ORGANIC ELECTROLUMINESCENT COMPONENT AND ORGANIC ELECTROLUMINESCENT DEVICE

Abstract

The present disclosure relates to an organic electroluminescent device comprising: a first electrode; a second electrode opposite the first electrode; a light-emitting layer between the first electrode and the second electrode; and a perforated conveyor belt between the first electrode and the light-emitting layer, wherein the perforated conveyor belt comprises a compound represented by Formula 1 below, and the light-emitting layer comprises a compound represented by Formulas 2 and 3. By using the compounds represented by Formulas 1, 2, and 3, the organic electroluminescent device according to the present disclosure can exhibit a low driving voltage and / or high current efficiency.

Description

Technical field

[0001] The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device. State of the art

[0002] An electroluminescent device (EL device) is a self-light-emitting display device that offers advantages such as a wider viewing angle, a higher contrast ratio, and a faster response time. The first organic EL device was developed by Eastman Kodak in 1987 using low-molecular-weight aromatic diamines and aluminum complexes as materials to form a light-emitting layer (see Appl. Phys. Lett. 51, 913, 1987).

[0003] An organic electroluminescent device consists of a multilayer structure with a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc., to increase its efficiency and stability. The selection of compounds contained in the hole transport layer, etc., is recognized as one of the means to improve device properties such as hole transport efficiency to the light-emitting layer, luminous efficacy, and lifetime.

[0004] To improve the luminous efficacy, drive voltage, and / or lifetime, various materials or concepts for a hole transport layer of an organic electroluminescent device have been proposed. However, these have not proven satisfactory in practical application. Accordingly, there is a continuing need for the development of organic electroluminescent devices with further improved performance, for example, improved drive voltage, luminous efficacy, power efficiency, and / or lifetime characteristics compared to previously disclosed organic electroluminescent devices. Disclosure of the invention Problems to be solved

[0005] The purpose of the present disclosure is, firstly, to provide an organic electroluminescent compound with which an organic electroluminescent device with improved drive voltage and / or current efficiency can be produced, and secondly, to provide an organic electroluminescent device with improved drive voltage and / or current efficiency. Solution to the tasks

[0006] As a result of intensive studies to solve the above technical problems, it was found in the course of the present invention that the above problem can be achieved by an organic electroluminescent device comprising a first electrode; a second electrode opposite the first electrode; a light-emitting layer between the first electrode and the second electrode; and a perforated conveyor belt between the first electrode and the light-emitting layer, wherein the perforated conveyor belt 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, thereby completing the present invention.

[0007] It is true that in Formula 1 X for -(CR9R 10 ) n - stands; R1 to R8 each independently for hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted (C1-C 30 )-Alkoxy, a substituted or unsubstituted tri-(C1-C 30 )-alkylsilyl, a substituted or unsubstituted di-(C1-C 30 )-alkyl-(Cr6-C 30 )-arylsilyl, a substituted or unsubstituted (C1-C 30 )-Alkyldi-(C6-C 30 )-arylsilyl, a substituted or unsubstituted tri-(C6-C 30 )arylsilyl, a substituted or unsubstituted fused ring consisting of an aliphatic (C3-C 30 )-ring and an aromatic (Cr6-C 30 )-ring, a substituted or unsubstituted mono- or di-(C1-C30 )-alkylamino, a substituted or unsubstituted mono- or di-(C6-C 30 )-arylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(C6-C 30 )-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)-heteroarylamino or a substituted or unsubstituted (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino are present; R9 and R 10 each independently for hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted mono- or di-(C1-C 30 )-alkylamino, a substituted or unsubstituted mono- or di-(C6-C 30)-arylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(C6-C 30 )-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)-heteroarylamino or a substituted or unsubstituted (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino can stand or be linked with the neighboring substituents to form one or more rings, with the proviso that at least one of R1 to R 10 represented by the following formula A: where L, L1 and L2 each independently for a single bond, a substituted or unsubstituted (C6-C 30 )-arylene, a substituted or unsubstituted (3- to 30-membered) heteroarylene or a substituted or unsubstituted (C3-C 30 )-Cycloalkylenes; and Ar1 and Ar2 each independently for hydrogen, deuterium, a substituted or unsubstituted (C6-C 30)-aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl or a substituted or unsubstituted (C3-C 30 )-Ccycloalkyl stand, provided that at least one of Ar1 and Ar2 is a substituted or unsubstituted (C3-C 30 )-Cycloalkyl is; and n represents an integer with a value of 1 or 2, and then, if n is 2, R9 and R 10 They can be the same or different.

[0008] It is true that in Formula 2 L 11 to L 13 each independently for a single bond, a substituted or unsubstituted (C6-C 30 )-arylene or a substituted or unsubstituted (3- to 30-membered) heteroarylene; Ar 11 for a substituted or unsubstituted (C6-C 30 )-aryl or a substituted or unsubstituted (3- to 30-membered) heteroaryl; and Ar 12and Ar 13 each independently for hydrogen, deuterium, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted (C1-C 30 )-Alkoxy, a substituted or unsubstituted tri-(C1-C 30 )-alkylsilyl, a substituted or unsubstituted di-(C1-C 30 )-alkyl-(C6-C 30 )-arylsilyl, a substituted or unsubstituted (C1-C 30 )-Alkyldi-(C6-C 30 )-arylsilyl, a substituted or unsubstituted tri-(C6-C 30 )-arylsilyl, a substituted or unsubstituted mono- or di-(C1-C 30 )-alkylamino, a substituted or unsubstituted mono- or di-(C2-C 30 )-alkenylamino, a substituted or unsubstituted (C1-C30 )-Alkyl-(C2-C 30 )-alkenylamino, a substituted or unsubstituted mono- or di-(C6-C 30 )-arylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(C6-C 30 )-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)-heteroarylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(3- to 30-membered)-heteroarylamino, a substituted or unsubstituted (C2-C 30 )-Alkenyl-(C6-C 30 )-arylamino, a substituted or unsubstituted (C2-C 30 )-Alkenyl-(3- to 30-membered)-heteroarylamino or a substituted or unsubstituted (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino are present.

[0009] It is true that in Formula 3 X1 to X3 each independently for N or CR 21 stand; provided that at least one of X1 to X3 is N; R 21each independently for hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted (C1-C 30 )Alkoxy, a substituted or unsubstituted tri-(C1-C 30 )-alkylsilyl, a substituted or unsubstituted di-(C1-C 30 )-alkyl-(C6-C 30 )-arylsilyl, a substituted or unsubstituted (C1-C 30 )-Alkyldi-(C6-C 30 )-arylsilyl, a substituted or unsubstituted tri-(C6-C 30 )-arylsilyl or a substituted or unsubstituted fused ring consisting of an aliphatic (C3-C 30 )-ring and an aromatic (C6-C 30 )-Ring stands; L 21 to L 23each independently for a single bond, a substituted or unsubstituted (C6-C 30 )-arylene or a substituted or unsubstituted (3- to 30-membered) heteroarylene; and Ar 21 to Ar 23 each independently for hydrogen, deuterium, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, a substituted or unsubstituted fused ring of an aliphatic (C3-C 30 )-ring and an aromatic (C6-C 30 )-ring, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted tri-(C1-C 30 )-alkylsilyl, a substituted or unsubstituted di-(C1-C 30 )-alkyl-(C6-C 30)-arylsilyl, a substituted or unsubstituted (C1-C 30 )-Alkyldi-(C6-C 30 )-arylsilyl or a substituted or unsubstituted tri-(C6-C 30 )-arylsilyl stand.

[0010] Furthermore, it was found in the course of the present invention that the above problem can be solved by an organic electroluminescent compound, which is represented by the following formula 1' and comprises at least one deuterium, thereby completing the present invention.

[0011] It is true that in Formula 1' X for -CR9R 10 - stands; R1 to R8 each independently for hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30)-Cycloalkyl, a substituted or unsubstituted (C1-C 30 )-Alkoxy, a substituted or unsubstituted tri-(C1-C 30 )-alkylsilyl, a substituted or unsubstituted di-(C1-C 30 )-alkyl-(Cr6-C 30 )-arylsilyl, a substituted or unsubstituted (C1-C 30 )-Alkyldi-(C6-C 30 )-arylsilyl, a substituted or unsubstituted tri-(C6-C 30 )-arylsilyl, a substituted or unsubstituted fused ring consisting of an aliphatic (C3-C 30 )-ring and an aromatic (Cr6-C 30 )-ring, a substituted or unsubstituted mono- or di-(C1-C 30 )-alkylamino, a substituted or unsubstituted mono- or di-(C6-C 30 )-arylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(C6-C 30)-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)-heteroarylamino or a substituted or unsubstituted (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino are present; and R9 and R 10 each independently for hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted mono- or di-(C1-C 30 )-alkylamino, a substituted or unsubstituted mono- or di-(C6-C 30 )-arylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(Cr6-C 30)-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)-heteroarylamino or a substituted or unsubstituted (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino can stand or be linked with the neighboring substituents to form one or more rings, with the proviso that at least one of R1 to R 10 represented by the following formula A: where L, L1 and L2 each independently for a single bond, a substituted or unsubstituted (C6-C 30 )-arylene, a substituted or unsubstituted (3- to 30-membered) heteroarylene or a substituted or unsubstituted (C3-C 30 )-Cycloalkylenes; and Ar1 and Ar2 each independently for hydrogen, deuterium, a substituted or unsubstituted (C6-C 30)-aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl or a substituted or unsubstituted (C3-C 30 )-Ccycloalkyl stand, with the proviso that at least one of Ar1 and Ar2 is used for a substituted or unsubstituted (C3-C 30 )-Cycloalkyl stands.

[0012] Furthermore, it was found in the course of the present invention that the above problem can be solved by an organic electroluminescent compound, which is represented by the following formula 4, thereby completing the present invention.

[0013] It is true that in Formula 4 X4 for -CR 49 R 50 - stands; and R 41 to R 50 each independently for hydrogen, halogen, cyano, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30)-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted mono- or di-(C1-C 30 )-alkylamino, a substituted or unsubstituted mono- or di-(C6-C 30 )-arylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(C6-C 30 )-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)-heteroarylamino or a substituted or unsubstituted (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino can stand or be linked with the neighboring substituents to form one or more rings, with the proviso that at least one of R 41 to R 48 represented by the following formula B: where L3 and L4 each independently for a single bond, a substituted or unsubstituted (C6-C 30)-arylene, a substituted or unsubstituted (3- to 30-membered) heteroarylene or a substituted or unsubstituted (C3-C 30 )-Cycloalkylenes; Ar3 and Ar4 each independently for hydrogen, a substituted or unsubstituted (C6-C 30 )-aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl or a substituted or unsubstituted (C3-C 30 )-Ccycloalkyl stand, with the proviso that at least one of Ar3 and Ar4 is a substituted or unsubstituted (C3-C 30 )-Cycloalkyl is; and R 51 to R 54 each independently for hydrogen, halogen, cyano, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30)-Cycloalkyl, a substituted or unsubstituted mono- or di-(C1-C 30 )-alkylamino, a substituted or unsubstituted mono- or di-(C6-C 30 )-arylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(C6-C 30 )-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)-heteroarylamino or a substituted or unsubstituted (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino are present; with the proviso that R 41 to R 54 , L3, L4, Ar3 and Ar4 do not contain deuterium. Advantageous effects of the invention

[0014] By using an organic electroluminescent compound according to the present disclosure, an organic electroluminescent device with improved driver voltage and / or current efficiency can be provided. Embodiments of the invention

[0015] The present disclosure is described in detail below. However, the following description is intended to explain the invention and not to limit its scope of protection in any way.

[0016] The present disclosure relates to an organic electroluminescent device comprising: a first electrode; a second electrode opposite the first electrode; a light-emitting layer between the first electrode and the second electrode; and a perforated conveyor belt between the first electrode and the light-emitting layer, wherein the perforated conveyor belt 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.

[0017] The present disclosure relates to an organic electroluminescent compound, which is represented by formula 1' and comprises at least one deuterium.

[0018] Furthermore, the present disclosure relates to an organic electroluminescent compound, which is represented by formula 4.

[0019] In the context of this disclosure, the term “organic electroluminescent compound” means a compound that can be used in an organic electroluminescent device and can be included, as required, in any layer from which an organic electroluminescent device is constructed.

[0020] In the context of this disclosure, the term "organic electroluminescent material" means a material that can be used in an organic electroluminescent device and may comprise at least one compound. The organic electroluminescent material may be included in any layer of the organic electroluminescent device, as required. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material (containing host and dopant materials), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.The hole transport belt material can be at least one of the group consisting of a hole transport material, a hole injection material, an electron blocking material, a hole auxiliary material and a light-emitting auxiliary material.

[0021] The organic electroluminescent material in the present disclosure may contain at least one compound represented by Formula 1. The compound of Formula 1 may be contained in at least one layer of the organic electroluminescent device and in at least one layer of the layers of the perforated conveyor belt, but is not limited thereto. If the compound of Formula 1 is contained in a perforated transport layer, a perforated auxiliary layer, an electron-blocking layer, a light-emitting layer, or a light-emitting auxiliary layer, it may be contained as a perforated transport material, a perforated auxiliary material, an electron-blocking material, a host material, or a light-emitting auxiliary material.

[0022] In the context of this disclosure, the term "electron transport band" refers to a zone in which electrons move between the light-emitting layer and the cathode. For example, the electron transport band can comprise a hole-blocking layer, an electron transport layer, and / or an electron injection layer, preferably an electron transport layer and / or an electron injection layer. The hole-blocking layer serves to prevent the entry of holes into the cathode through the light-emitting layer during the operation of the organic electroluminescent device.

[0023] In the context of this disclosure, the term "hole transport belt" means a zone in which holes move between the first electrode and the light-emitting layer. For example, the hole transport belt may include a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, and / or an electron blocking layer. The hole injection layer, hole transport layer, hole auxiliary layer, light-emitting auxiliary layer, and electron blocking layer may each be a single layer or multiple layers, with two or more layers or three or more layers stacked. According to an example in this disclosure, the hole transport belt may include a first hole transport layer and a second hole transport layer, and may further include a third hole transport layer.The second hole transport layer and the third hole transport layer can be at least one layer of several hole transport layers and can include a hole auxiliary layer, a light-emitting auxiliary layer, and / or an electron-blocking layer. Furthermore, according to another example of the present disclosure, the hole transport belt can include a first hole transport layer and a second hole transport layer; the first hole transport layer can be arranged between the first electrode and the light-emitting layer; the second hole transport layer can be arranged between the first hole transport layer and the light-emitting layer; and the second hole transport layer can be a layer that functions as a hole transport layer, light-emitting auxiliary layer, hole auxiliary layer, and / or electron-blocking layer.According to another example in the present disclosure, the hole transport belt can include a first hole transport layer, a second hole transport layer and a third hole transport layer; the first hole transport layer can be arranged between the first electrode and the light-emitting layer; the second hole transport layer can be arranged between the first hole transport layer and the light-emitting layer; the third hole transport layer can be arranged between the second hole transport layer and the light-emitting layer; and the third hole transport layer can be a layer that functions as a hole transport layer, light-emitting auxiliary layer, hole auxiliary layer and / or electron blocking layer.

