Organic electroluminescent compound, a plurality of host materials, and organic electroluminescent device comprising the same

Abstract

The present invention relates to a plurality of host materials comprising a first host material comprising a compound represented by Chemical Formula 1 and a second host material comprising a compound represented by Chemical Formula 2, and an organic electroluminescent device comprising the same. Additionally, the present invention relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. By including the organic electroluminescent compound according to the present invention and / or a specific combination of compounds as a host material, an organic electroluminescent device having high luminous efficiency and long lifespan characteristics can be manufactured.

Description

Technology Field

[0001] The present invention relates to an organic electroluminescent compound, a plurality of host materials, and an organic electroluminescent device comprising the same. Background Technology

[0002] Since Tang et al. at Eastman Kodak first developed a TPD / Alq3 bilayer small molecule green organic light-emitting diode (OLED) consisting of an emissive layer and a charge transport layer in 1987, research on organic light-emitting diodes has progressed rapidly, leading to their current commercialization. Currently, organic light-emitting diodes primarily utilize phosphorescent materials with excellent luminous efficiency for panel implementation. However, many applications, such as TVs and lighting, face the problem of insufficient OLED lifespan, and high efficiency is still required. Generally, the higher the brightness of an OLED, the shorter its lifespan. Therefore, OLEDs with high luminous efficiency and / or long lifespan are required for long-term display usage and high resolution.

[0003] Various materials or concepts have been proposed for the organic layer of organic electroluminescent devices to improve luminous efficiency, driving voltage, and / or lifespan, but they have not been satisfactory for practical use.

[0004] Korean Published Patent Application No. 10-2017-0022865 discloses an organic electroluminescent device using phenantrooxazole and phenantrothiazole compounds as hosts, but it does not specifically disclose an organic electroluminescent device using multiple types of host materials in a specific combination of the present invention, and there is still a need for the development of host materials to improve the performance of OLEDs.

[0005] Korean Published Patent Application No. 10-2020-0026079 discloses a compound containing a nitrogen-containing heteroaryl as one of a plurality of host materials, but does not disclose a compound substituted with a silyl group. Prior art literature

[0006] Korean Published Patent Application No. 10-2017-0022865 (March 2, 2017) Korean Published Patent Application No. 10-2020-0026079 (March 10, 2020) The problem to be solved

[0007] The object of the present invention is, first, to provide a plurality of host materials capable of manufacturing an organic electroluminescent device having high luminous efficiency and long lifespan characteristics, and second, to provide an organic electroluminescent compound of a new structure suitable for use as an organic electroluminescent material. In addition, another object of the present invention is to provide an organic electroluminescent device having high luminous efficiency and / or improved lifespan characteristics by including a compound according to the present invention as a single host material, or a specific combination of compounds according to the present invention as a plurality of host materials. means of solving the problem

[0008] As a result of diligent research to solve the above technical problem, the inventors have completed the present invention by discovering that a plurality of host materials, comprising a first host material comprising a compound represented by the following chemical formula 1 and a second host material comprising a compound represented by the following chemical formula 2, or an organic electroluminescent compound represented by the following chemical formula 3, achieve the above-described objective.

[0009] [Chemical Formula 1]

[0010]

[0011] In the above chemical formula 1,

[0012] X1 and Y1 are each independently -N=, -NR5-, -O-, or -S-, provided that one of X1 and Y1 is -N=, and the other of X1 and Y1 is -NR5-, -O-, or -S-;

[0013] R1 is a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3-30)heteroaryl;

[0014] R2 to R5 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, a fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, -NR 11 R 12, -SiR 13 R 14 R 15 or a combination thereof; adjacent substituents can be connected to each other to form a ring;

[0015] R 11 to R 15 Each is independently a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30)heteroaryl;

[0016] a and b are each independently integers of 1 or 2, and c is an integer from 1 to 4;

[0017] If a to c are integers of 2 or more, each R2 to each R4 may be the same or different from each other;

[0018] [Chemical Formula 2]

[0019]

[0020] In the above chemical formula 2,

[0021] Y is -O- or -S- and;

[0022] L2 is a single-bonded, substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30)heteroarylene;

[0023] HAr is a substituted or unsubstituted (3-30) heteroaryl containing one or more nitrogen atoms;

[0024] R8 and R9 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, -NR 16 R 17 , -SiR 18 R 19 R 20 , or a combination thereof; can be connected to adjacent substituents to form a ring;

[0025] R 16 to R 20 Each is independently a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30)heteroaryl;

[0026] e is an integer from 1 to 4, and f is an integer from 1 to 3;

[0027] If e and f are each integers greater than or equal to 2, then each R8 and each R9 may be the same or different from each other;

[0028] However, at least one of HAr, R8, and R9 comprises -L3-SiR'R''R''' or -L3-CR'R''R''';

[0029] L3 is a single bond, substituted or unsubstituted (C1-C30)alkylene, substituted or unsubstituted (C3-C30)cycloalkylene, substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (3-30)heteroarylene;

[0030] R', R'', and R''' are each independently a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3-30)heteroaryl.

[0031] [Chemical Formula 3]

[0032]

[0033] In the above chemical formula 3,

[0034] Y is O or S and;

[0035] A is Si or C;

[0036] L2 is phenylene, biphenylene, or naphthylene with a single bond, substituted or unsubstituted with deuterium;

[0037] R8 and R9 are each independently hydrogen or deuterium;

[0038] Ar3 is deuterium-substituted or unsubstituted phenyl, deuterium-substituted or unsubstituted biphenyl, deuterium-substituted or unsubstituted terphenyl, deuterium-substituted or unsubstituted naphthyl, deuterium-substituted or unsubstituted triphenylenyl, deuterium-substituted or unsubstituted phenanthrenyl, or a combination thereof;

[0039] L3 is deuterium-substituted or unsubstituted phenylene, deuterium-substituted or unsubstituted biphenylene, or deuterium-substituted or unsubstituted naphthylene;

[0040] R', R'', and R''' are each independently a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3-30)heteroaryl;

[0041] e is an integer from 1 to 4, and f is an integer from 1 to 3;

[0042] If e and f are each integers greater than or equal to 2, then each R8 and each R9 may be the same or different from each other. Effects of the invention

[0043] By using the organic electroluminescent compound according to the present invention and / or a specific combination of compounds as a host material, an organic electroluminescent device having high luminous efficiency and long lifespan characteristics can be manufactured. Specific details for implementing the invention

[0044] The present invention is described in more detail below, but this is for illustrative purposes only and should not be interpreted as limiting the scope of the present invention.

[0045] The present invention relates to a plurality of host materials comprising a first host material comprising one or more compounds represented by Chemical Formula 1 and a second host material comprising one or more compounds represented by Chemical Formula 2, and an organic electroluminescent device comprising said host materials.

[0046] The present invention relates to an organic electroluminescent compound represented by Chemical Formula 3, an organic electroluminescent material comprising the same, and an organic electroluminescent device comprising the organic electroluminescent material.

[0047] In this document, "organic electroluminescent compound" refers to a compound that can be used in an organic electroluminescent device and, if necessary, may be included in any material layer constituting the organic electroluminescent device.

[0048] In the present invention, "organic electroluminescent material" refers to a material that can be used in an organic electroluminescent device, may include one or more compounds, and may be included in any layer constituting the organic electroluminescent device as needed. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole assist material, a light-emitting assist material, an electron blocking material, a light-emitting material (including a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0049] In the present invention, "multiple types of organic electroluminescent materials" refers to an organic electroluminescent material composed of two or more compounds that may be included in any layer constituting an organic electroluminescent device, and may refer to both the material before (e.g., before deposition) and after (e.g., after deposition) inclusion in the organic electroluminescent device. For example, the multiple types of organic electroluminescent materials may be a combination of two or more compounds that may be included in one or more layers among a hole injection layer, a hole transport layer, a hole assist layer, a light-emitting assist layer, an electron blocking layer, a light-emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. These two or more compounds may be included in the same layer or different layers, may be mixed-deposited or co-deposited, or may be deposited individually.

[0050] In this invention, "multiple types of host materials" refers to an organic electroluminescent material composed of two or more types of host materials, and may refer to both the materials before (e.g., before deposition) and after (e.g., after deposition) inclusion in an organic electroluminescent device. The multiple types of host materials of this invention may be included in any light-emitting layer constituting an organic electroluminescent device, and the two or more compounds included in the multiple types of host materials may be included together in one light-emitting layer or each may be included in different light-emitting layers. When two or more types of host materials are included in one layer, for example, they may be mixed-deposited to form a layer, or they may be separately and simultaneously co-deposited to form a layer.

