Multiple host materials and organic electroluminescent devices comprising the same

Abstract

The present disclosure relates to a plurality of host materials, which include a first host material and a second host material, the first host material including a compound represented by Formula 1, and the second host material including a compound represented by Formula 2; and relates to an organic electroluminescent device including the plurality of host materials. By including a specific combination of compounds as the host materials, an organic electroluminescent device can be provided which, compared with a conventional organic electroluminescent device, has a low driving voltage, a high luminous efficiency, a high power efficiency, and / or improved service life characteristics.

Description

Technical Field

[0001] The present disclosure relates to a variety of host materials and an organic electroluminescent device including the same. Background Art

[0002] Small molecule green organic electroluminescent devices (OLEDs) were first developed in 1987 by Tang et al. of Eastman Kodak using a TPD / Alq3 bilayer consisting of a light-emitting layer and a charge transport layer. Since then, the development of OLEDs has been rapidly affected and OLEDs have been commercialized. Currently, OLEDs mainly use phosphorescent materials with excellent luminous efficiency in panel implementation. In many applications such as TVs and lighting devices, the lifespan of OLEDs is insufficient, and there is still a need for high-efficiency OLEDs. Typically, the higher the brightness of an OLED, the shorter its lifespan. Therefore, for long-term use and high-resolution displays, OLEDs with high luminous efficiency and / or long service life characteristics are required.

[0003] To enhance luminous efficiency, driving voltage, and / or service life, various materials or concepts for the organic layers of organic electroluminescent devices have been proposed. However, they are not satisfactory in actual use.

[0004] U.S. Patent No. US 9,397,307 B2 discloses an organic electroluminescent device that uses a compound containing carbazole, dibenzofuran, or dibenzothiophene as a host. However, the reference does not specifically disclose an organic electroluminescent device using a specific combination of the various host materials of the present disclosure. Additionally, there is still a need to develop host materials for improving the performance of OLEDs. Summary of the Invention

[0005] Technical Problem

[0006] An object of the present disclosure is to provide an organic electroluminescent device having low driving voltage, high luminous efficiency, high power efficiency, and / or improved service life characteristics by including a variety of host materials including a specific combination of compounds.

[0007] Solution to the Problem

[0008] The inventors of the present invention have found that the above object can be achieved by using a variety of host materials including a first host material and a second host material, the first host material including a compound represented by Formula 1, and the second host material including a compound represented by Formula 2:

[0009]

[0010] Wherein

[0011] X1 represents NR3, CR4R5, O, or S;

[0012] Each of R1 and R2 independently represents hydrogen, deuterium, a halogen, cyano, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tri-(C1-C30) alkylsilyl group, a substituted or unsubstituted di-(C1-C30) alkyl (C6-C30) arylsilyl group, a substituted or unsubstituted (C1-C30) alkyl di-(C6-C30) arylsilyl group, a substituted or unsubstituted tri-(C6-C30) arylsilyl group, or or two R1s, two R2s, or both of them may be connected to each other to form one or more rings;

[0013] R3 represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, or

[0014] Each L1 independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3- to 30-membered) heteroarylene group, where if there are multiple L1s, each L1 may be the same or different;

[0015] Each of Ar1 and Ar2 independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tri-(C1-C30) alkylsilyl group, a substituted or unsubstituted di-(C1-C30) alkyl (C6-C30) arylsilyl group, a substituted or unsubstituted (C1-C30) alkyl di-(C6-C30) arylsilyl group, a substituted or unsubstituted tri-(C6-C30) arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30) alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30) arylamino group, or a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino group, where if multiple Ar1s and multiple Ar2s independently exist, each Ar1 and each Ar2 may be the same or different;

[0016] R4 and R5 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or they may be joined to each other to form one or more rings; and

[0017] a and b each independently represent an integer from 1 to 4, provided that if a and b are integers of 2 or greater, then each R1 and each R2 may be the same or different;

[0018]

[0019] wherein

[0020] HAr represents

[0021] X3 represents O or S;

[0022] L3 represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3- to 30-membered) heteroarylene group, provided that if HAr represents then L3 represents a substituted or unsubstituted naphthylene group;

[0023] Y1 to Y 12 each independently represent CR 11 or N, provided that at least one of Y1 to Y8 in represents N, and 12 at least one of Y1 to Y3, Y6 to Y8, and Y9 to Y

[0024] R 10 and R 12each independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or two Rs 10 、two Rs 12 、or the two of them may be connected to each other to form one or more rings;

[0025] R 11 , Ar3 and Ar4 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, or a substituted or unsubstituted tris(C6-C30)arylsilyl group, where if there are multiple Rs 11 ,each R 11 may be the same or different;

[0026] d represents an integer from 1 to 4, and e represents an integer from 1 to 3, where if d and e are integers of 2 or greater, each R 10 and each R 12 may be the same or different; and

[0027] * represents a bonding site.

[0028] Advantages of the present invention

[0029] By including a variety of host materials according to the present disclosure, an organic electroluminescent device can be provided, which has a low driving voltage, high luminous efficiency, high power efficiency, and / or improved service life characteristics compared with conventional organic electroluminescent devices, and a display device or a lighting device can be produced using the organic electroluminescent device. Detailed Embodiments

[0030] In the following, the present disclosure will be described in detail. However, the following description is intended to explain the invention and is not meant to limit the scope of the invention in any way.

[0031] The term "organic electroluminescent material" in the present disclosure means a material that can be used in an organic electroluminescent device and can contain at least one compound. If necessary, the organic electroluminescent material can be included in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole assisting material, a light emission assisting material, an electron blocking material, a light emitting material (including a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0032] The term "plurality of organic electroluminescent materials" in the present disclosure means an organic electroluminescent material including a combination of at least two compounds, which can be included in any layer constituting the organic electroluminescent device. It can mean both a material before being included in the organic electroluminescent device (e.g., before vapor deposition) and a material after being included in the organic electroluminescent device (e.g., after vapor deposition). For example, the plurality of organic electroluminescent materials can be a combination of at least two compounds, which can be included in at least one of a hole injection layer, a hole transport layer, a hole assisting layer, a light emission assisting layer, an electron blocking layer, a light emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. These at least two compounds can be included in the same layer or different layers by methods used in the art, and can be, for example, co-evaporated or co-evaporated, or can be evaporated individually.

[0033] The term "plurality of host materials" in the present disclosure means a host material including a combination of at least two compounds, which can be included in any light emitting layer constituting the organic electroluminescent device. It can mean both a material before being included in the organic electroluminescent device (e.g., before vapor deposition) and a material after being included in the organic electroluminescent device (e.g., after vapor deposition). For example, the plurality of host materials of the present disclosure can be a combination of at least two host materials, and optionally can further include conventional materials included in the organic electroluminescent material. The plurality of host materials of the present disclosure can be included in any light emitting layer constituting the organic electroluminescent device, and by methods used in the art, at least two compounds included in the plurality of host materials can be included together in one light emitting layer or can be included separately in different light emitting layers. For example, the at least two compounds can be co-evaporated or co-evaporated, or can be evaporated individually.

