Organic electroluminescent compound and organic electroluminescent device containing the same

Abstract

The present disclosure relates to an organic electroluminescent compound represented by Formula 1 and an organic electroluminescent device including the same. By including the organic electroluminescent compound of the present disclosure, an organic electroluminescent device having improved driving voltage, luminous efficiency, lifespan characteristics, and / or power efficiency can be provided.

Description

Technical Field

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

[0002] Electroluminescent devices (EL devices) are self-luminous display devices that have the advantages of providing a wider viewing angle, a greater contrast ratio, and a faster response time. The first organic EL device was developed by Eastman Kodak in 1987 by using small aromatic diamine molecules and aluminum complexes as materials for forming the light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].

[0003] The most important factor that determines the luminous efficiency in an organic electroluminescent device (OLED) is the luminescent material. So far, fluorescent materials have been widely used as luminescent materials. However, in view of the electroluminescence mechanism, phosphorescent luminescent materials have been widely studied because they theoretically enhance the luminous efficiency by four (4) times compared to fluorescent luminescent materials. So far, iridium (III) complexes have been widely known as phosphorescent luminescent materials, including bis(2-(2'-benzothienyl)-pyridine-N, C-3')(acetylacetonato)iridium [(acac)Ir(btp)2], tris(2-phenylpyridine)iridium [Ir(ppy)3], and bis(4,6-difluorophenylpyridine-N, C2)picolinyliridium (Firpic), which are red, green, and blue luminescent materials, respectively.

[0004] 4,4'-N,N'-dicarbazole-biphenyl (CBP) is the most widely known phosphorescent host material. Recently, companies such as Pioneer Electronics (Japan) have developed high-performance OLEDs using hole-blocking materials such as bathocuproine (BCP) and aluminum(III) bis(2-methyl-8-quinolinolate)(4-phenylphenolate) (BAlq) as host materials.

[0005] However, although conventional materials provide good luminescence characteristics, they have the following disadvantages: (1) Due to their low glass transition temperature and poor thermal stability, they may degrade during the high-temperature deposition process in a vacuum and may shorten the life of the device. (2) The power efficiency of OLED is given by [(π / voltage)×current efficiency], and the power efficiency is inversely proportional to the voltage. Although OLEDs containing phosphorescent host materials provide higher current efficiency (cd / A) than OLEDs containing fluorescent materials, a relatively high driving voltage is required. Therefore, there is no advantage in power efficiency (lm / W). (3) In addition, the operating life of OLEDs is short, and there is still a need to improve the luminous efficiency.

[0006] In order to enhance luminous efficiency, driving voltage and / or lifespan characteristics, various materials or concepts for organic layers of organic electroluminescent devices have been proposed. However, they are not satisfactory in practical use.

[0007] Korean published patent applications Nos. 2014-0055137 and 2015-0126340 disclose fused carbazole derivatives. However, there is a continuing need to develop organic electroluminescent materials for improving the performance of OLEDs. Summary of the Invention

[0008] Technical issues

[0009] The present invention provides an organic electroluminescent compound that is effective in producing an organic electroluminescent device having improved driving voltage, luminous efficiency, lifespan characteristics, and / or power efficiency. Another object of the present invention is to provide an organic electroluminescent device comprising the organic electroluminescent compound.

[0010] Solution to the problem

[0011] Compounds having an aromatic moiety can exhibit high stability when used in electrical devices. The inventors of the present invention have found that phenanthrene-based compounds have higher HOMO, LUMO, and triplet energy gap (E) than anthracene-based compounds. T ), and therefore, a phenanthrene-based compound is introduced into an organic electroluminescent device. As a result, it is confirmed that the stability is higher than that of the case where an anthracene-based compound is introduced. This can also be explained by Clar's rule. That is, this higher stability seems to be due to the effect of the phenanthrene structure having lower bridge conjugation and steric hindrance compared to the anthracene structure. More specifically, the inventors of the present invention have found that the above purpose can be achieved by an organic electroluminescent compound represented by the following formula 1:

[0012]

[0013] in

[0014] Ring A is selected from the following formulae:

[0015]

[0016] X stands for NR 11 , CR 12 R 13 , O or S;

