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 comprising the same. By comprising a specific combination of the compounds according to the present disclosure as a plurality of host materials and / or the organic electroluminescent compound according to the present disclosure as a host material, an organic electroluminescent device having a low driving voltage and / or high luminous efficiency and / or a long lifespan characteristic can be provided compared to a conventional organic electroluminescent device.

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] The TPD / Alq3 double-layer small molecule organic electroluminescent device (OLED) with green light emission consisting of a light-emitting layer and a charge transport layer was first developed by Tang et al. of Eastman Kodak in 1987. Since then, research on organic electroluminescent devices has been rapidly carried out, and OLED has been commercialized since then. At present, OLED mainly uses phosphorescent materials with excellent luminous efficiency in panel implementation. In many applications such as TV and lighting equipment, OLED life is insufficient, and high OLED efficiency is still required. Typically, the higher the brightness of OLED becomes, the life of the OLED is correspondingly shortened. Therefore, for long-term use and high display resolution, an OLED with high luminous efficiency and / or long life characteristics is required.

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

[0004] However, Korean Patent Application Publication No. 2017-0137976 and WO 2021 / 025163 A1 disclose anthracene derivatives substituted with benzoxanthene or benzothioxanthene as host materials for a light-emitting layer, but do not specifically disclose a specific combination of host materials 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 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 according to the present disclosure as a variety of host materials and / or an organic electroluminescent compound according to the present disclosure as a host material.

[0007] Solution to the problem

[0008] As a result of in-depth research to solve the above technical problems, the inventors of the present invention found that the above-mentioned objectives can be achieved by a plurality of host materials comprising at least one first host compound represented by the following formula 1 and at least one second host compound represented by the following formula 2 (wherein the first host compound and the second host compound are different from each other), thereby completing the present invention.

[0009]

[0010] In formula 1,

[0011] R1 to R8 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C2-C 30 )alkenyl, 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 (C3-C 30 )cycloalkenyl, 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, (C3-C 30 ) aliphatic ring and (C6-C 30 ) substituted or unsubstituted condensed ring of an aromatic ring, substituted or unsubstituted mono- or di-(C1-C 30 )alkylamino, substituted or unsubstituted mono- or di-(C2-C 30 )alkenylamino, substituted or unsubstituted mono- or di-(C6-C 30 )arylamino, substituted or unsubstituted mono- or di-(3- to 30-membered) heteroarylamino, substituted or unsubstituted (C1-C 30 )alkyl(C2-C 30 )alkenylamino, substituted or unsubstituted (C1-C 30 )alkyl(C6-C 30 ) arylamino, substituted or unsubstituted (C1-C 30 )alkyl(3-30 membered)heteroarylamino, substituted or unsubstituted(C2-C 30)Alkenyl (C6-C 30 ) arylamino, substituted or unsubstituted (C2-C 30 )alkenyl (3- to 30-membered) heteroarylamino, substituted or unsubstituted (C6-C 30 )aryl(3-30-membered)heteroarylamino, and combinations thereof;

[0012] L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6-C 30 )arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene;

[0013] Ar1 represents a substituted or unsubstituted (C6-C 30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; and

[0014] Ar2 is represented by the following formula 1-A;

[0015]

[0016] In Formula 1-A,

[0017] X represents -O- or -S-;

[0018] R′1 to R′ 10 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C 30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; and

[0019] R′1 to R′ 10 Any one of them is connected to L2;

[0020]

[0021] In formula 2,

[0022] Ar 11 and Ar 12 Each independently represents a substituted or unsubstituted (C6-C 30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl;

[0023] L 11 and L 12 Each independently represents a single bond, a substituted or unsubstituted (C6-C 30 )arylene, or substituted or unsubstituted (3- to 30-membered)heteroarylene; and

[0024] R 11 To R 18 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30) alkyl, substituted or unsubstituted (C2-C 30 )alkenyl, 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 (C3-C 30 )cycloalkenyl, 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, or (C3-C 30 ) aliphatic ring and (C6-C 30 ) A substituted or unsubstituted condensed aromatic ring.

[0025] Beneficial Effects of the Invention

[0026] 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

[0027] 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.

[0028] 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 (different from the first host compound).

[0029] The present disclosure relates to an organic electroluminescent compound represented by Formula 11, 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.

[0030] The present disclosure relates to an organic electroluminescent compound represented by Formula 12, 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.

[0031] Herein, the term "organic electroluminescent compound" in the present disclosure means a compound that can be used in an organic electroluminescent device, and which can be contained in any material layer constituting the organic electroluminescent device as necessary.

[0032] Herein, the term "organic electroluminescent material" means a material that can be used in an organic electroluminescent device and which 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 (including 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.

[0033] 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 contained 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 contained in the same layer or in different layers, and may be mixed-evaporated or co-evaporated, or may be evaporated individually.

[0034] 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.

