Multiple host materials, organic electroluminescent compounds, and organic electroluminescent devices comprising same

Abstract

The present disclosure relates to various host materials, organic electroluminescent compounds, and organic electroluminescent devices. By comprising various host materials and / or organic electroluminescent compounds according to the present disclosure, it is possible to provide an organic electroluminescent device having low driving voltage and / or high luminous efficiency and / or long lifespan characteristics.

Description

Technical Field

[0001] The present disclosure relates to a variety of host materials, organic electroluminescent compounds, and organic electroluminescent devices comprising the same. Background Art

[0002] TPD / Alq with green light emission consisting of a light-emitting layer and a charge transport layer 3 Double-layer small molecule organic electroluminescent devices (OLEDs) were first developed by Tang et al. of Eastman Kodak in 1987. Since then, research on organic electroluminescent devices has been rapidly conducted, and OLEDs have been commercialized since then. Currently, OLEDs mainly use phosphorescent materials with excellent luminous efficiency in panel implementation. Therefore, for long-term use and high display resolution, OLEDs with high luminous efficiency and / or long life characteristics are required.

[0003] In order to improve the luminous efficiency, driving voltage and / or lifespan, various materials or concepts for the organic layer of the organic electroluminescent device have been proposed, but these are not satisfactory in actual use. Therefore, there is a continuous need to develop an organic electroluminescent device having improved performance such as improved driving voltage, luminous efficiency, power efficiency, and / or lifespan characteristics compared to previously disclosed organic electroluminescent devices.

[0004] Chinese Patent Application Publication No. 114702484 discloses an organic electroluminescent device containing an azole-based organic compound as a single host, but does not specifically disclose a plurality of host materials containing a specific combination of compounds as described in the present disclosure. Summary of the invention

[0005] Technical issues

[0006] The purpose of the present disclosure is first to provide a variety of host materials capable of producing organic electroluminescent devices with low driving voltage and / or high luminous efficiency and / or long life characteristics, and secondly, to provide an organic electroluminescent compound with a novel structure suitable for use as an organic electroluminescent device. In addition, another object of the present disclosure is to provide an organic electroluminescent device with low driving voltage and / or high luminous efficiency and / or long life characteristics by comprising a specific combination of compounds or according to the organic electroluminescent compound of the present disclosure.

[0007] Solution to the problem

[0008] As a result of intensive research to solve the above technical problems, the inventors of the present invention found that the above objectives can be achieved by a plurality of host materials comprising at least one first host compound represented by Formula 1 below and at least one second host compound represented by Formula 2 below, thereby completing the present invention.

[0009]

[0010] In formula 1,

[0011] X 1 and Y 1 Each independently represents -N=, -NR 7 , -O-, or -S-; provided that X 1 and Y 1 Any one of is -N=, and X 1 and Y 1 The other one is -NR 7 -, -O-, or -S-;

[0012] R 1 Indicates substituted or unsubstituted (C 6 -C 30 )aryl or substituted or unsubstituted (3- to 30-membered) heteroaryl;

[0013] R 2 To R 4 and R 7 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C 1 -C 30 ) alkyl, substituted or unsubstituted (C 6 -C 30 )aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C 3 -C 30 )cycloalkyl, substituted or unsubstituted (C 1 -C 30 ) alkoxy, substituted or unsubstituted tri(C 1 -C 30 )alkylsilyl, substituted or unsubstituted di(C 1 -C 30 )alkyl(C 6 -C 30 ) arylsilyl, substituted or unsubstituted (C 1 -C 30 )alkyldi(C 6 -C 30 ) arylsilyl, substituted or unsubstituted tri(C 6 -C 30 ) arylsilyl, (C 3 -C 30 ) aliphatic ring and (C 6 -C 30 ) a substituted or unsubstituted condensed ring of an aromatic ring, or -L 11 -N(Ar1 )(Ar 2 ) ; or may be connected to adjacent substituents to form one or more rings;

[0014] L 1 and L 11 Each independently represents a single bond, substituted or unsubstituted (C 6 -C 30 )arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene;

[0015] R 5 and R 6 Each independently represents a substituted or unsubstituted (C 6 -C 30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl;

[0016] Ar 1 and Ar 2 Each independently represents hydrogen, substituted or unsubstituted (C 1 -C 30 ) alkyl, substituted or unsubstituted (C 2 -C 30 ) alkenyl, (C 3 -C 30 ) aliphatic ring and (C 6 -C 30 ) a substituted or unsubstituted condensed ring of an aromatic ring, a substituted or unsubstituted (C 6 -C 30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; and

[0017] b and c each independently represent an integer of 1 or 2, d is an integer of 1 to 4, and when b to d are integers of 2 or more, R 2 To R 4 Each of can be the same or different.

[0018]

[0019] In formula 2,

[0020] Ring A and Ring B each independently represent a substituted or unsubstituted (C 6 -C 30 )arene, or substituted or unsubstituted (3- to 30-membered) heteroarene;

[0021] R 11 and R 12 Each independently represents a substituted or unsubstituted (C 1 -C 30 ) alkyl, substituted or unsubstituted (C 6 -C30 ) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; or may be connected to each other to form one or more rings;

[0022] X 2 and Y 2 Each independently represents -N=, -NR 24 , -O-, or -S-; provided that X 2 and Y 2 Any one of is -N=, and X 2 and Y 2 The other one is -NR 24 -, -O-, or -S-;

[0023] R 21 To R 24 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C 1 -C 30 ) alkyl, substituted or unsubstituted (C 6 -C 30 )aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C 3 -C 30 )cycloalkyl, substituted or unsubstituted (C 1 -C 30 ) alkoxy, substituted or unsubstituted tri(C 1 -C 30 )alkylsilyl, substituted or unsubstituted di(C 1 -C 30 )alkyl(C 6 -C 30 ) arylsilyl, substituted or unsubstituted (C 1 -C 30 )alkyldi(C 6 -C 30 ) arylsilyl, substituted or unsubstituted tri(C 6 -C 30 ) arylsilyl, (C 3 -C 30 ) aliphatic ring and (C 6 -C 30 ) a substituted or unsubstituted condensed ring of an aromatic ring, or -L 3 -HAr;

[0024] The premise is R 21 To R 24 At least one of them is -L 3 -HAr;

[0025] L 2 and L 3Each independently represents a single bond, substituted or unsubstituted (C 6 -C 30 )arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene;

[0026] HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group containing at least one nitrogen atom; and

[0027] n represents an integer of 1 to 4, m represents an integer of 1 to 8, and when n and m are integers of 2 or more, R 22 and R 23 Each of can be the same or different.

[0028] Beneficial Effects of the Invention

[0029] By including various host materials and / or organic electroluminescent compounds according to the present disclosure, an organic electroluminescent device having low driving voltage and / or high luminous efficiency and / or long life characteristics may be provided. DETAILED DESCRIPTION

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

[0031] The present disclosure relates to a plurality of host materials and an organic electroluminescent device including the plurality of host materials. The plurality of host materials include at least one first host compound represented by Formula 1 and at least one second host compound represented by Formula 2.

[0032] The present disclosure relates to an organic electroluminescent compound represented by Formula 2', an organic electroluminescent material including the organic electroluminescent compound, and an organic electroluminescent device including the organic electroluminescent compound and / or the organic electroluminescent material.

[0033] Herein, the term "organic electroluminescent compound" in the present disclosure means a compound that can be used in an organic electroluminescent device and, if necessary, can be contained in any material layer constituting the organic electroluminescent device.

[0034] Herein, the term "organic electroluminescent material" means a material that can be used in an organic electroluminescent device and can contain at least one compound. If necessary, the organic electroluminescent material can be contained 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 auxiliary material, a luminescence auxiliary material, an electron blocking material, a luminescent material (containing a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material, etc.

[0035] The term "multiple organic electroluminescent materials" in the present disclosure means an organic electroluminescent material comprising a combination of at least two compounds, which may be included in any layer constituting an organic electroluminescent device. It may mean both a material contained in an organic electroluminescent device before (e.g., before vapor deposition) and a material contained in an organic electroluminescent device after (e.g., after vapor deposition). For example, a plurality of organic electroluminescent materials may be a combination of at least two compounds, which may be included in at least one of the following layers: a hole injection layer, a hole transport layer, a hole auxiliary layer, a luminescent auxiliary 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. Therefore, at least two compounds may be included in the same layer or in different layers, and may be mixed-evaporated or co-evaporated, or may be evaporated individually.

[0036] Herein, the term "multiple host materials" means an organic electroluminescent material comprising a combination of at least two host materials. It may mean both a material before being included in an organic electroluminescent device (e.g., before vapor deposition) and a material after being included in an organic electroluminescent device (e.g., after vapor deposition). The various host materials disclosed herein may be included in any light-emitting layer constituting an organic electroluminescent device. At least two compounds included in the various host materials may be included in one light-emitting layer together, or may each be included in a separate light-emitting layer. When at least two compounds are included in one light-emitting layer, the at least two compounds may be mixed-evaporated to form a layer, or the at least two compounds may be co-evaporated individually and simultaneously to form a layer.

