Organic electroluminescence device and organic electroluminescence compound

Abstract

This disclosure relates to an organic electroluminescent device comprising: a first electrode; a second electrode opposite to the first electrode; a light-emitting layer between the first electrode and the second electrode; and a hole transport band between the first electrode and the light-emitting layer, wherein the hole transport band comprises a compound represented by Formula 1, and the light-emitting layer comprises compounds represented by Formulas 2 and 3. By using compounds represented by Formulas 1, 2, and 3, the organic electroluminescent device according to this disclosure can exhibit high current efficiency.

Description

Technical Field

[0001] This disclosure relates to an organic electroluminescent device and an organic electroluminescent compound. Background Technology

[0002] Electroluminescent devices (EL devices) are self-emissive display devices that offer 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 a low molecular weight aromatic diamine and an aluminum complex as the material for forming the luminescent layer (see Appl. Phys. Lett. 51, 913, 1987).

[0003] Organic electroluminescent devices are constructed with multilayer structures to enhance their efficiency and stability. These multilayer structures include hole injection layers, hole transport layers, light-emitting layers, electron transport layers, and electron injection layers. In this paper, the selection of compounds contained in the hole transport layers is considered as one of the means to improve device characteristics such as hole transport efficiency to the light-emitting layer, current efficiency, and lifetime characteristics.

[0004] Various materials or concepts for hole transport layers in organic electroluminescent devices have been proposed to improve luminous efficiency, driving voltage, and / or lifetime. However, these have not been satisfactory in practical applications. Therefore, there is an ongoing need to develop organic electroluminescent devices with significantly improved performance compared to previously disclosed organic electroluminescent devices, such as improved driving voltage, luminous efficiency, current efficiency, and / or lifetime characteristics.

[0005] Meanwhile, Korean Patent Application Publication Nos. 10-2024-0052660 and 10-2023-0174704 disclose organic electroluminescent devices comprising a host compound represented by benzo[a]phenanthrenefuran or benzo[a]phenanthrenethiophene, a host compound represented by triazine, and a host compound represented by phenanthroxazole or phenanthrenethiazole. However, as described herein, no organic electroluminescent device is disclosed that exhibits improved performance due to a specific combination of hole transport region compounds as described in this invention and various host materials. Summary of the Invention

[0006] Problems to be solved

[0007] The purpose of this disclosure is to provide organic electroluminescent devices and organic electroluminescent compounds with improved current efficiency. Solution to the problem

[0008] As a result of in-depth research into solving the above-mentioned technical problems, the inventors of this invention have discovered that the aforementioned objective can be achieved by an organic electroluminescent device comprising the following: a first electrode; a second electrode opposite to the first electrode; a light-emitting layer between the first electrode and the second electrode; and a hole transport band between the first electrode and the light-emitting layer, wherein the hole transport band comprises a compound represented by Formula 1, and the light-emitting layer comprises a compound represented by Formula 2 and a compound represented by Formula 3, thereby completing the present invention.

[0009] --- (1)

[0010] --- (1-A)

[0011] In equations 1 and 2,

[0012] X represents O, S, or CR9R 10 ;

[0013] R9 and R 10 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C) 30 )alkyl, substituted or unsubstituted (C6-C 30 ) aryl, substituted or unsubstituted (3 to 30 yuan) heteroaryl, or substituted or unsubstituted (C3-C 30 )cycloalkyl; or may be linked with adjacent substituents to form one or more rings; and

[0014] R1 to R8 and R'1 to R'4 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C4) groups. 30 )alkyl, substituted or unsubstituted (C6-C 30 )Aryl, substituted or unsubstituted (3 to 30 yuan) Heteroaryl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (C1-C 30 )alkoxy, substituted or unsubstituted tri(C1-C) 30 )alkylsilyl, substituted or unsubstituted di(C1-C2) 30 )alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 )alkyl di(C6-C 30 arylsilyl, substituted or unsubstituted tri(C6-C) 30 )arylsilyl, (C3-C 30 Aliphatic rings and (C6-C) 30 Aromatic rings, whether substituted or unsubstituted, fused rings, mono- or di-(C1-C2) rings, whether substituted or unsubstituted. 30)alkylamino, substituted or unsubstituted mono- or di-(C6-C) 30 ) arylamino, substituted or unsubstituted (C1-C 30 )alkyl (C6-C 30 ) arylamino, substituted or unsubstituted mono- or di-(3- to 30-membered) heteroarylamino, or substituted or unsubstituted (C6-C 30 )Aryl (3- to 30-membered) heteroarylamino;

[0015] The premise is that a pair of bonds selected from R5 and R6, R6 and R7, and R7 and R8 are bonded together to form Equation 1-A. - Forming a ring;

[0016] The premise is that at least one of R1 to R8 and R'1 to R'4 is represented by the following formula A:

[0017] --- (A)

[0018] In equation A,

[0019] L, L1, and L2 each independently represent single-bonded, substituted, or unsubstituted (C6-C) bonds. 30 ) arylene, substituted or unsubstituted (3 to 30 yuan) heteroarylene, or substituted or unsubstituted (C3-C 30 )cycloalkylene; and

[0020] Ar1 and Ar2 independently represent substituted or unsubstituted (C6-C) compounds. 30 )Aryl, or substituted or unsubstituted (3 to 30 yuan) heteroaryl,

[0021] The prerequisite is that at least one of L, L1, L2, Ar1, and Ar2 must represent substituted or unsubstituted (C3-C) compounds. 30 )cycloalkyl or substituted or unsubstituted (C1-C 30 )alkyl.

[0022] --- (2)

[0023] In Equation 2,

[0024] L 11 To L 13 Each can be independently represented as a single bond, substituted or unsubstituted (C6-C). 30 ) aryl, or substituted or unsubstituted (3 to 30 yuan) heteroaryl;

[0025] Ar 11 Indicates substituted or unsubstituted (3 to 30 yuan) heteroaryl groups; and

[0026] Ar 12 and Ar 13 Each independently represents substituted or unsubstituted (C1-C) 30 )alkyl, substituted or unsubstituted (C6-C 30 )Aryl, substituted or unsubstituted (3 to 30 yuan) Heteroaryl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (C1-C 30 )alkoxy, substituted or unsubstituted tri(C1-C) 30 )alkylsilyl, substituted or unsubstituted di(C1-C2) 30 )alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 )alkyl di(C6-C 30 arylsilyl, substituted or unsubstituted tri(C6-C) 30 ) arylsilyl, substituted or unsubstituted mono- or di(C1-C2) 30 )alkylamino, substituted or unsubstituted mono- or di(C2-C) 30 alkenylamino, substituted or unsubstituted (C1-C) 30 )alkyl (C2-C 30 alkenylamino, substituted or unsubstituted mono- or di(C6-C) 30 ) arylamino, substituted or unsubstituted (C1-C 30 )alkyl (C6-C 30 ) arylamino, substituted or unsubstituted mono- or di(3- to 30-membered) heteroarylamino, substituted or unsubstituted (C1-C 30 )alkyl (3- to 30-membered) heteroarylamino, substituted or unsubstituted (C2-C 30 )alkenyl (C6-C 30 ) arylamino, substituted or unsubstituted (C2-C 30 Alkenyl (3 to 30 nucleotides) heteroaryl amino groups, or substituted or unsubstituted (C6-C) 30 )Aryl (3 to 30) heteroarylamino.

[0027] --- (3)

[0028] In Equation 3,

[0029] X1 to X3 each independently represent N or CR 21 The premise is that at least one of X1 to X3 is N;

[0030] Each R 21 Independently representing hydrogen or deuterium;

[0031] L 21 To L 23 Each can be independently represented as a single bond, substituted or unsubstituted (C6-C). 30 ) aryl, or substituted or unsubstituted (3 to 30 yuan) heteroaryl; and

[0032] Ar 21 To Ar 23 Each independently represents substituted or unsubstituted (C1-C) 30 )alkyl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, (C3-C 30 Aliphatic rings and (C6-C) 30 Aromatic rings, whether substituted or unsubstituted, fused rings, substituted or unsubstituted (C6-C) 30 )Aryl, or substituted or unsubstituted (3 to 30 yuan) heteroaryl;

[0033] The premise is Ar 21 To Ar 23 At least one of them represents a substituted or unsubstituted (3 to 30) heteroaryl group.

[0034] Furthermore, the inventors of this invention have discovered that the aforementioned objective can be achieved by organic electroluminescent compounds represented by the following compounds, thereby completing this invention.

[0035]

[0036] Beneficial effects of the present invention

[0037] By using the organic electroluminescent compound according to the present disclosure, an organic electroluminescent device with improved current efficiency can be provided. Embodiments of the present invention

[0038] This disclosure will now be described in detail. However, the following description is intended to explain the invention and is not intended to limit the scope of the invention in any way.

[0039] As used in this disclosure, the term "organic electroluminescent compound" means a compound that can be used in an organic electroluminescent device and, if necessary, can be included in any layer constituting the organic electroluminescent device.

[0040] This disclosure relates to an organic electroluminescent device comprising: a first electrode; a second electrode opposite to the first electrode; a light-emitting layer between the first electrode and the second electrode; and a hole transport band between the first electrode and the light-emitting layer, wherein the hole transport band comprises a compound represented by Formula 1, and the light-emitting layer comprises a compound represented by Formula 2 and a compound represented by Formula 3.

[0041] As used in this disclosure, the term "organic electroluminescent material" means a material that can be used in an organic electroluminescent device and may contain at least one compound. If desired, the organic electroluminescent material may be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material (comprising a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc. The hole transport band material may be at least one selected from the group consisting of: hole transport materials, hole injection materials, electron blocking materials, hole auxiliary materials, and light-emitting auxiliary materials.

[0042] The organic electroluminescent material of this disclosure may comprise at least one compound represented by Formula 1. The compound having Formula 1 may be included in at least one layer constituting an organic electroluminescent device, and may be included in at least one layer constituting a hole transport band, but is not limited thereto. When the compound having Formula 1 is included in a hole transport layer, a hole auxiliary layer, an electron blocking layer, a light-emitting layer, or a light-emitting auxiliary layer, it may be included as a hole transport material, a hole auxiliary material, an electron blocking material, a host material, or a light-emitting auxiliary material.

[0043] The term "multiple host materials" in this disclosure refers to a host material comprising a combination of at least two compounds, which may be included in any light-emitting layer constituting an organic electroluminescent device. It can mean both materials included before (e.g., before vapor deposition) and materials included after (e.g., after vapor deposition) the organic electroluminescent device. For example, the multiple host materials of this disclosure are combinations of at least two host materials, and may optionally further include conventional materials included in organic electroluminescent materials. Using methods commonly employed in the art, the at least two compounds included in the multiple host materials of this disclosure may be included together in a single light-emitting layer, or may be included separately in different light-emitting layers. For example, the at least two host materials may be mixed and evaporated or co-evaporated, or may be evaporated individually.

[0044] As used in this disclosure, "electron transport band" means the region in which electrons move between the light-emitting layer and the cathode. For example, the electron transport band may include at least one of a hole-blocking layer, an electron transport layer, and an electron injection layer, preferably at least one of an electron transport layer and an electron injection layer. The hole-blocking layer is used to prevent holes from entering the cathode through the light-emitting layer when driving the organic electroluminescent device.

[0045] As used in this disclosure, "hole transport band" refers to a region in which holes move between the first electrode and the light-emitting layer. For example, the hole transport band may include at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, and an electron blocking layer. Each of the hole injection layer, hole transport layer, hole auxiliary layer, light-emitting auxiliary layer, and electron blocking layer may be a single layer or a multilayer in which two or more or three or more layers are stacked. According to one embodiment of this disclosure, the hole transport band may include a first hole transport layer and a second hole transport layer, and may further include a third hole transport layer. The second and third hole transport layers may be at least one of a plurality of hole transport layers, and may include at least one of a hole auxiliary layer, a light-emitting auxiliary layer, and an electron blocking layer. Furthermore, according to another embodiment of this disclosure, the hole transport band may include a first hole transport layer and a second hole transport layer. The first hole transport layer may be placed between the first electrode and the light-emitting layer, and the second hole transport layer may be placed between the first hole transport layer and the light-emitting layer. The second hole transport layer may serve as a hole transport layer, a light-emitting auxiliary layer, a hole auxiliary layer, and / or an electron blocking layer. According to yet another embodiment of this disclosure, the hole transport band may include a first hole transport layer, a second hole transport layer, and a third hole transport layer. The first hole transport layer may be placed between the first electrode and the light-emitting layer, the second hole transport layer may be placed between the first hole transport layer and the light-emitting layer, and the third hole transport layer may be placed between the second hole transport layer and the light-emitting layer. The third hole transport layer may serve as a hole transport layer, a light-emitting auxiliary layer, a hole auxiliary layer, and / or an electron blocking layer.

