Organic electroluminescent device and organic electroluminescent compound for the same

Abstract

To provide a compound effective for producing organic electroluminescent devices having high luminous efficiency and / or long lifespan characteristics and an organic electroluminescent material comprising the same.SOLUTION: An organic electroluminescent device comprises: a first electrode; a second electrode; a light-emitting layer between the first electrode and the second electrode; and at least one electron blocking layer between the first electrode and the light-emitting layer, the electron blocking layer comprising a compound represented by the following Formula 1, and the light-emitting layer comprising at least two kinds of compounds.SELECTED DRAWING: None

Description

Technical Field

[0001] The present disclosure relates to an organic electroluminescent device and an organic electroluminescent compound therefor.

Background Art

[0002] A green-emitting TPD / Alq bilayer small molecule organic electroluminescent device (OLED) composed of a light-emitting layer and a charge transport layer was first developed by Tang et al. of Eastman Kodak in 1987. Thereafter, research on organic electroluminescent devices has been rapidly advanced, and OLEDs have been commercialized. Currently, OLEDs mainly use phosphorescent materials having excellent luminous efficiency in panel mounting. Therefore, for long-term use and high display resolution, OLEDs having high luminous efficiency and / or long lifetime characteristics are required. 3 (Patent Document 1) discloses an organic electroluminescent device including a compound having phenanthrooxazole or phenanthrothiazole as a main core and a phenanthro derivative as a host material, but specifically does not disclose an organic electroluminescent device having improved performance such as high luminous efficiency and / or long lifetime characteristics by using a specific combination of a compound as an electron blocking layer and a host material for a light-emitting layer as in the present disclosure.

[0003] (Patent Document 1) discloses an organic electroluminescent device including a compound having phenanthrooxazole or phenanthrothiazole as a main core and a phenanthro derivative as a host material, but specifically does not disclose an organic electroluminescent device having improved performance such as high luminous efficiency and / or long lifetime characteristics by using a specific combination of a compound as an electron blocking layer and a host material for a light-emitting layer as in the present disclosure.

Summary of the Invention

Problems to be Solved by the Invention

[0004] An object of the present disclosure is to provide a compound effective for manufacturing an organic electroluminescent device having high luminous efficiency and / or long lifetime characteristics, and an organic electroluminescent material containing the same.

Means for Solving the Problems

[0005] As a result of intensive research to solve the above technical problems, the inventors of the present invention have found that the above object can be achieved by an organic electroluminescent device including a first electrode, a second electrode, a light-emitting layer between the first electrode and the second electrode, and at least one electron blocking layer between the first electrode and the light-emitting layer, wherein the electron blocking layer contains a compound represented by the following formula 1, and the light-emitting layer contains at least two kinds of compounds, thereby completing the present invention. [Chemical formula]

[0006] In Formula 1, R 1 ~R 10 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, a substituted or unsubstituted condensed ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, or *-L 1 -N(Ar 1 )(Ar 2 ), provided that at least one of R 1 ~R 10 is *-L 1 -N(Ar 1 )(Ar 2 ), L 1 represents a single bond, substituted or unsubstituted (C6-C30) arylene or substituted or unsubstituted (3-30 membered) heteroarylene, Ar 1 and Ar 2Each independently represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C2-C30) alkenyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl.

[0007] By including the compounds according to the present disclosure and / or the organic electroluminescent materials containing the same, it is possible to provide an organic electroluminescent device having high luminous efficiency and / or long life characteristics.

Mode for Carrying Out the Invention

[0008] The present disclosure will be described in detail hereinafter. However, the following description is intended to explain the present invention and is by no means intended to limit the scope of the present disclosure.

[0009] The organic electroluminescent device according to the present disclosure includes a first electrode, a second electrode, a light emitting layer between the first electrode and the second electrode, and at least one electron blocking layer between the first electrode and the light emitting layer. The electron blocking layer contains a compound represented by Formula 1, and the light emitting layer contains at least two kinds of compounds.

[0010] The organic electroluminescent device according to the present disclosure includes at least one hole auxiliary layer between the first electrode and the electron blocking layer.

[0011] The organic electroluminescent material according to the present disclosure includes at least one compound represented by Formula 2 and at least one compound represented by Formula 3.

[0012] The present disclosure provides an organic electroluminescent compound represented by Formula 1-1 as a compound for an organic electroluminescent device and an organic electroluminescent device containing the same.

[0013] The present disclosure provides an organic electroluminescent compound represented by Formula 3’ as a compound for an organic electroluminescent device and an organic electroluminescent device including the same.

[0014] As used herein, the term "organic electroluminescent compound" in the present disclosure means a compound that can be used in an organic electroluminescent device, which may be included in any material layer constituting the organic electroluminescent device as needed.

[0015] As used herein, the term "organic electroluminescent material" means a material that can be used in an organic electroluminescent device, which may contain at least one compound. The organic electroluminescent material 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 auxiliary material, a light emission auxiliary 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, or an electron injection material, etc.

[0016] The term "a plurality of organic electroluminescent materials" in the present disclosure means an organic electroluminescent material including a combination of at least two compounds that may be included in any layer constituting the organic electroluminescent device. This may mean both the material before being included in the organic electroluminescent device (e.g., before evaporation) and the material after being included in the organic electroluminescent device (e.g., after evaporation). For example, the plurality of organic electroluminescent materials may be a combination of at least two compounds that may be included in at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emission auxiliary layer, an electron blocking layer, a light emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. Such at least two compounds may be included in the same layer or different layers, and may be co-evaporated or co-evaporated, or evaporated individually.

[0017] In this specification, the term "plurality of host materials" means that the organic electroluminescent material includes a combination of at least two host materials. This can mean both the material before being included in the organic electroluminescent device (e.g., before evaporation) and the material after being included in the organic electroluminescent device (e.g., after evaporation). The plurality of host materials of the present disclosure can be included in any light-emitting layer constituting the organic electroluminescent device. At least two compounds included in the plurality of host materials may be included together in one light-emitting layer, or may be included in different light-emitting layers respectively. When at least two compounds are included in one light-emitting layer, the at least two compounds may be co-evaporated to form a layer, or may be co-evaporated simultaneously individually to form a layer.

