organic layers comprises the compound according to any one of claims 1 to 13.

15. 15. The organic electroluminescence device according to claim 14, wherein the organic layer containing the compound is selected from the group consisting of a light-emitting layer, a light-emitting auxiliary layer, a life-improving layer, an electron-transporting layer, and an electron-transporting auxiliary layer.

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