[0037] In this article, “(C 1 -C 30 "(C)alkylene" means a straight or branched alkyl group having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10. The above alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, etc. As used herein, the term "(C)alkylene" means a straight or branched alkyl group having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10. The above alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, etc. 3 -C 30 "(Cycloalkylene)" means a monocyclic hydrocarbon or polycyclic hydrocarbon having 3 to 30 ring skeleton carbon atoms, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The above-mentioned cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, etc. Herein, "(C 6 -C 30The "(sub)aryl" is a monocyclic or condensed ring group derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, wherein the number of ring backbone carbon atoms is preferably 6 to 20, more preferably 6 to 15, which may be partially saturated and may contain a spiro structure. Examples of the aryl group may specifically be phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthrenyl, triphenylenyl, phenylphenanthrenyl, anthracenyl, benzanthryl, indenyl, triphenylene, pyrenyl, naphthyl, peryl, Benzo The aryl group may be an aryl group, such as an o-tolyl group, an m-tolyl group, a p-tolyl group, a 2,3-xyl group, a 3,4-xyl group, a 2,5-xyl group, a mesityl group, an o-cumyl group, a m-cumyl group, a p-cumyl group, a p-tert-butylphenyl group, a p-(2-phenylpropyl)phenyl group, a 4′-methylbiphenyl group, a 4″-tert-butyl-p-terphenyl-4-yl group, an o-biphenyl group, a m-biphenyl group, a p-biphenyl group, an o-terphenyl group, a m-terphenyl-4-yl group, a m-terphenyl-3-yl group, a m-terphenyl-2-yl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl- Phenyl-2-yl, m-quaterphenyl, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 9-phenanthrenyl, 1- Base, 2- Base, 3- Base, 4- Base, 5- Base, 6- Benzo[c]phenanthrenyl, benzo[g] 1-triphenylene, 2-triphenylene, 3-triphenylene, 4-triphenylene, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, 11,11-dimethyl-1-benzo[a]fluorenyl, 11,11-dimethyl-2-benzo[a]fluorenyl, 11,11-dimethyl-3-benzo[a]fluorenyl, 11, 11-dimethyl-4-benzo[a]fluorenyl, 11,11-dimethyl-5-benzo[a]fluorenyl, 11,11-dimethyl-6-benzo[a]fluorenyl, 11,11-dimethyl-7-benzo[a]fluorenyl, 11,11-dimethyl-8-benzo[a]fluorenyl, 11,11-dimethyl-9-benzo[a]fluorenyl, 11,11- dimethyl-10-benzo[a]fluorenyl, 11,11-dimethyl-1-benzo[b]fluorenyl, 11,11-dimethyl-2-benzo[b]fluorenyl, 11,11-dimethyl-3-benzo[b]fluorenyl, 11,11-dimethyl-4-benzo[b]fluorenyl, 11,11-dimethyl-5-benzo[b]fluorenyl, 11,11-dimethyl 11,11-dimethyl-6-benzo[b]fluorenyl, 11,11-dimethyl-7-benzo[b]fluorenyl, 11,11-dimethyl-8-benzo[b]fluorenyl, 11,11-dimethyl-9-benzo[b]fluorenyl, 11,11-dimethyl-10-benzo[b]fluorenyl, 11,11-dimethyl-1-benzo[c]fluorenyl, 11,11-dimethyl- 2-Benzo[c]fluorenyl, 11,11-dimethyl-3-benzo[c]fluorenyl, 11,11-dimethyl-4-benzo[c]fluorenyl, 11,11-dimethyl-5-benzo[c]fluorenyl, 11,11-dimethyl-6-benzo[c]fluorenyl, 11,11-dimethyl-7-benzo[c]fluorenyl, 11,11-dimethyl-8-benzo[c]fluorenyl 11,11-dimethyl-9-benzo[c]fluorenyl, 11,11-dimethyl-10-benzo[c]fluorenyl, 11,11-diphenyl-1-benzo[a]fluorenyl, 11,11-diphenyl-2-benzo[a]fluorenyl, 11,11-diphenyl-3-benzo[a]fluorenyl, 11,11-diphenyl-4-benzo[ a]fluorenyl, 11,11-diphenyl-5-benzo[a]fluorenyl, 11,11-diphenyl-6-benzo[a]fluorenyl, 11,11-diphenyl-7-benzo[a]fluorenyl, 11,11-diphenyl-8-benzo[a]fluorenyl, 11,11-diphenyl-9-benzo[a]fluorenyl, 11,11-diphenyl-10-benzo[a] Fluorenyl, 11,11-diphenyl-1-benzo[b]fluorenyl, 11,11-diphenyl-2-benzo[b]fluorenyl, 11,11-diphenyl-3-benzo[b]fluorenyl, 11,11-diphenyl-4-benzo[b]fluorenyl, 11,11-diphenyl-5-benzo[b]fluorenyl, 11,11-diphenyl-6-benzo[b]fluorenyl,11,11-diphenyl-7-benzo[b]fluorenyl, 11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9-benzo[b]fluorenyl, 11,11-diphenyl-10-benzo[b]fluorenyl, 11,11-diphenyl-1-benzo[c]fluorenyl, 11,11-diphenyl-2-benzo[c]fluorenyl, 11,11-diphenyl-3-benzo[c]fluorenyl, 11,11-diphenyl-4-benzo[c]fluorenyl, 11,11-diphenyl-5-benzo[c]fluorenyl, 11,11-diphenyl-6-benzo[c]fluorenyl [c]fluorenyl, 11,11-diphenyl-7-benzo[c]fluorenyl, 11,11-diphenyl-8-benzo[c]fluorenyl, 11,11-diphenyl-9-benzo[c]fluorenyl, 11,11-diphenyl-10-benzo[c]fluorenyl, 9,9,10,10-tetramethyl-9,10-dihydro-1-phenanthryl, 9,9,10,10-tetramethyl-9,10-dihydro-2-phenanthryl, 9,9,10,10-tetramethyl-9,10-dihydro-3-phenanthryl, 9,9,10,10-tetramethyl-9,10-dihydro-4-phenanthryl, and the like. Herein, "(3- to 30-membered) (sub) heteroaryl" is an aryl group having 3 to 30 ring backbone atoms and including at least one, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, Si, P, Se and Ge, wherein the number of ring backbone carbon atoms is preferably 5 to 25. The above-mentioned (sub) heteroaryl group can be a monocyclic ring or a condensed ring condensed with at least one benzene ring; and can be partially saturated. In addition, herein, the above-mentioned heteroaryl group can be a heteroaryl group formed by connecting at least one heteroaryl group or aryl group to a heteroaryl group via one or more single bonds. Examples of heteroaryl groups specifically include monocyclic heteroaryl groups, including furanyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc.; and condensed ring heteroaryl groups, including benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothienyl, dibenzoselenophene, benzofuranoquinolyl, benzofuranoquinazolyl, benzofurano naphthyridinyl, benzofuranopyrimidinyl, naphthoxyfuranyl, etc. pyrimidinyl, benzothienoquinolyl, benzothienoquinazolinyl, benzothienonaphthyridinyl, benzothienopyrimidinyl, naphthothienopyrimidinyl, pyrimidoindolyl, benzopyrimidoindolyl, benzofuranopyrazinyl, naphthofuranopyrazinyl, benzothienopyrazinyl, naphthothienopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl,Carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, indolizidinyl, acridinyl, silafluorenyl, germafluorenyl, benzotriazolyl, phenazinyl, imidazopyridinyl, chromenoquinazolinyl, thiochromenoquinazolinyl, dimethylbenzopyrimidinyl, indolocarbazolyl, indenocarbazolyl, etc. More specifically, the heteroaryl group can be 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidyl, 4-pyrimidyl, 5-pyrimidyl, 6-pyrimidyl, 1,2,3-triazine-4-yl, 1,2,4-triazine-3-yl, 1,3,5-triazine-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolidinyl, 2-indolidinyl, 3-indolidinyl, 5-indolidinyl, 6-indolidinyl, 7-indolidinyl, 8-indolidinyl, 2-imidazopyridinyl, 3-imidazopyridin ...imidazopyridinyl, 3-imidazopyridinyl, 5-indolidinyl, 6-indolidinyl, 7-indolidinyl, 8-indolidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 8-indolidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 8-indolidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 8-indolidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, oxazolopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furanyl, 3-furanyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl yl, 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, azacarbazole-1-yl, azacarbazole-2-yl, azacarbazole-3-yl, azacarbazole-4-yl, carbazol-4-yl, azacarbazol-5-yl, azacarbazol-6-yl, azacarbazol-7-yl, azacarbazol-8-yl, azacarbazol-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl,2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2-tert-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4-tert-butyl-1-indolyl, 2-tert-butyl-3-indolyl, 4-tert-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl Thienyl, 4-dibenzothienyl, 1-naphtho-[1,2-b]-benzofuranyl, 2-naphtho-[1,2-b]-benzofuranyl, 3-naphtho-[1,2-b]-benzofuranyl, 4-naphtho-[1,2-b]-benzofuranyl, 5-naphtho-[1,2-b]-benzofuranyl, 6-naphtho-[1,2-b]-benzofuranyl furanyl, 7-naphtho-[1,2-b]-benzofuranyl, 8-naphtho-[1,2-b]-benzofuranyl, 9-naphtho-[1,2-b]-benzofuranyl, 10-naphtho-[1,2-b]-benzofuranyl, 1-naphtho-[2,3-b]-benzofuranyl, 2-naphtho-[2,3-b]-benzofuranyl, 3-naphtho-[1,2-b]-benzofuranyl, -[2,3-b]-benzofuranyl, 4-naphtho-[2,3-b]-benzofuranyl, 5-naphtho-[2,3-b]-benzofuranyl, 6-naphtho-[2,3-b]-benzofuranyl, 7-naphtho-[2,3-b]-benzofuranyl, 8-naphtho-[2,3-b]-benzofuranyl, 9-naphtho-[2,3-b]- benzofuranyl, 10-naphtho-[2,3-b]-benzofuranyl, 1-naphtho-[2,1-b]-benzofuranyl, 2-naphtho-[2,1-b]-benzofuranyl, 3-naphtho-[2,1-b]-benzofuranyl, 4-naphtho-[2,1-b]-benzofuranyl, 5-naphtho-[2,1-b]-benzofuranyl, 6- naphtho-[2,1-b]-benzofuranyl, 7-naphtho-[2,1-b]-benzofuranyl, 8-naphtho-[2,1-b]-benzofuranyl, 9-naphtho-[2,1-b]-benzofuranyl, 10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b]-benzothienyl, 2-naphtho-[1,2-b]-benzothiophene b]-benzothiophenyl, 3-naphtho-[1,2-b]-benzothiophenyl, 4-naphtho-[1,2-b]-benzothiophenyl, 5-naphtho-[1,2-b]-benzothiophenyl, 6-naphtho-[1,2-b]-benzothiophenyl, 7-naphtho-[1,2-b]-benzothiophenyl, 8-naphtho-[1,2-b]-benzothiophenyl,9-naphtho-[1,2-b]-benzothiophenyl, 10-naphtho-[1,2-b]-benzothiophenyl, 1-naphtho-[2,3-b]-benzothiophenyl, 2-naphtho-[2,3-b]-benzothiophenyl, 3-naphtho-[2,3-b]-benzothiophenyl, 4-naphtho-[2,3-b]-benzothiophenyl, 5-naphtho-[2,3-b]-benzothiophenyl, 1-naphtho-[2,1-b]-benzothiophenyl, 2-naphtho-[2,1-b]-benzothiophenyl, 3-naphtho-[2,1-b]-benzothiophenyl , 4-naphtho-[2,1-b]-benzothiophenyl, 5-naphtho-[2,1-b]-benzothiophenyl, 6-naphtho-[2,1-b]-benzothiophenyl, 7-naphtho-[2,1-b]-benzothiophenyl, 8-naphtho-[2,1-b]-benzothiophenyl, 9-naphtho-[2,1-b]-benzothiophenyl, 10-naphtho-[2,1-b]-benzothiophenyl, 2-benzofurano[3,2-d]pyrimidinyl, 6-benzofurano[3,2-d]pyrimidinyl, 7-benzofurano[3,2-d]pyrimidinyl, 8 -Benzofurano[3,2-d]pyrimidinyl, 9-Benzofurano[3,2-d]pyrimidinyl, 2-Benzothiol[3,2-d]pyrimidinyl, 6-Benzothiol[3,2-d]pyrimidinyl, 7-Benzothiol[3,2-d]pyrimidinyl, 8-Benzothiol[3,2-d]pyrimidinyl, 9-Benzothiol[3,2-d]pyrimidinyl, 2-Benzofurano[3,2-d]pyrazinyl, 6-Benzofurano[3,2-d]pyrazinyl, 7-Benzofurano[3,2-d]pyrazinyl, 8-Benzofurano[3,2-d]pyrazinyl yl, 9-benzofurano[3,2-d]pyrazinyl, 2-benzothio[3,2-d]pyrazinyl, 6-benzothio[3,2-d]pyrazinyl, 7-benzothio[3,2-d]pyrazinyl, 8-benzothio[3,2-d]pyrazinyl, 9-benzothio[3,2-d]pyrazinyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germanylfluorenyl, 2-germanylfluorenyl, 3-germanylfluorenyl, 4-germanylfluorenyl, 1-dibenzoselenophene, 2-dibenzoselenophene, 3-dibenzoselenophene, 4-dibenzoselenophene, etc. As used herein, the term “(C, 3 -C 30 ) aliphatic ring and (C 6 -C 30)Aromatic ring condensed ring means a ring formed by condensing at least one aliphatic ring having 3 to 30 ring skeleton carbon atoms (wherein the number of carbon atoms is preferably 3 to 25, more preferably 3 to 18) and at least one aromatic ring having 6 to 30 ring skeleton carbon atoms (wherein the number of carbon atoms is preferably 6 to 25, more preferably 6 to 18). For example, the condensed ring may be a condensed ring of at least one benzene and at least one cyclohexane, or a condensed ring of at least one naphthalene and at least one cyclopentane, etc. Herein, in (C 3 -C 30 ) aliphatic ring and (C 6 -C 30 ) The carbon atoms in the fused ring of the aromatic ring may be replaced by at least one heteroatom selected from B, N, O, S, Si and P, preferably at least one heteroatom selected from N, O and S. The term "halogen" in the present disclosure includes F, Cl, Br and I.

