Compound, organic electroluminescent material, and organic electroluminescent device comprising same

Abstract

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Description

Technical Field

[0001] The present disclosure relates to a compound and an organic electroluminescent material and an organic electroluminescent device comprising the same. Background Art

[0002] The TPD / Alq3 double-layer small molecule organic electroluminescent device (OLED) with green light emission consisting of a light-emitting layer and a charge transport layer was first developed by Tang et al. of Eastman Kodak in 1987. Since then, research on organic electroluminescent devices has been rapidly carried out, and OLED has been commercialized since then. At present, OLED mainly uses phosphorescent materials with excellent luminous efficiency in panel implementation. Therefore, for long-term use and high display resolution, OLEDs with high luminous efficiency and / or long life characteristics are required. Korean Patent Application Publication Nos. 2011-0052540, 2011-0075690, 2019-0113663, and 2015-0061975 disclose an organic light-emitting device using a nitrogen-containing heteroaryl group such as triazine and / or a carbazole derivative substituted with dibenzofuran, dibenzothiophene, etc. as a main material of a light-emitting layer, but do not specifically disclose an organic electroluminescent device having improved performance such as low driving voltage and / or long life characteristics due to the inclusion of a compound having a specific substituent at a specific position described in the present disclosure and an organic electroluminescent material including the compound. Summary of the invention

[0003] Technical issues

[0004] The object of the present disclosure is first to provide a compound effective for producing an organic electroluminescent device having low driving voltage and / or long life characteristics, and secondly to provide an organic electroluminescent material comprising the compound, and an organic electroluminescent device comprising the compound and / or the organic electroluminescent material according to the present disclosure.

[0005] Solution to the problem

[0006] As a result of in-depth research to solve the above technical problems, the inventors of the present invention found that the above-mentioned purpose can be achieved by a compound represented by the following formula 1, and / or an organic electroluminescent material comprising a compound represented by the following formula 1 and a compound represented by the following formula 2 or 3, thereby completing the present invention.

[0007]

[0008] In formula 1,

[0009] X1 to X3 each independently represent CR5 or N, provided that at least one of X1 to X3 is N;

[0010] Ar1 represents hydrogen, deuterium, halogen, cyano, amino, substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C6-C 30 )aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (C1-C 30 )alkoxy, -Si(R 11 )(R 12 )(R 13 ), or -N(R 14 )(R 15 );

[0011] R 11 To R 15 Each independently represents a substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C2-C 30 )alkenyl, substituted or unsubstituted (C6-C 30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl;

[0012] L1 represents a single bond, substituted or unsubstituted (C6-C 30 )arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene;

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

[0014] R1 to R5 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C6-C 30 )aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (C1-C 30 ) alkoxy, substituted or unsubstituted tri(C1-C 30 )alkylsilyl, substituted or unsubstituted di(C1-C 30 )alkyl(C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 )alkyldi(C6-C 30 ) arylsilyl, or substituted or unsubstituted tri(C6-C 30 ) arylsilyl; or may be connected to adjacent substituents to form one or more rings; and

[0015] a, b, and d each independently represent an integer of 1 to 4, c represents an integer of 1 to 3, and when a to d are integers of 2 or more, each of R1 to R4 may be the same as or different from each other.

[0016]

[0017] In formula 2,

[0018] A1 and A2 each independently represent a substituted or unsubstituted (C6-C 30 ) aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazolyl;

[0019] X 15 To X 18 Any one of 19 To X 22 Any of are connected to each other to form a single bond; and

[0020] X 11 To X 14 , X 23 To X 26 , and X that does not form a single bond 15 To X 22 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C 30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; or may be connected to adjacent substituents to form one or more rings.

[0021]

[0022] In formula 3,

[0023] A3 represents a substituted or unsubstituted (C6-C 30 ) aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, or substituted or unsubstituted carbazolyl;

[0024] L2 represents a single bond, or a substituted or unsubstituted (C6-C 30 ) arylene; and

[0025] A pair of adjacent X 35 To X 38 X connected to the following formula 3-A to form a ring, and not forming one or more rings 35 To X 38 and X 31 To X 34 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C 30)aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl.

[0026]

[0027] In Formula 3-A,

[0028] A4 represents a substituted or unsubstituted (C6-C 30 ) aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, or substituted or unsubstituted carbazolyl;

[0029] L3 represents a single bond, or a substituted or unsubstituted (C6-C 30 ) arylene; and

[0030] X 41 To X 44 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C 30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl.

[0031] Beneficial Effects of the Invention

[0032] By including the compound according to the present disclosure and / or an organic electroluminescent material including the compound, an organic electroluminescent device having low driving voltage and / or high luminous efficiency and / or long life characteristics may be provided. DETAILED DESCRIPTION

[0033] Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present invention and is not intended to limit the scope of the present invention in any way.

[0034] The present disclosure relates to a compound represented by the above Formula 1, an organic electroluminescent material including the compound, and an organic electroluminescent device including the compound and / or the organic electroluminescent material.

[0035] The organic electroluminescent material according to the present disclosure includes a compound represented by Formula 1 and a compound represented by Formula 2 or 3.

[0036] Herein, the term "organic electroluminescent compound" in the present disclosure means a compound that can be used in an organic electroluminescent device, and which can be contained in any material layer constituting the organic electroluminescent device as necessary.

[0037] Herein, the term "organic electroluminescent material" means a material that can be used in an organic electroluminescent device and which can include at least one compound. If necessary, the organic electroluminescent material can be included in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole auxiliary material, a luminescence auxiliary material, an electron blocking material, a luminescent material (including a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material, etc.

[0038] The term "multiple organic electroluminescent materials" in the present disclosure means an organic electroluminescent material comprising a combination of at least two compounds, which may be included in any layer constituting an organic electroluminescent device. It may mean both a material contained in an organic electroluminescent device before (e.g., before vapor deposition) and a material contained in an organic electroluminescent device after (e.g., after vapor deposition). For example, a plurality of organic electroluminescent materials may be a combination of at least two compounds, which may be contained in at least one of the following layers: a hole injection layer, a hole transport layer, a hole auxiliary layer, a luminescent auxiliary layer, an electron blocking layer, a luminescent layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. Therefore, at least two compounds may be contained in the same layer or in different layers, and may be mixed-evaporated or co-evaporated, or may be evaporated individually.

[0039] Herein, the term "multiple host materials" means an organic electroluminescent material comprising a combination of at least two host materials. It may mean both a material before being included in an organic electroluminescent device (e.g., before vapor deposition) and a material after being included in an organic electroluminescent device (e.g., after vapor deposition). The various host materials disclosed herein may be included in any light-emitting layer constituting an organic electroluminescent device. At least two compounds included in the various host materials may be included in one light-emitting layer together, or may each be included in a separate light-emitting layer. When at least two compounds are included in one light-emitting layer, the at least two compounds may be mixed-evaporated to form a layer, or the at least two compounds may be co-evaporated individually and simultaneously to form a layer.

