Organic electroluminescent compound, plural host materials, and organic electroluminescent device including the same

Abstract

To provide an organic electroluminescent compound, plural host materials, and an organic electroluminescent device including the organic electroluminescent compound and the host materials.SOLUTION: The present disclosure relates to an organic electroluminescent compound, a plurality of host materials, and an organic electroluminescent device having the host materials and the organic electroluminescent compound. By comprising a compound or a host material according to the present disclosure as host materials, an organic electroluminescent device having high luminous efficiency and / or long lifespan characteristics can be provided.SELECTED DRAWING: None

Description

[Technical Field]

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

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

[0003] The emitting material of an organic electroluminescent device is the most important factor determining the device's luminous efficiency. Emitting materials are required to have characteristics such as high quantum efficiency, high electron and hole mobility, and uniformity and stability of the formed luminescent material layer. Emitting materials are classified into host materials and dopant materials according to their function. A mixture of host and dopant can be used to improve color purity, luminous efficiency, and stability. Desirable properties of a host material, which functions as a solid-state solvent and energy carrier, include high purity and appropriate molecular weight to enable vacuum deposition. In addition, it must have a high glass transition temperature and a high thermal decomposition temperature to ensure thermal stability, high electrochemical stability for long lifetime, ease of forming amorphous thin films, and excellent adhesion to adjacent layer materials without interlayer migration. When such a dopant / host material system is used, the selection of the host material is important because it significantly affects the efficiency and lifetime of the luminescent device.

[0004] Although various compounds have been known as host materials, organic electroluminescent devices using the conventional materials have high driving voltages, low luminous efficiencies, and short lifetimes, so new materials have been needed. Therefore, there is a demand for the development of host materials that can realize organic electroluminescent devices that have excellent lifetime characteristics even when driven at low voltages and with high brightness.

[0005] Although Patent Document 1 discloses an organic electroluminescent device using phenanthroxazole and phenanthrothiazole compounds as hosts, it does not specifically disclose an organic electroluminescent device using a specific combination of multiple host materials as defined in this specification, and there is still a need to develop host materials to improve the performance of OLEDs.

[0006] Although Patent Document 2 discloses an organic electroluminescent device using a heterocyclic compound as a host or hole transport material, it does not specifically disclose an organic electroluminescent device using a specific combination of multiple host materials as defined in this specification, and there is still a need to develop host materials to improve the performance of OLEDs.

[0007] Patent Document 3 discloses an organic electroluminescent device containing a compound having a chrysene moiety in an emitting layer, but does not specifically disclose an organic electroluminescent device using a specific combination of multiple host materials as defined in this specification, and there is still a need to develop host materials to improve the performance of OLEDs. [Prior art documents] [Patent documents]

[0008] [Patent Document 1] Korean Patent Application Publication No. 10-2017-0022865 [Patent Document 2] Korean Patent Application Publication No. 10-2014-0057439 [Patent Document 3] Korean Patent Application Publication No. 10-1545774 [Patent Document 4] Korean Patent Application Publication No. 2018-0099487 [Patent Document 5] Korean Patent Application Publication No. 2021-0124018 [Patent Document 6] Korean Patent Application Publication No. 2021-0006283 [Non-patent literature]

[0009] [Non-Patent Document 1] Appl.Phys.Lett.51,913,1987) Summary of the Invention [Problem to be solved by the invention]

[0010] The objectives of the present disclosure are, first, to provide a plurality of host materials or organic electroluminescent compounds that enable the production of organic electroluminescent devices with high luminous efficiency and / or long life characteristics, and, second, to provide organic electroluminescent devices comprising the host materials. [Means for solving the problem]

[0011] As a result of intensive research to solve the above technical problems, the present inventors have found that the above object can be achieved by a first host material containing a compound represented by the following formula 1 and a second host material containing a compound represented by the following formula 2, or by a plurality of host materials containing an organic electroluminescent compound represented by any of the following formulas 3-1-1 to 3-4-1, and have completed the present disclosure. [ka]

[0012] In Equation 1, X represents O, S, or Se; HAr represents a substituted or unsubstituted (3-30 membered) heteroaryl containing one or more nitrogen atoms; L is a single bond, a substituted or unsubstituted (C6 to C 30 ) arylene, or substituted or unsubstituted (3 to 30-membered) heteroarylene; R1 and R2 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C 30 ) Alkyl, substituted or unsubstituted (C6-C 30 ) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C 30 ) cycloalkyl, substituted or unsubstituted (C1-C 30 ) alkoxy, substituted or unsubstituted tri(C1-C 30 ) alkylsilyl, substituted or unsubstituted di(C1-C 30 ) Alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 ) Alkyldi(C6~C 30 ) arylsilyl, or substituted or unsubstituted tri(C6-C 30 ) arylsilyl, or may be linked to adjacent substituents to form a ring, but at least one of R1 and R2 is a substituted or unsubstituted (C6-C 30 ) aryl or substituted or unsubstituted (3-30 membered) heteroaryl; a represents an integer of 1 to 3, b represents an integer of 1 to 4, and when a and b represent integers of 2 or greater, each R1 and each R2 may be the same as or different from each other. [ka]

[0013] In Equation 2, L1 to L3 each independently represent a single bond, a substituted or unsubstituted (C6 to C 30 ) arylene, or substituted or unsubstituted (3 to 30-membered) heteroarylene; Ar1 is a substituted or unsubstituted (C6 to C 30 ) aryl or substituted or unsubstituted (3 to 30 membered) heteroaryl; Ar2 and Ar3 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C 30 ) Alkyl, substituted or unsubstituted (C6-C 30 ) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C 30 ) cycloalkyl, substituted or unsubstituted (C1-C 30 ) alkoxy, substituted or unsubstituted tri(C1-C 30 ) alkylsilyl, substituted or unsubstituted di(C1-C 30 ) Alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 ) Alkyldi(C6~C 30 ) arylsilyl, substituted or unsubstituted tri(C6-C 30 ) arylsilyl, substituted or unsubstituted mono or di(C1-C 30 ) alkylamino, substituted or unsubstituted mono- or di-(C2-C 30 ) alkenylamino, substituted or unsubstituted (C1-C 30 ) Alkyl (C2-C 30 ) alkenylamino, substituted or unsubstituted mono- or di-(C6-C 30 ) arylamino, substituted or unsubstituted (C1-C 30 ) Alkyl (C6-C 30 )arylamino, substituted or unsubstituted mono- or di(3-30 membered)heteroarylamino, substituted or unsubstituted (C1-C 30 ) alkyl (3 to 30 membered) heteroaryl amino, substituted or unsubstituted (C2 to C 30 ) Alkenyl (C6-C 30 ) arylamino, substituted or unsubstituted (C2-C 30 ) alkenyl (3 to 30 membered) heteroarylamino, substituted or unsubstituted (C6 to C 30 ) aryl(3 to 30 membered)heteroarylamino, or (C3 to C 30) aliphatic ring and (C6~C 30 ) represents a substituted or unsubstituted condensed ring with an aromatic ring, or may be linked to adjacent substituents to form a ring. [ka]

[0014] In formulas 3-1-1 to 3-4-1, X2 represents O or S; L 21 and L 22 are each independently a single bond, a substituted or unsubstituted (C to C 30 ) arylene, or substituted or unsubstituted (3 to 30-membered) heteroarylene; L 23 represents unsubstituted or deuterium-substituted phenylene; Ar 22 is substituted or unsubstituted (C6-C 30 ) aryl, or substituted or unsubstituted (3 to 30 membered) heteroaryl; Ar 23 represents a phenyl-substituted naphthyl optionally further substituted with deuterium; R 23 ~R 30 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C 30 ) alkyl, substituted or unsubstituted (C3-C 30 ) cycloalkyl, substituted or unsubstituted (C6-C 30 ) aryl, substituted or unsubstituted (3 to 30 membered) heteroaryl, substituted or unsubstituted (C1 to C 30 ) alkoxy, substituted or unsubstituted tri(C1-C 30 ) alkylsilyl, substituted or unsubstituted di(C1-C 30 ) Alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 ) Alkyldi(C6~C 30 ) arylsilyl, substituted or unsubstituted tri(C6-C 30 ) arylsilyl, substituted or unsubstituted mono or di(C1-C30 ) alkylamino, substituted or unsubstituted mono- or di-(C2-C 30 ) alkenylamino, substituted or unsubstituted (C1-C 30 ) Alkyl (C2-C 30 ) alkenylamino, substituted or unsubstituted mono- or di-(C6-C 30 ) arylamino, substituted or unsubstituted (C1-C 30 ) Alkyl (C6-C 30 )arylamino, substituted or unsubstituted mono- or di(3-30 membered)heteroarylamino, substituted or unsubstituted (C1-C 30 ) alkyl (3 to 30 membered) heteroaryl amino, substituted or unsubstituted (C2 to C 30 ) Alkenyl (C6-C 30 ) arylamino, substituted or unsubstituted (C2-C 30 ) alkenyl (3 to 30 membered) heteroarylamino, substituted or unsubstituted (C6 to C 30 ) aryl(3 to 30 membered)heteroarylamino, or (C3 to C 30 ) aliphatic ring and (C6~C 30 ) represents a substituted or unsubstituted fused ring with an aromatic ring, and in each of formulas 3-1-1 to 3-4-1, R 23 ~R 26 At least one of the following is substituted or unsubstituted (C6 to C 30 ) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl.

[0015] Advantageous Effects of the Invention By including an organic electroluminescent compound and / or multiple host materials according to the present disclosure, an organic electroluminescent device having high luminous efficiency and / or long life characteristics can be provided. DETAILED DESCRIPTION OF THE INVENTION

[0016] The present disclosure will be described in detail below. However, the following description is intended to illustrate the present invention and is not intended to limit the scope of the present disclosure in any way.

[0017] The present disclosure relates to a plurality of host materials, including at least one first host material comprising a compound represented by Formula 1 and at least one second host material comprising a compound represented by Formula 2, and an organic electroluminescent device comprising the host materials. Additionally, the present disclosure relates to an organic electroluminescent material or an organic electroluminescent device comprising an organic electroluminescent compound represented by any of Formulas 3-1-1 to 3-4-1.

[0018] In this specification, the term "organic electroluminescent material" 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, a light-emitting auxiliary material, an electron blocking material, a light-emitting material (including a host and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material.

[0019] As used herein, the term "multiple host materials" refers to a host material containing a combination of at least two compounds that can be contained in any light-emitting layer constituting an organic electroluminescent device. This can refer to both the material before (e.g., before vapor deposition) it is contained in the organic electroluminescent device and the material after (e.g., after vapor deposition) it is contained in the organic electroluminescent device. In one embodiment, the multiple host materials of the present disclosure may be a combination of at least two host materials, and optionally, it may further contain a conventional material that is contained in an organic electroluminescent material. The at least two compounds contained in the multiple host materials may be contained together in one light-emitting layer by a method used in the art, or may be contained in separate light-emitting layers. For example, such at least two compounds may be mixed-deposited or co-deposited, or may be deposited separately.

[0020] In the present disclosure, the term "hole transport zone" refers to a region where holes travel between the first electrode and the light-emitting layer, and may include, for example, one or more of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, and an electron blocking layer. Each of the hole injection layer, the hole transport layer, the hole auxiliary layer, the light-emitting auxiliary layer, and the electron blocking layer may be a single layer, or may be two or more layers, or may be a plurality of layers in which three or more layers are stacked. In one embodiment, the hole transport zone may include a first hole transport layer and a second hole transport layer, and may further include a third hole transport layer. The second hole transport layer and the third hole transport layer may be one or more layers of a plurality of hole transport layers, which may include one or more of a hole auxiliary layer, a light-emitting auxiliary layer, and an electron blocking layer. In addition, in another embodiment, the hole transport zone may include a first hole transport layer and a second hole transport layer, where the first hole transport layer can be disposed between the first electrode and the light-emitting layer, and the second hole transport layer can be disposed between the first hole transport layer and the light-emitting layer, and the second hole transport layer can function as a hole transport layer, a light-emitting auxiliary layer, a hole auxiliary layer, and / or an electron blocking layer. In yet another embodiment, the hole transport zone may include a first hole transport layer, a second hole transport layer, and a third hole transport layer, where the first hole transport layer can be disposed between the first electrode and the light-emitting layer, the second hole transport layer can be disposed between the first hole transport layer and the light-emitting layer, and the third hole transport layer can be disposed between the second hole transport layer and the light-emitting layer, and the third hole transport layer can function as a hole transport layer, a light-emitting auxiliary layer, a hole auxiliary layer, and / or an electron blocking layer.

[0021] In this specification, "(C1 to C 30 The term "alkyl(ene)" refers to a straight or branched alkyl having 1 to 30 carbon atoms constituting the chain, where the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10. The alkyl may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, and the like.

[0022] In this specification, "(C3 to C 30 The term "cycloalkyl(ene)" refers to a mono- or poly-cyclic 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.

[0023] In this disclosure, "(C6-C 30The term "aryl(ene)" is intended to mean a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring skeletal carbon atoms, preferably 6 to 20, more preferably 6 to 15 ring skeletal carbon atoms. The aryl may be partially saturated or may contain a spiro structure. Specific examples of aryl include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthrenyl, benzophenanthrenyl, phenylphenanthrenyl, anthracenyl, benzanthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, benzochrysenyl, naphthacenyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, mesityl, cumenyl, spiro[fluorene-fluoren]yl, spiro[fluorene-benzofluoren]yl, azulenyl, and tetramethyl-dihydrophenanthrenyl. More specifically, aryl is o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, p-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-t-butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl- 4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, 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, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 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, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoran thenyl, benzofluoranthenyl, 11,11-dimethyl-1-benzo[a]fluorenyl, 11,11-dimethyl-2-benzo[a]fluorenyl, 11,11-dimethyl-3-benzo[a]fluorenyl, 11,11-dimethyl-4-benzo[a]fluorenyl, 11,11-dimethyl-5-benzo[a]fluorenyl, 11,11-dimethyl-6-benzo[a]fluorenyl, 11,11-dimethyl-7-benzo[a]fluorenyl, 11,11-dimethyl-8-benzo[a]fluorenyl, 11,11-dimethyl-9-benzo[a]fluorenyl, 11,11-dimethyl-10-benzo[a]fluorenyl, 11,11-dimethyl-1-benzo[b]fluorenyl, 11,11-dimethyl-2-benzo[b]fluorenyl, 11,11-dimethyl-3-benzo[b]fluorenyl, 11,11-dimethyl-4-benzo[b]fluorenyl, 11,11-dimethyl-5-benzo[b]fluorenyl, 11,11-dimethyl-6-benzo[b]fluorenyl, 11,11-dimethyl-7-benzo[b]fluorenyl, 11,11-dimethyl-8-benzo[b]fluorenyl, 11,11-dimethyl-9-benzo[b]fluorenyl benzo[b]fluorenyl, 11,11-dimethyl-10-benzo[b]fluorenyl, 11,11-dimethyl-1-benzo[c]fluorenyl, 11,11-dimethyl-2-benzo[c]fluorenyl, 11,11-dimethyl-3-benzo[c]fluorenyl, 11,11-dimethyl-4-benzo[c]fluorenyl, 11,11-dimethyl-5-benzo[c]fluorenyl, 11,11-dimethyl-6-benzo[c]fluorenyl, 11,11-dimethyl-7-benzo[c]fluorenyl, 11,11-dimethyl-8-benzo[c]fluorenyl, 11,11-dimethyl-9-benzo[c]fluorenyl, 11,11-dimethyl-10-benzo[c]fluorenyl, 11,11-diphenyl-1-benzo[a]fluorenyl, 11,11-diphenyl-2-benzo[a]fluorenyl, 11,11-diphenyl-3-benzo[a]fluorenyl, 11,11-diphenyl-4-benzo[a]fluorenyl, 11,11-diphenyl-5-benzo[a]fluorenyl, 11,11-diphenyl-6-benzo[a]fluorenyl, 11,11-diphenyl-7-benzo[a]fluorenyl, 11,11-diphenyl 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 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, etc.