[0038] In addition, "ortho-" ("o-"), "meta-" ("m-"), and "para-" ("p-") are meant to represent the substitution position of all substituents. The ortho-configuration describes a compound having substituents adjacent to each other, for example, at positions 1 and 2 on benzene. The meta-configuration indicates the next substitution position to the substitution position immediately adjacent, for example, the compound has substituents at positions 1 and 3 on benzene. The para-configuration indicates the next substitution position to the meta position, for example, the compound has substituents at positions 1 and 4 on benzene.

[0039] Herein, the term "ring formed by connecting to adjacent substituents" means a substituted or unsubstituted (3-30-membered) monocyclic or polycyclic alicyclic ring, aromatic ring, or a combination thereof formed by connecting or fusing two or more adjacent substituents, preferably, a substituted or unsubstituted (3-26-membered) monocyclic or polycyclic alicyclic ring, aromatic ring, or a combination thereof. In addition, the formed ring may include at least one heteroatom selected from the group consisting of B, N, O, S, Si and P, preferably N, O and S. According to one embodiment of the present disclosure, the number of atoms in the ring skeleton is 5 to 20; according to another embodiment of the present disclosure, the number of atoms in the ring skeleton is 5 to 15. In one embodiment, the fused ring can be, for example, 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, etc.

[0040] In addition, the expression "substituted or unsubstituted" in "substituted" means that the hydrogen atom in a functional group is replaced by another atom or functional group (i.e., a substituent), and also includes substitution by a group in which two or more of the above substituents are connected in the substituent. For example, "a substituent in which two or more substituents are connected" can be pyridine-triazine. That is, pyridine-triazine can be a heteroaryl group, or can be interpreted as a substituent in which two heteroaryls are connected. In the formula of the present disclosure, substituted alkyl, substituted (sub)aryl, substituted (sub)heteroaryl, substituted cycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, and substituted condensed rings of aliphatic rings and aromatic rings can each independently be substituted by at least one selected from the group consisting of: deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; (C 1 -C 30 ) alkyl; halo(C 1 -C 30 ) alkyl; (C 2 -C 30 ) alkenyl; (C 2 -C 30 ) alkynyl; (C 1 -C 30 ) alkoxy; (C 1 -C 30 ) alkylthio; (C 3 -C 30 )cycloalkyl; (C 3 -C 30 )cycloalkenyl; (3- to 7-membered)heterocycloalkyl; (C 6 -C 30 ) aryloxy; (C 6 -C 30 ) arylthio; unsubstituted or substituted by at least one (C 6 -C 30 ) aryl-substituted (3- to 30-membered) heteroaryl; unsubstituted or substituted by (C 1 -C 30 )alkyl and (3- to 30-membered)heteroaryl substituted with (C 6 -C 30 ) aryl; tri(C 1 -C 30 ) alkylsilyl; tri(C 6 -C 30 ) arylsilyl; di(C 1 -C 30 )alkyl(C 6 -C 30 ) arylsilyl; (C 1 -C30 )alkyldi(C 6 -C 30 ) arylsilyl; tri(C 6 -C 30 )Arylgermanyl; amino; mono- or di-(C 1 -C 30 ) alkylamino; mono- or di-(C 2 -C 30 )alkenylamino; unsubstituted or (C 1 -C 30 ) alkyl-substituted mono- or di-(C 6 -C 30 )arylamino; mono- or di-(3- to 30-membered) heteroarylamino; (C 1 -C 30 )alkyl(C 2 -C 30 )alkenylamino; (C 1 -C 30 )alkyl(C 6 -C 30 ) arylamino; (C 1 -C 30 )alkyl(3-30-membered)heteroarylamino; (C 2 -C 30 )Alkenyl (C 6 -C 30 ) arylamino; (C 2 -C 30 )alkenyl(3- to 30-membered)heteroarylamino; (C 6 -C 30 )aryl(3- to 30-membered)heteroarylamino; (C 1 -C 30 ) alkylcarbonyl; (C 1 -C 30 ) alkoxycarbonyl; (C 6 -C 30 ) arylcarbonyl; di(C 6 -C 30 ) aryl boron carbonyl; di(C 1 -C 30 ) alkyl boron carbonyl; (C 1 -C 30 )alkyl(C 6 -C 30 ) aryl borocarbonyl; (C 6 -C 30 )Aryl (C 1 -C 30 ) alkyl; and (C 1 -C 30 )alkyl(C 6 -C30 ) aromatic group, etc.

[0041] In the formulae of the present disclosure, when there are a plurality of substituents represented by the same symbol, each of these substituents represented by the same symbol may be the same or different.

[0042] Hereinafter, various host materials according to one embodiment will be described.

[0043] The plurality of host materials according to one embodiment include at least one first host compound and at least one second host compound, wherein the first host compound is represented by Formula 1, and the second host compound is represented by Formula 2.

[0044] According to one embodiment, the first host compound as a host material may be represented by Formula 1 below.

[0045]

[0046] In formula 1,

[0047] X 1 and Y 1 Each independently represents -N=, -NR 7 , -O-, or -S-; provided that X 1 and Y 1 Any one of is -N=, and X 1 and Y 1 The other one is -NR 7 -, -O-, or -S-;

[0048] R 1 Indicates substituted or unsubstituted (C 6 -C 30 )aryl or substituted or unsubstituted (3- to 30-membered) heteroaryl;

[0049] R 2 To R 4 and R 7 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C 1 -C 30 ) alkyl, substituted or unsubstituted (C 6 -C 30 )aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C 3 -C 30 )cycloalkyl, substituted or unsubstituted (C 1 -C 30 ) alkoxy, substituted or unsubstituted tri(C 1 -C 30 )alkylsilyl, substituted or unsubstituted di(C1 -C 30 )alkyl(C 6 -C 30 ) arylsilyl, substituted or unsubstituted (C 1 -C 30 )alkyldi(C 6 -C 30 ) arylsilyl, substituted or unsubstituted tri(C 6 -C 30 ) arylsilyl, (C 3 -C 30 ) aliphatic ring and (C 6 -C 30 ) a substituted or unsubstituted condensed ring of an aromatic ring, or -L 11 -N(Ar 1 )(Ar 2 ) ; or may be connected to adjacent substituents to form one or more rings;

[0050] L 1 and L 11 Each independently represents a single bond, substituted or unsubstituted (C 6 -C 30 )arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene;

[0051] R 5 and R 6 Each independently represents a substituted or unsubstituted (C 6 -C 30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl;

[0052] Ar 1 and Ar 2 Each independently represents hydrogen, substituted or unsubstituted (C 1 -C 30 ) alkyl, substituted or unsubstituted (C 2 -C 30 ) alkenyl, (C 3 -C 30 ) aliphatic ring and (C 6 -C 30 ) a substituted or unsubstituted condensed ring of an aromatic ring, a substituted or unsubstituted (C 6 -C 30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; and

[0053] b and c each independently represent an integer of 1 or 2, d represents an integer of 1 to 4, and when b to d are integers of 2 or more, R 2 To R 4Each of can be the same or different.

[0054] According to one embodiment, Formula 1 may be represented by any one of the following Formulas 1-1 to 1-4.

[0055]

[0056] In formulas 1-1 to 1-4,

[0057] d represents an integer of 1 to 3, and when d is an integer of 2 or more, each R 4 may be the same or different; and

[0058] X 1 , Y 1 , R 1 To R 6 , L 1 , b, and c are defined as in Formula 1.

[0059] In one embodiment, X 1 and Y 1 Any one of can be -N=, and X 1 and Y 1 The other in can be -O- or -S-. For example, X 1 Can be -N=, and Y 1 Can be -O-, or X 1 Can be -O-, and Y 1 Can be -N=, or X 1 Can be -S-, and Y 1 It can be -N=.

[0060] In one embodiment, R 1 It may be substituted or unsubstituted (C 6 -C 30 )aryl, or substituted or unsubstituted (5- to 30-membered) heteroaryl, preferably substituted or unsubstituted (C 6 -C 25 )aryl, or substituted or unsubstituted (5- to 25-membered) heteroaryl, more preferably substituted or unsubstituted (C 6 -C 18 )aryl, or substituted or unsubstituted (5- to 18-membered) heteroaryl. 1 It may be an unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted o-biphenyl group, an unsubstituted m-biphenyl group, an unsubstituted p-biphenyl group, or an unsubstituted pyridyl group.