[0018] As used herein, “(C1-C30)alkyl(ene)” means a straight-chain or branched alkyl having 1 to 30 carbon atoms constituting the chain, and the number of carbon atoms herein is preferably 1 to 20, more preferably 1 to 10. Examples of the above alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, etc. As used herein, “(C3-C30)cycloalkyl(ene)” means a monocyclic or polycyclic hydrocarbon having 3 to 30 ring-skeleton carbon atoms, and the number of carbon atoms herein is preferably 3 to 20, more preferably 3 to 7. Examples of the above cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, etc. In the present disclosure, “(3-7 membered)heterocycloalkyl” means a cycloalkyl having 3 to 7 ring-skeleton atoms, preferably 5 to 7 ring-skeleton atoms, and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably from the group consisting of O, S, and N. Examples thereof include tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, etc. In the present disclosure, “(C6-C30)aryl(ene)” means a monocyclic or fused-ring radical derived from an aromatic hydrocarbon having 6 to 30 ring-skeleton carbon atoms, and the number of ring-skeleton carbon atoms therein is preferably 6 to 20, more preferably 6 to 15. The above aryl may be partially saturated or may contain a spiro structure. Specific examples of aryl include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthrenyl, benzophenanthrenyl, phenylphenanthrenyl, anthracenyl, benzanthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, benzochrysenyl, naphthacenyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl,Examples include mesityl, cumenyl, spiro[fluorene-fluorene]yl, spiro[fluorene-benzofluorene]yl, azulenyl, tetramethyl-dihydrophenanthrenyl, etc. More specifically, aryl is o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, p-t-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-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-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-chrysenyl, 2-chrysenyl, 3-chrysenyl, 4-chrysenyl, 5-chrysenyl, 6-chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 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-6-benzo[b]fluorenyl, 11,11-dimethyl-7-benzo[b]fluorenyl, 11,11-dimethyl-8-benzo[b]fluorenyl, 11,11-dimethyl-9-benzo[b]fluorenyl, 11,11-dimethyl-10-benzo[b]fluorenyl, 11,11-dimethyl-1-benzo[c]fluorenyl, 11,11-dimethyl-2-benzo[c]fluorenyl, 11,11-dimethyl-3-benzo[c]fluorenyl, 11,11-dimethyl-4-benzo[c]fluorenyl, 11,11-dimethyl-5-benzo[c]fluorenyl, 11,11-dimethyl-6-benzo[c]fluorenyl, 11,11-dimethyl-7-benzo[c]fluorenyl, 11,11-dimethyl-8-benzo[c]fluorenyl, 11,11-dimethyl-9-benzo[c]fluorenyl, 11,11-dimethyl-10-benzo[c]fluorenyl, 11,11-diphenyl-1-benzo[a]fluorenyl, 11,11-diphenyl-2-benzo[a]fluorenyl, 11,11-diphenyl-3-benzo[a]fluorenyl, 11,11-diphenyl-4-benzo[a]fluorenyl, 11,11-diphenyl-5-benzo[a]fluorenyl, 11,11-diphenyl-6-benzo[a]fluorenyl, 11,11-diphenyl-7-benzo[a]fluorenyl, 11,11-diphenyl-8-benzo[a]fluorenyl, 11,11-diphenyl-9-benzo[a]fluorenyl, 11,11-diphenyl-10-benzo[a]fluorenyl, 11,11-diphenyl-1-benzo[b]fluorenyl, 11,11-diphenyl-2-benzo[b]fluorenyl, 11,11-diphenyl-3-benzo[b]fluorenyl, 11,11-diphenyl-4-benzo[b]fluorenyl,11,11-Diphenyl-5-benzo[b]fluorenyl, 11,11-diphenyl-6-benzo[b]fluorenyl, 11,11-diphenyl-7-benzo[b]fluorenyl, 11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9-benzo[b]fluorenyl, 11,11-diphenyl-10-benzo[b]fluorenyl, 11,11-diphenyl-1-benzo[c]fluorenyl, 11,11-diphenyl-2-benzo[c]fluorenyl, 11,11-diphenyl-3-benzo[c]fluorenyl, 11,11-diphenyl-4-benzo[c]fluorenyl, 11,11-diphenyl-5-benzo[c]fluorenyl, 11,11-diphenyl-6-benzo[c]fluorenyl, 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-9,10-dihydro-4-phenanthrenyl, etc. may be used. The "(3 to 30-membered) heteroaryl(ene)" in the present disclosure has 3 to 30 ring backbone atoms and is an aryl containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, P, Se, and Ge, where the number of ring backbone atoms is preferably 5 to 25. The number of heteroatoms in the heteroaryl is preferably 1 to 4. The above heteroaryl may be a monocyclic ring, or a condensed ring condensed with at least one benzene ring, and may also be partially saturated. Further, the heteroaryl in the present specification may be formed by bonding at least one heteroaryl group or aryl group to the heteroaryl group by a single bond. Examples of heteroaryl specifically include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl,Monocyclic heteroaryls such as oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl; and fused ring heteroaryls such as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, benzofuroquinolinyl, benzofuroquinazolinyl, benzofuronaphthyridinyl, benzofuropyrimidinyl, naphthofuropyrimidinyl, benzothienoquinolinyl, benzothienoquinazolinyl, benzothienonaphthyridinyl, benzothienopyrimidinyl, naphthothienopyrimidinyl, pyrimidylindolyl, benzopyrimidylindolyl, benzofuropyrazinyl, naphthofuropyrazinyl, benzothienopyrazinyl, naphthothienopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, indolizinyl, acridinyl, silafluorenyl, germafurenyl, benzotriazolyl, phenazinyl, imidazopyridinyl, chromenokuinazolinyl, thiochromenokuinazolinyl, dimethylbenzopyrimidinyl, indolocarbazolyl, indenocarbazolyl, etc. More specifically, heteroaryl is 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolizinyl, 2-indolizinyl, 3-indolizinyl, 5-indolizinyl, 6-indolizinyl, 7-indolizinyl, 8-indolizinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl,7-imidazopyridinyl, 8-imidazopyridinyl, 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-iso, Indolyl, 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, azacarbazol-1-yl, azacarbazol-2-yl, azacarbazol-3-yl, azacarbazol-4-yl, azacarbazol-5-yl, azacarbazol-6-yl, azacarbazol-7-yl, azacarbazol-8-yl, azacarbazol-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2-t-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-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]pyrazinyl, 6-benzothio[3,2-d]pyrazinyl, 7-benzothio[3,2-d]pyrazinyl, 8-benzothio[3,2-d]pyrazinyl, 9-benzothio[3,2-d]pyrazinyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafurenyl, 2-germafurenyl, 3-germafurenyl, 4-germafurenyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, and the like. Further, "heteroaryl(ene)" is,It can be classified as a heteroaryl(ene) having electronic properties or a heteroaryl(ene) having hole properties. The heteroaryl(ene) having electronic properties is a substituent in which electrons are relatively abundant in the parent nucleus, and examples thereof may include substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinolyl, and the like. The heteroaryl(ene) having hole properties is a substituent having relatively insufficient electrons in the parent nucleus, and examples thereof may include substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl. In the present specification, the “condensed ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring” has 3 to 30 ring skeleton carbon atoms, preferably 3 to 25 carbon atoms, more preferably 3 to 18 carbon atoms, and at least one aliphatic ring having 6 to 30 ring skeleton carbon atoms, preferably 6 to 25 carbon atoms, more preferably 6 to 18 carbon atoms, and at least one aromatic ring are condensed to form a ring. 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. In the present specification, the carbon atoms in the condensed ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring may be replaced by at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S. The “halogen” in the present disclosure includes F, Cl, Br, and I.,

[0019] Furthermore, “ortho (o-)”, “meta (m-)”, and “para (p-)” are all intended to indicate the substitution positions of all substituents. The ortho position represents, for example, a compound having substituents adjacent to each other at the 1-position and 2-position of benzene. The meta position indicates the substitution position next to the directly adjacent substitution position, for example, a compound having substituents at the 1-position and 3-position of benzene. The para position indicates the substitution position next to the meta position, for example, a compound having substituents at the 1-position and 4-position of benzene.

[0020] As used herein, the term "ring formed by linking adjacent substituents" means a substituted or unsubstituted (3- to 30-membered) monocyclic or polycyclic aliphatic ring, aromatic ring, or a combination thereof, formed by linking or condensing two or more adjacent substituents, preferably it may be a substituted or unsubstituted (3- to 26-membered) monocyclic or polycyclic aliphatic ring, aromatic ring, or a combination thereof. Further, 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 ring backbone atoms is 5 to 20, and according to another embodiment of the present disclosure, the number of ring backbone atoms is 5 to 15. In one embodiment, the fused ring may 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.

[0021] Furthermore, the term "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a specific functional group is replaced by another atom or another functional group, i.e., a substituent. Unless otherwise specified, the substituent does not have to be limited to the hydrogen at the position where the substituent can be substituted. When two or more hydrogen atoms in a functional group are each replaced by a substituent, the substituents may be the same as or different from each other. This also includes the case where a hydrogen atom is replaced by a group formed by the linkage of two or more of the above substituents. For example, the "group formed by the linkage of two or more substituents" may be pyridine-triazine. That is, pyridine-triazine may be a heteroaryl or may be interpreted as one substituent in which two heteroaryls are linked. For example, in the present disclosure, "phenylnaphthyl" means naphthalene substituted with a phenyl group, and "naphthylphenyl" means benzene substituted with a naphthyl group. Preferably, the substituted alkyl, substituted alkenyl, substituted cycloalkyl, substituted heterocycloalkyl, substituted aryl(en), substituted heteroaryl(en), substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted mono- or di-alkylamino, substituted mono- or di-arylamino, substituted alkylarylamino, and substituted condensed ring of an aliphatic ring and an aromatic ring in the formula of the present disclosure are each independently deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; (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; (3-30 membered)heteroaryl which is unsubstituted or substituted with at least one (C6-C30)aryl; (C6-C30)aryl which is unsubstituted or substituted with at least one of (C1-C30)alkyl and (3-30 membered)heteroaryl; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl;Di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; tri(C6-C30)arylgermanyl; amino; mono- or di-(C1-C30)alkylamino; mono- or di-(C2-C30)alkenylamino; mono- or di-(C6-C30)arylamino unsubstituted or substituted with (C1-C30)alkyl; mono- or di-(3-30 membered) heteroarylamino; (C1-C30)alkyl(C2-C30)alkenylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkyl(3-30 membered) heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30)alkenyl(3-30 membered) heteroarylamino; (C6-C30)aryl(3-30 membered) heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)ar(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl, etc., may be substituted with one or more selected from the group consisting of. For example, the substituent may be substituted with deuterium, cyano, methyl, phenyl, naphthyl, triphenylsilyl, pyridyl, dibenzofuranyl, or dibenzothiophenyl, etc.;

[0022] When a substituent is not shown in the chemical formulas or compound structures of the present disclosure, it may mean that all positions where it can be present as a substituent are hydrogen or deuterium. That is, in the case of deuterium, which is an isotope of hydrogen, some hydrogen atoms may be the isotope deuterium, and in this case, the deuterium content may be from 0% to 100%. When a substituent is not shown in the chemical formulas or compound structures of the present disclosure, hydrogen and deuterium can be used in combination in the compound when deuterium is not explicitly excluded. For example, when the deuterium content is 0%, the hydrogen content is 100%, and all substituents are hydrogen. Deuterium is an element having a deuteron composed of one proton and one neutron as its nucleus, is one of the isotopes of hydrogen, can be represented by hydrogen-2, and the element symbol can be D or 2 H. Isotopes having the same atomic number (Z) but different mass numbers (A) can also be interpreted as elements having the same number of protons but different numbers of neutrons.

[0023] As used herein, "their combinations" means combining one or more components of the corresponding list to form a known or chemically stable form that a person skilled in the art can conceive from the corresponding list. For example, an alkyl and deuterium can be combined to form a partially or fully deuterated alkyl group, a halogen and an alkyl can be combined to form a halogenated alkyl substituent, and a halogen, an alkyl, and an aryl can be combined to form a halogenated arylalkyl. For example, a preferred combination of substituents may contain up to 50 atoms excluding hydrogen and deuterium, or may contain up to 40 atoms excluding hydrogen and deuterium, or may contain up to 30 atoms excluding hydrogen and deuterium, or in many cases, a preferred combination of substituents may contain up to 20 atoms excluding hydrogen and deuterium.

