Multiple host materials and organic electroluminescent devices comprising the same

Abstract

The present disclosure relates to a plurality of host materials, the plurality of host materials including a first host material and a second host material, the first host material including a compound represented by Formula 1 below, and the second host material including a compound represented by Formula 2 below; and an organic electroluminescent device including the plurality of host materials. By including a specific combination of compounds as host materials, an organic electroluminescent device having higher luminous efficiency and / or improved lifetime characteristics compared to conventional organic electroluminescent devices can be provided.

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] In 1987, Tang et al. of Eastman Kodak first developed a small molecule green organic electroluminescent device (OLED) of a TPD / Alq3 bilayer composed of a light-emitting layer and a charge transport layer. Since then, research on OLEDs has been rapidly developed and it has been commercialized. Currently, phosphorescent materials provide excellent luminous efficiency in clear panels and are mainly used in organic electroluminescent devices. OLEDs with high luminous efficiency and / or long lifetime are required for long-term use and high-resolution displays.

[0003] In order to enhance luminous efficiency, driving voltage, and / or lifetime, various materials or concepts for the organic layers of organic electroluminescent devices have been proposed. However, they are not satisfactory in practical use.

[0004] U.S. Patent No. 9,397,307 discloses an organic electroluminescent device that uses a compound in which dibenzofuran or dibenzothiophene is directly bonded to a nitrogen-containing heteroaryl or bonded to a nitrogen-containing heteroaryl via a linker as a host. However, the reference does not specifically disclose a specific combination of the various host materials of the present disclosure, and 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 high luminous efficiency and / or improved lifetime characteristics by including a variety of host materials, the variety of host materials including a specific combination of compounds.

[0007] Solution to the Problem

[0008] The compound of Formula 1 of the present disclosure provides slow hole mobility due to a very deep HOMO (highest occupied molecular orbital) and fast electron mobility due to a nitrogen-containing moiety. Due to this imbalance in hole and electron mobilities, it is necessary to improve luminous efficiency and lifetime characteristics.

[0009] As a result of in-depth research, the inventors of the present invention found that introducing a combination of a compound of Formula 1 having fast hole mobility and a compound of Formula 2 can provide a positive effect on hole transport characteristics. As a result, by using a combination of the compounds of Formula 1 and Formula 2 in an OLED, high efficiency and long lifetime due to an increase in exciton formation in the light-emitting layer can be achieved.

[0010] The inventors of the present invention have found that the above object can be achieved by a variety of host materials, the 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 below, and the second host material including a compound represented by Formula 2 below:

[0011]

[0012] wherein

[0013] X represents O or S;

[0014] R1 to R8 each independently represent -L1-HAr, hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, -NR9R 10 、or -SiR 11 R 12 R 13 ; or may be connected to adjacent substituents to form a ring; provided that at least one of R1 to R8 is -L1-HAr;

[0015] L1 represents a single bond, substituted or unsubstituted (C1-C30) alkylene, substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (3- to 30-membered) heteroarylene, or substituted or unsubstituted (C3-C30) cycloalkylene, wherein if there are multiple L1s, each L1 may be the same or different;

[0016] HAr represents substituted or unsubstituted nitrogen-containing (3- to 30-membered) heteroaryl, wherein if there are multiple HArs, each HAr may be the same or different;

[0017]

[0018] wherein

[0019] L2 represents a single bond, substituted or unsubstituted (C1-C30) alkylene, substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (3- to 30-membered) heteroarylene, or substituted or unsubstituted (C3-C30) cycloalkylene;

[0020] Ar represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C3-C30) cycloalkenyl group, a substituted or unsubstituted (3- to 7-membered) heterocycloalkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, -NR9R 10 、 or -SiR 11 R 12 R 13 ; or may be connected to an adjacent substituent to form a ring;

[0021] is represented by Formula 3 or Formula 4 below;

[0022]

[0023] wherein

[0024] X1 to X 25 each independently represents N or CR 14 ;

[0025] R 14 each 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 adjacent Rs 14 may be connected to each other to form a ring, and wherein if there are multiple Rs 14 , then each R 14 may be the same or different;

[0026] R9 to R 13 each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; and

[0027] * represents the bonding site to L2.

[0028] Advantages of the present invention

[0029] By including various host materials of the present disclosure, an organic electroluminescent device having higher luminous efficiency and / or improved lifetime characteristics compared to a conventional organic electroluminescent device can be provided, and the organic electroluminescent device can be used to fabricate a display device or a lighting device. Detailed Description

[0030] Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present disclosure and does not mean to limit the scope of the present disclosure 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 include 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 luminescence assisting material, an electron blocking material, a luminescent 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 "various organic electroluminescent materials" in the present disclosure means an organic electroluminescent material including a combination of at least two compounds, and the material 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 various 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 luminescence assisting layer, an electron blocking layer, a luminescent 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 co-evaporated or co-evaporated, or can be evaporated individually.

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

[0034] Hereinafter, the compounds represented by Formulas 1 and 2 will be described in detail.

[0035] As used herein, the term "(C1-C30) (sub)alkyl" means a straight-chain or branched-chain (sub)alkyl having 1 to 30 carbon atoms forming the chain, wherein the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10. The above alkyl 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 having 2 to 30 carbon atoms forming the chain, wherein the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The above alkenyl 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 having 2 to 30 carbon atoms forming the chain, wherein the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The above alkynyl may include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc. The term "(C3-C30) (sub)cycloalkyl" means a monocyclic hydrocarbon or polycyclic hydrocarbon having 3 to 30 ring framework carbon atoms, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The above cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. The term "(3- to 7-membered) heterocycloalkyl" means a cycloalkyl having 3 to 7, preferably 5 to 7, ring framework atoms and containing 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 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 ring framework carbon atoms, wherein the number of ring framework carbon atoms is preferably 6 to 25, more preferably 6 to 18. The above (sub)aryl may be partially saturated and may contain a spiro structure. The above aryl may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, phenylphenanthryl, anthracenyl, indenyl, triphenylene, pyrenyl, tetracenyl, perylenyl, yl, naphthacenyl, fluoranthenyl, spirobifluorenyl, etc. More specifically, the above aryl may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthracenyl, 2-anthracenyl, 9-anthracenyl, benzanthracenyl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, 1- yl, 2- yl, 3- yl, 4- yl, 5- Group, 6- Group, benzo[c]phenanthryl, benzo[g] Group, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzofluorenyl, dibenzofluorenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, o-terphenyl-4-yl, 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-4-yl, 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'-methylbiphenyl-4-yl, 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.

[0036] The term “(3- to 30-membered)(hetero)aryl” means an aryl 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)aryl can be monocyclic, or a fused ring fused with at least one benzene ring; can be partially saturated; can be a (hetero)aryl formed by connecting at least one heteroaryl or aryl to a heteroaryl via one or more single bonds; and can contain a spiro structure. The above heteroaryl can include monocyclic heteroaryls such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl, and fused ring heteroaryls such as benzofuryl, benzothienyl, isobenzofuryl, dibenzofuryl, dibenzothienyl, benzonaphthofuryl, benzofurylthienyl, diazabenzofuryl, 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, dihydroacridinyl, etc. 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-furyl, 3-furyl, 2-benzofuryl, 3-benzofuryl, 4-benzofuryl, 5-benzofuryl, 6-benzofuryl, 7-benzofuryl, 1-isobenzofuryl, 3-isobenzofuryl, 4-isobenzofuryl, 5-isobenzofuryl, 6-isobenzofuryl, 7-isobenzofuryl, 2-quinolinyl, 3-quinolinyl, 4-quinolinyl,5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazol-1-yl, azacarbazol-2-yl, azacarbazol-3-yl, azacarbazol-4-yl, azacarbazol-5-yl, azacarbazol-6-yl, azacarbazol-7-yl, azacarbazol-8-yl, azacarbazol-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2-tert-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4-tert-butyl-1-indolyl, 2-tert-butyl-3-indolyl, 4-tert-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothienyl, 2-dibenzothienyl, 3-dibenzothienyl, 4-dibenzothienyl, 1-silafluorenyl group, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl group, 2-germafluorenyl, 3-germafluorenyl and 4-germafluorenyl. In addition, "halogen" includes F, Cl, Br and I.

