Organic electroluminescent device

Abstract

The present disclosure relates to an organic electroluminescent device. The organic electroluminescent device according to the present disclosure may have overall device stability by including a deuterated compound in an electron transport region.

Description

Technical Field

[0001] The present disclosure relates to an organic electroluminescent device comprising one or more deuterated compounds. Background Art

[0002] Small molecule green organic electroluminescent devices (OLEDs) were first developed in 1987 by Tang et al. of Eastman Kodak using a TPD / Alq3 bilayer consisting of a light-emitting layer and a charge transport layer. Since then, OLED development has progressed rapidly and commercialization has been achieved. Currently, OLEDs mainly use phosphorescent materials with excellent luminous efficiency in panel implementation. However, in various applications such as TVs and lighting devices, the lifespan of OLEDs is often insufficient, and higher OLED efficiency is still required. Generally, the lifespan of an OLED shortens as its brightness increases. Therefore, OLEDs with high luminous efficiency and / or extended lifespan are essential for long-term use and high-resolution displays.

[0003] To improve current efficiency and / or lifespan, various materials or concepts for the organic layers of organic electroluminescent devices have been proposed, but they have not proven satisfactory in actual use. In addition, there is a continuing need to develop organic electroluminescent devices with enhanced properties such as improved current efficiency and / or lifespan characteristics compared to combinations of previously disclosed specific compounds.

[0004] Meanwhile, Korean Patent Application Publication Nos. 2023-0046493, 2022-0081251, and 2022-0147537 disclose an organic electroluminescent device comprising one or more deuterated compounds. However, the foregoing references do not specifically disclose an organic electroluminescent device having overall device stability by including one or more deuterated compounds in the electron transport region. In addition, there is a continuing need to develop luminescent materials with enhanced properties such as improved lifespan characteristics compared to previously disclosed specific organic electroluminescent devices. Summary of the Invention

[0005] Technical Problem

[0006] An object of the present disclosure is to provide an organic electroluminescent device having improved current efficiency and / or lifespan characteristics compared to conventional organic electroluminescent devices.

[0007] Solution to the Problem

[0008] As a result of in-depth research to solve technical problems, the inventors of the present invention have found that the above object can be achieved by an organic electroluminescent device, which includes an anode, a hole transport region, a light-emitting layer, an electron transport region, and a cathode, wherein the hole transport region, the light-emitting layer, and the electron transport region each contain one or more deuterated compounds, and the structures of each of these compounds are the same as or different from each other.

[0009] Advantages of the present invention

[0010] The organic electroluminescent device of the present disclosure exhibits higher current efficiency and / or improved lifetime characteristics by including one or more deuterated compounds in each of the hole transport region, the light-emitting layer, and the electron transport region. Detailed implementation manners

[0011] Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present disclosure and does not mean to limit the scope of the present disclosure.

[0012] The term "organic electroluminescent compound" in the present disclosure refers to a compound that can be used in an organic electroluminescent device and can be incorporated into any layer constituting the organic electroluminescent device as needed.

[0013] The term "organic electroluminescent material" in the present disclosure refers to a material that can be used in an organic electroluminescent device and can contain at least one compound. If necessary, the organic electroluminescent material can be incorporated into any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material can be any one of the following: hole injection material, hole transport material, hole assisting material, light-emitting assisting material, electron blocking material, light-emitting material (including host material and dopant material), electron buffer material, hole blocking material, electron transport material, electron injection material, etc.

[0014] The term "multiple organic electroluminescent materials" in the present disclosure refers to one or more organic electroluminescent materials containing a combination of two or more compounds, and the organic electroluminescent materials can be incorporated into any layer constituting the organic electroluminescent device. It can mean both materials before being incorporated into the organic electroluminescent device (e.g., before vapor deposition) and materials after being incorporated into the organic electroluminescent device (e.g., after vapor deposition). For example, the multiple organic electroluminescent materials can be a combination of two or more compounds, and the two or more compounds can be included in at least one of the following layers: hole injection layer, hole transport layer, hole assisting layer, light-emitting assisting layer, electron blocking layer, light-emitting layer, electron buffer layer, hole blocking layer, electron transport layer, and electron injection layer. The two or more compounds can be included in the same layer or different layers, and can be co-evaporated or co-evaporated, or can be evaporated separately.

[0015] The term "multiple host materials" in the present disclosure means a host material comprising a combination of at least two compounds, which can be included in any light-emitting layer constituting an organic electroluminescent device. It can mean both the material before being included in the organic electroluminescent device (e.g., before vapor deposition) and the material after being included in the organic electroluminescent device (e.g., after vapor deposition). For example, the multiple host materials of the present disclosure are a combination of at least two host materials, and can optionally further include conventional materials included in the organic electroluminescent materials. At least two compounds included in the multiple host materials of the present disclosure can be included together in one light-emitting layer, or can be included separately in different light-emitting layers. For example, at least two host materials can be co-evaporated or co-evaporated, or can be evaporated separately.

[0016] As used herein, the term "(C1-C30)alkyl" means a straight-chain or branched-chain alkyl having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 10, and more preferably 1 to 6. The above alkyl can include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, etc. The term "(C3-C30)cycloalkyl" means a monocyclic hydrocarbon or polycyclic hydrocarbon having 3 to 30 ring skeleton carbon atoms, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The above cycloalkyl can include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, etc. The term "(3- to 7-membered)heterocycloalkyl" means a cycloalkyl having 3 to 7 ring skeleton atoms and including at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, and preferably selected from the group consisting of O, S, and N. The above heterocycloalkyl can include tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc. The terms "(C6-C30)aryl", "(C6-C30)arylene", and "(C6-C30)arylene triyl" mean monocyclic or fused-ring groups derived from an aromatic hydrocarbon having 6 to 30 ring skeleton carbon atoms, which aromatic hydrocarbon can be partially saturated. The above aryl, arylene, and arylene triyl can include a spiro structure. The above aryl can include phenyl, biphenyl, terphenyl, quinquephenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, benzophenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, groups, naphthacenyl, fluoranthenyl, spirobifluorenyl, spiro[fluorene-benzofluorene] group, spiro[cyclopentene-fluorene] group, spiro[indan-fluorene] group, azulenyl, tetramethyldihydrophenanthrenyl, etc. Specifically, the above aryl group may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, tetracenyl, pyrenyl, 1- group, 2- group, 3- group, 4- group, 5- group, 6- group, benzo[c]phenanthryl, benzo[g] Base, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo[a]fluorenyl, benzo[b]fluorenyl, benzo[c]fluorenyl, dibenzofluorenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, 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, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzo[a]fluoranthenyl, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, 4''-tert-butyl-p-terphenyl-4-yl, 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, 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.,

[0017] The terms “(3- to 30-membered) heteroaryl”, “(3- to 30-membered) heteroarylene” and “(3- to 30-membered) heteroarylidene” mean an aryl group having 3 to 30 ring backbone atoms and including at least one, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, Si, P, Se, Te and Ge. The above-mentioned heteroaryl may be a monocyclic ring, or a fused ring condensed with at least one benzene ring; it may be partially saturated; it may be a heteroaryl formed by connecting at least one heteroaryl or aryl group to a heteroaryl via one or more single bonds; and it may include a spiro structure. The above-mentioned heteroaryl may include monocyclic heteroaryls such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl and pyridazinyl, and fused-ring heteroaryls such as benzofuryl, benzothienyl, isobenzofuryl, dibenzofuryl, dibenzothienyl, dibenzoselenophenyl, naphthobenzofuryl, naphthobenzothienyl, naphthoxazolyl, benzofuroquinolinyl, benzofuroquinazolinyl, benzofuronaphthyridinyl, benzofuropyrimidinyl, naphthofuropyrimidinyl, benzothienoquinolinyl, benzothienoquinazolinyl, naphthyridinyl, benzothienonaphthyridinyl, benzothienopyrimidinyl, naphthothienopyrimidinyl, pyrimidoindolyl, benzopyrimidoindolyl, benzofuropyrazinyl, naphthofuropyrazinyl, benzothienopyrazinyl, naphthothienopyrazinyl, phenoxazolyl, phenothiazolyl, phenobenzofuryl, benzophenothienyl, pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, benzotriazolyl, phenazinyl, imidazopyridyl, benzopyranquinazolinyl, thiobenzopyranquinazolinyl, dimethylbenzoperimidinyl, indolocarbazolyl, indacarbazolyl, etc. More specifically, the above-mentioned heteroaryl may include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridyl, 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, 3-pyridinyl, 4-pyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuryl, 3-benzofuryl, 4-benzofuryl, 5-benzofuryl, 6-benzofuryl, 7-benzofuryl, 1-iso-benzofuryl, 3-iso-benzofuryl, 4-iso-benzofuryl, 5-iso-benzofuryl, 6-iso-benzofuryl, 7-iso-benzofuryl, 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-tert-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4-tert-butyl-1-indolyl, 2-tert-butyl-3-indolyl, 4-tert-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 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]-benzothienyl, 9-naphtho-[2,1-b]-benzothienyl, 10-naphtho-[2,1-b]-benzothienyl, 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-germaf luorenyl, 2-germaf luorenyl, 3-germaf luorenyl, 4-germaf luorenyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, etc. The "(hetero)aryl" can be classified into the (hetero)aryl with electron characteristics and the (hetero)aryl with hole characteristics. The (hetero)aryl with electron characteristics is a substituent relatively rich in electrons in the parent nucleus, such as substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinolinyl, etc. The (hetero)aryl with hole characteristics is a substituent with relatively insufficient electrons in the parent nucleus, such as substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, etc. In this article, the term "halogen" includes F, Cl, Br, and I.,

[0018] In addition, "ortho-" ("o-"), "meta-" ("m-"), and "para-" ("p-") are prefixes that each indicate the relative positions of substituents. The prefix "ortho-" indicates that two substituents are adjacent to each other, and for example, when two substituents in a benzene derivative occupy positions 1 and 2 or positions 2 and 3, this is called the "ortho-" configuration. The prefix "meta-" indicates that two substituents are at positions 1 and 3, and for example, when two substituents in a benzene derivative occupy positions 1 and 3, this is called the "meta-" configuration. The prefix "para-" indicates that two substituents are at positions 1 and 4, and for example, when two substituents in a benzene derivative occupy positions 1 and 4, this is called the "para-" configuration. Unless otherwise specified, a substituent can replace a hydrogen at a position where the substituent can be substituted, without limitation, and when two or more hydrogen atoms in a certain functional group are each replaced by a substituent, each substituent can be the same as or different from each other. The maximum number of substituents that can be substituted in a certain functional group can be the total number of valences that can be substituted for each atom forming the functional group.

