Organic electroluminescent device

Abstract

To provide an organic electroluminescent device.SOLUTION: The present disclosure relates to an organic electroluminescent device. The organic electroluminescent device according to the present disclosure can have overall device stability by including a deuterated compound in the electron transport zone.SELECTED DRAWING: None

Description

Technical Field

[0001] The present disclosure relates to an organic electroluminescent device containing a deuterated compound.

Background Art

[0002] The small molecule green organic electroluminescent device (OLED) was first developed in 1987 by Tang et al. of Eastman Kodak by using a TPD / ALq3 bilayer composed of a light emitting layer and a charge transport layer. Thereafter, the development of OLEDs has advanced rapidly and reached commercialization. Currently, OLEDs mainly use phosphorescent materials having excellent luminous efficiency in panel mounting. However, in various applications such as televisions and lighting, the lifespan of OLEDs is often insufficient, and further improvement in the efficiency of OLEDs is still required. Generally, the lifespan of an OLED becomes shorter as the luminance increases. Therefore, an OLED having high luminous efficiency and / or a long lifespan is essential for long-term use and high-resolution displays.

[0003] In order to improve current efficiency and / or lifespan, various materials or concepts have been proposed for the organic layers of organic electroluminescent devices, but they have not been satisfactory in actual use. In addition, compared with the combinations of specific compounds disclosed in the past, the development of organic electroluminescent devices with improved performance such as improved current efficiency and / or lifespan characteristics has been continuously demanded.

[0004] On the other hand, (Patent Document 1), (Patent Document 2), and (Patent Document 3) disclose organic electroluminescent devices containing deuterated compounds. Nevertheless, the above documents do not specifically disclose an organic electroluminescent device having the stability of the whole device by including a deuterated compound in the electron transport zone. In addition, compared with the specific organic electroluminescent devices disclosed in the past, the development of light emitting materials with improved performance such as improved lifespan characteristics has been continuously demanded.

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Patent Document 2

Patent Document 3

Patent Document 4

Patent Document 5

Summary of the Invention

Problems to be Solved by the Invention

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

Means for Solving the Problems

[0007] As a result of intensive studies to solve such technical problems, the present inventors have found that an organic electroluminescent device including an anode, a hole transport zone, a light emitting layer, an electron transport zone, and a cathode, wherein each of the hole transport zone, the light emitting layer, and the electron transport zone contains a deuterated compound, and the structures of the respective compounds are the same as or different from each other, can achieve the above object.

[0008] The organic electroluminescent device of the present disclosure contains a deuterated compound in each of the hole transport zone, the light emitting layer, and the electron transport zone, and thus exhibits higher current efficiency and / or improved lifetime characteristics.

Modes for Carrying Out the Invention

[0009] The present disclosure will be described in detail below. However, the following description is intended to explain the present disclosure and is in no way intended to limit the scope of the present disclosure.

[0010] 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, if necessary, into any layer constituting the organic electroluminescent device.

[0011] 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. The organic electroluminescent material can be incorporated, if necessary, into any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material can be any of a hole injection material, a hole transport material, a hole auxiliary material, a light emission auxiliary material, an electron blocking material, a light emitting material (including a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, and the like.

[0012] The term "plurality of organic electroluminescent materials" in the present disclosure means an organic electroluminescent material containing a combination of two or more compounds that can be incorporated into any layer constituting the organic electroluminescent device. This can mean both the material before being included in the organic electroluminescent device (e.g., before evaporation) and the material after being included in the organic electroluminescent device (e.g., after evaporation). For example, the plurality of organic electroluminescent materials can be a combination of two or more compounds contained in at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emission auxiliary layer, an electron blocking layer, a light emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. The two or more compounds can be contained in the same layer or different layers and can be co-evaporated or simultaneously evaporated, or can be evaporated individually.

[0013] As used herein, the term "plurality of host materials" means a host material comprising a combination of at least two compounds that 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 evaporation) and the material after being included in the organic electroluminescent device (e.g., after evaporation). For example, the plurality of host materials of the present disclosure is a combination of at least two host materials and can optionally further include conventional materials included in the organic electroluminescent material. The at least two compounds included in the plurality of host materials of the present disclosure can be included together in one light-emitting layer or can be included in different light-emitting layers, respectively. For example, at least two host materials can be co-evaporated or co-deposited, or can be evaporated individually.

[0014] As used herein, the term “(C1-C30)alkyl” means a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, where the number of carbon atoms is preferably 1 to 10, more preferably 1 to 6. The above alkyl may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, etc. The term “(C3-C30)cycloalkyl” means a monocyclic or polycyclic hydrocarbon having 3 to 30 ring skeleton carbon atoms, where the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7. Examples of the above cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, etc. The term “(3-7 membered)heterocycloalkyl” means a cycloalkyl having 3 to 7 ring skeleton atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably the group consisting of O, S, and N. The above heterocycloalkyl may include tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, etc. The terms “(C6-C30)aryl”, “(C6-C30)arylene”, and “(C6-C30)arenetriyl” mean monocyclic or fused ring radicals derived from aromatic hydrocarbons having 6 to 30 ring skeleton carbon atoms that are partially saturable. The above aryl, arylene, and arenetriyl may include a spiro structure. Examples of the above aryl may include phenyl, biphenyl, terphenyl, kink phenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, benzophenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, spiro[fluorene-benzofluorene]yl, spiro[cyclopentene-fluorene]yl, spiro[dihydroindene-fluorene]yl, azulhenyl, tetramethyldihydrophenanthrenyl, etc. Specifically,Examples of the aryl group include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthanthryl, pyrenyl, 1-chrysenyl, 2-chrysenyl, 3-chrysenyl, 4-chrysenyl, 5-chrysenyl, 6-chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 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-quarterphenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, 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. may be included.,

[0015] The terms “(3-30-membered) heteroaryl”, “(3-30-membered) heteroarylene” and “(3-30-membered) heteroalentriyl” are intended to be aryl(en) groups having 3 to 30 ring backbone atoms and containing at least 1, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, Si, P, Se, Te, and Ge. The above heteroaryl can be a monocyclic ring or a fused ring condensed with at least one benzene ring, can be partially saturated, and can be formed by bonding at least one heteroaryl or aryl group to the heteroaryl group via a single bond, and can contain a spiro structure. Examples of the above heteroaryl include monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl and pyridazinyl, and fused ring heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthoxazolyl, benzofuroquinolinyl, benzofuroquinazolinyl, benzofuronaphthyridinyl, benzofuropyrimidinyl, naphthofuropyrimidinyl, benzothienoquinolinyl, benzothienoquinazolinyl, naphthyridinyl, benzothienonaphthyridinyl, benzothienopyrimidinyl, naphthothienopyrimidinyl, pyrimidinoindolyl, benzopyrimidinoindolyl, benzofuropyrazinyl, naphthofuropyrazinyl, benzothienopyrazinyl, naphthothienopyrazinyl, phenanthroxazolyl, phenanthrothiazolyl, phenanthrobenzofuranyl, benzophenanthrothiophenyl, pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, carbazolyl, benzocarbazolyl,Examples thereof include dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, benzotriazolyl, phenazinyl, imidazopyridyl, chromenokazinolinyl, thiochromenokazinolinyl, dimethylbenzoperymidinyl, indolocarbazolyl, indenocarbazolyl, etc. More specifically, examples of the above heteroaryl 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-imidazopyridyl, 3-imidazopyridyl, 5-imidazopyridyl, 6-imidazopyridyl, 7-imidazopyridyl, 8-imidazopyridyl, 3-pyridyl, 4-pyridyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, 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]-benzothiophenyl, 9-Naphtho-[2,1-b]-benzothiophenyl, 10-Naphtho-[2,1-b]-benzothiophenyl, 2-Benzofuro[3,2-d]pyrimidinyl, 6-Benzofuro[3,2-d]pyrimidinyl, 7-Benzofuro[3,2-d]pyrimidinyl, 8-Benzofuro[3,2-d]pyrimidinyl,9-benzofuro[3,2-d]pyrimidinyl, 2-benzothieno[3,2-d]pyrimidinyl, 6-benzothieno[3,2-d]pyrimidinyl, 7-benzothieno[3,2-d]pyrimidinyl, 8-benzothieno[3,2-d]pyrimidinyl, 9-benzothieno[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-benzothieno[3,2-d]pyrazinyl, 6-benzothieno[3,2-d]pyrazinyl, 7-benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[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, and the like can be mentioned. "Heteroaryl(ene)" can be classified into heteroaryl(ene) having electron properties and heteroaryl(ene) having hole properties. Heteroaryl(ene) having electron properties has a nucleophilic substituent that is relatively rich in electrons, such as substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, or substituted or unsubstituted quinolyl, etc. Heteroaryl(ene) having hole properties has a nucleophilic substituent that is relatively poor in electrons, such as substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, etc. In the present disclosure, the term "halogen" includes F, Cl, Br, and I.,

