Organic compound and organic electroluminescent element comprising same

Abstract

The present invention relates to an organic compound and an organic electroluminescent element comprising the same, the compound of the present invention being used in an organic material layer, preferably an electron transport layer or an electron transport auxiliary layer, of an organic electroluminescent element, whereby the luminous efficiency, the driving voltage, the lifespan, and the like of the organic electroluminescent element can be improved. Specifically, the present invention can provide a compound represented by any one of the following Chemical Formulae 5 and 6: # imgabs0 #

Description

[0001] This application is a divisional application of the Chinese patent application with the application date of October 16, 2017, application number 201780066461.0, and invention name “Organic compounds and organic electroluminescent elements containing the same”. Technical Field

[0002] The present invention relates to a novel organic compound that can be used as a material for an organic electroluminescent device and an organic electroluminescent device containing the same. Background Art

[0003] Starting with Bernanose's observations of organic thin-film luminescence in the 1950s, research into organic electroluminescent (EL) devices progressed, with the development of blue electroluminescence from anthracene single crystals in 1965. This was followed by Tang's proposal in 1987 of an EL device with a stacked structure consisting of two functional layers: a vacancy layer and a light-emitting layer. Subsequently, in order to produce high-efficiency, long-life EL devices, the development of specialized organic layers within the device was developed, and specialized materials for this purpose were subsequently developed.

[0004] In organic electroluminescent devices, when voltage is applied between two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed. When these excitons transition to the ground state, light is emitted. The materials used in the organic layer can be categorized by their function as light-emitting materials, hole-injecting materials, hole-transporting materials, electron-transporting materials, and electron-injecting materials.

[0005] Luminescent materials can be divided into blue, green, and red luminescent materials according to the luminescent color, as well as yellow and orange luminescent materials for presenting more natural colors. In addition, in order to increase color purity and increase luminous efficiency through energy transfer, a host / dopant system can be used as a luminescent material.

[0006] Dopants can be categorized as fluorescent dopants using organic substances and phosphorescent dopants using metal coordination compounds containing heavy atoms such as Ir and Pt. Since the development of phosphorescent materials can theoretically increase luminous efficiency by up to four times compared to fluorescent materials, extensive research is being conducted not only on phosphorescent dopants but also on phosphorescent host materials.

[0007] To date, materials such as NPB, BCP, and Alq3 are widely known as materials for hole injection, hole transport, hole blocking, and electron transport layers. Anthracene derivatives have been reported as materials for light-emitting layers. Among light-emitting layer materials, Ir-containing metal complexes such as Firpic, Ir(ppy)3, and (acac)Ir(btp)2, which offer advantages in improving efficiency, have been used as blue, green, and red phosphorescent dopants, and 4,4-dicarbazolybiphenyl (CBP) has been used as a phosphorescent host material.

[0008]

[0009] However, while conventional organic layer materials have advantages in terms of luminescence properties, they have low glass transition temperatures and very poor thermal stability, making them unsatisfactory in terms of the lifespan of organic electroluminescent devices. Therefore, the development of organic layer materials with superior performance is needed. Summary of the Invention

[0010] Technical issues

[0011] An object of the present invention is to provide a novel organic compound that can be used in an organic electroluminescent device and has excellent hole and electron injection and transport capabilities, light emission capabilities, etc.

[0012] Another object of the present invention is to provide an organic electroluminescent element that exhibits low driving voltage, high luminous efficiency, and improved life by containing the novel organic compound.

[0013] Solutions to Problems

[0014] In order to achieve the above object, the present invention provides a compound represented by the following Chemical Formula 1:

[0015] [Chemical Formula 1]

[0016]

[0017] In the above chemical formula 1,

[0018] X1 to X4 are each independently N or C(R2);

[0019] R1 and R2 are each independently a substituent represented by the following chemical formula 2. When there are multiple R2s, they are the same or different from each other;

[0020] [Chemical Formula 2]

[0021]

[0022] In the above chemical formula 2,

[0023] * means the part that forms the bond;

[0024] L1 and L2 are each independently selected from a single bond, C6 to C 18 A group consisting of an arylene group and a heteroarylene group having 5 to 18 atomic nuclei;

[0025] R3 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C3~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 or combined with adjacent groups to form an aromatic ring with 5 to 50 atomic nuclei, a non-aromatic condensed polycyclic ring with 5 to 50 atomic nuclei, an aromatic heterocyclic ring with 5 to 50 atomic nuclei, or a non-aromatic condensed heteropolycyclic ring with 5 to 50 atomic nuclei;

[0026] The arylene and heteroarylene groups represented by L1 and L2, the alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamino, alkylsilyl, alkylsulfonyl, arylsulfonyl, alkylboryl, arylboryl, arylphosphyl, mono- or diarylphosphino, alkylcarbonyl, arylcarbonyl and arylsilyl groups represented by R3, and the aromatic ring, non-aromatic condensed polycyclic ring, aromatic heterocyclic ring and non-aromatic condensed heteropolycyclic ring formed by the combination of two adjacent R3 are each independently selected from deuterium, halogen, cyano, nitro, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C6~C60 aryl, heteroaryl with 5 to 60 atomic nuclei, C6~C 60 Aryloxy, C1~C 40 Alkoxy, C6~C 60 Arylamine, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C1~C 40 Alkylsilyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 The arylsilyl group may be substituted with or unsubstituted with one or more substituents. When substituted with a plurality of substituents, they may be the same as or different from each other.

[0027] The present invention provides an organic electroluminescent element comprising an anode, a cathode, and one or more organic layers between the anode and the cathode, wherein at least one of the one or more organic layers comprises the compound of Chemical Formula 1.

[0028] The "alkyl group" in the present invention is a monovalent substituent derived from a linear or side-chain saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include, but are not limited to, a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a pentyl group, an isopentyl group, and a hexyl group.

[0029] The "alkenyl group" in the present invention is a monovalent substituent derived from a linear or side-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include vinyl, allyl, isopropenyl, and 2-butenyl, but are not limited thereto.

[0030] The "alkynyl" in the present invention is a monovalent substituent derived from a linear or side-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples thereof include, but are not limited to, ethynyl and 2-propynyl.

[0031] In the present invention, "aryl" means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, which is a single ring or a combination of two or more rings. Furthermore, it also includes monovalent substituents in which two or more rings are condensed, the ring-forming atoms contain only carbon atoms (e.g., 8 to 60 carbon atoms), and the molecule as a whole is non-aromatic. Examples of such aryl groups include, but are not limited to, phenyl, naphthyl, phenanthrenyl, anthracenyl, and fluorenyl.

[0032] The "heteroaryl" in the present invention means a monovalent substituent derived from a monocyclic heterocyclic or polycyclic aromatic hydrocarbon having 5 to 60 atomic nuclei. In this case, one or more carbon atoms, preferably 1 to 3 carbon atoms, in the ring are substituted by heteroatoms selected from N, O, P, S and Se. In addition, it should be interpreted as also including monovalent groups in which two or more rings are simply attached (pendant) or condensed to each other, and the ring-forming atoms contain heteroatoms selected from N, O, P, S and Se in addition to carbon, and the molecule as a whole has non-aromatic properties (non-aromaticity). Examples of such heteroaryl groups include six-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; phenanthroline; and Polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; 2-furyl, N-imidazolyl, 2-isothiazolyl, oxazolyl, 2-pyridyl, 2-pyrimidinyl, etc., but are not limited thereto.

[0033] In the present invention, "aryloxy" means a monovalent substituent represented by RO-, where R is an aryl group having 5 to 60 carbon atoms. Examples of such aryloxy groups include, but are not limited to, phenoxy, naphthyloxy, and diphenoxy.

[0034] In the present invention, "alkoxy" means a monovalent substituent represented by R'O-, where R' is an alkyl group having 1 to 40 carbon atoms and should be interpreted as including linear, branched, or cyclic structures. Examples of such alkoxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, tert-butoxy, n-butoxy, and pentoxy.

[0035] The "arylamino group" in the present invention means an amino group substituted with an aryl group having 6 to 60 carbon atoms.

[0036] In the present invention, "cycloalkyl" means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl groups include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantyl.

[0037] In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclei, wherein 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 groups include, but are not limited to, morpholinyl and piperidinyl.

[0038] In the present invention, the "alkylsilyl group" means a silyl group substituted by an alkyl group having 1 to 40 carbon atoms, and the "arylsilyl group" means a silyl group substituted by an aryl group having 5 to 60 carbon atoms.

[0039] In the present invention, an "aromatic ring" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, which is a single ring or a combination of two or more rings. Examples of such aromatic rings include, but are not limited to, phenyl, naphthyl, phenanthrenyl, and anthracenyl.