[0035] In this article, “(C1-C 30"(C3-C4)alkyl" 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. Herein, "(C3-C4)alkyl" 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. 30 "(C6-C6-C6-yl)alkyl" means a monocyclic hydrocarbon or a 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, "(C6-C6-yl)alkyl" means a monocyclic hydrocarbon or a 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. 30 The "(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 [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-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, 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 etc.Herein, " (3 yuan to 30 yuan) (sub) heteroaryl " is the aryl of the heteroatoms of the group that has 3 to 30 ring skeleton atoms and includes at least one, preferably 1 to 4, selected from B, N, O, S, Si, P, Se and Ge, wherein the number of ring skeleton carbon atoms is preferably 5 to 25.Above-mentioned (sub) heteroaryl can be monocyclic or the condensed ring with at least one benzene ring, and can be partially saturated.In addition, herein, above-mentioned heteroaryl can be the heteroaryl formed by at least one heteroaryl or aryl being connected to heteroaryl 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 fused ring heteroaryl groups, including benzofuranyl, benzothienyl, isobenzofuranyl, , dibenzofuranyl, dibenzothienyl, dibenzoselenophene, benzofuranoquinolyl, benzofuranoquinazolinyl, benzofuranonaphthyridinyl, benzofuranopyrimidinyl, naphthofuranopyrimidinyl, benzothienoquinolyl, benzothienoquinazolinyl, benzothienonaphthyridinyl, benzothienopyrimidinyl, naphthothienopyrimidinyl, pyrimidoindolyl, benzopyrimidoindolyl, benzofuranopyrazinyl, naphthofuranopyrimidinyl oxazine, benzothienopyrazinyl, naphthiophenopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl The heteroaryl group may be 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 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-indolizidinyl, 2-indolizidinyl, 3-indolizidinyl, 5-indolizidinyl, 6-indolizidinyl, 7-indolizidinyl, 8-indolizidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl yl, 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-furyl, 3-furyl, 2- benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 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, azacarbazole-5-yl, azacarbazole-6-yl, azacarbazole-7-yl, azacarbazole-8-yl, azacarbazole-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, -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- 3-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-dibenzothiophene, 2-dibenzothiophene, 3-dibenzothiophene, 4-dibenzothiophene, 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, 7-naphtho-[1,2-b]-benzofuranyl , 8-naphtho-[1,2-b]-benzofuranyl, 9-naphtho-[1,2-b]-benzofuranyl, 10-naphtho-[1,2-b]-benzofuranyl, 1-naphtho-[2,3-b]-benzofuranyl, 2-naphtho-[2,3-b]-benzofuranyl, 3-naphtho-[2,3-b]-benzofuranyl, 4-naphtho-[2, 3-b]-benzofuranyl, 5-naphtho-[2,3-b]-benzofuranyl, 6-naphtho-[2,3-b]-benzofuranyl, 7-naphtho-[2,3-b]-benzofuranyl, 8-naphtho-[2,3-b]-benzofuranyl, 9-naphtho-[2,3-b]-benzofuranyl, 10-naphtho-[2,3-b]-benzofuranyl 1-naphtho-[2,1-b]-benzofuranyl, 2-naphtho-[2,1-b]-benzofuranyl, 3-naphtho-[2,1-b]-benzofuranyl, 4-naphtho-[2,1-b]-benzofuranyl, 5-naphtho-[2,1-b]-benzofuranyl, 6-naphtho-[2,1-b]-benzofuranyl, 7-naphtho-[2,1-b]-benzofuranyl, 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]-benzothiophene, 2-naphtho-[1,2-b]-benzothiophene, 3-naphtho-[1,2-b]-benzothiophene 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]-benzothiophene, 1-naphtho-[2,3-b]-benzothiophene, 2-naphtho-[2,3-b]-benzothiophene, 3-naphtho-[2,3-b]-benzothiophene, 4-naphtho-[2,3-b]-benzothiophene, 5-naphtho-[2,3-b]-benzothiophene, 1-naphtho-[2,1-b]-benzothiophene 1-b-benzothiophene, 2-naphtho-[2,1-b]-benzothiophene, 3-naphtho-[2,1-b]-benzothiophene, 4-naphtho-[2,1-b]-benzothiophene, 5-naphtho-[2,1-b]-benzothiophene, 6-naphtho-[2,1-b]-benzothiophene, 7-naphtho-[2,1-b]-benzothiophene, 8-naphtho-[2,1-b]-benzothiophene,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-benzothio[3,2-d]pyrimidinyl, 6-benzothio[3,2-d]pyrimidinyl, 7-benzothio[3,2-d]pyrimidinyl, 8-benzothio[3,2-d]pyrimidinyl, 9-benzothio[3,2-d]pyrimidinyl, 2-benzofurano[3,2-d]pyrimidinyl, , 6-benzofurano[3,2-d]pyrazinyl, 7-benzofurano[3,2-d]pyrazinyl, 8-benzofurano[3,2-d]pyrazinyl, 9-benzofurano[3,2-d]pyrazinyl, 2-benzothio[3,2-d]pyrazinyl, 6-benzothio[3,2-d]pyrazinyl, 7-benzothio[3,2-d]pyrazinyl In some embodiments, the term "heteroaryl" refers to a 1-dibenzothiophene group, a 2-dibenzothio[3,2-d]pyrazinyl group, a 9-benzothio[3,2-d]pyrazinyl group, a 1-silafluorenyl group, a 2-silafluorenyl group, a 3-silafluorenyl group, a 4-silafluorenyl group, a 1-germanylfluorenyl group, a 2-germanylfluorenyl group, a 3-germanylfluorenyl group, a 4-germanylfluorenyl group, a 1-dibenzoselenophene group, a 2-dibenzoselenophene group, a 3-dibenzoselenophene group, a 4-dibenzoselenophene group, etc. In addition, the "heteroaryl (sub) group" can be classified into a heteroaryl (sub) group having an electron characteristic and a heteroaryl (sub) group having a hole characteristic. The (sub)heteroaryl group having electron characteristics is a substituent having relatively abundant electrons in the parent nucleus, and for example, it can be a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazine group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinolyl group, etc. The (sub)heteroaryl group having hole characteristics is a substituent having relatively poor electrons in the parent nucleus, and for example, it can be a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophene group. Herein, the term "(C3-C, 30 ) aliphatic ring and (C6-C 30 The term "condensed ring of (C3-C4)" means a ring formed by fusing 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 (C3-C4) 30 ) aliphatic ring and (C6-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 "halogen" in the present disclosure includes F, Cl, Br and I.

[0036] 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 of the immediately adjacent substitution position, for example, the compound has substituents at positions 1 and 3 on benzene. The para-configuration indicates the next substitution position of the meta position, for example, the compound has substituents at positions 1 and 4 on benzene.

[0037] 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, and preferably, it may be a substituted or unsubstituted (3-26-membered) monocyclic or polycyclic alicyclic ring, aromatic ring, or a combination thereof. In addition, the formed ring may contain at least one heteroatom selected from the group consisting of B, N, O, S, Si and P, preferably, N, O and S. According to one embodiment of the present disclosure, the number of 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.