[0061] In one embodiment, R 2 To R 4 and R 7Each independently may be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C 1 -C 30 )alkyl, or substituted or unsubstituted (C 6 -C 30 ) aryl, preferably hydrogen, deuterium, halogen, cyano, or substituted or unsubstituted (C 6 -C 25 ) aryl, more preferably hydrogen, deuterium, or substituted or unsubstituted (C 6 -C 18 ) aryl. For example, R 2 To R 4 Each independently may be hydrogen or unsubstituted phenyl.

[0062] In one embodiment, L 1 It can be a single bond or substituted or unsubstituted (C 6 -C 30 ) arylene, preferably a single bond or substituted or unsubstituted (C 6 -C 25 )arylene, more preferably substituted or unsubstituted (C 6 -C 18 ) arylene. For example, L 1 It may be a single bond, or an unsubstituted phenylene group, or an unsubstituted naphthylene group.

[0063] In one embodiment, R 5 and R 6 Each independently may be substituted or unsubstituted (C 6 -C 30 )aryl, substituted or unsubstituted (5- to 30-membered) heteroaryl, or -L 11 -N(Ar 1 )(Ar 2 ), preferably substituted or unsubstituted (C 6 -C 25 )aryl, substituted or unsubstituted (5- to 25-membered) heteroaryl, or -L 11 -N(Ar 1 )(Ar 2 ), more preferably substituted or unsubstituted (C 6 -C 25 )aryl, substituted or unsubstituted (5- to 20-membered) heteroaryl, or -L 11 -N(Ar 1 )(Ar 2 ). For example, R 5 and R 6and each independently may be substituted or unsubstituted phenyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted o-quaterphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted C 22 The substituents in the substituted group may be substituted by at least one of the following: deuterium; methyl; tert-butyl; cyclohexyl; phenyl which is unsubstituted or substituted by at least one of methyl and tert-butyl; naphthyl; biphenyl; anthracenyl; fluoranthenyl; phenylfluorenyl; pyridyl which is unsubstituted or substituted by phenyl; phenoxazinyl; diphenylamino; benzimidazolyl substituted by phenyl; triphenylsilane; diphenylnaphthylsilane; and biphenyldiphenylsilane.

[0064] In one embodiment, L 11 It can be a single bond or substituted or unsubstituted (C 6 -C 30 ) arylene, preferably a single bond or substituted or unsubstituted (C 6 -C 25 )arylene, more preferably substituted or unsubstituted (C 6 -C 18 ) arylene. For example, L 11 It may be an unsubstituted phenylene group.

[0065] In one embodiment, Ar 1 and Ar 2 Each independently may be substituted or unsubstituted (C 6 -C 30 ) aryl, preferably substituted or unsubstituted (C 6 -C 25 ) aryl, more preferably substituted or unsubstituted (C 6 -C 18 ) aryl. For example, Ar 1 and Ar 2 Each independently may be substituted or unsubstituted phenyl.

[0066] According to one embodiment, the first host compound represented by Formula 1 may be more specifically illustrated by the following compounds, but is not limited thereto.

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074] The host compound represented by Formula 1 according to the present disclosure may be manufactured by referring to a synthesis method known to those skilled in the art, for example, by a synthesis method disclosed in Korean Patent Application Publication Nos. 2017-0022865 and 2018-0099487, and the like.

[0075] According to one embodiment, the second host compound as another host material may be represented by Formula 2 below.

[0076]

[0077] In formula 2,

[0078] Ring A and Ring B each independently represent a substituted or unsubstituted (C 6 -C 30 )arene, or substituted or unsubstituted (3- to 30-membered) heteroarene;

[0079] R 11 and R 12 Each independently represents a substituted or unsubstituted (C 1 -C 30 ) alkyl, substituted or unsubstituted (C 6 -C 30 ) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; or may be connected to each other to form one or more rings;

[0080] X 2 and Y 2 Each independently represents -N=, -NR 24 , -O-, or -S-; provided that X 2 and Y 2 Any one of is -N=, and X 2 and Y 2 The other one is -NR 24 -, -O-, or -S-;

[0081] R 21 To R24 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C 1 -C 30 ) alkyl, substituted or unsubstituted (C 6 -C 30 )aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C 3 -C 30 )cycloalkyl, substituted or unsubstituted (C 1 -C 30 ) alkoxy, substituted or unsubstituted tri(C 1 -C 30 )alkylsilyl, substituted or unsubstituted di(C 1 -C 30 )alkyl(C 6 -C 30 ) arylsilyl, substituted or unsubstituted (C 1 -C 30 )alkyldi(C 6 -C 30 ) arylsilyl, substituted or unsubstituted tri(C 6 -C 30 ) arylsilyl, (C 3 -C 30 ) aliphatic ring and (C 6 -C 30 ) a substituted or unsubstituted condensed ring of an aromatic ring, or -L 3 -HAr;

[0082] The premise is R 21 To R 24 At least one of them is -L 3 -HAr;

[0083] L 2 and L 3 Each independently represents a single bond, substituted or unsubstituted (C 6 -C 30 )arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene;

[0084] HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group containing at least one nitrogen atom; and

[0085] n represents an integer of 1 to 4, m represents an integer of 1 to 8, and when n and m are integers of 2 or more, R 22 and R 23 Each of can be the same or different.

[0086] In one embodiment, ring A may be a benzene ring or a naphthalene ring.

[0087] In one embodiment, ring B may be a benzene ring, a naphthalene ring, or a phenanthrene ring.

[0088] According to one embodiment, the host compound represented by Formula 2 may be represented by any one of the following Formulas 2-1 to 2-8.

[0089]

[0090] In formulas 2-1 to 2-8,

[0091] X 2 , Y 2 , R 11 , R 12 , R 21 To R 23 , L 2 , n, and m are as defined in Formula 2; and

[0092] n′ represents an integer of 1 or 2, m′ represents an integer of 1 to 4, and m″ represents an integer of 1 to 6.

[0093] According to another embodiment, the host compound represented by Formula 2 may be represented by the following Formula 2-1 or 2-9.

[0094]

[0095] In formulas 2-1 and 2-9,

[0096] X 2 , Y 2 , R 11 , R 12 , R 21 To R 23 , and L 2 is as defined in Equation 2; and

[0097] n′ represents an integer of 1 or 2, m′ represents an integer of 1 to 4, and m″ represents an integer of 1 to 6.

[0098] In one embodiment, R 11 and R 12 Each independently may be substituted or unsubstituted (C 1 -C 30 ) alkyl, preferably substituted or unsubstituted (C 1 -C 10 ) alkyl, more preferably substituted or unsubstituted (C 1 -C 4 ) alkyl. For example, R 11 and R 12 The methyl group may be substituted or unsubstituted.

[0099] In one embodiment, X 2 and Y 2 Any one of can be -N=, and X 2 and Y 2 Another one in can be -NR 24 -, -O-, or -S-.

[0100] In one embodiment, R 24 It may be substituted or unsubstituted (C 6 -C 30 ) aryl, for example substituted or unsubstituted phenyl.

[0101] In one embodiment, L 2 Can be a single bond.

[0102] In one embodiment, R 21 It may be substituted or unsubstituted (C 6 -C 30 ) aryl, for example unsubstituted or deuterium-substituted phenyl, or substituted or unsubstituted naphthyl.

[0103] In one embodiment, R 22 and R 23 Each independently may be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (5- to 30-membered) heteroaryl, or -L 3 -HAr, preferably hydrogen, deuterium, substituted or unsubstituted (5- to 25-membered) heteroaryl, or -L 3 -HAr, more preferably hydrogen, substituted or unsubstituted (5- to 18-membered) heteroaryl, or -L 3 -HAr. For example, R 22 and R 23 At least one of them can be -L 3 -HAr.

[0104] In one embodiment, L 3 It can be a single bond or substituted or unsubstituted (C 6 -C 30 ) arylene, preferably a single bond or substituted or unsubstituted (C 6 -C 25 )arylene, more preferably a single bond or substituted or unsubstituted (C 6 -C 18 ) arylene. For example, L 3 It may be a single bond or a substituted or unsubstituted phenylene group.

[0105] In one embodiment, HAr can be a substituted or unsubstituted (5- to 30-membered) heteroaryl group containing at least one nitrogen atom, preferably a substituted or unsubstituted (5- to 30-membered) heteroaryl group containing at least two nitrogen atoms, more preferably unsubstituted or substituted (C 6 -C 30 )aryl-substituted (5- to 30-membered) heteroaryl containing at least one nitrogen atom.

[0106] In one embodiment, HAr may be represented by Formula 3 or 4 below.

[0107]

[0108] In equations 3 and 4,

[0109] X a , X b , Y a , and Y b Each independently represents N or CR 33 ; The premise is X a and X b At least one of them is N, and Y a and Y b At least one of is N; and

[0110] R 31 To R 37 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C 1 -C 30 ) alkyl, substituted or unsubstituted (C 6 -C 50 )aryl, substituted or unsubstituted (3- to 50-membered) heteroaryl, substituted or unsubstituted (C 3 -C 30 )cycloalkyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C 1 -C 30 ) alkoxy, substituted or unsubstituted tri(C 1 -C 30 )alkylsilyl, substituted or unsubstituted di(C 1 -C 30 )alkyl(C 6 -C 30 ) arylsilyl, substituted or unsubstituted (C 1 -C 30 )alkyldi(C 6 -C 30 ) arylsilyl, substituted or unsubstituted tri(C 6 -C 30 ) arylsilyl, substituted or unsubstituted mono- or di-(C1 -C 30 ) alkylamino, substituted or unsubstituted mono- or di-(C 6 -C 30 ) arylamino, or substituted or unsubstituted (C 1 -C 30 )alkyl(C 6 -C 30 ) arylamino; or may be connected to adjacent substituents to form one or more rings.

[0111] In one embodiment, X a Can be N, and X b Can be CR 33 .

[0112] In one embodiment, X a and X b Both can be N.

[0113] In one embodiment, R 31 and R 32 Each independently may be substituted or unsubstituted (C 6 -C 50 )aryl, or substituted or unsubstituted (5- to 50-membered) heteroaryl, preferably substituted or unsubstituted (C 6 -C 30 )aryl, or substituted or unsubstituted (5- to 30-membered) heteroaryl, more preferably substituted or unsubstituted (C 6 -C 25 )aryl, or substituted or unsubstituted (5- to 25-membered) heteroaryl. 31 and R 32 Each independently may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or an unsubstituted or unsubstituted carbazolyl group.

