Organic electroluminescent compounds and organic electroluminescent devices

Abstract

We provide organic electroluminescent compounds and organic electroluminescent devices. [Solution] This disclosure relates to an organic electroluminescent device comprising: a first electrode; a second electrode facing the first electrode; a light-emitting layer between the first electrode and the second electrode; and a hole transport band between the light-emitting layer and the second electrode, wherein the hole transport band comprises a compound represented by formula 1, and the light-emitting layer comprises compounds represented by formulas 2 and 3. The organic electroluminescent device according to this disclosure can exhibit a low drive voltage and / or high current efficiency by using compounds represented by formulas 1, 2 and 3.

Description

[Technical Field]

[0001] This disclosure relates to organic electroluminescent compounds and organic electroluminescent devices. [Background technology]

[0002] Electroluminescent devices (EL devices) are self-emissive display devices that offer advantages in terms of providing a wider viewing angle, a higher contrast ratio, and a faster response time. In 1987, Eastman Kodak developed the first organic EL device by using low molecular weight aromatic diamine molecules and aluminum complexes as materials for forming the emissive layer (see Non-Patent Literature 1).

[0003] Organic electroluminescent devices are composed of a multilayer structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer to improve their efficiency and stability. In this specification, the selection of compounds included in the hole transport layer, etc., is recognized as one means of improving device characteristics such as hole transport efficiency to the light-emitting layer, light emission efficiency, and lifetime.

[0004] Various materials or concepts have been proposed for the hole transport layer of organic electroluminescent devices to improve luminescence efficiency, drive voltage, and / or lifetime. However, these have not been satisfactory in practical applications. Therefore, there has always been a need to develop organic electroluminescent devices with improved performance compared to previously disclosed devices, such as improved drive voltage, luminescence efficiency, power efficiency, and / or lifetime characteristics. [Prior art documents] [Patent Documents]

[0005] [Patent Document 1] Korean Patent Application Publication No. 2017-0022865 Specification [Patent Document 2] Korean Patent Application Publication No. 2018-0099487 Specification [Patent Document 3] Korean Patent Application Publication No. 2021-0124018 Specification [Patent Document 4] Korean Patent Application Publication No. 2021-0006283 Specification [Patent Document 5] Korean Patent No. 10-2283849 Specification [Patent Document 6] Korean Patent No. 10-1427457 Specification [Non-patent literature]

[0006] [Non-Patent Document 1] Appl.Phys.Lett.51,913,1987 [Overview of the project] [Problems that the invention aims to solve]

[0007] The object of this disclosure is, firstly, to provide an organic electroluminescent compound effective for manufacturing organic electroluminescent devices with improved drive voltage and / or current efficiency, and secondly, to provide an organic electroluminescent device with improved drive voltage and / or current efficiency. [Means for solving the problem]

[0008] As a result of intensive research to solve the above technical problems, the inventors have found that the aforementioned objective can be achieved by an organic electroluminescent device comprising: a first electrode; a second electrode facing the first electrode; a light-emitting layer between the first electrode and the second electrode; and a hole transport zone between the first electrode and the light-emitting layer, wherein the hole transport zone comprises a compound represented by the following formula 1, and the light-emitting layer comprises a compound represented by the following formula 2 and a compound represented by the following formula 3, thus completing the present invention. [ka]

[0009] In Formula 1, X is -(CR9R 30 , 30 , 30 ) n -; R1 to R8 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30 )alkyl, substituted or unsubstituted (C6-C 30 )aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (C1-C 30 )alkoxy, substituted or unsubstituted tri(C1-C 30 )alkylsilyl, substituted or unsubstituted di(C1-C 30 )alkyl(C6-C 30 )arylsilyl, substituted or unsubstituted (C1-C 30 )alkyldi(C6-C 30 )arylsilyl, substituted or unsubstituted tri(C6-C 30 )arylsilyl, (C3-C 30 )aliphatic ring and (C6-C 30 )aromatic ring substituted or unsubstituted condensed ring, substituted or unsubstituted mono- or di(C1-C 30 )alkylamino, substituted or unsubstituted mono- or di(C6-C 30 )arylamino, substituted or unsubstituted (C1-C 30 )alkyl(C6-C 30 )arylamino, substituted or unsubstituted mono- or di(3-30 member) heteroarylamino, or substituted or unsubstituted (C6-C 30 )aryl(3-30 member) heteroarylamino; R9 and R 10 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30 )alkyl, substituted or unsubstituted (C6-C 30 )aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C​)Cycloalkyl, substituted or unsubstituted mono or di(C1~C 30 ) Alkylamino, substituted or unsubstituted mono or di(C6~C 30 ) Arylamino, substituted or unsubstituted (C1~C 30 ) Alkyl (C6~C 30 )arylamino, substituted or unsubstituted mono or di(3-30 member) heteroarylamino, or substituted or unsubstituted (C6-C 30 ) represents an aryl (3-30 member) heteroarylamino; or it may be bonded to adjacent substituents to form a ring, However, R1~R 10 At least one of them is expressed by the following equation A: [ka] During the ceremony, L, L1, and L2 are each independently single bonds, substituted, or unsubstituted (C6~C 30 ) Arylene, substituted or unsubstituted (3-30 member) heteroarylene, or substituted or unsubstituted (C3-C 30 ) Represents cycloalkylene, Ar1 and Ar2 are independently hydrogen, deuterium, substituted or unsubstituted (C6~C 30 )aryl, substituted or unsubstituted (3-30 member) heteroaryl, or substituted or unsubstituted (C3-C 30 ) Represents cycloalkyl, However, at least one of Ar1 and Ar2 must be substituted or unsubstituted (C3~C 30 ) Provided that it is a cycloalkyl; n is an integer of 1 or 2, and if n is 2, R9 and R 10 Each of these may be the same or different.

[0010] [ka] In Equation 2, L 11 ~L 13Each of these can be independently single-bonded, substituted, or unsubstituted (C6~C 30 ) represents arylene or substituted or unsubstituted (3-30 member) heteroarylene; Ar 11 is either substitution or non-substitution (C6~C 30 ) Represents an aryl or a substituted or unsubstituted (3-30 member) heteroaryl; Ar 12 and Ar 13 These are, independently, hydrogen, deuterium, substituted or unsubstituted (C1~C 30 ) alkyl, substituted or unsubstituted (C6~C 30 ) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C 30 )Cycloalkyl, substituted or unsubstituted (C1~C 30 ) alkoxy, substituted or unsubstituted tri(C1~C30)alkylsilyl, substituted or unsubstituted di(C1~C 30 ) Alkyl (C6~C 30 ) Arylsilyl, substituted or unsubstituted (C1~C 30 ) Alkyl di(C6~C 30 ) Arylsilyl, substituted or unsubstituted tri(C6~C 30 ) Arylsilyl, substituted or unsubstituted mono or di(C1~C 30 ) Alkylamino, substituted or unsubstituted mono or di(C2~C 30 ) Alkenylamino, substituted or unsubstituted (C1~C 30 ) Alkyl (C2~C 30 ) Alkenylamino, substituted or unsubstituted mono or di(C6~C 30 ) Arylamino, substituted or unsubstituted (C1~C 30 ) Alkyl (C6~C 30 ) Arylamino, substituted or unsubstituted mono or di(3-30 member) heteroarylamino, substituted or unsubstituted (C1-C 30 ) Alkyl (3-30 member) heteroarylamino, substituted or unsubstituted (C2-C 30 ) Alkenil (C6~C 30 ) Arylamino, substituted or unsubstituted (C2~C 30) Alkenyl (3-30 member) heteroarylamino, or substituted or unsubstituted (C6-C 30 ) represents an aryl (3-30 member) heteroarylamino.

[0011] [ka] In Equation 3, X1 to X3 are each independently N or CR 21 This represents the following, provided that at least one of X1 to X3 is N; Each R 21 These are independently hydrogen, deuterium, halogens, cyano, substituted or unsubstituted (C1-C) 30 ) alkyl, substituted or unsubstituted (C6~C 30 ) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C 30 )Cycloalkyl, substituted or unsubstituted (C1~C 30 ) alkoxy, substituted or unsubstituted tri(C1~C 30 ) Alkylsilyl, substituted or unsubstituted di(C1~C 30 ) Alkyl (C6~C 30 ) Arylsilyl, substituted or unsubstituted (C1~C 30 ) Alkyl di(C6~C 30 ) Arylsilyl, substituted or unsubstituted tri(C6~C 30 ) Arylsilyl, or (C3~C 30 ) aliphatic ring and (C6~C 30 ) Represents a substituted or unsubstituted fused ring with an aromatic ring; L 21 ~L 23 Each of these can be independently single-bonded, substituted, or unsubstituted (C6~C 30 ) represents arylene, or substituted or unsubstituted (3-30 member) heteroarylene; Ar 21 ~Ar 23 These are, independently, hydrogen, deuterium, substituted or unsubstituted (C1~C 30 ) alkyl, substituted or unsubstituted (C3~C 30)Cycloalkyl, substituted or unsubstituted (3-7 member) heterocycloalkyl, (C3-C 30 ) aliphatic ring and (C6-C 30 ) substituted or unsubstituted fused ring of aromatic ring, substituted or unsubstituted (C6-C 30 ) aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted tri (C1-C 30 ) alkylsilyl, substituted or unsubstituted di (C1-C 30 ) alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 ) alkyldi (C6-C 30 ) arylsilyl, or substituted or unsubstituted tri (C6-C 30 ) represents arylsilyl.

[0012] In addition, the inventors have found that the above object can be achieved by an organic electroluminescent compound represented by the following formula 1' and containing at least one deuterium, and completed the present invention.

Chemical formula

[0013] In formula 1', X is -CR9R 10 -; R1 to R8 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C6-C 30 ) aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C 30 ) cycloalkyl, substituted or unsubstituted (C1-C 30 ) alkoxy, substituted or unsubstituted tri (C1-C 30 ) alkylsilyl, substituted or unsubstituted di (C1-C 30 ) alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 ) alkyldi (C6-C 30) Arylsilyl, substituted or unsubstituted tri(C6~C 30 ) Arylsilyl, (C3~C 30 ) aliphatic ring and (C6~C 30 ) A substituted or unsubstituted condensed ring with an aromatic ring, a substituted or unsubstituted mono or di(C1~C 30 ) Alkylamino, substituted or unsubstituted mono or di(C6~C 30 ) Arylamino, substituted or unsubstituted (C1~C 30 ) Alkyl (C6~C 30 )arylamino, substituted or unsubstituted mono or di(3-30 member) heteroarylamino, or substituted or unsubstituted mono(C6-C 30 ) Represents an aryl (3-30 member) heteroarylamino; R9 and R 10 These are, independently, hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C) 30 ) alkyl, substituted or unsubstituted (C6~C 30 ) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C 30 )Cycloalkyl, substituted or unsubstituted mono or di(C1~C 30 ) Alkylamino, substituted or unsubstituted mono or di(C6~C 30 ) Arylamino, substituted or unsubstituted (C1~C 30 ) Alkyl (C6~C 30 )arylamino, substituted or unsubstituted mono or di(3-30 member) heteroarylamino, or substituted or unsubstituted (C6-C 30 ) represents an aryl (3-30 member) heteroarylamino; or it may be bonded to adjacent substituents to form a ring, However, R1~R 10 At least one of them is expressed by the following equation A: [ka] During the ceremony, L, L1, and L2 are each independently single bonds, substituted, or unsubstituted (C6~C 30) Arylene, substituted or unsubstituted (3-30 member) heteroarylene, or substituted or unsubstituted (C3-C 30 ) Represents cycloalkylene; Ar1 and Ar2 are independently hydrogen, deuterium, substituted or unsubstituted (C6~C 30 )aryl, substituted or unsubstituted (3-30 member) heteroaryl, or substituted or unsubstituted (C3-C 30 ) Represents cycloalkyl, However, at least one of Ar1 and Ar2 must be substituted or unsubstituted (C3~C 30 ) The condition is that it is a cycloalkyl compound.

[0014] Furthermore, the inventors have discovered that the aforementioned objectives can be achieved by an organic electroluminescent compound represented by the following formula 4, and have completed the present invention. [ka]

[0015] In Equation 4, X4 is -CR 49 R 50 -and; R 41 ~R 50 These are, independently, hydrogen, halogen, cyano, substituted or unsubstituted (C1-C) 30 ) alkyl, substituted or unsubstituted (C6~C 30 ) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C 30 )Cycloalkyl, substituted or unsubstituted mono or di(C1~C 30 ) Alkylamino, substituted or unsubstituted mono or di(C6~C 30 ) Arylamino, substituted or unsubstituted (C1~C 30 ) Alkyl (C6~C 30 )arylamino, substituted or unsubstituted mono or di(3-30 member) heteroarylamino, or substituted or unsubstituted (C6-C 30) represents an aryl (3-30 member) heteroarylamino; or it may be bonded to adjacent substituents to form a ring, However, R 41 ~R 48 At least one of them is expressed by the following equation B: [ka] During the ceremony, L3 and L4 are independently single bonds, substituted or unsubstituted (C6~C 30 ) Arylene, substituted or unsubstituted (3-30 member) heteroarylene, or substituted or unsubstituted (C3-C 30 ) Represents cycloalkylene; Ar3 and Ar4 can each be independently hydrogen, substituted, or unsubstituted (C6~C 30 )aryl, substituted or unsubstituted (3-30 member) heteroaryl, or substituted or unsubstituted (C3-C 30 ) Represents cycloalkyl, However, at least one of Ar3 and Ar4 must be substituted or unsubstituted (C3~C 30 ) Provided that it is a cycloalkyl; R 51 ~R 54 These are, independently, hydrogen, halogen, cyano, substituted or unsubstituted (C1-C) 30 ) alkyl, substituted or unsubstituted (C6~C 30 ) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C 30 )Cycloalkyl, substituted or unsubstituted mono or di(C1~C 30 ) Alkylamino, substituted or unsubstituted mono or di(C6~C 30 ) Arylamino, substituted or unsubstituted (C1~C 30 ) Alkyl (C6~C 30 )arylamino, substituted or unsubstituted mono or di(3-30 member) heteroarylamino, or substituted or unsubstituted (C6-C 30 )It is an aryl (3-30 member) heteroarylamino; However, R 41~R 54 L3, L4, Ar3, and Ar4 are provided to be deuterium-free.

[0016] Effects of the invention By incorporating the organic electroluminescent compound according to this disclosure, it is possible to provide an organic electroluminescent device with improved drive voltage and / or current efficiency. [Modes for carrying out the invention]

[0017] The present disclosure will be described in detail below. However, the following description is intended to illustrate the present invention and is not intended to limit its scope.

[0018] This disclosure relates to an organic electroluminescent device comprising: a first electrode; a second electrode facing the first electrode; a light-emitting layer between the first electrode and the second electrode; and a hole transport zone between the first electrode and the light-emitting layer, wherein the hole transport zone comprises a compound represented by formula 1, and the light-emitting layer comprises a compound represented by formula 2 and a compound represented by formula 3.

[0019] This disclosure relates to an organic electroluminescent device represented by formula 1' and containing at least one deuterium.

[0020] In addition, this disclosure relates to an organic electroluminescent compound represented by Formula 4.

[0021] As used in this disclosure, the term “organic electroluminescent compound” means a compound that may be used in an organic electroluminescent device and, if necessary, may be included in any of the layers constituting the organic electroluminescent device.

[0022] As used in this disclosure, the term “organic electroluminescent material” means a material that can be used in an organic electroluminescent device and may contain at least one compound. The organic electroluminescent material may, as necessary, be included in any of the layers constituting the organic electroluminescent device. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light emission auxiliary material, an electron blocking material, a light emission material (including a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc. The hole transport band material may be at least one selected from the group consisting of a hole transport material, a hole injection material, an electron blocking material, a hole auxiliary material, and a light emission auxiliary material.

[0023] The organic electroluminescent materials of this disclosure may comprise at least one compound represented by Formula 1. The compound of Formula 1 may be, but is not limited to, comprise at least one layer comprising an organic electroluminescent device and at least one layer comprising a hole transport band. When the compound of Formula 1 is comprised of a hole transport layer, hole auxiliary layer, electron blocking layer, light-emitting layer, or light-emitting auxiliary layer, it may be comprised as a hole transport material, hole auxiliary material, electron blocking material, host material, or light-emitting auxiliary material.

[0024] As used in this disclosure, “electron transport band” means a band through which electrons move between the light-emitting layer and the cathode. For example, the electron transport band may include a hole blocking layer, an electron transport layer, and an electron injection layer, preferably at least one of the electron transport layer and the electron injection layer. The hole blocking layer functions to prevent holes from entering the cathode through the light-emitting layer in the operation of an organic electroluminescent device.