[0024] In the formulas 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.

[0025] An organic electroluminescent compound according to an embodiment will be described in more detail below.

[0026] The organic electroluminescent device according to the present disclosure includes a first electrode, a second electrode, a light-emitting layer between the first electrode and the second electrode, and at least one electron blocking layer between the first electrode and the light-emitting layer. The electron blocking layer contains a compound represented by the following formula 1, and the light-emitting layer contains at least two kinds of compounds. [Chemical formula]

[0027] In formula 1, R 1 ~R 10 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, a substituted or unsubstituted condensed ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, or *-L 1 -N(Ar 1 )(Ar 2 ), provided that at least one of R 1 ~R 10 is *-L 1 -N(Ar 1 )(Ar 2 ), L 1 represents a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3-30 membered) heteroarylene, Ar 1 and Ar 2Each independently represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C2-C30) alkenyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl.

[0028] In one embodiment, -L 1 -N(Ar 1 )(Ar 2 ) where R is not 1 ~R 10 Each independently may be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5-30 membered) heteroaryl, preferably hydrogen, deuterium, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5-25 membered) heteroaryl, more preferably hydrogen, deuterium, substituted or unsubstituted (C6-C18) aryl, or substituted or unsubstituted (5-18 membered) heteroaryl. For example, R 1 ~R 10 Each independently may be hydrogen, deuterium, phenyl which is unsubstituted or substituted with cyano, naphthyl which is unsubstituted or substituted with phenyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, or substituted or unsubstituted dibenzofuranyl. In one embodiment, L 1 Is a single bond or substituted or unsubstituted (C6-C30) arylene, preferably a single bond or substituted or unsubstituted (C6-C25) arylene, more preferably a single bond or substituted or unsubstituted (C6-C18) arylene. For example, L 1 May be a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted p-biphenylene, substituted or unsubstituted m-biphenylene, or substituted or unsubstituted o-biphenylene.

[0029] In one embodiment, Ar 1 And Ar2 is each independently a substituted or unsubstituted (C6 - C30) aryl or a substituted or unsubstituted (5 - 30 membered) heteroaryl, preferably a substituted or unsubstituted (C6 - C25) aryl or a substituted or unsubstituted (5 - 25 membered) heteroaryl, more preferably a substituted or unsubstituted (C6 - C18) aryl or a substituted or unsubstituted (5 - 18 membered) heteroaryl. For example, Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted p - biphenyl, a substituted or unsubstituted o - biphenyl, a substituted or unsubstituted m - terphenyl, a substituted or unsubstituted p - terphenyl, a substituted or unsubstituted o - terphenyl, a substituted or unsubstituted dimethylfluorenyl, a substituted or unsubstituted diethylfluorenyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted carbazolyl, or a substituted or unsubstituted benzonaphthothiophenyl. Here, the substituent is, for example, deuterium, tert - butyl, amino, phenyl, p - biphenyl, m - terphenyl, fluorenyl, triphenylsilyl, naphthyl, phenanthrenyl, pyridyl which is unsubstituted or substituted with phenyl, dibenzothiophenyl, dibenzofuranyl, and carbazolyl, and may be substituted with at least one of them.

[0030] According to one embodiment, the compound represented by Chemical Formula 1 can be more specifically exemplified by, but not limited to, the following compounds:

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chem.

Chem.

[0031] The compound represented by Formula 1 according to the present disclosure can be produced by referring to synthetic methods known to those skilled in the art, such as the synthetic methods disclosed in (Patent Document 2) and (Patent Document 3), etc., but is not limited thereto.

[0032] According to one embodiment, the light-emitting layer contains at least one compound represented by the following Formula 2 and at least one compound represented by the following Formula 3.

Chem.

[0033] In Formula 2, L 3 ~L 5 each independently represents a single bond, a substituted or unsubstituted (C1-C30) alkylene, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3-30 membered) heteroarylene, or a substituted or unsubstituted (C3-C30) cycloalkylene, Ar 3 ~Ar 5 each independently represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 membered) heteroaryl, a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (C1-C30) alkoxy, a substituted or unsubstituted tri(C1-C30) alkylsilyl, a substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, a substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, a substituted or unsubstituted tri(C6-C30) arylsilyl, or -N(Ar 11 )(Ar12 ) represents Ar 11 and Ar 12 each independently represents a substituted or unsubstituted (C1 - C30) alkyl, a substituted or unsubstituted (C2 - C30) alkenyl, a substituted or unsubstituted (C6 - C30) aryl, or a substituted or unsubstituted (3 - 30 membered) heteroaryl, provided that in Formula 2, when all of L 3 ~L 5 are single bonds and all of Ar 3 ~Ar 5 are hydrogen, this case is excluded.

[0034] In one embodiment, L 3 ~L 5 may each independently be a single bond, a substituted or unsubstituted (C6 - C30) arylene, or a substituted or unsubstituted (5 - 30 membered) heteroarylene, preferably a single bond, a substituted or unsubstituted (C6 - C25) arylene, or a substituted or unsubstituted (5 - 25 membered) heteroarylene, more preferably a single bond, a substituted or unsubstituted (C6 - C18) arylene, or a substituted or unsubstituted (5 - 18 membered) heteroarylene. For example, L 3 ~L 5 may each independently be a single bond, unsubstituted or substituted with phenyl or pyridyl phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthrenylene, substituted or unsubstituted o - biphenylene, substituted or unsubstituted m - biphenylene, substituted or unsubstituted p - biphenylene, substituted or unsubstituted pyridylene, or substituted or unsubstituted carbazolylene.

[0035] In one embodiment, Ar 3 ~Ar 5 each independently represents a substituted or unsubstituted (C1 - C30) alkyl, a substituted or unsubstituted (C6 - C30) aryl, a substituted or unsubstituted (5 - 30 membered) heteroaryl, a substituted or unsubstituted tri(C6 - C30) arylsilyl, or -N(Ar 11 )(Ar 12) may be, preferably, substituted or unsubstituted (C1-C10) alkyl, substituted or unsubstituted (C6-C25) aryl, substituted or unsubstituted (5-25 membered) heteroaryl, substituted or unsubstituted tri (C6-C25) arylsilyl, or -N(Ar 11 )(Ar 12 ) may be, more preferably, substituted or unsubstituted (C1-C4) alkyl, substituted or unsubstituted (C6-C18) aryl, substituted or unsubstituted (5-18 membered) heteroaryl, substituted or unsubstituted tri (C6-C18) arylsilyl, or -N(Ar 11 )(Ar 12 ) may be. In one embodiment, Ar 11 and Ar 12 may each independently be substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (5-30 membered) heteroaryl, preferably substituted or unsubstituted (C6-C25) aryl or substituted or unsubstituted (5-25 membered) heteroaryl, more preferably substituted or unsubstituted (C6-C18) aryl or substituted or unsubstituted (5-18 membered) heteroaryl. For example, Ar 3 to Ar 5is, independently of each other, phenyl which is unsubstituted or substituted with deuterium or cyano, isopropyl which is unsubstituted or substituted with phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted o-quaterphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted chrysenyl, fluorenyl which is unsubstituted or substituted with at least one methyl, fluorenyl which is unsubstituted or substituted with at least one phenyl, substituted or unsubstituted 9,9,10,10-tetramethylphenanthrenyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted pyridyl, carbazolyl, dibenzofuranyl which is unsubstituted or substituted with deuterium, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted phenanthrolinyl, substituted or unsubstituted dibenzoselenophenyl, or substituted or unsubstituted naphthobenzoselenophenyl. Here, the substituent may be further substituted with at least one of, for example, deuterium, methyl, and phenyl.

[0036] For example, Ar 11 and Ar 12 are, independently of each other, phenyl which is unsubstituted or substituted with diphenylamino, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted dibenzofuranyl.

[0037] According to one embodiment, at least one of Ar 3 ~Ar 5 can be represented by any one of the following formulas 2-1 to 2-3.