[0038] 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., substituent), and is replaced by a group in which two or more substituents are connected among the substituents. Unless otherwise specified, the substituent can replace the hydrogen at the position where the substituent can be replaced without limitation, and when two or more hydrogen atoms in the functional group are each replaced by a substituent, each substituent can be the same or different. The maximum number of substituents that can be replaced in a functional group can be the total number of valences that can be replaced for each atom forming the functional group. The substituted alkyl, substituted alkenyl, substituted (ene)aryl, substituted (ene)heteroaryl, substituted cycloalkyl, substituted cycloalkenyl, substituted heterocycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted condensed ring of aliphatic ring and aromatic ring, substituted mono- or dialkylamino, substituted mono- or dialkenylamino, substituted mono- or diarylamino, substituted mono- or diheteroarylamino, substituted alkylalkenylamino, substituted alkylarylamino, substituted alkylheteroarylamino, substituted alkenylarylamino, substituted alkenylheteroarylamino, and substituted arylheteroarylamino in the formula of the present disclosure may each independently be 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 substituted with at least one (C6-C 30 )aryl-substituted (3- to 30-membered) heteroaryl, unsubstituted or (C1-C 30 (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, tri(C6-C 30 ) arylgermanyl, amino, mono- or di-(C1-C 30 ) alkylamino, mono- or di-(C2-C 30 )alkenylamino, unsubstituted or (C1-C 30 ) alkyl-substituted mono- or di-(C6-C 30 )arylamino, mono- or di-(3- to 30-membered) heteroarylamino, (C1-C 30 )alkyl(C2-C 30 )alkenylamino, (C1-C 30 )alkyl(C6-C 30 ) arylamino, (C1-C 30 )alkyl(3-30 membered)heteroarylamino, (C2-C 30 )Alkenyl (C6-C 30 ) arylamino, (C2-C 30 )alkenyl (3- to 30-membered) heteroarylamino, (C6-C 30 )aryl (3- to 30-membered) heteroarylamino, (C1-C 30 )alkylcarbonyl, (C1-C 30 ) alkoxycarbonyl, (C6-C 30 ) arylcarbonyl, 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 ) aromatic group, etc.

[0039] When a substituent is not shown in the chemical formula or compound structure of the present disclosure, this may mean that all positions that can appear as a substituent are hydrogen or deuterium. That is, in the case of deuterium (an isotope of hydrogen), some hydrogen atoms may be deuterium, which is an isotope; and in this case, the content of deuterium may be 0% to 100%. In the case where a substituent is not shown in the chemical formula or compound structure of the present disclosure, when deuterium is not explicitly excluded (such as when the content of deuterium is 0%, the content of hydrogen is 100%, and all substituents are hydrogen), hydrogen and deuterium may be mixed and used in the compound. Deuterium is an element having a deuteron composed of one proton and one neutron as an atomic nucleus, which is one of the isotopes of hydrogen and can be represented by hydrogen-2, and the element symbol may be D or 2H. Although isotopes have the same atomic number (Z), isotopes with different mass numbers (A) mean that the same number of protons and neutrons can also be interpreted as having different numbers of elements.

[0040] In this document, "combinations thereof" means that one or more components of the corresponding list are combined to form known or chemically stable arrangements that can be imagined by a person skilled in the art from the corresponding list. For example, alkyl and deuterium can be combined to form partially or fully deuterated alkyl; halogen and alkyl can be combined to form haloalkyl substituents; and halogen, alkyl and aryl can be combined to form haloarylalkyl. For example, preferred combinations of substituents can include up to 50 atoms other than hydrogen and deuterium, or up to 40 atoms other than hydrogen and deuterium, or up to 30 atoms other than hydrogen and deuterium, or in many cases, preferred combinations of substituents can include up to 20 atoms other than hydrogen and deuterium.

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

[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 below, the second host compound is represented by Formula 2 below, and the first host compound and the second host compound are different from each other.

[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] R1 to R8 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C2-C 30 )alkenyl, 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 (C3-C 30 )cycloalkenyl, 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, (C3-C 30 ) aliphatic ring and (C6-C 30 ) substituted or unsubstituted condensed ring of an aromatic ring, substituted or unsubstituted mono- or di-(C1-C 30 )alkylamino, substituted or unsubstituted mono- or di-(C2-C 30 )alkenylamino, substituted or unsubstituted mono- or di-(C6-C 30 )arylamino, substituted or unsubstituted mono- or di-(3- to 30-membered) heteroarylamino, substituted or unsubstituted (C1-C 30 )alkyl(C2-C 30 )alkenylamino, substituted or unsubstituted (C1-C 30 )alkyl(C6-C 30 ) arylamino, substituted or unsubstituted (C1-C 30 )alkyl(3-30 membered)heteroarylamino, substituted or unsubstituted(C2-C 30 )Alkenyl (C6-C 30 ) arylamino, substituted or unsubstituted (C2-C 30 )alkenyl (3- to 30-membered) heteroarylamino, substituted or unsubstituted (C6-C 30 )aryl(3-30-membered)heteroarylamino, and combinations thereof;

[0048] L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6-C 30 )arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene;

[0049] Ar1 represents a substituted or unsubstituted (C6-C 30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; and

[0050] Ar2 is represented by the following formula 1-A;

[0051]

[0052] In Formula 1-A,

[0053] X represents -O- or -S-;

[0054] R′1 to R′ 10Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C 30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; and

[0055] R′1 to R′ 10 Any one of them is connected to L2.

[0056] In one embodiment, X may be -O-.

[0057] In one embodiment, R1 to R8 can each independently be hydrogen or deuterium.

[0058] In one embodiment, L1 and L2 are each independently a single bond or a substituted or unsubstituted (C6-C 30 )arylene, preferably a single bond or substituted or unsubstituted (C6-C 25 )arylene, more preferably a single bond or substituted or unsubstituted (C6-C 18 For example, L1 and L2 may each independently be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted anthracene group.

[0059] In one embodiment, Ar1 may be substituted or unsubstituted (C6-C 30 ) aryl, preferably substituted or unsubstituted (C6-C 25 ) aryl, more preferably substituted or unsubstituted (C6-C 18 ) aryl. For example, Ar1 can be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, or a combination thereof. For example, Ar1 can be substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted p-terphenyl, or substituted or unsubstituted phenanthryl, wherein the substituent of the substituted group can be deuterium, methyl, tert-butyl, phenyl or biphenyl.

[0060] According to one embodiment, Formula 1 may be represented by any one of the following Formulas 1-1 to 1-3.

[0061]

[0062] In formulas 1-1 to 1-3,

[0063] R1 to R8, L1, L2, Ar1, X, and R′1 to R′ 10 is defined as in Equation 1.