[0025] As used in this disclosure, the term “hole transport zone” means a zone through which holes move between the first electrode and the light-emitting layer. For example, a hole transport zone may include at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, and an electron blocking layer. Each of the hole injection layer, hole transport layer, hole auxiliary layer, light-emitting auxiliary layer, and electron blocking layer may be a single layer or a multilayer of two or more layers or three or more layers stacked together. According to one embodiment of this disclosure, a hole transport zone may include a first hole transport layer and a second hole transport layer, and may further include a third hole transport layer. The second and third hole transport layers may be at least one of a plurality of hole transport layers and may include at least one of a hole auxiliary layer, a light-emitting auxiliary layer, and an electron blocking layer. In addition, according to another embodiment of the present disclosure, the hole transport band may include a first hole transport layer and a second hole transport layer, the first hole transport layer may be located between a first electrode and a light-emitting layer, the second hole transport layer may be located between the first hole transport layer and a light-emitting layer, and the second hole transport layer may function as a hole transport layer, a light-emitting auxiliary layer, a hole auxiliary layer, and / or an electron blocking layer. According to yet another embodiment of the present disclosure, the hole transport band may include a first hole transport layer, a second hole transport layer, and a third hole transport layer, wherein the first hole transport layer may be located between a first electrode and a light-emitting layer, the second hole transport layer may be located between the first hole transport layer and a light-emitting layer, and the third hole transport layer may be located between the second hole transport layer and a light-emitting layer, and the third hole transport layer may be a layer that functions as a hole transport layer, a light-emitting auxiliary layer, a hole auxiliary layer, and / or an electron blocking layer.

[0026] In this disclosure, the term "(C1~C 30 "Alkyl" means a linear or branched alkyl group having 1 to 30 carbon atoms that make up the chain, in which case the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10. Specific examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and tert-butyl.

[0027] In this disclosure, the term "(C3~C 30 "Cycloalkyl" refers to a component of a saturated or partially unsaturated monocyclic or polycyclic cyclic hydrocarbon, meaning a monocyclic or polycyclic hydrocarbon having 3 to 30 carbon atoms in its ring skeleton, preferably 3 to 20, more preferably 3 to 7. Examples of cycloalkyls include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. Non-limiting examples of monocyclic cycloalkyls include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexenyl, cyclohexadienyl, cycloheptyl, cycloheptatrienyl, and cyclooctyl. Polycyclic cycloalkyls include spiro-rings, fused rings, and cross-linked rings. Cycloalkyl rings can be fused to aryl, heteroaryl, or heterocycloalkyl rings, and non-limiting examples of cycloalkyl rings include indanyl, tetrahydronaphthalenyl, and benzocycloheptenyl. The cycloalkyl of the crosslinking ring may contain one or more double bonds, but none of the rings have a fully conjugated π-electron system, and it means a 5-20 member, preferably 6-14 member, more preferably 7-10 member all-carbon polycyclic group having any two rings that share two carbon atoms that are not directly bonded. Depending on the number of rings formed, it can be classified as a bicyclic, tricyclic, tetracyclic, or polycyclic crosslinking cycloalkyl, preferably bicyclic, tricyclic, or tetracyclic, more preferably bicyclic or tricyclic. Examples of cycloalkyl of the crosslinking ring include adamantyl, norbornyl, norbornenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptanyl, and bicyclo[2.2.2]octyl.

[0028] In this disclosure, "(3-7 member) heterocycloalkyl" refers to a cycloalkyl having 3 to 7, preferably 5 to 7, ring skeleton atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably from the group consisting of O, S, and N. Examples of these include tetrahydrofuran, pyrrolidine, thiolane, and tetrahydropyran.

[0029] (C6~C 30"Aryl(ene)" is a monocyclic or fused ring group derived from an aromatic hydrocarbon having 6 to 30 carbon atoms in the ring skeleton, where the number of carbon atoms in the ring skeleton is preferably 6 to 25, more preferably 6 to 18, and may be partially saturated. The aryl may contain a spiro structure. Examples of aryls include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, dimethylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenantrenyl, phenylphenantrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracerenyl, perilenyl, crisenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, and the like. More specifically, examples of aryl compounds include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, 1-crisenyl, 2-crisenyl, 3-crisenyl, 4-crisenyl, 5-crisenyl, 6-crisenyl, benzo[c]phenanthryl, benzo[g]crisenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl Nyl, 9-Fluorenyl, Benzo[a]Fluorenyl, Benzo[b]Fluorenyl, Benzo[c]Fluorenyl, Dibenzofluorenyl, 2-Biphenyl, 3-Biphenyl, 4-Biphenyl, o-Terphenyl, m-Terphenyl-4-yl, m-Terphenyl-3-yl, m-Terphenyl-2-yl, p-Terphenyl-4-yl, p-Terphenyl-3-yl, p-Terphenyl-2-yl, m-Quaterphenyl, 3-Fluoranthenyl, 4-Fluoranthenyl, 8-Fluoranthenyl, 9-Fluoranthenyl, Benzofluoranthenyl, o-Tolyl, m-Tolyl, p-Tolyl, 2,3-Xylyl, 3,4-Xylyl, 2,5-Xylyl, Mesityl, o-Cumenyl, m-Cumenyl, p-Cumenyl, p-Tert-Butylphenyl, p-(2-Phenylpropyl)phenyl, 4'-Methylbiphenyl, 4"-Tert-Butyl-p-Terphenyl-4-yl, 9,9-Dimethyl-1-Fluorenyl, 9,9-Dimethyl-2-Fluorenyl, 9,9-Dimethyl-3-Fluorenyl, 9,9-Dimethyl-4-Fluorenyl, 9,9-Diphenyl-1-Fluorenyl, 9,9-Diphenyl-2-Fluorenyl, 9,9-Diphenyl-3-Fluorenyl, 9,9-Diphenyl-4- Fluorenyl, 11,11-dimethyl-1-benzo[a]fluorenyl, 11,11-dimethyl-2-benzo[a]fluorenyl, 11,11-dimethyl-3-benzo[a]fluorenyl, 11,11-dimethyl-4-benzo[a]fluorenyl, 11,11-dimethyl-5-benzo[a]fluorenyl, 11,11-dimethyl-6-benzo[a]fluorenyl, 11,11-dimethyl-7-benzo[a]fluorenyl, 11,11-dimethyl-8-benzo[a]fluorenyl, 11,11-dimethyl-9-benzo[a]fluorenyl, 11,11- Dimethyl-10-benzo[a]fluorenyl, 11,11-dimethyl-1-benzo[b]fluorenyl, 11,11-dimethyl-2-benzo[b]fluorenyl, 11,11-dimethyl-3-benzo[b]fluorenyl, 11,11-dimethyl-4-benzo[b]fluorenyl, 11,11-dimethyl-5-benzo[b]fluorenyl, 11,11-dimethyl-6-benzo[b]fluorenyl, 11,11-dimethyl-7-benzo[b]fluorenyl, 11,11-dimethyl-8-benzo[b]fluorenyl, 11,11-dimethyl-9-benzo[ [b]Fluorenyl, 11,11-dimethyl-10-benzo[b]Fluorenyl, 11,11-dimethyl-1-benzo[c]Fluorenyl, 11,11-dimethyl-2-benzo[c]Fluorenyl, 11,11-dimethyl-3-benzo[c]Fluorenyl, 11,11-dimethyl-4-benzo[c]Fluorenyl, 11,11-dimethyl-5-benzo[c]Fluorenyl, 11,11-dimethyl-6-benzo[c]Fluorenyl, 11,11-dimethyl-7-benzo[c]Fluorenyl, 11,11-dimethyl-8-benzo[c]Fluorenyl, 11,11-dimethyl-9-benzo[c]fluorenyl, 11,11-dimethyl-10-benzo[c]fluorenyl, 11,11-diphenyl-1-benzo[a]fluorenyl, 11,11-diphenyl-2-benzo[a]fluorenyl, 11,11-diphenyl-3-benzo[a]fluorenyl, 11,11-diphenyl-4-benzo[a]fluorenyl, 11,11-diphenyl-5-benzo[a]fluorenyl, 11,11-diphenyl-6-benzo[a]fluorenyl, 11,11-diphenyl-7-benzo[a]fluorenyl, 11,11-diphenyl Nyl-8-benzo[a]fluorenyl, 11,11-diphenyl-9-benzo[a]fluorenyl, 11,11-diphenyl-10-benzo[a]fluorenyl, 11,11-diphenyl-1-benzo[b]fluorenyl, 11,11-diphenyl-2-benzo[b]fluorenyl, 11,11-diphenyl-3-benzo[b]fluorenyl, 11,11-diphenyl-4-benzo[b]fluorenyl, 11,11-diphenyl-5-benzo[b]fluorenyl, 11,11-diphenyl-6-benzo[b]fluorenyl, 11,11-diphenyl-7 -Benzo[b]fluorenyl, 11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9-benzo[b]fluorenyl, 11,11-diphenyl-10-benzo[b]fluorenyl, 11,11-diphenyl-1-benzo[c]fluorenyl, 11,11-diphenyl-2-benzo[c]fluorenyl, 11,11-diphenyl-3-benzo[c]fluorenyl, 11,11-diphenyl-4-benzo[c]fluorenyl, 11,11-diphenyl-5-benzo[c]fluorenyl, 11,11-diphenyl-6-benzo [c]Fluorenyl, 11,11-diphenyl-7-benzo[c]Fluorenyl, 11,11-diphenyl-8-benzo[c]Fluorenyl, 11,11-diphenyl-9-benzo[c]Fluorenyl, 11,11-diphenyl-10-benzo[c]Fluorenyl, 9,9,10,10-tetramethyl-9,10-dihydro-1-phenanthryl, 9,9,10,10-tetramethyl-9,10-dihydro-2-phenanthryl, 9,9,10,10-tetramethyl-9,10-dihydro-3-phenanthryl, 9,9,10,10-tetramethyl-9,Examples include 10-dihydro-4-phenanthryl.

[0030] As used in this disclosure, the term "(3-30 member) heteroaryl(ene)" means an aryl(ene) having 3 to 30 ring skeleton atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, P, Se, Te, and Ge, which may be monocyclic or fused rings fused with at least one benzene ring, and may be partially saturated. The number of heteroatoms is preferably 1 to 4. Furthermore, heteroaryl(ene) in this disclosure may be formed by bonding at least one heteroaryl or aryl group to a heteroaryl(ene) group via a single bond, and may include a spiro structure.

[0031] Examples of heteroaryls include monocyclic heteroaryls such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetradinyl, triazolyl, tetrazolyl, flazanyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridadinyl, as well as benzofuranil, benzothiophenyl, isobenzofuranil, dibenzofuranil, benzophenanthrofuranil, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, and benzo Examples of condensed ring heteroaryls include phenanthrothiophenyl, benzoisoxazolyl, benzoxazolyl, phenanthroxazolyl, phenanthrothiazolyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphthilidinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthiazinyl, benzodioxolyl, and dihydroacridinyl. More specifically, examples of heteroaryls include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazine-4-yl, 1,2,4-triazine-3-yl, 1,3,5-triazine-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolidinyl, 2-indolidinyl, 3-indolidinyl, 5-indolidinyl, 6-indolidinyl, 7-indolidinyl, and 8-indolidinyl. Lu, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 3-pyridinyl, 4-pyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl,3-benzofuranil, 4-benzofuranil, 5-benzofuranil, 6-benzofuranil, 7-benzofuranil, 1-isobenzofuranil, 3-isobenzofuranil, 4-isobenzofuranil, 5-isobenzofuranil, 6-isobenzofuranil, 7-isobenzofuranil, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl Linyl, 6-Quinoxalinyl, 1-Carbazolyl, 2-Carbazolyl, 3-Carbazolyl, 4-Carbazolyl, 9-Carbazolyl, Azacarbazolyl-1-yl, Azacarbazolyl-2-yl, Azacarbazolyl-3-yl, Azacarbazolyl-4-yl, Azacarbazolyl-5-yl, Azacarbazolyl-6-yl, Azacarbazolyl-7-yl, Azacarbazolyl-8-yl, Azacarbazolyl-9-yl, 1-Phenantridinyl, 2-Phenantridinyl, 3-Phenantridinyl, 4-Phenantridinyl, 6-Phenantridinyl, 7-Phenantridinyl Phenantridinyl, 8-phenantridinyl, 9-phenantridinyl, 10-phenantridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-flazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrole-1-yl, 2-methylpyrrole-3-yl, 2-methylpyrrole-4-yl, 2-methylpyrrole-5-yl, 3-methylpyrrole-1-yl, 3-methylpyrrole-2-yl, 3-methylpyrrole-4-yl, 3-methylpyrrole-5-yl, 2-tert-butylpyrrole-4-yl, 3-(2-phenylpropyl)pyrrole-1-yl, 2-methyl-1-indolly, 4-methyl-1-indolly, 2-methyl-3-indolly, 4-methyl-3-indolly, 2-tert-butyl-1-indolly, 4-tert-butyl-1-indolly, 2-tert-butyl-3-indolly, 4-tert-butyl-3-indolly, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl,1-Dibenzothiophenyl, 2-Dibenzothiophenyl, 3-Dibenzothiophenyl, 4-Dibenzothiophenyl, 1-Naphtho[1,2-b]-Benzofuranyl, 2-Naphtho[1,2-b]-Benzofuranyl, 3-Naphtho[1,2-b]-Benzofuranyl, 4-Naphtho[1,2-b]-Benzofuranyl, 5-Naphtho[1,2-b]-Benzofuranyl, 6-Naphtho[1,2-b]-Benzofuranyl, 7-Naphtho[1,2-b]-Benzofuranyl, 8-Naphtho[1,2-b]-Benzofuranyl, 9-Naphtho[1,2-b]-Benzofuranyl, 10-Naphtho to[1,2-b]-benzofuranil, 1-naphtho[2,3-b]-benzofuranil, 2-naphtho[2,3-b]-benzofuranil, 3-naphtho[2,3-b]-benzofuranil, 4-naphtho[2,3-b]-benzofuranil, 5-naphtho[2,3-b]-benzofuranil, 6-naphtho[2,3-b]-benzofuranil, 7-naphtho[2,3-b]-benzofuranil, 8-naphtho[2,3-b]-benzofuranil, 9-naphtho[2,3-b]-benzofuranil, 10-naphtho[2,3-b]-benzofuranil, 1-naphtho[2,1-b]-benzofuranil Nyl, 2-naphtho[2,1-b]-benzofuranil, 3-naphtho[2,1-b]-benzofuranil, 4-naphtho[2,1-b]-benzofuranil, 5-naphtho[2,1-b]-benzofuranil, 6-naphtho[2,1-b]-benzofuranil, 7-naphtho[2,1-b]-benzofuranil, 8-naphtho[2,1-b]-benzofuranil, 9-naphtho[2,1-b]-benzofuranil, 10-naphtho[2,1-b]-benzofuranil, 1-naphtho[1,2-b]-benzothiophenyl, 2-naphtho[1,2-b]-benzothiophenyl, 3-naphtho[1 ,2-b]-benzothiophenyl, 4-naphtho[1,2-b]-benzothiophenyl, 5-naphtho[1,2-b]-benzothiophenyl, 6-naphtho[1,2-b]-benzothiophenyl, 7-naphtho[1,2-b]-benzothiophenyl, 8-naphtho[1,2-b]-benzothiophenyl, 9-naphtho[1,2-b]-benzothiophenyl, 10-naphtho[1,2-b]-benzothiophenyl, 1-naphtho[2,3-b]-benzothiophenyl, 2-naphtho[2,3-b]-benzothiophenyl, 3-naphtho[2,3-b]-benzothiophenyl,4-Naphtho[2,3-b]-benzothiophenyl, 5-Naphtho[2,3-b]-benzothiophenyl, 1-Naphtho[2,1-b]-benzothiophenyl, 2-Naphtho[2,1-b]-benzothiophenyl, 3-Naphtho[2,1-b]-benzothiophenyl, 4-Naphtho[2,1-b]-benzothiophenyl, 5-Naphtho[2,1-b]-benzothiophenyl, 6-Naphtho[2,1-b]-benzothiophenyl, 7-Naphtho[2,1-b]-benzothiophenyl, 8-Na Naphtho[2,1-b]-benzothiophenyl, 9-naphtho[2,1-b]-benzothiophenyl, 10-naphtho[2,1-b]-benzothiophenyl, 2-benzoflo[3,2-d]pyrimidinyl, 6-benzoflo[3,2-d]pyrimidinyl, 7-benzoflo[3,2-d]pyrimidinyl, 8-benzoflo[3,2-d]pyrimidinyl, 9-benzoflo[3,2-d]pyrimidinyl, 2-benzothio[3,2-d]pyrimidinyl, 6-benzothio[3,2-d]pyrimidinyl Nyl, 7-benzothio[3,2-d]pyrimidinyl, 8-benzothio[3,2-d]pyrimidinyl, 9-benzothio[3,2-d]pyrimidinyl, 2-benzoflo[3,2-d]pyradinyl, 6-benzoflo[3,2-d]pyradinyl, 7-benzoflo[3,2-d]pyradinyl, 8-benzoflo[3,2-d]pyradinyl, 9-benzoflo[3,2-d]pyradinyl, 2-benzothio[3,2-d]pyradinyl, 6-benzothio[3,2-d]pyradinyl, 7-ben Examples include zothio[3,2-d]pyrazinyl, 8-benzothio[3,2-d]pyrazinyl, 9-benzothio[3,2-d]pyrazinyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-germafluorenyl, 4-germafluorenyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, etc. Furthermore, "heteroaryl(enes)" can be classified into heteroaryl(enes) having electronic properties and heteroaryl(enes) having hole properties. Heteroaryl(enes) having electronic properties are substituents that are electron-rich compared to the parent nucleus, for example, substituted or unsubstituted pyridinyls, substituted or unsubstituted pyrimidinyls,These may be substituted or unsubstituted triazinyls, substituted or unsubstituted quinazolinyls, substituted or unsubstituted quinoxalinyls, substituted or unsubstituted quinolyls, etc. Hole-possessing heteroaryl(ene) substituents are electron-deficient substituents compared to the parent nucleus; for example, they may be substituted or unsubstituted carbazolyls, substituted or unsubstituted dibenzofuranyls, substituted or unsubstituted dibenzothiophenyls, etc. In this disclosure, the term "halogen" includes F, Cl, Br, and I.