Chemical formula

[0038] In Formula 2-1, X 1 and Y 1 each independently represents -N=, -NR 25 -, -O-, or -S-, provided that one of X 1 and Y 1 is -N=, and the other of X 1 and Y 1 is -NR 25 -, -O-, or -S-, R 21 represents a substituted or unsubstituted (C6 - C30) aryl or a substituted or unsubstituted (3 - 30-membered) heteroaryl, R 22 ~R 25 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 - C30) alkyl, substituted or unsubstituted (C6 - C30) aryl, substituted or unsubstituted (3 - 30-membered) heteroaryl, substituted or unsubstituted (C3 - C30) cycloalkyl, substituted or unsubstituted (C1 - C30) alkoxy, substituted or unsubstituted tri(C1 - C30) alkylsilyl, substituted or unsubstituted di(C1 - C30) alkyl(C6 - C30) arylsilyl, substituted or unsubstituted (C1 - C30) alkyldi(C6 - C30) arylsilyl, substituted or unsubstituted tri(C6 - C30) arylsilyl, substituted or unsubstituted mono- or di-(C1 - C30) alkylamino, substituted or unsubstituted mono- or di-(C6 - C30) arylamino, or substituted or unsubstituted (C1 - C30) alkyl(C6 - C30) arylamino, or may be linked with adjacent substituents to form a ring, a and b each independently represent an integer of 1 or 2, and c represents an integer of 1 - 3, when a - c are integers of 2 or more, each R 22 ~ each R 24 may be the same as or different from each other, * represents the linking position to L of Formula 2 3 ~L 5 in the formula. [Chemical formula]

[0039] In Formula 2-2, Y represents -O-, -S-, or -NR 39 and R 39 represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 membered) heteroaryl, R 31 ~R 38 each independently represents a linking position linked to L 3 ~L 5 in Formula 2, or represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, or may be linked to an adjacent substituent to form a ring. [Chemical formula]

[0040] In Formula 2-3, T represents -O-, -S-, -CR 45 R 46 , -NR 47 , or -Se-, and R 45 ~R 47Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C6-C30) aryl, R 41 ~R 44 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, or -N(Ar 21 )(Ar 22 ) or may be linked to adjacent substituents to form a ring, Ar 21 and Ar 22 Each independently represents substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl, d and g each independently represent an integer from 1 to 4, and e and f each independently represent an integer of 1 or 2, When d to g are integers of 2 or more, each R 41 ~each R 44 may be the same as or different from each other, * represents the linking position to L in Formula 2 3 ~L 5

[0041] According to one embodiment, the compound represented by Formula 2-3 can be represented by the following Formula 2-3-1 or 2-3-2.

Chemical formula

[0042] In Formula 2-3-1 or 2-3-2, T, R 41 ~R 44 and d to g are as defined in Formula 2-3.

[0043] In Formula 2-1, R 21 ​is a substituted or unsubstituted (C6 - C30) aryl or substituted or unsubstituted (5 - 30 membered) heteroaryl, for example phenyl which is unsubstituted or substituted with deuterium, substituted or unsubstituted naphthyl, substituted or unsubstituted o - biphenyl, substituted or unsubstituted m - biphenyl, substituted or unsubstituted p - biphenyl, or substituted or unsubstituted pyridyl.

[0044] In formula 2 - 1, R 22 ~R 25 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C6 - C30) aryl, or substituted or unsubstituted (5 - 30 membered) heteroaryl, preferably hydrogen, deuterium, substituted or unsubstituted (C6 - C25) aryl, or substituted or unsubstituted (5 - 25 membered) heteroaryl, more preferably hydrogen, deuterium, substituted or unsubstituted (C6 - C18) aryl, or substituted or unsubstituted (5 - 18 membered) heteroaryl. For example, R 22 ~R 25 are each independently hydrogen, deuterium, phenyl which is unsubstituted or substituted with naphthyl or triphenylsilyl, substituted or unsubstituted naphthyl, substituted or unsubstituted o - biphenyl, substituted or unsubstituted m - biphenyl, substituted or unsubstituted p - biphenyl, substituted or unsubstituted p - terphenyl, fluorenyl which is unsubstituted or substituted with at least one methyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzonaphthofuranyl, or substituted or unsubstituted benzonaphthothiophenyl.

[0045] In formula 2 - 2, one of R 31 ~R 38 may be the linking position linked to L 3 ~L 5 in formula 2.

[0046] In formula 2 - 3, T may be - O - or - S -.

[0047] In formula 2 - 3, R41 ~R 44 is, independently of one another, hydrogen, deuterium, a substituted or unsubstituted (C6-C30) aryl, or -N(Ar 21 )(Ar 22 ), and may be, for example, hydrogen, deuterium, a substituted or unsubstituted phenyl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted naphthyl, or a substituted or unsubstituted diphenylamine. For example, Ar 21 and Ar 22 may each independently be a substituted or unsubstituted phenyl.

[0048] According to one embodiment, the compound represented by Formula 2 can be more specifically exemplified by, but is not limited to, the following compounds.

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0049] In the above compound, D n means that n hydrogens are replaced by deuteriums, where n is an integer greater than or equal to 1, and the upper limit of n is determined by the number of hydrogens that can be substituted in each compound.

[0050] The compound represented by Formula 2 according to the present disclosure can be prepared by referring to synthetic methods known to those skilled in the art, such as the synthetic methods disclosed in (Patent Document 4), (Patent Document 5), and (Patent Document 6), etc., but is not limited thereto.

Chemical formula

[0051] In Formula 3, X 1 ~X 3 each independently represents N or CR 11 provided that at least one of X 1 ~X 3 represents N, L 7 ~L 9 each independently represents a single bond, a substituted or unsubstituted (C6 - C30) arylene, or a substituted or unsubstituted (3 - 30 membered) heteroarylene, R 11 represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 - C30) alkyl, substituted or unsubstituted (C6 - C30) aryl, substituted or unsubstituted (3 - 30 membered) heteroaryl, substituted or unsubstituted (C3 - C30) cycloalkyl, substituted or unsubstituted (C1 - C30) alkoxy, substituted or unsubstituted tri(C1 - C30) alkylsilyl, substituted or unsubstituted di(C1 - C30) alkyl(C6 - C30) arylsilyl, substituted or unsubstituted (C1 - C30) alkyldi(C6 - C30) arylsilyl, substituted or unsubstituted tri(C6 - C30) arylsilyl, or a substituted or unsubstituted condensed ring group of a (C3 - C30) aliphatic ring and a (C6 - C30) aromatic ring, Ar 7 ~Ar 9is, independently of each other, substituted or unsubstituted (C1 - C30) alkyl, substituted or unsubstituted (C3 - C30) cycloalkyl, substituted or unsubstituted (3 - 7-membered) heterocycloalkyl, substituted or unsubstituted condensed ring of (C3 - C30) aliphatic ring and (C6 - C30) aromatic ring, substituted or unsubstituted (C6 - C30) aryl, substituted or unsubstituted (3 - 30-membered) heteroaryl, substituted or unsubstituted tri(C1 - C30) alkylsilyl, substituted or unsubstituted di(C1 - C30) alkyl(C6 - C30) arylsilyl, substituted or unsubstituted (C1 - C30) alkyldi(C6 - C30) arylsilyl, substituted or unsubstituted tri(C6 - C30) arylsilyl, or *-L 21 -N(Ar 21 )(Ar 22 ), and L 21 represents a single bond, substituted or unsubstituted (C6 - C30) arylene or substituted or unsubstituted (3 - 30-membered) heteroarylene, Ar 21 and Ar 22 each independently represent substituted or unsubstituted (C1 - C30) alkyl, substituted or unsubstituted (C2 - C30) alkenyl, substituted or unsubstituted (C6 - C30) aryl, or substituted or unsubstituted (3 - 30-membered) heteroaryl.

[0052] In one embodiment, at least two of X 1 ~X 3 may be N.

[0053] In one embodiment, X 1 ~X 3 may all be N.

[0054] In one embodiment, L 7 ~L 9may each independently be a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5-30 membered) heteroarylene, preferably a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (5-25 membered) heteroarylene, more preferably a single bond, a substituted or unsubstituted (C6-C18) arylene, or a substituted or unsubstituted (5-18 membered) heteroarylene. For example, L 7 ~L 9 each independently represents a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylphenylene, a substituted or unsubstituted phenylnaphthylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted dibenzofuranylene, or a substituted or unsubstituted dibenzothiophenylene, and these substituents may be substituted with, for example, at least one deuterium.

[0055] In one embodiment, Ar 7 ~Ar 9 may each independently be a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5-30 membered) heteroaryl, preferably a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (5-25 membered) heteroaryl, more preferably a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (5-18 membered) heteroaryl.

[0056] In one embodiment, at least one of Ar 7 ~Ar 9 may be a substituted or unsubstituted (5-30 membered) heteroaryl, preferably at least two of Ar 7 ~Ar 9 may be a substituted or unsubstituted (5-30 membered) heteroaryl. For example, Ar 7 ~Ar 9is, independently of each other, optionally substituted or unsubstituted phenyl, optionally substituted or unsubstituted naphthyl, optionally substituted or unsubstituted p-biphenyl, optionally substituted or unsubstituted m-biphenyl, optionally substituted or unsubstituted o-terphenyl, optionally substituted or unsubstituted m-terphenyl, optionally substituted or unsubstituted p-terphenyl, optionally substituted or unsubstituted triphenylsilyl, optionally substituted or unsubstituted dibenzofuranyl, optionally substituted or unsubstituted dibenzothiophenyl, optionally substituted or unsubstituted phenanthrenyl, optionally substituted or unsubstituted benzophenanthrenyl, optionally substituted or unsubstituted chrysenyl, optionally substituted or unsubstituted triphenylenyl, optionally substituted or unsubstituted fluoranthenyl, or optionally substituted or unsubstituted benzonaphthofuranyl. Among these, the substituent may be substituted with at least one of, for example, deuterium, cyano, phenyl, and naphthyl.

[0057] According to one embodiment, Ar in Formula 3 7 ~Ar 9 at least one of can be represented by any one of the following Formulas 2-2, 3-1, and 3-2.

Chemical formula

[0058] In Formula 2-2, Y represents -O-, -S-, or -NR 39 and R 39 represents optionally substituted or unsubstituted (C6-C30) aryl, or optionally substituted or unsubstituted (3-30 membered) heteroaryl, R 31 ~R 38 are each independently L in Formula 3 7 ~L 9represents a linking position linked to , or represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, or may be linked with an adjacent substituent to form a ring.

