Organic electroluminescent compound, plurality of host materials, and organic electroluminescent device comprising the same

Abstract

Provided are an organic electroluminescent compound, a plurality of host materials, and an organic electroluminescent device comprising the same.SOLUTION: The present disclosure relates to an organic electroluminescent compound, a plurality of host materials comprising at least one first host compound and at least one second host compound, and an organic electroluminescent device comprising the same. By comprising the organic electroluminescent compound according to the present disclosure as a single host material, or a specific combination of the compounds according to the present disclosure as a plurality of host materials, it is possible to provide an organic electroluminescent device having improved driving voltage, luminous efficiency, power efficiency and / or lifespan characteristics.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present disclosure relates to organic electroluminescent compounds, host materials, and organic electroluminescent devices containing them. [Background technology]

[0002] Small molecule green organic electroluminescent devices (OLEDs) were first developed by Tang et al. at Eastman Kodak in 1987 by using a TPD / ALq3 bilayer consisting of an emissive layer and a charge transport layer. Since then, OLED development has been rapid, and OLEDs have been commercialized. Currently, OLEDs mainly use phosphorescent materials with excellent luminous efficiency in panel packaging. OLEDs with low driving voltage, high luminous efficiency, and / or long lifetime are required for long-term use and high resolution of displays.

[0003] Patent Document 1 discloses a composition for organic optoelectronic devices, comprising a compound having a dibenzofuran-based heteroaryl moiety and a carbazole-carbazole compound. However, the reference does not specifically disclose the specific combination of host materials claimed in the present disclosure. In addition, there remains a need for the development of light-emitting materials with improved performance, such as improved driving voltage, luminous efficiency, output efficiency, and / or lifetime characteristics, compared to the specific compound combinations disclosed in the aforementioned references. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Korean Patent Application Publication No. 2018-0038834 [Patent Document 2] Korean Patent Application Publication No. 2012-0033017 [Patent Document 3] Korean Patent Application Publication No. 2013-0128322 [Patent Document 4] Korean Patent Application Publication No. 2016-0038006 [Patent Document 5] Korean Patent Application Publication No. 2016-0049083 [Patent Document 6] U.S. Patent Application Publication No. 2016-0233436 [Patent Document 7] International Publication No. 2017 / 178311 Brochure Summary of the Invention [Problem to be solved by the invention]

[0005] An object of the present disclosure is to provide an organic electroluminescent compound having a novel structure suitable for application to an organic electroluminescent device. Another object of the present disclosure is to provide an improved organic electroluminescent material that can provide an organic electroluminescent device with improved driving voltage, luminous efficiency, and / or lifespan characteristics. A further object of the present disclosure is to provide an organic electroluminescent device with improved driving voltage, luminous efficiency, output efficiency, and / or lifespan characteristics by including a compound according to the present disclosure as a single host material or a specific combination of compounds according to the present disclosure as multiple host materials. [Means for solving the problem]

[0006] As a result of intensive research to solve the technical problem, the present inventors have discovered that the above object can be achieved by the compound of the following formula 1-A: [ka] [In Formula 1-A, X a represents O or S, R 41 ~R 48at least one of which is represented by the following formula A-1, and the others each independently represent hydrogen, deuterium, or (C6-C18)aryl unsubstituted or substituted with at least one of deuterium, (C1-C6)alkyl, and (C6-C18)aryl; [ka] (In Formula A-1, Ar a and Ar b each independently represents unsubstituted or phenyl substituted with at least one of deuterium and naphthyl, substituted or unsubstituted naphthyl, unsubstituted or deuterium-substituted biphenyl, unsubstituted or deuterium-substituted terphenyl, or a combination thereof; a and Ar b provided that at least one of represents substituted or unsubstituted naphthyl; However, in Formula 1-A, R 41 ~R 43 , and R 45 ~R 48 If all are hydrogen, R 44 is represented by formula A-1, and Ar a and Ar b represents unsubstituted naphthyl, and Ar a and Ar b the others represent unsubstituted or phenyl substituted with at least one of deuterium and naphthyl, substituted naphthyl, deuterium-substituted biphenyl, or unsubstituted or deuterium-substituted terphenyl. It has been found that this can be achieved by an organic electroluminescent compound represented by the formula:

[0007] In addition, the present inventors have found that the above object can be achieved by a plurality of host materials including at least one first host compound and at least one second host compound, wherein the first host compound is represented by the following Formula 1 and the second host compound is represented by the following Formula 2: [ka] In Equation 1, X represents O or S; R1 to R8 are each independently *-(L1) a -L2-(HAr) b , hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, -NR 22 R 23 , or -SiR 24 R 25 R 26 or may be joined to adjacent substituents to form a ring; However, at least one of R1 to R8 is *-(L1) a -L2-(HAr) b Provided that it represents; Each L1 independently represents a substituted or unsubstituted (C1 to C30) alkylene, a substituted or unsubstituted (C6 to C30) arylene, a substituted or unsubstituted (3 to 30-membered) heteroarylene, or a substituted or unsubstituted (C3 to C30) cycloalkylene; L2 represents an unsubstituted (3 to 30 membered) heteroarylene; Each HAr is independently deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, -NR 22 R 23 , or -SiR 24 R 25 R 26 represents; R 22 ~R 26each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl; or may be combined with adjacent substituents to form a ring; a represents an integer of 0 to 2, and b represents an integer of 1 to 4, where when a and b are each an integer of 2 or greater, each L1 and each HAr may be the same or different. [ka] In Equation 2, B1-B7 each independently represent a substituted or unsubstituted (C5-C20) ring, where a carbon atom of the ring may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur, provided that at least five of B1-B7 are present, and adjacent rings of B1-B7 are fused to each other; Y is -N(L3-(Ar) n )-, -O-, -S-, or -C(R 31 )(R 32 )-represents; L3 represents a single bond, a substituted or unsubstituted (C1 to C30) alkylene, a substituted or unsubstituted (C6 to C30) arylene, a substituted or unsubstituted (3 to 30-membered) heteroarylene, or a substituted or unsubstituted (C3 to C30) cycloalkylene; Ar is a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 membered) heteroaryl, or -NR 33 R 34 represents; R 31 ~R 34each 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, or substituted or unsubstituted (C3-C30) cycloalkyl; or may be combined with adjacent substituents to form a ring; n represents an integer of 1 or 2, where when n is 2, each of Ar can be the same or different.

[0008] Advantageous Effects of the Invention The organic electroluminescent compound according to the present disclosure shows suitable performance for its use in organic electroluminescent device.In addition, by including the compound according to the present disclosure as a single host material or a specific combination of the compounds according to the present disclosure as multiple host materials, it can provide an organic electroluminescent device with improved driving voltage, luminous efficiency, output efficiency and / or lifespan characteristics compared with conventional organic electroluminescent devices, and can manufacture a display system or lighting system using it. DETAILED DESCRIPTION OF THE INVENTION

[0009] The present disclosure will be described in detail hereinafter. However, the following description is intended to illustrate the present invention and is not meant to limit the scope of the present disclosure in any way.

[0010] The term "organic electroluminescent compound" in the present disclosure means a compound that can be used in an organic electroluminescent device and, if necessary, can be included in any layer that constitutes the organic electroluminescent device.

[0011] The term "organic electroluminescent material" in the present disclosure refers to a material that can be used in an organic electroluminescent device and can include at least one compound. The organic electroluminescent material can be included in any layer that constitutes an organic electroluminescent device, as needed. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole auxiliary material, an emitting auxiliary material, an electron blocking material, an 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.

[0012] The term "multiple organic electroluminescent materials" in the present disclosure refers to an organic electroluminescent material containing a combination of at least two compounds that can be included in any layer constituting an organic electroluminescent device. It can refer to both the material before being included in the organic electroluminescent device (e.g., before deposition) and the material after being included in the organic electroluminescent device (e.g., after deposition). For example, the multiple organic electroluminescent materials of the present disclosure can be a combination of at least two compounds that can be included in at least one layer of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. The at least two compounds can be included in the same layer or different layers, and can be mixed, evaporated together, or evaporated separately.

[0013] The term "multiple host materials" in the present disclosure refers to an organic electroluminescent material that includes a combination of at least two host materials. It can refer to both the material before being included in an organic electroluminescent device (for example, before vapor deposition) and the material after being included in an organic electroluminescent device (for example, after vapor deposition). The multiple host materials of the present disclosure can be included in any light-emitting layer that constitutes an organic electroluminescent device. The at least two compounds included in the multiple host materials of the present disclosure can be included together in one light-emitting layer, or can be included in different light-emitting layers. For example, when at least two host materials are included in one layer, they can be mixed and evaporated to form a layer, or can be simultaneously and separately co-evaporated to form a layer.

[0014] As used herein, the term "(C1-C30) alkyl(ene)" refers to a linear or branched alkyl(ene) 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, sec-butyl, tert-butyl, etc. The term "(C2-C30) alkenyl" refers to a linear 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, etc. The term "(C2-C30)alkynyl" refers to a linear or branched alkynyl having 2 to 30 carbon atoms constituting the chain, preferably 2 to 20, more preferably 2 to 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(ene)" refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 ring skeletal carbon atoms, preferably 3 to 20, more preferably 3 to 7. The cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, and the like. The term "(3- to 7-membered)heterocycloalkyl" refers to a cycloalkyl having 3 to 7, preferably 5 to 7, skeletal ring atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably the group consisting of O, S, and N. The heterocycloalkyl may include tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, etc. The term "(C6-C30)aryl(ene)" refers to a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 skeletal ring carbon atoms, where the number of skeletal ring carbon atoms is preferably 6 to 25.More preferably, it is 6 to 18. The aryl(ene) may be partially saturated and may include a spiro structure. Examples of the aryl include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, spiro[fluorene-benzofluorenyl]yl, azulenyl, and the like. More 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-biphenylenyl, phenylyl, 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 benzo[a]fluorenyl, 11,11-dimethyl-6-benzo[a]fluorenyl, 11,11-dimethyl-7-benzo[a]fluorenyl, 11,11-dimethyl-8-benzo[a]fluorenyl, 11,11-dimethyl-9-benzo[a]fluorenyl, 11,11-dimethyl-10-benzo[a]fluorenyl, 11,11-dimethyl-1-benzo[b]fluorenyl, 11,11-dimethyl-2-benzo[b]fluorenyl, 11,11-dimethyl-3-benzo[b]fluorenyl, 11,11-dimethyl-4-benzo[b]fluorenyl, 11 ,11-dimethyl-5-benzo[b]fluorenyl, 11,11-dimethyl-6-benzo[b]fluorenyl, 11,11-dimethyl-7-benzo[b]fluorenyl, 11,11-dimethyl-8-benzo[b]fluorenyl, 11,11-dimethyl-9-benzo[b]fluorenyl, 11,11-dimethyl-10-benzo[b]fluorenyl, 11,11-dimethyl-1-benzo[c]fluorenyl, 11,11-dimethyl-2-benzo[c]fluorenyl, 11,11-dimethyl-3-benzo[c]fluorenyl, 11,11-dimethyl-4-benzo 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.