[0024] The “(C1-C 30In the present disclosure, "alkyl" means a linear or branched alkyl chain with 1 to 30 carbon atoms, wherein the number of carbon atoms is preferably 1 to 20 and more preferably 1 to 10. Specific examples of the alkyl are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and tert-butyl, etc.

[0025] The term “(C3-C 30In the present disclosure, "cycloalkyl" means a cyclic hydrocarbon substituent consisting of saturated or partially unsaturated monocyclic or polycyclic rings, specifically a mono- or polycyclic hydrocarbon with 3 to 30 ring-structure carbon atoms, in which the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7. Examples of the cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. The monocyclic cycloalkyl includes, as non-limiting examples, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexenyl, cyclohexadienyl, cycloheptyl, cycloheptatrienyl, cyclooctyl, etc. The polycyclic cycloalkyl includes a cycloalkyl with spiroidal rings, fused rings, and cross-linked rings.The cycloalkyl ring can be fused to an aryl, heteroaryl, or heterocycloalkyl ring, and the cycloalkyl ring includes, as non-limiting examples, indanyl, tetrahydronaphthalenyl, benzocycloheptenyl, etc. The cycloalkyl with cross-linked rings means a 5- to 20-membered, preferably 6- to 14-membered, and more preferably 7- to 10-membered, all-carbon polycyclic group with any two rings sharing two non-directly bonded carbon atoms, which may contain one or more double bonds, but neither of the rings having a fully conjugated π-electron system. It can be classified, depending on the number of rings formed, as a bicyclic, tricyclic, tetracyclic, or polycyclic cross-linked cycloalkyl, preferably a bicyclic, tricyclic, or tetracyclic, and more preferably a bicyclic or tricyclic cross-linked cycloalkyl.The cycloalkyl with cross-linked rings includes, for example, adamantyl, norbornyl, norbornenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptanyl, bicyclo[2.2.2]octyl, etc.

[0026] In the present disclosure, the “(3- to 7-membered) heterocycloalkyl” means a cycloalkyl having 3 to 7 and preferably 5 to 7 ring framework atoms and containing at least one heteroatom from the group consisting of B, N, O, S, Si and P, preferably the group consisting of O, S and N, which includes, for example, tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, etc.

[0027] The “(C6-C30)-aryl(ene)” is a monocyclic or fused ring residue derived from an aromatic hydrocarbon with 6 to 30 ring framework carbon atoms, wherein the number of ring framework carbon atoms is preferably 6 to 25 and more preferably 6 to 18, and may be partially saturated. The aryl may contain a spiro structure. Examples of the aryl are phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, dimethylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, Pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl etc. Examples of aryl are specifically 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-Chrysenyl, 2-Chrysenyl,3-Chrysenyl, 4-Chrysenyl, 5-Chrysenyl, 6-Chrysenyl, Benzo[c]phenanthryl, Benzo[g]chrysenyl, 1-Triphenylenyl, 2-Triphenylenyl, 3-Triphenylenyl, 4-Triphenylenyl, 1-Fluorenyl, 2-Fluorenyl, 3-Fluorenyl, 4-Fluorenyl, 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-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-phenanthrenyl, 9,9,10,10-Tetramethyl-9,10-dihydro-2-phenanthrenyl, 9,9,10,10-Tetramethyl-9,10-dihydro-3-phenanthrenyl, 9,9,10,10-Tetramethyl-9,10-dihydro-4-phenanthrenyl usw.,

[0028] In the context of this disclosure, the term "(3- to 30-membered) heteroaryl(ene)" means an aryl(ene) group comprising 3 to 30 ring skeleton atoms and at least one heteroatom from the group consisting of B, N, O, S, Si, P, Se, Te, and Ge, which may be of the monocyclic type or of the type of an fused ring fused to at least one benzene ring and may be partially saturated. The number of heteroatoms is preferably 1 to 4. Furthermore, the heteroaryl(ene) referred to above in this disclosure may be a heteroaryl(ene) formed by linking at least one heteroaryl or aryl group to a heteroaryl(ene) group via one or more single bonds and may contain a spiro structure.

[0029] Beispiele für das Heteroaryl sind ein Heteroryl vom monocyclischen Typ einschließlich Furyl, Thiophenyl, Pyrrolyl, Imidazolyl, Pyrazolyl, Thiazolyl, Thiadiazolyl, Isothiazolyl, Isoxazolyl, Oxazolyl, Oxadiazolyl, Triazinyl, Tetrazinyl, Triazolyl, Tetrazolyl, Furazanyl, Pyridyl, Pyrazinyl, Pyrimidinyl, Pyridazinyl usw. und ein Heteroarylring vom Typ anellierter Ring einschließlich Benzofuranyl, Benzothiophenyl, Isobenzofuranyl, Dibenzofuranyl, Benzophenanthrofuranyl, Dibenzothiophenyl, Benzoimidazolyl, Benzothiazolyl, Benzoisothiazolyl, Benzophenanthrothiophenyl, Benzoisoxazolyl, Benzooxazolyl, Phenanthrooxazolyl, Phenanthrothiazolyl, Isoindolyl, Indolyl, Benzoindolyl, Indazolyl, Benzothiadiazolyl, Chinolyl, Isochinolyl, Cinnolinyl, Chinazolinyl, Benzochinazolinyl, Chinoxalinyl, Benzochinoxalinyl, Naphthyridinyl, Carbazolyl, Benzocarbazolyl, Dibenzocarbazolyl, Phenoxazinyl, Phenothiazinyl, Phenanthridinyl, Benzodioxolyl,Dihydroacridinyl usw. Beispiele für das Heteroaryl sind spezieller 1-Pyrrolyl, 2-Pyrrolyl, 3-Pyrrolyl, Pyrazinyl, 2-Pyridinyl, 2-Pyrimidinyl, 4-Pyrimidinyl, 5-Pyrimidinyl, 6-Pyrimidinyl, 1,2,3-Triazin-4-yl, 1,2,4-Triazin-3-yl, 1,3,5-Triazin-2-yl, 1-Imidazolyl, 2-Imidazolyl, 1-Pyrazolyl, 1-Indolidinyl, 2-Indolidinyl, 3-Indolidinyl, 5-Indolidinyl, 6-Indolidinyl, 7-Indolidinyl, 8-Indolidinyl, 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-Benzofuranyl, 4-Benzofuranyl, 5-Benzofuranyl, 6-Benzofuranyl, 7-Benzofuranyl, 1-Isobenzofuranyl, 3-Isobenzofuranyl, 4-Isobenzofuranyl, 5-Isobenzofuranyl, 6-Isobenzofuranyl, 7-Isobenzofuranyl, 2-Chinolyl, 3-Chinolyl, 4-Chinolyl, 5-Chinolyl,6-Chinolyl, 7-Chinolyl, 8-Chinolyl, 1-Isochinolyl, 3-Isochinolyl, 4-Isochinolyl, 5-Isochinolyl, 6-Isochinolyl, 7-Isochinolyl, 8-Isochinolyl, 2-Chinoxalinyl, 5-Chinoxalinyl, 6-Chinoxalinyl, 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-Phenanthridinyl, 2-Phenanthridinyl, 3-Phenanthridinyl, 4-Phenanthridinyl, 6-Phenanthridinyl, 7-Phenanthridinyl, 8-Phenanthridinyl, 9-Phenanthridinyl, 10-Phenanthridinyl, 1-Acridinyl, 2-Acridinyl, 3-Acridinyl, 4-Acridinyl, 9-Acridinyl, 2-Oxazolyl, 4-Oxazolyl, 5-Oxazolyl, 2-Oxadiazolyl, 5-Oxadiazolyl, 3-Furazanyl, 2-Thienyl, 3-Thienyl, 2-Methylpyrrol-1-yl, 2-Methylpyrrol-3-yl, 2-Methylpyrrol-4-yl, 2-Methylpyrrol-5-yl, 3-Methylpyrrol-1-yl, 3-Methylpyrrol-2-yl, 3-Methylpyrrol-4-yl, 3-Methylpyrrol-5-yl, 2-tert-Butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl,2-Methyl-1-indolyl, 4-Methyl-1-indolyl, 2-Methyl-3-indolyl, 4-Methyl-3-indolyl, 2-tert-Butyl-1-indolyl, 4-tert-Butyl-1-indolyl, 2-tert-Butyl-3-indolyl, 4-tert-Butyl-3-indolyl, 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-[1,2-b]-benzofuranyl, 1-Naphtho-[2,3-b]-benzofuranyl, 2-Naphtho-[2,3-b]-benzofuranyl, 3-Naphtho-[2,3-b]-benzofuranyl, 4-Naphtho-[2,3-b]-benzofuranyl, 5-Naphtho-[2,3-b]-benzofuranyl, 6-Naphtho-[2,3-b]-benzofuranyl, 7-Naphtho-[2,3-b]-benzofuranyl, 8-Naphtho-[2,3-b]-benzofuranyl, 9-Naphtho-[2,3-b]-benzofuranyl, 10-Naphtho-[2,3-b]-benzofuranyl, 1-Naphtho-[2,1-b]-benzofuranyl, 2-Naphtho-[2,1-b]-benzofuranyl, 3-Naphtho-[2,1-b]-benzofuranyl, 4-Naphtho-[2,1-b]-benzofuranyl, 5-Naphtho-[2,1-b]-benzofuranyl, 6-Naphtho-[2,1-b]-benzofuranyl, 7-Naphtho-[2,1-b]-benzofuranyl, 8-Naphtho-[2,1-b]-benzofuranyl, 9-Naphtho-[2,1-b]-benzofuranyl, 10-Naphtho-[2,1-b]-benzofuranyl, 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-Naphtho-[2,1-b]-benzothiophenyl, 9-Naphtho-[2,1-b]-benzothiophenyl, 10-Naphtho-[2,1-b]-benzothiophenyl, 2-Benzofuro[3,2-d]pyrimidinyl, 6-Benzofuro[3,2-d]pyrimidinyl, 7-Benzofuro[3,2-d]pyrimidinyl, 8-Benzofuro[3,2-d]pyrimidinyl, 9-Benzofuro[3,2-d]pyrimidinyl, 2-Benzothio[3,2-d]pyrimidinyl, 6-Benzothio[3,2-d]pyrimidinyl, 7-Benzothio[3,2-d]pyrimidinyl, 8-Benzothio[3,2-d]pyrimidinyl, 9-Benzothio[3,2-d]pyrimidinyl, 2-Benzofuro[3,2-d]pyrazinyl, 6-Benzofuro[3,2-d]pyrazinyl, 7-Benzofuro[3,2-d]pyrazinyl, 8-Benzofuro[3,2-d]pyrazinyl, 9-Benzofuro[3,2-d]pyrazinyl, 2-Benzothio[3,2-d]pyrazinyl, 6-Benzothio[3,2-d]pyrazinyl, 7-Benzothio[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. Additionally, "heteroaryl(ene)" can be classified into heteroaryls with electron properties and heteroaryls with hole properties. A heteroaryl with electron properties is a substituent that is electron-rich compared to the underlying nucleus and can be, for example, a substituted or unsubstituted pyridinyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinoxalinyl, or a substituted or unsubstituted quinolyl, etc. A heteroaryl with hole properties is a substituent that is electron-poor compared to the underlying nucleus and can be, for example, a substituted or unsubstituted carbazolyl,a substituted or unsubstituted dibenzofuranyl or a substituted or unsubstituted dibenzothiophenyl. The term "halogen" in this disclosure includes F, Cl, Br and I.

[0030] The term “an fused ring consisting of an aliphatic (C3-C 30 )-ring and an aromatic (C6-C 30In the context of this disclosure, ")-ring" means a functional group of a ring formed by the fusion of at least one aliphatic ring with 3 to 30, preferably 3 to 25, and more preferably 3 to 18 ring framework carbon atoms and at least one aromatic ring with 6 to 30, preferably 6 to 25, and more preferably 6 to 18 ring framework carbon atoms. For example, the fused ring can be an fused ring of at least one benzene and at least one cyclohexane, or an fused ring of at least one naphthalene and at least one cyclopentane, etc. Here, the carbon atoms in the fused ring can be from an aliphatic (C3-C) 30 )-ring and an aromatic (C6-C 30 )-ring may be replaced by at least one heteroatom selected from B, N, O, S, Si and P, preferably N, O and S.

[0031] Furthermore, "orfho-" ("o-"), "meta-" ("m-"), and "para" ("p-") are prefixes that indicate the relative positions of the substituents. The "ortho-" configuration describes a compound with substituents that are adjacent to each other, e.g., at positions 1 and 2 on benzene. The "meta-" configuration describes the next substitution position after the immediately adjacent substitution position, e.g., a compound with substituents at positions 1 and 3 on benzene. The "para" configuration describes the next substitution position after the meta-position, e.g., a compound with substituents at positions 1 and 4 on benzene.

[0032] In the context of this disclosure, the term "a ring formed by linking with a neighboring substituent" means a substituted or unsubstituted 3- to 30-membered mono- or polycyclic, alicyclic, aromatic ring, or a combination thereof, formed by linking or annulating two or more neighboring substituents, and may preferably be a substituted or unsubstituted 3- to 26-membered mono- or polycyclic, alicyclic, aromatic ring, or a combination thereof. Furthermore, the ring formed may contain at least one heteroatom from the group consisting of B, N, O, S, Si, and P, preferably N, O, and S.