[0032] As used in this specification, the term "(C3~C 30 ) aliphatic ring and (C6~C 30 The term "condensed ring with an aromatic ring" refers to the functional group of a ring formed by condensing at least one aliphatic ring having 3 to 30, preferably 3 to 25, more preferably 3 to 18 carbon atoms in its ring skeleton with at least one aromatic ring having 6 to 30, preferably 6 to 25, more preferably 6 to 18 carbon atoms in its ring skeleton. For example, the condensed ring may be a condensed ring of at least one benzene ring and at least one cyclohexane ring, or a condensed ring of at least one naphthalene ring and at least one cyclopentane ring, etc. In this specification, (C3~C 30 ) aliphatic ring and (C6~C 30 The carbon atoms in the fused ring with the aromatic ring can be replaced with at least one heteroatom selected from B, N, O, S, Si, and P, preferably N, O, and S.

[0033] In addition, "ortho-" ("o-"), "meta-" ("m-"), and "para-" ("p-") are prefixes that indicate the relative positions of substituents. The "ortho" configuration represents compounds with substituents adjacent to each other, for example, at positions 1 and 2 on benzene. The "meta" configuration represents compounds with substituents at the next substitution position after the directly adjacent substitution position, for example, at positions 1 and 3 of benzene. The "para" configuration represents compounds with substituents at the next substitution position after the meta position, for example, at positions 1 and 4 of benzene.

[0034] As used in this disclosure, the term “ring formed by bonding to adjacent substituents” means a substituted or unsubstituted 3- to 30-membered monocyclic or polycyclic aliphatic ring, aromatic ring, or combination thereof, formed by linking or condensing two or more adjacent substituents, preferably a substituted or unsubstituted 3- to 26-membered monocyclic or polycyclic aliphatic ring, aromatic ring, or combination thereof. Furthermore, the formed ring may contain at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably N, O, and S.

[0035] In addition, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a particular functional group is replaced by another atom or functional group, i.e., a substituent. Unless otherwise specified, substituents can replace hydrogen at any position where substitution is possible, and if two or more hydrogen atoms in a functional group are each replaced by substituents, the substituents may be the same or different. The maximum number of substituents that can be substituted for a given functional group may be the total number of valencies that can be substituted for each atom forming the functional group. In this specification, substituted alkyl, substituted aryl(ene), substituted heteroaryl(ene), substituted cycloalkyl(ene), substituted heterocycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, condensed ring of an fatty ring and an aromatic ring, substituted mono or dialkylamino, substituted mono or dialkenylamino, substituted alkylalkenylamino, substituted mono or diarylamino, substituted alkylarylamino, substituted alkylheteroarylamino, substituted alkenylarylamino, substituted alkenylheteroarylamino, substituted mono or diheteroarylamino, and substituted arylheteroarylamino are each independently deuterium, halogen, cyano, carboxy, nitro, hydroxy, (C1-C 30 ) Alkyl, Halo (C1~C 30 ) Alkyl, (C2~C 30 ) Alkenil, (C2~C 30 ) Alkinyl, (C1~C 30)alkoxy, (C1~C 30 ) alkylthio, (C3~C 30 )Cycloalkyl, (C3~C 30 )Cycloalkenyl, (3-7 member) heterocycloalkyl, (C6-C 30 ) Aryl oxy, (C6~C 30 ) Arylthio, (C6~C 30 (5-30 member) heteroaryls substituted with or unsubstituted with aryls, (5-30 member) heteroaryls substituted with or unsubstituted with (C6-C6) 30 )Aaryl, Tri (C1~C 30 ) Alkylsilyl, tri(C6~C 30 ) Arylsilyl, di(C1~C 30 ) Alkyl (C6~C 30 ) Arylsilyl, (C1~C 30 ) Alkyl di(C6~C 30 ) Arylsilyl, (C3~C 30 ) Fatty ring and (C6~C 30 ) A condensed ring with an aromatic ring, amino, mono or di(C1~C) 30 ) Alkylamino, substituted or unsubstituted mono or di(C6~C 30 ) Arylamino, (C1~C 30 ) Alkyl (C6~C 30 ) Arylamino, mono or di(3-30 member) heteroarylamino, (C1-C 30 )Alkyl (3-30 member) heteroarylamino, (C6-C 30 )aryl (3-30 member) heteroarylamino, (C1-C 30 ) Alkylcarbonyl, (C1~C 30 ) Alkoxycarbonyl, (C6~C 30 ) Arylcarbonyl, (C6~C 30 ) Arylphosfinyl, di(C6~C 30 ) Arylboronyl, di(C1~C 30 ) Alkylboronyl, (C1~C 30 ) Alkyl (C6~C 30 ) Arylboronyl, (C6~C 30 ) Alkyl (C1~C 30 ) alkyl, (C1~C 30) Alkyl (C6~C 30 ) are substituted with at least one selected from aryls and combinations thereof. According to one embodiment of the present disclosure, the substituted alkyls, etc., are each independently substituted with deuterium, cyano, (C1-C 30 ) alkyl, (C3~C 30 )Cycloalkyl, (C6~C 30 (5-30 member) heteroaryls substituted with or unsubstituted with aryls, (5-30 member) heteroaryls substituted with or unsubstituted with (C6-C6) 30 )aryl, substituted or unsubstituted mono or di(C6~C 30 ) may be substituted with at least one selected from the group consisting of arylaminos and combinations thereof. According to another embodiment of the present disclosure, the substituted alkyls, etc., may be independently deuterium, cyano, (C1-C 20 ) alkyl, (C3~C 20 )Cycloalkyl, (C6~C 20 (5-20 member) heteroaryls substituted with or unsubstituted with aryls, (5-20 member) heteroaryls substituted with or unsubstituted with (C6-C6) 20 )aryl, substituted or unsubstituted mono or di(C6~C 20 ) may be substituted with at least one selected from the group consisting of arylaminos and combinations thereof. For example, each substituted alkyl may be independently substituted with at least one selected from the group consisting of deuterium, cyano, methyl, deuterium-substituted or unsubstituted cyclohexyl, deuterium-substituted or unsubstituted phenyl, deuterium-substituted or unsubstituted naphthyl, biphenyl, phenantrenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, diphenylamino, carbazolyl, norbornyl, and adamantyl.

[0036] In this specification, if a substituent is not shown in the formula or compound structure, it may mean that all substituted positions are hydrogen or deuterium. That is, some hydrogen atoms may be deuterium, an isotope of hydrogen, where the deuterium content may range from 0% to 100%. In this specification, unless deuterium is explicitly excluded, such as when the deuterium content is 0%, the hydrogen content is 100%, or all substituents are explicitly stated as hydrogen, hydrogen and deuterium may coexist in the compound. Hydrogen can be represented as hydrogen-2, and its element symbol may also be D or 2 Deuterium, which can be represented as H, is an isotope of hydrogen and has a deuteron as its nucleus, consisting of one proton and one neutron. Isotopes refer to atoms with the same atomic number (Z) but different mass numbers (A), and can also be interpreted as elements that have the same number of protons but different numbers of neutrons.

[0037] The following describes an organic electroluminescent device according to one embodiment.

[0038] An organic electroluminescent device according to one embodiment includes a first electrode; a second electrode facing the first electrode; a light-emitting layer between the first electrode and the second electrode; and a hole transport zone between the first electrode and the light-emitting layer, wherein the hole transport zone contains a compound represented by the following formula 1. [ka]

[0039] In Equation 1, X is -(CR9R 10 ) n - is

[0040] In Equation 1, R1 to R8 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C 30 ) alkyl, substituted or unsubstituted (C6~C 30) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C 30 )Cycloalkyl, substituted or unsubstituted (C1~C 30 ) alkoxy, substituted or unsubstituted tri(C1~C 30 ) Alkylsilyl, substituted or unsubstituted di(C1~C 30 ) Alkyl (C6~C 30 ) Arylsilyl, substituted or unsubstituted (C1~C 30 ) Alkyl di(C6~C 30 ) Arylsilyl, substituted or unsubstituted tri(C6~C 30 ) Arylsilyl, (C3~C 30 ) aliphatic ring and (C6~C 30 ) A substituted or unsubstituted condensed ring with an aromatic ring, a substituted or unsubstituted mono or di(C1~C 30 ) Alkylamino, substituted or unsubstituted mono or di(C6~C 30 ) Arylamino, substituted or unsubstituted (C1~C 30 ) Alkyl (C6~C 30 )arylamino, substituted or unsubstituted mono or di(3-30 member) heteroarylamino, or substituted or unsubstituted (C6-C 30 ) represents an aryl (3-30 member) heteroarylamino. According to one embodiment of the present disclosure, R1 to R8 are each independently hydrogen, deuterium, substituted or unsubstituted (C6 to C 30 )aryl, substituted or unsubstituted mono or di(C6~C 30 ) Aryl, or substituted or unsubstituted (C6~C 30 )It may also be an aryl(3-30 member) heteroarylamino. According to another embodiment of the present disclosure, R1 to R8 may each independently be hydrogen, deuterium, phenyl, or be represented by the following formula A. [ka]

[0041] In formula A, L, L1, and L2 are each independently single bonds, substitutions, or non-substitutions (C6~C 30) Arylene, substituted or unsubstituted (3-30 member) heteroarylene, or substituted or unsubstituted (C3-C 30 ) represents a cycloalkylene. According to one embodiment of the present disclosure, L, L1 and L2 are each independently single bonds, substituted or unsubstituted (C6~C 30 ) may be arylene or substituted or unsubstituted (3-30 member) heteroarylene. According to another embodiment of the present disclosure, L, L1 and L2 are each independently single bonds, substituted or unsubstituted (C6-C 20 ) represents arylene or substituted or unsubstituted (3-20 member) heteroarylene. For example, L, L1 and L2 may each independently be a single bond, a methyl-substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted carbazoylene. The substituent may be substituted with at least one deuterium.

[0042] In formula A, Ar, Ar1, and Ar2 are each independently hydrogen, deuterium, substituted, or unsubstituted (C6~C 30 )aryl, substituted or unsubstituted (3-30 member) heteroaryl, or substituted or unsubstituted (C3-C 30 ) represents a cycloalkyl group. According to one embodiment of the present disclosure, Ar1 and Ar2 are independently substituted or unsubstituted (C6~C 30 )aryl, substituted or unsubstituted (3-30 member) heteroaryl, or substituted or unsubstituted (C3-C 30 )Cycloalkyl, preferably substituted or unsubstituted (C3~C 30 ) may be cycloalkyl. According to another embodiment of the present disclosure, Ar1 and Ar2 may each be independently substituted or unsubstituted (C6~C 20 )aryl, substituted or unsubstituted (3-20 member) heteroaryl, or substituted or unsubstituted (C3-C 20) represents a cycloalkyl group. For example, Ar1 and Ar2 are each independently a phenyl group substituted with or unsubstituted with at least one selected from the group consisting of substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted norbornyl, substituted or unsubstituted methyl, substituted or unsubstituted tert-butyl, and substituted or unsubstituted adamantyl; a biphenyl group substituted with or unsubstituted with at least one selected from the group consisting of substituted or unsubstituted methyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted norbornyl, and substituted or unsubstituted adamantyl; or a substituted or unsubstituted biphenyl group. Dimethylfluorenyl; substituted or unsubstituted diethylfluorenyl; substituted or unsubstituted o-terphenyl; substituted or unsubstituted m-terphenyl; substituted or unsubstituted phenantrenyl; substituted or unsubstituted spirobifluorenyl; substituted or unsubstituted dibenzofuranyl; substituted or unsubstituted dibenzothiophenyl; substituted or unsubstituted dibenzoselenophenyl; substituted or unsubstituted phenyl-substituted or unsubstituted carbazolyl; substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl; substituted or unsubstituted norbornyl; or substituted or unsubstituted adamantyl. The substituents may be substituted with at least one deuterium. Preferably, at least one of Ar1 and Ar2 may be substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted norbornyl, or substituted or unsubstituted adamantyl.

[0043] However, at least one of Ar1 and Ar2 is either substituted or unsubstituted (C3~C 30 It is a cycloalkyl compound.

[0044] On the other hand, in Equation 1, R9 and R 10 These are, independently, hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C) 30 ) alkyl, substituted or unsubstituted (C6~C 30 ) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C 30)Cycloalkyl, substituted or unsubstituted mono or di(C1~C 30 ) Alkylamino, substituted or unsubstituted mono or di(C6~C 30 ) Arylamino, substituted or unsubstituted (C1~C 30 ) Alkyl (C6~C 30 )arylamino, substituted or unsubstituted mono or di(3-30 member) heteroarylamino, or substituted or unsubstituted (C6-C 30 ) represents an aryl (3-30 membered) heteroarylamino; or may be bonded to adjacent substituents to form a ring. According to one embodiment of the present disclosure, R9 and R 10 These are, independently, hydrogen, deuterium, substituted or unsubstituted (C1~C 30 ) alkyl, or substituted or unsubstituted (C6~C 30 ) It could be an aryl. For example, R9 and R 10 Each of these may independently be hydrogen, deuterium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, or substituted or unsubstituted phenyl. The substituents may be substituted with at least one deuterium.

[0045] In Equation 1, R1~R 10 At least one of them is expressed by formula A. In formula 1, n is an integer of 1 or 2, and when n is 2, R9 and R 10 Each of them may be the same or different.

[0046] According to one embodiment of the present disclosure, formula 1 may be represented by any one of the following formulas 1-1 to 1-4. [ka]

[0047] In equations 1-1 to 1-4, R1 to R8, L, L1, L2, Ar1, and Ar2 are as defined above.

[0048] According to another embodiment of the present disclosure, formula 1 can be represented by formulas 1-5 or 1-6 below. [ka]

[0049] In equations 1-5 and 1-6, R9' and R 10 'Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1~C 30 ) alkyl, substituted or unsubstituted (C6~C 30 ) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C 30 )Cycloalkyl, substituted or unsubstituted mono or di(C1~C 30 ) Alkylamino, substituted or unsubstituted mono or di(C6~C 30 ) Arylamino, substituted or unsubstituted (C1~C 30 ) Alkyl (C6~C 30 )arylamino, substituted or unsubstituted mono or di(3-30 member) heteroarylamino, or substituted or unsubstituted (C6-C 30 ) represents an aryl (3-30 membered) heteroarylamino; or may be bonded to adjacent substituents to form a ring. According to one embodiment of the present disclosure, R9' and R 10 'Each is independently hydrogen, deuterium, or substituted or unsubstituted (C1~C 30 ) may be alkyl. For example, R9' and R 10 Each of these may independently be hydrogen, deuterium, or a deuterium-substituted or unsubstituted methyl molecule.

[0050] In equations 1-5 and 1-6, R1 to R 10 This is as defined above.

[0051] The compound represented by Formula 1 can be selected from, but is not limited to, the following compounds. [ka] [ka]

change

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[0052] In the above compound, D n means that n hydrogen atoms are replaced by deuterium, where n is an integer greater than or equal to 1 and an integer from 1 to the maximum number of hydrogen atoms in the compound.

[0053] Examples of the preparation method of the compound of Formula 1 according to the present disclosure are shown in the following Reaction Scheme 1-1 or 1-2, but are not limited thereto, and may also be prepared using synthetic methods known to those skilled in the art. [Reaction Scheme 1-1] [Chemistry] [Reaction Scheme 1-2] [Chemistry]

[0054] As described above, exemplary synthesis examples of the compound represented by Formula 1 are described, all of which are based on the Buchwald-Hartwig cross-coupling reaction, N-arylation reaction, H-mont-mediated etherification reaction, Miyaura borylation reaction, Suzuki cross-coupling reaction, intramolecular acid-induced cyclization reaction, Pd(II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, dehydration ring-closure reaction, S N 1 substitution reaction, S N 2 substitution reaction, phosphine-mediated reductive cyclization reaction, etc. It will be readily understood by those skilled in the art that the above reactions will proceed even when other substituents defined in Formula 1 other than the substituents described in the specific synthesis examples are attached.

[0055] In an organic electroluminescent device, the light-emitting layer contains a compound represented by the following formula 2. [ka]

[0056] In Equation 2, L 11 ~L 13 Each of these can be independently single-bonded, substituted, or unsubstituted (C6~C 30 ) represents arylene, or substituted or unsubstituted (3-30 member) heteroarylene. According to one embodiment of the present disclosure, L 11 ~L 13 Each of these can be independently single-bonded, substituted, or unsubstituted (C6~C 20 ) may be arylene or substituted or unsubstituted (3-20 member) heteroarylene. For example, L 11 ~L 13 Each of these can independently be a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted phenantrenylene, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted benzothiophenylene, a substituted or unsubstituted carbazoylene, or a substituted or unsubstituted pyridylene. The substituents may be substituted with at least one deuterium.