Chemical formula

[0059] In Formulas 3-1 and 3-2, R 51 ~R 64 each independently represents L in Formula 3 7 ~L 9represents a linking position linked to, or hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 - C30) alkyl, substituted or unsubstituted (C3 - C30) cycloalkyl, substituted or unsubstituted (3 - 7 membered) heterocycloalkyl, a substituted or unsubstituted condensed ring of a (C3 - C30) aliphatic ring and a (C6 - C30) aromatic ring, substituted or unsubstituted (C6 - C30) aryl, substituted or unsubstituted (3 - 30 membered) heteroaryl, substituted or unsubstituted tri(C1 - C30) alkylsilyl, substituted or unsubstituted di(C1 - C30) alkyl(C6 - C30) arylsilyl, substituted or unsubstituted (C1 - C30) alkyldi(C6 - C30) arylsilyl, substituted or unsubstituted tri(C6 - C30) arylsilyl, substituted or unsubstituted mono - or di-(C1 - C30) alkylamino, substituted or unsubstituted mono - or di-(C2 - C30) alkenylamino, substituted or unsubstituted (C1 - C30) alkyl(C2 - C30) alkenylamino, substituted or unsubstituted mono - or di-(C6 - C30) arylamino, substituted or unsubstituted (C1 - C30) alkyl(C6 - C30) arylamino, substituted or unsubstituted mono - or di-(3 - 30 membered) heteroarylamino, substituted or unsubstituted (C1 - C30) alkyl(3 - 30 membered) heteroarylamino, substituted or unsubstituted (C2 - C30) alkenyl(C6 - C30) arylamino, substituted or unsubstituted (C2 - C30) alkenyl(3 - 30 membered) heteroarylamino, or substituted or unsubstituted (C6 - C30) aryl(3 - 30 membered) heteroarylamino.

[0060] In Formula 2 - 2, R 31 ~R 38 One of them may be a linking position linked to L 7 ~L 9 in Formula 3.

[0061] In Formula 3 - 1, R 51 ~R 60 One of them may be a linking position linked to L 7 ~L 9 in Formula 3.

[0062] In Formula 3-2, R 51 ~R 58 and R 61 ~R 64 One of them may be a linking position linked to L 7 ~L 9 in Formula 3.

[0063] According to one embodiment, the compound represented by Formula 3 can be more specifically exemplified by, but not limited to, the following compounds:

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chem.

Chem.

Chem.

[0064] In the above compound, D n means that n hydrogens are replaced by deuteriums, where n is an integer of 1 or more, and the upper limit of n is determined by the number of hydrogens that may be substituted in each compound.

[0065] The compound represented by Formula 3 according to the present disclosure can be produced by referring to synthetic methods known to those skilled in the art, such as the synthetic methods disclosed in (Patent Document 6), (Patent Document 7), and (Patent Document 8), etc., but is not limited thereto.

[0066] According to another embodiment, the present disclosure provides an organic electroluminescent compound represented by the following Formula 1-1.

Chem.

[0067] In Formula 1-1, R 1 ~R 10are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, a substituted or unsubstituted condensed ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, or *-L 1 --N(Ar 1 )(Ar 2 ) represents, provided that at least one of R 1 ~R 10 is *-L 1 -N(Ar 1 )(Ar 2 )) subject to the condition that L 1 represents a single bond, substituted or unsubstituted (C6-C30) arylene or substituted or unsubstituted (3-30 membered) heteroarylene, Ar 1 and Ar 2 each independently represent substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl, provided that R 1 , R 2 , R 4 , R 5 , R 8 , or R 9 is *-L 1 -N(Ar 1 )(Ar 2 ), the following conditions are satisfied: (1) R 5 or R 8 is *-L 1 -N(Ar 1 )(Ar 2) when it is, Ar 1 and Ar 2 at least one of which is unsubstituted or phenyl substituted with deuterium; (2) R 1 or R 2 is *-L 1 -N(Ar 1 )(Ar 2 ) when it is, Ar 1 and Ar 2 at least one of which is substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted carbazolyl, or Ar 1 and Ar 2 all are substituted or unsubstituted (3-30 membered) heteroaryl; (3) R 4 or R 9 is *-L 1 -N(Ar 1 )(Ar 2 ) when it is, Ar 1 and Ar 2 all are substituted or unsubstituted (3-30 membered) heteroaryl; or Ar 1 and Ar 2 at least one of which is substituted or unsubstituted carbazolyl.

[0068] According to one embodiment, the organic electroluminescent compound represented by Formula 1-1 can be more specifically exemplified by, but not limited to, the following compounds:

Chemical formula

Chemical formula

Chemical formula

[0069] According to another embodiment, the present disclosure provides an organic electroluminescent compound represented by the following Formula 3'.

Chemical formula

[0070] In Formula 3, X 1 ~X 3 each independently represents N or CR 11 wherein, at least one of X 1 ~X 3 represents N, R 11 represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, or a substituted or unsubstituted condensed ring group of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, L 7 ~L 9 each independently represents a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3-30 membered) heteroarylene, Ar 7 ~Ar 9 each independently represents substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, a substituted or unsubstituted condensed ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, or -L 21 -N(Ar21 )(Ar 22 ) represents, but Ar 7 ~Ar 9 At least one of them is Formula 2-2: [Chemical formula] is subject to the condition that

[0071] In Formula 2-2, Y represents -O- or -S-, R 31 ~R 38 each independently represents the linking position linked to L of Formula 3 7 ~L 9 or hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, or may be linked to adjacent substituents to form a ring, but L 7 ~L 9 If one of them is an unsubstituted or deuterium- or cyano-substituted phenylene, Ar 7 ~Ar 9 At least one of them is an unsubstituted or deuterium- or cyano-substituted binaphthyl, and L 7 ~L 9 If one of them is an unsubstituted or deuterium- or cyano-substituted naphthylene, Ar 7 ~Ar9 At least one of them is phenylnaphthyl which is unsubstituted or substituted with deuterium or cyano.

[0072] In one embodiment, in Formula 3’, when L 7 ~L 9 one of them is phenylene which is unsubstituted or substituted with deuterium or cyano, Ar 7 ~Ar 9 at least one of them may be a substituent which is unsubstituted or substituted with deuterium or cyano and is represented as follows:

Chemical formula

[0073] In one embodiment, in Formula 3’, when L 7 ~L 9 one of them is naphthylene which is unsubstituted or substituted with deuterium or cyano, Ar 7 ~Ar 9 at least one of them may be a substituent which is unsubstituted or substituted with deuterium or cyano and is represented as follows:

Chemical formula

[0074] According to one embodiment, the compound represented by Formula 3’ can be more specifically exemplified by, but not limited to, the following compounds:

Chemical formula

Chemical formula

Chemical formula

[0075] In the above compound, D n means that n hydrogens are replaced by deuteriums, where n is an integer of 1 or more, and the upper limit of n is determined by the number of hydrogens that may be substituted in each compound.

[0076] Hereinafter, an organic electroluminescent device including the above-described compounds represented by Formulas 1 to 3, 1-1, and 3' will be described.

[0077] An organic electroluminescent device according to an embodiment includes a first electrode and a second electrode facing each other on a substrate, at least one light-emitting layer disposed between the first electrode and the second electrode, and at least one electron blocking layer disposed between the first electrode and the light-emitting layer.

[0078] According to an embodiment, the first electrode may be an anode, and the second electrode may be a cathode. In this case, the first electrode and the second electrode may be formed as a transmissive conductive material, a semi-transmissive conductive material, or a reflective conductive material, respectively. The organic electroluminescent device may be a top-emitting type, a bottom-emitting type, or a double-sided emitting type depending on the types of materials forming the first electrode and the second electrode.

[0079] The electron blocking layer is disposed between the first electrode and the light-emitting layer, preferably between the hole transport layer and the light-emitting layer, and more preferably, the electron blocking layer is in contact with the light-emitting layer. According to one example, the electron blocking layer can improve the efficiency of the organic electroluminescent device by suppressing the movement of electrons injected from the cathode toward the anode without recombination in the light-emitting layer. In addition, this can prevent light emission leakage by blocking the overflow of electrons from the light-emitting layer and confining excitons within the light-emitting layer.

[0080] According to one embodiment, the electron blocking layer contains a compound represented by Formula 1, and the light-emitting layer can contain a compound represented by Formula 2 as the first host compound and a compound represented by Formula 3 as the second host compound, respectively. Here, the weight ratio of the first host compound to the second host compound can 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, still more preferably about 40:60 to about 60:40, and still more preferably about 50:50 in the light-emitting layer.

[0081] According to one embodiment, the organic electroluminescent device contains at least one compound selected from Compounds H1-1 to H1-161 as the electron blocking layer material, at least one compound selected from Compounds H3-1 to H3-743 and H4-1 to H4-484, and at least one compound selected from Compounds H5-1 to H5-402 as the host material of the light-emitting layer, and these host materials may be contained in the same light-emitting layer or in different light-emitting layers, respectively.

[0082] According to one embodiment, the present invention provides an organic electroluminescent device containing an organic electroluminescent compound represented by Formula 1-1.

[0083] According to one embodiment, the present disclosure provides an organic electroluminescent device containing an organic electroluminescent material containing a compound represented by Formula 3'.