[0046] In this disclosure, "(C1-C" 30 "alkyl" means a straight-chain or branched alkyl group having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10. Specific examples of alkyl groups may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.

[0047] The term "(C3-C" in this disclosure 30"Cycloalkyl" refers to a cyclic hydrocarbon substituent of a saturated or partially unsaturated monocyclic or polycyclic ring, specifically a monocyclic or polycyclic hydrocarbon having 3 to 30 carbon atoms in its cyclic skeleton, wherein the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7. Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. As non-limiting examples, monocyclic cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexenyl, cyclohexadienyl, cycloheptyl, cyclohepttrienyl, cyclooctyl, etc. Polycyclic cycloalkyl groups include spirocyclic, fused-ring, and cross-linked cycloalkyl groups. As non-limiting examples, cycloalkyl rings can be fused to form aryl, heteroaryl, or heterocyclic alkyl rings, and cycloalkyl rings include indanyl, tetrahydronaphthyl, and benzo[a]cyclo[b]cyclo[c]. Heptenyl, etc. A cross-linked cycloalkyl group refers to a 5- to 20-membered, preferably 6- to 14-membered, and more preferably 7- to 10-membered all-carbon polycyclic group having any two rings sharing two non-directly bonded carbon atoms. It may include one or more double bonds, but none of these rings have a fully conjugated π-electron system. Depending on the number of rings formed, it can be classified as a bicyclic, tricyclic, tetracyclic, or polycyclic cross-linked cycloalkyl group, preferably bicyclic, tricyclic, or tetracyclic, and more preferably bicyclic or tricyclic. Cross-linked cycloalkyl groups include, for example, adamantyl, norbornyl, norbornenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, etc.

[0048] In this disclosure, "(3- to 7-membered) heterocyclic alkyl" means a cycloalkyl group having 3 to 7, preferably 5 to 7, cyclic skeletal atoms and including at least one heteroatom selected from the group consisting of B, N, O, S, Si and P, preferably from the group consisting of O, S and N, for example, including tetrahydrofuran, pyrrolidine, tetrahydrothiophene, tetrahydropyran, etc.

[0049] “(C6-C 30"(Aromatic)aryl" is a monocyclic or fused-ring group derived from an aromatic hydrocarbon having 6 to 30 carbon atoms in its ring skeleton, wherein the number of carbon atoms in the ring skeleton is preferably 6 to 25, more preferably 6 to 18, and may be partially saturated. The aryl group may contain a spirostructure. Examples of aryl groups include phenyl, biphenyl, terphenyl, naphthyl, binatyl, phenylnaphthyl, naphthylphenyl, phenyl terphenyl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, dimethylfluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthrene, phenylphenanthrene, anthracene, indene, triphenylene, pyrene, tetraphenyl, peryl, phenyl, tetraphenyl, fluoranyl, spirodifluorenyl, etc. Specifically, examples of aryl groups may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthrayl, 2-anthrayl 9-Anthracene, benzo[a]anthracene, 1-Phenylenyl, 2-Phenylenyl, 3-Phenylenyl, 4-Phenylenyl, 9-Phenylenyl, tetraphenyl, pyrene, 1-phenyl, 2-phenyl, 3-phenyl, 4-phenyl, 5-phenyl, 6-phenyl, benzo[c]phenyl, benzo[g]phenyl, 1-Tripylidene, 2-Tripylidene, 3-Tripylidene, 4-Tripylidene, 1-fluorenyl 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo[a]fluorenyl, benzo[b]fluorenyl, benzo[c]fluorenyl, dibenzo[a]fluorenyl, 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-Triphenyl-2-yl, m-Tetraphenyl, 3-Fluoranthryl, 4-Fluoranthryl, 8-Fluoranthryl, 9-Fluoranthryl, Benzofluoranthyl, o-Tolyl, m-Tolyl, p-Tolyl, 2,3-Xylyl, 3,4-Xylyl, 2,5-Xylyl, Trimethylyl, o-Isopropylphenyl, m-Isopropylphenyl, p-Isopropylphenyl, p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 4′-Methylbiphenyl, 4″-tert-butyl-p-Triphenyl-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-di Methyl-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 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 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-phenanthyl, 9,9,10,10-tetramethyl-9,10-dihydro-2-phenanthyl, 9,9,10,10-tetramethyl-9,10-dihydro-3-phenanthyl, 9,9,10,10-tetramethyl-9,10-dihydro-4-phenanthyl, etc.

[0050] As used in this disclosure, the term "(3- to 30-membered) (hypo)aryl" refers to an (hypo)aryl group having 3 to 30 ring skeleton atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, P, Se, Te, and Ge. This heteroatom can be monocyclic or fused-ring type condensed with at least one benzene ring and can be partially saturated. The number of heteroatoms is preferably 1 to 4. Furthermore, the (hypo)aryl group in this disclosure can comprise a (hypo)aryl group formed by linking at least one heteroaryl or aryl group to the (hypo)aryl group via one or more single bonds, and can contain a spirostructure. Examples of heteroaryl groups can include monocyclic heteroaryl groups such as furanyl, thiopheneyl, pyrroleyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetraazinyl, triazolyl, tetraazolyl, furazanyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and fused-ring heteroaryl groups such as benzofuranyl, benzothiopheneyl, isobenzofuranyl, dibenzofuranyl, benzophenanthrenefuranyl, dibenzothiopheneyl, benzimidazolyl, etc. Benzothiazolyl, benzoisothiazolyl, benzophenanthrenethiophene, benzoisoxazolyl, benzoxazolyl, phenanthrenexazolyl, phenanthrenethiazolyl, isoindolyl, indolyl, benzoindolyl, indazole, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphridinyl, carbazole, benzocarbazole, dibenzocarbazole, phenoxazinyl, phenthiaazinyl, phenanthridine, benzodioxacyclopentenyl, dihydroacridinyl, etc. More specifically, examples of heteroaryl groups may include 1-pyrrolithyl, 2-pyrrolithyl, 3-pyrrolithyl, pyrazinyl, 2-pyridyl, 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-indololinyl, 2-indololinyl, 3-indololinyl, 5-indololinyl, 6-indololinyl, 7-indololinyl, 8-indololinyl, 2-imidazopyridyl, 3-imidazopyridyl, 5-imidazopyridyl, 6-imidazopyridyl, 7-imidazopyridyl, 8-imidazopyridyl, 3-pyridyl, 4-pyridyl 1-Indole, 2-Indole, 3-Indole, 4-Indole, 5-Indole, 6-Indole, 7-Indole, 1-Isoindole, 2-Isoindole, 3-Isoindole, 4-Isoindole, 5-Isoindole, 6-Isoindole, 7-Isoindole, 2-Furanyl, 3-Furanyl, 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-Quinolinyl, 3-Quinolinyl, 4-Quinolinyl, 5-Quinolinyl, 6-Quinolinyl7-quinolinyl, 8-quinolinyl, 1-isoquinolinyl, 3-isoquinolinyl, 4-isoquinolinyl, 5-isoquinolinyl, 6-isoquinolinyl, 7-isoquinolinyl, 8-isoquinolinyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazoleyl, 2-carbazoleyl, 3-carbazoleyl, 4-carbazoleyl, 9-carbazoleyl, azacarbazole-1-yl, azacarbazole Azoxy-2-yl, azacarbazolyl-3-yl, azacarbazolyl-4-yl, azacarbazolyl-5-yl, azacarbazolyl-6-yl, azacarbazolyl-7-yl, azacarbazolyl-8-yl, azacarbazolyl-9-yl, 1-phenanthridyl, 2-phenanthridyl, 3-phenanthridyl, 4-phenanthridyl, 6-phenanthridyl, 7-phenanthridyl, 8-phenanthridyl, 9-phenanthridyl 10-Phenyridyl, 1-Acridinel, 2-Acridinel, 3-Acridinel, 4-Acridinel, 9-Acridinel, 2-Oxazolyl, 4-Oxazolyl, 5-Oxazolyl, 2-Oxadiazolyl, 5-Oxadiazolyl, 3-Furazonyl, 2-Thienyl, 3-Thienyl, 2-Methylpyrrole-1-yl, 2-Methylpyrrole-3-yl, 2-Methylpyrrole-4-yl, 2-Methylpyrrole 5-ylpyrrolo-1-yl, 3-methylpyrrolo-2-yl, 3-methylpyrrolo-4-yl, 3-methylpyrrolo-5-yl, 2-tert-butylpyrrolo-4-yl, 3-(2-phenylpropyl)pyrrolo-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 [-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 ]-Benzofuranyl, 8-naphtho-[2,1-b]-benzofuranyl, 9-naphtho-[2,1-b]-benzofuranyl, 10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b]-benzothiophene, 2-naphtho-[1,2-b]-benzothiophene, 3-naphtho-[1,2-b]-benzothiophene, 4- Naphtho-[1,2-b]-benzothiophene, 5-naphtho-[1,2-b]-benzothiophene, 6-naphtho-[1,2-b]-benzothiophene, 7-naphtho-[1,2-b]-benzothiophene, 8-naphtho-[1,2-b]-benzothiophene, 9-naphtho-[1,2-b]-benzothiophene, 10-naphtho-[1,2-b] -Benzothiophene, 1-naphtho-[2,3-b]-benzothiophene, 2-naphtho-[2,3-b]-benzothiophene, 3-naphtho-[2,3-b]-benzothiophene, 4-naphtho-[2,3-b]-benzothiophene, 5-naphtho-[2,3-b]-benzothiophene, 1-naphtho-[2,1-b]-benzothiophene, 2-naphtho-[2,3-b]-benzothiophene -[2,1-b]-benzothiophene, 3-naphtho-[2,1-b]-benzothiophene, 4-naphtho-[2,1-b]-benzothiophene, 5-naphtho-[2,1-b]-benzothiophene, 6-naphtho-[2,1-b]-benzothiophene, 7-naphtho-[2,1-b]-benzothiophene, 8-naphtho-[2,1-b]-benzothiophene Thiophene, 9-naphtho-[2,1-b]-benzothiophene, 10-naphtho-[2,1-b]-benzothiophene, 2-benzofurano[3,2-d]pyrimidinyl, 6-benzofurano[3,2-d]pyrimidinyl, 7-benzofurano[3,2-d]pyrimidinyl, 8-benzofurano[3,2-d]pyrimidinyl, 9-benzofurano[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-benzofurano[3,2-d]pyrazinyl, 6-benzofurano[3,2-d] Pyrazinyl, 7-benzofurano[3,2-d]pyrazinyl, 8-benzofurano[3,2-d]pyrazinyl, 9-benzofurano[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-silylfluorenyl, 2-silylfluorenyl, 3-silylfluorenyl, 4-silylfluorenyl, 1-germaniumfluorenyl, 2-germaniumfluorenyl, 3-germaniumfluorenyl, 4-germaniumfluorenyl, 1-dibenzoselenyl, 2-dibenzoselenyl, 3-dibenzoselenyl, 4-dibenzoselenyl, etc. Furthermore, "(hybrid)aryl" can be classified into (hybrid)aryl groups with electronic properties and (hybrid)aryl groups with hole properties. (Hybrid)aryl groups with electronic properties are electron-rich substituents relative to the parent nucleus, and for example, can be substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazine, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinolinyl, etc. Hole-dependent (hetero)aryl groups are electron-deficient substituents relative to the parent nucleus, and can be, for example, substituted or unsubstituted carbazole groups, substituted or unsubstituted dibenzofuran groups, substituted or unsubstituted dibenzothiophene groups, etc. In this disclosure, the term "halogen" includes F, Cl, Br, and I.