[0015] The term "(3- to 30-membered)heteroaryl(ene)" refers to an aryl(ene) having 3 to 30 skeletal ring atoms and containing at least one, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, Si, and P. The heteroaryl(ene) may be a monocyclic ring or a fused ring fused with at least one benzene ring; may be partially saturated; may be formed by bonding at least one heteroaryl or aryl group to a heteroaryl group via a single bond; or may include a spiro structure. Examples of the heteroaryl include monocyclic heteroaryls such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl, as well as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, benzonaphthofuranyl, dibenzothiophenyl, benzonaphthothiophenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, and benzoquinoxalinyl. benzofuropyridyl, naphthyridinyl, pyridopyrazinyl, carbazolyl, benzocarbazolyl, phenoxazinyl, phenanthridinyl, phenanthrooxazolyl, benzodioxolyl, dihydroacridinyl, benzofuropyridyl, benzofuropyrimidinyl, dibenzoselenophenyl, benzofuroquinolinyl, benzofuroquinazolinyl, benzofuronaphthyridinyl, naphthofuropyrimidinyl, benzothienoquinolinyl, benzothieno quinazolinyl, benzothienonaphthyridinyl, benzothienopyrimidinyl, naphthothienopyrimidinyl, pyrimidoindolyl, benzopyrimidoindolyl, benzofuropyrazinyl, naphthofuropyrazinyl, benzothienopyrazinyl, naphthothienopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzotriazolephenazinyl, imidazopyridyl, chromenoquinazolinyl, thiochromenoquinazolinyl,The heteroaryl may include fused ring heteroaryls such as dimethylbenzopyrimidinyl, indolocarbazolyl, indenocarbazolyl, etc. More specifically, the heteroaryls may include 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, etc. inyl, 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, 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-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl,4-Phenanthridinyl, 6-Phenanthridinyl, 7-Phenanthridinyl, 8-Phenanthridinyl, 9-Phenanthridinyl, 10-Phenanthridinyl, 1-Acridinyl, 2-Acridinyl, 3-Acridinyl, 4-Acridinyl, 9-Acridinyl, 2-Oxazolyl, 4-Oxazolyl, 5-Oxazolyl, 2-Oxadiazolyl, 5-Oxadiazolyl, 3-Furazanyl, 2-Thienyl, 3-Thienyl, 2-Methylpyrrol-1-yl, 2-Methylpyrrol-3-yl, 2-Methylpyrrol-4-yl, 2-Methylpyrrol-5-yl, 3 -methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2-tert-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4-tert-butyl-1-indolyl, 2-tert-butyl-3-indolyl, 4-tert-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzyl benzofuranyl, 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 benzofuranyl, 9-naphtho-[1,2-b]-benzofuranyl, 10-naphtho-[1,2-b]-benzofuranyl, 1-naphtho-[2,3-b]-benzofuranyl, 2-naphtho-[2,3-b]-benzofuranyl, 3-naphtho-[2,3-b]-benzofuranyl, 4-naphtho-[2,3-b]-benzofuranyl, 5-naphtho-[2,3-b]-benzofuranyl, 6-naphtho-[2,3-b]-benzofuranyl, 7-naphtho-[2,3-b]-benzofuranyl, 8-naphtho-[2,3-b]-benzofuranyl, 9-naphtho-[2,3-b]-benzofuranyl,10-naphtho-[2,3-b]-benzofuranyl, 1-naphtho-[2,1-b]-benzofuranyl, 2-naphtho-[2,1-b]-benzofuranyl, 3-naphtho-[2,1-b]-benzofuranyl, 4-naphtho-[2,1-b]-benzofuranyl, 5-naphtho-[2,1-b]-benzofuranyl, 6-naphtho-[2,1-b]-benzofuranyl, 7-naphtho-[2,1-b]-benzofuranyl, 8-naphtho-[2,1-b]-benzofuranyl, 9-naphtho-[2,1-b]-benzofuranyl, 10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho 1-naphtho-[1,2-b]-benzothiophenyl, 2-naphtho-[1,2-b]-benzothiophenyl, 3-naphtho-[1,2-b]-benzothiophenyl, 4-naphtho-[1,2-b]-benzothiophenyl, 5-naphtho-[1,2-b]-benzothiophenyl, 6-naphtho-[1,2-b]-benzothiophenyl, 7-naphtho-[1,2-b]-benzothiophenyl, 8-naphtho-[1,2-b]-benzothiophenyl, 9-naphtho-[1,2-b]-benzothiophenyl, 10-naphtho-[1,2-b]-benzothiophenyl, 1-naphtho-[2,3- b]-benzothiophenyl, 2-naphtho-[2,3-b]-benzothiophenyl, 3-naphtho-[2,3-b]-benzothiophenyl, 4-naphtho-[2,3-b]-benzothiophenyl, 5-naphtho-[2,3-b]-benzothiophenyl, 1-naphtho-[2,1-b]-benzothiophenyl, 2-naphtho-[2,1-b]-benzothiophenyl, 3-naphtho-[2,1-b]-benzothiophenyl, 4-naphtho-[2,1-b]-benzothiophenyl, 5-naphtho-[2,1-b]-benzothiophenyl, 6-naphtho-[2,1-b]-benzothio phenyl, 7-naphtho-[2,1-b]-benzothiophenyl, 8-naphtho-[2,1-b]-benzothiophenyl, 9-naphtho-[2,1-b]-benzothiophenyl, 10-naphtho-[2,1-b]-benzothiophenyl, 2-benzofuro[3,2-d]pyrimidinyl, 6-benzofuro[3,2-d]pyrimidinyl, 7-benzofuro[3,2-d]pyrimidinyl, 8-benzofuro[3,2-d]pyrimidinyl, 9-benzofuro[3,2-d]pyrimidinyl, 2-benzothio[3,2-d]pyrimidinyl, 6-benzothio[3,2-d]pyrimidinyl,7-benzothio[3,2-d]pyrimidinyl, 8-benzothio[3,2-d]pyrimidinyl, 9-benzothio[3,2-d]pyrimidinyl, 2-benzofuro[3,2-d]pyrazinyl, 6-benzofuro[3,2-d]pyrazinyl, 7-benzofuro[3,2-d]pyrazinyl, 8-benzofuro[3,2-d]pyrazinyl, 9-benzofuro[3,2-d]pyrazinyl, 2-benzothio[3,2-d]pyrazinyl, 6-benzothio[3,2-d]pyrazinyl, 7-benzothio Examples of suitable silafluorenyls include thio[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, and the like. Furthermore, "halogen" includes F, Cl, Br, and I.

[0016] In addition, "ortho (o-)", "meta (m-)", and "para (p-)" are prefixes that respectively indicate the relative positions of substituents. Ortho indicates that two substituents are adjacent to each other; for example, when two substituents in a benzene derivative occupy the 1st and 2nd positions, it is called the ortho position. Meta indicates that two substituents are at the 1st and 3rd positions; for example, when two substituents in a benzene derivative occupy the 1st and 3rd positions, it is called the meta position. Para indicates that two substituents are at the 1st and 4th positions; for example, when two substituents in a benzene derivative occupy the 1st and 4th positions, it is called the para position.

[0017] In this specification, the ring formed by the bonding of adjacent substituents may be a substituted or unsubstituted, monocyclic or polycyclic, (3 to 30-membered) aliphatic or aromatic ring, or a combination thereof, where two or more adjacent substituents are bonded or fused together. Preferably, the ring may be a substituted or unsubstituted, monocyclic or polycyclic, (3 to 26-membered) aliphatic or aromatic ring, or a combination thereof. More preferably, the ring may be an unsubstituted, monocyclic or polycyclic, (5 to 20-membered) aromatic ring. In addition, the formed ring may contain at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S. For example, the ring may be a substituted or unsubstituted benzene, naphthalene, phenanthrene, fluorene, indene, indole, benzoindole, benzofuran, benzothiophene, dibenzothiophene, dibenzofuran, carbazole ring, etc.

[0018] As used herein, the term "substituted" in the phrase "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, and also includes a hydrogen atom being replaced with a group formed by the bonding of two or more of the above-mentioned substituents. For example, the "group formed by the bonding of two or more substituents" may be pyridine-triazine. That is, pyridine-triazine may be interpreted as one heteroaryl substituent or as a substituent to which two heteroaryl substituents are bonded. In this specification, the substituents of substituted alkyl, substituted alkylene, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted cycloalkyl, substituted cycloalkylene, substituted cycloalkenyl, substituted heterocycloalkyl, and substituted rings 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- to 7-membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; unsubstituted or at least one of (C1-C30) alkyl and (C6-C30) aryl. (3-30 membered) heteroaryl substituted with one atom; (C6-C30) aryl substituted with at least one of unsubstituted or deuterium, C1-C30) alkyl, (3-30 membered) heteroaryl, and mono- or di-(C6-C30) arylamino; 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; 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 at least one selected from the group consisting of: (C6-C30)arylcarbonyl; (C6-C30)arylphosphine; 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 at least one selected from the group consisting of deuterium; (C1-C20) alkyl; (5-30 membered) heteroaryl unsubstituted or substituted with (C6-C25) aryl; (C6-C25) aryl unsubstituted or substituted with at least one of deuterium, (C1-C20) alkyl, (5-30 membered) heteroaryl, and di(C6-C25) arylamino; and mono- or di-(C6-C25) arylamino. According to another embodiment of the present disclosure, the substituents are each independently at least one selected from the group consisting of deuterium, (C1-C10) alkyl, (5-26-membered) heteroaryl unsubstituted or substituted with (C6-C18) aryl, (C6-C18) aryl unsubstituted or substituted with at least one of deuterium, (C1-C10) alkyl, (5-26-membered) heteroaryl, and di(C6-C18) arylamino, and di(C6-C18) arylamino. For example, the substituents are each independently at least one selected from the group consisting of deuterium, methyl, phenyl unsubstituted or substituted with at least one of deuterium, dibenzofuranyl, carbazolyl, phenylquinoxalyl, 26-membered heteroaryl, and diphenylamino, naphthyl, biphenyl, naphthylphenyl, phenylnaphthyl, phenanthrenyl, dimethylfluorenyl, dimethylbenzofluorenyl, terphenyl, triphenylenyl,It may be at least one selected from the group consisting of unsubstituted or phenyl-substituted pyridyl; phenyl-substituted triazinyl; phenylquinoxalinyl; dibenzothiophenyl; dibenzofuranyl; unsubstituted or phenyl-substituted carbazole; 26-membered heteroaryl; and diphenylamino.