[0017] R1 each independently represents hydrogen, deuterium, halogen, or cyano;

[0018] R 11represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- to 30-membered)heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino;

[0019] R 12 and R 13 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino; or are linked to form a ring;

[0020] R 21 represents -L1-Ar1, where if R 21 If there are multiple, then each R 21 can be the same or different;

[0021] L1 each independently represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3-membered to 30-membered)heteroarylene group;

[0022] Ar1 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- to 30-membered)heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino;

[0023] a represents an integer from 1 to 4, and b represents an integer from 1 to 10, wherein if a and b are integers of 2 or greater, each R1 and each R 21 can be the same or different;

[0024] * indicates the site of fusion with the 5-membered ring containing X;

[0025] The premise is that if X is NR 11 , then ring A is not

[0026] Beneficial effects of the present invention

[0027] By using the organic electroluminescent compound of the present disclosure, an organic electroluminescent device having low driving voltage, high luminous efficiency, excellent lifespan characteristics, and / or high power efficiency can be produced. DETAILED DESCRIPTION

[0028] Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present disclosure and is not intended to limit the scope of the present disclosure in any way.

[0029] The term "organic electroluminescent compound" in the present disclosure means a compound that can be used in an organic electroluminescent device. If necessary, the organic electroluminescent compound may be contained in any layer constituting the organic electroluminescent device.

[0030] The term "organic electroluminescent material" in the present disclosure means a material that can be used in an organic electroluminescent device and that can include at least one compound. If necessary, the organic electroluminescent material can be included in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole assist material, a luminescence assist material, an electron blocking material, a luminescent material (including a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0031] The organic electroluminescent material of the present disclosure may include at least one compound represented by Formula 1. The compound represented by Formula 1 may be included in a hole injection layer, a hole transport layer, a hole auxiliary layer, a luminescent auxiliary layer, an electron blocking layer, a luminescent layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and / or an electron injection layer, etc., but is not limited thereto. The compound represented by Formula 1 may be included in at least one of the layers constituting the hole transport zone, but is not limited thereto. When included in a hole transport layer, a hole auxiliary layer or a luminescent auxiliary layer in the hole transport zone, the compound represented by Formula 1 may be included as a hole transport material, a hole auxiliary material, or a luminescent auxiliary material. In addition, when included in a luminescent layer, the compound represented by Formula 1 may be included as a host material, but is not limited thereto. In this article, the host material may be a host material of a blue, green, or red organic electroluminescent device.

[0032] Hereinafter, the compound represented by Formula 1 will be described in more detail.

[0033] Herein, the term "(C1-C30) alkyl" means a straight or branched chain alkyl group having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10. The above-mentioned alkyl group may include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, and the like. The term "(C2-C30) alkenyl" means a straight or branched chain alkenyl group having 2 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The above-mentioned alkenyl group may include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 2-methylbut-2-enyl group, and the like. The term "(C2-C30) alkynyl" means a straight or branched chain alkynyl group having 2 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The above-mentioned alkynyl group may include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, and the like. The term "(C3-C30) cycloalkyl" means a monocyclic hydrocarbon or polycyclic hydrocarbon having 3 to 30 ring backbone carbon atoms, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The above-mentioned cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, and the like. The term "(3- to 7-membered) heterocycloalkyl" means a cycloalkyl group having 3 to 7, preferably 5 to 7 ring backbone atoms and containing at least one heteroatom, the heteroatom being selected from the group consisting of B, N, O, S, Si and P, and preferably the group consisting of O, S and N. The above-mentioned heterocycloalkyl group may include tetrahydrofuran, pyrrolidine, tetrahydrothiophene (thiolan), tetrahydropyran and the like. The term "(C6-C30) (sub)aryl" means a monocyclic or condensed ring group derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, wherein the number of ring backbone carbon atoms is preferably 6 to 25, and more preferably 6 to 18. The above-mentioned (sub)aryl group may be partially saturated and may contain a spiro structure. The above-mentioned aryl groups may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylene, pyrenyl, naphthacene, perylene, More specifically, the aryl groups may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 9-phenanthrenyl, naphthacetyl, pyrenyl, 1- Base, 2- Base, 3- Base, 4- Base, 5- Base, 6- Benzo[c]phenanthrenyl, benzo[g] 1-triphenylene, 2-triphenylene, 3-triphenylene, 4-triphenylene, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo[a]fluorenyl, benzo[b]fluorenyl, benzo[c]fluorenyl, dibenzofluorenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylene phenyl, 4'-methylbiphenyl, 4"-tert-butyl-4-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-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-dimethyl-2 ... 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-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 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 ] fluorenyl, 11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9-benzo[b]fluorenyl, 11,11-diphenyl-10-benzo[b]fluorenyl, 11,11-diphenyl-1-benzo[c]fluorenyl, 11,11-diphenyl-2-benzo[c]fluorenyl, 11,11-diphenyl-3-benzo[c]fluorenyl, 11,11-diphenyl-4-benzo[c]fluorenyl, 11,11-diphenyl-5-benzo[c]fluorenyl, 11,11-diphenyl-6-benzo[c]fluorenyl, 11 ,11-diphenyl-7-benzo[c]fluorenyl, 11,11-diphenyl-8-benzo[c]fluorenyl, 11,11-diphenyl-9-benzo[c]fluorenyl, 11,11-diphenyl-10-benzo[c]fluorenyl, 9,9,10,10-tetramethyl-9,10-dihydro-1-phenanthryl, 9,9,10,10-tetramethyl-9,10-dihydro-2-phenanthryl, 9,9,10,10-tetramethyl-9,10-dihydro-3-phenanthryl, 9,9,10,10-tetramethyl-9,10-dihydro-4-phenanthryl, etc.