[0037] In this text, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is replaced by another atom or functional group (i.e., a substituent). The substituents of substituted alkyl, substituted alkylene, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted cycloalkyl, substituted cycloalkylene, substituted cycloalkenyl, substituted heterocycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted mono- or di-alkylamino, substituted mono- or di-arylamino, 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; hydroxyl; (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 one or more (C1-C30)alkyl, one or more (3- to 30-membered)heteroaryl, and one or more di(C6-C30)arylamino; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; 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)arylborylcarbonyl; di(C1-C30)alkylborylcarbonyl; (C1-C30)alkyl(C6-C30)arylborylcarbonyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl. Preferably, the substituents are each independently at least one selected from the group consisting of: (C1-C10)alkyl; (C6-C20)aryl unsubstituted or substituted with at least one of one or more (C1-C10)alkyl, one or more (3- to 20-membered)heteroaryl, and one or more di(C6-C20)arylamino; (3- to 20-membered)heteroaryl unsubstituted or substituted with one or more (C6-C20)aryl; and di(C6-C20)arylamino.More preferably, each substituent is independently at least one selected from the group consisting of: (C1-C6) alkyl; (C6-C20) aryl which is unsubstituted or substituted by at least one of (C1-C6) alkyl, (5- to 15-membered) heteroaryl, and di(C6-C12) arylamino; (5- to 15-membered) heteroaryl which is unsubstituted or substituted by (C6-C12) aryl; and di(C6-C12) arylamino. For example, the substituent may be at least one of the following: methyl, phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, triphenylene, naphthylphenyl, phenylnaphthyl, dimethylfluorenyl, dimethylbenzoindenyl, phenyl substituted by phenylquinoxalinyl, carbazolylphenyl, dibenzofuranyl phenyl, phenyl substituted by diphenylamino, phenylquinoxalinyl, carbazolyl, phenylcarbazolyl, dibenzofuranyl, and diphenylamino.

[0038] In the formulae of the present disclosure, if adjacent substituents are connected to each other to form a ring, the ring may be a substituted or unsubstituted, monocyclic or polycyclic (3- to 30-membered) alicyclic or aromatic ring or a combination thereof formed by connecting two or more adjacent substituents, and the formed ring may contain a heteroatom selected from at least one of B, N, O, S, Si, and P, preferably N, O, and S. 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.

[0039] In the formulae of the present disclosure, the heteroaryl or heteroarylene may each independently contain at least one heteroatom selected from B, N, O, S, Si, and P. In addition, 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- 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) alkyl di(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, and substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino.

[0040] In Formula 1, X represents O or S.

[0041] In Formula 1, R1 to R8 each independently represent -L1-HAr, hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, -NR9R 10 , or -SiR 11 R 12 R 13 ; or may be connected to adjacent substituents to form a ring; provided that at least one of R1 to R8 is -L1-HAr. According to one embodiment of the present disclosure, one of R1 to R8 is -L1-HAr, and the others are hydrogen.

[0042] In Formula 1, L1 represents a single bond, substituted or unsubstituted (C1-C30) alkylene, substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (3- to 30-membered) heteroarylene, or substituted or unsubstituted (C3-C30) cycloalkylene, where if there are multiple L1s, each L1 may be the same or different. According to one embodiment of the present disclosure, L1 represents a single bond, or substituted or unsubstituted (C6-C20) arylene. According to another embodiment of the present disclosure, L1 represents a single bond or unsubstituted (C6-C20) arylene. Specifically, L1 may represent a single bond, phenylene, naphthylene, biphenylene, naphthylphenylene, phenylnaphthylene, etc.

[0043] In Formula 1, HAr represents a substituted or unsubstituted nitrogen-containing (3- to 30-membered) heteroaryl group, and if there are multiple HArs, each HAr can be the same or different. According to one embodiment of the present disclosure, HAr represents a substituted or unsubstituted nitrogen-containing (5- to 15-membered) heteroaryl group. According to another embodiment of the present disclosure, HAr represents a substituted or unsubstituted nitrogen-containing (5- to 15-membered) heteroaryl group, and the substituents of the substituted nitrogen-containing (5- to 15-membered) heteroaryl group can be at least one unsubstituted or substituted (C6-C20) aryl group substituted by at least one of one or more (C1-C6) alkyl groups, one or more (5- to 15-membered) heteroaryl groups, and one or more di(C6-C12)arylamino groups; a (5- to 15-membered) heteroaryl group that is unsubstituted or substituted by one or more (C6-C12) aryl groups. Specifically, HAr can represent a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted benzoquinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted benzoisoquinolinyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted phenanthridinyl group, a substituted or unsubstituted benzothienopyrimidinyl group, etc. For example, HAr can represent a triazinyl group, a quinazolinyl group, a quinoxalinyl group, a naphthyridinyl group, a phenanthridinyl group, a benzoquinazolinyl group, a benzoquinoxalinyl group, etc. The triazinyl group can be substituted by at least one of a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a naphthylphenyl group, a dimethylbenzo[h]fluorenyl group, a dibenzofuran-2-ylphenyl group, and a dibenzofuranyl group; the quinazolinyl group can be substituted by at least one of a phenyl group and a naphthyl group; the quinoxalinyl group can be substituted by at least one of a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a phenanthrenyl group, a triphenylene group, a naphthylphenyl group, a phenylnaphthyl group, a dimethylfluorenyl group, a dimethylbenzo[h]fluorenyl group, a phenyl group substituted by a phenylquinoxalinyl group, a carbazol-9-ylphenyl group, a dibenzofuran-2-ylphenyl group, a phenyl group substituted by a diphenylamino group, a phenylcarbazol-9-yl group, and a dibenzofuranyl group; the naphthyridinyl group can be substituted by at least one of a phenyl group, a naphthyl group, a biphenyl group, a dimethylfluorenyl group, a dimethylbenzo[h]fluorenyl group, and a carbazol-9-ylphenyl group; the phenanthridinyl group can be substituted by at least one phenyl group; the benzoquinazolinyl group can be substituted by at least one biphenyl group; and the benzoquinoxalinyl group can be substituted by at least one of a phenyl group, a naphthyl group, a biphenyl group, and a naphthylphenyl group.

[0044] According to one embodiment of the present disclosure, Formula 1 can be represented by at least one of Formulas 1-1 to 1-4 below.

[0045]

[0046] Wherein

[0047] R1 to R8, X, L1, and HAr are as defined in Formula 1.