[0019] In this text, a substituted alkyl, substituted alkenyl, substituted cycloalkyl, substituted cycloalkenyl, substituted heterocycloalkyl, substituted silyl, substituted (sub)aryl, substituted (sub)heteroaryl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted fused ring group of one or more aliphatic rings and one or more aromatic rings, substituted mono- or di-alkylamino, substituted mono- or di-alkenylamino, substituted mono- or di-arylamino, substituted mono- or di-heteroarylamino, substituted alkylalkenylamino, substituted alkylarylamino, substituted alkylheteroarylamino, substituted alkenylarylamino, substituted alkenylheteroarylamino, substituted arylheteroarylamino, substituted dibenzofuranyl, substituted dibenzothiophenyl, or substituted carbazolyl may each independently be substituted by at least one selected from the group consisting of: deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; phosphine oxide; (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- to 7-membered)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (C6-C30)aryl unsubstituted or substituted by at least one of (C1-C30)alkyl, (C6-C30)aryl, and (3- to 30-membered)heteroaryl; (3- to 30-membered)heteroaryl unsubstituted or substituted by one or more (C6-C30)aryl; tris(C1-C30)alkylsilyl; one or more tris(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; fused ring group of one or more (C3-C30)aliphatic rings and one or more (C6-C30)aromatic rings; amino; mono- or di-(C1-C30)alkylamino; mono- or di-(C2-C30)alkenylamino; mono- or di-(C6-C30)arylamino unsubstituted or substituted by one or more (C1-C30)alkyl; mono- or di-((3- to 30-membered)heteroarylamino; (C1-C30)alkyl(C2-C30)alkenylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkyl(3- to 30-membered)heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30)alkenyl(3- to 30-membered)heteroarylamino; (C6-C30)aryl(3- to 30-membered)heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylboronyl;Bis(C1-C30)alkylboronylcarbonyl; (C1-C30)alkyl(C6-C30)arylboronylcarbonyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl. According to one embodiment of the present disclosure, the substituted alkyl and the like are each independently substituted with at least one selected from the group consisting of: (C1-C25)alkyl; (C3-C25)cycloalkyl; (C6-C25)aryl unsubstituted or substituted with at least one of (C1-C30)alkyl, (C6-C30)aryl, and (3- to 30-membered) heteroaryl; (3- to 25-membered) heteroaryl unsubstituted or substituted with one or more (C6-C30)aryl; and mono- or di-(C6-C25)arylamino unsubstituted or substituted with one or more (C6-C30)aryl. For example, the substituted alkyl and the like may be substituted with at least one selected from the group consisting of: methyl, phenyl, biphenyl, terphenyl, naphthyl, naphthyl substituted with one or more phenyl, naphthyl substituted with one or more naphthyl, naphthyl substituted with one or more dibenzofuranyl, phenanthryl, triphenylene, benzofluorene, benzofluorene substituted with one or more methyl, benzofluorene substituted with one or more phenyl, carbazolyl, carbazolyl substituted with one or more phenyl, dibenzofuranyl, dibenzothiophenyl, diphenylamino, phenylbiphenylamino, etc.;

[0020] In the present disclosure, if no substituent is indicated in the formula or compound structure, this may mean that all possible positions of the substituent are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be the isotope deuterium, and in this case, the content of deuterium may be 0% to 100%. In the present disclosure, in the case where no substituent is indicated in the formula or compound structure, if no substituent such as 0% deuterium and 100% hydrogen is explicitly excluded and all substituents are hydrogen, hydrogen and deuterium may be used in combination in the compound. Deuterium is one of the isotopes of hydrogen and is an element having a deuteron as its nucleus, and the deuteron consists of a proton and a neutron. It can be represented as hydrogen-2, and its element symbol can also be written as D or 2 H. Isotopes are atoms with the same atomic number (Z) but different mass numbers (A), and can also be interpreted as elements with the same number of protons but different numbers of neutrons.

[0021] In the present disclosure, "a combination thereof" refers to a combination of one or more elements from the corresponding list to form a known or chemically stable arrangement that a person skilled in the art can envision from the corresponding list. For example, an alkyl group and deuterium can be combined to form a partially or fully deuterated alkyl group; a halogen and an alkyl group can be combined to form a haloalkyl substituent; and a halogen, an alkyl group, and an aryl group can be combined to form a haloarylalkyl group. For example, preferred substituent combinations include up to 50 atoms that are not hydrogen or deuterium, up to 40 atoms that are not hydrogen or deuterium, or up to 30 atoms that are not hydrogen or deuterium. However, in many cases, preferred substituent combinations can contain up to 20 atoms that are not hydrogen or deuterium.

[0022] In the formulas of the present disclosure, when there are multiple substituents represented by the same symbol, each substituent represented by the same symbol can be the same as or different from each other.

[0023] In the formulas of the present disclosure, when a ring is formed by connecting to adjacent substituents, the ring can be connected to two or more adjacent substituents to form a substituted or unsubstituted, monocyclic or polycyclic (3-membered to 30-membered) alicyclic or aromatic ring, or a combination thereof. In addition, the formed ring can contain at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S. According to one embodiment of the present disclosure, the number of ring backbone atoms is (5-membered to 20-membered), and according to another embodiment of the present disclosure, the number of ring backbone atoms is (5-membered to 15-membered).

[0024] The present disclosure relates to an organic electroluminescent device comprising an anode, a hole transport region, a light-emitting layer, an electron transport region, and a cathode, wherein the hole transport region, the light-emitting layer, and the electron transport region each contain one or more deuterated compounds, and the structures of each of these compounds are the same as or different from each other.

[0025] According to one embodiment of the present disclosure, there is provided an organic electroluminescent device, wherein the hole transport region is configured by sequentially stacking a hole injection layer, a hole transport layer composed of one or more layers, and a hole assisting layer or an electron blocking layer on the anode, and at least one of these layers contains one or more deuterated compounds.

[0026] According to one embodiment of the present disclosure, there is provided an organic electroluminescent device, wherein the electron transport region is configured by sequentially stacking an electron buffer layer or a hole blocking layer composed of one or more layers, an electron transport layer composed of one or more layers, and an electron injection layer on the light-emitting layer, and at least one of these layers contains one or more deuterated compounds.

[0027] According to an embodiment of the present disclosure, there is provided an organic electroluminescent device in which a light-emitting layer is composed of one or more layers, and at least one of the light-emitting layers contains one or more deuterated compounds as a host.

[0028] According to an embodiment of the present disclosure, there is provided an organic electroluminescent device in which a light-emitting layer contains a phosphorescent or fluorescent light-emitting compound, and the compound contains an iridium (Ir), platinum (Pt), or boron (B) atom.

[0029] According to an embodiment of the present disclosure, the organic electroluminescent device according to the present disclosure may include at least one layer in a hole transport region, and at least one layer in the hole transport region contains a compound represented by the following Formula 1.

[0030]

[0031] In Formula 1,

[0032] Ar 1 to Ar 3 each independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3-membered to 30-membered) heteroaryl group, a substituted or unsubstituted mono- or di-(C6-C30) arylamino group, a mono- or di-(C1-C30) alkylamino group, a mono- or di-(C2-C30) alkenylamino group, a (C1-C30) alkyl(C6-C30) arylamino group, a mono- or di-(3-membered to 30-membered) heteroarylamino group, or a (C6-C30) aryl(3-membered to 30-membered) heteroarylamino group, provided that each Ar 1 to each Ar 3 contains at least one of a substituted or unsubstituted (C6-C30) aryl group or a substituted or unsubstituted (3-membered to 30-membered) heteroaryl group;

[0033] L 1 to L 3 each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-membered to 30-membered) heteroarylene group; and

[0034] D n represents that n number of hydrogens are replaced by deuterium, and n represents an integer of 1 or greater and has an upper limit of the number of hydrogen atoms in the non-deuterated compound.

[0035] According to an embodiment of the present disclosure, Ar 1 to Ar 3each independently represents hydrogen, deuterium, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3-membered to 30-membered) heteroaryl group, or a substituted or unsubstituted mono- or di-(C6-C30) arylamino; preferably hydrogen, deuterium, a substituted or unsubstituted (C6-C26) aryl group, a substituted or unsubstituted (3-membered to 13-membered) heteroaryl group, or a substituted or unsubstituted mono- or di-(C6-C12) arylamino, provided that each Ar 1 to each Ar 3 may contain at least one of a substituted or unsubstituted (C6-C30) aryl group or a substituted or unsubstituted (3-membered to 30-membered) heteroaryl group. More preferably, at least one of Ar 1 to Ar 3 represents a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzo[9,10]fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group. For example, each of Ar 1 to Ar 3 independently represents a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzo[9,10]fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted diphenylamino group, or a substituted or unsubstituted phenylbiphenylamino group, etc., provided that each Ar 1 to each Ar 3 may contain at least one of a substituted or unsubstituted (C6-C30) aryl group or a substituted or unsubstituted (3-membered to 30-membered) heteroaryl group. In the above, the substituent of the substituted group may be at least one selected from deuterium, methyl, phenyl, biphenyl, phenanthryl, benzo[9,10]fluorenyl substituted with one or more methyl groups, benzo[9,10]fluorenyl substituted with one or more phenyl groups, carbazolyl, carbazolyl substituted with one or more phenyl groups, dibenzofuranyl, diphenylamino, and phenylbiphenylamino.

[0036] According to one embodiment of the present disclosure, each of L 1 to L 3 independently may represent a single bond, a substituted or unsubstituted (C6-C25) arylene group, or a substituted or unsubstituted (3-membered to 25-membered) heteroarylene group. Preferably, each of L 1 to L 3 independently may represent a single bond, a substituted or unsubstituted (C6-C12) arylene group, or a substituted or unsubstituted (3-membered to 13-membered) heteroarylene group. For example, each of L 1 to L 3Each independently may be a single bond, a substituted or unsubstituted phenylene, biphenylene, substituted or unsubstituted carbazolylene, dibenzothiophenylene or dibenzofuranylene, etc. Among the above, the substituent of the substituted one may be at least one selected from deuterium, phenyl, carbazolyl, carbazolyl substituted with one or more phenyl groups, dibenzofuranyl and dibenzothiophenyl.