[0051] As used in this disclosure, the term "(C3-C)" refers to... 30 Aliphatic rings and (C6-C) 30 "Fused ring of aromatic ring" refers to a functional group of a ring formed by fusion of at least one aliphatic ring having 3 to 30, preferably 3 to 25, and more preferably 3 to 18 carbon atoms in the ring skeleton and at least one aromatic ring having 6 to 30, preferably 6 to 25, and more preferably 6 to 18 carbon atoms in the ring skeleton. For example, a fused ring can be a fused ring of at least one benzene and at least one cyclohexane, or a fused ring of at least one naphthalene and at least one cyclopentane, etc. In this document, (C3-C 30 Aliphatic rings and (C6-C) 30 The carbon atom in the fused ring of the aromatic ring may be replaced by at least one heteroatom selected from B, N, O, S, Si, and P, preferably N, O, and S. In this disclosure, the term "halogen" includes F, Cl, Br, and I.

[0052] Furthermore, "ortho-", "(o-)", "meta-", "(m-)", and "para-", "(p-)" are each prefixes indicating the relative positions of substituents. The "ortho-" configuration describes a compound with substituents adjacent to each other, for example, at positions 1 and 2 on benzene. The "meta-" configuration describes the next substitution position after the immediately adjacent substitution position, for example, a compound with substituents at positions 1 and 3 on benzene. The "para-" configuration describes the next substitution position after the "meta" position, for example, a compound with substituents at positions 1 and 4 on benzene.

[0053] As used in this disclosure, the term "ring formed by connection with adjacent substituents" means a substituted or unsubstituted 3- to 30-membered monocyclic or polycyclic alicyclic ring, aromatic ring, or combination thereof formed by connecting or fused two or more adjacent substituents, and preferably, it can be a substituted or unsubstituted 3- to 26-membered monocyclic or polycyclic alicyclic ring, aromatic ring, or combination thereof. Furthermore, the formed ring may contain at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably N, O, and S.

[0054] Furthermore, the term "substituted" in the phrase "substituted or unsubstituted" means that a hydrogen atom in a functional group is replaced by another atom or functional group (i.e., a substituent). Unless otherwise specified, a substituent may replace hydrogen atoms at positions where it can be substituted without restriction, and when two or more hydrogen atoms in a functional group are each substituted by a substituent, each substituent may be the same or different. The maximum number of substituted substituents in a functional group can be the total number of substituted valences of each atom forming that functional group. In this document, substituted alkyl, substituted (aryl), substituted (heteroaryl), substituted (cycloalkyl), substituted (heteroaryl), substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted fused rings of aliphatic and aromatic rings, substituted mono- or dialkylamino, substituted mono- or di-enylamino, substituted alkylenylamino, substituted mono- or di-arylamino, substituted alkylarylamino, substituted alkylheteroarylamino, substituted alkenylarylamino, substituted alkenylheteroarylamino, substituted mono- or di-heteroarylamino, and substituted arylheteroarylamino are each independently selected from at least one of the following groups: deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C 30 alkyl, halogenated (C1-C) 30 )alkyl, (C2-C 30 )alkenyl, (C2-C 30 ) ynyl group, (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 group, (C6-C 30 )Aromatic thiols, surrounded by (C6-C 30 )Aryl-substituted or unsubstituted (3 to 30 yuan) heteroaryl, substituted or unsubstituted (C6-C) heteroaryl 30 )Aromatic, tri(C1-C30 )alkylsilyl, tri(C6-C 30 )arylsilyl, di(C1-C 30 )alkyl (C6-C 30 )arylsilyl, (C1-C 30 )alkyl di(C6-C 30 )arylsilyl, (C3-C 30 Aliphatic rings and (C6-C) 30 Fused rings of aromatic compounds, amino groups, mono- or di-(C1-C2) rings 30 )alkylamino, 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 )alkyl carbonyl, (C1-C 30 )alkoxycarbonyl, (C6-C 30 ) aryl carbonyl, (C6-C 30 )aryloxyphosphine, di(C6-C 30 )arylboronyl, di(C1-C 30 )alkylboronyl, (C1-C 30 )alkyl (C6-C 30 )arylboronyl, (C6-C 30 )Aryl(C1-C 30 )alkyl, (C1-C 30 )alkyl (C6-C 30 ) aryl, and combinations thereof. According to one embodiment of this disclosure, the substituted alkyl groups, etc., may each be independently substituted by at least one selected from the group consisting of: deuterium, cyano, (C1-C 30 )alkyl, (C3-C 30 )cycloalkyl, surrounded by (C6-C 30 Aryl-substituted or unsubstituted heteroaryl groups (priced between 5 and 30 yuan), and heteroaryl groups substituted or unsubstituted (priced between 5 and 30 yuan) (C6-C) 30 ) aryl, substituted or unsubstituted mono- or di-(C6-C) 30 ) arylamino groups and combinations thereof. According to another embodiment of this disclosure, the substituted alkyl groups, etc., may each be independently substituted with at least one group selected from the group consisting of: deuterium, cyano, (C1-C2) alkyl groups, etc. 20 )alkyl, (C3-C 20 )cycloalkyl, surrounded by (C6-C20 Aryl-substituted or unsubstituted heteroaryl groups (priced between 5 and 20 yuan), and heteroaryl groups substituted or unsubstituted (priced between 5 and 20 yuan) (C6-C) 20 ) aryl, substituted or unsubstituted mono- or di-(C6-C) 20 )Arylamino, and combinations thereof. For example, substituted alkyl groups may be independently substituted by at least one of the following groups: deuterium, cyano, unsubstituted or deuterated methyl, unsubstituted or deuterated isopropyl, tert-butyl, unsubstituted or deuterated cyclohexyl, unsubstituted or deuterated phenyl, deuterated, phenyl, or unsubstituted or deuterated naphthyl-substituted or unsubstituted naphthyl, biphenyl, phenanthrene, dibenzofuranyl, dibenzothiopheneyl, pyridyl, diphenylamino, carbazolyl, norbornyl, bicyclo[2.2.1]heptyl, cyclohexyl, and adamantyl.

[0055] In this document, when no substituents are indicated in the formula or compound structure, it may mean that all positions that can be substituted are either hydrogen or deuterium. That is, some hydrogen atoms can be deuterium, an isotope of hydrogen, where the deuterium content can be 0% to 100%. In this document, when no substituents are indicated in the formula or compound structure, hydrogen and deuterium can coexist in the compound 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 its element symbol can also be written as D or 2 H is one of the isotopes of hydrogen and has a deuterium nucleus consisting of one proton and one neutron. Isotopes refer to elements with the same atomic number (Z) but different mass numbers (A), and can also be interpreted as elements with the same number of protons but different numbers of neutrons.

[0056] An organic electroluminescent device according to one embodiment will be described below.

[0057] An organic electroluminescent device according to one embodiment includes a first electrode; a second electrode opposite to the first electrode; a light-emitting layer between the first electrode and the second electrode; and a hole transport band between the first electrode and the light-emitting layer, wherein the hole transport band contains a compound represented by Formula 1.

[0058] --- (1)

[0059] --- (1-A)

[0060] In Equation 1, X represents O, S, or CR9R. 10 .

[0061] In Equation 1, R9 and R 10Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C) 30 )alkyl, substituted or unsubstituted (C6-C 30 ) aryl, substituted or unsubstituted (3 to 30 yuan) heteroaryl, or substituted or unsubstituted (C3-C 30 )cycloalkyl; or may be linked with adjacent substituents to form one or more rings. According to one embodiment of this disclosure, R9 and R 10 They can be hydrogen, deuterium, substituted or unsubstituted (C1-C) independently. 30 )alkyl-substituted or unsubstituted (C6-C 30 The aryl group can be linked with adjacent substituents to form one or more rings. For example, R9 and R 10 They can each be methyl, ethyl, or phenyl independently, or they can be linked together to form a cyclopentane ring, and each can be independently substituted with deuterium.

[0062] In Formulas 1 and 1-A, R1 to R8 and R'1 to R'4 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C4) groups. 30 )alkyl, substituted or unsubstituted (C6-C 30 )Aryl, substituted or unsubstituted (3 to 30 yuan) Heteroaryl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (C1-C 30 )alkoxy, substituted or unsubstituted tri(C1-C) 30 )alkylsilyl, substituted or unsubstituted di(C1-C2) 30 )alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 )alkyl di(C6-C 30 arylsilyl, substituted or unsubstituted tri(C6-C) 30 )arylsilyl, (C3-C 30 Aliphatic rings and (C6-C) 30 Aromatic rings, whether substituted or unsubstituted, fused rings, mono- or di-(C1-C2) rings, whether substituted or unsubstituted. 30 )alkylamino, substituted or unsubstituted mono- or di-(C6-C) 30 ) arylamino, substituted or unsubstituted (C1-C 30 )alkyl (C6-C 30 ) arylamino, substituted or unsubstituted mono- or di-(3- to 30-membered) heteroarylamino, or substituted or unsubstituted (C6-C 30)aryl (3- to 30-membered) heteroarylamino; provided that it is selected from a pair of R5 and R6, R6 and R7, and R7 and R8 bonded together to form a compound of formula 1-A. - A ring is formed; provided that at least one of R1 to R8 and R'1 to R'4 is represented by the following formula A. According to one embodiment of this disclosure, R1 to R8 and R'1 to R'4 may each be independently hydrogen, deuterium, substituted or unsubstituted (C6-C4). 30 ) aryl, substituted or unsubstituted mono- or di-(C6-C) 30 ) arylamino, substituted or unsubstituted (C6-C 30 )aryl (3- to 30-membered) heteroarylamino or formula A. According to another embodiment of this disclosure, R1 to R8 and R'1 to R'4 can each independently be hydrogen, deuterium, phenyl or formula A below, and can be substituted with deuterium. The premise is that a pair selected from R5 and R6, R6 and R7, and R7 and R8 are bonded together to form a compound of formula 1-A. - A ring is formed.

[0063] --- (A)

[0064] In formula A, L, L1, and L2 independently represent single bonds, substituted bonds, or unsubstituted bonds (C6-C). 30 ) arylene, substituted or unsubstituted (3 to 30 yuan) heteroarylene, or substituted or unsubstituted (C3-C 30 ) Cycloalkylene. According to one embodiment of this disclosure, L, L1, and L2 each independently represent a single bond, substituted or unsubstituted (C6-C) 20 ) arylene, or substituted or unsubstituted (3- to 20-membered) heteroarylene. According to another embodiment of this disclosure, L, L1, and L2 each independently represent a single bond, or substituted or unsubstituted (C6-C) 12 ) arylene. For example, L, L1, and L2 can each be a single bond independently; unsubstituted or methyl-substituted phenylene, either unsubstituted or substituted with deuterium, tert-butyl, or naphthyl; unsubstituted or methyl-substituted biphenylene, etc., and each can be independently substituted with deuterium.

[0065] In formula A, Ar1 and Ar2 independently represent substituted or unsubstituted (C6-C) compounds. 30 Aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl. According to one embodiment of this disclosure, Ar1 and Ar2 each independently represent substituted or unsubstituted (C6-C6) heteroaryl groups. 20 Aryl or substituted or unsubstituted (3- to 20-membered) heteroaryl groups. According to another embodiment of this disclosure, Ar1 and Ar2 each independently represent substituted or unsubstituted (C6-C6) heteroaryl groups.18 Aryl. For example, Ar1 and Ar2 can each be independently unsubstituted or substituted with the following phenyl groups: methyl, ethyl, unsubstituted or substituted with methyl, phenyl, or biphenyl naphthyl, unsubstituted or substituted with deuterium isopropyl, tert-butyl, bicyclo[2,2,1]heptyl, adamantyl, or cyclohexyl; unsubstituted or substituted with unsubstituted or substituted with deuterium, isopropyl, tert-butyl, cyclopentyl, or naphthyl biphenyl; unsubstituted or substituted with methyl or phenyl terphenyl; unsubstituted or substituted with phenyl or methyl naphthyl; or substituted or unsubstituted tetraphenyl, etc., and each can be independently substituted with deuterium.