[0034] The term "(3- to 30-membered) (sub)heteroaryl" means an aryl group having 3 to 30 ring skeleton atoms and including at least one, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, Si and P. The above-mentioned heteroaryl group may be a monocyclic ring, or a condensed ring condensed with at least one benzene ring; may be partially saturated; may be a heteroaryl group formed by connecting at least one heteroaryl group or aryl group to a heteroaryl group via one or more single bonds; and may contain a spiro structure. The above-mentioned heteroaryl group may include monocyclic heteroaryl groups such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl, and condensed ring heteroaryl groups such as benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, benzothiophenyl, benzofuranyl, benzothiophenyl, benzofuranyl, di ... benzofuranyl, dibenzothiophenyl, dibenzoselenophene, naphthobenzofuranyl, naphthobenzothiophenyl, benzofuranoquinolyl, benzofuranoquinazolinyl, benzofuranonaphthyridinyl, benzofuranopyrimidinyl, naphthofuranopyrimidinyl, benzothienoquinolyl, benzothienoquinazolinyl, benzothienonaphthyridinyl, benzothienopyrimidinyl, naphthothienopyrimidinyl, pyrimidoindolyl, benzopyrimidindolyl, benzofuropyrazinyl, naphthofuropyrazinyl, benzothienopyrazinyl, naphthienopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinolinyl oxazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, benzotriazolphenazinyl, imidazopyridinyl, benzopyranoquinazolinyl, thiobenzopyranoquinazolinyl, dimethylbenzopyrimidinyl, indolecarbazolyl, indenocarbazolyl, etc. More specifically, the above-mentioned heteroaryl groups may include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridyl, 2-pyrimidyl, 4-pyrimidyl, 5-pyrimidyl, 6-pyrimidyl, 1,2,3-triazine-4-yl, 1,2,4-triazine-3-yl, 1,3,5-triazine-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolyl, 2-indolyl, 3-indolyl, 5-indolyl, 6-indolyl, indolyl, 7-indolyl, 8-indolyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 3-pyridinyl, 4-pyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl,5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl 1-[4-[4-[4-[4-[4-[4-[4-]-benzofuranyl]]]], 2-[4-[4-[4-[4-[4-]-benzofuranyl]]], 3-[4-[4-[4-[4-]-benzofuranyl]], 4-[4-[4-[4-]-benzofuranyl]], 2-[4-[4-[4-]-benzofuranyl]], 3-[4-[4-]-quinolyl]], 4-[4-[4-]-quinolyl]], 5-[4-[4-]-quinolyl]], 6-[4-[4-]-quinolyl]], 7-[4-]-quinolyl], 8-[4-[4-]-quinolyl]], 2-[4-]-quinoxalinyl], 5-[4-]-quinoxalinyl], 6-[4-]-quinoxalinyl], 