Host materials and organic electroluminescent devices containing the same

Abstract

To provide multiple host materials and an organic electroluminescent device comprising the same.SOLUTION: The present disclosure relates to multiple host materials including a first host material comprising a compound represented by a specific formula 1, and a second host material comprising a compound represented by a specific formula 2, and to an organic electroluminescent device comprising the same. By comprising a specific combination of compounds of the present disclosure as host materials, it is possible to provide an organic electroluminescent device having higher luminous efficiency and / or longer lifetime properties than a conventional organic electroluminescent device.SELECTED DRAWING: None

Description

[Technical Field]

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

[0002] In 1987, Tang et al. at Eastman Kodak first developed a small-molecule green organic electroluminescent device (OLED) using a TPD / Alq3 bilayer consisting of an emissive layer and a charge-transport layer. Since then, research on OLEDs has progressed rapidly, and they have become commercially available. Currently, phosphorescent materials, which provide excellent luminous efficiency in panel fabrication, are mainly used in organic electroluminescent devices. Therefore, OLEDs with high luminous efficiency and / or long life are required for long-term use and high resolution of displays.

[0003] Patent Documents 1, 2, and 3 disclose several host materials using carbazole derivative compounds. However, the aforementioned references do not specifically disclose the several host materials described in the present disclosure. Furthermore, there is a need for the development of light-emitting materials having improved performance, such as improved luminous efficiency and / or lifetime characteristics, compared to the host materials disclosed in the aforementioned references. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Korean Patent Application Publication No. 2015-0086721 [Patent Document 2] Korean Patent Application Publication No. 2014-0096203 [Patent Document 3] Korean Patent Application Publication No. 2015-0116776 [Patent Document 4] Korean Patent Application Publication No. 2015-0135109 [Patent Document 5] Korean Patent Application Publication No. 2016-0099471 [Patent Document 6] Korean Patent Application Publication No. 2015-0077513 [Patent Document 7] Korean Patent Application Publication No. 2017-0129599 Summary of the Invention [Problem to be solved by the invention]

[0005] An object of the present disclosure is to provide an organic electroluminescent device having higher luminous efficiency and / or longer lifetime characteristics by including a specific combination of compounds as a host material. [Means for solving the problem]

[0006] The inventors have found that the compound of formula 1 below: [ka] (In the formula, ring A, ring B, and ring C each independently represent a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring; Y represents O, S, or NRa; Ra represents -L2-Ar2, Ar1 and Ar2 each independently represent a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 membered) heteroaryl containing at least one of nitrogen, oxygen, and sulfur, or a substituted or unsubstituted di(C6-C30) arylamino; L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30-membered) heteroarylene; and n represents an integer of 0 or 1, provided that when n is 0, both ring A and ring B are substituted or unsubstituted naphthalene rings. [ka] (In the formula, HAr represents a substituted or unsubstituted nitrogen-containing (3- to 30-membered) heteroaryl; L3 represents unsubstituted or deuterium-substituted naphthylene, unsubstituted or deuterium-substituted biphenylene, unsubstituted or deuterium-substituted terphenylene, or unsubstituted or deuterium-substituted -phenylene-naphthylene-; and a second host material containing a compound represented by the formula (I), wherein R1 to R8 each independently represent hydrogen, deuterium, or a (C6-C30)aryl that is unsubstituted or substituted with at least one of deuterium and (C6-C30)aryl.

[0007] Advantageous Effects of the Invention By including a specific combination of compounds of the present disclosure as a host material, it is possible to provide an organic electroluminescent device having higher luminous efficiency and / or longer life characteristics compared to conventional organic electroluminescent devices, and to use the same to manufacture a display system or a light system. DETAILED DESCRIPTION OF THE INVENTION

[0008] The present disclosure will be described in detail hereinafter. However, the following description is intended to illustrate the present disclosure and is not intended to limit the scope of the present disclosure in any way.

[0009] The term "organic electroluminescent material" in this disclosure refers to a material that can be used in an organic electroluminescent device and can contain at least one compound. The organic electroluminescent material can be included in any layer that constitutes an organic electroluminescent device, as needed. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole auxiliary material, an emitting auxiliary material, an electron blocking material, an emitting material (including a host and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0010] The term "multiple organic electroluminescent materials" in the present disclosure refers to an organic electroluminescent material including a combination of at least two compounds that can be included in any layer constituting an organic electroluminescent device. It can refer to both a material before being included in an organic electroluminescent device (e.g., before deposition) and a material after being included in an organic electroluminescent device (e.g., after deposition). For example, the multiple organic electroluminescent materials can be a combination of at least two compounds that can be included in at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. The at least two compounds can be included in the same layer or different layers, and can be mixedly evaporated or simultaneously evaporated, or can be evaporated separately.

[0011] The term "multiple host materials" in the present disclosure refers to an organic electroluminescent material comprising a combination of at least two host materials. It can refer to both the material before being included in an organic electroluminescent device (e.g., before vapor deposition) and the material after being included in an organic electroluminescent device (e.g., after vapor deposition). The multiple host materials of the present disclosure can be included in any light-emitting layer constituting an organic electroluminescent device. Two or more compounds included in the multiple host materials of the present disclosure can be included in one light-emitting layer, or can be included in different light-emitting layers. For example, two or more host materials can be mixed and evaporated to form a layer, or separately and simultaneously evaporated to form a layer.

[0012] As used herein, the term "(C6-C30)aryl" or "(C6-C30)arylene" refers to a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring skeletal carbon atoms. The number of ring skeletal carbon atoms is preferably 6 to 20, more preferably 6 to 15. The aryl or arylene may be partially saturated and may include a spiro structure. Examples of the aryl include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, spiro[fluorene-benzofluorenyl]yl, azulenyl, and the like.More specifically, aryl includes phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, 1-chrysenyl, 2-chrysenyl, 3-chrysenyl, 4-chrysenyl, 5-chrysenyl, 6-chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, Lysenyl, 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, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl -4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, p-tert-butylphenyl, p-(2-phenylpropyl) phenyl, 4'-methylbiphenylyl, 4''-tert-butyl-p-terphenyl-4-yl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, and the like.

[0013] The term "(3- to 50-membered)heteroaryl" or "(3- to 30-membered)heteroarylene" refers to an aryl or arylene having 3 to 50 or 3 to 30 skeletal ring atoms, where the number of skeletal ring atoms is preferably 3 to 30, more preferably 5 to 20, and includes at least one, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, Si, and P. The heteroaryl(ene) may be a monocyclic ring or a fused ring fused with at least one benzene ring, may be partially saturated, may be formed by bonding at least one heteroaryl or aryl group to a heteroaryl group via a single bond, or may include a spiro structure. Examples of the heteroaryl include monocyclic heteroaryls such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl, as well as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, benzonaphthofuranyl, and dibenzothiophene. condensed ring heteroaryls such as phenyl, benzonaphthothiophenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthrooxazolyl, benzodioxolyl, and the like. More specifically, heteroaryl includes 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolizinyl, 2-indolizinyl, 3-indolizinyl, 5-indolizinyl, 6-indolizinyl, 7-indolizinyl, 8-indolizinyl,2-Imidazopyridinyl, 3-Imidazopyridinyl, 5-Imidazopyridinyl, 6-Imidazopyridinyl, 7-Imidazopyridinyl, 8-Imidazopyridinyl, 3-Pyridinyl, 4-Pyridinyl, 1-Indolyl, 2-Indolyl, 3-Indolyl, 4-Indolyl, 5-Indolyl, 6-Indolyl, 7-Indolyl, 1-Isoindolyl, 2-Isoindolyl, 3-Isoindolyl, 4-Isoindolyl, 5-Isoindolyl, 6-Isoindolyl, 7-Isoindolyl, 2-Furyl, 3-Furyl, 2-Benzofuranyl, 3-Benzofuranyl, 4-Benzenyl Zofuranil, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazol-1-yl, azacarbazol-2-yl, azacarbazol-3-yl, azacarbazol-4-yl, azacarbazol-5-yl, azacarbazol-6-yl, azacarbazol-7-yl, azacarbazol-8-yl, azacarbazol-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl Lysinyl, 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, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-germafluorenyl, 4-germafluorenyl, etc. "Halogen" includes F, Cl, Br, and I.

[0014] In addition, "ortho (o-)", "meta (m-)", and "para (p-)" are prefixes that indicate the relative positions of substituents, respectively. Ortho indicates that two substituents are adjacent to each other; for example, when two substituents in a benzene derivative occupy the 1st and 2nd positions, it is called the ortho position. Meta indicates that two substituents are at the 1st and 3rd positions; for example, when two substituents in a benzene derivative occupy the 1st and 3rd positions, it is called the meta position. Para indicates that two substituents are at the 1st and 4th positions; for example, when two substituents in a benzene derivative occupy the 1st and 4th positions, it is called the para position.