[0066] The prerequisite is that at least one of L, L1, L2, Ar1, and Ar2 must be substituted or unsubstituted (C3-C). 30 )cycloalkyl or substituted or unsubstituted (C1-C 30 Alkyl substitution.

[0067] According to one embodiment of this disclosure, at least one of L, L1, L2, Ar1, and Ar2 may be either substituted or unsubstituted (C3-C). 25 )cycloalkyl or substituted or unsubstituted (C1-C 25 Alkyl substitution. For example, at least one of L, L1, L2, Ar1, and Ar2 may be substituted with an unsubstituted or deuterated methyl, an unsubstituted or deuterated isopropyl, tert-butyl, bicyclo[2,2,1]heptyl, cyclohexyl, or adamantyl, which may be deuterated.

[0068] According to one embodiment of this disclosure, among the alkyl or cycloalkyl groups that must be substituted in Formula 1, the cycloalkyl group is a substituted or unsubstituted cyclohexyl, a substituted or unsubstituted norbornel, a substituted or unsubstituted adamantyl, or a substituted or unsubstituted cyclopentyl; and the alkyl group is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, and 3-pentyl, each of which is unsubstituted or deuterated.

[0069] According to one embodiment of this disclosure, Formula 1 can be represented by Formula 1-1 below.

[0070] --- (1-1)

[0071] In Equation 1-1, R1 to R4, R8 to R 10 R'1 to R'4, L, L1, L2, Ar1, and Ar2 are as defined above.

[0072] According to one embodiment of this disclosure, R9 and R 10Each can independently represent methyl, ethyl, phenyl, or a group consisting of these.

[0073] According to one embodiment of this disclosure, L can represent a single bond.

[0074] The compound represented by Formula 1 may be selected from, but is not limited to, the following compounds.

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088] In each of the above compounds, hydrogen can be replaced by deuterium.

[0089] The compound represented by Formula 1 according to this disclosure can be synthesized by reference to synthetic methods known to those skilled in the art, and in particular, synthetic methods disclosed in many patent documents can be used. For example, it can be synthesized by reference to synthetic methods disclosed in Korean Patent Application Publication Nos. 2015-0066202 (published on June 16, 2015) and 2017-0124957 (published on November 13, 2017), but is not limited thereto.

[0090] In the above organic electroluminescent devices, the light-emitting layer contains a compound represented by Formula 2 below.

[0091] --- (2)

[0092] In Equation 2, L11 To L 13 Each can be independently represented as a single bond, substituted or unsubstituted (C6-C). 30 ) arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene. According to one embodiment of this disclosure, L 11 To L 13 Each can be a single bond, substituted, or unsubstituted (C6-C) independently. 20 ) arylene, or substituted or unsubstituted (3 to 20) heteroarylene. For example, L 11 To L 13 Each of these components can be independently a single bond, an unsubstituted or deuterated phenylene, an unsubstituted or deuterated biphenylene, an unsubstituted or deuterated terphenylene, an unsubstituted or deuterated naphthylene, phenanthrene, dibenzofuranyl, dibenzothiopheneyl, carbazoyl, or pyridinyl, and each can be independently substituted with deuterium.

[0093] In Equation 2, Ar 11 This indicates substituted or unsubstituted (3- to 30-membered) heteroaryl groups. According to one embodiment of this disclosure, Ar... 11 It can be a substituted or unsubstituted (3- to 25-membered) heteroaryl group. According to another embodiment of this disclosure, Ar... 11 It can be a substituted or unsubstituted (3- to 30-membered) heteroaryl group having four or more rings. According to another embodiment of this disclosure, Ar... 11 It can be a substituted or unsubstituted (3- to 30-membered) heteroaryl group having four or more fused rings, which must contain an oxygen atom. According to another embodiment of this disclosure, Ar... 11 It can be represented by the following formula 2-1 or 2-2.

[0094] --- (2-1)

[0095] --- (2-2)

[0096] In equations 2-1 and 2-2, T1 and T2 independently represent -N= and -NR, respectively. 20 -, -O-, or -S-, provided that one of T1 and T2 represents -N=, and the other of T1 and T2 represents -NR. 20 -, -O-, or -S-. For example, T1 and T2 can each be independently -N=, -O-, or -S-.

[0097] In Equation 2-2, T3 represents O or S. For example, T3 can be O.

[0098] In Equation 2-1, R 11Indicates whether it is substituted or not substituted (C6-C) 30 ) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl. According to one embodiment of this disclosure, R 11 It can be substituted or unsubstituted (C6-C) 15 )Aryl or substituted or unsubstituted (3 to 10) heteroaryl groups. For example, R 11 It can be phenyl, naphthyl, biphenyl, or pyridyl, and can be further substituted with deuterium.

[0099] In equations 2-1 and 2-2, R 12 To R 19 and R 22 To R 33 Each independently with L 11 A link, or a symbol representing hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C) 30 )alkyl, substituted or unsubstituted (C6-C 30 )Aryl, substituted or unsubstituted (3 to 30 yuan) Heteroaryl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (C1-C 30 )alkoxy, substituted or unsubstituted tri(C1-C) 30 )alkylsilyl, substituted or unsubstituted di(C1-C2) 30 )alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 )alkyl di(C6-C 30 arylsilyl, substituted or unsubstituted tri(C6-C) 30 )arylsilyl, (C3-C 30 Aliphatic rings and (C6-C) 30 Aromatic rings, whether substituted or unsubstituted, fused rings, mono- or di-(C1-C2) rings, whether substituted or unsubstituted. 30 )alkylamino, substituted or unsubstituted mono- or di-(C2-C) 30 alkenylamino, substituted or unsubstituted (C1-C) 30 )alkyl (C2-C 30 alkenylamino, substituted or unsubstituted (C1-C) 30 )alkyl (C6-C 30 ) arylamino, substituted or unsubstituted (C1-C 30 )alkyl (3- to 30-membered) heteroarylamino, substituted or unsubstituted (C2-C 30 )alkenyl (C6-C 30 ) arylamino, substituted or unsubstituted (C2-C 30Alkenyl (3 to 30 quinones) heteroarylamino, substituted or unsubstituted mono- or di-(C6-C) 30 ) arylamino, substituted or unsubstituted mono- or di-(3- to 30-membered) heteroarylamino, or substituted or unsubstituted (C6-C 30 )aryl (3- to 30-membered) heteroarylamino; or may be linked with adjacent substituents to form one or more rings. According to one embodiment of this disclosure, R 12 To R 19 and R 22 To R 33 They can be hydrogen, deuterium, substituted or unsubstituted (C1-C) independently. 30 )alkyl, substituted or unsubstituted (C6-C 30 )Aryl, substituted or unsubstituted (3 to 30 yuan) Heteroaryl, substituted or unsubstituted (C3-C 30 )cycloalkyl, (C3-C 30 Aliphatic rings and (C6-C) 30 Aromatic rings, whether substituted or unsubstituted, fused rings, substituted or unsubstituted (C1-C2) rings 30 )alkyl (C6-C 30 ) arylamino, substituted or unsubstituted (C1-C 30 )alkyl (3- to 30-membered) heteroarylamino, substituted or unsubstituted mono- or di-(C6-C) 30 ) arylamino, substituted or unsubstituted mono- or di-(3- to 30-membered) heteroarylamino, or substituted or unsubstituted (C6-C 30 Aryl (3 to 30 members) heteroarylamino groups, or can be linked with adjacent substituents to form one or more rings. For example, R 12 To R 19 and R 22 To R 33 It can be either hydrogen or deuterium, each independently.

[0100] The premise is that R in Equation 2-1 12 To R 19 any one of them with L 11 Connect, and R in Equation 2-2 22 To R 33 any one of them with L 11 connect.

[0101] In Equation 2, Ar 12 and Ar 13 Each independently represents substituted or unsubstituted (C1-C) 30 )alkyl, substituted or unsubstituted (C6-C 30 )Aryl, substituted or unsubstituted (3 to 30 yuan) Heteroaryl, substituted or unsubstituted (C3-C30 )cycloalkyl, substituted or unsubstituted (C1-C 30 )alkoxy, substituted or unsubstituted tri(C1-C) 30 )alkylsilyl, substituted or unsubstituted di(C1-C2) 30 )alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 )alkyl di(C6-C 30 arylsilyl, substituted or unsubstituted tri(C6-C) 30 ) arylsilyl, substituted or unsubstituted mono- or di-(C1-C) 30 )alkylamino, substituted or unsubstituted mono- or di-(C2-C) 30 alkenylamino, substituted or unsubstituted (C1-C) 30 )alkyl (C2-C 30 alkenylamino, substituted or unsubstituted mono- or di-(C6-C) 30 ) arylamino, substituted or unsubstituted (C1-C 30 )alkyl (C6-C 30 ) arylamino, substituted or unsubstituted mono- or di-(3- to 30-membered) heteroarylamino, substituted or unsubstituted (C1-C 30 )alkyl (3- to 30-membered) heteroarylamino, substituted or unsubstituted (C2-C 30 )alkenyl (C6-C 30 ) arylamino, substituted or unsubstituted (C2-C 30 Alkenyl (3 to 30 nucleotides) heteroaryl amino groups, or substituted or unsubstituted (C6-C) 30 Aryl (3- to 30-membered) heteroarylamino. According to one embodiment of this disclosure, Ar... 12 and Ar 13 Each can be substituted or unsubstituted independently (C1-C). 30 )alkyl, substituted or unsubstituted (C6-C 30 )Aryl, substituted or unsubstituted (3 to 30 yuan) Heteroaryl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted mono- or di-(C6-C 30 ) arylamino, or substituted or unsubstituted (C6-C 30 Aryl (3- to 30-membered) heteroarylamino. According to another embodiment of this disclosure, Ar... 12 and Ar 13 Each can be substituted or unsubstituted (C6-C) independently. 30 )Aryl, substituted or unsubstituted (3 to 30 yuan) heteroaryl, substituted or unsubstituted mono- or di-(C6-C30 ) arylamino, or substituted or unsubstituted (C6-C 30 )Aryl (3- to 30-membered) heteroarylamino. For example, Ar 12 and Ar 13 It can be unsubstituted or unsubstituted or deuterated, cyano, unsubstituted or deuterated phenyl, biphenyl, unsubstituted or deuterated or phenyl-substituted naphthyl, phenanthryl, dibenzofuranyl, or carbazolyl substituted phenyl; unsubstituted or deuterated or phenyl-substituted biphenyl; unsubstituted or deuterated, unsubstituted or deuterated phenyl, or pyridyl-substituted naphthyl; unsubstituted or deuterated or phenyl-substituted phenanthryl; dimethylfluorenyl; dimethylbenzofluorenyl; unsubstituted or deuterated diphenylfluorenyl; unsubstituted or deuterated o-terphenyl; meta-terphenyl; unsubstituted or deuterated p-terphenyl; 2,6-dimethylphenyl; tert-butylphenyl; fluoranthyl; anthranyl; spirodifluorenyl; unsubstituted Tetraphenyl or deuterated tetraphenyl; unsubstituted or deuterated triphenylene; unsubstituted or deuterated, phenyl, or pyridyl dibenzofuranyl; unsubstituted or deuterated or phenyl-substituted dibenzothiophenyl; unsubstituted or phenyl-substituted pyridyl; benzonaphthofuranyl; benzonaphthothiophenyl; unsubstituted or phenyl- or biphenyl-substituted carbazoyl; phenoxazinyl; unsubstituted or phenyl-substituted benzimidazolyl; triphenylsilyl; dibenzoselenyl; methyl-substituted 14-membered heteroaryl; 22-membered heteroaryl; benzophenanthryl; benzonaphthoselenyl; diphenylamino; phenylbiphenylamino; phenyldibenzofuranylamino; phenyldibenzothiophenylamino; or phenylpyridylamino, and may be further substituted with deuterium.

[0102] The compound represented by Formula 2 may be selected from, but is not limited to, the following compounds.

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125] In the above compounds, D n This means that n hydrogen atoms are replaced by deuterium, where n is an integer from 1 to the maximum number of hydrogen atoms in the compound.