[0016] In addition, "ortho-" ("o-"), "meta-" ("m-"), and "para-" ("p-") are prefixes that represent the relative positions of substituents. The prefix "ortho-" indicates that two substituents are adjacent to each other. For example, when two substituents of a benzene derivative occupy the 1st and 2nd positions or the 2nd and 3rd positions, it is called the ortho arrangement. The prefix "meta-" represents that two substituents are at the 1st and 3rd positions. For example, when two substituents of a benzene derivative occupy the 1st and 3rd positions, this is called the "meta-" arrangement. The prefix "para-" represents that two substituents are at the 1st and 4th positions. For example, when two substituents of a benzene derivative occupy the 1st and 4th positions, this is called the "para-" arrangement. Unless otherwise specified, the substituent may replace hydrogen at the positions where the substituent can replace without limitation. When two or more hydrogen atoms in a specific functional group are each replaced by a substituent, each substituent may be the same as or different from each other. The maximum number of substituents that can be substituted for a certain functional group may be the total number of valences that can be substituted for each atom forming the functional group.

[0017] In this specification, substituted alkyl, substituted alkenyl, substituted cycloalkyl, substituted cycloalkenyl, substituted heterocycloalkyl, substituted silyl, substituted aryl(en), substituted heteroaryl(en), substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted condensed ring groups of aliphatic and 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 are each independently 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; (3-7 membered)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (C6-C30)aryl substituted with at least one of unsubstituted or (C1-C30)alkyl, (C6-C30)aryl and (3-30 membered)heteroaryl; (3-30 membered)heteroaryl substituted with unsubstituted or (C6-C30)aryl; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; (C3-C30)condensed ring group of aliphatic and (C6-C30)aromatic rings; amino; mono- or di-(C1-C30)alkylamino; mono- or di-(C2-C30)alkenylamino; mono- or di-(C6-C30)arylamino substituted with unsubstituted or (C1-C30)alkyl; mono- or di-((3-30 membered)heteroarylamino;(C1-C30) alkyl (C2-C30) alkenylamino; (C1-C30) alkyl (C6-C30) arylamino; (C1-C30) alkyl (3-30 membered) heteroarylamino; (C2-C30) alkenyl (C6-C30) arylamino; (C2-C30) alkenyl (3-30 membered) heteroarylamino; (C6-C30) aryl (3-30 membered) heteroarylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; di(C6-C30) arylboronyl; di(C1-C30) alkylboronyl; (C1-C30) alkyl (C6-C30) arylboronyl; (C6-C30) aryl (C1-C30) alkyl; and may be substituted by at least one selected from the group consisting of (C1-C30) alkyl (C6-C30) aryl. According to one embodiment of the present disclosure, substituted alkyl and the like are each independently (C1-C25) alkyl; (C3-C25) cycloalkyl; unsubstituted or (C6-C25) aryl substituted by at least one of (C1-C30) alkyl, (C6-C30) aryl and (3-30 membered) heteroaryl; (3-25 membered) heteroaryl unsubstituted or substituted by (C6-C30) aryl; and may be substituted by at least one selected from the group consisting of mono- or di-(C6-C25) arylamino unsubstituted or substituted by (C6-C30) aryl. For example, substituted alkyl and the like may be substituted by at least one selected from the group consisting of methyl, phenyl, biphenyl, terphenyl, naphthyl, naphthyl substituted by phenyl, naphthyl substituted by naphthyl, naphthyl substituted by dibenzofuranyl, phenanthrenyl, triphenylene, benzofluorenyl, benzofluorenyl substituted by methyl, benzofluorenyl substituted by phenyl, carbazolyl, carbazolyl substituted by phenyl, dibenzofuranyl, dibenzothiophenyl, diphenylamino, phenylbiphenylamino, etc.;

[0018] In the present disclosure, when a substituent is not shown in a formula or a compound structure, it may mean that all positions where the substituent can be present 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. In this case, the deuterium content may be from 0% to 100%. In the present disclosure, when a substituent is not shown in a formula or a compound structure, hydrogen and deuterium may be mixed in the compound, such as 0% deuterium, 100% hydrogen, and all substituents being hydrogen, unless the substituent is explicitly excluded. Deuterium is one of the isotopes of hydrogen and is an element having a deuteron composed of one proton and one neutron as its nucleus. This can be represented as hydrogen-2, and its element symbol can be written as D or 2 H. Isotopes are atoms having the same atomic number (Z) but different mass numbers (A), and can also be interpreted as elements having the same number of protons but different numbers of neutrons.

[0019] In the present disclosure, "their combinations" refers to combinations of one or more elements from the corresponding lists to form known or chemically stable arrangements that can be assumed by those skilled in the art from the corresponding lists. For example, alkyl and deuterium can be combined to form a partially or fully deuterated alkyl group; halogen and alkyl can be combined to form a halogenated alkyl substituent; halogen, alkyl, and aryl can be combined to form a halogenated arylalkyl. For example, preferred combinations of substituents 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. In many cases, preferred combinations of substituents may include up to 20 atoms that are not hydrogen or deuterium.

[0020] In the formula of the present disclosure, when there are a plurality of substituents represented by the same symbol, each of the substituents represented by the same symbol may be the same as or different from each other.

[0021] In the formula of the present disclosure, when adjacent substituents are linked to form a ring, the ring can be linked 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 may contain at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably at least one heteroatom selected from the group consisting of N, O, and S. According to one embodiment of the present disclosure, the number of ring backbone atoms is (5 to 20 members), and according to another embodiment of the present disclosure, the number of ring backbone atoms is (5 to 15 members).

[0022] The present disclosure relates to an organic electroluminescent device including an anode, a hole transport zone, a light-emitting layer, an electron transport zone, and a cathode, wherein each of the hole transport zone, the light-emitting layer, and the electron transport zone contains a deuterated compound, and the structures of the compounds are the same as or different from each other.

[0023] According to one embodiment of the present disclosure, a hole transport zone is formed by sequentially laminating a hole injection layer, a hole transport layer including one or more layers, and a hole auxiliary layer or an electron blocking layer including one or more layers on the anode, and an organic electroluminescent device in which at least one layer contains a deuterated compound is provided.

[0024] According to one embodiment of the present disclosure, an electron transport zone is formed by sequentially laminating an electron buffer layer or a hole blocking layer including one or more layers, an electron transport layer including one or more layers, and an electron injection layer on the light-emitting layer, and an organic electroluminescent device in which at least one layer contains a deuterated compound is provided.

[0025] According to one embodiment of the present disclosure, a light-emitting layer includes one or more layers, and at least one of the light-emitting layers contains one or more deuterated compounds as a host, and an organic electroluminescent device is provided.

[0026] According to one 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.

[0027] According to one embodiment of the present disclosure, the organic electroluminescent device according to the present disclosure may include at least one layer of a hole transport zone containing a compound represented by the following formula 1.

Chemical formula

[0028] According to one embodiment of the present disclosure, each of Ar1 to Ar3 is independently hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, or substituted or unsubstituted mono- or di-(C6-C30) arylamino; preferably hydrogen, deuterium, substituted or unsubstituted (C6-C26) aryl, substituted or unsubstituted (3-13 membered) heteroaryl, or substituted or unsubstituted mono- or di-(C6-C12) arylamino, provided that each of Ar1 to Ar3 may contain at least one of substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (3-30 membered) heteroaryl. More preferably, at least one of Ar1 to Ar3 represents substituted or unsubstituted phenanthrenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl. For example, each of Ar1 to Ar3 is independently substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted diphenylamino, or substituted or unsubstituted phenylbiphenylamino, provided that each of Ar1 to Ar3 may contain at least one of substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (3-30 membered) heteroaryl. In the above, the substituent of the substituted one may be at least one selected from deuterium, methyl, phenyl, biphenyl, phenanthrenyl, benzofluorenyl substituted with methyl, benzofluorenyl substituted with phenyl, carbazolyl, carbazolyl substituted with phenyl, dibenzofuranyl, diphenylamino, and phenylbiphenylamino.