[0084] An organic electroluminescent device according to an embodiment includes, in addition to an electron blocking layer and a light emitting layer, a hole injection layer, a hole transport layer, a hole auxiliary layer, an electron transport layer, and an electron injection layer as organic layers disposed between a first electrode and a second electrode, and may further include one or more layers selected from a light emitting auxiliary layer, an intermediate layer, a hole blocking layer, and an electron buffer layer. The 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 disclosure. Specifically, the hole injection layer, the hole transport layer, the hole auxiliary layer, the light emitting layer, the light emitting auxiliary layer, or the electron blocking layer may include, as a hole injection material, a hole transport material, a hole auxiliary material, a light emitting material, a light emitting auxiliary material, and an electron blocking material, an amine-based compound, such as an arylamine-based compound or a styrylarylamine-based compound. Further, an azine-based compound as an electron transport material, an electron injection material, an electron buffer material, and a hole blocking material may be included in the electron transport layer, the electron injection layer, the electron buffer layer, and the hole blocking layer. The organic layer may further include at least one metal selected from the group consisting of an organic metal of a Group 1 metal, a Group 2 metal, a transition metal of the fourth period, a transition metal of the fifth period, a lanthanide, and a d-transition element of the periodic table or at least one complex compound containing such a metal.

[0085] 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 may be multilayered to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, and in this case, two compounds may be used simultaneously in each of the multilayer. Further, the hole injection layer may be doped as a p-dopant.

[0086] The hole transport layer or the electron blocking layer according to an embodiment may be a plurality of layers, and each of the layers may use a plurality of compounds.

[0087] The hole auxiliary layer is disposed between the hole transport layer and the electron blocking layer (or the light-emitting layer), and can exhibit the effect of promoting or blocking the hole transport rate (or injection rate), thereby controlling the charge balance so as to effectively reduce the driving voltage of the organic electroluminescent device. When the organic electroluminescent device includes two or more hole transport layers, the additionally included hole transport layer can also be used as a hole auxiliary layer or an electron blocking layer.

[0088] The electron buffer layer, hole blocking layer, electron transport layer, electron injection layer, or a combination thereof can be used between the light-emitting layer and the cathode. The electron buffer layer may be a plurality of layers to control the injection of electrons and improve the interfacial characteristics between the light-emitting layer and the electron injection layer. In this case, two kinds of compounds can be used simultaneously in each of the plurality of layers. A hole blocking layer is disposed between the electron transport layer (or electron injection layer) and the light-emitting layer to prevent the arrival of holes at the cathode, thereby improving 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 multi-layer, and in this case, a plurality of compounds can be used in each layer. Further, the electron injection layer can be doped with an n-dopant.

[0089] The organic electroluminescent device of the present disclosure may further include a light-emitting auxiliary layer disposed between the anode and the light-emitting layer or between the cathode and the light-emitting layer. When the light-emitting auxiliary layer is disposed 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 light-emitting auxiliary layer is disposed 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. The light-emitting auxiliary layer, hole auxiliary layer, or electron blocking layer may have the effect of improving the efficiency and / or lifetime of the organic electroluminescent device.

[0090] An organic electroluminescent material according to an embodiment can be used as a light-emitting material for a white organic light-emitting device. 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., depending on the arrangement of R (red), G (green), YG (yellow-green), or B (blue) light-emitting units. In addition, the compound or organic electroluminescent material according to an embodiment can also be applied to an organic electroluminescent device containing QD (quantum dots).

[0091] In the organic electroluminescent device of the present disclosure, preferably, at least one layer (hereinafter referred to as "surface layer") selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer can be disposed on the inner surface of one or both of the pair of electrodes. Specifically, a chalcogenide (including oxide) layer of silicon and aluminum is preferably disposed on the anode surface of the electroluminescent medium layer, and a metal halide layer or a metal oxide layer is preferably disposed on the cathode surface of the electroluminescent medium layer. The operating stability of the organic electroluminescent device can be obtained by the surface layer. Preferably, as the chalcogenide, SiO X (1 ≤ X ≤ 2), AlO X (1 ≤ X ≤ 1.5), SiON, SiAlON, etc. are mentioned, and as the metal halide, LiF, MgF 2 , CaF 2 , rare earth metal fluorides, etc. are mentioned, and as the metal oxide, Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc. are mentioned.

[0092] An organic electroluminescent device according to an 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 an embodiment, a single light-emitting unit (light-emitting unit) may be formed in a structure in which two or more units are connected by a charge generation layer. The organic electroluminescent device includes a first electrode and a second electrode facing each other on a substrate, and a light-emitting layer laminated between the first electrode and the second electrode and emitting light in a specific wavelength range. It may include two or more light-emitting units, for example, three or more light-emitting units. According to one embodiment, the organic electroluminescent device may include a plurality of light-emitting units, and each of the light-emitting units may include a hole transport zone, a light-emitting layer, and an electron transport zone. The hole transport zone may include a hole injection layer and a hole transport layer, and the electron transport 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. The plurality of light-emitting units may emit the same color or different colors. In addition, one light-emitting unit may include one or more light-emitting layers, and the plurality of light-emitting layers may be light-emitting layers of the same color or different colors. This may include one or more charge generation layers disposed between each light-emitting unit. The 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 can be disposed between each light-emitting unit. Here, the plurality of charge generation layers may be the same as or different from each other. By disposing the charge generation layer between the light-emitting units, the current efficiency can be increased in each light-emitting unit, and the charge can be smoothly distributed. Specifically, the charge generation layer can be provided between two adjacent stacks and can be useful for driving a tandem organic electroluminescent device using only a pair of an anode and a cathode without a separate internal electrode disposed between the stacks.

[0093] The charge generation layer may be composed of an n-type charge generation layer and a p-type charge generation layer. 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 can include one selected from the group consisting of Li, Na, K, Rb, Cs, Fr, Yb, and combinations thereof, and the alkaline earth metal can include one selected from the group consisting of Be, Mg, Ca, Sr, Ba, Ra, and combinations thereof. The p-type charge generation layer can be manufactured from a metal or an organic material doped with a p-type dopant. For example, the metal can be 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. Moreover, commonly used materials can be used as a host material for p-type dopants and p-type doped organic materials.

[0094] In addition, in the organic electroluminescent device of the present disclosure, a mixed region of an electron transport compound and a reducing dopant, or a mixed region of a hole transport compound and an oxidizing dopant can be disposed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, and as a result, it becomes easier to inject and transport electrons from the mixed region to the electroluminescent medium. Further, the hole transport compound is oxidized to a cation, and as a result, it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium. Preferably, the oxidizing dopant includes various Lewis acids and acceptor compounds, and the reducing dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. Also, an organic electroluminescent device having two or more light-emitting layers and emitting white light can be prepared by using a reducing dopant layer as a charge generation layer.

[0095] The organic electroluminescent device according to one embodiment may further include at least one dopant in the light-emitting layer.

[0096] The dopants included in the organic electroluminescent device of the present disclosure may be at least one phosphorescent 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 is preferably a metallated complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably an orthometalated complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably an orthometalated iridium complex compound.

[0097] As the dopant included in the organic electroluminescent device of the present disclosure, the compound represented by the following formula 101 can be used, but is not limited thereto.

Chemical formula

[0098] In formula 101, L is any one of the following structures 1 to 3:

Chemical formula

[0099] In particular, specific examples of the dopant compound include, but are not limited to, the following.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

[0100] The organic electroluminescent device of the present disclosure can be manufactured by forming a first electrode or a second electrode on a substrate, and then forming an organic layer using any one of dry deposition methods such as vacuum evaporation, sputtering, plasma, or ion plating, or wet deposition methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, or flow coating, and then forming a second electrode or a first electrode thereon. When using a wet film-forming method, the thin film can be formed by dissolving or dispersing the material for forming each layer in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent may be any solvent in which the material for forming each layer can be dissolved or dispersed and there is no problem with the film-forming ability.

[0101] When forming a layer with an organic electroluminescent compound according to an embodiment, the layer can be formed by the methods listed above and can often be formed by co-evaporation or co-evaporation of mixtures. Co-evaporation is a co-evaporation method in which two or more materials are placed in their respective individual crucible sources and current is passed through both cells simultaneously to evaporate the materials; co-evaporation of mixtures is a co-evaporation method in which two or more materials are mixed in one crucible source before evaporation and then current is passed through one cell to evaporate the materials.

[0102] According to one embodiment, the present disclosure can provide a display device including a compound represented by Formulas 1 to 3 as an organic electroluminescent material. In addition, the organic electroluminescent device of the present disclosure can be used for the production of display devices such as smartphones, tablets, notebooks, PCs, TVs, etc., or display devices for vehicles, or lighting devices such as outdoor or indoor lighting.

Example

[0103] [Example 1] Synthesis of Compound H1-149

Chemical formula

[0104]

Table 1

[0105] [Example 2] Synthesis of Compound H1-146 [Chemical Formula] Compound 2-1 (2.4 g, 8.482 mmol), Compound 1-2 (3 g, 7.068 mmol), Pd 2 (dba) 3 (0.32 g, 0.353 mmol), NaOt-Bu (1 g, 10.60 mmol), and s-phos (0.29 g, 0.706 mmol) were added to 35 mL of o-xylene and stirred at 120 °C for 2 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered through celite, and distilled under reduced pressure. Next, it was separated by column chromatography to obtain Compound H1-146 (4.2 g, yield: 87%).