1-[4-]-quinoxalinyl], -carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazolyl-1-yl, azacarbazolyl-2-yl, azacarbazolyl-3-yl, azacarbazolyl-4-yl, azacarbazolyl-5-yl, azacarbazolyl-6-yl, azacarbazolyl-7-yl, azacarbazolyl-8-yl, azacarbazolyl-9-yl, 1-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 pyranyl, 1-dibenzothiophene, 2-dibenzothiophene, 3-dibenzothiophene, 4-dibenzothiophene, 1-naphtho-[1,2-b]-benzofuranyl, 2-naphtho-[1,2-b]-benzofuranyl, 3-naphtho-[1,2-b]-benzofuranyl, 4-naphtho-[1,2-b]-benzofuranyl, 5-naphtho-[1,2 -b]-benzofuranyl, 6-naphtho-[1,2-b]-benzofuranyl, 7-naphtho-[1,2-b]-benzofuranyl, 8-naphtho-[1,2-b]-benzofuranyl, 9-naphtho-[1,2-b]-benzofuranyl, 10-naphtho-[1,2-b]-benzofuranyl, 1-naphtho-[2,3-b]-benzofuranyl,2-naphtho-[2,3-b]-benzofuranyl, 3-naphtho-[2,3-b]-benzofuranyl, 4-naphtho-[2,3-b]-benzofuranyl, 5-naphtho-[2,3-b]-benzofuranyl, 6-naphtho-[2,3-b]-benzofuranyl, 7-naphtho-[2,3-b]-benzofuranyl, 8-naphtho-[2,3 -b]-benzofuranyl, 9-naphtho-[2,3-b]-benzofuranyl, 10-naphtho-[2,3-b]-benzofuranyl, 1-naphtho-[2,1-b]-benzofuranyl, 2-naphtho-[2,1-b]-benzofuranyl, 3-naphtho-[2,1-b]-benzofuranyl, 4-naphtho-[2,1-b]-benzofuranyl yl, 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]-benzothiophene, 2-naphtho-[1,2-b]-benzothiophene, 3-naphtho-[1,2-b]-benzothiophene, 4-naphtho-[1,2-b]-benzothiophene, 5-naphtho-[1,2-b]-benzothiophene, 6-naphtho-[1,2-b]-benzothiophene, 7-naphtho-[1,2-b]-benzothiophene Thienyl, 8-naphtho-[1,2-b]-benzothienyl, 9-naphtho-[1,2-b]-benzothienyl, 10-naphtho-[1,2-b]-benzothienyl, 1-naphtho-[2,3-b]-benzothienyl, 2-naphtho-[2,3-b]-benzothienyl, 3-naphtho-[2,3-b]-benzothienyl, 4-naphtho-[1,2-b]-benzothienyl -[2,3-b]-benzothiophene, 5-naphtho-[2,3-b]-benzothiophene, 1-naphtho-[2,1-b]-benzothiophene, 2-naphtho-[2,1-b]-benzothiophene, 3-naphtho-[2,1-b]-benzothiophene, 4-naphtho-[2,1-b]-benzothiophene, 5-naphtho-[2,1-b]- benzothiophene, 6-naphtho-[2,1-b]-benzothiophene, 7-naphtho-[2,1-b]-benzothiophene, 8-naphtho-[2,1-b]-benzothiophene, 9-naphtho-[2,1-b]-benzothiophene, 10-naphtho-[2,1-b]-benzothiophene, 2-benzofurano[3,2-d]pyrimidinyl, 6-benzo 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-Benzofuro[3,2-d]pyrazinyl, 7-Benzofuro[3,2-d]pyrazinyl 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-germaniumfluorenyl, 2-germaniumfluorenyl, 3-germaniumfluorenyl, 4-germaniumfluorenyl, 1-dibenzoselenophene, 2-dibenzoselenophene, 3-dibenzoselenophene, 4-dibenzoselenophene, etc. In addition, the term "halogen" includes F, Cl, Br and I.