[0015] As used herein, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a particular functional group has been replaced with another atom or another functional group, i.e., a substituent.In the present disclosure, the substituents of substituted benzene, substituted naphthalene, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted alkyl, 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 are each independently deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C 30) alkyl, halo(C1-C30)alkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C1-C30)alkoxy, (C1-C30)alkylthio, (C3-C30)cycloalkyl, (C3-C30)cycloalkenyl, (3-7 membered)heterocycloalkyl, (C6-C30)aryloxy, (C6-C30)arylthio, (3-50 membered)heteroaryl unsubstituted or substituted with at least one of (C1-C30)alkyl, (C6-C30)aryl, and di(C6-C30)arylamino. (C6-C30)aryl substituted with at least one of aryl, unsubstituted or deuterium, cyano, (C1-C30)alkyl, (3- to 50-membered)heteroaryl, di(C6-C30)arylamino, and tri(C6-C30)arylsilyl, 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-( At least one selected from the group consisting of (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, the substituent may be at least one selected from the group consisting of deuterium, (C1-C20) alkyl, unsubstituted or deuterium, (C1-C20) alkyl, (3-30-membered) heteroaryl, and (C6-C25) aryl substituted with at least one of di(C6-C25) arylamino, unsubstituted or (3-30-membered) heteroaryl substituted with at least one of (C1-C20) alkyl and (C6-C25) aryl, and di(C6-C20) arylamino. More preferably, the substituent may be at least one selected from the group consisting of deuterium, (C1-C10) alkyl, and unsubstituted or deuterium-substituted (C6-C20) aryl. For example, the substituent may be at least one selected from the group consisting of deuterium, methyl, unsubstituted or deuterium-substituted phenyl, naphthyl, biphenyl, and terphenyl.

[0016] In the formulas of the present disclosure, heteroaryl, heteroarylene, and heterocycloalkyl may each independently contain at least one heteroatom selected from B, N, O, S, Si, and P. Furthermore, the heteroatom may be selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl. silyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, and substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino.

[0017] In Formula 1, ring A, ring B, and ring C each independently represent a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring. According to one embodiment of the present disclosure, ring A, ring B, and ring C each independently may be an unsubstituted benzene ring or an unsubstituted naphthalene ring.

[0018] In Formula 1, n represents an integer of 0 or 1, Y represents O, S, or NRa, and Ra represents -L2-Ar2. When n is 0, both ring A and ring B represent substituted or unsubstituted naphthalene rings, preferably unsubstituted naphthalene rings.

[0019] Ar1 and Ar2 each independently represent a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 membered) heteroaryl containing at least one of nitrogen, oxygen, and sulfur, or a substituted or unsubstituted di(C6-C30) arylamino. According to one embodiment of the present disclosure, Ar1 and Ar2 each independently represent a substituted or unsubstituted (C6-C25) aryl, a substituted or unsubstituted (5-25 membered) heteroaryl containing at least one of nitrogen, oxygen, and sulfur, or a substituted or unsubstituted di(C6-C25) arylamino. According to another embodiment of the present disclosure, Ar1 and Ar2 each independently represent a (C6-C25)aryl which is unsubstituted or substituted with a (C1-C10)alkyl, a (5-20 membered)heteroaryl which is unsubstituted or substituted with a (C6-C18)aryl containing at least one of nitrogen, oxygen, and sulfur, or a di(C6-C18)arylamino which is unsubstituted or substituted with a (C6-C18)aryl. Specifically, Ar1 is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted benzofuropyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted dibenzyl, substituted or unsubstituted dibenzo ... The alkyl group may be benzothiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted naphthylphenylamino, or substituted or unsubstituted biphenylphenylamino.For example, Ar1 and Ar2 can each independently represent phenyl, naphthyl, biphenyl, terphenyl, dimethylfluorenyl, dimethylbenzofluorenyl, spirobifluorenyl, pyridyl substituted with phenyl, pyrimidinyl substituted with phenyl, triazinyl substituted with phenyl, quinolyl substituted with phenyl, quinazolinyl substituted with at least one of phenyl and naphthyl, quinoxalinyl substituted with at least one of phenyl and naphthyl, naphthyridinyl substituted with phenyl, dibenzothiophenyl, dibenzothiofuranyl, carbazolyl substituted with phenyl, benzofuropyrimidinyl substituted with phenyl, benzoquinazolinyl substituted with phenyl, benzoquinoxalinyl substituted with phenyl, benzocarbazolyl substituted with phenyl, diphenylamino, phenylnaphthylamino, phenylbiphenylamino, diphenylamino substituted with naphthyl, phenylbiphenylamino substituted with naphthyl, or the like.

[0020] L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene. According to one embodiment of the present disclosure, L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (5-25 membered) heteroarylene. According to another embodiment of the present disclosure, L1 and L2 each independently represent a single bond, an unsubstituted (C6-C18) arylene, or a (5-20 membered) heteroarylene unsubstituted or substituted with a (C6-C18) aryl. For example, L1 and L2 can each independently represent a single bond, phenylene, naphthylene, biphenylene, triazinylene substituted with phenyl, pyrimidinylene substituted with phenyl, quinolylene, unsubstituted or phenyl-substituted quinazolinylene, unsubstituted or phenyl-substituted quinoxalinylene, naphthyridinylene, benzofuropyrimidinylene, benzoquinazolinylene, carbazolylene, benzoquinoxalinylene, benzocarbazolylene, or the like.

[0021] Formula 1 can be expressed by any one of the following formulas 1-1 to 1-7. [ka]

[0022] In formulas 1-1 to 1-7, Ar1, L1, and Y are as defined in formula 1.

[0023] In Formula 1-1 to Formula 1-7, R 11 ~R 27 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino. For example, R 11 ~R 27 can represent hydrogen.

[0024] In formulas 1-1 to 1-7, a, d, h, m, q, and r each independently represent an integer of 1 to 6, b, c, e, f, g, i, j, k, l, o, and p each independently represent an integer of 1 to 4, and a to m and o to r each independently represent an integer of 2 or more. 11 Each of the following: 12 Each of R 13 Each of R 14 Each of R 15 Each of R 16 Each of R 17 Each of R 18 Each of R 19Each of R 20 Each of R 21 Each of R 22 Each of R 23 Each of R 24 Each of R 25 Each of R 26 and R 27 Each of may be the same or different.

[0025] In Formula 2, HAr represents a substituted or unsubstituted N-containing (3-30 membered) heteroaryl. According to one embodiment of the present disclosure, HAr represents a substituted or unsubstituted (5-25 membered) heteroaryl containing at least one nitrogen. According to another embodiment of the present disclosure, HAr represents a (5-20 membered) heteroaryl substituted with a (C6-C30) aryl and containing at least one nitrogen. Specifically, HAr represents a 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 quinolyl, substituted or unsubstituted benzoquinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted benzoisoquinolyl, It can represent substituted or unsubstituted triazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted naphthyridinyl, or substituted or unsubstituted benzothienopyrimidinyl. For example, HAr can represent substituted triazinyl, in which case the substituents of the substituted triazinyl can be at least one, preferably two, selected from the group consisting of phenyl, deuterium-substituted phenyl, naphthyl, biphenyl, and terphenyl.

[0026] In Formula 2, L3 represents unsubstituted or deuterium-substituted naphthylene, unsubstituted or deuterium-substituted biphenylene, unsubstituted or deuterium-substituted terphenylene, or unsubstituted or deuterium-substituted -phenylene-naphthylene-. According to one embodiment of the present disclosure, L3 represents unsubstituted or deuterium-substituted naphthylene, unsubstituted biphenylene, or unsubstituted -phenylene-naphthylene-. -phenylene-naphthylene- indicates that the phenylene therein can be bonded to HAr, or the naphthylene therein can be bonded to HAr.

[0027] In Formula 2, R1-R8 each independently represent hydrogen, deuterium, or a (C6-C30)aryl that is unsubstituted or substituted with at least one of deuterium and (C6-C30)aryl. According to one embodiment of the present disclosure, R1-R8 each independently represent hydrogen, deuterium, or a (C6-C25)aryl that is unsubstituted or substituted with a (C6-C30)aryl. According to another embodiment of the present disclosure, R1-R8 each independently represent hydrogen, deuterium, or an unsubstituted (C6-C18)aryl. R1-R8 can be the same or different from one another. For example, R1-R8 can each independently represent hydrogen, deuterium, phenyl, naphthyl, or biphenyl.

[0028] In one embodiment of the present disclosure, Equation 2 can be expressed as Equation 3 below: [ka]

[0029] In Equation 3, Ar 21 and Ar 22 each independently represents unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted biphenyl, unsubstituted or deuterium-substituted terphenyl, or unsubstituted or deuterium-substituted naphthyl; L 21represents unsubstituted or deuterium-substituted naphthylene or unsubstituted or deuterium-substituted biphenylene; R1, R4, R5, and R8 each independently represent hydrogen, deuterium, unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted biphenyl, unsubstituted or deuterium-substituted terphenyl, or unsubstituted or deuterium-substituted naphthyl; R2, R3, R6, and R7 each independently represent hydrogen or deuterium; provided that Ar 21 and Ar 22 represent phenyl, provided that at least one of R1, R4, R5, and R8 is not hydrogen or deuterium.