[0051] In the present invention, "(C1-C30)alkyl" refers to a straight-chain or branched-chain alkyl having 1 to 30 carbon atoms constituting the chain, wherein 1 to 20 carbon atoms are preferred, and 1 to 10 carbon atoms are more preferred. Specific examples of the above alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert -butyl, secExamples include butyl, etc. In this document, "(C3-C30)cycloalkyl" refers to a single-ring or polycyclic hydrocarbon having 3 to 30 carbon atoms in its ring skeleton, wherein the number of carbon atoms is preferably 3 to 20 and more preferably 3 to 7. Examples of the above-mentioned cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, etc. In this document, "(C6-C30)aryl(len)" refers to a single-ring or fused-ring radical derived from an aromatic hydrocarbon having 6 to 30 carbon atoms in its ring skeleton, which may be partially saturated, wherein the number of carbon atoms in its ring skeleton is preferably 6 to 20 and more preferably 6 to 15. The above-mentioned aryl includes those having a spiro structure. Examples of the above aryls include phenyl, biphenyl, terphenyl, quaternphenyl, naphthyl, non-naphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzoflurenyl, diphenylbenzoflurenyl, dibenzoflurenyl, phenanthrenyl, benzophenanthrenyl, phenylphenanthrenyl, anthracenyl, benzanthrenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, crisenyl, benzocrisenyl, naphthacenyl, fluoranthenyl, benzoflurenthenyl, tolyl, xylyl, mesityl, coumenyl, spiro[fluorene-fluorene]yl, spiro[fluorene-benzofluren]yl, azulenyl, Examples include tetramethyl-dihydrophenanthrenyl, etc. More specifically, examples of the above aryls include o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesithyl, o-coumenyl, m-coumenyl, p-coumenyl, pt-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-t-butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaternphenyl, 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-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-crisenyl, 2-crisenyl, 3-crisenyl, 4-crisenyl, 5-Crysenyl, 6-Crysenyl, benzo[c]phenanthryl, benzo[g]crisenyl, 1-triphenyllenyl, 2-triphenyllenyl, 3-triphenyllenyl, 4-triphenyllenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluranthenyl, 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-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-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, 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-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-2-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-3-phenanthrenyl, 9,9,10,10-tetramethyl-9,Examples include 10-dihydro-4-phenanthrenyl. In this document, "(3-30-membered)heteroaryl(len)" refers to an aryl group having 3 to 30 ring skeleton atoms and containing one or more heteroatoms selected from the group consisting of B, N, O, S, Si, P, Se, and Ge. Here, it is preferable that the number of ring skeleton atoms be 3 to 30, and more preferable that it be 5 to 20. The number of heteroatoms is preferably 1 to 4, and may be a single ring system or a fused ring system condensed with one or more benzene rings, and may be partially saturated. Additionally, in this document, the heteroaryl or heteroarylene includes a form in which one or more heteroaryl or aryl groups are connected to the heteroaryl group by a single bond, and also includes those having a spiro structure. Examples of the above heteroaryls include single-ring heteroaryls such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, benzofuroquinolinyl, benzofuroquinazolinyl, benzofuronaphthiridinyl, benzofuropyrimidinyl, naphthopyrimidinyl, benzothienoquinolinyl, benzothienoquinazolinyl, Benzothienonaphthiridinyl, Benzothienopyrimidinyl, Naphthothienopyrimidinyl, Pyrimidoindolyl, Benzopyrimidoindolyl, Benzopyrimidolyl, Benzopyramidyl, Naphthopyramidyl, Benzothienopyramidyl, Naphthothienopyramidyl, Pyrazinoindolyl, Benzopyramidolyl, Benzomidazolyl, Benzothiazolyl, Benzisothiazolyl, Benzisoxazolyl, Benzoxazolyl, Imidazopyrimidinyl, Isoindolyl, Indolyl, Benzodolyl, Indazolyl, Benzothiadiazolyl, Quinolyl, Isoquinolyl, Sinolinyl, Quinazolinyl, Quinoxalinyl, Carbazolyl, Azacarbazolyl, Benzocabazolyl, Dibenzocabazolyl, Phenoxazinyl, Phenanthridinyl, benzodioxolyl, indolizidinyl, acridinyl, silafluorenyl,There are fused cyclic heteroaryls such as germaneflorrenyl, benzotriazolyl, fenazinyl, imidazopyridinyl, chromenoquinazolinyl, thiochromenoquinazolinyl, dimethylbenzopyrimidinyl, indolocarbazolyl, and indenocarbazolyl. More specifically, the heteroaryl is 1-pyrrolill, 2-pyrrolill, 3-pyrrolill, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 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, 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-Benzofuranil, 3-Benzofuranil, 4-Benzofuranil, 5-Benzofuranil, 6-Benzofuranil, 7-Benzofuranil, 1-Isobenzofuranil, 3-Isobenzofuranil, 4-Isobenzofuranil, 5-Isobenzofuranil, 6-Isobenzofuranil, 7-Isobenzofuranil, 2-Quinolyl, 3-Quinolyl, 4-Quinolyl, 5-Quinolyl, 6-Quinolyl, 7-Quinolyl, 8-Quinolyl, 1-Isoquinolil, 3-Isoquinolil, 4-Isoquinolil, 5-Isoquinolil, 6-Isoquinolil, 7-Isoquinolil, 8-Isoquinolil, 2-Quinoxalinil, 5-Quinoxalinil, 6-Quinoxalinil, 1-Carbazolyl, 2-Carbazolyl, 3-Carbazolyl, 4-Carbazolyl, 9-Carbazolyl, Azacarbazolyl-1-yl, Azacarbazolyl-2-yl, Azacarbazolyl-3-yl, Azacarbazolyl-4-yl, Azacarbazolyl-5-yl, Azacarbazolyl-6-yl, Azacarbazolyl-7-yl, Azacarbazolyl-8-yl, Azacarbazolyl-9-yl, 1-phenantridinyl, 2-phenantridinyl, 3-phenantridinyl, 4-phenantridinyl,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-Methylpyrrole-1-yl, 2-Methylpyrrole-3-yl, 2-Methylpyrrole-4-yl, 2-Methylpyrrole-5-yl, 3-Methylpyrrole-1-yl, 3-Methylpyrrole-2-yl, 3-Methylpyrrole-4-yl, 3-Methylpyrrole-5-yl, 2-t-butylpyrrole-4-yl, 3-(2-phenylpropyl)pyrrole-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-t-butyl-1-indolyl, 4-t-butyl-1-indolyl, 2-t-butyl-3-indolyl, 4-t-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 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, 8-naphtho-[2,1-b]-benzofuranyl, 9-naphtho-[2,1-b]-benzofuranyl, 10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b]-benzothiophenyl, 2-naphtho-[1,2-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-Benzofuro[3,2-d]Pyrimidinyl, 6-Benzofuro[3,2-d]Pyrimidinyl, 7-Benzofuro[3,2-d]Pyrimidinyl, 8-Benzofuro[3,2-d]pyrimidinyl, 9-Benzofuro[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-Benzofuro[3,2-d]pyrazinyl, 6-Benzofuro[3,2-d]pyrazinyl, 7-Benzofuro[3,2-d]pyrazinyl, 8-Benzofuro[3,2-d]pyrazinyl, 9-Benzofuro[3,2-d]pyrazinyl, 2-Benzothio[3,2-d]pyrizinil, 6-Benzothio[3,Examples include 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-germafluorenyl, 2-germafluorenyl, 3-germafluorenyl, 4-germafluorenyl, 1-dibenzoselenphenyl, 2-dibenzoselenphenyl, 3-dibenzoselenphenyl, 4-dibenzoselenphenyl, etc. In this invention, "a fused ring of (C3-C30) aliphatic rings and (C6-C30) aromatic rings" refers to a functional group of a ring in which one or more aliphatic rings having 3 to 30 carbon atoms in the ring skeleton, preferably 3 to 25, more preferably 3 to 18, and one or more aromatic rings having 6 to 30 carbon atoms in the ring skeleton, preferably 6 to 25, more preferably 6 to 18, are fused. Examples include a fused ring of one or more benzenes and one or more cyclohexanes, or a fused ring of one or more naphthalenes and one or more cyclopentanes. In this invention, the carbon atoms of the fused ring of (C3-C30) aliphatic rings and (C6-C30) aromatic rings may be replaced with one or more heteroatoms selected from B, N, O, S, Si, and P, preferably one or more heteroatoms selected from N, O, and S. In this document, "halogen" includes F, Cl, Br, and I atoms.

[0052] In addition, "ortho (o-)", "meta (m-)", and "para (p-)" are prefixes indicating the relative positions of substituents, respectively. Ortho indicates that two substituents are adjacent to each other; for example, in benzene-substituents, when the substituents are at the 1st and 2nd positions, it is called the ortho position. Meta indicates that two substituents are at the 1st and 3rd positions; for example, in benzene-substituents, when the substituents are at the 1st and 3rd positions, it is called the meta position. Para indicates that two substituents are at the 1st and 4th positions; for example, in benzene-substituents, when the substituents are at the 1st and 4th positions, it is called the para position.

[0053] In the present invention, "a ring formed by connecting adjacent substituents" refers to a substituted or unsubstituted (3-30) single-ring or polycyclic ring of alicyclic, aromatic, or a combination thereof formed by connecting or fusing two or more adjacent substituents, and preferably may be a substituted or unsubstituted (5-25) single-ring or polycyclic ring of alicyclic, aromatic, or a combination thereof. Additionally, the formed ring may include one or more heteroatoms selected from B, N, O, S, Si, and P, preferably one or more heteroatoms selected from N, O, and S. According to one example of the present invention, the number of ring skeleton atoms is (5-20), and according to another example of the present invention, the number of ring skeleton atoms is (5-15). For example, the fused ring may be in the form of, for instance, 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 benzofuren 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.