[0040] In the present invention, a "non-aromatic condensed polycyclic ring" refers to a monovalent group (e.g., having 8 to 60 carbon atoms) in which two or more rings are condensed, the ring-forming atoms consist only of carbon, and the molecule as a whole has non-aromatic properties. Examples of such non-aromatic condensed polycyclic rings include, but are not limited to, fluorenyl.

[0041] The "aromatic heterocycle" in the present invention means a monocyclic or polycyclic aromatic hydrocarbon having 5 to 60 atomic nuclei. In this case, one or more carbon atoms, preferably 1 to 3 carbon atoms, in the ring are substituted by heteroatoms selected from N, O, P, S and Se. In addition, two or more rings are simply attached (pendant) or condensed to each other, and as ring-forming atoms, they contain heteroatoms selected from N, O, P, S and Se in addition to carbon atoms. Examples of such heteroaryl groups include six-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and triazinyl; phenanthroline; Polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; 2-furyl, N-imidazolyl, 2-isothiazolyl, oxazolyl, 2-pyridyl, 2-pyrimidinyl, etc., but are not limited thereto.

[0042] In the present invention, a "non-aromatic condensed heteropolycyclic ring" refers to a group in which two or more rings are condensed, the ring-forming atoms include, in addition to carbon, a heteroatom selected from N, O, P, and S, and the molecule as a whole has non-aromatic properties (e.g., having 2 to 60 carbon atoms). Examples of such non-aromatic condensed heteropolycyclic rings include, but are not limited to, carbazolyl.

[0043] The "condensed ring" in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed aliphatic heterocycle, a condensed aromatic heterocycle, or a combination thereof.

[0044] Effects of the Invention

[0045] The compound of the present invention is excellent in thermal stability, carrier transporting ability, luminescence ability, etc., and therefore can be effectively used as an organic layer material of an organic electroluminescent device.

[0046] Furthermore, an organic electroluminescent device containing the compound of the present invention in its organic layer has greatly improved luminescence performance, driving voltage, lifespan, efficiency, etc., and can therefore be effectively applied to full-color display panels and the like. BRIEF DESCRIPTION OF THE DRAWINGS

[0047] Figure 1 A cross-sectional view showing an organic electroluminescent element according to an embodiment of the present invention.

[0048] Figure 2 A cross-sectional view showing an organic electroluminescent element according to an embodiment of the present invention.

[0049] 10: Anode 20: Cathode

[0050] 30: Organic layer 31: Hole transport layer

[0051] 32: Light-emitting layer 33: Hole transport auxiliary layer

[0052] 34: Electron transport layer 35: Electron transport auxiliary layer

[0053] 36: Electron injection layer 37: Hole injection layer DETAILED DESCRIPTION

[0054] The novel compound of the present invention can be represented by the following chemical formula 1:

[0055] [Chemical Formula 1]

[0056]

[0057] In the above chemical formula 1,

[0058] X1 to X4 are each independently N or C(R2);

[0059] R1 and R2 are each independently a substituent represented by the following chemical formula 2. When there are multiple R2s, they are the same or different from each other;

[0060] [Chemical Formula 2]

[0061]

[0062] In the above chemical formula 2,

[0063] * means the part that forms the bond;

[0064] L1 and L2 are each independently selected from a single bond, C6 to C 18 A group consisting of an arylene group and a heteroarylene group having 5 to 18 atomic nuclei;

[0065] R3 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C3~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 or combined with adjacent groups to form an aromatic ring with 5 to 50 atomic nuclei, a non-aromatic condensed polycyclic ring with 5 to 50 atomic nuclei, an aromatic heterocyclic ring with 5 to 50 atomic nuclei, or a non-aromatic condensed heteropolycyclic ring with 5 to 50 atomic nuclei;

[0066] The arylene and heteroarylene groups represented by L1 and L2, the alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamino, alkylsilyl, alkylsulfonyl, arylsulfonyl, alkylboryl, arylboryl, arylphosphyl, mono- or diarylphosphino, alkylcarbonyl, arylcarbonyl and arylsilyl groups represented by R3, and the aromatic ring, non-aromatic condensed polycyclic ring, aromatic heterocyclic ring and non-aromatic condensed heteropolycyclic ring formed by the combination of two adjacent R3 are each independently selected from deuterium, halogen, cyano, nitro, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C6~C 60 Aryloxy, C1~C 40 Alkoxy, C6~C 60 Arylamine, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C1~C 40 Alkylsilyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 The arylsilyl group may be substituted with or unsubstituted with one or more substituents. When substituted with a plurality of substituents, they may be the same as or different from each other.

[0067] Best Practice

[0068] Hereinafter, the present invention will be described in detail.

[0069] 1. New organic compounds

[0070] The novel compound of the present invention can be represented by the following chemical formula 1:

[0071] [Chemical Formula 1]

[0072]

[0073] In the above chemical formula 1,

[0074] X1 to X4 are each independently N or C(R2);

[0075] R1 and R2 are each independently a substituent represented by the following chemical formula 2. When there are multiple R2s, they are the same or different from each other;

[0076] [Chemical Formula 2]

[0077]

[0078] In the above chemical formula 2,

[0079] * means the part that forms the bond;

[0080] L1 and L2 are each independently selected from a single bond, C6 to C 18 A group consisting of an arylene group and a heteroarylene group having 5 to 18 atomic nuclei;

[0081] R3 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C3~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 or combined with adjacent groups to form an aromatic ring with 5 to 50 atomic nuclei, a non-aromatic condensed polycyclic ring with 5 to 50 atomic nuclei, an aromatic heterocyclic ring with 5 to 50 atomic nuclei, or a non-aromatic condensed heteropolycyclic ring with 5 to 50 atomic nuclei;

[0082] The arylene and heteroarylene groups of L1 and L2, the alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamino, alkylsilyl, alkylsulfonyl, arylsulfonyl, alkylboryl, arylboryl, arylphosphyl, mono- or diarylphosphino, alkylcarbonyl, arylcarbonyl and arylsilyl groups of R3, and the aromatic ring, non-aromatic condensed polycyclic, aromatic heterocyclic and non-aromatic condensed heteropolycyclic formed by the combination of two adjacent R3 are each independently selected from deuterium, halogen, cyano, nitro, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C6~C 60 Aryloxy, C1~C 40 Alkoxy, C6~C 60 Arylamine, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C1~C 40 Alkylsilyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 The arylsilyl group may be substituted with or unsubstituted with one or more substituents. When substituted with a plurality of substituents, they may be the same as or different from each other.

[0083] In the present invention, the EWG (electron-pulling group) characteristics of the compound represented by the above-mentioned chemical formula 1 are excellent. Compared with the six-membered heterocyclic structure known in the past, it is not only electrochemically stable and has excellent electron mobility, but also has a high glass transition temperature and excellent thermal stability. Thus, the electron transport ability and luminescent properties of the compound represented by the chemical formula 1 of the present invention are excellent, and therefore it can be used as a material for any layer of the organic layer of the organic electroluminescent element, i.e., the hole injection layer, the hole transport layer, the light-emitting layer, the electron transport layer and the electron injection layer. It is preferably a material that can be used as any layer of the light-emitting layer, the electron transport layer and the electron transport auxiliary layer stacked on the electron transport layer, and more preferably a material that can be used as an electron transport layer or an electron transport auxiliary layer.

[0084] Therefore, when the compound of the chemical formula 1 structure of the present invention is used in an organic electroluminescent element, not only can excellent thermal stability and carrier transport ability (especially electron transport ability and luminescence ability) be expected, but also the driving voltage, efficiency, life, etc. of the element can be improved. With the help of high triplet energy, as a material for the latest organic electroluminescent element, it can show excellent efficiency improvement.

[0085] According to a preferred embodiment of the present invention, the compound represented by the above Chemical Formula 1 may be a compound represented by any one of the following Chemical Formulas 3 to 6:

[0086] [Chemical Formula 3]

[0087]

[0088] [Chemical Formula 4]

[0089]

[0090] [Chemical Formula 5]

[0091]

[0092] [Chemical Formula 6]

[0093]

[0094] In the above chemical formulas 3 to 6,

[0095] R1 and R4 to R7 may each independently be a substituent represented by the above Chemical Formula 2.

[0096] According to a preferred embodiment of the present invention, one or more of R4 and R5, R5 and R6, and R6 and R7 are combined with each other to form an aromatic ring having 5 to 50 atomic nuclei, a non-aromatic condensed polycyclic ring having 5 to 50 atomic nuclei, an aromatic heterocyclic ring having 5 to 50 atomic nuclei, or a non-aromatic condensed heteropolycyclic ring having 5 to 50 atomic nuclei;

[0097] The aromatic ring, non-aromatic condensed polycyclic ring, aromatic heterocyclic ring and non-aromatic condensed heterocyclic ring formed by the combination of R4 and R5, R5 and R6, and R6 and R7 are independently selected from deuterium, halogen, cyano, nitro, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C6~C 60 Aryloxy, C1~C 40 Alkoxy, C6~C 60 Arylamine, C3~C40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C1~C 40 Alkylsilyl, C1~C 40 Alkyl boron, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 The arylsilyl group may be substituted with or unsubstituted with one or more substituents. When substituted with a plurality of substituents, they may be the same as or different from each other.