[0064] In one embodiment, R'1 to R' 10 Each independently may be hydrogen, deuterium, or substituted or unsubstituted (C6-C 30 ) aryl, preferably hydrogen, deuterium, or substituted or unsubstituted (C6-C 25 ) aryl, more preferably hydrogen, deuterium, or substituted or unsubstituted (C6-C 18 ) aryl. For example, R'1 to R' 10 Each independently may be hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted biphenyl.

[0065] According to one embodiment, the first host compound represented by Formula 1 may be a compound wherein R1 to R8 each independently represent hydrogen or deuterium, R′1 to R′ 10 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C 15 )aryl, or substituted or unsubstituted (3- to 15-membered) heteroaryl.

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

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082] Among them, "D n " means that n number of hydrogens are replaced by deuterium, wherein n represents an integer of 1 or more and the upper limit of n is determined by the number of hydrogens that can be replaced in each compound.

[0083] According to one embodiment, the second host compound as another host material may be represented by Formula 2 below.

[0084]

[0085] In formula 2,

[0086] L 11 and L 12 Each independently represents a single bond, a substituted or unsubstituted (C6-C 30 )arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene;

[0087] Ar 11 and Ar 12 Each independently represents a substituted or unsubstituted (C6-C 30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; and

[0088] R 11 To R 18 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C2-C 30 )alkenyl, 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 (C3-C 30 )cycloalkenyl, 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, or (C3-C 30 ) aliphatic ring and (C6-C 30) A substituted or unsubstituted condensed aromatic ring.

[0089] In one embodiment, R 11 To R 18 Each independently can be hydrogen or deuterium.

[0090] In one embodiment, L 11 and L 12 Each independently may be a single bond, or substituted or unsubstituted (C6-C 30 )arylene, preferably a single bond, or substituted or unsubstituted (C6-C 25 )arylene, more preferably unsubstituted or substituted with deuterium or (C6-C 30 ) aryl substituted (C6-C 18 ) arylene. For example, L 11 and L 12 Each independently may be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted phenanthrenyl group, wherein the substituents may be replaced by one or more deuterium atoms.

[0091] In one embodiment, Ar 11 and Ar 12 Each independently may be substituted or unsubstituted (C6-C 30 )aryl or substituted or unsubstituted (5- to 30-membered) heteroaryl, preferably substituted or unsubstituted (C6-C 25 )aryl, or substituted or unsubstituted (5- to 25-membered) heteroaryl, more preferably substituted or unsubstituted (C6-C 18 )aryl, or substituted or unsubstituted (5- to 18-membered) heteroaryl. 11 and Ar 12 Each independently may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, or a substituent represented by the following formula 2-A. For example, Ar 11 and Ar 12 Each independently may be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, or a substituted or unsubstituted phenanthryl, or may be represented by the following formula 2-A, wherein the substituent of the substituted group may be deuterium, phenyl, biphenyl, terphenyl, naphthyl or phenanthryl.

[0092]

[0093] In Formula 2-A,

[0094] T1 represents -O-, -S-, or -CR 27 R 28 ;

[0095] R 19 To R 28 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C6-C 30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; and

[0096] R 19 To R 26 Any one of them and L 11 or L 12 connect.

[0097] In one embodiment, R 19 To R 26 Each independently may be hydrogen, deuterium, or substituted or unsubstituted (C6-C 30 ) aryl, preferably hydrogen, deuterium, or substituted or unsubstituted (C6-C 25 ) aryl, more preferably hydrogen, deuterium, or substituted or unsubstituted (C6-C 18 ) aryl. For example, R 19 To R 26 Each independently may be hydrogen, deuterium, or substituted or unsubstituted phenyl.

[0098] 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.

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110] Among them, "D n " means that n number of hydrogens are replaced by deuterium, wherein n represents an integer of 1 or more and the upper limit of n is determined by the number of hydrogens that can be replaced in each compound.

[0111] The compound represented by Formula 1 or 2 according to the present disclosure can 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. 2021-0046437 and 2010-0109060, Chinese Patent Application Publication No. 110294663, etc., but is not limited thereto.

[0112] In addition, the deuterated compounds of Formulas 1 and 2 can be prepared in a similar manner using deuterated precursor materials, or more generally can be prepared by treating non-deuterated compounds with a deuterated solvent D6-benzene in the presence of a Lewis acid H / D exchange catalyst (such as aluminum chloride or ethylaluminum chloride). In addition, the degree of deuteration can be controlled by changing the reaction conditions (such as reaction temperature). For example, the number of deuterium in Formulas 1 and 2 can be adjusted by controlling the reaction temperature and time, acid equivalents, etc.

[0113] According to another embodiment of the present disclosure, the present disclosure provides an organic electroluminescent compound represented by the following Formula 11.

[0114]

[0115] In formula 11,

[0116] R1 to R8 each independently represent hydrogen or deuterium; provided that at least one of R1 to R8 is deuterium,

[0117] L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6-C 30 )arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene;

[0118] Ar1 represents a substituted or unsubstituted (C6-C 30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; and

[0119] Ar2 is represented by the following formula 1-A;

[0120]

[0121] In Formula 1-A

[0122] X represents -NR"-, -Se-, -O- or -S-;

[0123] R′1 to R′ 10 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C 30 ) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; or may be connected to an adjacent substituent to form a substituted or unsubstituted (3- to 30-membered) monocyclic or polycyclic alicyclic ring, aromatic ring, or a combination thereof; provided that R′1 to R′ 10 At least one of is deuterium; and

[0124] R′1 to R′ 10 Any one of them is connected to L2;

[0125] This is based on the assumption that all hydrogen in the compound is replaced by deuterium.

[0126] In one embodiment, at least one of R1, R4, R5, and R8 in Formula 11 may be hydrogen.

[0127] In one embodiment, the residual rate of hydrogen in Formula 11 can be 20% to 60%, 30% to 60% or 40% to 60% of the total amount of hydrogen. When the residual rate of hydrogen in the compound is within the above range, the bond dissociation energy is increased due to deuteration, thereby improving the stability of the compound. In addition, when the organic electroluminescent compound according to the present invention is used in an organic electroluminescent device with only minimal deuterium substitution, the life characteristics can be improved.

[0128] In one embodiment, the residual rate of hydrogen in Formula 11 may be 30% to 50% of the total amount of hydrogen.

[0129] In one embodiment, the residual rate of hydrogen in Formula 11 may be 20% to 30% of the total amount of hydrogen.