[0029] According to one embodiment of the present disclosure, L1 to L3 may each independently represent a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (3-25 membered) heteroarylene. L1 to L3 may each independently represent a single bond, a substituted or unsubstituted (C6-C12) arylene, or a substituted or unsubstituted (3-13 membered) heteroarylene. For example, L1 to L3 may each independently be a single bond, a substituted or unsubstituted phenylene, biphenylene, a substituted or unsubstituted carbazolylene, dibenzothiophenylene, or dibenzofuranylene, etc. In the above, the substituent of the substituted one may be at least one selected from deuterium, phenyl, carbazolyl, carbazolyl substituted with phenyl, dibenzofuranyl, and dibenzothiophenyl.

[0030] 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%, still more preferably 30% to 95%, and still more preferably 40% to 95%.

[0031] According to one embodiment of the present disclosure, the deuterated compound may be more specifically exemplified by, but not limited to, the following compounds.

Chemical formula

Chemical formula

[0032] According to one embodiment of the present disclosure, the organic electroluminescent device of the present disclosure may contain a compound represented by the following formula 2 or formula 3 in at least one layer of the electron transport zone.

Chemical formula

[0033] According to one embodiment of the present disclosure, L 11 and L 12 each independently represents a single bond or a substituted or unsubstituted (C6-C30) arylene; preferably, a single bond or a substituted or unsubstituted (C6-C25) arylene; more preferably, a single bond or a substituted or unsubstituted (C6-C18) arylene. For example, L 11 and L 12 each independently may be a single bond or phenylene.

[0034] According to one embodiment of the present disclosure, Ar 11 and Ar 12 each independently represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (5-30 membered) heteroaryl; preferably, a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (5-25 membered) heteroaryl; more preferably, a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (5-20 membered) heteroaryl. For example, Ar 11 and Ar 12 each independently is a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted p-biphenyl, or a substituted or unsubstituted benzimidazolyl, and is represented by the following Formula 2-1 or 2-2.

[0035] 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%, still more preferably 30% to 95%, and still more preferably 40% to 95%.

Chemical formula

[0036] According to one embodiment of the present disclosure, L’1 can represent a single bond or a substituted or unsubstituted (C6-C30) arylene; preferably, a single bond or a substituted or unsubstituted (C6-C25) arylene; more preferably a single bond or a substituted or unsubstituted (C6-C18) arylene. For example, L’1 can be a single bond or phenylene.

[0037] According to one embodiment of the present disclosure, R’1 to R’4 can each independently represent hydrogen or deuterium.

[0038] According to one embodiment of the present disclosure, R’5 can represent a substituted or unsubstituted (C1-C30) alkyl or a substituted or unsubstituted (C6-C30) aryl; preferably, a substituted or unsubstituted (C1-C10) alkyl or a substituted or unsubstituted (C6-C25) aryl; more preferably, a substituted or unsubstituted (C1-C4) alkyl or a substituted or unsubstituted (C6-C18) aryl. For example, R’5 can be ethyl, phenyl, naphthyl, or biphenyl.

[0039] According to one embodiment of the present disclosure, R 11 ~R 18 can each independently represent hydrogen, deuterium, or a substituted or unsubstituted benzimidazolyl represented by the following formula 2-1 or 2-2.

[0040] According to one embodiment of the present disclosure, at least one of R 11 ~R 18 , Ar 11 and Ar 12 can be a substituted or unsubstituted benzimidazolyl represented by the above formula 2-1 or 2-2. [Chemical formula] In formula 3, X 21 ~X 23 each independently represents CR’ or N, provided that at least two of X 21 ~X 23 represent N; R’ represents hydrogen or deuterium; L 21 ~L 23 each independently represents a single bond, a substituted or unsubstituted (C6 - C30) arylene, or a substituted or unsubstituted (3 - 30 membered) heteroarylene; Ar 21 ~Ar 23 each independently represents a substituted or unsubstituted (C6 - C30) aryl or a substituted or unsubstituted (3 - 30 membered) heteroaryl, provided that at least one of Ar 21 ~Ar 23 contains deuterium; p, q, and r each independently represent an integer from 1 to 3, where when p, q, and r represent integers greater than or equal to 2, each of L 21 ~L 23 may be the same or different; and D n represents that n hydrogens are substituted with deuterium, n is an integer greater than or equal to 1, and is the upper limit of the number of hydrogen atoms in the non - deuterated compound.

[0041] According to one embodiment of the present disclosure, at least two of X 21 ~X 23 represent N, and preferably, all of X 21 ~X 23 may represent N.

[0042] According to one embodiment of the present disclosure, L 21 ~L 23 each independently may represent a single bond, or a substituted or unsubstituted (C6 - C30) arylene. Preferably, L 21 ~L 23Each independently represents a single bond or a substituted or unsubstituted (C6-C25) arylene. More preferably, L 21 ~L 23 Each independently represents a single bond or a substituted or unsubstituted (C6-C18) arylene. For example, L 21 ~L 23 Each independently can be a single bond, or a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted o-biphenylene, a substituted or unsubstituted m-biphenylene, or a substituted or unsubstituted o-terphenylen. In the above, the substituent of the substituted one can be at least one selected from deuterium, phenanthrenyl, pyridyl substituted by at least one of unsubstituted or methyl or phenyl, and quinolinyl.

[0043] According to one embodiment of the present disclosure, Ar 21 ~Ar 23 Each independently is a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (5-30 membered) heteroaryl; preferably, a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (5-26 membered) heteroaryl; more preferably, it can represent a substituted or unsubstituted (C6-C18) aryl or a substituted or unsubstituted (5-26 membered) heteroaryl. Preferably, at least one of Ar 21 ~Ar 23 can contain a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted benzofluorenyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted dibenzofuran, or a substituted or unsubstituted dibenzothiophenyl, provided that at least one of Ar 21 ~Ar 23 contains deuterium. For example, Ar 21 ~Ar 23Each is independently a substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted phenanthrenyl, 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.

[0044] 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%, still more preferably 30% to 95%, and even more preferably 40% to 95%.

[0045] According to one embodiment of the present disclosure, the deuterated compound can be more specifically exemplified by, but not limited to, the following compounds.

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0046] According to one embodiment of the present disclosure, the organic electroluminescent device according to the present disclosure may include at least one layer containing a compound represented by the following formula 4 or formula 5 in the light-emitting layer.

Chemical formula

[0047] According to one embodiment of the present disclosure, A1 and A2 may each independently represent a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted dibenzofuranyl. Preferably, A1 and A2 may each independently represent a substituted or unsubstituted (C6-C18) aryl or a substituted or unsubstituted dibenzofuranyl. For example, A1 and A2 may each independently be a substituted or unsubstituted phenyl, biphenyl, substituted or unsubstituted naphthyl, terphenyl, triphenylene, or substituted or unsubstituted dibenzofuranyl. The substituents of the above substituted ones may be at least one selected from deuterium, phenyl, naphthyl, triphenylene, and dibenzofuran.

[0048] 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%, still more preferably 30% to 95%, and still more preferably 40% to 95%.

Chemical formula

Chemical formula

Chemical formula

[0049] According to one embodiment of the present disclosure, R 51 ~R 53 and R’ 51 ~R’ 59 are each independently hydrogen, deuterium, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 membered) heteroaryl, a (C3-C30) aliphatic ring and a substituted or unsubstituted condensed ring group of a (C6-C30) aromatic ring, a substituted or unsubstituted mono- or di-(C6-C30) arylamino, or a substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, or may combine with adjacent substituents to form a ring. Preferably, R 51 ~R 53 and R’ 51 ~R’ 59 are each independently a substituted or unsubstituted (C6-C25) aryl, a substituted or unsubstituted (5-25 membered) heteroaryl, a substituted or unsubstituted condensed ring group of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted mono- or di-(C6-C18) arylamino, or may combine with adjacent substituents to form a ring. For example, R 51 ~R 53 and R’ 51 ~R’ 59 are each independently unsubstituted phenyl or phenyl substituted by phenyl, naphthyl, biphenyl, terphenyl, phenanthrenyl, 23-membered heteroaryl, dibenzofuranyl, dibenzothiophenyl, diphenylamino, phenylbiphenylamino, phenylnaphthylamino, diphenylamino, Formula 5-1 or Formula 5-2, etc., or may combine with adjacent substituents to form a benzoindolecarbazole ring such as Formula 5-3 or Formula 5-4, and may be further substituted by one or more deuterium atoms.