[0019] In the formulas of the present disclosure, heteroaryl, heteroarylene, and heterocycloalkyl can each independently contain at least one heteroatom selected from B, N, O, S, Si, and P. In addition, the heteroatom can be selected from 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) aryl. It may be bonded to at least one selected from the group consisting of silyl, 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, and substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino.

[0020] In formula 1, X represents O or S.

[0021] In formula 1, R1 to R8 each independently represent *-(L1) a -L2-(HAr) b, hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, -NR 22 R 23 , or -SiR 24 R 25 R 26 or may combine with adjacent substituents to form a ring, but at least one of R1 to R8 represents *-(L1) a -L2-(HAr) b According to one embodiment of the present disclosure, R1 to R8 are each independently hydrogen, deuterium, substituted or unsubstituted (C6-C18) aryl, or *-(L1) a -L2-(HAr) b However, at least one of R1 to R8 is *-(L1) a -L2-(HAr) b According to another embodiment of the present disclosure, any one of R1 to R8 represents *-(L1) a -L2-(HAr) b and the others each independently represent hydrogen, deuterium, or (C6-C18)aryl unsubstituted or substituted with at least one of deuterium, (C1-C6)alkyl, and (C6-C18)aryl. For example, any one of R1-R8 may be *-(L1) a -L2-(HAr) b and the others may each independently be hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, biphenyl, phenanthrenyl, chrysenyl, terphenyl, or triphenylenyl, etc., where the substituents of the substituted phenyl and substituted naphthyl may be at least one selected from the group consisting of phenyl, naphthyl, and phenanthrenyl.

[0022] Each L1 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. According to one embodiment of the present disclosure, each L1 independently represents a substituted or unsubstituted (C6-C25) arylene. According to another embodiment of the present disclosure, each L1 independently represents an unsubstituted (C6-C18) arylene. For example, each L1 independently may be phenylene, naphthylene, biphenylene, phenylnaphthylene, naphthylphenylene, or the like.

[0023] L2 represents an unsubstituted (3- to 30-membered) heteroarylene. According to one embodiment of the present disclosure, L2 represents an unsubstituted (5- to 25-membered) heteroarylene. According to another embodiment of the present disclosure, L2 represents an unsubstituted (5- to 20-membered) heteroarylene. Specifically, L2 may be triazinylene, pyridylene, pyrimidinylene, quinazolinylene, benzoquinazolinylene, quinoxalinylene, benzoquinoxalinylene, quinolylene, benzoquinolylene, isoquinolylene, benzoisoquinolylene, triazolylene, pyrazolylene, naphthyridinylene, triazanaphthylene, pyridopyrazinylene, benzothienopyrimidinylene, etc. For example, L2 can be triazinylene, quinazolinylene, benzoquinazolinylene, quinoxalinylene, benzoquinoxalinylene, naphthyridinylene, or pyridopyrazinylene, and the like.

[0024] Each HAr is independently deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, -NR 22 R 23 , or -SiR 24 R 25 R 26According to one embodiment of the present disclosure, each HAr independently represents a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (5-25-membered) heteroaryl. According to another embodiment of the present disclosure, each HAr independently represents a (C6-C18) aryl that is unsubstituted or substituted with at least one of a (C1-C10) alkyl, a (10-20-membered) heteroaryl, and a di(C6-C18) arylamino; or a (5-20-membered) heteroaryl that is unsubstituted or substituted with a (C6-C18) aryl. For example, each HAr independently may be a phenyl that is unsubstituted or substituted with at least one of dibenzofuranyl, carbazolyl, phenylquinoxalinyl, and diphenylamino; naphthyl; biphenyl; phenanthrenyl; dimethylfluorenyl; dimethylbenzofluorenyl; naphthylphenyl; phenylnaphthyl; terphenyl; triphenylenyl; dibenzofuranyl; or phenylcarbazolyl, etc.

[0025] R 22 ~R 26 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl; or may be combined with adjacent substituents to form a ring. According to one embodiment of the present disclosure, R 22 ~R 26 each independently represents hydrogen, a substituted or unsubstituted (C1 to C20) alkyl, a substituted or unsubstituted (C6 to C25) aryl, or a substituted or unsubstituted (5 to 25 membered) heteroaryl. a represents an integer of 0 to 2, and when a is 2, each L1 may be the same or different. b represents an integer of 1 to 4, and when b is an integer of 2 or greater, each HAr may be the same or different. According to one embodiment of the present disclosure, b represents an integer of 1 or 2, and when b is 2, each HAr may be the same or different.

[0026] Formula 1 can be represented by at least one of the following formulas 1-1 to 1-4. [ka]

[0027] In formulas 1-1 to 1-4, R1 to R8 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C3 to C30) cycloalkyl, substituted or unsubstituted (C3 to C30) cycloalkenyl, substituted or unsubstituted (3 to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6 to C30) aryl, substituted or unsubstituted (3 to 30-membered) heteroaryl, -NR 22 R 23 , or -SiR 24 R 25 R 26 or may be joined to adjacent substituents to form a ring. For example, R1 to R8 can be hydrogen.

[0028] In formulas 1-1 to 1-4, X, L1, L2, HAr, a, b, and R 22 ~R 26 is as defined in Equation 1.

[0029] In Formula 2, B1 to B7 each independently represent an absent or substituted or unsubstituted (C5 to C20) ring, preferably a substituted or unsubstituted (C5 to C13) ring, where a carbon atom of this ring may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur, provided that at least five of B1 to B7 are present, and adjacent rings B1 to B7 are fused to each other. As used herein, "adjacent rings B1 to B7 are fused to each other" means that ring B1 and ring B2, ring B2 and ring B3, ring B3 and ring B4, ring B4 and ring B5, ring B5 and ring B6, or ring B6 and ring B7 are fused to each other. According to one embodiment of the present disclosure, when any one of B1 to B7 represents (C6-C20)aryl, the adjacent ring may be absent or may be a C5 ring, wherein a carbon atom of this ring may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur. According to another embodiment of the present disclosure, B1 to B7 each independently represent absent or a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted pyrrole ring, a substituted or unsubstituted furan ring, a substituted or unsubstituted thiophene ring, a substituted or unsubstituted cyclopentadiene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted pyridine ring, or a substituted or unsubstituted dibenzofuran ring. For example, B1 to B7 may each independently be absent or may represent a benzene ring that is unsubstituted or substituted with phenyl, naphthyl, and / or diphenyltriazinyl; a naphthalene ring; an unsubstituted or methyl-substituted cyclopentadiene ring; a methyl-substituted fluorene ring; a pyrrole ring substituted with unsubstituted phenyl, phenyl substituted with at least one deuterium, biphenyl, and / or pyridyl; a furan ring; a thiophene ring; a pyridine ring; or an unsubstituted or diphenyltriazinyl-substituted dibenzofuran ring.

[0030] In Formula 2, Y is -N(L-(Ar) n )-, -O-, -S-, or -C(R 31 )(R 32According to one embodiment of the present disclosure, Y represents -N(L-(Ar) n )- represents.

[0031] L3 represents a single bond, substituted or unsubstituted (C1-C30) alkylene, substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (3-30 membered) heteroarylene, or substituted or unsubstituted (C3-C30) cycloalkylene. According to one embodiment of the present disclosure, L3 represents a single bond, substituted or unsubstituted (C6-C25) arylene, or substituted or unsubstituted (3-30 membered) heteroarylene. According to another embodiment of the present disclosure, L3 represents a single bond, unsubstituted (C6-C18) arylene, or unsubstituted (5-25 membered) heteroarylene. For example, L3 can be a single bond, phenylene, naphthylene, biphenylene, pyridylene, pyrimidinylene, triazinylene, quinoxalinylene, quinazolinylene, dibenzofuranylene, benzofuropyrimidinylene, benzothienopyrimidinylene, indolopyrimidinylene, or benzoquinoxalinylene.

[0032] Ar is a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 membered) heteroaryl, or -NR 33 R 34 According to one embodiment of the present disclosure, Ar represents a substituted or unsubstituted (C6-C25) aryl, a substituted or unsubstituted (5-25 membered) heteroaryl, or -NR 33 R 34 According to another embodiment of the present disclosure, Ar represents (C6-C25)aryl unsubstituted or substituted with at least one of deuterium, (C1-C6)alkyl, and (3-30 membered)heteroaryl; (5-25 membered)heteroaryl unsubstituted or substituted with at least one of deuterium, (C6-C18)aryl, and (3-30 membered)heteroaryl; or -NR 33 R 34For example, Ar represents unsubstituted phenyl, phenyl substituted with at least one deuterium, phenyl substituted with a 26-membered heteroaryl, naphthyl, biphenyl, methyl-substituted fluorenyl, spirobifluorenyl, terphenyl, triphenylenyl, unsubstituted and phenyl-substituted pyridyl, phenyl-substituted pyrimidinyl, substituted triazinyl, substituted quinoxalinyl, substituted quinazolinyl, phenyl-substituted benzoquinoxalinyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, phenyl-substituted benzofuropyrimidinyl, phenyl-substituted benzothienopyrimidinyl, phenyl-substituted indolopyrimidinyl, or -NR 33 R 34 The substituents of the substituted triazinyl, substituted quinoxalinyl, and substituted quinazolinyl may each independently be at least one selected from the group consisting of unsubstituted or substituted with at least one of deuterium and a 26-membered heteroaryl, naphthyl, biphenyl, terphenyl, dibenzofuranyl, phenyl-substituted pyridyl, dimethylfluorenyl, and dibenzothiophenyl.

[0033] R 31 ~R 34 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, or substituted or unsubstituted (C3-C30) cycloalkyl; or may be joined with adjacent substituents to form a ring. According to one embodiment of the present disclosure, R 31 ~R 34 each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C20) alkyl, or substituted or unsubstituted (C6-C25) aryl. 31 and R 32 each independently represents an unsubstituted (C1-C10) alkyl; R 33 and R 34 Each independently represents an unsubstituted (C6-C18) aryl. For example, R 31 and R32 can be methyl, R 33 and R 34 can be phenyl.