[0057] In equation 2, Ar 11 is either substitution or non-substitution (C6~C 30 ) represents an aryl or a substituted or unsubstituted (3-30 member) heteroaryl. According to one embodiment of the present disclosure, Ar 11 is either substitution or non-substitution (C6~C 20 ) may be an aryl, or a substituted or unsubstituted (3-25 member) heteroaryl. According to another embodiment of the present disclosure, Ar 11 This may be a substituted or unsubstituted (3-30 membered) heteroaryl having four or more rings. According to another embodiment of the present disclosure, Ar 11 This can be expressed by the following equations 2-1 or 2-2. [ka]

[0058] In Equation 2-1, T1 and T2 are independently -N= and -NR 20 -, -O-, or -S- represent -, where one of T1 and T2 is -N= and the other of T1 and T2 is -NR 20 The condition is that it is -, -O-, or -S-. For example, T1 and T2 can independently be -N=, -O-, or -S-.

[0059] In equation 2-2, T3 represents -O- or -S-. For example, T3 may be -O-.

[0060] In Equation 2-1, R 11 is either substitution or non-substitution (C6~C 30 ) represents an aryl, or a substituted or unsubstituted (3-30 member) heteroaryl. According to one embodiment of the present disclosure, R 11 is either substitution or non-substitution (C6~C 15 ) It may be an aryl or a substituted or unsubstituted (3-10 member) heteroaryl. For example, R 11 This may be a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted pyridyl. The substituent may be substituted with at least one deuterium.

[0061] In equations 2-1 and 2-2, R 12 ~R 19 and R 22 ~R 33 Each is independent of L 11 They may be bonded to hydrogen, deuterium, halogens, cyano, substituted or unsubstituted (C1~C 30 ) alkyl, substituted or unsubstituted (C6~C 30 ) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C 30 )Cycloalkyl, substituted or unsubstituted (C1~C 30) alkoxy, substituted or unsubstituted tri(C1~C 30 ) Alkylsilyl, substituted or unsubstituted di(C1~C 30 ) Alkyl (C6~C 30 ) Arylsilyl, substituted or unsubstituted (C1~C 30 ) Alkyl di(C6~C 30 ) Arylsilyl, substituted or unsubstituted tri(C6~C 30 ) Arylsilyl, (C3~C 30 ) aliphatic ring and (C6~C 30 ) A substituted or unsubstituted condensed ring with an aromatic ring, a substituted or unsubstituted mono or di(C1~C 30 ) alkylamino, substituted or unsubstituted mono or di(C2~C 30 ) Alkenylamino, substituted or unsubstituted (C1~C 30 ) Alkyl (C2~C 30 ) Alkenylamino, substituted or unsubstituted (C1~C 30 ) Alkyl (C6~C 30 ) Arylamino, substituted or unsubstituted (C1~C 30 ) Alkyl (3-30 member) heteroarylamino, substituted or unsubstituted (C2-C 30 ) Alkenil (C6~C 30 ) Arylamino, substituted or unsubstituted (C2~C 30 ) Alkenyl (3-30 member) heteroarylamino, substituted or unsubstituted mono or di(C6-C) 30 )arylamino, substituted or unsubstituted mono or di(3-30 member) heteroarylamino, or substituted or unsubstituted (C6-C 30 ) is an aryl (3-30 membered) heteroarylamino; or can bond with adjacent substituents to form a ring. According to one embodiment of the present disclosure, R 12 ~R 31 These are, independently, hydrogen, deuterium, substituted or unsubstituted (C1~C 30 ) alkyl, substituted or unsubstituted (C6~C 30 ) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C 30 )Cycloalkyl, (C3~C 30 ) aliphatic ring and (C6~C30 ) A substituted or unsubstituted fused ring with an aromatic ring, substituted or unsubstituted (C1~C 30 ) Alkyl (C6~C 30 ) Arylamino, substituted or unsubstituted (C1~C 30 )alkyl (3-30 member) heteroarylamino, substituted or unsubstituted mono or di(C6-C) 30 )arylamino, substituted or unsubstituted mono or di(3-30 member) heteroarylamino, or substituted or unsubstituted (C6-C 30 ) Represents a heteroarylamino (3-30 member) heteroarylamino; or may bond with adjacent substituents to form a ring. For example, R 12 ~R 31 Each of these may independently be hydrogen or deuterium, however, in formula 2-1, R 12 ~R 19 One of them is L 11 They are linked, and in equation 2-2, R 22 ~R 33 One of them is L 11 The condition is that it is connected to [the specified element].

[0062] In equation 2, Ar 12 and Ar 13 These are, independently, hydrogen, deuterium, substituted or unsubstituted (C1~C 30 ) alkyl, substituted or unsubstituted (C6~C 30 ) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C 30 )Cycloalkyl, substituted or unsubstituted (C1~C 30 ) alkoxy, substituted or unsubstituted tri(C1~C 30 ) Alkylsilyl, substituted or unsubstituted di(C1~C 30 ) Alkyl (C6~C 30 ) Arylsilyl, substituted or unsubstituted (C1~C 30 ) Alkyl di(C6~C 30 ) Arylsilyl, substituted or unsubstituted tri(C6~C 30 ) Arylsilyl, substituted or unsubstituted mono or di(C1~C 30) Alkylamino, substituted or unsubstituted mono or di(C2~C 30 ) Alkenylamino, substituted or unsubstituted (C1~C 30 ) Alkyl (C2~C 30 ) Alkenylamino, substituted or unsubstituted mono or di(C6~C 30 ) Arylamino, substituted or unsubstituted (C1~C 30 ) Alkyl (C6~C 30 ) Arylamino, substituted or unsubstituted mono or di(3-30 member) heteroarylamino, substituted or unsubstituted (C1-C 30 ) Alkyl (3-30 member) heteroarylamino, substituted or unsubstituted (C2-C 30 ) Alkenil (C6~C 30 ) Arylamino, substituted or unsubstituted (C2~C 30 ) Alkenyl (3-30 member) heteroarylamino, or substituted or unsubstituted (C6-C 30 ) represents an aryl (3-30 member) heteroarylamino. According to one embodiment of the present disclosure, Ar 12 and Ar 13 These are, independently, hydrogen, deuterium, substituted or unsubstituted (C1~C 30 ) alkyl, substituted or unsubstituted (C6~C 30 ) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C 30 )Cycloalkyl, substituted or unsubstituted mono or di(C6~C 30 ) Arylamino, or substituted or unsubstituted (C6~C 30 ) may be an aryl (3-30 member) heteroarylamino. According to another embodiment of the present disclosure, Ar 12 and Ar 13 These can be substituted or not substituted independently (C6~C 30 )aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted mono or di(C6-C) 30 ) Arylamino, or substituted or unsubstituted (C6~C 30 ) It can be an aryl (3-30 member) heteroarylamino. For example, Ar 12 and Ar13This includes phenyl substituted with or unsubstituted with at least one selected from the group consisting of deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenantrenyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted carbazolyl; biphenyl substituted with or unsubstituted with deuterium or substituted or unsubstituted phenyl; naphthyl substituted with or unsubstituted with at least one selected from the group consisting of deuterium, substituted or unsubstituted phenyl, and substituted or unsubstituted pyridyl; and deuterium, substituted or unsubstituted. Phenantrenyl substituted with or unsubstituted with at least one selected from the group consisting of substituted phenyl and substituted or unsubstituted pyridyl; substituted or unsubstituted dimethylfluorenyl; substituted or unsubstituted dimethylbenzofluorenyl; substituted or unsubstituted diphenylfluorenyl; substituted or unsubstituted o-terphenyl; substituted or unsubstituted m-terphenyl; substituted or unsubstituted p-terphenyl; substituted or unsubstituted 2,6-dimethylphenyl; substituted or unsubstituted tert-butylphenyl; substituted or unsubstituted fluoranthenyl; substituted or unsubstituted anthracenyl; substituted or unsubstituted s Pyrobifluorenyl; substituted or unsubstituted quaterphenyl; substituted or unsubstituted triphenylenyl; dibenzofuranyl substituted with at least one selected from the group consisting of deuterium, substituted or unsubstituted phenyl, and substituted or unsubstituted pyridyl; dibenzothiophenyl substituted with deuterium or substituted or unsubstituted phenyl, or unsubstituted; pyridyl substituted with substituted or unsubstituted phenyl, or unsubstituted; substituted or unsubstituted benzonaphthofuranyl; substituted or unsubstituted benzonaphthothiophenyl; substituted or unsubstituted phenyl or substituted or unsubstituted Carbazolyls substituted with or unsubstituted with substituted biphenyls; phenoxadinyls substituted with or unsubstituted phenyls; benzimidazolyls substituted with or unsubstituted phenyls; substituted or unsubstituted triphenylsilyls; substituted or unsubstituted dibenzoselenophenyls; 14-membered heteroaryls substituted with or unsubstituted methyls; substituted or unsubstituted 22-membered heteroaryls; substituted or unsubstituted benzophenantrenyls; substituted or unsubstituted benzonaphthoselenophenyls; substituted or unsubstituted diphenylaminos; substituted or unsubstituted phenylbiphenylaminos;It may be a substituted or unsubstituted phenyldibenzofuranylamino; a substituted or unsubstituted phenyldibenzothiophenylamino; or a substituted or unsubstituted phenylpyridylamino. The substituent may be substituted with at least one deuterium.

[0063] The compound represented by formula 2 can be selected from, but is not limited to, the following compounds. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0064] In the above compound, D n This means that n hydrogen atoms are substituted with deuterium, where n is an integer greater than or equal to 1 and ranging from 1 to the maximum number of hydrogen atoms in the compound.

[0065] The compounds represented by Formula 2 according to this disclosure can be prepared by synthetic methods known to those skilled in the art, and in particular, synthetic methods disclosed in numerous patent documents can be used. For example, the compounds represented by Formula 2-1 according to this disclosure can be prepared by referring to (Patent Document 1) (published March 2, 2017) and (Patent Document 2) (published September 5, 2018), but are not limited to these. For example, the compounds represented by Formula 2 can be prepared as shown in the following reaction scheme 2, but are not limited to these, and can also be prepared by synthetic methods known to those skilled in the art. [Reaction Scheme 2] [ka]

[0066] In the above reaction scheme 2, Ar 12 and Ar 13 T3 is defined as in Equation 2-2, T3 is defined as in Equation 2, and R is R as in Equation 2-2. 22 ~R 33 As defined.

[0067] In addition, the light-emitting layer of the organic electroluminescent device includes not only the compound represented by Equation 2, but also the compound represented by Equation 3 below: [ka]

[0068] In Equation 3, X1 to X3 are each independently either N or CR. 21 This represents the following, provided that at least one of X1 to X3 is N. For example, X1 to X3 are N, and each is independently N.

[0069] In Equation 3, each R 21 This includes hydrogen, deuterium, halogens, cyano, substituted or unsubstituted (C1-C) 30 ) alkyl, substituted or unsubstituted (C6~C 30 ) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C 30 )Cycloalkyl, substituted or unsubstituted (C1~C 30 ) alkoxy, substituted or unsubstituted tri(C1~C 30 ) Alkylsilyl, substituted or unsubstituted di(C1~C 30 ) Alkyl (C6~C 30 ) Arylsilyl, substituted or unsubstituted (C1~C 30 ) Alkyl di(C6~C 30 ) Arylsilyl, substituted or unsubstituted tri(C6~C 30 ) Arylsilyl, or (C3~C 30 ) aliphatic ring and (C6~C 30 ) Represents a substituted or unsubstituted fused ring with an aromatic ring. According to one embodiment of the present disclosure, each R 21 These are, independently, hydrogen, deuterium, substituted or unsubstituted (C1~C 30 ) alkyl, or substituted or unsubstituted (C6~C 30 ) It could be an allele.

[0070] In Equation 3, L 21 ~L 23 Each of these can be independently single-bonded, substituted, or unsubstituted (C6~C30 ) represents arylene, or substituted or unsubstituted (3-30 member) heteroarylene. According to one embodiment of the present disclosure, L 21 ~L 23 Each of these can be independently single-bonded, substituted, or unsubstituted (C6~C 20 ) may be arylene, or substituted or unsubstituted (3-20 member) heteroarylene. For example, L 21 ~L 23 Each of these can independently be a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted phenantrenylene, a substituted or unsubstituted dibenzofuranylene, or a substituted or unsubstituted dibenzothiophenylene. The substituents may be substituted with at least one deuterium.

[0071] In equation 3, Ar 21 ~Ar 23 These are, independently, hydrogen, deuterium, substituted or unsubstituted (C1~C 30 ) alkyl, substituted or unsubstituted (C3~C 30 )Cycloalkyl, substituted or unsubstituted (3-7 member) heterocycloalkyl, (C3-C 30 ) aliphatic ring and (C6~C 30 ) A substituted or unsubstituted fused ring with an aromatic ring, substituted or unsubstituted (C6~C 30 ) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted tri(C1-C 30 ) Alkylsilyl, substituted or unsubstituted di(C1~C 30 ) Alkyl (C6~C 30 ) Arylsilyl, substituted or unsubstituted (C1~C 30 ) Alkyl di(C6~C 30 ) Arylsilyl, or substituted or unsubstituted tri(C6~C 30 ) may represent arylsilyl. According to one embodiment of the present disclosure, Ar 21 ~Ar 23 These can be substituted or not substituted independently (C6~C 30) may be an aryl or a substituted or unsubstituted (3-30 member) heteroaryl. For example, Ar 21 ~Ar 23 Each of these is independently a phenyl substituted with at least one selected from the group consisting of deuterium, substituted or unsubstituted naphthyl, substituted or unsubstituted phenantrenyl, and substituted or unsubstituted dibenzofuranyl; a biphenyl substituted with at least one selected from the group consisting of deuterium, substituted or unsubstituted naphthyl, and substituted or unsubstituted dibenzofuranyl; a substituted or unsubstituted triphenylenyl; a substituted or unsubstituted triphenylsilyl; a substituted or unsubstituted o-terphenyl; a substituted or unsubstituted m-terphenyl; a substituted or unsubstituted p-terphenyl; a phenantrenyl substituted with a substituted or unsubstituted phenyl or substituted or unsubstituted naphthyl; a substituted or unsubstituted be These may be: phenanthrenyl; naphthyl substituted with at least one selected from the group consisting of deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophenyl; substituted or unsubstituted quaterphenyl; substituted or unsubstituted fluoranthenyl; dibenzofuranyl substituted with at least one selected from the group consisting of deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, and substituted or unsubstituted triphenylenyl; or dibenzothiophenyl substituted with substituted or unsubstituted phenyl. The substituent may be substituted with at least one deuterium.

[0072] According to one embodiment of the present disclosure, formula 3 may be represented by any one of the following formulas 3-1 to 3-4. [ka]

[0073] In equations 3-1 to 3-4, Y is O, S, or NR. 36 For example, Y is either O or S.

[0074] In equations 3-1 to 3-4, R 34 ~R 36 These are, independently, hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C) 30 ) alkyl, substituted or unsubstituted (C6~C 30 ) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C 30 )Cycloalkyl, substituted or unsubstituted (C1~C 30 ) alkoxy, substituted or unsubstituted tri(C1~C 30 ) Alkylsilyl, substituted or unsubstituted di(C1~C 30 ) Alkyl (C6~C 30 ) Arylsilyl, substituted or unsubstituted (C1~C 30 ) Alkyl di(C6~C 30 ) Arylsilyl, substituted or unsubstituted tri(C6~C 30 ) Arylsilyl, substituted or unsubstituted mono or di(C1~C 30 ) Alkylamino, substituted or unsubstituted mono or di(C6~C 30 ) Arylamino, or substituted or unsubstituted (C1~C 30 ) Alkyl (C6~C 30 ) may represent an arylamino; or may bond to an adjacent substituent to form a ring. According to one embodiment of the present disclosure, R 34 ~R 36 Each is independently hydrogen, deuterium, or substituted or unsubstituted (C6~C) 30 ) may represent an aryl. According to another embodiment of the present disclosure, R 34 ~R 36 These are, independently, hydrogen, deuterium, or substituted or unsubstituted (C6~C) 20 ) can represent an aryl. For example, R 34 ~R 36 Each of these is independently hydrogen; deuterium; phenyl substituted with or without substituted naphthyl; naphthyl substituted with or without substituted phenyl; substituted or without substituted biphenyl; or substituted or without substituted phenantrenyl.

[0075] In equations 3-1 to 3-4, L 21 ~L 23 Ar 22 , and Ar 23 This is as defined in Equation 3.

[0076] In equations 3-1 to 3-4, n represents an integer between 1 and 3, m represents an integer between 1 and 4, and when n and m represent integers greater than or equal to 2, R 34 Each of and R 35 Each of them may be the same as or different from the others.

[0077] The compound represented by formula 3 can be selected from, but is not limited to, the following compounds. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0078] In the above compound, D n This means that n hydrogen atoms are substituted with deuterium, where n is an integer greater than or equal to 1 and ranging from 1 to the maximum number of hydrogen atoms in the compound.

[0079] The compounds represented by Formula 3 according to this disclosure can be prepared by referring to (Patent Document 3) (published October 14, 2021) and (Patent Document 4) (published January 18, 2021), but are not limited to these.