[0130] According to one embodiment, the compound represented by Formula 11 may be more specifically illustrated by the following compounds, but is not limited thereto.

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138] Among them, "D n " means that n number of hydrogens are replaced by deuterium, wherein n represents an integer of 1 or more and the upper limit of n is determined by the number of hydrogens that can be replaced in each compound.

[0139] According to another embodiment, the present disclosure provides an organic electroluminescent compound represented by Formula 12 below.

[0140]

[0141] In formula 12,

[0142] R1 to R8 each independently represent hydrogen or deuterium;

[0143] L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6-C 30 )arylene, or substituted or unsubstituted (3- to 30-membered)heteroarylene; and

[0144] Ar1 is represented by the following formula 1-B or 1-C;

[0145]

[0146] In formulas 1-B and 1-C,

[0147] a represents an integer from 1 to 3, and b and c each independently represent an integer from 0 to 3;

[0148] represents the attachment site to L1; and

[0149] Ar2 is represented by the following formula 1-A;

[0150]

[0151] In Formula 1-A,

[0152] X represents -NR"-, -Se-, -O- or -S-;

[0153] R′1 to R′ 10 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C 30 ) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; or may be connected to adjacent substituents to form a substituted or unsubstituted (3- to 30-membered) monocyclic or polycyclic alicyclic ring, aromatic ring, or a combination thereof; and

[0154] R′1 to R′ 10 Any one of them is connected to L2.

[0155] According to one embodiment, the organic electroluminescent compound represented by the above Formula 12 may be more specifically illustrated by the following compounds, but is not limited thereto.

[0156]

[0157]

[0158] Hereinafter, an organic electroluminescent device to which the aforementioned various host materials and / or organic electroluminescent compounds are applied will be described.

[0159] An organic electroluminescent device according to an embodiment includes a first electrode, a second electrode, and at least one organic layer interposed 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 first host compound and the second host compound are different from each other.

[0160] According to one embodiment, the plurality of host materials disclosed herein include at least one compound of compounds H1-1 to H1-310 as a first host compound and at least one compound of compounds H2-1 to H2-366 as a second host compound. The 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.

[0161] According to one embodiment, the light-emitting layer may include an organic electroluminescent compound represented by Formula 11 or an organic electroluminescent compound represented by Formula 12 as a host material. For example, the organic electroluminescent device according to the present disclosure may include at least one of compounds H1-156 to H1-310, or at least one of compounds H1-21 to H1-28, H1-56 to H1-63, H1-98 to H1-104, and H1-143 to H1-149 as a host material in the light-emitting layer.

[0162] In addition to the light-emitting layer, the organic layer may further include at least one layer selected from the following: hole injection layer, hole transport layer, hole auxiliary layer, luminescence 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, luminescence 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, luminescence 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.

[0163] 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).

[0164] One of the first electrode and the second electrode may be an anode, and the other may be a cathode, wherein 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 types of materials forming the first electrode and the second electrode, the organic electroluminescent device may be a top emission type, a bottom emission type, or a double-sided emission type.

[0165] 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.

[0166] An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof can be used between the light-emitting layer and the cathode. The electron buffer layer can be 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 can use two compounds at the same time. The hole blocking layer can 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 can also be multilayered, wherein each layer can use a variety of compounds. In addition, the electron injection layer can be doped with an n-type dopant.

[0167] 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 further included hole transport layer 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.

[0168] 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 the inner surface of one or both 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, MgF2, CaF2, rare earth metal fluorides, etc.; and metal oxides include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0169] The organic electroluminescent device according to one embodiment of the present disclosure may be an organic electroluminescent device having a tandem structure. In the case of a tandem organic electroluminescent device according to one embodiment, a single light-emitting unit (light-emitting unit) may be formed into a structure in which two or more units are connected by a charge generation layer. The organic electroluminescent device may include a plurality of two or more light-emitting units, for example, a plurality of three or more light-emitting units, the light-emitting unit having a first electrode and a second electrode opposite to each other on a substrate and a light-emitting layer stacked between the first electrode and the second electrode and emitting light within a specific wavelength range. According to one embodiment, the organic electroluminescent device may include a plurality of light-emitting units, and each of these light-emitting units may include a hole transport band, a light-emitting layer, and an electron transport band, and the hole transport band may include a hole injection layer and a hole transport layer, and the electron transfer zone may include an electron transport layer and an electron injection layer. According to one embodiment, three or more light-emitting layers may be included in the light-emitting unit. Multiple light-emitting units may emit the same color or different colors. In addition, a light-emitting unit may include one or more light-emitting layers, and the multiple light-emitting layers may be light-emitting layers of the same or different colors. It may include one or more charge generation layers located between each light-emitting unit. A charge generation layer refers to a layer that generates holes and electrons when a voltage is applied. When there are three or more light-emitting units, the charge generation layer may be located between the light-emitting units. At this time, the multiple charge generation layers may be the same as or different from each other. By arranging the charge generation layer between the light-emitting units, the current efficiency in each light-emitting unit is increased, and the charge can be evenly distributed. Specifically, the charge generation layer is arranged between two adjacent stacks, and can be used to drive a tandem organic electroluminescent device using only a pair of anodes and cathodes, without the need for a separate internal electrode located between the stacks.

[0170] The charge generation layer may be composed of an n-type charge generation layer and a p-type charge generation layer, and the n-type charge generation layer may be doped with an alkali metal, an alkaline earth metal, or a compound of an alkali metal and an alkaline earth metal. The alkali metal may include one selected from the group consisting of Li, Na, K, Rb, Cs, Fr, Yb, and combinations thereof, and the alkaline earth metal may include one selected from the group consisting of Be, Mg, Ca, Sr, Ba, Ra, and combinations thereof. The p-type charge generation layer may be made of a metal or an organic material doped with a p-type dopant. For example, the metal may be made of one or two or more alloys selected from the group consisting of: Al, Cu, Fe, Pb, Zn, Au, Pt, W, In, Mo, Ni, and Ti. In addition, commonly used materials may be used as p-type dopants and host materials used in p-type doped organic materials.

[0171] 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.

[0172] The organic electroluminescent device according to one embodiment may further include at least one dopant in the light emitting layer.