[0098] According to a preferred embodiment of the present invention, in the compounds represented by the above Chemical Formulas 3 to 6, one or more of R4 and R5, R5 and R6, and R6 and R7 can each independently form a condensed ring with a ring represented by any one of the following Chemical Formulas 7 to 11:

[0099] [Chemical Formula 7]

[0100]

[0101] [Chemical Formula 8]

[0102]

[0103] [Chemical Formula 9]

[0104]

[0105] [Chemical Formula 10]

[0106]

[0107] [Chemical Formula 11]

[0108]

[0109] In the above chemical formulas 7 to 11,

[0110] The dotted lines mean the parts that form the condensation;

[0111] Y1 to Y4 are each independently N or C(Ar1), and when there are multiple Ar1s, they are the same or different from each other;

[0112] X5 and X6 are each independently selected from the group consisting of a single bond, O, N, C(Ar2)(Ar3), S, Si(Ar4)(Ar5) and P(=O)(Ar6), but X5 and X6 are not both single bonds;

[0113] X7 is O, N(Ar7) or S;

[0114] Ar1 to Ar7 and R8 to R 13 Each is independently a substituent represented by the following Chemical Formula 12;

[0115] [Chemical Formula 12]

[0116]

[0117] In the above chemical formula 12,

[0118] * means the part that forms the bond;

[0119] L3 and L4 are each independently selected from a single bond, C6 to C 18 A group consisting of an arylene group and a heteroarylene group having 5 to 18 atomic nuclei;

[0120] R 14 Selected from hydrogen, deuterium, halogen, cyano, nitro, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C3~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60or combined with adjacent groups to form an aromatic ring with 5 to 50 atomic nuclei, a non-aromatic condensed polycyclic ring with 5 to 50 atomic nuclei, an aromatic heterocyclic ring with 5 to 50 atomic nuclei, or a non-aromatic condensed heteropolycyclic ring with 5 to 50 atomic nuclei;

[0121] The arylene and heteroarylene groups of L3 and L4, the R 14 The alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamino, alkylsilyl, alkylsulfonyl, arylsulfonyl, alkylboryl, arylboryl, arylphosphyl, mono- or diarylphosphino, alkylcarbonyl, arylcarbonyl and arylsilyl groups, and aromatic rings, non-aromatic condensed polycyclic rings, aromatic heterocyclic rings and non-aromatic condensed heteropolycyclic rings formed by two adjacent substituents are each independently selected from deuterium, halogen, cyano, nitro, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C6~C 60 Aryloxy, C1~C 40 Alkoxy, C6~C 60 Arylamine, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C1~C 40 Alkylsilyl, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 The arylsilyl group may be substituted with or unsubstituted with one or more substituents. When substituted with a plurality of substituents, they may be the same as or different from each other.

[0122] According to a preferred embodiment of the present invention, the ring represented by the above Chemical Formula 7 can be represented by the following Chemical Formula 13 or 14:

[0123] [Chemical Formula 13]

[0124]

[0125] [Chemical Formula 14]

[0126]

[0127] In the above chemical formulas 13 and 14,

[0128] The dotted lines mean the parts that form the condensation;

[0129] R 15 to R 18 Each is independently a substituent represented by the following Chemical Formula 15;

[0130] [Chemical Formula 15]

[0131]

[0132] In the above chemical formula 15,

[0133] * means the part that forms the bond;

[0134] L5 and L6 are each independently selected from a single bond, C6 to C 18 A group consisting of an arylene group and a heteroarylene group having 5 to 18 atomic nuclei;

[0135] R 19 Selected from hydrogen, deuterium, halogen, cyano, nitro, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C3~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 or combined with adjacent groups to form an aromatic ring with 5 to 50 atomic nuclei, a non-aromatic condensed polycyclic ring with 5 to 50 atomic nuclei, an aromatic heterocyclic ring with 5 to 50 atomic nuclei, or a non-aromatic condensed heteropolycyclic ring with 5 to 50 atomic nuclei;

[0136] The arylene and heteroarylene groups of L5 and L6, the R 19 The alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamino, alkylsilyl, alkylsulfonyl, arylsulfonyl, alkylboryl, arylboryl, arylphosphyl, mono- or diarylphosphino, alkylcarbonyl, arylcarbonyl and arylsilyl groups, and aromatic rings, non-aromatic condensed polycyclic rings, aromatic heterocyclic rings and non-aromatic condensed heteropolycyclic rings formed by two adjacent substituents are each independently selected from deuterium, halogen, cyano, nitro, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C6~C 60 Aryloxy, C1~C 40 Alkoxy, C6~C 60 Arylamine, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C1~C 40 Alkylsilyl, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 The arylsilyl group may be substituted with or unsubstituted with one or more substituents. When substituted with a plurality of substituents, they may be the same as or different from each other.

[0137] According to a preferred embodiment of the present invention, in the rings represented by the above chemical formulas 13 and 14, R 15 and R 16 、R 16 and R 17 , and R 17 and R 18 One or more of the groups can independently form a condensed ring with the ring represented by the following Chemical Formula 16:

[0138] [Chemical Formula 16]

[0139]

[0140] In the above chemical formula 16,

[0141] The dotted lines mean the parts that form the condensation;

[0142] R 20 to R 23 Each is independently a substituent represented by the following Chemical Formula 17;

[0143] [Chemical Formula 17]

[0144]

[0145] In the above chemical formula 17,

[0146] * means the part that forms the bond;

[0147] L7 and L8 are each independently selected from a single bond, C6 to C 18 A group consisting of an arylene group and a heteroarylene group having 5 to 18 atomic nuclei;

[0148] R 24 Selected from hydrogen, deuterium, halogen, cyano, nitro, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C3~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 A group consisting of an arylamine group;

[0149] The arylene and heteroarylene groups of L7 and L8, and the R 24The alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamine, alkylsilyl, alkylsulfonyl, arylsulfonyl, alkylboryl, arylboryl, arylphosphyl, mono- or diarylphosphino, alkylcarbonyl, arylcarbonyl and arylsilyl groups are each independently selected from deuterium, halogen, cyano, nitro, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C6~C 60 Aryloxy, C1~C 40 Alkoxy, C6~C 60 Arylamine, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C1~C 40 Alkylsilyl, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 The arylsilyl group may be substituted with or unsubstituted with one or more substituents. When substituted with a plurality of substituents, they may be the same as or different from each other.

[0150] According to a preferred embodiment of the present invention, in the ring represented by the chemical formula 8, R8 and R9 are independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C3~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C1~C 40 Alkyl boron, C6~C 60Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 A group consisting of an arylamine group;

[0151] The alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamino, alkylsilyl, alkylboryl, arylboryl, arylphosphoryl, mono- or diarylphosphino, alkylcarbonyl, arylcarbonyl and arylsilyl groups of R8 and R9 are each independently selected from deuterium, halogen, cyano, nitro, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C6~C 60 Aryloxy, C1~C 40 Alkoxy, C6~C 60 Arylamine, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C1~C 40 Alkylsilyl, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 The arylsilyl group may be substituted with or unsubstituted with one or more substituents. When substituted with a plurality of substituents, they may be the same as or different from each other.

[0152] According to a preferred embodiment of the present invention, the ring represented by the above Chemical Formula 8 can be represented by the following Chemical Formula 18:

[0153] [Chemical Formula 18]

[0154]

[0155] In the above chemical formula 18,

[0156] The dotted lines mean the parts that form the condensation;

[0157] R25 to R 29 Each is independently a substituent represented by the following Chemical Formula 15;

[0158] [Chemical Formula 15]

[0159]

[0160] In the above chemical formula 15,

[0161] * means the part that forms the bond;

[0162] L5 and L6 are each independently selected from a single bond, C6 to C 18 A group consisting of an arylene group and a heteroarylene group having 5 to 18 atomic nuclei;

[0163] R 19 Selected from hydrogen, deuterium, halogen, cyano, nitro, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C3~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 or combined with adjacent groups to form an aromatic ring with 5 to 50 atomic nuclei, a non-aromatic condensed polycyclic ring with 5 to 50 atomic nuclei, an aromatic heterocyclic ring with 5 to 50 atomic nuclei, or a non-aromatic condensed heteropolycyclic ring with 5 to 50 atomic nuclei;

[0164] The arylene and heteroarylene groups of L5 and L6, the R 19The alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamino, alkylsilyl, alkylsulfonyl, arylsulfonyl, alkylboryl, arylboryl, arylphosphyl, mono- or diarylphosphino, alkylcarbonyl, arylcarbonyl and arylsilyl groups, and aromatic rings, non-aromatic condensed polycyclic rings, aromatic heterocyclic rings and non-aromatic condensed heteropolycyclic rings formed by two adjacent substituents are each independently selected from deuterium, halogen, cyano, nitro, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C6~C 60 Aryloxy, C1~C 40 Alkoxy, C6~C 60 Arylamine, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C1~C 40 Alkylsilyl, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 The arylsilyl group may be substituted with or unsubstituted with one or more substituents. When substituted with a plurality of substituents, they may be the same as or different from each other.

