Organic electro-luminescent compound and organic electro-luminescent device

Abstract

To provide an organic electro-luminescent compound and an organic electro-luminescent device.SOLUTION: The present invention relates to an organic electro-luminescent compound and an organic electro-luminescent device expressed by formula 1. The organic electro-luminescent device includes chemical compounds with different structures in a first hole transfer layer, a second hole transfer layer, and a third hole transfer layer, and second hole transfer layer includes a fluorenamine structure, a benzofluorene-amine structure, and a naphthofluorene-amine structure. In that way, a low driving voltage and a high current efficiency can be achieved.SELECTED DRAWING: None

Description

[Technical field]

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

[0002] Electroluminescent devices (EL devices) are self-emitting display devices that have the advantages of providing wider viewing angles, greater contrast ratios, and faster response times. In 1987, Eastman Kodak developed the first organic EL device by using small aromatic diamine molecules and aluminum complexes as materials for forming the light-emitting layer (see Non-Patent Document 1).

[0003] Organic electroluminescent devices have a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer to increase their efficiency and stability. Selection of the compound contained in the hole transport layer, etc. is recognized as one of the means to improve the characteristics of the device, such as the hole transport efficiency to the light emitting layer, the light emitting efficiency, and the lifespan.

[0004] In order to improve the luminous efficiency, driving voltage, and / or life span, various materials or concepts have been proposed for the hole transport layer of organic electroluminescent devices, but they have not been satisfactory in practical use.Therefore, there is a continuing demand for developing organic electroluminescent devices with improved performance, such as improved driving voltage, luminous efficiency, power efficiency, and / or life span characteristics, compared with the organic electroluminescent devices disclosed so far.

[0005] On the other hand, although amine compounds are disclosed in (Patent Document 1) and (Patent Document 2), the structures of the compounds contained in the first hole transport layer, the second hole transport layer, and the third hole transport layer of the organic electroluminescent device according to the present disclosure are different from each other, and the second hole transport layer does not contain a compound having a fluorene-amine structure, a benzofluorene-amine structure, or a naphthofluorene-amine structure.Therefore, there is still a continuous demand for improving the performance of OLED. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] JP 2023-021983 A [Patent Document 2] International Publication No. 2015 / 061198 Brochure [Patent Document 3] Korean Patent Application Publication No. 2015-0066202 [Patent Document 4] Korean Patent Application Publication No. 2015-0076129 [Patent Document 5] Korean Patent Application Publication No. 2017-0043439 [Patent Document 6] Korean Patent Application Publication No. 2019-0090695 [Patent Document 7] Korean Patent Application Publication No. 2020-0004257 [Patent Document 8] Korean Patent Application Publication No. 2020-0018275 [Patent Document 9] Korean Patent Application Publication No. 2020-0090091 [Non-patent literature]

[0007] [Non-Patent Document 1] Appl. Phys. Lett. 51, 913, 1987 Summary of the Invention [Problem to be solved by the invention]

[0008] The object of the present disclosure is, first, to provide an organic electroluminescent compound that is useful for producing an organic electroluminescent device having improved driving voltage and / or current efficiency, and, second, to provide an organic electroluminescent device having improved driving voltage and / or current efficiency. [Means for solving the problem]

[0009] As a result of intensive research to solve the above technical problems, the present inventors have found that the above object can be achieved by an organic electroluminescent device comprising: a first electrode; a second electrode opposed to the first electrode; and a structure in which a hole injection layer, a first hole transport layer, a second hole transport layer, a third transport layer, and a light-emitting layer are laminated in this order between the first electrode and the second electrode; wherein the structures of compounds contained in the first hole transport layer, the second hole transport layer, and the third hole transport layer are different from each other; and the second hole transport layer contains a compound having a fluorene-amine structure, a benzofluorene-amine structure, or a naphthofluorene-amine structure.

[0010] Furthermore, the present inventors have found that the above object can be achieved by an organic electroluminescent compound represented by the following Chemical Formula 1: [ka]

[0011] In formula 1, Ring A represents a substituted or unsubstituted benzene, a substituted or unsubstituted naphthalene, or a substituted or unsubstituted phenanthrene; Ar1 and Ar2 each independently represent a substituted or unsubstituted (C2 to C30) alkyl; R and R1 to R4 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C3 to C30) cycloalkyl, substituted or unsubstituted (C6 to C30) aryl, substituted or unsubstituted (3 to 30 membered) heteroaryl, or substituted or unsubstituted (C1 to C30) alkoxy, or may be linked to adjacent substituents to form a ring, with the proviso that at least one of R and R1 to R4 is represented by -L1-NAr3Ar4; L1 represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; Ar3 and Ar4 each independently represent a substituted or unsubstituted (C6 to C30) aryl or a substituted or unsubstituted (3 to 30 membered) heteroaryl; n represents an integer of 1 to 8, and when n is a plurality of n's, each n may be the same or different.

[0012] Furthermore, the present inventors have found that the above object can be achieved by an organic electroluminescent compound represented by the following chemical formula 3: [ka]

[0013] In Equation 3, R a ~R j At least one of the following formula 3-1 [ka] Represented by; In formulas 3 and 3-1, R a ~R m each independently represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl; [ka] represents a bond between Formula 3 and Formula 3-1; L6 to L8 each independently represent a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30-membered) heteroarylene; Ar8 represents a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (C3-C30) cycloalkyl, or a substituted or unsubstituted (3-30 membered) heteroaryl; k and l each independently represent an integer of 1 to 5, and m represents an integer of 1 to 3; When k~m are integers of 2 or more, R k ~R m may be the same or different from one another.

[0014] Advantageous Effects of the Invention By using the organic electroluminescent compounds of the present disclosure, it is possible to provide organic electroluminescent devices with improved driving voltage and / or power efficiency. [Brief description of the drawings]

[0015] [Figure 1] 1 is a representative formula of an organic electroluminescent compound according to the present disclosure. [Diagram 2] 1 is a representative formula of an organic electroluminescent compound according to the present disclosure. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0016] The present disclosure will be described in detail below. However, the following description is intended to explain the present disclosure, and is in no way intended to limit the scope of the present disclosure.

[0017] The present disclosure relates to an organic electroluminescent device including: a first electrode; a second electrode opposite to the first electrode; and a structure in which a hole injection layer, a first hole transport layer, a second hole transport layer, a third transport layer, and a light emitting layer are stacked in this order between the first electrode and the second electrode; wherein the structures of compounds contained in the first hole transport layer, the second hole transport layer, and the third hole transport layer are different from each other; and the second hole transport layer contains a compound having a fluorene-amine structure, a benzofluorene-amine structure, or a naphthofluorene-amine structure.

[0018] The term "organic electroluminescent compound" in this disclosure means a compound that can be used in an organic electroluminescent device and, if necessary, can be included in any layer that makes up the organic electroluminescent device.

[0019] The term "organic electroluminescent material" in the present disclosure means a material that can include at least one compound that can be used in an organic electroluminescent device. The organic electroluminescent material can be included in any layer that constitutes an organic electroluminescent device as necessary. For example, the organic electroluminescent material can 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 (including a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc. The hole transport zone material can be at least one selected from the group consisting of a hole transport material, a hole injection material, an electron blocking material, a hole auxiliary material, and a light-emitting auxiliary material.

[0020] The organic electroluminescent material of the present disclosure may include at least one compound represented by the above formula 1. The compound of formula 1 can be included in at least one of the layers constituting an organic electroluminescent device, but is not limited thereto, and may be included in at least one of the layers constituting a hole transport layer. When the compound of formula 1 is included in a hole transport layer, a hole auxiliary layer, an electron blocking layer, an emitting layer, or an emitting auxiliary layer, it can be included as a hole transport material, a hole auxiliary material, an electron blocking material, a host material, or an emitting auxiliary material.

[0021] The term "electron transport zone" in the present disclosure refers to the region where electrons move between the light-emitting layer and the cathode. For example, it can include at least one of a hole-blocking layer, an electron-transporting layer, and an electron-injecting layer, preferably at least one of an electron-transporting layer and an electron-injecting layer. The hole-blocking layer has the function of preventing holes from passing through the light-emitting layer to the cathode when the organic electroluminescent device is operated.

[0022] The term "hole transport zone" in the present disclosure means a region where holes move between the first electrode and the light-emitting layer, and 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, the hole transport layer, the hole auxiliary layer, the light-emitting auxiliary layer, and the electron blocking layer may be a single layer, or may be a multilayer in which two or more layers, or three or more layers, are stacked. According to one embodiment of the present disclosure, the hole transport zone may include a first hole transport layer and a second hole transport layer, and may further include a third hole transport layer. The second hole transport layer and the third hole transport layer may be at least one layer of a plurality of hole transport layers, and may include at least one of a hole auxiliary layer, a light-emitting auxiliary layer, and an electron blocking layer. In addition, according to another embodiment of the present disclosure, the hole transport zone can include a first hole transport layer and a second hole transport layer, the first hole transport layer can be disposed between the first electrode and the light emitting layer, the second hole transport layer can be disposed between the first hole transport layer and the light emitting layer, and the second hole transport layer can be a layer functioning as a hole transport layer, a light emitting auxiliary layer, a hole auxiliary layer, and / or an electron blocking layer. According to another embodiment of the present disclosure, the hole transport zone may include a first hole transport layer, a second hole transport layer, and a third hole transport layer, where the first hole transport layer may be disposed between the first electrode and the light emitting layer, the second hole transport layer may be disposed between the first hole transport layer and the light emitting layer, the third hole transport layer may be disposed between the second hole transport layer and the light emitting layer, and the third hole transport layer may be a layer functioning as a hole transport layer, a light emitting auxiliary layer, a hole auxiliary layer, and / or an electron blocking layer.