[0034] Herein, the term “(C1-C30)alkyl” means a straight-chain or branched-chain (sub)alkyl group having 1 to 30 carbon atoms constituting the chain, where the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10. The above alkyl groups may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. The term “(C2-C30)alkenyl” means a straight-chain or branched-chain alkenyl group having 2 to 30 carbon atoms constituting the chain, where the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The above alkenyl groups may include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc. The term “(C2-C30)alkynyl” means a straight-chain or branched-chain alkynyl group having 2 to 30 carbon atoms constituting the chain, where the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The above alkynyl groups may include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc. The term “(C3-C30)cycloalkyl” means a monocyclic or polycyclic hydrocarbon having 3 to 30 carbon atoms in the ring skeleton, where the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The above cycloalkyl groups may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. The term “(3- to 7-membered)heterocycloalkyl” means a cycloalkyl group having 3 to 7, preferably 5 to 7, ring skeleton atoms and including at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, and preferably consisting of the group of O, S, and N. The above heterocycloalkyl groups may include tetrahydrofuran, pyrrolidine, tetrahydrothiophene (thiolan), tetrahydropyran, etc. The term “(C6-C30)(sub)aryl” means a monocyclic or fused-ring group derived from an aromatic hydrocarbon having 6 to 30 carbon atoms in the ring skeleton, where the number of carbon atoms in the ring skeleton is preferably 6 to 20. The above (sub)aryl may be partially saturated and may contain a spiro structure. The above aryl groups may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, phenylphenanthryl, anthryl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, a base, naphthacenyl, fluoranthenyl, spirobifluorenyl, etc. More specifically, the above aryl groups may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, tetracenyl, pyrenyl, 1-chrysenyl, 2-chrysenyl, 3-chrysenyl, 4-chrysenyl, 5-chrysenyl, 6-chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, 1-benzophenanthryl, 2-benzophenanthryl, 3-benzophenanthryl, 4-benzophenanthryl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzofluorenyl, dibenzofluorenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, o-terphenyl group, 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 group, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenylyl, 4''-tert-butyl-p-terphenyl-4-yl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, etc.

[0035] The term “(3- to 30-membered) hetero(arylene)” means an aryl group having 3 to 30 ring backbone atoms and including at least one, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, Si, and P. The above hetero(arylene) can be monocyclic or a fused ring condensed with at least one benzene ring; can be partially saturated; can be a hetero(arylene) formed by connecting at least one heteroaryl or aryl group to a heteroaryl via one or more single bonds; and can contain a spiro structure. The above heteroaryl can include monocyclic heteroaryl groups such as furanyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl, as well as fused ring heteroaryl groups such as benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothienyl, benzonaphthofuranyl, benzofuranylthienyl, diazabenzofuranyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphthyridinyl, triazanaphthyl, benzothienopyrimidinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, and dihydroacridinyl. More specifically, the above heteroaryl can include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolinyl, 2-indolinyl, 3-indolinyl, 5-indolinyl, 6-indolinyl, 7-indolinyl, 8-indolinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 3-pyridyl, 4-pyridyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furanyl, 3-furanyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolinyl, 3-quinolinyl,4 - quinolinyl, 5 - quinolinyl, 6 - quinolinyl, 7 - quinolinyl, 8 - quinolinyl, 1 - isoquinolinyl, 3 - isoquinolinyl, 4 - isoquinolinyl, 5 - isoquinolinyl, 6 - isoquinolinyl, 7 - isoquinolinyl, 8 - isoquinolinyl, 2 - quinoxalinyl, 5 - quinoxalinyl, 6 - quinoxalinyl, 1 - carbazolyl, 2 - carbazolyl, 3 - carbazolyl, 4 - carbazolyl, 9 - carbazolyl, azacarbazol - 1 - yl, azacarbazol - 2 - yl, azacarbazol - 3 - yl, azacarbazol - 4 - yl, azacarbazol - 5 - yl, azacarbazol - 6 - yl, azacarbazol - 7 - yl, azacarbazol - 8 - yl, azacarbazol - 9 - yl, 1 - phenanthridinyl, 2 - phenanthridinyl, 3 - phenanthridinyl, 4 - phenanthridinyl, 6 - phenanthridinyl, 7 - phenanthridinyl, 8 - phenanthridinyl, 9 - phenanthridinyl, 10 - phenanthridinyl, 1 - acridinyl, 2 - acridinyl, 3 - acridinyl, 4 - acridinyl, 9 - acridinyl, 2 - oxazolyl, 4 - oxazolyl, 5 - oxazolyl, 2 - oxadiazolyl, 5 - oxadiazolyl, 3 - furazanyl, 2 - thienyl, 3 - thienyl, 2 - methylpyrrol - 1 - yl, 2 - methylpyrrol - 3 - yl, 2 - methylpyrrol - 4 - yl, 2 - methylpyrrol - 5 - yl, 3 - methylpyrrol - 1 - yl, 3 - methylpyrrol - 2 - yl, 3 - methylpyrrol - 4 - yl, 3 - methylpyrrol - 5 - yl, 2 - tert - butylpyrrol - 4 - yl, 3-(2 - phenylpropyl)pyrrol - 1 - yl, 2 - methyl - 1 - indolyl, 4 - methyl - 1 - indolyl, 2 - methyl - 3 - indolyl, 4 - methyl - 3 - indolyl, 2 - tert - butyl - 1 - indolyl, 4 - tert - butyl - 1 - indolyl, 2 - tert - butyl - 3 - indolyl, 4 - tert - butyl - 3 - indolyl, 1 - dibenzofuranyl, 2 - dibenzofuranyl, 3 - dibenzofuranyl, 4 - dibenzofuranyl, 1 - dibenzothiophenyl, 2 - dibenzothiophenyl, 3 - dibenzothiophenyl, 4 - dibenzothiophenyl, 1 - silafluorenyl group, 2 - silafluorenyl, 3 - silafluorenyl, 4 - silafluorenyl, 1 - germafluorenylgroup, 2 - germafluorenyl, 3 - germafluorenyl, and 4 - germafluorenyl. In addition, "halogen" includes F, Cl, Br, and I.

[0036] As used herein, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a functional group is replaced by another atom or another functional group (i.e., a substituent). The substituents of substituted alkyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted cycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted mono- or di-alkylamino, substituted mono- or di-aryl amino, and substituted alkylarylamino in the formulas of the present disclosure are each independently at least one selected from the group consisting of: deuterium; halogen; cyano; carboxyl; nitro; hydroxy; (C1-C30)alkyl; halo(C1-C30)alkyl; (C2-C30)alkenyl; (C2-C30)alkynyl; (C1-C30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl; (3- to 7-membered)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; unsubstituted or (3- to 30-membered)heteroaryl substituted with one or more (C6-C30)aryl groups; (C6-C30)aryl unsubstituted or substituted with at least one of (C1-C30)alkyl and (3- to 30-membered)heteroaryl; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; amino; mono- or di-(C1-C30)alkylamino; mono- or di-(C6-C30)arylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl; preferably, at least one selected from the group consisting of: (C1-C6)alkyl, substituted or unsubstituted (C6-C20)aryl, substituted or unsubstituted (3- to 15-membered)heteroaryl, and di(C6-C12)arylamino; more preferably, at least one selected from the group consisting of: (C1-C6)alkyl, (C6-C20)aryl unsubstituted or substituted with one or more (C1-C6)alkyl groups, (3- to 15-membered)heteroaryl unsubstituted or substituted with one or more (C6-C12)aryl groups, and di(C6-C12)arylamino; and for example, at least one selected from the group consisting of: methyl, phenyl, naphthyl, terphenyl, dimethylfluorenyl, phenylquinoxalinyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, and diphenylamino.