[0037] According to one embodiment of the present disclosure, the deuterium substitution rate is preferably 20% to 100% of the total number of hydrogens, more preferably 20% to 95%, even more preferably 30% to 95%, and even more preferably 40% to 95%.

[0038] According to one embodiment of the present disclosure, the deuterated compound may be more specifically exemplified by the following compounds, but is not limited thereto.

[0039]

[0040]

[0041] According to one embodiment of the present disclosure, the organic electroluminescent device of the present disclosure may include a compound represented by the following formula 2 or formula 3 in at least one layer of the electron transport region.

[0042]

[0043] In formula 2,

[0044] L 11 and L 12 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-membered to 30-membered) heteroarylene;

[0045] Ar 11 and Ar 12 Each independently represents a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-membered to 30-membered) heteroaryl;

[0046] R 11 to R 18each independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C2-C30)alkenylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, a substituted or unsubstituted mono- or di-(3- to 30-membered) heteroarylamino group, a substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino group, a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group, a substituted or unsubstituted (C1-C30)alkyl(3- to 30-membered) heteroarylamino group, a substituted or unsubstituted (C2-C30)alkenyl(C6-C30)arylamino group, a substituted or unsubstituted (C2-C30)alkenyl(3- to 30-membered) heteroarylamino group, or a substituted or unsubstituted (C6-C 30 ) aryl(3- to 30-membered) heteroarylamino group;

[0047] R 11 and R 14 to R 16 at least one of which represents deuterium; and

[0048] D n represents that n numbers of hydrogens are replaced by deuteriums, and n represents an integer of 1 or greater and has an upper limit of the number of hydrogen atoms in the non-deuterated compound.

[0049] According to one embodiment of the present disclosure, L 11 and L 12 each independently may represent a single bond, or a substituted or unsubstituted (C6-C30) arylene group; preferably a single bond, or a substituted or unsubstituted (C6-C25) arylene group; more preferably a single bond, or a substituted or unsubstituted (C6-C18) arylene group. For example, L 11 and L 12 each independently may be a single bond or a phenylene group.

[0050] According to one embodiment of the present disclosure, Ar 11 and Ar 12Each independently may represent a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5-membered to 30-membered) heteroaryl group; preferably a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5-membered to 25-membered) heteroaryl group; more preferably a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5-membered to 20-membered) heteroaryl group. For example, Ar 11 and Ar 12 Each independently may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted m-biphenyl group, a substituted or unsubstituted p-biphenyl group, or a substituted or unsubstituted benzimidazolyl group represented by the following Formula 2-1 or 2-2.

[0051] According to one embodiment of the present disclosure, the deuterium substitution rate is preferably 20% to 100% of the total number of hydrogens, more preferably 20% to 95%, even more preferably 30% to 95%, and even more preferably 40% to 95%.

[0052]

[0053] In Formulas 2-1 and 2-2,

[0054] L' 1 represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-membered to 30-membered) heteroarylene group; and

[0055] R' 1 to R' 5 Each independently represents hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-membered to 30-membered) heteroaryl group.

[0056] According to one embodiment of the present disclosure, L' 1 may represent a single bond, or a substituted or unsubstituted (C6-C30) arylene group; preferably a single bond, or a substituted or unsubstituted (C6-C25) arylene group; more preferably a single bond, or a substituted or unsubstituted (C6-C18) arylene group. For example, L' 1 may be a single bond or a phenylene group.

[0057] According to one embodiment of the present disclosure, R' 1 to R' 4 Each independently may represent hydrogen or deuterium.

[0058] According to one embodiment of the present disclosure, R' 5may represent a substituted or unsubstituted (C1-C30) alkyl group, or a substituted or unsubstituted (C6-C30) aryl group; preferably a substituted or unsubstituted (C1-C10) alkyl group, or a substituted or unsubstituted (C6-C25) aryl group; more preferably a substituted or unsubstituted (C1-C4) alkyl group, or a substituted or unsubstituted (C6-C18) aryl group. For example, R' 5 may be ethyl, phenyl, naphthyl or biphenyl.

[0059] According to one embodiment of the present disclosure, R 11 to R 18 each independently may represent hydrogen, deuterium, or a substituted or unsubstituted benzimidazolyl group represented by the following Formula 2-1 or 2-2.

[0060] According to one embodiment of the present disclosure, at least one of R 11 to R 18 , Ar 11 and Ar 12 may be a substituted or unsubstituted benzimidazolyl group represented by the above Formula 2-1 or 2-2.

[0061]

[0062] In Formula 3,

[0063] X 21 to X 23 each independently represents CR' or N, provided that at least two of X 21 to X 23 represent N;

[0064] R' represents hydrogen or deuterium;

[0065] L 21 to L 23 each independently represents a single bond, a substituted or unsubstituted (C6-C 30 ) arylene group, or a substituted or unsubstituted (3-membered to 30-membered) heteroarylene group;

[0066] Ar 21 to Ar 23 each independently represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-membered to 30-membered) heteroaryl group, provided that at least one of Ar 21 to Ar 23 contains deuterium;

[0067] p, q and r each independently represent an integer from 1 to 3, where if p, q and r represent an integer of 2 or greater, then each L 21 to each L 23 may be the same or different; and

[0068] D n represents that n hydrogens are replaced by deuteriums, and n represents an integer of 1 or greater and has an upper limit of the number of hydrogen atoms in the non-deuterated compound.

[0069] According to one embodiment of the present disclosure, X 21 to X 23 at least two of which represent N, and preferably, X 21 to X 23 all can represent N.

[0070] According to one embodiment of the present disclosure, L 21 to L 23 each independently can represent a single bond, or a substituted or unsubstituted (C6-C30) arylene group. Preferably, L 21 to L 23 each independently represents a single bond, or a substituted or unsubstituted (C6-C25) arylene group. More preferably, L 21 to L 23 each independently can represent a single bond, or a substituted or unsubstituted (C6-C18) arylene group. For example, L 21 to L 23 each independently can be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted p-biphenylene group, a substituted or unsubstituted m-biphenylene group, or a substituted or unsubstituted o-terphenyl group. Among the above, the substituents of the substituted ones can be at least one selected from deuterium, phenanthryl group, a pyridyl group which is unsubstituted or substituted by at least one of methyl or phenyl, and a quinolinyl group.

[0071] According to one embodiment of the present disclosure, Ar 21 to Ar 23 each independently can represent a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5-membered to 30-membered) heteroaryl group; preferably a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5-membered to 26-membered) heteroaryl group; and more preferably a substituted or unsubstituted (C6-C18) aryl group, or a substituted or unsubstituted (5-membered to 26-membered) heteroaryl group. Preferably, at least one of Ar 21 to Ar 23 can contain a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzo[9,10]fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuran group or a substituted or unsubstituted dibenzothiophene group, provided that at least one of Ar 21 to Ar 23 contains deuterium. For example, Ar 21 to Ar 23Each independently represents a substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted p-biphenylyl, substituted or unsubstituted m-biphenylyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted spiro[fluorene-9,9'-xanthene]yl or a 22-membered heteroaryl, and the substituent of the substituted one can be at least one selected from deuterium, cyano, methyl, phenyl, biphenyl and naphthyl.

[0072] According to one embodiment of the present disclosure, the deuterium substitution rate is preferably 20% to 100% of the total number of hydrogens, more preferably 20% to 95%, even more preferably 30% to 95%, and even more preferably 40% to 95%.

[0073] According to one embodiment of the present disclosure, the deuterated compound can be more specifically exemplified by the following compounds, but is not limited thereto.

[0074]

[0075]

[0076]

[0077]

[0078] According to one embodiment of the present disclosure, the organic electroluminescent device according to the present disclosure may include at least one layer in the light-emitting layer, and the at least one layer contains a compound represented by the following Formula 4 or Formula 5.

[0079]

[0080] In Formula 4,

[0081] A 1 and A 2 each independently represents a substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazolyl;

[0082] X' 15 to X' 18 any one of and X' 19 to X' 22 any one of which is connected to each other to form a single bond;

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

[0084] X' 11 , X' 18 , X' 19 or X' 26 At least one of represents deuterium; and

[0085] D n It means that n number of hydrogen atoms are substituted with deuterium, and n represents an integer of 1 or more and has an upper limit on the number of hydrogen atoms in the non-deuterated compound.

[0086] According to one embodiment of the present disclosure, A 1 and A 2 Each independently may represent a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted dibenzofuranyl group. Preferably, A 1 and A 2 Each independently may represent a substituted or unsubstituted (C6-C18) aryl group, or a substituted or unsubstituted dibenzofuranyl group. 1 and A 2 Each independently may be a substituted or unsubstituted phenyl, biphenyl, substituted or unsubstituted naphthyl, terphenyl, triphenylene, or substituted or unsubstituted dibenzofuranyl. The substituent of the substituted one may be at least one selected from deuterium, phenyl, naphthyl, triphenylene, and dibenzofuranyl.

[0087] According to one embodiment of the present disclosure, the deuterium substitution rate is preferably 20% to 100%, more preferably 20% to 95%, even more preferably 30% to 95%, and even more preferably 40% to 95% of the total number of hydrogen.