[0024] In the present disclosure, the term "(3- to 30-membered) heteroaryl(ene)" refers to an aryl having 3 to 30 ring skeletal atoms including at least one heteroatom selected from the group consisting of B, N, O, S, Si, P, Se, and Ge. The number of ring skeletal atoms is preferably 3 to 30, more preferably 5 to 20. The number of heteroatoms in the heteroaryl is preferably 1 to 4. The heteroaryl or heteroarylene may be a monocyclic ring or a fused ring fused with at least one benzene ring, and may be partially saturated. Furthermore, the heteroaryl or heteroarylene in this specification may be formed by bonding at least one heteroaryl or aryl group to a heteroaryl group via a single bond, and may also include a spiro structure. Specific examples of 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; and benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, benzofuroquinolinyl, benzofuroquinazolinyl, benzofuronaphthyridinyl, benzofuropyrimidinyl, naphthofuropyrimidinyl, benzothienoquinolinyl, benzothienoquinazolinyl, and benzothienophenyl. nonaphthyridinyl, benzothienopyrimidinyl, naphthothienopyrimidinyl, pyrimidoindolyl, benzopyrimidindolyl, benzofuropyrazinyl, naphthofuropyrazinyl, benzothienopyrazinyl, naphthothienopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl,Examples of fused ring heteroaryls include benzodioxolyl, indolizinyl, acridinyl, silafluorenyl, germafluorenyl, benzotriazolyl, phenazinyl, imidazopyridinyl, chromenoquinazolinyl, thiochromenoquinazolinyl, dimethylbenzopyrimidinyl, indolocarbazolyl, and indenocarbazolyl. More specifically, heteroaryl is 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolizidinyl, 2-indolizidinyl, 3-indolizidinyl, 5-indolizidinyl, 6-indoliz ...6-indolizinyl, 6-indolizinyl, 6-indolizinyl, 6-indolizinyl, 6-indolizinyl, 6-indolizinyl, 6-indolizinyl, 6-indolizinyl, 6-indolizinyl, 6-indolizinyl, 6-indolizinyl, 6-indolizinyl, 6-indolizinyl, 6-indolizinyl, 6-indolizinyl, 6-indolizinyl, 6-indolizinyl, 6-indolizinyl, 6-indolizinyl, 6-indoliz -Indolizidinyl, 6-Indolizidinyl, 7-Indolizidinyl, 8-Indolizidinyl, 2-Imidazopyridinyl, 3-Imidazopyridinyl, 5-Imidazopyridinyl, 6-Imidazopyridinyl, 7-Imidazopyridinyl, 8-Imidazopyridinyl, 1-Indolyl, 2-Indolyl, 3-Indolyl, 4-Indolyl, 5-Indolyl, 6-Indolyl, 7-Indolyl, 1-Isoindolyl, 2-Isoindolyl, 3-Isoindolyl, 4-Isoindolyl benzofuranyl, 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 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 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-t-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-t-butyl-1-indolyl, 4-t-butyl-1-indolyl, 2-t-butyl-3-indolyl, 4-t-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-naphtho-[1,2-b]-benzofuranyl, 2-naphtho-[1,2-b]-benzofuranyl, 3-naphtho-[1,2-b]-benzofuranyl nyl, 4-naphtho-[1,2-b]-benzofuranyl, 5-naphtho-[1,2-b]-benzofuranyl, 6-naphtho-[1,2-b]-benzofuranyl, 7-naphtho-[1,2-b]-benzofuranyl, 8-naphtho-[1,2-b]-benzofuranyl, 9-naphtho-[1,2-b]-benzofuranyl, 10-naphtho-[1,2-b]-benzofuranyl, 1-naphtho-[2,3-b]-benzofuranyl, 2-naphtho-[2,3-b]-benzofuranyl, 3-naphtho-[2,3-b]-benzofuranyl, 4-naphtho-[2,3-b]-benzofuranyl,5-naphtho-[2,3-b]-benzofuranyl, 6-naphtho-[2,3-b]-benzofuranyl, 7-naphtho-[2,3-b]-benzofuranyl, 8-naphtho-[2,3-b]-benzofuranyl, 9-naphtho-[2,3-b]-benzofuranyl, 10-naphtho-[2,3-b]-benzofuranyl, 1-naphtho-[2,1-b]-benzofuranyl, 2-naphtho-[2,1-b]-benzofuranyl, 3-naphtho-[2,1-b]-benzofuranyl, 4-naphtho-[2,1-b]-benzofuranyl, 5-naphtho-[2,1-b]-benzofuranyl, 6-naphtho- [2,1-b]-benzofuranyl, 7-naphtho-[2,1-b]-benzofuranyl, 8-naphtho-[2,1-b]-benzofuranyl, 9-naphtho-[2,1-b]-benzofuranyl, 10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b]-benzothiophenyl, 2-naphtho-[1,2-b]-benzothiophenyl, 3-naphtho-[1,2-b]-benzothiophenyl, 4-naphtho-[1,2-b]-benzothiophenyl, 5-naphtho-[1,2-b]-benzothiophenyl, 6-naphtho-[1,2-b]-benzothiophenyl, 7 -naphtho-[1,2-b]-benzothiophenyl, 8-naphtho-[1,2-b]-benzothiophenyl, 9-naphtho-[1,2-b]-benzothiophenyl, 10-naphtho-[1,2-b]-benzothiophenyl, 1-naphtho-[2,3-b]-benzothiophenyl, 2-naphtho-[2,3-b]-benzothiophenyl, 3-naphtho-[2,3-b]-benzothiophenyl, 4-naphtho-[2,3-b]-benzothiophenyl, 5-naphtho-[2,3-b]-benzothiophenyl, 1-naphtho-[2,1-b]-benzothiophenyl, 2-naphtho-[2, 1-b]-benzothiophenyl, 3-naphtho-[2,1-b]-benzothiophenyl, 4-naphtho-[2,1-b]-benzothiophenyl, 5-naphtho-[2,1-b]-benzothiophenyl, 6-naphtho-[2,1-b]-benzothiophenyl, 7-naphtho-[2,1-b]-benzothiophenyl, 8-naphtho-[2,1-b]-benzothiophenyl, 9-naphtho-[2,1-b]-benzothiophenyl, 10-naphtho-[2,1-b]-benzothiophenyl, 2-benzofuro[3,2-d]pyrimidinyl, 6-benzofuro[3,2-d]pyrimidinyl,7-Benzofuro[3,2-d]pyrimidinyl, 8-benzofuro[3,2-d]pyrimidinyl, 9-benzofuro[3,2-d]pyrimidinyl, 2-benzothio[3,2-d]pyrimidinyl, 6-benzothio[3,2-d]pyrimidinyl, 7-benzothio[3,2-d]pyrimidinyl, 8-benzothio[3,2-d]pyrimidinyl, 9-benzothio[3,2-d]pyrimidinyl, 2-benzofuro[3,2-d]pyrazinyl, 6-benzofuro[3,2-d]pyrazinyl, 7-benzofuro[3,2-d]pyrazinyl, 8-benzofuro[3,2-d]pyrazinyl, 9-benzofuro[3,2-d] It may be pyrazinyl, 2-benzothio[3,2-d]pyrazinyl, 6-benzothio[3,2-d]pyrazinyl, 7-benzothio[3,2-d]pyrazinyl, 8-benzothio[3,2-d]pyrazinyl, 9-benzothio[3,2-d]pyrazinyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-germafluorenyl, 4-germafluorenyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, etc. Furthermore, "heteroaryl(ene)" can be classified into heteroaryl(ene)s having electronic properties and heteroaryl(ene)s having hole properties. Heteroaryl(ene)s with electron properties are substituents that are relatively electron-rich in the core, such as substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinolyl, etc. Heteroaryl(ene)s with hole properties are substituents that are relatively electron-deficient in the core, such as substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.

[0025] In this specification, "(C3 to C 30 ) aliphatic ring and (C6~C 30The term "fused ring with an aromatic ring" refers to a ring formed by condensing at least one aliphatic ring having 3 to 30 ring skeletal carbon atoms, preferably 3 to 25, more preferably 3 to 18 carbon atoms, with at least one aromatic ring having 6 to 30 ring skeletal carbon atoms, preferably 6 to 25, more preferably 6 to 18 carbon atoms. For example, the fused ring may be a fused ring of at least one benzene and at least one cyclohexane, or a fused ring of at least one naphthalene and at least one cyclopentane. In this specification, the term "(C3 to C 30 ) aliphatic ring and (C6~C 30 ) Carbon atoms in the fused ring with the aromatic ring may be replaced with at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S. "Halogen" in this disclosure includes F, Cl, Br, and I.

[0026] Furthermore, "ortho (o-)," "meta (m-)," and "para (p-)" are intended to indicate the substitution positions of all substituents. The ortho position refers to, for example, a compound having substituents adjacent to each other at the 1- and 2-positions of a benzene. The meta position refers to the substitution position next to the immediately adjacent substitution position, for example, a compound having substituents at the 1- and 3-positions of a benzene. The para position refers to the substitution position next to the meta position, for example, a compound having substituents at the 1- and 4-positions of a benzene.

[0027] As used herein, the term "ring formed by linking adjacent substituents" refers to a substituted or unsubstituted (3-50 membered) monocyclic or polycyclic aliphatic ring, aromatic ring, or combination thereof formed by linking or condensing two or more adjacent substituents. Preferably, this ring is a substituted or unsubstituted (5-40 membered) monocyclic or polycyclic aliphatic ring, aromatic ring, or combination thereof. Furthermore, the formed ring may contain at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably N, O, and S. According to one embodiment of the present disclosure, the number of ring skeletal atoms is 5 to 35. According to another embodiment of the present disclosure, the number of ring skeletal atoms is 5 to 30. In one embodiment, the fused ring may be, for example, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted benzofluorene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted benzene ring, or a substituted or unsubstituted carbazole ring.

[0028] Additionally, in the description of "substituted or unsubstituted" herein, the term "substituted" refers to a hydrogen atom in a functional group that has been replaced with another atom or another functional group (i.e., a substituent). Unless otherwise specified, a substituent may replace a hydrogen atom at a position that can be substituted, and when two or more hydrogen atoms in a functional group are each replaced with a substituent, the substituents may be the same or different from each other. The maximum number of substituents that can be substituted for a certain functional group can be the total number of valences that can be substituted for each atom that forms the functional group. Preferably, the substituted alkyl, substituted aryl(ene), substituted heteroaryl(ene), substituted cycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, and substituted triarylsilyl in the formulas of the present disclosure each independently represent deuterium; halogen; cyano; carboxyl; nitro; hydroxy; phosphine oxide; (C1-C 30 ) Alkyl, halo (C1-C 30 ) Alkyl, (C2-C 30 ) alkenyl, (C2-C 30 ) alkynyl, (C1-C 30 ) alkoxy, (C1-C 30 ) Alkylthio, (C3-C 30 ) cycloalkyl, (C3-C 30 ) cycloalkenyl, (3-7 membered) heterocycloalkyl, (C6-C 30 ) Aryloxy, (C6-C 30 ) arylthio, unsubstituted or (C6-C 30 ) aryl-substituted (5-30 membered) heteroaryl, unsubstituted or (5-30 membered) heteroaryl-substituted (C6-C 30 ) aryl, tri(C1-C 30 ) Alkylsilyl, Tri(C6-C 30 ) arylsilyl, di(C1-C 30 ) Alkyl (C6-C 30 ) arylsilyl, (C1-C 30 ) Alkyldi(C6~C 30 ) arylsilyl, amino, mono or di (C1-C 30) alkylamino, unsubstituted or (C1-C 30 ) alkyl-substituted mono- or di-(C6-C 30 ) arylamino, (C1-C 30 ) Alkyl (C6-C 30 ) arylamino, (C1-C 30 ) alkylcarbonyl, (C1-C 30 ) alkoxycarbonyl, (C6-C 30 ) arylcarbonyl, (C6-C 30 ) arylphosphinyl, di(C6-C 30 ) arylboronyl, di(C1-C 30 ) alkylboronyl, (C1-C 30 ) Alkyl (C6-C 30 ) arylboronyl, (C6-C 30 )ar(C1~C 30 ) alkyl, and (C1-C 30 ) Alkyl (C6-C 30For example, the substituent may be deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted benzonaphthalenyl, substituted or unsubstituted benzophenanthryl, substituted or unsubstituted chrysenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted dibenzonaphthocycloheptanyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzyl, or substituted or unsubstituted dibenzoyl. and the like, and the substituted amino may be substituted with one or more members selected from the group consisting of phenyl, biphenyl, naphthyl, pyridyl, dibenzofuranyl, and dibenzothiophenyl.

[0029] If a substituent is not shown in a chemical formula or compound structure, it may mean that all positions that can exist as a substituent are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be the isotope deuterium, in which case the deuterium content may be 0% to 100%. If a substituent is not shown in a chemical formula or compound structure, unless deuterium is explicitly excluded, hydrogen and deuterium can be used in combination in the compound. For example, when the deuterium content is 0%, the hydrogen content is 100%, and all substituents are hydrogen. Deuterium is an element with a deuteron consisting of one proton and one neutron as the atomic nucleus. It is one of the isotopes of hydrogen and can be represented by hydrogen-2, and its element symbol is D or 2 It can be H. Isotopes with the same atomic number (Z) but different mass numbers (A) can also be interpreted as elements with the same number of protons but different numbers of neutrons.