[0048] In Formula 2, Ar represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, -NR9R 10 、or -SiR 11 R 12 R 13 ; or may be linked to an adjacent substituent to form a ring. According to one embodiment of the present disclosure, Ar represents substituted or unsubstituted (C6-C25) aryl, substituted or unsubstituted (5- to 15-membered) heteroaryl, or -NR9R 10 . Herein, R9 and R 10 each independently represent substituted or unsubstituted (C6-C12) aryl. According to another embodiment of the present disclosure, Ar represents (C6-C25) aryl that is unsubstituted or substituted with at least one (C1-C6) alkyl, (5- to 15-membered) heteroaryl that is unsubstituted or substituted with at least one (C6-C12) aryl, or -NR9R 10 . Herein, R9 and R 10Each independently represents an unsubstituted (C6-C12) aryl group. Specifically, Ar can represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthylphenyl group, a substituted or unsubstituted phenylnaphthyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted dibenzocarbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzonaphthothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzonaphthofuranyl group, a substituted or unsubstituted diazodibenzofuranyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted benzoquinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted benzoisoquinolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzothienopyrimidinyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted phenylnaphthylamino group, a substituted or unsubstituted phenylbiphenylamino group, a substituted or unsubstituted naphthylbiphenylamino group, a substituted or unsubstituted dibiphenylamino group, a substituted or unsubstituted biphenylfluorenylamino group, or a substituted or unsubstituted biphenyldibenzofuranylamino group, etc. For example, Ar can represent a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a spirobifluorenyl group, a dimethylfluorenyl group, a dimethylbenzofluorenyl group, a phenylpyridyl group, a diphenylpyrimidinyl group, a dimethyltriazinyl group, a phenylquinolyl group, a diphenylquinazolinyl group, a biphenylquinazolinyl group, a phenylquinoxalinyl group, a diphenylquinoxalinyl group, a naphthylquinoxalinyl group, a phenylnaphthyridinyl group, a carbazolyl group, a phenylcarbazolyl group, a dibenzofuranyl group, a phenyldibenzofuranyl group, a dibenzothiophenyl group, a phenyldiazodibenzofuranyl group, a phenylbenzoquinazolinyl group, a phenylbenzoquinoxalinyl group, a diphenylamino group, a phenylnaphthylamino group, a phenylbiphenylamino group, etc.

[0049] In Formulas 3 and 4, X1 to X 25 each independently represents N or CR 14 . According to one embodiment of the present disclosure, X1 to X 25 are all CR 14 .

[0050] In Formulas 3 and 4, R 14each 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 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 adjacent Rs 14 may be joined to each other to form a ring, and wherein if there are a plurality of Rs 14 , then each R 14 may be the same or different. According to one embodiment of the present disclosure, Rs 14 may each independently represent hydrogen, or a substituted or unsubstituted (C6-C12) aryl group, or adjacent Rs 14 may be joined to each other to form a ring. According to another embodiment of the present disclosure, Rs 14 each independently represent hydrogen, or an unsubstituted (C6-C12) aryl group, or adjacent Rs 14 may be joined to each other to form a benzene ring. Specifically, Rs 14 may each independently represent hydrogen, phenyl, etc., or adjacent Rs 14 may be joined to each other to form a benzene ring.

[0051] In Formula 2, L2 represents a single bond, a substituted or unsubstituted (C1-C30) alkylene group, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstituted (3- to 30-membered) heteroarylene group, or a substituted or unsubstituted (C3-C30) cycloalkylene group. According to one embodiment of the present disclosure, L2 represents a single bond, a substituted or unsubstituted (C6-C12) arylene group, or a substituted or unsubstituted (5- to 15-membered) heteroarylene group. According to another embodiment of the present disclosure, L2 represents a single bond, an unsubstituted (C6-C12) arylene group, or an unsubstituted or (5- to 15-membered) heteroarylene group substituted with one or more (C6-C12) aryl groups. Specifically, L2 may represent a single bond, a phenylene group, a naphthylene group, a biphenylene group, a phenylpyridyl group, a phenyltriazinyl group, a quinolinylene group, a quinazolinylene group, a phenylquinazolinylene group, a quinoxalinylene group, a phenylquinoxalinylene group, a naphthyridinylene group, a carbazolylene group, a dibenzofuranylene group, a benzquinazolinylene group, a benzquinoxalinylene group, a diazabenzofuranylene group, etc.

[0052] In Formulas 1 and 2, R9 to R 13 each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group. According to one embodiment of the present disclosure, R9 and R 10 each independently represents a substituted or unsubstituted (C6-C12) aryl group. According to another embodiment of the present disclosure, R9 and R 10 each independently represents an unsubstituted (C6-C12) aryl group. Specifically, R9 and R 10 each independently represents a phenyl group, a naphthyl group, a biphenyl group, etc.

[0053] According to one embodiment of the present disclosure, Formula 3 can be represented by the following Formula 3-1:

[0054]

[0055] wherein

[0056] R 31 to R 33 each 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 may be connected to an adjacent substituent to form a ring; and

[0057] aa represents an integer from 1 to 3, ab represents an integer from 1 to 4, ac represents an integer from 1 to 5, wherein if aa, ab, and ac are integers of 2 or greater, then each R 31 each R 32 and each R 33 may be the same or different.

[0058] According to one embodiment of the present disclosure, Formula 4 can be represented by the following Formula 4-1:

[0059]

[0060] wherein

[0061] R 41 to R 44 each 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 may be linked to an adjacent substituent to form a ring; and

[0062] ba represents an integer from 1 to 3, bb and bc each independently represent an integer from 1 to 4, bd represents 1 or 2, where if ba, bb, bc, and bd are integers of 2 or greater, then each R 41 、each R 42 、each R 43 and each R 44 may be the same or different.

[0063] The compounds represented by Formula 1 include the following compounds, but are not limited thereto.

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071] The compounds represented by Formula 2 include the following compounds, but are not limited thereto.

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078] One or more of Compounds E-1 to E-135 and one or more of Compounds H-1 to H-122 may be combined and used in an organic electroluminescent device.

[0079] The compound represented by Formula 1 according to the present disclosure can be prepared by a synthesis method known to those skilled in the art. For example, it can be prepared by referring to Korean Patent Application Publication Nos. 2012-0033017, 2013-0128322, 2016-0038006, 2015-0122343, and 2016-0049083; US Patent Application Publication No. 2016 / 0233436; International Publication No. WO 2017 / 178311, etc., but is not limited thereto.

[0080] 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. For example, it can be prepared by referring to the following Reaction Scheme 1 of Korean Patent Application Publication No. 2018-0012709, etc., but is not limited thereto.

[0081] [Reaction Scheme 1]

[0082]

[0083] wherein, X1 to X 12 , L2, and Ar are as defined in Formulas 2 and 3, and OTf represents trifluoromethanesulfonate.

[0084] The organic electroluminescent device according to the present disclosure includes a first electrode; a second electrode; and at least one organic layer between the first electrode and the second electrode.

[0085] One of the first electrode and the second electrode may be an anode, and the other may be a cathode. The organic layer includes a light-emitting layer, and may further include at least one layer selected from the following: a hole injection layer, a hole transport layer, a hole assisting layer, a light-emitting assisting 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. Herein, the second electrode may be a transmissive reflective electrode or a reflective electrode, and depending on the materials used, may be a top emission, bottom emission, or both-side emission type. Further, 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.

[0086] 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. 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.

[0087] The light-emitting layer includes a host and a dopant, and the host includes a variety of host materials. 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. Herein, 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.

[0088] The light-emitting layer is a layer from which light is emitted, and may be a single layer or a multi-layer in which two or more layers are stacked. Among the variety of host materials according to the present disclosure, the first and second host materials may be included in one layer simultaneously or may be included in different light-emitting layers respectively. According to one embodiment of the present disclosure, the doping concentration of the dopant compound may be less than 20 wt% with respect to the host compound of the light-emitting layer.

[0089] 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 assisting layer, a light emitting assisting 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. In 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 assisting material, a light emitting material, a light emitting assisting material, and an electron blocking material. In addition, in 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.