[0040] In this article, “(C1-C 30 "(C3-C4)alkyl" means a straight or branched alkyl group having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10. The above alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, etc. Herein, "(C3-C4)alkyl" means a straight or branched alkyl group having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10. The above alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, etc. 30"(C6-C7-membered)heterocycloalkyl" means a cycloalkyl group having 3 to 7 ring backbone atoms, preferably 5 to 7 ring backbone atoms and at least one heteroatom selected from the group consisting of B, N, O, S, Si and P, preferably O, S and N, and includes tetrahydrofuran, pyrrolidine, tetrahydrothiophene (thiolan), tetrahydropyran and the like. In the present disclosure, "(C6-C7-membered)heterocycloalkyl" means a cycloalkyl group having 3 to 7 ring backbone atoms, preferably 5 to 7 ring backbone atoms and at least one heteroatom selected from the group consisting of B, N, O, S, Si and P, preferably O, S and N, and includes tetrahydrofuran, pyrrolidine, tetrahydrothiophene (thiolan), tetrahydropyran and the like. In the present disclosure, "(C6-C7-membered)heterocycloalkyl" means a cycloalkyl group having 3 to 7 ring backbone atoms, preferably 5 to 7 ring backbone atoms and at least one heteroatom selected from the group consisting of B, N, O, S, Si and P, preferably O, S and N. 30 The term "(y)aryl" means a monocyclic or condensed ring group derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, wherein the number of ring backbone carbon atoms is preferably 6 to 20, more preferably 6 to 15, and may be partially saturated and may contain a spiro structure. Examples of the aryl group specifically include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthrenyl, triphenylenyl, phenylphenanthrenyl, anthracenyl, benzanthryl, indenyl, triphenylene, pyrenyl, naphthyl, peryl, Benzo yl, naphthacetyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, mesityl, cumenyl, spiro[fluorene-fluorene]yl, spiro[fluorene-benzofluorene]yl, azulenyl, tetramethyl-dihydrophenanthryl, and the like. More specifically, the aryl group may be o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumyl, m-cumyl, p-cumyl, p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 4′-methylbiphenyl, 4″-tert-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-quaterphenyl, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 9-phenanthrenyl, 1- Base, 2- Base, 3- Base, 4- Base, 5- Base, 6- Benzo[c]phenanthrenyl, benzo[g] 1-triphenylene, 2-triphenylene, 3-triphenylene, 4-triphenylene, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, 11,11-dimethyl-1-benzo[a]fluorenyl, 11,11-dimethyl-2-benzo[a]fluorenyl, 11,11-dimethyl-3-benzo[a]fluorenyl, 11, 11-dimethyl-4-benzo[a]fluorenyl, 11,11-dimethyl-5-benzo[a]fluorenyl, 11,11-dimethyl-6-benzo[a]fluorenyl, 11,11-dimethyl-7-benzo[a]fluorenyl, 11,11-dimethyl-8-benzo[a]fluorenyl, 11,11-dimethyl-9-benzo[a]fluorenyl, 11,11- dimethyl-10-benzo[a]fluorenyl, 11,11-dimethyl-1-benzo[b]fluorenyl, 11,11-dimethyl-2-benzo[b]fluorenyl, 11,11-dimethyl-3-benzo[b]fluorenyl, 11,11-dimethyl-4-benzo[b]fluorenyl, 11,11-dimethyl-5-benzo[b]fluorenyl, 11,11-dimethyl 11,11-dimethyl-6-benzo[b]fluorenyl, 11,11-dimethyl-7-benzo[b]fluorenyl, 11,11-dimethyl-8-benzo[b]fluorenyl, 11,11-dimethyl-9-benzo[b]fluorenyl, 11,11-dimethyl-10-benzo[b]fluorenyl, 11,11-dimethyl-1-benzo[c]fluorenyl, 11,11-dimethyl-2 -benzo[c]fluorenyl, 11,11-dimethyl-3-benzo[c]fluorenyl, 11,11-dimethyl-4-benzo[c]fluorenyl, 11,11-dimethyl-5-benzo[c]fluorenyl, 11,11-dimethyl-6-benzo[c]fluorenyl, 11,11-dimethyl-7-benzo[c]fluorenyl, 11,11-dimethyl-8-benzo[c]fluorenyl [c]fluorenyl, 11,11-dimethyl-9-benzo[c]fluorenyl, 11,11-dimethyl-10-benzo[c]fluorenyl, 11,11-diphenyl-1-benzo[a]fluorenyl, 11,11-diphenyl-2-benzo[a]fluorenyl, 11,11-diphenyl-3-benzo[a]fluorenyl, 11,11-diphenyl-4-benzo[a] Fluorenyl, 11,11-diphenyl-5-benzo[a]fluorenyl, 11,11-diphenyl-6-benzo[a]fluorenyl, 11,11-diphenyl-7-benzo[a]fluorenyl, 11,11-diphenyl-8-benzo[a]fluorenyl, 11,11-diphenyl-9-benzo[a]fluorenyl, 11,11-diphenyl-10-benzo[a]fluorenyl , 11,11-diphenyl-1-benzo[b]fluorenyl, 11,11-diphenyl-2-benzo[b]fluorenyl, 11,11-diphenyl-3-benzo[b]fluorenyl, 11,11-diphenyl-4-benzo[b]fluorenyl, 11,11-diphenyl-5-benzo[b]fluorenyl, 11,11-diphenyl-6-benzo[b]fluorenyl, 11,11-diphenyl-11-diphenyl-7-benzo[b]fluorenyl, 11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9-benzo[b]fluorenyl, 11,11-diphenyl-10-benzo[b]fluorenyl, 11,11-diphenyl-1-benzo[c]fluorenyl, 11,11-diphenyl-2-benzo[c]fluorenyl, 11,11-diphenyl-3-benzo[c]fluorenyl, 11,11-diphenyl-4-benzo[c]fluorenyl, 11,11-diphenyl-5-benzo[c]fluorenyl, 11,11-diphenyl- 6-Benzo[c]fluorenyl, 11,11-diphenyl-7-benzo[c]fluorenyl, 11,11-diphenyl-8-benzo[c]fluorenyl, 11,11-diphenyl-9-benzo[c]fluorenyl, 11,11-diphenyl-10-benzo[c]fluorenyl, 9,9,10,10-tetramethyl-9,10-dihydro-1-phenanthryl, 9,9,10,10-tetramethyl-9,10-dihydro-2-phenanthryl, 9,9,10,10-tetramethyl-9,10-dihydro-3-phenanthryl, 9,9,10,10-tetramethyl-9,10-dihydro-4-phenanthrenyl etc.In the present disclosure, " (3 yuan to 30 yuan) (sub) heteroaryl " is an aryl with 3 to 30 ring skeleton atoms, and these ring skeleton atoms include at least one heteroatom selected from the group consisting of B, N, O, S, Si, P, Se and Ge, wherein the number of ring skeleton carbon atoms is preferably 5 to 25. The number of heteroatoms in the heteroaryl is preferably 1 to 4. The above-mentioned heteroaryl can be a monocyclic or condensed ring with at least one benzene ring, and can be partially saturated. In addition, herein, the above-mentioned heteroaryl can be a heteroaryl formed by connecting at least one heteroaryl or aryl to a heteroaryl via one or more single bonds. Examples of heteroaryl groups specifically include monocyclic heteroaryl groups, including furanyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc.; and condensed ring heteroaryl groups, including benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, phenyl, dibenzothienyl, dibenzoselenophenyl, benzofuranoquinolyl, benzofuranoquinazolinyl, benzofurano naphthyridinyl, benzofuranopyrimidinyl, naphthyridinyl, benzothienoquinolyl, benzothienoquinazolinyl, benzothienonaphthyridinyl, benzothienopyrimidinyl, naphthyridinyl, pyrimidinyl, naphthyridinyl, pyrimidindolyl, benzopyrimidindolyl, benzofuranopyrazinyl, naphthyridinyl, benzothienopyrazinyl, naphthothiophenopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolane The heteroaryl group may be 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazine-4-yl, 1,2,4-triazine-3-yl, 1,3,5-triazine-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolizidinyl, 2-indolizidinyl, 3-indolizidinyl, 5-indolizidinyl, 6-indolizidinyl, 7-indolizidinyl, 8-indolizidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl yl, 7-imidazopyridinyl, 8-imidazopyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2- benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazole-1- yl, azacarbazole-2-yl, azacarbazole-3-yl, azacarbazole-4-yl, azacarbazole-5-yl, azacarbazole-6-yl, azacarbazole-7-yl, azacarbazole-8-yl, azacarbazole-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, -phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol- 3-Methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2-tert-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4-tert-butyl-1-indolyl, 2-tert-butyl-3-indolyl, 4-tert-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophene, 2-dibenzothiophene, 3-dibenzothiophene, 4-dibenzothiophene, 1-naphtho-[1,2-b]-benzofuranyl, 2-naphtho-[1,2-b]-benzofuranyl, 3-naphtho-[1,2-b]-benzofuranyl, 4-naphtho-[1,2-b]-benzofuranyl, 5-naphtho-[1,2-b]-benzofuranyl, 6-naphtho-[1,2-b]-benzofuranyl, 7-naphtho-[1,2-b]-benzofuranyl , 8-naphtho-[1,2-b]-benzofuranyl, 9-naphtho-[1,2-b]-benzofuranyl, 10-naphtho-[1,2-b]-benzofuranyl, 1-naphtho-[2,3-b]-benzofuranyl, 2-naphtho-[2,3-b]-benzofuranyl, 3-naphtho-[2,3-b]-benzofuranyl, 4-naphtho-[2, 3-b]-benzofuranyl, 5-naphtho-[2,3-b]-benzofuranyl, 6-naphtho-[2,3-b]-benzofuranyl, 7-naphtho-[2,3-b]-benzofuranyl, 8-naphtho-[2,3-b]-benzofuranyl, 9-naphtho-[2,3-b]-benzofuranyl, 10-naphtho-[2,3-b]-benzofuranyl 1-naphtho-[2,1-b]-benzofuranyl, 2-naphtho-[2,1-b]-benzofuranyl, 3-naphtho-[2,1-b]-benzofuranyl, 4-naphtho-[2,1-b]-benzofuranyl, 5-naphtho-[2,1-b]-benzofuranyl, 6-naphtho-[2,1-b]-benzofuranyl, 7-naphtho-[2,1-b]-benzofuranyl, 1-b]-benzofuranyl, 8-naphtho-[2,1-b]-benzofuranyl, 9-naphtho-[2,1-b]-benzofuranyl, 10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b]-benzothiophene, 2-naphtho-[1,2-b]-benzothiophene, 3-naphtho-[1,2-b]-benzothiophene 4-naphtho-[1,2-b]-benzothiophenyl, 5-naphtho-[1,2-b]-benzothiophenyl, 6-naphtho-[1,2-b]-benzothiophenyl, 7-naphtho-[1,2-b]-benzothiophenyl, 8-naphtho-[1,2-b]-benzothiophenyl, 9-naphtho-[1,2-b]-benzothiophenyl, 10-naphtho-[1 ,2-b]-benzothiophene, 1-naphtho-[2,3-b]-benzothiophene, 2-naphtho-[2,3-b]-benzothiophene, 3-naphtho-[2,3-b]-benzothiophene, 4-naphtho-[2,3-b]-benzothiophene, 5-naphtho-[2,3-b]-benzothiophene, 1-naphtho-[2,1-b]-benzothiophene 1-b-benzothiophene, 2-naphtho-[2,1-b]-benzothiophene, 3-naphtho-[2,1-b]-benzothiophene, 4-naphtho-[2,1-b]-benzothiophene, 5-naphtho-[2,1-b]-benzothiophene, 6-naphtho-[2,1-b]-benzothiophene, 7-naphtho-[2,1-b]-benzothiophene, 8-naphtho-[2,1-b]-benzothiophene,1-b]-benzothiophenyl, 9-naphtho-[2,1-b]-benzothiophenyl, 10-naphtho-[2,1-b]-benzothiophenyl, 2-benzofurano[3,2-d]pyrimidinyl, 6-benzofurano[3,2-d]pyrimidinyl, 7-benzofurano[3,2-d]pyrimidinyl, 8-benzofurano[3,2-d]pyrimidinyl, 9-benzofurano[3,2-d]pyrimidinyl, 2-benzothio[3,2-d]pyrimidinyl, 6-benzothio[3,2-d]pyrimidinyl, 7-benzothio[3,2-d]pyrimidinyl, 8-benzothio[3,2-d]pyrimidinyl, 9-benzothio[3,2-d]pyrimidinyl, 2-benzofurano[3,2-d]pyrimidinyl, 6-benzothio[3,2-d]pyrimidinyl, 7-benzothio[3,2-d]pyrimidinyl, 8-benzothio[3,2-d]pyrimidinyl, 9-benzothio[3,2-d]pyrimidinyl, 2-benzofurano[3,2-d]pyrimidinyl, -Benzofuranyl, 7-Benzofuranyl, 8-Benzofuranyl, 9-Benzofuranyl, 2-Benzothiol[3,2-d]pyrazinyl, 6-Benzothiol[3,2-d]pyrazinyl, 7-Benzothiol[3,2-d]pyrazinyl, 8-benzothio[3,2-d]pyrazinyl, 9-benzothio[3,2-d]pyrazinyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germanylfluorenyl, 2-germanylfluorenyl, 3-germanylfluorenyl, 4-germanylfluorenyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, etc. In addition, the "heteroaryl group" may be classified into a heteroaryl group having electron characteristics or a heteroaryl group having hole characteristics. The (sub)heteroaryl with electron characteristics is a substituent with relatively abundant electrons in the parent nucleus, and for example, it can be a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidyl, a substituted or unsubstituted triazine, a substituted or unsubstituted quinazoline, a substituted or unsubstituted quinoxaline, a substituted or unsubstituted quinolyl, etc. The (sub)heteroaryl with hole characteristics is a substituent with relatively deficient electrons in the parent nucleus, and for example, it can be a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophene, or a substituted or unsubstituted dibenzoselenophenyl. Herein, “(C3-C, 30 ) aliphatic ring and (C6-C 30 The term "condensed ring of (C3-C4) aromatic ring" means a ring formed by fusing at least one aliphatic ring having 3 to 30 ring skeleton carbon atoms (wherein the number of carbon atoms is preferably 3 to 25, more preferably 3 to 18) and at least one aromatic ring having 6 to 30 ring skeleton carbon atoms (wherein the number of carbon atoms is preferably 6 to 25, more preferably 6 to 18). For example, the condensed ring may be a condensed ring of at least one benzene and at least one cyclohexane, or a condensed ring of at least one naphthalene and at least one cyclopentane, etc. Herein, (C3-C4) aromatic ring means a ring formed by fusing at least one aliphatic ring having 3 to 30 ring skeleton carbon atoms (wherein the number of carbon atoms is preferably 3 to 25, more preferably 3 to 18) and at least one aromatic ring having 6 to 30 ring skeleton carbon atoms (wherein the number of carbon atoms is preferably 6 to 25, more preferably 6 to 18). 30 ) aliphatic ring and (C6-C 30) The carbon atoms in the fused ring of the aromatic ring may be replaced by at least one heteroatom selected from B, N, O, S, Si and P, preferably at least one heteroatom selected from N, O and S. In the present disclosure, "halogen" includes F, Cl, Br, and I.