[0030] As used herein, "combinations thereof" means combining one or more members of the corresponding list to form a known or chemically stable configuration that one skilled in the art would contemplate from the corresponding list. For example, alkyl and deuterium can be combined to form a partially or fully deuterated alkyl group, halogen and alkyl can be combined to form a halogenated alkyl substituent, and halogen, alkyl and aryl can be combined to form a halogenated arylalkyl. For example, preferred combinations of substituents can contain up to 50 atoms excluding hydrogen and deuterium, or can contain up to 40 atoms excluding hydrogen and deuterium, or can contain up to 30 atoms excluding hydrogen and deuterium, or in many cases, preferred combinations of substituents can contain up to 20 atoms excluding hydrogen and deuterium.

[0031] In the formulae of the present disclosure, when multiple substituents are represented by the same symbol, each of these substituents represented by the same symbol may be the same or different from one another.

[0032] The host material according to one embodiment will be described in detail below.

[0033] According to one embodiment, the plurality of host materials includes a first host material comprising a compound represented by Formula 1 and a second host material comprising a compound represented by Formula 2, which may be included in at least one light-emitting layer of the organic electroluminescent device according to one embodiment.

[0034] The first host material, which is a host material according to one embodiment, can include a compound represented by Formula 1 below: [ka]

[0035] In Equation 1, X represents O, S, or Se; HAr represents a substituted or unsubstituted (3-30 membered) heteroaryl containing one or more nitrogen atoms; L is a single bond, a substituted or unsubstituted (C6 to C 30 ) arylene, or substituted or unsubstituted (3 to 30-membered) heteroarylene; R1 and R2 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C 30 ) Alkyl, substituted or unsubstituted (C6-C 30 ) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C 30 ) cycloalkyl, substituted or unsubstituted (C1-C 30 ) alkoxy, substituted or unsubstituted tri(C1-C 30 ) alkylsilyl, substituted or unsubstituted di(C1-C 30 ) Alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 ) Alkyldi(C6~C 30 ) arylsilyl, or substituted or unsubstituted tri(C6-C 30) arylsilyl, or may be linked to adjacent substituents to form a ring, but at least one of R1 and R2 is a substituted or unsubstituted (C6-C 30 ) aryl or substituted or unsubstituted (3-30 membered) heteroaryl; a represents an integer of 1 to 3, b represents an integer of 1 to 4, and when a and b represent integers of 2 or greater, each R1 and each R2 may be the same as or different from each other.

[0036] In one embodiment, X can be O or S.

[0037] In one embodiment, HAr may be a substituted or unsubstituted (3- to 30-membered) heteroaryl containing one or more nitrogen atoms, and preferably, HAr may be a substituted or unsubstituted (3- to 25-membered) heteroaryl containing one or more nitrogen atoms. For example, HAr may be a substituted or unsubstituted triazinyl, and the substituted triazinyl is a (C6 to C 30 (3- to 30-membered)aryl and (3- to 30-membered)heteroaryl, which may be further substituted with deuterium. For example, the substituted triazinyl may be substituted with one or more selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted chrysenyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzophenanthrofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzonaphthoselenophenyl, and substituted or unsubstituted triphenylsilyl, which may be further substituted with one or more selected from the group consisting of deuterium, phenyl, naphthyl, phenylnaphthyl, and naphthylphenyl.

[0038] In one embodiment, L is a single bond or a substituted or unsubstituted (C6-C 30 ) arylene, and preferably L is a single bond or a substituted or unsubstituted (C6 to C 25 For example, L may be a single bond, substituted or unsubstituted phenylene, or substituted or unsubstituted naphthylene.

[0039] In one embodiment, R1 and R2 are each independently hydrogen, substituted or unsubstituted (C6-C 30 )aryl, substituted or unsubstituted (3-30 membered)heteroaryl, or substituted or unsubstituted (C3-C 30 ) cycloalkyl, but at least one of R1 and R2 is substituted or unsubstituted (C6-C 30 Preferably, R1 and R2 are each independently hydrogen, deuterium, a substituted or unsubstituted (C1-C2) aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl. 25 ) Alkyl, substituted or unsubstituted (C6-C 25 )aryl, substituted or unsubstituted (3 to 25 membered)heteroaryl, or substituted or unsubstituted (C3 to C 25 ) cycloalkyl, but at least one of R1 and R2 is substituted or unsubstituted (C6-C 25provided that R1 and R2 may each independently be hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted benzophenanthrenyl, substituted or unsubstituted chrysenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzoxazolyl, or substituted or unsubstituted benzothiazolyl, which may be further substituted with one or more selected from the group consisting of deuterium, phenyl, and naphthyl.

[0040] In one embodiment, R1 is a substituted or unsubstituted (C6-C 30 ) represents aryl.

[0041] In one embodiment, a represents an integer of 1 to 3, b represents an integer of 1 to 4, and when a and b represent integers of 2 or greater, each R1 and each R2 may be the same as or different from each other.

[0042] The compound represented by formula 1 can be represented by any one of the following formulas 1-1 to 1-4. [ka]

[0043] In formulas 1-1 to 1-4, R 1a ~R 1d and R 2a ~R 2d are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C 30 ) Alkyl, substituted or unsubstituted (C6-C 30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C 30 ) cycloalkyl, substituted or unsubstituted (C1-C 30 ) alkoxy, substituted or unsubstituted tri(C1-C 30 ) alkylsilyl, substituted or unsubstituted di(C1-C 30 ) Alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 ) Alkyldi(C6~C 30 ) arylsilyl, or substituted or unsubstituted tri(C6-C 30 ) arylsilyl, or may be linked to adjacent substituents to form a ring, but in each of formulas 1-1 to 1-4, R 1a ~R 1d and R 2a ~R 2d At least one of the following is substituted or unsubstituted (C6 to C 30 ) aryl or substituted or unsubstituted (3-30 membered) heteroaryl; X, L, and HAr are as defined in Formula 1.

[0044] According to one embodiment, the first host material can be more specifically exemplified by, but not limited to, the following compounds: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0045] Compounds of formula 1 according to the present disclosure can be prepared as shown in, but not limited to, the following reaction schemes 1-4. [Reaction Scheme 1] [ka]

[0046] In Reaction Scheme 1, X, R1, R2, Ar 22 , R 21, L, HAr, a, and b are as defined in Formula 1, and R is hydrogen or (C1 to C 30 ) alkyl, and Hal means halogen.

[0047] Another host material, the second host material, according to one embodiment can include a compound represented by Formula 2: [ka]

[0048] In Equation 2, L1 to L3 each independently represent a single bond, a substituted or unsubstituted (C6 to C 30 ) arylene, or substituted or unsubstituted (3 to 30-membered) heteroarylene; Ar1 is a substituted or unsubstituted (C6 to C 30 ) aryl, or substituted or unsubstituted (3 to 30 membered) heteroaryl; Ar2 and Ar3 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C 30 ) Alkyl, substituted or unsubstituted (C6-C 30 ) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C 30 ) cycloalkyl, substituted or unsubstituted (C1-C 30 ) alkoxy, substituted or unsubstituted tri(C1-C 30 ) alkylsilyl, substituted or unsubstituted di(C1-C 30 ) Alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 ) Alkyldi(C6~C 30 ) arylsilyl, substituted or unsubstituted tri(C6-C 30 ) arylsilyl, substituted or unsubstituted mono or di(C1-C 30 ) alkylamino, substituted or unsubstituted mono- or di-(C2-C 30 ) alkenylamino, substituted or unsubstituted (C1-C 30 ) Alkyl (C2-C 30) alkenylamino, substituted or unsubstituted mono- or di-(C6-C 30 ) arylamino, substituted or unsubstituted (C1-C 30 ) Alkyl (C6-C 30 )arylamino, substituted or unsubstituted mono- or di(3-30 membered)heteroarylamino, substituted or unsubstituted (C1-C 30 ) alkyl (3 to 30 membered) heteroaryl amino, substituted or unsubstituted (C2 to C 30 ) Alkenyl (C6-C 30 ) arylamino, substituted or unsubstituted (C2-C 30 ) alkenyl (3 to 30 membered) heteroarylamino, substituted or unsubstituted (C6 to C 30 ) aryl(3 to 30 membered)heteroarylamino, or (C3 to C 30 ) aliphatic ring and (C6~C 30 ) represents a substituted or unsubstituted condensed ring with an aromatic ring, or may be linked to adjacent substituents to form a ring.

[0049] In one embodiment, L1 to L3 each independently represent a single bond, a substituted or unsubstituted (C6 to C 30 ) arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene, and preferably, L1 to L3 are each independently a single bond, a substituted or unsubstituted (C6 to C 25 ) arylene, or substituted or unsubstituted (3- to 25-membered) heteroarylene. For example, L1 to L3 are each independently a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthrene, substituted or unsubstituted pyridinylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, or substituted or unsubstituted carbazolylene, which may be substituted with one or more selected from the group consisting of deuterium, phenyl, and naphthyl.

[0050] In one embodiment, Ar1 is a substituted or unsubstituted (C6-C 30) aryl, or substituted or unsubstituted (3 to 30 membered) heteroaryl, preferably Ar1 is substituted or unsubstituted (C6 to C 25 )aryl, or substituted or unsubstituted (3- to 25-membered)heteroaryl. For example, Ar1 may be substituted or unsubstituted phenanthrenyl, substituted or unsubstituted chrysenyl, substituted or unsubstituted benzophenanthrenyl, substituted or unsubstituted phenanthrooxazolyl, substituted or unsubstituted phenanthrothiazolyl, substituted or unsubstituted benzonaphthofuranyl, or substituted or unsubstituted benzonaphthothiophenyl.

[0051] In one embodiment, Ar2 and Ar3 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C6-C 30 ) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C 30 ) cycloalkyl, tri(C6-C 30 ) arylsilyl, substituted or unsubstituted mono or di(C6-C 30 )arylamino, substituted or unsubstituted mono- or di(3-30 membered)heteroarylamino, substituted or unsubstituted (C6-C 30 ) aryl(3 to 30 membered)heteroarylamino, or (C3 to C 30 ) aliphatic ring and (C6~C 30For example, Ar2 and Ar3 may each independently be a substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted chrysenyl, substituted or unsubstituted benzonaphthalenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted dibenzonaphthocycloheptanyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzyl, The substituted amino group may be benzonaphthofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzofuropyridinyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted benzonaphthoselenophenyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted triphenylsilyl, or unsubstituted amino which is substituted or substituted with one or two substituents, and these may be substituted with one or more selected from the group consisting of deuterium, phenyl, naphthyl, and biphenyl, and the substituted amino groups may each independently be substituted with one or more selected from the group consisting of phenyl, biphenyl, naphthyl, pyridinyl, dibenzofuranyl, and dibenzothiophenyl.

[0052] According to one embodiment, the compound represented by formula 2 can be represented by any one of the following formulas 2-1 to 2-3. [ka]

[0053] In formulas 2-1 to 2-3, T1 and T2 each independently represent -N=, -NR7-, -O-, or -S-, provided that one of T1 and T2 is -N= and the other of T1 and T2 is -NR7-, -O-, or -S-; T3 represents -O- or -S-; Ring A represents a substituted or unsubstituted phenanthrene; Ring B represents substituted or unsubstituted benzene or substituted or unsubstituted naphthalene; R3 is a substituted or unsubstituted (C6 to C 30 ) aryl, or substituted or unsubstituted (3 to 30 membered) heteroaryl; R4~R 12 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C 30 ) Alkyl, substituted or unsubstituted (C6-C 30 ) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C 30 ) cycloalkyl, substituted or unsubstituted (C1-C 30 ) alkoxy, substituted or unsubstituted tri(C1-C 30 ) alkylsilyl, substituted or unsubstituted di(C1-C 30 ) Alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 ) Alkyldi(C6~C 30 ) arylsilyl, substituted or unsubstituted tri(C6-C 30 ) Arylsilyl, (C3-C 30 ) aliphatic ring and (C6~C 30 ) substituted or unsubstituted fused rings with aromatic rings, substituted or unsubstituted mono- or di-(C1-C 30 ) alkylamino, substituted or unsubstituted mono- or di-(C2-C 30 ) alkenylamino, substituted or unsubstituted (C1-C 30 ) Alkyl (C2-C 30 ) alkenylamino, substituted or unsubstituted (C1-C 30 ) Alkyl (C6-C 30 ) arylamino, substituted or unsubstituted (C1-C 30) alkyl (3 to 30 membered) heteroaryl amino, substituted or unsubstituted (C2 to C 30 ) Alkenyl (C6-C 30 ) arylamino, substituted or unsubstituted (C2-C 30 ) alkenyl (3 to 30 membered) heteroarylamino, substituted or unsubstituted mono or di (C6 to C 30 )arylamino, substituted or unsubstituted mono- or di(3-30 membered)heteroarylamino, or substituted or unsubstituted (C6-C 30 ) aryl(3 to 30-membered)heteroarylamino, or may be linked to adjacent substituents to form a ring; c, d, and h each independently represent an integer of 1 or 2, e, f, and i each independently represent an integer of 1 to 4, g is an integer of 1 to 7, and j is an integer of 1 to 6; When c to j are integers of 2 or more, each of R4 to R6 and each of R8 to R 12 may be identical to or different from each other; L1 to L3, Ar2, and Ar3 are as defined in formula 2.

[0054] According to one embodiment, when L3 in formula 2-1 is substituted or unsubstituted phenylene, formula 2-1 can be represented by the following formula 2-1-a: [ka]

[0055] In formula 2-1-a, Ar4 to Ar8 are each as defined for Ar3 in Formula 2, provided that Ar6 is not a substituted or unsubstituted heteroaryl; T1, T2, R3 to R6, and c to e are each as defined in Formula 2-1. L1, L2, and Ar2 are each as defined in Formula 2.

[0056] According to one embodiment, the compound represented by formula 2-2 can be represented by any one of formulas 2-2a to 2-2c below. [ka]

[0057] In formulas 2-2a to 2-2c, T3, R8, R9, L1 to L3, Ar2, Ar3, f, and g are as defined in formula 2-2.

[0058] According to one embodiment, the compound represented by formula 2-3 can be represented by any one of formulas 2-3a to 2-3d below. [ka]

[0059] In formulas 2-3a to 2-3d, j' is an integer from 1 to 4; When j' is an integer equal to or greater than 2, R 12 may be the same as or different from one another; R 10 ~R 12 , L1 to L3, Ar2, Ar3, and h to j are as defined in formula 2-3.