[0090] The dopant included in the organic electroluminescent device according to the present disclosure may be at least one phosphorescent or fluorescent dopant, and preferably a phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particularly limited, but may be selected from metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), preferably ortho-metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and more preferably ortho-metallated iridium complex compounds.

[0091] The dopant included in the organic electroluminescent device of the present disclosure may include, but is not limited to, the compound represented by Formula 101.

[0092]

[0093] In Formula 101, L is selected from the following Structures 1 and 2:

[0094]

[0095] R 100 to R 103 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 cyano group, a substituted or unsubstituted (3-membered to 30-membered) heteroaryl group, or a substituted or unsubstituted (C1-C30) alkoxy group; or may be connected to an adjacent substituent to form a ring together with pyridine, such as a substituted or unsubstituted quinoline, benzofuranopyridine, benzothiophenopyridine, benzothienoquinoline, or indenoquinoline ring;

[0096] R 104 to R 107Each independently represents hydrogen, deuterium, a halogen, an unsubstituted or one or more 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 an adjacent substituent to form a ring together with the benzene, such as a substituted or unsubstituted naphthyl group, fluorene, dibenzothiophene, dibenzofuran, indolopyridine, benzofuranopyridine, or benzothiophenopyridine ring;

[0097] R 201 to R 211 Each independently represents hydrogen, deuterium, a halogen, an unsubstituted or one or more 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 an adjacent substituent to form a ring; and

[0098] n represents an integer from 1 to 3.

[0099] Specific examples of the dopant compound are as follows, but are not limited thereto.

[0100]

[0101]

[0102]

[0103]

[0104] 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. Multiple hole injection layers may be used to reduce the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer. Two compounds may be used simultaneously for each layer. The hole transport layer or the electron blocking layer may also be formed of multiple layers.

[0105] In addition, 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. Multiple electron buffer layers may be used to control electron injection and enhance the interfacial characteristics between the light emitting layer and the electron injection layer. Two compounds may be used simultaneously for each layer. The hole blocking layer or the electron transport layer may also be formed of multiple layers, and each layer may contain two or more compounds.

[0106] In addition, the organic electroluminescent compound or multiple host materials according to the present disclosure may also be used in an organic electroluminescent device including quantum dots (QDs).

[0107] To form each layer of the organic electroluminescent device of the present disclosure, dry film-forming methods such as vacuum evaporation, sputtering, plasma, and ion plating methods, or wet film-forming methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, and flow coating methods can be used.

[0108] When a solvent is used in the wet film-forming method, a thin film can be formed by dissolving or diffusing the materials for forming each layer into any suitable solvent (such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.). The solvent can be any solvent in which the materials for forming each layer can be dissolved or diffused, and there are no problems in terms of film-forming ability.

[0109] In addition, the first and second host compounds of the present disclosure can be formed into a film in the methods listed above, usually by co-evaporation method or mixed evaporation method. Co-evaporation is a mixed deposition method in which two or more materials are placed in corresponding individual crucible sources and current is applied to two chambers 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 evaporation and current is applied to the chamber to evaporate the materials. In addition, if the first and second host compounds are present in the same layer or different layers of the organic electroluminescent device, the two host compounds can be formed into a film individually. For example, the second host compound can be deposited after depositing the first host compound.

[0110] The present disclosure can provide a display device by using a plurality of host materials including the compound represented by Formula 1 and the compound represented by Formula 2. That is, a display system or a lighting system can be manufactured by using the plurality of host materials of the present disclosure. Specifically, a display system can be produced by using the plurality of host materials of the present disclosure, such as a display system for a smartphone, a tablet computer, a laptop computer, a PC, a TV, or an automobile; or a lighting system, such as an outdoor or indoor lighting system.

[0111] Hereinafter, the preparation method and characteristics of the compounds of the present disclosure, as well as the characteristics of the organic electroluminescent device including the plurality of host materials of the present disclosure, will be explained in detail with reference to the representative compounds of the present disclosure. However, the present disclosure is not limited to the following examples.

[0112] Synthesis Example 1: Preparation of Compound H-49

[0113]

[0114] Synthesis of Compound 1

[0115] In a flask, 70 g of 2-nitro-1-naphthol (370 mmol) and 4.5 g of 4-dimethylaminopyridine (DMAP) (37 mmol) were dissolved in 1800 mL of dichloromethane (MC). 62 mL of triethylamine (TEA) (444 mmol) was added dropwise at 0 °C and stirred for 20 minutes. 125.3 g of trifluoromethanesulfonic anhydride (444 mmol) was slowly added dropwise to the reactants at the same temperature and stirred for 1 hour. After the reaction was completed, the organic layer was extracted with MC, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 96.2 g of Compound 1 (yield: 81%).

[0116] Synthesis of Compound 2

[0117] In a flask, 96.2 g of Compound 1 (299 mmol), 72.1 g of 2-bromophenylboronic acid (359 mmol), 17.3 g of tetrakis(triphenylphosphine)palladium(0) (15 mmol), and 79.3 g of sodium carbonate (749 mmol) were dissolved in 1400 mL of toluene, 350 mL of ethanol, and 350 mL of water, and refluxed for 1 hour. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 98 g of Compound 2 (yield: 99%).

[0118] Synthesis of Compound 3

[0119] In a flask, 98 g of Compound 2 (299 mmol), 78.5 g of 2-aminophenylboronic acid pinacol ester (358 mmol), 17.2 g of tetrakis(triphenylphosphine)palladium(0) (15 mmol), and 103 g of potassium carbonate (747 mmol) were dissolved in 1300 mL of toluene, 350 mL of ethanol, and 350 mL of water, and refluxed for 20 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 54 g of Compound 3 (yield: 53%).

[0120] Synthesis of Compound 4

[0121] In a flask, 25 g of Compound 3 (73 mmol) was dissolved in 250 mL of acetic acid and 25 mL of sulfuric acid. 6.5 g of sodium nitrite (95 mmol) was slowly added dropwise at 0 °C and stirred for 40 minutes. After the reaction was completed, the reaction product was added dropwise to water, and filtered to remove the moisture. The residue was dried and separated by column chromatography to obtain 2 g of Compound 4 (yield: 8.4%).

[0122] Synthesis of Compound 5

[0123] In a flask, 4.7 g of Compound 4 (15 mmol) was dissolved in 48 mL of triethyl phosphite and 48 mL of 1,2-dichlorobenzene, and the mixture was refluxed for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 2.7 g of Compound 5 (yield: 63%).

[0124] Synthesis of Compound H-49

[0125] In a flask, 2.1 g of Compound 5 (7 mmol), 3.1 g of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (8 mmol), 0.81 g of palladium(II) acetate (0.36 mmol), 0.3 g of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-Phos) (0.7 mmol), and 1.7 g of sodium tert-butoxide (18 mmol) were dissolved in 72 mL of 1,2-xylene, and the mixture was refluxed for 4 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 2.5 g of Compound H-49 (yield: 58%).

[0126] Compound MW UV PL Melting Point Tg H-49 598.71 308 nm 495 nm 285℃ 132.37℃

[0127] Synthesis Example 2: Preparation of Compound H-6

[0128]

[0129] Synthesis of Compound 6

[0130] 155 mL of toluene was added to 9 g of Compound 5 (30.89 mmol), 10.6 g of 1-bromo-3-iodobenzene (61.78 mmol), 3 g of CuI (15.44 mmol), 1.8 g of ethylenediamine (EDA) (30.89 mmol), and 16.4 g of K3PO4 (77.22 mmol), and the mixture was stirred under reflux for one day. After the reaction was completed, the reaction product was cooled to room temperature, and the resulting solid was filtered under reduced pressure. The solid was dissolved in CHCl3 and separated by column chromatography using MC / Hex to obtain 10 g of Compound 6 (yield: 75%).