[0088]

[0089] In formula 5,

[0090] R 51 To R 53 At least one of them contains the following formula 5-1 or formula 5-2:

[0091]

[0092]

[0093] Or, L 51 and L 52 can be a single bond, and R 51 and R52 may be connected to each other and represented by any one of the following Formulas 5-3 to 5-5:

[0094]

[0095] R 51 to R 53 and R' 51 to R' 59 each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tris(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 tris(C6-C30)arylsilyl, a substituted or unsubstituted fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, 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- to 30-membered) heteroarylamino, substituted or unsubstituted (C1-C30)alkyl(3- to 30-membered) heteroarylamino, substituted or unsubstituted (C2-C30)alkenyl(C6-C30)arylamino, substituted or unsubstituted (C2-C30)alkenyl(3- to 30-membered) heteroarylamino, or substituted or unsubstituted (C6-C30)aryl(3- to 30-membered) heteroarylamino, or may be connected to one or more adjacent substituents to form one or more rings;

[0096] L 51 to L 53 each independently represents a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene;

[0097] X” represents O or S;

[0098] a, b, e and f each independently represent an integer of 1 or 2, c, d and g represent an integer of 1 to 4, wherein if a to g represent an integer of 2 or greater, then each R' 51 to each R' 59may be the same or different; and

[0099] D n represents that n hydrogens are replaced by deuteriums, and n represents an integer of 1 or greater and has an upper limit of the number of hydrogen atoms in the non-deuterated compound.

[0100] According to one embodiment of the present disclosure, R 51 to R 53 and R' 51 to R' 59 each independently may represent hydrogen, deuterium, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3-membered to 30-membered) heteroaryl group, a substituted or unsubstituted fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, a substituted or unsubstituted mono- or di-(C6-C30) arylamino group, or a substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino group, or may be connected to one or more adjacent substituents to form one or more rings. Preferably, R 51 to R 53 and R' 51 to R' 59 each independently may represent a substituted or unsubstituted (C6-C25) aryl group, a substituted or unsubstituted (5-membered to 25-membered) heteroaryl group, a substituted or unsubstituted fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, a substituted or unsubstituted mono- or di-(C6-C18) arylamino group, or may be connected to one or more adjacent substituents to form one or more rings. For example, R 51 to R 53 and R' 51 to R' 59 each independently may be an unsubstituted phenyl group or a phenyl group substituted with: phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, 23-membered heteroaryl, dibenzofuranyl, dibenzothiophenyl, diphenylamino, phenylbiphenylamino, phenylnaphthylamino, dibiphenylamino, Formula 5-1 or Formula 5-2, etc., or may be connected to one or more adjacent substituents to form a benzoindolocarbazole ring, such as Formula 5-3 or Formula 5-4, which may be further substituted with one or more deuterium atoms.

[0101] According to one embodiment of the present disclosure, X” may represent O.

[0102] According to one embodiment of the present disclosure, L 51 to L 53 each independently may represent a single bond, or a substituted or unsubstituted (C6-C30) arylene group. Preferably, L 51 to L 53Each independently may represent a single bond or a substituted or unsubstituted (C6-C12) arylene group. For example, L 51 to L 53 Each independently may be a single bond, phenyl group, biphenyl group, etc., which may be further substituted by one or more deuterium atoms.

[0103] According to one embodiment of the present disclosure, the deuterium substitution rate is preferably 20% to 100% of the total number of hydrogens, more preferably 20% to 95%, even more preferably 30% to 95%, and even more preferably 40% to 95%.

[0104] According to one embodiment of the present disclosure, the deuterated compound may be more specifically exemplified by the following compounds, but is not limited thereto.

[0105]

[0106]

[0107]

[0108]

[0109] According to one embodiment of the present disclosure, the organic electroluminescent device according to the present disclosure may include at least one layer in the light-emitting layer, and the at least one layer contains two or more compounds, wherein the two or more compounds contain a compound represented by Formula 6 or Formula 7 below.

[0110]

[0111] In Formula 6 and Formula 7,

[0112] X 61 represents O or S;

[0113] HAr 61 and HAr 62 Each independently represents a substituted or unsubstituted (3-membered to 30-membered) heteroaryl group containing one or more nitrogen atoms;

[0114] L 61 and L 62 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-membered to 30-membered) heteroarylene group;

[0115] R 61 to R 64 Each independently represents hydrogen, deuterium, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-membered to 30-membered) heteroaryl group; or may be connected to one or more adjacent substituents to form one or more rings;

[0116] h to k each independently represent an integer from 1 to 4, where if h to k represent an integer of 2 or greater, then each R 61 to each R 64 may be the same or different; and

[0117] D n represents that n hydrogen atoms are replaced by deuterium, and n represents an integer of 1 or greater and has an upper limit of the number of hydrogen atoms in the non-deuterated compound.

[0118] According to one embodiment of the present disclosure, HAr 61 and HAr 62 each independently may represent a substituted or unsubstituted (3-membered to 15-membered) heteroaryl containing one or more nitrogen atoms. For example, HAr 61 and HAr 62 each independently may be a substituted triazinyl group, where one or more substituents of the substituted triazinyl group may be selected from at least one, preferably two, of naphthyl, biphenyl, terphenyl, naphthyl substituted with one or more phenyl groups, naphthyl substituted with one or more naphthyl groups, naphthyl substituted with dibenzofuranyl, and dibenzofuranyl, which may be further substituted with one or more deuterium atoms.

[0119] According to one embodiment of the present disclosure, L 61 and L 62 each independently may represent a single bond, or a substituted or unsubstituted (C6-C15) arylene group. Preferably, L 61 and L 62 each independently may represent a single bond, or a substituted or unsubstituted (C6-C10) arylene group. For example, L 61 and L 62 each independently may be a single bond, phenylene, naphthylene, etc., which may be further substituted with one or more deuterium atoms.

[0120] According to one embodiment of the present disclosure, R 61 to R 64 each independently may represent hydrogen, deuterium, a substituted or unsubstituted (C6-C20) aryl group, or a substituted or unsubstituted (3-membered to 20-membered) heteroaryl group; or may be connected to one or more adjacent substituents to form one or more rings. Preferably, R 61 to R 64 each independently may represent hydrogen, deuterium, a substituted or unsubstituted (C6-C18) aryl group, or a substituted or unsubstituted (3-membered to 20-membered) heteroaryl group; or may be connected to one or more adjacent substituents to form one or more rings. For example, R 61 to R 64Each independently may be hydrogen, deuterium, naphthyl, carbazolyl, dibenzothienyl, dibenzofuranyl, etc., or may be linked to one or more adjacent substituents to form an indole ring, benzothiophene ring or benzene ring substituted with one or more phenyl groups or one or more biphenyl groups, etc., which may be further substituted with one or more deuterium atoms.

[0121] According to one embodiment of the present disclosure, the deuterium substitution rate is preferably 20% to 100% of the total number of hydrogens, more preferably 20% to 95%, even more preferably 30% to 95%, and even more preferably 40% to 95%.

[0122] According to one embodiment of the present disclosure, the deuterated compound may be more specifically exemplified by the following compounds, but is not limited thereto.

[0123]

[0124]

[0125] According to one embodiment of the present disclosure, the organic electroluminescent device of the present disclosure may include at least one layer in the light-emitting layer, and the at least one layer contains a compound represented by the following formula 8.

[0126]

[0127] In formula 8,

[0128] Ar 81 represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-membered to 30-membered) heteroaryl group;

[0129] R 81 to R 88 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl group, substituted or unsubstituted (C2-C30) alkenyl group, substituted or unsubstituted (C6-C30) aryl group, substituted or unsubstituted (3-membered to 30-membered) heteroaryl group, substituted or unsubstituted (C3-C30) cycloalkyl group, substituted or unsubstituted (C3-C30) cycloalkenyl group, substituted or unsubstituted (3-membered to 7-membered) heterocycloalkyl group, substituted or unsubstituted (C1-C30) alkoxy group, substituted or unsubstituted tris(C1-C30) alkylsilyl group, substituted or unsubstituted bis(C1-C30) alkyl(C6-C30) arylsilyl group, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl group, substituted or unsubstituted tris(C6-C30) arylsilyl group, or a substituted or unsubstituted fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings;

[0130] ArA represents a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3- to 30-membered) heteroaryl, or is represented by the following formula A-1;

[0131] D n represents that n hydrogens are replaced by deuterium, and n represents an integer of 1 or greater and has an upper limit of the number of hydrogen atoms in the non-deuterated compound;

[0132]

[0133] T 1 represents O, S or CR l R m ;

[0134] R' 81 to R' 88 each independently is a site connected to L 82 or represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tris(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 tris(C6-C30)arylsilyl, a substituted or unsubstituted fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or -L 83 -N(Ar 83 )(Ar 84 );

[0135] R l and R m each independently represents substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C6-C30) aryl, or may be connected to each other to form one or more rings;

[0136] L 81 to L 83 each independently represents a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene; and

[0137] Ar 83 and Ar 84Each independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3-membered to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C3-C30) cycloalkenyl group, a substituted or unsubstituted (3-membered to 7-membered) heterocycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted fused ring group having one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, or a substituted or unsubstituted tris(C6-C30)arylsilyl group.

[0138] According to one embodiment of the present disclosure, Ar 81 may represent a substituted or unsubstituted (C6-C30) aryl group. Preferably, Ar 81 may represent a substituted or unsubstituted (C6-C18) aryl group. For example, Ar 81 may be an unsubstituted phenyl group, naphthyl group or biphenyl group substituted with one or more naphthyl groups, etc., which may be further substituted with one or more deuterium atoms.

[0139] According to one embodiment of the present disclosure, R 81 to R 88 Each independently may represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3-membered to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, or a substituted or unsubstituted (C3-C30) cycloalkenyl group. Preferably, R 81 to R 88 Each independently may represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-membered to 30-membered) heteroaryl group. For example, R 81 to R 88 Each independently may be hydrogen or deuterium.

[0140] According to one embodiment of the present disclosure, Ar A may represent a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5-membered to 20-membered) heteroaryl group, or may be represented by the above formula A-1. Preferably, ArA may represent a substituted or unsubstituted (C6-C13) aryl group, or a substituted or unsubstituted (13- to 17-membered) heteroaryl group, or may be represented by Formula A-1. For example, Ar A may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted benzofluorenyl group, dibenzofuranyl group or benzonaphthofuranyl group, or may be Formula A-1, wherein the substituent of the above-mentioned substituted group may be at least one selected from deuterium, methyl, phenyl, naphthyl and dibenzofuranyl groups.

[0141] According to an embodiment of the present disclosure, T 1 may represent O or S. For example, T 1 may be O.