[0050] According to one embodiment of the present disclosure, X’’ may represent O.

[0051] According to one embodiment of the present disclosure, L 51 ~L 53 may each independently represent a single bond, or a substituted or unsubstituted (C6-C30) arylene. Preferably, L 51 ~L 53 may each independently represent a single bond, or a substituted or unsubstituted (C6-C12) arylene. For example, L 51 ~L 53 may each independently be a single bond, phenyl, biphenyl, etc., which may be further substituted by one or more deuterium atoms.

[0052] 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%, still more preferably 30% to 95%, and still more preferably 40% to 95%.

[0053] According to one embodiment of the present disclosure, the deuterated compound may be more specifically exemplified by, but not limited to, the following compounds.

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0054] According to one embodiment of the present disclosure, the organic electroluminescent device according to the present disclosure may include at least one layer containing two or more compounds represented by the following Formula 6 or Formula 7 in the light-emitting layer.

Chemical formula

[0055] According to one embodiment of the present disclosure, HAr 61 and HAr 62 may each independently represent a substituted or unsubstituted (3- to 15-membered) heteroaryl containing at least one or more nitrogens. For example, HAr 61 and HAr 62 may each independently be a substituted triazinyl, and the substituents of the substituted triazinyl may be at least one, preferably two, selected from naphthyl, biphenyl, terphenyl, naphthyl substituted with phenyl, naphthyl substituted with naphthyl, naphthyl substituted with dibenzofuranyl, and dibenzofuran, and these may be further substituted with one or more deuterium atoms.

[0056] According to one embodiment of the present disclosure, L 61 and L 62Each independently may represent a single bond, or a substituted or unsubstituted (C6-C15) arylene. L 61 and L 62 Each independently may represent a single bond or a substituted or unsubstituted (C6-C10) arylene. For example, L 61 and L 62 Each independently may be a single bond, phenylene, naphthylene, etc., and these may be further substituted with one or more deuterium atoms.

[0057] According to one embodiment of the present disclosure, R 61 ~R 64 Each independently represents hydrogen, deuterium, a substituted or unsubstituted (C6-C20) aryl, or a substituted or unsubstituted (3-20 membered) heteroaryl, or may combine with adjacent substituents to form a ring. Preferably, X 61 ~X 64 Each independently represents hydrogen, deuterium, a substituted or unsubstituted (C6-C18) aryl, or a substituted or unsubstituted (3-20 membered) heteroaryl, or may combine with adjacent substituents to form a ring. For example, R 61 ~R 64 Each independently may be hydrogen, deuterium, naphthyl, carbazolyl, dibenzothiophenyl, dibenzofuranyl, etc., or may combine with adjacent substituents to form an indole ring, benzothiophene ring, or benzene ring substituted with phenyl or biphenyl, etc., and these may be further substituted with one or more deuterium atoms.

[0058] 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%, still more preferably 30% to 95%, and still more preferably 40% to 95%.

[0059] According to one embodiment of the present disclosure, the deuterated compound may be more specifically exemplified by, but not limited to, the following compounds.

Chemical formula

[0060] According to one embodiment of the present disclosure, the organic electroluminescent device of the present disclosure may include at least one layer containing a compound represented by the following formula 8 in the light-emitting layer. [Chemical formula] In formula 8, Ar 81 represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 membered) heteroaryl; R 81 ~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 (3-30 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) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, or a substituted or unsubstituted condensed ring group of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring; Ar A represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 membered) heteroaryl, or is represented by the following formula A-1; D n represents that n hydrogens are substituted with deuterium, n is an integer of 1 or more, and has an upper limit of the number of hydrogen atoms in the non-deuterated compound; [Chemical formula] T1 is O, S, or CR l R m represents; R’ 81 ~R’ 88 each independently represents a site bonded to L 82 or 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) 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 condensed ring group of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, or -L 83 -N(Ar 83 )(Ar 84 ) and; R l and R m each independently represents substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C6-C30) aryl, or may be bonded to each other to form a ring; L 81 and L 83 each independently represents a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3-30 membered) heteroarylene; Ar 83 and Ar 84is, independently of one another, 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) alkoxy, a substituted or unsubstituted condensed ring group of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, 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, or substituted or unsubstituted tri(C6-C30) arylsilyl.

[0061] According to one embodiment of the present disclosure, Ar 81 may represent substituted or unsubstituted (C6-C30) aryl. Preferably, Ar 81 may represent substituted or unsubstituted (C6-C18) aryl. For example, Ar 81 may be unsubstituted phenyl, or phenyl substituted with naphthyl, naphthyl, naphthyl, or biphenyl, etc., and these may be further substituted with one or more deuterium atoms.

[0062] According to one embodiment of the present disclosure, R 81 ~R 88 are, independently of one another, 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, or substituted or unsubstituted (C3-C30) cycloalkenyl. R 81 ~R 88may each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl. For example, R 81 ~R 88 may each independently be hydrogen or deuterium.

[0063] According to one embodiment of the present disclosure, Ar A may represent substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5-20 membered) heteroaryl, or may be represented by the above formula A-1. Preferably, Ar A represents substituted or unsubstituted (C6-C13) aryl, or substituted or unsubstituted (13-17 membered) heteroaryl, or may be represented by the above formula A-1. For example, Ar A may be substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted benzofluorenyl, dibenzofuranyl, or benzonaphthofuranyl, or may be the above formula A-1, and the substituents of the above substituted ones may be at least one selected from deuterium, methyl, phenyl, naphthyl, and dibenzofuran.

[0064] According to one embodiment of the present disclosure, T1 may represent O or S. For example, T1 may be O.

[0065] According to one embodiment of the present disclosure, R’ 81 ~R’ 88 may each independently be a site bonded to L 82 or may represent 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, or substituted or unsubstituted (C3-C30) cycloalkyl. Preferably, R’ 81 ~R’ 88 may each independently be a site bonded to L 82It may be a site combined with, or may represent hydrogen, deuterium, or unsubstituted (C6-C18) aryl. For example, R’ 81 ~R’ 88 may each independently be a site combined with L 82 , or hydrogen, deuterium, or phenyl, etc., and these may be further substituted with one or more deuterium atoms.

[0066] According to one embodiment of the present disclosure, L 81 ~L 83 may each independently represent a single bond, or substituted or unsubstituted (C6-C30) arylene. Preferably, L 81 ~L 83 may each independently represent a single bond, or substituted or unsubstituted (C6-C15) arylene. For example, L 81 ~L 83 may each independently represent a single bond, phenylene, naphthylene, or phenanthrenylene, etc., and these may be further substituted with one or more deuterium atoms.

[0067] 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%, still more preferably 30% to 95%, and still more preferably 40% to 95%.

[0068] According to one embodiment of the present disclosure, the deuterated compound can be more specifically exemplified by, but not limited to, the following compounds.

Chemical formula

Chemical formula

[0069] According to one embodiment of the present disclosure, the organic electroluminescent device of the present disclosure may include at least one layer containing a compound represented by the following formula 9 in the light-emitting layer.

Chemical formula

[0070] According to one embodiment of the present disclosure, A1 and A3 may each independently represent a substituted or unsubstituted (C6-C18) aryl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted carbazolyl. For example, A1 and A3 may each independently be a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenyl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted m-terphenyl, a substituted or unsubstituted o-terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted carbazolyl, etc., and the substituents of the above substituted ones may be at least one selected from deuterium, phenyl, unsubstituted carbazolyl, or carbazolyl substituted with phenyl, and naphthyl.

[0071] According to one embodiment of the present disclosure, L3 and L5 may each independently represent a single bond, or a substituted or unsubstituted (C6-C12) arylene. For example, L3 and L5 may each independently represent a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted p-biphenylene, a substituted or unsubstituted m-biphenylene, a substituted or unsubstituted o-biphenylene, or a substituted or unsubstituted naphthylene, etc., and the substituents of the above substituted ones may be at least one selected from deuterium and carbazolyl.

[0072] According to one embodiment of the present disclosure, X that does not form a ring 15 ~X 18 、X 11 ~X 14 、and X 31 ~X 34 may each independently represent hydrogen or deuterium.

[0073] 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%, still more preferably 30% to 95%, and still more preferably 40% to 95%.

[0074] 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.

[0075] 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.

Chemical formula

Chemical formula

[0076] According to one embodiment of the present disclosure, the deuterated compound may be exemplified more specifically by, but not limited to, the following compounds.