[0131] Synthesis of Compound H-6

[0132] 50 mL of toluene, 13 mL of EtOH, and 13 mL of purified water were added to 5.7 g of compound 6 (12.77 mmol), 0.73 g of Pd(PPh3)4 (0.638 mmol), and 3.5 g of K2CO3 (25.54 mmol), and the mixture was stirred under reflux for 2 h. After the reaction was completed, the reaction product was cooled to room temperature, and the resulting solid was filtered under reduced pressure. The solid was dissolved in CHCl3 and separated by column chromatography using MC / Hex to obtain 2.9 g of compound H-6 (yield: 43%).

[0133] 1 H NMR (600 MHz, DMSO-d6, δ) 8.232 - 8.206 (m, 3H), 8.111 - 8.098 (d, 1H), 7.962 - 7.946 (m, 1H), 7.929 - 7.903 (m, 3H), 7.896 - 7.882 (d, 1H), 7.806 - 7.802 (d, 2H), 7.783 - 7.759 (t, 2H), 7.738 - 7.723 (d, 1H), 7.635 - 7.620 (m, 1H), 7.581 - 7.548 (m, 2H), 7.513 - 7.440 (m, 6H)

[0134] Compound MW Tg Melting Point H-6 533.6 119℃ 208℃

[0135] Synthesis Example 3: Preparation of Compound H-7

[0136]

[0137] 6.6 g of compound 6 (14.78 mmol), 3.4 g of dibenzo[b,d]furan-1-ylboronic acid (16.24 mmol), 0.85 g of Pd(PPh3)4 (0.739 mmol), and 4 g of K2CO3 (29.57 mmol) were added to 60 mL of toluene, 15 mL of ethanol, and 15 mL of purified water, and the mixture was stirred under reflux for one day. After the reaction was completed, the reaction product was cooled to room temperature, and the resulting solid was filtered under reduced pressure. The filtered solid was dissolved in CHCl3, extracted with MC / Hex, and separated by column chromatography to obtain 3.5 g of compound H-7 (yield: 45%).

[0138] 11H NMR (600 MHz, DMSO, δ) 7.953 - 7.927 (m, 2H), 7.896 - 7.872 (t, 2H), 7.848 - 7.810 (m, 3H), 7.793 - 7.746 (m, 4H), 7.656 - 7.601 (m, 4H), 7.539 - 7.511 (t, 1H), 7.485 - 7.443 (m, 4H), 7.419 - 7.393 (t, 1H), 7.369 - 7.356 (d, 1H), 7.294 - 7.269 (t, 1H)

[0139] Synthesis Example 4: Preparation of Compound H-1

[0140]

[0141] 86 mL of o - xylene was added to 5 g of Compound 5 (17.16 mmol), 5.3 g of 4 - bromo - 1,1':2',1'' - terphenyl (17.16 mmol), 0.8 g of Pd2(dba)3 (0.858 mmol), 0.7 g of 2 - (dicyclohexylphosphino) - 2',6' - dimethoxybiphenyl (s - phos) (1.716 mmol), and 5 g of NaOt - Bu (51.48 mmol), and the mixture was stirred under reflux for 2 hours. After the reaction was completed, the reaction product was cooled to room temperature, and the resulting solid was filtered under reduced pressure. The filtered solid was dissolved in CHCl3, extracted with MC / Hex, and separated by column chromatography to obtain 2.4 g of Compound H - 1 (yield: 26%).

[0142] 1 1H NMR (DMSO - d6) δ: 7.92 - 7.88 (m, 1H), 7.87 - 7.83 (m, 1H), 7.79 (d, J = 9.1 Hz, 1H), 7.74 (t, J = 8.3 Hz, 2H), 7.59 - 7.54 (m, 2H), 7.53 - 7.49 (m, 2H), 7.48 - 7.41 (m, 6H), 7.38 (d, J = 2.3 Hz, 1H), 7.36 (d, J = 2.1 Hz, 2H), 7.34 - 7.31 (m, 2H), 7.30 - 7.25 (m, 2H), 7.21 - 7.17 (m, 2H), 7.12 (dd, J = 8.1, 0.6 Hz, 1H)

[0143] Synthesis Example 5: Preparation of Compound H-122

[0144]

[0145] 90 mL of o-xylene was added to 5 g of Compound 5 (17.16 mmol), 7 g of 1-(3-bromophenyl)dibenzo[b,d]thiophene (20.59 mmol), 0.16 g of CuI (0.858 mmol), 1 g of ethylenediamine (EDA) (17.16 mmol), and 9.1 g of K3PO4 (42.90 mmol), and the mixture was stirred under reflux for 2 h. After completion of the reaction, the reaction product was cooled to room temperature, and the resulting solid was filtered under reduced pressure. The filtered solid was dissolved in CHCl3, extracted with MC / Hex, and separated by column chromatography to obtain 2.2 g of Compound H-122 (yield: 22%).

[0146] 1 H NMR (DMSO-d6) δ: 8.09 (dd, J = 8.0, 1.1 Hz, 1H), 8.04 (ddd, J = 8.0, 1.1, 0.7 Hz, 1H), 7.92 - 7.87 (m, 2H), 7.85 - 7.82 (m, 1H), 7.80 (ddd, J = 8.0, 2.1, 1.2 Hz, 1H), 7.78 - 7.71 (m, 3H), 7.68 - 7.63 (m, 2H), 7.60 - 7.52 (m, 3H), 7.48 - 7.38 (m, 5H), 7.36 - 7.24 (m, 4H)

[0147] Synthesis Example 6: Preparation of Compound H-16

[0148]

[0149] In a flask, 70 mL of toluene was added dropwise to 4.0 g of Compound 5 (14 mmol), 4.87 g of 9-(3-bromophenyl)-9H-carbazole (15 mmol), 1.307 g of CuI (7 mmol), 1.647 g of EDA (27 mmol), and 5.83 g of K3PO4 (27 mmol), and the mixture was stirred at 180 °C under reflux for 4 h. After completion of the reaction, the reaction product was extracted with ethyl acetate (EA) and dried over MgSO4. The residue was separated by column chromatography, and the resulting solid was filtered under reduced pressure by adding methanol thereto to obtain 2.3 g of Compound H-16 (yield: 31.5%).

[0150] 11H NMR (600 MHz, DMSO-d6, δ) 8.27 (d, J = 7.8 Hz, 2H), 8.01 (t, J = 8.0 Hz, 1H), 7.95 - 7.92 (m, 1H), 7.91 - 7.84 (m, 4H), 7.83 (d, J = 6.9 Hz, 1H), 7.81 - 7.77 (m, 2H), 7.66 (d, J = 8.9 Hz, 1H), 7.63 - 7.57 (m, 3H), 7.51 - 7.44 (m, 5H), 7.44 - 7.40 (m, 2H), 7.35 - 7.30 (m, 2H)

[0151] Synthesis Example 7: Preparation of Compound H-104

[0152]

[0153] Synthesis of Compound 7-1

[0154] In a flask, 70 g of Compound 5 (240 mmol) and 40.6 g of N-bromosuccinimide (255 mmol) were dissolved in 1200 mL of dimethylformamide and stirred at 0 °C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate and the residual moisture was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 68 g of Compound 7-1 (yield: 76%).

[0155] Synthesis of Compound 7-2

[0156] In a flask, 47.3 g of Compound 7-1 (127 mmol), 42 g of bis(pinacolato)diboron (166 mmol), 4.5 g of bis(triphenylphosphine)palladium(II) dichloride (6.4 mmol), and 25 g of potassium acetate (255 mmol) were dissolved in 635 mL of 1,4-dioxane and refluxed for 4 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate after distillation under reduced pressure and the residual moisture was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 31.5 g of Compound 7-2 (yield: 59%).