[0126] The compounds represented by Formula 2 according to this disclosure can be synthesized by reference to synthetic methods known to those skilled in the art, and in particular, synthetic methods disclosed in many patent documents can be used. For example, the compounds represented by Formula 2-1 according to this disclosure can be synthesized by reference to synthetic methods disclosed in Korean Patent Application Publication Nos. 2017-0022865 (published March 2, 2017) and 2018-0099487 (published September 6, 2018), but are not limited thereto. For example, the compounds represented by Formula 2-2 can be prepared as shown in reaction scheme 2 below, but are not limited thereto, and can also be prepared by synthetic methods known to those skilled in the art.

[0127] [Reaction Scheme 2]

[0128]

[0129] In reaction scheme 2 above, Ar 12 and Ar 13As defined in Equation 2, T3 is defined in Equation 2-2, and R is R in Equation 2-2. 22 To R 33 Defined in [the document / reference].

[0130] Furthermore, the light-emitting layer of the organic electroluminescent device contains not only the compound represented by Formula 2, but also the compound represented by Formula 3.

[0131]

[0132] In Equation 3, X1 to X3 each independently represent N or CR. 21 This is provided that at least one of X1 to X3 is N. For example, X1 to X3 are each N independently.

[0133] In Equation 3, each R 21 Independently represents hydrogen or deuterium.

[0134] In Equation 3, L 21 To L 23 Each can be independently represented as a single bond, substituted or unsubstituted (C6-C). 30 ) arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene. According to one embodiment of this disclosure, L 21 To L 23 Each can be a single bond, substituted, or unsubstituted (C6-C) independently. 20 ) arylene, or substituted or unsubstituted (3 to 20) heteroarylene. For example, L 21 To L 23 Each of these components can be independently a single bond, an unsubstituted or deuterated phenylene, an unsubstituted or deuterated biphenylene, a terphenylene, an unsubstituted or deuterated naphthylene, a phenanthrylene, a dibenzofuranylene, or a dibenzothiopheneylene, and can be further substituted with deuterium.

[0135] In Equation 3, Ar 21 To Ar 23 Each independently represents substituted or unsubstituted (C1-C) 30 )alkyl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, (C3-C 30 Aliphatic rings and (C6-C) 30 Aromatic rings, whether substituted or unsubstituted, fused rings, substituted or unsubstituted (C6-C) 30 ) aryl, substituted or unsubstituted (3 to 30) heteroaryl, provided that Ar 21 To Ar 23At least one of them represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group. According to one embodiment of this disclosure, Ar 21 To Ar 23 Each can be substituted or unsubstituted (C6-C) independently. 30 Aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl. According to another embodiment of this disclosure, Ar... 21 To Ar 23 At least one of them can be independently a substituted or unsubstituted (3-membered to 30-membered) heteroaryl group, preferably a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophene, or a substituted or unsubstituted carbazoleylaryl. For example, Ar 21 To Ar 23 Each of these can be an unsubstituted or substituted phenyl group: deuterium, unsubstituted or deuterated naphthyl, or unsubstituted or substituted naphthyl with phenyl, phenanthryl, or dibenzofuranyl; unsubstituted or substituted biphenyl with deuterium, naphthyl, or dibenzofuranyl; triphenylene; triphenylsilyl; o-terphenyl; m-terphenyl; unsubstituted or deuterated p-terphenyl; unsubstituted or substituted phenanthryl with phenyl or naphthyl; unsubstituted... Benzophenanthryl or deuterated; unsubstituted or deuterated, unsubstituted or deuterated phenyl, unsubstituted or deuterated naphthyl, unsubstituted or deuterated biphenyl, dibenzofuranyl, or dibenzothiophene-substituted naphthyl; tetraphenyl; fluoranthyl; unsubstituted or deuterated, phenyl, biphenyl, naphthyl, phenanthryl, or triphenylene-substituted dibenzofuranyl; or unsubstituted or phenyl-substituted dibenzothiophene, which may be further deuterated.

[0136] According to one embodiment of this disclosure, formula 3 can be represented by any one of formulas 3-1 to 3-4 below.

[0137] --- (3-1)

[0138] --- (3-2)

[0139] --- (3-3)

[0140] --- (3-4)

[0141] In equations 3-1 to 3-4, Y represents O, S, or NR. 36 For example, Y is -O- or -S-.

[0142] In equations 3-1 to 3-4, R 34 To R 36Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C) 30 )alkyl, substituted or unsubstituted (C6-C 30 )Aryl, substituted or unsubstituted (3 to 30 yuan) Heteroaryl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (C1-C 30 )alkoxy, substituted or unsubstituted tri(C1-C) 30 )alkylsilyl, substituted or unsubstituted di(C1-C2) 30 )alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 )alkyl di(C6-C 30 arylsilyl, substituted or unsubstituted tri(C6-C) 30 ) arylsilyl, substituted or unsubstituted mono- or di-(C1-C) 30 )alkylamino, substituted or unsubstituted mono- or di-(C6-C) 30 ) arylamino, or substituted or unsubstituted (C1-C 30 )alkyl (C6-C 30 ) arylamino; or may be linked with adjacent substituents to form one or more rings. According to one embodiment of this disclosure, R 34 To R 36 Each can be independently hydrogen, deuterium, or substituted or unsubstituted (C6-C) 30 Aryl. According to another embodiment of this disclosure, R 34 To R 36 Each can be independently hydrogen, deuterium, or substituted or unsubstituted (C6-C) 20 )Aryl. For example, R 34 To R 36 It can be hydrogen, deuterium, unsubstituted or naphthyl-substituted phenyl, unsubstituted or phenyl-substituted naphthyl, biphenyl, or phenanthrene, and can be further substituted with deuterium.

[0143] In equations 3-1 to 3-4, L 21 To L 23 Ar 22 And Ar 23 Same as defined in Equation 3.

[0144] In equations 3-1 to 3-4, n is an integer from 1 to 3, m is an integer from 1 to 4, and when n and m are integers of 2 or greater, each R 34 and each R 35 They can be the same as or different from each other.

[0145] The compound represented by Formula 3 may be selected from, but is not limited to, the following compounds.

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172] In the above compounds, D n This means that n hydrogen atoms are replaced by deuterium, where n is an integer from 1 to the maximum number of hydrogen atoms in the compound.

[0173] The compound represented by Formula 3 according to this disclosure can be synthesized by referring to the synthetic methods disclosed in Korean Patent Application Publication Nos. 2021-0124018 (published on October 14, 2021) and 2021-0006283 (published on January 18, 2021), but is not limited thereto.

[0174] The layer containing the compound represented by Formula 1 in the hole transport band of the above organic electroluminescent device can be a hole transport layer, a hole auxiliary layer, an electron blocking layer, or a light-emitting auxiliary layer.

[0175] The light-emitting layer of the above organic electroluminescent device may further contain other compounds different from those represented by Formulas 2 and 3.

[0176] In the above organic electroluminescent devices, the light-emitting layer may include a light-emitting layer that emits red light.

[0177] According to one embodiment of this disclosure, the present invention includes organic electroluminescent compounds represented by the following compounds.

[0178]

[0179]

[0180] According to one embodiment of this disclosure, this disclosure may include organic electroluminescent materials comprising the organic electroluminescent compounds described above.

[0181] According to one embodiment of this disclosure, this disclosure may include an organic electroluminescent device comprising the organic electroluminescent compound described above.

[0182] According to one embodiment of this disclosure, the disclosure may include an organic electroluminescent device that includes the organic electroluminescent compound described above 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.

[0183] Compounds C-6, C-9, C-10, C-61, C-64, C-65, C-136, C-139, C-140, C-166, C-167, C-168, C-171, C-172, C-173, C-176, C-186, C-187, C-303, C-304, C-305, C-306, and C-307 disclosed herein can be synthesized by referring to synthetic methods known to those skilled in the art, and in particular, synthetic methods disclosed in numerous patent documents can be used. For example, it can be synthesized by referring to synthetic methods disclosed in Korean Patent Application Publication Nos. 2015-0066202 (published June 16, 2015) and 2017-0124957 (published November 13, 2017), but is not limited thereto.

[0184] An organic electroluminescent device according to an embodiment of the present disclosure may include an organic electroluminescent compound represented by Formula 1 and containing at least one deuterium in at least one of the following layers: an emissive layer, a first hole transport layer, a second hole transport layer, a hole auxiliary layer, an electron blocking layer, and an emissive auxiliary layer. The emissive layer may contain one or more host materials and one or more dopants. If desired, the emissive layer may contain a co-host material, i.e., two or more host materials.

[0185] The host compound used in this invention can be a phosphorescent host compound or a fluorescent host compound, and there are no particular limitations on these host compounds.

[0186] As a dopant included in the organic electroluminescent device of this disclosure, one or more phosphorescent or fluorescent dopants may be used, with phosphorescent dopants being preferred. There are no particular limitations on the phosphorescent dopant material used in the organic electroluminescent device of this disclosure, 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, one or more ortho-metallized complex compounds of one or more metal atoms selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt) are preferred, and in some cases, one or more ortho-metallized iridium complex compounds are more preferred.

[0187] The dopants included in the organic electroluminescent devices of this disclosure may be compounds represented by formula 101 or 102, but are not limited thereto.

[0188]

[0189] In equations 101 and 102,

[0190] L' is selected from any one of the following structures 1 to 3:

[0191] --- Structure (1) --- Structure (2)

[0192] --- Structure (3)

[0193] R 100 To R 103 Each independently represents hydrogen, deuterium, halogen, substituted with deuterium and / or halogen or unsubstituted (C1-C). 30 )alkyl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (C6-C 30 ) aryl, cyano, substituted or unsubstituted (3 to 30 ppm) heteroaryl, or substituted or unsubstituted (C1-C2) 30 Alkoxy; or may be linked with adjacent substituents to form one or more rings, such as with pyridine to form one or more rings, such as substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted thienopyridine, substituted or unsubstituted benzofuranopyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted indenepyridine, substituted or unsubstituted benzofuranoquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indenequinoline;

[0194] R 104 To R 107 Each independently represents hydrogen, deuterium, halogen, substituted with deuterium and / or halogen or unsubstituted (C1-C). 30 )alkyl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (C6-C 30 )Aryl, substituted or unsubstituted (3 to 30 ppm) heteroaryl, cyano, substituted or unsubstituted (C1-C2) 30 )alkoxy, or substituted or unsubstituted di(C1-C) 30 Alkylamino; or may be linked with one or more adjacent substituents to form one or more rings, such as forming one or more rings with benzene, for example, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indopyridine, substituted or unsubstituted benzofuran-pyridine, or substituted or unsubstituted benzothiophene-pyridine;

[0195] R 201 To R 220 Each independently represents hydrogen, deuterium, halogen, substituted with deuterium and / or halogen or unsubstituted (C1-C). 30 )alkyl, substituted or unsubstituted (C3-C 30)cycloalkyl, substituted or unsubstituted (C6-C 30 ) aryl, substituted or unsubstituted (C1-C 30 )alkoxy, or substituted or unsubstituted di(C1-C) 30 Alkylamino; or may be connected to one or more adjacent substituents to form one or more substituted or unsubstituted rings; for example, to form one or more rings, such as substituted or unsubstituted pentane, substituted or unsubstituted propane, substituted or unsubstituted isobutane, substituted or unsubstituted 3-methylpentane, or substituted or unsubstituted trifluoro-2-methylpropane;

[0196] Z1 to Z3 each independently represent N or CK1;

[0197] K1 independently represents hydrogen, deuterium, halogen, substituted with deuterium and / or halogen or unsubstituted (C1-C). 30 )alkyl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (C6-C 30 ) aryl, cyano, substituted or unsubstituted (3 to 30 ppm) heteroaryl, or substituted or unsubstituted (C1-C2) 30 )alkoxy; or may be linked with one or more adjacent substituents to form one or more substituted or unsubstituted rings, for example, to form one or more rings, such as substituted or unsubstituted benzoquinazoline, substituted or unsubstituted benzoquinoxaline, substituted or unsubstituted quinoxaline, substituted or unsubstituted benzothienopyrimidine, substituted or unsubstituted benzothienopyrimidine, substituted or unsubstituted thienopyrimidine, substituted or unsubstituted thienopyrimidine, or substituted or unsubstituted benzothienopyridazine; and

[0198] s represents an integer from 1 to 3.