[0037] In the formulas of the present disclosure, if a substituent is connected to an adjacent substituent to form a ring or two adjacent substituents are connected to each other to form a ring, the ring may be a substituted or unsubstituted monocyclic or polycyclic (3-membered to 30-membered) alicyclic ring or aromatic ring, or a combination thereof, wherein the formed ring may contain at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S. According to one embodiment of the present disclosure, the number of ring skeleton atoms is 5 to 20. According to another embodiment of the present disclosure, the number of ring skeleton atoms is 5 to 15. For example, the fused ring may be 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 fluorene 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.

[0038] In the formulas of the present disclosure, a heteroaryl or heteroarylene may each independently contain at least one heteroatom selected from B, N, O, S, Si, and P. Additionally, the heteroatom may be bonded to at least one selected from the group consisting of: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-membered to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tris(C1-C30)alkylsilyl, substituted or unsubstituted bis(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tris(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, and substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino.

[0039] Hereinafter, the compounds represented by Formulas 1 and 2 will be described in more detail.

[0040] In Formula 1, X1 represents NR3, CR4R5, O, or S.

[0041] Here, R3 represents substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-membered to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, or According to one embodiment of the present disclosure, R3 represents a substituted or unsubstituted (C6-C30) aryl, or According to another embodiment of the present disclosure, R3 represents an unsubstituted or (C6-C30) aryl substituted by one or more (C6-C20) aryls or one or more (5- to 15-membered) heteroaryls; or Specifically, R3 may be naphthylphenyl, terphenylnaphthyl, dibenzofuranylnaphthyl, etc.

[0042] R4 and R5 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (C1-C30) alkoxy, a substituted or unsubstituted tris(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tris(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30) alkyl(C6-C30)arylamino; or may be connected to each other to form one or more rings. According to one embodiment of the present disclosure, R4 and R5 each independently represent a substituted or unsubstituted (C1-C6) alkyl, or a substituted or unsubstituted (C6-C12) aryl. According to another embodiment of the present disclosure, R4 and R5 each independently represent an unsubstituted (C1-C6) alkyl, or an unsubstituted (C6-C12) aryl. Specifically, R4 and R5 may each independently be methyl, phenyl, etc. R4 and R5 may be the same or different. According to one embodiment of the present disclosure, R4 and R5 may be the same.

[0043] In Formula 1, R1 and R2 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (C1-C30) alkoxy, a substituted or unsubstituted tris(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tris(C6-C30)arylsilyl, or Or two R1s, two R2s, or both of them can be connected to each other to form one or more rings. According to one embodiment of the present disclosure, each of R1 and R2 independently represents hydrogen, a substituted or unsubstituted (C6-C12) aryl group, a substituted or unsubstituted (5-membered to 15-membered) heteroaryl group, or Or two R1s, two R2s, or both of them can be connected to each other to form one or more rings. According to another embodiment of the present disclosure, each of R1 and R2 independently represents hydrogen, an unsubstituted (C6-C12) aryl group, an unsubstituted (5-membered to 15-membered) heteroaryl group, or Or two R1s, two R2s, or both of them can be connected to each other to form one or more rings. Specifically, each of R1 and R2 can independently be hydrogen, phenyl, dibenzothienyl, etc.; or two R1s, two R2s, or both of them can be connected to each other to form Or one or more benzene rings, where X2 represents NR7, CR8R9, O, or S; R6 has the same definition as R1 and R2; R7 has the same definition as R3; R8 and R9 each independently have the same definition as R4 and R5; c represents an integer from 1 to 4, where if c is an integer of 2 or greater, each R6 can be the same or different; and * represents the bonding site. According to one embodiment of the present disclosure, R6 is hydrogen.

[0044] In , each of L1 independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-membered to 30-membered) heteroarylene group, where if there are multiple L1s, each L1 can be the same or different. According to one embodiment of the present disclosure, each of L1 independently represents a single bond, or a substituted or unsubstituted (C6-C15) arylene group. According to another embodiment of the present disclosure, each of L1 independently represents a single bond; or an unsubstituted or (3-membered to 30-membered) heteroarylene group- or one or more bis(C6-C12) arylamino-substituted (C6-C15) arylene group. Specifically, each of L1 can independently be a single bond, phenylene, naphthylene, biphenylene, dibenzothienylphenylene, phenylene substituted with diphenylamino, etc.

[0045] In In formula (1), Ar1 and Ar2 each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group, wherein if multiple Ar1s and multiple Ar2s are each independently present, each Ar1 and each Ar2 may be the same or different. According to one embodiment of the present disclosure, Ar1 and Ar2 each independently represent a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5- to 15-membered) heteroaryl group. According to another embodiment of the present disclosure, Ar1 and Ar2 each independently represent an unsubstituted (C6-C25) aryl group substituted with at least one of one or more (C1-C6) alkyl groups and one or more (C6-C12) aryl groups; or an unsubstituted (5- to 15-membered) heteroaryl group. Specifically, Ar1 and Ar2 may each independently be phenyl, naphthyl, biphenyl, naphthylphenyl, dimethylfluorenyl, diphenylfluorenyl, phenyl substituted with dimethylfluorenyl, dibenzofuranyl, etc.

[0046] In formula (1), a and b each independently represent an integer from 1 to 4, wherein if a and b are integers of 2 or greater, each R1 and each R2 may be the same or different.

[0047] According to one embodiment of the present disclosure, formula (1) may be represented by at least one of the following formulas (1-1) to (1-3):

[0048]

[0049] wherein

[0050] X1, R1, R2, L1, Ar1, Ar2, a, and b are as defined in formula (1);

[0051] X2 represents NR7, CR8R9, O, or S;

[0052] R6 has the same definition as R1 and R2;

[0053] R7 has the same definition as R3;

[0054] R8 and R9 are each independently the same as defined for R4 and R5;

[0055] b' represents an integer from 1 to 3, b" represents 1 or 2, and c represents an integer from 1 to 4, where if b', b", and c are integers of 2 or greater, each R2 and each R6 may be the same or different; and

[0056] * represents a bonding site.

[0057] In Formula 2, HAr represents and X3 represents O or S.

[0058] In Formula 2, L3 represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-membered to 30-membered) heteroarylene, provided that if HAr represents then L3 represents a substituted or unsubstituted naphthylene. According to one embodiment of the present disclosure, L3 represents a single bond, or a substituted or unsubstituted (C6-C15) arylene. According to another embodiment of the present disclosure, L3 represents a single bond, or an unsubstituted (C6-C15) arylene. Specifically, L3 can be a single bond, phenylene, naphthylene, biphenylene, etc.

[0059] In Formula 2, Y1 to Y 12 each independently represents CR 11 or N, provided that at least one of Y1 to Y8 in represents N, and 12 at least one of Y1 to Y3, Y6 to Y8, and Y9 to Y in represents N. According to one embodiment of the present disclosure, 12 at least two of Y1 to Y8 in

[0060] represents N, and 10 and R 12Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or two Rs 10 、two Rs 12 、or both of them may be connected to each other to form one or more rings. According to one embodiment of the present disclosure, R 10 and R 12 each independently represents hydrogen.