[0033] Furthermore, in the expression "substituted or unsubstituted," "substituted" means that a hydrogen atom in a given functional group is replaced by another atom or functional group, i.e., a substituent. Unless otherwise specified, the substituent can replace hydrogen without restriction at any position where the substituent can be substituted, and if two or more hydrogen atoms in a functional group are each replaced by a substituent, each substituent can be the same or different. The maximum number of substituents that can be substituted for a given functional group can be the total number of valences that can be substituted for each atom forming the functional group.Here are 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 substituted fused ring consisting of an aliphatic 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 each independently substituted by at least one substituent from the group consisting of deuterium, halogen, cyano, carboxyl, nitro, hydroxy, (C1-C.30 )-Alkyl, halogen-(C1-C 30 )-alkyl, (C2-C 30 )-Alkenyl, (C2-C 30 )-Alkynyl, (C1-C 30 )-Alkoxy, (C1-C 30 )-Alkylthio, (C3-C 30 )-Cycloalkyl, (C3-C 30 )-Cycloalkenyl, (3- to 7-membered) heterocycloalkyl, (C6-C 30 )-Aryloxy, (C6-C 30 )-Arylthio, (5- to 30-membered)heteroaryl, unsubstituted or modified by (C6-C 30 )-aryl is substituted, (C6-C 30 )-Aryl, which is unsubstituted or substituted by (5- to 30-membered) heteroaryl, Tri-(C1-C 30 )-alkylsilyl, Tri-(C6-C 30 )-arylsilyl, Di-(C1-C 30 )-alkyl-(C6-C 30 )-arylSilyl, (C1-C 30 )-Alkyldi-(C6-C 30 )-arylSilyl, an fused ring consisting of an aliphatic (C3-C 30 )-ring and an aromatic (C6-C 30 ) ring, amino, mono- or di-(C1-C 30 )-alkylamino, a substituted or unsubstituted mono- or di-(C6-C 30)-arylamino, (C1-C 30 )-Alkyl-(C6-C 30 )-arylamino, mono- or di-(3- to 30-membered)-heteroarylamino, (C1-C 30 )-Alkyl-(3- to 30-membered)-heteroarylamino, (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino, (C1-C 30 )-Alkylcarbonyl, (C1-C 30 )-Alkoxycarbonyl, (C6-C 30 )-Arylcarbonyl, (C6-C 30 )-Arylphosphinyl, Di-(C6-C 30 )-arylboronyl, Di-(C1-C 30 )-alkylboronyl, (C1-C 30 )-Alkyl-(C6-C 30 )-arylbOronyl, (C6-C 30 )-Ar-(C1-C 30 )-alkyl, (C1-C 30 )-Alkyl-(C6-C 30 )-aryl and a combination thereof. According to one embodiment of the present disclosure, the substituted alkyl, etc., can each be independently substituted by at least one substituent from the group consisting of deuterium, cyano, (C1-C 30 )-Alkyl, (C3-C 30)-Cycloalkyl, (5- to 30-membered) heteroaryl, unsubstituted or modified by (C6-C 30 )-aryl is substituted, (C6-C 30 )-aryl, unsubstituted or substituted by (5- to 30-membered) heteroaryl, a substituted or unsubstituted mono- or di-(C6-C 30 )arylamino and a combination thereof. According to another embodiment of the present disclosure, the substituted alkyl etc. can each be independently substituted by at least one substituent from the group consisting of deuterium, cyano, (C1-C 20 )-Alkyl, (C3-C 20 )-Cycloalkyl, (5- to 20-membered) heteroaryl, unsubstituted or modified by (C6-C 20 )-aryl is substituted, (C6-C 20 )-aryl, unsubstituted or substituted by (5- to 20-membered) heteroaryl, a substituted or unsubstituted mono- or di-(C6-C 20)arylamino and a combination thereof. For example, the substituted alkyl, etc., may each be independently substituted by at least one substituent selected from the group consisting of deuterium, cyano, methyl, cyclohexyl (unsubstituted or substituted by deuterium), phenyl (unsubstituted or substituted by deuterium), naphthyl (unsubstituted or substituted by deuterium), biphenyl, phenanthrenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, diphenylamino, carbazolyl, norbornyl, adamantyl, etc.

[0034] If no substituent is specified in the formula or compound structure, this can mean that all substitutable positions are hydrogen or deuterium. This means that some of the hydrogen atoms may be deuterium, which is an isotope of hydrogen, with a deuterium content ranging from 0% to 100%. If no substituent is indicated in the formula or compound structure, hydrogen and deuterium can be present in the compound simultaneously, unless deuterium is explicitly excluded, such as when the deuterium content is 0%, the hydrogen content is 100%, or all substituents are specified as hydrogen. Deuterium, which can be represented as hydrogen-2 and whose element symbol is also D, is... 2Hydrogen, which can be written as H, is one of the isotopes of hydrogen and has a deuteron, consisting of one proton and one neutron, as its nucleus. Isotopes, which mean elements with the same atomic number (Z) but different mass numbers (A), can also be interpreted as elements with the same number of protons but different numbers of neutrons.

[0035] The following describes an organic electroluminescent device according to one embodiment.

[0036] An organic electroluminescent device according to one embodiment comprises a first electrode; a second electrode opposite the first electrode; a light-emitting layer between the first electrode and the second electrode; and a perforated conveyor belt between the first electrode and the light-emitting layer, wherein the perforated conveyor belt comprises a compound represented by the following formula 1:

[0037] In Formula 1, X stands for -(CR9R 10 ) n -

[0038] In formula 1, R1 to R8 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted (C1-C 30 )-Alkoxy, a substituted or unsubstituted tri-(C1-C 30 )-alkylsilyl, a substituted or unsubstituted di-(C1-C 30 )-alkyl-(Cr6-C 30 )-arylsilyl, a substituted or unsubstituted (C1-C 30 )-Alkyldi-(C6-C 30 )-arylsilyl, a substituted or unsubstituted tri-(C6-C 30 )arylsilyl, a substituted or unsubstituted fused ring consisting of an aliphatic (C3-C30 )-ring and an aromatic (Cr6-C 30 )-ring, a substituted or unsubstituted mono- or di-(C1-C 30 )-alkylamino, a substituted or unsubstituted mono- or di-(C6-C 30 )-arylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(C6-C 30 )-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)-heteroarylamino or a substituted or unsubstituted (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino. According to one embodiment of the present disclosure, R1 to R8 can each independently combine hydrogen, deuterium, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted mono- or di-(C6-C 30 )-arylamino or a substituted or unsubstituted (C6-C 30)-aryl-(3- to 30-membered)-heteroarylamino. According to another embodiment of the present disclosure, R1 to R8 can each independently be hydrogen, deuterium or phenyl, or be represented by the following formula A:

[0039] In formula A, L, L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6-C 30 )-arylene, a substituted or unsubstituted (3- to 30-membered) heteroarylene or a substituted or unsubstituted (C3-C 30 )-Cycloalkylene . According to one embodiment of the present disclosure, L, L1 and L2 can each independently form a single bond, a substituted or unsubstituted (C6-C 30)-arylene or a substituted or unsubstituted (3- to 30-membered) heteroarylene. According to another embodiment of the present disclosure, L, L1 and L2 can each independently form a single bond, a substituted or unsubstituted (C6-C 20 The substituents can be an )-arylene or a substituted or unsubstituted (3- to 20-membered) heteroarylene. For example, L, L1, and L2 can each independently be a single bond, phenylene (unsubstituted or methyl-substituted), a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted carbazolylene. The substituents can be substituted by at least one deuterium group.

[0040] In formula A, Ar1 and Ar2 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C6-C 30)-aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl or a substituted or unsubstituted (C3-C 30 )-Cycloalkyl. According to one embodiment of the present disclosure, Ar1 and Ar2 can each independently form substituted or unsubstituted (C6-C 30 )-aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl or a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, preferably a substituted or unsubstituted (C3-C 30 )-cycloalkyl, according to another embodiment of the present disclosure, Ar1 and Ar2 can each independently form a substituted or unsubstituted (C6-C 20 )-aryl, a substituted or unsubstituted (3- to 20-membered) heteroaryl or a substituted or unsubstituted (C3-C 20)-Cycloalkyl. For example, Ar1 and Ar2 can each independently be phenyl, unsubstituted or substituted by at least one substituent from the group consisting of a substituted or unsubstituted cyclopentyl, a substituted or unsubstituted cyclohexyl, a substituted or unsubstituted norbornyl, a substituted or unsubstituted methyl, a substituted or unsubstituted tert-butyl, and a substituted or unsubstituted adamantyl; biphenyl, unsubstituted or substituted by at least one substituent from the group consisting of a substituted or unsubstituted methyl, a substituted or unsubstituted cyclohexyl, a substituted or unsubstituted norbornyl, and a substituted or unsubstituted adamantyl; a substituted or unsubstituted dimethylfluorenyl; a substituted or unsubstituted diethylfluorenyl;a substituted or unsubstituted o-terphenyl; a substituted or unsubstituted m-terphenyl; a substituted or unsubstituted phenanthrenyl; a substituted or unsubstituted spirobifluorenyl; a substituted or unsubstituted dibenzofuranyl; a substituted or unsubstituted dibenzothiophenyl; a substituted or unsubstituted dibenzoselenophenyl; carbazolyl, unsubstituted or substituted by a substituted or unsubstituted phenyl; a substituted or unsubstituted cyclopentyl; a substituted or unsubstituted cyclohexyl;Ar1 and Ar2 may be a substituted or unsubstituted norbornyl or a substituted or unsubstituted adamantyl. The substituents may be substituted by at least one deuterium. Preferably, at least one of Ar1 and Ar2 may be a substituted or unsubstituted cyclopentyl, a substituted or unsubstituted cyclohexyl, a substituted or unsubstituted norbornyl, or a substituted or unsubstituted adamantyl.

[0041] However, at least one of Ar1 and Ar2 is a substituted or unsubstituted (C3-C 30 )-Cycloalkyl.

[0042] Meanwhile, in Formula 1, the R9 and R 10 each independently for hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30)-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted mono- or di-(C1-C 30 )-alkylamino, a substituted or unsubstituted mono- or di-(C6-C 30 )-arylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(C6-C 30 )-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)-heteroarylamino or a substituted or unsubstituted (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino or can be linked with the neighboring substituents to form one or more rings. According to one embodiment of the present disclosure, R9 and R 10 each independently for hydrogen, deuterium, a substituted or unsubstituted (C1-C 30 )-Alkyl or a substituted or unsubstituted (C6-C 30)-Aryl. For example, R9 and R 10 Each can be independently hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, or a substituted or unsubstituted phenyl group. The substituents can be at least one deuterium group.

[0043] In Formula 1, at least one of the R1 to R 10 represented by formula A. In formula 1, n represents an integer with a value of 1 or 2, and then, if n is 2, R9 and R can be used. 10 They can be the same or different.

[0044] According to one embodiment of the present invention, formula 1 can be represented by one of the following formulas 1-1 to 1-4:

[0045] In formulas 1-1 to 1-4, X, R1 to R8, L, L1, L2, Ar1 and Ar2 are defined as above.

[0046] According to another embodiment of the present disclosure, formula 1 can be represented by formula 1-5 or 1-6:

[0047] In Formulas 1-5 and 1-6, R9' and R 10 ' each independently for hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted mono- or di-(C1-C 30 )-alkylamino, a substituted or unsubstituted mono- or di-(C6-C 30 )-arylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(C6-C 30 )-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)-heteroarylamino or a substituted or unsubstituted (C6-C 30)-Aryl-(3- to 30-membered)-heteroarylamino or can be linked with the neighboring substituents to form one or more rings. According to one embodiment of the present disclosure, R9' and R can 10 'each independently hydrogen, deuterium or a substituted or unsubstituted (C1-C 30 )-alkyl. For example, R9' and R 10 'each be independent hydrogen, deuterium or methyl, unsubstituted or substituted by deuterium.

[0048] In formulas 1-5 and 1-6, R1 to R 10 as defined above.

[0049] The compound represented by formula 1 may be selected from the following compounds, but is not limited to them.

[0050] In the compounds above, D'' 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 up to the maximum number of hydrogen atoms in the compound.

[0051] Examples of the manufacturing process for formula 1 according to the present invention are shown in the following reaction schemes 1-1 and 1-2, but are not limited thereto, and can also be produced using a synthesis process known to those skilled in the art.

[0052] As described above, exemplary synthesis examples of the compounds represented by Formula 1 are described, but these are based on a 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, cyclodehydration reaction, SN1 substitution reaction, SN2 substitution reaction, and phosphine-mediated reductive cyclization reaction, etc. It will be readily apparent to those skilled in the art that the above reaction proceeds even when other substituents defined in Formula 1, different from those described in the specific synthesis examples, are bound.

[0053] In the organic electroluminescent device, the light-emitting layer comprises a compound represented by the following formula 2:

[0054] In Formula 2, L 11 to L 13 each independently for a single bond, a substituted or unsubstituted (C6-C 30 )-arylene or a substituted or unsubstituted (3- to 30-membered) heteroarylene. According to one embodiment of the present disclosure, L 11 to L 13 Each independently a single bond, a substituted or unsubstituted (C6-C 20 )-arylene or a substituted or unsubstituted (3- to 20-membered) heteroarylene. For example, L 11 to L 13Each can be independently 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 phenanthrenylene, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted dibenzothiophenylene, a substituted or unsubstituted carbazolylene, or a substituted or unsubstituted pyridylene. The substituents can be substituted by at least one deuterium group.

[0055] In Formula 2, Ar 11 for a substituted or unsubstituted (C6-C 30 )-aryl or a substituted or unsubstituted (3- to 30-membered) heteroaryl. According to one embodiment of the present disclosure, Ar 11 a substituted or unsubstituted (C6-C 20)-aryl or a substituted or unsubstituted (3- to 25-membered) heteroaryl. According to another embodiment of the present disclosure, Ar 11 a substituted or unsubstituted (3- to 30-membered) heteroaryl with 4 or more rings. According to another embodiment of the present disclosure, Ar can be 11 represented by the following formula 2-1 or 2-2:

[0056] In formula 2-1, T1 and T2 each represent -N=, -NR independently. 20 -, -O- or -S-, with the proviso that one of T1 and T2 is -N= and the other of T1 and T2 is -NR 20 -, -O- or -S-. For example, T1 and T2 can each be independently -N=, -O- or -S-.

[0057] In formula 2-2, T3 represents -O- or -S-. For example, T3 can be -O-.

[0058] In Formula 2-1, R 11 for a substituted or unsubstituted (C6-C 30)-aryl or a substituted or unsubstituted (3- to 30-membered) heteroaryl. According to one embodiment of the present disclosure, R 11 a substituted or unsubstituted (C6-C 15 )-aryl or a substituted or unsubstituted (3- to 10-membered) heteroaryl. For example, R 11 The substituents can be a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted pyridyl. The substituents can be substituted by at least one deuterium.