[0080] In the hole transport band of an organic electroluminescent device, the layer containing the compound represented by Formula 1 may be a hole transport layer, a hole auxiliary layer, an electron blocking layer, or a light emission auxiliary layer.

[0081] The light-emitting layer of the organic electroluminescent device may further contain additional compounds different from those represented by formulas 2 and 3.

[0082] In organic electroluminescent devices, the light-emitting layer may include a red light-emitting layer.

[0083] An organic electroluminescent compound according to one embodiment is described below.

[0084] This disclosure provides an organic electroluminescent compound represented by the following formula 1' and containing at least one deuterium. [ka]

[0085] In equation 1', X is -CR9R 10 - is

[0086] In formula 1', R1 to R8 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C 30 ) alkyl, substituted or unsubstituted (C6~C 30 ) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C 30 )Cycloalkyl, substituted or unsubstituted (C1~C 30 ) alkoxy, substituted or unsubstituted tri(C1~C 30 ) Alkylsilyl, substituted or unsubstituted di(C1~C 30 ) Alkyl (C6~C 30 ) Arylsilyl, substituted or unsubstituted (C1~C 30 ) Alkyl di(C6~C 30 ) Arylsilyl, substituted or unsubstituted tri(C6~C 30 ) Arylsilyl, (C3~C 30 ) aliphatic ring and (C6~C 30 ) A substituted or unsubstituted condensed ring with an aromatic ring, a substituted or unsubstituted mono or di(C1~C 30 ) Alkylamino, substituted or unsubstituted mono or di(C6~C30 ) Arylamino, substituted or unsubstituted (C1~C 30 ) Alkyl (C6~C 30 )arylamino, substituted or unsubstituted mono or di(3-30 member) heteroarylamino, or substituted or unsubstituted mono(C6-C 30 ) represents an aryl (3-30 member) heteroarylamino. According to one embodiment of the present disclosure, R1 to R8 are each independently hydrogen, deuterium, substituted or unsubstituted (C6 to C 30 )aryl, substituted or unsubstituted mono or di(C6~C 30 ) Aryl, or substituted or unsubstituted (C6~C 30 ) may be an aryl (3-30 member) heteroarylamino. According to another embodiment of the present disclosure, R1 to R8 can each be independently deuterium or represented by the following formula A. [ka]

[0087] In formula A, L, L1, and L2 are each independently single bonds, substitutions, or non-substitutions (C6~C 30 ) Arylene, substituted or unsubstituted (3-30 member) heteroarylene, or substituted or unsubstituted (C3-C 30 ) represents a cycloalkylene. According to one embodiment of the present disclosure, L, L1 and L2 are each independently single bonds, or substituted or unsubstituted (C6~C 30 ) may be arylene. According to another embodiment of the present disclosure, L, L1 and L2 are each independently single bonds, or substituted or unsubstituted (C6~C 20 ) may be arylene. For example, L, L1, and L2 may each be independently single-bonded, deuterium-substituted, or unsubstituted phenylene.

[0088] In formula A, Ar1 and Ar2 are independently hydrogen, deuterium, substituted or unsubstituted (C6~C 30 )aryl, substituted or unsubstituted (3-30 member) heteroaryl, or substituted or unsubstituted (C3-C30 ) represents a cycloalkyl group. According to one embodiment of the present disclosure, Ar1 and Ar2 are independently substituted or unsubstituted (C6~C 30 ) Aryl, or substituted or unsubstituted (C3~C 30 )Cycloalkyl, preferably substituted (C3~C 30 ) may be a cycloalkyl, and the substituents of the substituted cycloalkyl may include at least one deuterium. According to another embodiment of the present disclosure, Ar1 and Ar2 may each be independently substituted or unsubstituted (C6~C 20 ) Aryl, or substituted or unsubstituted (C3~C 20 )Cycloalkyl, preferably substituted (C3~C 20 ) may be a cycloalkyl, and the substituents of a substituted cycloalkyl may contain at least one deuterium. For example, Ar1 and Ar2 may each independently be a deuterium-substituted or unsubstituted cyclohexyl, a deuterium-substituted or unsubstituted norbornyl, or a deuterium-substituted or unsubstituted adamantyl, provided that at least one of Ar1 and Ar2 is substituted or unsubstituted (C3~C 30 ) The condition is that it is a cycloalkyl compound.

[0089] On the other hand, in equation 1', R9 and R 10 These are, independently, hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C) 30 ) alkyl, substituted or unsubstituted (C6~C 30 ) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C 30 )Cycloalkyl, substituted or unsubstituted mono or di(C1~C 30 ) Alkylamino, substituted or unsubstituted mono or di(C6~C 30 ) Arylamino, substituted or unsubstituted (C1~C 30 ) Alkyl (C6~C 30 )arylamino, substituted or unsubstituted mono or di(3-30 member) heteroarylamino, or substituted or unsubstituted (C6-C 30) represents an aryl (3-30 membered) heteroarylamino; or may be bonded to adjacent substituents to form a ring. According to one embodiment of the present disclosure, R9 and R 10 These are, independently, hydrogen, deuterium, or substituted or unsubstituted (C1-C) 30 ) represents alkyl. According to another embodiment of the present disclosure, R9 and R 10 These are, independently, substitution or non-substitution (C1~C 30 ) Represents alkyl. For example, R9 and R 10 Each of these can independently be a deuterium-substituted methyl group.

[0090] In equation 1', R1~R 10 At least one of them is represented by equation A.

[0091] According to one embodiment of the present disclosure, formula 1' can be represented by any one of the following formulas 1'-1 to 1'-4: [ka]

[0092] In equations 1'-1 to 1'-4, X, R1 to R8, L, L1, L2, Ar1, and Ar2 are the same as those defined above.

[0093] According to one embodiment of the present disclosure, formula A may be represented by the following formula B: [ka]

[0094] In equation B, R 51 ~R 54 These are, independently, hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C) 30 ) alkyl, substituted or unsubstituted (C6~C 30 ) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C 30 )Cycloalkyl, substituted or unsubstituted mono or di(C1~C 30) Alkylamino, substituted or unsubstituted mono or di(C6~C 30 ) Arylamino, substituted or unsubstituted (C1~C 30 ) Alkyl (C6~C 30 )arylamino, substituted or unsubstituted mono or di(3-30 member) heteroarylamino, or substituted or unsubstituted (C6-C 30 ) represents an aryl (3-30 member) heteroarylamino. According to one embodiment of the present disclosure, R 51 ~R 54 These are, independently, hydrogen, deuterium, substituted or unsubstituted (C1~C 30 ) alkyl, or substituted or unsubstituted (C6~C 30 ) Represents an arrow. For example, R 51 ~R 54 These can each be independently hydrogen or deuterium.

[0095] In equation B, L1, L2, Ar1, and Ar2 are the same as those defined in equation A.

[0096] The compound represented by formula 1' can be selected from, but is not limited to, the following compounds. [ka]

[0097] In the above compound, D n This means that n hydrogen atoms are substituted with deuterium, where n is an integer greater than or equal to 1 and ranging from 1 to the maximum number of hydrogen atoms in the compound.

[0098] This disclosure provides an organic electroluminescent compound represented by the following formula 4: [ka]

[0099] In equation 4, X4 is -CR 49 R 50 - represents

[0100] In Equation 4, R 41 ~R 50 These are, independently, hydrogen, halogen, cyano, substituted or unsubstituted (C1-C) 30 ) alkyl, substituted or unsubstituted (C6~C 30 ) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C 30 )Cycloalkyl, substituted or unsubstituted mono or di(C1~C 30 ) Alkylamino, substituted or unsubstituted mono or di(C6~C 30 ) Arylamino, substituted or unsubstituted (C1~C 30 ) Alkyl (C6~C 30 )arylamino, substituted or unsubstituted mono or di(3-30 member) heteroarylamino, or substituted or unsubstituted (C6-C 30 ) represents an aryl (3-30 member) heteroarylamino; or it may be bonded to adjacent substituents to form a ring.

[0101] According to one embodiment of this disclosure, R 41 ~R 50 These are, independently, hydrogen, substituted or unsubstituted (C1~C 30 ) alkyl, substituted or unsubstituted (C6~C 30 ) It may be an aryl, or a substituted or unsubstituted (3-30 member) heteroaryl. For example, R 41 ~R 50 Each of these can independently be hydrogen, substituted or unsubstituted methyl, or substituted or unsubstituted phenyl.

[0102] In Equation 4, R 41 ~R 48 At least one of them can be expressed by the following equation B: [ka]

[0103] In formula B, L3 and L4 are independently single bonds, substitutions, or non-substitutions (C6~C30 ) Arylene, substituted or unsubstituted (3-30 member) heteroarylene, or substituted or unsubstituted (C3-C 30 ) represents a cycloalkylene. According to one embodiment of the present disclosure, L3 and L4 are independently single bonds, substituted or unsubstituted (C6~C 30 ) may be arylene, or substituted or unsubstituted (3-30 member) heteroarylene. According to another embodiment of the present disclosure, L3 and L4 may each be independently single bonds, substituted or unsubstituted (C6-C 20 ) represents an arylene, or a substituted or unsubstituted (3-20 member) heteroarylene. For example, L3 and L4 may each be independently a single bond or a substituted or unsubstituted phenylene.

[0104] In formula B, Ar3 and Ar4 are independently hydrogen, substituted or unsubstituted (C6~C 30 )aryl, substituted or unsubstituted (3-30 member) heteroaryl, or substituted or unsubstituted (C3-C 30 ) represents a cycloalkyl group. According to one embodiment of the present disclosure, Ar3 and Ar4 are independently substituted or unsubstituted (C6~C 30 )aryl, substituted or unsubstituted (3-30 member) heteroaryl, or substituted or unsubstituted (C3-C 30 )Cycloalkyl, preferably substituted or unsubstituted (C3~C 30 ) may be cycloalkyl. According to another embodiment of the present disclosure, Ar3 and Ar4 may each be independently substituted or unsubstituted (C6~C 20 )aryl, substituted or unsubstituted (3-20 member) heteroaryl, or substituted or unsubstituted (C3-C 20 ) may be a cycloalkyl group. For example, Ar3 and Ar4 may each independently be a substituted or unsubstituted cyclohexyl, a substituted or unsubstituted norbornyl, or a substituted or unsubstituted adamantyl, provided that at least one of Ar3 and Ar4 is a substituted or unsubstituted (C3~C 30 ) The condition is that it is a cycloalkyl compound.

[0105] In equation B, R51 ~R 54 These are, independently, hydrogen, halogen, cyano, substituted or unsubstituted (C1-C) 30 ) alkyl, substituted or unsubstituted (C6~C 30 ) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C 30 )Cycloalkyl, substituted or unsubstituted mono or di(C1~C 30 ) Alkylamino, substituted or unsubstituted mono or di(C6~C 30 ) Arylamino, substituted or unsubstituted (C1~C 30 ) Alkyl (C6~C 30 )arylamino, substituted or unsubstituted mono or di(3-30 member) heteroarylamino, or substituted or unsubstituted (C6-C 30 ) represents an aryl (3-30 member) heteroarylamino. According to one embodiment of the present disclosure, R 51 ~R 54 These are, independently, hydrogen, substituted or unsubstituted (C1~C 30 ) alkyl, or substituted or unsubstituted (C6~C 30 ) It could be an aryl. For example, R 51 ~R 54 R can be hydrogen, but 41 ~R 54 The condition is that L3, L4, Ar3, and Ar4 do not contain deuterium.

[0106] The organic electroluminescent compound represented by formula 4 can be selected from, but is not limited to, the following compounds. [ka] [ka] [ka]

[0107] An organic electroluminescent material according to one embodiment of the present disclosure may include an organic electroluminescent compound represented by formula 1' and containing at least one deuterium, or an organic electroluminescent compound represented by formula 4.

[0108] An organic electroluminescent device according to one embodiment of the present disclosure may include an organic electroluminescent compound represented by formula 1' and containing at least one deuterium, or an organic electroluminescent compound represented by formula 4.

[0109] An organic electroluminescent device according to one embodiment of the present disclosure comprises an emissive layer, a first hole transport layer, a second hole transport layer, a hole auxiliary layer, an electron blocking layer, and at least one of the emissive auxiliary layers may contain an organic electroluminescent compound represented by formula 1' and containing at least one deuterium, or an organic electroluminescent compound represented by formula 4. The emissive layer may contain one or more hosts and one or more dopants. Optionally, the emissive layer may contain co-host materials, i.e., two or more host materials.

[0110] The host used in the present invention may be a phosphorescent host compound or a fluorescent host compound, and these host compounds are not particularly limited.

[0111] According to one embodiment of the present disclosure, the doping concentration of the dopant compound to the host compound in the light-emitting layer may be less than 20% by weight. One or more phosphorescent or fluorescent dopants may be used as dopants in the organic electroluminescent device of the present disclosure, with phosphorescent dopants being preferred. The phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particularly limited, but may be a complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), optionally preferably an orthometallated complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), optionally and even more preferably an orthometallated iridium complex compound.

[0112] The dopants included in the organic electroluminescent devices of this disclosure may be compounds represented by the following formulas 101 or 102, but are not limited to them. [ka]

[0113] In equations 101 and 102, L' is one of the following structures 1-3: [ka]

[0114] R 100 ~R 103 Each of these is independently hydrogen, deuterium, halogen, deuterium and / or halogen-substituted, or unsubstituted (C1~C 30 ) alkyl, substituted or unsubstituted (C3~C 30 )Cycloalkyl, substituted or unsubstituted (C6~C 30 )aryl, cyano, substituted or unsubstituted (3-30 member) heteroaryl, or substituted or unsubstituted (C1-C 30 ) may represent an alkoxy; or may bond to an adjacent substituent to form a ring, for example, with pyridines such as substituted or unsubstituted quinolines, substituted or unsubstituted isoquinolines, substituted or unsubstituted thienopyridines, substituted or unsubstituted benzoflopyridines, substituted or unsubstituted benzothienopyridines, substituted or unsubstituted indenopyridines, substituted or unsubstituted benzoflopyridines, substituted or unsubstituted benzothienoquinolines, or substituted or unsubstituted indenoquinolines; R 104 ~R 107 Each of these is independently hydrogen, deuterium, halogen, deuterium and / or halogen-substituted, or unsubstituted (C1~C 30 ) alkyl, substituted or unsubstituted (C3~C 30 )Cycloalkyl, substituted or unsubstituted (C6~C 30)aryl, substituted or unsubstituted (3-30 member) heteroaryl, cyano, or substituted or unsubstituted (C1-C 30 ) alkoxide, or substituted or unsubstituted di(C1~C 30 ) may represent an alkylamino; or may bond to an adjacent substituent to form a substituted or unsubstituted ring, for example, with benzene such as substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzoflopyridine, or substituted or unsubstituted benzothienopyridine; R 201 ~R 220 Each of these is independently hydrogen, deuterium, halogen, deuterium and / or halogen-substituted, or unsubstituted (C1~C 30 ) alkyl, substituted or unsubstituted (C3~C 30 )Cycloalkyl, substituted or unsubstituted (C6~C 30 ) Aryl, substituted or unsubstituted (C1~C 30 ) alkoxide, or substituted or unsubstituted di(C1~C 30 ) may represent an alkylamino; or may bond to an adjacent substituent to form a substituted or unsubstituted ring; for example, a ring may form a substituted or unsubstituted benzene, substituted or unsubstituted fluorene, substituted or unsubstituted benzofuran, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted phlopyridine, or substituted or unsubstituted thiophene; Z1 to Z4 each independently represent either N or CK1; K1 is independently hydrogen, deuterium, halogen, deuterium and / or halogen-substituted, or unsubstituted (C1~C 30 ) alkyl, substituted or unsubstituted (C3~C 30 )Cycloalkyl, substituted or unsubstituted (C6~C 30 )aryl, cyano, substituted or unsubstituted (3-30 member) heteroaryl, or substituted or unsubstituted (C1-C 30) may represent an alkoxy; or may bond to an adjacent substituent to form a substituted or unsubstituted ring; for example, a ring may form a substituted or unsubstituted benzene, a substituted or unsubstituted naphthalene, a substituted or unsubstituted thiophene, a substituted or unsubstituted benzothiophene, a substituted or unsubstituted fluorene, a substituted or unsubstituted dibenzofuran, or a substituted or unsubstituted bezinzothiophene; S represents an integer between 1 and 3.

[0115] Specifically, concrete examples of dopant compounds include, but are not limited to, the following: [ka] [ka] [ka] [ka] [ka] [ka]

[0116] The organic electroluminescent device according to this disclosure comprises an anode; a cathode; and at least one organic layer interposed between the anode and the cathode. The organic layer includes an emissive layer and may further include at least one layer selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, an emissive layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer. Each layer may further consist of several layers.

[0117] The anode and cathode can be formed from a transparent conductive material, or from a translucent or reflective conductive material, respectively. Depending on the type of material forming the anode and cathode, the organic electroluminescent device may be top-emitting, bottom-emitting, or double-emitting. In addition, the hole injection layer may be further doped with a p-type dopant, and the electron injection layer may be further doped with an n-type dopant.

[0118] The organic layer may further contain at least one compound selected from the group consisting of arylamine compounds and styrylarylamine compounds. The organic layer may further contain at least one metal selected from the group consisting of metals of Group 1, Group 2, transition metals of Period 4, transition metals of Period 5, lanthanides, and organometallic d-transition elements, or at least one complex compound containing such metals.