[0061] In Formula 2, R 11 , Ar3 and Ar4 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or substituted or unsubstituted tri(C6-C30)arylsilyl, wherein if there are multiple Rs 11 ,then each R 11 may be the same or different. According to one embodiment of the present disclosure, R 11 represents hydrogen, substituted or unsubstituted (C6-C20) aryl, or substituted or unsubstituted (5- to 15-membered) heteroaryl. According to another embodiment of the present disclosure, R 11 represents hydrogen; (C6-C20) aryl that is unsubstituted or substituted by at least one of one or more (C1-C6) alkyls, one or more (C6-C12) aryls, one or more (5- to 20-membered) heteroaryls, and one or more di(C6-C12)arylaminos; or (5- to 15-membered) heteroaryl that is unsubstituted or substituted by one or more (C6-C12) aryls. Specifically, R 11It may be hydrogen, phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, benzophenanthryl, naphthylphenyl, phenylnaphthyl, dimethylfluorenyl, dimethylbenzofluorenyl, phenyl substituted with phenylquinoxalinyl, carbazolylphenyl, dibenzofuranylphenyl, phenyl substituted with diphenylamino, dibenzofuranyl, phenylcarbazolyl, etc. According to an embodiment of the present disclosure, Ar3 and Ar4 each independently represent a substituted or unsubstituted (C6-C20) aryl group. According to another embodiment of the present disclosure, Ar3 and Ar4 each independently represent an unsubstituted (C6-C20) aryl group. Specifically, Ar3 and Ar4 may each independently be an unsubstituted phenyl, an unsubstituted naphthyl, an unsubstituted biphenyl, an unsubstituted terphenyl, etc.

[0062] In Formula 2, d represents an integer from 1 to 4, and e represents an integer from 1 to 3, where if d and e are integers of 2 or greater, then each R 10 and each R 12 may be the same or different.

[0063] In Formulas 1 and 2, * represents a bonding site.

[0064] According to an embodiment of the present disclosure, Formula 2 may be represented by at least one of Formulas 2-1 to 2-10 below:

[0065]

[0066]

[0067] where

[0068] Y1 to Y8, Y 10 and Y 11 each independently represent CR 11 or N; and X3, L3, R 10 to R 12 and d and e are as defined in Formula 2.

[0069] According to an embodiment of the present disclosure, Formula 2 may be represented by Formula 2-11 below.

[0070]

[0071] where

[0072] X3 represents O or S;

[0073] L3 represents an unsubstituted naphthylene; and

[0074] Ar3 and Ar4 each independently represent an unsubstituted phenyl, an unsubstituted naphthyl, an unsubstituted biphenyl, or an unsubstituted terphenyl.

[0075] The compounds represented by Formula 1 include, but are not limited to, the following compounds.

[0076]

[0077]

[0078]

[0079] The compounds represented by Formula 2 include, but are not limited to, the following compounds.

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090] At least one of Compounds H-1-1 to H-1-53 and at least one of Compounds H-2-1 to H-2-212 can be combined and used in an organic electroluminescent device.

[0091] The compounds represented by Formula 1 according to the present disclosure can be produced by synthesis methods known to those skilled in the art, and for example, can be produced according to the methods disclosed in Korean Patent Application Publication Nos. 2013-0106255 (September 27, 2013), 2012-0042633 (May 3, 2012), and 2015-0066202 (June 16, 2015) (but not limited thereto).

[0092] The compounds represented by Formula 2 according to the present disclosure can be produced by synthesis methods known to those skilled in the art, and for example, can be produced according to the following Reaction Scheme 1, but not limited thereto:

[0093] [Reaction Scheme 1]

[0094]

[0095] In Reaction Scheme 1, X3, L3, HAr, R 10 , R 12 , d, and e are as defined in Formula 2.

[0096] The organic electroluminescent device of the present disclosure may include a first electrode, a second electrode, and at least one organic layer between the first electrode and the second electrode.

[0097] One of the first electrode and the second electrode may be an anode, and the other may be a cathode. The organic layer may include a light-emitting layer, and may further include at least one layer selected from a hole injection layer, a hole transport layer, a hole assist layer, a light-emitting assist layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer. The second electrode may be a semi-transmissive reflective electrode or a reflective electrode, and depending on the type of material, may be a top-emission type, a bottom-emission type, or a double-sided emission type. Additionally, the hole injection layer may be further doped with a p-type dopant, and the electron injection layer may be further doped with an n-type dopant.

[0098] The organic electroluminescent device according to the present disclosure may include an anode, a cathode, and at least one organic layer between the anode and the cathode, wherein the organic layer may include a variety of organic electroluminescent materials, which include a compound represented by Formula 1 as a first organic electroluminescent material and a compound represented by Formula 2 as a second organic electroluminescent material. According to an embodiment of the present disclosure, the organic electroluminescent device according to the present disclosure may include an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein the light-emitting layer may include a compound represented by Formula 1 and a compound represented by Formula 2.

[0099] The light-emitting layer includes a host and a dopant, wherein the host includes a variety of host materials, and the compound represented by Formula 1 may be included as a first host compound of the variety of host materials, and the compound represented by Formula 2 may be included as a second host compound of the variety of host materials. The weight ratio of the first host compound to the second host compound is from about 1:99 to about 99:1, preferably from about 10:90 to about 90:10, more preferably from about 30:70 to about 70:30, even more preferably from about 40:60 to about 60:40, and still more preferably about 50:50.

[0100] Here, the light-emitting layer is the layer from which light is emitted and can be a single layer or a multi-layer in which two or more layers are stacked. All of the first host material and the second host material may be included in one layer, or the first host material and the second host material may be included in respective different light-emitting layers. According to one embodiment of the present disclosure, the doping concentration of the dopant compound may be less than 20 wt% relative to the host compound in the light-emitting layer.

[0101] The organic electroluminescent device of the present disclosure may further include at least one layer selected from a hole injection layer, a hole transport layer, a hole assist layer, a light emission assist layer, an electron transport layer, an electron injection layer, an intermediate layer, an electron buffer layer, a hole blocking layer, and an electron blocking layer. According to one embodiment of the present disclosure, the organic electroluminescent device of the present disclosure may further include an amine-based compound other than the various host materials of the present disclosure as at least one of a hole injection material, a hole transport material, a hole assist material, a light emission material, a light emission assist material, and an electron blocking material. In addition, according to one embodiment of the present disclosure, the organic electroluminescent device of the present disclosure may further include an azine-based compound other than the various host materials of the present disclosure as at least one of an electron transport material, an electron injection material, an electron buffer material, and a hole blocking material.

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

[0103] The dopant included in the organic electroluminescent device of the present disclosure may include, but is not limited to, a compound represented by Formula 101 below.