[0030] The compound represented by formula 1 can be exemplified by, but not limited to, the following compounds: [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0031] The compound represented by formula 2 may be exemplified by, but not limited to, any one of the following compounds: [ka] [ka] [ka] [ka]

[0032] A combination of at least one of compounds H1-1 to H1-150 and at least one of compounds H2-1 to H2-55 can be used in an organic electroluminescent device.

[0033] According to one embodiment of the present disclosure, the present disclosure provides an organic electroluminescent compound represented by Formula 3. Specific examples of the compound represented by Formula 3 include, but are not limited to, compounds H2-2 to H2-13, H2-15 to H2-22, H2-24 to H2-28, H2-32 to H2-35, H2-43, H2-46, H2-47, and H2-50 to H2-55. Furthermore, the present disclosure can provide an organic electroluminescent device comprising the organic electroluminescent compound represented by Formula 3.

[0034] The compound represented by Formula 1 according to the present disclosure can be prepared by a synthetic method known to those skilled in the art, as shown in the following Reaction Scheme 1. For example, the compound represented by Formula 1 can be prepared by referring to, but not limited to, Patent Document 4 (published December 2, 2015), Patent Document 5 (published August 22, 2016), Patent Document 6 (published July 8, 2015), and Patent Document 7 (published November 27, 2017). [Reaction Scheme 1] [ka]

[0035] Compounds of formula 2 or 3 according to the present disclosure can be prepared by synthetic methods known to those skilled in the art, including, but not limited to, as shown in Reaction Scheme 2 below. [Reaction Scheme 2] [ka]

[0036] In Reaction Schemes 1 and 2, Ar1, L1, Ra, R 18 ~R 20 , h to j, R1 to R8, L3, and HAr are as defined in formulas 1, 1-4, and 2, and Hal represents I, Br, Cl, ONf (nonafluorobutanesulfonyl), or OTf (triflate).

[0037] Illustrative synthetic examples of compounds represented by Formulas 1-3 are described above. Those skilled in the art will readily recognize that all of these reactions, including those based on Buchwald-Hartwig cross-coupling reactions, N-arylation reactions, H-Mont-mediated etherification reactions, Miyaura borylation reactions, Suzuki cross-coupling reactions, intramolecular acid-induced cyclization reactions, Pd(II)-catalyzed oxidative cyclization reactions, Grignard reactions, Heck reactions, cyclodehydration reactions, SN1 substitution reactions, SN2 substitution reactions, and phosphine-mediated reductive cyclization reactions, are also possible. While defined by Formulas 1-3 above, the reactions may proceed even when substituents not specified in a particular synthetic example are present. For example, deuterium-containing compounds of Formulas 1-3 can be prepared by treating the non-deuterated compounds with a deuterated solvent or D6-benzene in the presence of an H / D exchange catalyst, such as a Lewis acid, e.g., aluminum trichloride or ethyl aluminum chloride, trifluoromethanesulfonic acid, or trifluoromethanesulfonic acid-D. Furthermore, the degree of deuteration can be controlled by adjusting reaction conditions such as reaction temperature, reaction time, and acid equivalent.

[0038] An organic electroluminescent device according to the present disclosure includes an anode, a cathode, and at least one organic layer between the anode and the cathode. The organic layer can include a plurality of organic electroluminescent materials, where the compound represented by Formula 1 is included as a first organic electroluminescent material and the compound represented by Formula 2 is included as a second organic electroluminescent material. According to one embodiment of the present disclosure, the organic electroluminescent device includes an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, where the light-emitting layer includes the compound represented by Formula 1 and the compound represented by Formula 2.

[0039] The electrodes can be semi-transparent or reflective and, depending on the materials, can be top-emitting, bottom-emitting, or dual-emitting. The hole injection layer can be further doped with a p-dopant, and the electron injection layer can be further doped with an n-dopant.

[0040] The light-emitting layer includes a host and a dopant. The host includes multiple host materials. The compound represented by Formula 1 can be included as a first host compound of the multiple host materials, and the compound represented by Formula 2 can be included as a second host compound of the multiple host materials. The weight ratio of the first host compound to the second host compound is in the range of about 1:99 to about 99:1, preferably about 10:90 to about 90:10, more preferably about 30:70 to about 70:30, even more preferably about 40:60 to about 60:40, and even more preferably about 50:50. When two or more materials are included in one layer, they can be mixed and evaporated to form a layer, or they can be separately and simultaneously evaporated to form a layer.

[0041] The light-emitting layer is a layer that emits light, and can be a single layer or a multi-layer structure in which two or more layers are stacked. In the multiple host materials according to the present disclosure, the first and second host materials can be included in one layer, or can be included in different light-emitting layers. According to one embodiment of the present disclosure, the doping concentration of the dopant compound relative to the host compound in the light-emitting layer is less than about 20% by weight.

[0042] The organic electroluminescent device of the present disclosure may further include at least one layer selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron injection layer, an intermediate layer, an electron buffer layer, a hole blocking layer, and an electron blocking layer. According to one embodiment of the present disclosure, the organic electroluminescent device may further include an amine-based compound as at least one of the hole injection material, the hole transport material, the hole auxiliary material, the light-emitting material, the light-emitting auxiliary material, and the electron blocking material, in addition to the plurality of host materials of the present disclosure. Also, according to one embodiment of the present disclosure, the organic electroluminescent device may further include an azine-based compound as at least one of the electron transport material, the electron injection material, the electron buffer material, and the hole blocking material, in addition to the plurality of host materials of the present disclosure.

[0043] The dopant contained in the organic electroluminescent device according to the present disclosure can be at least one phosphorescent or fluorescent dopant, preferably at least one phosphorescent dopant.The phosphorescent dopant material applied to the organic electroluminescent device according to the present disclosure is not particularly limited, but can be selected from metallized complex compounds of iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), preferably from ortho-metallized complex compounds of iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), more preferably from ortho-metallized iridium complex compounds.

[0044] Dopants included in the organic electroluminescent devices of the present disclosure can include, but are not limited to, compounds represented by Formula 101 below: [ka] In Formula 101, L is selected from the following structures 1 and 2: [ka] is selected from.

[0045] R100 ~R 103 each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium and / or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (3-30 membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy, or R 100 ~R 103 can be combined with adjacent ones of the formula (I) to form a ring with the pyridine, for example, a substituted or unsubstituted quinoline, benzofuropyridine, benzothienopyridine, indenopyridine, benzofuroquinoline, benzothienoquinoline, or indenoquinoline ring.

[0046] R 104 ~R 107 each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium and / or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy, or R 104 ~R 107 can be combined with adjacent ones of to form a ring with benzene, for example a substituted or unsubstituted naphthalene, fluorene, dibenzothiophene, dibenzofuran, indenopyridine, benzofuropyridine or benzothienopyridine ring; R 201 ~R 211 each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium and / or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C6-C30) aryl, or R 201 ~R 211 can be joined to adjacent ones of to form a ring, n represents an integer of 1 to 3.

[0047] Specific examples of the dopant compound are as follows, but are not limited to these. [ka] [ka] [ka] [ka] [ka]

[0048] To form each layer of the organic electroluminescent device of the present disclosure, dry deposition methods such as vacuum deposition, sputtering, plasma and ion plating methods, or wet deposition methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating and flow coating methods can be used.

[0049] In the wet film-forming method, a thin film can be formed by dissolving or diffusing the material for forming each layer in any appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent can be any solvent as long as it can dissolve or diffuse the material for forming each layer and does not cause any problems in film-forming ability.

[0050] Furthermore, the compound represented by Formula 1 and the compound represented by Formula 2 or 3 can be deposited as a film by the above method, typically by a co-evaporation process or a mixed evaporation process. Co-evaporation is a mixed evaporation method in which two or more materials are placed in separate crucible sources and current is applied to both cells simultaneously to evaporate the materials. Mixed evaporation is a mixed evaporation method in which two or more materials are mixed in a single crucible source before evaporating them and current is applied to the cells to evaporate the materials.

[0051] The organic electroluminescent material according to the present disclosure can be used as a light-emitting material for a white organic light-emitting device. White organic light-emitting devices have been proposed to have various structures, such as a parallel structure or a stacked structure, depending on the arrangement of R (red), G (green), or YG (yellow-green), and B (blue) light-emitting components, or a color conversion material (CCM) method, and the present disclosure can also be applied to such white organic light-emitting devices.

[0052] Furthermore, the organic electroluminescent materials according to the present disclosure may also be used in organic electroluminescent devices that include quantum dots (QDs).