[0035] In addition, "ortho (o-)", "meta (m-)", and "para (p-)" are prefixes that indicate the relative positions of substituents, respectively. Ortho means that two substituents are adjacent to each other, and for example, when two substituents in a benzene derivative occupy positions 1 and 2, it is referred to as the ortho position. Meta means that two substituents are at positions 1 and 3, and for example, when two substituents in a benzene derivative occupy positions 1 and 3, it is referred to as the meta position. Para means that two substituents are at positions 1 and 4, and for example, when two substituents in a benzene derivative occupy positions 1 and 4, it is referred to as the para position.

[0036] As used herein, the term "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a functional group is replaced by another atom or another functional group (i.e., a substituent), as well as a substituent in which two or more substituents are linked. For example, a "substituent in which two or more substituents are linked" may be pyridine-triazine. That is, pyridine-triazine may be a heteroaryl group or may be interpreted as a substituent in which two heteroaryl groups are linked. In the formulae of the present disclosure, the substituents of the substituted alkyl, substituted cycloalkyl, substituted heterocycloalkyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted silyl, and substituted amino are each independently at least one selected from the group consisting of: deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; phosphine oxide; (C1-C30)alkyl; halo(C1-C30)alkyl; (C2-C30)alkenyl; (C2-C30)alkynyl; (C1-C30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkane; alkyl; (C3-C30)cycloalkenyl; (3- to 7-membered)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (3- to 30-membered)heteroaryl, unsubstituted or substituted by one or more (C6-C30)aryl groups; (C6-C30)aryl, unsubstituted or substituted by at least one of one or more (C1-C30)alkyl groups and one or more (3- to 30-membered)heteroaryl groups; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylmethyl Silyl; (C1-C30)alkyldi(C6-C30)arylsilyl; amino; mono- or di-(C1-C30)alkylamino; mono- or di-(C2-C30)alkenylamino; mono- or di-(C6-C30)arylamino; mono- or di-(3- to 30-membered)heteroarylamino; (C1-C30)alkyl(C2-C30)alkenylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkyl(3- to 30-membered)heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino ; (C2-C30)alkenyl(3- to 30-membered)heteroarylamino; (C6-C30)aryl(3- to 30-membered)heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; (C6-C30)arylphosphine; di(C6-C30)arylborylcarbonyl; di(C1-C30)alkylborylcarbonyl; (C1-C30)alkyl(C6-C30)arylborylcarbonyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl.According to one embodiment of the present disclosure, the substituents are each independently selected from at least one of the following groups: (C1-C6) alkyl, (C6-C20) aryl, unsubstituted or substituted by one or more (C6-C15) aryl (5- to 15-membered) heteroaryl, di(C6-C12) arylamino, and (C1-C6) alkyl (C6-C15) aryl. Specifically, the substituents are each independently selected from at least one of the following groups: methyl, phenyl, naphthyl, biphenyl, phenanthrenyl, triphenylenyl, dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, diphenyltriazinyl, phenylnaphthyltriazinyl, phenylcarbazolyl, and diphenylamino.

[0037] In Formula 1, Ring A is selected from the following formulae.

[0038]

[0039] According to another embodiment of the present disclosure, ring A is selected from the following formulae.

[0040]

[0041] According to yet another embodiment of the present disclosure, ring A is selected from the following formulae.

[0042]

[0043] According to yet another embodiment of the present disclosure, Ring A is selected from the following formulae.

[0044]

[0045] In Formula 1, X represents NR 11 , CR 12 R 13 , O or S.