[0104]

[0105] In Formula 101, L is selected from the following Structures 1 and 2:

[0106]

[0107] R 100 to R 103Each independently represents hydrogen, deuterium, a halogen, an unsubstituted or halogen-substituted (C1-C30) alkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C6-C30) aryl group, a cyano group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, or a substituted or unsubstituted (C1-C30) alkoxy group; or may be linked to adjacent substituents to form one or more rings together with the pyridine, such as a substituted or unsubstituted quinoline, benzofuropyridine, benzothienopyridine, indolopyridine, benzofuroquinoline, benzothienoquinoline, or indoloquinoline ring;

[0108] R 104 to R 107 Each independently represents hydrogen, deuterium, a halogen, an unsubstituted or halogen-substituted (C1-C30) alkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a cyano group, or a substituted or unsubstituted (C1-C30) alkoxy group; or may be linked to adjacent substituents to form one or more rings together with the benzene, such as a substituted or unsubstituted naphthyl group, fluorene, dibenzothiophene, dibenzofuran, indolopyridine, benzofuropyridine, or benzothienopyridine ring;

[0109] R 201 to R 211 Each independently represents hydrogen, deuterium, a halogen, an unsubstituted or halogen-substituted (C1-C30) alkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, or a substituted or unsubstituted (C6-C30) aryl group; or may be linked to adjacent substituents to form one or more rings; and

[0110] s represents an integer from 1 to 3.

[0111] Specific examples of the dopant compounds are as follows, but are not limited thereto.

[0112]

[0113]

[0114]

[0115]

[0116] In the organic electroluminescent device of the present disclosure, a hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof may be used between the anode and the light-emitting layer. The hole injection layer may be a multi-layer to reduce the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, where each of the multi-layers may use two compounds simultaneously. The hole transport layer or the electron blocking layer may also be a multi-layer.

[0117] An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be used between the light-emitting layer and the cathode. The electron buffer layer may be a multi-layer to control the injection of electrons and improve the interfacial properties between the light-emitting layer and the electron injection layer, where each of the multi-layers may use two compounds simultaneously. The hole blocking layer or the electron transport layer may also be a multi-layer, where each of the multi-layers may use multiple compounds.

[0118] In addition, the organic electroluminescent compound or a plurality of host materials according to the present disclosure may also be used in an organic electroluminescent device including QD (quantum dot).

[0119] 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 method, etc., or a wet film-forming method such as inkjet printing, nozzle printing, slot die coating, spin coating, dip coating, flow coating method, etc. may be used.

[0120] When using the wet film-forming method, a thin film may be formed by dissolving or diffusing the material for forming each layer in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent may be any solvent in which the material for forming each layer can be dissolved or diffused and there is no problem in film-forming ability.

[0121] The first and second host compounds of the present disclosure may be formed into a film by the methods listed above, generally by co-evaporation method or mixed evaporation method. Co-evaporation is a mixed deposition method in which two or more materials are placed in respective separate crucible sources and a current is applied to both units simultaneously to evaporate the materials. Mixed evaporation is a mixed deposition method in which two or more materials are mixed in one crucible source before evaporating them, and a current is applied to the unit to evaporate the materials. In addition, if the first host compound and the second host compound are present in the same layer or different layers in the organic electroluminescent device, the two host compounds may be formed into a film individually. For example, the second host compound may be deposited after depositing the first host compound.

[0122] The present disclosure can provide a display device by using a plurality of host materials including a compound represented by Formula 1 and a compound represented by Formula 2. That is, by using the plurality of host materials of the present disclosure, a display system or an illumination system can be manufactured. Specifically, by using the plurality of host materials of the present disclosure, a display system for, for example, a white organic light-emitting device, a smartphone, a tablet computer, a notebook, a PC, a TV, or an automobile can be produced; or an illumination system such as an outdoor or indoor illumination system.

[0123] Hereinafter, the preparation method and characteristics of the compounds of the present disclosure, and the characteristics of an organic electroluminescent device including the plurality of host materials of the present disclosure will be explained in detail with reference to representative compounds of the present disclosure. However, the present disclosure is not limited to the following examples.

[0124] Example 1: Preparation of Compound H-2-80

[0125]

[0126] Synthesis of Compound 1-1

[0127] 550 mL of toluene, 200 mL of EtOH, and 200 mL of H2O were added dropwise to 40.0 g of dibenzo[b,d]furan-1-ylboronic acid (189 mmol), 80.06 g of 1-bromo-4-iodobenzene (283 mmol), 10.90 g of Pd(PPh3)4 (9 mmol), and 49.99 g of Na2CO3 (472 mmol) in a flask, and the mixture was stirred at 150 °C under reflux for 2 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA) and dried over MgSO4. The residue was separated by column chromatography and MeOH was added thereto. The resulting solid was filtered under reduced pressure to obtain 30.1 g of Compound 1-1 (yield: 49.3%).

[0128] Synthesis of Compound 1-2

[0129] 150 mL of 1,4-dioxane was added dropwise to 9.0 g of Compound 1-1 (28 mmol), 10.61 g of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (42 mmol), 0.977 g of PdCl2(PPh3)2 (1 mmol), and 6.832 g of KOAc (70 mmol) in a flask, and the mixture was stirred at 140 °C under reflux for 1 hour. After the reaction was completed, the organic layer was extracted with EA and dried over MgSO4. The residue was separated by column chromatography and MeOH was added thereto. The resulting solid was filtered under reduced pressure to obtain 10.2 g of Compound 1-2 (yield: 98.93%).

[0130] Synthesis of Compound H-2-80

[0131] 10 mL of toluene, 3 mL of EtOH, and 3 mL of H2O were added dropwise to 2.50 g of 2,3-dichloroquinoxaline (13 mmol), 10.23 g of compound 1-2 (28 mmol), 1.451 g of Pd(PPh3)4 (1 mmol), and 8.680 g of K2CO3 (63 mmol) in a flask, and the mixture was stirred at 150 °C under reflux for 2 h. After the reaction was completed, the organic layer was extracted with EA and dried over MgSO4. The residue was separated by column chromatography and MeOH was added thereto. The resulting solid was filtered under reduced pressure to obtain 1.6 g of compound H-2-80 (yield: 20.0%).

[0132] 1 H NMR (600 MHz, DMSO-d6, δ) 8.28 (dd, J = 6.3, 3.4 Hz, 2H), 7.98 (dd, J = 6.3, 3.4 Hz, 2H), 7.85 - 7.80 (m, 4H), 7.77 (dd, J = 8.3, 0.9 Hz, 2H), 7.73 - 7.68 (m, 4H), 7.66 (d, J = 8.1 Hz, 2H), 7.63 (dd, J = 8.2, 7.4 Hz, 2H), 7.42 (dt, J = 7.9, 0.9 Hz, 2H), 7.37 (dd, J = 7.4, 0.9 Hz, 2H), 7.30 (ddd, J = 8.4, 7.2, 1.3 Hz, 2H), 6.91 (td, J = 7.6, 1.0 Hz, 2H)

[0133] Compound MW Melting Point H-2-80 614.70 231℃

[0134] Example 2: Preparation of Compound H-2-12

[0135]

[0136] 50 mL of toluene, 20 mL of EtOH, and 20 mL of H2O were added dropwise to 4.0 g of compound 2-1 (17 mmol), 8.38 g of 2-chloro-3-phenylquinoxaline (20 mmol), 0.960 g of Pd(PPh3)4 (0.83 mmol), and 6.89 g of K2CO3 (50 mmol) in a flask, and the mixture was stirred at 140 °C under reflux for 2 h. After the reaction was completed, the organic layer was extracted with EA and dried over MgSO4. The residue was separated by column chromatography and MeOH was added thereto. The resulting solid was filtered under reduced pressure to obtain 3.2 g of compound H-2-12 (yield: 38.6%).