[0157] Synthesis of Compound 7-3

[0158] In a flask, 4.5 g of compound 7-2 (10.7 mmol), 1.9 g of 1-bromobenzene (11.85 mmol), 0.63 g of tetrakis(triphenylphosphine)palladium(0) (0.54 mmol), and 3.7 g of potassium carbonate (26.95 mmol) were dissolved in 54 mL of toluene, 13 mL of ethanol, and 13 mL of water, and refluxed for 12 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 2.2 g of compound 7-3 (yield: 56%).

[0159] Synthesis of Compound H-104

[0160] In a flask, 2.2 g of compound 7-3 (5.9 mmol), 1.58 g of 2-chloro-3-phenylquinoxaline (6.57 mmol), 3.89 g of cesium carbonate (11.96 mmol), and 0.36 g of 4-dimethylaminopyridine (2.99 mmol) were dissolved in 30 mL of dimethyl sulfoxide, and stirred at 100 °C for 4 hours. After the reaction was completed, the reaction product was cooled to room temperature, and distilled water was added thereto. The organic layer was extracted with ethyl acetate, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 2.9 g of compound H-104 (yield: 85%).

[0161] Compound MW Melting Point Tg H-104 571.68 210℃ 167℃

[0162] Synthesis Example 8: Preparation of Compound H-11

[0163]

[0164] In a flask, 60 mL of toluene was added to 5.0 g of compound 6 (11.2 mmol), 3.0 g of N-phenyl-[1,1'-biphenyl]-4-amine (12.3 mmol), 0.5 g of Pd2(dba)3 (0.56 mmol), 0.46 g of s-phos (1.12 mmol), and 2.7 g of NaOtBu (28 mmol), and stirred under reflux for 6 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and stirred at room temperature. The solid formed by adding MeOH thereto was filtered under reduced pressure and separated by column chromatography using MC / Hex to obtain 2.3 g of compound H-11 (yield: 34%).

[0165] Compound MW Melting Point H-11 610.8 132℃

[0166] Synthesis Example 9: Preparation of Compound H-120

[0167]

[0168] In a flask, 80 mL of o-xylene was added to 5.0 g of 14H-7b,14-diazadibenzo[3,4:5,6]azulen[7,8,1-lma]fluorene (11.2 mmol), 5.4 g of 4-bromo-N,N-diphenylaniline (16.7 mmol), 0.7 g of Pd2(dba)3 (0.76 mmol), 0.6 g of s-phos (1.52 mmol), and 2.9 g of NaOtBu (30.4 mmol), and the mixture was stirred under reflux for 4 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and stirred at room temperature. The solid formed by adding MeOH thereto was filtered under reduced pressure and separated by column chromatography using MC / Hex to obtain 4.0 g of compound H-120 (yield: 46%).

[0169] Compound MW Melting Point H-120 573.7 317℃

[0170] Synthesis Example 10: Preparation of Compound H-121

[0171]

[0172] In a flask, 160 mL of toluene was added to 14.0 g of compound 6 (31.4 mmol), 7.78 g of N-phenyl-[1,1'-biphenyl]-3-amine (31.7 mmol), 1.44 g of Pd2(dba)3 (1.57 mmol), 635 mg of t-Bu3P (3.14 mmol), and 6.04 g of t-BuONa (62.8 mmol), 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 filtered under reduced pressure and separated by column chromatography using MC / Hex to obtain 14.6 g of compound H-121 (yield: 76%).

[0173] Compound MW Melting Point H-121 610.7 141℃

[0174] Synthesis Example 11: Preparation of Compound H-119

[0175]

[0176] In a flask, 170 mL of toluene was added to 10 g of Compound 5 (34.3 mmol), 12.7 g of 3-bromodibenz[b,d]furan (51.45 mmol), 3.3 g of CuI (17.15 mmol), 4.6 mL of ethylenediamine (EDA) (68.8 mmol), and 21.8 g of K3PO4 (102.9 mmol), and the mixture was stirred under reflux for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and stirred at room temperature. The solid formed by adding MeOH thereto was filtered under reduced pressure and separated by column chromatography using MC / Hex to obtain 8.3 g of Compound H-119 (yield: 53%).

[0177] Compound MW Melting Point H-119 457.53 255.4℃

[0178] Synthesis Example 12: Preparation of Compound H-12

[0179]

[0180] Synthesis of Compound 12-1

[0181] 10.0 g of 3H-3-azadibenz[g,ij]naphtho[2,1,8-cde]azulene (34.3 mmol), 14.6 g of 1-bromo-4-iodobenzene (51.5 mmol), 3.28 g of CuI (17.2 mmol), 4.12 g of EDA (68.6 mmol), 14.6 g of K3PO4 (68.6 mmol), and 170 mL of toluene were introduced into a flask and stirred at 145 °C under reflux for 3 hours. After the reaction was completed, the reaction product was extracted with MC and dried over MgSO4. The residue was separated by column chromatography, and the solid formed was filtered under reduced pressure by adding MeOH thereto to obtain 9.0 g of Compound 12-1 (yield: 59%).

[0182] Synthesis of Compound H-12

[0183] 5.0 g of Compound 12-1 (11 mmol), 3.3 g of N-phenyl-[1,1'-biphenyl]-4-amine (13 mmol), 0.513 g of Pd2(dba)3 (0.56 mmol), 0.460 g of s-phos (1 mmol), 2.691 g of NaOt-Bu (28 mmol), and 60 mL of toluene were introduced into a flask and stirred at 100 °C under reflux for 0.5 h. After completion of the reaction, the reaction product was extracted with MC and dried over MgSO4. The residue was separated by column chromatography, and the resulting solid was filtered under reduced pressure by adding MeOH thereto to obtain 1.3 g of Compound H-12 (yield: 19%).

[0184] Compound MW Melting Point H-12 610.76 168℃

[0185] Synthesis Example 13: Preparation of Compound H-35

[0186]

[0187] In a flask, 75 mL of o-xylene was added to 5.0 g of 14H-7b,14-diazadibenzo[3,4:5,6]azuleno[7,8,1-lma]fluorene (15.1 mmol), 4.1 g of 2-bromodibenzo[b,d]furan (16.6 mmol), 0.691 g of Pd2(dba)3 (0.755 mmol), 0.620 g of s-phos (1.51 mmol), and 3.63 g of NaOtBu (37.8 mmol), and stirred under reflux for 6 h. After completion of the reaction, the reaction mixture was cooled to room temperature and stirred at room temperature. The solid formed by adding MeOH thereto was filtered under reduced pressure and separated by column chromatography using MC / Hex to obtain 1.9 g of Compound H-35 (yield: 25%).

[0188] Compound MW Melting Point H-35 496.56 280℃

[0189] Synthesis Example 14: Preparation of Compound E-112

[0190]

[0191] Synthesis of Compound 14-1

[0192] In a flask, 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) were dissolved in 470 mL of toluene, 235 mL of ethanol and 235 mL of water, and refluxed at 140 °C for 4 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 20 g of compound 14-1 (yield: 56.8%).

[0193] Synthesis of Compound 14-2

[0194] In a flask, 20 g of compound 14-1 (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) were dissolved in 270 mL of 1,4-dioxane, and refluxed at 150 °C for 4 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 23 g of compound 14-2 (yield: 100%).

[0195] Synthesis of Compound E-112

[0196] In a flask, 7 g of compound 14-2 (16.6 mmol), 7.35 g of 2-chloro-4,6-bis(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) were dissolved in 83 mL of toluene, and refluxed at 130 °C for 18 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 2 g of compound E-112 (yield: 19.2%).