[0119] In addition, the organic electroluminescent devices of this disclosure can emit white light by further comprising one or more light-emitting layers containing, in addition to the compounds of this disclosure, blue, red, or green light-emitting compounds known in the art. Furthermore, a yellow or orange light-emitting layer may be further included as needed.

[0120] In the organic electroluminescent device of this disclosure, preferably, at least one layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter referred to as a "surface layer") may be placed on at least one of the inner surfaces of a pair of electrodes. Specifically, it is preferable to place a silicon and aluminum chalcogenide (including oxide) layer on the anode surface on the light-emitting medium layer side, and it is preferable to place a metal halide layer or a metal oxide layer on the cathode surface of the light-emitting medium layer. Operational stability for the organic electroluminescent device can be obtained by the surface layer. Preferably, as the chalcogenide, SiO X (1≦X≦2), AlO XExamples of metal halides (1≦X≦1.5) include SiON and SiAlON, while examples of metal halides include LiF, MgF2, CaF2, and rare earth metal fluorides, and examples of metal oxides include Cs2O, Li2O, MgO, SrO, BaO, and CaO.

[0121] A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof can be used between the anode and the light-emitting layer. The hole injection layer may consist of multiple layers to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or electron blocking layer, where each of the multiple layers may use two compounds simultaneously. Furthermore, the hole transport layer or electron blocking layer may also consist of multiple layers.

[0122] An electron buffer layer, hole blocking layer, electron transport layer, electron injection layer, or a combination thereof can be used between the light-emitting layer and the cathode. The electron buffer layer may consist of multiple layers to control electron injection and improve the interfacial properties between the light-emitting layer and the electron injection layer, where each of the multiple layers may use two compounds simultaneously. The hole blocking layer or electron transport layer may consist of multiple layers, in which case each of the multiple layers may use multiple compounds.

[0123] An auxiliary luminescence layer can be placed between the anode and the luminescent layer, or between the cathode and the luminescent layer. When the auxiliary luminescence layer is placed between the anode and the luminescent layer, it can be used to facilitate hole injection and / or hole transport, or to prevent electron overflow. When the auxiliary luminescence layer is placed between the cathode and the luminescent layer, it can be used to facilitate electron injection and / or electron transport, or to prevent hole overflow. In addition, a hole auxiliary layer can be placed between the hole transport layer (or hole injection layer) and the luminescent layer and may be effective in facilitating or blocking the hole transport rate (or hole injection rate), thereby allowing for control of charge balance. Furthermore, an electron blocking layer can be placed between the hole transport layer (or hole injection layer) and the luminescent layer and can prevent luminescence leakage by confining excitons within the luminescent layer by blocking electron overflow from the luminescent layer. If the organic electroluminescent device includes two or more hole transport layers, the additional layers may be used as hole auxiliary layers or electron blocking layers. A light-emitting auxiliary layer, a hole-auxiliary layer, or an electron-blocking layer has the effect of improving the efficiency and / or lifespan of an organic electroluminescent device.

[0124] Furthermore, in the organic electroluminescent devices of this disclosure, a mixed region of an electron transport compound and a reducing dopant, or a mixed region of a hole transport compound and an oxidizing dopant, can be arranged on at least one surface of the electrode pair. In this case, the electron transport compound is reduced to anions, thus facilitating the injection and transport of electrons from the mixed region to the light-emitting medium. Furthermore, the hole transport compound is oxidized to cations, thus facilitating the injection and transport of holes from the mixed region to the light-emitting medium. Preferably, the oxidizing dopant includes various Lewis acids and acceptor compounds, and the reducing dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. An organic electroluminescent device having two or more light-emitting layers and emitting white light can also be manufactured by using a reducing dopant layer as a charge-generating layer.

[0125] An organic electroluminescent device according to one embodiment of the present disclosure may be an organic electroluminescent device having a tandem structure. In the case of a tandem organic electroluminescent device according to one embodiment, a single light-emitting unit (light-emitting portion) may be formed in a structure in which two or more units are coupled by a charge-generating layer. The organic electroluminescent device may include a plurality of two or more light-emitting units, for example a plurality of three or more light-emitting units, each having a first electrode and a second electrode facing each other on a substrate, and a light-emitting layer laminated between the first electrode and the second electrode that emits light in a specific wavelength range. The organic electroluminescent device may include a plurality of light-emitting units, where each light-emitting unit may include a hole transport band, a light-emitting layer, and a hole transport band, the hole transport band may include a hole injection layer and a hole transport layer, and the electron transport band may include an electron transport layer and an electron injection layer. According to one embodiment, three or more light-emitting layers may be included in a light-emitting unit. The plurality of light-emitting units may emit the same color or different colors. Furthermore, a single light-emitting unit may include one or more light-emitting layers, and these layers may be the same or different colors. It may also include one or more charge-generating layers positioned between each light-emitting unit. A charge-generating layer is a layer that produces holes and electrons when a voltage is applied. If there are three or more light-emitting units, charge-generating layers may be positioned between each light-emitting unit. Here, the charge-generating layers may be the same or different from each other. By positioning charge-generating layers between light-emitting units, the current efficiency in each light-emitting unit can be increased and the charge can be distributed smoothly. Specifically, charge-generating layers can be provided between two adjacent stacks and can help drive a tandem organic electroluminescent device using only anode-cathode pairs without the need for separate internal electrodes positioned between the stacks.

[0126] The charge generation layer may consist of an N-type charge generation layer and a P-type charge generation layer. The N-type charge generation layer may be doped with alkali metals, alkaline earth metals, or compounds of alkali metals and alkaline earth metals. Alkali metals may include one selected from the group consisting of Li, Na, K, Rb, Cs, Fr, Yb, and combinations thereof, and alkaline earth metals may include one selected from the group consisting of Be, Mg, Ca, Sr, Ba, Ra, and combinations thereof. The P-type charge generation layer may consist of a metal or organic material doped with a P-type dopant. For example, the metal may consist of one or more alloys selected from the group consisting of Al, Cu, Fe, Pb, Zn, Au, Pt, W, In, Mo, Ni, and Ti. Furthermore, commonly used materials may be used as host materials for P-type dopants and P-type doped organic materials.

[0127] An organic electroluminescent material according to one embodiment of the present disclosure can be used as a light-emitting material for white organic light-emitting devices. Various structures such as side-by-side structures and layered structures have been proposed for white organic light-emitting devices, depending on the arrangement of R (red), G (green), YG (yellow-green), and B (blue) light-emitting units, or the color conversion material (CCM) method. In addition, the organic electroluminescent material according to one embodiment of the present disclosure can also be applied to organic electroluminescent devices that include QDs (quantum dots).

[0128] To form each layer of the organic electroluminescent device of this disclosure, dry film formation methods such as vacuum evaporation, sputtering, plasma, and ion plating, or wet film formation methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, and flow coating can be applied. When the first and second host compounds of this disclosure are used to form a film, this process is carried out by co-evaporation or mixed evaporation.

[0129] When using a wet film deposition method, thin films can be formed by dissolving or diffusing the materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, or dioxane. The solvent can be any solvent that allows the materials forming each layer to dissolve or diffuse and that does not pose a problem in terms of film formation ability.

[0130] In addition, by using the organic electroluminescent compounds of this disclosure, it is possible to manufacture display devices such as smartphones, tablets, notebooks, PCs, and TVs, or display devices for vehicles, or lighting devices such as outdoor or indoor lighting.

[0131] To gain a detailed understanding of this disclosure, the following describes the preparation methods and physical properties of the compounds according to this disclosure, as well as the driving voltage and current efficiency of OLEDs containing the organic electroluminescent compounds according to this disclosure, using representative compounds of this disclosure. The following examples are intended only to illustrate the properties of the compounds according to this disclosure and OLEDs containing them in order to gain a detailed understanding of this disclosure, and this disclosure is not limited to the following examples.

[0132] In the following, for a detailed understanding of this disclosure, the methods for preparing compounds according to this disclosure will be described using examples of synthesis methods for representative compounds or intermediate compounds of this disclosure. [Examples]

[0133] [Example 1] Synthesis of compound C-51 [ka] 1) Synthesis of compound 1-1 9,9-dimethyl-9H-fluoren-2-amine (32.5 g, 155.2 mmol), 2-(4-bromophenyl)bicyclo[2.2.1]heptane (30 g, 119.4 mmol), palladium(II) acetate (Pd(OAc)2) (1.3 g, 5.97 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos) (4.9 g, 11.9 mmol), and sodium t-butoxide (NaOt-Bu) (22.9 g, 238.8 mmol) were added to a flask, dissolved in 600 mL of xylene, and stirred under reflux at 160°C for 1 hour. After the reaction was complete, the reaction solution was cooled to room temperature, the solvent was removed using a rotary evaporator, and then the solution was purified by column chromatography to obtain a viscous liquid compound 1-1 (45 g, yield: 100%).

[0134] 2) Synthesis of compound C-51 Compound 1-1 (45.0 g, 119 mmol), 1-(4-bromophenyl)adamantane (38 g, 130 mmol), tris(dibenzylideneacetone)dipalladium(0)(Pd2(dba)3) (5.43 g, 5.93 mmol), tri-t-butylphosphine (P(t-Bu)3) (5.85 mL, 11.9 mmol, in 50% xylene solution), and NaOt-Bu (22.8 g, 237 mmol) were added to a flask, dissolved in 600 mL of toluene, and stirred under reflux at 120°C for 1 hour. After the reaction was complete, the reaction solution was cooled to room temperature, the solvent was removed using a rotary evaporator, and then purified by column chromatography to obtain compound C-51 (27.7 g, yield: 39.6%) as a white solid.

[0135] [Table 1]

[0136] [Example 2] Synthesis of compound C-53-D7 [ka] Compound C-51 was synthesized by selecting one of the deuteration methods disclosed in (Patent Document 5) and (Patent Document 6), etc., and compound C-53-D7 (18g, yield: 78.3%) was obtained.

[0137] [Table 2]

[0138] [Example 3] Synthesis of compound C-372 [ka] 1) Synthesis of compound 3-1 2-Bromo-9,9,10,10-tetramethyl-9,10-dihydrophenanthrene (40.0 g, 127 mmol), (2-chlorophenyl)boronic acid (25.8 g, 165 mmol), tetrakis(triphenylphosphine)palladium(0)(Pd(PPh3)4) (7.33 g, 6.34 mmol), potassium carbonate (K2CO3) (35.1 g, 254 mmol), 400 mL of toluene, 200 mL of ethanol, and 200 mL of distilled water were added to a flask and dissolved. The mixture was then stirred under reflux at 140°C for 2 hours. After the reaction was complete, compound 3-1 (40.4 g, yield: 91.8%) was obtained by separation using column chromatography.

[0139] 2) Synthesis of compound 3-2 Compound 3-1 (12.0 g, 34.6 mmol), (4-(adamantan-1-yl)phenyl)-12-azein (11.8 g, 51.9 mmol), Pd(OAc)2 (0.388 g, 1.73 mmol), SPhos (1.42 g, 3.46 mmol), and NaOt-Bu (4.99 g, 51.9 mmol) were added to 300 mL of xylene and stirred under reflux for 2 hours. After the reaction was complete, methanol was added to the reaction solution, and the resulting solid was filtered under reduced pressure and separated by column chromatography to obtain compound 3-2 (11.8 g, yield: 63%).

[0140] 3) Synthesis of compound C-372 Compound 3-2 (11.8 g, 21.9 mmol), 2-(4-bromophenyl)-norbornyl (6.06 g, 24.1 mmol), Pd2(dba)3 (1.00 g, 1.10 mmol), P(t-Bu)3 (1.08 mL, 2.19 mmol, in 50% xylene solution), and NaOt-Bu (4.22 g, 43.9 mmol) were added to 200 mL of toluene and stirred under reflux for 1 hour. After the reaction was complete, methanol was added to the reaction solution, and the resulting solid was filtered under reduced pressure and separated by column chromatography to obtain compound C-372 (5.40 g, yield: 34.8%).

[0141] [Table 3]

[0142] [Example 4] Synthesis of compound C-351 [ka] Compound 4-1 (7.00 g, 20.2 mmol), bis(4-(adamantan-1-yl)phenyl)amine (9.71 g, 22.2 mmol), Pd2(dba)3 (0.924 g, 1.01 mmol), P(t-Bu)3 (0.99 mL, 2.02 mmol, in 50% xylene solution), and NaOt-Bu (3.88 g, 40.4 mmol) were added to 200 mL of toluene and stirred under reflux for 1 hour. After the reaction was complete, methanol was added to the reaction solution, and the resulting solid was filtered under reduced pressure and separated by column chromatography to obtain compound C-351 (4.20 g, yield: 27.8%).

[0143] [Table 4]

[0144] [Example 5] Synthesis of compound C-370 [ka] 1) Synthesis of compound 5-1 2-(4-bromophenyl)norbornyl (5.0 g, 99.5 mmol), 4-cyclohexylaniline (22.7 g, 129 mmol), Pd(OAc)2 (1.12 g, 4.98 mmol), SPhos (3.27 g, 7.96 mmol), and NaOt-Bu (14.3 g, 149 mmol) were added to 1000 mL of toluene and stirred under reflux for 1 hour. After the reaction was complete, methanol was added to the reaction solution, and the resulting solid was filtered under reduced pressure and separated by column chromatography to obtain compound 5-1 (7.90 g, yield: 23.0%).

[0145] 2) Synthesis of compound C-370 Compound 5-1 (7.20 g, 20.8 mmol), Compound 5-2 (7.90 g, 22.9 mmol), Pd2(dba)3 (0.950 g, 1.04 mmol), P(t-Bu)3 (1.03 mL, 2.08 mmol, in 50% xylene solution), and NaOt-Bu (3.99 g, 41.5 mmol) were added to 230 mL of toluene and stirred under reflux for 1 hour. After the reaction was complete, methanol was added to the reaction solution, and the resulting solid was filtered under reduced pressure and separated by column chromatography to obtain Compound C-370 (5.60 g, yield: 41.4%).

[0146] [Table 5]

[0147] [Example 6] Synthesis of compound C-326 [ka] 1) Synthesis of compound 6-1 2-Bromo-9,9-dimethyl-9H-fluorene (20.0 g, 73.2 mmol), (2-chlorophenyl)boronic acid (14.9 g, 95.2 mmol), Pd(PPh3)4 (4.2 g, 3.66 mmol), K2CO3 (20.0 g, 146 mmol), 292 mL of toluene, 73 mL of ethanol, and 73 mL of distilled water were added to a flask and dissolved. The mixture was then refluxed at 140°C for 4 hours. After the reaction was complete, compound 6-1 (21 g, yield: 95%) was obtained by separation using column chromatography.

[0148] 2) Synthesis of compound C-326 Compound 6-1 (16.0 g, 52.5 mmol), 4-(adamantan-1-yl)-N-(4-(norbornyl-2-yl)phenyl)aniline (18.8 g, 47.3 mmol), Pd2(dba)3 (2.4 g, 2.60 mmol), P(t-Bu)3 (2.6 mL, 5.25 mmol, in 50% xylene solution), and NaOt-Bu (10.0 g, 105 mmol) were added to 263 mL of toluene and stirred under reflux for 4 hours. After the reaction was complete, methanol was added to the reaction solution, and the resulting solid was filtered under reduced pressure and separated by column chromatography to obtain compound C-326 (17 g, yield: 54%).

[0149] [Table 6]

[0150] [Device Example 1] Preparation of a red light-emitting OLED according to the present disclosure An OLED was fabricated according to this disclosure. First, a transparent electrode indium tin (ITO) thin film (10 Ω / sq) on a glass substrate for the OLED (Geomatec Co., Ltd., Japan) was sequentially subjected to ultrasonic cleaning with acetone and isopropyl alcohol, and then stored in isopropyl alcohol before use. Next, the ITO substrate was mounted in the substrate holder of a vacuum deposition apparatus. Then, compound HI-1 was introduced into one cell of the vacuum deposition apparatus, and compound HT-1 was introduced into another cell. These two materials were evaporated at different rates, and compound HI-1 was deposited with a doping amount of 5% by weight based on the total amount of compound HI-1 and compound HT-1 to form a hole injection layer with a thickness of 10 nm. Next, compound HT-1 was deposited on the hole injection layer as a first hole transport layer with a thickness of 90 nm. Next, compound C-51 from Table 1 below was introduced into another cell of the vacuum deposition apparatus, and an electric current was passed through the cell to evaporate it, thereby forming a second hole transport layer with a thickness of 60 nm on the first hole transport layer. Then, compound HT-3 was introduced into another cell of the vacuum deposition apparatus, and an electric current was passed through the cell to evaporate it, thereby forming a third hole transport layer with a thickness of 7.5 nm on the second hole transport layer. After forming the hole injection layer and the hole transport layer, an emissive layer was formed on top of them as follows:

[0151] Compounds H1-10 and H3-28 from Table 1 below were introduced into two cells of a vacuum deposition apparatus as hosts for the light-emitting layer, and compound D-39 was introduced into another cell as a dopant. The two host compounds H1-10 and H3-28 were evaporated in a 4:6 ratio, and simultaneously the dopant material was evaporated in different ratios. The dopant was deposited at a doping amount of 2 wt% based on the total amount of host and dopant, forming a light-emitting layer with a thickness of 36 nm on the third hole transport layer. Next, compound B-3 was deposited on the light-emitting layer as an electron buffer layer with a thickness of 5 nm. Then, compounds ET-1 and EI-1 were deposited as an electron transport layer in a weight ratio of 2:1 to a thickness of 25 nm. After depositing compound EI-1 on the electron transport layer as an electron injection layer with a thickness of 2 nm, an Al cathode with a thickness of 80 nm was deposited on the electron injection layer using another vacuum deposition apparatus. In this way, an OLED was fabricated. Each compound was 10 -6 It was purified by vacuum sublimation under Toll's conditions.