[0137] 1 1H NMR (600 MHz, DMSO-d6, δ) 8.34 - 8.29 (m, 1H), 8.25 (d, J = 7.8 Hz, 1H), 8.04 - 7.95 (m, 2H), 7.87 (dd, J = 8.3, 0.9 Hz, 1H), 7.76 - 7.69 (m, 4H), 7.62 (d, J = 7.2 Hz, 1H), 7.54 (d, J = 7.5 Hz, 2H), 7.48 - 7.39 (m, 4H), 7.37 (s, 1H), 7.30 (dt, J = 26.1, 7.6 Hz, 3H), 7.19 (s, 1H), 7.03 (t, J = 7.5 Hz, 1H)

[0138] Compound MW Melting Point H-2-12 498.59 245℃

[0139] Example 3: Preparation of Compound H-2-9

[0140]

[0141] Synthesis of Compound 1-1

[0142] 550 mL of toluene, 200 mL of EtOH and 200 mL of H2O were added dropwise to 80.0 g of dibenzo[b,d]furan-1-ylboronic acid (377 mmol), 160.13 g of 1-bromo-4-iodobenzene (566 mmol), 21.80 g of Pd(PPh3)4 (19 mmol) and 99.99 g of Na2CO3 (943 mmol) in a flask, and the mixture was stirred at 150 °C under reflux for 2.5 h. After the reaction was completed, the organic layer was extracted with EA and dried over MgSO4. The residue was separated by column chromatography and MeOH was added thereto. The resulting solid was filtered under reduced pressure to obtain 51.8 g of Compound 1-1 (yield: 42.5%).

[0143] Synthesis of Compound 1-2

[0144] 150 mL of 1,4-dioxane was added dropwise to 30.0 g of Compound 1-1 (93 mmol), 35.4 g of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (139 mmol), 3.26 g of PdCl2(PPh3)2 (5 mmol), and 22.77 g of KOAc (232 mmol) in a flask, and the mixture was stirred at 140 °C under reflux for 1 hour. After the reaction was completed, the organic layer was extracted with EA and dried over MgSO4. The residue was separated by column chromatography, and MeOH was added thereto. The resulting solid was filtered under reduced pressure to obtain 23.3 g of Compound 1-2 (yield: 67.8%).

[0145] Synthesis of Compound H-2-9

[0146] 40 mL of toluene, 15 mL of EtOH, and 15 mL of H2O were added dropwise to 4.28 g of 6-chloro-2,4-diphenylquinazoline (14 mmol), 6.00 g of Compound 1-2 (16 mmol), 0.780 g of Pd(PPh3)4 (0.675 mmol), and 4.67 g of K2CO3 (34 mmol) in a flask, and the mixture was stirred at 150 °C under reflux for 2 hours. After the reaction was completed, the organic layer was extracted with EA and dried over MgSO4. The residue was separated by column chromatography, and MeOH was added thereto. The resulting solid was filtered under reduced pressure to obtain 4.3 g of Compound H-2-9 (yield: 60.7%).

[0147] 1 H NMR (600 MHz, DMSO-d6, δ) 8.69 - 8.64 (m, 2H), 8.54 (dd, J = 8.7, 2.0 Hz, 1H), 8.42 (d, J = 2.0 Hz, 1H), 8.31 (d, J = 8.7 Hz, 1H), 8.03 (dd, J = 21.1, 7.3 Hz, 4H), 7.83 - 7.69 (m, 7H), 7.66 - 7.56 (m, 5H), 7.51 (t, J = 7.7 Hz, 1H), 7.37 (d, J = 7.4 Hz, 1H), 7.25 (t, J = 7.6 Hz, 1H)

[0148] Compound MW Melting Point H-2-9 524.62 242℃

[0149] Example 4: Preparation of Compound H-2-7

[0150]

[0151] 70 mL of o-xylene was added dropwise to 6.00 g of Compound 1-2 (16 mmol), 4.28 g of 6-chloro-2,3-diphenylquinoxaline (14 mmol), 0.618 g of Pd(PPh3)4 (0.83 mmol), 0.554 g of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (sphos) (1 mmol), and 3.24 g of K2CO3 (34 mmol) in a flask, and the mixture was stirred at 140 °C under reflux for 2 hours. After the reaction was completed, the organic layer was extracted with EA and dried over MgSO4. The residue was separated by column chromatography, and MeOH was added thereto. The resulting solid was filtered under reduced pressure to obtain 4.6 g of Compound H-2-7 (yield: 64.9%).

[0152] 1 H NMR (600 MHz, DMSO-d6, δ) 8.59 (d, J = 2.1 Hz, 1H), 8.41 (dd, J = 8.7, 2.1 Hz, 1H), 8.30 (d, J = 8.7 Hz, 1H), 8.21 (d, J = 8.2 Hz, 2H), 7.87 - 7.83 (m, 2H), 7.81 - 7.74 (m, 2H), 7.68 - 7.62 (m, 2H), 7.57 - 7.50 (m, 5H), 7.45 - 7.36 (m, 7H), 7.27 (t, J = 7.6 Hz, 1H)

[0153] Compound MW Melting Point H-2-7 524.62 225℃

[0154] Example 5: Preparation of Compound H-2-89

[0155]

[0156] 3.0 g of dibenzo[b,d]furan-1-ylboronic acid (14.2 mmol), 6.3 g of 2-(4-bromonaphthalen-1-yl)-4,6-biphenyl-1,3,5-triazine (14.2 mmol), 0.82 g of tetrakis(triphenylphosphine)palladium(0) (0.71 mmol), and 3.9 g of sodium carbonate (28.4 mmol) were dissolved in 30 mL of toluene, 8 mL of ethanol, and 15 mL of water in a flask, and the mixture was refluxed for 2 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the remaining moisture was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 1.9 g of Compound H-2-89 (yield: 26%).

[0157] Compound MW Melting Point H-2-89 525.6 203℃

[0158] Example 6: Preparation of Compound H-2-91

[0159]

[0160] Synthesis of Compound 6-1

[0161] Dissolve 20 g of dibenzo[b,d]furan-1-ylboronic acid (94.3 mmol), 53.9 g of 1,4-dibromonaphthalene (188.67 mmol), 32.6 g of K2CO3 (235.75 mmol) and 5.4 g of Pd(PPh3)4 (4.7 mmol) in 470 mL of toluene, 235 mL of ethanol and 235 mL of water in a flask, and reflux the mixture at 140 °C for 4 hours. After the reaction is completed, extract the organic layer with ethyl acetate and remove the remaining moisture using magnesium sulfate. Dry the residue and separate it by column chromatography to obtain 20 g of compound 6-1 (yield: 56.8%).

[0162] Synthesis of Compound 6-2

[0163] Dissolve 20 g of compound 6-1 (53.6 mmol), 16.3 g of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (64.3 mmol), 3.76 g of PdCl2(PPh3)2 (5.36 mmol) and 10.5 g of KOAc (107.2 mmol) in 270 mL of 1,4-dioxane in a flask, and reflux the mixture at 150 °C for 4 hours. After the reaction is completed, extract the organic layer with ethyl acetate and remove the remaining moisture using magnesium sulfate. Dry the residue and separate it by column chromatography to obtain 23 g of compound 6-2 (yield: 100%).