[0054] In addition, in the description of "substituted or non-substituted" in the present invention, "substituted" means that a hydrogen atom in a functional group is replaced by another atom or another functional group (i.e., a substituent), and includes substitution by a group in which two or more substituents are connected. For example, "a substituent in which two or more substituents are connected" may be pyridine-triazine. That is, pyridine-triazine may be a heteroaryl, or it may be interpreted as a substituent in which two heteroaryls are connected.In the formulas of the present invention, the substituents of the substituted alkyl, substituted cycloalkyl, substituted cycloalkenyl, substituted heterocycloalkyl, substituted aryl(len), substituted heteroaryl(len), and substituted nitrogen-containing heteroaryl are each independently deuterium; halogen; cyano; carboxyl; nitro; hydroxy; (C1-C30)alkyl; halo(C1-C30)alkyl; (C2-C30)alkenyl; (C2-C30)alkynyl; (C1-C30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl; (3-7-membered)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (C6-C30)aryl substituted or unsubstituted (3-30)heteroaryl; (C6-C30)aryl substituted or unsubstituted with one or more of (C1-C30)alkyl and (3-30)heteroaryl; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; amino; mono- or di-(C1-C30)alkylamino; mono- or di-(C6-C30)arylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; It is preferable that one or more are selected from the group consisting of di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)ar(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl, and for example, the substituents of the above substituents may be deuterium, cyano, methyl, phenyl, biphenyl, naphthyl, carbazolyl, dibenzofuranyl, etc.

[0055] Hereinafter, multiple types of host materials according to one embodiment are described.

[0056] A plurality of host materials according to one embodiment may include a first host material comprising a compound represented by Chemical Formula 1 and a second host material comprising a compound represented by Chemical Formula 2, and may be included in the light-emitting layer of an organic electroluminescent device according to one example.

[0057] A first host material, which is a host material according to one embodiment, comprises a compound represented by the following chemical formula 1.

[0058] [Chemical Formula 1]

[0059]

[0060] In the above chemical formula 1,

[0061] X1 and Y1 are each independently -N=, -NR5-, -O-, or -S-, provided that one of X1 and Y1 is -N=, and the other of X1 and Y1 is -NR5-, -O-, or -S-;

[0062] R1 is a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3-30)heteroaryl;

[0063] R2 to R5 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, a fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, -NR 11 R 12, -SiR 13 R 14 R 15 or a combination thereof; adjacent substituents can be connected to each other to form a ring;

[0064] R 11 to R 15Each is independently a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30)heteroaryl;

[0065] a and b are each independently integers of 1 or 2, and c is an integer from 1 to 4;

[0066] If a to c are integers of 2 or more, each R2 to each R4 may be the same or different from each other.

[0067] For example, X1 and Y1 are each independently -N=, -NR5-, -O-, or -S-, provided that either X1 or Y1 is -N= and the other is -NR5-, -O-, or -S-. For example, X1 can be -N= and Y1 can be -O-, or Y1 can be -N= and X1 can be -O- or -S-.

[0068] For example, R1 may be a substituted or unsubstituted (C6-C30)aryl, preferably a substituted or unsubstituted (C6-C25)aryl, and more preferably a substituted or unsubstituted (C6-C18)aryl. For example, R1 may be a substituted or unsubstituted phenyl or a substituted or unsubstituted biphenyl.

[0069] For example, at least one of R2 to R4 is a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5-30)heteroaryl, a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or -NR 11 R 12 It may be, preferably, at least one of R2 to R4 is a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted (5-25) heteroaryl, a fused ring of a substituted or unsubstituted (C5-C25) aliphatic ring and a (C6-C25) aromatic ring, or -NR 11 R 12 -It may be, more preferably, a (C6-C18)aryl in which at least one of R2 to R4 is substituted or unsubstituted, a (5-18) heteroaryl in which the (C5-C10) aliphatic ring and the (C6-C18) aromatic ring are fused in which the (C5-C10) aliphatic ring and the (C6-C18) aromatic ring are substituted or unsubstituted, or -NR 11 R 12 It could be.

[0070] For example, R2, R3, and R5 can all be hydrogen.

[0071] For example, R4 is hydrogen, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5-30)heteroaryl, a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or -NR 11 R 12 It may be, preferably, hydrogen, a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted (5-25) heteroaryl, a fused ring of a substituted or unsubstituted (C5-C25) aliphatic ring and a (C6-C25) aromatic ring, or -NR 11 R 12 It may be, more preferably, hydrogen, a substituted or unsubstituted (C6-C18)aryl, a substituted or unsubstituted (5-18) heteroaryl, a fused ring of a substituted or unsubstituted (C5-C10) aliphatic ring and a (C6-C18) aromatic ring, or -NR 11 R 12 It could be.

[0072] For example, R 11 to R 15 Each may independently be a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (5-30)heteroaryl, preferably a substituted or unsubstituted (C6-C25)aryl or a substituted or unsubstituted (5-25)heteroaryl, and more preferably a substituted or unsubstituted (C6-C18)aryl or a substituted or unsubstituted (5-18)heteroaryl. For example, R11 to R 15 Each of the may be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted o-terphenyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, or a substituted or unsubstituted benzonaphtofuranyl, and for example, the substituent of the said substituent may be methyl or phenyl.

[0073] A compound represented by Chemical Formula 1 according to one example may be represented by the following Chemical Formula 1-1 or 1-2.

[0074] [Chemical Formula 1-1] [Chemical Formula 1-2]

[0075]

[0076] In the above chemical formulas 1-1 and 1-2,

[0077] L1 is a single bond or a substituted or unsubstituted (C6-C30)arylene;

[0078] Ar1 is a deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and an (C6-C30) aromatic ring, -NR 11 R 12 , -SiR 13 R 14 R 15 , or a combination thereof;

[0079] c is an integer from 1 to 3;

[0080] X1, Y1, R1 to R4, R11 to R 15 , a, and b are identical to their definitions in Chemical Formula 1.

[0081] For example, L1 may be a single-bonded, substituted, or unsubstituted (C6-C30)arylene, preferably a single-bonded, substituted, or unsubstituted (C6-C25)arylene, and more preferably a single-bonded, substituted, or unsubstituted (C6-C18)arylene. For example, L1 may be a single-bonded, substituted, or unsubstituted phenylene, a substituted or unsubstituted p-phenylene, or a substituted or unsubstituted m-biphenylene.

[0082] For example, Ar1 is a substituted or unsubstituted (C6-C30)aryl, a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or -NR 11 R 12 It may be, preferably, a substituted or unsubstituted (C6-C25)aryl, a fused ring of a substituted or unsubstituted (C5-C30) aliphatic ring and a (C6-C25) aromatic ring, or -NR 11 R 12It may be a substituted or unsubstituted (C6-C25)aryl, more preferably a fused ring of a substituted or unsubstituted (C5-C10) aliphatic ring and an (C6-C18) aromatic ring, a substituted or unsubstituted di(C6-C30)arylamino, a substituted or unsubstituted di(5-30)heteroarylamino, or a substituted or unsubstituted (C6-C30)aryl(5-30)heteroarylamino. For example, Ar1 is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthylphenyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted benzophenanthrenyl, substituted or unsubstituted crisenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted spiro[cyclopentane-fluorene]yl, substituted or unsubstituted spiro[fluorene-benzofluorene]yl, or substituted or unsubstituted spiro[indane-fluorene]yl; It may be an amino group substituted with at least one of phenyl, naphthyl, biphenyl, terphenyl, substituted or unsubstituted fluorenyl, phenanthrenyl, phenyl-substituted or unsubstituted dibenzofuranyl, dibenzothiophenyl, phenyl-substituted or unsubstituted carbazolyl, and benzonaphtofuranyl.Specifically, Ar1 is, for example, 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 phenanthrenyl, substituted or unsubstituted benzophenanthrenyl, substituted or unsubstituted crisenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzoflurenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted spiro[cyclopentane-fluorene]yl, substituted or unsubstituted spiro[indane-fluorene]yl; Substituted or unsubstituted diphenylamino, substituted or unsubstituted phenylbiphenylamino, substituted or unsubstituted phenylnaphthylamino, substituted or unsubstituted phenylterphenylamino, substituted or unsubstituted phenylfluorenylamino, substituted or unsubstituted phenylphenanthrenylamino, substituted or unsubstituted naphthylbiphenylamino, substituted or unsubstituted naphthylterphenylamino, substituted or unsubstituted naphthylphenanthrenylamino, substituted or unsubstituted dinaphthylamino, substituted or unsubstituted dibiphenylamino, substituted or unsubstituted biphenylfluorenylamino, substituted or unsubstituted difluorenylamino, substituted or unsubstituted phenylcarbazolylamino, substituted or unsubstituted biphenyldibenzofuranylamino, substituted or unsubstituted biphenyldibenzothiophenylamino, substituted or unsubstituted dibenzofuranyldibenzothiophenylamino, substituted or unsubstituted dibenzofuranylterphenylamino, substituted or unsubstituted dibenzofuranylnaphthylamino, The substituted or unsubstituted dibenzofuranyl-dibenzofuranylamino, substituted or unsubstituted dibenzothiophenyl-dibenzothiophenylamino, substituted or unsubstituted dibenzofuranylphenanthrenylamino, substituted or unsubstituted dibenzofuranylbenzonaphthofuranylamino, etc., may be, for example, the substituents of the above substituents may be methyl, phenyl, or naphthyl.