[0165] According to a preferred embodiment of the present invention, in the ring represented by the above chemical formula 9, any one of X5 and X6 is a single bond, and the other one is O, N, C(Ar2)(Ar3), S, Si(Ar4)(Ar5) or P(=O)(Ar6);

[0166] wherein the above Ar2 to Ar6 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60Aryloxy, C3~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 A group consisting of an arylamine group;

[0167] The alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamino, alkylsilyl, alkylsulfonyl, arylsulfonyl, alkylboryl, arylboryl, arylphosphino, mono- or diarylphosphino, alkylcarbonyl, arylcarbonyl and arylsilyl groups of Ar2 to Ar6 are each independently selected from deuterium, halogen, cyano, nitro, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C6~C 60 Aryloxy, C1~C 40 Alkoxy, C6~C 60 Arylamine, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C1~C 40 Alkylsilyl, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 The arylsilyl group may be substituted with or unsubstituted with one or more substituents. When substituted with a plurality of substituents, they may be the same as or different from each other.

[0168] According to a preferred embodiment of the present invention, the ring represented by the above Chemical Formula 9 can be represented by the following Chemical Formula 19 or 20:

[0169] [Chemical Formula 19]

[0170]

[0171] [Chemical Formula 20]

[0172]

[0173] In the above chemical formulas 19 and 20,

[0174] The dotted lines mean the parts that form the condensation;

[0175] X5 is O, N, C(Ar2)(Ar3), S, Si(Ar4)(Ar5) or P(=O)(Ar6);

[0176] The above Ar2 to Ar6 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C3~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 A group consisting of an arylamine group;

[0177] The alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamino, alkylsilyl, alkylsulfonyl, arylsulfonyl, alkylboryl, arylboryl, arylphosphino, mono- or diarylphosphino, alkylcarbonyl, arylcarbonyl and arylsilyl groups of Ar2 to Ar6 are each independently selected from deuterium, halogen, cyano, nitro, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C6~C60 aryl, heteroaryl with 5 to 60 atomic nuclei, C6~C 60 Aryloxy, C1~C 40 Alkoxy, C6~C 60 Arylamine, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C1~C 40 Alkylsilyl, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 The arylsilyl group is substituted or unsubstituted with one or more substituents, and when substituted with multiple substituents, they are the same or different from each other;

[0178] R 30 to R 41 Each is independently a substituent represented by the following Chemical Formula 15;

[0179] [Chemical Formula 15]

[0180]

[0181] In the above chemical formula 15,

[0182] * means the part that forms the bond;

[0183] L5 and L6 are each independently selected from a single bond, C6 to C 18 A group consisting of an arylene group and a heteroarylene group having 5 to 18 atomic nuclei;

[0184] R 19 Selected from hydrogen, deuterium, halogen, cyano, nitro, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C3~C 40 Alkylsilyl, C6~C 60Aryl silyl, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 or combined with adjacent groups to form an aromatic ring with 5 to 50 atomic nuclei, a non-aromatic condensed polycyclic ring with 5 to 50 atomic nuclei, an aromatic heterocyclic ring with 5 to 50 atomic nuclei, or a non-aromatic condensed heteropolycyclic ring with 5 to 50 atomic nuclei;

[0185] The arylene and heteroarylene groups of L5 and L6, the R 19 The alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamino, alkylsilyl, alkylsulfonyl, arylsulfonyl, alkylboryl, arylboryl, arylphosphyl, mono- or diarylphosphino, alkylcarbonyl, arylcarbonyl and arylsilyl groups, and aromatic rings, non-aromatic condensed polycyclic rings, aromatic heterocyclic rings and non-aromatic condensed heteropolycyclic rings formed by two adjacent substituents are each independently selected from deuterium, halogen, cyano, nitro, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C6~C 60 Aryloxy, C1~C 40 Alkoxy, C6~C 60 Arylamine, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C1~C 40 Alkylsilyl, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60The arylsilyl group may be substituted with or unsubstituted with one or more substituents. When substituted with a plurality of substituents, they may be the same as or different from each other.

[0186] According to a preferred embodiment of the present invention, the compound represented by the above Chemical Formula 1 can be represented by the following Chemical Formula 21:

[0187] [Chemical Formula 21]

[0188]

[0189] In the above chemical formula 21,

[0190] L9 is selected from a single bond, C6~C 18 A group consisting of an arylene group and a heteroarylene group having 5 to 18 atomic nuclei;

[0191] X1 to X4 are each the same as defined in claim 1, but two X1 to X4 may be the same as or different from each other.

[0192] According to a preferred embodiment of the present invention, L1 to L8 are each independently selected from the group consisting of phenylene, biphenylene, naphthyl, quinazolinyl, carbazolyl and fluorenyl.

[0193] According to a preferred embodiment of the present invention, each of L1 to L8 can be independently a linking group represented by any one of the following chemical formulas A-1 to A-6:

[0194]

[0195] In the above chemical formulas A-1 to A-6,

[0196] * means the part that forms the bond;

[0197] p is an integer from 0 to 4;

[0198] A1 is selected from deuterium, halogen, cyano, nitro, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C3~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkylsulfonyl, C6~C 60Arylsulfonyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 When there are multiple A1, they are the same or different from each other;

[0199] Z1 to Z8 are each independently N or C(Ar8);

[0200] In the above chemical formula A-3, any one of Z1 to Z4 and any one of Z5 to Z8 that form a bond as a linking group is C(Ar8), and in this case, the above Ar8 is absent;

[0201] In the above chemical formula A-4, any two of Z1 to Z4 that form a bond as a linking group are C(Ar8), and in this case, the above Ar8 is absent;

[0202] X8 is each independently O, S, N(Ar9) or C(Ar 10 )(Ar 11 );

[0203] X9 is N or C(Ar 12 );

[0204] Ar8 to Ar 12 Each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C3~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 When the above Ar8 is multiple, they are the same or different from each other;

[0205] The above A1 and Ar8 to Ar 12 The alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamine, alkylsilyl, alkylsulfonyl, arylsulfonyl, alkylboryl, arylboryl, arylphosphyl, mono- or diarylphosphino, alkylcarbonyl, arylcarbonyl and arylsilyl groups are each independently selected from deuterium, halogen, cyano, nitro, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C6~C 60 Aryloxy, C1~C 40 Alkoxy, C6~C 60 Arylamine, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C1~C 40 Alkylsilyl, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 The arylsilyl group may be substituted with or unsubstituted with one or more substituents. When substituted with a plurality of substituents, they may be the same as or different from each other.

[0206] According to a preferred embodiment of the present invention, the above R1, R3, R 14 、R 19 and R 24 Any one of C2~C 40 Alkenyl, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C3~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C1~C 40Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 A group consisting of arylamine groups,

[0207] The above R1, R3, R 14 、R 19 and R 24 The alkenyl, aryl, heteroaryl, arylamine, alkylsilyl, alkylsulfonyl, arylsulfonyl, alkylboryl, arylboryl, arylphosphino, mono- or diarylphosphino, alkylcarbonyl, arylcarbonyl and arylsilyl groups are each independently selected from halogen, cyano, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C6~C 60 The present invention may be substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group having 5 to 60 atomic nuclei and a heteroaryl group having 5 to 60 atomic nuclei. When substituted with multiple substituents, they may be the same as or different from each other.

[0208] According to a preferred embodiment of the present invention, at least one of the above R1 and R3 is independently selected from C2 to C 40 Alkenyl, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C3~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 A group consisting of arylamine groups,

[0209] The alkenyl, aryl, heteroaryl, arylamino, alkylsilyl, alkylsulfonyl, arylsulfonyl, alkylboryl, arylboryl, arylphosphino, mono- or diarylphosphino, alkylcarbonyl, arylcarbonyl and arylsilyl groups of R1 and R3 are each independently selected from halogen, cyano, C1-C 40 Alkyl, C2~C40 Alkenyl, C2~C 40 Alkynyl, C6~C 60 The present invention may be substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group having 5 to 60 atomic nuclei and a heteroaryl group having 5 to 60 atomic nuclei. When substituted with multiple substituents, they may be the same as or different from each other.