[0142] According to an embodiment of the present disclosure, R' 81 to R' 88 each independently may be a site connected to L 82 or may represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl group, substituted or unsubstituted (C2-C30) alkenyl group, substituted or unsubstituted (C6-C30) aryl group, substituted or unsubstituted (3- to 30-membered) heteroaryl group, or substituted or unsubstituted (C3-C30) cycloalkyl group. Preferably, R' 81 to R' 88 each independently may be a site connected to L 82 or may represent hydrogen, deuterium or unsubstituted (C6-C18) aryl group. For example, R' 81 to R' 88 each independently may be a site connected to L 82 or hydrogen, deuterium or phenyl, etc., which may be further substituted by one or more deuterium atoms.

[0143] According to an embodiment of the present disclosure, L 81 to L 83 each independently may represent a single bond, or a substituted or unsubstituted (C6-C30) arylene group. Preferably, L 81 to L 83 each independently may represent a single bond, or a substituted or unsubstituted (C6-C15) arylene group. For example, L 81 to L 83 each independently may represent a single bond, phenylene, naphthylene or phenanthrylene, etc., which may be further substituted by one or more deuterium atoms.

[0144] According to an embodiment of the present disclosure, the deuterium substitution rate is preferably 20% to 100% of the total number of hydrogens, more preferably 20% to 95%, even more preferably 30% to 95%, and even more preferably 40% to 95%.

[0145] According to an embodiment of the present disclosure, the deuterated compound can be more specifically exemplified by the following compounds, but is not limited thereto.

[0146]

[0147]

[0148] According to an embodiment of the present disclosure, the organic electroluminescent device of the present disclosure may include at least one layer in the light-emitting layer, and the at least one layer contains a compound represented by the following formula 9.

[0149]

[0150] In formula 9,

[0151] X 15 to X 18 Any adjacent pair of which is connected to the following formula 9-A to form one or more rings, and the X 15 to X 18 , X 11 to X 14 , and X 31 to X 34 each independently represents hydrogen, deuterium, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group;

[0152]

[0153] In formula 9 and formula 9-A,

[0154] A 1 and A 3 each independently represents a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group;

[0155] L 3 and L 5 each independently represents a single bond, or a substituted or unsubstituted (C6-C30) arylene group; and

[0156] D n represents that n hydrogen atoms are replaced by deuterium, and n represents an integer of 1 or greater and has an upper limit of the number of hydrogen atoms in the non-deuterated compound.

[0157] According to an embodiment of the present disclosure, A 1 and A 3Each independently may represent a substituted or unsubstituted (C6-C18) aryl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolyl group. For example, A 1 and A 3 Each independently may be a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted p-biphenyl group, a substituted or unsubstituted m-biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolyl group, etc., wherein the substituents of the above-mentioned substituted ones may be at least one selected from deuterium, phenyl group, an unsubstituted or phenyl-substituted carbazolyl group and a naphthyl group.

[0158] According to one embodiment of the present disclosure, L 3 and L 5 Each independently may represent a single bond, or a substituted or unsubstituted (C6-C12) arylene group. For example, L 3 and L 5 Each independently may represent a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted p-biphenylene group, a substituted or unsubstituted m-biphenylene group, a substituted or unsubstituted o-biphenylene group, or a substituted or unsubstituted naphthylene group, etc., wherein the substituents of the above-mentioned substituted ones may be at least one selected from deuterium and a carbazolyl group.

[0159] According to one embodiment of the present disclosure, X 15 to X 18 , X 11 to X 14 , and X 31 to X 34 Each independently may represent hydrogen or deuterium.

[0160] According to one embodiment of the present disclosure, the deuterium substitution rate is preferably 20% to 100% of the total number of hydrogens, more preferably 20% to 95%, even more preferably 30% to 95%, and even more preferably 40% to 95%.

[0161] According to one embodiment of the present disclosure, in the organic electroluminescent device of the present disclosure, X 11 or X 31 may represent deuterium.

[0162] According to one embodiment of the present disclosure, the compound represented by Formula 9 may be represented by any one of the following Formulas 9-1 to 9-6.

[0163]

[0164]

[0165] In Formulas 9-1 to 9-6, A 1 , A 3 , L 3 , L 5 , X 11 to X 18 , X 31 to X 34 and D n are defined as in Formulas 9 and 9-A.

[0166] According to one embodiment of the present disclosure, the deuterated compound can be more specifically exemplified by the following compounds, but is not limited thereto.

[0167]

[0168]

[0169]

[0170]

[0171] In the above compounds, D n represents that n numbers of hydrogens are replaced by deuteriums, and n represents an integer of 1 or greater and has an upper limit of the number of hydrogen atoms in the non-deuterated compound.

[0172] In the synthesis of the compounds represented by the above Formulas 1 to 9, those skilled in the art will be able to easily understand that these are all based on Buchwald-Hartwig cross-coupling reaction, N-arylation reaction, acidified montmorillonite (H-mont)-mediated etherification reaction, Miyaura borylation reaction, Suzuki cross-coupling reaction, intramolecular acid-induced cyclization reaction, Pd(II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, dehydration cyclization reaction, S N 1 substitution reaction, S N 2 substitution reaction, phosphine-mediated reductive cyclization reaction, and Wittig reaction, etc., and even when substituents defined in Formulas 1 to 9 other than those specified in the specific synthesis examples are bonded, the above reactions proceed.

[0173] Hereinafter, the above-mentioned compounds and the organic electroluminescent device containing the same will be described.

[0174] The organic layer of the present disclosure may include at least one layer selected from the following layers: a hole transport layer, a light-emitting layer, a hole injection layer, a hole assisting layer, a light-emitting assisting layer, an electron transport layer, an electron injection layer, an intermediate layer, a hole blocking layer, an electron blocking layer, and an electron buffer layer. The organic layer may further contain an amine-based compound and / or an azine-based compound. Specifically, the hole injection layer, the hole transport layer, the hole assisting layer, the light-emitting layer, the light-emitting assisting layer, or the electron blocking layer may contain an amine-based compound (e.g., an arylamine-based compound, a styrylarylamine-based compound, etc.) as a hole injection material, a hole transport material, a hole assisting material, a light-emitting material, a light-emitting assisting material, and an electron blocking material. In addition, the electron transport layer, the electron injection layer, the electron buffer layer, and the hole blocking layer may contain an azine-based compound as an electron transport material, an electron injection material, an electron buffer material, and a hole blocking material. Further, the organic layer may further contain at least one metal selected from the group consisting of metals of Group 1 of the periodic table, metals of Group 2 of the periodic table, transition metals of the 4th period, transition metals of the 5th period, lanthanides, and organometals of d-transition elements, or at least one complex compound containing a metal therein.

[0175] A hole transport region including a hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof is included between the anode and the light-emitting layer. For the purpose of reducing the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, the hole injection layer may be composed of multiple layers, and two compounds may be used simultaneously for each layer. In addition, the hole injection layer may be doped with a p-type dopant. The electron blocking layer may be placed between the hole transport layer (or the hole injection layer) and the light-emitting layer, and may block the electron spillover from the light-emitting layer and confine the excitons in the light-emitting layer to prevent light leakage. The hole transport layer or the electron blocking layer may use multiple layers, and multiple compounds may be used in each layer.

[0176] An electron transport region including an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof is included between the light-emitting layer and the cathode. The electron buffer layer may be multiple layers to control the injection of electrons and improve the interfacial characteristics between the light-emitting layer and the electron injection layer, and two compounds may be used simultaneously for each of the multiple layers. The hole blocking layer is located between the electron transport layer (or the electron injection layer) and the light-emitting layer, and is a layer that blocks holes from reaching the cathode, thereby increasing the probability of recombination of electrons and holes in the light-emitting layer. The hole blocking layer or the electron transport layer may also use multiple layers, and multiple compounds may be used in each layer. In addition, the electron injection layer may be doped with an n-type dopant.

[0177] The light-emitting auxiliary layer can be a layer placed between the anode and the light-emitting layer, or a layer between the cathode and the light-emitting layer. When the light-emitting auxiliary layer is placed between the anode and the light-emitting layer, the light-emitting auxiliary layer can be used to facilitate hole injection and / or hole transport or to block the overflow of electrons. When the light-emitting auxiliary layer is placed between the cathode and the light-emitting layer, the light-emitting auxiliary layer can be used to facilitate electron injection and / or electron transport or to block the overflow of holes. In addition, a hole auxiliary layer can be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can exhibit the effect of promoting or blocking the hole transport rate (or hole injection rate), and thus can adjust the charge balance. When the organic electroluminescent device includes two or more hole transport layers, the further included hole transport layer can be used as a hole auxiliary layer or an electron blocking layer. The light-emitting auxiliary layer, the hole auxiliary layer or the electron blocking layer can have the effect of improving the efficiency and / or lifetime of the organic electroluminescent device.

[0178] In the organic electroluminescent device of the present disclosure, it is preferable to provide at least one layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter referred to as a "surface layer") on at least one inner surface of a pair of electrodes. Specifically, it is preferable to place a chalcogenide (including oxide) layer of silicon and aluminum on the anode surface on the side of the electroluminescent medium layer, and it is preferable to place a metal halide layer or a metal oxide layer on the cathode surface on the side of the electroluminescent medium layer. The driving stability of the organic electroluminescent device can be obtained through the surface layer. Preferred examples of the chalcogenide include SiO X (1 ≤ X ≤ 2), AlO X (1 ≤ X ≤ 1.5), SiON, SiAlON, etc., preferred examples of the metal halide include LiF, MgF 2 , CaF 2 , rare earth metal fluorides, etc., and preferred examples of the metal oxide include Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.

[0179] 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 may 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 thus it becomes easier to inject and transport electrons from the mixed region to the light-emitting medium. In addition, the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the light-emitting medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds, and preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, an organic electroluminescent device having at least two light-emitting layers and emitting white light can be manufactured by using a reducing dopant layer as a charge generation layer.