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0077] In the above compounds, D n represents that n hydrogens are replaced by deuterium, and n represents an integer of 1 or more, which has an upper limit of the number of hydrogen atoms in the non-deuterated compound.

[0078] In the synthesis of the compounds represented by the above formulas 1 to 9, those skilled in the art will recognize that all of them are based on backward Hartwig cross-coupling reactions, N-arylation reactions, H-mont-mediated etherification reactions, Miyaura borylation reactions, Suzuki cross-coupling reactions, intramolecular acid-induced cyclization reactions, Pd(II)-catalyzed oxidative cyclization reactions, Grignard reactions, Heck reactions, dehydration ring-closing reactions, S N 1-substitution reactions, S N 2-substitution reactions, and phosphine-mediated reductive cyclization reactions and Wittig reactions, etc., and even when substituents defined by formulas 1 to 9 other than those specified in the specific synthesis examples are bonded, it will be easily understood that the above reactions will proceed.

[0079] Hereinafter, the above compounds and organic electroluminescent devices using the same will be described.

[0080] The organic layer of the present disclosure may further include at least one layer selected from a hole transport layer, a light-emitting layer, a hole injection layer, a hole auxiliary layer, a light-emitting auxiliary 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 include an amine-based compound and / or an azine-based compound. Specifically, the hole injection layer, the hole transport layer, the hole auxiliary layer, the light-emitting layer, the light-emitting auxiliary layer, or the electron blocking layer may include an amine-based compound, for example, an arylamine-based compound, a styrylarylamine-based compound, etc., as a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting material, a light-emitting auxiliary material, and an electron blocking material. Further, an azine-based compound as an electron transport material, an electron injection material, an electron buffer material, and a hole blocking material may be included in the electron transport layer, the electron injection layer, the electron buffer layer, and the hole blocking layer. Further, the organic layer may further include at least one metal selected from the group consisting of metals of Group 1, Group 2, transition metals of the fourth period, transition metals of the fifth period, lanthanides, and organometals of d-transition elements in the periodic table, or at least one complex compound containing a metal.

[0081] A hole transport zone 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. The hole injection layer may be composed of multiple layers 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, and each layer may use two compounds simultaneously. In addition, the hole injection layer may be doped with a p-type dopant. The electron blocking layer may be disposed between the hole transport layer (or hole injection layer) and the light emitting layer, and may prevent the overflow of electrons from the light emitting layer, confine excitons in the light emitting layer, and prevent light leakage. The hole transport layer or the electron blocking layer may use multiple layers, and multiple compounds may be used for each layer.

[0082] An electron transport zone 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 for controlling the injection of electrons and improving the interfacial properties between the light emitting layer and the electron injection layer. In this case, two compounds may be used simultaneously in each of the multiple layers. A hole blocking layer is disposed between the electron transport layer (or electron injection layer) and the light emitting layer, which is a layer that blocks the arrival of holes at the cathode, thereby improving the probability of recombination of electrons and holes in the light emitting layer. Also, the hole blocking layer or the electron transport layer may use multiple layers, and multiple compounds may be used for each layer. In addition, the electron injection layer may be doped with an n-type dopant.

[0083] The light-emitting auxiliary layer can be a layer disposed between the anode and the light-emitting layer, between the cathode and the light-emitting layer, or between the cathode and the light-emitting layer. When the light-emitting auxiliary layer is disposed between the anode and the light-emitting layer, the light-emitting auxiliary layer can be used to promote hole injection and / or hole transport, or to prevent electron overflow. When the light-emitting auxiliary layer is disposed between the cathode and the light-emitting layer, the light-emitting auxiliary layer can be used to promote electron injection and / or electron transport, or to prevent hole overflow. In addition, the hole auxiliary layer is disposed 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), thereby adjusting 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 lifespan of the organic electroluminescent device.

[0084] In the organic electroluminescent device of the present disclosure, at least one layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter referred to as "surface layer") is preferably disposed on the inner surface of at least one of the pair of electrodes. Specifically, the chalcogenide (including oxide) layer of silicon and aluminum is preferably disposed on the anode surface on the electroluminescent medium layer side, and the metal halide layer or the metal oxide layer is preferably disposed on the cathode surface on the electroluminescent medium layer side. The driving stability in the organic electroluminescent device can be obtained by 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, MgF2, CaF2, rare earth metal fluorides, etc., and preferred examples of the metal oxide include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0085] In addition, in the organic electroluminescent device of the present disclosure, the mixed region of the electron transport compound and the reducing dopant or the mixed region of the hole transport compound and the oxidizing dopant can be disposed on at least one surface of the pair of electrodes. In this case, the electron transport compound is reduced to an anion, and as a result, it becomes easier to inject and transport electrons from the mixed region to the light-emitting medium. Further, the hole transport compound is oxidized to a cation, and as a result, it becomes easier to inject and transport holes from the mixed region to the 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, by using the reducing dopant layer as a charge generation layer, an organic electroluminescent device having at least two light-emitting layers and emitting white light can be manufactured.

[0086] 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 one embodiment, a single light-emitting unit (light-emitting portion) may be formed in a structure in which two or more units are connected by a charge generation layer. The organic electroluminescent device includes a first electrode and a second electrode facing each other on a substrate, and a light-emitting layer laminated between the first electrode and the second electrode and emitting light in a specific wavelength range. It may include a plurality of two or more light-emitting units, for example, a plurality of three or more light-emitting units. This may include a plurality of light-emitting units, and each of the light-emitting units may include a hole transport zone, a light-emitting layer, and an electron transport zone. The hole transport zone may include a hole injection layer and a hole transport layer, and the electron transport zone may include an electron transport layer and an electron injection layer. According to one embodiment 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. This may include one or more charge generation layers disposed between each light-emitting unit. The charge generation layer refers to a layer in which holes and electrons are generated when a voltage is applied. When there are three or more light-emitting units, the charge generation layer can be disposed between each light-emitting unit. Here, the plurality of charge generation layers may be the same as or different from each other. By disposing the charge generation layer between the light-emitting units, the current efficiency can be increased in each light-emitting unit, and the charge can be smoothly distributed. Specifically, the charge generation layer is provided between two adjacent stacks and can help drive a tandem organic electroluminescent device using only a pair of an anode and a cathode without a separate internal electrode disposed between the stacks.

[0087] The charge generation layer may be composed of an N-type charge generation layer and a P-type charge generation layer. The N-type charge generation layer may be doped with an alkali metal, an alkaline earth metal, or a compound of an alkali metal and an alkaline earth metal. The alkali metal can include one selected from the group consisting of Li, Na, K, Rb, Cs, Fr, Yb, and combinations thereof, and the alkaline earth metal can include one selected from the group consisting of Be, Mg, Ca, Sr, Ba, Ra, and combinations thereof. The P-type charge generation layer can be manufactured from a metal or an organic material doped with a p-type dopant. For example, the metal may be made of one or two or more alloys selected from the group consisting of Al, Cu, Fe, Pb, Zn, Au, Pt, W, In, Mo, Ni, and Ti. Moreover, commonly used materials can be used as the host materials for p-type dopants and p-type doped organic materials.

[0088] The manufacturing method of the organic electroluminescent device of the present disclosure is not limited. The manufacturing methods of the device examples described below are merely examples and the methods are not limited thereto. Those skilled in the art can reasonably modify the manufacturing methods of the device examples described below by relying on existing technologies. For example, there are no specific restrictions on the mixing ratio of the first compound and the second compound, and those skilled in the art can reasonably select it within a certain range according to existing technologies. 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, and the weight ratio of the first compound to the second compound is 1:99 - 99:1. The weight ratio of the first compound to the second compound may be 20:80 - 99:1, or the weight ratio of the first compound to the second compound may be 50:50 - 90:10. In the manufacture of the device, when forming the light-emitting layer by co-depositing two or more host materials and a light-emitting material, the two or more host materials and the light-emitting material can be respectively 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 can 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 can be respectively 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 can 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.

[0089] To form each layer of the organic electroluminescent device of the present disclosure, dry film formation methods such as vacuum evaporation, sputtering, plasma, ion plating method, etc., or wet film formation methods such as spin coating, dip coating, flow coating method, etc. can be used. When using a wet film formation method, the thin film can be formed by dissolving or diffusing the material for forming each layer in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent may be any solvent in which the material for forming each layer can be dissolved or diffused and there is no problem with film forming ability.