[0059] In formulas 2-1 and 2-2, R 12 to R 19 and R 22 to R 33 each independently at L 11 be bound or for hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30)-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted (C1-C 30 )-Alkoxy, a substituted or unsubstituted tri-(C1-C 30 )-alkylsilyl, a substituted or unsubstituted di-(C1-C 30 )-alkyl-(C6-C 30 )-arylsilyl, a substituted or unsubstituted (C1-C 30 )-Alkyldi-(C6-C 30 )-arylsilyl, a substituted or unsubstituted tri-(C6-C 30 )-arylsilyl, a substituted or unsubstituted fused ring consisting of an aliphatic (C3-C 30 )-ring and an aromatic (C6-C 30 )-ring, a substituted or unsubstituted mono- or di-(C1-C 30 )-alkylamino, a substituted or unsubstituted mono- or di-(C2-C 30 )-alkenylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(C2-C 30)-alkenylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(C6-C 30 )-arylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(3- to 30-membered)-heteroarylamino, a substituted or unsubstituted (C2-C 30 )-Alkenyl-(C6-C 30 -arylamino, a substituted or unsubstituted (C2-C 30 )-Alkenyl-(3- to 30-membered)-heteroarylamino, a substituted or unsubstituted mono- or di-(C6-C 30 )-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)-heteroarylamino or a substituted or unsubstituted (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino stands alone or is linked with the neighboring substituents to form one or more rings. According to one embodiment of the present disclosure, R 12 to R 31each independently for hydrogen, deuterium, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted fused ring consisting of an aliphatic (C3-C 30 )-ring and an aromatic (C6-C 30 )-ring, a substituted or unsubstituted (C1-C 30 )-Akyl-(C6-C 30 )-arylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(3- to 30-membered)-heteroarylamino, a substituted or unsubstituted mono- or di-(C6-C 30 )-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)-heteroarylamino or a substituted or unsubstituted (C6-C 30)-Aryl-(3- to 30-membered)-heteroarylamino or can be linked with the neighboring substituents to form one or more rings. For example, R 12 to R 31 each be independent hydrogen or deuterium, with the proviso that in formula 2-1 one of R 12 to R 19 an L 11 is bound and in formula 2-2 one of R 22 to R 33 an L 11 is bound.

[0060] In Formula 2, Ar 12 and Ar 13 each independently for hydrogen, deuterium, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted (C1-C 30 )-Alkoxy, a substituted or unsubstituted tri-(C1-C 30)-alkylsilyl, a substituted or unsubstituted di-(C1-C 30 )-alkyl-(Cr6-C 30 )-arylsilyl, a substituted or unsubstituted (C1-C 30 )-Alkyldi-(C6-C 30 )-arylsilyl, a substituted or unsubstituted tri-(C6-C 30 )-arylsilyl, a substituted or unsubstituted mono- or di-(C1-C 30 )-alkylamino, a substituted or unsubstituted mono- or di-(C2-C 30 )-alkenylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(C2-C 30 )-alkenylamino, a substituted or unsubstituted mono- or di-(C6-C 30 )-arylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(C6-C 30 )-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)-heteroarylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(3- to 30-membered)-heteroarylamino, a substituted or unsubstituted (C2-C30 )-Alkenyl-(C6-C 30 )-arylamino, a substituted or unsubstituted (C2-C 30 )-Alkenyl-(3- to 30-membered)-heteroarylamino or a substituted or unsubstituted (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino. According to one embodiment of the present disclosure, Ar 12 and Ar 13 Each independently hydrogen, deuterium, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted mono- or di-(C6-C 30 )-arylamino or a substituted or unsubstituted (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino. According to another embodiment of the present disclosure, Ar 12 and Ar13 each independently a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted mono- or di-(C6-C 30 )-arylamino or a substituted or unsubstituted (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino. For example, Ar 12 and Ar 13Phenyl that is unsubstituted or substituted by at least one substituent from the group consisting of deuterium, cyano, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted dibenzofuranyl, and a substituted or unsubstituted carbazolyl; biphenyl that is unsubstituted or substituted by deuterium, or a substituted or unsubstituted phenyl; naphthyl that is unsubstituted or substituted by at least one substituent from the group consisting of deuterium, a substituted or unsubstituted phenyl, and a substituted or unsubstituted pyridyl;Phenanthrenyl, which is unsubstituted or substituted by at least one substituent from the group consisting of deuterium, a substituted or unsubstituted phenyl, and a substituted or unsubstituted pyridyl; a substituted or unsubstituted dimethylfluorenyl; a substituted or unsubstituted dimethylbenzofluorenyl; a substituted or unsubstituted diphenylfluorenyl; a substituted or unsubstituted o-terphenyl; a substituted or unsubstituted m-terphenyl; a substituted or unsubstituted p-terphenyl; a substituted or unsubstituted 2,6-dimethylphenyl; a substituted or unsubstituted tert-butylphenyl; a substituted or unsubstituted fluoranthenyl; a substituted or unsubstituted anthracenyl; a substituted or unsubstituted spirobifluorenyl; a substituted or unsubstituted quaterphenyl; a substituted or unsubstituted triphenylenyl;Dibenzofuranyl, unsubstituted or substituted by at least one substituent from the group consisting of deuterium, a substituted or unsubstituted phenyl, and a substituted or unsubstituted pyridyl; dibenzothiophenyl, unsubstituted or substituted by deuterium or a substituted or unsubstituted phenyl; pyridyl, unsubstituted or substituted by a substituted or unsubstituted phenyl; a substituted or unsubstituted benzonaphthofuranyl; a substituted or unsubstituted benzonaphthothiophenyl; carbazolyl, unsubstituted or substituted by a substituted or unsubstituted phenyl or a substituted or unsubstituted biphenyl; a substituted or unsubstituted phenoxazinyl; Benzoimidazolyl, unsubstituted or substituted by a substituted or unsubstituted phenyl; a substituted or unsubstituted triphenylsilyl;a substituted or unsubstituted dibenzoselenophenyl; a 14-membered heteroaryl substituted by a substituted or unsubstituted methyl; a substituted or unsubstituted 22-membered heteroaryl; a substituted or unsubstituted benzophenanthrenyl; a substituted or unsubstituted benzonaphthoselenophenyl; a substituted or unsubstituted diphenylamino; a substituted or unsubstituted phenylbiphenylamino; a substituted or unsubstituted phenyldibenzofuranylamino; a substituted or unsubstituted phenyldibenzothiophenylamino; or a substituted or unsubstituted phenylpyridylamino. The substituents may be substituted by at least one deuterium.

[0061] The compound represented by formula 2 can be selected from the following compounds, but is not limited to them.

[0062] In the above connections, D means n, that n hydrogen atoms are replaced by deuterium, where n is an integer greater than or equal to 1 and is an integer from 1 up to the maximum number of hydrogen atoms in the compound.

[0063] The compound represented by Formula 2 according to the present disclosure can be prepared by a synthesis method known to a person skilled in the art, and in particular, a synthesis method disclosed in a number of patent specifications can be used. For example, the compound represented by Formula 2-1 according to the present disclosure can be prepared by reference to Korean patent applications No. 2017-0022865 (published on March 2, 2017) and 2018-0099487 (published on September 5, 2018), but is not limited to this. For example, the compound represented by Formula 2-2 can be prepared as in reaction scheme 2 below, but is not limited to this, and can also be prepared by synthesis methods known to a person skilled in the art.

[0064] In reaction scheme 2 above, Ar 12 and Ar 13 As defined in formula 2, T3 is as defined in formula 2-2 and R is as defined in R22 to R 33 defined by formula 2-2.

[0065] Furthermore, the light-emitting layer of the organic electroluminescent device includes not only the compound represented by formula 2, but also the compound represented by formula 3:

[0066] In Formula 3, X1 to X3 each independently represent N or CR. 21 , provided that at least one of X1 to X3 is N. For example, X1 to X3 are each independently N.

[0067] In Formula 3, R 21 each independently for hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted (C1-C 30)Alkoxy, a substituted or unsubstituted tri-(C1-C 30 )-alkylsilyl, a substituted or unsubstituted di-(C1-C 30 )-alkyl-(C6-C 30 )-arylsilyl, a substituted or unsubstituted (C1-C 30 )-Alkyldi-(C6-C 30 )-arylsilyl, a substituted or unsubstituted tri-(C6-C 30 )-arylsilyl or a substituted or unsubstituted fused ring consisting of an aliphatic (C3-C 30 )-ring and an aromatic (C6-C 30 )-ring. According to one embodiment of the present disclosure, R 21 Each independently hydrogen, deuterium, a substituted or unsubstituted (C1-C 30 )-Alkyl or a substituted or unsubstituted (C6-C 30 )-Aryl be.

[0068] In Formula 3, L 21 to L 23 each independently for a single bond, a substituted or unsubstituted (C6-C 30)-arylene or a substituted or unsubstituted (3- to 30-membered) heteroarylene. According to one embodiment of the present disclosure, L 21 to L 23 Each independently a single bond, a substituted or unsubstituted (C6-C 20 )-arylene or a substituted or unsubstituted (3- to 20-membered) heteroarylene. For example, L 21 to L 23 Each can be independently 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 phenanthrenylene, a substituted or unsubstituted dibenzofuranylene, or a substituted or unsubstituted dibenzothiophenylene. The substituents can be substituted by at least one deuterium group.

[0069] In Formula 3, Ar 21 to Ar 23 each independently for hydrogen, deuterium, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, a substituted or unsubstituted fused ring of an aliphatic (C3-C 30 )-ring and an aromatic (C6-C 30 )-ring, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted tri-(C1-C 30 )-alkylsilyl, a substituted or unsubstituted di-(C1-C 30 )-alkyl-(C6-C 30 )-arylsilyl, a substituted or unsubstituted (C1-C 30 )-Alkyldi-(C6-C 30 )-arylsilyl or a substituted or unsubstituted tri-(C6-C 30)-arylsilyl stand. According to one embodiment of the present invention, Ar 21 to Ar 23 each independently a substituted or unsubstituted (C6-C 30 )-aryl or a substituted or unsubstituted (3- to 30-membered) heteroaryl. For example, Ar 21 to Ar 23each independently phenyl, which is unsubstituted or substituted by at least one substituent from the group consisting of deuterium, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthrenyl and a substituted or unsubstituted dibenzofuranyl; biphenyl, which is unsubstituted or substituted by at least one substituent from the group consisting of deuterium, a substituted or unsubstituted naphthyl and a 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;Phenanthrenyl, unsubstituted or substituted by a substituted or unsubstituted phenyl or a substituted or unsubstituted naphthyl; a substituted or unsubstituted benzophenanthrenyl; naphthyl, unsubstituted or substituted by at least one substituent from the group consisting of deuterium, a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted dibenzofuranyl, and a substituted or unsubstituted dibenzothiophenyl; a substituted or unsubstituted quaterphenyl; a substituted or unsubstituted fluoranthenyl;Dibenzofuranyl, which is unsubstituted or substituted by at least one substituent from the group consisting of deuterium, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthrenyl, and a substituted or unsubstituted triphenylenyl; or dibenzothiophenyl, which is unsubstituted or substituted by a substituted or unsubstituted phenyl. The substituents may be substituted by at least one deuterium.

[0070] According to one embodiment of the present invention, formula 3 can be represented by one of the following formulas 3-1 to 3-4:

[0071] In formulas 3-1 to 3-4, YO, S, or NR is used. 36 For example, Y stands for O or S.

[0072] In formulas 3-1 to 3-4, R 34 to R 36each independently for hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted (C1-C 30 )-Alkoxy, a substituted or unsubstituted tri-(C1-C 30 )-alkylsilyl, a substituted or unsubstituted di-(C1-C 30 )-alkyl-(C6-C 30 )-arylsilyl, a substituted or unsubstituted (C1-C 30 )-Alkyldi-(C6-C 30 )-arylsilyl, a substituted or unsubstituted tri-(C6-C 30 )-arylsilyl, a substituted or unsubstituted mono- or di-(C1-C 30 )-alkylamino, a substituted or unsubstituted mono- or di(C6-C 30 )-arylamino or a substituted or unsubstituted (C1-C30 )-Alkyl-(C6-C 30 )-arylamino or can be linked with the neighboring substituents to form one or more rings. According to one embodiment of the present disclosure, R 34 to R 36 each independently hydrogen, deuterium or a substituted or unsubstituted (C6-C 30 )-Aryl be. According to another embodiment of the present disclosure, R 34 to R 36 each independently for hydrogen, deuterium or a substituted or unsubstituted (C6-C 20 )-Aryl. For example, R 34 to R 36each independently hydrogen; deuterium; phenyl, unsubstituted or substituted by a substituted or unsubstituted naphthyl; naphthyl, unsubstituted or substituted by a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl or a substituted or unsubstituted phenanthrenyl.

[0073] In formulas 3-1 to 3-4, L 21 to L 23 , Ar 22 and Ar 23 as defined in Formula 3.

[0074] In formulas 3-1 to 3-4, n is an integer from 1 to 3, m is an integer from 1 to 4, and then, if n and m are integers with a value of 2 or more, each of R can be 34 and each of R 35 be the same or different from each other.

[0075] The compound represented by formula 3 can be selected from the following compounds, but is not limited to them.

[0076] In the above connections, D means n , that n hydrogen atoms are replaced by deuterium, where n is an integer greater than or equal to 1 and is an integer from 1 up to the maximum number of hydrogen atoms in the compound.

[0077] The compound represented by formula 3 according to the present disclosure can be established by reference to Korean patent applications no. 2021-0124018 (published on October 14, 2021) and 2021-0006283 (published on January 18, 2021), but is not limited thereto.

[0078] The layer comprising the compound represented by formula 1 in the hole transport belt of the organic electroluminescent device can be a hole transport layer, a hole auxiliary layer, an electron blocking layer, or a light-emitting auxiliary layer.

[0079] The light-emitting layer of the organic electroluminescent device may further comprise an additional compound different from the compounds represented by Formula 2 and Formula 3.

[0080] In the organic electroluminescent device, the light-emitting layer can contain a red light-emitting layer. An organic electroluminescent compound according to one embodiment is described below.

[0081] The present disclosure provides an organic electroluminescent compound, which is represented by the following formula 1' and comprises at least one deuterium.