[0053] The present disclosure may provide a display system comprising a plurality of host materials of the present disclosure.Furthermore, the organic electroluminescent device of the present disclosure may be used to prepare a display system or a lighting system.Specifically, the organic electroluminescent device of the present disclosure may be used to prepare a display system, such as a display system for a smartphone, a tablet, a notebook, a PC, a television, or an automobile, or a lighting system, such as an outdoor or indoor lighting system.

[0054] Hereinafter, the present disclosure will be described in detail with reference to representative compounds of the present disclosure, including methods for preparing the compounds and their properties. However, the present disclosure is not limited by the following examples. [Example]

[0055] Example 1: Preparation of Compound H1-131 [ka] Synthesis of Compound 1 7H-Dibenzo[c,g]carbazole (60 g, 224 mmol) was dissolved in 900 mL of N,N-dimethylformamide (DMF) in a flask, and the mixture was cooled to 0 °C and stirred. N-Bromosuccinimide (NBS) (36 g, 202 mmol) was dissolved in 220 mL of DMF and then added dropwise to the mixture over 2.5 hours. The resulting mixture was stirred at room temperature for 2 hours. After the reaction was completed, the reaction product was washed with an aqueous NaSO solution and water. The organic layer was extracted with ethyl acetate, and residual water was removed with MgSO. The residue was dried and separated using a silica filter to obtain compound 1 (79 g, yield: 79%).

[0056] Synthesis of compound 2 Compound 1 (76 g, 220 mmol), iodobenzene (90 g, 439 mmol), CuI (20.90 g, 110 mmol), ethylenediamine (EDA) (13 g, 110 mmol), and KPO (139 g, 659 mmol) were added to 1.1 L of toluene, and the mixture was stirred under reflux for 2.5 hours. MeOH was added to the mixture, and the resulting solid was filtered under reduced pressure. The residue was separated by column chromatography to give compound 2 (55.1 g, yield: 60%).

[0057] Synthesis of compound 3 Compound 2 (54.6 g, 129 mmol), 2-chloroaniline (20 g, 155 mmol), Pd(OAc) (2.9 g, 13 mmol), P(t-Bu) (5.2 g, 26 mmol), sodium tert-butoxide (NaOt-Bu) (31 g, 323 mmol), and 650 mL of toluene were stirred under reflux for 4 hours. The mixture was cooled to room temperature, and NH Cl (aq) was added to it. The reaction product was extracted with ethyl acetate (EA) and dried over magnesium sulfate. The residue was distilled under reduced pressure and separated by column chromatography to give compound 3 (47.9 g, yield: 79%).

[0058] Synthesis of compound 4 Compound 3 (48 g, 103 mmol), Pd(OAc) (2.3 g, 10 mmol), ligand (tricyclohexylphosphonium tetrafluoroborate) (7.6 g, 21 mmol), CsCO (100 g, 308 mmol), and 400 mL of N,N-dimethylacetamide (DMA) were heated under reflux for 1 hour. The reaction mixture was cooled to room temperature, and NHCl (aqueous) was added. The organic layer was extracted with methylene chloride (MC) and dried over magnesium sulfate. The residue was distilled under reduced pressure and separated by column chromatography to give compound 4 (44 g, 79% yield).

[0059] Synthesis of compound H1-131 Compound 4 (5 g, 12 mmol), iodobenzene (3.5 g, 17 mmol), CuI (1.1 g, 6 mmol), 1,2-diaminocyclohexane (2.6 g, 23 mmol), and KPO (4.9 g, 23 mmol) were added to 60 mL of o-xylene, and the mixture was stirred under reflux for 1 day. The reaction mixture was cooled to room temperature and filtered through Celite using MC. The filtrate was distilled under reduced pressure and separated by column chromatography using MC / Hex to give compound H1-131 (1.3 g, yield: 22%). 1 H NMR(600MHz,DMSO,δ)9.16-9.15(d,1H),8.99-8.98(d,1H),8.14-8.13(d,1H),7.94-7.93(d,1H),7.94-7.68(m,9H ),7.65-7.61(m,3H),7.60-7.54(m,3H),7.25-7.21(m,2H),7.08-7.07(d,1H),6.78-6.76(m,1H)5.95-5.94(d,1H)

[0060] [Table 1]

[0061] Example 2: Preparation of Compound H1-132 [ka] Compound 4 (7 g, 16 mmol), 2-bromonaphthalene (6.7 g, 32 mmol), CuI (1.5 g, 8 mmol), 1,2-diaminocyclohexane (3.7 g, 32 mmol), and KPO (10.3 g, 49 mmol) were added to 80 mL of o-xylene, and the mixture was stirred under reflux for 1 day. The reaction mixture was cooled to room temperature and filtered through a Celite pad using MC. The filtrate was distilled under reduced pressure and separated by column chromatography using MC / Hex to give compound H1-132 (1.3 g, yield: 22%). 1 H NMR(600MHz,DMSO,δ)9.17-9.15(d,1H),9.00-8.99(d,1H),8.31-8.30(m,2H),8.20-8.18(d,1H),8.15-8.14(d,1H),8.11-8.10(d,1H),7.95-7 .94(d,1H),7.83-7.79(m,5H),7.73-7.69(m,4H),7.60-7.57(m,4H),7. 21-7.18(m,2H),7.14-7.13(d,1H),6.78-6.77(t,1H)5.98-5.96(d,1H)

[0062] [Table 2]

[0063] Example 3: Preparation of Compound H1-134 [ka] Synthesis of compound 5 Compound 1 (15 g, 220 mmol), 3-iodo-1,1'-biphenyl (18 g, 65 mmol), CuI (4.1 g, 22 mmol), ethylenediamine (2.6 g, 43 mmol), and KPO (23 g, 108 mmol) were added to 216 mL of toluene, and the mixture was stirred under reflux for 4 hours. MeOH was added to the mixture, and the resulting solid was filtered under reduced pressure. The filtrate was separated by column chromatography to give compound 5 (16 g, yield: 74%).

[0064] Synthesis of compound 6 Compound 5 (15 g, 30 mmol), 2-chloroaniline (7.7 g, 60 mmol), Pd(OAc) (0.67 g, 3 mmol), P(t-Bu) (1.2 g, 6 mmol), NaOt-Bu (7.2 g, 75 mmol), and 150 mL of toluene were stirred under reflux for 2 hours. The reaction mixture was cooled to room temperature, and NH4Cl (aq) was added. The organic layer was extracted with EA and dried over magnesium sulfate. The residue was distilled under reduced pressure and separated by column chromatography to give compound 6 (10.1 g, yield: 62%).

[0065] Synthesis of compound 7 Compound 6 (10 g, 18 mmol), Pd(OAc) (0.41 g, 1.8 mmol), ligand (tricyclohexylphosphonium tetrafluoroborate) (1.35 g, 3.7 mmol), CsCO (18 g, 55 mmol), and 92 mL of DMA were stirred under reflux for 1 hour. The reaction mixture was cooled to room temperature, and NHCl (aqueous) was added. The organic layer was extracted with MC and dried over magnesium sulfate. The residue was distilled under reduced pressure and separated by column chromatography to give compound 7 (7.1 g, yield: 76%).

[0066] Synthesis of compound H1-134 Compound 7 (6.7 g, 13 mmol), 3-iodo-1,1'-biphenyl (7.4 g, 26 mmol), Cu powder (0.42 g, 7 mmol), and K2CO3 (3.6 g, 26 mmol) were added to 70 mL of o-dichlorobenzene, and the mixture was stirred under reflux for 1 day. The reaction mixture was cooled to room temperature and filtered through Celite using MC. The filtrate was distilled under reduced pressure and separated by column chromatography using MC / Hex to give compound H1-134 (3.1 g, yield: 36%). 1H NMR(600MHz,DMSO,δ)9.18-9.17(d,1H),9.01-9.00(d,1H),8.16-8.15(d,1H),8.11-8.09(d,1H),8.06-8.05(m,2H),8.00-7 .79(m,7H),7.73-7.57(m,8H),7.48-7.38(m,6H),7.30-7.28(t,1H),7.22-7.18(m,2H),6.80-6.78(t,1H),6.07-6.06(d,1H)

[0067] [Table 3]

[0068] Example 4: Preparation of Compound H1-133 [ka] Compound 4 (4 g, 9.25 mmol), 3-iodo-1,1'-biphenyl (3.1 g, 11.1 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (0.42 g, 0.46 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (esphos) (0.38 g, 0.92 mmol), and NaOt-Bu (2.2 g, 23.13 mmol) were added to 46 mL of o-xylene, and the mixture was stirred under reflux for 1 day. The reaction product was extracted with MC, distilled under reduced pressure, and separated by column chromatography using MC / Hex to obtain compound H1-133 (1.2 g, 23% yield). 1H NMR(600MHz,DMSO,δ)9.17-9.15(d,1H),9.00-8.98(d,1H),8.15-8.13(d,1H),8.07-8.06 (d,1H),7.98(m,1H),7.95-7.94(d,1H),7.88-7.86(t,1H),7.82-7.80(m,7H),7.71-7.67 (m,2H),7.65-7.61(m,2H),7.60-7.55(m,2H),7.49-7.47(t,2H),7.42-7.39(t,1H),7.30 -7.27(t,1H),7.26-7.23(t,1H),7.20-7.19(d,1H),6.80-6.77(t,1H),5.97-5.95(d,1H)

[0069] [Table 4]

[0070] Example 5: Preparation of Compound H1-135 [ka] Synthesis of Compound 1 7H-Dibenzo[c,g]carbazole (50 g, 187 mmol) was dissolved in 750 mL of DMF in a flask, and the mixture was cooled to 0 °C and stirred. NBS (30 g, 168 mmol) was dissolved in 250 mL of DMF and then added dropwise to the mixture over 1 h. The resulting mixture was stirred at room temperature for 2 h. After the reaction was completed, the reaction product was washed with an aqueous NaSO solution and water, and the organic layer was extracted with ethyl acetate. The remaining water was removed with MgSO. The residue was dried and separated on a silica filter to obtain compound 1 (40 g, yield: 62%).