[0041] In addition, "ortho-(o-)", "meta-(m-)", and "para-(p-)" are meant to represent the substitution position of all substituents. The ortho-configuration describes a compound having substituents adjacent to each other, for example, at positions 1 and 2 on benzene. The meta-configuration indicates the next substitution position of the immediately adjacent substitution position, for example, the compound has substituents at positions 1 and 3 on benzene. The para-configuration indicates the next substitution position of the meta position, for example, the compound has substituents at positions 1 and 4 on benzene.

[0042] Herein, "a ring formed by connecting to an adjacent substituent" means a substituted or unsubstituted (3- to 30-membered) monocyclic or polycyclic alicyclic ring, aromatic ring, or a combination thereof formed by connecting or fusing two or more adjacent substituents, and preferably, it may be a substituted or unsubstituted (3- to 26-membered) monocyclic or polycyclic alicyclic ring, aromatic ring, or a combination thereof. In addition, the formed ring may contain at least one heteroatom selected from the group consisting of B, N, O, S, Si and P, preferably, N, O and S. According to one embodiment of the present disclosure, the number of atoms in the ring skeleton is 5 to 20; according to another embodiment of the present disclosure, the number of atoms in the ring skeleton is 5 to 15. In one embodiment, the fused ring can be, for example, a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted benzene ring, or a substituted or unsubstituted carbazole ring, etc.

[0043] In addition, the term "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a functional group is replaced by another atom or functional group (i.e., a substituent). Unless otherwise specified, at a position where a substituent can be substituted, the substituent may not be limited to hydrogen, and when two or more hydrogen atoms in a functional group are each replaced by a substituent, the substituent may be the same or different from each other. 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 may be interpreted as a substituent in which two heteroaryls are connected. Preferably, the substituted alkyl, substituted alkenyl, substituted cycloalkyl, substituted heterocycloalkyl, substituted (ene)aryl, substituted (ene)heteroaryl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, and substituted triarylsilyl in the formulas of the present disclosure are each independently substituted by at least one selected from the group consisting of deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C 30 ) alkyl, halogenated (C1-C 30 )alkyl, (C2-C 30 )alkenyl, (C2-C 30 ) alkynyl, (C1-C 30 ) alkoxy, (C1-C 30 )alkylthio, (C3-C 30 )cycloalkyl, (C3-C 30 )cycloalkenyl, (3- to 7-membered)heterocycloalkyl, (C6-C 30 ) aryloxy, (C6-C 30 ) arylthio, unsubstituted or substituted with at least one (C6-C 30 )aryl-substituted (3- to 30-membered) heteroaryl, unsubstituted or (C1-C 30 (C6-C 30 )aryl, tri(C1-C 30 ) alkylsilyl, tri(C6-C 30 ) arylsilyl, di(C1-C 30 )alkyl(C6-C 30 ) arylsilyl, (C1-C 30 )alkyldi(C6-C 30 ) arylsilyl, tri(C6-C 30 ) arylgermanyl, amino, mono- or di-(C1-C 30 ) alkylamino, mono- or di-(C2-C 30 )alkenylamino, unsubstituted or (C1-C 30 ) alkyl-substituted mono- or di-(C6-C 30)arylamino, mono- or di-(3- to 30-membered) heteroarylamino, (C1-C 30 )alkyl(C2-C 30 )alkenylamino, (C1-C 30 )alkyl(C6-C 30 ) arylamino, (C1-C 30 )alkyl(3-30 membered)heteroarylamino, (C2-C 30 )Alkenyl (C6-C 30 ) arylamino, (C2-C 30 )alkenyl (3- to 30-membered) heteroarylamino, (C6-C 30 )aryl (3- to 30-membered) heteroarylamino, (C1-C 30 )alkylcarbonyl, (C1-C 30 ) alkoxycarbonyl, (C6-C 30 ) arylcarbonyl, di(C6-C 30 ) aryl boron carbonyl, di(C1-C 30 ) alkyl boron carbonyl, (C1-C 30 )alkyl(C6-C 30 ) aryl boron carbonyl, (C6-C 30 )Aryl (C1-C 30 )alkyl, (C1-C 30 )alkyl(C6-C 30 ) aryl, etc. For example, the substituent may be substituted by deuterium, methyl, tert-butyl, phenyl, or naphthyl, etc.