[0060] According to one embodiment, the second host material can be more specifically exemplified by, but not limited to, the following compounds: [ka] [ka] [ka] [ka] [ka]

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

[0061] The compound represented by formula 2 according to the present disclosure can be prepared by a synthesis method known to those skilled in the art, and in particular, synthesis methods disclosed in numerous patent documents can be used. For example, the compound represented by formula 2-1 according to the present disclosure can be prepared with reference to, but not limited to, Patent Document 1 (published March 2, 2017) and Patent Document 4 (published September 5, 2018). For example, the compound represented by formula 2-2 can be synthesized as shown in the following reaction scheme 2, but is not limited thereto. For example, the compound represented by formula 2-3 can be prepared by a synthesis method known to those skilled in the art. [Reaction Scheme 2] [ka]

[0062] In Reaction Scheme 2, the definitions of each substituent are as defined in Formula 2-2. As described above, exemplary synthetic examples of compounds represented by Formula 2-2 according to the present disclosure are described. These examples are based on Suzuki cross-coupling reactions, Wittig reactions, Buchwald-Hartwig cross-coupling reactions, Miyaura borylation reactions, N-arylation reactions, H-mont-mediated etherification 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, and the like. It will be understood by those skilled in the art that the above reactions will proceed even when other substituents defined in Formula 2-2 other than the substituents described in the specific synthetic examples are bonded.

[0063] The plurality of host materials according to one embodiment may further include a third host material comprising a compound represented by Formula 3: [ka]

[0064] In Equation 3, X 21 ~X 23 are each independently N or CR20 represents, but X 21 ~X 23 with the proviso that at least one of represents N; R 20 is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30 ) Alkyl, substituted or unsubstituted (C6-C 30 ) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C 30 ) cycloalkyl, substituted or unsubstituted (C1-C 30 ) alkoxy, substituted or unsubstituted tri(C1-C 30 ) alkylsilyl, substituted or unsubstituted di(C1-C 30 ) Alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 ) Alkyldi(C6~C 30 ) arylsilyl, substituted or unsubstituted tri(C6-C 30 ) arylsilyl, or (C3-C 30 ) aliphatic ring and (C6~C 30 ) represents a substituted or unsubstituted fused ring with an aromatic ring; L 21 ~L 23 are each independently a single bond, a substituted or unsubstituted (C6 to C 30 ) arylene, or substituted or unsubstituted (3 to 30-membered) heteroarylene; Ar 21 ~Ar 23 are each independently substituted or unsubstituted (C1 to C 30 ) alkyl, substituted or unsubstituted (C3-C 30 ) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, (C3-C 30 ) aliphatic ring and (C6~C 30 ) Substituted or unsubstituted fused ring with aromatic ring, substituted or unsubstituted (C6-C 30 )aryl, substituted or unsubstituted (3 to 30 membered)heteroaryl, substituted or unsubstituted tri(C1 to C 30 ) alkylsilyl, substituted or unsubstituted di(C1-C 30) Alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 ) Alkyldi(C6~C 30 ) arylsilyl, or substituted or unsubstituted tri(C6-C 30 ) arylsilyl.

[0065] In one embodiment, L 21 is a single bond or a substituted or unsubstituted (C6 to C 30 ) arylene, preferably L 21 is a single bond or a substituted or unsubstituted (C6 to C 25 ) arylene. For example, L 21 may be a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted phenylnaphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, or substituted or unsubstituted naphthylphenylene.

[0066] In one embodiment, L 22 and L 23 are each independently a single bond or a substituted or unsubstituted (C6 to C 30 ) arylene, preferably L 22 and L 23 are each independently a single bond or a substituted or unsubstituted (C6 to C 25 ) arylene. For example, L 22 and L 23 may each independently be a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, or substituted or unsubstituted phenanthrylene.

[0067] In one embodiment, Ar 21 may be a substituted or unsubstituted (3- to 30-membered) heteroaryl, preferably Ar 21 may be a substituted or unsubstituted (3-25 membered) heteroaryl. For example, Ar 21 may be substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl.

[0068] In one embodiment, Ar 22 and Ar 23 are each independently substituted or unsubstituted (C6 to C 30 ) aryl, or substituted or unsubstituted (5-30 membered) heteroaryl, preferably Ar 22 and Ar 23 are each independently substituted or unsubstituted (C6 to C 25 ) aryl, or substituted or unsubstituted (5-25 membered) heteroaryl. For example, Ar 22 and Ar 23 may each independently be substituted or unsubstituted phenyl, unsubstituted or deuterium-substituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted naphthylphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracenyl, substituted or unsubstituted chrysenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted carbazolyl, unsubstituted or phenyl-substituted carbazolyl, substituted or unsubstituted dibenzofuranyl, unsubstituted or deuterium-substituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted benzonaphthofuranyl.

[0069] According to one embodiment, the compound represented by formula 3 can be represented by any one of the following formulas 3-1 to 3-4. [ka]

[0070] In formulas 3-1 to 3-4, X2 represents O or S; R 21a ~R 21d and R22a ~R 22d are each independently hydrogen, deuterium, substituted or unsubstituted (C6 to C 30 ) aryl, or substituted or unsubstituted (3 to 30 membered) heteroaryl; L 21 ~L 23 , Ar 22 , and Ar 23 is as defined in Equation 3.

[0071] In one embodiment, R 21a ~R 21d and R 22a ~R 22d are each independently hydrogen, deuterium, or a substituted or unsubstituted (C6 to C 30 ) aryl, preferably each independently hydrogen, deuterium, or a substituted or unsubstituted (C6-C 25 ) aryl. For example, R 21a ~R 21d and R 22a ~R 22d may each independently be hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted naphthylphenyl, or substituted or unsubstituted phenanthrenyl.

[0072] The compound represented by formula 3 according to the present disclosure can be prepared by a synthesis method known to those skilled in the art, and in particular, the synthesis methods disclosed in numerous patent documents can be used. For example, the compound represented by formula 3 can be synthesized by referring to, but not limited to, the methods disclosed in (Patent Document 5) (published October 14, 2021) and (Patent Document 6) (published January 18, 2021).

[0073] According to one embodiment, the third host material can be more specifically exemplified by, but not limited to, the following compounds: [ka]

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

[0074] An organic electroluminescent compound according to one embodiment will be described below.

[0075] The organic electroluminescent compound according to one embodiment can be represented by any of the following formulas 3-1-1 to 3-4-1. [ka]

[0076] In formulas 3-1-1 to 3-4-1, X2 represents O or S; L 21 and L 22 are each independently a single bond, a substituted or unsubstituted (C6 to C 30 ) arylene, or substituted or unsubstituted (3 to 30-membered) heteroarylene; L 23 represents unsubstituted or deuterium-substituted phenylene; Ar 22 is substituted or unsubstituted (C6 30 ) aryl, or substituted or unsubstituted (3 to 30 membered) heteroaryl; Ar 23 represents a phenyl-substituted naphthyl optionally further substituted with deuterium; R 23 ~R 30 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C 30 ) alkyl, substituted or unsubstituted (C3-C 30 ) cycloalkyl, substituted or unsubstituted (C6-C 30) aryl, substituted or unsubstituted (3 to 30 membered) heteroaryl, substituted or unsubstituted (C1 to C 30 ) alkoxy, substituted or unsubstituted tri(C1-C 30 ) alkylsilyl, substituted or unsubstituted di(C1-C 30 ) Alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 ) Alkyldi(C6~C 30 ) arylsilyl, substituted or unsubstituted tri(C6-C 30 ) arylsilyl, substituted or unsubstituted mono or di(C1-C 30 ) alkylamino, substituted or unsubstituted mono- or di-(C2-C 30 ) alkenylamino, substituted or unsubstituted (C1-C 30 ) Alkyl (C2-C 30 ) alkenylamino, substituted or unsubstituted mono- or di-(C6-C 30 ) arylamino, substituted or unsubstituted (C1-C 30 ) Alkyl (C6-C 30 )arylamino, substituted or unsubstituted mono- or di(3-30 membered)heteroarylamino, substituted or unsubstituted (C1-C 30 ) alkyl (3 to 30 membered) heteroaryl amino, substituted or unsubstituted (C2 to C 30 ) Alkenyl (C6-C 30 ) arylamino, substituted or unsubstituted (C2-C 30 ) alkenyl (3 to 30 membered) heteroarylamino, substituted or unsubstituted (C6 to C 30 ) aryl(3 to 30 membered)heteroarylamino, or (C3 to C 30 ) aliphatic ring and (C6~C 30 ) represents a substituted or unsubstituted fused ring with an aromatic ring, and in each of formulas 3-1-1 to 3-4-1, R 23 ~R 30 At least one of the following is substituted or unsubstituted (C6 to C 30 ) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl.

[0077] In one embodiment, X can be O.

[0078] In one embodiment, L 21 and L 22 may each independently be a single bond.

[0079] In one embodiment, Ar 22 is substituted or unsubstituted (C6-C 25 ) aryl, preferably unsubstituted or deuterium-substituted (C6-C 18 ) aryl. For example, Ar 22 can be unsubstituted or deuterium-substituted phenyl.

[0080] In one embodiment, R 23 ~R 30 are each independently hydrogen, deuterium, or a substituted or unsubstituted (C6 to C 25 ) aryl, preferably hydrogen, deuterium, or unsubstituted or deuterium-substituted (C6-C 18 ) aryl. For example, R 23 ~R 30 may each independently be hydrogen, deuterium, or unsubstituted or deuterium-substituted phenyl.

[0081] In one embodiment, in each of formulas 3-1-1 to 3-4-1, R 23 ~R 30 At least one of the following is substituted or unsubstituted (C6 to C 30 ) aryl, preferably unsubstituted or deuterium-substituted (C6-C 25 ) aryl. For example, in each of formulas 3-1-1 to 3-4-1, R 23 ~R 30 At least one of may be unsubstituted or deuterium-substituted phenyl.

[0082] In one embodiment, Ar 23 can be expressed by the following formula A. [ka]

[0083] In formula A, any one of A1 to A8 is L 23 is bonded to L 23 A1 to A8 that are not bonded to each independently represent hydrogen, deuterium, or substituted or unsubstituted phenyl, provided that at least one of A1 to A8 is substituted or unsubstituted phenyl. The phenyl may be substituted with deuterium.

[0084] The compounds represented by any one of formulas 3-1-1 to 3-4-1 according to the present disclosure can be prepared as shown in Reaction Scheme 3 below, but are not limited thereto. [Reaction Scheme 3] [ka]

[0085] In Reaction Scheme 3, X2, L 21 ~L 23 , Ar 22 , and Ar 23 is as defined in Equations 3-1-1 to 3-4-1, and R 21 is expressed in equations 3-1-1 to 3-4-1. 27 ~R 30 is as defined for R 22 is 3-1-1~3-4-1 R 23 ~R 26 wherein Hal means halogen, n is an integer of 1 to 3, and m is an integer of 1 to 4; and when each of n and m is an integer of 2 or greater, each R 21 and each R 22 may be the same or different from each other.

[0086] According to one embodiment, the compounds represented by formulas 3-1-1 to 3-4-1 can be more specifically exemplified by, but not limited to, the following compounds: [ka] [ka] [ka] [ka]

[0087] Hereinafter, an organic electroluminescent device in which the above-mentioned multiple host materials are applied will be described.

[0088] An organic electroluminescent device according to one embodiment comprises a first electrode, a second electrode, and at least one organic layer sandwiched between the first and second electrodes. According to one embodiment, the first host material comprising the compound represented by Formula 1 and the second host material comprising the compound represented by Formula 2 can be contained in the same organic layer or in different organic layers.

[0089] The organic layer includes at least one light-emitting layer, and the at least one light-emitting layer may include multiple host materials including at least one first host material including a compound represented by Formula 1 and at least one second host material including a compound represented by Formula 2. According to one embodiment, the light-emitting layer may include at least one compound selected from compounds H1-1 to H1-437, which is the first host material represented by Formula 1, and at least one compound selected from compounds H2-1 to H2-391, H3-1 to H3-299, and H4-1 to H4-171, which is the second host material represented by Formula 2.

[0090] One of the first electrode and the second electrode may be an anode, and the other may be a cathode. In this case, the first electrode and the second electrode may be formed as a transparent conductive material, a semi-transparent conductive material, or a reflective conductive material, respectively. In addition to the light-emitting layer, the organic layer may further include at least one layer selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron injection layer, an intermediate layer, a hole blocking layer, an electron blocking layer, and an electron buffer layer.

[0091] The organic layer may further contain an amine-based compound and / or an azine-based compound in addition to the light-emitting material according to the present disclosure. Specifically, the hole injection layer, hole transport layer, hole auxiliary layer, light-emitting layer, light-emitting auxiliary layer, or electron-blocking layer may contain an amine-based compound, such as an arylamine-based compound or a styrylarylamine-based compound, as a hole injection material, hole transport material, hole auxiliary material, light-emitting material, light-emitting auxiliary material, or electron-blocking material. The electron transport layer, electron injection layer, electron buffer layer, or hole-blocking layer may contain an azine-based compound as an electron transport material, electron injection material, electron buffer material, or hole-blocking material. The organic layer may further contain at least one metal selected from the group consisting of metals from Group 1 of the periodic table, metals from Group 2, transition metals from Period 4, transition metals from Period 5, lanthanides, and organometallic d-transition elements, or at least one complex compound containing such a metal.

[0092] The host materials according to one embodiment can be used as emissive materials for white organic light-emitting devices. Various structures of white organic light-emitting devices have been proposed, such as parallel side-by-side arrangement, stacked arrangement, or color conversion material (CCM) arrangement, depending on the arrangement of R (red), G (green), YG (yellow-green), or B (blue) light-emitting units. Furthermore, the host materials according to one embodiment can also be applied to organic electroluminescent devices containing quantum dots (QDs).

[0093] A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof can be used between the anode and the light-emitting layer. The hole injection layer may be a multilayer to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or electron blocking layer. In this case, two types of compounds may be used simultaneously in each of the multiple layers. The hole injection layer may also be doped with a p-dopant. An electron blocking layer may also be disposed between the hole transport layer (or hole injection layer) and the light-emitting layer. By preventing electrons from overflowing from the light-emitting layer, excitons can be trapped within the light-emitting layer, preventing light leakage. The hole transport layer or electron blocking layer may be a multilayer, in which case multiple compounds can be used in each layer.

[0094] An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof can be used between the light-emitting layer and the cathode. The electron buffer layer can be multi-layered to control electron injection and improve the interface characteristics between the light-emitting layer and the electron injection layer, and in this case, two types of compounds can be used simultaneously in each of the multiple layers. The hole blocking layer or the electron transport layer can also be multi-layered, and in this case, multiple compounds can be used in each layer. The electron injection layer can also be doped with an n-dopant.

[0095] The light-emitting auxiliary layer can be disposed between the anode and the light-emitting layer or between the cathode and the light-emitting layer. When the light-emitting auxiliary layer is disposed between the anode and the light-emitting layer, it can be used to promote hole injection and / or hole transport or to prevent electron overflow. When the light-emitting auxiliary layer is disposed between the cathode and the light-emitting layer, it can be used to promote electron injection and / or electron transport or to prevent hole overflow. In addition, a hole-auxiliary layer may be disposed between the hole-transport layer (or hole-injection layer) and the light-emitting layer and can be effective in promoting or blocking the hole transport rate (or hole injection rate), thereby allowing the charge balance to be controlled. When an organic electroluminescent device includes two or more hole-transport layers, the additional hole-transport layer can be used as a hole-auxiliary layer or an electron-blocking layer. The light-emitting auxiliary layer, hole-auxiliary layer, or electron-blocking layer can have the effect of improving the efficiency and / or life of the organic electroluminescent device.