[0071] Synthesis of compound 8 Compound 1 (11 g, 32 mmol), 4-iodo-1,1'-biphenyl (17.8 g, 64 mmol), CuI (3.0 g, 15.9 mmol), ethylenediamine (1.91 g, 31.8 mmol), and KPO (20.3 g, 95 mmol) were added to 160 mL of toluene, and the mixture was stirred under reflux for 4 hours. MeOH was added to the mixture, and the resulting solid was filtered under reduced pressure. The filtrate was separated by column chromatography to give compound 8 (13.0 g, 82% yield).

[0072] Synthesis of compound 9 Compound 8 (13.0 g, 26 mmol), 2-chloroaniline (6.7 g, 52 mmol), Pd(OAc) (0.59 g, 2.6 mmol), P(t-Bu) (1.1 g, 5.2 mmol), NaOt-Bu (6.3 g, 65 mmol), and 130 mL of toluene were stirred under reflux for 4 hours. The reaction mixture was cooled to room temperature, and NH4Cl (aq) was added to it. The organic layer was extracted with EA and dried over magnesium sulfate. The residue was distilled under reduced pressure and separated by column chromatography to give compound 9 (9.2 g, yield: 65%).

[0073] Synthesis of compound 10 Compound 9 (9.2 g, 17 mmol), Pd(OAc) (0.38 g, 2 mmol), ligand (tricyclohexylphosphonium tetrafluoroborate) (1.2 g, 3 mmol), CsCO (138 g, 42 mmol), and 70 mL of DMA were stirred under reflux for 1 hour. The reaction mixture was cooled to room temperature, and NHCl (aqueous) was added. The resulting solid was distilled under reduced pressure and separated by column chromatography to give compound 10 (6.0 g, 70% yield).

[0074] Synthesis of compound H1-135 Compound 10 (6 g, 12 mmol), 2-bromonaphthalene (4.9 g, 24 mmol), CuI (1.1 g, 6 mmol), 1,2-diaminocyclohexane (2.7 g, 24 mmol), and K3PO4 (7.5 g, 35 mmol) were added to 60 mL of o-xylene, and the mixture was stirred under reflux for 1 day. The reaction mixture was cooled to room temperature. Ethyl acetate and water were then added, and the organic layer was separated and dried over magnesium sulfate. The residue was filtered through a Celite filter using MC. The filtrate was distilled under reduced pressure and separated by column chromatography using MC / Hex to obtain compound H1-135 (2.1 g, yield: 28%). 1 H NMR(600MHz,DMSO,δ)9.18-9.17(d,1H),9.01-8.99(d,1H),8.33-8.31(m,2H ),8.20-8.19(d,1H),8.17-8.15(d,1H),8.12-8.08(m,3H),7.98-7.97(d,1H ),7.93-7.89(m,4H),7.70-7.68(m,5H),7.63-7.57(m,5H)7.50-7.48(t,1H) ,7.22-7.19(t,1H),7.15-7.13(d,1H),6.77-6.74(td,1H),6.16-6.15(d,1H)

[0075] [Table 5]

[0076] Example 6: Preparation of Compound H1-11 [ka] Compound 1-1 (7 g, 13 mmol), dibenzo[b,d]furan-1-ylboronic acid (3 g, 14.3 mmol), K2CO3 (5.4 g, 39 mmol), and Pd(PPh3)4 (0.75 g, 0.65 mmol) were dissolved in 30 mL of HO, 60 mL of toluene, and 30 mL of EtOH in a flask, and the mixture was refluxed at 120 °C for 3 h. After the reaction was completed, the organic layer was extracted with ethyl acetate, and residual water was removed with magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound H1-11 (5.7 g, yield: 70%). 1 H NMR(600MHz,CDCl3,δ)9.305(s,1H),9.049-9.035(d,J=8.4Hz,1H),8.379-8.367(d,J=7.2Hz,1 H),8.022-8.008(d,J=8.4Hz,1H)7.816-7.705(m,6H),7.699-7.392(m,16H)7.195-7.127(m,2H)

[0077] [Table 6]

[0078] Example 7: Preparation of Compound H1-54 [ka] Compound 1-2 (5.7 g, 10.6 mmol), dibenzo[b,d]furan-1-ylboronic acid (2.5 g, 11.7 mmol), K2CO3 (4.4 g, 31.8 mmol), and Pd(PPh3)4 (0.61 g, 0.653 mmol) were dissolved in 30 mL of HO, 60 mL of toluene, and 30 mL of EtOH in a flask, and the mixture was refluxed at 120 °C for 3 h. After the reaction was completed, the organic layer was extracted with ethyl acetate and the residual water was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound H1-54 (1.2 g, yield: 18%). 1H NMR(600MHz,CDCl3,δ)8.880(s,1H),8.378-8.364(d,J=8.4Hz,1H),8.297-8.284(d,J=7.8Hz,1H ),8.000-7.987(d,J=7.8Hz,1H)7.777-7.702(m,5H),7.615-7.332(m,15H),7.189-7.127(m,4H)

[0079] [Table 7]

[0080] Example 8: Preparation of Compound H1-53 [ka] Compound 1-2 (5.0 g, 9.3 mmol), dibenzo[b,d]furan-4-ylboronic acid (2.2 g, 10.2 mmol), Pd(PPh3)4 (0.54 g, 0.47 mmol), and K2CO3 (2.6 g, 18.6 mmol) were dissolved in 20 mL of toluene, 8 mL of EtOH, and 10 mL of HO in a flask, and the mixture was refluxed at 120 °C for 3 h. After the reaction was completed, the organic layer was extracted with ethyl acetate and the residual water was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound H1-53 (3.5 g, yield: 60%). 1 H NMR(600MHz,DMSO3,δ)9.210(s,1H),8.516-8.502(d,1H),8.408-8.395(d,1H),8.219- 8.198(m,2H),8.115-8.109(t,1H),8.087-8.073(d,1H),8.040-8.028(d,1H),7.856-7. 842(d,1H),7.833-7.807(t,1H),7.733-7.611(m,9H),7.562-7.531(m,2H),7.515-7.4 90(t,1H),7.451-7.426(t,1H),7.293-7.279(d,1H),7.258-7.232(t,1H),7.119(s,1H)

[0081] [Table 8]

[0082] Example 9: Preparation of Compound H1-13 [ka] 7-Phenyl-7,9-dihydrobenzo[g]indolo[2,3-b]carbazole (3.6 g, 9.285 mmol), 1-(4-bromophenyl)dibenzo[b,d]furan (3 g, 9.285 mmol), CuI (0.08 g, 0.464 mmol), EDA (0.5 g, 9.285 mmol), and KPO (4.9 g, 23.21 mmol) were added to 50 mL of xylene and the mixture was stirred for 1 day. After the reaction was complete, the reaction product was cooled to room temperature and extracted with distilled water and MeOH. The extracted product was separated by column chromatography using MC / Hex to obtain compound H1-13 (2.7 g, 47% yield). 1 H NMR(DMSO-d6)δ:9.69(s,1H),9.26(d,J=8.3Hz,1H),8.69(dd,J=7.7,1.2Hz, 1H),8.14(dd,J=8.0,1.1Hz,1H),7.97(d,J=8.8Hz,1H),7.92(s,4H),7.88(d dd,J=8.2,6.9,1.3Hz,1H),7.82-7.76(m,4H),7.73(t,J=7.8Hz,2H),7.70-7 .48(m,8H),7.48-7.44(m,2H),7.42(td,J=7.3,1.0Hz,1H),7.26-7.20(m,1H)

[0083] [Table 9]