[0044] When a substituent is not shown in the chemical formula or compound structure of the present disclosure, this may mean that all positions that can appear as a substituent are hydrogen or deuterium. That is, in the case of deuterium (an isotope of hydrogen), some hydrogen atoms may be deuterium, which is an isotope; and in this case, the content of deuterium may be 0% to 100%. In the case where a substituent is not shown in the chemical formula or compound structure of the present disclosure, when deuterium is not explicitly excluded (such as when the content of deuterium is 0%, the content of hydrogen is 100%, and all substituents are hydrogen), hydrogen and deuterium may be mixed and used in the compound. Deuterium is an element having a deuteron composed of one proton and one neutron as an atomic nucleus, deuterium is one of the isotopes of hydrogen, and can be represented by hydrogen-2, and the element symbol may be D or 2 H. Although isotopes have the same atomic number (Z), isotopes with different mass numbers (A) mean that the same number of protons and neutrons can also be interpreted as having different numbers of elements.

[0045] In this document, "combinations thereof" means that one or more components of the corresponding list are combined to form known or chemically stable arrangements that can be imagined by a person skilled in the art from the corresponding list. For example, alkyl and deuterium can be combined to form partially or fully deuterated alkyl; halogen and alkyl can be combined to form haloalkyl substituents; and halogen, alkyl and aryl can be combined to form haloarylalkyl. For example, preferred combinations of substituents can include up to 50 atoms other than hydrogen and deuterium, or up to 40 atoms other than hydrogen and deuterium, or up to 30 atoms other than hydrogen and deuterium, or in many cases, preferred combinations of substituents can include up to 20 atoms other than hydrogen and deuterium.

[0046] In the formulae of the present disclosure, when a plurality of substituents are represented by the same symbol, each of these substituents represented by the same symbol may be the same as or different from each other.

[0047] Hereinafter, a compound according to one embodiment will be described.

[0048] The compound according to one embodiment of the present disclosure is represented by Formula 1 below.

[0049]

[0050] In formula 1,

[0051] X1 to X3 each independently represent CR5 or N, provided that at least one of X1 to X3 is N;

[0052] Ar1 represents hydrogen, deuterium, halogen, cyano, amino, substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C6-C 30 )aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (C1-C 30 )alkoxy, -Si(R 11 )(R 12 )(R 13 ), or -N(R 14 )(R 15 );

[0053] R 11 To R 15 Each independently represents a substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C2-C 30 )alkenyl, substituted or unsubstituted (C6-C 30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl;

[0054] L1 represents a single bond, substituted or unsubstituted (C6-C 30 )arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene;

[0055] R1 to R5 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C6-C 30 )aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (C1-C 30 ) alkoxy, substituted or unsubstituted tri(C1-C 30 )alkylsilyl, substituted or unsubstituted di(C1-C 30 )alkyl(C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 )alkyldi(C6-C 30 ) arylsilyl, or substituted or unsubstituted tri(C6-C 30 ) arylsilyl; or may be connected to adjacent substituents to form one or more rings;

[0056] Ar represents a substituted or unsubstituted (C6-C 30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; and

[0057] a, b, and d each independently represent an integer of 1 to 4, c represents an integer of 1 to 3, and when a to d are integers of 2 or more, each of R1 to R4 may be the same as or different from each other.

[0058] In one embodiment, at least two of X1 to X3 may be N.

[0059] In one embodiment, X1 to X3 can all be N.

[0060] In one embodiment, Ar1 may be substituted or unsubstituted (C6-C 30 )aryl or substituted or unsubstituted (5- to 30-membered) heteroaryl, preferably unsubstituted or substituted with (C1-C 30 ) alkyl substituted (C6-C 25 )aryl or substituted or unsubstituted (5- to 25-membered) heteroaryl, more preferably unsubstituted or substituted with (C1-C 10 ) alkyl substituted (C6-C 18)aryl or substituted or unsubstituted (5- to 18-membered) heteroaryl. For example, Ar1 can be phenyl which is unsubstituted or substituted with at least one of methyl, dimethyl, and tert-butyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted p-terphenyl, unsubstituted or substituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted The substituents may be further substituted with at least one deuterium.

[0061] In one embodiment, L1 can be a single bond or a substituted or unsubstituted (C6-C 30 )arylene, preferably a single bond or substituted or unsubstituted (C6-C 25 )arylene, more preferably a single bond or substituted or unsubstituted (C6-C 18 For example, L1 may be a single bond, an unsubstituted or phenylene group substituted with a phenyl group, or a substituted or unsubstituted biphenylene group.

[0062] In one embodiment, R1 to R5 are each independently hydrogen, deuterium, halogen, cyano, or substituted or unsubstituted (C6-C 30 ) aryl. For example, R1, R2, and R5 can each independently be hydrogen or deuterium, and R3 and R4 can each independently be hydrogen, deuterium, or substituted or unsubstituted phenyl.

[0063] In one embodiment, Ar can be substituted or unsubstituted (C6-C 30 )aryl or substituted or unsubstituted (5-30-membered) heteroaryl, preferably a substituted or unsubstituted (5-30-membered) heteroaryl having a hole characteristic. For example, Ar can be a dibenzofuranyl unsubstituted or substituted with methyl or phenyl, a substituted or unsubstituted dibenzothienyl, or a substituted or unsubstituted dibenzoselenophenyl.

[0064] According to one embodiment, the compound represented by Formula 1 may be represented by the following Formula 1-1.

[0065]

[0066] In formula 1-1,

[0067] R1 to R4, X1 to X3, Ar1, L1, and a to d are as defined in Formula 1;

[0068] X represents O, S, or Se;

[0069] R6 and R7 are as defined for R1 in Formula 1; and

[0070] e represents an integer of 1 to 3, f represents an integer of 1 to 4, and when e and f are integers of 2 or more, each R6 and each R7 may be the same as or different from each other.

[0071] According to one embodiment, the compound represented by Formula 1 can be more specifically illustrated by the following compounds, but is not limited thereto:

[0072]

[0073]

[0074]

[0075]

[0076] Among them, "D n " means that n number of hydrogens are replaced by deuterium, wherein n represents an integer of 1 or more, and the upper limit of n is determined by the number of hydrogens that can be replaced in each compound.

[0077] The compound represented by Formula 1 according to the present disclosure may be prepared by a synthetic method known to those skilled in the art.

[0078] According to another embodiment, the present disclosure provides an organic electroluminescent material including a compound represented by Formula 1 above and a compound represented by Formula 2 below.

[0079]

[0080] In formula 2,

[0081] A1 and A2 each independently represent a substituted or unsubstituted (C6-C 30 ) aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazolyl;

[0082] X 15 To X 18 Any one of 19 To X 22 Any of are connected to each other to form a single bond; and

[0083] X 11 To X 14 , X 23 To X 26 , and X that does not form a single bond 15 To X 22 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; or may be connected to adjacent substituents to form one or more rings.

[0084] In one embodiment, A1 and A2 are each independently substituted or unsubstituted (C6-C 25 )aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazolyl. For example, A1 and A2 can each independently be unsubstituted or deuterated phenyl; unsubstituted or deuterated biphenyl; unsubstituted or deuterated terphenyl; unsubstituted or deuterated naphthyl; unsubstituted or deuterated, (C1-C 30 ) alkyl, and (C6-C 30 ) aryl substituted with at least one fluorenyl; unsubstituted or deuterated, (C1-C 30 ) alkyl, and (C6-C 30 ) at least one substituted benzofluorenyl group in the aromatic group; an unsubstituted or deuterium substituted triphenylene group; an unsubstituted or deuterium substituted fluoranthene group; an unsubstituted or deuterium substituted phenanthryl group; an unsubstituted or deuterium substituted dibenzofuranyl group; an unsubstituted or deuterium substituted dibenzothienyl group; an unsubstituted or deuterium substituted carbazolyl group; or a combination thereof. For example, A1 and A2 can each independently be substituted or unsubstituted phenyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, unsubstituted or phenyl-substituted naphthyl, substituted or unsubstituted fluorenyl, unsubstituted or phenyl-substituted benzofluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluoranthene, substituted or unsubstituted phenanthrenyl, unsubstituted or phenyl-substituted triphenylene, unsubstituted or phenyl-substituted dibenzofuranyl, unsubstituted or phenyl-substituted dibenzothiophenyl, or unsubstituted or phenyl- or naphthyl-substituted carbazolyl.

[0085] Wherein, A1 and A2 can be independently deuterated, (C6-C 30 )aryl, and (3- to 30-membered) heteroaryl, for example, may be substituted with deuterium, (C6-C 18 )aryl, and (5- to 20-membered) heteroaryl. For example, A1 and A2 may each independently be substituted by at least one of phenyl, naphthyl, triphenylene, dibenzofuranyl, and dibenzothienyl, and may be further substituted by at least one deuterium.

[0086] According to one embodiment, the compound represented by Formula 2 may be represented by any one of the following Formulas 2-1 to 2-8.

[0087]

[0088]

[0089] In formulas 2-1 to 2-8,

[0090] A1, A2, and X 11 To X 26 is defined as in Equation 2.