[0096] In the organic electroluminescent device of the present disclosure, at least one layer (hereinafter referred to as "surface layer") selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer may be disposed on one or both inner surfaces of a pair of electrodes. Specifically, a silicon and aluminum chalcogenide (including oxide) layer is preferably disposed on the anode side of the electroluminescent medium layer, and a metal halide or metal oxide layer is preferably disposed on the cathode side of the electroluminescent medium layer. The surface layer can provide operational stability for the organic electroluminescent device. Preferably, the chalcogenide is SiO X (1≦X≦2), AlO X (1≦X≦1.5), SiON, SiAlON, etc., metal halides include LiF, MgF2, CaF2, rare earth metal fluorides, etc., and metal oxides include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0097] An organic electroluminescent device according to an embodiment of the present disclosure may be an organic electroluminescent device having a tandem structure. In a tandem organic electroluminescent device according to an embodiment, a single light-emitting unit (light-emitting unit) may be formed by connecting two or more units via a charge-generating layer. The organic electroluminescent device may include a plurality of two or more light-emitting units, for example, a plurality of three or more light-emitting units. The light-emitting units have a first electrode and a second electrode facing each other on a substrate, and an emitting layer stacked between the first electrode and the second electrode and emitting light in a specific wavelength range. Each light-emitting unit may include a hole-transporting zone, an emitting layer, and an electron-transporting zone. The hole-transporting zone may include a hole-injection layer and a hole-transporting layer, and the electron-transporting zone may include an electron-transporting layer and an electron-injection layer. According to an embodiment, three or more light-emitting layers may be included in the light-emitting unit. The multiple light-emitting units may emit the same color or different colors. In addition, one light-emitting unit can include one or more light-emitting layers, and the multiple light-emitting layers can be light-emitting layers of the same color or different colors. This can include one or more charge-generating layers disposed between each light-emitting unit. A charge-generating layer refers to a layer that generates holes and electrons when a voltage is applied. When three or more light-emitting units are present, a charge-generating layer can be disposed between each light-emitting unit. In this case, the multiple charge-generating layers can be the same or different. By disposing a charge-generating layer between the light-emitting units, the current efficiency in each light-emitting unit can be improved and charge can be smoothly distributed. Specifically, a charge-generating layer disposed between two adjacent stacks can be useful for driving a tandem organic electroluminescent device using only an anode-cathode pair without a separate internal electrode disposed between the stacks.

[0098] An organic electroluminescent device according to one embodiment may have two or more organic layers, and may further include one or more charge generating layers, and the charge generating layers may be disposed between each organic layer, and when two or more organic layers are included, each charge generating layer may be the same or different. Because the charge generating layer is disposed between the organic layers, the organic electroluminescent device can be driven by only a pair of anode and cathode, without disposing another independent internal electrode between the organic layers.

[0099] The charge generation layer may be composed of an N-type charge generation layer and a P-type charge generation layer. The N-type charge generation layer may be doped with an alkali metal, an alkaline earth metal, or a compound of an alkali metal and an alkaline earth metal. The alkali metal may include one selected from the group consisting of Li, Na, K, Rb, Cs, Fr, Yb, and combinations thereof. The alkaline earth metal may include one selected from the group consisting of Be, Mg, Ca, Sr, Ba, Ra, and combinations thereof.

[0100] In addition, in the organic electroluminescent device of the present disclosure, a mixed region of an electron transport compound and a reductive dopant or a mixed region of a hole transport compound and an oxidative dopant can be disposed on the surface of at least one of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, thereby making it easier to inject and transport electrons from the mixed region into the electroluminescent medium. Furthermore, the hole transport compound is oxidized to a cation, thereby making it easier to inject and transport holes from the mixed region into the electroluminescent medium. Preferably, the oxidative dopant includes various Lewis acids and acceptor compounds, and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. Furthermore, an organic electroluminescent device having two or more light-emitting layers and emitting white light can be fabricated using a reductive dopant layer as a charge generation layer.

[0101] The light-emitting layer of the organic electroluminescent device according to one embodiment can be a single light-emitting layer, or can be a multi-layer structure of two or more layers stacked together.The light-emitting layer can further comprise one or more dopants, and the doping concentration of the dopant compound relative to the host compound of the light-emitting layer can be less than 20% by weight, preferably less than 10% by weight.

[0102] The dopant contained in the organic electroluminescent device of the present disclosure can be at least one phosphorescent or fluorescent dopant, preferably phosphorescent dopant.The phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particularly limited, but can be preferably a metal complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), more preferably an ortho-metal complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and even more preferably an ortho-metal iridium complex compound.

[0103] The dopant contained in the organic electroluminescent device of the present disclosure may be, but is not limited to, a compound represented by the following formula 101: [ka]

[0104] In Equation 101, L is the following structure 1 to 3: [ka] is one selected from R 100 ~R 103 are each independently hydrogen, deuterium, halogen, unsubstituted or substituted with deuterium and / or halogen (C1-C 30 ) alkyl, substituted or unsubstituted (C3-C 30 ) cycloalkyl, substituted or unsubstituted (C6-C 30)aryl, cyano, substituted or unsubstituted (3 to 30 membered)heteroaryl, or substituted or unsubstituted (C1 to C 30 ) alkoxy, or may be linked to adjacent substituents to form a ring, for example, with pyridine to form a ring such as substituted or unsubstituted quinoline, substituted or unsubstituted benzofuropyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuroquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indenoquinoline; R 104 ~R 107 are each independently hydrogen, deuterium, halogen, unsubstituted or substituted with deuterium and / or halogen (C1-C 30 ) alkyl, substituted or unsubstituted (C3-C 30 ) cycloalkyl, substituted or unsubstituted (C6-C 30 )aryl, substituted or unsubstituted (3 to 30 membered)heteroaryl, cyano, or substituted or unsubstituted (1 to C 30 ) alkoxy, or may be linked to adjacent substituents to form a substituted or unsubstituted ring, for example, with benzene to form a substituted or unsubstituted ring, such as substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuropyridine, or substituted or unsubstituted benzothienopyridine; R 201 ~R 220 are each independently hydrogen, deuterium, halogen, unsubstituted or substituted with deuterium and / or halogen (C1-C 30 ) alkyl, substituted or unsubstituted (C3-C 30 ) cycloalkyl, or substituted or unsubstituted (C6-C 30 ) aryl, or may be joined with adjacent substituents to form a substituted or unsubstituted ring; s represents an integer of 1 to 3.

[0105] In particular, specific examples of dopant compounds include, but are not limited to, the following: [ka] [ka] [ka] [ka] [ka] [ka]

[0106] To form each layer of the organic electroluminescent device of the present disclosure, a dry film-forming method such as vacuum evaporation, sputtering, plasma, ion plating, etc., or a wet film-forming method such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating, etc., can be used. When using a wet film-forming method, a thin film can be formed by dissolving or dispersing the material forming each layer in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent can be any solvent that can dissolve or disperse the material forming each layer and has no problem in film-forming ability.

[0107] According to one embodiment, when the first host material and the second host material are present in the same layer or different layers of an organic electroluminescent device, the two host materials can be deposited separately. For example, the second host material can be deposited after the first host material is deposited.

[0108] According to one embodiment, when each layer of an organic electroluminescent device is formed, a film can be formed by the above-mentioned method, and the film can be formed by a co-evaporation process, a mixed deposition process, and / or a process that combines the co-evaporation process and the mixed deposition process. For example, co-evaporation can be a method of depositing two or more isomeric materials by placing the isomeric materials in individual evaporation sources, such as crucible sources, and simultaneously applying current to two cells to evaporate the materials. Furthermore, for example, mixed deposition can be a method of mixing two or more isomeric materials in one evaporation source, such as a crucible source, before deposition, and then evaporating the materials by applying current to one cell. Furthermore, for example, a process using co-evaporation and mixed deposition can be a process of mixing a first host material and a second host material in one evaporation source, such as a crucible source, placing another material in another evaporation source, such as a crucible source, and then simultaneously applying current to two cells to evaporate and deposit each material. When a film is formed using a process that uses mixed deposition and / or co-deposition and mixed deposition together, the number of evaporation sources used can be reduced.

[0109] According to one embodiment, the present disclosure can provide a compound obtained by depositing an organic layer in a manufacturing process of an organic electroluminescent device, and then recovering and purifying the organic layer material attached to the deposition apparatus. The recovered compound can be subjected to a purification process and / or a recrystallization process, and the purity of the purified and / or recrystallized compound obtained therefrom can be 99.9% or more.

[0110] According to one embodiment, the present disclosure provides a method for recovering a plurality of host materials, the method comprising: vapor-depositing a plurality of host materials comprising at least one first host material comprising a compound represented by Formula 1 and at least one second host material comprising a compound represented by Formula 2; recovering the plurality of host materials deposited on the vapor deposition apparatus; and purifying and / or recrystallizing the recovered plurality of host materials to obtain a plurality of host materials having a purity of 99.9% or greater.

[0111] According to one embodiment, the present disclosure can provide a display device, such as a display device for a smartphone, tablet, laptop, PC, TV, or vehicle, or a lighting device, such as an outdoor or indoor lighting device, using multiple host materials including a compound represented by Formula 1 and a compound represented by Formula 2.

[0112] Hereinafter, methods for preparing compounds according to the present disclosure and their physical properties will be described with reference to methods for synthesizing representative compounds or intermediate compounds of the present disclosure. [Example]

[0113] [Example 1] Preparation of Compound H1-72 [ka]

[0114] 1. Synthesis of Compound 1-2 Compound 1-1 (15 g, 47 mmol), 2-(3-chlorodibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (17 g, 51 mmol), tetrakis(triphenylphosphine) (2.7 g, 2.3 mmol), and calcium carbonate (13 g, 94 mmol) were placed in a flask. To this was added 141 mL of toluene, 47 mL of ethanol, and 47 mL of distilled water. The mixture was then stirred under reflux at 120 °C for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, the organic layer was separated, and the remaining water was removed with magnesium sulfate. The solvent was then distilled under reduced pressure. The residue was then purified by column chromatography to give compound 1-2 (14 g, yield: 61%).

[0115] 2. Synthesis of Compound H1-72 Compound 1-2 (7 g, 14.4 mmol), compound 1-3 (4.36 g, 15.9 mmol), tris(dibenzylideneacetone)dipalladium(0) (1.32 g, 1.4 mmol), dicyclohexyl[2',6'-dimethoxy-[1,1'-biphenyl]-2-yl]phosphane ("SPhos") (1.2 g, 2.8 mmol), potassium triphosphate (7.7 g, 3.6 mmol), and 100 mL of xylene were dissolved in a flask and stirred under reflux at 160 °C for 3 hours. After the reaction was complete, the mixture was cooled to room temperature, the organic layer was separated, and residual water was removed with magnesium sulfate. The residue was then purified by column chromatography to give compound H1-72 (2.3 g, 23% yield).

[0116] [Table 1]

[0117] [Example 2] Preparation of Compound H1-85 [ka]

[0118] 1. Synthesis of Compound 2-2 Compound 2-1 (7.65 g, 23.28 mmol), 2-(4-chlorodibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (9.99 g, 27.94 mmol), tetrakis(triphenylphosphine)palladium(0) (1.35 g, 1.16 mmol), and potassium carbonate (9.65 g, 69.84 mmol) were placed in a flask, dissolved in 116 mL of toluene, 26 mL of ethanol, and 26 mL of distilled water, and then stirred under reflux at 130 °C for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, and the formed solid was filtered. Compound 2-2 (10 g, yield: 82%) was obtained by separation using column chromatography.

[0119] 2. Synthesis of Compound H1-85 Compound 2-2 (10 g, 19.09 mmol), phenylboronic acid (3.49 g, 28.63 mmol), tris(dibenzylideneacetone)dipalladium(0) (1.75 g, 1.91 mmol), SPhos (1.57 g, 3.82 mmol), cesium carbonate (18.66 g, 57.26 mmol), and 95 mL of xylene were dissolved in a flask and stirred under reflux at 160 °C for 1 h. After the reaction was complete, the mixture was cooled to room temperature, the organic layer was extracted, and residual water was removed with magnesium sulfate. The residue was then purified by column chromatography to give compound H1-85 (2.3 g, 21.3% yield).

[0120] [Table 2]

[0121] [Example 3] Preparation of compound H1-97 [ka] Compound 3-1 (5 g, 9.543 mmol), compound 3-2 (1.8 g, 14.31 mmol), Pd(OAc) (0.21 g, 0.954 mmol), SPhos (0.78 g, 1.908 mmol), cesium carbonate (9.3 g, 28.63 mmol), o-xylene (60 mL), 1,4-dioxane (15 mL), and distilled water (15 mL) were dissolved in a flask and stirred under reflux at 160 °C for 3 h. After the reaction was completed, the mixture was cooled to room temperature, methanol was added, and the solid was filtered, dissolved in chlorobenzene, and filtered through silica to give compound H1-97 (2.4 g, 44% yield).

[0122] [Table 3]

[0123] [Example 4] Preparation of Compound H1-86 [ka] Compound 4-1 (5.8 g, 10.74 mmol), compound 4-2 (2 g, 16.11 mmol), Pd(OAc) (0.24 g, 1.074 mmol), SPhos (0.88 g, 2.148 mmol), cesium carbonate (10.5 g, 32.22 mmol), o-xylene (60 mL), 1,4-dioxane (15 mL), and distilled water (15 mL) were dissolved in a flask and stirred at 160 °C for 3 h. After the reaction was complete, the mixture was cooled to room temperature, methanol was added, and the solid was filtered, dissolved in chlorobenzene, and filtered through silica to give compound H1-86 (1.9 g, 30% yield).

[0124] [Table 4]

[0125] [Example 5] Preparation of compound H1-191 [ka] Compound 5-1 (3.8 g, 7.2 mmol), 4,4,5,5-tetramethyl-2-(7-phenylnaphthalen-2-yl)1,3,2-dioxaborolane (3.6 g, 11 mmol), Pd2(dba)3 (412 mg, 0.65 mmol), SPhos (0.53 g, 1.29 mmol), and NaOtBu (2.1 g, 22.5 mmol) were dissolved in 36 mL of o-xylene and stirred at reflux for 40 min at 160 °C. After the reaction was complete, the mixture was cooled to room temperature and filtered through Celite to obtain a solid. The solid was then separated using column chromatography to obtain compound H1-191 (2.5 g, yield: 50.2%).