[0046] In this paper, R 11 represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino. According to one embodiment of the present disclosure, R 11 represents a substituted or unsubstituted (C6-C15) aryl group, or a substituted or unsubstituted (5- to 15-membered) heteroaryl group containing one or more nitrogen atoms. According to another embodiment of the present disclosure, R 11represents a (C6-C15) aryl group substituted by at least one of one or more (5- to 15-membered) heteroaryl groups containing one or more nitrogen atoms and one or more di(C6-C15) arylamino groups; or a (5- to 15-membered) heteroaryl group containing one or more nitrogen atoms substituted by at least one of one or more (C6-C20) aryl groups and one or more (5- to 15-membered) heteroaryl groups. According to another embodiment of the present disclosure, R 11 to R 13 The substituted or unsubstituted (3- to 30-membered) heteroaryl groups each independently represent a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinolyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted dibenzoquinolyl group, a substituted or unsubstituted dibenzoquinazolinyl group, a substituted or unsubstituted dibenzoquinoxalinyl, substituted or unsubstituted indenopyridinyl, substituted or unsubstituted indenopyrimidinyl, substituted or unsubstituted indenopyrazinyl, substituted or unsubstituted benzofuranopyridinyl, substituted or unsubstituted benzofuranopyrimidinyl, substituted or unsubstituted benzofuranopyrazinyl, substituted or unsubstituted benzothienopyridinyl, substituted or unsubstituted benzothienopyrimidinyl, substituted or unsubstituted benzothienopyrazinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothienyl. Specifically, R 11 It may represent a phenyl group substituted by a diphenyltriazinyl group or a diphenylamino group; a naphthyl group substituted by a diphenyltriazinyl group or a phenylnaphthyltriazinyl group; a triazinyl group, a quinazolinyl group, a quinoxalinyl group, or a benzoquinoxalinyl group substituted by at least one of one or more phenyl groups, one or more naphthyl groups, one or more biphenyl groups, one or more phenanthrenyl groups, one or more triphenylenyl groups, one or more dibenzofuranyl groups, one or more dibenzothienyl groups, and one or more phenylcarbazolyl groups; etc.

[0047] In addition, R 12 and R 13 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino; or are connected to form a ring. According to one embodiment of the present disclosure, R 12 and R 13 Each independently represents a methyl group, an ethyl group, or a propyl group.

[0048] In formula 1, R 21 Indicates -L1-Ar1. If R 21 If there are multiple, then each R 21 Can be the same or different.

[0049] Herein, L1 each independently represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group. According to one embodiment of the present disclosure, L1 each independently represents a single bond, a substituted or unsubstituted (C6-C15)arylene group, or a substituted or unsubstituted (5- to 15-membered)heteroarylene group. According to another embodiment of the present disclosure, L1 each independently represents a single bond, an unsubstituted (C6-C15)arylene group or a substituted (C6-C15)arylene group substituted with one or more (C6-C15)aryl groups, or an unsubstituted (5- to 15-membered)heteroarylene group. According to another embodiment of the present disclosure, L1 each independently represents a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenylene group, or a substituted or unsubstituted pyridinylene group. Specifically, L1 can each independently represent a single bond, a phenylene group, a naphthylene group, a biphenylene group, a phenylene group substituted with a phenyl group, a pyridinylene group, and the like.

[0050] In addition, Ar1 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino. According to one embodiment of the present disclosure, Ar1 each independently represents hydrogen, substituted or unsubstituted (5-15 membered) heteroaryl containing one or more nitrogen atoms, or substituted or unsubstituted amino. According to another embodiment of the present disclosure, Ar1 each independently represents hydrogen; a (5- to 15-membered) heteroaryl group substituted by at least one of one or more (C6-C15) aryl groups, one or more (5- to 15-membered) heteroaryl groups, and one or more (C1-C6) alkyl (C6-C15) aryl groups; or an amino group substituted by at least one of one or more (C6-C15) aryl groups, one or more (5- to 15-membered) heteroaryl groups, and one or more (C1-C6) alkyl (C6-C15) aryl groups. According to yet another embodiment of the present disclosure, the substituted or unsubstituted (3- to 30-membered) heteroaryl groups of Ar1 each independently represent a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinolyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted dibenzoquinolyl group, a substituted or unsubstituted dibenzoquinazolinyl group , substituted or unsubstituted dibenzoquinoxalinyl, substituted or unsubstituted indenopyridinyl, substituted or unsubstituted indenopyrimidinyl, substituted or unsubstituted indenopyrazinyl, substituted or unsubstituted benzofuranopyridinyl, substituted or unsubstituted benzofuranopyrimidinyl, substituted or unsubstituted benzofuranopyrazinyl, substituted or unsubstituted benzothienopyridinyl, substituted or unsubstituted benzothienopyrimidinyl, substituted or unsubstituted benzothienopyrazinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothienyl. Specifically, Ar1 can each independently represent hydrogen; a triazine group, a quinazoline group, a quinoxaline group, or a benzoquinoxaline group, which is substituted by at least one of one or more phenyl groups, one or more naphthyl groups, one or more biphenyl groups, one or more phenanthrenyl groups, one or more dimethylfluorenyl groups, one or more dibenzofuranyl groups, and one or more dibenzothiophenyl groups; an amino group, which is substituted by at least one of one or more phenyl groups, one or more naphthyl groups, one or more biphenyl groups, one or more dimethylfluorenyl groups, one or more dibenzofuranyl groups, one or more dibenzothiophenyl groups, and one or more phenylcarbazolyl groups, etc.