[0199] Specifically, examples of dopant compounds include, but are not limited to, the following.

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207] The organic electroluminescent device according to this disclosure has an anode; a cathode; and at least one organic layer inserted between the anode and the cathode. The organic layer includes a light-emitting layer and may further include at least one layer selected from: a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary 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 these layers may additionally consist of multiple layers.

[0208] The anode and cathode can each be formed from transparent, semi-transparent, or reflective conductive materials. Depending on the types of materials used to form the anode and cathode, the organic electroluminescent device can be a top-emitting, bottom-emitting, or dual-sided emitting type. Furthermore, the hole injection layer can be further doped with p-type dopant, and the electron injection layer can be additionally doped with n-type dopant.

[0209] The organic layer may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds. Furthermore, the organic layer may further comprise at least one metal selected from the group consisting of: metals of Group 1, Group 2, transition metals of Period 4, transition metals of Period 5, lanthanides, and organometallic compounds of d-transition elements, or at least one complex compound comprising such metal.

[0210] In addition to the compounds disclosed herein, the organic electroluminescent device of this disclosure may emit white light by further including one or more light-emitting layers containing compounds known in the art that emit blue, red, or green light. Additionally, if desired, a layer emitting yellow or orange light may be further included.

[0211] In the organic electroluminescent device disclosed herein, preferably, at least one layer selected from chalcogenide layers, metal halide layers, and metal oxide layers (hereinafter, "surface layer") can be placed on at least one of one or more inner surfaces of a pair of electrodes. Specifically, it is preferred to place silicon and aluminum chalcogenide (including oxide) layers on the anode surface on the light-emitting medium layer side, and it is also preferred to place the metal halide layer or metal oxide layer on the cathode surface on the light-emitting medium layer side. The operational stability of the organic electroluminescent device can be obtained through the surface layer. Preferably, the chalcogenide includes SiO2. X (1 ≤ X ≤ 2), AlO X (1 ≤ X ≤ 1.5), SiON, SiAlON, etc.; metal halides include LiF, MgF2, CaF2, rare earth metal fluorides, etc.; and metal oxides include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0212] 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. Multiple hole injection layers can be used to reduce the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or electron blocking layer, wherein each of these layers can use two compounds simultaneously. Furthermore, multiple hole transport layers or electron blocking layers can be used.

[0213] 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. Multiple electron buffer layers can be used to control electron injection and improve the interface properties between the light-emitting layer and the electron injection layer, where each of these layers can simultaneously utilize two compounds. Furthermore, multiple hole blocking or electron transport layers can be used, where each layer can utilize multiple compounds.

[0214] A light-emitting auxiliary layer can be placed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer. When placed between the anode and the light-emitting layer, it can promote hole injection and / or hole transport, or prevent electron leakage. When placed between the cathode and the light-emitting layer, it can promote electron injection and / or electron transport, or prevent hole leakage. Furthermore, placing a hole auxiliary layer between the hole transport layer (or hole injection layer) and the light-emitting layer can effectively promote or limit the hole transport rate (or hole injection rate), thereby enabling charge balance control. Additionally, placing an electron blocking layer between the hole transport layer (or hole injection layer) and the light-emitting layer can confine excitons within the light-emitting layer by blocking electron leakage from the light-emitting layer, preventing light leakage. When the organic electroluminescent device includes two or more hole transport layers, the further included layer can serve as a hole auxiliary layer or an electron blocking layer. The light-emitting auxiliary layer, hole auxiliary layer, or electron blocking layer improves the efficiency and / or lifetime of the organic electroluminescent device.

[0215] Furthermore, in the organic electroluminescent device of this disclosure, a mixed region of electron transport compound and reducing dopant, or a mixed region of hole transport compound and oxidizing dopant, can be placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to anion, and thus it becomes easier to inject and transport electrons from the mixed region into the light-emitting medium. Furthermore, the hole transport compound is oxidized to cation, and thus it becomes easier to inject and transport holes from the mixed region into the light-emitting medium. Preferably, the oxidizing dopant includes various Lewis acids and acceptor compounds, and the reducing dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. Additionally, the reducing dopant layer 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.

[0216] An organic electroluminescent device according to an embodiment of this disclosure may be an organic electroluminescent device having a series structure. In the case of a series organic electroluminescent device according to an embodiment, a single light-emitting unit (light-emitting component) may be formed in a structure in which two or more units are connected by a charge-generating layer. The organic electroluminescent device may include a plurality of two or more light-emitting units, for example, a plurality of three or more light-emitting units, each light-emitting unit having a first electrode and a second electrode opposite to each other on a substrate and a light-emitting layer stacked between the first electrode and the second electrode to emit light within a specific wavelength range. The organic electroluminescent device may include a plurality of light-emitting units, and each of these light-emitting units may include a hole transport band, a light-emitting layer, and an electron transport band, and the hole transport band may include a hole injection layer and a hole transport layer, and the electron transport band may include an electron transport layer and an electron injection layer. According to one embodiment, a light-emitting unit may include three or more light-emitting layers. The plurality of light-emitting units may emit the same color or different colors. Furthermore, a light-emitting unit may include one or more light-emitting layers, and the plurality of light-emitting layers may be light-emitting layers of the same color or different colors. It may include one or more charge-generating layers placed between each light-emitting unit. A charge generation layer is a layer that generates holes and electrons when a voltage is applied. When there are three or more light-emitting units, the charge generation layer can be placed between each light-emitting unit. Here, the multiple charge generation layers can be the same or different from each other. By placing the charge generation layer between the light-emitting units, the current efficiency in each light-emitting unit is increased, and the charge can be distributed uniformly. Specifically, the charge generation layer is disposed between two adjacent stacks and can be used to drive a series organic electroluminescent device using only a pair of anodes and cathodes, without the need for separate internal electrodes placed between the stacks.

[0217] 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 an alkali metal, an alkaline earth metal, or a compound of an alkali metal and an alkaline earth metal. Alkali metals can include one selected from the group consisting of Li, Na, K, Rb, Cs, Fr, Yb, and combinations thereof, and alkaline earth metals can include one selected from the group consisting of Be, Mg, Ca, Sr, Ba, Ra, and combinations thereof. The P-type charge-generating layer can be composed of a metal or an organic material doped with a P-type dopant. For example, the metal can be composed of one or more alloys selected from the group consisting of Al, Cu, Fe, Pb, Zn, Au, Pt, W, In, Mo, Ni, and Ti. Furthermore, commonly used materials can be used as both the P-type dopant and the host material in P-type doped organic materials.

[0218] According to one embodiment of this disclosure, organic electroluminescent materials can be used as luminescent materials for white organic light-emitting devices. Various structures of white organic light-emitting devices have been proposed, such as side-by-side structures, stacked structures, depending on the arrangement of R (red), G (green) or YG (yellow-green), B (blue) luminescent units, or color conversion material (CCM) methods, etc. Furthermore, according to one embodiment of this disclosure, organic electroluminescent materials can also be used in organic electroluminescent devices incorporating QDs (quantum dots).

[0219] To form each layer of the organic electroluminescent device of this disclosure, dry film deposition methods such as vacuum evaporation, sputtering, plasma, and ion plating, or wet film deposition methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, and flow coating can be used. When the first and second host compounds of this disclosure are used to form films, the method is performed by co-deposition or co-deposition.

[0220] When using a wet film-forming method, a thin film can be formed by dissolving or diffusing the material forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent can be any solvent in which the material forming each layer can dissolve or diffuse and in which there are no issues with film-forming ability.

[0221] Furthermore, display devices such as smartphones, tablets, laptops, PCs, TVs, or vehicle displays, or lighting devices such as outdoor or indoor lighting, can be produced using the organic electroluminescent devices disclosed herein.

[0222] In the following, to provide a detailed understanding of this disclosure, representative compounds of this disclosure are used to test the preparation methods of the compounds according to this disclosure, their physical properties, and the current efficiency of OLEDs comprising organic electroluminescent compounds according to this disclosure. The following examples are intended only to explain the properties of the compounds according to this disclosure and OLEDs comprising them in order to provide a detailed understanding of this disclosure, and this disclosure is not limited to the following examples.

[0223] In the following, in order to understand this disclosure in detail, methods for synthesizing representative compounds or intermediate compounds of this disclosure will be used as examples to describe methods for preparing compounds according to this disclosure.

[0224] [Example 1] Synthesis of compound H1-145

[0225]

[0226] Compound 1-1 (15 g, 36.4 mmol), compound 1-2 (10.9 g, 33.1 mmol), Pd2(dba)3 (1.56 g, 1.7 mmol), SPhos (1.35 g, 3.31 mmol), NaOtBu (6.36 g, 66.2 mmol), and 170 mL of xylene were mixed in a flask and stirred at 130°C for 2 hours. After the reaction was complete, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate and the remaining water was removed with magnesium sulfate. Subsequently, the organic layer was dried and separated by column chromatography to obtain compound H1-145 (4.3 g, yield: 18%).

[0227]

[0228] [Example 2] Synthesis of compound H3-463

[0229]

[0230] Compound 2-1 (10 g, 23.79 mmol), compound 2-2 (8.5 g, 23.79 mmol), tetrakis(triphenylphosphine)palladium (0.8 g, 0.71 mmol), potassium carbonate (8.2 g, 59.48 mmol), 120 mL of toluene, 30 mL of ethanol, and 30 mL of distilled water were added to a flask, and the mixture was stirred at 120°C for 2 hours. After the reaction was complete, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. The residue was then purified by column chromatography to obtain compound H3-463 (1.8 g, yield: 12%).

[0231]

[0232] [Example 3] Synthesis of compound H2-159

[0233]

[0234] Compound 3-1 (5.08 g, 16.77 mmol), compound 3-2 (7.0 g, 17.66 mmol), Pd2(dba)3 (0.77 g, 0.84 mmol), SPhos (0.7 g, 1.68 mmol), and NaOtBu (2.42 g, 25.15 mmol) were dissolved in 84 mL of o-xylene in a flask and stirred under reflux at 160°C for 4 hours. After the reaction was complete, the mixture was cooled to room temperature, and the layers were separated (EA / H2O), filtered with diatomaceous earth, filtered through a silica filter to form a solid, and filtered again to obtain compound H2-159 (4.7 g, yield: 40%).

[0235]

[0236] [Example 4] Synthesis of compound H3-466

[0237]

[0238] Compound 4-1 (14 g, 23.3 mmol), compound 4-2 (3.5 g, 27.96 mmol), Pd2(dba)3 (1 g, 1.165 mmol), and SPhos (765 mg, 1.86 mmol) were dissolved in 120 mL of xylene in a flask and stirred under reflux at 160°C for 1 hour. After the reaction was complete, the mixture was washed with distilled water, and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. The residue was then purified by column chromatography to obtain compound H3-466 (3 g, yield: 20%).

[0239]

[0240] [Example 5] Synthesis of compound H3-467

[0241]

[0242] Compound 5-1 (5 g, 11.16 mmol), compound 5-2 (2.8 g, 11.27 mmol), tetrakis(triphenylphosphine)palladium(0) (0.64 g, 0.56 mmol), potassium carbonate (3.8 g, 27.9 mmol), 60 mL of o-xylene, 15 mL of ethanol, and 15 mL of distilled water were added to a flask and stirred under reflux for 3 hours. After the reaction was complete, the mixture was added dropwise to methanol, and the resulting solid was filtered. The resulting solid was purified by column chromatography to obtain compound H3-467 (5.5 g, yield: 80%).

[0243]

[0244] [Example 6] Synthesis of compound C-24

[0245]

[0246] Compound 6-1 (11 g, 22.56 mmol), compound 6-2 (7.72 g, 45.11 mmol), Pd2(dba)3 (1.03 g, 1.128 mmol), NaOtBu (6.5 g, 67.68 mmol), and P(tBu)3 (456 mg, 2.256 mmol) were dissolved in toluene (113 mL, 0.2 M) in a flask and refluxed at 120°C for 12 hours. After the reaction was complete, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate and the remaining water was removed with magnesium sulfate. Subsequently, the organic layer was dried and separated by column chromatography to obtain compound C-24 (11.4 g, yield: 87%).