[0114] In one embodiment, Y a Can be N and Y b Can be CR 33。

[0115] In one embodiment, Y a Can be CR 33 , and Y b It can be N.

[0116] In one embodiment, R 34 To R 37 Each independently may be hydrogen or deuterium, preferably hydrogen.

[0117] In one embodiment, R 33 It may be hydrogen or substituted or unsubstituted (C 6 -C 30 ) aryl, for example hydrogen or substituted or unsubstituted phenyl.

[0118] According to one embodiment, the compound represented by the above Formula 2 may be more specifically illustrated by the following compounds, but is not limited thereto.

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131] For example, the compound represented by Formula 2 according to the present disclosure may be prepared by referring to the following Reaction Scheme 1, but is not limited thereto.

[0132] [Reaction Scheme 1]

[0133]

[0134] In Reaction Scheme 1, the definition of each substituent is as defined in Formula 2, and Hal means halogen.

[0135] As described above, exemplary synthesis examples of the compound represented by Formula 2 according to the present disclosure are described, but they are based on Buchwald-Hartwig cross-coupling reaction, N-arylation reaction, acidified montmorillonite (H-mont) mediated etherification reaction, Miyaura borylation reaction, Suzuki cross-coupling reaction, intramolecular acid-induced cyclization reaction, Pd (II) catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, dehydration cyclization reaction, S N 1 Substitution reaction, S N 2 substitution reaction, phosphine-mediated reductive cyclization reaction, etc. It should be understood by those skilled in the art that the above reaction continues even if other substituents defined in Formula 2 other than the substituents described in the specific synthetic example are bonded.

[0136] According to another embodiment, the present disclosure provides an organic electroluminescent compound represented by the following Formula 2'.

[0137]

[0138] In formula 2′,

[0139] Ring A and Ring B each independently represent a substituted or unsubstituted (C 6 -C 30 )arene, or substituted or unsubstituted (3- to 30-membered) heteroarene;

[0140] R 11 and R 12 Each independently represents a substituted or unsubstituted (C 1 -C 30 ) alkyl, substituted or unsubstituted (C 6 -C 30 ) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; or may be connected to each other to form one or more rings;

[0141] X 2 and Y 2 Each independently represents -N=, -NR 24 , -O-, or -S-; provided that X 2 and Y 2 Any one of is -N=, and X 2 and Y 2 The other one is -NR 24 -, -O-, or -S-;

[0142] R 21 and R 24 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 -C 30 ) alkyl, substituted or unsubstituted (C 6 -C 30 )aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C 3 -C 30 )cycloalkyl, substituted or unsubstituted (C 1 -C 30 ) alkoxy, substituted or unsubstituted tri(C 1 -C 30 )alkylsilyl, substituted or unsubstituted di(C 1 -C 30 )alkyl(C 6 -C 30 ) arylsilyl, substituted or unsubstituted (C 1 -C 30 )alkyldi(C 6 -C 30 ) arylsilyl, substituted or unsubstituted tri(C 6 -C 30 ) arylsilyl, (C 3 -C 30 ) aliphatic ring and (C 6 -C 30 ) a substituted or unsubstituted condensed ring of an aromatic ring, or -L 3 -HAr;

[0143] The premise is R 21 To R 24 At least one of them is -L 3 -HAr; and if R 23 Yes-L 3 -HAr, then the case where both ring A and ring B are substituted or unsubstituted benzene is excluded;

[0144] L 2 and L 3 Each independently represents a single bond, substituted or unsubstituted (C 6 -C 30 )arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene;

[0145] HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group containing at least one nitrogen atom; and

[0146] n represents an integer of 1 to 4, m represents an integer of 1 to 8, and when n and m are integers of 2 or more, R 22 and R 23 Each of can be the same or different.

[0147] According to one embodiment, the organic electroluminescent compound represented by Formula 2' may be represented by any one of the following Formulae 2-1a and 2-2 to 2-8.

[0148]

[0149]

[0150] In Formulas 2-1a and 2-2 to 2-8,

[0151] R 21′ and R 22′ Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C 1 -C 30 ) alkyl, substituted or unsubstituted (C 6 -C 30 )aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C 3 -C 30 )cycloalkyl, substituted or unsubstituted (C 1 -C 30 ) alkoxy, substituted or unsubstituted tri(C 1 -C 30 )alkylsilyl, substituted or unsubstituted di(C 1 -C 30 )alkyl(C 6 -C 30 ) arylsilyl, substituted or unsubstituted (C 1 -C 30 )alkyldi(C 6 -C 30 ) arylsilyl, substituted or unsubstituted tri(C 6 -C 30 ) arylsilyl, (C 3 -C 30 ) aliphatic ring and (C 6 -C 30 ) a substituted or unsubstituted condensed ring of an aromatic ring, or -L 3 -HAr; the premise is R 21′ and R 22′ Any one of -L 3 -HAr;

[0152] R 23′ represents hydrogen, deuterium, or unsubstituted or substituted with deuterium (C 6 -C 30 ) aryl;

[0153] n′ represents an integer of 1 or 2, m′ represents an integer of 1 to 4, and m″ represents an integer of 1 to 6; and

[0154] X 2 , Y 2 , R 11 , R 12 , R 21 To R 23 , L 2 , n, and m are as defined in Formula 2'.

[0155] According to another embodiment, the organic electroluminescent compound represented by Formula 2' may be represented by the following Formula 2-9.

[0156]

[0157] In formula 2-9,

[0158] X 2 , Y 2 , R 11 , R 12 , R 21 To R 23 , and L 2 is as defined in Formula 2′; and

[0159] n′ represents an integer of 1 or 2, and m″ represents an integer of 1 to 6.

[0160] According to one embodiment, the organic electroluminescent compound represented by the above Formula 2' may be more specifically illustrated by the following compounds, but is not limited thereto.

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170] Hereinafter, an organic electroluminescent device to which the aforementioned various host materials and / or organic electroluminescent compounds are applied will be described.

[0171] An organic electroluminescent device according to an embodiment includes a first electrode; a second electrode; and at least one organic layer inserted between the first electrode and the second electrode. The organic layer may include a light-emitting layer, and the light-emitting layer may include a plurality of host materials, the plurality of host materials including at least one first host compound represented by Formula 1 and at least one second host compound represented by Formula 2. Wherein, the weight ratio of the first host compound to the second host compound in the light-emitting layer may be 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, more preferably about 40:60 to about 60:40, and even more preferably may be about 50:50.

[0172] According to one embodiment, the organic electroluminescent material of the present disclosure includes at least one compound of compounds H1-1 to H1-193 as a first host compound and at least one compound of compounds H2-1 to H2-240 as a second host compound. A plurality of host materials may be included in the same organic layer, such as the same light-emitting layer, or may be included in different light-emitting layers.

[0173] According to another embodiment, the organic electroluminescent material of the present disclosure includes an organic electroluminescent compound represented by Formula 2′ alone or in combination of two or more, and such an organic electroluminescent material may be included in an organic layer of an organic electroluminescent device, for example: an electron transport layer, an electron buffer layer, a hole blocking layer, or a light-emitting layer.

[0174] In addition to the light-emitting layer, the organic layer may also include at least one layer selected from the following: hole injection layer, hole transport layer, hole auxiliary layer, luminescent auxiliary layer, electron transport layer, electron injection layer, intermediate layer, hole blocking layer, electron blocking layer and electron buffer layer. In addition to the light-emitting material according to the present disclosure, the organic layer may further include amine-based compounds and / or azine-based compounds. Specifically, the hole injection layer, hole transport layer, hole auxiliary layer, light-emitting layer, luminescent auxiliary layer, or electron blocking layer may contain amine-based compounds (e.g., arylamine-based compounds and styrylarylamine-based compounds, etc.) as hole injection materials, hole transport materials, hole auxiliary materials, luminescent materials, luminescent auxiliary materials, or electron blocking materials. In addition, the electron transport layer, electron injection layer, electron buffer layer, or hole blocking layer may contain azine-based compounds as electron transport materials, electron injection materials, electron buffer materials, or hole blocking materials. In addition, the organic layer may further contain at least one metal selected from the group consisting of metals of Group 1 of the periodic table, metals of Group 2, transition metals of Period 4, transition metals of Period 5, lanthanide elements and organometallic d-transition elements, or at least one complex compound containing such a metal.

[0175] According to one embodiment, a variety of host materials can be used as light-emitting materials for white organic light-emitting devices. According to the arrangement of R (red), G (green), YG (yellow-green), or B (blue) light-emitting units, various structures have been proposed for white organic light-emitting devices, such as a parallel side-by-side arrangement method, a stacked arrangement method, a CCM (color conversion material) method, etc. In addition, a variety of host materials and / or organic electroluminescent materials according to one embodiment can also be applied to an organic electroluminescent device containing QD (quantum dots).

[0176] One of the first electrode and the second electrode may be an anode, and the other may be a cathode. The first electrode and the second electrode may each be formed as a transmissive conductive material, a semi-transmissive reflective conductive material, or a reflective conductive material. Depending on the type of material forming the first electrode and the second electrode, the organic electroluminescent device may be a top-emitting type, a bottom-emitting type, or a double-sided emitting type.

[0177] A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof can be used between the anode and the light-emitting layer. The hole injection layer can be multilayered to reduce the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, wherein each of the multilayers can use two compounds at the same time. In addition, the hole injection layer can be doped with a p-type dopant. In addition, the electron blocking layer can be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and the excitons can be confined in the light-emitting layer by blocking the electrons from overflowing from the light-emitting layer to prevent light leakage. The hole transport layer or the electron blocking layer can be multilayered, and each layer can use a variety of compounds.

[0178] An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be used between the light-emitting layer and the cathode. The electron buffer layer may be multilayered to control the injection of electrons and improve the interface characteristics between the light-emitting layer and the electron injection layer, wherein each of the multiple layers may use two compounds at the same time. The hole blocking layer may be placed between the electron transport layer (or electron injection layer) and the light-emitting layer, and blocks holes from reaching the cathode, thereby increasing the probability of recombination of electrons and holes in the light-emitting layer. The hole blocking layer or the electron transport layer may also be multilayered, wherein each layer may use a variety of compounds. In addition, the electron injection layer may be doped with an n-type dopant.

[0179] The luminescence auxiliary layer can be placed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer. When the luminescence auxiliary layer is placed between the anode and the light-emitting layer, it can be used to promote hole injection and / or hole transport, or to prevent electron overflow. When the luminescence auxiliary layer is placed between the cathode and the light-emitting layer, it can be used to promote electron injection and / or electron transport, or to prevent hole overflow. In addition, the hole auxiliary layer can be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can effectively promote or limit the hole transport rate (or hole injection rate), so that the charge balance can be controlled. When the organic electroluminescent device includes two or more hole transport layers, the hole transport layer further included can be used as a hole auxiliary layer or an electron blocking layer. The luminescence auxiliary layer, the hole auxiliary layer, or the electron blocking layer can have the effect of improving the efficiency and / or life of the organic electroluminescent device.