[0082] In Formula 1, X stands for -CR9R 10 -

[0083] In Formula 1', R1 to R8 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C 30)-Alkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted (C1-C 30 )-Alkoxy, a substituted or unsubstituted tri-(C1-C 30 )-alkylsilyl, a substituted or unsubstituted di-(C1-C 30 )-alkyl-(Cr6-C 30 )-arylsilyl, a substituted or unsubstituted (C1-C 30 )-Alkyldi-(C6-C 30 )-arylsilyl, a substituted or unsubstituted tri-(C6-C 30 )-arylsilyl, a substituted or unsubstituted fused ring consisting of an aliphatic (C3-C 30 )-ring and an aromatic (C6-C 30 )-ring, a substituted or unsubstituted mono- or di-(C1-C 30 )-alkylamino, a substituted or unsubstituted mono- or di-(C6-C 30)-arylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(C6-C 30 )-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)-heteroarylamino or a substituted or unsubstituted (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino. According to one embodiment of the present disclosure, R1 to R8 can each independently combine hydrogen, deuterium, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted mono- or di-(C6-C 30 )-arylamino or a substituted or unsubstituted (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino. According to another embodiment of the present disclosure, R1 to R8 can each be independently deuterium or be represented by the following formula A:

[0084] In formula A, L, L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6-C 30 )-arylene, a substituted or unsubstituted (3- to 30-membered) heteroarylene or a substituted or unsubstituted (C3-C 30 )-Cycloalkylene . According to one embodiment of the present disclosure, L, L1 and L2 can each independently form a single bond or a substituted or unsubstituted (C6-C 30 )-arylene. According to another embodiment of the present disclosure, L, L1 and L2 can each independently form a single bond or a substituted or unsubstituted (C6-C 20 )-arylene. For example, L, L1 and L2 can each independently be a single bond or phenylene that is unsubstituted or substituted by deuterium.

[0085] In formula A, Ar1 and Ar2 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C6-C 30 )-aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl or a substituted or unsubstituted (C3-C 30 )-Cycloalkyl. According to one embodiment of the present disclosure, Ar1 and Ar2 can each independently form a substituted or unsubstituted (C6-C 30 )-aryl or a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, preferably a substituted (C3-C 30 )-cycloalkyl, and the substituents of the substituted cycloalkyl may contain at least one deuterium. According to another embodiment of the present disclosure, Ar1 and Ar2 may each independently constitute a substituted or unsubstituted (C6-C 20 )-aryl or a substituted or unsubstituted (C3-C 20 )-Cycloalkyl, preferably a substituted (C3-C 20)Cycloalkyl, and the substituents of the substituted cycloalkyl may contain at least one deuterium. For example, Ar1 and Ar2 may each independently be cyclohexyl, unsubstituted or substituted by deuterium, norbornyl, unsubstituted or substituted by deuterium, or adamantyl, unsubstituted or substituted by deuterium, provided that at least one of Ar1 and Ar2 is a substituted or unsubstituted (C3-C 30 )-Cycloalkyl is.

[0086] Meanwhile, in Formula 1, the R9 and R 10 each independently for hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30)-Cycloalkyl, a substituted or unsubstituted mono- or di-(C1-C 30 )-alkylamino, a substituted or unsubstituted mono- or di-(C6-C 30 )-arylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(C6-C 30 )-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)-heteroarylamino or a substituted or unsubstituted (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino or can be linked with the neighboring substituents to form one or more rings. According to one embodiment of the present disclosure, R9 and R 10 each independently hydrogen, deuterium or a substituted or unsubstituted (C1-C 30 )-alkyl. According to another embodiment of the present disclosure, R9 and R can be 10 each independently a substituted or unsubstituted (C1-C 30)-alkyl. For example, R9 and R 10 Each is an independent methyl group substituted by deuterium.

[0087] In Formula 1, at least one of the R1 to R 10 represented by Formula A.

[0088] According to one embodiment of the present invention, formula 1' can be represented by one of the following formulas 1'-1 to 1'-4:

[0089] In formulas 1'-1 to 1'-4, X, R1 to R8, L, L1, L2, Ar1 and Ar2 are defined as above.

[0090] According to one embodiment of the present disclosure, formula A is represented by the following formula B:

[0091] In Formula B, R 51 and R 54 each independently for hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30)-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted mono- or di-(C1-C 30 )-alkylamino, a substituted or unsubstituted mono- or di-(C6-C 3o )-arylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(C6-C 30 )-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)-heteroarylamino or a substituted or unsubstituted (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino. According to one embodiment of the present disclosure, R 51 to R 54 each independently for hydrogen, deuterium, a substituted or unsubstituted (C1-C 30 )-Alkyl or a substituted or unsubstituted (C6-C 30 )-Aryl. For example, R 51 to R 54Each can be either hydrogen or deuterium, independently of each other.

[0092] In formula B, L1, L2, Ar1 and Ar2 are defined as in formula A.

[0093] The compound represented by formula 1' may be selected from the following compounds, but is not necessarily limited to them.

[0094] In the above connections, D means n , that n hydrogen atoms are replaced by deuterium, where n is an integer greater than or equal to 1 and is an integer from 1 up to the maximum number of hydrogen atoms in the compound.

[0095] The present disclosure provides an organic electroluminescent compound, which is represented by the following formula 4:

[0096] In Formula 4, X4 stands for -CR 49 R 50 -

[0097] In Formula 4, R 41 to R 50each independently for hydrogen, halogen, cyano, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted mono- or di-(C1-C 30 )-alkylamino, a substituted or unsubstituted mono- or di-(C6-C 3o )-arylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(C6-C 30 )-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)-heteroarylamino or a substituted or unsubstituted (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino or can be linked with the neighboring substituents to form one or more rings.

[0098] According to one embodiment of the present disclosure, R41 to R 50 each independently for hydrogen, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30 )-aryl or a substituted or unsubstituted (3- to 30-membered) heteroaryl. For example, R 41 to R 50 Each can be independent hydrogen, a substituted or unsubstituted methyl, or a substituted or unsubstituted phenyl.

[0099] In Formula 4, at least one of R can be 41 to R 48 represented by the following formula B:

[0100] In formula B, L3 and L4 each independently represent a single bond, a substituted or unsubstituted (C6-C 30 )-arylene, a substituted or unsubstituted (3- to 30-membered) heteroarylene or a substituted or unsubstituted (C3-C 30)-Cycloalkylenes. According to one embodiment of the present disclosure, L3 and L4 can each independently form a single bond, a substituted or unsubstituted (C6-C 30 )-arylene or a substituted or unsubstituted (3- to 30-membered) heteroarylene. According to another embodiment of the present disclosure, L3 and L4 can each independently form a single bond, a substituted or unsubstituted (C6-C 20 L3 and L4 can each be a single bond or a substituted or unsubstituted (3- to 20-membered) heteroarylene. For example, L3 and L4 can each independently be a single bond or a substituted or unsubstituted phenylene.

[0101] In formula B, Ar3 and Ar4 each independently represent hydrogen, a substituted or unsubstituted (C6-C 30 )-aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl or a substituted or unsubstituted (C3-C 30)-Cycloalkyl. According to one embodiment of the present disclosure, Ar3 and Ar4 can each independently form a substituted or unsubstituted (C6-C 30 )-aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl or a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, preferably a substituted or unsubstituted (C3-C 30 )-cycloalkyl, according to another embodiment of the present invention, Ar3 and Ar4 can each independently form a substituted or unsubstituted (C6-C 20 )-Aryl, a substituted or unsubstituted (3- to 20-membered) hteroaryl or a substituted or unsubstituted (C3-C 20)-cycloalkyl. For example, Ar3 and Ar4 can 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 )-Cycloalkyl is.

[0102] In Formula B, R 51 and R 54 each independently for hydrogen, halogen, cyano, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted mono- or di-(C1-C 30 )-alkylamino, a substituted or unsubstituted mono- or di-(C6-C 3o)-arylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(C6-C 30 )-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)-heteroarylamino or a substituted or unsubstituted (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino. According to one embodiment of the present disclosure, R 51 to R 54 each independently for hydrogen, a substituted or unsubstituted (C1-C 30 )-Alkyl or a substituted or unsubstituted (C6-C 30 )-Aryl. For example, R 51 to R 54 be hydrogen, with the proviso that R 41 to R 54 , L3, L4, Ar3 and Ar4 do not contain deuterium.

[0103] The organic electroluminescent compound represented by formula 4 may be selected from the following compounds, but is not necessarily limited to them.

[0104] An organic electroluminescent material according to an embodiment of the present disclosure may contain an organic electroluminescent compound represented by formula 1' which contains at least one deuterium or an organic electroluminescent compound represented by formula 4.

[0105] An organic electroluminescent device according to an embodiment of the present disclosure may contain an organic electroluminescent compound represented by formula 1', comprising at least one deuterium, or an organic electroluminescent compound represented by formula 4.

[0106] An organic electroluminescent device according to one embodiment of the present disclosure may comprise an organic electroluminescent compound, represented by formula 1', comprising at least one deuterium element, or an organic electroluminescent compound, represented by formula 4, in at least one layer comprising 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. The light-emitting layer may contain one or more hosts and one or more dopants. Optionally, the light-emitting layer may comprise a co-host material, i.e., two or more of several host materials.

[0107] The host used in the present invention can be a phosphorescent host compound or a fluorescent host compound, and these host compounds are not subject to any special restrictions.

[0108] According to one embodiment of the present disclosure, the doping concentration of the dopant compound, based on the host compound of the light-emitting layer, can be less than 20 wt.%. One or more phosphorescent or fluorescent dopants can be used as the dopant in the organic electroluminescent device of the present disclosure, and a phosphorescent dopant is preferred.The phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not subject to any particular restrictions, but it may be one or more complex compounds of one or more metal atoms selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), in some cases preferably one or more ortho-metallated complex compounds of one or more metal atoms selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and in some cases further preferably one or more ortho-metallated iridium complex compounds.

[0109] The dopant contained in the organic electroluminescent device of the present disclosure may use, but is not limited to, the compound represented by formula 101 or 102 below.

[0110] It is true that in Formula 101 and 102

[0111] L' is selected from one of the following structures 1 to 3:

[0112] R 100 to R 103 each independently for hydrogen, deuterium, halogen, (C1-C 30 )-Alkyl, unsubstituted or substituted by deuterium and / or halogen, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, cyano, a substituted or unsubstituted (3- to 30-membered) heteroaryl or a substituted or unsubstituted (C1-C 30)-alkoxy or may be linked to the neighboring substituents to form one or more rings, for example to form one or more rings with a pyridine, e.g. a substituted or unsubstituted quinoline, a substituted or unsubstituted isoquinoline, a substituted or unsubstituted thienopyridine, a substituted or unsubstituted benzofuropyridine, a substituted or unsubstituted benzothienopyridine, a substituted or unsubstituted indenopyridine, a substituted or unsubstituted benzofuroquinoline, a substituted or unsubstituted benzothienoquinoline or a substituted or unsubstituted indenoquinoline;

[0113] R 104 to R 107 each independently for hydrogen, deuterium, halogen, (C1-C 30 )-Alkyl, unsubstituted or substituted by deuterium and / or halogen, a substituted or unsubstituted (C3-C 30)-Cycloalkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, cyano, a substituted or unsubstituted (C1-C 30 )-Alkoxy or a substituted or unsubstituted di-(C1-C 30 )-alkylamino or may be linked to one or more neighboring substituents to form one or more substituted or unsubstituted rings, for example to form one or more rings with a benzene, e.g. a substituted or unsubstituted naphthalene, a substituted or unsubstituted fluorene, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted indenopyridine, a substituted or unsubstituted benzofuropyridine or a substituted or unsubstituted benzothienopyridine;

[0114] R 201 to R220 each independently for hydrogen, deuterium, halogen, (C1-C 30 )-Alkyl, unsubstituted or substituted by deuterium and / or halogen, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (C1-C 30 )-Alkoxy or a substituted or unsubstituted di-(C1-C 30)-alkylamino or may be linked to one or more neighboring substituents to form one or more substituted or unsubstituted rings, for example to form one or more rings, e.g. a substituted or unsubstituted benzene, a substituted or unsubstituted fluorene, a substituted or unsubstituted benzofuran, a substituted or unsubstituted benzothiophene, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted furopyridine or a substituted or unsubstituted thiophene;

[0115] Z1 to Z4 each stand independently for N or CK1;

[0116] K1 each independently for hydrogen, deuterium, halogen, (C1-C 30 )-Alkyl, unsubstituted or substituted by deuterium and / or halogen, a substituted or unsubstituted (C3-C 30)-Cycloalkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, cyano, a substituted or unsubstituted (3- to 30-membered) heteroaryl or a substituted or unsubstituted (C1-C 30 )-Alkoxy may be linked to one or more neighboring substituents to form one or more substituted or unsubstituted rings, for example, to one or more rings, e.g., 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 dibenzothiophene; and

[0117] S stands for an integer from 1 to 3.

[0118] Specifically, the following are examples of dopant compounds, but they are not limited to them:

[0119] An organic electroluminescent device according to the present disclosure comprises an anode, a cathode, and at least one organic layer between the anode and the cathode. The organic layer contains a light-emitting layer and may further comprise at least one layer selected from a hole injection layer, a hole transport layer, a hole support layer, a light-emitting support 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 of the layers may additionally consist of several layers.

[0120] The anode and cathode can each be made of a transparent conductive material or a semi-transparent or reflective conductive material. Depending on the type of material used for the anode and cathode, the organic electroluminescent device can be of the top-emission, bottom-emission, or bi-side-emission type. Furthermore, the hole injection layer can be doped with a p-type dopant, and the electron injection layer can be additionally doped with an n-type dopant.

[0121] The organic layer may furthermore contain at least one compound from the group consisting of arylamine-based compounds and styrylarylamine-based compounds. In addition, the organic layer may furthermore contain at least one metal from the group consisting of Group 1 metals, Group 2 metals, transition metals of the 4th period, transition metals of the 5th period, lanthanides, and organic metals of the d-transition elements of the periodic table, or at least one complex compound containing such metals.

[0122] Furthermore, the organic electroluminescent device of the present disclosure can emit white light by including, in addition to the compound of the present disclosure, one or more light-emitting layers containing a blue, red, or green light-emitting compound known in the art. Optionally, a yellow or orange light-emitting layer may also be included.

[0123] In the organic electroluminescent device of the present disclosure, at least one layer (hereinafter referred to as "a surface layer"), selected from a chalcogenide layer, a halogenated metal layer, and a metal oxide layer, can preferably be arranged on at least one inner surface of a pair of electrodes. Specifically, a layer of chalcogenides (including oxides) of silicon and aluminum is preferably arranged on an anode surface of one side of a layer of a light-emitting medium, and a halogenated metal layer or a metal oxide layer is preferably arranged on a cathode surface of one side of a layer of a light-emitting medium. The surface layer ensures operational stability for the organic electroluminescent device. Preferably, the chalcogenide SiO₂ X (1≤X≤2), AlO X{1≤X≤1,5), SiON, SiAlON etc., includes the halogenated metal LiF, MgF2, CaF2, a rare earth metal fluoride etc. and includes the metal oxide Cs2O, Li2O, MgO, SrO, BaO, CaO etc.