[0247]

[0248] [Example 7] Synthesis of compound H3-345

[0249]

[0250] Compound 7-1 (5.8 g, 13.37 mmol), compound 7-2 (4.9 g, 13.37 mmol), tetrakis(triphenylphosphine)palladium (0.77 g, 0.67 mmol), potassium carbonate (5.5 g, 40.10 mmol), 80 mL of toluene, 20 mL of ethanol, and 20 mL of distilled water were added to a reaction vessel, and the mixture was stirred at 120°C for 2 hours. After the reaction was complete, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. The residue was then purified by column chromatography to obtain compound H3-345 (5.6 g, yield: 64%).

[0251]

[0252] [Example 8] Synthesis of compound H3-456

[0253]

[0254] Compound 8-1 (9.8 g, 22.59 mmol), compound 8-2 (7.46 g, 22.59 mmol), tetrakis(triphenylphosphine)palladium (1.3 g, 1.129 mmol), potassium carbonate (9.3 g, 67.76 mmol), 120 mL of toluene, 30 mL of ethanol, and 30 mL of distilled water were added to a reaction vessel, and the mixture was stirred at 120°C for 2 hours. After the reaction was complete, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. The residue was then purified by column chromatography to obtain compound H3-456 (6.8 g, yield: 50%).

[0255]

[0256] [Example 9] Synthesis of compound H1-163

[0257]

[0258] Compound 9-1 (7.6 g, 23.05 mmol), compound 9-2 (10.08 g, 25.35 mmol), Pd2(dba)3 (1.06 g, 1.15 mmol), SPhos (0.95 g, 2.30 mmol), NaOtBu (3.32 g, 34.57 mmol), and 115 mL of xylene were mixed in a flask and stirred at 130°C for 2 hours. After the reaction was complete, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The remaining water was removed with magnesium sulfate, and the solvent was removed using a rotary evaporator. The residue was then purified by column chromatography to obtain compound H1-163 (11.2 g, yield: 70%).

[0259]

[0260] [Apparatus Examples 1-1 to 11-1] Fabrication of OLEDs according to the present disclosure

[0261] The OLED is produced according to this disclosure. First, a transparent electrode indium tin oxide (ITO) film (10 Ω / sq) (GEOMATEC CO., LTD., Japan) on a glass substrate used in the OLED is subjected to ultrasonic washing sequentially with acetone and isopropanol, and then stored in isopropanol for use. Next, the ITO substrate is mounted on a substrate holder of a vacuum vapor deposition apparatus. Then, compound HI-1 from Table 2 is introduced into one chamber of the vacuum vapor deposition apparatus, while compound HT-1 is introduced into another chamber. The two materials are evaporated at different rates, and compound HI-1 is deposited at a doping amount of 3 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. Then, compound HT-1 is deposited on the hole injection layer as a first hole transport layer with a thickness of 80 nm. The compounds from Table 1 were then introduced into another chamber of the vacuum vapor deposition apparatus, and evaporated by applying an electric current to the chamber, thereby forming a second hole transport layer with a thickness of 60 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, an emitting layer was formed thereon as follows: the compounds described in Table 1 were introduced as the host into two chambers of the vacuum vapor deposition apparatus, and compound D-39 was introduced as the dopant into another chamber. The host compound was evaporated at a 1:1 ratio, while the dopant material was evaporated at a different ratio, and the dopant was deposited at a doping amount of 3 wt% based on the total amount of the host and dopant to form an emitting layer with a thickness of 40 nm on the second hole transport layer. Next, compounds ET-1 and EI-1 were deposited on the emitting layer at a weight ratio of 50:50 as an electron transport layer to a thickness of 35 nm. After depositing compound EI-1 as a 2 nm thick electron injection layer on the electron transport layer, an 80 nm thick Al cathode was deposited on the electron injection layer using another vacuum vapor deposition apparatus. This produced an OLED. Each compound was processed through 10... -6 Purification is achieved through vacuum sublimation.

[0262] [Comparative Examples of Apparatus 1-1 to 11-1 and 1-2 to 11-2] Fabrication of OLEDs Not Based on This Disclosure

[0263] The OLED was produced in the same manner as in Device Example 1-1, except that the compounds in Table 1 below were used as materials for the second hole transport layer.

[0264] The current efficiency of the organic electroluminescent devices manufactured as described above according to device examples 1-1 to 11-1 and device comparative examples 1-1 to 11-1 and 1-2 to 11-2 was measured at a brightness of 1,000 nits, and the results are shown in Table 1 below.

[0265] [Table 1]

[0266]

[0267] As can be seen from Table 1 above, compared with organic electroluminescent devices not based on this disclosure, the organic electroluminescent devices based on this disclosure exhibit high current efficiency characteristics.

[0268] [Table 2] Compounds used in comparative apparatus examples 1-1 to 11-1 and 1-2 to 11-2, and in apparatus examples 1-1 to 11-1.

[0269]

[0270] [Device Examples 12-1 and 12-2] Fabrication of OLEDs according to the present disclosure

[0271] The OLED is manufactured according to this disclosure. First, a transparent electrode indium tin oxide (ITO) film (10 Ω / sq) (Geoma Co., Ltd., Japan) on a glass substrate used in the OLED is subjected to ultrasonic washing sequentially with acetone and isopropanol, and then stored in isopropanol for use. Next, the ITO substrate is mounted on a substrate holder of a vacuum vapor deposition apparatus. Then, compound HI-1 from Table 5 is introduced into one chamber of the vacuum vapor deposition apparatus, while compound HT-3 is introduced into another chamber. The two materials are evaporated at different rates, and compound HI-1 is deposited with a doping amount of 3 wt% based on the total amount of compounds HI-1 and HT-3 to form a hole injection layer with a thickness of 10 nm. Then, compound HT-3 is deposited on the hole injection layer as a first hole transport layer with a thickness of 90 nm. Then, the compound from Table 3 below is introduced into another chamber of the vacuum vapor deposition apparatus, and the compound is evaporated by applying current to the chamber, thereby forming a second hole transport layer with a thickness of 60 nm on the first hole transport layer. Compound HT-4 was then introduced into another chamber of the vacuum vapor deposition apparatus, and evaporated by applying current to the chamber, thereby forming a third hole transport layer with a thickness of 5 nm on the second hole transport layer. After forming the hole injection layer and the hole transport layer, an emitting layer was formed thereon as follows: the compounds described in Table 3 below were introduced as the host into two chambers of the vacuum vapor deposition apparatus, and compound D-162 was introduced as the dopant into another chamber. The host compounds were evaporated at a ratio of 35:65, while the dopant material was evaporated at a different ratio, and the dopant was deposited at a doping amount of 2 wt% based on the total amount of the host and dopant to form an emitting layer with a thickness of 40 nm on the third hole transport layer. Next, compound ET-2 was deposited on the emitting layer as a buffer layer with a thickness of 5 nm. Next, compounds ET-3 and EI-1 were deposited on the buffer layer at a weight ratio of 2:1 to form an electron transport layer with a thickness of 25 nm. After depositing Yb as an electron injection layer with a thickness of 2 nm on the electron transport layer, an Al cathode with a thickness of 80 nm was deposited on the electron injection layer using another vacuum vapor deposition apparatus. This produces an OLED. Each compound is processed through 10... -6 Purification is achieved through vacuum sublimation.

[0272] The current efficiency of the organic electroluminescent device according to the device example described above was measured at a brightness of 5,000 nits, and the results are shown in Table 3 below.

[0273] [Table 3]

[0274]

[0275] As can be seen from Table 3 above, the current efficiency of the organic electroluminescent device containing the compound according to the present disclosure as the hole transport band and host material is excellent.

[0276] [Device Examples 13-1 to 13-5] Fabrication of OLEDs according to the present disclosure

[0277] The OLED is manufactured according to this disclosure. First, a transparent electrode indium tin oxide (ITO) film (10 Ω / sq) (Geoma Co., Ltd., Japan) on a glass substrate used in the OLED is subjected to ultrasonic washing sequentially with acetone and isopropanol, and then stored in isopropanol for use. Next, the ITO substrate is mounted on a substrate holder of a vacuum vapor deposition apparatus. Then, compound HI-1 from Table 5 is introduced into one chamber of the vacuum vapor deposition apparatus, while compound HT-5 is introduced into another chamber. The two materials are evaporated at different rates, and compound HI-1 is deposited with a doping amount of 3 wt% based on the total amount of compounds HI-1 and HT-5 to form a hole injection layer with a thickness of 10 nm. Then, compound HT-5 is deposited on the hole injection layer as a first hole transport layer with a thickness of 80 nm. Then, the compound from Table 4 below is introduced into another chamber of the vacuum vapor deposition apparatus, and the compound is evaporated by applying current to the chamber, thereby forming a second hole transport layer with a thickness of 55 nm on the first hole transport layer. Compound HT-6 was then introduced into another chamber of the vacuum vapor deposition apparatus, and evaporated by applying current to the chamber, thereby forming a third hole transport layer with a thickness of 5 nm on the second hole transport layer. After forming the hole injection layer and the hole transport layer, an emitting layer was formed thereon as follows: the compounds described in Table 4 below were introduced as the host into two chambers of the vacuum vapor deposition apparatus, and compound D-162 was introduced as the dopant into another chamber. The host compounds were evaporated at a 1:1 ratio, while the dopant materials were evaporated at different ratios, and the dopant was deposited at a doping amount of 3 wt% based on the total amount of the host and dopant to form an emitting layer with a thickness of 40 nm on the third hole transport layer. Next, compound ET-4 was deposited on the emitting layer as a buffer layer with a thickness of 5 nm. Next, compounds ET-5 and EI-1 were deposited on the buffer layer at a weight ratio of 50:50 to form an electron transport layer with a thickness of 30 nm. After depositing compound EI-1 on an electron transport layer as an electron injection layer with a thickness of 2 nm, an Al cathode with a thickness of 80 nm was deposited on the electron injection layer using another vacuum phase deposition apparatus. This resulted in the production of an OLED. Each compound was processed through 10... -6 Purification is achieved through vacuum sublimation.

[0278] The current efficiency of the organic electroluminescent device according to the device example described above was measured at a brightness of 5,000 nits, and the results are shown in Table 4 below.

[0279] [Table 4]

[0280]

[0281] As can be seen from Table 4 above, the current efficiency of the organic electroluminescent device containing the compound according to the present disclosure as the hole transport band and host material is excellent.

[0282] [Table 5] Compounds used in apparatus examples 12-1, 12-2, and 13-1 to 13-5

[0283]

[0284] .