[0126] [Table 5]

[0127] [Example 6] Preparation of compound H1-201 [ka] Compound 6-1 (5 g, 11.52 mmol), compound 6-2 (2.9 g, 11.52 mmol), Pd(OAc) (0.25 g, 1.152 mmol), SPhos (0.94 g, 2.305 mmol), cesium carbonate (11.2 g, 34.57 mmol), 80 mL of o-xylene, 20 mL of 1,4-dioxane, and 20 mL of distilled water were dissolved in a flask and stirred under reflux at 160 °C for 1 h. After the reaction was completed, the mixture was cooled to room temperature, methanol was added, and the solid was filtered, dissolved in o-xylene, and filtered through silica to give compound H1-201 (2.5 g, 36% yield).

[0128] [Table 6]

[0129] [Example 7] Preparation of compound H1-202 [ka] Compound 7-1 (9.4 g, 21.80 mmol), compound 7-2 (7.2 g, 21.80 mmol), Pd(OAc) (0.5 g, 2.180 mmol), SPhos (1.8 g, 4.360 mmol), cesium carbonate (21.3 g, 65.41 mmol), 140 mL of o-xylene, 35 mL of 1,4-dioxane, and 35 mL of distilled water were dissolved in a flask and stirred under reflux at 160 °C for 1 h. After the reaction was complete, the mixture was cooled to room temperature, methanol was added, and the solid was filtered, dissolved in o-xylene, and filtered through silica to give compound H1-202 (3.3 g, 25% yield).

[0130] [Table 7]

[0131] [Example 8] Preparation of compound H1-43 [ka] Compound 8-1 (8.3 g, 14.45 mmol), compound 8-2 (4.6 g, 36.14 mmol), Pd(OAc) (0.32 g, 1.445 mmol), SPhos (1.2 g, 2.891 mmol), cesium carbonate (14.1 g, 43.37 mmol), 80 mL of o-xylene, 20 mL of 1,4-dioxane, and 20 mL of distilled water were dissolved in a flask and stirred under reflux at 160 °C for 3 h. After the reaction was completed, the mixture was cooled to room temperature, methanol was added, and the solid was filtered, dissolved in chlorobenzene, and filtered through silica to give compound H1-43 (2.5 g, 28% yield).

[0132] [Table 8]

[0133] [Example 9] Preparation of compound H1-194 [ka] Compound 9-1 (5.2 g, 9.737 mmol), compound 9-2 (3.7 g, 29.21 mmol), Pd(OAc) (0.2 g, 0.973 mmol), SPhos (0.8 g, 1.947 mmol), cesium carbonate (9.5 g, 29.21 mmol), 60 mL of o-xylene, 15 mL of 1,4-dioxane, and 15 mL of distilled water were dissolved in a flask and stirred under reflux at 150 °C for 24 h. After the reaction was completed, the mixture was cooled to room temperature, methanol was added, and the solid was filtered, dissolved in o-xylene, and filtered through silica to give compound H1-194 (3.5 g, 62% yield).

[0134] [Table 9]

[0135] [Example 10] Preparation of compound H1-225 [ka] Compound 10-1 (5.1 g, 16.1 mmol), compound 10-2 (7.5 g, 17.7 mmol), tetrakis(triphenylphosphine)palladium (1.0 g, 0.8 mmol), potassium carbonate (4.4 g, 32.1 mmol), 80 mL of toluene, 20 mL of ethanol, and 20 mL of distilled water were added to a flask and stirred under reflux at 120 °C for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, methanol was added, and the solid was filtered. The resulting solid was then purified using column chromatography to give compound H1-225 (6.6 g, yield: 66%).

[0136] [Table 10]

[0137] [Example 11] Preparation of compound H1-73 [ka] Compound 11-1 (15 g, 28.63 mmol), compound 11-2 (7.4 g, 42.94 mmol), palladium(II) acetate (0.64 g, 2.86 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (2.4 g, 5.73 mmol), cesium carbonate (27.98 g, 85.88 mmol), o-xylene (140 mL), and 1,4-dioxane (36 mL) were placed in a flask, and 36 mL of distilled water was added. The mixture was then refluxed at 160 °C for 3 h. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. The residue was then purified using column chromatography to give compound H1-73 (4.8 g, yield: 27%).

[0138] [Table 11]

[0139] [Example 12] Preparation of compound H1-77 [ka] Compound 12-1 (10 g, 23.79 mmol), compound 12-2 (8.5 g, 23.79 mmol), tetrakis(triphenylphosphine)palladium (0.8 g, 0.71 mmol), potassium carbonate (8.2 g, 59.48 mmol), 120 mL of toluene, 30 mL of ethanol, and 30 mL of distilled water were added to a flask and stirred under reflux at 120 °C for 2 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. The residue was then purified using column chromatography to give compound H1-77 (1.8 g, yield: 12%).

[0140] [Table 12]

[0141] [Example 13] Preparation of compound H1-226 [ka] Compound 13-1 (5.4 g, 10.00 mmol), compound 13-2 (2.2 g, 15.00 mmol), Pd(OAc)2 (0.22 g, 1.000 mmol), SPhos (0.82 g, 2.000 mmol), cesium carbonate (9.7 g, 30.00 mmol), 60 mL of o-xylene, 15 mL of 1,4-dioxane, and 15 mL of distilled water were dissolved in a flask and stirred under reflux at 160 °C for 4 h. After the reaction was completed, the reaction mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. The residue was then purified using column chromatography to give compound H1-226 (4.5 g, yield: 73%).

[0142] [Table 13]

[0143] [Example 14] Preparation of compound H1-230 [ka] Compound 14-1 (15.7 g, 37.35 mmol), compound 14-2 (11 g, 29.88 mmol), Pd(pph3)4 (2.1 g, 1.867 mmol), K2CO3 (15.4 g, 112.0 mmol), 55 mL of EtOH, 55 mL of distilled water, and 220 mL of toluene were dissolved in a flask and stirred under reflux at 130 °C for 2 h. After the reaction was completed, the mixture was cooled to room temperature, methanol was added, and the solid was filtered, dissolved in chlorobenzene, and then filtered through silica to give compound H1-230 (4 g, 17% yield).

[0144] [Table 14]

[0145] [Example 15] Preparation of compound H1-233 [ka] Compound 15-1 (5 g, 11.52 mmol), compound 15-2 (4.5 g, 14.98 mmol), Pd(OAc) (0.25 g, 1.152 mmol), SPhos (0.94 g, 2.305 mmol), cesium carbonate (11.2 g, 34.57 mmol), 80 mL of o-xylene, 20 mL of 1,4-dioxane, and 20 mL of distilled water were dissolved in a flask and stirred under reflux at 160 °C for 2 h. After the reaction was completed, the mixture was cooled to room temperature, methanol was added, and the solid was filtered, dissolved in o-xylene, and filtered through silica to give compound H1-233 (2.5 g, 37% yield).

[0146] [Table 15]

[0147] [Example 16] Preparation of compound H1-237 [ka]

[0148] 1. Synthesis of Compound 16-2 Compound 16-1 (15 g, 53.28 mmol), bis(pinacolato)diboron (20.02 g, 79.92 mmol), PdCl2(PPh3)2 (3.73 g, 5.3 mmol), and potassium acetate (13.07 g, 133.2 mmol) were added to a flask containing 266 mL of 1,4-dioxane, which was then stirred under reflux at 150 °C for 4 h. After completion of the reaction, the mixture was cooled to room temperature and filtered through Celite. After vacuum distillation, the residue was separated by column chromatography to give compound 16-2 (8.3 g, 47.4% yield).

[0149] 2. Synthesis of Compound 16-4 Compound 16-2 (6.8 g, 20.6 mmol), compound 16-3 (8.5 g, 23.7 mmol), Pd(PPh3)4 (1.2 g, 1.03 mmol), and potassium carbonate (7.1 g, 51.7 mmol) were added to a flask containing 90 mL of toluene, 23 mL of ethanol, and 23 mL of distilled water. The mixture was then stirred under reflux at 130 °C for 3.5 h. After the reaction was completed, the mixture was cooled to room temperature, and the solid was filtered off with methanol. The solid was then dissolved in chloroform and separated by column chromatography to give compound 16-4 (9.1 g, 83.9% yield).

[0150] 3. Synthesis of Compound H1-237 Compound 16-4 (3.8 g, 7.2 mmol), compound 16-5 (1.7 g, 8.7 mmol), Pd2(dba)3 (0.3 g, 0.36 mmol), Xantphos (0.3 g, 0.7 mmol), and K3PO4 (4 g, 18.1 mmol) were added to a flask containing 40 mL of xylene, which was then stirred under reflux at 160 °C for 3.5 h. After the reaction was complete, the mixture was cooled to room temperature, and the solid was filtered off with methanol. The solid was then dissolved in chloroform and separated by column chromatography to give compound H1-237 (3.0 g, yield: 65.2%).

[0151] [Table 16]

[0152] [Example 17] Preparation of compound H1-239 [ka]

[0153] 1. Synthesis of Compound 17-2 Compound 17-1 (15 g, 53.28 mmol), bis(pinacolato)diboron (20.02 g, 79.92 mmol), PdCl2(PPh3)2 (3.73 g, 5.3 mmol), and potassium acetate (13.07 g, 133.2 mmol) were added to a flask containing 266 mL of 1,4-dioxane, which was then stirred under reflux at 150 °C for 4 h. After completion of the reaction, the mixture was cooled to room temperature and filtered through Celite. After vacuum distillation, the residue was separated by column chromatography to give compound 17-2 (8.3 g, 47.4% yield).

[0154] 2. Synthesis of Compound 17-4 To a flask containing compound 17-2 (6.8 g, 20.6 mmol), compound 17-3 (8.5 g, 23.7 mmol), Pd(PPh3)4 (1.2 g, 1.03 mmol), and potassium carbonate (7.1 g, 51.7 mmol), 90 mL of toluene, 23 mL of ethanol, and 23 mL of distilled water were added, and the mixture was stirred under reflux at 130 °C for 3.5 h. After the reaction was completed, the mixture was cooled to room temperature and the solid was filtered with methanol. The solid was then dissolved in chloroform and separated by column chromatography to obtain compound 17-4 (9.1 g, yield: 83.9%).

[0155] 3. Synthesis of Compound H1-239 Compound 17-4 (4 g, 7.6 mmol), compound 17-5 (1.02 g, 8.3 mmol), Pd2(dba)3 (0.3 g, 0.38 mmol), SPhos (0.3 g, 0.76 mmol), and K3PO4 (4.1 g, 19.0 mmol) were added to a flask containing 40 mL of xylene and stirred under reflux at 160 °C for 3 h. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the organic layer was extracted with ethyl acetate. The solvent was then removed by distillation under reduced pressure, and the solid was filtered and dried. It was then dissolved in chloroform and separated by column chromatography to obtain compound H1-239 (2.3 g, yield: 53.4%).

[0156] [Table 17]

[0157] [Example 18] Preparation of compound H1-198 [ka] Compound 18-1 (7.5 g, 15.49 mmol), compound 18-2 (3.5 g, 20.14 mmol), Pd(OAc) (0.34 g, 1.549 mmol), SPhos (1.27 g, 3.099 mmol), cesium carbonate (15.1 g, 46.49 mmol), 80 mL of o-xylene, 20 mL of 1,4-dioxane, and 20 mL of distilled water were dissolved in a flask and stirred under reflux at 160 °C for 2 h. After the reaction was completed, the mixture was cooled to room temperature, methanol was added, and the solid was filtered, dissolved in o-xylene, and filtered through silica to give compound H1-198 (4.2 g, 47% yield).

[0158] [Table 18]

[0159] [Example 19] Preparation of compound H1-69 [ka]

[0160] 1. Synthesis of Compound 19-1 2-Bromo-4-chlorodibenzofuran (20.0 g, 71.05 mmol), bis(pinacolato)diboron (21.6 g, 85.26 mmol), PdCl(pph) (5.0 g, 7.09 mmol), and KOAc (21.0 g, 213.2 mmol) were dissolved in 360 mL of 1,4-dioxane in a flask, which was then stirred under reflux at 150 °C for 4 hours. After the reaction was complete, the mixture was cooled to room temperature, and the layers (EA / HO) were separated and filtered through Celite and then silica to obtain a solid. The solid was filtered to give compound 19-1 (19.8 g, 85% yield).

[0161] 2. Synthesis of Compound 19-3 Compound 19-1 (9.4 g, 28.6 mmol), compound 19-2 (7.6 g, 23.84 mmol), Pd(pph3)4 (0.83 g, 0.72 mmol), and potassium carbonate (8.2 g, 59.6 mmol) were added to a flask containing 120 mL of toluene, 30 mL of EtOH, and 30 mL of distilled water. The mixture was then stirred at 130 °C under reflux for 4 h. After the reaction was complete, the mixture was cooled to room temperature, and HO was added to the solid reaction product. The mixture was then stirred for 30 min, filtered, and purified by column chromatography to give compound 19-3 (10.4 g, 72% yield).

[0162] 3. Synthesis of Compound H1-69 Compound 19-3 (10.4 g, 21.5 mmol), compound 19-4 (5.5 g, 32.25 mmol), Pd(OAc) (0.97 g, 4.3 mmol), SPhos (3.5 g, 8.6 mmol), and cesium carbonate (28.0 g, 86.0 mmol) were dissolved in 215 mL of o-xylene, 27 mL of 1,4-dioxane, and 27 mL of distilled water in a flask, and the mixture was stirred under reflux at 160 °C for 4 h. After the reaction was complete, the mixture was cooled to room temperature, and the layers (EA / HO) were separated and filtered through Celite and then silica to obtain a solid. The solid was then filtered to give compound H1-69 (5.0 g, yield: 40.0%).

[0163] [Table 19]

[0164] [Example 20] Preparation of compound H1-58 [ka] Compound 20-1 (5.4 g, 10.31 mmol), compound 20-2 (3.0 g, 15.46 mmol), Pd(OAc) (0.23 g, 1.03 mmol), SPhos (0.85 g, 2.06 mmol), and cesium carbonate (10.1 g, 30.93 mmol) were dissolved in 51 mL of o-xylene, 13 mL of 1,4-dioxane, and 13 mL of distilled water in a flask and then stirred under reflux at 160 °C for 4 h. After the reaction was complete, the mixture was cooled to room temperature, and the layers (EA / HO) were separated and filtered through Celite and then silica to obtain a solid. The solid was then filtered to obtain compound H1-58 (2.0 g, yield: 30.0%).