[0083] According to one example, the first host material comprising a compound represented by the above chemical formula 1 may be more specifically exemplified as the following compounds, but is not limited thereto.

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107] The compound represented by Chemical Formula 1 of the present invention can be prepared by synthesis methods known to those skilled in the art, for example, by referring to Korean Published Patent Application No. 2017-0022865 (published March 2, 2017), but is not limited thereto.

[0108] A second host material, which is another host material according to one embodiment, comprises a compound represented by the following chemical formula 2.

[0109] [Chemical Formula 2]

[0110]

[0111] In the above chemical formula 2,

[0112] Y is -O- or -S- and;

[0113] L2 is a single-bonded, substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30)heteroarylene;

[0114] HAr is a substituted or unsubstituted (3-30) heteroaryl containing one or more nitrogen atoms;

[0115] R8 and R9 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, -NR 16 R 17 , -SiR 18 R 19 R 20 , or a combination thereof; can be connected to adjacent substituents to form a ring;

[0116] R 16 to R 20Each is independently a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30)heteroaryl;

[0117] e is an integer from 1 to 4, and f is an integer from 1 to 3;

[0118] If e and f are each integers greater than or equal to 2, then each R8 and each R9 may be the same or different from each other;

[0119] However, at least one of HAr, R8, and R9 comprises -L3-SiR'R''R''' or -L3-CR'R''R''';

[0120] L3 is a single bond, substituted or unsubstituted (C1-C30)alkylene, substituted or unsubstituted (C3-C30)cycloalkylene, substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (3-30)heteroarylene;

[0121] R', R'', and R''' are each independently a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3-30)heteroaryl.

[0122] For example, L2 may be a single bond or substituted or unsubstituted (C6-C30)arylene, preferably a single bond or substituted or unsubstituted (C6-C25)arylene, and more preferably a single bond or substituted or unsubstituted (C6-C18)arylene. For example, L2 may be a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted p-biphenylene, substituted or unsubstituted m-biphenylene, substituted or unsubstituted o-biphenylene, or substituted or unsubstituted naphthylene.

[0123] For example, at least one of HAr, R8, and R9 comprises -L3-SiR'R''R''' or -L3-CR'R''R''', and for example, R8 and R9 are hydrogen or deuterium, and HAr may comprise -L3-SiR'R''R''' or -L3-CR'R''R'''.

[0124] For example, HAr may be a substituted or unsubstituted (5-30) heteroaryl containing one or more nitrogen atoms, preferably a substituted or unsubstituted (5-30) heteroaryl containing at least two nitrogen atoms, and more preferably a (5-30) heteroaryl containing at least three nitrogen atoms substituted with -L3-SiR'R''R'''. For example, HAr may be substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted benzoquinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted benzisoquinolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted naphthiridinyl, substituted or unsubstituted benzopropyrimidinyl, substituted or unsubstituted benzothienopyrimidinyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted pyridopyrazinyl, for example, the substituents of the above substituents are -L3-SiR'R''R'' or -L3-CR'R''R''' could be

[0125] For example, L3 may be a substituted or unsubstituted (C6-C30)arylene, preferably a substituted or unsubstituted (C6-C25)arylene, and more preferably a substituted or unsubstituted (C6-C18)arylene. For example, L3 may be a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthalenylene, a substituted or unsubstituted p-biphenylene, or a substituted or unsubstituted m-biphenylene.

[0126] For example, R', R'', and R''' may each independently be a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (5-30)heteroaryl, preferably a substituted or unsubstituted (C6-C25)aryl or a substituted or unsubstituted (5-25)heteroaryl, and more preferably a substituted or unsubstituted (C6-C18)aryl or a substituted or unsubstituted (5-18)heteroaryl. For example, R', R'', and R''' may each independently be substituted or unsubstituted phenyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl, and for example, the substituents of the said substituents may be cyano, methyl, or phenyl.

[0127] A compound represented by Chemical Formula 2 according to one example can be represented by the following Chemical Formula 2-1.

[0128] [Chemical Formula 2-1]

[0129]

[0130] In the above chemical formula 2-1,

[0131] Z1 to Z3 are each independently N or CH; provided that at least one of Z1 to Z3 is N;

[0132] A is Si or C;

[0133] Ar3 is a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3-30)heteroaryl;

[0134] Y, R8, R9, L2, L3, R', R'', R''', e, and f are the same as defined in Chemical Formula 2.

[0135] For example, at least two of Z1 to Z3 may be N, and preferably, Z1 to Z3 may all be N.

[0136] For example, Ar3 may be a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (5-30) heteroaryl, preferably a substituted or unsubstituted (C6-C25)aryl or a substituted or unsubstituted (5-25) heteroaryl, and more preferably a substituted or unsubstituted (C6-C18)aryl or a substituted or unsubstituted (5-18) heteroaryl. For example, Ar3 may 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, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted chrysenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted phenanthrooxazolyl, or substituted or unsubstituted naphthoisoxazolyl, and the substituents of the said substituents may be, for example, deuterium, cyano, methyl, phenyl, naphthyl, or It could be dibenzofuranil.

[0137] According to one example, a second host material comprising a compound represented by the above chemical formula 2 may be more specifically exemplified as the following compounds, but is not limited thereto.

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156] A compound represented by Chemical Formula 2 according to one example can be prepared by referring to a synthesis method known to those skilled in the art.

[0157] According to another embodiment of the present invention, the present invention provides an organic electroluminescent compound represented by the following chemical formula 3.

[0158] [Chemical Formula 3]

[0159]

[0160] In the above chemical formula 3,

[0161] Y is O or S and;

[0162] A is Si or C;

[0163] L2 is single-bonded, deuterium-substituted or unsubstituted phenylene, deuterium-substituted or unsubstituted biphenylene, or deuterium-substituted or unsubstituted naphthylene;

[0164] R8 and R9 are each independently hydrogen or deuterium;

[0165] Ar3 is deuterium-substituted or unsubstituted phenyl, deuterium-substituted or unsubstituted biphenyl, deuterium-substituted or unsubstituted terphenyl, deuterium-substituted or unsubstituted naphthyl, deuterium-substituted or unsubstituted triphenylenyl, deuterium-substituted or unsubstituted phenanthrenyl, or a combination thereof;

[0166] L3 is deuterium-substituted or unsubstituted phenylene, deuterium-substituted or unsubstituted biphenylene, or deuterium-substituted or unsubstituted naphthylene;

[0167] R', R'', and R''' are each independently a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3-30)heteroaryl;

[0168] e is an integer from 1 to 4, and f is an integer from 1 to 3;

[0169] If e and f are each integers greater than or equal to 2, then each R8 and each R9 may be the same or different from each other.

[0170] According to one example, the organic electroluminescent compound represented by the above chemical formula 3 may be more specifically exemplified as the following compounds, but is not limited thereto.

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186] Hereinafter, an organic electroluminescent device to which the aforementioned multiple types of host materials and / or organic electroluminescent compounds are applied will be described.

[0187] An organic electroluminescent device according to one embodiment has a first electrode; a second electrode; and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layer includes a emitting layer, and the emitting layer may include a plurality of host materials including one or more first host materials represented by Chemical Formula 1 and one or more second host materials represented by Chemical Formula 2. According to another embodiment of the present invention, the emitting layer may include an organic electroluminescent compound represented by Chemical Formula 3 alone.

[0188] According to one example, the organic electroluminescent material of the present invention comprises at least one compound among compounds H1-1 to H1-115, which are a first host material, and at least one compound among compounds C-1 to C-90, which are a second host material, and these multiple types of host materials may be included in the same organic layer, for example, a emitting layer, or each may be included in different emitting layers.

[0189] According to another example, the organic electroluminescent material of the present invention comprises an organic electroluminescent compound represented by Chemical Formula 3 alone or in combination of two or more, and such organic electroluminescent material may be included in an organic layer of an organic electroluminescent device, for example, a light-emitting layer or an electronic buffer layer.