[0173] The dopant included in the organic electroluminescent device of the present disclosure may be at least one phosphorescent dopant or a fluorescent dopant, preferably a fluorescent 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.

[0174] The dopant included in the organic electroluminescent device of the present disclosure may use a compound represented by the following Formula D, but is not limited thereto.

[0175]

[0176] In formula D,

[0177] R 101 To R 111 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, or -L'4-N-(Ar'4)(Ar'5), or may be linked to adjacent substituents to form one or more rings;

[0178] Y′1 represents B;

[0179] X′1 and X′2 each independently represent NR′;

[0180] R′ 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, or -L'4-N-(Ar'4)(Ar'5); or may be connected to R 101 , R 108 , R 109 and R 111forming one or more rings on at least one of the

[0181] L′4 represents a single bond, substituted or unsubstituted (C6-C 30 )arylene, or substituted or unsubstituted (3- to 30-membered)heteroarylene; and

[0182] Ar'4 and Ar'5 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.

[0183] Preferably, R 101 To R 111 Each independently may be hydrogen, deuterium, substituted or unsubstituted (C1-C 20 ) alkyl, substituted or unsubstituted (C6-C 25 )aryl, substituted or unsubstituted (5- to 20-membered) heteroaryl, or -L'4-N-(Ar'4)(Ar'5), or may be connected to adjacent substituents to form one or more rings.

[0184] More preferably, R 101 To R 111 Each independently may be hydrogen, deuterium, unsubstituted (C1-C 10 ) alkyl; unsubstituted or substituted by (C1-C 10 )alkyl, (13- to 18-membered)heteroaryl and di(C6-C 18 ) arylamino group substituted with at least one (C6-C 18 ) aryl; unsubstituted or substituted with at least one (C1-C 10 ) aryl-substituted (5- to 18-membered) heteroaryl; or -L'4-N-(Ar'4)(Ar'5), or may be connected to adjacent substituents to form one or more rings. For example, R 101 To R 111Each independently may be hydrogen, methyl, tert-butyl, substituted or unsubstituted phenyl, biphenyl, terphenyl, triphenylene, carbazolyl, phenoxazinyl, phenothiazinyl, dimethylacridinyl, dimethylxanthenyl, unsubstituted or diphenylamino substituted with at least one of methyl and diphenylamino, phenylnaphthylamino, dibiphenylamino, phenylamino substituted with phenylcarbazolyl or dibenzofuranyl, (17-21-membered) heteroaryl substituted with at least one of methyl and phenyl; or may be connected to an adjacent substituent to form a benzene ring, an indole ring substituted with at least one of phenyl and diphenylamino, a benzofuran ring, a benzothiophene ring, or a 19-membered heterocyclic ring substituted with at least one methyl. The substituent of the substituted phenyl may be at least one of methyl, carbazolyl, dibenzofuranyl, diphenylamino, phenoxazinyl, phenothiazinyl, and dimethylacridinyl.

[0185] According to one embodiment, specific examples of the dopant compound include the following, but are not limited thereto.

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193] In the above compounds, D2 to D5 each mean that 2 to 5 hydrogens are replaced by deuterium.

[0194] 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.

[0195] When a layer is formed by the first host compound and the second host compound according to one 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 mixed deposition is a method in which two or more materials are mixed in one crucible source before being deposited and then current is applied to one chamber to evaporate the materials.

[0196] 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, the two host compounds may be formed separately. For example, after depositing the first host compound, the second host compound may be deposited.

[0197] 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, by using the organic electroluminescent device of the present disclosure, a display device such as a smartphone, a tablet computer, a notebook computer, a PC, a TV, or a display device for a vehicle, or a lighting device such as outdoor or indoor lighting may be prepared.

[0198] Hereinafter, the preparation method of the subject compound according to the present disclosure will be explained with reference to the synthesis method of representative compounds or intermediate compounds in order to understand the present disclosure in detail.

[0199] [Example 1] Preparation of Compound H1-31

[0200]

[0201] 1) Synthesis of Compound 1-1

[0202] Compound A (23.5 g, 126 mmol), compound B (30 g, 105 mmol), tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) (6 g, 5.25 mmol), 131 mL of 2M K2CO3, 524 mL of toluene, and 131 mL of ethanol (EtOH) were added to a flask and dissolved, and then reacted at 80°C for 1 hour. 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 (31 g, yield: 85%).

[0203] 2) Synthesis of Compound 1-2

[0204] Compound 1-1 (30.5 g, 87.7 mmol) was dissolved in 88 mL of dichloromethane (DCM), the reactor temperature was lowered to 0 ° C, and 132 mL of 1 M boron tribromide (BBr3) was slowly added dropwise. After 30 minutes, the reactor was warmed to room temperature and stirred for 16 hours. The mixture was neutralized by adding potassium carbonate aqueous solution to the reactor, the organic layer was extracted with sodium thiosulfate aqueous solution, residual moisture was removed using magnesium sulfate, then dried, and then separated by column chromatography to obtain compound 1-2 (24.7 g, yield: 84%).

[0205] 3) Synthesis of Compound 1-3

[0206] Compound 1-2 (23.7 g, 71 mmol), CuI (13.5 g, 71 mmol), Cs2CO3 (69 g, 213 mmol), and 355 mL of o-xylene were added to a flask and dissolved, and then reacted at 160° 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 1-3 (12.11 g, yield: 67%).

[0207] 4) Synthesis of Compound H1-31

[0208] Compound 1-3 (6 g, 24 mmol), (10-phenylanthracene-9-yl) boronic acid (8.5 g, 28 mmol), Pd (OAc) 2 (377 mg, 7 mmol), ligand (tricyclohexylphosphine tetrafluoroborate) (1.5 g, 0.36 mmol), K 3 PO 4 (15 g, 72 mmol), toluene (480 mL), isopropanol (120 mL) and distilled water (120 mL) were added to a flask and dissolved, and then refluxed at 120 ° C for 3 hours. Next, the reaction mixture was cooled to room temperature, the organic layer was extracted with ethyl acetate, and magnesium sulfate was used to remove residual moisture, followed by drying. Thereafter, distillation was performed under reduced pressure, and then column chromatography was performed to obtain compound H1-31 (4.7 g, yield: 42%).