[0210] According to a preferred embodiment of the present invention, the above R 14 Choose from C2~C 40 Alkenyl, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C3~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 A group consisting of arylamine groups,

[0211] The above R 14 The alkenyl, aryl, heteroaryl, arylamine, alkylsilyl, alkylsulfonyl, arylsulfonyl, alkylboryl, arylboryl, arylphosphino, mono- or diarylphosphino, alkylcarbonyl, arylcarbonyl and arylsilyl groups are each independently selected from halogen, cyano, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C6~C 60 The present invention may be substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group having 5 to 60 atomic nuclei and a heteroaryl group having 5 to 60 atomic nuclei. When substituted with multiple substituents, they may be the same as or different from each other.

[0212] According to a preferred embodiment of the present invention, the above R 19 Choose from C2~C 40 Alkenyl, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C3~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C1~C 40Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 A group consisting of arylamine groups,

[0213] The above R 19 The alkenyl, aryl, heteroaryl, arylamine, alkylsilyl, alkylsulfonyl, arylsulfonyl, alkylboryl, arylboryl, arylphosphino, mono- or diarylphosphino, alkylcarbonyl, arylcarbonyl and arylsilyl groups are each independently selected from halogen, cyano, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C6~C 60 The present invention may be substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group having 5 to 60 atomic nuclei and a heteroaryl group having 5 to 60 atomic nuclei. When substituted with multiple substituents, they may be the same as or different from each other.

[0214] According to a preferred embodiment of the present invention, the above R 24 Choose from C2~C 40 Alkenyl, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C3~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 A group consisting of arylamine groups,

[0215] The above R 24 The alkenyl, aryl, heteroaryl, arylamine, alkylsilyl, alkylsulfonyl, arylsulfonyl, alkylboryl, arylboryl, arylphosphino, mono- or diarylphosphino, alkylcarbonyl, arylcarbonyl and arylsilyl groups are each independently selected from halogen, cyano, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40Alkynyl, C6~C 60 The present invention may be substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group having 5 to 60 atomic nuclei and a heteroaryl group having 5 to 60 atomic nuclei. When substituted with multiple substituents, they may be the same as or different from each other.

[0216] According to a preferred embodiment of the present invention, the above R1, R3, R 14 、R 19 and R 24 At least one of them can be independently a substituent represented by any one of Chemical Formulas B-1 to B-7:

[0217]

[0218] In the above chemical formulas B-1 to B-7,

[0219] * means the part that forms the bond;

[0220] Z9 to Z 13 Each independently is N or C(Ar 13 );

[0221] In the above chemical formula B-4, Z9 to Z 12 Any one of them is C(Ar 13 ), at this time, the above Ar 13 does not exist;

[0222] T1 and T2 are each independently selected from a single bond, C(Ar 14 )(Ar 15 )、N(Ar 16 ), O, S, S(=O)(=0), B(Ar 17 ) and Si(Ar 18 )(Ar 19 ), but T1 and T2 are not single bonds at the same time;

[0223] T3 is N(Ar 20 ) or O;

[0224] q and r are each independently an integer from 0 to 4;

[0225] A2 and A3 are each independently selected from deuterium, halogen, cyano, nitro, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C60 Aryloxy, C3~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 When A2 and A3 are plural in number, they are the same as or different from each other;

[0226] B1 and Ar 13 to Ar 20 Each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C3~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 When the above Ar 13 to Ar 19 When each is plural, they are the same as or different from each other;

[0227] A2, A3, B1 and Ar 13 to Ar 20The alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamine, alkylsilyl, alkylsulfonyl, arylsulfonyl, alkylboryl, arylboryl, arylphosphyl, mono- or diarylphosphino, alkylcarbonyl, arylcarbonyl and arylsilyl groups are each independently selected from deuterium, halogen, cyano, nitro, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C6~C 60 Aryloxy, C1~C 40 Alkoxy, C6~C 60 Arylamine, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C1~C 40 Alkylsilyl, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphoryl, C6~C 60 Mono- or diarylphosphino, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 The arylsilyl group may be substituted with or unsubstituted with one or more substituents. When substituted with a plurality of substituents, they may be the same as or different from each other.

[0228] The compound represented by Chemical Formula 1 of the present invention can be represented by the following compounds, but is not limited thereto:

[0229]

[0230]

[0231]

[0232] The compound of Chemical Formula 1 of the present invention can be synthesized according to conventional synthesis methods (see Chem. Rev., 60:313 (1960); J. Chem. Soc. 4482 (1955); Chem. Rev. 95:2457 (1995)). The detailed synthesis process of the compound of the present invention will be described in detail in the synthesis examples described below.

[0233] 2. Organic electroluminescent elements

[0234] On the other hand, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by Chemical Formula 1 of the present invention.

[0235] Specifically, the present invention provides an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises the compound represented by Chemical Formula 1. These compounds may be used alone or in combination of two or more.

[0236] The one or more organic layers may be any one or more of a hole injection layer, a hole transport layer, a light-emitting layer, a light-emitting auxiliary layer, a lifespan improvement layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, wherein at least one organic layer may contain the compound represented by the above Chemical Formula 1.

[0237] The structure of the organic electroluminescent element of the present invention is not particularly limited. As an example, refer to Figure 1 , for example, comprising an anode 10 and a cathode 20 facing each other, and an organic layer 30 located between the anode 10 and the cathode 20. The organic layer 30 may include a hole transport layer 31, a light-emitting layer 32, and an electron transport layer 34. In addition, a hole transport auxiliary layer 33 may be included between the hole transport layer 31 and the light-emitting layer 32, and an electron transport auxiliary layer 35 may be included between the electron transport layer 34 and the light-emitting layer 32.

[0238] As another example of the present invention, refer to Figure 2 The organic layer 30 may further include a hole injection layer 37 between the hole transport layer 31 and the anode 10 , and may further include an electron injection layer 36 between the electron transport layer 34 and the cathode 20 .

[0239] In the present invention, the hole injection layer 37 stacked between the above-mentioned hole transport layer 31 and the anode 10 is a layer that not only improves the interface characteristics between the ITO used as the anode and the organic substance used as the hole transport layer 31, but also is coated on the upper part of the ITO with an uneven surface to play the role of making the surface of the ITO flat. As long as it is a substance commonly used in this field, it can be used without special restrictions. For example, amine compounds can be used, but it is not limited to this.

[0240] In addition, the above-mentioned electron injection layer 36 is a layer stacked on the upper part of the electron transport layer and plays the function of facilitating the injection of electrons from the cathode and ultimately improving power efficiency. As long as it is a substance commonly used in this field, it can be used without special restrictions. For example, LiF, Liq, NaCl, CsF, Li2O, BaO and other substances can be used.

[0241] In addition, although not shown in the figure, in the present invention, a further luminescence-assisting layer may be included between the hole-transport-assisting layer 33 and the luminescent layer 32. The luminescence-assisting layer serves to transport holes to the luminescent layer 32 and can also serve to adjust the thickness of the organic layer 30. The luminescence-assisting layer may contain a hole-transporting substance and may be formed of the same substance as the hole-transporting layer 31.

[0242] In addition, although not shown in the figure, a lifetime improvement layer may be further included between the electron-transport assisting layer 35 and the light-emitting layer 32. Holes that cross the ionization potential level in the organic light-emitting element and migrate toward the light-emitting layer 32 are blocked by the high energy barrier of the lifetime improvement layer, preventing them from diffusing or migrating toward the electron-transporting layer. This confinement of holes within the light-emitting layer prevents them from diffusing toward the electron-transporting layer, where electrons migrate due to reduction. This prevents lifetime reduction caused by irreversible oxidative decomposition reactions and helps improve the lifespan of the organic light-emitting element.

[0243] In the present invention, the EWG (electron-pulling group) characteristics of the compound represented by the above-mentioned chemical formula 1 are excellent. Compared with the six-membered heterocyclic structure known in the past, it is not only electrochemically stable and has excellent electron mobility, but also has a high glass transition temperature and excellent thermal stability. Thus, the electron transport ability and luminescent properties of the compound represented by the chemical formula 1 of the present invention are excellent, and therefore it can be used as a material for any layer of the organic layer of the organic electroluminescent element, i.e., the hole injection layer, the hole transport layer, the light-emitting layer, the electron transport layer and the electron injection layer. It is preferably a material that can be used as any layer of the light-emitting layer, the electron transport layer and the electron transport auxiliary layer stacked on the electron transport layer, and more preferably a material that can be used as an electron transport layer or an electron transport auxiliary layer.

[0244] In addition, when the compound of the present invention is used as a light-emitting layer material, specifically, the compound represented by the above chemical formula 1 can be used as a phosphorescent host, fluorescent host or doping material of the light-emitting layer, preferably as a phosphorescent host (blue, green and / or red phosphorescent host material).

[0245] Furthermore, in the present invention, the organic electroluminescent element may not only include an anode, one or more organic layers, and a cathode stacked in sequence as described above, but may also further include an insulating layer or an adhesive layer at the interface between the electrode and the organic layer.