[0190] In addition to the light-emitting layer and the electron buffer layer, the above organic layer may further include one or more layers selected from a hole injection layer, a hole transport layer, a hole assist layer, a light-emitting assist layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer. The above organic layer may further include an amine-based compound and / or an azine-based compound in addition to the light-emitting material of the present invention. Specifically, the hole injection layer, hole transport layer, hole assist layer, light-emitting layer, light-emitting assist layer, or electron blocking layer may include an amine-based compound, for example, an arylamine-based compound, a styrylamine-based compound, etc., as a hole injection material, a hole transport material, a hole assist material, a light-emitting material, a light-emitting assist material, and an electron blocking material. Furthermore, the above electron transport layer, electron injection layer, electron buffer layer, and hole blocking layer may include an azine-based compound as an electron transport material, an electron injection material, an electron buffer material, and a hole blocking material. In addition, the organic layer may further include one or more metals selected from the group consisting of organometals of Group 1, Group 2, Period 4 transition metals, Period 5 transition metals, lanthanide metals, and d-transition elements, or one or more complex compounds containing such metals.

[0191] An organic electroluminescent compound and a plurality of host materials according to one example can be used as light-emitting materials for a white organic light-emitting device. Various structures of the white organic light-emitting device are proposed, such as a side-by-side arrangement, a stacking arrangement, or a color conversion material (CCM) arrangement, depending on the arrangement of R (red), G (green), YG (yellow-green), and B (blue) light-emitting parts. In addition, the organic electroluminescent material according to one example can also be used in an organic electroluminescent device containing quantum dots (QDs).

[0192] One of the first electrode and the second electrode may be an anode and the other may be a cathode. In this case, the first electrode and the second electrode may each be formed of a transparent conductive material, or a semi-transparent or reflective conductive material. Depending on the type of material forming the first electrode and the second electrode, the organic electroluminescent device may be a front-emitting type, a back-emitting type, or a double-sided emitting type.

[0193] A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof may be used between the anode and the emissive layer. Multiple layers of the hole injection layer may be used to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, and two compounds may be used simultaneously in each layer. Additionally, the hole injection layer may be doped with a p-dopant. The electron blocking layer is located between the hole transport layer (or hole injection layer) and the emissive layer and can prevent light leakage by blocking the overflow of electrons from the emissive layer and trapping excitons within the emissive layer. Multiple layers of the hole transport layer or electron blocking layer may be used, and multiple compounds may be used in each layer.

[0194] 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 emitting layer and the cathode. Multiple layers of the electron buffer layer may be used to control electron injection and improve the interface characteristics between the emitting layer and the electron injection layer, and two compounds may be used simultaneously in each layer. The hole blocking layer is a layer located between the electron transport layer (or electron injection layer) and the emitting layer that prevents holes from reaching the cathode, thereby improving the recombination probability of electrons and holes within the emitting layer. Multiple layers of the hole blocking layer or electron transport layer may also be used, and multiple compounds may be used in each layer. Additionally, the electron injection layer may be doped with an n-dopant.

[0195] The light-emitting auxiliary layer is a layer located between an anode and a light-emitting layer, or between a cathode and a light-emitting layer. When the light-emitting auxiliary layer is located between the anode and the light-emitting layer, it can be used to facilitate the injection and / or transport of holes or to block electron overflow. When the light-emitting auxiliary layer is located between the cathode and the light-emitting layer, it can be used to facilitate the injection and / or transport of electrons or to block hole overflow. Additionally, the hole auxiliary layer is located between the hole transport layer (or hole injection layer) and the light-emitting layer and can exhibit the effect of facilitating or blocking the transport speed (or injection speed) of holes, thereby allowing for the adjustment of charge balance. When the organic electroluminescent device includes two or more hole transport layers, the additionally included hole transport layer can be used as a hole auxiliary layer or an electron blocking layer. The light-emitting auxiliary layer, the hole auxiliary layer, or the electron blocking layer may have the effect of improving the efficiency and / or lifespan of the organic electroluminescent device.

[0196] In the organic electroluminescent device of the present invention, it is preferable to arrange one or more layers selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter referred to as "surface layers") on the inner surface of at least one of a pair of electrodes. Specifically, it is preferable to arrange a chalcogenide layer (including oxides) of silicon and aluminum on the anode surface on the side of the light-emitting medium layer, and a metal halide layer or a metal oxide layer on the cathode surface on the side of the light-emitting medium layer. The operation stabilization of the organic electroluminescent device can be obtained through the surface layers. A preferred example of the chalcogenide is SiO₂. X (1≤X≤2), AlO X Examples include (1≤X≤1.5), SiON, SiAlON, etc., and preferred examples of metal halides include LiF, MgF2, CaF2, rare earth metal fluorides, etc., and preferred examples of metal oxides include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0197] In addition, in the organic electroluminescent device of the present invention, it is also preferable to arrange a mixed region of an electron transfer compound and a reducing dopant or a mixed region of a hole transfer compound and an oxidizing dopant on the surface of at least one of a pair of electrodes. In this manner, the electron transfer compound is reduced to an anion, making it easier to inject and transfer electrons from the mixed region to the light-emitting medium. In addition, the hole transfer compound is oxidized to a cation, making it easier to inject and transfer holes from the mixed region to the light-emitting medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds, and preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. Furthermore, an organic electroluminescent device that emits white light can be manufactured having two or more light-emitting layers by using the reducing dopant layer as a charge generation layer.

[0198] An organic electroluminescent device according to one example may further include one or more dopants in the light-emitting layer.

[0199] One or more phosphorescent or fluorescent dopants may be used as dopants included in the organic electroluminescent device of the present invention, and a phosphorescent dopant is preferred. The phosphorescent dopant material applied to the organic electroluminescent device of the present invention is not particularly limited, but may be a complex compound of metal atoms selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and in some cases, preferably, may be an orthometallated complex compound of metal atoms selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and in some cases, more preferably, may be an orthometallated iridium complex compound.

[0200] A compound represented by the following chemical formula 101 may be used as a dopant included in the organic electroluminescent device of the present invention, but is not limited thereto.

[0201] [Chemical Formula 101]

[0202]

[0203] In the above chemical formula 101,

[0204] L is any one selected from the following structures 1 to 3;

[0205] [Structure 1] [Structure 2] [Structure 3]

[0206]

[0207] R 100 to R 103Each is independently a (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C6-C30)aryl, cyano, substituted or unsubstituted (3-30)heteroaryl, or substituted or unsubstituted (C1-C30)alkoxy, which are hydrogen, deuterium, halogen, deuterium and / or halogen-substituted (C1-C30)alkoxy; and may be connected to adjacent substituents to form a ring, and may, for example with pyridine, form a substituted or unsubstituted quinoline, substituted or unsubstituted benzopropyridine, substituted or unsubstituted benzothyenopyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzopropyquinoline, substituted or unsubstituted benzothyenoquinoline, or substituted or unsubstituted indenopyridine;

[0208] R 104 to R 107 Each is independently a (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, cyano, or substituted or unsubstituted (C1-C30)alkoxy; may be connected to an adjacent substituent to form a substituted or unsubstituted ring, for example, with benzene to form a substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzopyridine, or substituted or unsubstituted benzothiopyridine;

[0209] R 201 to R 220Each is independently a (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C6-C30)aryl, which is a hydrogen, deuterium, halogen, deuterium and / or halogen-substituted or unsubstituted (C1-C30)alkyl; or may be connected to an adjacent substituent to form a substituted or unsubstituted ring;

[0210] s is an integer from 1 to 3.

[0211] Specific examples of the above-mentioned dopant compounds are as follows, but are not limited thereto.

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245] The formation of each layer of the organic electroluminescent device of the present invention may be achieved using any one of the following methods: dry deposition methods such as vacuum deposition, sputtering, plasma, or ion plating, or wet deposition methods such as spin coating, dip coating, or flow coating. In the case of wet deposition methods, a thin film is formed by dissolving or dispersing the material forming each layer in a suitable solvent such as ethanol, chloroform, tetrahydrofuran, or dioxane. Any solvent may be used as long as the material forming each layer can be dissolved or dispersed in it and there is no problem with the filmability.

[0246] When forming a film of a first host material and a second host material according to one example, the film can be formed using the methods listed above, and commonly, the film can be formed by a co-deposition or mixed deposition process. The co-deposition is a method of placing two or more materials into separate crucible sources and applying current to two cells simultaneously to evaporate the materials and perform mixed deposition, and the mixed deposition is a method of mixing two or more materials in a single crucible source before deposition and then applying current to one cell to evaporate the materials and perform mixed deposition.

[0247] According to one example, when the first host material and the second host material exist in the same layer or different layers within an organic electroluminescent device, the two host compounds can each be deposited individually. For example, the second host material may be deposited after the first host material has been deposited.

[0248] According to one embodiment, the present invention may provide a display device comprising a plurality of host materials including a first host material comprising a compound represented by Formula 1 and a second host material comprising a compound represented by Formula 2, or an organic electroluminescent compound represented by Formula 2. In addition, it is possible to manufacture a display device, for example, a display device for a smartphone, tablet, laptop, PC, TV, or vehicle, or a lighting device, for example, an outdoor or indoor lighting device, using the organic electroluminescent element of the present invention.

[0249] Hereinafter, for a detailed understanding of the present invention, a method for manufacturing a compound according to the present invention is described by citing a method for synthesizing a representative compound or an intermediate compound of the present invention as an example.