[0091] In one embodiment, X 11 To X 14 , X 23 To X 26 , and X that does not form a single bond 15 To X 22 Each independently may be hydrogen, deuterium, substituted or unsubstituted (C6-C 30 )aryl, or substituted or unsubstituted (5- to 30-membered) heteroaryl, or may be connected to adjacent substituents to form one or more rings, preferably hydrogen, deuterium, substituted or unsubstituted (C6-C 25 )aryl, or substituted or unsubstituted (5- to 25-membered) heteroaryl, more preferably hydrogen or deuterium. For example, X 11 To X 14 , X 23 To X 26 , and X that does not form a single bond 15 To X 22 At least four of the may be deuterium.

[0092] In one embodiment, X 11 , X 18 , X 19 , and X 26 At least one of may be deuterium.

[0093] In one embodiment, X 11 , X 18 , X 19 , and X 26 At least two of may be deuterium.

[0094] In one embodiment, X 11 , X 18 , X 19 , and X 26 At least three of may be deuterium.

[0095] In one embodiment, X 11 , X 18 , X 19 , and X 26 All can be deuterium.

[0096] In one embodiment, when X 16 and X 21 When connected to each other to form a single bond, X 11 , X 18 , X 19 , and X 26 All can be deuterium, and when X 18 and X 19 When connected to each other to form a single bond, X 11 and X 26 It could be deuterium.

[0097] In one embodiment, X 11 To X 26 The deuterium substitution rate may be 25% to 100%, such as 35% to 100%, such as 45% to 100%, or such as 55% to 100%. The upper limit of the deuterium substitution rate may be 100%, but may also be less than 100%, such as about 99%.

[0098] According to one embodiment, in the compound represented by Formula 2, the deuterium substitution rate may be 40% to 100%, such as 50% to 100%, such as 60% to 100%, or such as 70% to 100%. The upper limit of the deuterium substitution rate may be 100%, but may also be less than 100%, such as about 99%. That is, the compound represented by Formula 2 may be a compound in which all hydrogens at the substitutable positions are substituted by deuterium, or a compound in which hydrogens at the substitutable positions are partially substituted by deuterium.

[0099] When the compound represented by Formula 2 contains deuterium substituted according to the above number or ratio, bond dissociation energy according to deuteration increases, thereby increasing the stability of the compound represented by Formula 2. When such a compound represented by Formula 2 is used in an organic electroluminescent device, it can exhibit improved lifespan characteristics.

[0100] According to one embodiment, the compound represented by Formula 2 may be more specifically illustrated by the following compounds, but is not limited thereto.

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114] In the above compounds, D n This means that n number of hydrogens are replaced by deuterium.

[0115] The compound represented by Formula 2 according to the present disclosure may be prepared by referring to Japanese Patent No. 3139321, etc. In addition, some of the compounds represented by Formula 2 according to the present disclosure may be prepared as shown in the following Reaction Scheme 1, but are not limited thereto.

[0116] [Reaction Scheme 1]

[0117]

[0118] In reaction scheme 1, A1, A2 and X 11 To X 26 is defined as in Equation 2, and D n This means that n number of hydrogens are replaced by deuterium.

[0119] As described above, exemplary synthesis examples of the compound represented by Formula 2 according to the present disclosure are described, but they are based on Buchwald-Hartwig cross-coupling reaction, N-arylation reaction, acidified montmorillonite (H-mont) mediated etherification reaction, Miyaura borylation reaction, Suzuki cross-coupling reaction, intramolecular acid-induced cyclization reaction, Pd (II) catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, dehydration cyclization reaction, S N 1 Substitution reaction, S N 2 substitution reaction, phosphine-mediated reductive cyclization reaction, etc. It should be understood by those skilled in the art that the above reaction continues even if other substituents defined in Formula 2 other than the substituents described in the specific synthetic example are bonded.

[0120] According to another embodiment, the present disclosure provides an organic electroluminescent material including a compound represented by Formula 1 above and a compound represented by Formula 3 below.

[0121]

[0122] In formula 3,

[0123] A3 represents a substituted or unsubstituted (C6-C 30 ) aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, or substituted or unsubstituted carbazolyl;

[0124] L2 represents a single bond, or a substituted or unsubstituted (C6-C 30 ) arylene;

[0125] A pair of adjacent X 35 To X 38 Connected to the following formula 3-A to form one or more rings, and X that does not form a ring 35 To X 38 and X 31 To X 34 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C 30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl;

[0126]

[0127] In Formula 3-A,

[0128] A4 represents a substituted or unsubstituted (C6-C 30 ) aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, or substituted or unsubstituted carbazolyl;

[0129] L3 represents a single bond, or a substituted or unsubstituted (C6-C 30 ) arylene; and

[0130] X 41 To X 44 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C 30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl.

[0131] In one embodiment, L2 and L3 can each independently be a single bond or a substituted or unsubstituted (C6-C 30 )arylene, preferably a single bond or substituted or unsubstituted (C6-C 25 )arylene, more preferably a single bond or substituted or unsubstituted (C6-C 18For example, L2 and L3 can each independently be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

[0132] In one embodiment, A3 and A4 are each independently substituted or unsubstituted (C6-C 25 ) aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, or substituted or unsubstituted carbazolyl. For example, A3 and A4 can each independently be phenyl which is unsubstituted or substituted with naphthyl or triphenylene, naphthyl which is unsubstituted or substituted with phenyl, substituted or unsubstituted p-biphenylyl, substituted or unsubstituted m-biphenylyl, substituted or unsubstituted o-biphenylyl, substituted or unsubstituted p-terphenylyl, substituted or unsubstituted m-terphenylyl, substituted or unsubstituted o-terphenylyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted dibenzoselenophenyl.

[0133] In one embodiment, a pair of adjacent X 35 To X 38 Connected to the above formula 3-A to form a ring, which can be represented by any one of the following formulae 3-1 to 3-6.

[0134]

[0135] In formulas 3-1 to 3-6,

[0136] A3, A4, L2, L3, X 31 To X 38 and X 41 To X 44 is defined as in Equation 3.

[0137] In one embodiment, X that does not form a ring 35 To X 38 , X 31 To X 34 and X 41 To X 44 Each independently can be hydrogen or deuterium.

[0138] According to one embodiment, in the compound represented by Formula 3, the deuterium substitution rate may be 40% to 100%, such as 50% to 100%, such as 60% to 100%, or such as 70% to 100%. The upper limit of the deuterium substitution rate may be 100%, but may also be less than 100%, such as about 99%. That is, the compound represented by Formula 3 may be a compound in which all hydrogens at the substitutable positions are substituted by deuterium, or a compound in which hydrogens at the substitutable positions are partially substituted by deuterium.

[0139] When the compound represented by Formula 3 contains deuterium substituted according to the above number or ratio, bond dissociation energy according to deuteration increases, thereby increasing the stability of the compound represented by Formula 3. When such a compound represented by Formula 3 is used in an organic electroluminescent device, it can exhibit improved lifespan characteristics.

[0140] According to one embodiment, the compound represented by Formula 3 may be more specifically illustrated by the following compounds, but is not limited thereto.

[0141]

[0142]

[0143]

[0144]

[0145]

[0146] In the above compounds, D n It means that n number of hydrogens are replaced by deuterium, wherein n is an integer of 1 or more, and the upper limit of n is determined according to the number of hydrogens that can be replaced in each compound.

[0147] Hereinafter, an organic electroluminescent device using the aforementioned compound and / or an organic electroluminescent compound including the same will be described.

[0148] An organic electroluminescent device according to an embodiment includes a first electrode, a second electrode, and at least one organic layer between the first electrode and the second electrode. The organic layer includes at least one light-emitting layer.

[0149] According to one embodiment, at least one light-emitting layer may include a compound represented by Formula 1. According to another embodiment, at least one light-emitting layer may include a compound represented by Formula 1 as a first host compound and a compound represented by Formula 2 or 3 as a second host compound, respectively, wherein a weight ratio of the first host compound to the second host compound in the light-emitting layer may be in the range of about 1:99 to about 99:1, preferably about 10:90 to about 90:10, more preferably about 30:70 to about 70:30, more preferably about 40:60 to about 60:40, and even more preferably about 50:50.

[0150] According to one embodiment, the organic electroluminescent material of the present disclosure includes at least one compound of compounds C-1 to C-100, and at least one compound of compounds H2-1 to H2-290 or at least one compound of compounds H1-1 to H1-125. The organic electroluminescent materials may be included in the same organic layer, such as the same light-emitting layer, or may be included in different light-emitting layers.