[0023] In this specification, the term "(C1-C30) alkyl" is intended to refer to a straight-chain or branched alkyl having 1 to 30 carbon atoms constituting the chain, preferably 1 to 20, more preferably 1 to 10. The alkyl may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, and the like. The term "(C2-C30) alkenyl" in the present disclosure is intended to refer to a straight-chain or branched alkenyl having 2 to 30 carbon atoms constituting the chain, preferably 2 to 20, more preferably 2 to 10. The alkenyl may include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, and the like. The term "(C2-C30)alkynyl" in the present disclosure is intended to refer to a straight or branched alkynyl having 2-30 carbon atoms constituting the chain, preferably 2-20, more preferably 2-10. The alkynyl may include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, and the like. The term "(C3-C30)cycloalkyl" is intended to refer to a monocyclic or polycyclic hydrocarbon having 3-30 ring skeletal carbon atoms, preferably 3-20, more preferably 3-7 carbon atoms. The cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like. The term "(3-7 membered)heterocycloalkyl" in the present disclosure is intended to refer to a cycloalkyl having 3-7, preferably 5-7, ring skeletal atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably at least one heteroatom selected from the group consisting of O, S, and N. The heterocycloalkyl may include tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, and the like. The terms "(C6-C30)aryl(ene)" and "(C6-C30)arene" in the present disclosure are ...It is intended to refer to a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring skeletal carbon atoms, which may be partially saturated. The number of ring skeletal carbon atoms is preferably 6 to 25, more preferably 6 to 18. The aryl(ene) may include a spiro structure. The aryl may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, benzofluorenyl, diphenylfluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, and the like. Specifically, the aryl includes phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, 1-chrysenyl, 2-chrysenyl, 3-chrysenyl, 4-chrysenyl, 5-chrysenyl, 6-chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo[a]fluorenyl, benzo[b]fluorenyl, benzo[c ]fluorenyl, dibenzofluorenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenylyl,4''-tert-butyl-p-terphenyl-4-yl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, 11,11-dimethyl-1-benzo[a]fluorenyl, 11,11-dimethyl-2-benzo[a]fluorenyl, 11,11-dimethyl-3-benzo[a] fluorenyl, 11,11-dimethyl-4-benzo[a]fluorenyl, 11,11-dimethyl-5-benzo[a]fluorenyl, 11,11-dimethyl-6-benzo[a]fluorenyl, 11,11-dimethyl-7-benzo[a]fluorenyl, 11,11-dimethyl-8-benzo[a]fluorenyl, 11,11-dimethyl-9-benzo[a]fluorenyl, 11,11-dimethyl-10-benzo[a]fluorenyl, 11,11-dimethyl-1-benzo[b]fluorenyl, 11,11-dimethyl-2-benzo[b]fluorenyl, 11,1 1-Dimethyl-3-benzo[b]fluorenyl, 11,11-dimethyl-4-benzo[b]fluorenyl, 11,11-dimethyl-5-benzo[b]fluorenyl, 11,11-dimethyl-6-benzo[b]fluorenyl, 11,11-dimethyl-7-benzo[b]fluorenyl, 11,11-dimethyl-8-benzo[b]fluorenyl, 11,11-dimethyl-9-benzo[b]fluorenyl, 11,11-dimethyl-10-benzo[b]fluorenyl, 11,11-dimethyl-1-benzo[c]fluorenyl, 11,11-dimethyl-2-benzo[b]fluorenyl 11,11-dimethyl-3-benzo[c]fluorenyl, 11,11-dimethyl-4-benzo[c]fluorenyl, 11,11-dimethyl-5-benzo[c]fluorenyl, 11,11-dimethyl-6-benzo[c]fluorenyl, 11,11-dimethyl-7-benzo[c]fluorenyl, 11,11-dimethyl-8-benzo[c]fluorenyl, 11,11-dimethyl-9-benzo[c]fluorenyl, 11,11-dimethyl-10-benzo[c]fluorenyl, 11,11-diphenyl-1-benzo[a]fluorenyl,11,11-diphenyl-2-benzo[a]fluorenyl, 11,11-diphenyl-3-benzo[a]fluorenyl, 11,11-diphenyl-4-benzo[a]fluorenyl, 11,11-diphenyl-5-benzo[a]fluorenyl, 11,11-diphenyl-6-benzo[a]fluorenyl, 11,11-diphenyl-7-benzo[a]fluorenyl, 11,11-diphenyl-8-benzo[a]fluorenyl, 11,11-diphenyl-9-benzo[a]fluorenyl, 11,11-diphenyl-10-benzo[a ]fluorenyl, 11,11-diphenyl-1-benzo[b]fluorenyl, 11,11-diphenyl-2-benzo[b]fluorenyl, 11,11-diphenyl-3-benzo[b]fluorenyl, 11,11-diphenyl-4-benzo[b]fluorenyl, 11,11-diphenyl-5-benzo[b]fluorenyl, 11,11-diphenyl-6-benzo[b]fluorenyl, 11,11-diphenyl-7-benzo[b]fluorenyl, 11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9 -benzo[b]fluorenyl, 11,11-diphenyl-10-benzo[b]fluorenyl, 11,11-diphenyl-1-benzo[c]fluorenyl, 11,11-diphenyl-2-benzo[c]fluorenyl, 11,11-diphenyl-3-benzo[c]fluorenyl, 11,11-diphenyl-4-benzo[c]fluorenyl, 11,11-diphenyl-5-benzo[c]fluorenyl, 11,11-diphenyl-6-benzo[c]fluorenyl, 11,11-diphenyl-7-benzo[c]fluorenyl, 11,11 -diphenyl-8-benzo[c]fluorenyl, 11,11-diphenyl-9-benzo[c]fluorenyl, 11,11-diphenyl-10-benzo[c]fluorenyl, 9,9,10,10-tetramethyl-9,10-dihydro-1-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-2-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-3-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-4-phenanthrenyl, and the like.

[0024] The terms "(3-30 membered) heteroaryl(ene)" and "(3-30 membered) heteroarene" in the present disclosure are intended to refer to an aryl(ene) having 3-30 ring skeletal atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, P, Se, Te, and Ge. The number of heteroatoms is preferably 1-4. The heteroaryl(ene) may be a single ring or a fused ring fused with at least one benzene ring; it may be partially saturated. In addition, the heteroaryl(ene) may be formed by binding at least one heteroaryl or aryl group to a heteroaryl(ene) group via a single bond, and may include a spiro structure. Examples of the heteroaryl include monocyclic heteroaryls such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl, and benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, benzophenanthrofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, and benzophenone. Examples of fused ring heteroaryls include anthrothiophenyl, benzisoxazolyl, benzoxazolyl, phenanthrooxazolyl, phenanthrothiazolyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, and dihydroacridinyl. More specifically, heteroaryl includes 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 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-Indolizinyl, 2-Indolizinyl, 3-Indolizinyl, 5-Indolizinyl, 6-Indolizinyl, 7-Indolizinyl, 8-Indolizinyl, 2-Imidazopyridyl, 3-Imidazopyridyl, 5-Imidazopyridyl, 6-Imidazopyridyl, 7-Imidazopyridyl, 8-Imidazopyridyl, 3-Pyridyl, 4-Pyridyl, 1-Indolyl, 2-Indolyl, 3-Indolyl, 4-Indolyl, 5-Indolyl, 6-Indolyl, 7-Indolyl, 1-Isoindolyl, 2-Isoindolyl, 3-Isoindolyl Indolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-Isoquinolyl, 4-Isoquinolyl, 5-Isoquinolyl, 6-Isoquinolyl, 7-Isoquinolyl, 8-Isoquinolyl, 2-Quinoxalinyl, 5-Quinoxalinyl, 6-Quinoxalinyl, 1-Carbazolyl, 2-Carbazolyl, 3-Carbazolyl, 4-Carbazolyl, 9-Carbazolyl, azacarbazol-1-yl, azacarbazol-2-yl, azacarbazol-3-yl, azacarbazol-4-yl, azacarbazol-5-yl, azacarbazol-6-yl, azacarbazol-7-yl, azacarbazol-8-yl, azacarbazol pyrrol-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl,2-Methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2-tert-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4-tert-butyl-1-indolyl, 2-ter t-Butyl-3-indolyl, 4-tert-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-naphtho-[1,2-b]-benzofuranyl, 2-naphtho-[1,2-b]-benzofuranyl, 3-naphtho-[1,2-b]-benzofuranyl, 4-naphtho-[1,2-b]-benzofuranyl, 5-naphtho-[1,2-b]-benzofuranyl, 6-naphtho-[1,2 -b]-benzofuranyl, 7-naphtho-[1,2-b]-benzofuranyl, 8-naphtho-[1,2-b]-benzofuranyl, 9-naphtho-[1,2-b]-benzofuranyl, 10-naphtho-[1,2-b]-benzofuranyl, 1-naphtho-[2,3-b]-benzofuranyl, 2-naphtho-[2,3-b]-benzofuranyl, 3-naphtho-[2,3-b]-benzofuranyl, 4-naphtho-[2,3-b]-benzofuranyl, 5-naphtho-[2,3-b]-benzofuranyl, 6-naphtho-[2,3-b]-benzofuranyl, 7-naphtho-[2,3-b]-benzofuranyl Zofuranil, 8-naphtho-[2,3-b]-benzofuranyl, 9-naphtho-[2,3-b]-benzofuranyl, 10-naphtho-[2,3-b]-benzofuranyl, 1-naphtho-[2,1-b]-benzofuranyl, 2-naphtho-[2,1-b]-benzofuranyl, 3-naphtho-[2,1-b]-benzofuranyl, 4-naphtho-[2,1-b]-benzofuranyl, 5-naphtho-[2,1-b]-benzofuranyl, 6-naphtho-[2,1-b]-benzofuranyl, 7-naphtho-[2,1-b]-benzofuranyl, 8-naphtho-[2,1-b]-benzofuranyl,9-naphtho-[2,1-b]-benzofuranyl, 10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b]-benzothiophenyl, 2-naphtho-[1,2-b]-benzothiophenyl, 3-naphtho-[1,2-b]-benzothiophenyl, 4-naphtho-[1,2-b]-benzothiophenyl, 5-naphtho-[1,2-b]-benzothiophenyl, 6-naphtho-[1,2-b]-benzothiophenyl, 7-naphtho-[1,2-b]-benzothiophenyl, 8-naphtho-[1,2-b]-benzothiophenyl, 9-naphtho-[1,2-b ]-benzothiophenyl, 10-naphtho-[1,2-b]-benzothiophenyl, 1-naphtho-[2,3-b]-benzothiophenyl, 2-naphtho-[2,3-b]-benzothiophenyl, 3-naphtho-[2,3-b]-benzothiophenyl, 4-naphtho-[2,3-b]-benzothiophenyl, 5-naphtho-[2,3-b]-benzothiophenyl, 1-naphtho-[2,1-b]-benzothiophenyl, 2-naphtho-[2,1-b]-benzothiophenyl, 3-naphtho-[2,1-b]-benzothiophenyl, 4-naphtho-[2,1-b]-benzothiof phenyl, 5-naphtho-[2,1-b]-benzothiophenyl, 6-naphtho-[2,1-b]-benzothiophenyl, 7-naphtho-[2,1-b]-benzothiophenyl, 8-naphtho-[2,1-b]-benzothiophenyl, 9-naphtho-[2,1-b]-benzothiophenyl, 10-naphtho-[2,1-b]-benzothiophenyl, 2-benzofuro[3,2-d]pyrimidinyl, 6-benzofuro[3,2-d]pyrimidinyl, 7-benzofuro[3,2-d]pyrimidinyl, 8-benzofuro[3,2-d]pyrimidinyl, 9-benzofuro[3,2-d]pyrimidinyl 2-benzothio[3,2-d]pyrimidinyl, 6-benzothio[3,2-d]pyrimidinyl, 7-benzothio[3,2-d]pyrimidinyl, 8-benzothio[3,2-d]pyrimidinyl, 9-benzothio[3,2-d]pyrimidinyl, 2-benzofuro[3,2-d]pyrazinyl, 6-benzofuro[3,2-d]pyrazinyl, 7-benzofuro[3,2-d]pyrazinyl, 8-benzofuro[3,2-d]pyrazinyl, 9-benzofuro[3,2-d]pyrazinyl, 2-benzothio[3,2-d]pyrazinyl, 6-benzothio[3,2-d]pyrazinyl,Examples of the heteroaryl group include 7-benzothio[3,2-d]pyrazinyl, 8-benzothio[3,2-d]pyrazinyl, 9-benzothio[3,2-d]pyrazinyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-germafluorenyl, 4-germafluorenyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, etc. Furthermore, "heteroaryl(ene)" can be classified into heteroaryl(ene) having electronic properties and heteroaryl(ene) having hole properties. Heteroaryl(ene)s with electronic character are those where the parent nucleus is relatively electron-rich, such as substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, or substituted or unsubstituted quinolyl. Heteroaryl(ene)s with hole character are those where the parent nucleus is relatively electron-poor, such as substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, etc. In this disclosure, the term "halogen" includes F, Cl, Br, and I.

[0025] In addition, "ortho-", "meta-", and "para-" are prefixes that indicate the relative positions of the substituents. The prefix "ortho-" indicates that two substituents are adjacent to each other, for example, when the two substituents of a benzene derivative occupy the 1st and 2nd positions, this is called the "ortho-" configuration. The prefix "meta-" indicates that two substituents are at the 1st and 3rd positions, for example, when the two substituents of a benzene derivative occupy the 1st and 3rd positions, this is called the "meta-" configuration. The prefix "para-" indicates that two substituents are at the 1st and 4th positions, for example, when the two substituents of a benzene derivative occupy the 1st and 4th positions, this is called the "para-" configuration.