[0197] Synthesis Example 15: Preparation of Compound E-117

[0198]

[0199] Synthesis of Compound 15-1

[0200] In a flask, 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) were dissolved in 400 mL of toluene and refluxed at 140 °C for 4 h. After the reaction was completed, the organic layer was extracted with ethyl acetate and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 20 g of compound 15-1 (yield: 46.6%).

[0201] Synthesis of Compound E-117

[0202] In a flask, 7 g of compound 15-1 (13 mmol), 4.6 g of 2-(dibenzo[b,d]furan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (15.6 mmol), 4.5 g of K2CO3 (32.5 mmol) and 0.75 g of Pd(PPh3)4 (0.65 mmol) were dissolved in 65 mL of toluene, 32.5 mL of ethanol and 32.5 mL of water and refluxed at 130 °C for 3 h. After the reaction was completed, the organic layer was extracted with ethyl acetate and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 3.4 g of compound E-117 (yield: 41%).

[0203] Synthesis Example 16: Preparation of Compound E-130

[0204]

[0205] In a flask, 4.4 g of compound 15-1 (12.3 mmol), 5 g of 2-(dibenzo[b,d]furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (13.5 mmol), 4.5 g of Cs2CO3 (32.5 mmol) and 0.75 g of Pd(PPh3)4 (0.65 mmol) were dissolved in 60 mL of toluene, 30 mL of ethanol and 30 mL of water and refluxed at 130 °C for 3 h. After the reaction was completed, the organic layer was extracted with ethyl acetate and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 4 g of compound E-130 (yield: 49%).

[0206] Synthesis Example 17: Preparation of Compound E-111

[0207]

[0208] In a flask, 64 mL of toluene, 16 mL of EtOH, and 16 mL of purified water were added to 6 g of compound 14-2 (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), 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 filtered under reduced pressure and separated by column chromatography using MC / Hex to obtain 4 g of compound E-111 (yield: 44%).

[0209] 1 H NMR (DMSO-d6) δ: 9.42 (d, J = 1.3 Hz, 1H), 9.29 - 9.24 (m, 1H), 8.83 (td, J = 8.6, 1.5 Hz, 3H), 8.72 (d, J = 7.3 Hz, 1H), 8.30 (d, J = 8.0 Hz, 1H), 8.22 (d, J = 8.7 Hz, 1H), 8.12 - 8.07 (m, 1H), 7.92 (dd, J = 8.3, 0.8 Hz, 1H), 7.89 (d, J = 7.3 Hz, 1H), 7.81 - 7.72 (m, 6H), 7.72 - 7.65 (m, 2H), 7.65 - 7.60 (m, 1H), 7.54 - 7.41 (m, 3H), 7.04 (ddd, J = 8.1, 7.3, 0.9 Hz, 1H), 6.53 (dt, J = 8.0, 0.9 Hz, 1H)

[0210] Compound MW Melting Point E-111 575.6 131.3℃

[0211] Synthesis Example 18: Preparation of Compound E-90

[0212]

[0213] Synthesis of Compound 18-1

[0214] In a flask, 150 mL of toluene and 30 mL of purified water were added to 10 g of 2,4,6-trichloro-1,3,5-triazine (54.22 mmol), 20.7 g of dibenzo[b,d]furan-1-ylboronic acid (97.60 mmol), 0.76 g of PdCl2(PPh3)2 (1.084 mmol), and 5.7 g of Na2CO3 (54.22 mmol), and the mixture was stirred for 2 days. After the reaction was completed, the mixture was cooled to room temperature and extracted with distilled water and MeOH to obtain 3.4 g of compound 18-1 (yield: 14%).

[0215] Synthesis of Compound E-90

[0216] In a flask, 32 mL of toluene, 8 mL of EtOH, and 8 mL of purified water were added to 3.4 g of Compound 18-1 (7.592 mmol), 1.5 g of naphthalene-2-ylboronic acid (9.111 mmol), 0.4 g of Pd(PPh3)4 (0.379 mmol), and 2 g of K2CO3 (15.18 mmol), and the mixture was stirred at 140 °C under reflux for 1 hour. After the reaction was completed, the mixture was concentrated under reduced pressure and extracted with MC, and the organic layer was concentrated. The concentrated organic layer was separated by column chromatography using MC / Hex to obtain 0.88 g of Compound E-90 (yield: 21%).

[0217] 1 H NMR (DMSO-d6) δ: 9.35 (d, J = 1.6 Hz, 1H), 8.74 (dd, J = 8.6, 1.7 Hz, 1H), 8.71 (dd, J = 7.7, 1.2 Hz, 2H), 8.51 (dd, J = 7.7, 1.0 Hz, 2H), 8.20 (d, J = 8.7 Hz, 1H), 8.13 - 8.07 (m, 4H), 7.86 - 7.80 (m, 4H), 7.75 - 7.70 (m, 1H), 7.66 (dd, J = 8.5, 7.0 Hz, 1H), 7.59 (ddd, J = 8.4, 7.2, 1.3 Hz, 2H), 7.18 (ddd, J = 8.1, 7.1, 1.0 Hz, 2H)

[0218] Compound MW Melting Point E-90 539.5 282.1℃

[0219] Synthesis Example 19: Preparation of Compound E-125

[0220]

[0221] In a flask, 3.0 g of dibenzo[b,d]furan-1-ylboronic acid (14.2 mmol), 7.3 g of 2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (15.6 mmol), 0.8 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, and the mixture was refluxed for 2 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 2.7 g of Compound E-125 (yield: 35%).

[0222] Compound MW Melting Point E-125 551.6 233℃

[0223] Synthesis Example 20: Preparation of Compound E-106

[0224]

[0225] In a flask, 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-diphenyl-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, and refluxed for 2 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 1.9 g of compound E-106 (yield: 26%).

[0226] Compound MW Melting Point E-106 525.6 203℃

[0227] Synthesis Example 21: Preparation of Compound E-91

[0228]

[0229] In a flask, 1.6 g of 2,4-dichloro-6-(4-(naphthalen-2-yl)phenyl)-1,3,5-triazine (4.54 mmol), 2.12 g of dibenzo[b,d]furan-1-ylboronic acid (10 mmol), 0.26 g of tetrakis(triphenylphosphine)palladium(0) (0.23 mmol), and 1.3 g of sodium carbonate (9.0 mmol) were dissolved in 16 mL of toluene, 1 mL of ethanol, and 1 mL of water, and refluxed for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 1.0 g of compound E-91 (yield: 36%).

[0230] Compound MW Melting Point E-91 615.7 304℃

[0231] Synthesis Example 22: Preparation of Compound E-110

[0232]

[0233] In a flask, 4.0 g of 2-(4-(dibenzo[b,d]furan-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (10.8 mmol), 4.4 g of 2-chloro-4,6-di(naphthalen-2-yl)-1,3,5-triazine (11.9 mmol), 0.6 g of tetrakis(triphenylphosphine)palladium(0) (0.54 mmol) and 3.0 g of sodium carbonate (21.6 mmol) were dissolved in 30 mL of toluene, 7 mL of ethanol and 10 mL of water, and refluxed for 7 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 4.0 g of compound E-110 (yield: 65%).