[0180] In the organic electroluminescent device of the present disclosure, at least one layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter, "surface layer") may be preferably placed on one or more inner surfaces of one electrode or both electrodes of a pair of electrodes. Specifically, a chalcogenide (including oxide) layer of silicon and aluminum is preferably placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or a metal oxide layer is preferably placed on the cathode surface of the electroluminescent medium layer. The operational stability of the organic electroluminescent device can be obtained by the surface layer. Preferably, the chalcogenide includes SiO x (1≤x≤2), AlO x (1≤x≤1.5), SiON, SiAlON, etc.; metal halides include LiF, MgF 2 , CaF 2 , rare earth metal fluorides, etc.; and metal oxides include Cs 2 O. Li 2 O, MgO, SrO, BaO, CaO, etc.

[0181] In addition, in the organic electroluminescent device of the present disclosure, a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant can be placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to anions, and thus it becomes easier to inject and transport electrons from the mixed region to the electroluminescent medium. In addition, the hole transport compound is oxidized to cations, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium. Preferably, the oxidative dopant includes various Lewis acids and acceptor compounds, and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, the reductive dopant layer can be used as a charge generation layer to prepare an organic electroluminescent device having two or more light-emitting layers and emitting white light.

[0182] The organic electroluminescent device according to one embodiment may further include at least one dopant in the light emitting layer.

[0183] The dopant included in the organic electroluminescent device of the present disclosure may be at least one phosphorescent dopant or fluorescent dopant, preferably a phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particularly limited, but may preferably be one or more metallized complex compounds of one or more metal atoms selected from the following: iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably one or more ortho-metallized complex compounds of one or more metal atoms selected from the following: iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably one or more ortho-metallized iridium complex compounds.

[0184] The dopant included in the organic electroluminescent device of the present disclosure may use a compound represented by the following Formula 101, but is not limited thereto.

[0185]

[0186] In formula 101,

[0187] L is selected from any one of the following structures 1 to 3;

[0188]

[0189] R 100 To R 103 Each independently represents hydrogen, deuterium, halogen, unsubstituted or substituted by deuterium and / or halogen (C 1 -C 30 ) alkyl, substituted or unsubstituted (C 3 -C 30 )cycloalkyl, substituted or unsubstituted (C6 -C 30 )aryl, cyano, substituted or unsubstituted (3- to 30-membered) heteroaryl, or substituted or unsubstituted (C 1 -C 30 ) alkoxy; or may be connected to an adjacent substituent to form one or more rings, for example, to form one or more substituted or unsubstituted rings with pyridine, such as substituted or unsubstituted quinoline, substituted or unsubstituted benzopyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuranoquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indenoquinoline;

[0190] R 104 To R 107 Each independently represents hydrogen, deuterium, halogen, unsubstituted or substituted by deuterium and / or halogen (C 1 -C 30 ) alkyl, substituted or unsubstituted (C 3 -C 30 )cycloalkyl, substituted or unsubstituted (C 6 -C 30 )aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, cyano, or substituted or unsubstituted (C 1 -C 30 ) alkoxy; or may be connected to an adjacent substituent to form one or more substituted or unsubstituted rings, for example, to form one or more substituted or unsubstituted rings with benzene, such as substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuranopyridine, or substituted or unsubstituted benzothienopyridine;

[0191] R 201 To R 220 Each independently represents hydrogen, deuterium, halogen, unsubstituted or substituted by deuterium and / or halogen (C 1 -C 30 ) alkyl, substituted or unsubstituted (C 3 -C 30 )cycloalkyl, or substituted or unsubstituted (C 6 -C 30 ) aryl; or may be connected to adjacent substituents to form one or more substituted or unsubstituted rings; and

[0192] s represents an integer of 1 to 3.

[0193] Specifically, specific examples of the dopant compound include the following, but are not limited thereto.

[0194]

[0195]

[0196]

[0197]

[0198]

[0199] In order to form each layer of the organic electroluminescent device of the present disclosure, a dry film forming method such as vacuum evaporation, sputtering, plasma, ion plating method, etc., or a wet film forming method such as spin coating, dip coating, flow coating method, etc. can be used. When a wet film forming method is used, a thin film can be formed by dissolving or diffusing the material forming each layer into any suitable solvent (such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.). The solvent can be any solvent in which the material forming each layer can be dissolved or diffused and there is no problem in film forming ability.

[0200] When a layer is formed by the first host compound and the second host compound according to an embodiment, the layer can be formed by the methods listed above, and can generally be formed by co-deposition or mixed deposition. Co-deposition is a mixed deposition method in which two or more materials are placed in a corresponding single crucible source and current is applied to two chambers at the same time to evaporate the materials and perform mixed deposition; and mixed deposition is a method in which two or more materials are mixed in one crucible source before deposition, and then current is applied to one chamber to evaporate the materials.

[0201] According to one embodiment, when the first host compound and the second host compound exist in the same layer or different layers in the organic electroluminescent device, a layer may be formed separately from the two host compounds. For example, after depositing the first host compound, the second host compound may be deposited.

[0202] According to one embodiment, the present disclosure may provide a display device including a plurality of host materials including a first host compound represented by Formula 1 and a second host compound represented by Formula 2. In addition, the organic electroluminescent device of the present disclosure may be used to manufacture a display device such as a smartphone, a tablet computer, a notebook computer, a PC, a TV, or a display device of a vehicle, or a lighting device such as outdoor or indoor lighting.

[0203] Hereinafter, a preparation method of a host material according to the present disclosure will be explained with reference to a synthesis method of a representative compound or an intermediate compound in order to understand the present disclosure in detail.

[0204] [Example 1] Preparation of Compound H2-73

[0205]

[0206] 1) Synthesis of Compound 1-1

[0207] 2-Bromo-7-chloro-11,11-dimethyl-11H-benzo[b]fluorene (50 g, 140 mmol), benzamide (17 g, 140 mmol), CuI (40 g, 210 mmol), ethylenediamine (28.3 mL, 419 mmol), K 3 PO 4 (59 g, 280 mmol), 350 mL of toluene, and 350 mL of xylene were added to a flask and dissolved, and then refluxed at 135° C. for 24 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, then dried, and then separated by column chromatography to obtain compound 1-1 (50 g, yield: 90%).

[0208] 2) Synthesis of Compound 1-2

[0209] Compound 1-1 (10 g, 25 mmol) and Cu(OTf) 2 (13.6 g, 37 mmol) was added to a flask and dissolved in 312 mL of 1,2-dichlorobenzene (1,2-DCB), and then refluxed at 170° C. for 48 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, then dried, and then separated by column chromatography to obtain compound 1-2 (2.4 g, yield: 24%).

[0210] 3) Synthesis of Compound 1-3

[0211] Compound 1-2 (3 g, 7.5 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bis(1,3,2-dioxaborolane) (5.7 g, 22.7 mmol), Pd 2 dba 3 (694 mg, 0.7 mmol), SPhos (622 mg, 1.5 mmol), and KOAc (2.2 g, 22.7 mmol) were added to a flask and dissolved in 50 mL of 1,4-dioxane, and then refluxed at 100° C. for 24 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, then dried, and then separated by column chromatography to obtain compound 1-3 (2.8 g, yield: 75%).

[0212] 4) Synthesis of Compound H2-73

[0213] Compound 1-3 (2.7 g, 5.5 mmol), 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (2.0 g, 5.5 mmol), Pd(PPh 3 ) 4 (0.32 g, 0.27 mmol), K 2 CO 3 (1.9 g, 14 mmol), 28 mL of toluene, 7 mL of ethanol, and 7 mL of H 2 O was added to the flask, and then stirred under reflux for 5 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, followed by drying, and then column chromatography separation was performed to obtain compound H2-73 (2.4 g, yield: 64%).

[0214] MW MP H2-73 682.78 333℃

[0215] [Example 2] Preparation of Compound H2-5

[0216]

[0217] 1) Synthesis of compound 2-1

[0218] 2-Bromo-9,9-dimethyl-9H-fluorene (30 g, 110 mmol), benzamide (13.3 g, 110 mmol), CuI (31.3 g, 165 mmol), ethylenediamine (22.2 mL, 330 mmol), K 3 PO 4 (46.6 g, 220 mmol), and 550 mL of xylene were added to a flask and dissolved, and then refluxed at 150° C. for 24 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, then dried, and then separated by column chromatography to obtain compound 2-1 (26.4 g, yield: 77%).

[0219] 2) Synthesis of Compound 2-2

[0220] Compound 2-1 (25 g, 80 mmol) and Cu(OTf) 2 (43.2 g, 120 mmol) was added to a flask and dissolved in 1,000 mL of 1,2-DCB, and then refluxed at 170° C. for 24 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, then dried, and then separated by column chromatography to obtain compound 2-2 (5.1 g, yield: 20%).

[0221] 3) Synthesis of Compound 2-3

[0222] Compound 2-2 (5 g, 16 mmol) and NBS (5.7 g, 32 mmol) were dissolved in 160 mL of DMF, and then refluxed at 100° C. for 5 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, then dried, and then separated by column chromatography to obtain compound 2-3 (5.0 g, yield: 79%).

[0223] 4) Synthesis of Compound 2-4

[0224] Compound 2-3 (2.2 g, 5.6 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bis(1,3,2-dioxaborolane) (2.8 g, 11 mmol), PdCl 2 (PPh 3 ) 2 (395 mg, 0.5 mmol), and KOAc (1.1 g, 11 mmol) were dissolved in 37 mL of 1,4-dioxane, and then refluxed at 100° C. for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, then dried, and then separated by column chromatography to obtain compound 2-4 (1.9 g, yield: 76%).

[0225] 5) Synthesis of Compound H2-5

[0226] Compound 2-4 (1.8 g, 4.1 mmol), 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (1.6 g, 4.5 mmol), Pd(PPh 3 ) 4 (0.24 g, 0.2 mmol), K 2 CO 3 (1.4 g, 10 mmol), 20 mL of toluene, 5 mL of ethanol, and 5 mL of H 2 O was added to the flask, and then stirred under reflux for 1.5 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, followed by drying, and then column chromatography separation was performed to obtain compound H2-5 (2.2 g, yield: 84%).