[0124] 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 can be multilayered to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or electron blocking layer, with two compounds being used simultaneously in each layer. The hole transport layer or the electron blocking layer can also be multilayered.

[0125] An electron buffer layer, a hole-blocking layer, an electron transport layer, an electron injection layer, or a combination thereof can be used between the light-emitting layer and the cathode. The electron buffer layer can be multilayered to control electron injection and improve the interface properties between the light-emitting layer and the electron injection layer, with two compounds being used simultaneously in each of the multiple layers. The hole-blocking layer or the electron transport layer can also be multilayered, with multiple compounds being used in each layer.

[0126] The light-emitting auxiliary layer can be positioned between the anode and the light-emitting layer or between the cathode and the light-emitting layer. When positioned between the anode and the light-emitting layer, the auxiliary layer can be used to promote hole injection and / or hole transport, or to prevent electron overflow. Similarly, when positioned between the cathode and the light-emitting layer, the auxiliary layer can promote electron injection and / or electron transport, or to prevent hole overflow. Furthermore, the hole auxiliary layer can be positioned between the hole transport layer (or hole injection layer) and the light-emitting layer and can either promote or inhibit the hole transport rate (or hole injection rate), thereby controlling the charge balance.Furthermore, the electron-blocking layer is positioned between the hole transport layer (or hole injection layer) and the light-emitting layer. It can restrict the excitons in the light-emitting layer by blocking the overflow of electrons from the light-emitting layer, thus preventing light emission leakage. If an organic electroluminescent device contains two or more hole transport layers, the layer furthest from the others can be used as either the hole auxiliary layer or the electron-blocking layer. The light-emitting auxiliary layer, the hole auxiliary layer, or the electron-blocking layer improves the efficiency and / or lifetime of the organic electroluminescent device.

[0127] Furthermore, in the organic electroluminescent device of the present disclosure, a mixed region consisting of an electron transport compound and a reductive dopant, or a mixed region consisting of a hole transport compound and an oxidative dopant, can be arranged on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, making it easier to inject and transport electrons from the mixed region into a light-emitting medium. Furthermore, the hole transport compound is oxidized to a cation, making it easier to inject and transport holes from the mixed region into a light-emitting medium.Preferably, the oxidative dopant comprises various Lewis acid and acceptor compounds, and the reductive dopant comprises alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. Furthermore, a layer of reductive dopant can be used as a charge-generating layer to fabricate an organic electroluminescent device having two or more light-emitting layers and emitting white light.

[0128] According to one embodiment of the present disclosure, the organic electroluminescent device can be an organic electroluminescent device with a tandem structure. In the case of an organic electroluminescent tandem device, according to one embodiment, a single light-emitting unit (light-emitting part) can be formed in a structure in which two or more units are connected by a charge-generating layer. The organic electroluminescent device can include a plurality of two or more light-emitting units, for example, a plurality of three or more light-emitting units, with a first electrode and a second electrode facing each other on a substrate, and a light-emitting layer arranged between the first electrode and the second electrode, which emits light in a specific wavelength range.The organic electroluminescent device can contain multiple light-emitting units, each of which can contain a perforated transport belt, a light-emitting layer, and an electron transport belt. The perforated transport belt can contain a perforated injection layer and a perforated transport layer, and the electron transport belt can contain an electron transport layer and an electron injection layer. According to one embodiment, the light-emitting unit can contain three or more light-emitting layers. Multiple light-emitting units can emit the same color or different colors. Additionally, a light-emitting unit can contain one or more light-emitting layers, and the multiple light-emitting layers can be light-emitting layers of the same color or different colors.It can contain one or more charge-generating layers positioned between each light-emitting unit. A charge-generating layer is the layer where holes and electrons are generated when a voltage is applied. With three or more light-emitting units, a charge-generating layer can be positioned between each unit. These multiple charge-generating layers can be identical or different. Positioning the charge-generating layer between light-emitting units increases the current efficiency in each unit and facilitates charge distribution.Specifically, the charge generation layer is provided between two adjacent stacks and can be used to operate an organic electroluminescent tandem device using only one pair of anodes and cathodes without a separate internal electrode between the stacks.

[0129] The charge-generating layer can consist of an N-type charge-generating layer and a P-type charge-generating layer, and the N-type charge-generating layer can be doped with alkali metals, alkaline earth metals, or compounds of alkali metals and alkaline earth metals. The alkali metals can include one from the group consisting of Li, Na, K, Rb, Cs, Fr, Yb, and combinations thereof, and the alkaline earth metals can include one from the group consisting of Be, Mg, Ca, Sr, Ba, Ra, and combinations thereof. The P-type charge-generating layer can consist of metals or organic materials doped with a P-type dopant. For example, the metals can consist of one, two, or more alloys from the group consisting of Al, Cu, Fe, Pb, Zn, Au, Pt, W, In, Mo, Ni, and Ti.Additionally, commonly used materials can be used as P-type dopants and host materials used in P-type doped organic materials.

[0130] The organic electroluminescent material according to one embodiment of the present disclosure can be used as a light-emitting material for a white organic light-emitting device. Various structures have been proposed for the white organic light-emitting device, such as a side-by-side structure, a stacked structure according to the arrangement of red (R), green (G), or yellowish-green (YG) and blue (B) light-emitting units, or a method using color conversion material (CCM), etc. Furthermore, the organic electroluminescent material according to one embodiment of the present disclosure can also be used in the organic electroluminescent device with a quantum dot (QD).

[0131] Dry film formation processes such as vacuum evaporation, sputtering, plasma, ion plating, etc., or wet film formation processes such as inkjet printing, nozzle printing, spray coating, spin coating, dip coating, flooding, etc., can be used to form each layer of the organic electroluminescent device of the present disclosure. When using the first and second host compounds of the present disclosure to form a film, the process is carried out by co-deposition or mixed deposition.

[0132] Using a wet film formation process, a thin film can be formed by dissolving or diffusing each layer-forming material in a suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent can be any solvent in which the layer-forming materials can be dissolved or diffused and in which there are no problems regarding film-forming ability.

[0133] Furthermore, by using the organic electroluminescent device of the present disclosure, display devices such as smartphones, tablets, notebooks, PCs, televisions or display devices for vehicles or lighting devices such as outdoor or indoor lighting can be manufactured.

[0134] For a detailed understanding of the present disclosure, a representative compound from the present disclosure is used below to examine the manufacturing process of the compound according to the present disclosure, its physical properties, and the driving voltage and current efficiency of an OLED comprising an organic electroluminescent compound according to the present disclosure. However, the following examples are intended only to illustrate the properties of compounds according to the present disclosure and the OLEDs containing them, in order to understand the present disclosure in detail, and the present disclosure is not limited to the following examples.

[0135] For a detailed understanding of the present disclosure, a method for producing a compound according to the present disclosure will be explained below using the example of a synthesis method for a representative compound or intermediate of the present disclosure. [Example 1] Synthesis of compound C-51 1) Synthesis of compound 1-1

[0136] 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 tert-butoxide (NaOt-Bu) (22.9 g, 238.8 mmol) were placed in the flask, dissolved in 600 ml of xylene and stirred under reflux for 1 hour at 160 °C. After completion of the reaction, the reaction solution was cooled to room temperature, the solvent was removed by rotary evaporator and then purified by column chromatography, giving a liquid compound 1-1 (45 g, yield: 100 %) with viscosity. 2) Synthesis of compound C-51

[0137] 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, 50% solution in xylene), and NaOt-Bu (22.8 g, 237 mmol) were placed in the flask, dissolved in 600 mL of toluene, and stirred under reflux at 120 °C for 1 hour. After completion of the reaction, the solution was cooled to room temperature, the solvent was removed by rotary evaporator, and then purified by column chromatography, giving a white solid compound, C-51 (27.7 g, yield: 39.6%). MG Fp. C-51 589,87 208 °C [Example 2] Synthesis of compound C-53-D7

[0138] Compound C-51 was prepared by selecting from the deuteration methods disclosed in Korean patent registration publications No. 10-2283849 and No. 10-1427457, etc., giving compound C-53-D7 (18 g, yield: 78.3 %). MG Fp. C-53-D7 596,91 240 °C [Example 3] Synthesis of compound C-372 1) Synthesis of compound 3-1

[0139] 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 toluene, 200 ml ethanol, and 200 ml distilled water were dissolved in a flask and then stirred under reflux at 140 °C for 2 hours. Upon completion of the reaction, compound 3-1 (40.4 g, yield: 91.8%) was obtained by separation by column chromatography. 2) Synthesis of compound 3-2

[0140] 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 completion of the reaction, methanol was added to the reaction solution, and the resulting solid was filtered off under reduced pressure and separated by column chromatography, yielding compound 3-2 (11.8 g, yield: 63%). 3) Synthesis of compound C-372

[0141] 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, 50% solution in xylene), and NaOt-Bu (4.22 g, 43.9 mmol) were added to 200 ml of toluene and stirred under reflux for 1 hour. After completion of the reaction, methanol was added to the reaction solution, and the resulting solid was filtered off under reduced pressure and separated by column chromatography, giving compound C-372 (5.40 g, yield: 34.8%). MG Fp. C-372 708,03 230,6 °C [Example 4] Synthesis of compound C-351

[0142] 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, 50% solution in xylene), and NaOt-Bu (3.88 g, 40.4 mmol) were added to 200 ml of toluene and stirred under reflux for 1 hour. After completion of the reaction, methanol was added to the reaction solution, and the resulting solid was filtered off under reduced pressure and separated by column chromatography, giving compound C-351 (4.20 g, yield: 27.8%). MG Fp. C-351 748,09 273,5 °C [Example 5] Synthesis of compound C-370 1) Synthesis of compound 5-1

[0143] 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 completion of the reaction, methanol was added to the reaction solution, and the resulting solid was filtered off under reduced pressure and separated by column chromatography, giving compound 5-1 (7.90 g, yield: 23.0%). 2) Synthesis of compound C-370

[0144] 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, 50% solution in xylene) and NaOt-Bu (3.99 g, 41.5 mmol) were added to 230 ml of toluene and stirred under reflux for 1 hour.

[0145] After completion of the reaction, methanol was added to the reaction solution and the resulting solid was filtered off under reduced pressure and separated by column chromatography, giving compound C-370 (5.60 g, yield: 41.4%). MG Fp. C-370 655,95 162,7 °C [Example 6] Synthesis of compound C-326 1) Synthesis of compound 6-1

[0146] 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 toluene, 73 ml ethanol, and 73 ml distilled water were dissolved in a flask and then heated under reflux at 140 °C for 4 hours. Upon completion of the reaction, compound 6-1 (21 g, yield: 95%) was obtained by separation by column chromatography. 2) Synthesis of compound C-326

[0147] 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, 50% solution in xylene), and NaOt-Bu (10.0 g, 105 mmol) were added to 263 ml of toluene and stirred under reflux for 4 hours. After completion of the reaction, methanol was added to the reaction solution, and the resulting solid was filtered off under reduced pressure and separated by column chromatography, giving compound C-326 (17 g, yield: 54%). MG Fp. C-326 665,96 258,0 °C [Device Example 1] Production of a red light-emitting OLED according to the present disclosure

[0148] An OLED was fabricated according to the present disclosure. First, a transparent electrode thin film of indium tin oxide (ITO) (10 Ω / sq) on a glass substrate for an OLED (GEOMATEC CO., LTD., Japan) was successively subjected to ultrasonic washing with acetone and isopropyl alcohol, and subsequently stored and used in isopropyl alcohol. Next, the ITO substrate was mounted on a substrate holder of a vacuum vapor deposition (VAC) apparatus. Then, compound HI-1 was introduced into one cell of the VAC apparatus, while compound HT-1 was introduced into another cell. The two materials were vaporized at different rates, and compound HI-1 was deposited at a doping rate of 5 wt%, based on the total amount of compounds HI-1 and HT-1, to form a hole injection layer with a thickness of 10 nm.Compound HT-1 was then deposited as the first hole transport layer, 90 nm thick, on the hole injection layer. Next, compound C-51, shown below in Table 1, was introduced into another cell of the vacuum vapor deposition apparatus and vaporized by applying an electric current to the cell, forming a second hole transport layer, 60 nm thick, on top of the first hole transport layer. Then, compound HT-3 was introduced into another cell of the vacuum vapor deposition apparatus and vaporized by applying an electric current to the cell, forming a third hole transport layer, 7.5 nm thick, on top of the second hole transport layer. After the formation of the hole injection layer and the hole transport layers, a light-emitting layer was formed on top of them as follows: Compounds H1-10 and H3-28 from Table 1 below were introduced into two cells of the vacuum vapor deposition apparatus as hosts of the light-emitting layer, and compound D-39 was introduced into another cell as a dopant. The host materials H1-10 and H3-28 were evaporated at a rate of 4:6, and simultaneously the dopant material was evaporated at a different rate and deposited at a doping rate of 2 wt%, based on the total amount of hosts and dopant, to form a light-emitting layer 36 nm thick on the third hole transport layer. Next, compound B-3 was deposited as an electron buffer material 5 nm thick on the light-emitting layer. Then, compounds ET-1 and EI-1 were deposited as an electron transport layer 2:1 at a weight ratio of 2:1 to a thickness of 25 nm.After depositing compound EI-1 as a 2 nm thick electron injection layer on the electron transport layer, an 80 nm thick aluminum cathode was deposited on the electron injection layer using a further vacuum vapor deposition apparatus. This fabricated an OLED. Each compound was desealed by vacuum sublimation under 10°C. -6 Torr cleaned. [Device comparison examples 1 and 2] Production of red light emitting OLEDs that do not conform to the present disclosure

[0149] OLEDs were fabricated in the same way as in Device Example 1, except that the compounds from Table 1 below were used as materials for the second hole transport layer.

[0150] The driver voltage, current efficiency and CIE color coordinates at a luminance of 1000 nits for the organic electroluminescent devices according to Device Example 1 and Device Comparison Examples 1 and 2, which were manufactured as described above, were measured and the results are shown in Table 1 below. Table 1 Second hole transport layer light-emitting layer Driver voltage (V) Power efficiency [cd / A] CIE color coordinates (x, y) First Innkeeper Second innkeeper Device example 1 C-51 H1-10 H3-28 2,8 32,8 (0,660, 0,339) Device comparison example 1 HT2-1 H1-10 H3-28 3,9 30,5 (0,661, 0,339) Device comparison example 2 HT2-2 H1-10 H3-28 2,7 29,6 (0,661, 0,339)

[0151] It can be seen from Table 1 above that the organic electroluminescent device according to the present disclosure has a low driving voltage and / or a high current efficiency compared to the organic electroluminescent device in which a conventional compound was used as the second hole transport layer. [Device Example 2] Production of a red light-emitting OLED according to the present disclosure

[0152] An OLED was fabricated in the same manner as in Device Example 1, except that the host compounds from Table 2 below were used as host materials for the light-emitting layer. [Device comparison examples 3 and 4] Production of red light emitting OLEDs that do not conform to the present disclosure

[0153] OLEDs were fabricated in the same way as in Device Example 2, except that the compounds from Table 2 below were used as materials for the second hole transport layer.