[0106] [Table 2]

[0107] [Example 3] Synthesis of Compound H1-161 [Chemical Formula] Compound 3-1 (10.0 g, 30.0 mmol), Compound 3-2 (10.53 g, 31.5 mmol), Pd 2 (dba) 3 (1.4 g, 1.5 mmol), S-phos (1.2 g, 3.0 mmol), and NaOtBu (4.3 g, 45.0 mmol) were added to 150 mL of o-xylene, and then stirred for 1 hour while refluxing at 120 °C. After the reaction was completed, the mixture was cooled to room temperature and the layers were separated (EA / H 2 O). Next, it was filtered through celite and then through silica to form a solid. Then, it was filtered to obtain Compound H1-161 (2.4 g, yield: 14%).

[0108] [Table 3]

[0109] [Example 4] Synthesis of Compound H1-147 [Chemical Formula] Compound 4-1 (3.3 g, 11.4 mmol), Compound 1-2 (4.65 g, 11.4 mmol), NaOtBu (1.64 g, 17.1 mmol), S-Phos (374 mg, 0.912 mmol), Pd 2 (dba) 3 (522 mg, 0.57 mmol), and 57 mL of xylene were placed in a flask and dissolved, and the mixture was stirred for 30 minutes while refluxing at 160 °C. After the reaction was completed, the organic layer was extracted with ethyl acetate, and residual moisture was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain Compound H1-147 (4 g, yield: 51%).

[0110] [Table 4]

[0111] Hereinafter, in order to understand the present disclosure in detail, a method for manufacturing an organic electroluminescent device including a compound according to the present disclosure, a method for manufacturing an organic electroluminescent material including the compound, and their device characteristics will be described.

[0112] [Device Example 1] Manufacture of an OLED Containing a Compound According to the Present Disclosure An OLED according to the present disclosure was prepared. First, an indium tin oxide (ITO) thin film (10 Ω / sq) (Geomatic Co., Ltd., Japan) on a glass substrate for the OLED was subjected to ultrasonic cleaning sequentially with acetone and isopropyl alcohol, and then stored in isopropyl alcohol and then used. Thereafter, the ITO substrate was mounted on the substrate holder of a vacuum deposition apparatus. Thereafter, Compound HI-1 was placed in one cell of the vacuum deposition apparatus, and Compound HT-1 was placed in another cell. The two materials were evaporated at different rates, and Compound HI-1 was deposited at a doping amount of 3 wt% based on the total amount of Compound HI-1 and Compound HT-1 to form a hole injection layer with a thickness of 10 nm. Thereafter, Compound HT-1 was deposited on the hole injection layer to form a first hole transport layer with a thickness of 80 nm. Next, Compound HT2-1 was introduced into another cell of the vacuum deposition apparatus and evaporated by passing a current through the cell, thereby forming a second hole transport layer with a thickness of 55 nm on the first hole transport layer. Next, Compound H1-42 was introduced as an electron blocking layer material, and an electron blocking layer with a thickness of 5 nm was deposited on the second hole transport layer. The first host compound and the second host compound described in Table 1 below as hosts were respectively introduced into two cells of the vacuum deposition apparatus, and Compound D-39 as a dopant was introduced into another cell. Thereafter, the two host materials were evaporated at a ratio of 1:1, and at the same time the dopant material was evaporated at a different rate, and deposited at a doping amount of 3 wt% with respect to the total amount of the host and the dopant to form a light-emitting layer with a thickness of 40 nm on the electron blocking layer. Next, Compound ETL-1 and Compound EIL-1 were evaporated as electron transport materials at a weight ratio of 50:50 to deposit an electron transport layer with a thickness of 35 nm on the light-emitting layer. Next, Compound EIL-1 was deposited to a thickness of 2 nm for the electron injection layer on the electron transport layer, and then an Al cathode with a thickness of 80 nm was deposited on the electron injection layer using another vacuum deposition apparatus. An OLED was manufactured in this way. Each compound used for all the materials was purified by vacuum sublimation at 10-6 Torr.

[0113] [Device Examples 2 to 22]: Manufacture of an OLED Containing a Compound According to the Present Disclosure An OLED was fabricated in the same manner as in Device Example 1, except that the compounds shown in Tables 1 to 4 below were used as the second hole transport layer material and the host material of the light-emitting layer.

[0114] [Comparative Examples 1 to 22] Fabrication of OLEDs without an electron blocking layer An OLED was fabricated in the same manner as in Device Example 1, except that the compounds shown in Tables 1 to 4 below were used as the second hole transport layer material and the host material of the light-emitting layer, no electron blocking layer was included, and a second hole transport layer with a thickness of 60 nm was deposited.

[0115] The driving voltage, luminous efficiency, and emission color of the OLEDs of Device Examples 1 to 22 and Comparative Examples 1 to 22 fabricated as described above at a luminance of 5,000 nits, and the time required for the luminance to decrease from 100% to 95% at a luminance of 10,000 nits (lifetime: T95) were measured. The results are shown in Table 4 below.

[0116]

Table 5

[0117]

Table 6

[0118]

Table 7

[0119]

Table 8

[0120]

Table 9

[0121] From Tables 1 to 4 above, it can be confirmed that the organic electroluminescent devices (Device Examples 1 to 22) containing the compounds according to the present disclosure as the electron blocking layer material and containing specific combinations of the compounds according to the present invention as the host material exhibit light emission efficiency equal to or higher than that of the organic electroluminescent devices (Comparative Examples 1 to 22) not containing an electron blocking layer, and particularly have significantly improved lifetime characteristics.

[0122] [Device Examples 23 to 28] Fabrication of OLEDs Containing Compounds According to the Present Invention An OLED was fabricated in the same manner as in Device Example 1, except that the compounds shown in Table 5 below were used as the second hole transport layer material and the host material of the light emitting layer, no electron blocking layer was included, and a second hole transport layer with a thickness of 60 nm was deposited.

[0123] [Comparative Example 23] Fabrication of an OLED Not Containing an Electron Blocking Layer An OLED was fabricated in the same manner as in Device Example 1, except that the compounds shown in Table 5 below were used as the second hole transport layer material and the host material of the light emitting layer, no electron blocking layer was included, a second hole transport layer with a thickness of 60 nm was deposited, the second host compound described in Table 5 was introduced into one cell in a vacuum deposition apparatus, compound D-39 was introduced into another cell as a dopant, and then a light emitting layer with a thickness of 40 nm was formed on the second hole transport layer by deposition at a doping amount of 3 wt% based on the total amount of the host and the dopant.

[0124] The driving voltage, light emission efficiency, and emission color of the OLEDs of Device Examples 23 to 28 and Comparative Example 23 fabricated as described above at a luminance of 5,000 nits, and the time required for the light emission to decrease from 100% to 95% at a luminance of 10,000 nits (lifetime: T95) were measured. The results are shown in Table 5 below.

[0125]

Table 10

[0126] From Table 5 above, it can be confirmed that the organic electroluminescent devices (Device Examples 23 to 28) containing specific combinations of the compounds according to the present disclosure as the light-emitting layer materials exhibit a lower driving voltage, a higher luminous efficiency, and particularly significantly improved lifetime characteristics as compared with Comparative Example 23.

[0127] The compounds used in the device examples and comparative examples are shown in Table 6 below.

[0128] [Table 11]

[0129] [Table 12]

[0130] [Table 13]

[0131] [Table 14]

Claims

1. A first electrode; A second electrode; and a light emitting layer between the first electrode and the second electrode; at least one electron blocking layer between the first electrode and the light-emitting layer, The electron blocking layer has the following formula 1: 【Chemistry 1】 (In the formula, R １ ~R １０ each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, or *-L １ -N(Ar １ ) (Ar ２ ), but R １ ~R １０ At least one of is *-L １ -N(Ar １ ) (Ar ２ ) L １ represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; Ar １ and Ar ２ each independently represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C2-C30) alkenyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl. and the light-emitting layer comprises at least two compounds.

2. 10. The organic electroluminescent device of claim 1, further comprising at least one hole-assisting layer between the first electrode and the electron-blocking layer.