[0026] In this specification, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a specific functional group is replaced with another atom or another functional group, i.e., a substituent. Unless otherwise specified, a substituent may replace hydrogen at the place where the substituent can be replaced without limitation, and when two or more hydrogen atoms in a specific functional group are each replaced with a substituent, each substituent may be the same or different from each other. The maximum number of substituents that can be replaced for a certain functional group may be the total number of valences that can be replaced for each atom that forms the functional group. As used herein, substituted alkyl, substituted alkenyl, substituted aryl(ene), substituted heteroaryl(ene), substituted cycloalkyl, and substituted alkoxy each independently represent deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; phosphine oxide; (C1-C30) alkyl; halo(C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3-7 membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (C6-C30) aryl that is unsubstituted or substituted with at least one of (C1-C30) alkyl and di(C6-C30) arylamino; unsubstituted or (C6-C30) aryl. (3-30 membered)heteroaryl substituted with at least one of the following: tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; (C3-C30)aliphatic ring and (C6-C30)aromatic ring fused ring; amino; mono- or di(C1-C30)alkylamino; mono No- or di(C2-C30)alkenylamino; unsubstituted or (C1-C30)alkyl-substituted mono- or di(C6-C30)arylamino; mono- or di(3-30 membered)heteroarylamino; (C1-C30)alkyl(C2-C30)alkenylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkyl(3-30 membered)heteroarylamino;At least one selected from the group consisting of (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30)alkenyl(3-30 membered)heteroarylamino; (C6-C30)aryl(3-30 membered)heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl. According to one embodiment of the present disclosure, the substituents are each independently selected from deuterium; (C1-C30) alkyl; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3-membered to 7-membered) heterocycloalkyl; (C6-C30) aryl which is unsubstituted or substituted with at least one of (C1-C30) alkyl and di(C6-C30) arylamino; (3-membered to 30-membered) heteroaryl which is unsubstituted or substituted with at least one of (C6-C30) aryl; a fused ring group of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring; amino; mono- or di(C1-C30) alkylamino; mono- or di(C2-C30) alkenylamino; unsubstituted. or mono- or di(C6-C30)arylamino substituted with (C1-C30)alkyl; mono- or di(3-30 membered)heteroarylamino; (C1-C30)alkyl(C2-C30)alkenylamino; (C1-C30)alkyl(C6-C30)arylamino; C1-C30)alkyl(3-30 membered)heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30)alkenyl(3-30 membered)heteroarylamino; (C6-C30)aryl(3-30 membered)heteroarylamino; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl. According to another embodiment of the present disclosure, the substituents are each independently selected from the group consisting of deuterium; (C1-C20) alkyl; (C3-C20) cycloalkyl; (3-7 membered) heterocycloalkyl;(C6-C20) aryl which is unsubstituted or substituted with at least one of (C1-C30) alkyl and di(C6-C30) arylamino; (3-20 membered) heteroaryl which is unsubstituted or substituted with at least one of (C6-C30) aryl; fused ring group of (C3-C30) aliphatic ring and (C6-C30) aromatic ring; mono- or di(C6-C20) arylamino which is unsubstituted or substituted with (C1-C30) alkyl; mono- or di(3-20 membered) heteroaryl Heteroarylamino; (C1-C20) alkyl (C6-C20) arylamino; (C1-C20) alkyl (3-20 membered) heteroarylamino; (C2-C20) alkenyl (C6-C20) arylamino; (C2-C20) alkenyl (3-20 membered) heteroarylamino; (C6-C20) aryl (3-20 membered) heteroarylamino; (C6-C30) aryl (C1-C30) alkyl; and (C1-C30) alkyl (C6-C30) aryl. For example, the substituents may each independently be at least one selected from the group consisting of deuterium, methyl, naphthyl, phenanthrenyl, dibenzofuranyl, unsubstituted or deuterium-substituted phenyl, phenanthrylene, dimethylfluorenyl, benzonaphthofuranyl, benzonaphthothiophenyl, phenyldimethylfluorenylamino, and adamantyl.

[0027] In the present disclosure, if a substituent is not shown in a chemical formula or compound structure, it may mean that all positions where a substituent may be present are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be isotopic deuterium, in which case the content of deuterium may be 0% to 100%. In the present disclosure, if a substituent is not shown in a chemical formula or compound structure, hydrogen and deuterium may be mixed in the compound unless the substituent is explicitly excluded, such as 0% deuterium, 100% hydrogen, and all substituents are hydrogen. Deuterium is one of the isotopes of hydrogen, and is an element that has a deuteron consisting of one proton and one neutron as its nucleus. It can be represented as hydrogen-2, and its element symbol can also be written as D or 2H. Isotopes can also be interpreted as atoms with the same atomic number (Z) but different mass numbers (A), and elements with the same number of protons but different numbers of neutrons.

[0028] In the present disclosure, "combinations thereof" refers to combinations of one or more elements from the corresponding list to form known or chemically stable configurations that can be envisioned by a person skilled in the art from the corresponding list. For example, alkyl and deuterium can be combined to form partially or fully deuterated alkyl groups; halogen and alkyl can be combined to form halogenated alkyl substituents; halogen, alkyl and aryl can be combined to form halogenated aryl alkyl. For example, preferred combinations of substituents may include up to 50 atoms that are not hydrogen or deuterium, or up to 40 atoms that are not hydrogen or deuterium, or up to 30 atoms that are not hydrogen or deuterium, or in many cases, preferred combinations of substituents may include up to 20 atoms that are not hydrogen or deuterium.

[0029] Organic electroluminescent devices are described in more detail below.

[0030] According to one embodiment of the present disclosure, an organic electroluminescent device is provided, which includes a first electrode; a second electrode facing the first electrode; and a structure in which a hole injection layer, a first hole transport layer, a second hole transport layer, a third transport layer, and a light emitting layer are stacked in order between the first electrode and the second electrode.Specifically, in the organic electroluminescent device according to one embodiment of the present disclosure, the structures of the compounds contained in the first hole transport layer, the second hole transport layer, and the third hole transport layer are different from each other; the second hole transport layer contains a compound having a fluorene-amine structure, a benzofluorene-amine structure, or a naphthofluorene-amine structure.

[0031] A compound containing a fluorene-amine structure, a benzofluorene-amine structure, or a naphthofluorene-amine structure can be represented by the following formula 1. [ka]

[0032] In formula 1, Ring A represents a substituted or unsubstituted benzene, a substituted or unsubstituted naphthalene, or a substituted or unsubstituted phenanthrene; Ar1 and Ar2 each independently represent a substituted or unsubstituted (C1 to C30) alkyl, a substituted or unsubstituted (C6 to C30) aryl, or may be linked together to form a ring; R and R1 to R4 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C3 to C30) cycloalkyl, substituted or unsubstituted (C6 to C30) aryl, substituted or unsubstituted (3 to 30 membered) heteroaryl, or substituted or unsubstituted (C1 to C30) alkoxy, or may be linked to adjacent substituents to form a ring, with the proviso that at least one of R and R1 to R4 is represented by -L1-NAr3Ar4; L1 represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; Ar3 and Ar4 each independently represent a substituted or unsubstituted (C6 to C30) aryl or a substituted or unsubstituted (3 to 30 membered) heteroaryl; n represents an integer of 1 to 8, and when n is a plurality of n's, each n may be the same or different.

[0033] According to one embodiment of the present disclosure, the compound represented by formula 1 can be represented by any one of the following formulas 1-1 to 1-11: [ka] [ka]

[0034] In formulas 1-1 to 1-11, Ar1 and Ar2 may each independently represent a substituted or unsubstituted (C1-C30) alkyl or a substituted or unsubstituted (C6-C30) aryl, or may be linked together to form a fused ring. According to one embodiment of the present disclosure, Ar1 and Ar2 may each independently represent a substituted or unsubstituted (C1-C20) alkyl or a substituted or unsubstituted (C6-C20) aryl, or may be linked together to form a fused ring. According to another embodiment of the present disclosure, Ar1 and Ar2 may each independently represent a substituted or unsubstituted (C1-C10) alkyl or a substituted or unsubstituted (C6-C10) aryl, or may be linked together to form a fused ring. For example, Ar1 and Ar2 may each independently represent methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, or phenyl, or may be linked together to form a (C13) aryl, which may be substituted with at least one deuterium.

[0035] R1~R 16each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy, or may be linked to adjacent substituents to form a ring, with the proviso that R1 to R 16 According to one embodiment of the present disclosure, at least one of R1 to R 16 each independently represents hydrogen, deuterium, a substituted or unsubstituted (C1-C20) alkyl, or a substituted or unsubstituted (C6-C20) aryl, or may be linked to an adjacent substituent to form a ring, provided that R1 to R 16 At least one of R1 to R3 is represented by -L1-NAr3Ar4. 16 may each independently be hydrogen, deuterium, unsubstituted or deuterium substituted phenyl, or -L1-NAr3Ar4.

[0036] L1 represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene. According to one embodiment of the present disclosure, L1 may represent a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (3-25 membered) heteroarylene. For example, L1 represents a single bond, phenylene, or phenanthrenylene, which may be substituted with at least one deuterium.

[0037] Ar3 and Ar4 each independently represent a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 membered) heteroaryl. According to an embodiment of the present disclosure, Ar3 and Ar4 each independently represent a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-25 membered) heteroaryl. For example, Ar3 and Ar4 each independently represent benzonaphthofuranyl; benzonaphthothiophenyl; unsubstituted or methyl-substituted biphenyl; dibenzofuranyl; dibenzothiophenyl; unsubstituted or phenyl-substituted dimethylfluorenyl; diethylfluorenyl; diphenylfluorenyl; dipropylfluorenyl; dibutylfluorenyl; dipentylfluorenyl; dihexylfluorenyl; diheptylfluorenyl; dioctylfluorenyl; unsubstituted or phenyl-substituted dimethylbenzofluorenyl; diethylbenzofluorenyl; unsubstituted or phenyl-substituted diphenylbenzofluorenyl; unsubstituted or It may represent naphthyl, phenyl (unsubstituted or substituted with deuterium), dibenzofuranyl, or phenanthrenyl substituted with phenyldimethylfluorenylamino; phenyl unsubstituted or substituted with naphthyl, benzonaphthofuranyl, benzonaphthothiophenyl, or methyl; naphthyl; quaterphenyl; o-terphenyl; m-terphenyl; p-terphenyl; or carbazolyl unsubstituted or substituted with phenyl (unsubstituted or substituted with methyl or adamantyl), naphthyl (unsubstituted or substituted with methyl), or biphenyl, which may be substituted with at least one deuterium.

[0038] The compound represented by formula 1 may be at least one selected from the following compounds, but is not limited thereto: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0039] In the above compound, Dn represents that n hydrogen atoms are replaced with deuterium atoms, and n represents an integer of 1 or more, which is an integer from 1 to the maximum number of hydrogen atoms in the compound.

[0040] Examples of the method for producing the compound represented by any one of formulas 1 or 1-1 to 1-11 according to the present disclosure are shown in the following reaction scheme 1 and reaction schemes 1-1 to 1-4, but are not limited thereto. The compound can be produced by a synthetic method known to those skilled in the art. [Reaction Scheme 1] [ka] [Reaction Scheme 1-1] [ka] [Reaction Scheme 1-2] [ka] [Reaction Scheme 1-3] [ka] [Reaction Scheme 1-4] [ka]

[0041] In the above reaction scheme, R and n are as defined in Formula 1, and R1 to R 12 , L1, and Ar1 to Ar4 are as defined in Formulas 1-1 to 1-11, respectively.

[0042] Illustrative synthetic examples of the compounds represented by formulae 1-1 to 1-11 are described above, but those skilled in the art will easily understand that all of these are based on Buchwald-Hartwig cross-coupling reactions, N-arylation reactions, H-mont mediated etherification reactions, Miyaura boronation reactions, Suzuki cross-coupling reactions, intramolecular acid-induced cyclization reactions, Pd(II)-catalyzed oxidative cyclization reactions, Grignard reactions, Heck reactions, dehydration ring-closing reactions, SN1 substitution reactions, SN2 substitution reactions, phosphine-mediated reductive cyclization reactions, and the like, and that the above reactions proceed even when substituents defined in formulae 1-1 to 1-11 but not specified in the specific synthetic examples are bonded.