[0152] [Device Comparison Examples 1 and 2] Preparation of red light-emitting OLEDs not according to this disclosure An OLED was fabricated in the same manner as in Device Example 1, except that the compounds listed in Table 1 below were used as materials for the second hole transport layer.

[0153] The driving voltage, current efficiency, and CIE color coordinates of the organic electroluminescent devices of Device Example 1 and Device Comparative Examples 1 and 2, fabricated as described above, were measured at a brightness of 1,000 nits, and the results are shown in Table 1 below.

[0154] [Table 7]

[0155] From Table 1 above, it can be seen that the organic electroluminescent device according to this disclosure exhibits lower drive voltage and / or higher current efficiency characteristics compared to conventional organic electroluminescent devices that use a compound as a second hole transport layer.

[0156] [Device Example 2] Preparation of a red light-emitting OLED according to the present disclosure An OLED was fabricated in the same manner as in Device Example 1, except that the host compounds listed in Table 2 below were used as the host material for the light-emitting layer.

[0157] [Device Comparison Examples 3 and 4] Preparation of red light-emitting OLEDs not according to this disclosure An OLED was fabricated in the same manner as in Device Example 2, except that the compounds listed in Table 2 below were used as materials for the second hole transport layer.

[0158] The driving voltage, current efficiency, and CIE color coordinates of the organic electroluminescent devices of Device Example 2 and Device Comparative Examples 3 and 4, fabricated as described above, were measured at a brightness of 1,000 nits, and the results are shown in Table 2 below.

[0159] [Table 8]

[0160] Table 2 above shows that the organic electroluminescent device according to this disclosure exhibits lower drive voltage and / or higher current efficiency characteristics compared to conventional organic electroluminescent devices that use a compound as a second hole transport layer.

[0161] [Device Example 3] Preparation of a red light-emitting OLED according to the present disclosure An OLED was fabricated in the same manner as in Device Example 1, except that the host compounds listed in Table 3 below were used as the host material for the light-emitting layer.

[0162] [Device Comparison Examples 5 and 6] Preparation of Red Emitting OLED Devices Not According to This Disclosure An OLED was fabricated in the same manner as in Device Example 3, except that the compounds listed in Table 3 below were used as materials for the second hole transport layer.

[0163] The driving voltage, current efficiency, and CIE color coordinates of the organic electroluminescent devices manufactured as described above in Example 3 and Comparative Examples 5 and 6 were measured at a brightness of 1,000 nits, and the results are shown in Table 3 below.

[0164] [Table 9]

[0165] From Table 3 above, it can be seen that the organic electroluminescent device according to this disclosure exhibits lower drive voltage and / or higher current efficiency characteristics compared to conventional organic electroluminescent devices that use a compound as a second hole transport layer.

[0166] [Device Examples 4-7] Preparation of Red Emitting OLEDs According to the Present Disclosure An OLED was fabricated in the same manner as in Device Example 1, except that the host compounds listed in Table 4 below were used as the host material for the light-emitting layer, and the compounds listed in Table 4 below were used as the material for the second hole transport layer.

[0167] [Device Comparison Examples 7 and 8] Preparation of red light-emitting OLEDs not according to the present disclosure An OLED was fabricated in the same manner as in Device Example 4, except that the host compounds listed in Table 4 below were used as the material for the second hole transport layer.

[0168] The driving voltage, current efficiency, and CIE color coordinates of the organic electroluminescent devices fabricated as described above (Device Examples 4-7 and Device Comparative Examples 7 and 8) at a brightness of 1,000 nits were measured, and the results are shown in Table 4 below.

[0169] [Table 10]

[0170] Table 4 above shows that the organic electroluminescent device according to this disclosure exhibits lower drive voltage and / or higher current efficiency characteristics compared to conventional organic electroluminescent devices that use a compound as a second hole transport layer.

[0171] [Device Examples 8-11] Preparation of Red Emitting OLEDs According to the Present Disclosure An OLED was fabricated in the same manner as in Device Example 1, except that the host compounds listed in Table 5 below were used as the host material for the light-emitting layer, and the compounds listed in Table 5 below were used as the material for the second hole transport layer.

[0172] [Device Comparative Examples 9 and 10] Preparation of red light-emitting OLEDs not according to the present disclosure An OLED was fabricated in the same manner as in Device Example 8, except that the compounds listed in Table 5 below were used as materials for the second hole transport layer.

[0173] The driving voltage, current efficiency, and CIE color coordinates of the organic electroluminescent devices fabricated as described above (Device Examples 8-11 and Device Comparative Examples 9 and 10) at a brightness of 1,000 nits were measured, and the results are shown in Table 5 below.

[0174] [Table 11]

[0175] Table 5 above shows that the organic electroluminescent device according to this disclosure exhibits characteristics of lower drive voltage and / or higher current efficiency compared to conventional organic electroluminescent devices that use a compound as the second hole transport layer.

[0176] [Device Examples 12-15] Preparation of Red Emitting OLEDs According to the Present Disclosure An OLED was fabricated in the same manner as in Device Example 1, except that the host compounds listed in Table 6 below were used as the host material for the light-emitting layer, and the compounds listed in Table 6 below were used as the material for the second hole transport layer.

[0177] [Comparative Examples 11 and 12] Preparation of red light-emitting OLEDs not according to the present disclosure An OLED was fabricated in the same manner as in Device Example 12, except that the compounds listed in Table 6 below were used as materials for the second hole transport layer.

[0178] The driving voltage, current efficiency, and CIE color coordinates of the organic electroluminescent devices prepared as described above in Examples 12-15 and Comparative Examples 11 and 12 were measured at a brightness of 1,000 nits, and the results are shown in Table 6 below.

[0179] [Table 12]

[0180] Table 6 above shows that the organic electroluminescent device according to this disclosure exhibits characteristics of lower drive voltage and / or higher current efficiency compared to conventional organic electroluminescent devices that use a compound as a second hole transport layer.

[0181] [Device Example 16]: Preparation of a red light-emitting OLED according to the present disclosure An OLED was fabricated in the same manner as in Device Example 1, except that the compounds listed in Table 7 below were used as materials for the second hole transport layer.

[0182] The lifetime at a brightness of 1,000 nits and the relative lifetime to Comparative Example 1 of the organic electroluminescent devices fabricated as described above were measured, and the results are shown in Table 7 below.

[0183] [Table 13]

[0184] Table 7 above shows that the organic electroluminescent device according to this disclosure exhibits a longer lifetime compared to conventional organic electroluminescent devices that use a compound as the second hole transport layer.

[0185] The compounds used in the above-mentioned Device Examples 1-16 and Device Comparative Examples 1-12 are shown in Table 8 below.

[0186] [Table 14]

[0187] [Table 15]

[0188] [Table 16]

Claims

1. An organic electroluminescent device comprising: a first electrode; a second electrode facing the first electrode; a light-emitting layer between the first electrode and the second electrode; and a hole transport band between the first electrode and the light-emitting layer, The hole transport zone contains a compound represented by the following formula 1, The light-emitting layer comprises compounds represented by the following formulas 2 and 3: 【Chemistry 1】 During the ceremony, X is -(CR ９ R １０ ) ｎ - and; R １ to R ８ each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C １ to C ３０ )alkyl, substituted or unsubstituted (C ６ to C ３０ )aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C ３ to C ３０ )cycloalkyl, substituted or unsubstituted (C １ to C ３０ )alkoxy, substituted or unsubstituted tri(C １ to C ３０ )alkylsilyl, substituted or unsubstituted di(C １ to C ３０ )alkyl(C ６ to C ３０ )arylsilyl, substituted or unsubstituted (C １ to C ３０ )alkyldi(C ６ to C ３０ )arylsilyl, substituted or unsubstituted tri(C ６ to C ３０ )arylsilyl, (C ３ to C ３０ )aliphatic ring and (C ６ to C ３０ )aromatic ring substituted or unsubstituted condensed ring, substituted or unsubstituted mono- or di(C １ to C ３０ )alkylamino, substituted or unsubstituted mono- or di(C ６ to C ３０ )arylamino, substituted or unsubstituted (C １ to C ３０ )alkyl(C ６ to C ３０ )arylamino, substituted or unsubstituted mono- or di(3- to 30-membered) heteroarylamino, or substituted or unsubstituted mono(C ６ to C ３０ )aryl(3- to 30-membered) heteroarylamino; R ９ and R １０ Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C) １ ~C ３０ ) alkyl, substituted or unsubstituted (C ６ ~C ３０ ) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C ３ ~C ３０ ) Cycloalkyl, substituted or unsubstituted mono or di(C) １ ~C ３０ ) alkylamino, substituted or unsubstituted mono or di(C ６ ~C ３０ ) Arylamino, substituted or unsubstituted (C １ ~C ３０ ) Alkyl (C ６ ~C ３０ ) arylamino, substituted or unsubstituted mono or di(3-30 member) heteroarylamino, or substituted or unsubstituted (C ６ ~C ３０ ) represents an aryl (3-30 membered) heteroarylamino; or it may be bonded to an adjacent substituent to form a ring; However, R １ ~R １０ At least one of them is expressed by the following formula A: 【Chemistry 2】 During the ceremony, L, L １ and L ２ Each of these can be independently a single bond, a substitution, or an unsubstituted (C) ６ ~C ３０ ) Arylene, substituted or unsubstituted (3-30 member) heteroarylene, or substituted or unsubstituted (C ３ ~C ３０ ) Represents cycloalkylene; Ar １ and Ar ２ Each is independently hydrogen, deuterium, substituted or unsubstituted (C ６ ~C ３０ )aryl, substituted or unsubstituted (3-30 member) heteroaryl, or substituted or unsubstituted (C ３ ~C ３０ ) Represents cycloalkyl, However, Ar １ and Ar ２ At least one of them is substituted or non-substituted (C ３ ~C ３０ ) Provided that it represents a cycloalkyl group; n is an integer of 1 or 2, and if n is 2, R ９ and R １０ Each of them may be the same or different; 【Transformation 3】 During the ceremony, L １１ ~L １３ Each of these can be independently a single bond, a substitution, or an unsubstituted (C) ６ ~C ３０ ) represents arylene or substituted or unsubstituted (3-30 member) heteroarylene; Ar １１ is either substitution or non-substitution (C ６ ~C ３０ ) represents an aryl or a substituted or unsubstituted (3-30 member) heteroaryl; Ar １２ and Ar １３ are each independently hydrogen, deuterium, substituted or unsubstituted (C １ ~C ３０ )-alkyl, substituted or unsubstituted (C ６ ~C ３０ )-aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C ３ ~C ３０ )-cycloalkyl, substituted or unsubstituted (C １ ~C ３０ )-alkoxy, substituted or unsubstituted tri(C １ ~C ３０ )-alkylsilyl, substituted or unsubstituted di(C １ ~C ３０ )-alkyl(C ６ ~C ３０ )-arylsilyl, substituted or unsubstituted (C １ ~C ３０ )-alkyldi(C ６ ~C ３０ )-arylsilyl, substituted or unsubstituted tri(C ６ ~C ３０ )-arylsilyl, substituted or unsubstituted mono- or di(C １ ~C ３０ )-alkylamino, substituted or unsubstituted mono- or di(C ２ ~C ３０ )-alkenylamino, substituted or unsubstituted (C １ ~C ３０ )-alkyl(C ２ ~C ３０ )-alkenylamino, substituted or unsubstituted mono- or di(C ６ ~C ３０ )-arylamino, substituted or unsubstituted (C １ ~C ３０ )-alkyl(C ６ ~C ３０ )-arylamino, substituted or unsubstituted mono- or di(3-30 member) heteroarylamino, substituted or unsubstituted (C １ ~C ３０ )-alkyl(3-30 member) heteroarylamino, substituted or unsubstituted (C ２ ~C ３０ )-alkenyl(C ６ ~C ３０ ) Arylamino, substituted or unsubstituted (C ２ ~C ３０ ) Alkenyl (3-30 member) heteroarylamino, or substituted or unsubstituted (C ６ ~C ３０ ) Represents an aryl (3-30 member) heteroarylamino; 【Chemistry 4】 During the ceremony, X １ ~X ３ Each of these is independently N or CR ２１ This represents, however, X １ ~X ３ Provided that at least one of them is N; R ２１ Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C) １ ~C ３０ ) alkyl, substituted or unsubstituted (C ６ ~C ３０ ) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C ３ ~C ３０ ) Cycloalkyl, substituted or unsubstituted (C １ ~C ３０ ) alkoxy, substituted or unsubstituted tri(C １ ~C ３０ ) alkylsilyl, substituted or unsubstituted di(C １ ~C ３０ ) Alkyl (C ６ ~C ３０ ) Arylsilyl, substituted or unsubstituted (C １ ~C ３０ ) Alkyl di(C ６ ~C ３０ ) Arylsilyl, substituted or unsubstituted tri(C ６ ~C ３０ ) Arylsilyl, or (C ３ ~C ３０ ) Aliphatic rings and (C ６ ~C ３０ ) Represents a substituted or unsubstituted fused ring with an aromatic ring; L ２１ ~L ２３ Each of these can be independently a single bond, a substitution, or an unsubstituted (C) ６ ~C ３０ ) represents arylene, or substituted or unsubstituted (3-30 member) heteroarylene; Ar ２１ ~Ar ２３ Each is independently hydrogen, deuterium, substituted or unsubstituted (C １ ~C ３０ ) alkyl, substituted or unsubstituted (C ３ ~C ３０ ) Cycloalkyl, substituted or unsubstituted (3-7 member) heterocycloalkyl, (C ３ ~C ３０ ) Aliphatic rings and (C ６ ~C ３０ ) A substituted or unsubstituted fused ring with an aromatic ring, substituted or unsubstituted (C ６ ~C ３０ ) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted tri(C １ ~C ３０ ) alkylsilyl, substituted or unsubstituted di(C １ ~C ３０ ) Alkyl (C ６ ~C ３０ ) Arylsilyl, substituted or unsubstituted (C １ ~C ３０ ) Alkyl di(C ６ ~C ３０ ) Arylsilyl, or substituted or unsubstituted tri(C ６ ~C ３０ ) Represents aryl silyl, Organic electroluminescent device.

2. The substituted alkyl, the substituted aryl(ene), the substituted heteroaryl(ene), the substituted cycloalkyl(ene), the substituted heterocycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, the condensed ring of an fatty ring and an aromatic ring, the substituted mono or dialkylamino, the substituted mono or dialkenylamino, the substituted alkylalkenylamino, the substituted mono or diarylamino, the substituted alkylarylamino, the substituted alkylheteroarylamino, the substituted alkenylarylamino, the substituted alkenylheteroarylamino, the substituted mono or diheteroarylamino, and the substituted arylheteroarylamino are each independently of deuterium, halogen, cyano, carboxy, nitro, hydroxy, (C １ ~C ３０ ) alkyl, halo(C １ ~C ３０ ) alkyl, (C ２ ~C ３０ ) Alkenil, (C ２ ~C ３０ ) Alkinyl, (C １ ~C ３０ ) Alkoxy, (C １ ~C ３０ ) alkylthio, (C ３ ~C ３０ ) Cycloalkyl, (C ３ ~C ３０ ) Cycloalkenyl, (3-7 member) heterocycloalkyl, (C ６ ~C ３０ ) Aryloxy, (C ６ ~C ３０ ) Arylthio, (C ６ ~C ３０ ) aryl-substituted or unsubstituted (5-30 member) heteroaryls, (5-30 member) heteroaryl-substituted or unsubstituted (C ６ ~C ３０ ) Ariel, Tori (C １ ~C ３０ ) Alkylsilyl, tri(C ６ ~C ３０ ) Aryl silyl, di(C １ ~C ３０ ) Alkyl (C ６ ~C ３０ ) Aryl silyl, (C １ ~C ３０ ) Alkyl di(C ６ ~C ３０ ) Aryl silyl, (C ３ ~C ３０ ) Fatty ring and (C ６ ~C ３０ ) A condensed ring with an aromatic ring, amino, mono or di(C) １ ~C ３０ ) Alkylamino, substituted or unsubstituted mono or di(C) ６ ~C ３０ ) arylamino, (C １ ~C ３０ ) Alkyl (C ６ ~C ３０ ) Arylamino, mono or di(3-30 member) heteroarylamino, (C １ ~C ３０ ) alkyl (3-30 member) heteroarylamino, (C ６ ~C ３０ ) Aryl (3-30 member) heteroarylamino, (C １ ~C ３０ ) Alkylcarbonyl, (C １ ~C ３０ ) Alkoxycarbonyl, (C ６ ~C ３０ ) Arylcarbonyl, (C ６ ~C ３０ ) Arylphosfinyl, di(C ６ ~C ３０ ) Arylboronyl, di(C １ ~C ３０ ) alkylboronyl, (C １ ~C ３０ ) Alkyl (C ６ ~C ３０ ) Arylboronyl, (C ６ ~C ３０ ) Alkyl (C １ ~C ３０ ) alkyl, (C １ ~C ３０ ) Alkyl (C ６ ~C ３０ The organic electroluminescent device according to claim 1, which is substituted with at least one selected from aryls and combinations thereof.