[0034] n represents an integer of 1 or 2, where when n is 2, each of Ar can be the same or different.

[0035] Formula 2 can be represented by at least one of the following formulas 2-1 to 2-4. [ka]

[0036] In formulas 2-1 to 2-4, Y1, Y2, Y3, and Y4 are each independently the same as the definition of Y in formula 2, and when a plurality of Ar are present, each of the Ar may be the same or different; X1 to X 12 are each independently -N= or -C(R a ) = represents ;R a 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, or substituted or unsubstituted (C3-C30) cycloalkyl; or an adjacent R a may be bonded to each other to form a ring, where multiple R a If there is R a Each of the can be the same or different.

[0037] According to one embodiment of the present disclosure, R a represents hydrogen, deuterium, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5-25 membered) heteroaryl; or an adjacent R a may be bonded to each other to form a ring. According to another embodiment of the present disclosure, R a represents hydrogen, unsubstituted (C6-C18) aryl, or (5-25 membered) heteroaryl substituted with (C6-C18) aryl; or an adjacent R amay be linked to each other to form a benzene ring, a methyl-substituted indene ring, or an unsubstituted or diphenyltriazinyl-substituted benzofuran ring.

[0038] In any one of formulas 2-1 to 2-4, Ar and R a At least one of may independently be at least one selected from those listed in Group 1 below. [Group 1] [ka]

[0039] In Group 1, D1 and D2 each independently represent a benzene ring or a naphthalene ring; X 21 are O, S, NR 35 , or CR 36 R 37 represents ;X 22 are each independently 38 or N, but X 22 X represents N; 23 are each independently 39 or N; L 11 ~L 18 each independently represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30-membered) heteroarylene; R 11 ~R 21 and R 35 ~R 39 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, or substituted or unsubstituted (C3-C30) cycloalkyl, or can be combined with adjacent substituents to form a ring; aa, ff, and gg each independently represent an integer of 1 to 5, bb represents an integer of 1 to 7, cc, dd, and ee each independently represent an integer of 1 to 4, where each of aa to gg represents an integer of 2 or greater, and each R 11~R 17 Each of the can be the same or different.

[0040] According to one embodiment of the present disclosure, D1 can be a benzene ring; X 21 is O, S, or CR 36 R 37 It can be;L 11 ~L 18 may each independently be a single bond; R 11 ~R 21 and R 35 ~R 39 are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5-25 membered) heteroaryl, or can be joined with adjacent substituents to form a ring; aa, bb, ff, and gg can each independently be an integer from 1 to 5; cc, dd, and ee can each independently be an integer from 1 to 4. For example, R 11 can be hydrogen, deuterium, phenyl, biphenyl, or a 26-membered heteroaryl; R 12 can be hydrogen, or an adjacent R 12 may be bonded to each other to form a benzene ring; R 13 , R 16 , and R 17 can be hydrogen; R 18 and R 19 can be hydrogen or phenyl; R 21 can be phenyl; R 36 and R 37 can be methyl; R 38 can be hydrogen, phenyl, biphenyl, dibenzofuranyl, or dibenzothiophenyl, or an adjacent R 38 may be bonded to each other to form a benzene ring; R 39can be hydrogen, unsubstituted phenyl, phenyl substituted with at least one deuterium, phenyl substituted with a 26-membered heteroaryl, naphthyl, biphenyl, dimethylfluorenyl, terphenyl, phenyl-substituted pyridyl, dibenzofuranyl, or dibenzothiophenyl; aa can be an integer of 1 or 5; bb can be an integer of 1 or 4; and cc can be 1.

[0041] In any one of formulas 2-1 to 2-4, Ar and R a At least one of may independently be at least one selected from those listed in Group 2 below. [Group 2] [ka] [ka] [ka] [ka]

[0042] In Group 2, L represents a single bond, substituted or unsubstituted (C1-C30) alkylene, substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (3-30-membered) heteroarylene, or substituted or unsubstituted (C3-C30) cycloalkylene; A1 to A3 each independently represent a substituted or unsubstituted (C1-C30) alkyl or a substituted or unsubstituted (C6-C30) aryl. According to one embodiment of the present disclosure, L represents a single bond, substituted or unsubstituted (C6-C25) arylene, or substituted or unsubstituted (3-25-membered) heteroarylene; A1 to A3 each independently represent a substituted or unsubstituted (C1-C20) alkyl or a substituted or unsubstituted (C6-C25) aryl. A1 and A2 can be the same or different. For example, A1 and A2 can each independently be methyl or phenyl.

[0043] In any one of formulas 2-1 to 2-4, Ar and R a At least one of may independently be at least one selected from those listed in Group 3 below. [Group 3] [ka] [ka] [ka]

[0044] The compound represented by formula 1 can be at least one selected from the following compounds, but is not limited thereto: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0045] The compound represented by formula 2 can 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]

[0046] A combination of at least one of compounds E-1 to E-196 and at least one of compounds C-1 to C-300 can be used in an organic electroluminescent device.

[0047] According to one embodiment of the present disclosure, the present disclosure may provide a compound represented by Formula 1 or a compound represented by Formula 2. Specifically, the present disclosure may provide at least one compound selected from the group consisting of Compounds E-1 to E-196 and Compounds C-1 to C-300.

[0048] Formula 1 of the present disclosure can be represented by the following formula 1-A: In addition, according to one embodiment of the present disclosure, the present disclosure can provide an organic electroluminescent compound represented by formula 1-A. [ka]

[0049] In Formula 1-A, X a represents O or S; R 41 ~R 48 at least one of which is represented by the following formula A-1, and the others each independently represent hydrogen, deuterium, or (C6-C18)aryl unsubstituted or substituted with at least one of deuterium, (C1-C6)alkyl, and (C6-C18)aryl; [ka] In formula (A-1), Ar a and Ar b each independently represents unsubstituted or phenyl substituted with at least one of deuterium and naphthyl, substituted or unsubstituted naphthyl, unsubstituted or deuterium-substituted biphenyl, unsubstituted or deuterium-substituted terphenyl, or a combination thereof; a and Ar b represents substituted or unsubstituted naphthyl; However, in Formula 1-A, R 41 ~R 43 , and R 45 ~R 48 If all are hydrogen, R 44 is represented by formula A-1, and Ar a and Ar brepresents unsubstituted naphthyl, and Ar a and Ar b Others represent unsubstituted or phenyl substituted with at least one of deuterium and naphthyl, substituted naphthyl, deuterium-substituted biphenyl, or unsubstituted or deuterium-substituted terphenyl.

[0050] The substituent of the substituted naphthyl can be at least one selected from the group consisting of deuterium, unsubstituted or deuterium-substituted phenyl, and unsubstituted or deuterium-substituted naphthyl.

[0051] According to one embodiment of the present disclosure, R 41 ~R 48 The (C6-C18)aryl in the formula (I) is preferably phenyl, naphthyl, biphenyl, terphenyl, fluorenyl, chrysenyl, triphenylenyl, or phenanthrenyl, and more preferably phenyl, naphthyl, biphenyl, terphenyl, chrysenyl, triphenylenyl, or phenanthrenyl.

[0052] According to one embodiment of the present disclosure, Ar a and Ar b can be represented by any one of those listed in Group 4 below. In Group 4, hydrogens can each independently be replaced with deuterium. [Group 4] [ka]

[0053] Specifically, the compound represented by formula 1-A can be exemplified by, but not limited to, the following compounds: [ka] [ka] [ka] [ka]

[0054] According to one embodiment of the present disclosure, the compounds represented by formula 1-A can be used alone or in combination of two or more in an organic electroluminescent device.

[0055] The compounds of Formula 1 and the compounds of Formula 1-A according to the present disclosure can be prepared by synthetic methods known to those skilled in the art, and by referring to, for example, Patent Document 2 (published April 6, 2012), Patent Document 3 (published November 26, 2013), Patent Document 4 (published April 6, 2016), and Patent Document 5 (published May 9, 2016), Patent Document 6 (published August 11, 2016), and Patent Document 7 (published October 19, 2017), or according to the following Reaction Schemes A and B, but are not limited thereto.

[0056] [Reaction Scheme A] [ka]

[0057] [Reaction Scheme B] [ka]

[0058] In Reaction Schemes A and B, Xa, R 41 ~R 48 , Ar a , and Ar b is as defined in Equation 1-A.

[0059] Compounds of formula 2 of the present disclosure can be prepared by synthetic methods known to those skilled in the art, and for example, but not limited to, according to the following reaction schemes 1-4. [Reaction Scheme 1] [ka] [Reaction Scheme 2] [ka] [Reaction Scheme 3] [ka] [Reaction Scheme 4] [ka]

[0060] In Reaction Schemes 1 to 4, Y1 to Y4 and X1 to X 12 is as defined in formulas 2-1 to 2-4.

[0061] While exemplary synthetic examples of compounds represented by formula 2 of the present disclosure are described above, one skilled in the art will readily understand that all of them are based on Buchwald-Hartwig cross-coupling reactions, N-arylation reactions, H-mont mediated etherification reactions, Miyaura borylation reactions, Suzuki cross-coupling reactions, intramolecular acid-induced cyclization reactions, Pd(II)-catalyzed oxidative cyclization reactions, Grignard reactions, Heck reactions, cyclodehydration reactions, SN1 substitution reactions, SN2 substitution reactions, phosphine-mediated reductive cyclization reactions, etc., and that the above reactions will proceed even when substituents defined in formula 2 above but not specified in the specific synthetic examples are attached.

[0062] In addition, the present disclosure provides an organic electroluminescent material comprising the compound represented by Formula 1-A, and an organic electroluminescent device comprising this material. This material can consist solely of the organic electroluminescent compound of the present disclosure, or can further comprise conventional materials contained in organic electroluminescent materials.

[0063] The organic electroluminescent compound represented by Formula 1-A can be included in any one of the following layers: light-emitting layer, hole-injection layer, hole-transporting layer, hole-assisting layer, light-emitting auxiliary layer, electron-transporting layer, electron buffer layer, electron-injecting layer, intermediate layer, hole-blocking layer, and electron-blocking layer. Preferably, the organic electroluminescent compound represented by Formula 1-A can be included in at least one of the light-emitting layer, hole-transporting layer, hole-assisting layer, light-emitting auxiliary layer, electron-transporting layer, electron buffer layer, hole-blocking layer, and electron-blocking layer, if necessary. When used in the electron-transporting layer, the organic electroluminescent compound represented by Formula 1-A and conventional materials can be included in a weight ratio of about 1:1.