[0043] In the organic electroluminescent device, the light-emitting layer emits any one of blue, green, or red light, except when the light-emitting layer emits blue or green light, R2 or R7 in formula 1-1 is -L1-NAr3Ar4.

[0044] In the organic electroluminescent device, the third hole transport layer comprises a compound represented by Formula 2: [ka]

[0045] In formula 2, L2 to L4 each independently represent a single bond, a substituted or unsubstituted (C1-C30) alkylene, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3-30 membered) heteroarylene, or a substituted or unsubstituted (C3-C30) cycloalkylene. According to one embodiment of the present disclosure, L2 to L4 each independently represent a single bond, a substituted or unsubstituted (C5-C25) alkylene, or a substituted or unsubstituted (C6-C25) arylene. According to another embodiment of the present disclosure, L2 to L4 each independently represent a single bond or a substituted or unsubstituted (C6-C25) arylene. For example, L2 to L4 each independently represent a single bond, an unsubstituted or deuterium-substituted phenylene, a biphenylene, a terphenylene, or a naphthylene, which may be substituted with at least one deuterium.

[0046] R5 to R7 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di(C1-C30) alkylamino, substituted or unsubstituted mono- or di(C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino. According to one embodiment of the present disclosure, Ar5 to Ar7 may each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C25) alkyl, substituted or unsubstituted (C6-C25) aryl, substituted or unsubstituted (3-membered to 25-membered) heteroaryl, substituted or unsubstituted (C3-C25) cycloalkyl, substituted or unsubstituted (C1-C25) alkoxy, substituted or unsubstituted tri(C1-C25) alkylsilyl, substituted or unsubstituted di(C1-C25) alkyl(C6-C25) arylsilyl, or substituted or unsubstituted tri(C6-C25) arylsilyl. For example, Ar5 to Ar7 each independently represent phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, dimethylfluorenyl, diethylfluorenyl, diphenylfluorenyl, diphenylbenzofluorenyl, spirobifluorenyl, carbazolyl which is unsubstituted or substituted with phenyl or naphthyl, phenanthrenyl which is unsubstituted or substituted with phenyl or naphthyl, o-terphenyl, m-terphenyl, p-terphenyl, adamantyl, or any one of the following formulae 2-1 to 2-6, which may be substituted with at least one deuterium.

[0047] However, the case where all of L2 to L4 are single bonds and all of Ar5 to Ar7 are hydrogen is excluded.

[0048] In the organic electroluminescent device, Ar5 in formula 2 is represented by any one of the following formulas 2-1 to 2-6. [ka]

[0049] In formulas 2-1 to 2-6, L5 represents a single bond, a substituted or unsubstituted (C1-C30) alkylene, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3-30 membered) heteroarylene, or a substituted or unsubstituted (C3-C30) cycloalkylene. According to one embodiment of the present disclosure, L5 may represent a single bond, a substituted or unsubstituted (C1-C30) alkylene, or a substituted or unsubstituted (C6-C30) arylene. According to another embodiment of the present disclosure, L5 may represent a single bond, a substituted or unsubstituted (C1-C20) alkylene, or a substituted or unsubstituted (C6-C20) arylene. For example, L5 may represent a single bond or phenylene, which may be substituted with at least one deuterium.

[0050] Ar8 is linked to L2 in formula 2, or is selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C 30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino. According to one embodiment of the present disclosure, R8 may be linked to L2 in formula 2, or may represent hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl. According to one embodiment of the present disclosure, R8 may be linked to L2 in formula 2, or may represent hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl. For example, Ar8 may be linked to L2 in formula 2 or may represent phenyl or naphthyl, which may be substituted with at least one deuterium.

[0051] R 17 ~R 68are connected to L2 in formula 2, or each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6- According to one embodiment of the present disclosure, R represents a substituted or unsubstituted (C1-C30)arylsilyl, a substituted or unsubstituted (C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di(C1-C30)alkylamino, a substituted or unsubstituted mono- or di(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, or may be linked to an adjacent substituent to form a ring. 17 ~R 68 may be linked to L2 in formula 2, or may each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, or may be linked to adjacent substituents to form a ring. 17 ~R 68 may be linked to L2 in formula 2, or each independently represent hydrogen, deuterium, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (3-25 membered) heteroaryl. For example, R 17 ~R 68 may be linked to L2 in formula 2, or each independently may represent hydrogen, deuterium, phenyl, or naphthyl.

[0052] However, Ar8 and R 17 ~R 68is connected to L2 in formula 2.

[0053] In the organic electroluminescent device, formula 2-3 is represented by any one of the following formulas 2-3-a to 2-3-c, or formula 2-4 is represented by any one of the following formulas 2-4-a to 2-4-c. [ka]

[0054] In formulae 2-3-a to 2-3-c and formulae 2-4-a to 2-4-c, R 35 ~R 50 is as defined in Formulas 2-1 to 2-6.

[0055] R 69 ~R 72 are connected to L2 in formula 2, or each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C 30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di(C1-C30) alkylamino, substituted or unsubstituted mono- or di(C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, or may be linked to adjacent substituents to form a ring. 69 ~R 72may be linked to L2 in formula 2, or each independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl. For example, R 69 ~R 72 may be linked to L2 in formula 2, or each independently may represent hydrogen.

[0056] However, R 35 ~R 50 , and R 69 ~R 72 is connected to L2 in formula 2.

[0057] The compound represented by formula 2 may be at least one selected from the following compounds, but is not limited thereto: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0058] In the above compound, Dn represents that n hydrogen atoms are replaced with deuterium atoms, and n represents an integer of 1 or more, which is an integer from 1 to the maximum number of hydrogen atoms in the compound.

[0059] The compound represented by formula 2 according to the present disclosure can be synthesized by referring to synthesis methods known to those skilled in the art, for example, methods disclosed in (Patent Document 3) (published June 16, 2015), (Patent Document 4) (published July 6, 2015), (Patent Document 5) (published April 21, 2017), (Patent Document 6) (published August 2, 2019), (Patent Document 7) (published January 13, 2020), (Patent Document 8) (published February 19, 2020), and (Patent Document 9) (published July 28, 2020), but is not limited thereto.

[0060] In the organic electroluminescent device, the light-emitting layer includes a red light-emitting layer.

[0061] Hereinafter, the organic electroluminescent compound according to one embodiment of the present disclosure will be described in detail.

[0062] The present disclosure provides an organic electroluminescent compound represented by the following formula 1: [ka]

[0063] In formula 1, Ring A represents a substituted or unsubstituted benzene, a substituted or unsubstituted naphthalene, or a substituted or unsubstituted phenanthrene; Ar1 and Ar2 each independently represent a substituted or unsubstituted (C2 to C30) alkyl; R and R1 to R4 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C3 to C30) cycloalkyl, substituted or unsubstituted (C6 to C30) aryl, substituted or unsubstituted (3 to 30 membered) heteroaryl, or substituted or unsubstituted (C1 to C30) alkoxy, or may be linked to adjacent substituents to form a ring, with the proviso that at least one of R and R1 to R4 is represented by -L1-NAr3Ar4; L1 represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; Ar3 and Ar4 each independently represent a substituted or unsubstituted (C6 to C30) aryl or a substituted or unsubstituted (3 to 30 membered) heteroaryl; n represents an integer of 1 to 8, and when n is a plurality of n's, each n may be the same or different.

[0064] Formula 1 can be represented by any one of the following formulas 1-1 to 1-11. [ka] [ka]

[0065] In formulas 1-1 to 1-11, Ar1 and Ar2 each independently represent a substituted or unsubstituted (C2-C30) alkyl. According to one embodiment of the present disclosure, Ar1 and Ar2 each independently represent a substituted or unsubstituted (C2-C20) alkyl. According to another embodiment of the present disclosure, Ar1 and Ar2 each independently represent a substituted or unsubstituted (C2-C10) alkyl. For example, Ar1 and Ar2 each independently may be methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, or octyl, which may be substituted with at least one deuterium.

[0066] R1~R16 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy, or may be linked to adjacent substituents to form a ring, with the proviso that R1 to R 16 According to one embodiment of the present disclosure, at least one of R1 to R 16 each independently represents hydrogen, deuterium, a substituted or unsubstituted (C1-C20) alkyl, or a substituted or unsubstituted (C6-C20) aryl, or may be linked to an adjacent substituent to form a ring, provided that R1 to R 16 At least one of R1 to R3 is represented by -L1-NAr3Ar4. 16 each independently represents hydrogen, deuterium, or -L1-NAr3Ar4.

[0067] L1 represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene. According to one embodiment of the present disclosure, L1 can represent a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (3-25 membered) heteroarylene. For example, L1 can represent a single bond or phenylene.

[0068] Ar3 and Ar4 each independently represent a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 membered) heteroaryl. According to one embodiment of the present disclosure, Ar3 and Ar4 each independently represent a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-25 membered) heteroaryl. For example, Ar3 and Ar4 can each independently represent benzonaphthofuranyl; benzonaphthothiophenyl; biphenyl; dibenzofuranyl; dibenzothiophenyl; dimethylfluorenyl; diethylfluorenyl; diphenylfluorenyl; dimethylbenzofluorenyl; diethylbenzofluorenyl; dipropylfluorenyl; dibutylfluorenyl; dipentylfluorenyl; dihexylfluorenyl; diheptylfluorenyl; dioctylfluorenyl; diphenylbenzofluorenyl; naphthyl; phenanthrenyl unsubstituted or substituted with naphthyl, phenyl, deuterium-substituted phenyl, dibenzofuranyl, or phenyldimethylfluorenylamino; phenyl unsubstituted or substituted with methyl, naphthyl, benzonaphthofuranyl, or benzonaphthothiophenyl; quaterphenyl; o-terphenyl; or p-terphenyl, which may be substituted with at least one deuterium.

[0069] Ar3 in formula 1 is represented by any one of the following formulas. [ka]

[0070] In the above formula, X is O, S, or NR 73 , or CR 74 R 75 For example, X represents O, S, or CR. 74 R 75 can be represented as follows.

[0071] R' and R 73 ~R 75are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C According to one embodiment of the present disclosure, R′ and R each represent a substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di(C1-C30) alkylamino, a substituted or unsubstituted mono- or di(C6-C30) arylamino, or a substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, or may be linked to adjacent substituents to form a substituted or unsubstituted (3- to 30-membered) monocyclic or polycyclic ring. 73 ~R 75 Each independently represents hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl, or a substituted or unsubstituted (C6-C30) aryl. According to another embodiment of the present disclosure, R′ and R 73 ~R 75 Each independently represents hydrogen, deuterium, a substituted or unsubstituted (C1-C20) alkyl, or a substituted or unsubstituted (C6-C20) aryl. For example, R' and R 73 ~R 75 may each independently represent hydrogen; deuterium; unsubstituted or deuterium-substituted methyl; unsubstituted or deuterium-substituted ethyl; unsubstituted or deuterium-substituted propyl; unsubstituted or deuterium-substituted butyl; unsubstituted or deuterium-substituted pentyl; unsubstituted or deuterium-substituted hexyl; unsubstituted or deuterium-substituted heptyl; unsubstituted or deuterium-substituted octyl; or unsubstituted or deuterium-substituted phenyl.

[0072] In each formula, any one of R' is linked to L1 in formula 1.

[0073] In each formula, a and b each independently represent an integer of 1 to 4, c and d each independently represent an integer of 1 to 6, e represents an integer of 1 to 10, and when a to e represent an integer of 2 or greater, each R' may be the same as or different from each other.

[0074] The compound represented by formula 1 may be at least one selected from the following compounds, but is not limited thereto: [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0075] In the above compound, Dn represents that n hydrogen atoms are replaced with deuterium atoms, and n represents an integer of 1 or more, which is an integer from 1 to the maximum number of hydrogen atoms in the compound.