[0227] MW MP H2-5 632.72 269℃

[0228] [Example 3] Preparation of Compound H2-75

[0229]

[0230] 1) Synthesis of compound 3-1

[0231] 2-Bromo-11,11-dimethyl-11H-benzo[b]fluorene (50 g, 154 mmol), benzamide (18.7 g, 154 mmol), CuI (44 g, 232 mmol), ethylenediamine (31 mL, 464 mmol), K 3 PO 4 (65.6 g, 309 mmol), and 770 mL of xylene were added to a flask and dissolved, and then refluxed at 150° C. for 24 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, then dried, and then separated by column chromatography to obtain compound 3-1 (53 g, yield: 94%).

[0232] 2) Synthesis of Compound 3-2

[0233] Compound 3-1 (30 g, 82 mmol) and Cu(OTf) 2 (44.7 g, 123 mmol) was dissolved in 1,000 mL of 1,2-DCB, and then refluxed at 170° C. for 48 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, then dried, and then separated by column chromatography to obtain compound 3-2 (7.5 g, yield: 25%).

[0234] 3) Synthesis of Compound 3-3

[0235] Compound 3-2 (6.5 g, 18 mmol) and NBS (3.2 g, 18 mmol) were dissolved in 180 mL of DMF, and then refluxed at 50° C. for 6 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, then dried, and then separated by column chromatography to obtain compound 3-3 (6.5 g, yield: 71%).

[0236] 4) Synthesis of Compound H2-75

[0237] Compound 3-3 (2.9 g, 6.6 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (3.4 g, 7.9 mmol), Pd(PPh 3 ) 4 (0.38 g, 0.33 mmol), K 2 CO 3 (2.3 g, 16 mmol), 32 mL of toluene, 8 mL of ethanol, and 8 mL of H 2O was added to the flask, and then stirred under reflux for 1.5 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, followed by drying, and then column chromatography separation was performed to obtain compound H2-75 (1.7 g, yield: 38%).

[0238] MW MP H2-75 668.8 317℃

[0239] [Example 4] Preparation of Compound H2-74

[0240]

[0241] 1) Synthesis of Compound 3-4

[0242] Compound 3-3 (6.5 g, 14.7 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bis(1,3,2-dioxaborolane) (11.2 g, 44 mmol), PdCl 2 (PPh 3 ) 2 (1000 mg, 1.5 mmol), and KOAc (2.9 g, 30 mmol) were dissolved in 100 mL of 1,4-dioxane, and then refluxed at 100° C. for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, then dried, and then separated by column chromatography to obtain compound 3-4 (7 g, yield: 97%).

[0243] 2) Synthesis of compound H2-74

[0244] Compound 3-4 (4 g, 8.2 mmol), 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (3.2 g, 9 mmol), Pd(PPh 3 ) 4 (0.47 g, 0.41 mmol), K 2 CO 3 (2.8 g, 20 mmol), 40 mL of toluene, 10 mL of ethanol, and 10 mL of H 2 O was added to the flask, and then stirred under reflux for 1.5 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, followed by drying, and then column chromatography separation was performed to obtain compound H2-74 (1.8 g, yield: 32%).

[0245] MW MP H2-74 682.78 274.2℃

[0246] [Device Examples 1 to 4] Preparation of OLED by Co-depositing the First Host Compound and the Second Host Compound According to the Present Disclosure

[0247] An OLED according to the present disclosure is produced. First, a transparent electrode indium tin oxide (ITO) film (10Ω / sq) (GEOMATEC CO., LTD., Japan) on a glass substrate for an OLED is subjected to ultrasonic washing with acetone and isopropanol in sequence, and thereafter stored in isopropanol and used. Next, the ITO substrate is mounted on a substrate holder of a vacuum vapor deposition device. Then, compound HI-1 is introduced into a chamber of the vacuum vapor deposition device, while compound HT-1 is introduced into another chamber. The two materials are evaporated at different rates, and compound HI-1 is deposited at a doping amount of 3wt% based on the total amount of compound HI-1 and compound HT-1 to form a hole injection layer having a thickness of 10nm. Next, compound HT-1 is deposited to form a first hole transport layer having a thickness of 80nm on the hole injection layer. Next, compound HT-2 is then introduced into another chamber of a vacuum vapor deposition apparatus, and the compound is evaporated by applying an electric current to the chamber, thereby forming a second hole transport layer having a thickness of 60nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light-emitting layer is formed thereon as follows: each of the first host compound and the second host compound described in Table 1 below is introduced as a host into two chambers of a vacuum vapor deposition apparatus, respectively, and compound D-39 is introduced into another chamber as a dopant. The two host materials are evaporated at a ratio of 1:1, and the dopant materials are evaporated at different ratios at the same time, and the dopant is deposited at a doping amount of 3wt% based on the total amount of the host and the dopant to form a light-emitting layer having a thickness of 40nm on the second hole transport layer. Next, compounds ET-1 and EI-1 are deposited as electron transport materials at a weight ratio of 50:50 to form an electron transport layer having a thickness of 35nm on the light-emitting layer. After compound EI-1 was deposited as an electron injection layer with a thickness of 2 nm on the electron transport layer, an Al cathode with a thickness of 80 nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus. In this way, an OLED was produced. Each compound for all materials was deposited at 10 -6 Purify by vacuum sublimation under vacuum.

[0248] [Device Comparative Example 1] Preparation of OLEDs containing a single host

[0249] An OLED was manufactured in the same manner as in Device Example 1, except that the second host compound described in the following Table 1 was used alone as a host for the light-emitting layer.

[0250] The driving voltage, current efficiency and emission color of the OLEDs of Device Examples 1 to 4 and Device Comparative Example 1 produced as described above at a luminance of 1,000 nits, and the time taken for the luminance to decrease from 100% to 95% at a luminance of 10,000 nits (lifetime: T 95 ), and the results are shown in Table 1 below.

[0251] Table 1

[0252]

[0253] As can be seen from Table 1 above, compared with an organic electroluminescent device including only a single host material, an organic electroluminescent device including a specific combination of host materials according to the present disclosure exhibits lower driving voltage and / or higher luminous efficiency, and in particular, exhibits significantly improved lifespan characteristics.

[0254] The compounds used in Device Examples 1 to 4 and Device Comparative Example 1 are specifically shown in Table 2 below.

[0255] Table 2

[0256]

[0257]

[0258] [Device Examples 5 and 6] Preparation of an organic electroluminescent device emitting blue light comprising an organic electroluminescent compound according to the present disclosure as an electron buffer layer material

[0259] OLED according to the present disclosure was produced. First, a transparent electrode indium tin oxide (ITO) film (10Ω / sq) (Giomar Co., Ltd., Japan) on a glass substrate for OLED was subjected to ultrasonic washing with acetone and isopropanol in sequence, and thereafter stored in isopropanol and then used. The ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Then, compound HI-2 was introduced into a small chamber of the vacuum vapor deposition apparatus. The vacuum was evacuated until the vacuum degree in the chamber reached 10 -7After the support, the compound was evaporated by applying an electric current to the chamber, thereby forming a first hole injection layer with a thickness of 60nm on the ITO substrate. Next, the compound HI-3 was introduced into another chamber of the vacuum vapor deposition device, and the compound was evaporated by applying an electric current to the chamber, thereby forming a second hole injection layer with a thickness of 5nm on the first hole injection layer. Then, the compound HT-1 was introduced into another chamber of the vacuum vapor deposition device, and the compound was evaporated by applying an electric current to the chamber, thereby forming a first hole transport layer with a thickness of 20nm on the second hole injection layer. Next, the compound HT-3 was introduced into another chamber of the vacuum vapor deposition device and the compound was evaporated by applying an electric current to the chamber, thereby forming a second hole transport layer with a thickness of 5nm on the first hole transport layer. After the hole injection layer and the hole transport layer are formed, a light-emitting layer is formed thereon as follows: the compound BH-1 is introduced into a chamber of the vacuum vapor deposition device as the main body, and the compound BD-1 is introduced into another chamber as a dopant. The two materials were evaporated at different rates, and the dopant was deposited at a doping amount of 2wt% based on the total amount of the host and the dopant to form a light-emitting layer with a thickness of 20nm on the second hole transport layer. Next, the compounds listed in Table 3 were deposited as an electron buffer material with a thickness of 5nm on the light-emitting layer, and then compound ET-1 was introduced into a small chamber as an electron transport material and evaporated to deposit an electron transport layer with a thickness of 30nm. Next, after compound EI-1 was deposited as an electron injection layer with a thickness of 2nm on the electron transport layer, an Al cathode with a thickness of 80nm was deposited by another vacuum vapor deposition device. In this way, an OLED was produced. Each compound used for all materials was heated to 10 -6 Purify by vacuum sublimation under vacuum.

[0260] [Device Comparative Example 2] Preparation of an organic electroluminescent device emitting blue light containing a comparative compound as an electron buffer layer material

[0261] An OLED was manufactured in the same manner as in Device Example 5, except that the electron buffer material shown in the following Table 3 was used as the electron buffer material.

[0262] The driving voltage, luminous efficiency, and luminescent color of the OLEDs of Device Examples 5 and 6 and Device Comparative Example 2 produced as described above at a luminance of 1,000 nit were measured, and the results thereof are shown in Table 3 below.

[0263] Table 3

[0264]

[0265] As can be seen from the above Table 3, the organic electroluminescent device containing the compound according to the present disclosure as an electron buffer material exhibits low driving voltage and / or high luminous efficiency compared to the organic electroluminescent device using the comparative compound as an electron buffer material.

[0266] The compounds used in Device Examples 5 and 6 and Comparative Example 2 are shown in Table 4 below.