[0151] In addition to the light-emitting layer, the organic layer may also include at least one layer selected from the following: hole injection layer, hole transport layer, hole auxiliary layer, luminescent auxiliary layer, electron transport layer, electron injection layer, intermediate layer, hole blocking layer, electron blocking layer and electron buffer layer. In addition to the light-emitting material according to the present disclosure, the organic layer may further include amine-based compounds and / or azine-based compounds. Specifically, the hole injection layer, hole transport layer, hole auxiliary layer, light-emitting layer, luminescent auxiliary layer, or electron blocking layer may contain amine-based compounds (e.g., arylamine-based compounds and styrylarylamine-based compounds, etc.) as hole injection materials, hole transport materials, hole auxiliary materials, luminescent materials, luminescent auxiliary materials, or electron blocking materials. In addition, the electron transport layer, electron injection layer, electron buffer layer, or hole blocking layer may contain azine-based compounds as electron transport materials, electron injection materials, electron buffer materials, or hole blocking materials. In addition, the organic layer may further contain at least one metal selected from the group consisting of metals of Group 1 of the periodic table, metals of Group 2, transition metals of Period 4, transition metals of Period 5, lanthanoids and organometallics of d-transition elements, or at least one complex compound containing such a metal.

[0152] The organic electroluminescent material according to one embodiment can be used as a light-emitting material for a white organic light-emitting device. According to the arrangement of R (red), G (green), YG (yellow-green), or B (blue) light-emitting units, the white organic light-emitting device has various proposed structures, such as a parallel side-by-side arrangement method, a stacked arrangement method, or a CCM (color conversion material) method, etc. In addition, according to one embodiment, the organic electroluminescent material can also be applied to an organic electroluminescent device containing QD (quantum dots).

[0153] One of the first electrode and the second electrode may be an anode, and the other may be a cathode, wherein the first electrode and the second electrode may each be formed as a transmissive conductive material, a semi-transmissive reflective conductive material, or a reflective conductive material. Depending on the type of material forming the first electrode and the second electrode, the organic electroluminescent device may be a top emission type, a bottom emission type, or a double-sided emission type.

[0154] A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof can be used between the anode and the light-emitting layer. The hole injection layer can be a multilayer in order to reduce the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, wherein each of the multilayers can use two compounds at the same time. In addition, the hole injection layer can be doped with a p-type dopant. In addition, the electron blocking layer can be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and the excitons can be confined in the light-emitting layer by blocking the electrons from overflowing from the light-emitting layer to prevent light leakage. The hole transport layer or the electron blocking layer can be a multilayer, wherein each layer can use a variety of compounds.

[0155] An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be used between the light-emitting layer and the cathode. The electron buffer layer may be a multilayer to control the injection of electrons and improve the interface characteristics between the light-emitting layer and the electron injection layer, wherein each of the multilayers may use two compounds simultaneously. The hole blocking layer may be placed between the electron transport layer (or electron injection layer) and the light-emitting layer, and blocks holes from reaching the cathode, thereby increasing the probability of recombination of electrons and holes in the light-emitting layer. The hole blocking layer or the electron transport layer may also be a multilayer, wherein each layer may use a variety of compounds. In addition, the electron injection layer may be doped with an n-type dopant.

[0156] The luminescence auxiliary layer can be placed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer. When the luminescence auxiliary layer is placed between the anode and the light-emitting layer, it can be used to promote hole injection and / or hole transport, or to prevent electron overflow. When the luminescence auxiliary layer is placed between the cathode and the light-emitting layer, it can be used to promote electron injection and / or electron transport, or to prevent hole overflow. In addition, the hole auxiliary layer can be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can effectively promote or limit the hole transport rate (or hole injection rate), so that the charge balance can be controlled. When the organic electroluminescent device includes two or more hole transport layers, the hole transport layer further included can be used as a hole auxiliary layer or an electron blocking layer. The luminescence auxiliary layer, the hole auxiliary layer, or the electron blocking layer can have the effect of improving the efficiency and / or life of the organic electroluminescent device.

[0157] In the organic electroluminescent device of the present disclosure, at least one layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter, "surface layer") may be preferably placed on one or more inner surfaces of one electrode or both electrodes of a pair of electrodes. Specifically, a chalcogenide (including oxide) layer of silicon and aluminum is preferably placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or a metal oxide layer is preferably placed on the cathode surface of the electroluminescent medium layer. The operational stability of the organic electroluminescent device can be obtained by the surface layer. Preferably, the chalcogenide includes SiO X (1≤X≤2), AlO X (1≤X≤1.5), SiON, SiAlON, etc.; metal halides include LiF, MgF2, CaF2, rare earth metal fluorides, etc.; and metal oxides include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0158] In addition, in the organic electroluminescent device of the present disclosure, a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant can be placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to anions, and thus it becomes easier to inject and transport electrons from the mixed region to the electroluminescent medium. In addition, the hole transport compound is oxidized to a cation; therefore, it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium. Preferably, the oxidative dopant includes various Lewis acids and acceptor compounds, and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, the reductive dopant layer can be used as a charge generation layer to prepare an organic electroluminescent device having two or more light-emitting layers and emitting white light.

[0159] The organic electroluminescent device according to one embodiment of the present disclosure may be an organic electroluminescent device having a tandem structure. In the case of a tandem organic electroluminescent device according to one embodiment, a single light-emitting unit (light-emitting unit) may be formed into a structure in which two or more units are connected by a charge generation layer. The organic electroluminescent device may include a plurality of two or more light-emitting units, for example, a plurality of three or more light-emitting units, the light-emitting unit having a first electrode and a second electrode opposite to each other on a substrate and a light-emitting layer stacked between the first electrode and the second electrode and emitting light within a specific wavelength range. According to one embodiment, the organic electroluminescent device may include a plurality of light-emitting units, and each of these light-emitting units may include a hole transport band, a light-emitting layer, and an electron transport band, and the hole transport band may include a hole injection layer and a hole transport layer, and the electron transfer zone may include an electron transport layer and an electron injection layer. According to one embodiment, three or more light-emitting layers may be included in the light-emitting unit. Multiple light-emitting units may emit the same color or different colors. In addition, a light-emitting unit may include one or more light-emitting layers, and multiple light-emitting layers may be light-emitting layers of the same or different colors. It may include one or more charge generation layers located between each light-emitting unit. A charge generation layer refers to a layer that generates holes and electrons when a voltage is applied. When there are three or more light-emitting units, the charge generation layer may be located between the light-emitting units. Here, the multiple charge generation layers may be the same as or different from each other. By arranging the charge generation layer between the light-emitting units, the current efficiency in each light-emitting unit is increased, and the charge can be evenly distributed. Specifically, the charge generation layer is disposed between two adjacent stacks, and can be used to drive a tandem organic electroluminescent device using only a pair of anodes and cathodes, without the need for a separate internal electrode located between the stacks.

[0160] The charge generation layer may be composed of an n-type charge generation layer and a p-type charge generation layer, and the n-type charge generation layer may be doped with an alkali metal, an alkaline earth metal, or a compound of an alkali metal and an alkaline earth metal. The alkali metal may include one selected from the group consisting of Li, Na, K, Rb, Cs, Fr, Yb, and combinations thereof, and the alkaline earth metal may include one selected from the group consisting of Be, Mg, Ca, Sr, Ba, Ra, and combinations thereof. The p-type charge generation layer may be made of a metal or an organic material doped with a p-type dopant. For example, the metal may be made of one or two or more alloys selected from the group consisting of: Al, Cu, Fe, Pb, Zn, Au, Pt, W, In, Mo, Ni, and Ti. In addition, commonly used materials may be used as p-type dopants and host materials used in p-type doped organic materials.

[0161] The organic electroluminescent device according to one embodiment may further include at least one dopant in the light emitting layer.

[0162] The dopant included in the organic electroluminescent device of the present disclosure may be at least one phosphorescent dopant or fluorescent dopant, preferably a phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particularly limited, but may preferably be one or more metallized complex compounds of one or more metal atoms selected from the following: iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably one or more ortho-metallized complex compounds of one or more metal atoms selected from the following: iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably one or more ortho-metallized iridium complex compounds.

[0163] The dopant included in the organic electroluminescent device of the present disclosure may use a compound represented by the following Formula 101, but is not limited thereto.

[0164]

[0165] In formula 101,

[0166] L is any one selected from the following structures 1 to 3:

[0167]

[0168] In structures 1 to 3,

[0169] R 100 To R 103 Each independently represents hydrogen, deuterium, halogen, unsubstituted or substituted by deuterium and / or halogen (C1-C 30 ) alkyl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (C6-C 30 )aryl, cyano, substituted or unsubstituted (3- to 30-membered) heteroaryl, or substituted or unsubstituted (C1-C 30 ) alkoxy; or may be attached to an adjacent substituent to form one or more rings, such as forming one or more rings with pyridine, for example, substituted or unsubstituted quinoline, substituted or unsubstituted benzofuranopyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuranoquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indenoquinoline;

[0170] R 104 To R 107 Each independently represents hydrogen, deuterium, halogen, unsubstituted or substituted by deuterium and / or halogen (C1-C 30 ) alkyl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (C6-C30 )aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, cyano, or substituted or unsubstituted (C1-C 30 ) alkoxy; or may be connected to one or more adjacent substituents to form one or more substituted or unsubstituted rings, such as forming one or more substituted or unsubstituted rings with benzene, for example, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuranopyridine, or substituted or unsubstituted benzothienopyridine;

[0171] R 201 To R 220 Each independently represents hydrogen, deuterium, halogen, unsubstituted or substituted by deuterium and / or halogen (C1-C 30 ) alkyl, substituted or unsubstituted (C3-C 30 )cycloalkyl, or substituted or unsubstituted (C6-C 30 ) aryl; or may be attached to one or more adjacent substituents to form one or more substituted or unsubstituted rings; and

[0172] s represents an integer of 1 to 3.