[0234] Compound MW Melting Point E-110 575.2 261℃

[0235] Device Examples 1 to 10: Production of OLEDs Containing Various Host Materials According to the Present Disclosure

[0236] Producing an organic electroluminescent device (OLED) according to the present disclosure comprising a plurality of host materials according to the present disclosure. The indium tin oxide (ITO) thin film (10 Ω / sq) (Geomatec, Japan) on the glass substrate for the OLED was ultrasonically washed sequentially with trichloroethylene, acetone, ethanol, and distilled water, and then stored in isopropyl alcohol. Next, the ITO substrate was mounted on the substrate holder of the 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 -6Thereafter, an electric current is applied to the chamber to evaporate the materials introduced above, thereby forming a first hole injection layer with a thickness of 80 nm on the ITO substrate. Then, compound HI-2 is introduced into another chamber of the vacuum vapor deposition apparatus, and the compound is 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. Compound HT-1 is introduced into another chamber of the vacuum vapor deposition apparatus, and the compound is 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. Compound HT-2 is introduced into another chamber of the vacuum vapor deposition apparatus, and the compound is 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, the light-emitting layer is then deposited as follows. The first and second host compounds shown in Table 1 below are introduced as hosts into two chambers of the vacuum vapor deposition apparatus, and compound D-39 is introduced into another chamber. The two host materials are evaporated at a rate of 1:1, and the dopant material is evaporated simultaneously at a different rate, and these are deposited at a doping amount of 3 wt% based on the total amount of the host and the dopant to form a light-emitting layer with a thickness of 40 nm on the second hole transport layer. Then, compound ET-1 and compound EI-1 are introduced into two additional chambers, evaporated at a rate of 1:1, and deposited to form an electron transport layer with a thickness of 35 nm on the light-emitting layer. Next, 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 is deposited on the electron injection layer by another vacuum vapor deposition apparatus. Thus, an OLED is produced.

[0237] Comparative Examples 1 and 2: Production of OLEDs Not According to the Present Disclosure

[0238] An OLED is produced in the same manner as in Device Example 1, except that only one compound (i.e., the first host compound listed in Table 1 below) is used instead of two hosts.

[0239] Table 1 below provides the luminous efficiency of the OLED devices produced in the device examples and the comparative examples at a brightness of 1,000 nits, and the time (lifetime; T95) taken for the brightness to decrease from 100% to 95% at a constant current at a brightness of 5,000 nits.

[0240] [Table 1]

[0241]

[0242] It is confirmed from Table 1 that, compared with conventional organic electroluminescent devices, the organic electroluminescent device containing a plurality of host materials has improved efficiency and / or lifetime characteristics, and the plurality of host materials includes a specific combination of compounds according to the present disclosure.

[0243] The compounds used in the device examples and comparative examples are shown in Table 2 below.

[0244] [Table 2]

[0245]

Claims

1. A plurality of host materials, the plurality of host materials comprising a first host material and a second host material, the first host material comprising a compound represented by Formula 1, and the second host material comprising a compound represented by Formula 2: Wherein X represents O or S; R1 to R8 each independently represent -L1-HAr, hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-membered to 30-membered) heteroaryl; or may be connected to adjacent substituents to form a ring; provided that at least one of R1 to R8 is -L1-HAr; L1 represents a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3-membered to 30-membered) heteroarylene, where if there are multiple L1s, each L1 may be the same or different; HAr represents substituted or unsubstituted nitrogen-containing (3-membered to 30-membered) heteroaryl, where if there are multiple HArs, each HAr may be the same or different; Among them, HAr represents substituted or unsubstituted triazinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted triazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted phenanthridinyl, or substituted or unsubstituted benzothienopyrimidinyl; Wherein L2 represents a single bond, substituted or unsubstituted (C1-C30) alkylene, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3-membered to 30-membered) heteroarylene; Ar represents a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthylphenyl, a substituted or unsubstituted phenylnaphthyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted benzocarbazolyl, a substituted or unsubstituted dibenzocarbazolyl, a substituted or unsubstituted dibenzothienyl, a substituted or unsubstituted benzothienyl, a substituted or unsubstituted benzonaphthothienyl, a substituted or unsubstituted dibenzofuryl, a substituted or unsubstituted benzofuryl, a substituted or unsubstituted benzonaphthofuryl, a substituted or unsubstituted diazabenzofuryl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted benzquinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted benzquinoxalinyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted naphthyridinyl, a substituted or unsubstituted benzothienopyrimidinyl, a substituted or unsubstituted diphenylamino, a substituted or unsubstituted phenylnaphthylamino, a substituted or unsubstituted phenylbiphenylamino, a substituted or unsubstituted naphthylbiphenylamino, a substituted or unsubstituted biphenylamino, a substituted or unsubstituted biphenylfluorenylamino, or a substituted or unsubstituted biphenyldibenzofurylamino; represented by the following formula 3; wherein X1 to X 12 each independently represents N or CR 14 ; R 14 each 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 adjacent R 14 may be joined to each other to form a ring, and wherein if there are a plurality of R 14 , then each R 14 may be the same or different; and * represents the bonding site with L2.

2. The multiple main materials according to claim 1, wherein, R1 to R 14 , the substituents of the substituted alkyl, substituted alkylene, 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-arylamino and substituted alkylarylamino, substituted triazinyl, substituted pyridinyl, substituted pyrimidinyl, substituted quinazolinyl, substituted benzquinazolinyl, substituted quinoxalinyl, substituted benzquinoxalinyl, substituted quinolinyl, substituted benzquinolinyl, substituted isoquinolinyl, substituted benzisoquinolinyl, substituted triazolyl, substituted pyrazolyl, substituted naphthyridinyl, substituted cinnolinyl, or substituted benzothienopyrimidinyl, substituted phenyl, substituted naphthyl, substituted biphenyl, substituted naphthylphenyl, substituted phenylnaphthyl, substituted terphenyl, substituted carbazolyl, substituted benzcarbazolyl, substituted dibenzcarbazolyl, substituted dibenzothienyl, substituted benzothienyl, substituted benzonaphthothienyl, substituted dibenzofuranyl, substituted benzofuranyl, substituted benzonaphthofuranyl, substituted diazabenzofuranyl, substituted triazinyl, substituted quinazolinyl, substituted benzquinazolinyl, substituted quinoxalinyl, substituted benzquinoxalinyl, substituted triazolyl, substituted pyrazolyl, substituted naphthyridinyl, substituted benzothienopyrimidinyl, substituted diphenylamino, substituted phenylnaphthylamino, substituted phenylbiphenylamino, substituted naphthylbiphenylamino, substituted biphenylamino, substituted biphenylfluorenylamino, or substituted biphenyldibenzofuranylamino 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 substituted by one or more (C6-C30)aryl (3- to 30-membered)heteroaryl; unsubstituted or substituted by at least one of one or more (C1-C30)alkyl, one or more (3- to 30-membered)heteroaryl and one or more di(C6-C30)arylamino (C6-C30)aryl; 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)aryl amino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; bis(C6-C30)arylboronylcarbonyl; bis(C1-C30)alkylboronylcarbonyl; (C1-C30)alkyl(C6-C30)arylboronylcarbonyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl.; 3. The plurality of host materials according to claim 1, wherein, Formula 1 is represented by at least one of Formulas 1-1 to 1-4 below: wherein R1 to R8, X, L1 and HAr are as defined in claim 1.

4. The multiple main materials according to claim 1, wherein, Formula 3 is represented by Formula 3-1 below: wherein R 31 to R 33 each 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 may be linked to an adjacent substituent to form a ring; and aa represents an integer from 1 to 3, ab represents an integer from 1 to 4, and ac represents an integer from 1 to 5, where if aa, ab, and ac are integers of 2 or greater, then each R 31 each R 32 and each R 33 can be the same or different.

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

6. The plurality of matrix materials according to claim 1, wherein, The compound represented by Formula 2 is at least one selected from the following compounds:

7. 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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