[0250] [Example 1] Synthesis of Compound H1-104

[0251]

[0252] 1) Synthesis of Compound 1

[0253] In a flask, dibenzofuran-2-amine (20 g, 144.7 mmol), 2-bromodibenzofuran (23.8 g, 96.47 mmol), palladium(II) acetate (Pd(OAc)2) (1.1 g, 4.82 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl(S-Phos) (3.9 g, 9.65 mmol), sodium tert 13.9 g, 144.7 mmol of β-butoxide (NaOt-Bu) and 485 mL of β-xylene were added and stirred at 160°C for 3 hours. After the reaction was complete, the mixture was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, and the mixture was dried and separated by column chromatography to obtain the compound. 1 (4.9 g, yield: 10%) was obtained.

[0254] 2) Synthesis of Compound H1-104

[0255] Compound in the flask 1 (4.9 g, 12.76 mmol), compound 2 65 mL of Tris(dibenzylideneacetone)dipalladium(O)(Pd2(dba)3) (4.2 g, 14.0 mmol), Tris(dibenzylideneacetone)dipalladium(O)(Pd2(dba)3) (0.584 g, 0.638 mmol), S-Phos (0.523 g, 1.276 mmol), NaOt-Bu (1.8 g, 19.14 mmol), and o-xylene were added and stirred at 160°C for 2 hours. After the reaction was complete, the mixture was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, and the mixture was dried. The compounds were then separated by column chromatography. H1-104 (5.6 g, yield: 68.3%) was obtained.

[0256]

[0257] [Example 2] Synthesis of Compound H1-88

[0258]

[0259] Compound in the flask 3(25 g, 74.48 mmol), compound 2 (42.58 g, 81.93 mmol), Pd(OAc)2(0.16 g, 7.5 mmol), tri tert 0.28 g, 7.5 mmol, β-butylphosphine (P(t-Bu)3) and 284.09 mL of NaOt-Bu (14.31 g, 150 mmol) and o-xylene were added, and the mixture was stirred at 160°C for 2 hours. After the reaction was complete, the mixture was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, and the mixture was dried. The compounds were then separated by column chromatography. H1-88 (23.4 g, yield: 50%) was obtained.

[0260]

[0261] [Example 3] Synthesis of Compound H1-94

[0262]

[0263] Compound in the flask 4 (20 g, 56.96 mmol), compound 2 P(Oc)2 (18.8 g, 57.13 mmol), P(Oc)2 (0.13 g, 5.7 mmol), P(t-Bu)3 (0.22 g, 5.7 mmol), NaOt-Bu (11 g, 113.92 mmol), and 227.27 mL of o-xylene were added, and the mixture was stirred at 160°C for 2 hours. After the reaction was complete, the mixture was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, and the mixture was dried. The compounds were then separated by column chromatography. H1-94 (12.5 g, yield: 34%) was obtained.

[0264]

[0265] [Example 4] Synthesis of Compound H1-85

[0266]

[0267] 1) Synthesis of Compound 5

[0268] 3-aminobiphenyl (54 g, 319 mmol), 3-bromobiphenyl (70 g, 301 mmol), Pd(OAc)2 (0.33 g, 1.47 mmol), tricyclohexylphosphine (P(Cy)3) (0.84 g, 2.8 mmol), NaOt-Bu (57 g, 593 mmol), and 280 mL of toluene were added to a flask and stirred at 95°C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, and the mixture was dried. The compounds were then separated by column chromatography. 5 (60.23 g, yield: 85%) was obtained.

[0269] 2) Synthesis of Compound H1-85

[0270] Compound in the flask 5 (60.23 g, 187.5 mmol), compound 2 300 mL of (60 g, 182.33 mmol), Pd(OAc)2 (0.41 g, 1.83 mmol), S-phos (1.74 g, 4.23 mmol), NaOt-Bu (26.23 g, 272 mmol), and xylene were added and stirred at 110°C for 10 hours. After the reaction was complete, the mixture was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, and the mixture was dried. The compounds were then separated by column chromatography. H1-85 (36.9 g, yield: 33%) was obtained.

[0271]

[0272] [Example 5] Synthesis of Compound H1-115

[0273]

[0274] 1) Synthesis of Compound 6

[0275] Dibenzofuran-2-amine (29.24 g, 159.7 mmol), 2-bromodibenzothiophene (40 g, 152.7 mmol), Pd(OAc)2 (0.17 g, 0.75 mmol), P(Cy)3 (0.43 g, 1.45 mmol), NaOt-Bu (29.22 g, 304 mmol), and 250 mL of toluene were added to a flask and stirred at 95°C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, and the mixture was dried. The compounds were then separated by column chromatography. 6 (17.12 g, yield: 86%) was obtained.

[0276] 2) Synthesis of Compound H1-115

[0277] Compound in the flask 6 (17.12 g, 46.89 mmol), compound 2 75 mL of (15 g, 45.58 mmol), Pd(OAc)2 (0.05 g, 0.22 mmol), S-phos (0.22 g, 0.535 mmol), NaOt-Bu (6.56 g, 68.2 mmol), and xylene were added and stirred at 110°C for 10 hours. After the reaction was complete, the mixture was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, and the mixture was dried and separated by column chromatography to obtain the compounds. H1-115 (10.2 g, yield: 34%) was obtained.

[0278]

[0279] [Example 6] Synthesis of Compound H1-86

[0280]

[0281] Compound in the flask 2Pd(OAc)2 (5.0 g, 15.2 mmol), di([1,1'-biphenyl]-4-nyl)amine (4.9 g, 15.2 mmol), Pd(OAc)2 (0.2 g, 0.8 mmol), P(t-Bu)3 (0.8 mL, 1.5 mmol), NaOt-Bu (2.9 g, 30.4 mmol), and 76 mL of xylene were added, and the mixture was stirred at 160°C for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, and the precipitated solid was washed with distilled water and methanol. Subsequently, the compounds were separated by column chromatography. H1-86 (5.5 g, yield: 59%) was obtained.

[0282] [Example 7] Synthesis of Compound H1-51

[0283]

[0284] Compound in the flask 2 (4 g, 12 mmol), bis(biphenyl-4-yl)[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl]amine (6.8 g, 13 mmol), Pd(OAc)2 (0.3 g, 1 mmol), S-Phos (0.9 g, 2 mmol), cesium carbonate (Cs2CO3) (11.5 g, 35 mmol), 60 mL of o-xylene, 15 mL of EtOH, and 15 mL of distilled water were added, and the mixture was refluxed and stirred at 150°C for 3 hours. After the reaction was complete, the mixture was cooled to room temperature, washed with distilled water, extracted with ethyl acetate, and the organic layer was dried after removing residual moisture with magnesium sulfate. Subsequently, the compounds were separated by column chromatography. H1-51 (2.2 g, yield: 27%) was obtained.

[0285] [Example 8] Synthesis of Compound H1-68

[0286]

[0287] Compound in the flask 7N-(4-bromophenyl)-N-phenyl-[1,1'-biphenyl]-4-amine (4.8 g, 11.34 mmol), tetrakis(triphenylphosphine)palladium(O)(Pd(PPh3)4) (0.4 g, 0.34 mmol), Na2CO3 (3.0 g, 28.35 mmol), 57 mL of toluene, 14 mL of ethanol, and 14 mL of distilled water were added, and the mixture was stirred at 120°C for 4 hours. After the reaction was complete, the mixture was added dropwise to methanol, and the resulting solid was filtered. The resulting solid was purified by column chromatography to obtain the compound H1-68 (1.4 g, yield: 20.0%) was obtained.

[0288] [Example 9] Preparation of Compound H1-87

[0289]

[0290] 1) Synthesis of Compound 8

[0291] Compound in the flask 2 (10.0 g, 30.3 mmol), [1,1'-biphenyl]-3-amine (6.7 g, 39.4 mmol), Pd(OAc)2 (0.34 g, 1.5 mmol), P(t-Bu)3 (1.5 mL, 3.03 mmol), NaOt-Bu (5.8 g, 60.6 mmol), and 150 mL of xylene were added, and the mixture was stirred at 160°C for 6 hours. After the reaction was complete, the mixture was cooled to room temperature, washed with distilled water, the organic layer was extracted with ethyl acetate, and dried with magnesium sulfate. Subsequently, the solvent was removed using a rotary evaporator, and the compounds were separated by column chromatography. 8 (10.8 g, yield: 36%) was obtained.

[0292] 2) Synthesis of Compound H1-87

[0293] Compound in the flask 860 mL of (5.0 g, 10.8 mmol), 3-bromodibenzofuran (3.2 g, 12.9 mmol), Pd2(dba)3 (0.5 g, 0.54 mmol), S-Phos (0.45 g, 1.08 mmol), NaOt-Bu (2.0 g, 21.6 mmol), and o-xylene were added, and the mixture was stirred at 160°C for 6 hours. After the reaction was complete, the mixture was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, and the mixture was dried. Subsequently, the compounds were separated by column chromatography. H1-87 (1.45 g, yield: 21%) was obtained.