[0173] Specifically, specific examples of the dopant compound include the following, but are not limited thereto.

[0174]

[0175]

[0176]

[0177]

[0178]

[0179] In order to form each layer of the organic electroluminescent device of the present disclosure, a dry film-forming method such as vacuum evaporation, sputtering, plasma, ion plating method, etc., or a wet film-forming method such as spin coating, dip coating, flow coating method, etc. can be used. When a wet film-forming method is used, a thin film can be formed by dissolving or diffusing the material forming each layer in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent can be any solvent in which the material forming each layer can be dissolved or diffused and there is no problem in film-forming ability.

[0180] When a layer is formed by an organic electroluminescent material according to an embodiment, the layer may be formed by the methods listed above, and may generally be formed by co-deposition or mixed deposition. Co-deposition is a mixed deposition method in which two or more materials are put into a corresponding single crucible source and current is applied to two chambers at the same time to evaporate the materials and perform mixed deposition; and mixed deposition is a mixed deposition method in which two or more materials are mixed in one crucible source before being deposited and then current is applied to one chamber to evaporate the materials.

[0181] According to one embodiment, the present disclosure may provide a display device including a compound represented by Formula 1 and / or a display device including an organic electroluminescent material including a first host compound represented by Formula 1 and a second host compound represented by Formula 2 or 3. In addition, the organic electroluminescent device of the present disclosure may be used to manufacture a display device such as a display device of a smartphone, a tablet computer, a notebook computer, a PC, a TV, or a vehicle, or a lighting device such as outdoor or indoor lighting.

[0182] Hereinafter, the preparation method of the compound according to the present disclosure will be explained with reference to the synthesis method of representative compounds or intermediate compounds in order to understand the present disclosure in detail.

[0183] [Example 1] Synthesis of Compound C-32

[0184]

[0185] Compound A (6.0 g, 11.21 mmol), 9-(4-chloro-6-phenyl-1,3,5-triazine-2-yl)-9H-carbazole (4.4 g, 12.33 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (0.4 g, 0.34 mmol), potassium carbonate (K2CO3) (3.8 g, 28.01 mmol), 56 mL of toluene, 14 mL of ethanol and 14 mL of distilled water were added to a flask and dissolved, and then stirred under reflux for 4 hours. When the reaction was completed, the organic layer was extracted with ethyl acetate and separated by column chromatography to obtain compound C-32 (4.8 g, yield: 58%).

[0186] MW MP C-32 729.84 273℃

[0187] Hereinafter, a preparation method of an organic electroluminescent device including the compound according to the present disclosure and an organic electroluminescent material including the compound and device characteristics thereof will be explained in order to understand the present disclosure in detail.

[0188] [Device Example 1] Preparation of a green-light-emitting OLED deposited with an organic electroluminescent material according to the present disclosure

[0189] An OLED according to the present disclosure is prepared. First, a transparent electrode indium tin oxide (ITO) film (10Ω / sq) (GEOMATEC CO., LTD., Japan) on a glass substrate for OLED is subjected to ultrasonic washing with acetone and isopropanol in sequence, and thereafter stored in isopropanol and then used. Thereafter, the ITO substrate is mounted on a substrate holder of a vacuum vapor deposition device. Then, compound HI-1 is introduced into a chamber of the vacuum vapor deposition device, and compound HT-1 is introduced into another chamber. The two materials are evaporated at different rates, and compound HI-1 is deposited at a doping amount of 3wt% based on the total amount of compounds HI-1 and HT-1 to form a hole injection layer having a thickness of 10nm. Next, compound HT-1 is deposited on the hole injection layer as a first hole transport layer having a thickness of 80nm. Then the compound HT-2 is introduced into another chamber of the vacuum vapor deposition equipment, and the compound is evaporated by applying an electric current to the chamber, thereby forming a second hole transport layer with a thickness of 30nm on the first hole transport layer. After the hole injection layer and the hole transport layer are formed, a light-emitting layer is formed thereon as follows: each of the first host compound and the second host compound described in Table 1 below is introduced as a host into two chambers of the vacuum vapor deposition equipment, and the compound D-130 is introduced into another chamber as a dopant. The two host materials are evaporated at a ratio of 1:2 (first host: second host), and the dopant material is evaporated at different ratios and deposited at a doping amount of 10wt% based on the total amount of the host and the dopant to form a light-emitting layer with a thickness of 40nm on the second hole transport layer. Next, the compounds ETL-1 and EIL-1 are deposited as electron transport materials at a weight ratio of 40:60 to form an electron transport layer with a thickness of 35nm on the light-emitting layer. After the compound EIL-1 was deposited as an electron injection layer with a thickness of 2 nm on the electron transport layer, an Al cathode with a thickness of 80 nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus. Thus, an OLED was produced. Each compound for all materials was deposited by 10 -6 Purify by vacuum sublimation.

[0190] [Comparative Example 1] Preparation of OLED containing comparative compound as host

[0191] An OLED was manufactured in the same manner as in Device Example 1, except that Compound A-1 was used as the first host of the light-emitting layer.

[0192] [Comparative Example 2] Preparation of OLED containing comparative compound as host

[0193] An OLED was manufactured in the same manner as in Device Example 1, except that Compound A-2 was used as the first host of the light-emitting layer.

[0194] The driving voltage and emission color of the OLEDs of Device Example 1 and Comparative Examples 1 and 2 produced as described above at a luminance of 1,000 nits and the time taken for the luminance to decrease from 100% to 80% at a luminance of 60,000 nits (lifetime: T 80 ), and the results are shown in Table 1 below.

[0195] Table 1

[0196]

[0197]

[0198] [Device Example 2] Preparation of a green-light-emitting OLED deposited with an organic electroluminescent material according to the present disclosure

[0199] An OLED was manufactured in the same manner as in Device Example 1, except that Compound H2-2-D23 was used as the second host of the light-emitting layer.

[0200] [Comparative Example 3] Preparation of OLED containing comparative compound as host

[0201] An OLED was manufactured in the same manner as in Device Example 2, except that Compound A-1 was used as the first host of the light-emitting layer.

[0202] [Comparative Example 4] Preparation of OLED containing comparative compound as host

[0203] An OLED was manufactured in the same manner as in Device Example 2, except that Compound A-2 was used as the first host of the light-emitting layer.

[0204] The driving voltage and emission color of the OLEDs of Device Example 2 and Comparative Examples 3 and 4 produced as described above at a luminance of 1,000 nits and the time taken for the luminance to decrease from 100% to 80% at a luminance of 60,000 nits (lifetime: T 80 ), and the results are shown in Table 2 below.

[0205] Table 2

[0206]

[0207] As shown in Tables 1 and 2 above, it was confirmed that the organic electroluminescent devices including the organic electroluminescent material according to the present disclosure (Device Examples 1 and 2) exhibited excellent lifespan characteristics compared to organic electroluminescent devices including conventional host combinations (Comparative Examples 1 to 4).

[0208] The life of an organic electroluminescent device that emits green light is generally shorter than that of an organic electroluminescent device that emits red light. In order to improve the life characteristics of an organic electroluminescent device that emits green light, a compound with a novel structure and a compound that introduces a deuterium-modified portion are used in the present disclosure. Without being limited by theory, when an organic electroluminescent compound is substituted with deuterium, the zero-point vibrational energy of the compound is reduced, thereby increasing the bond dissociation energy (BDE) in the compound. As a result, the stability of the compound can be increased.

[0209] [Device Example 3] Preparation of OLEDs containing compounds according to the present disclosure as a single host material

[0210] Prepare an OLED according to the present disclosure. First, a transparent electrode indium tin oxide (ITO) film (10Ω / sq) (Giomar Co., Ltd., Japan) on a glass substrate for OLED is subjected to ultrasonic washing with acetone and isopropanol in sequence, and thereafter stored in isopropanol and then used. Thereafter, the ITO substrate is mounted on a substrate holder of a vacuum vapor deposition device. Then, compound HI-1 is introduced into a chamber of the vacuum vapor deposition device, and compound HT-1 is introduced into another chamber. The two materials are evaporated at different rates, and compound HI-1 is deposited at a doping amount of 3wt% based on the total amount of compound HI-1 and HT-1 to form a hole injection layer with a thickness of 10nm. Next, compound HT-1 is deposited on the hole injection layer as a first hole transport layer with a thickness of 80nm. Compound HT-2 is then introduced into another chamber of the vacuum vapor deposition device, and the compound is evaporated by applying an electric current to the chamber, thereby forming a second hole transport layer with a thickness of 30nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light-emitting layer was formed thereon as follows: Compound C-32 was introduced as a host into a chamber of a vacuum vapor deposition device, and compound D-130 was introduced as a dopant into another chamber. The dopant materials were evaporated simultaneously at different rates and deposited at a doping amount of 10wt% based on the total amount of the host and the dopant to form a light-emitting layer with a thickness of 40nm on the second hole transport layer. Next, compounds ETL-1 and EIL-1 were deposited as electron transport materials at a weight ratio of 40:60 to form an electron transport layer with a thickness of 35nm on the light-emitting layer. After compound EIL-1 was deposited as an electron injection layer with a thickness of 2nm on the electron transport layer, an Al cathode with a thickness of 80nm was deposited on the electron injection layer by another vacuum vapor deposition device. Thus, an OLED was produced. Each compound used for all materials was deposited by 10 -6 Purify by vacuum sublimation.