[0064] An organic electroluminescent device according to the present disclosure may include an anode, a cathode, and at least one organic layer between the anode and the cathode, where the organic layer may include a plurality of organic electroluminescent materials, including a compound represented by Formula 1 as a first organic electroluminescent material and a compound represented by Formula 2 as a second organic electroluminescent material. According to one embodiment of the present disclosure, an organic electroluminescent device according to the present disclosure may include an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, where at least one of the light-emitting layers may include a compound represented by Formula 1 and a compound represented by Formula 2, preferably a plurality of host materials of the present disclosure.

[0065] In this specification, the electrode may be a semi-transparent electrode or a reflective electrode, and may be a top-emitting, bottom-emitting, or dual-emitting type depending on the material. 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.

[0066] The light-emitting layer includes a host and a dopant. The host includes multiple host materials, and the compound represented by Formula 1 can be included as a first host compound among the multiple host materials, and the compound represented by Formula 2 can be included as a second host compound among the multiple host materials. The weight ratio of the first host compound to the second host compound is about 1:99 to about 99:1, preferably about 10:90 to about 90:10, more preferably about 30:70 to about 70:30, even more preferably about 40:60 to about 60:40, and even more preferably about 50:50. When at least two materials are included in one layer, they can be evaporated together to form a layer, or they can be evaporated separately and simultaneously to form a layer.

[0067] In the present disclosure, the light-emitting layer is a layer that emits light, and may be a single layer or a multilayer structure in which two or more layers are stacked. The first host material and the second host material may all be included in one layer, or the first host material and the second host material may each be included in a different light-emitting layer. According to one embodiment of the present disclosure, the doping concentration of the dopant compound relative to the host compound in the light-emitting layer may be less than 20% by weight.

[0068] The organic electroluminescent device of the present disclosure 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 injection layer, an intermediate layer, an electron buffer layer, a hole blocking layer, and an electron blocking layer. According to one embodiment of the present disclosure, the organic electroluminescent device of the present disclosure may further include an amine-based compound as at least one of the hole injection material, the hole transport material, the hole auxiliary material, the emitting material, the emitting auxiliary material, and the electron blocking material in addition to the plurality of host materials of the present disclosure. Furthermore, according to one embodiment of the present disclosure, the organic electroluminescent device of the present disclosure may further include an azine-based compound as at least one of the electron transport material, the electron injection material, the electron buffer material, and the hole blocking material in addition to the plurality of host materials of the present disclosure.

[0069] The dopant that is included in the organic electroluminescent device of the present disclosure can be at least one phosphorescent or fluorescent dopant, and is preferably phosphorescent dopant.The phosphorescent dopant material that is used in the organic electroluminescent device of the present disclosure is not particularly limited, but can be preferably selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt) metallized complex compound, more preferably selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt) ortho-metallized complex compound, and even more preferably be ortho-metallized iridium complex compound.

[0070] Dopants included in OLEDs of the present disclosure can include, but are not limited to, compounds represented by Formula 101 below: [ka]

[0071] In formula 101, L is one of the following structures 1-3: [ka] Selected from; R 100 ~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, cyano, substituted or unsubstituted (3-30 membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; or may be combined with adjacent substituents to form a ring, for example, R 100 ~R 103 may be joined together with the pyridine to form a substituted or unsubstituted quinoline, isoquinoline, benzofuropyridine, benzothienopyridine, indenopyridine, benzofuroquinoline, benzothienoquinoline, or indenoquinoline, and R 104 ~R 107may, together with benzene, be linked to adjacent substituents to form a substituted or unsubstituted naphthalene, fluorene, dibenzothiophene, dibenzofuran, indenopyridine, benzofuropyridine, or benzothienopyridine; R 201 ~R 220 each independently represent 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 combined with adjacent substituents to form a ring; n' represents an integer of 1 to 3.

[0072] Specific examples of dopant compounds include, but are not limited to, the following: [ka] [ka] [ka] [ka] [ka]

[0073] According to one embodiment of the present disclosure, an organic electroluminescent device according to the present disclosure may include an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein at least one of the light-emitting layers may include a plurality of host materials of the present disclosure and a compound represented by the following formula 3: [ka]

[0074] In Equation 3, R 11 ~R 13each independently represents a substituted or unsubstituted (C1-C5) alkyl, and R 14 represents a substituted or unsubstituted (C1-C5) alkyl, or a phenyl that is unsubstituted or substituted with a (C1-C5) alkyl.

[0075] To form each layer of the organic electroluminescent device of the present disclosure, dry film formation methods such as vacuum evaporation, sputtering, plasma, ion plating, etc., or wet film formation methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating, etc. can be used.

[0076] When using a wet film formation method, a thin film can be formed by dissolving or dispersing the materials that form each layer in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent can be any solvent as long as it can dissolve or disperse the materials that form each layer and does not pose a problem in terms of film formation ability.

[0077] Additionally, the compounds of Formula 1 and Formula 2 can be formed into films by the methods listed above, generally by a co-evaporation process or a mixed evaporation process. Co-evaporation is a mixed evaporation method in which two or more materials are placed in separate crucible sources and current is passed through both cells simultaneously to evaporate the materials. Mixed evaporation is a mixed evaporation method in which two or more materials are mixed in a single crucible source before evaporating them and current is passed through the cells to evaporate the materials.

[0078] The organic electroluminescent material according to the present disclosure can be used as a light-emitting material for a white organic light-emitting device. White organic light-emitting devices have been proposed to have various structures, such as a parallel arrangement (side-by-side) method, a stacking method, or a color conversion material (CCM) method, depending on the arrangement of the R (red), G (green), YG (yellow-green), or B (blue) light-emitting units. The present disclosure can also be applied to white organic light-emitting devices. In addition, the organic electroluminescent material according to the present disclosure can also be used in organic electroluminescent devices containing quantum dots (QDs).

[0079] The present disclosure can provide a display system comprising a plurality of host materials of the present disclosure.In addition, the organic electroluminescent device of the present disclosure can be used to manufacture a display system or a lighting system.Specifically, the organic electroluminescent device of the present disclosure can be used to manufacture a display system, such as a display system for a smartphone, a tablet, a notebook, a PC, a TV, or an automobile; or a lighting system, such as an outdoor or indoor lighting system.

[0080] Hereinafter, the preparation methods of compounds according to the present disclosure and their properties will be described in detail with reference to representative compounds of the present disclosure. However, the present disclosure is not limited by the following examples. [Example]

[0081] Example 1: Preparation of Compound C-1 [ka]

[0082] Synthesis of Compound 1-1 In a flask, (9-phenyl-9H-carbazol-4-yl)boronic acid (96 g, 334.3 mmol), 2-bromo-1-chloro-3-nitrobenzene (71.8 g, 304 mmol), Pd(dba) (15 g, 16.71 mmol), S-Phos (10.9 g, 26.76 mmol), and KPO (315 g, 1.64 mmol) were dissolved in 1500 mL of toluene, and the mixture was stirred at 130 °C for 4 h. After the reaction was completed, the organic layer was extracted with ethyl acetate and the residual water was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound 1-1 (67 g, yield: 56.6%).

[0083] Synthesis of Compound 1-2 In a flask, compound 1-1 (23.5 g, 58.9 mmol), (2-chlorophenyl)boronic acid (18.4 g, 117.8 mmol), Pd(dba) (2.7 g, 2.95 mmol), S-Phos (2.4 g, 5.89 mmol), and KPO (63 g, 294.5 mmol) were dissolved in 300 mL of toluene, and the mixture was stirred at 130 °C for 12 h. After the reaction was completed, the organic layer was extracted with ethyl acetate and magnesium sulfate was used to remove residual water. The residue was dried and separated by column chromatography to obtain compound 1-2 (14 g, yield: 50%).

[0084] Synthesis of compounds 1-3 In a flask, compound 1-2 (13 g, 27.4 mmol) and triphenylphosphine (21.5 g, 82.1 mmol) were dissolved in 140 mL of o-DCB, and the mixture was stirred at 220° C. for 7 hours. After completion of the reaction, the reaction mixture was distilled and separated by column chromatography to obtain compound 1-3 (4 g, yield: 32%).

[0085] Synthesis of compounds 1-4 In a flask, compound 1-3 (10 g, 22.5 mmol), Pd(OAc) (505 mg, 2.25 mmol), PCy-HBF (1.63 g, 4.5 mmol), and CsCO (22 g, 67.5 mmol) were dissolved in 113 mL of o-xylene, and the mixture was stirred at 160 °C for 4 h. After the reaction was completed, the organic layer was extracted with ethyl acetate and magnesium sulfate was used to remove residual water. The residue was dried and separated by column chromatography to obtain compound 1-4 (1 g, yield: 11%).

[0086] Synthesis of compound C-1 In a flask, compound 1-4 (4.5 g, 11.06 mmol), 2-chloro-3-phenylquinoxaline (4 g, 16.6 mmol), 4-dimethylaminopyridine (DMAP) (67 mg, 0.553 mmol), and Cs2CO3 (10.8 g, 331.8 mmol) were dissolved in 60 mL of dimethyl sulfoxide (DMSO), and the mixture was refluxed at 140 °C for 4 h. After the reaction was completed, the organic layer was extracted with ethyl acetate and magnesium sulfate was used to remove residual water. The residue was dried and separated by column chromatography to obtain compound C-1 (2.5 g, yield: 37%).

[0087] [Table 1]

[0088] Example 2: Preparation of Compound C-29 [ka] In a flask, compound 1-4 (4 g, 9.84 mmol), 3-bromo-1,1':2',1''-terphenyl (3.65 g, 11.8 mmol), Pd2(dba)3 (448 mg, 0.492 mmol), S-Phos (448 mg, 0.984 mmol), and NaOtBu (2.84 g, 29.52 mmol) were dissolved in 50 mL of o-xylene, and the mixture was stirred at 170 °C for 4 h. After the reaction was completed, the organic layer was extracted with ethyl acetate and the residual water was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound C-29 (1.5 g, yield: 24%).

[0089] [Table 2]

[0090] Example 3: Preparation of Compound C-196 [ka]

[0091] Synthesis of Compound 3-1 Compound A (60 g, 283 mmol), compound B (100 g, 424 mmol), tetrakis(triphenylphosphine)palladium (16.3 g, 14.1 mmol), cesium carbonate (276 g, 849 mmol), 1400 mL of toluene, 350 mL of ethanol, and 350 mL of distilled water were added to a reaction vessel, and the mixture was stirred at 130 °C for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was then removed using a rotary evaporator. The residue was separated by column chromatography to obtain compound 3-1 (38 g, yield: 41%).