[0084] Example 10: Preparation of Compound H1-5 [ka] 7-Phenyl-7,9-dihydrobenzo[g]indolo[2,3-b]carbazole (7.6 g, 18.88 mmol), 3-chloro-1,1':2',1''-terphenyl (5 g, 18.88 mmol), Pd2(dba)3 (0.86 g, 0.940 mmol), NaOt-Bu (4.5 g, 47.22 mmol), and P(t-Bu)3 (0.38 g, 1.888 mmol) were added to 100 mL of toluene, and the mixture was stirred for 1 day. After the reaction was completed, the reaction product was cooled to room temperature and extracted with distilled water and MeOH. The extracted product was separated by column chromatography using MC / Hex to obtain compound H1-5 (0.7 g, yield: 6.2%). 1 H NMR(DMSO-d6)δ:9.58(s,1H),9.20(d,J=8.4Hz,1H),8.57(d,J=7.8Hz,1H),8.11(d,J=8.3Hz,1H),7.94(d,J=8.9Hz,1H),7.84(ddd,J= 8.3,6.8,1.3Hz,1H),7.72(d,J=6.2Hz,4H),7.64-7.47(m,8H),7.44(dt,J=6.0,1.9Hz,1H),7.40-7.17(m,10H),6.50(d,J=7.9Hz,1H)

[0085] [Table 10]

[0086] Example 11: Preparation of Compound H1-19 [ka] 7-Phenyl-7,9-dihydrobenzo[g]indolo[2,3-b]carbazole (5.1 g, 13 mmol), 9-(3-bromophenyl)-9H-carbazole (4.7 g, 14.6 mmol), Pd(dba) (0.604 g, 0.66 mmol), esphos (0.546 g, 1.33 mmol), and NaOt-Bu (3.20 g, 33.3 mmol) were added to 50 mL of xylene in a flask, and the mixture was stirred under reflux at 190 °C for 2 h. After the reaction was completed, the organic layer was extracted with EA, dried over MgSO, and separated by column chromatography. Then, MeOH was added to the separated product, and the resulting solid was filtered under reduced pressure to give compound H1-19 (4.4 g, yield: 53.0%). 1 H NMR(600MHz,DMSO-d6,δ)9.66(s,1H),9.24(d,J=8.4Hz,1H),8.66(d,J=7.7Hz,1H),8.2 6(d,J=7.8Hz,2H),8.13(d,J=8.1Hz,1H),8.01-7.94(m,2H),7.91-7.84(m,3H),7.79(d d,J=8.2,1.8Hz,1H),7.77-7.74(m,2H),7.69(t,J=7.6Hz,2H),7.62-7.55(m,3H),7.53 (d,J=8.1Hz,1H),7.49-7.45(m,2H),7.39(dd,J=14.4,6.9Hz,5H)7.31(t,J=7.5Hz,2H)

[0087] [Table 11]

[0088] Example 12: Preparation of Compound H1-6 [ka] 7-Phenyl-7,9-dihydrobenzo[g]indolo[2,3-b]carbazole (5.0 g, 13 mmol), 4'-bromo-1,1':3',1''-terphenyl (6.06 g, 20 mmol), Cu powder (1.307 g, 0.65 mmol), and K2CO3 (3.4 g, 26 mmol) were added to 60 mL of o-dichlorobenzene (o-DCB) in a flask, and the mixture was stirred under reflux at 230 °C for 12 h. After the reaction was completed, the organic layer was extracted with EA, dried over MgSO4, and separated by column chromatography. Then, MeOH was added to the separated product, and the resulting solid was filtered under reduced pressure to give compound H1-6 (1.3 g, yield: 16.3%). 1 H NMR(600MHz,DMSO-d6,δ)9.51(s,1H),9.16(d,J=8.3Hz,1H),8.57(d,J=7.8Hz,1H),8. 10(d,J=8.0Hz,1H),7.98-7.85(m,6H),7.83(t,J=7.6Hz,1H),7.76(s,1H),7.70(d,J= 8.1Hz,1H),7.61-7.51(m,5H),7.51-7.42(m,3H),7.38(t,J=7.8Hz,1H),7.31(t,J=7. 3Hz,1H),7.25(d,J=8.0Hz,1H),7.13-7.06(m,4H),7.03(d,J=6.8Hz,1H),6.79(s,1H)

[0089] [Table 12]

[0090] Example 13: Preparation of Compound H1-22 [ka] Synthesis of compound 11 7-Phenyl-7,9-dihydrobenzo[g]indolo[2,3-b]carbazole (10 g, 26.14 mmol), 1-bromo-3-iodobenzene (14.8 g, 52.29 mmol), CuI (2.5 g, 13.07 mmol), EDA (1.57 g, 26.14 mmol), and KPO (13.8 g, 65.36 mmol) were added to 130 mL of toluene and the mixture was stirred for 1 day. After the reaction was complete, the reaction product was cooled to room temperature and extracted with distilled water and MeOH. The extracted product was separated by column chromatography using MC / Hex to obtain compound 11 (9 g, 64% yield).

[0091] Synthesis of compound 12 Compound 11 (9 g, 16.74 mmol) was added to 85 mL of THF and stirred at -78 °C for 1 h. Then, n-BuLi (2.5 M) (8.7 mL, 21.77 mmol) was slowly added to the mixture. B(Oi-pr) (5.7 mL, 25.12 mmol) was added to the mixture, which was then stirred for 1 day. After the reaction was completed, NH4Cl and distilled water were added to the reaction product, and the mixture was stirred for 30 min. The resulting product was then extracted with distilled water and EA, and the organic layer was concentrated to give compound 12 (6.8 g, yield: 80%).

[0092] Synthesis of Compound H1-22 Compound 12 (6.8 g, 13.53 mmol), 4-bromo-9,9-dimethyl-9H-fluorene (3.7 g, 13.53 mmol), Pd(PPh3)4 (0.8 g, 0.676 mmol), and K2CO3 (3.7 g, 27.07 mmol) were added to 60 mL of toluene, 15 mL of EtOH, and 15 mL of distilled water, and the mixture was stirred under reflux for 3 h. After completion of the reaction, the reaction product 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 compound H1-22 (1.5 g, 17% yield). 1H NMR(DMSO-d6)δ:9.64(s,1H),9.22(d,J=8.4Hz,1H),8.64(dt,J=7.6,0.9Hz,1H),8.14-8.10(m,1H),7.94(d,J=8.9Hz,1H),7.90-7.77(m,3H),7.6 8(s,3H),7.65-7.53(m,7H),7.53-7.33(m,6H),7.27(td,J=7.4,1.1Hz,1 H),7.17(d,J=7.6Hz,1H),6.92(d,J=47.9Hz,2H),1.49(d,J=17.3Hz,6H)

[0093] [Table 13]

[0094] Example 14: Preparation of Compound H1-4 [ka] 7-Phenyl-7,9-dihydrobenzo[g]indolo[2,3-b]carbazole (5 g, 13.07 mmol), 4-bromo-1,1':2',1''-terphenyl (4 g, 13.07 mmol), Pd2(dba)3 (0.6 g, 0.653 mmol), NaOt-Bu (3.8 g, 39.21 mmol), and esphos (0.5 g, 1.307 mmol) were added to 70 mL of o-xylene, and the mixture was stirred for 1 day. After the reaction was completed, the reaction product was cooled to room temperature and extracted with distilled water and MeOH. The extracted product was separated by column chromatography using MC / Hex to obtain compound H1-4 (6.3 g, 78% yield). NMR(DMSO-d6)δ:9.63(s,1H),9.23(d,J=8.3Hz,1H),8.63(dd,J=7.7,1.1Hz, 1H),8.12(d,J=8.2Hz,1H),7.95(d,J=8.9Hz,1H),7.85(ddd,J=8.2,6.8,1.4H z,1H),7.79-7.73(m,2H),7.72-7.66(m,3H),7.60-7.47(m,8H),7.44(ddd,J= 8.2,7.1,1.3Hz,1H),7.38-7.33(m,3H),7.32-7.24(m,2H),7.22-7.14(m,5H)

[0095] [Table 14]

[0096] Example 15: Preparation of Compound H1-12 [ka] Synthesis of compound 13 Dibenzo[b,d]thiophen-1-ylboronic acid (20 g, 87.71 mmol), 1-bromo-3-iodobenzene (50 g, 175.4 mmol), Pd(PPh3)4 (5 g, 4.385 mmol), and Na2CO3 (18 g, 175.4 mmol) were added to 360 mL of toluene, 90 mL of distilled water, and 90 mL of EtOH, and the mixture was stirred under reflux for 3 h. After completion of the reaction, the reaction product was cooled to room temperature and extracted with distilled water and EA. The organic layer was evaporated under reduced pressure and separated by column chromatography using Hexafluoroethanol to give compound 13 (20 g, 67% yield).