[0294]

[0295] [Example 10] Synthesis of Compound H1-96

[0296]

[0297] Compound in the flask 1-1 (33 g, 100 mmol), compound CPPO 500 mL of (45.3 g, 110 mmol), Pd2(dba)3 (4.5 g, 5 mmol), S-Phos (4.1 g, 10 mmol), NaOt-Bu (19.2 g, 200 mmol), and o-xylene were added, and the mixture was stirred at 160°C for 2 hours. After the reaction was complete, the mixture was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, and the mixture was dried. Subsequently, the compounds were separated by column chromatography. H1-96 (52 g, yield: 73.7%) was obtained.

[0298]

[0299] [Example 11] Synthesis of Compound H1-103

[0300]

[0301] 1) Synthesis of Compound 1-2

[0302] 4-Bromo-1,1'2,1"-terphenyl (10.0 g, 32.34 mmol), 8-aminodibenzo[b,d]furan-2-yl (8.8 g, 48.51 mmol), bis(di- tert 2.3 g, 3.23 mmol of β-butyl(4-dimethylminophenyl)phosphine)dichloropalladium(II)(PdCl2(Amphos)2) and 4.6 g, 48.51 mmol of NaOt-Bu (4.6 g, 48.51 mmol) were dissolved in 161 mL of o-xylene and stirred under reflux for 2 hours. After the reaction was complete, the mixture was cooled to room temperature, and the reaction mixture was filtered using a Celite filter to obtain the compound. 1-2 (8.6 g, yield: 64.6%) was obtained.

[0303] 2) Synthesis of Compound H1-103

[0304] compound 1-2 (8.6 g, 20.90 mmol), compound CPPO (8.3 g, 25.08 mmol), Pd2(dba)3 (1.0 g, 1.05 mmol), S-Phos (900 mg, 2.09 mmol), and NaOt-Bu (5.0 g, 52.25 mmol) were dissolved in 140 mL of oxylene and stirred under reflux for 3 hours. After the reaction was complete, the mixture was cooled to room temperature and filtered through a Celite filter to obtain a solid, which was then separated by column chromatography to obtain the compound. H1-103 (5.8 g, yield: 39.4%) was obtained.

[0305]

[0306] [Example 12] Synthesis of Compound H1-95

[0307]

[0308] 1) Synthesis of Compounds 1-3

[0309] [1,1'-Biphenyl]-4-amine (60 g, 354 mmol), 2-bromodibenzo[b,d]furan (58.5 g, 236 mmol), Pd(OAc)2 (0.54 g, 3.23 mmol), P(Cy)3 (1.35 g, 3 mmol), and NaOt-Bu (40.9 g, 425.5 mmol) were dissolved in 600 mL of toluene and stirred under reflux for 2 hours. After the reaction was complete, the mixture was cooled to room temperature and filtered through a Celite filter to obtain a solid. The solid was then separated by column chromatography to obtain compounds 1-3 (65.7 g, yield: 83%).

[0310] 2) Synthesis of Compound H1-95

[0311] compound 1-3 (20g g, 59.6 mmol), compound CPPO (19.7 g, 59.7 mmol), Pd2(dba)3 (0.55 g, 0.6 mmol), X-Phos (0.57 g, 1.2 mmol), and NaOt-Bu (11.5 g, 119.6 mmol) were dissolved in 200 mL of oxylene and stirred under reflux for 3 hours. After the reaction was complete, the mixture was cooled to room temperature and filtered through a Celite filter to obtain a solid, which was then separated by column chromatography to obtain the compound. H1-95 (12.7 g, yield: 34%) was obtained.

[0312]

[0313] [Example 13] Synthesis of Compound C-9

[0314]

[0315] 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-(naphthalene-2-yl)-1,3,5-triazine (10 g, 24.5 mmol), (4-(triphenylsilyl)phenyl)boronic acid (10.2 g, 26.9 mmol), Pd(pph3)4 (1.4 g, 1.23 mmol), potassium carbonate (K2CO3) (8.4 g, 61.2 mmol), 125 mL of toluene, 30 mL of EtOH, and 30 mL of H2O were added to a flask and stirred at 160°C. After the reaction was complete, methanol (MeOH) and water were added to the reaction mixture and stirred, after which the solvent was removed by vacuum filtration. Subsequently, the mixture was separated by column chromatography, and the resulting solid was vacuum filtered with the addition of MeOH to obtain the compound. C-9 (16.9 g, yield: 97%) was obtained.

[0316]

[0317] [Example 14] Synthesis of Compound C-15

[0318]

[0319] 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-(dibenzo[b,d]furan-1-yl)-1,3,5-triazine (10 g, 23.0 mmol), (4-(triphenylsilyl)phenyl)boronic acid (9.6 g, 25.3 mmol), Pd(pph3)4 (1.3 g, 1.15 mmol), K2CO3 (7.9 g, 57.5 mmol), 120 mL of toluene, 30 mL of EtOH, and 30 mL of H2O were added to a flask and stirred at 160°C. After the reaction was complete, MeOH and water were added to the reaction mixture and stirred, and the solvent was removed by vacuum filtration. Subsequently, the mixture was separated by column chromatography, and the resulting solid was vacuum filtered with the addition of MeOH to obtain the compound. C-15 (17 g, yield: 97%) was obtained.

[0320]

[0321] [Example 15] Synthesis of Compound C-59

[0322]

[0323] Compound in the flask 11 (8.0 g, 22.4 mmol), compound 12 (14.9 g, 32.1 mmol), Pd(PPh3)4 (1.3 g, 1.12 mmol), K2CO3 (6.2 g, 44.8 mmol), 114 mL of toluene (Tol), 30 mL of ethanol (EtOH), and 31 mL of water (H2O) were dissolved and stirred under reflux for 4 hours and 20 minutes. After the reaction was complete, the mixture was cooled to room temperature, extracted with ethyl acetate (EA), and separated by column chromatography to obtain the compound. C-59 (9.5 g, yield: 65%) was obtained.

[0324]

[0325] [Example 16] Synthesis of Compound C-6

[0326]

[0327] Compound in the flask 13 (9.5 g, 24.56 mmol), compound 14 (7 g, 292.56 mmol), Pd(PPh3)4 (1.4 g, 1.228 mmol), K2CO3 (8.48 g, 61.4 mmol), 120 mL of toluene (Tol), 60 mL of EtOH, and 60 mL of H2O were added and dissolved, then refluxed at 120°C for 2 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, and the mixture was dried. The compounds were then separated by column chromatography. C-6 (4.5 g, yield: 25.9%) was obtained.

[0328]

[0329] Hereinafter, for a detailed understanding of the present invention, a method for manufacturing an organic electroluminescent device comprising a plurality of host materials according to the present invention and the characteristics thereof are described.

[0330] [Device Examples 1 to 4] Manufacturing of an OLED by co-depositing the first host material and the second host material according to the present invention

[0331] An OLED according to the present invention was manufactured. First, a transparent electrode ITO thin film (10Ω / □) on an OLED glass substrate (manufactured by Geomatec) was ultrasonically cleaned using acetone and isopropyl alcohol sequentially, and then stored in isopropyl alcohol before use. Next, the ITO substrate was mounted on the substrate holder of a vacuum deposition apparatus, and then a compound was placed in the cell inside the vacuum deposition apparatus. HI-1 Insert, and in another cell, a compound HT-1 After adding, the two substances are evaporated at different rates to form a compound HI-1 and compounds HT-1 Compounds with respect to the total amount of HI-1 A 10 nm thick hole injection layer was deposited by doping with an amount of 3 wt%. Subsequently, the compound HT-1 A first hole transport layer with a thickness of 80 nm was formed by depositing it on the hole injection layer. Subsequently, a compound was placed in another cell within the vacuum deposition equipment. HT-2 [The material] was added, and a current was applied to the cell to evaporate it, thereby depositing a second hole transport layer with a thickness of 60 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, an emissive layer was deposited thereon as follows. The first host material and the second host material listed in Table 1 below were placed as hosts in two locations within the vacuum deposition apparatus, and a compound was placed as a dopant in another cell. D-39 After adding, a 40 nm thick emissive layer was deposited on the second hole transport layer by evaporating the two host materials at a 1:1 rate and simultaneously evaporating the dopant material at a different rate, thereby doping the dopant to an amount of 3 wt% relative to the total amount of the host and dopant. Subsequently, a compound was placed on the emissive layer as an electron transport material. ET-1 and compounds EI-1 An electron transport layer with a thickness of 35 nm was deposited by doping at a weight ratio of 50:50. Subsequently, a compound was used as the electron injection layer. EI-1After depositing the above electron transport layer to a thickness of 2 nm, an OLED was fabricated by depositing an Al cathode to a thickness of 80 nm on the electron injection layer using a different vacuum deposition equipment. For each material, each compound was 10 -6 It was purified by vacuum sublimation under torr conditions and used.

[0332] [Device Comparative Example 1] Preparation of an OLED containing a comparative compound as a host

[0333] An OLED was manufactured in the same manner as in Device Example 1, except that Compound A of Table 1 below was used as one of the host materials of the light-emitting layer.