[0092] Synthesis of compound 3-2 Compound 3-1 (38 g, 117 mmol), phenylboronic acid (35 g, 234 mmol), tris(dibenzylideneacetone)dipalladium (5.3 g, 5.86 mmol), S-Phos (4.8 g, 11.7 mmol), potassium phosphate tripotassium (62 g, 293 mmol), and 600 mL of toluene were added to a reaction vessel, and the mixture was stirred under reflux for 2 hours. After completion of the reaction, the reaction mixture was washed with distilled water and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was then removed by rotary evaporation. The residue was separated by column chromatography to give compound 3-2 (31 g, yield: 67%).

[0093] Synthesis of compound 3-3 Compound 3-2 (21 g, 53.7 mmol), triphenyl phosphite (70 mL, 268 mmol), and 180 mL of dichlorobenzene (DCB) were added to a reaction vessel, and the mixture was stirred at 200 °C for 12 hours. After the reaction was completed, the reaction mixture was distilled under reduced pressure to remove DCB, washed with distilled water, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and then the solvent was removed by rotary evaporation. The residue was separated by column chromatography to obtain compound 3-3 (10 g, yield: 55%).

[0094] Synthesis of Compound 3-4 Compound 3-3 (6.6 g, 17.9 mmol), palladium(II) acetate (0.2 g, 0.89 mmol), PCy3-BF4 (1.3 g, 3.58 mmol), cesium carbonate (17 g, 53.7 mmol), and 90 mL of o-xylene were added to a reaction vessel, and the mixture was stirred under reflux at 160 °C for 4 h. After completion of the reaction, the reaction mixture was washed with distilled water and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and then the solvent was removed by rotary evaporation. The residue was separated by column chromatography to give compound 3-4 (1.8 g, yield: 32%).

[0095] Synthesis of compound C-196 Compound 3-4 (1.8 g, 5.43 mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (2.3 g, 5.97 mmol), tris(dibenzylideneacetone)dipalladium (0.2 g, 0.27 mmol), tri-tert-butylphosphine (0.3 mL, 0.54 mmol), sodium tert-butoxide (1.3 g, 13.5 mmol), and 30 mL of toluene were added to a reaction vessel, and the mixture was stirred under reflux for 3 hours. After completion of the reaction, the reaction mixture was washed with distilled water and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was then removed by rotary evaporation. The residue was separated by column chromatography to obtain compound C-196 (3.3 g, yield: 95%).

[0096] [Table 3]

[0097] Example 4: Preparation of Compound C-36 [ka] In a flask, compound 1-4 (4.0 g, 9.84 mmol), 4-bromo-N,N-diphenylaniline (3.2 g, 9.84 mmol), Pd(dba) (0.45 g, 0.5 mmol), s-phos (0.4 g, 0.98 mmol), and NaOtBu (1.9 g, 19.7 mmol) were dissolved in 50 mL of o-xylene, and the mixture was stirred under reflux for 5 h. After completion of the reaction, the organic layer was extracted with ethyl acetate and separated by column chromatography to give compound C-36 (2.67 g, 42% yield).

[0098] [Table 4]

[0099] Example 5: Preparation of Compound C-32 [ka] In a flask, compound 4-1 (4.0 g, 9.84 mmol), 2-bromodibenzo[b,d]furan (1.7 g, 9.84 mmol), Pd(dba) (0.45 g, 0.5 mmol), s-phos (0.4 g, 0.98 mmol), and NaOtBu (1.9 g, 19.7 mmol) were dissolved in 50 mL of o-xylene, and the mixture was stirred under reflux for 5 h. After completion of the reaction, the organic layer was extracted with ethyl acetate and separated by column chromatography to give compound C-32 (1.68 g, 30% yield).

[0100] [Table 5]

[0101] Example 6: Preparation of Compound E-112 [ka]

[0102] Synthesis of compound 14-1 In a flask, dibenzo[b,d]furan-1-ylboronic acid (20 g, 94.3 mmol), 1,4-dibromonaphthalene (53.9 g, 188.67 mmol), K2CO3 (32.6 g, 235.75 mmol), and Pd(PPh3)4 (5.4 g, 4.7 mmol) were dissolved in 470 mL of toluene, 235 mL of ethanol, and 235 mL of water, and the mixture was refluxed at 140 °C for 4 h. After the reaction was completed, the organic layer was extracted with ethyl acetate and the residual water was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound 14-1 (20 g, yield: 56.8%).

[0103] Synthesis of compound 14-2 In a flask, compound 14-1 (20 g, 53.6 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolene) (16.3 g, 64.3 mmol), PdCl2(PPh3)2 (3.76 g, 5.36 mmol), and KOAc (10.5 g, 107.2 mmol) were dissolved in 270 mL of 1,4-dioxane, and the mixture was refluxed at 150 °C for 4 h. After the reaction was completed, the organic layer was extracted with ethyl acetate and magnesium sulfate was used to remove residual water. The residue was dried and separated by column chromatography to obtain compound 14-2 (23 g, yield: 100%).

[0104] Synthesis of compound E-112 In a flask, compound 14-2 (7 g, 16.6 mmol), 2-chloro-4,6-di(naphthalen-2-yl)-1,3,5-triazine (7.35 g, 19.9 mmol), Cs2CO3 (13.5 g, 41.5 mmol), and Pd(PPh3)4 (959 mg, 0.83 mmol) were dissolved in 83 mL of toluene, and the mixture was refluxed at 130 °C for 18 h. After the reaction was completed, the organic layer was extracted with ethyl acetate and magnesium sulfate was used to remove residual water. The residue was dried and separated by column chromatography to obtain compound E-112 (2 g, yield: 19.2%).

[0105] Example 7: Preparation of Compound E-117 [ka]

[0106] Synthesis of compound 15-1 In a flask, 2-chloro-4,6-di(naphthalen-2-yl)-1,3,5-triazine (32.2 g, 87.7 mmol), (4-bromonaphthalen-1-yl)boronic acid (20 g, 79.7 mmol), Cs2CO3 (65 g, 199.25 mmol), and Pd(PPh3)4 (4.6 g, 3.985 mmol) were dissolved in 400 mL of toluene, and the mixture was refluxed at 140 °C for 4 h. After the reaction was completed, the organic layer was extracted with ethyl acetate and magnesium sulfate was used to remove residual water. The residue was dried and separated by column chromatography to obtain compound 15-1 (20 g, yield: 46.6%).

[0107] Synthesis of compound E-117 In a flask, compound 15-1 (7 g, 13 mmol), 2-(dibenzo[b,d]furan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.6 g, 15.6 mmol), K2CO3 (4.5 g, 32.5 mmol), and Pd(PPh3)4 (0.75 g, 0.65 mmol) were dissolved in 65 mL of toluene, 32.5 mL of ethanol, and 32.5 mL of HO. The mixture was refluxed at 130 °C for 3 h. After the reaction was completed, the organic layer was extracted with ethyl acetate and the residual water was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound E-117 (3.4 g, yield: 41%).

[0108] Example 8: Preparation of Compound E-129 [ka] In a flask, compound 15-1 (4.4 g, 12.3 mmol), 2-(dibenzo[b,d]furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (5 g, 13.5 mmol), Cs2CO3 (4.5 g, 32.5 mmol), and Pd(PPh3)4 (0.75 g, 0.65 mmol) were dissolved in 60 mL of toluene, 30 mL of ethanol, and 30 mL of HO. The mixture was refluxed at 130 °C for 3 h. After the reaction was completed, the organic layer was extracted with ethyl acetate and magnesium sulfate was used to remove residual water. The residue was dried and separated by column chromatography to obtain compound E-129 (4 g, yield: 49%).

[0109] Example 9: Preparation of Compound E-111 [ka] In a flask, 64 mL of toluene, 16 mL of EtOH, and 16 mL of distilled water were added to compound 14-2 (6 g, 14.16 mmol), 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (5 g, 15.73 mmol), Pd(PPh3)4 (0.9 g, 0.786 mmol), and K2CO3 (4.3 g, 31.47 mmol), and the mixture was stirred under reflux for 2 h. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with distilled water and ethyl acetate (EA). The organic layer was distilled under reduced pressure and separated by column chromatography using MC / Hex to give compound E-111 (4 g, yield: 44%). 1H NMR(DMSO-d6)δ:9.42(d,J=1.3Hz,1H),9.29-9.24(m,1H),8.83(td,J=8.6,1.5Hz,3H),8.7 2(d,J=7.3Hz,1H),8.30(d,J=8.0Hz,1H),8.22(d,J=8.7Hz,1H),8.12-8.07(m,1H),7.92(d d,J=8.3,0.8Hz,1H),7.89(d,J=7.3Hz,1H),7.81-7.72(m,6H),7.72-7.65(m,2H),7.65-7. 60(m,1H),7.54-7.41(m,3H),7.04(ddd,J=8.1,7.3,0.9Hz,1H),6.53(dt,J=8.0,0.9Hz,1H)

[0110] [Table 6]

[0111] Example 10: Preparation of Compound E-90 [ka]

[0112] Synthesis of compound 18-1 In a flask, 150 mL of toluene and 30 mL of distilled water were added to 2,4,6-trichloro-1,3,5-triazine (10 g, 54.22 mmol), dibenzo[b,d]furan-1-ylboronic acid (20.7 g, 97.60 mmol), PdCl(PPh) (0.76 g, 1.084 mmol), and NaCO (5.7 g, 54.22 mmol), and the mixture was stirred for 2 days. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with distilled water and MeOH to give compound 18-1 (3.4 g, 14% yield).