[0246] The organic electroluminescent element of the present invention is formed in such a way that at least one of the above-mentioned organic layers (for example, the electron transport auxiliary layer) contains the compound represented by the above-mentioned Chemical Formula 1. In addition, other organic layers and electrodes can be formed and manufactured using materials and methods known in the art.

[0247] The organic layer may be formed by vacuum deposition or solution coating, such as spin coating, dip coating, doctor blade coating, inkjet printing, or thermal transfer, but is not limited thereto.

[0248] The substrate that can be used in the present invention is not particularly limited, and a silicon wafer, quartz, a glass plate, a metal plate, a plastic film or sheet, or the like can be used.

[0249] In addition, as the anode material, for example, it can be formed of a conductor with a high work function to facilitate hole injection, including metals such as vanadium, chromium, copper, zinc, 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 SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline; and carbon black, etc., but not limited to these.

[0250] In addition, as a cathode material, for example, it can be formed by a conductor with a low work function to facilitate electron injection, including metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead, or alloys thereof; and multilayer structure materials such as LiF / Al or LiO2 / Al, etc., but is not limited to these.

[0251] Hereinafter, the present invention will be described in detail by way of examples, which are as follows. However, the following examples are merely illustrative of the present invention and the present invention is not limited thereto.

[0252] [Preparation Example 1] Synthesis of A-1

[0253] <Step 1> Synthesis of [(1-isoquinolylamino)thioxomethyl]-ethyl ester (9CI)

[0254]

[0255] Add 10 mL of dichloromethane to isoquinolin-1-amine (1.44 g, 10 mmol). Cool to 0°C, and slowly add ethoxycarbonyl isothiocyanate (1.31 g, 10 mmol) dropwise over 15 minutes. Warm the reaction mixture to room temperature and stir for 20 hours. Remove the solvent by vacuum distillation and filter. After drying with warm air, 2.47 g of the title compound (90% yield) was obtained.

[0256] 1 H-NMR: δ1.26(t,3H),4.18(q,2H),7.08(d,1H),7.43(t,1H),7.60(m,2H),8.30(m,2H),11.46(s,1H),12.41(s,1H)

[0257] <Step 2> Synthesis of [1,2,4]triazolo[5,1-a]isoquinolin-2-amine

[0258]

[0259] A mixed solvent of EtOH / MeOH (1:1, 20 mL) was added to hydroxylamine hydrochloride (2.77 g, 40 mmol). Triethylamine (3.03 g, 30 mmol) was added to the reaction solution and stirred for 1 hour. [(1-isoquinolylamino)thioxomethyl]-, ethyl ester (9CI) (2.75 g, 10 mmol) was added and the temperature was slowly increased, and the mixture was heated under reflux for 3 hours. The temperature was cooled to room temperature and the generated solid was filtered. The obtained solid products were combined, washed with purified water, EtOH / MeOH mixed solvent and n-hexane, and dried with warm air to obtain the target compound [1,2,4]triazolo[5,1-a]isoquinolin-2-amine (1.65 g, yield 90%).

[0260] 1 H-NMR: δ6.31(s,1H),7.60(m,4H),7.99(d,1H),8.45(d,1H),7.97(s,1H),8.59(d,1H),8.98(t,1H)

[0261] <Step 3> Synthesis of A-1

[0262]

[0263] CuBr2 (0.67 g, 3 mmol) and THF 20 mL were added to [1,2,4]triazolo[5,1-a]isoquinolin-2-amine (1.84 g, 10 mmol). The reaction solution was cooled to 0°C, HBr 20 mL was slowly added, and NaNO2 (1.72 g, 25 mmol) was dissolved in purified water 10 mL and then slowly added dropwise. The reaction solution was stirred at room temperature for 12 hours. 10 mL of sodium hydroxide aqueous solution was added to the reaction solution, and after stirring for 1 hour, the mixture was extracted with E.A 50 mL and then washed with distilled water. The obtained organic layer was dried over anhydrous MgSO4, distilled under reduced pressure and purified by silica gel column chromatography to obtain the target compound A-1 (1.48 g, yield 60%).

[0264] 1 H-NMR: δ7.60(m,4H),7.99(d,1H),8.45(d,1H)

[0265] [Preparation Example 2] Synthesis of A-2

[0266]

[0267] The same procedure as in [Preparation Example 1] was carried out except that isoquinolin-3-amine (1.44 g, 10 mmol) was used as a reactant instead of isoquinolin-1-amine to obtain the target compound A-2 (1.46 g, yield 59%).

[0268] 1 H-NMR: δ7.45(m,2H),7.64(m,2H),8.11(d,1H),9.15(s,1H)

[0269] [Preparation Example 3] Synthesis of A-3

[0270]

[0271] The same procedure as in [Preparation Example 1] was carried out except that quinolin-2-amine (1.44 g, 10 mmol) was used as a reactant instead of isoquinolin-1-amine to obtain the target compound A-3 (1.43 g, yield 58%).

[0272] 1H-NMR: δ7.69(t,1H),7.85(m,2H),8.09(m,2H),8.29(d,1H)

[0273] [Preparation Example 4] Synthesis of A-4

[0274]

[0275] The same procedure as in [Preparation Example 1] was carried out except that phenanthridin-6-amine (1.94 g, 10 mmol) was used as a reactant instead of isoquinolin-1-amine to obtain the target compound A-4 (1.69 g, yield 57%).

[0276] 1H-NMR: δ7.63(m,3H),7.84(m,2H),7.99(d,1H),8.10(m,2H)

[0277] [Preparation Example 5] Synthesis of A-5

[0278]

[0279] The same procedure as in [Preparation Example 1] was carried out except that 4-bromoisoquinolin-1-amine (2.23 g, 10 mmol) was used instead of isoquinolin-1-amine as a reactant to obtain the target compound A-5 (1.83 g, yield 56%).

[0280] 1 H-NMR: δ7.63(t,1H),7.90(m,3H),8.74(s,1H)

[0281] [Preparation Example 6] Synthesis of A-6

[0282]

[0283] The same procedure as in [Preparation Example 1] was carried out except that 4-bromophenanthridin-6-amine (2.73 g, 10 mmol) was used as a reactant instead of isoquinolin-1-amine to obtain the target compound A-6 (2.07 g, yield 55%).

[0284] 1 H-NMR: δ7.43(t,1H),7.61(m,2H),7.83(d,1H),7.99(d,1H),8.01(d,1H),8.37(d,1H)

[0285] [Preparation Example 7] Synthesis of A-7

[0286]

[0287] The same procedure as in [Preparation Example 1] was carried out except that 1,6-naphthyridin-5-amine (1.45 g, 10 mmol) was used as a reactant instead of isoquinolin-1-amine to obtain the target compound A-7 (1.34 g, yield 54%).

[0288] 1 H-NMR: δ7.46(t,1H),7.70(d,1H),8.23(d,1H),8.78(d,1H),9.14(d,1H)

[0289] [Preparation Example 8] Synthesis of A-8

[0290]

[0291] The same procedure as in [Preparation Example 1] was carried out except that 7-bromoquinoxaline-2-amine (2.24 g, 10 mmol) was used as a reactant instead of isoquinolin-1-amine to obtain the target compound A-8 (1.73 g, yield 53%).

[0292] 1 H-NMR: δ7.56(d,1H),7.85(d,1H),8.24(s,1H),8.74(s,1H)

[0293] [Preparation Example 9] Synthesis of A-9

[0294]

[0295] As a reactant, except that 9-chloro-2-methylbenzo[h][1,6]naphthyridin-5-amine (2.43 g, 10 mmol) was used instead of isoquinolin-1-amine, the same process as [Preparation Example 1] was carried out to obtain the target compound A-9 (1.80 g, yield 52%).

[0296] 1 H-NMR: δ2.76(s,3H),7.35(d,1H),7.66(s,1H),7.98(m,2H),8.22(d,1H)

[0297] [Preparation Example 10] Synthesis of A-10

[0298]

[0299] The same procedure as in [Preparation Example 1] was carried out except that 1-phenyl-1H-imidazo[4,5-c]quinolin-4-amine (2.60 g, 10 mmol) was used as a reactant instead of isoquinolin-1-amine to obtain the target compound A-10 (1.85 g, yield 51%).

[0300] 1 H-NMR: δ7.15(s,1H),7.40(m,4H),7.62(t,1H),7.85(m,2H),8.08(d,1H),8.36(d,1H)

[0301] [Preparation Example 11] Synthesis of A-11

[0302]

[0303] As a reactant, 9-phenyl-9H-pyrimido[4,5-b]indol-4-amine (2.60 g, 10 mmol) was used instead of isoquinolin-1-amine, and the same process as [Preparation Example 1] was carried out to obtain the target compound A-11 (1.82 g, yield 50%).