3. The light-emitting layer is a compound represented by the following formula 2: 【Chemistry 2】 (In the formula, L ３ ~L ５ each independently represents a single bond, a substituted or unsubstituted (C1-C30) alkylene, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3-30 membered) heteroarylene, or a substituted or unsubstituted (C3-C30) cycloalkylene; Ar ３ ~Ar ５ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, or -N(Ar １１ ) (Ar １２ ) Ar １１ and Ar １２ each independently represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C2-C30) alkenyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl; In formula 2, L ３ ~L ５ are all single bonds, and Ar ３ ~Ar ５ (Excluding cases where all of are hydrogen) and at least one compound represented by the following formula 3: 【Chemistry 3】 (In the formula, X １ ~X ３ are each independently N or CR ａ However, X １ ~X ３ is N; R １１ represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, or a substituted or unsubstituted fused ring group of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, L ７ ~L ９ each independently represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; Ar ７ ~Ar ９ each independently represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (3-7 membered) heterocycloalkyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 membered) heteroaryl, a substituted or unsubstituted tri(C1-C30) alkylsilyl, a substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, a substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, a substituted or unsubstituted tri(C6-C30) arylsilyl, or *-L ２１ -N(Ar ２１ ) (Ar ２２ ) L ２１ represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; Ar ２１ and Ar ２２ each independently represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C2-C30) alkenyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl. and at least one compound represented by the formula:

4. Ar in Formula 2 ３ ~Ar ５ At least one of the following formulas 2-1 to 2-3: 【Chemistry 4】 (In the formula, X １ and Y １ are each independently -N=, -NR ２５ represents -, -O-, or -S-, but X １ and Y １ One of them is -N=, and X １ and Y １ The other is -NR ２５ -, -O-, or -S-; R ２１ is L in Equation 2 ３ ~L ５ represents a linking position where the aryl group is linked to the heteroaryl group, or represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 membered) heteroaryl; R ２２ ~R ２５ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, aryl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, or may be linked to adjacent substituents to form a ring, a and b each independently represent an integer of 1 or 2, and c represents an integer of 1 to 3; When a to c are integers of 2 or more, each R ２２ ~Each R ２４ may be the same or different, * is L in formula 2 ３ ~L ５ represents the position of connection to 【Chemistry 5】 (In the formula, Y is -O-, -S-, or -NR ３９ represents R ３９ represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 membered) heteroaryl; R ３１ ~R ３８ are each independently represented by the formula 2 ３ ~L ５ or represents a linking position where the aryl group is linked to the aryl group, or represents a hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) a arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, or may be linked to adjacent substituents to form a ring); 【Chemistry 6】 (In the formula, T is -O-, -S-, -CR ４５ R ４６ , -NR ４７ or -Se-, R ４５ ~R ４７ each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C6-C30) aryl; R ４１ ~R ４４ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, or -N(Ar ２１ ) (Ar ２２ ) or may be linked to adjacent substituents to form a ring, Ar ２１ and Ar ２２ each independently represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C2-C30) alkenyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl; d and g each independently represent an integer from 1 to 4, and e and f each independently represent an integer of 1 or 2; When f and g are integers of 2 or more, each R ４１ ~Each R ４４ may be the same or different from each other, * is L in formula 2 ３ ~L ５ (Indicates the connection position to 4. The organic electroluminescent device according to claim 3, wherein the organic electroluminescent device is represented by any one of the following formulas:

5. Ar in Formula 3 ７ ~Ar ７ At least one of the following formulas 2-2, 3-1, and 3-2: 【Chemistry 7】 (In the formula, Y is -O-, -S-, or -NR ３９ represents R ３９ represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 membered) heteroaryl; R ３１ ~R ３８ each independently represents L in formula 3 ７ ~L ９ or represents a linking position where the aryl group is linked to the aryl group, or represents a hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) a arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, or may be linked to adjacent substituents to form a ring); 【Chemistry 8】 (In the formula, R ５１ ~R ６４ each independently represents L in formula 3 ７ ~L ９ or represents a linking position where the alkyl group is linked to the alkyl group, or represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) ) alkylamino, substituted or unsubstituted mono- or di-(C2-C30) alkenylamino, substituted or unsubstituted (C1-C30) alkyl(C2-C30) alkenylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, substituted or unsubstituted mono- or di-(3-30 membered) heteroarylamino, substituted or unsubstituted (C1-C30) alkyl(3-30 membered) heteroarylamino, substituted or unsubstituted (C2-C30) alkenyl(C6-C30) arylamino, substituted or unsubstituted (C2-C30) alkenyl(3-30 membered) heteroarylamino, or substituted or unsubstituted (C6-C30) aryl(3-30 membered) heteroarylamino).

4. The organic electroluminescent device according to claim 3, wherein the organic electroluminescent device is represented by any one of the following formulas:

6. The compound represented by formula 1 is the following compound: 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 2. The organic electroluminescent device of claim 1, wherein the organic electroluminescent device is selected from the group consisting of

7. The compound represented by formula 2 is the following compound: 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemical 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemistry 27】 【Chemistry 28】 【Chemical 29】 【Chemistry 30】 【Chemistry 31】 【Chemistry 32】 【Chemical 33】 【Chemical 34】 【Chemistry 35】 【Chemical 36】 【Chemical 37】 【Chemical Formula 38】 【Chemical 39】 【Chemistry 40】 【Chemistry 41】 【Chemistry 42】 【Chemistry 43】 【Chemistry 44】 【Chemistry 45】 【Chemistry 46】 【Chemistry 47】 【Chemistry 48】 【Chemistry 49】 【Chemistry 50】 【Chemistry 51】 【Chemistry 52】 【Chemistry 53】 【Chemical 54】 【Chemistry 55】 【Chemistry 56】 【Chemistry 57】 【Chemistry 58】 (In the above compound, D ｎ means that n hydrogens are replaced with deuterium, where n is an integer equal to or greater than 1, and the upper limit of n is determined by the number of hydrogens that can be replaced in each compound.

4. The organic electroluminescent device of claim 3, wherein the organic electroluminescent device is selected from the group consisting of

8. The compound represented by formula 3 is the following compound: 【Chemistry 59】 【Chemistry 60】 【Chemistry 61】 【Chemistry 62】 【Chemistry 63】 【Chemistry 64】 【Chemistry 65】 【Chemistry 66】 【Chemistry 67】 【Chemistry 68】 【Chemistry 69】 【Chemistry 70】 【Chemistry 71】 【Chemical 72】 【Chemical 73】 【Chemical 74】 【Chemistry 75】 【Chemical Formula 76】 (In the above compound, D ｎ means that n hydrogens are replaced with deuterium, where n is an integer equal to or greater than 1, and the upper limit of n is determined by the number of hydrogens that can be replaced in each compound.

4. The organic electroluminescent device of claim 3, wherein the organic electroluminescent device is selected from the group consisting of

9. The following formula 1-1: 【Chemical 77】 (In the formula, R １ ~R １０ each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, or *-L １ -N(Ar １ ) (Ar ２ ), but R １ ~R １０ At least one of the following is *-L １ -N(Ar １ ) (Ar ２ ) L １ represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; Ar １ and Ar ２ each independently represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C2-C30) alkenyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl; R １ , R ２ , R ４ , R ５ , R ８ , or R ９ Ga*-L １ -N(Ar １ ) (Ar ２ ), provided that the following conditions are met: (1) R ５ Or R ８ Ga*-L １ -N(Ar １ ) (Ar ２ ), then Ar １ and Ar ２ at least one of is unsubstituted or deuterium substituted phenyl; (2) R １ Or R ２ Ga*-L １ -N(Ar １ ) (Ar ２ ), then Ar １ and Ar ２ At least one of Ar is substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted carbazolyl, １ and Ar ２ all of are substituted or unsubstituted (3-30 membered) heteroaryl; (3) R ４ Or R ９ Ga*-L １ -N(Ar １ ) (Ar ２ ), then Ar １ and Ar ２ all of are substituted or unsubstituted (3-30 membered) heteroaryl; or Ar １ and Ar ２ At least one of is a substituted or unsubstituted carbazolyl. The organic electroluminescent compound represented by the formula:

10. The organic luminescent compound represented by formula 1-1 is the following compound: 【Chemical 78】 【Chemical Formula 79】 【Chemistry 80】 10. The organic electroluminescent compound according to claim 9, selected from:

11. An organic electroluminescent device comprising the organic electroluminescent compound of claim 9.

12. The following formula 3': 【Chemistry 81】 (In the formula, X １ ~X ３ are each independently N or CR ａ However, X １ ~X ３ represents N; R １１ represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, or a substituted or unsubstituted fused ring group of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, L ７ ~L ９ each independently represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; Ar ７ ~Ar ９ each independently represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (3-7 membered) heterocycloalkyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 membered) heteroaryl, a substituted or unsubstituted tri(C1-C30) alkylsilyl, a substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, a substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, a substituted or unsubstituted tri(C6-C30) arylsilyl, or -L ２１ -N(Ar ２１ ) (Ar ２２ ), but R ７ ~R ９ At least one of the formulas 2-2: 【Chemistry 82】 Provided that, In formula 2-2, Y represents -O- or -S-; R ３１ ~R ３８ each independently represents L in formula 3 ７ ~L ９ or represents a linking position where the aryl group is linked to the aryl group, or represents a hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) a arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, or may be linked to an adjacent substituent to form a ring, L ７ ~L ９ When one of Ar is unsubstituted or deuterium- or cyano-substituted phenylene, ７ ~Ar ９ at least one of L is unsubstituted or deuterium- or cyano-substituted binaphthyl; ７ ~L ９ When one of Ar is unsubstituted or deuterium- or cyano-substituted naphthylene, ７ ~Ar ９ at least one of which is unsubstituted or substituted with deuterium or cyano. The organic electroluminescent compound represented by the formula:

13. The organic luminescent compound represented by formula 3' is the following compound: 【Chemistry 83】 【Chemistry 84】 【Chemistry 85】 【Chemistry 86】 【Chemistry 87】 (In the above compound, D ｎ means that n hydrogens are replaced with deuterium, where n is an integer equal to or greater than 1, and the upper limit of n is determined by the number of hydrogens that can be replaced in each compound. The organic electroluminescent compound according to claim 12, selected from:

14. An organic electroluminescent device comprising the organic electroluminescent compound of claim 12.

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