[0209] MW MP H1-31 470.17 271℃

[0210] [Example 2] Preparation of Compound H1-186

[0211]

[0212] Compound H1-31 was synthesized by selecting the deuteration method disclosed in Korean Patent Nos. 10-2283849 and 10-1427457, etc. to obtain compound H1-186 (8.0 g, yield: 72%, MS: [M+H] +=483.17).

[0213] MW MP H1-186 483.17 272℃

[0214] Hereinafter, a preparation method of an organic electroluminescent device including various host materials and / or organic electroluminescent compounds according to the present disclosure and device characteristics thereof will be explained in order to understand the present disclosure in detail.

[0215] [Device Examples 1 to 5] Preparation of OLEDs containing various host materials according to the present disclosure

[0216] Prepare an OLED according to the present disclosure. First, a transparent electrode indium tin oxide (ITO) film (10Ω / sq) (GEOMATEC CO., LTD., Japan) on a glass substrate for OLED is subjected to ultrasonic washing with acetone and isopropanol in sequence, and thereafter stored in isopropanol and then used. Thereafter, 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, and 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 5wt% based on the total amount of compound HI-1 and HT-1 to form a hole injection layer with a thickness of 10nm. Next, compound HT-1 is deposited on the hole injection layer as a first hole transport layer with a thickness of 80nm. Compound HT-2 is then introduced into another chamber of the vacuum vapor deposition device, and the compound is evaporated by applying an electric current to the chamber, thereby forming a second hole transport layer with a thickness of 15nm 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 device at a ratio of 1:1, and compound BD is introduced into another chamber as a dopant. The two materials are evaporated at different rates and 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 22.5nm on the second hole transport layer. Next, compound ET-1 is deposited on the light-emitting layer to form an electron buffer layer with a thickness of 5nm. Next, compound EI-1 and compound EI-2 are added to the other two chambers and evaporated at a ratio of 2:1 to form an electron transport layer with a thickness of 25nm on the electron buffer layer. Next, compound Yb:LiF is added to the other two chambers as an electron injection layer and evaporated at a ratio of 2:1 to form an electron injection layer with a thickness of 1nm on the electron transport layer. Next, an Al cathode having 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 added at 10 -6 Purify by vacuum sublimation under vacuum.

[0217] [Device Comparative Example 1] Preparation of OLED containing a single host material

[0218] An OLED was manufactured in the same manner as in Device Example 1, except that Compound H1-31 was used alone as a host material of the light-emitting layer.

[0219] The OLEDs of Device Examples 1 to 5 and Device Comparative Example 1 produced as described above were measured for driving voltage at a luminance of 1,000 nits and the shortest time taken for the luminance to decrease from 100% to 95% at a luminance according to the conversion efficiency standard (lifetime: T 95 ), and the results are shown in Table 1 below.

[0220] Table 1

[0221]

[0222] As shown in Table 1 above, it can be confirmed that the organic electroluminescent device including multiple host materials according to the present disclosure exhibits lower voltage and / or higher luminous efficiency and / or longer life characteristics than the organic electroluminescent device including only a single host material.

[0223] [Device Example 6] Preparation of OLED containing a single host material

[0224] An OLED was manufactured in the same manner as in Device Example 1, except that Compound H1-186 described in the following Table 2 was used alone as a host material for the light-emitting layer.

[0225] The driving voltage of the OLED of Device Example 6 produced as described above at a luminance of 1,000 nits and the shortest time taken for the luminance to decrease from 100% to 95% at a luminance according to the conversion efficiency standard (lifetime: T 95 ), and the results are shown in Table 2 below.

[0226] Table 2

[0227]

[0228] The compounds used in Device Examples 1 to 6 and Device Comparative Example 1 are specifically shown in Table 3 below.

[0229] Table 3

[0230]

[0231]

Claims

1. A plurality of host materials comprising at least one first host compound and at least one second host compound, wherein the first host compound is represented by the following formula 1, the second host compound is represented by the following formula 2, and the first host compound and the second host compound are different from each other: in, R1 to R8 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C2-C 30 )alkenyl, 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 (C3-C 30 )cycloalkenyl, 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, (C3-C 30 ) aliphatic ring and (C6-C 30 ) substituted or unsubstituted condensed ring of an aromatic ring, substituted or unsubstituted mono- or di-(C1-C 30 )alkylamino, substituted or unsubstituted mono- or di-(C2-C 30 )alkenylamino, substituted or unsubstituted mono- or di-(C6-C 30 )arylamino, substituted or unsubstituted mono- or di-(3- to 30-membered) heteroarylamino, substituted or unsubstituted (C1-C 30 )alkyl(C2-C 30 )alkenylamino, substituted or unsubstituted (C1-C 30 )alkyl(C6-C 30 ) arylamino, substituted or unsubstituted (C1-C 30 )alkyl(3-30 membered)heteroarylamino, substituted or unsubstituted(C2-C 30 )Alkenyl (C6-C 30 ) arylamino, substituted or unsubstituted (C2-C 30 )alkenyl (3- to 30-membered) heteroarylamino, substituted or unsubstituted (C6-C 30 )aryl(3-30-membered)heteroarylamino, and combinations thereof; L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6-C 30 )arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene; Ar1 represents a substituted or unsubstituted (C6-C 30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; and Ar2 is represented by the following formula 1-A: in, X represents -O- or -S-; R′1 to R′ 10 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C 30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; and R′1 to R′ 10 Any one of them is connected with L2: in, L 11 and L 12 Each independently represents a single bond, a substituted or unsubstituted (C6-C 30 )arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene; Ar 11 and Ar 12 Each independently represents a substituted or unsubstituted (C6-C 30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; and R 11 To R 18 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C2-C 30 )alkenyl, 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 (C3-C 30 )cycloalkenyl, 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, or (C3-C 30 ) aliphatic ring and (C6-C 30 ) A substituted or unsubstituted condensed aromatic ring.

2. The plurality of host materials according to claim 1, wherein: Formula 1 is represented by any one of the following formulas 1-1 to 1-3: in, R1 to R8, L1, L2, Ar1, X, and R′1 to R′ 10 As defined in claim 1.

3. The plurality of host materials according to claim 1, wherein: In formula 1, R1 to R8 each independently represent hydrogen or deuterium; and R′1 to R′ 10 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C 15 )aryl, or substituted or unsubstituted (3- to 15-membered) heteroaryl.