[0076] An organic electroluminescent device according to an embodiment of the present disclosure may include an organic electroluminescent compound represented by Formula 1:

[0077] In addition, the present disclosure provides an organic electroluminescent compound represented by the following formula 3: [ka]

[0078] In Equation 3, R a ~R j At least one of the following formula 3-1 [ka] It is expressed as:

[0079] In formulas 3 and 3-1, R a ~R m each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl. a ~R m may each independently represent hydrogen, deuterium, a substituted or unsubstituted (C6-C20) aryl, or a substituted or unsubstituted (3-20 membered) heteroaryl. For example, R a ~R m may each independently represent hydrogen, deuterium, unsubstituted or deuterium-substituted phenyl, naphthyl, unsubstituted or deuterium-substituted biphenyl, or unsubstituted or deuterium-substituted m-terphenyl.

[0080] [ka] represents a bond between formula 3 and formula 3-1.

[0081] Each of L6 to L8 independently represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene. According to an embodiment of the present disclosure, each of L6 to L8 independently represents a single bond, or a substituted or unsubstituted (C6 to C20) arylene. For example, each of L6 to L8 independently represents a single bond, unsubstituted or deuterium-substituted phenylene, naphthylene, unsubstituted or deuterium-substituted biphenylene, or unsubstituted or deuterium-substituted m-terphenylene.

[0082] Ar8 represents a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (C3-C30) cycloalkyl, or a substituted or unsubstituted (3-30 membered) heteroaryl. According to an embodiment of the present disclosure, Ar8 may represent a substituted or unsubstituted (C6-C20) aryl, a substituted or unsubstituted (C3-C20) cycloalkyl, or a substituted or unsubstituted (3-20 membered) heteroaryl. For example, Ar8 may represent unsubstituted or deuterium- or naphthyl-substituted phenyl, unsubstituted or deuterium-substituted biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, dimethylfluorenyl, diphenylfluorenyl, dibenzoselenophenyl, spirobifluorenyl, o-terphenyl, m-terphenyl, or adamantyl.

[0083] k and l each independently represent an integer of 1 to 5, and m represents an integer of 1 to 3. For example, k and l each independently represent an integer of 5, and m represents an integer of 3.

[0084] When k~m are integers of 2 or more, R k ~R m may be the same or different from each other.

[0085] According to one embodiment of the present disclosure, the compound represented by formula 3-1 is represented by any one of the following formulas 3-1a to 3-1f. [ka] [ka]

[0086] In formulas 3-1a to 3-1f, [ka] represents a linking group linked to formula 3; L6~L8, Ar8, and R k ~R m is as defined in Equation 3 and Equation 3-1; k and l each independently represent an integer of 1 to 5, and m represents an integer of 1 to 3; When k~m are integers of 2 or more, R k ~R m may be the same or different from one another.

[0087] The compound represented by formula 3 may be at least one selected from the following compounds, but is not limited thereto: [ka] [ka] [ka] [ka] [ka] [ka]

[0088] In the above compound, Dn represents that n hydrogen atoms are replaced with deuterium atoms, and n represents an integer of 1 or more, which is an integer from 1 to the maximum number of hydrogen atoms in the compound.

[0089] Exemplary methods for preparing compounds of formula 3 according to the present disclosure are shown below, but are not limited to, in Reaction Scheme 2 and Reaction Scheme 3. Such compounds can be prepared by synthetic methods known to those skilled in the art. [Reaction Scheme 2] [ka] [Reaction Scheme 3] [ka]

[0090] In the above Reaction Scheme 2 and Reaction Scheme 3, R a ~R m , L6 to L8, Ar8, and km are as defined in Formula 3 and Formula 3-1.

[0091] An organic electroluminescent device according to the present disclosure may include an organic electroluminescent compound represented by Formula 3.

[0092] The light-emitting layer can include one or more hosts and one or more dopants. If necessary, the light-emitting layer can include co-host materials, i.e., multiple host materials. The host used in the present invention can be a phosphorescent host compound or a fluorescent host compound, and these host compounds are not particularly limited thereto.

[0093] According to one embodiment of the present disclosure, the doping concentration of the dopant compound relative to the host compound of the light-emitting layer can be less than 20% by weight.The dopant contained in the organic electroluminescent device of the present disclosure can be at least one phosphorescent or fluorescent dopant, and is preferably a phosphorescent dopant.The phosphorescent dopant material applied to the organic electroluminescent device according to the present disclosure can be, but is not limited to, a metallized complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), preferably an ortho-metallized complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), more preferably an ortho-metallized iridium complex compound.

[0094] The dopant included in the organic electroluminescent device of the present disclosure can be, but is not limited to, a compound represented by Formula 101 below: [ka]

[0095] In formula 101, L is the following structure 1 to 3: [ka] One of the following is selected from the R 100 ~R 103 each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium and / or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (3-30 membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy, or may be linked with adjacent substituents to form a ring together with pyridine, such as substituted or unsubstituted quinoline, benzofuropyridine, benzothienopyridine, indenopyridine, benzofuroquinoline, benzothienoquinoline, or indenoquinoline; R 104 ~R 107 each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium and / or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy, or may be linked with adjacent substituents to form a substituted or unsubstituted ring, for example, substituted or unsubstituted naphthalene, fluorene, dibenzothiophene, dibenzofuran, indenopyridine, benzofuropyridine, or benzothienopyridine together with benzene; R 201 ~R 220 each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium and / or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C6-C30) aryl, or may be bonded to adjacent substituents to form a substituted or unsubstituted ring; s represents an integer of 1 to 3.

[0096] Specific examples of the dopant compound are as follows, but are not limited thereto. [ka] [ka] [ka] [ka] [ka] [ka]

[0097] The organic electroluminescent device according to the present disclosure includes an anode, a cathode, and at least one organic layer between the anode and the cathode. The organic layer includes an emitting layer, and may further include at least one layer selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, an 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 the layers may further be configured as a plurality of layers.

[0098] Each of the anode and cathode may be made of a transparent conductive material, or may be made of a semi-transparent or reflective conductive material. Depending on the type of material that forms the anode and cathode, the organic electroluminescent device may be top-emitting, bottom-emitting, or double-sided emitting. In addition, the hole injection layer may be further doped with a p-type dopant, and the electron injection layer may be further doped with an n-type dopant.

[0099] The organic layer may further include at least one compound selected from the group consisting of arylamine compounds and styrylarylamine compounds. Furthermore, the organic material layer may further include at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of Period 4, transition metals of Period 5, lanthanides, and organometallic elements of d-transition elements of the periodic table, or at least one complex compound containing the metal.

[0100] In addition, the organic electroluminescent device of the present disclosure can emit white light by further comprising at least one light-emitting layer that comprises the blue, red or green light-emitting compound known in the art in addition to the compound of the present disclosure.In addition, if necessary, it can also comprise a yellow or orange light-emitting layer.

[0101] In the organic electroluminescent device of the present disclosure, at least one layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter referred to as a "surface layer") is preferably disposed on the inner surface of at least one of a pair of electrodes. Specifically, a chalcogenide (including oxide) layer of silicon and aluminum is preferably disposed on the anode surface on the electroluminescent medium layer side, and a metal halide layer or a metal oxide layer is preferably disposed on the cathode surface on the electroluminescent medium layer side. The driving stability of the organic electroluminescent device can be obtained by the surface layer. A preferred example of the chalcogenide is SiO X (1≦X≦2), AlO X (1≦X≦1.5), SiON, SiAlON, etc.; preferred examples of metal halides include LiF, MgF2, CaF2, rare earth metal fluorides, etc., and preferred examples of metal oxides include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0102] A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof can be used between the anode and the light emitting layer. The hole injection layer can be multi-layered to reduce the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, and two kinds of compounds can be used simultaneously in each of the multi-layered layers. The hole transport layer or the electron blocking layer can be multi-layered.

[0103] An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be used between the light emitting layer and the cathode. The electron buffer layer may be multi-layered for the purpose of controlling electron injection and improving the interface properties between the light emitting layer and the electron injection layer, and two kinds of compounds may be used simultaneously in each of the multi-layered layers. The hole blocking layer or the electron transport layer may be multi-layered, and multiple compounds may be used in each of the multi-layered layers.

[0104] The light-emitting auxiliary layer can be a layer disposed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer, or between the cathode and the light-emitting layer. When disposed between the anode and the light-emitting layer, the light-emitting auxiliary layer can be used to promote hole injection and / or hole transport, or to block electron overflow. When disposed between the cathode and the light-emitting layer, the light-emitting auxiliary layer can be used to promote electron injection and / or electron transport, or to block hole overflow. In addition, the hole auxiliary layer can be disposed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can exhibit the effect of promoting or blocking the transport rate of holes (or hole injection rate), thereby adjusting the charge balance. Furthermore, the electron blocking layer can be disposed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can block the overflow of electrons from the light-emitting layer and confine excitons in the light-emitting layer to prevent light leakage. When the organic electroluminescent device comprises two or more hole transport layers, the further comprised hole transport layer can be used as a hole auxiliary layer or an electron blocking layer. The light emitting auxiliary layer, the hole auxiliary layer, or the electron blocking layer can have the effect of improving the efficiency and / or life of the organic electroluminescent device.

[0105] In addition, in the organic electroluminescent device of the present disclosure, the mixed region of the electron transport compound and the reductive dopant or the mixed region of the hole transport compound and the oxidative dopant can be disposed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to anion, so that it is easier to inject and transport electrons from the mixed region to the luminescent medium. Furthermore, the hole transport compound is oxidized to cation, so that it is easier to inject and transport holes from the mixed region to the luminescent medium. Preferred oxidative dopants include various Lewis acids and acceptor compounds, and preferred reductive dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, by using a reductive dopant layer as a charge generating layer, an organic electroluminescent device having at least two luminescent layers and emitting white light can be manufactured.

[0106] The organic electroluminescent device according to the present disclosure may be an organic electroluminescent device having a tandem structure. In the case of a tandem organic electroluminescent device according to an embodiment, a single light-emitting unit (light-emitting portion) 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 having a first electrode and a second electrode facing each other on a substrate, and a light-emitting layer stacked between the first electrode and the second electrode and emitting in a specific wavelength range. It may include a plurality of light-emitting units, each of which may include a hole transport zone, a light-emitting layer, and an electron transport zone, the hole transport zone may include a hole injection layer and a hole transport layer, and the electron transport zone may include an electron transport layer and an electron injection layer. According to an embodiment of the present disclosure, three or more light-emitting layers may be included in the light-emitting unit. The multiple light-emitting units may emit the same color or different colors. In addition, one light-emitting unit can also include one or more light-emitting layers, and the multiple light-emitting layers can be light-emitting layers of the same color or different colors. It can include one or more charge-generating layers disposed between each light-emitting unit. The charge-generating layer refers to a layer in which holes and electrons are generated when a voltage is applied. When there are three or more light-emitting units, a charge-generating layer can be disposed between each light-emitting unit. At this time, the multiple charge-generating layers can be the same or different from each other. By disposing the charge-generating layer between the light-emitting units, the current efficiency can be enhanced in each light-emitting unit and the charge can be distributed smoothly. Specifically, the charge-generating layer can be provided between two adjacent stacks, which can be useful for driving the tandem organic electroluminescent device using only a pair of anode and cathode without a separate internal electrode disposed between the stacks.

[0107] The charge generation layer may be composed of an n-type charge generation layer and a p-type charge generation layer, and the n-type charge generation layer may be doped with an alkali metal, an alkaline earth metal, or a compound of an alkali metal and an alkaline earth metal. The alkali metal may include one selected from the group consisting of Li, Na, K, Rb, Cs, Fr, Yb, and combinations thereof, and the alkaline earth metal may include one selected from the group consisting of Be, Mg, Ca, Sr, Ba, Ra, and combinations thereof. The p-type charge generation layer may be made of a metal or an organic material doped with a p-type dopant. For example, the metal may be made of one or an alloy of two or more selected from the group consisting of Al, Cu, Fe, Pb, Zn, Au, Pt, W, In, Mo, Ni, and Ti. Moreover, commonly used materials may be used as host materials for p-type dopants and p-type doped organic materials.