[0154] The driver voltage, current efficiency and CIE color coordinates at a luminance of 1000 nits for the organic electroluminescent devices according to Device Example 2 and Device Comparison Examples 3 and 4, which were manufactured as described above, were measured and the results are shown in Table 2 below. Table 2 Second hole transport layer light-emitting layer Driver voltage (V) Power efficiency [cd / A] CIE color coordinates (x, y) First Innkeeper Second innkeeper Device example 2 C-51 H1-163 H3-345 2,8 32,4 (0,661, 0,339) Device comparison example 3 HT2-1 H1-163 H3-345 3,8 30,8 (0,661, 0,338) Device comparison example 4 HT2-2 H1-163 H3-345 2,7 29,7 (0,662, 0,338)

[0155] It can be seen from Table 2 above that the organic electroluminescent device according to the present disclosure has a low driving voltage and / or a high current efficiency compared to the organic electroluminescent device in which a conventional compound was used as the second hole transport layer. [Device Example 3] Production of a red light-emitting OLED according to the present disclosure

[0156] An OLED was fabricated in the same manner as in Device Example 1, except that the host compounds from Table 3 below were used as host materials for the light-emitting layer. [Device comparison examples 5 and 6] Production of red light emitting OLEDs that do not conform to the present disclosure

[0157] OLEDs were fabricated in the same way as in Device Example 3, except that the compounds from Table 3 below were used as materials for the second hole transport layer.

[0158] The driver voltage, current efficiency and CIE color coordinates at a luminance of 1000 nits for the organic electroluminescent devices according to Device Example 3 and Device Comparison Examples 5 and 6, which were manufactured as described above, were measured and the results are shown in Table 3 below. Table 3 Second hole transport layer light-emitting layer Driver voltage (V) Power efficiency [cd / A] CIE color coordinates (x, y) First Innkeeper Second Innkeeper Device example 3 C-51 H2-159 H3-352 2,8 32,7 (0,660, 0,339) Device comparison example 5 HT2-1 H2-159 H3-352 3,9 30,8 (0,661, 0,338) Device comparison example 6 HT2-2 H2-159 H3-352 2,7 30,1 (0,661, 0,338)

[0159] It can be seen from Table 3 above that the organic electroluminescent device according to the present disclosure has a low driving voltage and / or a high current efficiency compared to the organic electroluminescent device in which a conventional compound was used as the second hole transport layer. [Examples of devices 4 to 7] Production of red light-emitting OLEDs according to the present disclosure

[0160] OLEDs were fabricated in the same way as Device Example 1, except that the host compounds from Table 4 below were used as host materials for the light-emitting layer and the compounds from Table 4 below were used as materials for the second hole transport layer. [Device comparison examples 7 and 8] Production of red light emitting OLEDs that do not conform to the present disclosure

[0161] OLEDs were fabricated in the same manner as in Device Example 4, except that the compounds from Table 4 below were used as materials for the second hole transport layer.

[0162] The driver voltage, current efficiency and CIE color coordinates at a luminance of 1000 nits for the organic electroluminescent devices according to Device Examples 4 to 7 and Device Comparison Examples 7 and 8, which were manufactured as described above, were measured and the results are shown in Table 4 below. Table 4 Second hole transport layer light-emitting layer Driver voltage (V) Power efficiency [cd / A] CIE color coordinates (x, y) First Innkeeper Second Innkeeper Device example 4 C-326 H1-10 H3-28 2,8 34,4 (0,662, 0,338) Device example 5 C-351 H1-10 H3-28 2,9 34,6 (0,661, 0,339) Device example 6 C-370 H1-10 H3-28 2,9 34,9 (0,661, 0,338) Device example 7 C-372 H1-10 H3-28 2,9 34,6 (0,661, 0,338) Device comparison example 7 HT2-3 H1-10 H3-28 4,2 32,0 (0,662, 0,337) Device comparison example 8 HT2-4 H1-10 H3-28 3,0 30,9 (0,660, 0,339)

[0163] It can be seen from Table 4 above that the organic electroluminescent device according to the present disclosure has a low driving voltage and / or a high current efficiency compared to the organic electroluminescent device in which a conventional compound was used as the second hole transport layer. [Examples of devices 8 to 11] Production of red light-emitting OLEDs according to the present disclosure

[0164] OLEDs were fabricated in the same way as Device Example 1, except that the host compounds from Table 5 below were used as host materials for the light-emitting layer and the compounds from Table 5 below were used as materials for the second hole transport layer. [Device comparison examples 9 and 10] Production of red light emitting OLEDs that do not conform to the present disclosure

[0165] OLEDs were fabricated in the same way as in Device Example 8, except that the compounds from Table 5 below were used as materials for the second hole transport layer.

[0166] The driver voltage, current efficiency and CIE color coordinates at a luminance of 1000 nits for the organic electroluminescent devices according to Device Examples 8 to 11 and Device Comparison Examples 9 and 10, which were manufactured as described above, were measured and the results are shown in Table 5. Table 5 Second hole transport layer light-emitting layer Driver voltage (V) Power efficiency [cd / A] CIE color coordinates (x, y) First Innkeeper Second Innkeeper Device example 8 C-326 H1-163 H3-345 2,8 33,9 (0,662, 0,338) Device example 9 C-351 H1-163 H3-345 2,9 34,0 (0,662, 0,338) Device example 10 C-370 H1-163 H3-345 2,8 34,6 (0,662, 0,338) Device example 11 C-372 H1-163 H3-345 2,9 34,1 (0,661, 0,338) Device comparison example 9 HT2-3 H1-163 H3-345 4,6 31,9 (0,662, 0,337) Device comparison example 10 HT2-4 H1-163 H3-345 3,0 31,6 (0,661, 0,339)

[0167] It can be seen from Table 5 above that the organic electroluminescent device according to the present disclosure has a low driving voltage and / or a high current efficiency compared to the organic electroluminescent device in which a conventional compound was used as the second hole transport layer. [Examples of devices 12 to 15] Production of red light emitting OLEDs according to the present disclosure

[0168] OLEDs were fabricated in the same way as Device Example 1, except that the host compounds from Table 6 below were used as host materials for the light-emitting layer and the compounds from Table 6 below were used as materials for the second hole transport layer. [Comparative Examples 11 and 12] Production of red light-emitting OLEDs that do not conform to the present disclosure

[0169] OLEDs were fabricated in the same manner as in Device Example 12, except that the compounds from Table 6 below were used as materials for the second hole transport layer.

[0170] The driver voltage, current efficiency and CIE color coordinates at a luminance of 1000 nits for the organic electroluminescent devices according to Device Examples 12 to 15 and Device Comparison Examples 11 and 12, which were manufactured as described above, were measured and the results are shown in Table 6. Table 6 Second hole transport layer light-emitting layer Driver voltage (V) Power efficiency [cd / A] CIE color coordinates (x, y) First innkeeper Second Innkeeper Device example 12 C-326 H2-159 H3-352 2,8 34,6 (0,662, 0,338) Device example 13 C-351 H2-159 H3-352 2,9 34,4 (0,661, 0,338) Device example 14 C-370 H2-159 H3-352 2,8 34,8 (0,661, 0,338) Device example 15 C-372 H2-159 H3-352 2,8 34,4 (0,661, 0,338) Device comparison example 11 HT2-3 H2-159 H3-352 4,1 31,7 (0,662, 0,337) Device comparison example 12 HT2-4 H2-159 H3-352 3,0 31,6 (0,661, 0,339)

[0171] It can be seen from Table 6 above that the organic electroluminescent device according to the present disclosure has a low driving voltage and / or a high current efficiency compared to the organic electroluminescent device in which a conventional compound was used as the second hole transport layer. [Device Example 16] Production of a red light-emitting OLED according to the present disclosure

[0172] An OLED was fabricated in the same way as in Device Example 1, except that the compound from Table 7 below was used as the material for the second hole transport layer.

[0173] The lifetime and relative lifetime with respect to Comparative Example 1 at a luminance of 1000 nits for the organic electroluminescent devices according to Device Example 16 and Device Comparative Example 1, which were manufactured as described above, were measured, and the results are shown below in Table 7. Table 7 Second hole transport layer Light-emitting layer Lifespan (T 95 )[h] RelativeLebensdauer(T 95 )[%] First innkeeper Second innkeeper Device example 16 C-53-D7 H1-10 H3-28 41,5 2626,6 Device comparison example 1 HT2-1 H1-10 H3-28 1,58 100

[0174] It can be seen from Table 7 above that the organic electroluminescent device according to the present disclosure has a long lifetime compared to the organic electroluminescent device in which a conventional compound was used as the second hole transport layer.

[0175] The connections used in device examples 1 to 16 and device comparison examples 1 to 12 above are shown in Table 8 below. Table 8 Hole injection layer / hole transport layer Light-emitting layer Electron buffer layer / Electron transport layer Electron injection layer QUOTES INCLUDED IN THE DESCRIPTION

[0000] This list of documents cited by the applicant was automatically generated and is included solely for the reader's convenience. The list is not part of the German patent or utility model application. The DPMA accepts no liability for any errors or omissions. Cited patent literature

[0000] KR 2021-0124018

[0077] KR 2021-0006283

[0077] Cited non-patent literature

[0000] Appl. Phys. Lett. 51, 913, 1987

[0002]