4. The plurality of host materials according to claim 1, wherein: In Formula 1, Ar1 represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, or a combination thereof.

5. The plurality of host materials according to claim 1, wherein: In formula 2, Ar 11 and Ar 12 Each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, or the following formula 2-A: in, T1 represents -O-, -S-, or -CR 27 R 28 ; R 19 To R 28 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C6-C 30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; and R 19 To R 26 Any one of them and L 11 or L 12 connect.

6. The plurality of host materials according to claim 1, wherein: The substituted alkyl, the substituted alkenyl, the substituted (ene) aryl, the substituted heteroaryl, the substituted cycloalkyl, the substituted cycloalkenyl, the substituted heterocycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, the substituted condensed ring of the aliphatic ring and the aromatic ring, the substituted mono- or dialkylamino, the substituted mono- The substituted mono- or diarylamino, the substituted mono- or diheteroarylamino, the substituted alkylalkenylamino, the substituted alkylarylamino, the substituted alkylheteroarylamino, the substituted alkenylarylamino, the substituted alkenylheteroarylamino, and the substituted arylheteroarylamino are each independently substituted by at least one selected from the group consisting of: deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; phosphine oxide; unsubstituted or deuterated (C1-C 30 )alkyl; halo(C1-C 30 ) alkyl; (C2-C 30 )alkenyl; (C2-C 30 ) alkynyl; (C1-C 30 ) alkoxy; (C1-C 30 )alkylthio; (C3-C 30 )cycloalkyl; (C3-C 30 )cycloalkenyl; (3- to 7-membered)heterocycloalkyl; (C6-C 30 ) aryloxy; (C6-C 30 ) arylthio; unsubstituted or deuterated and (C6-C 30 )aryl, at least one substituted (3- to 30-membered) heteroaryl; unsubstituted or substituted with deuterium, (C1-C 30 ) alkyl, (C6-C 30 (C6-C 30 )aryl; tri(C1-C 30 ) alkylsilyl; tri(C6-C 30 ) arylsilyl; di(C1-C 30 )alkyl(C6-C 30 ) arylsilyl; (C1-C 30 )alkyldi(C6-C 30 )Arylsilyl; Amino; Mono- or Di-(C1-C 30 ) alkylamino; mono- or di-(C2-C 30 )alkenylamino; mono- or di-(C6-C 30 )arylamino; mono- or di-(3- to 30-membered) heteroarylamino; (C1-C 30 )alkyl(C2-C 30 )alkenylamino; (C1-C 30 )alkyl(C6-C 30 ) arylamino; (C1-C 30 )alkyl(3-30-membered)heteroarylamino; (C2-C 30 )Alkenyl (C6-C 30 ) arylamino; (C2-C 30 )alkenyl(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; di(C6-C 30 ) aryl borocarbonyl; (C6-C 30 ) arylphosphinyl; di(C1-C 30 ) alkyl boron carbonyl; (C1-C 30 )alkyl(C6-C 30 ) aryl borocarbonyl; (C6-C 30 )Aryl (C1-C 30 ) alkyl; and (C1-C 30 )alkyl(C6-C 30 )aryl.

7. The plurality of host materials according to claim 1, wherein: The first host compound represented by Formula 1 is selected from the following compounds: Among them, "D n " means that n number of hydrogens are replaced by deuterium, wherein n represents an integer of 1 or more and the upper limit of n is determined by the number of hydrogens that can be replaced in each compound.

8. The plurality of host materials of claim 1, wherein: The second host compound represented by Formula 2 is selected from the following compounds: Among them, "D n " means that n number of hydrogens are replaced by deuterium, wherein n represents an integer of 1 or more and the upper limit of n is determined by the number of hydrogens that can be replaced in each compound. 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, which is represented by the following formula 11: in, R1 to R8 each independently represent hydrogen or deuterium; provided that at least one of R1 to R8 is deuterium, L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6-C 30 )arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene; Ar1 represents a substituted or unsubstituted (C6-C 30 )aryl or substituted or unsubstituted (3- to 30-membered) heteroaryl; and Ar2 is represented by the following formula 1-A; in, X represents -NR"-, -Se-, -O- or -S-; R′1 to R′ 10 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C 30 ) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; or may be connected to an adjacent substituent to form a substituted or unsubstituted (3- to 30-membered) monocyclic or polycyclic alicyclic ring, aromatic ring, or a combination thereof; provided that R′1 to R′ 10 At least one of is deuterium; and R′1 to R′ 10 Any one of them is connected to L2; This is based on the assumption that all hydrogen in the compound is replaced by deuterium.

11. The organic electroluminescent compound according to claim 10, wherein At least one of R1, R4, R5 and R8 is hydrogen.

12. The organic electroluminescent compound according to claim 10, wherein The residual ratio of hydrogen in the compound is 20% to 60% of the total amount of hydrogen.

13. The organic electroluminescent compound according to claim 10, wherein The residual ratio of hydrogen in the compound is 40% to 60% of the total amount of hydrogen.

14. The organic electroluminescent compound according to claim 10, wherein The compound represented by Formula 11 is selected from the following compounds: Among them, "D n " means that n number of hydrogens are replaced by deuterium, wherein n represents an integer of 1 or more and the upper limit of n is determined by the number of hydrogens that can be replaced in each compound.

15. An organic electroluminescent compound, which is represented by the following formula 12: in, R1 to R8 each independently represent hydrogen or deuterium; L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6-C 30 )arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene; Ar1 is represented by the following formula 1-B or 1-C; in, a represents an integer from 1 to 3, and b and c each independently represent an integer from 0 to 3; represents the attachment site to L1; and Ar2 is represented by the following formula 1-A; in, X represents -NR"-, -Se-, -O- or -S-; R′1 to R′ 10 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C 30 ) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; or may be connected to adjacent substituents to form a substituted or unsubstituted (3- to 30-membered) monocyclic or polycyclic alicyclic ring, aromatic ring, or a combination thereof; and R′1 to R′ 10 Any one of them is connected to L2.

16. The organic electroluminescent compound according to claim 15, wherein The organic electroluminescent compound represented by Formula 12 is selected from the following compounds: 17 . An organic electroluminescent device comprising the organic electroluminescent compound according to claim 10 .

18. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 15.

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