[0090] 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 mixed deposition method in which two or more materials are placed in another crucible source and current is passed through two cells simultaneously to evaporate the materials; mixed deposition is a method in which two or more materials are mixed in one crucible source before deposition and then current is passed through one cell to evaporate the materials.

[0091] Hereinafter, for a detailed understanding of the present disclosure, the method for preparing a compound according to the present disclosure will be described using the synthesis of representative compounds or intermediate compounds of the present disclosure as examples.

Examples

[0092] Example 1: Preparation of Compound HT-47

Chemical formula

[0093]

Table 1

[0094] Example 2: Preparation of Compound H1-55

Chemical formula

[0095]

Table 2

[0096] Example 3: Preparation of Compound H2-35

Chemical formula

[0097]

Table 3

[0098] Example 4: Preparation of Compound ET-60

Chemical formula

[0099]

Table 4

[0100] Example 5: Preparation of Compound HT-39

Chemical formula

[0101]

Table 5

[0102] Example 6: Preparation of Compound H2-61

Chemical Structure

[0103]

Table 6

[0104] Example 7: Preparation of Compound H1-15

Chemical Structure

[0105]

Table 7

[0106] Example 8: Preparation of Compound ET-1

Chemical Structure

[0107]

Table 8

[0108] Example 9: Preparation of Compound H3-7

Chem.

[0109]

Table 9

[0110] Example 10: Preparation of Compound H3-20

Chem.

[0111]

Table 10

[0112] Example 11: Preparation of Compound C-52

Chem.

[0113]

Table 11

[0114] Device Example 1: Manufacture of an OLED Depositing a Compound According to the Present Disclosure An OLED according to the present disclosure was manufactured. First, an indium tin oxide (ITO) thin film (10 Ω / sq) (Daiomatic Co., Ltd., Japan) on a glass substrate for the OLED was successively subjected to ultrasonic cleaning with acetone and isopropyl alcohol and then stored in isopropyl alcohol. The ITO substrate was mounted on the substrate holder of a vacuum deposition apparatus. Compound HI (p-dopant) was introduced into a cell of the vacuum deposition apparatus, and compound HT'-1 was introduced into another cell. The two materials were evaporated at different rates, and compound HI was 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 with a thickness of 10 nm. Thereafter, compound HT'-1 was deposited on the hole injection layer to form a first hole transport layer with a thickness of 80 nm. Next, the compound shown in Table 1 was introduced into another cell of the vacuum deposition apparatus, and a current was passed through the cell to evaporate it, thereby depositing a second hole transport layer with a thickness of 30 nm. After forming the hole injection layer and the hole transport layer, an emission layer was deposited thereon as follows. The compound shown in Table 1 below was introduced into one cell of the vacuum deposition apparatus at a ratio of 1:2 as a host, and compound GD was introduced into another cell as a dopant. The materials were evaporated at different rates, and the dopant was deposited at a doping amount of 10 wt% based on the total amount of the host and the dopant to form an emission layer with a thickness of 40 nm on the second hole transport layer. The compound shown in Table 1 was deposited with a thickness of 5 nm as an electron buffer layer. Next, compounds EI-1 and Liq were introduced into another two cells and evaporated at a ratio of 1:1 to deposit an electron transport layer with a thickness of 30 nm on the electron buffer layer. Compound Liq was introduced and deposited with a thickness of 2 nm as an electron injection layer on the electron transport layer. Thereafter, an Al cathode was deposited with a thickness of 80 nm by using another vacuum deposition apparatus, thereby manufacturing an OLED. All the materials used for manufacturing the OLED were purified by vacuum sublimation in toluene. -6 Purified by vacuum sublimation in toluene.

[0115] Comparative Example 1: Manufacture of an OLED Containing a Conventional Compound An OLED was fabricated 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 were fabricated using light hydrogen materials.

[0116] The current efficiency at a luminance of 1,000 nits and the time required for the luminance to decrease from 100% to 95% at a luminance of 40,000 nits (lifetime: T 95 ) of the OLEDs of Device Example 1 and Comparative Example 1 fabricated as described above are shown in Table 1 below.

[0117]

Table 12

[0118] From Table 1 above, it can be confirmed that the organic electroluminescent device according to the present disclosure exhibits long-life characteristics while maintaining current efficiency characteristics as compared with conventional organic electroluminescent devices.

[0119] Device Example 2: Fabrication of an OLED Deposited with a Compound According to the Present Disclosure as a Host An OLED according to the present disclosure was fabricated. First, an indium tin oxide (ITO) thin film (10 Ω / sq) (manufactured by Geomatech Co., Ltd., Japan) on a glass substrate for the OLED was sequentially subjected to ultrasonic cleaning with acetone and isopropyl alcohol, and then stored in isopropyl alcohol. The ITO substrate was mounted on the substrate holder of a vacuum evaporation apparatus. Compound HI (p-dopant) was introduced into the cell of the vacuum evaporation apparatus, and compound HT'-1 was introduced into another cell. The two materials were evaporated at different rates, and compound HI was 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 with a thickness of 10 nm. Thereafter, compound HT'-1 was deposited on the hole injection layer to form a first hole transport layer with a thickness of 90 nm. Next, the compound shown in Table 2 was introduced into another cell of the vacuum evaporation apparatus as the second hole transport layer, and evaporated by passing an electric current, thereby depositing it on the first hole transport layer with a thickness of 60 nm. After forming the hole injection layer and the hole transport layer, an emission layer was deposited thereon as follows. The compounds shown in Table 2 below were introduced into one cell of the vacuum evaporation apparatus as a host at a ratio of 1:1, and compound RD was introduced into another cell as a dopant. The materials were evaporated at different rates, and the dopant was deposited at a doping amount of 3 wt% based on the total amount of the host and the dopant to form an emission layer with a thickness of 40 nm on the second hole transport layer. The compound shown in Table 2 was deposited with a thickness of 5 nm as an electron buffer layer, and then compound EI-1 and compound Liq were introduced into another two cells, evaporated at a ratio of 1:1, and an electron transport layer with a thickness of 30 nm was deposited on the emission layer. After introducing compound Liq with a thickness of 2 nm as an electron injection layer on the electron transport layer, an Al cathode was deposited with a thickness of 80 nm by using another vacuum evaporation apparatus, thereby fabricating the OLED. All the materials used for fabricating the OLED were purified by vacuum sublimation in toluene. -6 Purified by vacuum sublimation in toluene.

[0120] Comparative Example 2: Fabrication of an OLED Containing a Conventional Compound An OLED was fabricated in the same manner as in Device Example 2, except that the hole transport layer, the host material of the emission layer, and the electron buffer layer were fabricated from light hydrogen materials.

[0121] The current efficiency at a brightness of 1,000 nits and the time required for the brightness to decrease from 100% to 97% at a brightness of 10,000 nits (lifetime: T 97 ) of the OLEDs of Device Example 2 and Comparative Example 2 manufactured as described above are shown in Table 2 below.

[0122]

Table 13

[0123] From Table 2 above, it can be confirmed that the organic electroluminescent device according to the present disclosure exhibits higher current efficiency and much longer lifetime compared to the conventional organic electroluminescent device.

[0124] Device Example 3: Manufacture of an OLED Depositing a Compound According to the Present Disclosure An OLED was manufactured in the same manner as in Device Example 2, except that no electron buffer layer was used, and the compounds shown in Table 3 and compound Liq were introduced into two separate cells and evaporated at a ratio of 1:1 to deposit an electron transport layer with a thickness of 35 nm on the light-emitting layer.

[0125] Comparative Example 3: Manufacture of an OLED Containing a Conventional Compound An OLED was manufactured 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 transport layer were manufactured using light hydrogen materials.

[0126] The current efficiency at a brightness of 1,000 nits and the time required for the brightness to decrease from 100% to 97% at a brightness of 10,000 nits (lifetime: T 97 ) of the OLEDs of Device Example 3 and Comparative Example 3 manufactured as described above are shown in Table 3 below.

[0127]

Table 14

[0128] From Table 3 above, it can be confirmed that the organic electroluminescent device according to the present disclosure exhibits a longer lifespan while maintaining current efficiency characteristics as compared with conventional organic electroluminescent devices.