Claims

[1] Organic electroluminescent device comprising a first electrode; a second electrode opposite the first electrode; a light-emitting layer between the first electrode and the second electrode; and a perforated conveyor belt between the first electrode and the light-emitting layer; wherein the perforated conveyor belt comprises a connection represented by the following formula 1 and the light-emitting layer comprises a compound represented by the following formulas 2 and 3: where X for -(CR9R 10 ) n - stands; R1 to R8 each independently for hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30)-Cycloalkyl, a substituted or unsubstituted (C1-C 30 )-Alkoxy, a substituted or unsubstituted tri-(C1-C 30 )-alkylsilyl, a substituted or unsubstituted di-(C1-C 30 )-alkyl-(Cr6-C 30 )-arylsilyl, a substituted or unsubstituted (C1-C 30 )-Alkyldi-(C6-C 30 )-arylsilyl, a substituted or unsubstituted tri-(C6-C 30 )-arylsilyl, a substituted or unsubstituted fused ring consisting of an aliphatic (C3-C 30 )-ring and an aromatic (C6-C 30 )-ring, a substituted or unsubstituted mono- or di-(C1-C 30 )-alkylamino, a substituted or unsubstituted mono- or di-(C6-C 30 )-arylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(C6-C 30)-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)-heteroarylamino or a substituted or unsubstituted (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino are present; R9 and R 10 each independently for hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted mono- or di-(C1-C 30 )-alkylamino, a substituted or unsubstituted mono- or di-(C6-C 3o )-arylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(C6-C 30)-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)-heteroarylamino or a substituted or unsubstituted (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino can stand or be linked with the neighboring substituents to form one or more rings; with the proviso that at least one of R1 to R 10 represented by the following formula A: where L, L1 and L2 each independently for a single bond, a substituted or unsubstituted (C6-C 30 )-arylene, a substituted or unsubstituted (3- to 30-membered) heteroarylene or a substituted or unsubstituted (C3-C 30 )-Cycloalkylenes; and Ar1 and Ar2 each independently for hydrogen, deuterium, a substituted or unsubstituted (C6-C 30)-aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl or a substituted or unsubstituted (C3-C 30 )-Cycloalkyl stand, with the proviso that at least one of Ar1 and Ar2 is used for a substituted or unsubstituted (C3-C 30 )-Cycloalkyl stands; and n represents an integer with a value of 1 or 2, and then, if n is 2, R9 and R 10 They may be the same or different; where L 11 to L 13 each independently for a single bond, a substituted or unsubstituted (C6-C 30 )-arylene or a substituted or unsubstituted (3- to 30-membered) heteroarylene; Ar 11 for a substituted or unsubstituted (C6-C 30 )-aryl or a substituted or unsubstituted (3- to 30-membered) heteroaryl; and Ar 12 and Ar 13each independently for hydrogen, deuterium, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted (C1-C 30 )-Alkoxy, a substituted or unsubstituted tri-(C1-C 30 )-alkylsilyl, a substituted or unsubstituted di-(C1-C 30 )-alkyl-(C6-C 30 )-arylsilyl, a substituted or unsubstituted (C1-C 30 )-Alkyldi-(C6-C 30 )-arylsilyl, a substituted or unsubstituted tri-(C6-C 30 )-arylsilyl, a substituted or unsubstituted mono- or di-(C1-C 30 )-alkylamino, a substituted or unsubstituted mono- or di-(C2-C 30 )-alkenylamino, a substituted or unsubstituted (C1-C 30)-Alkyl-(C2-C 30 )-alkenylamino, a substituted or unsubstituted mono- or di-(C6-C 30 )-arylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(C6-C 30 )-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)-heteroarylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(3- to 30-membered)-heteroarylamino, a substituted or unsubstituted (C2-C 30 )-Alkenyl-(C6-C 30 )-arylamino, a substituted or unsubstituted (C2-C 30 )-Alkenyl-(3- to 30-membered)-heteroarylamino or a substituted or unsubstituted (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino are present; where X1 to X3 each independently for N or CR 21 stand; provided that at least one of X1 to X3 is N; R 21each independently for hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted (C1-C 30 )-Alkoxy, a substituted or unsubstituted tri-(C1-C 30 )-alkylsilyl, a substituted or unsubstituted di-(C1-C 30 )-alkyl-(C6-C 30 )-arylsilyl, a substituted or unsubstituted (C1-C 30 )-Alkyldi-(C6-C 30 )-arylsilyl, a substituted or unsubstituted tri-(C6-C 30 )-arylsilyl or a substituted or unsubstituted fused ring consisting of an aliphatic (C3-C 30 )-ring and an aromatic (C6-C 30 )-Ring stands; L 21 to L 23each independently for a single bond, a substituted or unsubstituted (C6-C 30 )-arylene or a substituted or unsubstituted (3- to 30-membered) heteroarylene; and Ar 21 to Ar 23 each independently for hydrogen, deuterium, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, a substituted or unsubstituted fused ring of an aliphatic (C3-C 30 )-ring and an aromatic (C6-C 30 )-ring, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted tri-(C1-C 30 )-alkylsilyl, a substituted or unsubstituted di-(C1-C 30 )-alkyl-(C6-C 30)-arylsilyl, a substituted or unsubstituted (C1-C 30 )-Alkyldi-(C6-C 30 )-arylsilyl or a substituted or unsubstituted tri-(C6-C 3o )-arylsilyl stand. [2] Organic electroluminescent device according to claim 1, wherein 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 substituted fused ring of an aliphatic 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 substituted by at least one substituent,the group consisting of deuterium, halogen, cyano, carboxyl, nitro, hydroxy, (C1-C, 30 )-Alkyl, halogen-(C1-C 30 )-alkyl, (C2-C 30 )-Alkenyl, (C2-C 30 )-Alkynyl, (C1-C 30 )-Alkoxy, (C1-C 30 )-Alkylthio, (C3-C 30 )-Cycloalkyl, (C3-C 30 )-Cycloalkenyl, (3- to 7-membered) heterocycloalkyl, (C6-C 30 )-Aryloxy, (C6-C 30 )-Arylthio, (5- to 30-membered)heteroaryl, unsubstituted or modified by (C6-C 30 )-aryl is substituted, (C6-C 30 )-Aryl, which is unsubstituted or substituted by (5- to 30-membered) heteroaryl, Tri-(C1-C 30 )-alkylsilyl, Tri-(C6-C 30 )-arylsilyl, Di-(C1-C 30 )-alkyl-(C6-C 30 )-arylsilyl, (C1-C 30 )-Alkyldi-(C6-C 30 )-arylsilyl, an fused ring consisting of an aliphatic (C3-C 30 )-ring and an aromatic (C6-C 30 ) ring, amino, mono- or di-(C1-C 30)-alkylamino, a substituted or unsubstituted mono- or di-(C6-C 30 )-arylamino, (C1-C 30 )-Alkyl-(C6-C 30 )-arylamino, mono- or di-(3- to 30-membered)-heteroarylamino, (C1-C 30 )-Alkyl-(3- to 30-membered)-heteroarylamino, (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino, (C1-C 30 )-Alkylcarbonyl, (C1-C 30 )-Alkoxycarbonyl, (C6-C 30 )-Arylcarbonyl, (C6-C 30 )-Arylphosphinyl, Di-(C6-C 30 )-arylboronyl, Di-(C1-C 30 )-alkylboronyl, (C1-C 30 )-Alkyl-(C6-C 30 ) - arylboronyl, (C6-C 30 )-Ar-(C1-C 30 )-alkyl, (C1-C 30 )-Alkyl-(C6-C 30 )-aryl and a combination thereof is selected. [3] Organic electroluminescent device according to claim 1, wherein formula 1 is represented by one of the following formulas 1-1 to 1-4: wherein X, R1 to R8, L, L1, L2, Ar1 and Ar2 as defined in claim 1. [4] Organic electroluminescent device according to claim 1, wherein formula 1 is represented by formula 1-5 or 1-6: where R9' and R 10 ' each independently for hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted mono- or di-(C1-C 30 )-alkylamino, a substituted or unsubstituted mono- or di-(C6-C 3o )-arylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(C6-C 30)-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)-heteroarylamino or a substituted or unsubstituted (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino can stand alone or be linked with the neighboring substituents to form one or more rings; and R1 to R 10 as defined in claim 1. [5] Organic electroluminescent device according to claim 1, wherein Ar1 and Ar2 in formula A each independently for a substituted or unsubstituted (C3-C 30 )-Cycloalkyl stand. [6] Organic electroluminescent device according to claim 1, wherein at least one of Ar1 and Ar2 in formula A represents a substituted or unsubstituted cyclohexyl, a substituted or unsubstituted cyclopentyl, a substituted or unsubstituted norbornyl, or a substituted or unsubstituted adamantyl. [7] Organic electroluminescent device according to claim 1, wherein Ar 11 in formula 2 stands for a substituted or unsubstituted (3- to 30-membered) heteroaryl with 4 or more rings. [8] Organic electroluminescent device according to claim 1, wherein Ar 11 in Formula 2 is represented by Formula 2-1 or 2-2: where T1 and T2 are each independent for -N=, -NR 20 -, -O- or -S- stand for, with the proviso that one of T1 and T2 stands for -N= and the other of T1 and T2 for -NR 20 -, -O- or -S- stands; T3 stands for -O- or -S-; R 11 for a substituted or unsubstituted (C6-C 30 )-aryl or a substituted or unsubstituted (3- to 30-membered) heteroaryl is present; R 12 to R 19 and R 22 to R 33 each independently at L 11are bound or for hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted (C1-C 30 )-Alkoxy, a substituted or unsubstituted tri-(C1-C 30 )-alkylsilyl, a substituted or unsubstituted di-(C1-C 30 )-alkyl-(C6-C 30 )-arylsilyl, a substituted or unsubstituted (C1-C 30 )-Alkyldi-(C6-C 30 )-arylsilyl, a substituted or unsubstituted tri-(C6-C 30 )-arylsilyl, a substituted or unsubstituted fused ring consisting of an aliphatic (C3-C 30 )-ring and an aromatic (C6-C 30 )-ring, a substituted or unsubstituted mono- or di-(C1-C 30)-alkylamino, a substituted or unsubstituted mono- or di-(C2-C 30 )-alkenylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(C2-C 30 )-alkenylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(C6-C 30 )-arylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(3- to 30-membered)-heteroarylamino, a substituted or unsubstituted (C2-C 30 )-Alkenyl-(C6-C 30 )-arylamino, a substituted or unsubstituted (C2-C 30 )-Alkenyl-(3- to 30-membered)-heteroarylamino, a substituted or unsubstituted mono- or di-(C6-C 30 )-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)-heteroarylamino or a substituted or unsubstituted (C6-C 30)-Aryl-(3- to 30-membered)-heteroarylamino can stand or be linked with the neighboring substituents to form one or more rings, with the proviso that one of R 12 to R 19 in Formula 2-1 at L 11 is bound and one of R 22 to R 33 in Formula 2-2 at L 11 is bound. [9] Organic electroluminescent device according to claim 1, wherein formula 3 is represented by one of formulas 3-1 to 3-4: where YO, S or NR 36 is; R 34 to R 36 each independently for hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30)-Cycloalkyl, a substituted or unsubstituted (C1-C 30 )-Alkoxy, a substituted or unsubstituted tri-(C1-C 30 )-alkylsilyl, a substituted or unsubstituted di-(C1-C 30 )-alkyl-(C6-C 30 )-arylsilyl, a substituted or unsubstituted (C1-C 30 )-Alkyldi-(C6-C 30 )-arylsilyl, a substituted or unsubstituted tri-(C6-C 30 )-arylsilyl, a substituted or unsubstituted mono- or di(C1-C 30 )-alkylamino, a substituted or unsubstituted mono- or di-(C6-C 30 )-arylamino or a substituted or unsubstituted (C1-C 30 )-Alkyl(C6-C 30 )-arylamino or may be linked with the neighboring substituents to form one or more rings; L 21 to L 23 , Ar 22 and Ar 23 as defined in claim 1; n is an integer from 1 to 3, m is an integer from 1 to 4 and then, if n and m represent integers with a value of 2 or more, each of R 34 and each of R 35 They can be the same or different. [10] Organic electroluminescent device according to claim 1, wherein the compound represented by formula 1 is selected from the following compounds: where in the above compounds D'' means that n hydrogen atoms are replaced by deuterium, where n is an integer greater than or equal to 1 and is an integer from 1 to the maximum number of hydrogen atoms in the compound. [11] Organic electroluminescent device according to claim 1, wherein the compound represented by formula 2 is selected from the following compounds: where in the above compounds D'' means that n hydrogen atoms are replaced by deuterium, where n is an integer greater than or equal to 1 and is an integer from 1 to the maximum number of hydrogen atoms in the compound. [12] Organic electroluminescent device according to claim 1, wherein the compound represented by formula 3 is selected from the following compounds: where in the above compounds D'' means that n hydrogen atoms are replaced by deuterium, where n is an integer greater than or equal to 1 and is an integer from 1 to the maximum number of hydrogen atoms in the compound. [13] Organic electroluminescent device according to claim 1, wherein the layer comprising the compound represented by formula 1 in the hole transport belt is a hole transport layer, a hole auxiliary layer, an electron blocking layer or a light-emitting auxiliary layer. [14] Organic electroluminescent device according to claim 1, further comprising an additional compound in the light-emitting layer which is different from the compound represented by formulas 2 and 3. [15] Organic electroluminescent device according to claim 1, wherein the light-emitting layer includes a red light-emitting layer. [16] Organic electroluminescent device represented by the following formula 1' and comprising at least one deuterium: wherein X for -CR9R 10 - stands; R1 to R8 each independently for hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted (C1-C 30 )-Alkoxy, a substituted or unsubstituted tri-(C1-C 30 )-alkylsilyl, a substituted or unsubstituted di-(C1-C 30 )-alkyl-(C6-C 30 )-arylsilyl, a substituted or unsubstituted (C1-C 30 )-Alkyldi-(C6-C 30 )-arylsilyl, a substituted or unsubstituted tri-(C6-C 30 )-arylsilyl, a substituted or unsubstituted fused ring consisting of an aliphatic (C3-C 30 )-ring and an aromatic (C6-C 30 )-ring, a substituted or unsubstituted mono- or di-(C1-C30 )-alkylamino, a substituted or unsubstituted mono- or di-(C6-C 3o )-arylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(C6-C 30 )-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)-heteroarylamino or a substituted or unsubstituted (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino are present; and R9 and R 10 each independently for hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted mono- or di-(C1-C 30 )-alkylamino, a substituted or unsubstituted mono- or di-(C6-C 3o)-arylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(C6-C 30 )-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)-heteroarylamino or a substituted or unsubstituted (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino can stand or be linked with the neighboring substituents to form one or more rings; with the proviso that at least one of R1 to R 10 represented by the following formula A: where L, L1 and L2 each independently for a single bond, a substituted or unsubstituted (C6-C 30 )-arylene, a substituted or unsubstituted (3- to 30-membered) heteroarylene or a substituted or unsubstituted (C3-C 30 )-Cycloalkylenes; and Ar1 and Ar2 each independently for hydrogen, deuterium, a substituted or unsubstituted (C6-C 30)-aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl or a substituted or unsubstituted (C3-C 30 )-Cycloalkyl stand, with the proviso that at least one of Ar1 and Ar2 is used for a substituted or unsubstituted (C3-C 30 )-Cycloalkyl stands. [17] Organic electroluminescent compound according to claim 16, wherein formula 1' is represented by one of formulas 1'-1 to 1'-4: wherein X, R1 to R8, L, L1, L2, Ar1 and Ar2 as defined in claim 16. [18] Organic electroluminescent compound according to claim 16, wherein Ar1 in formula A is a substituted (C3-C 30 )-Cycloalkyl and one or more substituents of the substituted cycloalkyl comprise(s) at least one deuterium. [19] Organic electroluminescent compound according to claim 16, wherein formula A is represented by the following formula B: where R 51 to R 54 each independently for hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30 )-Cycloalkyl, a substituted or unsubstituted mono- or di-(C1-C 30 )-alkylamino, a substituted or unsubstituted mono- or di-(C6-C 3o )-arylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(C6-C 30 )-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)-heteroarylamino or a substituted or unsubstituted (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino are present; and L1, L2, Ar1 and Ar2 as defined in claim 16. [20] Organic electroluminescent compound according to claim 16, wherein the compound represented by formula 1' is selected from the following compounds: wherein in the above compounds D'' means that n hydrogen atoms are replaced by deuterium, where n is an integer greater than or equal to 1 and is an integer from 1 to the maximum number of hydrogen atoms in the compound. [21] Organic electroluminescent material comprising the organic electroluminescent compound according to claim 16. [22] Organic electroluminescent device comprising the organic electroluminescent compound according to claim 16. [23] Organic electroluminescent device comprising the 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] Organic electroluminescent compound represented by the following formula 4: wherein X4 for -CR 49 R 50 - stands; and R 41 to R 50 each independently for hydrogen, halogen, cyano, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30)-Cycloalkyl, a substituted or unsubstituted mono- or di-(C1-C 30 )-alkylamino, a substituted or unsubstituted mono- or di-(C6-C 3o )-arylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(C6-C 30 )-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)-heteroarylamino or a substituted or unsubstituted (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino can stand or be linked with the neighboring substituents to form one or more rings; with the proviso that at least one of R 41 to R 48 represented by the following formula B: where L3 and L4 each independently for a single bond, a substituted or unsubstituted (C6-C 30)-arylene, a substituted or unsubstituted (3- to 30-membered) heteroarylene or a substituted or unsubstituted (C3-C 30 )-Cycloalkylenes; Ar3 and Ar4 each independently for hydrogen, a substituted or unsubstituted (C6-C 30 )-aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl or a substituted or unsubstituted (C3-C 30 )-Cycloalkyl stand, with the proviso that at least one of Ar3 and Ar4 is used for a substituted or unsubstituted (C3-C 30 )-Cycloalkyl stands; and R 51 to R 54 each independently for hydrogen, halogen, cyano, a substituted or unsubstituted (C1-C 30 )-Alkyl, a substituted or unsubstituted (C6-C 30 )-Aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C 30)-Cycloalkyl, a substituted or unsubstituted mono- or di-(C1-C 30 )-alkylamino, a substituted or unsubstituted mono- or di-(C6-C 3o )-arylamino, a substituted or unsubstituted (C1-C 30 )-Alkyl-(C6-C 30 )-arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)-heteroarylamino or a substituted or unsubstituted (C6-C 30 )-Aryl-(3- to 30-membered)-heteroarylamino are present, with the proviso that R 41 to R 54 , L3, L4, Ar3 and Ar4 do not contain deuterium. [25] Organic electroluminescent compound according to claim 24, wherein Ar3 and Ar4 each independently for a substituted or unsubstituted (C3-C 30 )-Cycloalkyl stand. [26] Organic electroluminescent compound according to claim 24, wherein the compound represented by formula 4 is selected from the following compounds: [27] Organic electroluminescent material comprising the organic electroluminescent compound according to claim 24. [28] Organic electroluminescent device comprising the organic electroluminescent compound according to claim 24. [29] Organic electroluminescent device comprising the 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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