[0180] The organic electroluminescent device according to 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 part) may be formed in a structure in which two or more units are connected by a charge generation layer. The organic electroluminescent device may include a plurality of two or more light-emitting units, for example, a plurality of three or more light-emitting units, the light-emitting unit having a first electrode and a second electrode facing each other on a substrate and a light-emitting layer stacked between the first electrode and the second electrode and emitting light in a specific wavelength range. The organic electroluminescent device may include a plurality of light-emitting units, and each of these light-emitting units may include a hole transport region, a light-emitting layer, and an electron transport region, and the hole transport region may include a hole injection layer and a hole transport layer, and the electron transport region may include an electron transport layer and an electron injection layer. According to an embodiment of the present disclosure, 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. It may include one or more charge generation layers located 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 may be located between each light-emitting unit. Here, the plurality of charge generation layers may be the same as or different from each other. By providing a charge generation layer between the light-emitting units, the current efficiency in each light-emitting unit increases, and the charge can be evenly distributed. Specifically, the charge generation layer is provided between two adjacent stacks and can be used to drive the tandem organic electroluminescent device using only a pair of anodes and cathodes without the need for a separate internal electrode located between the stacks.

[0181] The charge generation layer may be composed of an N-type charge generation layer and a P-type charge generation layer, and the N-type charge generation layer may be doped with an alkali metal, an alkaline earth metal, or a compound of an alkali metal and an alkaline earth metal. The alkali metal may include one selected from the group consisting of Li, Na, K, Rb, Cs, Fr, Yb, and combinations thereof, and the alkaline earth metal may include one selected from the group consisting of Be, Mg, Ca, Sr, Ba, Ra, and combinations thereof. The P-type charge generation layer may be made of a metal or an organic material doped with a P-type dopant. For example, the metal may be made of an alloy of one or two or more selected from the group consisting of: Al, Cu, Fe, Pb, Zn, Au, Pt, W, In, Mo, Ni, and Ti. In addition, commonly used materials may be used as the P-type dopant and the host material used in the P-type doped organic material.

[0182] The manufacturing method of the organic electroluminescent device of the present disclosure is not limited, and the manufacturing method of the device examples described below is only an example, and the method is not limited thereto. Those skilled in the art can reasonably modify the manufacturing method of the device examples described below based on the prior art. For example, there is no particular limitation on the mixing ratio of the first compound and the second compound, and thus those skilled in the art can reasonably select this ratio within a certain range according to the prior art. For example, based on the total weight of the light-emitting layer material, the total weight of the first compound and the second compound accounts for 99.5% - 80.0% of the total weight of the light-emitting layer, the weight ratio of the first compound and the second compound is between 1:99 and 99:1, the weight ratio of the first compound and the second compound may be between 20:80 and 99:1, or the weight ratio of the first compound and the second compound may be between 50:50 and 90:10. In the manufacture of the device, when the light-emitting layer is formed by co-depositing two or more host materials and a light-emitting material, the two or more host materials and the light-emitting material may be placed in different evaporation sources and co-deposited to form the light-emitting layer, or a pre-mixed mixture of two or more host materials may be placed on the same evaporation source and then co-deposited with the light-emitting material placed on another evaporation source to form the light-emitting layer. This pre-mixing method can further save evaporation sources. According to one embodiment, the first compound, the second compound, and the light-emitting material of the present disclosure may be placed in different evaporation sources and co-deposited to form the light-emitting layer, or a pre-mixed mixture of the first compound and the second compound may be placed in the same evaporation source, and then co-deposited with the light-emitting material placed in another evaporation source to form the light-emitting layer.

[0183] To form each layer of the organic electroluminescent device of the present disclosure, a dry film-forming method such as vacuum evaporation, sputtering, plasma, ion plating method, etc., or a wet film-forming method such as spin coating, dip coating, flow coating method, etc. can be used. When using a wet film-forming method, a thin film can be formed by dissolving or diffusing the material for forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent can be any solvent in which the material for forming each layer can be dissolved or diffused and there is no problem in film-forming ability.

[0184] When forming a film of an organic electroluminescent material according to an embodiment, the film can be formed by the methods listed above and can generally be formed by a co-deposition or mixed deposition process. Co-deposition is a method of mixing and depositing two or more materials by placing two or more materials in separate crucible sources and applying current to both chambers simultaneously to evaporate the materials, and mixed deposition is a method of mixing two or more materials in one crucible source before deposition and then applying current to one chamber to evaporate the materials.

[0185] Hereinafter, to understand the present disclosure in detail, the preparation method of the compounds according to the present disclosure will be described by taking the synthesis of representative compounds or intermediate compounds of the present disclosure as an example.

[0186] Example 1: Preparation of Compound HT-47

[0187]

[0188] The deuteration method disclosed in Korean Patent Publication Nos. 10-2283849, 10-1427457, etc. was used to synthesize compound HT-ref1 to obtain compound HT-47 (17 g, yield: 65%).

[0189] MW M.P. HT-47 660 200℃

[0190] Example 2: Preparation of Compound H1-55

[0191]

[0192] The deuteration method disclosed in Korean Patent Publication Nos. 10-2283849, 10-1427457, etc. was used to synthesize compound H1-ref1 to obtain compound H1-55 (53 g, yield: 84%).

[0193] MW M.P. H1-55 590 335℃

[0194] Example 3: Preparation of Compound H2-35

[0195]

[0196] The deuteration method disclosed in Korean Patent Publication Nos. 10-2283849, 10-1427457, etc. was used to synthesize compound H2-ref1 to obtain compound H2-35 (66 g, yield: 91%).

[0197] MW M.P. H2-35 662 200℃

[0198] Example 4: Preparation of Compound ET-60

[0199]

[0200] The deuteration method disclosed in Korean Patent Publication Nos. 10-2283849, 10-1427457, etc. was used to synthesize compound ET-ref1 to obtain compound ET-60 (12 g, yield: 87%).

[0201] MW M.P. ET-60 660 281℃

[0202] Example 5: Preparation of Compound HT-39

[0203]

[0204] The deuteration method disclosed in Korean Patent Publication Nos. 10-2283849, 10-1427457, etc. was used to synthesize compound HT-ref2 to obtain compound HT-39 (7.6 g, yield: 63%).

[0205] MW M.P. HT-39 657 221℃

[0206] Example 6: Preparation of Compound H2-61

[0207]

[0208] The deuteration method disclosed in Korean Patent Publication Nos. 10-2283849, 10-1427457, etc. was used to synthesize compound H2-ref2 to obtain compound H2-61 (8.1 g, yield: 75%).

[0209] MW M.P. H2-61 718 244℃

[0210] Example 7: Preparation of Compound H1-15

[0211]

[0212] The deuteration method disclosed in Korean Patent Publication Nos. 10-2283849, 10-1427457, etc. was used to synthesize compound H1-ref2 to obtain compound H1-15 (32 g, yield: 84%).

[0213] MW M.P. H1-15 586 242℃

[0214] Example 8: Preparation of Compound ET-1

[0215]

[0216] The deuteration method disclosed in Korean Patent Publication Nos. 10-2283849, 10-1427457, etc. was used to synthesize compound ET-ref2 to obtain compound ET-1 (5 g, yield: 88%).

[0217] MW M.P. ET-1 717 360℃

[0218] Example 9: Preparation of Compound H3-7

[0219]

[0220] The deuteration method disclosed in Korean Patent Publication Nos. 10-2283849, 10-1427457, etc. was used to synthesize compound H3-ref1 to obtain compound H3-7 (12 g, yield: 77%).

[0221] MW M.P. H3-7 530 275℃

[0222] Example 10: Preparation of Compound H3-20

[0223]

[0224] The deuteration method disclosed in Korean Patent Publication Nos. 10-2283849, 10-1427457, etc. was used to synthesize compound H3-ref2 to obtain compound H3-20 (14 g, yield: 79%).

[0225] MW M.P. H3-20 514 330℃

[0226] Example 11: Preparation of Compound C-52

[0227]

[0228] The deuteration method disclosed in Korean Patent Publication Nos. 10-2283849, 10-1427457, etc. was used to synthesize compound C-52-ref to obtain compound C-52 (24.4 g, yield: 94%).

[0229] MW M.P. C-52 580 151℃

[0230] Device Example 1: Production of an OLED Deposited with a Compound According to the Present Disclosure

[0231] Manufacture an OLED according to the present disclosure. First, a transparent electrode indium tin oxide (ITO) thin film (10 Ω / sq) (GEOMATEC CO., LTD., Japan) on a glass substrate for an OLED is ultrasonically washed successively with acetone and isopropyl alcohol, and then stored in isopropyl alcohol. The ITO substrate is mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI (p-dopant) is introduced into one chamber of the vacuum vapor deposition apparatus, and compound HT'-1 is introduced into another chamber. The two materials are evaporated at different rates, and compound HI is deposited with a doping amount of 3 wt% based on the total amount of compound HI and compound HT'-1 to form a hole injection layer with a thickness of 10 nm. Subsequently, compound HT'-1 is deposited on the hole injection layer to form a first hole transport layer with a thickness of 80 nm. Next, the compounds shown in Table 1 are introduced into another chamber of the vacuum vapor deposition apparatus and evaporated by applying a current to this chamber, thereby depositing a second hole transport layer with a thickness of 30 nm. After forming the hole injection layer and the hole transport layer, a light-emitting layer is deposited thereon as follows: the compounds shown in Table 1 below are introduced into one chamber of the vacuum vapor deposition apparatus as a host at a ratio of 1:2, and compound GD is introduced into another chamber as a dopant. The materials are evaporated at different rates, and the dopant is deposited with a doping amount of 10 wt% based on the total amount of the host and the dopant to form a light-emitting layer with a thickness of 40 nm on the second hole transport layer. The compounds shown in Table 1 are deposited as an electron buffer layer with a thickness of 5 nm, and then compounds EI-1 and Liq are introduced into two other chambers and evaporated at a rate of 1:1 to deposit an electron transport layer with a thickness of 30 nm on the electron buffer layer. After introducing compound Liq as an electron injection layer and depositing it with a thickness of 2 nm on the electron transport layer, an Al cathode with a thickness of 80 nm is deposited by using another vacuum vapor deposition apparatus, thereby manufacturing the OLED. All materials used for manufacturing the OLED are purified by vacuum sublimation at 10 -6 Torr.

[0232] Comparative Example 1: Production of an OLED Containing a Conventional Compound

[0233] An OLED is manufactured in the same manner as in Device Example 1, except that the hole transport layer, the host material of the light-emitting layer, and the electron buffer layer are made of light hydrogen materials.