[0129] Device Examples 4 and 5: Fabrication of an OLED Depositing a Compound According to the Present Disclosure An OLED according to the present disclosure was fabricated. First, a transparent electrode indium tin oxide (ITO) thin film (10 Ω / sq) (Diomatic Co., Ltd., Japan) on a glass substrate for the OLED was subjected to ultrasonic cleaning sequentially with acetone and isopropyl alcohol, and then stored in isopropyl alcohol. The ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus. Compound HI (p-dopant) was introduced into a cell of the vacuum deposition apparatus, and compound HT'-1 was introduced into another cell. The two materials were evaporated at different rates, and compound HI was 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 with a thickness of 10 nm. Thereafter, compound HT'-1 was deposited on the hole injection layer to form a first hole transport layer with a thickness of 80 nm. Next, the compound shown in Table 4 was introduced into another cell of the vacuum deposition apparatus as a second hole transport layer, and current was passed through the cell to evaporate it, thereby depositing it on the first hole transport layer with a thickness of 5 nm. After forming the hole injection layer and the hole transport layer, an emission layer was deposited thereon as follows. After introducing the compound shown in Table 4 as a host into a cell in the vacuum deposition apparatus, the two materials were evaporated at different rates, and the dopant was deposited at a doping amount of 2 wt% based on the total amount of the host and the dopant to form an emission layer with a thickness of 20 nm on the second hole transport layer. Next, the compound shown in Table 4 and compound Liq were introduced into two other cells and evaporated at a ratio of 1:1 to deposit an electron transport layer with a thickness of 35 nm on the emission layer. After introducing and depositing compound Liq with a thickness of 2 nm as an electron injection layer on the electron transport layer, an Al cathode was deposited with a thickness of 80 nm by using another vacuum deposition apparatus, thereby fabricating an OLED. All the materials used for fabricating the OLED were -6 purified by vacuum sublimation in toluene.

[0130] Comparative Examples 4 and 5: Fabrication of OLEDs Containing Conventional Compounds An OLED was fabricated 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 were fabricated using protium materials.

[0131] The current efficiency, CIE color coordinates, and the time required for the luminance to decrease from 100% to 97% at a luminance of 10,000 nits based on the CIE color coordinates of the OLEDs of Device Examples 4 and 5 and Comparative Examples 4 and 5 fabricated as described above (lifetime: T 97 ) are shown in Table 4 below.

[0132]

Table 15

[0133] It can be confirmed from Table 4 above that the organic electroluminescent device according to the present disclosure exhibits higher current efficiency and much longer lifetime as compared with conventional organic electroluminescent devices.

[0134] Device Example 6: Fabrication of an OLED Depositing a Compound According to the Present Disclosure An OLED according to the present disclosure was fabricated. First, an indium tin oxide (ITO) thin film (10 Ω / sq) (manufactured by Geomatic Co., Ltd., Japan) on a glass substrate for the OLED was subjected to ultrasonic cleaning sequentially with acetone and isopropyl alcohol, and then stored in isopropyl alcohol. The ITO substrate was mounted on the substrate holder of a vacuum evaporation apparatus. Compound HI (p-dopant) was introduced into the cell of the vacuum evaporation apparatus, and compound HT’-1 was introduced into another cell. The two materials were evaporated at different rates, and compound HI was 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 with a thickness of 10 nm. Thereafter, compound HT’-1 was deposited on the hole injection layer to form a first hole transport layer with a thickness of 80 nm. Next, the compound shown in Table 5 was introduced into another cell of the vacuum evaporation apparatus as the second hole transport layer, and current was passed through the cell to evaporate it, thereby depositing it with a thickness of 30 nm. After forming the hole injection layer and the hole transport layer, an emission layer was deposited thereon as follows. The compound shown in Table 5 below was introduced into the cell of the vacuum evaporation apparatus at a ratio of 2:1 as a host, and compound GD was introduced into another cell as a dopant. The materials were evaporated at different rates, and the dopant was deposited at a doping amount of 10 wt% based on the total amount of the host and the dopant to form an emission layer having a thickness of 40 nm on the second hole transport layer. The compound shown in Table 5 was deposited with a thickness of 5 nm as an electron buffer layer, and then compound EI-1 and compound Liq were introduced into two different cells and evaporated at a ratio of 1:1 to deposit an electron transport layer having a thickness of 35 nm on the emission layer. Compound Liq was introduced and deposited with a thickness of 2 nm as an electron injection layer on the electron transport layer, and then an Al cathode was deposited with a thickness of 80 nm by using another vacuum evaporation apparatus, thereby fabricating the OLED. All the materials used for fabricating the OLED were purified by vacuum sublimation in toluene. -6 Purified by vacuum sublimation in toluene.

[0135] Comparative Example 6: Fabrication of an OLED Containing a Conventional Compound An OLED was fabricated in the same manner as in Device Example 6, except that the hole transport layer, the host material of the emission layer, and the electron buffer layer were fabricated from light hydrogen materials.

[0136] The current efficiency at a luminance of 1,000 nits and the time required for the luminance to decrease from 100% to 95% at a luminance of 1,000 nits (lifetime: T 95 ) of the OLEDs of Device Example 6 and Comparative Example 6 manufactured as described above are shown in Table 5 below.

[0137]

Table 16

[0138] From Table 5 above, it can be confirmed that the organic electroluminescent device according to the present disclosure exhibits a higher lifetime while maintaining current efficiency characteristics as compared with conventional organic electroluminescent devices.

[0139] The compounds used in the above device examples and comparative examples are shown in Table 6 below.

[0140]

Table 17

Claims

1. An organic electroluminescent device comprising an anode, a hole transport zone, an emissive layer, an electron transport zone and a cathode, wherein the hole transport zone, the emissive layer and the electron transport zone each comprise a deuterated compound, and the structures of each of the compounds are the same or different from each other.

2. 2. The organic electroluminescent device of claim 1, wherein the hole transport zone is formed by sequentially stacking on the anode a hole injection layer, a hole transport layer consisting of one or more layers, and a hole auxiliary layer or electron blocking layer consisting of one or more layers, and at least one of the layers contains a deuterated compound.

3. 2. The organic electroluminescent device of claim 1, wherein the electron transport zone is formed by sequentially stacking on the light-emitting layer an electron buffer layer or hole blocking layer composed of one or more layers, an electron transport layer composed of one or more layers, and an electron injection layer, and at least one of the layers contains a deuterated compound.

4. 2. 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 hosts.

5. 2. The organic electroluminescent device of claim 1, wherein the light-emitting layer comprises a phosphorescent or fluorescent compound, and the compound comprises an iridium (Ir) atom, a platinum (Pt) atom, or a boron (B) atom.

6. At least one layer of the hole transport zone has Formula 1: 【Chemistry 1】 In the formula (1), Ar １ ~Ar ３ each independently represents 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 (3-30 membered) heteroaryl, substituted or unsubstituted mono- or di-(6-30 membered) arylamino, mono- or di-(C1-C30) alkylamino, mono- or di-(C2-C30) alkenylamino, (C1-C30) alkyl(C6-C30) arylamino, mono- or di-(3-30 membered) heteroarylamino, or (C6-C30) aryl(3-30 membered) heteroarylamino, with the proviso that Ar １ ~Ar ３ each comprises at least one of substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (3-30 membered) heteroaryl; L １ and L ３ each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene; D ｎ represents that n hydrogen atoms are replaced with deuterium, where n is an integer of 1 or more and is the upper limit of the number of hydrogen atoms in a non-deuterated compound; 3. The organic electroluminescent device of claim 2.

7. Ar １ ~Ar ３ 7. The organic electroluminescent device of claim 6, wherein at least one of comprises substituted or unsubstituted phenanthrenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.

8. At least one layer of the electron transport zone has Formula 2 or Formula 3: 【Chemistry 2】 In the formula (2), L １１ and L １２ each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene; Ar １１ and Ar １２ each independently represents a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl; R １１ ~R １８ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C2-C30)alkenylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, substituted or unsubstituted mono- or di-(3-30 membered)heteroarylamino, substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, substituted or unsubstituted (C1-C30)alkyl(3-30 membered)heteroarylamino, substituted or unsubstituted (C2-C30)alkenyl(C6-C30)arylamino, substituted or unsubstituted (C2-C30)alkenyl(3-30 membered)heteroarylamino, or substituted or unsubstituted (C6-C30)aryl(3-30 membered)heteroarylamino; R １１ and R １４ ~R １６ represents deuterium; and D ｎ represents the replacement of n hydrogens with deuterium, where n is an integer equal to or greater than 1 and has an upper limit on the number of hydrogen atoms in the non-deuterated compound; 【Chemistry 3】 In formula (3), X ２１ ~X ２３ each independently represents CR′ or N, provided that X ２１ ~X ２３ at least two of represent N; R' represents hydrogen or deuterium; L ２１ ~L ２３ each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene; Ar ２１ ~Ar ２３ each independently represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 membered) heteroaryl, provided that Ar ２１ ~Ar ２３ at least one of which contains deuterium; p, q, and r each independently represent an integer of 1 to 3, where, when p, q, and r each represent an integer of 2 or more, L ２１ ~L ２３ may be the same or different; and D ｎ The organic electroluminescent device of claim 3 , wherein n hydrogen atoms are replaced with deuterium atoms, and n is an integer of 1 or more and is the upper limit of the number of hydrogen atoms in the non-deuterated compound.