[0108] The organic electroluminescent material according to an embodiment of the present disclosure can be used as the light-emitting material for white organic light-emitting devices. The white organic light-emitting devices have been proposed to have various structures, such as side-by-side arrangement method, stacked arrangement method, or color conversion material (CCM) method, etc., depending on the arrangement of R (red), G (green) or YG (yellow-green) and B (blue) light-emitting units. In addition, the organic electroluminescent material according to an embodiment of the present disclosure can also be used in organic electroluminescent devices that include quantum dots (QDs).

[0109] To form each layer of the organic electroluminescent device of the present disclosure, dry film forming methods such as vacuum evaporation, sputtering, plasma, ion plating, etc., or wet film forming methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating, etc. can be used. When forming a film of the first host compound and the second host compound of the present disclosure, co-evaporation or mixed deposition is carried out.

[0110] When using a wet film-forming method, the thin film can be formed by dissolving or dispersing the material forming each layer in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent can be any solvent in which the material forming each layer can be dissolved or dispersed and which has no problem in film-forming ability.

[0111] In addition, the organic electroluminescent devices of the present disclosure can be used to manufacture display systems, such as display systems for smartphones, tablets, notebooks, PCs, TVs, or automobiles; or lighting systems, such as outdoor or indoor lighting systems.

[0112] Hereinafter, the preparation method of the compound of the present disclosure and their properties, and the driving voltage and luminous efficiency of the organic electroluminescent device (OLED) that comprises the organic electroluminescent compound of the present disclosure will be described in detail with respect to the representative compound of the present disclosure.However, the following examples only describe the properties of the compound of the present disclosure and the OLED that comprises it, and the present disclosure is not limited to the following examples.

[0113] In the following, the preparation method of the host material according to the present disclosure will be described with reference to the synthesis method of representative compounds or intermediate compounds in order to understand the present disclosure in detail. EXAMPLES

[0114] Example 1: Preparation of compound C-86 [ka] Compound 1-1 (CAS: 373390-07-9) (10.5 g, 33.5 mmol), compound 1-2 (CAS: 2408008-08-0) (10.0 g, 37.2 mmol), tris(dibenzylideneacetone)dipalladium(0) (1.70 g, 1.86 mmol), tri-t-butylphosphine (1.84 mL, 3.72 mmol, 50% toluene solution), sodium t-butoxide (7.15 g, 74.4 mmol), and 186 mL of toluene were placed in a flask and refluxed for 2 hours. The reaction solution was cooled to room temperature, and the solvent was removed using a rotary evaporator, and then the mixture was purified by column chromatography to obtain compound C-86 (11.5 g, yield: 57%) as a white solid.

[0115] Example 2: Preparation of compound C-111 [ka] Compound 1-1 (CAS: 373390-07-9) (11.2 g, 35.6 mmol), compound 1-3 (CAS: 2305687-93-6) (10.0 g, 39.6 mmol), tris(dibenzylideneacetone)dipalladium(0) (1.81 g, 1.98 mmol), tri-t-butylphosphine (1.95 mL, 3.96 mmol, 50% toluene solution), sodium t-butoxide (7.61 g, 79.1 mmol), and 198 mL of toluene were placed in a flask and refluxed for 2 hours. The reaction solution was cooled to room temperature, and the solvent was removed using a rotary evaporator, and then the mixture was purified by column chromatography to obtain compound C-111 (5.2 g, yield: 28%) as a white solid.

[0116] Example 3: Preparation of compound C-1 [ka] Compound 1-1 (CAS: 373390-07-9) (10.0 g, 32.0 mmol), compound 1-4 (CAS: 2397634-76-1) (9.7 g, 35.0 mmol), tris(dibenzylideneacetone)dipalladium(0) (1.5 g, 1.60 mmol), tri-t-butylphosphine (1.58 mL, 3.20 mmol, 50% toluene solution), sodium t-butoxide (6.15 g, 64.0 mmol), and 160 mL of toluene were added to a flask and refluxed for 1 hour. The reaction solution was cooled to room temperature, and the solvent was removed using a rotary evaporator, and then the mixture was purified by column chromatography to obtain compound C-1 (8.9 g, yield: 50%) as a white solid.

[0117] Example 4: Preparation of compound C-36 [ka] Compound 1-1 (CAS: 373390-07-9) (8.0 g, 26.0 mmol), compound 1-5 (CAS: 2412522-09-7) (12.3 g, 31.0 mmol), tris(dibenzylideneacetone)dipalladium(0) (1.20 g, 1.30 mmol), tri-t-butylphosphine (1.30 mL, 2.60 mmol, 50% toluene solution), sodium t-butoxide (4.9 g, 52.0 mmol), and 130 mL of toluene were added to a flask and refluxed for 1 hour. The reaction solution was cooled to room temperature, and the solvent was removed using a rotary evaporator, and then the mixture was purified by column chromatography to obtain compound C-36 (15.4 g, yield: 89%) as a white solid.

[0118] [Table 1]

[0119] Example 5: Preparation of Compound C-279 [ka] Compound 1-6 (CAS: 1776936-11-8) (3.0 g, 9.33 mmol), compound 1-7 (CAS: 1198396-39-2) (4.2 g, 13.1 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.43 g, 0.47 mmol), tri-t-butylphosphine (0.45 mL, 0.93 mmol, 50% toluene solution), sodium t-butoxide (1.35 g, 14.0 mmol), and 48 mL of toluene were placed in a flask and refluxed for 1 hour. The reaction solution was cooled to room temperature, and the solvent was removed using a rotary evaporator, and then the mixture was purified by column chromatography to obtain compound C-279 (5.3 g, yield: 98%) as a white solid.

[0120] [Table 2]

[0121] Device Example 1: Fabrication of a Red-Emitting OLED According to the Present Disclosure An OLED according to the present disclosure was manufactured. First, a transparent electrode indium tin oxide (ITO) thin film (10 Ω / sq) on a glass substrate for an OLED (Geomatec Co., Ltd., Japan) was subjected to ultrasonic cleaning in acetone and isopropyl alcohol, successively, and then stored in isopropyl alcohol. The ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus. Compound HI-1 shown in Table 2 as a first hole injection compound was introduced into a cell of the vacuum deposition apparatus, and compound HT-1 shown in Table 2 as a first hole transport compound was introduced into another cell. The two materials were evaporated at different rates, and the first hole injection compound was evaporated with a doping amount of 3 wt % based on the total amount of the first hole injection compound and the first hole transport compound to form a first hole injection layer having a thickness of 10 nm. Compound HT-1 was then evaporated on the first hole injection layer to form a first hole transport layer having a thickness of 90 nm. Next, compound C-86 shown in Table 2 as a second hole transport compound was introduced into another cell of the vacuum deposition apparatus, and evaporated by passing a current through the cell, thereby depositing a second hole transport layer having a thickness of 55 nm on the first hole transport layer. Next, compound H-31 shown in Table 2 as a third hole transport compound was introduced into another cell of the vacuum deposition apparatus, and evaporated by passing a current through the cell, thereby depositing a third hole transport layer having a thickness of 5 nm on the second hole transport layer. After forming the hole injection layer and the hole transport layer, the light-emitting layer was deposited thereon as follows: compound A-1 and compound B-1 were introduced into two cells of the vacuum deposition apparatus as hosts for the light-emitting layer, and compound A-1 and compound B-1 were evaporated in a ratio of 1:1. Compound D-39 was introduced as a dopant into another cell, and then the dopant was evaporated in a doping amount of 2 wt% based on the total amount of the host and the dopant to form a 40 nm thick light-emitting layer on the third hole transport layer. Compound B-2 was then evaporated on the light-emitting layer as an electron buffer material to a thickness of 5 nm. Compound ET-1 and compound EI-1 were then doped in a weight ratio of 5:5 to form an electron transport layer, and evaporated to a thickness of 30 nm.Compound EI-1 was deposited on the electron transport layer as an electron injection layer with a thickness of 2 nm, and then an Al cathode was deposited on the electron injection layer with a thickness of 80 nm by using another vacuum deposition apparatus, thereby fabricating an OLED.

[0122] Device Examples 2 and 3: Fabrication of Red-Emitting OLEDs According to the Present Disclosure An OLED was fabricated in the same manner as in Device Example 1, except that compounds C-111 and C-1 shown in Table 2 were used in the second hole-transporting layer as the second hole-transporting compound instead of compound C-86.

[0123] Device Example 4: Fabrication of a Red-Emitting OLED According to the Present Disclosure An OLED was fabricated in the same manner as Device Example 1, except that compound C-36 shown in Table 2 was used in the second hole-transporting layer as the second hole-transporting compound instead of compound C-86, and compound H-1 shown in Table 2 was used in the third hole-transporting layer as the third hole-transporting compound instead of compound H-31.

[0124] Comparative Example 1: Fabrication of a red-emitting OLED not according to the present disclosure An OLED was fabricated in the same manner as Device Example 1, except that a single compound, H-31, was deposited at 60 nm instead of using each compound in the second and third hole-transporting layers.

[0125] Comparative Example 2: Fabrication of a red-emitting OLED not according to the present disclosure An OLED was fabricated in the same manner as Device Example 1, except that a single compound H-1 was deposited at 60 nm instead of using each compound in the second and third hole-transporting layers.

[0126] The driving voltage, current efficiency, and CIE color coordinates at a luminance of 1,000 nits of the OLED devices of device Examples 1 to 4 and Comparative Examples 1 and 2 prepared as above were measured, and the results are shown in Table 1 below.

[0127] [Table 3]

[0128] From Table 1 above, it can be seen that the OLED according to the present disclosure exhibits characteristics of lower driving voltage and higher current efficiency compared to the OLED using conventional compounds in the second and third hole transport layers.

[0129] The compounds used in Device Examples 1-4 and Comparative Examples 1 and 2 are shown in Table 2 below.

[0130] [Table 4]

[0131] [Table 5]

[0132] [Table 6]

[0133] Device Example 5: Fabrication of a Red-Emitting OLED According to the Present Disclosure An OLED according to the present disclosure was manufactured. First, a transparent electrode indium tin oxide (ITO) thin film (10 Ω / sq) on a glass substrate for an OLED (Geomatec Co., Ltd., Japan) was subjected to ultrasonic cleaning in acetone and isopropyl alcohol, successively, and then stored in isopropyl alcohol. The ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus. Compound HI-1 shown in Table 4 as a first hole injection compound was introduced into a cell of the vacuum deposition apparatus, and compound HT-2 shown in Table 4 as a first hole transport compound was introduced into another cell. The two materials were evaporated at different rates, and the first hole injection compound was evaporated with a doping amount of 5 wt % based on the total amount of the first hole injection compound and the first hole transport compound to form a first hole injection layer having a thickness of 10 nm. Compound HT-2 was then evaporated on the first hole injection layer to form a first hole transport layer having a thickness of 90 nm. Next, compound C-279 shown in Table 4 as a second hole transport compound was introduced into another cell of the vacuum deposition apparatus, and evaporated by passing a current through the cell, thereby depositing a second hole transport layer having a thickness of 60 nm on the first hole transport layer. Next, compound H-56 shown in Table 4 as a third hole transport compound was introduced into another cell of the vacuum deposition apparatus, and evaporated by passing a current through the cell, thereby depositing a third hole transport layer having a thickness of 7.5 nm on the second hole transport layer. After forming the hole injection layer and the hole transport layer, the light-emitting layer was deposited thereon as follows: compound A-2 and compound B-1 were introduced into two cells of the vacuum deposition apparatus as hosts for the light-emitting layer, and compound A-2 and compound B-1 were evaporated in a ratio of 1:1. Compound D-39 was introduced as a dopant into another cell, and then the dopant was evaporated with a doping amount of 2 wt% based on the total amount of the host and the dopant to form a 36 nm thick light-emitting layer on the third hole transport layer. Compound B-3 was then evaporated on the light-emitting layer as an electron buffer material to a thickness of 5 nm. Compounds ET-2 and EI-1 were then doped in a weight ratio of 2:1 to form an electron transport layer, and evaporated to a thickness of 25 nm.Compound EI-1 was deposited on the electron transport layer as an electron injection layer with a thickness of 2 nm, and then an Al cathode was deposited on the electron injection layer with a thickness of 80 nm by using another vacuum deposition apparatus, thereby fabricating an OLED.