[0097] Synthesis of Compounds H1-12 Compound 13 (4.4 g, 13.07 mmol), 7-phenyl-7,9-dihydrobenzo[g]indolo[2,3-b]carbazole (5 g, 13.07 mmol), Pd2(dba)3 (0.6 g, 0.653 mmol), esphos (0.5 g, 1.307 mmol), and NaOt-Bu (3.7 g, 39.21 mmol) were added to 70 mL of o-xylene and the mixture was stirred under reflux for 2 h. After completion of the reaction, the reaction product was cooled to room temperature and extracted with MeOH. The extracted product was separated by column chromatography using MC / Hex to give compound H1-12 (5.1 g, 60% yield). 1 H NMR(DMSO-d6)δ:9.63(s,1H),9.22(d,J=8.4Hz,1H),8.64(dd,J=7.5,1.2Hz,1H),8.14- 8.09(m,2H),8.07(dt,J=8.1,0.9Hz,1H),7.94(d,J=8.9Hz,1H),7.91-7.82(m,3H),7.72 (d,J=2.0Hz,1H),7.67(d,J=7.6Hz,2H),7.63-7.48(m,8H),7.48-7.41(m,2H),7.40(d, J=6.1Hz,1H),7.36(td,J=7.4,1.0Hz,1H),7.33(d,J=7.3Hz,1H),7.09(d,J=49.0Hz,2H)

[0098] [Table 15]

[0099] Example 16: Preparation of Compound H2-3 [ka] Synthesis of Compound 2-1 2-Chloro-4,6-di(naphthalen-2-yl)-1,3,5-triazine (20 g, 79.7 mmol), (4-bromonaphthalen-1-yl)boronic acid (32.2 g, 87.7 mmol), Pd(PPh3)4 (4.6 g, 3.985 mmol), and Cs2CO3 (65 g, 199.25 mmol) were added to 400 mL of toluene in a flask, and the mixture was stirred under reflux for 4 hours. After the reaction was complete, the reaction product was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The remaining water was removed with magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound 2-1 (30 g, yield: 74%).

[0100] Synthesis of compound H2-3 Compound 2-1 (10 g, 19.7 mmol), 9H-carbazole (3.0 g, 17.9 mmol), Pd(dba) (0.8 g, 0.9 mmol), esphos (0.73 g, 1.79 mmol), and NaOt-Bu (4.3 g, 44.75 mmol) were dissolved in 90 mL of o-xylene in a flask, and the mixture was stirred under reflux for 4 h. After completion of the reaction, the reaction product was extracted with ethyl acetate and separated by column chromatography to obtain compound H2-3 (1.5 g, yield: 13%).

[0101] [Table 16]

[0102] Example 17: Preparation of Compound H2-10 [ka] Synthesis of compound 2-2 4-Bromo-9H-carbazole (10 g, 40.6 mmol), phenylboronic acid (6.2 g, 48.7 mmol), Pd(PPh3)4 (2.3 g, 2.03 mmol), and Na2CO3 (13 g, 121.8 mmol) were added to 200 mL of toluene, 100 mL of ethanol, and 100 mL of water in a flask, and the mixture was stirred under reflux for 3 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The remaining water was removed with magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound 2-2 (9 g, yield: 91%).

[0103] Synthesis of compound H2-10 Compound 2-1 (8.5 g, 13.5 mmol), compound 2-2 (3.0 g, 12.3 mmol), Pd(dba) (0.56 g, 0.615 mmol), esphos (0.51 g, 1.23 mmol), and NaOt-Bu (2.9 g, 30.75 mmol) were dissolved in 60 mL of o-xylene in a flask, and the mixture was stirred under reflux for 4 hours. After completion of the reaction, the reaction product was extracted with ethyl acetate and separated by column chromatography to obtain compound H2-10 (2.8 g, yield: 32.5%).

[0104] [Table 17]

[0105] Example 18: Preparation of Compound H2-8 [ka] 4-Phenyl-9H-carbazole (3.0 g, 12.3 mmol), 2-(4-bromonaphthalen-1-yl)-4,6-diphenyl-1,3,5-triazine (5.4 g, 12.3 mmol), Pd2(dba)3 (0.56 g, 0.62 mmol), esphos (0.51 g, 1.23 mmol), and NaOt-Bu (2.4 g, 24.7 mmol) were added to 62 mL of o-xylene in a flask, and the mixture was stirred under reflux for 6 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and then MeOH was added to it with stirring at room temperature. The resulting solid was filtered under reduced pressure, and the filtrate was separated by column chromatography to obtain compound H2-8 (3.3 g, yield: 45%).

[0106] [Table 18]

[0107] Example 19: Preparation of Compound H2-2 [ka] Compound A (8.0 g, 16.4 mmol), 9H-carbazole (3.0 g, 18.0 mmol), Pd(dba) (0.9 g, 0.8 mmol), esphos (0.7 g, 1.64 mmol), and NaOt-Bu (2.4 g, 24.6 mmol) were added to 82 mL of o-xylene in a flask, and the mixture was stirred under reflux for 4 hours. After the reaction was completed, the reaction product was extracted with ethyl acetate and separated by column chromatography to obtain compound H2-2 (6.0 g, yield: 69%).

[0108] [Table 19]

[0109] Example 20: Preparation of Compound H2-11 [ka] Synthesis of Compound 2-3 1-Bromo-9H-carbazole (10 g, 40.6 mmol), phenylboronic acid (6.2 g, 48.7 mmol), Pd(PPh3)4 (2.3 g, 2.03 mmol), and Na2CO3 (13 g, 121.8 mmol) were added to 200 mL of toluene, 100 mL of ethanol, and 100 mL of water in a flask, and the mixture was stirred under reflux for 3 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The remaining water was removed with magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound 2-3 (9 g, yield: 96%).

[0110] Synthesis of compound H2-11 Compound 2-3 (3.0 g, 12.3 mmol), compound A (8 g, 18.5 mmol), Cu powder (0.39 g, 6.15 mmol), and K2CO3 (3.4 g, 24.6 mmol) were added to 60 mL of dichlorobenzene (DCB) in a flask, and the mixture was stirred under reflux for 24 hours. After the reaction was completed, the reaction product was cooled to room temperature, and MeOH was added to it while stirring at room temperature. The resulting solid was filtered under reduced pressure, and the filtrate was separated by column chromatography to obtain compound H2-11 (1.1 g, yield: 14.8%).

[0111] [Table 20]

[0112] The luminous efficiency and lifetime characteristics of the OLED according to the present disclosure will be described in detail below. However, the following examples only serve to describe the characteristics of the OLED according to the present disclosure in detail, and the present disclosure is not limited to the following examples.

[0113] Device Examples 1-1 to 1-3: Fabrication of OLEDs Co-deposited with a First Host Compound and a Second Host Compound According to the Present Disclosure An OLED according to the present disclosure was fabricated as follows. A transparent indium tin oxide (ITO) thin film (10 Ω / sq) electrode on an OLED glass substrate (Geomatec Co., Ltd., Japan) was ultrasonically cleaned sequentially with acetone and isopropyl alcohol, and then stored in isopropanol. The ITO substrate was attached to a substrate holder in a vacuum evaporation system. Compound HI-1, shown in Table 3 below, was introduced into one cell of the vacuum evaporation system as a first hole injection compound, and compound HT-1, shown in Table 3 below, was introduced into another cell of the vacuum evaporation system as a first hole transport compound. The two materials were evaporated and deposited at different rates with a doping amount of the first hole injection compound of 3 wt % based on the total amount of the first hole injection compound and the first hole transport compound, to form a first hole injection layer with a thickness of 10 nm on the ITO substrate. Next, compound HT-1 was evaporated onto the first hole injection layer as a first hole transport layer with a thickness of 80 nm. Next, compound HT-2 was introduced into another cell of the vacuum evaporation system and evaporated by passing a current through the cell, thereby forming a 60-nm-thick second hole-transporting layer on the first hole-transporting layer. After forming the hole-injection layer and hole-transporting layer, an emitting layer was formed thereon as follows. The first and second host compounds shown in Table 1 below were introduced into two cells of the vacuum evaporation system as hosts, respectively, and compound D-39 was introduced into another cell as a dopant. The two host materials were evaporated in a 1:1 ratio, and simultaneously the dopant materials were evaporated in different ratios to form a 40-nm-thick emitting layer on the second hole-transporting layer with a doping amount of 3 wt % based on the total amount of host and dopant. Next, compounds ET-1 and EI-1 were evaporated in a 50:50 weight ratio as electron-transporting materials on the emitting layer to form a 35-nm-thick electron-transporting layer. After depositing the compound EI-1 as an electron injection layer with a thickness of 2 nm on the electron transport layer, an 80 nm thick Al cathode was deposited on the electron injection layer using another vacuum deposition device. In this way, an OLED was fabricated. All materials used to fabricate the OLED were used in 10 -6 It was purified by vacuum sublimation at torr.

[0114] Comparative Examples 1-1 to 1-3: Preparation of OLEDs containing comparative compounds as hosts An OLED was fabricated in the same manner as in Device Example 1-1, except that the second host compound shown in Table 1 below was used alone as the host in the emissive layer.