9. R in Formula 2 １１ ~R １８ , Ar １１ and Ar １２ At least one of the following formulas 2-1 or 2-2: 【Chemistry 4】 In formulas 21 and 22, L'1 represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene; and R' １ ~R' ５ 9. The organic electroluminescent device of claim 8, wherein each independently represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl.

10. Ar ２１ ~Ar ２３ at least one of Ar includes substituted or unsubstituted phenanthrenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl, with the proviso that Ar ２１ ~Ar ２３ 9. The organic electroluminescent device of claim 8, wherein at least one of comprises deuterium.

11. At least one layer in the light-emitting layer is a compound represented by the following formula 4 or 5: 【Chemistry 5】 In the formula (4), A １ and A ２ each independently represents a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, or a substituted or unsubstituted carbazolyl; X' １５ ~X' １８ and X' １９ ~X' ２２ are joined together to form a single bond; does not form a single bond, X' １１ ~X' １４ , X' ２３ ~X' ２６ and X' １５ ~X' ２２ each independently represent hydrogen, deuterium, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl, or may be joined to adjacent substituents to form a ring; X' １１ , X' １８ , X' １９ , or X' ２６ represents deuterium; and D ｎ represents the replacement of n hydrogens with deuterium, where n is an integer equal to or greater than 1 and has an upper limit on the number of hydrogen atoms in the non-deuterated compound; 【Chemistry 6】 In formula (5), R ５１ ~R ５３ At least one of the following formulas 5-1 or 5-2 is included: 【Chemistry 7】 Or L ５１ and L ５２ is a single bond, R ５１ and R ５２ may be bonded to each other and represented by any one of the following formulas 5-3 to 5-5: 【Chemistry 8】 R ５１ ~R ５３ and R' ５１ ~R' ５９ each independently represents hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-membered to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (C1-C30) alkoxy, a substituted or unsubstituted tri(C1-C30) alkylsilyl, a substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, a substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, a substituted or unsubstituted tri(C6-C30) arylsilyl, a substituted or unsubstituted fused ring group of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted mono- or di-(C1-C30) alkylamino, a substituted or unsubstituted mono- or di- -(C2-C30)alkenylamino, substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, substituted or unsubstituted mono- or di-(3-30 membered)heteroarylamino, substituted or unsubstituted (C1-C30)alkyl(3-30 membered)heteroarylamino, substituted or unsubstituted (C2-C30)alkenyl(C6-C30)arylamino, substituted or unsubstituted (C2-C30)alkenyl(3-30 membered)heteroarylamino, or substituted or unsubstituted (C6-C30)aryl(3-30 membered)heteroarylamino, or may be combined with adjacent substituents to form a ring; L ５１ ~L ５３ each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene; X″ represents 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, and when a to g each independently represent an integer of 2 or more, R' ５１ ~R' ５９ may be the same or different; and D ｎ The organic electroluminescent device of claim 4, wherein n hydrogen atoms are replaced with deuterium atoms, and n is an integer of 1 or more and is the upper limit of the number of hydrogen atoms in the non-deuterated compound.

12. In the case where at least one layer in the light-emitting layer contains two or more compounds, the two or more compounds are each represented by the following formula 6 or 7: 【Chemistry 9】 In the formula 6 and formula 7, X ６１ represents O or S; H.A.R. ６１ and H.A.R. ６２ each independently represents a substituted or unsubstituted (3-30 membered) heteroaryl containing one or more nitrogen atoms; L ６１ and L ６２ each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene; R ６１ ~R ６４ each independently represent hydrogen, deuterium, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl, or may be joined to adjacent substituents to form a ring; h to k each independently represent an integer of 1 to 4. When h to k each represent an integer of 2 or more, R ６１ ~R ６４ may be the same or different; and D ｎ The organic electroluminescent device of claim 4, wherein n hydrogen atoms are replaced with deuterium atoms, and n is an integer of 1 or more and is the upper limit of the number of hydrogen atoms in the non-deuterated compound.

13. At least one layer in the light-emitting layer is a layer represented by the following formula 8: 【Chemistry 10】 In the formula (8), Ar ８１ represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 membered) heteroaryl; R ８１ ~R ８８ are each independently 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, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, or a substituted or unsubstituted fused ring group of a (C3-C30)aliphatic ring and a (C6-C30)aromatic ring; Ar Ａ represents a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl, or is represented by the following formula A-1: D ｎ represents the replacement of n hydrogens with deuterium, where n is an integer equal to or greater than 1 and has an upper limit on the number of hydrogen atoms in the non-deuterated compound; 【Chemistry 11】 T １ is O, S, or CR ｌ R ｍ represents; R' ８１ ~R' ８８ are each independently L ８２ or represents a bond to a site bonded to 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. , a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted fused ring group of a (C3-C30)aliphatic ring and a (C6-C30)aromatic ring, or -L ８３ -N(Ar ８３ ) (Ar ８４ ) and R ｌ and R ｍ each independently represent a substituted or unsubstituted (C1-C30) alkyl, or a substituted or unsubstituted (C6-C30) aryl, or may be joined together to form a ring; L ８１ ~L ８３ each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene; Ar ８３ and Ar ８４ are each independently 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-C 30) The organic electroluminescent device according to claim 4, wherein the aryl group is selected from the group consisting of alkoxy, a substituted or unsubstituted fused ring group of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted tri(C1-C30) alkylsilyl, a substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, a substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, or a substituted or unsubstituted tri(C6-C30) arylsilyl.

14. 7. The organic electroluminescent device of claim 6, wherein the compound represented by Formula 1 is at least one selected from the following compounds: 【Chemistry 12】 【Chemistry 13】

15. 9. The organic electroluminescent device of claim 8, wherein the compound represented by formula 2 or formula 3 is at least one selected from the following compounds: 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】

16. 12. The organic electroluminescent device of claim 11, wherein the compound represented by formula 4 or formula 5 is at least one selected from the following compounds: 【Chemistry 17】 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】

17. 13. The organic electroluminescent device of claim 12, wherein the compound represented by formula 6 or formula 7 is at least one selected from the following compounds: 【Chemistry 21】 【Chemical 22】 【Chemistry 23】

18. 14. The organic electroluminescent device of claim 13, wherein the compound represented by formula 8 is at least one selected from the following compounds: 【Chemistry 24】

19. At least one of the light-emitting layers is a layer having the following formula 9: 【Chemistry 25】 In the formula (9), X １５ ~X １８ Any adjacent pair of X is bonded to the following formula 9-A to form a ring, and if no ring is formed, X １５ ~X １８ , X １１ ~X １４ , and X ３１ ~X ３４ each independently represents hydrogen, deuterium, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl; 【Chemistry 26】 In formulas 9 and 9-A, A １ and A ３ each independently represents a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, or a substituted or unsubstituted carbazolyl; L ３ and L ５ each independently represents a single bond or a substituted or unsubstituted (C6-C30) arylene; and D ｎ The organic electroluminescent device of claim 4, wherein n hydrogen atoms are replaced with deuterium atoms, and n is an integer of 1 or more and is the upper limit of the number of hydrogen atoms in the non-deuterated compound.

20. X １１ Or X ３１ 20. The organic electroluminescent device of claim 19, wherein is deuterium.

21. The compound represented by formula 9 is represented by the following formulas 9-1 to 9-6: 【Chemical 27】 【Chemistry 28】 (In formulas 9-1 to 9-6, A １ , A ３ , L ３ , L ５ , X １１ ~X １８ , and X ３１ ~X ３４ and D. ｎ The organic electroluminescent device according to claim 19, wherein the organic electroluminescent device is represented by any one of the following formulas:

22. 20. The organic electroluminescent device of claim 19, wherein the compound represented by formula 9 is at least one selected from the following compounds: 【Chemical 29】 【Chemistry 30】 【Chemistry 31】

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