[0234] For the OLEDs of Device Example 1 and Comparative Example 1 described above, Table 1 below shows the current efficiency at a brightness of 1,000 nits and the time taken for the brightness to decrease from 100% to 95% at a brightness of 40,000 nits (lifetime: T 95 ).

[0235] [Table 1]

[0236]

[0237] As can be confirmed from Table 1 above, the organic electroluminescent device according to the present disclosure exhibits a longer lifetime characteristic while maintaining the current efficiency characteristic as compared with a conventional organic electroluminescent device.

[0238] Device Example 2: Production of an OLED Deposited with a Compound According to the Present Disclosure as a Host

[0239] To produce an OLED according to the present disclosure. First, an indium tin oxide (ITO) thin film (10 Ω / sq) (Giaoma Co., Ltd., Japan) of a transparent electrode on a glass substrate for the OLED is ultrasonically washed successively with acetone and isopropyl alcohol, and then stored in isopropyl alcohol. The ITO substrate is mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI (p-dopant) is introduced into one chamber of the vacuum vapor deposition apparatus, and compound HT'-1 is introduced into another chamber. The two materials are evaporated at different rates, and compound HI is deposited at a doping amount of 3 wt% based on the total amount of compound HI and compound HT'-1 to form a hole injection layer having a thickness of 10 nm. Subsequently, compound HT'-1 is deposited on the hole injection layer to form a first hole transport layer having a thickness of 90 nm. Next, the compound shown in Table 2 is introduced into another chamber of the vacuum vapor deposition apparatus as a second hole transport layer, and is evaporated by applying current to the chamber, thereby depositing a thickness of 60 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light-emitting layer is deposited thereon as follows: the compound shown in Table 2 below is introduced into one chamber of the vacuum vapor deposition apparatus at a ratio of 1:1 as a host, and compound RD is introduced into another chamber as a dopant. The materials are evaporated at different rates, and the dopant is deposited at a doping amount of 3 wt% based on the total amount of the host and the dopant to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer. The compound shown in Table 2 is deposited as an electron buffer layer with a thickness of 5 nm, and then compound EI-1 and compound Liq are introduced into two other chambers and evaporated at a rate of 1:1 to deposit an electron transport layer having a thickness of 30 nm on the light-emitting layer. After introducing compound Liq as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 80 nm is deposited by using another vacuum vapor deposition apparatus, thereby producing an OLED. All materials used for producing the OLED are purified by vacuum sublimation under 10 -6 Torr.

[0240] Comparative Example 2: Production of an OLED Containing a Conventional Compound

[0241] An OLED is produced in the same manner as in Device Example 2, except that the hole transport layer, the host material of the light-emitting layer, and the electron buffer layer are made of light hydrogen materials.

[0242] For the OLEDs of Device Example 2 and Comparative Example 2 described above, Table 2 below shows the current efficiency at a brightness of 1,000 nits and the time taken for the brightness to decrease from 100% to 97% at a brightness of 10,000 nits (lifetime: T 97 ).

[0243] [Table 2]

[0244]

[0245]

[0246] It can be confirmed from Table 2 above that, compared with conventional organic electroluminescent devices, the organic electroluminescent devices according to the present disclosure exhibit higher current efficiency and much longer lifetime.

[0247] Device Example 3: Production of an OLED Deposited with a Compound According to the Present Disclosure

[0248] An OLED is produced in the same manner as in Device Example 2, except that the compounds shown in Table 3 and the compound Liq are introduced into two other chambers and evaporated at a rate of 1:1 to deposit an electron transport layer with a thickness of 35 nm on the light-emitting layer without depositing an electron buffer layer.

[0249] Comparative Example 3: Production of an OLED Containing a Conventional Compound

[0250] An OLED is produced in the same manner as in Device Example 3, except that the hole transport layer, the host material of the light-emitting layer, and the electron buffer layer are made of light hydrogen materials.

[0251] For the OLEDs of Device Example 3 and Comparative Example 3 described above, Table 3 below shows the current efficiency at a brightness of 1,000 nits and the time taken for the brightness to decrease from 100% to 97% at a brightness of 10,000 nits (lifetime: T 97 ).

[0252] [Table 3]

[0253]

[0254]

[0255] It can be confirmed from Table 3 above that, compared with conventional organic electroluminescent devices, the organic electroluminescent devices according to the present disclosure exhibit longer lifetime while maintaining the current efficiency.

[0256] Device Examples 4 and 5: Production of an OLED Deposited with a Compound According to the Present Disclosure

[0257] Manufacture an OLED according to the present disclosure. First, the indium tin oxide (ITO) thin film (10 Ω / sq) (manufactured by Geomatec Co., Ltd., Japan) of the transparent electrode on the glass substrate for the OLED is ultrasonically washed successively with acetone and isopropyl alcohol, and then stored in isopropyl alcohol. Mount the ITO substrate on the substrate holder of the vacuum vapor deposition apparatus. Introduce the compound HI (p-dopant) into one chamber of the vacuum vapor deposition apparatus, and introduce the compound HT'-1 into another chamber. Evaporate the two materials at different rates, and deposit the compound HI with a doping amount of 3 wt% based on the total amount of the compound HI and the compound HT'-1 to form a hole injection layer with a thickness of 10 nm. Subsequently, deposit the compound HT'-1 on the hole injection layer to form a first hole transport layer with a thickness of 80 nm. Next, introduce the compound shown in Table 4 as the second hole transport layer into another chamber of the vacuum vapor deposition apparatus, and evaporate it by applying current to the chamber, thereby depositing a layer with a thickness of 5 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, deposit the light-emitting layer thereon as follows: After introducing the compound shown in Table 4 as the host into one chamber of the vacuum vapor deposition apparatus, evaporate the two materials at different rates, and deposit the dopant with a doping amount of 2 wt% based on the total amount of the host and the dopant to form a light-emitting layer with a thickness of 20 nm on the second hole transport layer. Then introduce the compound shown in Table 4 and the compound Liq into two other chambers and evaporate them at a rate of 1:1 to deposit an electron transport layer with a thickness of 35 nm on the light-emitting layer. After introducing the compound Liq as the electron injection layer and depositing it with a thickness of 2 nm on the electron transport layer, deposit an Al cathode with a thickness of 80 nm by using another vacuum vapor deposition apparatus, thereby manufacturing the OLED. All materials used for manufacturing the OLED are purified by vacuum sublimation under 10 -6 Torr.

[0258] Comparative Examples 4 and 5: Production of an OLED Containing a Conventional Compound

[0259] Manufacture the OLED in the same manner as in Device Example 4, except that the hole transport layer, the host material of the light-emitting layer, and the electron buffer layer are made of light hydrogen materials.

[0260] For the OLEDs of Device Example 4 and Device Example 5 and Comparative Example 4 and Comparative Example 5 described above, Table 4 below shows the current efficiency at a brightness of 1,000 nits according to the CIE color coordinates and the time taken for the brightness to decrease from 100% to 97% at a brightness of 10,000 nits according to the CIE color coordinates (lifetime: T 97 ).

[0261] [Table 4]

[0262]

[0263]

[0264] As can be confirmed from Table 4 above, compared with a conventional organic electroluminescent device, the organic electroluminescent device according to the present disclosure exhibits higher current efficiency and much longer lifetime.

[0265] Device Example 6: Production of an OLED Deposited with a Compound According to the Present Disclosure

[0266] To produce an OLED according to the present disclosure. First, an indium tin oxide (ITO) thin film (10 Ω / sq) (manufactured by Geomatec Co., Ltd., Japan) of a transparent electrode on a glass substrate for the OLED is ultrasonically washed successively with acetone and isopropyl alcohol, and then stored in isopropyl alcohol. The ITO substrate is mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI (p-dopant) is introduced into one chamber of the vacuum vapor deposition apparatus, and compound HT'-1 is introduced into another chamber. The two materials are evaporated at different rates, and compound HI is deposited at a doping amount of 3 wt% based on the total amount of compound HI and compound HT'-1 to form a hole injection layer having a thickness of 10 nm. Subsequently, compound HT'-1 is deposited on the hole injection layer to form a first hole transport layer having a thickness of 80 nm. Next, the compound shown in Table 5 is introduced into another chamber of the vacuum vapor deposition apparatus as a second hole transport layer, and is evaporated by applying current to the chamber, thereby depositing it with a thickness of 30 nm. After forming the hole injection layer and the hole transport layer, a light-emitting layer is deposited thereon as follows: the compound shown in Table 5 below is introduced into one chamber of the vacuum vapor deposition apparatus as a host at a ratio of 2:1, and compound GD is introduced into another chamber as a dopant. The materials are evaporated at different rates, and the dopant is deposited at a doping amount of 10 wt% based on the total amount of the host and the dopant to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer. The compound shown in Table 5 is deposited as an electron buffer layer with a thickness of 5 nm, and then compound EI-1 and compound Liq are introduced into two other chambers and evaporated at a rate of 1:1 to deposit an electron transport layer having a thickness of 35 nm on the light-emitting layer. After introducing compound Liq as an electron injection layer and depositing it with a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 80 nm is deposited by using another vacuum vapor deposition apparatus, thereby producing the OLED. All materials used for producing the OLED are purified by vacuum sublimation under 10 -6 Torr.

[0267] Comparative Example 6: Production of an OLED Containing a Conventional Compound

[0268] An OLED is produced in the same manner as in Device Example 6, except that the hole transport layer, the host material of the light-emitting layer, and the electron buffer layer are made of a light hydrogen material.

[0269] For the OLEDs of Device Example 6 and Comparative Example 6 as described above, Table 5 below shows the current efficiency at a brightness of 1,000 nits and the time taken for the brightness to decrease from 100% to 95% at a brightness of 1,000 nits (lifetime: T 95 ).

[0270] [Table 5]

[0271]

[0272]

[0273] It can be confirmed from Table 5 above that, compared with a conventional organic electroluminescent device, the organic electroluminescent device according to the present disclosure exhibits a higher lifetime while maintaining the current efficiency.

[0274] The compounds used in the above device examples and comparative examples are shown in Table 6 below.

[0275] [Table 6] Compounds Used in Device Examples and Comparative Examples

[0276]

Claims

1. An organic electroluminescent device comprising an anode, a hole transport region, a light emitting layer, an electron transport region and a cathode, wherein the hole transport region, the light emitting layer and the electron transport region each comprise one or more deuterated compounds, and the structure of each of the compounds is the same as or different from each other.