[0165] [Table 20]

[0166] [Example 21] Preparation of compound H1-240 [ka]

[0167] 1. Synthesis of Compound 21-1 6-Chloro-2-phenylbenzoxazole (10.0 g, 43.54 mmol), bis(pinacolato)diboron (14.37 g, 56.61 mmol), Pd(dba) (2.0 g, 2.18 mmol), SPhos (1.8 g, 4.35 mmol), and KOAc (12.8 g, 130.62 mmol) were dissolved in 220 mL of 1,4-dioxane in a flask and stirred under reflux at 150 °C for 3 h. After the reaction was complete, the mixture was cooled to room temperature, and the layers (EA / HO) were separated and filtered through Celite and then silica to obtain a solid. The solid was then filtered to give compound 21-1 (17.2 g, 16.0% yield).

[0168] 2. Synthesis of Compound 21-2 Compound 21-1 (17.2 g, 53.28 mmol), 2-bromo-7-chlorodibenzofuran (18 g, 63.93 mmol), Pd(pph3)4 (1.85 g, 1.6 mmol), and potassium carbonate (18.4 g, 133.2 mmol) were dissolved in 266 mL of toluene, 66 mL of EtOH, and 66 mL of distilled water in a flask, and then the mixture was stirred under reflux at 130 °C for 4 h. After the reaction was completed, the mixture was cooled to room temperature, and HO was added to the solid reaction product. The mixture was stirred for 30 min, filtered, and then separated by column chromatography to give compound 21-2 (11.8 g, yield: 56.0%).

[0169] 3. Synthesis of Compound 21-3 In a flask, compound 21-2 (11.8 g, 29.81 mmol), bis(pinacolato)diboron (9.8 g, 38.75 mmol), Pd(dba) (1.36 g, 1.49 mmol), SPhos (1.2 g, 2.98 mmol), and KOAc (8.7 g, 89.43 mmol) were dissolved in 150 mL of 1,4-dioxane and then stirred under reflux at 150 °C for 3 h. After the reaction was complete, the mixture was cooled to room temperature, and the layers (EA / HO) were separated and filtered through Celite and then silica to obtain a solid. The solid was then filtered to give compound 21-3 (9.0 g, yield: 61.9%).

[0170] 4. Synthesis of Compound H1-240 Compound 21-3 (9.0 g, 18.47 mmol), compound 21-4 (5.9 g, 22.16 mmol), Pd(pph3)4 (0.6 g, 0.554 mmol), and potassium carbonate (6.4 g, 46.18 mmol) were dissolved in 100 mL of toluene, 25 mL of EtOH, and 25 mL of distilled water in a flask and then stirred under reflux for 4 h. After the reaction was complete, the mixture was cooled to room temperature, and HO was added to the solid reaction product. The mixture was then stirred at reflux for 30 min at 130 °C. After the reaction was complete, the mixture was cooled to room temperature, filtered, and then separated by column chromatography to obtain compound H1-240 (1.7 g, yield: 16.0%).

[0171] [Table 21]

[0172] [Example 22] Preparation of compound H1-262 [ka] Compound 22-1 (14 g, 23.3 mmol), compound 22-2 (3.5 g, 27.96 mmol), Pd2(dba)3 (1 g, 1.165 mmol), SPhos (765 mg, 1.86 mmol), and 120 mL of xylene were dissolved in a flask and stirred under reflux at 160 °C for 1 h. After the reaction was completed, the mixture was cooled to room temperature and washed with distilled water. The organic layer was extracted with ethyl acetate, dried over magnesium sulfate, and the solvent was removed. The residue was then purified by column chromatography to give compound H1-262 (3 g, yield: 20%).

[0173] [Table 22]

[0174] [Example 23] Preparation of compound H1-63 [ka] Compound 23-1 (6.43 g, 12.2 mmol), [1,1'-biphenyl]-4-ylboronic acid (3.65 g, 18.4 mmol), Pd2(dba)3 (1.13 g, 1.2 mmol), SPhos (1.01 g, 2.4 mmol), and cesium carbonate (12 g, 36.8 mmol) were added to a flask containing 61 mL of xylene, 16 mL of 1,4-dioxane, and 16 mL of distilled water. The mixture was then stirred at 170 °C under reflux for 2 h. After the reaction was complete, the mixture was cooled to room temperature, and the resulting solid was filtered, washed with methanol, and dried. The solid was then purified by column chromatography to give compound H1-63 (2.23 g, 28.2% yield).

[0175] [Table 23]

[0176] [Example 24] Preparation of compound H1-341 [ka] Compound 24-1 (8 g, 17 mmol), compound 24-2 (6.9 g, 18.7 mmol), Pd(PPh3)4 (982 mg, 0.85 mmol), and K2CO3 (3.5 g, 22.5 mmol) were dissolved in 85 mL of toluene, 42.5 mL of EtOH, and 42.5 mL of distilled water in a flask, and the mixture was stirred under reflux at 130 °C for 1.5 h. After the reaction was completed, the mixture was cooled to room temperature, and HO was added to the solid reaction product. The mixture was stirred for 30 min, filtered, and then recrystallized to give compound H1-341 (3.7 g, 32% yield).

[0177] [Table 24]

[0178] Hereinafter, methods for fabricating organic electroluminescent devices containing multiple host materials according to the present disclosure and the device characteristics thereof will be described.

[0179] [Device Examples 1-13] Fabrication of OLEDs Co-deposited with a First Host Compound and a Second Host Compound According to the Present Disclosure An OLED according to the present disclosure was fabricated. First, a transparent indium tin oxide (ITO) thin film (10 Ω / sq) (Geomatec Co., Ltd., Japan) on a glass substrate for the OLED was subjected to ultrasonic cleaning in acetone and isopropyl alcohol, then stored in isopropyl alcohol, and then used. The ITO substrate was then mounted on a substrate holder in a vacuum evaporation system. Compound HI-1 was then placed in one cell of the vacuum evaporation system, and compound HT-1 was placed in another cell. 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 compounds HI-1 and HT-1 to form a first hole injection layer with a thickness of 10 nm. Compound HT-1 was then deposited on the first hole injection layer to form a first hole transport layer with a thickness of 80 nm. Next, compound HT-2 was introduced into another cell of the vacuum evaporation apparatus, and evaporated by passing a current through the cell, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer.

[0180] After forming the hole injection layer and hole transport layer, an emitting layer was formed thereon as follows: the first host compound and the second host compound listed in Table 1 below were introduced into two cells of a vacuum evaporation apparatus as hosts, respectively, and compound D-39 was introduced into another cell as a dopant. The two host materials were evaporated in a 1:1 ratio, while the dopant material was simultaneously evaporated in a different ratio. The dopant was deposited at a doping amount of 3 wt % based on the total amount of the host and dopant, forming an emitting layer with a thickness of 40 nm on the second hole transport layer. Next, compounds ET-1 and EI-1 were evaporated in a weight ratio of 50:50 as electron transport materials to form an electron transport layer with a thickness of 35 nm on the emitting layer. Compound EI-1 was evaporated 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 evaporated on the electron injection layer using a separate vacuum evaporation apparatus. Thus, an OLED was fabricated. All materials used to fabricate the OLED were 10 -6 It was purified by vacuum sublimation at torr.

[0181] [Comparative Examples 1-3] Fabrication of OLEDs containing conventional compounds as hosts OLEDs were fabricated in the same manner as in Device Example 1, except that the compounds in Table 1 below were used as the first host material in the light-emitting layer, respectively.

[0182] The driving voltage, current efficiency, emission color at a luminance of 1,000 nits, and the time required for the luminance to decrease from 100% to 95% at a luminance of 10,000 nits (lifetime: T 95 The results are shown in Table 1 below.

[0183] [Table 25]

[0184] From Table 1 above, it can be seen that an organic electroluminescent device comprising a combination of specific compounds according to the present disclosure as a host material has, for example, higher luminous efficiency and / or longer lifetime than an organic electroluminescent device using a conventional host material.

[0185] Device Examples 14-31: Fabrication of OLEDs Containing Multiple Host Materials According to the Present Disclosure An OLED was fabricated in the same manner as in Device Example 1, except that compound HT-3 was used for the first hole injection layer, compound HT-4 was used to form a 55 nm thick second hole transport layer, compound HT-5 was deposited thereon to form a 5 nm thick third hole transport layer, the thickness of the electron transport layer was reduced to 30 nm, the first host, second host, and third host listed in Table 2 below were deposited as host materials for the light-emitting layer in a ratio of 2.5:5:2.5, compound Ir-D was used as a dopant, compound BF-1 was deposited between the light-emitting layer and the electron transport layer to form a 5 nm thick electron buffer layer, and compound ET-2 was used for the electron transport layer.

[0186] The driving voltage, current efficiency, emission color at a luminance of 1,000 nits, and the time it took for the luminance to decrease from 100% to 95% at a luminance of 15,000 nits (lifetime: T 95 The results are shown in Table 2 below.

[0187] [Table 26]

[0188] The compounds used in the device examples and comparative examples are specifically shown in Table 3 below.

[0189] [Table 27]

[0190] [Table 28]

[0191] [Table 29]

Claims

1. Formula 1 below: 【Chemical 1】 (In formula 1, X represents O, S, or Se; HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl containing one or more nitrogen atoms; L is a single bond, a substituted or unsubstituted (C ６ ~C ３０ ) arylene, or substituted or unsubstituted (3 to 30 membered) heteroarylene; R １ and R ２ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C １ ~C ３０ ) alkyl, substituted or unsubstituted (C ６ ~C ３０ ) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C ３ ~C ３０ ) cycloalkyl, substituted or unsubstituted (C １ ~C ３０ ) alkoxy, substituted or unsubstituted tri(C １ ~C ３０ ) alkylsilyl, substituted or unsubstituted di(C １ ~C ３０ ) alkyl(C ６ ~C ３０ ) arylsilyl, substituted or unsubstituted (C １ ~C ３０ ) alkyldi(C ６ ~C ３０ ) arylsilyl, or substituted or unsubstituted tri(C ６ ~C ３０ ) arylsilyl, or may be linked to adjacent substituents to form a ring, but R １ and R ２ At least one of the following is substituted or unsubstituted (C ６ ~C ３０ ) aryl or substituted or unsubstituted (3-30 membered) heteroaryl; a represents an integer of 1 to 3, b represents an integer of 1 to 4, and when a and b represent an integer of 2 or more, R １ and R ２ may be the same or different from each other) a first host material comprising a compound represented by the formula: Formula 2 below: 【Chemistry 2】 (In Equation 2, L １ ~L ３ are each independently a single bond, a substituted or unsubstituted group (C ６ ~C ３０ ) arylene, or substituted or unsubstituted (3 to 30 membered) heteroarylene; Ar １ is substituted or unsubstituted (C ６ ~C ３０ ) aryl or substituted or unsubstituted (3 to 30 membered) heteroaryl; Ar ２ and Ar ３ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C １ ~C ３０ ) alkyl, substituted or unsubstituted (C ６ ~C ３０ ) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C ３ ~C ３０ ) cycloalkyl, substituted or unsubstituted (C １ ~C ３０ ) alkoxy, substituted or unsubstituted tri(C １ ~C ３０ ) alkylsilyl, substituted or unsubstituted di(C １ ~C ３０ ) alkyl(C ６ ~C ３０ ) arylsilyl, substituted or unsubstituted (C １ ~C ３０ ) alkyldi(C ６ ~C ３０ ) arylsilyl, substituted or unsubstituted tri(C ６ ~C ３０ ) arylsilyl, substituted or unsubstituted mono- or di-(C １ ~C ３０ ) alkylamino, substituted or unsubstituted mono- or di-(C ２ ~C ３０ ) alkenylamino, substituted or unsubstituted (C １ ~C ３０ ) alkyl(C ２ ~C ３０ ) alkenylamino, substituted or unsubstituted mono- or di-(C ６ ~C ３０ ) arylamino, substituted or unsubstituted (C １ ~C ３０ ) alkyl(C ６ ~C ３０ ) arylamino, substituted or unsubstituted mono- or di(3- to 30-membered)heteroarylamino, substituted or unsubstituted (C １ ~C ３０ ) alkyl (3 to 30 membered) heteroaryl amino, substituted or unsubstituted (C ２ ~C ３０ ) alkenyl (C ６ ~C ３０ ) arylamino, substituted or unsubstituted (C ２ ~C ３０ ) alkenyl (3 to 30 membered) heteroarylamino, substituted or unsubstituted (C ６ ~C ３０ ) aryl(3-30 membered)heteroarylamino, or (C ３ ~C ３０ ) an aliphatic ring and (C ６ ~C ３０ ) represents a substituted or unsubstituted condensed ring with an aromatic ring, or may be linked to adjacent substituents to form a ring) and a second host material comprising a compound represented by the formula:

2. The substituted alkyl, the substituted aryl(ene), the substituted heteroaryl(ene), the substituted cycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, the substituted mono- or di-alkylamino, the substituted mono- or di-alkenylamino, the substituted alkylalkenylamino, the substituted mono- or di-arylamino, the substituted alkylarylamino, the substituted mono- or di-heteroarylamino, the substituted alkylheteroarylamino, the substituted alkenylarylamino, the substituted alkenylheteroarylamino, the substituted arylheteroarylamino, and the substituted fused ring of an aliphatic ring and an aromatic ring each independently represent deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C １ ~C ３０ ) alkyl, halo (C １ ~C ３０ ) alkyl, (C ２ ~C ３０ ) alkenyl, (C ２ ~C ３０ ) alkynyl, (C １ ~C ３０ ) alkoxy, (C １ ~C ３０ ) alkylthio, (C ３ ~C ３０ ) cycloalkyl, (C ３ ~C ３０ ) cycloalkenyl, (3- to 7-membered) heterocycloalkyl, (C ６ ~C ３０ ) aryloxy, (C ６ ~C ３０ ) arylthio, unsubstituted or (C ６ ~C ３０ ) aryl-substituted (5- to 30-membered) heteroaryl, unsubstituted or (5- to 30-membered) heteroaryl-substituted (C ６ ~C ３０ ) aryl, tri(C １ ~C ３０ ) alkylsilyl, tri(C ６ ~C ３０ ) arylsilyl, di(C １ ~C ３０ ) alkyl(C ６ ~C ３０ ) arylsilyl, (C １ ~C ３０ ) alkyldi(C ６ ~C ３０ ) arylsilyl, (C ３ ~C ３０ ) an aliphatic ring and (C ６ ~C ３０ ) condensed ring with an aromatic ring, amino, mono- or di-(C １ ~C ３０ ) alkylamino, unsubstituted or (C １ ~C ３０ ) alkyl-substituted mono- or di-(C ６ ~C ３０ ) arylamino, (C １ ~C ３０ ) alkyl(C ６ ~C ３０ ) arylamino, mono- or di(3- to 30-membered) heteroarylamino, (C １ ~C ３０ ) alkyl(3-30 membered)heteroarylamino, (C ６ ~C ３０ ) aryl(3-30 membered)heteroarylamino, (C １ ~C ３０ ) alkylcarbonyl, (C １ ~C ３０ ) alkoxycarbonyl, (C ６ ~C ３０ ) arylcarbonyl, (C ６ ~C ３０ ) arylphosphinyl, di(C ６ ~C ３０ ) arylboronyl, di(C １ ~C ３０ ) alkylboronyl, (C １ ~C ３０ ) alkyl(C ６ ~C ３０ ) arylboronyl, (C ６ ~C ３０ )ar(C １ ~C ３０ ) alkyl, and (C １ ~C ３０ ) alkyl(C ６ ~C ３０ 10. The host materials of claim 1, wherein the host materials are substituted with at least one selected from the group consisting of:

3. Formula 1 is the following formulas 1-1 to 1-4: 【Chemistry 3】 (In formulas 1-1 to 1-4, R １ａ ~R １ｄ and R ２ａ ~R ２ｄ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C １ ~C ３０ ) alkyl, substituted or unsubstituted (C ６ ~C ３０ ) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C ３ ~C ３０ ) cycloalkyl, substituted or unsubstituted (C １ ~C ３０ ) alkoxy, substituted or unsubstituted tri(C １ ~C ３０ ) alkylsilyl, substituted or unsubstituted di(C １ ~C ３０ ) alkyl(C ６ ~C ３０ ) arylsilyl, substituted or unsubstituted (C １ ~C ３０ ) alkyldi(C ６ ~C ３０ ) arylsilyl, or substituted or unsubstituted tri(C ６ ~C ３０ ) arylsilyl, or may be linked to adjacent substituents to form a ring, but in each of formulas 1-1 to 1-4, R １ａ ~R １ｄ and R ２ａ ~R ２ｄ At least one of the groups is substituted or unsubstituted (C ６ ~C ３０ ) aryl or substituted or unsubstituted (3-30 membered) heteroaryl; X, L, and HAr are as defined in claim 1.