[0211] [Comparative Example 5] Preparation of OLED containing conventional compounds as a host

[0212] An OLED was manufactured in the same manner as in Device Example 3, except that Compound A-1 was used as a host of the light-emitting layer.

[0213] [Comparative Example 6] Preparation of OLED containing conventional compounds as a host

[0214] An OLED was manufactured in the same manner as in Device Example 3, except that Compound A-2 was used as a host of the light-emitting layer.

[0215] The driving voltage and emission color of the OLEDs of device Example 3 and Comparative Examples 5 and 6 produced as described above at a luminance of 1,000 nits and the time taken for the luminance to decrease from 100% to 80% at a luminance of 20,000 nits (lifetime: T 80 ), and the results are shown in Table 3 below.

[0216] Table 3

[0217]

[0218] It can be confirmed from Table 3 above that, compared with organic electroluminescent devices containing conventional host compounds (Comparative Examples 5 and 6), the organic electroluminescent device (Device Example 3) containing the compound with a novel structure according to the present disclosure as the host material of the light-emitting layer exhibits lower driving voltage and / or excellent life characteristics.

[0219] The compounds used in the device examples and comparative examples are specifically shown in Table 4 below.

[0220] Table 4

[0221]

[0222]

[0223] [Device Example 4] Preparation of a green-light-emitting OLED deposited with an organic electroluminescent material according to the present disclosure

[0224] An OLED was manufactured in the same manner as in Device Example 1, except that Compound H1-7 was used as the second host of the light-emitting layer.

[0225] [Device Example 5] Preparation of a green-light-emitting OLED deposited with an organic electroluminescent material according to the present disclosure

[0226] An OLED was manufactured in the same manner as in Device Example 1, except that Compound H1-97-D20 was used as the second host of the light-emitting layer.

[0227] [Comparative Example 7] Preparation of OLED containing comparative compound as host

[0228] An OLED was manufactured in the same manner as in Device Example 4, except that Compound A-2 was used as the first host of the light-emitting layer.

[0229] [Comparative Example 8] Preparation of OLED containing comparative compound as host

[0230] An OLED was manufactured in the same manner as in Device Example 5, except that Compound A-2 was used as the first host of the light-emitting layer.

[0231] The driving voltage, luminous efficiency, and luminescent color of the OLEDs of Device Examples 4 and 5 and Comparative Examples 7 and 8 produced as described above at a luminance of 1,000 nit were measured, and the results thereof are shown in Table 5 below.

[0232] Table 5

[0233]

[0234] As shown in Table 5 above, it is confirmed that the organic electroluminescent devices (Device Examples 4 and 5) containing the organic electroluminescent material according to the present disclosure exhibit lower driving voltage and / or excellent efficiency characteristics compared to the organic electroluminescent devices (Device Comparative Examples 7 and 8) containing conventional host combinations.

[0235] The compounds used in the device examples and the device comparative examples are specifically shown in Table 6 below.

[0236] Table 6

[0237]

[0238]

Claims

1. A compound represented by the following formula 1: in, X1 to X3 each independently represent CR5 or N, provided that at least one of X1 to X3 is N; Ar1 represents hydrogen, deuterium, halogen, cyano, amino, substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C6-C 30 )aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (C1-C 30 )alkoxy, -Si(R 11 )(R 12 )(R 13 ), or -N(R 14 )(R 15 ); R 11 To R 15 Each independently represents a substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C2-C 30 )alkenyl, substituted or unsubstituted (C6-C 30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; L1 represents a single bond, substituted or unsubstituted (C6-C 30 )arylene, or substituted or unsubstituted (3- to 30-membered)heteroarylene; Ar represents a substituted or unsubstituted (C6-C 30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; R1 to R5 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C6-C 30 )aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (C1-C 30 ) alkoxy, substituted or unsubstituted tri(C1-C 30 )alkylsilyl, substituted or unsubstituted di(C1-C 30 )alkyl(C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 )alkyldi(C6-C 30 ) arylsilyl, or substituted or unsubstituted tri(C6-C 30 ) arylsilyl; or may be connected to adjacent substituents to form one or more rings; and a, b, and d each independently represent an integer of 1 to 4, c represents an integer of 1 to 3, and when a to d are integers of 2 or more, each of R1 to R4 may be the same as or different from each other.

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

3. The compound according to claim 1, wherein Formula 1 is represented by the following formula 1-1: in, R1 to R4, X1 to X3, Ar1, L1, and a to d are as defined in claim 1; X represents O, S, or Se; R6 and R7 are as defined in claim 1 as R1; and e represents an integer of 1 to 3, f represents an integer of 1 to 4, and when e and f are integers of 2 or more, each R6 and each R7 may be the same as or different from each other.

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

5. An organic electroluminescent material comprising the compound represented by Formula 1 according to claim 1, and a compound represented by the following Formula 2 or 3: in, A1 and A2 each independently represent a substituted or unsubstituted (C6-C 30 ) aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazolyl; X 15 To X 18 Any one of 19 To X 22 Any of are connected to each other to form a single bond; and X 11 To X 14 , X 23 To X 26 , and X that does not form a single bond 15 To X 22 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C 30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; or may be connected to adjacent substituents to form one or more rings; in, A3 represents a substituted or unsubstituted (C6-C 30 ) aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, or substituted or unsubstituted carbazolyl; L2 represents a single bond, or a substituted or unsubstituted (C6-C 30 ) arylene; A pair of adjacent X 35 To X 38 Connected to the following formula 3-A to form a ring, and X which does not form a ring 35 To X 38 and X 31 To X 34 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C 30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; and in, A4 represents a substituted or unsubstituted (C6-C 30 ) aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, or substituted or unsubstituted carbazolyl; L3 represents a single bond, or a substituted or unsubstituted (C6-C 30 ) arylene; and X 41 To X 44 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C 30 )aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl.

6. The organic electroluminescent material according to claim 5, wherein X in Formula 2 11 , X 18 , X 19 , and X 26 At least one of them is deuterium.

7. The organic electroluminescent material according to claim 5, wherein X in Formula 2 11 To X 26 The deuterium substitution rate is 25% to 100%.

8. The organic electroluminescent material according to claim 5, wherein The deuterium substitution rate of the compound represented by Formula 2 or 3 is 40% to 100%.

9. The organic electroluminescent material according to claim 5, wherein: Formula 2 is represented by any one of the following Formulas 2-1 to 2-8: in, A1, A2, and X 11 To X 26 Each independently is as defined in claim 5.

10. The organic electroluminescent material according to claim 5, wherein A1 and A2 in Formula 2 each independently represent an unsubstituted or deuterated phenyl group; an unsubstituted or deuterated biphenyl group; an unsubstituted or deuterated terphenyl group; an unsubstituted or deuterated naphthyl group; an unsubstituted or deuterated (C1-C 30 ) alkyl, and (C6-C 30 ) aryl substituted with at least one fluorenyl; unsubstituted or deuterated, (C1-C 30 ) alkyl, and (C6-C 30 ) at least one substituted benzofluorenyl group in the aromatic group; an unsubstituted or deuterium substituted triphenylene group; an unsubstituted or deuterium substituted fluoranthene group; an unsubstituted or deuterium substituted phenanthryl group; an unsubstituted or deuterium substituted dibenzofuranyl group; an unsubstituted or deuterium substituted dibenzothienyl group; an unsubstituted or deuterium substituted carbazolyl group; or a combination thereof.

11. The organic electroluminescent material according to claim 5, wherein: Formula 3 is represented by any one of the following Formulas 3-1 to 3-6: in, A3, A4, L2, L3, X 31 To X 38 and X 41 To X 44 As defined in claim 5.

12. The organic electroluminescent material according to claim 5, wherein: The compound represented by Formula 2 is selected from the following compounds: Among them, "D n ” means that n number of hydrogens are replaced by deuterium.

13. The organic electroluminescent material according to claim 5, wherein: The compound represented by Formula 3 is selected from the following compounds: Among them, "D n " means that n number of hydrogens are replaced by deuterium, wherein n represents an integer of 1 or more, and the upper limit of n is determined by the number of hydrogens that can be replaced in each compound. 14 . 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 the compound according to claim 1 . 15 . 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 the organic electroluminescent material according to claim 5 .

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