[0113] Synthesis of compound E-90 In a flask, 32 mL of toluene, 8 mL of EtOH, and 8 mL of distilled water were added to compound 18-1 (3.4 g, 7.592 mmol), naphthalen-2-ylboronic acid (1.5 g, 9.111 mmol), Pd(PPh3)4 (0.4 g, 0.379 mmol), and K2CO3 (2 g, 15.18 mmol), and the mixture was stirred under reflux at 140 °C for 1 h. After completion of the reaction, the reaction mixture was concentrated under reduced pressure and extracted with MC. The organic layer was concentrated and separated by column chromatography using MC / Hex to give compound E-90 (0.88 g, yield: 21%). 1 H NMR(DMSO-d6)δ:9.35(d,J=1.6Hz,1H),8.74(dd,J=8.6,1.7Hz,1H),8.71(dd,J=7.7,1.2Hz,2H),8.51(dd,J=7.7,1.0Hz,2H),8.20(d,J=8.7Hz,1H),8. 13-8.07(m,4H),7.86-7.80(m,4H),7.75-7.70(m,1H),7.66(dd,J=8.5,7.0 Hz,1H),7.59(ddd,J=8.4,7.2,1.3Hz,2H),7.18(ddd,J=8.1,7.1,1.0Hz,2H)

[0114] [Table 7]

[0115] Example 11: Preparation of Compound E-125 [ka] In a flask, dibenzo[b,d]furan-1-ylboronic acid (3.0 g, 14.2 mmol), 2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (7.3 g, 15.6 mmol), tetrakis(triphenylphosphine)palladium(0) (0.8 g, 0.71 mmol), and sodium carbonate (3.9 g, 28.4 mmol) were dissolved in 30 mL of toluene, 8 mL of ethanol, and 15 mL of water, and the mixture was refluxed for 2 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate and magnesium sulfate was used to remove residual water. The residue was dried and separated by column chromatography to obtain compound E-125 (2.7 g, 35% yield).

[0116] [Table 8]

[0117] Example 12: Preparation of Compound E-106 [ka] In a flask, dibenzo[b,d]furan-1-ylboronic acid (3.0 g, 14.2 mmol), 2-(4-bromonaphthalen-1-yl)-4,6-diphenyl-1,3,5-triazine (6.3 g, 14.2 mmol), tetrakis(triphenylphosphine)palladium(0) (0.82 g, 0.71 mmol), and sodium carbonate (3.9 g, 28.4 mmol) were dissolved in 30 mL of toluene, 8 mL of ethanol, and 15 mL of water, and the mixture was refluxed for 2 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate and magnesium sulfate was used to remove residual water. The residue was dried and separated by column chromatography to obtain compound E-106 (1.9 g, yield: 26%).

[0118] [Table 9]

[0119] Example 13: Preparation of Compound E-91 [ka] In a flask, 2,4-dichloro-6-(4-(naphthalen-2-yl)phenyl)-1,3,5-triazine (1.6 g, 4.54 mmol), dibenzo[b,d]furan-1-ylboronic acid (2.12 g, 10 mmol), tetrakis(triphenylphosphine)palladium(0) (0.26 g, 0.23 mmol), and sodium carbonate (1.3 g, 9.0 mmol) were dissolved in 16 mL of toluene, 1 mL of ethanol, and 4 mL of water, and the mixture was refluxed for 3 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate and magnesium sulfate was used to remove residual water. The residue was dried and separated by column chromatography to obtain compound E-91 (1.0 g, yield: 36%).

[0120] [Table 10]

[0121] Example 14: Preparation of Compound E-110 [ka] In a flask, 2-(4-(dibenzo[b,d]furan-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.0 g, 10.8 mmol), 2-chloro-4,6-di(naphthalen-2-yl)-1,3,5-triazine (4.4 g, 11.9 mmol), tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.54 mmol), and sodium carbonate (3.0 g, 21.6 mmol) were dissolved in 30 mL of toluene, 7 mL of ethanol, and 10 mL of water, and the mixture was refluxed for 7 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate and magnesium sulfate was used to remove residual water. The residue was dried and separated by column chromatography to obtain compound E-110 (4.0 g, yield: 65%).

[0122] [Table 11]

[0123] Example 15: Preparation of Compound E-130 [ka] In a flask, 2-chloro-2,4-dinaphthalenyl-1,3,5-triazine (6.7 g, 18.3 mmol), dibenzo[b,d]thiophen-1-ylboronic acid (5 g, 21.92 mmol), Pd(PPh3)4 (1.05 g, 0.915 mmol), and K2CO3 (6.3 g, 45.75 mmol) were dissolved in 90 mL of toluene, 22.5 mL of ethanol, and 22.5 mL of water, and the mixture was refluxed at 130 °C for 4 h. After the reaction was completed, the organic layer was extracted with ethyl acetate and magnesium sulfate was used to remove residual water. The residue was dried and separated by column chromatography to obtain compound E-130 (7.9 g, yield: 83.7%).

[0124] [Table 12]

[0125] Example 16: Preparation of Compound E-132 [ka] In a flask, 2-chloro-2,4-dinaphthalenyl-1,3,5-triazine (8.6 g, 23.58 mmol), dibenzo[b,d]furan-1-ylboronic acid (6 g, 28.3 mmol), Pd(PPh3)4 (1.4 g, 1.179 mmol), and K2CO3 (8.1 g, 58.95 mmol) were dissolved in 117 mL of toluene, 27 mL of ethanol, and 39 mL of water, and the mixture was refluxed at 130 °C for 4 h. After the reaction was completed, the organic layer was extracted with ethyl acetate and magnesium sulfate was used to remove residual water. The residue was dried and separated by column chromatography to obtain compound E-132 (7.0 g, yield: 59.47%).

[0126] [Table 13]

[0127] Example 17: Preparation of Compound E-131 [ka]

[0128] Synthesis of compound 19-1 In a flask, 2,4-dichloro-6-(naphthalen-2-yl)-1,3,5-triazine (58 g, 212 mmol), dibenzo[b,d]furan-1-ylboronic acid (30 g, 141 mmol), Na2CO3 (45 g, 424 mmol), and Pd(PPh3)4 (4.9 g, 7.05 mmol) were dissolved in 1.4 L of toluene and 352 mL of HO, and the mixture was refluxed at 100 °C for 18 h. After the reaction was completed, the organic layer was extracted with ethyl acetate and magnesium sulfate was used to remove residual water. The residue was dried and separated by column chromatography to obtain compound 19-1 (30 g, yield: 52%).

[0129] Synthesis of compound E-131 In a flask, compound 19-1 (6 g, 14.7 mmol), 4-(naphthalen-2-yl)-phenylboronic acid (5.8 g, 17.64 mmol), K2CO3 (5.0 g, 36.75 mmol), and Pd(PPh3)4 (0.85 mg, 0.73 mmol) were dissolved in 70 mL of toluene, 35 mL of EtOH, and 35 mL of HO, and the mixture was refluxed at 130 °C for 4 h. After the reaction was completed, the organic layer was extracted with ethyl acetate and magnesium sulfate was used to remove residual water. The residue was dried and separated by column chromatography to obtain compound E-131 (4.9 g, yield: 58%).

[0130] [Table 14]

[0131] Example 18: Preparation of Compound E-145 [ka]

[0132] Synthesis of compound 20-1 In a flask, 2,6-dibromonaphthalene (20 g, 70 mmol), phenylboronic acid (9 g, 73.4 mmol), K2CO3 (24 g, 175 mmol), and Pd(PPh3)4 (4 g, 3.5 mmol) were dissolved in 350 mL of toluene, 170 mL of HO, and 170 mL of EtOH, and the mixture was refluxed at 130 °C for 1 h. After the reaction was completed, the organic layer was extracted with ethyl acetate and magnesium sulfate was used to remove residual water. The residue was dried and separated by column chromatography to obtain compound 20-1 (13 g, yield: 67%).

[0133] Synthesis of compound 20-2 In a flask, compound 20-1 (13 g, 45.9 mmol), (4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (17.5 g, 68.8 mmol), KOAc (11.3 g, 114.75 mmol), and PdCl2(PPh3)2 (3.2 g, 4.59 mmol) were dissolved in 230 mL of 1,4-dioxane, and the mixture was refluxed at 150 °C for 2 h. After the reaction was completed, the organic layer was extracted with ethyl acetate and the residual water was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound 20-2 (9 g, yield: 59.3%).

[0134] Synthesis of compound E-145 In a flask, compound 20-2 (6.4 g, 19.16 mmol), compound 19-1 (6.5 g, 15.96 mmol), K2CO3 (5.5 g, 39.9 mmol), and Pd(PPh3)4 (922 mg, 0.798 mmol) were dissolved in 80 mL of toluene, 40 mL of EtOH, and 40 mL of HO, and the mixture was refluxed at 130 °C for 2 h. After the reaction was completed, the organic layer was extracted with ethyl acetate and magnesium sulfate was used to remove residual water. The residue was dried and separated by column chromatography to obtain compound E-145 (4.9 g, yield: 53.3%).

[0135] [Table 15]

[0136] Hereinafter, the manufacturing method of the organic electroluminescent device (OLED) according to the present disclosure and its luminous efficiency and lifespan characteristics will be described in detail. However, the present disclosure is not limited by the following examples.

[0137] Device Examples 1 and 2: Fabrication of OLEDs According to the Present Disclosure An OLED according to the present disclosure was fabricated. A transparent indium tin oxide (ITO) thin film (10 Ω / sq) (Geomatec Co., Ltd., Japan) on a glass substrate for OLEDs was subjected to ultrasonic cleaning in acetone and isopropyl alcohol, followed by storage in isopropanol. The ITO substrate was then attached to a substrate holder in a vacuum evaporation system. Compound HI-1, listed in Table 3, was introduced into one cell of the vacuum evaporation system, and compound HT-1, listed in Table 3, was introduced into another cell of the vacuum evaporation system. The two materials were evaporated at different rates, and compound HI-1 was deposited at a doping amount of 3 wt. % based on the total amount of compound HI-1 and compound HT-1 to form a hole injection layer with a thickness of 10 nm on the ITO substrate. Compound HT-1 was then deposited on the hole injection layer to form a first hole transport layer with a thickness of 80 nm on the hole injection layer. Next, compound HT-2 was introduced into another cell of the vacuum evaporation system and evaporated by passing a current through the cell, thereby forming a second hole-transporting layer with a thickness of 60 nm on the first hole-transporting layer. After forming the hole-injection layer and hole-transporting layer, an emitting layer was formed thereon as follows: the first and second host compounds shown in Table 1 below were introduced into two cells of the vacuum evaporation system as hosts, and compound D-39 was introduced into another cell as a dopant. The two host materials were evaporated in a 1:1 ratio, and the dopant materials were simultaneously evaporated in different ratios. The dopant was evaporated at a doping amount of 3 wt % based on the total amount of host and dopant to form an emitting layer with a thickness of 40 nm on the second hole-transporting layer. Compounds ETL-1 and EIL-1 were evaporated in a 50:50 weight ratio to form an electron-transporting layer with a thickness of 35 nm on the emitting layer. Compound EIL-1 was deposited on the electron transport layer as an electron injection layer with a thickness of 2 nm, and then an Al cathode with a thickness of 80 nm was deposited on the electron injection layer using another vacuum deposition device. In this way, an OLED was fabricated. All materials used to fabricate the OLED were 10 -6 It was purified by vacuum sublimation at torr.