10. The host material of claim 1, wherein

4. The compound represented by formula 2 is represented by the following formulas 2-1 to 2-3: 【Chemistry 4】 (In formulas 2-1 to 2-3, T １ and T ２ are each independently -N=, -NR ７ represents -, -O-, or -S-, but T １ and T ２ One of them is -N=, and T １ and T ２ The other is -NR ７ -, -O-, or -S-; T ３ represents —O— or —S—; Ring A represents a substituted or unsubstituted phenanthrene; Ring B represents substituted or unsubstituted benzene or substituted or unsubstituted naphthalene; R ３ is substituted or unsubstituted (C ６ ~C ３０ ) aryl, or substituted or unsubstituted (3 to 30 membered) heteroaryl; R ４ ~R １２ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C １ ~C ３０ ) alkyl, substituted or unsubstituted (C ６ ~C ３０ ) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C ３ ~C ３０ ) cycloalkyl, substituted or unsubstituted (C １ ~C ３０ ) alkoxy, substituted or unsubstituted tri(C １ ~C ３０ ) alkylsilyl, substituted or unsubstituted di(C １ ~C ３０ ) alkyl(C ６ ~C ３０ ) arylsilyl, substituted or unsubstituted (C １ ~C ３０ ) alkyldi(C ６ ~C ３０ ) arylsilyl, substituted or unsubstituted tri(C ６ ~C ３０ ) arylsilyl, (C ３ ~C ３０ ) an aliphatic ring and (C ６ ~C ３０ ) a substituted or unsubstituted fused ring with an aromatic ring, a substituted or unsubstituted mono- or di-(C １ ~C ３０ ) alkylamino, substituted or unsubstituted mono- or di-(C ２ ~C ３０ ) alkenylamino, substituted or unsubstituted (C １ ~C ３０ ) alkyl(C ２ ~C ３０ ) alkenylamino, substituted or unsubstituted (C １ ~C ３０ ) alkyl(C ６ ~C ３０ ) arylamino, substituted or unsubstituted (C １ ~C ３０ ) alkyl (3 to 30 membered) heteroaryl amino, substituted or unsubstituted (C ２ ~C ３０ ) alkenyl (C ６ ~C ３０ ) arylamino, substituted or unsubstituted (C ２ ~C ３０ ) alkenyl (3 to 30 membered) heteroarylamino, substituted or unsubstituted mono- or di-(C ６ ~C ３０ )arylamino, substituted or unsubstituted mono- or di(3- to 30-membered)heteroarylamino, or substituted or unsubstituted (C ６ ~C ３０ ) aryl(3 to 30 membered)heteroarylamino, or may be linked to adjacent substituents to form a ring; c, d, and h each independently represent an integer of 1 or 2, e, f, and i each independently represent an integer of 1 to 4, g is an integer of 1 to 7, and j is an integer of 1 to 6; When c to j are integers of 2 or more, each R ４ ~Each R ６ , and each R ８ ~Each R １２ may be the same or different from each other; L １ ~L ３ , Ar ２ , and Ar ３ is as defined in claim 1) 2. The host material of claim 1, wherein the host material is one of:

5. L in Formula 2-1 ３ is a substituted or unsubstituted phenylene, the formula 2-1 is the following formula 2-1-a: 【Chemistry 5】 (In formula 2-1-a, Ar ４ ~Ar ８ are Ar in claim 1, respectively. ３ as defined for Ar ６ is not substituted or unsubstituted heteroaryl; T １ , T ２ , R ３ ~R ６ and c to e are as defined in claim 4, L １ , L ２ , and Ar ２ are each as defined in claim 1) 5. The plurality of host materials of claim 4, represented by:

6. The compound represented by formula 2-2 is represented by the following formulas 2-2a to 2-2c: 【Chemistry 6】 (In formulas 2-2a to 2-2c, T ３ , R ８ , R ９ , L １ ~L ３ , Ar ２ , Ar ３ , f, and g are as defined in claim 4) 5. The host material of claim 4, wherein the host material is represented by any one of:

7. The compound represented by formula 2-3 is represented by the following formulas 2-3a to 2-3d: 【Chemistry 7】 (In formulas 2-3a to 2-3d, j' is an integer from 1 to 4; When j′ is an integer of 2 or more, R １２ may be the same as or different from one another; R １０ ~R １２ , L １ ~L ３ , Ar ２ , Ar ３ and h to j are as defined in claim 4) 5. The host material of claim 4, wherein the host material is represented by any one of:

8. Formula 3 below: 【Chemistry 8】 (In Equation 3, X ２１ ~X ２３ are each independently N or CR ２０ represents, but X ２１ ~X ２３ represents N; R ２０ is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C １ ~C ３０ ) alkyl, substituted or unsubstituted (C ６ ~C ３０ ) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C ３ ~C ３０ ) cycloalkyl, substituted or unsubstituted (C １ ~C ３０ ) alkoxy, substituted or unsubstituted tri(C １ ~C ３０ ) alkylsilyl, substituted or unsubstituted di(C １ ~C ３０ ) alkyl(C ６ ~C ３０ ) arylsilyl, substituted or unsubstituted (C １ ~C ３０ ) alkyldi(C ６ ~C ３０ ) arylsilyl, substituted or unsubstituted tri(C ６ ~C ３０ ) arylsilyl, or (C ３ ~C ３０ ) an aliphatic ring and (C ６ ~C ３０ ) represents a substituted or unsubstituted fused ring with an aromatic ring; L ２１ ~L ２３ are each independently a single bond, a substituted or unsubstituted group (C ６ ~C ３０ ) arylene, or substituted or unsubstituted (3 to 30 membered) heteroarylene; Ar ２１ ~Ar ２３ are each independently substituted or unsubstituted (C １ ~C ３０ ) alkyl, substituted or unsubstituted (C ３ ~C ３０ ) cycloalkyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, (C ３ ~C ３０ ) an aliphatic ring and (C ６ ~C ３０ ) a substituted or unsubstituted fused ring with an aromatic ring, a substituted or unsubstituted (C ６ ~C ３０ )aryl, substituted or unsubstituted (3- to 30-membered)heteroaryl, substituted or unsubstituted tri(C １ ~C ３０ ) alkylsilyl, substituted or unsubstituted di(C １ ~C ３０ ) alkyl(C ６ ~C ３０ ) arylsilyl, substituted or unsubstituted (C １ ~C ３０ ) alkyldi(C ６ ~C ３０ ) arylsilyl, or substituted or unsubstituted tri(C ６ ~C ３０ ) represents arylsilyl) The plurality of host materials according to claim 1 , further comprising a third host material comprising a compound represented by the formula:

9. Formula 3 is the following formulas 3-1 to 3-4: 【Chemistry 9】 (In formulas 3-1 to 3-4, X ２ represents O or S; R ２１ａ ~R ２１ｄ and R ２２ａ ~R ２２ｄ are each independently hydrogen, deuterium, substituted or unsubstituted (C ６ ~C ３０ ) aryl, or substituted or unsubstituted (3 to 30 membered) heteroaryl; L ２１ ~L ２３ , Ar ２２ , and Ar ２３ is as defined in claim 1) 9. The host material of claim 8, wherein the host material is represented by any one of:

10. The compound represented by formula 1 is the following compound: 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】 【Chemical 21】 【Chemical 22】 【Chemical 23】 【Chemistry 24】 【Chemistry 25】 【Chemical formula 26】 【Chemical 27】 【Chemical Formula 28】 【Chemical Formula 29】 10. The plurality of host materials of claim 1 selected from:

11. The compound represented by formula 2 is the following compound: 【Chemistry 30】 【Chemical 31】 【Chemical 32】 【Chemical 33】 【Chemical Formula 34】 【Chemical 35】 【Chemical 36】 【Chemical 37】 【Chemical Formula 38】 【Chemical 39】 【Chemistry 40】 【Chemistry 41】 【Chemistry 42】 【Chemistry 43】 【Chemical Formula 44】 【Chemistry 45】 【Chemistry 46】 【Chemistry 47】 【Chemistry 48】 【Chemistry 49】 【Chemistry 50】 【Chemistry 51】 【Chemistry 52】 【Chemistry 53】 【Chemical 54】 【Chemistry 55】 【Chemical 56】 【Chemical 57】 【Chemistry 58】 【Chemical Formula 59】 【Chemistry 60】 【Hua 61】 【Hua 62】 【Chemistry 63】 【Hua 64】 【Chemistry 65】 【Hua 66】 【Hua 67】 10. The plurality of host materials of claim 1 selected from:

12. The compound represented by formula 3 is the following compound: 【Chemistry 68】 【Chemical Formula 69】 【Chemistry 70】 【Chemical 71】 【Chemical 72】 【Chemical 73】 【Chemical 74】 【Chemistry 75】 【Chemical Formula 76】 【Chemical 77】 【Chemical 78】 【Chemical 79】 【Chemistry 80】 【Chemistry 81】 【Chemistry 82】 【Chemistry 83】 【Chemistry 84】 【Chemistry 85】 【Chemistry 86】 【Hua 87】 【Hua 88】 9. The plurality of host materials of claim 8 selected from:

13. 10. An organic electroluminescent device comprising: a first electrode, a second electrode, and at least one light-emitting layer between the first electrode and the second electrode, wherein the at least one light-emitting layer comprises a plurality of host materials according to claim 1.

14. 10. An organic electroluminescent device comprising: a first electrode, a second electrode, and at least one light-emitting layer between the first electrode and the second electrode, wherein the at least one light-emitting layer comprises a plurality of host materials according to claim 8.

15. The following formulas 3-1-1 to 3-4-1: 【Chemistry 89】 (In formulas 3-1-1 to 3-4-1, X ２ represents O or S; L ２１ and L ２２ are each independently a single bond, a substituted or unsubstituted group (C ６ ~C ３０ ) arylene, or substituted or unsubstituted (3 to 30 membered) heteroarylene; L ２３ represents unsubstituted or deuterium-substituted phenylene; Ar ２２ is substituted or unsubstituted (C ６ ~C ３０ ) aryl, or substituted or unsubstituted (3 to 30 membered) heteroaryl; Ar ２３ represents a phenyl-substituted naphthyl optionally further substituted with deuterium; R ２３ ~R ３０ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C １ ~C ３０ ) alkyl, substituted or unsubstituted (C ３ ~C ３０ ) cycloalkyl, substituted or unsubstituted (C ６ ~C ３０ ) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C １ ~C ３０ ) alkoxy, substituted or unsubstituted tri(C １ ~C ３０ ) alkylsilyl, substituted or unsubstituted di(C １ ~C ３０ ) alkyl(C ６ ~C ３０ ) arylsilyl, substituted or unsubstituted (C １ ~C ３０ ) alkyldi(C ６ ~C ３０ ) arylsilyl, substituted or unsubstituted tri(C ６ ~C ３０ ) arylsilyl, substituted or unsubstituted mono- or di-(C １ ~C ３０ ) alkylamino, substituted or unsubstituted mono- or di-(C ２ ~C ３０ ) alkenylamino, substituted or unsubstituted (C １ ~C ３０ ) alkyl(C ２ ~C ３０ ) alkenylamino, substituted or unsubstituted mono- or di-(C ６ ~C ３０ ) arylamino, substituted or unsubstituted (C １ ~C ３０ ) alkyl(C ６ ~C ３０ ) arylamino, substituted or unsubstituted mono- or di(3- to 30-membered)heteroarylamino, substituted or unsubstituted (C １ ~C ３０ ) alkyl (3 to 30 membered) heteroaryl amino, substituted or unsubstituted (C ２ ~C ３０ ) alkenyl (C ６ ~C ３０ ) arylamino, substituted or unsubstituted (C ２ ~C ３０ ) alkenyl (3 to 30 membered) heteroarylamino, substituted or unsubstituted (C ６ ~C ３０ ) aryl(3-30 membered)heteroarylamino, or (C ３ ~C ３０ ) an aliphatic ring and (C ６ ~C ３０ ) represents a substituted or unsubstituted fused ring with an aromatic ring, and in each of formulas 3-1-1 to 3-4-1, R ２３ ~R ３０ At least one of the groups is substituted or unsubstituted (C ６ ~C ３０ ) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl) An organic electroluminescent compound represented by any one of the following:

16. Ar ２３ is of the following formula A: 【Chemistry 90】 (In Formula A, A １ ~A ８ One of the following is L ２３ is bonded to L ２３ A not bound to １ ~A ８ each independently represents hydrogen, deuterium, or a substituted or unsubstituted phenyl, １ ~A ８ and (b) at least one of (a) and (b) is substituted or unsubstituted phenyl.

16. The organic electroluminescent compound according to claim 15, wherein

17. The compound represented by any one of formulas 3-1-1 to 3-4-1 is the following compound: 【Chemistry 91】 【Chemistry 92】 【Chemistry 93】 【Chemistry 94】 【Chemistry 95】 16. The organic electroluminescent compound according to claim 15, selected from:

18. An organic electroluminescent material comprising the organic electroluminescent compound of claim 15.

19. 16. An organic electroluminescent device comprising the organic electroluminescent compound of claim 15.

Images