[0334] The driving voltage, luminous efficiency, luminous color, and the time taken for the light intensity to drop from 100% to 95% (lifetime: T95) at a luminance of 1,000 nits were measured for the organic electroluminescent devices of Examples 1 to 4 and Comparative Example 1 manufactured as described above, respectively, and the results are shown in Table 1 below.

[0335]

[0336] From Table 1 above, it can be seen that an organic electroluminescent device comprising a specific combination of compounds according to the present invention as a host material exhibits high luminous efficiency and, in particular, significantly improved lifespan.

[0337] [Device Examples 5 and 6] Preparation of an OLED comprising an organic electroluminescent compound according to the present invention

[0338] An OLED according to the present invention was manufactured. First, a transparent electrode ITO thin film (10Ω / □) on an OLED glass substrate (manufactured by Geomatec) was ultrasonically cleaned using acetone and isopropyl alcohol sequentially, and then stored in isopropanol before use. Next, the ITO substrate was mounted on the substrate holder of a vacuum deposition apparatus, and then a compound was placed in the cell inside the vacuum deposition apparatus. HI-1 Insert, and in another cell, a compound HT-1 After adding, the two substances are evaporated at different rates to form a compound HI-1 class compound HT-1 Compounds with respect to the total amount of HI-1 A 10 nm thick hole injection layer was deposited by doping with an amount of 3 wt%. Subsequently, a compound was used as the first hole transport layer. HT-1 The compound was deposited to a thickness of 80 nm on the hole injection layer. Subsequently, the compound was placed in another cell within the vacuum deposition apparatus. HT-3 A compound was added, and current was applied to the cell to evaporate it, thereby depositing a second hole transport layer with a thickness of 5 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, an emissive layer was deposited thereon as follows: a compound as a host in the cell within the vacuum deposition apparatus. BH Insert, and in another cell, a compound as a dopant BD After adding, a 20 nm thick emissive layer was deposited on the second hole transport layer by doping the two materials at different rates to an amount of 8 wt% of the dopant relative to the total amount of the host and dopant. Subsequently, a 5 nm thick electron buffer layer was deposited on the emissive layer by doping with a compound listed in Table 2 below as an electron buffer layer. Subsequently, a compound was deposited on the electron buffer layer as an electron transport layer. ET-1 : EI-1 30 nm was deposited by doping at a 50:50 weight ratio. Subsequently, a compound was deposited as the electron injection layer. EI-1 After depositing the above electron transport layer to a thickness of 2 nm, an OLED was fabricated by depositing an Al cathode to a thickness of 80 nm on the electron injection layer using a different vacuum deposition equipment. For each material, each compound was 10 -6 It was purified by vacuum sublimation under torr conditions and used.

[0339] [Device Comparative Example 2] Preparation of an OLED containing a comparative compound as an electronic buffer layer material

[0340] An OLED was manufactured in the same manner as in Device Example 5, except that the compound listed in Table 2 below was used as the electronic buffer layer material.

[0341] The driving voltage, luminous efficiency, and luminous color at a luminance of 1,000 nits were measured for the organic electroluminescent devices according to Examples 5 and 6 and Comparative Example 2 manufactured as described above, respectively, and the results are shown in Table 2 below.

[0342]

[0343] From Table 2 above, it can be confirmed that an organic electroluminescent device containing an organic electroluminescent compound according to the present invention as an electronic buffer material exhibits a lower driving voltage and higher luminous efficiency compared to a conventional organic electroluminescent device.

[0344] The compounds used in device Examples 1 to 6 and device Comparative Examples 1 and 2 are specifically shown in Table 3 below.

[0345]

[0346]

Claims

Claim 1 A plurality of host materials comprising a first host material comprising a compound represented by the following chemical formula 1-2 and a second host material comprising a compound represented by the following chemical formula 2-1: [Chemical Formula 1-2] In the above chemical formula 1-2, X1 and Y1 are each independently -N=, -NR5-, -O-, or -S-, provided that either X1 or Y1 is -N= and the other of X1 and Y1 is -NR5-, -O-, or -S-; R1 is a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3-30)heteroaryl; and R2 to R5 are each independently hydrogen, deuterium, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted (3-7)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3-30)heteroaryl, a substituted or unsubstituted Fusion ring of the (C3-C30) aliphatic ring and the (C6-C30) aromatic ring, -NR 11 R 12, -SiR 13 R 14 R 15 or a combination thereof; adjacent substituents can be connected to each other to form a ring; R 11 to R 15 are each independently a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30)heteroaryl; L1 is a single bond or a substituted or unsubstituted (C6-C30)arylene; Ar1 ​​is a deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted (3-7)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3-30)heteroaryl, a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and an (C6-C30) aromatic ring, -NR 11 R 12 , -SiR 13 R 14 R 15 , or a combination thereof; a and b are each independently an integer of 1 or 2, and c is an integer from 1 to 3; where a to c are integers of 2 or more, each R2 to each R4 may be the same or different from each other; [Chemical Formula 2-1] In the above chemical formula 2-1, Y is -O- or -S-; L2 is a single-bonded, substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30)heteroarylene; Z1 to Z3 are each independently N or CH; provided that at least one of Z1 to Z3 is N; and A is Si or C; Ar3 is a substituted or unsubstituted (C6-C30)aryl; L3 is a single bond, a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C3-C30)cycloalkylene, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30)heteroarylene; R', R'', and R''' are each independently a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3-30)heteroaryl; R8 and R9 are each independently hydrogen, deuterium, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted (3-7)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, -NR 16 R 17 , -SiR 18 R 19 R 20 , or a combination thereof; can be connected to adjacent substituents to form a ring; R 16 to R 20 Each is independently a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30)heteroaryl; e is an integer from 1 to 4, and f is an integer from 1 to 3; where e and f are each integers of 2 or more, each R8 and each R9 may be the same or different from each other. Claim 2 In claim 1, the substituents of the substituted alkyl(len), substituted cycloalkyl(len), substituted cycloalkenyl, substituted heterocycloalkyl, substituted aryl(len), and substituted heteroaryl(len) are each independently deuterium; halogen; cyano; carboxyl; nitro; hydroxy; (C1-C30)alkyl; halo(C1-C30)alkyl; (C2-C30)alkenyl; (C2-C30)alkynyl; (C1-C30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl; (3-7-membered)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (C6-C30)aryl substituted or unsubstituted (3-30)heteroaryl; (C6-C30)aryl substituted or unsubstituted with one or more of (C1-C30)alkyl and (3-30)heteroaryl; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; amino; mono- or di-(C1-C30)alkylamino; mono- or di-(C6-C30)arylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; A plurality of host materials, one or more selected from the group consisting of di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)ar(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl. Claim 3 delete Claim 4 In claim 1, the Ar1 is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthylphenyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted benzophenanthrenyl, substituted or unsubstituted crisenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzoflurenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted spiro[cyclopentane-fluorene]yl, substituted or unsubstituted spiro[indane-fluorene]yl, substituted or unsubstituted spiro[fluorene-benzofluren]yl, or phenyl; naphthyl; biphenyl; terphenyl; substituted or unsubstituted fluorenyl; phenanthrenyl; A plurality of host materials, wherein the host material is an amino substituted with at least one of phenyl-substituted or unsubstituted dibenzofuranyl; dibenzothiophenyl; phenyl-substituted or unsubstituted carbazolyl; and benzonaphtofuranyl. Claim 5 delete Claim 6 delete Claim 7 In claim 1, a plurality of host materials, wherein the compound represented by the chemical formula 1-2 is selected from the following compounds. Claim 8 In claim 1, a plurality of host materials, wherein the compound represented by Chemical Formula 2-1 is selected from the following compounds. Claim 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. Claim 10 Organic electroluminescent compound represented by the following chemical formula 3: [Chemical Formula 3] In the above chemical formula 3, Y is O or S; A is Si or C; L2 is a single bond, deuterium-substituted or unsubstituted phenylene, deuterium-substituted or unsubstituted biphenylene, or deuterium-substituted or unsubstituted naphthylene; R8 and R9 are each independently hydrogen or deuterium; Ar3 is deuterium-substituted or unsubstituted phenyl, deuterium-substituted or unsubstituted biphenyl, deuterium-substituted or unsubstituted terphenyl, deuterium-substituted or unsubstituted naphthyl, deuterium-substituted or unsubstituted triphenylenyl, deuterium-substituted or unsubstituted phenanthrenyl, or a combination thereof; L3 is deuterium-substituted or unsubstituted phenylene, deuterium-substituted or unsubstituted biphenylene, or deuterium-substituted or unsubstituted naphthylene; R', R'', and R''' are each independently a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3-30)heteroaryl; e is an integer from 1 to 4, and f is an integer from 1 to 3; where e and f are each integers of 2 or more, each R8 and each R9 may be the same or different from each other. Claim 11 In claim 10, the organic electroluminescent compound represented by the above chemical formula 3 is selected from the following compounds. Claim 12 An organic electroluminescent material comprising an organic electroluminescent compound according to paragraph 10. Claim 13 In claim 12, an organic field-emitting device comprising the above organic field-emitting material.

Images