3. Equation 1 is expressed by one of the following equations 1-1 to 1-4: 【Transformation 5】 During the ceremony, X, R １ ~R ８ L, L １ , L ２ Ar １ and Ar ２ This is as defined in claim 1. The organic electroluminescent device according to claim 1.

4. Equation 1 is represented by the following equations 1-5 or 1-6: 【Transformation 6】 During the ceremony, R ９ 'and R １０ ' is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C １ ~C ３０ ) alkyl, substituted or unsubstituted (C ６ ~C ３０ ) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C ３ ~C ３０ ) Cycloalkyl, substituted or unsubstituted mono or di(C) １ ~C ３０ ) alkylamino, substituted or unsubstituted mono or di(C ６ ~C ３０ ) Arylamino, substituted or unsubstituted (C １ ~C ３０ ) Alkyl (C ６ ~C ３０ ) arylamino, substituted or unsubstituted mono or di(3-30 member) heteroarylamino, or substituted or unsubstituted (C ６ ~C ３０ ) represents an aryl (3-30 membered) heteroarylamino; or it may be bonded to adjacent substituents to form a ring; R １ ~R １０ This is as defined in claim 1, The organic electroluminescent device according to claim 1.

5. Ar of equation A １ and Ar ２ These are, independently, substitution or non-substitution (C ３ ~C ３０ The organic electroluminescent device according to claim 1, which represents a cycloalkyl group.

6. Ar of equation A １ and Ar ２ The organic electroluminescent device according to claim 1, wherein at least one of represents substituted or unsubstituted cyclohexyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted norbornyl, or substituted or unsubstituted adamantyl.

7. Ar in Equation 2 １１ The organic electroluminescent device according to claim 1, wherein is a substituted or unsubstituted (3 to 30 membered) heteroaryl having four or more rings.

8. Ar in Equation 2 １１ This is expressed by equation 2-1 or 2-2: 【Transformation 7】 During the ceremony, T １ and T ２ These are independently -N= and -NR ２０ It represents -, -O-, or -S-, however, T １ and T ２ One of them represents -N=, T １ and T ２ The other of the two is -NR ２０ Provided that it represents -, -O-, or -S-; T ３ represents -O- or -S-; R １１ is either substitution or non-substitution (C ６ ~C ３０ ) represents an aryl, or a substituted or unsubstituted (3-30 member) heteroaryl; R １２ ~R １９ and R ２２ ~R ３３ Each is independent of L １１ It is bonded to hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C １ ~C ３０ ) alkyl, substituted or unsubstituted (C ６ ~C ３０ ) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C ３ ~C ３０ ) Cycloalkyl, substituted or unsubstituted (C １ ~C ３０ ) alkoxy, substituted or unsubstituted tri(C １ ~C ３０ ) alkylsilyl, substituted or unsubstituted di(C １ ~C ３０ ) Alkyl (C ６ ~C ３０ ) Arylsilyl, substituted or unsubstituted (C １ ~C ３０ ) Alkyl di(C ６ ~C ３０ ) Arylsilyl, substituted or unsubstituted tri(C ６ ~C ３０ ) Aryl silyl, (C ３ ~C ３０ ) Aliphatic rings and (C ６ ~C ３０ ) A substituted or unsubstituted fused ring with an aromatic ring, a substituted or unsubstituted mono or di(C) １ ~C ３０ ) alkylamino, substituted or unsubstituted mono or di(C ２ ~C ３０ ) Alkenylamino, substituted or unsubstituted (C １ ~C ３０ ) Alkyl (C ２ ~C ３０ ) Alkenylamino, substituted or unsubstituted (C １ ~C ３０ ) Alkyl (C ６ ~C ３０ ) Arylamino, substituted or unsubstituted (C １ ~C ３０ ) Alkyl (3-30 member) heteroarylamino, substituted or unsubstituted (C ２ ~C ３０ ) Alkenil (C ６ ~C ３０ ) Arylamino, substituted or unsubstituted (C ２ ~C ３０ ) Alkenyl (3-30 member) heteroarylamino, substituted or unsubstituted mono or di(C) ６ ~C ３０ ) arylamino, substituted or unsubstituted mono or di(3-30 member) heteroarylamino, or substituted or unsubstituted (C ６ ~C ３０ ) It is an aryl (3-30 membered) heteroarylamino; or it may bond with adjacent substituents to form a ring, However, R in Equation 2-1 １２ ~R １９ One of them is L １１ It is connected, R in Equation 2-2 ２２ ~R ３３ One of them is L １１ Conditional on being joined, The organic electroluminescent device according to claim 1.

9. Equation 3 can be expressed as any one of Equations 3-1 to 3-4: 【Transformation 8】 During the ceremony, Y is O, S, or NR ３６ And; R ３４ ~R ３６ Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C) １ ~C ３０ ) alkyl, substituted or unsubstituted (C ６ ~C ３０ ) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C ３ ~C ３０ ) Cycloalkyl, substituted or unsubstituted (C １ ~C ３０ ) alkoxy, substituted or unsubstituted tri(C １ ~C ３０ ) alkylsilyl, substituted or unsubstituted di(C １ ~C ３０ ) Alkyl (C ６ ~C ３０ ) Arylsilyl, substituted or unsubstituted (C １ ~C ３０ ) Alkyl di(C ６ ~C ３０ ) Arylsilyl, substituted or unsubstituted tri(C ６ ~C ３０ ) Arylsilyl, substituted or unsubstituted mono or di(C １ ~C ３０ ) alkylamino, substituted or unsubstituted mono or di(C ６ ~C ３０ ) Arylamino, or substituted or unsubstituted (C １ ~C ３０ ) Alkyl (C ６ ~C ３０ ) Represents an arylamino; or may bond to an adjacent substituent to form a ring; L ２１ ~L ２３ Ar ２２ , and Ar ２３ is the same as defined in claim 1; n is an integer between 1 and 3, and m is an integer between 1 and 4; If n and m are integers greater than or equal to 2, then R ３４ and R ３５ Each of them may be the same or different. The organic electroluminescent device according to claim 1.

10. The compound represented by formula 1 above is selected from the following compounds: 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 [Chemistry 18] 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemistry 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemistry 27】 【Chemistry 28】 【Chemistry 29】 【Transformation 30】 In the above formula, D ｎ This means that n hydrogen atoms are substituted with deuterium, where n is an integer greater than or equal to 1 and up to the maximum number of hydrogen atoms in the compound. The organic electroluminescent device according to claim 1.

11. The compound represented by formula 2 is selected from the following compounds: 【Chemistry 31】 【Chemistry 32】 【Transformation 33】 【Transformation 34】 【Chemistry 35】 【Transformation 36】 【Chemistry 37】 【Transformation 38】 【Chemistry 39】 【Chemistry 40】 【Chemistry 41】 【Chemistry 42】 【Chemistry 43】 【Chemistry 44】 【Chemistry 45】 【Chemistry 46】 【Chemistry 47】 【Chemistry 48】 【Chemistry 49】 [Transformation 50] In the above formula, D ｎ This means that n hydrogen atoms are substituted with deuterium, where n is an integer greater than or equal to 1 and ranges from 1 to the maximum number of hydrogen atoms in the compound. The organic electroluminescent device according to claim 1.

12. The compound represented by formula 3 above is selected from the following compounds: 【Chemistry 51】 【Chemistry 52】 【Chemistry 53】 【Chemistry 54】 【Transformation 55】 【Transformation 56】 【Chemistry 57】 【Transformation 58】 【Chemistry 59】 【Transformation 60】 【Chemistry 61】 【Transformation 62】 【Transformation 63】 【Chemistry 64】 【Transformation 65】 【Chemical Formula 66】 【Transformation 67】 【Transformation 68】 【Transformation 69】 【Transformation 70】 【Chemistry 71】 【Chemistry 72】 In the above formula, D ｎ This means that n hydrogen atoms are substituted with deuterium, where n is an integer greater than or equal to 1 and ranges from 1 to the maximum number of hydrogen atoms in the compound. The organic electroluminescent device according to claim 1.

13. The organic electroluminescent device according to claim 1, wherein the layer containing the compound represented by formula 1 in the hole transport band is a hole transport layer, a hole auxiliary layer, an electron blocking layer, or a light emission auxiliary layer.

14. The organic electroluminescent device according to claim 1, further comprising additional compounds in the light-emitting layer that are different from the compounds represented by formulas 2 and 3.

15. The organic electroluminescent device according to claim 1, wherein the light-emitting layer is a red light-emitting layer.

16. An organic electroluminescent compound represented by the following formula 1' and containing at least one deuterium: 【Transformation 73】 During the ceremony, X is -CR ９ R １０ - and; R １ ~R ８ Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C) １ ~C ３０ ) alkyl, substituted or unsubstituted (C ６ ~C ３０ ) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C ３ ~C ３０ ) Cycloalkyl, substituted or unsubstituted (C １ ~C ３０ ) alkoxy, substituted or unsubstituted tri(C １ ~C ３０ ) alkylsilyl, substituted or unsubstituted di(C １ ~C ３０ ) Alkyl (C ６ ~C ３０ ) Arylsilyl, substituted or unsubstituted (C １ ~C ３０ ) Alkyl di(C ６ ~C ３０ ) Arylsilyl, substituted or unsubstituted tri(C ６ ~C ３０ ) Aryl silyl, (C ３ ~C ３０ ) Aliphatic rings and (C ６ ~C ３０ ) A substituted or unsubstituted fused ring with an aromatic ring, a substituted or unsubstituted mono or di(C) １ ~C ３０ ) alkylamino, substituted or unsubstituted mono or di(C ６ ~C ３０ ) Arylamino, substituted or unsubstituted (C １ ~C ３０ ) Alkyl (C ６ ~C ３０ ) arylamino, substituted or unsubstituted mono or di(3-30 member) heteroarylamino, or substituted or unsubstituted mono(C ６ ~C ３０ ) Represents an aryl (3-30 member) heteroarylamino; R ９ and R １０ Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C) １ ~C ３０ ) alkyl, substituted or unsubstituted (C ６ ~C ３０ ) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C ３ ~C ３０ ) Cycloalkyl, substituted or unsubstituted mono or di(C) １ ~C ３０ ) alkylamino, substituted or unsubstituted mono or di(C ６ ~C ３０ ) Arylamino, substituted or unsubstituted (C １ ~C ３０ ) Alkyl (C ６ ~C ３０ ) arylamino, substituted or unsubstituted mono or di(3-30 member) heteroarylamino, or substituted or unsubstituted (C ６ ~C ３０ ) represents an aryl (3-30 membered) heteroarylamino; or it may be bonded to an adjacent substituent to form a ring; However, R １ ~R １０ At least one of them is represented by the following formula A; 【Chemistry 74】 During the ceremony, L, L １ and L ２ Each of these can be independently a single bond, a substitution, or an unsubstituted (C) ６ ~C ３０ ) Arylene, substituted or unsubstituted (3-30 member) heteroarylene, or substituted or unsubstituted (C ３ ~C ３０ ) Represents cycloalkylene; Ar １ and Ar ２ Each is independently hydrogen, deuterium, substituted or unsubstituted (C ６ ~C ３０ )aryl, substituted or unsubstituted (3-30 member) heteroaryl, or substituted or unsubstituted (C ３ ~C ３０ ) Represents cycloalkyl, However, Ar １ and Ar ２ At least one of them is substituted or non-substituted (C ３ ~C ３０ ) Provided that it represents a cycloalkyl group, Organic electroluminescent compounds.

17. Equation 1' can be expressed as one of the following equations: 【Chemistry 75】 During the ceremony, X, R １ ~R ８ L, L １ , L ２ Ar １ and Ar ２ The organic electroluminescent compound according to claim 16, which is defined as in claim 16.

18. Ar of equation A １ is substitution (C ３ ~C ３０ The organic electroluminescent compound according to claim 16, wherein the substituent of the substituted cycloalkyl comprises at least one deuterium.

19. Equation A is expressed by the following equation B: 【Transformation 76】 During the ceremony, R ５１ ~R ５４ Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C) １ ~C ３０ ) alkyl, substituted or unsubstituted (C ６ ~C ３０ ) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C ３ ~C ３０ ) Cycloalkyl, substituted or unsubstituted mono or di(C) １ ~C ３０ ) alkylamino, substituted or unsubstituted mono or di(C ６ ~C ３０ ) Arylamino, substituted or unsubstituted (C １ ~C ３０ ) Alkyl (C ６ ~C ３０ ) arylamino, substituted or unsubstituted mono or di(3-30 member) heteroarylamino, or substituted or unsubstituted (C ６ ~C ３０ ) Represents an aryl (3-30 member) heteroarylamino; L １ , L ２ Ar １ , and Ar ２ The organic electroluminescent compound according to claim 16, wherein is as defined in claim 16.

20. The compound represented by formula 1' above is selected from the following compounds: 【Chemical 77】 In the above compound, D ｎ The organic electroluminescent compound according to claim 16, wherein n hydrogen atoms are substituted with deuterium, where n is an integer greater than or equal to 1 and from 1 to the maximum number of hydrogen atoms in the compound.

21. An organic electroluminescent material comprising the organic electroluminescent compound described in claim 16.

22. An organic electroluminescent device comprising the organic electroluminescent compound described in claim 16.

23. An organic electroluminescent device comprising an organic electroluminescent compound according to claim 16 in at least one layer selected from a light-emitting layer, a first hole transport layer, a second hole transport layer, a hole auxiliary layer, an electron blocking layer, and a light-emitting auxiliary layer.

24. An organic electroluminescent compound represented by the following formula 4: 【Transformation 78】 During the ceremony, X ４ is, -CR ４９ R ５０ - and; R ４１ ~R ５０ Each is independently hydrogen, halogen, cyano, substituted or unsubstituted (C １ ~C ３０ ) alkyl, substituted or unsubstituted (C ６ ~C ３０ ) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C ３ ~C ３０ ) Cycloalkyl, substituted or unsubstituted mono or di(C) １ ~C ３０ ) alkylamino, substituted or unsubstituted mono or di(C ６ ~C ３０ ) Arylamino, substituted or unsubstituted (C １ ~C ３０ ) Alkyl (C ６ ~C ３０ ) arylamino, substituted or unsubstituted mono or di(3-30 member) heteroarylamino, or substituted or unsubstituted (C ６ ~C ３０ ) represents an aryl (3-30 membered) heteroarylamino; or it may be bonded to an adjacent substituent to form a ring, However, R １１ ~R ４８ At least one of them is expressed by the following formula B: 【Chemistry 79】 During the ceremony, L ３ and L ４ Each of these can be independently a single bond, a substitution, or an unsubstituted (C) ６ ~C ３０ ) Arylene, substituted or unsubstituted (3-30 member) heteroarylene, or substituted or unsubstituted (C ３ ~C ３０ ) Represents cycloalkylene; Ar ３ and Ar ４ These are, independently, hydrogen, substituted or unsubstituted (C ６ ~C ３０ )aryl, substituted or unsubstituted (3-30 member) heteroaryl, or substituted or unsubstituted (C ３ ~C ３０ ) Represents cycloalkyl, However, Ar ３ and Ar ４ At least one of them is substituted or non-substituted (C ３ ~C ３０ ) Provided that it represents a cycloalkyl group; R ５１ ~R ５４ Each is independently hydrogen, halogen, cyano, substituted or unsubstituted (C １ ~C ３０ ) alkyl, substituted or unsubstituted (C ６ ~C ３０ ) Aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C ３ ~C ３０ ) Cycloalkyl, substituted or unsubstituted mono or di(C) １ ~C ３０ ) alkylamino, substituted or unsubstituted mono or di(C ６ ~C ３０ ) Arylamino, substituted or unsubstituted (C １ ~C ３０ ) Alkyl (C ６ ~C ３０ ) arylamino, substituted or unsubstituted mono or di(3-30 member) heteroarylamino, or substituted or unsubstituted (C ６ ~C ３０ ) Represents aryl (3-30 member) heteroarylamino; However, R ４１ ~R ５４ , L ３ , L ４ Ar ３ and Ar ４ This is subject to the condition that it does not contain deuterium. Organic electroluminescent compounds.

25. Ar ３ and Ar ４ These are, independently, substitution or non-substitution (C ３ ~C ３０ The organic electroluminescent compound according to claim 24, which represents a cycloalkyl group.

26. The organic electroluminescent compound according to claim 24, wherein the compound represented by formula 4 is selected from the following compounds: 【Chemistry 80】 【Chemistry 81】 【Chemistry 82】

27. An organic electroluminescent material comprising the organic electroluminescent compound described in claim 24.

28. An organic electroluminescent device comprising the organic electroluminescent compound described in claim 24.

29. An organic electroluminescent device comprising an organic electroluminescent compound according to claim 24 in at least one layer selected from a light-emitting layer, a first hole transport layer, a second hole transport layer, a hole auxiliary layer, an electron blocking layer, and a light-emitting auxiliary layer.

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