[0115] Comparative Examples 1-4: Fabrication of OLEDs containing comparative compounds as hosts An OLED was fabricated in the same manner as in Device Example 1-1, except that the first host compound and the second host compound shown in Table 1 below were used as hosts in the light-emitting layer.

[0116] The driving voltage, luminous efficiency, and emission color at a luminance of 1,000 nits, and the time it takes for the luminance to decrease from 100% to 95% at a luminance of 5,500 nits (T95) for the OLEDs fabricated in Device Examples 1-1 to 1-3 and Comparative Examples 1-1 to 1-4 are shown in Table 1 below.

[0117] [Table 21]

[0118] From Table 1 above, it can be seen that the organic electroluminescent device containing the specific combination of compounds of the present disclosure as a host material has a significantly reduced driving voltage and significantly improved luminous efficiency and lifespan characteristics compared to conventional organic electroluminescent devices.

[0119] Device Examples 2-1 to 2-3: Fabrication of OLEDs According to the Present Disclosure An OLED was fabricated in the same manner as in Device Example 1-1, except that the light-emitting layer was formed as follows: The compound shown in Table 2 below as a host was introduced into one cell of a vacuum deposition apparatus, and Compound D-39 was introduced as a dopant into another cell of the vacuum deposition apparatus. The two materials were evaporated at different rates and deposited at a doping amount of 3 wt % based on the total amount of the host and dopant to form a light-emitting layer with a thickness of 40 nm on the second hole-transporting layer.

[0120] Comparative Example 2-1: Preparation of an OLED containing a comparative compound An OLED was fabricated in the same manner as in Device Example 2-1, except that Compound A-1 shown in Table 3 below was used as the host in the emissive layer.

[0121] Table 2 below shows the time it takes for the OLEDs fabricated in Device Examples 2-1 to 2-3 and Comparative Example 2-1 to decrease from an initial luminance of 100% to 95% at a luminance of 5500 nits (T95).

[0122] [Table 22]

[0123] From Table 2 above, it can be seen that the organic electroluminescent device containing the compound according to the present disclosure as a host material has longer life characteristics compared to conventional organic electroluminescent devices.

[0124] The compounds used in the device examples and comparative examples are shown in Table 3 below.

[0125] [Table 23]

Claims

1. Formula 1 below: 【Chemistry 1】 (In the formula, ring A and ring C each independently represent a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring; Ring B represents a deuterium-substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring; Y represents O, S, or NRa; Ra is -L ２ -Ar ２ represents Ar １ and Ar ２ each independently represent a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3-30 membered)heteroaryl containing at least one of nitrogen, oxygen, and sulfur, or a substituted or unsubstituted di(C6-C30)arylamino, wherein the (3-30 membered)heteroaryl is selected from the group consisting of carbazolyl, benzocarbazolyl, dibenzothiophenyl, benzothiophenyl, dibenzofuranyl, benzofuranyl, benzonaphthofuranyl, and benzonaphthothiophenyl; L １ and L ２ each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a deuterated or unsubstituted (3-30 membered) heteroarylene; n represents an integer of 0 or 1, provided that when n is 0, both ring A and ring B are substituted or unsubstituted naphthalene rings. a first host material containing a compound represented by Formula 2 below: 【Chemistry 2】 (In the formula, HAr represents a substituted or unsubstituted nitrogen-containing (3- to 30-membered) heteroaryl, wherein the substituent of the substituted nitrogen-containing (3- to 30-membered) heteroaryl is at least one selected from the group consisting of deuterium and (C6-C30)aryl; L ３ represents unsubstituted or deuterium-substituted naphthylene, unsubstituted or deuterium-substituted biphenylene, unsubstituted or deuterium-substituted terphenylene, or unsubstituted or deuterium-substituted -phenylene-naphthylene-; R １ ~R ８ each independently represents hydrogen, deuterium, or (C6-C30)aryl unsubstituted or substituted with at least one of deuterium and (C6-C30)aryl. a second host material containing a compound represented by A plurality of host materials including:

2. Substituents of the substituted benzene, the substituted naphthalene, the substituted aryl, the substituted arylene, the substituted heteroaryl, the substituted heteroarylene, and the diarylamino are each independently deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1 to C30) alkyl, halo(C1 to C30) alkyl, (C2 to C30) alkenyl, (C2 to C30) alkynyl, (C1 to C30) alkoxy, (C1 to C30) alkylthio, (C3 to C30) cycloalkyl, (C3-C30)cycloalkenyl, (3- to 7-membered)heterocycloalkyl, (C6-C30)aryloxy, (C6-C30)arylthio, (3- to 50-membered)heteroaryl unsubstituted or substituted with at least one of (C1-C30)alkyl, (C6-C30)aryl, and di(C6-C30)arylamino, unsubstituted or deuterium, cyano, (C1-C30)alkyl, (3- to 50-membered)heteroaryl, di(C6-C30)arylamino, and tri(C6-C30)aryl. (C6-C30)aryl substituted with at least one (C6-C30)arylsilyl, 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 10. The plurality of host materials of claim 1, wherein the alkyl group is at least one selected from the group consisting of (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 formula 1 is represented by the following formulas 1-1 to 1-7: 【Transformation 3】 (In the formula, Ar １ , L １ and Y are as defined in claim 1, R １１ ~R ２７ 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, 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; a, d, h, m, q, and r each independently represent an integer of 1 to 6, b, c, e, f, g, i, j, k, l, o, and p each independently represent an integer of 1 to 4, and a to m and o to r each independently represent an integer of 2 or more, R １１ Each of R １２ Each of R １３ Each of R １４ Each of R １５ Each of R １６ Each of R １７ Each of R １８ Each of R １９ Each of R ２０ Each of R ２１ Each of R ２２ Each of R ２３ Each of R ２４ Each of R ２５ Each of R ２６ and R ２７ may be the same or different) 2. The host material of claim 1, wherein the host material is one of:

4. Ar １ represents substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted naphthylphenylamino, or substituted or unsubstituted biphenylphenylamino.

5. The formula 2 can be converted into the following formula 3: 【Chemistry 4】 (In the formula, Ar ２１ and Ar ２２ each independently represent unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted biphenyl, unsubstituted or deuterium-substituted terphenyl, or unsubstituted or deuterium-substituted naphthyl; L ２１ represents unsubstituted or deuterium-substituted naphthylene or unsubstituted or deuterium-substituted biphenylene; R １ , R ４ , R ５ , and R ８ each independently represent hydrogen, deuterium, unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted biphenyl, unsubstituted or deuterium-substituted terphenyl, or unsubstituted or deuterium-substituted naphthyl; R ２ , R ３ , R ６ , and R ７ each independently represents hydrogen or deuterium; However, Ar ２１ and Ar ２２ When both represent phenyl, R １ , R ４ , R ５ , and R ８ (Provided that at least one of the following is not hydrogen or deuterium) 2. The host material of claim 1, wherein:

6. 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 quinolyl, substituted or unsubstituted benzoquinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted benzoisoquinolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted naphthyridinyl, or substituted or unsubstituted benzothienopyrimidinyl; 2. The host materials of claim 1 , wherein a substituent of the triazinyl, the substituted pyridyl, the substituted pyrimidinyl, the substituted quinazolinyl, the substituted benzoquinazolinyl, the substituted quinoxalinyl, the substituted benzoquinoxalinyl, the substituted quinolyl, the substituted benzoquinolyl, the substituted isoquinolyl, the substituted benzoisoquinolyl, the substituted triazolyl, the substituted pyrazolyl, the substituted naphthyridinyl, and the substituted benzothienopyrimidinyl is at least one selected from the group consisting of deuterium and (C6-C30)aryl.

7. The compound represented by formula 1 is the following compound: 【Transformation 5】 【Transformation 6】 【Transformation 7】 【Transformation 8】 【Chemistry 9】 10. The plurality of host materials of claim 1, wherein the host material is at least one selected from:

8. The compound represented by formula 2 is the following compound: 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 10. The plurality of host materials of claim 1, wherein the host material is at least one selected from:

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

10. Formula 3 below: 【Chemistry 13】 (In the formula, Ar ２１ represents unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted biphenyl, unsubstituted or deuterium-substituted terphenyl, or unsubstituted or deuterium-substituted naphthyl; Ar 22 represents unsubstituted or deuterium-substituted naphthyl; L ２１ represents unsubstituted or deuterium-substituted naphthylene; R １ , R ４ , R ５ , and R ８ each independently represent hydrogen, deuterium, unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted biphenyl, unsubstituted or deuterium-substituted terphenyl, or unsubstituted or deuterium-substituted naphthyl; R ２ , R ３ , R ６ , and R ７ each independently represents hydrogen or deuterium. An organic electroluminescent compound represented by the formula:

11. A compound of the following: 【Chemistry 14】 【Chemistry 15】 The organic electroluminescent compound is at least one selected from:

12. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 10 or 11.

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