2. The organic electroluminescent device according to claim 1, wherein: The hole transport region is configured by sequentially stacking a hole injection layer, a hole transport layer consisting of one or more layers, and a hole auxiliary layer or an electron blocking layer consisting of one or more layers on the anode, and wherein at least one of the layers contains one or more deuterated compounds.

3. The organic electroluminescent device according to claim 1, wherein: The electron transport region is configured by sequentially stacking an electron buffer layer or a hole blocking layer consisting of one or more layers, an electron transport layer consisting of one or more layers, and an electron injection layer on the light emitting layer, and at least one of the layers contains one or more deuterated compounds.

4. The organic electroluminescent device according to claim 1, wherein: The light-emitting layer is composed of one or more layers, and at least one layer in the light-emitting layer contains one or more deuterated compounds as a host.

5. The organic electroluminescent device according to claim 1, wherein: The light emitting layer includes a phosphorescent or fluorescent light emitting compound, and the compound includes iridium (Ir), platinum (Pt), or boron (B) atoms.

6. The organic electroluminescent device according to claim 2, wherein: At least one layer in the hole transport region includes a compound represented by the following Formula 1: In formula 1, Ar1 to Ar3 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted mono- or di-(C6-C30) arylamino, mono- or di-(C1-C30) alkane alkylamino, mono- or di-(C2-C30)alkenylamino, (C1-C30)alkyl(C6-C30)arylamino, mono- or di-(3- to 30-membered)heteroarylamino, or (C6-C30)aryl(3- to 30-membered)heteroarylamino, provided that each Ar1 to each Ar3 comprises at least one of a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered)heteroaryl group; L1 to L3 each independently represent a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3-membered to 30-membered)heteroarylene group; and D n It means that n number of hydrogen atoms are substituted with deuterium, and n represents an integer of 1 or more and has an upper limit on the number of hydrogen atoms in the non-deuterated compound.

7. The organic electroluminescent device according to claim 6, wherein: At least one of Ar1 to Ar3 includes a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

8. The organic electroluminescent device according to claim 3, wherein: At least one layer in the electron transport region includes a compound represented by the following Formula 2 or Formula 3: In Formula 2, L 11 and L 12 each independently represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group; Ar 11 and Ar 12 Each independently represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; R 11 To R 18 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 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 a mono- or di-(C2-C30)alkenylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, a substituted or unsubstituted mono- or di-(3- to 30-membered)heteroarylamino group, a substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino group, a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group, a substituted or unsubstituted (C1-C30)alkyl(3- to 30-membered)heteroarylamino group, a substituted or unsubstituted (C2-C30)alkenyl(C6-C30)arylamino group, a substituted or unsubstituted (C2-C30)alkenyl(3- to 30-membered)heteroarylamino group, or a substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino group; R 11 and R 14 To R 16 At least one of represents deuterium; and D n represents that n number of hydrogen atoms are replaced by deuterium, and n represents an integer of 1 or more and has an upper limit on the number of hydrogen atoms in the non-deuterated compound; And where in Formula 3, X 21 To X 23 Each independently represents CR' or N, provided that X 21 To X 23 At least two of them represent N; R' represents hydrogen or deuterium; L 21 To L 23 each independently represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group; Ar 21 To Ar 23 Each independently represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group, provided that Ar 21 To Ar 23 at least one of which contains deuterium; p, q and r each independently represent an integer of 1 to 3, wherein if p, q and r represent an integer of 2 or more, each L 21 To each L 23 may be the same or different; and D n It means that n number of hydrogen atoms are substituted with deuterium, and n represents an integer of 1 or more and has an upper limit on the number of hydrogen atoms in the non-deuterated compound.

9. The organic electroluminescent device according to claim 8, wherein: R in Formula 2 11 To R 18 ,Ar 11 and Ar 12 At least one of is represented by the following formula 2-1 or formula 2-2: In Formula 2-1 and Formula 2-2, L'1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group; and R'1 to R'5 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-membered to 30-membered) heteroaryl group.

10. The organic electroluminescent device according to claim 8, wherein: Ar 21 To Ar 23 At least one of the following comprises a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, provided that Ar 21 To Ar 23 At least one of the comprises deuterium.

11. The organic electroluminescent device according to claim 4, wherein: At least one of the light-emitting layers comprises a compound represented by the following Formula 4 or Formula 5: In formula 4, A1 and A2 each independently represent a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group; X' 15 To X' 18 Any one of X' 19 To X' 22 Any of them are connected to each other to form a single bond; X' that does not form a single bond 11 To X' 14 , X' 23 To X' 26 , and X' 15 To X' 22 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl, or may be linked to one or more adjacent substituents to form one or more rings; X' 11 , X' 18 , X' 19 or X' 26 At least one of represents deuterium; and D n represents that n number of hydrogen atoms are replaced by deuterium, and n represents an integer of 1 or more and has an upper limit on the number of hydrogen atoms in the non-deuterated compound; And where in Formula 5, R 51 To R 53 At least one of them contains the following formula 5-1 or formula 5-2: or L 51 and L 52 can be a single bond, and R 51 and R 52 can be connected to each other to be expressed by any one of the following formulas 5-3 to 5-5: R 51 To R 53 and R' 51 To R' 59 each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 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, a substituted or unsubstituted condensed ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or a substituted or unsubstituted mono- or di-(C1-C30) alkylamino group; , 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- to 30-membered)heteroarylamino, substituted or unsubstituted (C1-C30)alkyl(3- to 30-membered)heteroarylamino, substituted or unsubstituted (C2-C30)alkenyl(C6-C30)arylamino, substituted or unsubstituted (C2-C30)alkenyl(3- to 30-membered)heteroarylamino, or substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino, or may be linked to one or more adjacent substituents to form one or more rings; L 51 To L 53 each independently represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group; "X" means O or S; a, b, e and f each independently represent an integer of 1 or 2, c, d and g each independently represent an integer of 1 to 4, wherein if a to g represent an integer of 2 or more, each R' 51 To each R' 59 may be the same or different; and D n It means that n number of hydrogen atoms are substituted with deuterium, and n represents an integer of 1 or more and has an upper limit on the number of hydrogen atoms in the non-deuterated compound.

12. The organic electroluminescent device according to claim 4, wherein: If the at least one layer in the light emitting layer includes two or more compounds, the two or more compounds include a compound represented by the following Formula 6 or Formula 7: In equations 6 and 7, X 61 Indicates O or S; HAR 61 and HAr 62 each independently represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group containing one or more nitrogen atoms; L 61 and L 62 each independently represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group; R 61 To R 64 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; or may be linked to one or more adjacent substituents to form one or more rings; h to k each independently represent an integer of 1 to 4, wherein if h to k represent an integer of 2 or more, each R 61 To each R 64 may be the same or different; and D n It means that n number of hydrogen atoms are substituted with deuterium, and n represents an integer of 1 or more and has an upper limit on the number of hydrogen atoms in the non-deuterated compound.

13. The organic electroluminescent device according to claim 4, wherein: At least one layer of the light-emitting layer includes a compound represented by the following Formula 8: In formula 8, Ar 81 represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; R 81 To R 88 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C1-C30) alkane oxy, 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 one or more (C3-C30)aliphatic rings and one or more (C6-C30)aromatic rings; Ar A represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group, or is represented by the following formula A-1; and D n represents that n number of hydrogen atoms are replaced by deuterium, and n represents an integer of 1 or more and has an upper limit on the number of hydrogen atoms in the non-deuterated compound; T1 means O, S or CR l R m ; R' 81 To R' 88 Each is independently related to L 82 The site of attachment, or represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C1-C30) alkane oxy, 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, a substituted or unsubstituted condensed ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or -L 83 -N(Ar 83 )(Ar 84 ); R l and R m Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, or a substituted or unsubstituted (C6-C30) aryl group, or may be linked to each other to form one or more rings; L 81 To L 83 each independently represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group; and Ar 83 and Ar 84 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, one or more (C3-C 30 ) aliphatic ring and one or more (C6-C30) aromatic rings, a substituted or unsubstituted fused ring group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, or a substituted or unsubstituted tri(C6-C 30 )Arylsilyl.

14. The organic electroluminescent device according to claim 6, wherein: The compound represented by Formula 1 is at least one selected from the following compounds:

15. The organic electroluminescent device according to claim 8, wherein: The compound represented by Formula 2 or Formula 3 is at least one selected from the following compounds:

16. The organic electroluminescent device according to claim 11, wherein: The compound represented by Formula 4 or Formula 5 is at least one selected from the following compounds:

17. The organic electroluminescent device according to claim 12, wherein: The compound represented by Formula 6 or Formula 7 is at least one selected from the following compounds:

18. The organic electroluminescent device according to claim 13, wherein: The compound represented by Formula 8 is at least one selected from the following compounds:

19. The organic electroluminescent device according to claim 4, wherein: At least one layer of the light-emitting layer includes a compound represented by the following Formula 9: In formula 9, X 15 To X 18 Any adjacent pairs in the following formula 9-A are connected to form one or more rings, and X that does not form a ring 15 To X 18 , X 11 To X 14 , and X 31 To X 34 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; Wherein in Formula 9 and Formula 9-A, A1 and A3 each independently represent a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted carbazolyl group; L3 and L5 each independently represent a single bond, or a substituted or unsubstituted (C6-C30)arylene group; and D n It means that n number of hydrogen atoms are substituted with deuterium, and n represents an integer of 1 or more and has an upper limit on the number of hydrogen atoms in the non-deuterated compound.

20. The organic electroluminescent device according to claim 19, wherein: X 11 or X 31 Denotes deuterium.

21. The organic electroluminescent device according to claim 19, wherein: The compound represented by Formula 9 is represented by any one of the following Formulas 9-1 to 9-6: In Formula 9-1 to Formula 9-6, A1, A3, L3, L5, X 11 To X 18 , X 31 To X 34 , and D n As defined in claim 19.

22. The organic electroluminescent device according to claim 19, wherein: The compound represented by Formula 9 is at least one selected from the following compounds:

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