[0267] Table 4

[0268]

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 the following formula 1, and the second host material comprising a compound represented by the following formula 2: in, X1 and Y1 each independently represent -N=, -NR7, -O-, or -S-; provided that either one of X1 and Y1 is -N=, and the other of X1 and Y1 is -NR7-, -O-, or -S-; R1 represents a substituted or unsubstituted (C6-C 30 )aryl or substituted or unsubstituted (3- to 30-membered) heteroaryl; R2 to R4 and R7 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C6-C 30 )aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (C1-C 30 ) alkoxy, substituted or unsubstituted tri(C1-C 30 )alkylsilyl, substituted or unsubstituted di(C1-C 30 )alkyl(C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 )alkyldi(C6-C 30 ) arylsilyl, substituted or unsubstituted tri(C6-C 30 ) arylsilyl, (C3-C 30 ) aliphatic ring and (C6-C 30 ) a substituted or unsubstituted condensed ring of an aromatic ring, or -L 11 -N(Ar1)(Ar2); or may be linked to adjacent substituents to form one or more rings; L1 and L 11 Each independently represents a single bond, a substituted or unsubstituted (C6-C 30 )arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene; Ar1 and Ar2 each independently represent hydrogen, substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C2-C 30 )alkenyl, (C3-C 30 ) aliphatic ring and (C6-C 30 ) a substituted or unsubstituted condensed aromatic ring, a substituted or unsubstituted (C6-C 30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; R5 and R6 each independently represent a substituted or unsubstituted (C6-C 30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; and b and c each independently represent an integer of 1 or 2, d represents an integer of 1 to 4, and when b to d are integers of 2 or more, each of R2 to R4 may be the same or different; in, Ring A and Ring B each independently represent a substituted or unsubstituted (C6-C 30 )arene, or substituted or unsubstituted (3- to 30-membered) heteroarene; R 11 and R 12 Each independently represents a substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C6-C 30 ) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; or may be connected to each other to form one or more rings; X2 and Y2 each independently represent -N=, -NR 24 , -O-, or -S-; provided that any one of X2 and Y2 is -N=, and the other of X2 and Y2 is -NR 24 -, -O-, or -S-; R 21 To R 24 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C6-C 30 )aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (C1-C 30 ) alkoxy, substituted or unsubstituted tri(C1-C 30 )alkylsilyl, substituted or unsubstituted di(C1-C 30 )alkyl(C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 )alkyldi(C6-C 30 ) arylsilyl, substituted or unsubstituted tri(C6-C 30 ) arylsilyl, (C3-C 30 ) aliphatic ring and (C6-C 30 ) a substituted or unsubstituted condensed aromatic ring, or -L3-HAr; The premise is R 21 To R 24 At least one of them is -L3-HAr; L2 and L3 each independently represent a single bond, a substituted or unsubstituted (C6-C 30 )arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene; HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group containing at least one nitrogen atom; and n represents an integer of 1 to 4, m represents an integer of 1 to 8, and when n and m are integers of 2 or more, R 22 and R 23 Each of can be the same or different.

2. The plurality of host materials according to claim 1, wherein: The substituted alkyl, the substituted (ene) aryl, the substituted (ene) heteroaryl, the substituted cycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, and the substituted condensed ring of the aliphatic ring and the aromatic ring are each independently substituted by at least one selected from the group consisting of deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C 30 ) alkyl, halogenated (C1-C 30 )alkyl, (C2-C 30 )alkenyl, (C2-C 30 ) alkynyl, (C1-C 30 ) alkoxy, (C1-C 30 )alkylthio, (C3-C 30 )cycloalkyl, (C3-C 30 )cycloalkenyl, (3- to 7-membered)heterocycloalkyl, (C6-C 30 ) aryloxy, (C6-C 30 ) arylthio, unsubstituted or (C6-C 30 )aryl-substituted (5- to 30-membered) heteroaryl, unsubstituted or (5- to 30-membered) heteroaryl-substituted (C6-C 30 )aryl, tri(C1-C 30 ) alkylsilyl, tri(C6-C 30 ) arylsilyl, di(C1-C 30 )alkyl(C6-C 30 ) arylsilyl, (C1-C 30 )alkyldi(C6-C 30 ) arylsilyl, (C3-C 30 ) aliphatic ring and (C6-C 30 ) fused aromatic ring, amino, mono- or di-(C1-C 30 ) alkylamino, substituted or unsubstituted mono- or di-(C6-C 30 ) arylamino, (C1-C 30 )alkyl(C6-C 30 )arylamino, mono- or di-(3- to 30-membered) heteroarylamino, (C1-C 30 )alkyl (3-30 membered) heteroarylamino, (C6-C 30 )aryl (3- to 30-membered) heteroarylamino, (C1-C 30 )alkylcarbonyl, (C1-C 30 ) alkoxycarbonyl, (C6-C 30 ) arylcarbonyl, (C6-C 30 ) aryl phosphinyl, di(C6-C 30 ) aryl boron carbonyl, di(C1-C 30 ) alkyl boron carbonyl, (C1-C 30 )alkyl(C6-C 30 ) aryl boron carbonyl, (C6-C 30 )Aryl (C1-C 30 )alkyl, and (C1-C 30 )alkyl(C6-C 30 )aryl.

3. The plurality of host materials according to claim 1, wherein: HAr in Formula 2 is represented by the following Formula 3 or 4: Among them, X a , X b , Y a , and Y b Each independently represents N or CR 33 ; The premise is X a and X b At least one of them is N, and Y a and Y b At least one of is N; and R 31 To R 37 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C6-C 50 )aryl, substituted or unsubstituted (3- to 50-membered) heteroaryl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C1-C 30 ) alkoxy, substituted or unsubstituted tri(C1-C 30 )alkylsilyl, substituted or unsubstituted di(C1-C 30 )alkyl(C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 )alkyldi(C6-C 30 ) arylsilyl, or substituted or unsubstituted tri(C6-C 30 ) arylsilyl; or may be connected to adjacent substituents to form one or more rings.

4. The plurality of host materials according to claim 1, wherein: Formula 2 is represented by any one of the following Formulas 2-1 to 2-8: in, X2, Y2, R 11 , R 12 , R 21 To R 23 , L2, n, and m are as defined in claim 1; and n′ represents an integer of 1 or 2, m′ represents an integer of 1 to 4, and m″ represents an integer of 1 to 6.

5. The plurality of host materials according to claim 1, wherein: Formula 2 is represented by any one of the following Formulas 2-1 and 2-9: in, X2, Y2, R 11 and R 12 , R 21 To R 23 , and L2 are as defined in claim 1; and n′ represents an integer of 1 or 2, m′ represents an integer of 1 to 4, and m″ represents an integer of 1 to 6.

6. The plurality of host materials according to claim 1, wherein: Formula 1 is represented by any one of the following formulas 1-1 to 1-4: in, d represents an integer of 1 to 3, and when d is an integer of 2 or more, each R4 may be the same or different; and X1, Y1, R1 to R6, L1, b, and c are as defined in claim 1.

7. The plurality of host materials according to claim 1, wherein: The compound represented by Formula 1 is selected from the following compounds:

8. The plurality of host materials of claim 1, wherein: The compound represented by Formula 2 is selected from the following compounds: 9 . An organic electroluminescent device comprising a first electrode; a second electrode; and at least one light-emitting layer between the first electrode and the second electrode, wherein the at least one light-emitting layer comprises a plurality of host materials according to claim 1 .

10. An organic electroluminescent compound represented by the following formula 2′: in, Ring A and Ring B each independently represent a substituted or unsubstituted (C6-C 30 )arene, or substituted or unsubstituted (3- to 30-membered) heteroarene; R 11 and R 12 Each independently represents a substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C6-C 30 ) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; or may be connected to each other to form one or more rings; X2 and Y2 each independently represent -N=, -NR 24 , -O-, or -S-; provided that any one of X2 and Y2 is -N=, and the other of X2 and Y2 is -NR 24 -, -O-, or -S-; R 21 and R 24 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C6-C 30 )aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (C1-C 30 ) alkoxy, substituted or unsubstituted tri(C1-C 30 )alkylsilyl, substituted or unsubstituted di(C1-C 30 )alkyl(C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 )alkyldi(C6-C 30 ) arylsilyl, substituted or unsubstituted tri(C6-C 30 ) arylsilyl, (C3-C 30 ) aliphatic ring and (C6-C 30 ) a substituted or unsubstituted condensed aromatic ring, or -L3-HAr; The premise is R 21 To R 24 At least one of is -L3-HAr; and if R 23 is -L3-HAr, then the case where both ring A and ring B are substituted or unsubstituted benzene is excluded; L2 and L3 each independently represent a single bond, a substituted or unsubstituted (C6-C 30 )arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene; HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group containing at least one nitrogen atom; and n represents an integer of 1 to 4, m represents an integer of 1 to 8, and when n and m are integers of 2 or more, R 22 and R 23 Each of can be the same or different.

11. The organic electroluminescent compound according to claim 10, wherein HAr in Formula 2 is represented by the following Formula 3 or 4: Among them, X a , X b , Y a , and Y b Each independently represents N or CR 33 ; The premise is X a and X b Any one of is N, and Y a and Y b At least one of is N; and R 31 To R 37 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C6-C 50 )aryl, substituted or unsubstituted (3- to 50-membered) heteroaryl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C1-C 30 ) alkoxy, substituted or unsubstituted tri(C1-C 30 )alkylsilyl, substituted or unsubstituted di(C1-C 30 )alkyl(C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 )alkyldi(C6-C 30 ) arylsilyl, substituted or unsubstituted tri(C6-C 30 ) arylsilyl, substituted or unsubstituted mono- or di-(C1-C 30 ) alkylamino, substituted or unsubstituted mono- or di-(C6-C 30 ) arylamino, or substituted or unsubstituted (C1-C 30 )alkyl(C6-C 30 ) arylamino; or may be connected to adjacent substituents to form one or more rings.

12. The organic electroluminescent compound according to claim 10, wherein Formula 2′ is represented by any one of the following formulae 2-1a and 2-2 to 2-8: in, R 21′ and R 22′ Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C6-C 30 )aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (C1-C 30 ) alkoxy, substituted or unsubstituted tri(C1-C 30 )alkylsilyl, substituted or unsubstituted di(C1-C 30 )alkyl(C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 )alkyldi(C6-C 30 ) arylsilyl, substituted or unsubstituted tri(C6-C 30 ) arylsilyl, (C3-C 30 ) aliphatic ring and (C6-C 30 ) a substituted or unsubstituted fused aromatic ring, or -L3-HAr; provided that R 21′ and R 22′ At least one of them is -L3-HAr; R 23′ represents hydrogen, deuterium, or unsubstituted or not substituted by deuterium (C6-C 30 ) aryl; n′ represents an integer of 1 or 2, m′ represents an integer of 1 to 4, and m″ represents an integer of 1 to 6; and X2, Y2, R 11 , R 12 , R 21 To R 23 , L2, n, and m are as defined in claim 10.

13. The organic electroluminescent compound according to claim 10, wherein Formula 2′ is represented by the following formula 2-9: in, X2, Y2, R 11 , R 12 , R 21 To R 23 , and L2 are as defined in claim 10; and n′ represents an integer of 1 or 2, and m″ represents an integer of 1 to 6.

14. The organic electroluminescent compound according to claim 10, wherein The compound represented by formula 2' is selected from the following compounds: 15 . An organic electroluminescent material comprising the organic electroluminescent compound according to claim 10 . 16 . An organic electroluminescent device comprising the organic electroluminescent compound according to claim 10 .

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