[0134] Device Example 6: Fabrication of a Red-Emitting OLED According to the Present Disclosure An OLED was fabricated in the same manner as Device Example 5, except that compound A-3 shown in Table 4 was used in the light-emitting layer as the light-emitting compound instead of compound A-2.

[0135] Comparative Example 3: Fabrication of a Red-Emitting OLED Device Not According to the Present Disclosure An OLED was fabricated in the same manner as Device Example 5, except that a single compound, H-56, was deposited at 67.5 nm instead of using each compound in the second and third hole-transporting layers.

[0136] Comparative Example 4: Fabrication of a Red-Emitting OLED Device Not According to the Present Disclosure An OLED was fabricated in the same manner as in Device Example 5, except that instead of using each compound in the second and third hole transport layers, a single compound H-56 was evaporated at 67.5 nm, and compound A-3 shown in Table 4 was used in the emissive layer as the emissive compound instead of compound A-2.

[0137] The driving voltage, current efficiency, and CIE color coordinates at a luminance of 1,000 nits of the OLED devices of device Examples 5 and 6, and Comparative Examples 3 and 4 prepared as above were measured, and the results are shown in Table 3 below.

[0138] [Table 7]

[0139] From Table 3 above, it can be seen that the OLED according to the present disclosure exhibits characteristics of lower driving voltage and higher current efficiency compared to the OLED using conventional compounds in the second and third hole transport layers.

[0140] The compounds used in Device Examples 5 and 6 and Comparative Examples 3 and 4 are shown in Table 4 below.

[0141] [Table 8]

[0142] [Table 9]

[0143] Device Example 7: Fabrication of a Red-Emitting OLED According to the Present Disclosure An OLED according to the present disclosure was manufactured. First, a transparent electrode indium tin oxide (ITO) thin film (10 Ω / sq) on a glass substrate for an OLED (Geomatec Co., Ltd., Japan) was subjected to ultrasonic cleaning in acetone and isopropyl alcohol, successively, and then stored in isopropyl alcohol. The ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus. Compound HI-1 shown in Table 6 as a first hole injection compound was introduced into a cell of the vacuum deposition apparatus, and compound HT-1 shown in Table 6 as a first hole transport compound was introduced into another cell. The two materials were evaporated at different rates, and the first hole injection compound was evaporated with a doping amount of 3 wt % based on the total amount of the first hole injection compound and the first hole transport compound to form a first hole injection layer having a thickness of 10 nm. Compound HT-1 was then evaporated on the first hole injection layer to form a first hole transport layer having a thickness of 90 nm. Next, compound C-1 shown in Table 6 as a second hole transport compound was introduced into another cell of the vacuum deposition apparatus, and evaporated by passing a current through the cell, thereby depositing a second hole transport layer having a thickness of 55 nm on the first hole transport layer. Next, compound H-13 shown in Table 6 as a third hole transport compound was introduced into another cell of the vacuum deposition apparatus, and evaporated by passing a current through the cell, thereby depositing a third hole transport layer having a thickness of 5 nm on the second hole transport layer. After forming the hole injection layer and the hole transport layer, the light-emitting layer was deposited thereon as follows: compound A-1 and compound B-1 were introduced into two cells of the vacuum deposition apparatus as hosts for the light-emitting layer, and compound A-1 and compound B-1 were evaporated in a ratio of 4:6. Compound D-39 was introduced as a dopant into another cell, and then the dopant was evaporated in a doping amount of 2 wt% based on the total amount of the host and the dopant to form a 40 nm thick light-emitting layer on the third hole transport layer. Compound B-2 was then evaporated on the light-emitting layer as an electron buffer material to a thickness of 5 nm. Compound ET-1 and compound EI-1 were then doped in a weight ratio of 5:5 to form an electron transport layer, and evaporated to a thickness of 30 nm.Compound EI-1 was deposited on the electron transport layer as an electron injection layer with a thickness of 2 nm, and then an Al cathode was deposited on the electron injection layer with a thickness of 80 nm by using another vacuum deposition apparatus, thereby fabricating an OLED.

[0144] Device Examples 8 and 9: Fabrication of Red-Emitting OLEDs According to the Present Disclosure An OLED was fabricated in the same manner as in Device Example 7, except that compounds H-5 and H-114 shown in Table 5 were used in the third hole-transporting layer as the third hole-transporting compound instead of compound H-13.

[0145] The driving voltage, current efficiency, and CIE color coordinates at a luminance of 1,000 nits of the OLED devices of Device Examples 7 to 9 prepared as above were measured, and the results are shown in Table 5 below.

[0146] [Table 10]

[0147] From Table 5 above, it can be seen that the OLED according to the present disclosure exhibits the characteristics of low driving voltage and high current efficiency.

[0148] The compounds used in Device Examples 7-9 are shown in Table 6 below.

[0149] [Table 11]

[0150] [Table 12]

[0151] Device Example 10: Fabrication of a Red-Emitting OLED According to the Present Disclosure An OLED according to the present disclosure was manufactured. First, a transparent electrode indium tin oxide (ITO) thin film (10 Ω / sq) on a glass substrate for an OLED (Geomatec Co., Ltd., Japan) was subjected to ultrasonic cleaning in acetone and isopropyl alcohol, successively, and then stored in isopropyl alcohol. The ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus. Compound HI-1 shown in Table 8 as a first hole injection compound was introduced into a cell of the vacuum deposition apparatus, and compound HT-1 shown in Table 8 as a first hole transport compound was introduced into another cell. The two materials were evaporated at different rates, and the first hole injection compound was evaporated with a doping amount of 3 wt % based on the total amount of the first hole injection compound and the first hole transport compound to form a first hole injection layer having a thickness of 10 nm. Compound HT-1 was then evaporated on the first hole injection layer to form a first hole transport layer having a thickness of 90 nm. Next, compound C-351 shown in Table 8 as a second hole transport compound was introduced into another cell of the vacuum deposition apparatus, and evaporated by passing a current through the cell, thereby depositing a second hole transport layer having a thickness of 55 nm on the first hole transport layer. Next, compound H-5 shown in Table 8 as a third hole transport compound was introduced into another cell of the vacuum deposition apparatus, and evaporated by passing a current through the cell, thereby depositing a third hole transport layer having a thickness of 5 nm on the second hole transport layer. After forming the hole injection layer and the hole transport layer, the light-emitting layer was deposited thereon as follows: compound A-1 and compound B-1 were introduced into two cells of the vacuum deposition apparatus as hosts for the light-emitting layer, and compound A-1 and compound B-1 were evaporated in a ratio of 1:1. Compound D-39 was introduced as a dopant into another cell, and then the dopant was evaporated in a doping amount of 2 wt% based on the total amount of the host and the dopant to form a 40 nm thick light-emitting layer on the third hole transport layer. Compound B-2 was then evaporated on the light-emitting layer as an electron buffer material to a thickness of 5 nm. Compound ET-1 and compound EI-1 were then doped in a weight ratio of 5:5 to form an electron transport layer, and evaporated to a thickness of 30 nm.Compound EI-1 was deposited on the electron transport layer as an electron injection layer with a thickness of 2 nm, and then an Al cathode was deposited on the electron injection layer with a thickness of 80 nm by using another vacuum deposition apparatus, thereby fabricating an OLED.

[0152] Device Examples 11 and 12: Fabrication of Red-Emitting OLEDs According to the Present Disclosure An OLED was fabricated in the same manner as Device Example 10, except that compounds C-164 and C-163 shown in Table 7 were used in the second hole-transporting layer as the second hole-transporting compound instead of compound C-351.

[0153] The driving voltage, current efficiency, and CIE color coordinates at a luminance of 1,000 nits of the OLED devices of Device Examples 10 to 12 prepared as above were measured, and the results are shown in Table 7 below.

[0154] [Table 13]

[0155] From Table 7 above, it can be seen that the OLED according to the present disclosure exhibits the characteristics of low driving voltage and high current efficiency.

[0156] The compounds used in Device Examples 10-12 are shown in Table 8 below.

[0157] [Table 14]

[0158] [Table 15]

[0159] Device Example 13: Fabrication of a Red-Emitting OLED According to the Present Disclosure An OLED according to the present disclosure was manufactured. First, a transparent electrode indium tin oxide (ITO) thin film (10 Ω / sq) on a glass substrate for an OLED (Geomatec Co., Ltd., Japan) was subjected to ultrasonic cleaning in acetone and isopropyl alcohol, successively, and then stored in isopropyl alcohol. The ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus. Compound HI-1 shown in Table 10 as a first hole injection compound was introduced into a cell of the vacuum deposition apparatus, and compound HT-2 shown in Table 10 as a first hole transport compound was introduced into another cell. The two materials were evaporated at different rates, and the first hole injection compound was evaporated with a doping amount of 5 wt % based on the total amount of the first hole injection compound and the first hole transport compound to form a first hole injection layer having a thickness of 10 nm. Compound HT-2 was then evaporated on the first hole injection layer to form a first hole transport layer having a thickness of 90 nm. Next, compound C-272 shown in Table 10 as a second hole transport compound was introduced into another cell of the vacuum deposition apparatus, and evaporated by passing a current through the cell, thereby depositing a second hole transport layer having a thickness of 60 nm on the first hole transport layer. Next, compound H-56 shown in Table 10 as a third hole transport compound was introduced into another cell of the vacuum deposition apparatus, and evaporated by passing a current through the cell, thereby depositing a third hole transport layer having a thickness of 7.5 nm on the second hole transport layer. After forming the hole injection layer and the hole transport layer, the light-emitting layer was deposited thereon as follows: compound A-2 and compound B-1 were introduced into two cells of the vacuum deposition apparatus as hosts for the light-emitting layer, and compound A-2 and compound B-1 were evaporated in a ratio of 1:1. Compound D-39 was introduced as a dopant into another cell, and then the dopant was evaporated in a doping amount of 2 wt% based on the total amount of the host and the dopant to form a 36 nm thick light-emitting layer on the third hole transport layer. Compound B-3 was then evaporated on the light-emitting layer as an electron buffer material to a thickness of 5 nm. Compound ET-2 and compound EI-1 were then doped in a weight ratio of 2:1 to form an electron transport layer, and evaporated to a thickness of 25 nm.Compound EI-1 was deposited on the electron transport layer as an electron injection layer with a thickness of 2 nm, and then an Al cathode was deposited on the electron injection layer with a thickness of 80 nm by using another vacuum deposition apparatus, thereby fabricating an OLED.

[0160] Device Examples 14-23: Fabrication of Red-Emitting OLEDs According to the Present Disclosure An OLED was fabricated in the same manner as Device Example 13, except that each of the compounds shown in Table 9 was used in the second hole-transporting layer as the second hole-transporting compound instead of compound C-272.

[0161] The driving voltage, current efficiency, and CIE color coordinates at a luminance of 1,000 nits of the OLED devices of Device Examples 10 to 12 prepared as above were measured, and the results are shown in Table 9 below.

[0162] [Table 16]

[0163] From Table 9 above, it can be seen that the OLED according to the present disclosure exhibits the characteristics of low driving voltage and high current efficiency.

[0164] The compounds used in Device Examples 13-23 are shown in Table 10 below.