[0164] Synthesis of Compound H-2-91

[0165] Dissolve 7 g of compound 6-2 (16.6 mmol), 7.35 g of 2-chloro-4,6-di(naphthalen-2-yl)-1,3,5-triazine (19.9 mmol), 13.5 g of Cs2CO3 (41.5 mmol) and 959 mg of Pd(PPh3)4 (0.83 mmol) in 83 mL of toluene in a flask, and reflux the mixture at 130 °C for 18 hours. After the reaction is completed, extract the organic layer with ethyl acetate and remove the remaining moisture using magnesium sulfate. Dry the residue and separate it by column chromatography to obtain 2 g of compound H-2-91 (yield: 19.2%).

[0166] Compound MW Melting Point H-2-91 625.73 150℃

[0167] Example 7: Preparation of Compound H-2-94

[0168]

[0169] Synthesis of Compound 7-1

[0170] Dissolve 32.2 g of 2-chloro-4,6-bis(naphthalen-2-yl)-1,3,5-triazine (87.7 mmol), 20 g of (4-bromonaphthalen-1-yl)boronic acid (79.7 mmol), 65 g of Cs2CO3 (199.25 mmol) and 4.6 g of Pd(PPh3)4 (3.985 mmol) in 400 mL of toluene in a flask, and reflux the mixture at 140 °C for 4 h. After completion of the reaction, extract the organic layer with ethyl acetate and remove the remaining moisture using magnesium sulfate. Dry the residue and separate it by column chromatography to obtain 20 g of compound 7-1 (yield: 46.6%).

[0171] Synthesis of Compound H-2-94

[0172] Dissolve 7 g of compound 7-1 (13 mmol), 4.6 g of compound 2-2 (15.6 mmol), 4.5 g of K2CO3 (32.5 mmol) and 0.75 g of Pd(PPh3)4 (0.65 mmol) in 65 mL of toluene, 32.5 mL of ethanol and 32.5 mL of H2O in a flask, and reflux the mixture at 130 °C for 3 h. After completion of the reaction, extract the organic layer with ethyl acetate and remove the remaining moisture using magnesium sulfate. Dry the residue and separate it by column chromatography to obtain 3.4 g of compound H-2-94 (yield: 41%).

[0173] Compound MW Melting Point H-2-94 625.73 250℃

[0174] Example 8: Preparation of Compound H-2-108

[0175]

[0176] Synthesis of Compound 8-1

[0177] Dissolve 5 g of 3-bromodibenzofuran (20 mmol), 7.6 g of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (30 mmol), 1.4 g of PdCl2(PPh3)2 (2 mmol) and 3.9 g of KOAc (50 mmol) in 100 mL of 1,4-dioxane in a flask, and reflux the mixture at 150 °C for 4 h. After completion of the reaction, extract the organic layer with ethyl acetate and remove the remaining moisture using magnesium sulfate. Dry the residue and separate it by column chromatography to obtain 5 g of compound 8-1 (yield: 85%).

[0178] Synthesis of Compound H-2-108

[0179] Dissolve 4.4 g of compound 7-1 (12.3 mmol), 5 g of compound 8-1 (13.5 mmol), 4.5 g of K2CO3 (32.5 mmol), and 0.75 g of Pd(PPh3)4 (0.65 mmol) in 60 mL of toluene, 30 mL of ethanol, and 30 mL of H2O in a flask, and reflux the mixture at 130 °C for 3 hours. After the reaction is completed, extract the organic layer with ethyl acetate and remove the remaining moisture using magnesium sulfate. Dry the residue and separate it by column chromatography to obtain 4 g of compound H-2-108 (yield: 49%).

[0180] Example 9: Preparation of Compound H-2-90

[0181]

[0182] Synthesis of Compound 6-1

[0183] Add 20 g of dibenzo[b,d]furan-1-ylboronic acid (94.33 mmol), 54 g of 1,4-dibromonaphthalene (188.6 mmol), 5.4 g of Pd(PPh3)4 (4.716 mmol), and 26 g of K2CO3 (188.6 mmol) to 380 mL of toluene, 95 mL of EtOH, and 95 mL of purified water in a flask, and stir the mixture under reflux for 3 hours. After the reaction is completed, cool the mixture to room temperature and extract it with distilled water and EA. Distill the organic layer under reduced pressure and separate it by column chromatography using MC / Hex to obtain 20 g of compound 6-1 (yield: 55%).

[0184] Synthesis of Compound 6-2

[0185] Add 3.7 g of PdCl2(PPh3)2 (53.59 mmol), 10.5 g of KOAc (107.1 mmol), 17.7 g of bis(pinacolato)diboron (69.66 mmol), and 270 mL of 1,4-dioxane to 20 g of compound 6-1 (53.59 mmol) in a flask, and stir the mixture under reflux for 2 hours. After the reaction is completed, filter the mixture through diatomaceous earth and extract it with MC. Distill the organic layer under reduced pressure and separate it by column chromatography using MC / Hex to obtain 20 g of compound 6-2 (yield: 88%).

[0186] Synthesis of Compound H-2-90

[0187] 6 g of Compound 6-2 (14.16 mmol), 5 g of 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (15.73 mmol), 0.9 g of Pd(PPh3)4 (0.786 mmol), and 4.3 g of K2CO3 (31.47 mmol) were added to 64 mL of toluene, 16 mL of EtOH, and 16 mL of purified water in a flask, and the mixture was stirred under reflux for 2 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with distilled water and EA. The organic layer was distilled under reduced pressure and separated by column chromatography using MC / Hex to obtain 4 g of Compound H-2-90 (yield: 44%).

[0188] Compound MW Melting Point H-2-90 575.6 131.3℃

[0189] Device Examples 1 to 5: Production of OLEDs Containing Multiple Host Materials According to the Present Disclosure

[0190] Produce an OLED according to the present disclosure. The indium tin oxide (ITO) thin film (10 Ω / sq) (GEOMATEC CO., LTD., Japan) on the glass substrate of the OLED was subjected to ultrasonic washing successively with acetone, trichloroethylene, acetone, ethanol, and distilled water, and then stored in isopropanol. Then the ITO substrate was mounted on the substrate holder of a vacuum vapor deposition apparatus. Compound HI-1 was introduced into the chamber of the vacuum vapor deposition apparatus, and then the pressure in the chamber of the apparatus was controlled to 10 -6Next, an electric current was applied to the chamber to evaporate the above-introduced material, thereby forming a first hole injection layer with a thickness of 80 nm on the ITO substrate. Next, compound HI-2 was introduced into another chamber of the vacuum vapor deposition apparatus, and the compound was evaporated by applying an electric current to the chamber, thereby forming a second hole injection layer with a thickness of 5 nm on the first hole injection layer. Then, compound HT-1 was introduced into the chamber of the vacuum vapor deposition apparatus, and the compound was evaporated by applying an electric current to the chamber, thereby forming a first hole transport layer with a thickness of 10 nm on the second hole injection layer. Then, compound HT-2 was introduced into another chamber of the vacuum vapor deposition apparatus, and the compound was evaporated by applying an electric current to the chamber, thereby forming a second hole transport layer with a thickness of 60 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, an emission layer was formed thereon as follows: The first host compound and the second host compound shown in Table 1 or 2 below were introduced as hosts into two chambers of the vacuum vapor deposition apparatus, and compound D-39 was introduced as a dopant into another chamber. The two host materials were evaporated at a rate of 1:1, and the dopant material was simultaneously evaporated at a different rate, and the dopant was deposited at a doping amount of 3 wt% based on the total amount of the host and the dopant to form an emission layer with a thickness of 40 nm on the second hole transport layer. Compound ET-1 and compound EI-1 were introduced into two chambers and evaporated at a ratio of 1:1 to form an electron transport layer with a thickness of 35 nm on the emission layer. After depositing compound EI-1 as an electron injection layer with a thickness of 2 nm on the electron transport layer, an Al cathode with a thickness of 80 nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus. Thus, an OLED was produced.