[0304] 1 H-NMR: δ7.16(t,1H),7.35(t,1H),7.60(m,5H),7.94(d,1H),8.55(d,1H),9.54(s,1H)

[0305] [Preparation Example 12] Synthesis of A-12

[0306]

[0307] The same procedure as in [Preparation Example 1] was carried out except that 2-(pyridin-3-yl)furo[3,2-c]pyridin-4-amine (2.11 g, 10 mmol) was used as a reactant instead of isoquinolin-1-amine to obtain the target compound A-12 (1.60 g, yield 51%).

[0308] 1 H-NMR: δ6.56(s,1H),7.57(t,1H),7.86(d,1H),8.42(d,1H),8.59(d,1H),8.70(d,1H),9.24(s,1H)

[0309] [Preparation Example 13] Synthesis of A-13

[0310]

[0311] The same procedure as in [Preparation Example 1] was carried out except that 3-bromothieno[3,2-c]pyridin-4-amine (2.29 g, 10 mmol) was used as a reactant instead of isoquinolin-1-amine to obtain the target compound A-13 (1.73 g, yield 52%).

[0312] 1 H-NMR: δ7.38(d,1H),8.55(m,2H)

[0313] [Preparation Example 14] Synthesis of A-14

[0314]

[0315] The same procedure as in [Preparation Example 1] was carried out except that 11H-indeno[1,2-c]isoquinolin-5-amine (2.32 g, 10 mmol) was used as a reactant instead of isoquinolin-1-amine to obtain the target compound A-14 (1.78 g, yield 53%).

[0316] 1 H-NMR: δ3.81(s,2H),7.27(t,1H),7.38(m,2H),7.59(t,1H),7.70(t,1H),8.00(m,3H)

[0317] [Synthesis Example 1] Synthesis of J-1

[0318]

[0319] Under a nitrogen flow, A-1 (2.48 g, 10 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)-1,3,5-triazine (4.35 g, 10 mmol), Pd(OAc)2 (0.11 g, 5 mol%), Xphos (0.47 g, 2 mmol), Cs2CO3 (6.51 g, 20 mmol), and toluene / EtOH / H2O (80 ml / 40 ml / 20 ml) were mixed and stirred at 110°C for 6 hours. After completion of the reaction, the mixture was extracted with dichloromethane, and MgSO4 was added and filtered. The solvent of the filtered organic layer was removed, and the target compound J-1 (2.57 g, 54% yield) was obtained by column chromatography.

[0320] [LCMS]: 476

[0321] [Synthesis Example 2] Synthesis of J-2

[0322]

[0323] A-2 (2.48 g, 10.0 mmol) was used instead of A-1, and 2,4-diphenyl-6-(3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-[1,1'-biphenyl]-3-yl)-1,3,5-triazine (5.11 g, 10.0 mmol) was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)-1,3,5-triazine. Except for this, the same process as in Synthesis Example 1 was carried out to obtain the target compound J-2 (3.03 g, yield 55%).

[0324] [LCMS]: 552

[0325] [Synthesis Example 3] Synthesis of J-3

[0326]

[0327] A-3 (2.48 g, 10.0 mmol) was used instead of A-1, and 10-phenyl-2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-10H-spiro[acridine-9,9'-fluorene] (5.33 g, 10.0 mmol) was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)-1,3,5-triazine. Except for this, the same process as in Synthesis Example 1 was carried out to obtain the target compound J-3 (3.21 g, yield 56%).

[0328] [LCMS]: 574

[0329] [Synthesis Example 4] Synthesis of J-4

[0330]

[0331] A-4 (2.98 g, 10.0 mmol) was used instead of A-1, and 2-([1,1'-biphenyl]-4-yl)-4-(4-fluorophenyl)-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)pyrimidine (5.28 g, 10.0 mmol) was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)-1,3,5-triazine. Except for this, the same process as in Synthesis Example 1 was carried out to obtain the target compound J-4 (3.53 g, yield 57%).

[0332] [LCMS]: 619

[0333] [Synthesis Example 5] Synthesis of J-5

[0334]

[0335] A-5 (3.26 g, 10.0 mmol) was used instead of A-1, and 4,4,5,5-tetramethyl-2-(4-(1,2,2-triphenylvinyl)phenyl)-1,3,2-dioxaborolane (9.16 g, 20.0 mmol) was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)-1,3,5-triazine. Except for this, the same process as in Synthesis Example 1 was carried out to obtain the target compound J-5 (4.81 g, yield 58%).

[0336] [LCMS]: 830

[0337] [Synthesis Example 6] Synthesis of J-6

[0338]

[0339] A-6 (3.77 g, 10.0 mmol) was used instead of A-1, and 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (8.68 g, 20.0 mmol) was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine. Except for this, the same process as in Synthesis Example 1 was carried out to obtain the target compound J-6 (4.90 g, yield 59%).

[0340] [LCMS]: 831

[0341] [Synthesis Example 7] Synthesis of J-7

[0342]

[0343] A-7 (2.49 g, 10.0 mmol) was used instead of A-1, and (3-(triphenyl-2-yl)phenyl)boric acid (3.48 g, 10.0 mmol) was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)-1,3,5-triazine. Except for this, the same process as in Synthesis Example 1 was carried out to obtain the target compound J-7 (2.83 g, yield 60%).

[0344] [LCMS]: 472

[0345] [Synthesis Example 8] Synthesis of J-8

[0346]

[0347] A-8 (3.27 g, 10.0 mmol) was used instead of A-1, and (4-(diphenylamino)phenyl)boric acid (5.78 g, 20.0 mmol) was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)-1,3,5-triazine. Except for this, the same process as in Synthesis Example 1 was carried out to obtain the target compound J-8 (3.87 g, yield 59%).

[0348] [LCMS]: 656

[0349] [Synthesis Example 9] Synthesis of J-9

[0350]

[0351] A-9 (3.47 g, 10.0 mmol) was used instead of A-1, and (9-phenyl-9H-carbazole-3-yl)boric acid (5.74 g, 20.0 mmol) was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)-1,3,5-triazine. Except for this, the same process as in Synthesis Example 1 was carried out to obtain the target compound J-9 (4.15 g, yield 58%).

[0352] [LCMS]: 716

[0353] [Synthesis Example 10] Synthesis of J-10

[0354]

[0355] Under a nitrogen stream, A-10 (3.64 g, 10 mmol), 9-phenyl-9H,9'H-3,3'-dicarbazole (4.08 g, 10 mmol), Pd(OAc)2 (0.11 g, 5 mol%), P(t-Bu)3 (0.20 g, 1 mmol), NaO(t-Bu) (1.92 g, 20 mmol), and toluene (200 ml) were mixed and stirred at 110°C for 12 hours. After completion of the reaction, the mixture was extracted with dichloromethane, and then MgSO4 was added and filtered. After removing the solvent from the obtained organic layer, the target compound J-10 (3.94 g, 57% yield) was obtained by column chromatography.

[0356] [LCMS]: 691

[0357] [Synthesis Example 11] Synthesis of J-11

[0358]

[0359] A-11 (3.64 g, 10.0 mmol) was used instead of A-10, and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluorene-2-amine (3.61 g, 10.0 mmol) was used instead of 9-phenyl-9H,9'H-3,3'-dicarbazole. Except for this, the same process as in Synthesis Example 10 was carried out to obtain the target compound J-11 (3.61 g, yield 56%).

[0360] [LCMS]: 644

[0361] [Synthesis Example 12] Synthesis of J-12

[0362]

[0363] A-12 (3.15 g, 10.0 mmol) was used instead of A-1, and diphenyl (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)phosphine oxide (4.04 g, 10.0 mmol) was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine. Except for this, the same process as in Synthesis Example 1 was carried out to obtain the target compound J-12 (2.81 g, yield 55%).

[0364] [LCMS]: 512

[0365] [Synthesis Example 13] Synthesis of J-13

[0366]

[0367] A-13 (3.33 g, 10.0 mmol) was used instead of A-1, and 4-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)quinazoline (6.64 g, 20.0 mmol) was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)-1,3,5-triazine. Except for this, the same process as in Synthesis Example 1 was carried out to obtain the target compound J-13 (3.15 g, yield 54%).

[0368] [LCMS]: 583

[0369] [Synthesis Example 14] Synthesis of J-14

[0370]

[0371] A-14 (3.36 g, 10.0 mmol) was used instead of A-1, and 2-(9,9'-spirobi[fluorene]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.42 g, 10.0 mmol) was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)-1,3,5-triazine. Except for this, the same process as in Synthesis Example 1 was carried out to obtain the target compound J-14 (3.02 g, yield 53%).