[0165] [Table 17]

[0166] [Table 18]

[0167] [Table 19]

Claims

1. An organic electroluminescent device comprising: a first electrode; a second electrode opposed to the first electrode; and a structure in which a hole injection layer, a first hole transport layer, a second hole transport layer, a third transport layer, and a light emitting layer are laminated in this order between the first electrode and the second electrode, the structures of compounds contained in the first hole transport layer, the second hole transport layer, and the third hole transport layer are different from each other; The organic electroluminescent device, wherein the second hole transport layer contains a compound containing a fluorene-amine structure, a benzofluorene-amine structure, or a naphthofluorene-amine structure.

2. 2. The organic electroluminescent device of claim 1, wherein the compound containing a fluorene-amine structure, a benzofluorene-amine structure, or a naphthofluorene-amine structure is represented by the following formula 1: 【Chemistry 1】 (In formula 1, Ring A represents a substituted or unsubstituted benzene, a substituted or unsubstituted naphthalene, or a substituted or unsubstituted phenanthrene; Ar １ and Ar ２ each independently represents a substituted or unsubstituted (C1 to C30) alkyl, a substituted or unsubstituted (C6 to C30) aryl, or may be linked together to form a ring; R and R １ ~R ４ each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy, or may be linked to adjacent substituents to form a ring, with the proviso that R and R １ ~R ４ At least one of is -L １ -NAr ３ Ar ４ It is represented by: L １ represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; Ar ３ and Ar ４ each independently represents a substituted or unsubstituted (C6 to C30) aryl, or a substituted or unsubstituted (3 to 30 membered) heteroaryl; n represents an integer of 1 to 8, and when n is a plurality of n's, each n may be the same or different.

3. The organic electroluminescent compound according to claim 2, wherein the compound represented by formula 1 is represented by any one of the following formulas 1-1 to 1-11: 【Chemistry 2】 【Chemistry 3】 (In Formulas 1-1 to 1-11, Ar １ and Ar ２ each independently represents a substituted or unsubstituted (C1 to C30) alkyl or a substituted or unsubstituted (C6 to C30) aryl, or may be linked together to form a fused ring; R １ ~R １６ each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy, or may be linked to adjacent substituents to form a ring, with the proviso that R １ ~R １６ At least one of the -L １ -NAr ３ Ar ４ It is represented by: L １ represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; Ar ３ and Ar ４ each independently represents a substituted or unsubstituted (C6 to C30) aryl, or a substituted or unsubstituted (3 to 30 membered) heteroaryl.

4. 3. The organic electroluminescent device of claim 2, wherein the compound represented by formula 1 is at least one selected from the following compounds: 【Chemistry 4】 【Chemistry 5】 【Chemistry 6】 【Chemistry 7】 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 (In the above compound, Dn represents that n hydrogens are replaced with deuterium, and n represents an integer of 1 or more, which is an integer from 1 to the maximum number of hydrogens in the compound).

5. The substituents of the substituted alkyl, the substituted alkenyl, the substituted aryl(ene), the substituted heteroaryl(ene), the substituted cycloalkyl, and the substituted alkoxy are each independently deuterium; halogen; cyano; carboxyl; nitro; hydroxy; phosphine oxide; (C1-C30) alkyl; halo(C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3-7 membered)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (C6-C30)aryl unsubstituted or substituted with at least one of (C1-C30)alkyl and di(C6-C30)arylamino; (3-30 membered)heteroaryl unsubstituted or substituted with at least one of (C6-C30)aryl; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6- C30)arylsilyl; a condensed ring group of a (C3-C30)aliphatic ring and a (C6-C30)aromatic ring; amino; mono- or di(C1-C30)alkylamino; mono- or di(C2-C30)alkenylamino; mono- or di(C6-C30)arylamino unsubstituted or substituted with (C1-C30)alkyl; mono- or di(3-30 membered)heteroarylamino; (C1-C30)alkyl(C2-C30)alkenylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkyl(3-30 membered) )heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30)alkenyl(3-30 membered)heteroarylamino; (C6-C30)aryl(3-30 membered)heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)aryl(C1-C30)alkyl;3. The organic electroluminescent device of claim 2, wherein the alkyl group is at least one selected from the group consisting of (C1-C30) alkyl, (C6-C30) aryl, and (C1-C30) alkyl.

6. The light-emitting layer emits light of any one of blue, green, and red. When the light-emitting layer emits light of blue or green, R ２ Or R ７ Ga-L １ -NAr ３ Ar ４ 4. The organic electroluminescent device according to claim 3, wherein the case of

7. 2. The organic electroluminescent device of claim 1, wherein the third hole transport layer comprises a compound represented by Formula 2: 【Chemistry 18】 (In formula 2, L ２ ~L ４ each independently represents a single bond, a substituted or unsubstituted (C1-C30) alkylene, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3-30 membered) heteroarylene, or a substituted or unsubstituted (C3-C30) cycloalkylene; Ar ５ ~Ar ７ each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di(C1-C30) alkylamino, substituted or unsubstituted mono- or di(C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino; L ２ ~L ４ are all single bonds and Ar ５ ~Ar ７ are all hydrogen).

8. The Ar in Formula 2 ５ The organic electroluminescent device according to claim 7, wherein is represented by any one of the following formulas 2-1 to 2-6: 【Chemistry 19】 (In Formulas 2-1 to 2-6, L ５ represents a single bond, a substituted or unsubstituted (C1-C30) alkylene, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3-30 membered) heteroarylene, or a substituted or unsubstituted (C3-C30) cycloalkylene; X ８ is L in Equation 2 ２ or represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di(C1-C30) alkylamino, substituted or unsubstituted mono- or di(C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino; R １７ ~R ６８ is L in Equation 2 ２ or each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) )arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di(C1-C30)alkylamino, substituted or unsubstituted mono- or di(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, or may be linked to adjacent substituents to form a ring; However, Ar ８ and R １７ ~R ６８ At least one of the L ２ (Provided that the

9. The organic electroluminescent device according to claim 8, wherein formula 2-3 is represented by any one of formulas 2-3-a to 2-3-c below, or formula 2-4 is represented by any one of formulas 2-4-a to 2-4-c below: 【Chemistry 20】 (In formulas 2-3-a to 2-3-c and formulas 2-4-a to 2-4-c, R ３５ ~R ５０ is as defined in claim 8; R ６９ ~R ７２ is L in Equation 2 ２ or each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) )arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di(C1-C30)alkylamino, substituted or unsubstituted mono- or di(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, or may be linked to adjacent substituents to form a ring; However, R ３５ ~R ５０ and R ６９ ~R ７２ At least one of the L ２ (Provided that the

10. 8. The organic electroluminescent device of claim 7, wherein the compound represented by formula 2 is at least one selected from the following compounds: 【Chemistry 21】 【Chemical 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemical 27】 【Chemistry 28】 【Chemical 29】 (In the above compound, Dn represents that n hydrogens are replaced with deuterium, and n represents an integer of 1 or more, which is an integer from 1 to the maximum number of hydrogens in the compound).

11. 10. The organic electroluminescent device of claim 1, wherein the light-emitting layer comprises a red-emitting light-emitting layer.

12. An organic electroluminescent compound represented by the following formula 1: 【Chemistry 30】 (In formula 1, Ring A represents a substituted or unsubstituted benzene, a substituted or unsubstituted naphthalene, or a substituted or unsubstituted phenanthrene; Ar １ and Ar ２ each independently represents a substituted or unsubstituted (C2-C30) alkyl; R and R １ ~R ４ each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy, or may be linked to adjacent substituents to form a ring, with the proviso that R and R １ ~R ４ At least one of is -L １ -NAr ３ Ar ４ It is represented by: L １ represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; Ar ３ and Ar ４ each independently represents a substituted or unsubstituted (C6 to C30) aryl, or a substituted or unsubstituted (3 to 30 membered) heteroaryl; n represents an integer of 1 to 8, and when n is a plurality of n's, each n may be the same or different.

13. The organic electroluminescent compound according to claim 12, wherein formula 1 is represented by any one of the following formulas 1-1 to 1-11: 【Chemistry 31】 【Chemistry 32】 (In Formulas 1-1 to 1-11, Ar １ and Ar ２ each independently represents a substituted or unsubstituted (C2-C30) alkyl; R １ ~R １６ each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy, or may be linked to adjacent substituents to form a ring, with the proviso that R １ ~R １６ At least one of the -L １ -NAr ３ Ar ４ It is represented by: L １ represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; Ar ３ and Ar ４ each independently represents a substituted or unsubstituted (C6 to C30) aryl, or a substituted or unsubstituted (3 to 30 membered) heteroaryl.

14. Ar in Formula 1 ３ The organic electroluminescent compound according to claim 12, wherein is represented by any one of the following formulas: 【Chemical 33】 (In the above formula, X is O, S, NR ７３ , or C.R. ７４ R ７５ represents; R′ and R ７３ ~R ７５ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted ( represents a substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, a substituted or unsubstituted tri(C6-C30) arylsilyl, a substituted or unsubstituted mono- or di(C1-C30) alkylamino, a substituted or unsubstituted mono- or di(C6-C30) arylamino, or a substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, or may be linked with adjacent substituents to form a substituted or unsubstituted (3- to 30-membered) monocyclic or polycyclic ring; In each formula, any one of R′ is L of formula 1 １ is connected to; a and b each independently represent an integer of 1 to 4, c and d each independently represent an integer of 1 to 6, e represents an integer of 1 to 10, and when a to e each represent an integer of 2 or more, each R' may be the same as or different from each other.

15. 13. The organic electroluminescent compound according to claim 12, wherein the compound represented by formula 1 is at least one selected from the following compounds: 【Chemical 34】 【Chemistry 35】 【Chemical 36】 【Chemical 37】 【Chemical 38】 【Chemical 39】 【Chemistry 40】 (In the above compound, Dn represents that n hydrogens are replaced with deuterium, and n represents an integer of 1 or more, which is an integer from 1 to the maximum number of hydrogens in the compound).

16. An organic electroluminescent device comprising the organic electroluminescent compound of claim 12.

17. An organic electroluminescent compound represented by the following formula 3: 【Chemistry 41】 (In formula 3, R ａ ~R ｊ At least one of the following formula 3-1: 【Chemistry 42】 It is represented by: In formulas 3 and 3-1, R ａ ~R ｍ each independently represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl; 【Chemistry 43】 represents a bond between Formula 3 and Formula 3-1; L ６ ~L ８ each independently represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; Ar ８ represents a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (C3-C30) cycloalkyl, or a substituted or unsubstituted (3-30 membered) heteroaryl; k and l each independently represent an integer of 1 to 5, and m represents an integer of 1 to 3; When k to m are integers of 2 or more, R ｋ ~R ｍ may be the same or different from each other).

18. The organic electroluminescent compound according to claim 17, wherein the compound represented by formula 3-1 is represented by any one of the following formulas 3-1a to 3-1f: 【Chemistry 44】 【Chemistry 45】 (In formulas 3-1a to 3-1f, 【Chemistry 46】 represents a linking group connected to formula 3; L ６ ~L ８ , Ar ８、 and R ｋ ~R ｍ is as defined in claim 17; k and l each independently represent an integer of 1 to 5, and m represents an integer of 1 to 3; When k to m are integers of 2 or more, R ｋ ~R ｍ may be the same or different from each other).

19. 18. The organic electroluminescent compound according to claim 17, wherein the compound represented by formula 3 is at least one selected from the following compounds: 【Chemistry 47】 【Chemistry 48】 【Chemistry 49】 【Chemistry 50】 【Chemistry 51】 (In the above compound, Dn represents that n hydrogens are replaced with deuterium, and n represents an integer of 1 or more, which is an integer from 1 to the maximum number of hydrogens in the compound).

20. 20. An organic electroluminescent device comprising the organic electroluminescent compound of claim 17.

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