[0191] Comparative Examples 1 to 5: Production of OLEDs Not According to the Present Disclosure

[0192] An OLED was produced in the same manner as in Device Examples 1 to 5, except that the host materials shown in Table 1 or 2 below were used instead of the host combination of the present disclosure.

[0193] Table 1 below provides the driving voltage, luminous efficiency, growth rate of luminous efficiency, and power efficiency of the OLEDs produced in Device Examples 1 and 2 and Comparative Examples 1 and 2 at a brightness of 5,000 nits, and the time (service life; T90) taken for the brightness to decrease from 100% to 90% at a brightness of 5,000 nits.

[0194] [Table 1]

[0195]

[0196] In addition, Table 2 below provides the power efficiency of the OLEDs produced in Device Examples 3 to 5 and Comparative Examples 3 to 5 at a brightness of 1,000 nits, and / or the time taken for the brightness to decrease from 100% to 98% at a brightness of 5,000 nits and a constant current (service life; T98).

[0197] [Table 2]

[0198]

[0199] As can be seen from Table 1 above, compared with conventional OLEDs, the OLEDs comprising a plurality of host materials including a specific combination of compounds according to the present disclosure have a low driving voltage and significantly improved luminous efficiency, power efficiency, and service life characteristics.

[0200] Furthermore, as can be seen from Table 2 above, compared with conventional OLEDs, the OLEDs comprising a plurality of host materials including a specific combination of compounds according to the present disclosure exhibit significantly improved service life characteristics while having equal or higher power efficiency.

[0201] The compounds used in the device examples and comparative examples are shown in Table 3 below.

[0202] [Table 3]

[0203]

Claims

1. A plurality of host materials, said plurality of host materials comprising a first host material and a second host material, said first host material comprising a compound represented by Formula 1 below, and said second host material comprising a compound represented by Formula 2 below: Wherein X1 represents NR3, CR4R5, O or S; Each of R1 and R2 independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tris(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tris(C6-C30)arylsilyl, or or two R1s, two R2s, or both thereof may be connected to each other to form one or more rings; R3 represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, or L1 each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3- to 30-membered) heteroarylene group, where if there are multiple L1s, each L1 can be the same or different; Ar1 and Ar2 each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted bis(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group, where if multiple Ar1s and multiple Ar2s independently exist, each Ar1 and each Ar2 can be the same or different; R4 and R5 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted bis(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or they can be connected to each other to form one or more rings; and a and b each independently represent an integer from 1 to 4, where if a and b are integers of 2 or greater, each R1 and each R2 can be the same or different; Wherein HAr represents X3 represents O or S; L3 represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3- to 30-membered) heteroarylene group, provided that if HAr represents then L3 represents a substituted or unsubstituted naphthylene group; Y1 to Y 12 each independently represents CR 11 or N, provided that at least one of Y1 to Y8 in represents N, and 12 at least one of Y1 to Y3, Y6 to Y8, and Y9 to Y in R 10 represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, an unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or two Rs 10 , two Rs 12 , or both of them may be connected to each other to form one or more rings; R 12 represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tris(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tris(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or two Rs 10 , two Rs 12 , or both thereof may be joined to each other to form one or more rings; R 11 、 Ar3 and Ar4 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, or a substituted or unsubstituted tri(C6-C30)arylsilyl group, where if there are multiple Rs 11 , then each R 11 may be the same or different; d represents an integer from 1 to 4, and e represents an integer from 1 to 3, where each R, if d and e are integers of 2 or greater 10 and each R 12 can be the same or different; and * represents the bonding site.

2. The various main materials according to claim 1, wherein, R1 to R5, R 10 to R 12 , L1, L3, and the substituents of the substituted alkyl, the substituted aryl, the substituted arylene, the substituted heteroaryl, the substituted heteroarylene, 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-arylamino, and the substituted alkylarylamino in Ar1 to Ar4 are each independently at least one selected from the group consisting of: deuterium; halogen; cyano; carboxyl; nitro; hydroxy; (C1-C30)alkyl; halo(C1-C30)alkyl; (C2-C30)alkenyl; (C2-C30)alkynyl; (C1-C30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl; (3- to 7-membered)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; unsubstituted or (3- to 30-membered)heteroaryl substituted with one or more (C6-C30)aryl; (C6-C30)aryl unsubstituted or substituted with at least one of (C1-C30)alkyl and (3- to 30-membered)heteroaryl; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; amino; mono- or di-(C1-C30)alkylamino; mono- or di-(C6-C30)arylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl.

3. The multiple main materials according to claim 1, wherein In the definitions of R1 and R2, if two R1s, two R2s, or both of them are connected to each other to form one or more rings, the rings formed are or one or more benzene rings; X2 represents NR7, CR8R9, O or S; R6 has the same definition as R1 and R2; R7 has the same definition as R3; R8 and R9 each independently have the same definition as R4 and R5; c represents an integer from 1 to 4, where if c is an integer of 2 or greater, each R6 may be the same or different; and * represents a bonding site.

4. The multiple main materials according to claim 1, wherein Formula 1 is represented by at least one of Formulas 1-1 to 1-3: where X1, R1, R2, L1, Ar1, Ar2, a, and b are as defined in claim 1; X2 represents NR7, CR8R9, O, or S; R6 has the same definition as R1 and R2; R7 has the same definition as R3; R8 and R9 are each independently the same as the definition of R4 and R5; b' represents an integer from 1 to 3, b" represents 1 or 2, and c represents an integer from 1 to 4, where if b', b", and c are integers of 2 or greater, each R2 and each R6 may be the same or different; and * represents a bonding site.

5. The multiple main body materials according to claim 1, wherein, Formula 2 is represented by at least one of Formulas 2-1 to 2-10: where Y1 to Y8, Y 10 , and Y 11 each independently represents CR 11 or N; and X3, L3, R 10 to R 12 , d and e are as defined in claim 1.

6. The multiple main materials according to claim 1, wherein Formula 2 is represented by Formula 2-11: where X3 represents O or S; L3 represents unsubstituted naphthylene; and Ar3 and Ar4 each independently represent unsubstituted phenyl, unsubstituted naphthyl, unsubstituted biphenyl, or unsubstituted terphenyl.

7. The multiple main materials according to claim 1, wherein, The compound represented by Formula 1 is at least one selected from the following compounds: and 8. The multiple main materials according to claim 1, wherein The compound represented by Formula 2 is at least one selected from the following compounds:

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

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