[0138] Comparative Examples 1 and 2: Preparation of OLEDs containing comparative compounds as hosts OLEDs were fabricated in the same manner as in Device Example 1, except that the compounds shown in Table 1 below were used alone as the first or second host in the emissive layer.

[0139] The driving voltage, luminous efficiency, and emission color at a luminance of 1,000 nits, as well as the time required for the luminance to decrease from 100% to 95% (lifetime; T95) at a luminance of 5,000 nits, of the OLEDs fabricated in Comparative Examples 1 and 2 and Device Examples 1 and 2 are shown in Table 1 below.

[0140] [Table 16]

[0141] From Table 1 above, it can be seen that an OLED comprising multiple host materials according to the present disclosure has improved driving voltage, luminous efficiency, and / or lifetime characteristics compared to conventional OLEDs. It is believed that by using the compound represented by Formula 1 of the present disclosure in combination with the compound represented by Formula 2 of the present disclosure, the balance between holes and electrons and the formation of excitons can be improved compared to using a single host, thereby improving the driving voltage, luminous efficiency, and / or lifetime characteristics of the OLED.

[0142] Device Examples 3 and 4: Fabrication of OLEDs According to the Present Disclosure An OLED according to the present disclosure was fabricated. A transparent indium tin oxide (ITO) thin film (10 Ω / sq) (Geomatec Co., Ltd., Japan) on a glass substrate for OLEDs was subjected to ultrasonic cleaning in acetone and isopropyl alcohol, followed by storage in isopropanol. The ITO substrate was then attached to a substrate holder in a vacuum evaporation system. Compound HI-1, listed in Table 3, was introduced into one cell of the vacuum evaporation system, and compound HT-1, listed in Table 3, was introduced into another cell of the vacuum evaporation system. The two materials were evaporated at different rates, and compound HI-1 was deposited at a doping amount of 3 wt. % based on the total amount of compound HI-1 and compound HT-1 to form a hole injection layer with a thickness of 10 nm on the ITO substrate. Compound HT-1 was then deposited on the hole injection layer to form a first hole transport layer with a thickness of 70 nm on the hole injection layer. Next, compound HT-3 was introduced into another cell of the vacuum evaporation system and evaporated by passing a current through the cell, thereby forming a second hole-transporting layer with a thickness of 5 nm on the first hole-transporting layer. After forming the hole-injection layer and hole-transporting layer, an emitting layer was formed thereon as follows: compound BH shown in Table 3 was introduced into one cell of the vacuum evaporation system as a host, and compound BD was introduced into another cell as a dopant. The host material and dopant material were evaporated at different rates, and the dopant was evaporated at a doping amount of 3 wt % based on the total amount of host and dopant to form an emitting layer with a thickness of 20 nm on the second hole-transporting layer. Compound B-1 was evaporated to form an electron buffer layer with a thickness of 5 nm on the emitting layer. The compounds shown in Table 2 below were evaporated in a 50:50 weight ratio to form an electron-transporting layer with a thickness of 30 nm on the electron buffer layer. Compound EIL-1 was deposited on the electron transport layer as an electron injection layer with a thickness of 2 nm, and then an Al cathode with a thickness of 80 nm was deposited on the electron injection layer using another vacuum deposition device. In this way, an OLED was fabricated. All materials used to fabricate the OLED were 10 -6 It was purified by vacuum sublimation at torr.

[0143] Comparative Example 3: Fabrication of an OLED containing a comparative compound as an electron transport layer OLEDs were fabricated in the same manner as in Device Example 3, except that the compounds shown in Table 2 below were used as the electron transport layer.

[0144] The driving voltage and emission color at a luminance of 1,000 nits, and the time required for the luminance to decrease from 100% to 50% (lifetime; T50) at a luminance of 2,000 nits for the OLEDs fabricated in Comparative Example 3 and Device Examples 3 and 4 are shown in Table 2 below.

[0145] [Table 17]

[0146] From Table 2 above, it can be seen that the OLEDs comprising the compounds according to the present disclosure in the electron transport layer have improved lifetime characteristics compared to conventional OLEDs.

[0147] The compounds used in the device examples and comparative examples are shown in Table 3.

[0148] [Table 18]

[0149] [Table 19]

Claims

1. A plurality of host materials comprising at least one first host compound and at least one second host compound, wherein the first host compound is represented by the following Formula 1: 【Chemistry 1】 (In formula 1, X represents O or S; R １ ~R ８ are each independently *-(L １ ) ａ -L ２ -(HAr) ｂ , hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, -NR ２２ R ２３ , or -SiR ２４ R ２５ R ２６ or may be joined to adjacent substituents to form a ring; However, R １ ~R ８ At least one of *-(L １ ) ａ -L ２ -(HAr) ｂ provided that it represents L １ each independently represents 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; L ２ represents an unsubstituted (3- to 30-membered) heteroarylene; Each HAr is independently deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, -NR ２２ R ２３ , or -SiR ２４ R ２５ R ２６ represents; R ２２ ~R ２６ each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl; or can be combined with adjacent substituents to form a ring; a represents an integer of 0 to 2, and b represents an integer of 1 to 4. When a and b are each an integer of 2 or more, L １ and each HAr may be the same or different. is expressed as The second host compound is represented by the following formulas 2-1 to 2-3: 【Chemistry 2】 (In formulas 2-1 to 2-3, Y １ , Y ２ , Y ３ , and Y ４ are each independently -N(L ３ -(Ar) ｎ )-, -O-, -S-, or -C(R ３１ ) (R ３２ )-, where if more than one Ar is present, each Ar may be the same or different; X １ ~X １２ are each independently -N= or -C(R ａ ) =; R ａ each independently represents hydrogen or deuterium, and when a plurality of Ra are present, R ａ each of which may be the same or different; L ３ 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 is a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 membered) heteroaryl, or —NR ３３ R ３４ represents; R ３１ ~R ３４ 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, or substituted or unsubstituted (C3-C30) cycloalkyl; or can be joined with adjacent substituents to form a ring; n represents an integer of 1 or 2, where when n is 2, each of Ar can be the same or different. The host material is represented by at least one of:

2. Substituents of the substituted alkyl, the substituted alkylene, the substituted aryl, the substituted arylene, the substituted heteroaryl, the substituted heteroarylene, the substituted cycloalkyl, the substituted cycloalkylene, the substituted cycloalkenyl, and the substituted heterocycloalkyl are each independently selected from 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-C 30) Alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3-7 membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (3-30 membered) heteroaryl unsubstituted or substituted with at least one of (C1-C30) alkyl and (C6-C30) aryl; (C6-C30) aryl unsubstituted or substituted with at least one of deuterium, (C1-C30) alkyl, (3-30 membered) heteroaryl, and mono- or di-(C6-C30) arylamino; tri (C1-C30) alkylsilyl; tri(C6-C30) arylsilyl; di(C1-C30) alkyl(C6-C30) arylsilyl; (C1-C30) alkyldi(C6-C30) arylsilyl; fused ring groups of a (C3-C30) aliphatic rings and (C6-C30) aromatic rings; amino; mono- or di-(C1-C30) alkylamino; mono- or di-(C2-C30) alkenylamino; mono- or di-(C6-C30) arylamino; mono- or di-(3- to 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; (C6-C30) arylphosphine; di(C6-C30) arylboronyl;10. The plurality of host materials of claim 1, wherein the plurality of host materials is at least one selected from the group consisting of di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl;

3. The formula 1 is represented by the following formulas 1-1 to 1-4: 【Transformation 3】 (In formulas 1-1 to 1-4, R １ ~R ８ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, —NR ２２ R ２３ , or -SiR ２４ R ２５ R ２６ or may be joined to adjacent substituents to form a ring; X, L １ , L ２ , HAr, a, b, and R ２２ ~R ２６ is as defined in claim 1) 10. The host material of claim 1, wherein the host material is represented by at least one of:

4. L in Formula 1 ２ 10. The plurality of host materials of claim 1, wherein: represents triazinylene, pyridylene, pyrimidinylene, quinazolinylene, benzoquinazolinylene, quinoxalinylene, benzoquinoxalinylene, quinolylene, benzoquinolylene, isoquinolylene, benzoisoquinolylene, triazolylene, pyrazolylene, naphthyridinylene, triazanaphthylene, pyridopyrazinylene, or benzothienopyrimidinylene.

5. At least one Ar is independently selected from the following Group 1: [Group 1] 【Chemistry 4】 (In Group 1, D1 and D2 each independently represent a benzene ring or a naphthalene ring; X ２１ is O, S, NR ３５ , or CR ３６ R ３７ represents; X ２２ are each independently CR ３８ or N, but X ２２ represents N; X ２３ are each independently CR ３９ or N; L １１ ~L １８ each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene; R １１ ~R ２１ and R ３５ ~R ３９ 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, or substituted or unsubstituted (C3-C30) cycloalkyl, or can be joined with adjacent substituents to form a ring; aa, ff, and gg each independently represent an integer of 1 to 5, bb represents an integer of 1 to 7, cc, dd, and ee each independently represent an integer of 1 to 4, where each of aa to gg represents an integer of 2 or more, and each R １１ ~R １７ may be the same or different) 10. The plurality of host materials of claim 1, wherein the host materials are at least one selected from those listed in

6. At least one Ar is independently selected from the following groups 2 and 3: [Group 2] 【Transformation 5】 【Transformation 6】 【Transformation 7】 【Transformation 8】 [Group 3] 【Chemistry 9】 【Chemistry 10】 (In Group 2, L 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; A １ ~A ３ each independently represents a substituted or unsubstituted (C1-C30) alkyl, or a substituted or unsubstituted (C6-C30) aryl.

10. The plurality of host materials of claim 1, wherein the host materials are at least one selected from those listed in

7. The compound of formula 1 is the following compound: 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 [Chemistry 18] 【Chemistry 19】 10. The plurality of host materials of claim 1, wherein the host material is at least one selected from:

8. The compound represented by at least one of formulas 2-1 to 2-3 is the following compound: 【Chemistry 20】 【Chemistry 21】 【Chemistry 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemistry 27】 【Chemistry 28】 10. The plurality of host materials of claim 1, wherein the host material is at least one selected from:

9. 10. An organic electroluminescent device comprising an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein at least one of the light-emitting layers comprises a plurality of host materials according to claim 1.

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