[0372] [LCMS]: 571

[0373] [Examples 1 to 7] Preparation of blue organic electroluminescent elements

[0374] Compounds J-1 to 7 synthesized in the synthesis examples were purified by sublimation to high purity by a commonly known method, and then blue organic electroluminescent devices were prepared as follows.

[0375] First, we will A glass substrate coated with a thin film of indium tin oxide (ITO) was ultrasonically cleaned with distilled water. After the distilled water wash, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a UV OZONE cleaning machine (Power sonic 405, HwashinTech) for 5 minutes using UV light. The substrate was then transferred to a vacuum deposition machine.

[0376] On the ITO transparent electrode prepared as above, DS-205 (Doosan Electronics, 80nm) / NPB (15nm) / ADN+5% DS-405 (Doosan Electronics, 30nm) / compounds J-1 to 7 (30nm) / LiF (1nm) / Al (200nm) were sequentially vapor-deposited to produce an organic electroluminescent element.

[0377] [Comparative Example 1] Preparation of a blue organic electroluminescent element

[0378] A blue organic electroluminescent element was produced in the same manner as in Example 1 except that Alq3 was used as the electron transport layer material instead of Compound J-1.

[0379] [Comparative Example 2] Preparation of a blue organic electroluminescent element

[0380] A blue organic electroluminescent device was produced in the same manner as in Example 1 except that Compound J-1 was not used as the electron transport layer material.

[0381] The structures of NPB, AND, and Alq3 used in Examples 1 to 7 and Comparative Examples 1 and 2 are as follows.

[0382]

[0383] [Evaluation Example 1]

[0384] The current density of the blue organic electroluminescent devices prepared in Examples 1 to 7 and Comparative Examples 1 and 2 was measured at 10 mA / cm 2 The driving voltage, current efficiency, and emission wavelength at the time of irradiation are shown in the following Table 1.

[0385] [Table 1]

[0386]

[0387] As shown in Table 1 above, it can be seen that the blue organic electroluminescent element using the compound of the present invention for the electron transport layer (Examples 1 to 7) shows excellent performance in terms of driving voltage, luminescence peak and current efficiency compared with the previous blue organic electroluminescent element using Alq3 for the electron transport layer (Comparative Example 1) and the blue organic electroluminescent element without an electron transport layer (Comparative Example 2).

[0388] [Examples 8 to 14] Preparation of blue organic electroluminescent elements

[0389] Compounds J-8 to 14 synthesized in the synthesis examples were purified by sublimation to high purity using a commonly known method, and then blue organic electroluminescent devices were prepared according to the following process.

[0390] First, we will A glass substrate coated with a thin film of indium tin oxide (ITO) was ultrasonically cleaned with distilled water. After the distilled water wash, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a UV OZONE cleaning machine (Power sonic 405, HwashinTech) for 5 minutes using UV light. The substrate was then transferred to a vacuum deposition machine.

[0391] On the ITO transparent electrode prepared as above, DS-205 (Doosan Electronics, 80 nm) / NPB (15 nm) / ADN+5% DS-405 (Doosan Electronics, 30 nm) / Compound J-8~14 (5 nm) / Alq3 (25 nm) / LiF (1 nm) / Al (200 nm) were sequentially deposited to produce an organic electroluminescent element.

[0392] [Comparative Example 3] Preparation of a blue organic electroluminescent element

[0393] A blue organic electroluminescent device was produced in the same manner as in Example 8, except that Compound J-8 was not used as the electron transport assisting layer material and Alq3 was deposited in a thickness of 30 nm instead of 25 nm.

[0394] [Evaluation Example 2]

[0395] The current density of the organic electroluminescent devices manufactured in Examples 8 to 14 and Comparative Example 3 was measured at 10 mA / cm 2 The driving voltage, emission wavelength, and current efficiency at the time of irradiation are shown in Table 2 below.

[0396] [Table 2]

[0397]

[0398] As shown in Table 2 above, it can be seen that the blue organic electroluminescent elements (Examples 8 to 14) using the compounds of the present invention as electron transport assisting layers show excellent performance in current efficiency, luminescence peak and driving voltage compared with the blue organic electroluminescent element without an electron transport assisting layer (Comparative Example 3).

[0399] Industrial applicability

[0400] The present invention can provide a novel organic compound that can be used as a material for an organic electroluminescent device and an organic electroluminescent device containing the same.

Claims

1. A compound represented by any one of the following chemical formulas 5 and 6: [Chemical Formula 5] [Chemical Formula 6] In the chemical formulas 5 and 6, R1 and R4 to R6 are each independently a substituent represented by the following Chemical Formula 2; [Chemical Formula 2] In the chemical formula 2, * means the part that forms the bond; The L1 and L2 are each independently selected from the group consisting of a single bond, a phenylene group, a biphenylene group, a naphthyl group, a quinazolinyl group, a carbazolyl group and a fluorenyl group, R3 is selected from hydrogen, deuterium, halogen, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C6~C 60 Arylphosphoryl, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 or combined with adjacent groups to form an aromatic ring with 5 to 50 atomic nuclei, a non-aromatic condensed polycyclic ring with 5 to 50 atomic nuclei, an aromatic heterocyclic ring with 5 to 50 atomic nuclei, or a non-aromatic condensed heteropolycyclic ring with 5 to 50 atomic nuclei; The alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamino, alkylsulfonyl, arylsulfonyl, arylphosphoryl, alkylcarbonyl, arylcarbonyl, and the aromatic ring, non-aromatic condensed polycyclic, aromatic heterocyclic and non-aromatic condensed heteropolycyclic formed by the combination of two adjacent R3 are independently selected from deuterium, halogen, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C6~C 60 Aryloxy, C1~C 40 Alkoxy, C6~C 60 Arylamine, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 Arylphosphoryl, C1~C 40 Alkyl carbonyl, C6~C 60 The arylcarbonyl group is substituted or unsubstituted with one or more substituents. When substituted with multiple substituents, they are the same or different from each other. The group of R4 and R5, and R5 and R6 each independently forms a condensed ring with a ring represented by any one of the following chemical formulas 10, 13, and 14: [Chemical Formula 10] [Chemical Formula 13] [Chemical Formula 14] In the chemical formula 10, The dotted lines mean the parts that form the condensation; Y1 is N or C(Ar1); X7 is O, NH or S; Ar1 and R8 are each independently selected from hydrogen, deuterium, halogen, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C6~C 60 Arylphosphoryl, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 A group consisting of an arylamine group; The alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamino, alkylsulfonyl, arylsulfonyl, arylphosphoryl, alkylcarbonyl, arylcarbonyl of Ar1 and R8 are independently selected from deuterium, halogen, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C6~C 60 Aryloxy, C1~C 40 Alkoxy, C6~C 60 Arylamine, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C6~C 60 Arylphosphoryl, C1~C 40 Alkyl carbonyl, C6~C 60 The arylcarbonyl group is substituted or unsubstituted with one or more substituents. When substituted with multiple substituents, they are the same or different from each other. In the chemical formulas 13 and 14, The dotted lines mean the parts that form the condensation; R 15 to R 18 Each independently selected from hydrogen, deuterium, halogen, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C6~C 60 Arylphosphoryl, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 A group consisting of an arylamine group; R 15 to R 18 The alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamino, alkylsulfonyl, arylsulfonyl, arylphosphoryl, alkylcarbonyl, arylcarbonyl are each independently selected from deuterium, halogen, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C6~C 60 Aryloxy, C1~C 40 Alkoxy, C6~C 60 Arylamine, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C6~C 60 Arylphosphoryl, C1~C 40 Alkyl carbonyl, C6~C 60 The arylcarbonyl group may be substituted with or unsubstituted with one or more substituents. When substituted with a plurality of substituents, they may be the same as or different from each other.

2. The compound according to claim 1, wherein At least one of R1 and R3 is independently selected from C2 to C 40 Alkenyl, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkylsulfonyl, C6~C 60 Arylsulfonyl, C6~C 60 Arylphosphoryl, C1~C 40 Alkyl carbonyl, C6~C 60 Arylcarbonyl and C6~C 60 The alkenyl, aryl, heteroaryl, arylamine, alkylsulfonyl, arylsulfonyl, arylphosphoryl, alkylcarbonyl, arylcarbonyl of R1 and R3 are independently selected from halogen, cyano, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C6~C 60 The present invention may be substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group having 5 to 60 atomic nuclei and a heteroaryl group having 5 to 60 atomic nuclei. When substituted with multiple substituents, they may be the same as or different from each other.

3. A compound selected from the group consisting of:

4. An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) one or more organic layers between the anode and the cathode, in, At least one of the one or more organic layers comprises the compounds represented by Chemical Formulas 5 and 6 according to claim 1 .

5. The organic electroluminescent element according to claim 4, wherein The organic layer containing the compound is selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron transport auxiliary layer, an electron injection layer, a lifespan improvement layer, a light emitting layer, and a light emitting auxiliary layer.

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