Claims

1. An organic electroluminescent device, comprising: a first electrode; a second electrode opposite to the first electrode; a light-emitting layer between the first electrode and the second electrode; and a hole transport band between the first electrode and the light-emitting layer. The hole transport band described herein comprises a compound represented by Formula 1, and The luminescent layer comprises a compound represented by Formula 2 and a compound represented by Formula 3: --- (1) --- (1-A) In equations 1 and 1-A, X represents O, S, or CR9R 10 ; R9 and R 10 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C) 30 )alkyl, substituted or unsubstituted (C6-C 30 ) aryl, substituted or unsubstituted (3 to 30 yuan) heteroaryl, or substituted or unsubstituted (C3-C 30 )cycloalkyl; or may be linked with adjacent substituents to form one or more rings; and R1 to R8 and R'1 to R'4 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C4) groups. 30 )alkyl, substituted or unsubstituted (C6-C 30 )Aryl, substituted or unsubstituted (3 to 30 yuan) Heteroaryl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (C1-C 30 )alkoxy, substituted or unsubstituted tri(C1-C) 30 )alkylsilyl, substituted or unsubstituted di(C1-C2) 30 )alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 )alkyl di(C6-C 30 arylsilyl, substituted or unsubstituted tri(C6-C) 30 )arylsilyl, (C3-C 30 Aliphatic rings and (C6-C) 30 Aromatic rings, whether substituted or unsubstituted, fused rings, mono- or di-(C1-C2) rings, whether substituted or unsubstituted. 30 )alkylamino, substituted or unsubstituted mono- or di-(C6-C) 30 ) arylamino, substituted or unsubstituted (C1-C 30 )alkyl (C6-C 30 ) arylamino, substituted or unsubstituted mono- or di-(3- to 30-membered) heteroarylamino, or substituted or unsubstituted (C6-C 30 )Aryl (3- to 30-membered) heteroarylamino; The premise is that a pair of bonds selected from R5 and R6, R6 and R7, and R7 and R8 are bonded together to form Equation 1-A. - Forming a ring; The premise is that at least one of R1 to R8 and R'1 to R'4 is represented by the following formula A; --- (A) In equation A, L, L1, and L2 each independently represent single-bonded, substituted, or unsubstituted (C6-C) bonds. 30 ) arylene, substituted or unsubstituted (3 to 30 yuan) heteroarylene, or substituted or unsubstituted (C3-C 30 )cycloalkylene; and Ar1 and Ar2 independently represent substituted or unsubstituted (C6-C) compounds. 30 )Aryl, or substituted or unsubstituted (3 to 30 yuan) heteroaryl, The prerequisite is that at least one of L, L1, L2, Ar1, and Ar2 must be substituted or unsubstituted (C3-C). 30 )cycloalkyl or substituted or unsubstituted (C1-C 30 Alkyl substitution; and --- (2) In Equation 2, L 11 To L 13 Each can be independently represented as a single bond, substituted or unsubstituted (C6-C). 30 ) aryl, or substituted or unsubstituted (3 to 30 yuan) heteroaryl; Ar 11 Indicates substituted or unsubstituted (3 to 30 yuan) heteroaryl groups; and Ar 12 and Ar 13 Each independently represents substituted or unsubstituted (C1-C) 30 )alkyl, substituted or unsubstituted (C6-C 30 )Aryl, substituted or unsubstituted (3 to 30 yuan) Heteroaryl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (C1-C 30 )alkoxy, substituted or unsubstituted tri(C1-C) 30 )alkylsilyl, substituted or unsubstituted di(C1-C2) 30 )alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 )alkyl di(C6-C 30 arylsilyl, substituted or unsubstituted tri(C6-C) 30 ) arylsilyl, substituted or unsubstituted mono- or di-(C1-C) 30 )alkylamino, substituted or unsubstituted mono- or di-(C2-C) 30 alkenylamino, substituted or unsubstituted (C1-C) 30 )alkyl (C2-C 30 alkenylamino, substituted or unsubstituted mono- or di-(C6-C) 30 ) arylamino, substituted or unsubstituted (C1-C 30 )alkyl (C6-C 30 ) arylamino, substituted or unsubstituted mono- or di-(3- to 30-membered) heteroarylamino, substituted or unsubstituted (C1-C 30 )alkyl (3- to 30-membered) heteroarylamino, substituted or unsubstituted (C2-C 30 )alkenyl (C6-C 30 ) arylamino, substituted or unsubstituted (C2-C 30 Alkenyl (3 to 30 nucleotides) heteroaryl amino groups, or substituted or unsubstituted (C6-C) 30 )Aryl (3- to 30-membered) heteroarylamino; --- (3) In Equation 3, X1 to X3 each independently represent N or CR 21 The premise is that at least one of X1 to X3 is N; Each R 21 Independently representing hydrogen or deuterium; L 21 To L 23 Each can be independently represented as a single bond, substituted or unsubstituted (C6-C). 30 ) aryl, or substituted or unsubstituted (3 to 30 yuan) heteroaryl; and Ar 21 To Ar 23 Each independently represents substituted or unsubstituted (C1-C) 30 )alkyl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, (C3-C 30 Aliphatic rings and (C6-C) 30 Aromatic rings, whether substituted or unsubstituted, fused rings, substituted or unsubstituted (C6-C) 30 )Aryl, or substituted or unsubstituted (3 to 30 yuan) heteroaryl; The premise is Ar 21 To Ar 23 At least one of them represents a substituted or unsubstituted (3 to 30) heteroaryl group.

2. The organic electroluminescent device according to claim 1, wherein, The substituted alkyl, the substituted (aryl) group, the substituted (heteroaryl) group, the substituted (cycloalkyl) group, the substituted (heteroaryl) group, the substituted alkoxy group, the substituted trialkylsilyl group, the substituted dialkylarylsilyl group, the substituted alkyldiarylsilyl group, the substituted triarylsilyl group, the substituted fused ring of aliphatic and aromatic rings, the substituted mono- or di-alkylamino group, the substituted mono- or di-enylamino group, the substituted alkylenylamino group, the substituted mono- or di-arylamino group, the substituted alkylarylamino group, the substituted alkylheteroarylamino group, the substituted alkenylarylamino group, the substituted alkenylheteroarylamino group, the substituted mono- or di-heteroarylamino group, and the substituted arylheteroarylamino group are each independently selected from at least one of the following groups: deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C 30 alkyl, halogenated (C1-C) 30 )alkyl, (C2-C 30 )alkenyl, (C2-C 30 ) ynyl group, (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 group, (C6-C 30 )Aromatic thiols, surrounded by (C6-C 30 )Aryl-substituted or unsubstituted (3 to 30 yuan) heteroaryl, substituted or unsubstituted (C6-C) heteroaryl 30 )Aromatic, tri(C1-C 30 )alkylsilyl, tri(C6-C 30 )arylsilyl, di(C1-C 30 )alkyl (C6-C 30 )arylsilyl, (C1-C 30 )alkyl di(C6-C 30 )arylsilyl, (C3-C 30 Aliphatic rings and (C6-C) 30 Fused rings of aromatic compounds, amino groups, mono- or di-(C1-C2) rings 30 )alkylamino, 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 )alkyl carbonyl, (C1-C 30 )alkoxycarbonyl, (C6-C 30 ) aryl carbonyl, (C6-C 30 )aryloxyphosphine, di(C6-C 30 )arylboronyl, di(C1-C 30 )alkylboronyl, (C1-C 30 )alkyl (C6-C 30 )arylboronyl, (C6-C 30 )Aryl(C1-C 30 )alkyl, (C1-C 30 )alkyl (C6-C 30 )Aromatic groups and their combinations.

3. The organic electroluminescent device according to claim 1, wherein, Equation 1 is represented by the following equation 1-1: --- (1-1) In Equation 1-1, R1 to R4, R8 to R 10 R'1 to R'4, L, L1, L2, Ar1, and Ar2 are as defined in claim 1.

4. The organic electroluminescent device according to claim 1, wherein, Among the alkyl or cycloalkyl groups that must be substituted in Formula 1, The cycloalkyl group is a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted norbornel group, a substituted or unsubstituted adamantyl group, or a substituted or unsubstituted cyclopentyl group; and The alkyl group is selected from the group consisting of: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, and 3-pentyl, each of which is unsubstituted or deuterated.

5. The organic electroluminescent device according to claim 1, wherein, Ar in Equation 2 11 It is a heteroaryl group with four or more fused rings and must contain substituted or unsubstituted oxygen atoms (3 to 30 aryl groups).

6. The organic electroluminescent device according to claim 1, wherein, Ar in Equation 2 11 It can be represented by the following formula 2-1 or 2-2: In equations 2-1 and 2-2, T1 and T2 independently represent -N= and -NR, respectively. 20 -, -O-, or -S-, provided that one of T1 and T2 represents -N=, and the other of T1 and T2 represents -NR. 20 -、-O-、or -S-; T3 indicates O or S; R 11 Indicates whether it is substituted or not substituted (C6-C) 30 )Aryl, or substituted or unsubstituted (3 to 30 yuan) heteroaryl; R 12 To R 19 and R 22 To R 33 Each independently with L 11 A link, or a symbol representing hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C) 30 )alkyl, substituted or unsubstituted (C6-C 30 )Aryl, substituted or unsubstituted (3 to 30 yuan) Heteroaryl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (C1-C 30 )alkoxy, substituted or unsubstituted tri(C1-C) 30 )alkylsilyl, substituted or unsubstituted di(C1-C2) 30 )alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 )alkyl di(C6-C 30 arylsilyl, substituted or unsubstituted tri(C6-C) 30 )arylsilyl, (C3-C 30 Aliphatic rings and (C6-C) 30 Aromatic rings, whether substituted or unsubstituted, fused rings, mono- or di-(C1-C2) rings, whether substituted or unsubstituted. 30 )alkylamino, substituted or unsubstituted mono- or di-(C2-C) 30 alkenylamino, substituted or unsubstituted (C1-C) 30 )alkyl (C2-C 30 alkenylamino, substituted or unsubstituted (C1-C) 30 )alkyl (C6-C 30 ) arylamino, substituted or unsubstituted (C1-C 30 )alkyl (3- to 30-membered) heteroarylamino, substituted or unsubstituted (C2-C 30 )alkenyl (C6-C 30 ) arylamino, substituted or unsubstituted (C2-C 30 Alkenyl (3 to 30 quinones) heteroarylamino, substituted or unsubstituted mono- or di-(C6-C) 30 ) arylamino, substituted or unsubstituted mono- or di-(3- to 30-membered) heteroarylamino, or substituted or unsubstituted (C6-C 30 aryl (3- to 30-membered) heteroarylamino; or may be linked with adjacent substituents to form one or more rings, The premise is that R in Equation 2-1 12 To R 19 any one of them with L 11 Connect, and R in Equation 2-2 22 To R 33 any one of them with L 11 connect.

7. The organic electroluminescent device according to claim 1, wherein, Equation 3 is represented by any one of the following equations 3-1 to 3-4: In equations 3-1 to 3-4, Y represents O, S, or NR. 36 ; R 34 To R 36 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C) 30 )alkyl, substituted or unsubstituted (C6-C 30 )Aryl, substituted or unsubstituted (3 to 30 yuan) Heteroaryl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (C1-C 30 )alkoxy, substituted or unsubstituted tri(C1-C) 30 )alkylsilyl, substituted or unsubstituted di(C1-C2) 30 )alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 )alkyl di(C6-C 30 arylsilyl, substituted or unsubstituted tri(C6-C) 30 ) arylsilyl, substituted or unsubstituted mono- or di-(C1-C) 30 )alkylamino, substituted or unsubstituted mono- or di-(C6-C) 30 ) arylamino, or substituted or unsubstituted (C1-C 30 )alkyl (C6-C 30 )Arylamino; or may be linked with adjacent substituents to form one or more rings; L 21 To L 23 Ar 22 And Ar 23 Same as defined in claim 1; n is an integer from 1 to 3, and m is an integer from 1 to 4; and When n and m are integers of 2 or greater, each R 34 and each R 35 They can be the same or different.

8. The organic electroluminescent device according to claim 1, wherein, The compound represented by Formula 1 is selected from the following compounds: In each of the compounds described above, hydrogen can be replaced by deuterium.

9. The organic electroluminescent device according to claim 1, wherein, The compound represented by Formula 2 is selected from the following compounds: In the compounds described above, D n This means that n hydrogen atoms are replaced by deuterium, where n is an integer from 1 to the maximum number of hydrogen atoms in the compound.

10. The organic electroluminescent device according to claim 1, wherein, The compound represented by Formula 3 is selected from the following compounds: and In the compounds described above, D n This means that n hydrogen atoms are replaced by deuterium, where n is an integer from 1 to the maximum number of hydrogen atoms in the compound.

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

12. The organic electroluminescent device according to claim 1, further comprising an additional compound in the light-emitting layer, said additional compound being different from the compound represented by formulas 2 and 3.

13. The organic electroluminescent device according to claim 1, wherein, The light-emitting layer includes a red light-emitting layer.

14. An organic electroluminescent compound, represented by the following compounds: 。 15. An organic electroluminescent material comprising the organic electroluminescent compound according to claim 14.

16. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 14.

17. The organic electroluminescent device according to claim 16, wherein, The organic electroluminescent compound is contained in at least one layer selected from the light-emitting layer, the first hole transport layer, the second hole transport layer, the hole auxiliary layer, the electron blocking layer, and the light-emitting auxiliary layer.

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