[0051] In Formula 1, a represents an integer from 1 to 4, and b represents an integer from 1 to 10, wherein if a and b are integers of 2 or greater, each R1 and each R 21 Can be the same or different.

[0052] According to one embodiment of the present disclosure, R 11 represents a substituted or unsubstituted (C6-C15)aryl group, or a substituted or unsubstituted (5- to 15-membered)heteroaryl group containing one or more nitrogen atoms; L1 each independently represents a single bond, a substituted or unsubstituted (C6-C15)arylene group, or a substituted or unsubstituted (5- to 15-membered)heteroarylene group; and Ar1 each independently represents hydrogen, a substituted or unsubstituted (5- to 15-membered)heteroaryl group containing one or more nitrogen atoms, or a substituted or unsubstituted amino group.

[0053] According to another embodiment of the present disclosure, R 11 represents a (C6-C15) aryl group which is unsubstituted or substituted by at least one of one or more (5- to 15-membered) heteroaryl groups containing one or more nitrogen atoms and one or more di(C6-C15) arylamino groups; or a (5- to 15-membered) heteroaryl group containing one or more nitrogen atoms which is substituted by at least one of one or more (C6-C20) aryl groups and one or more (5- to 15-membered) heteroaryl groups; L1 each independently represents a single bond, is unsubstituted or substituted by one or more (C6-C15) aryl groups. Ar1 each independently represents hydrogen; a (5- to 15-membered) heteroaryl group substituted by at least one of one or more (C6-C15) aryl groups, one or more (5- to 15-membered) heteroaryl groups, and one or more (C1-C6) alkyl (C6-C15) aryl groups; or an amino group substituted by at least one of one or more (C6-C15) aryl groups, one or more (5- to 15-membered) heteroaryl groups, and one or more (C1-C6) alkyl (C6-C15) aryl groups.

[0054] In the formula of the present disclosure, if a substituent is connected to an adjacent substituent or two adjacent substituents are connected to each other to form a ring, the ring can be a substituted or unsubstituted monocyclic or polycyclic (3 to 30 yuan) aliphatic ring or aromatic ring or a combination thereof. In addition, the formed ring can contain at least one heteroatom selected from B, N, O, S, Si and P, preferably at least one heteroatom selected from N, O and S. According to one embodiment of the present disclosure, the number of ring skeleton atoms is 5 to 20. According to another embodiment of the present disclosure, the number of ring skeleton atoms is 5 to 15. For example, the fused ring can be a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted benzene ring or a substituted or unsubstituted carbazole ring.

[0055] In the formulae of the present disclosure, the heterocycloalkyl group and the (ene)heteroaryl group may each independently contain at least one heteroatom selected from B, N, O, S, Si and P. In addition, the heteroatom may be bonded to at least one substituent selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, and substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino.

[0056] The compound represented by Formula 1 may be one selected from the following compounds, but is not limited thereto.

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091] The compound represented by Formula 1 of the present disclosure can be produced by a synthetic method known to those skilled in the art, and for example, according to the following Reaction Schemes 1 to 7.

[0092] [Reaction Scheme 1]

[0093]

[0094] [Reaction Scheme 2]

[0095]

[0096] [Reaction Scheme 3]

[0097]

[0098] [Reaction Scheme 4]

[0099]

[0100] [Reaction Scheme 5]

[0101]

[0102] [Reaction Scheme 6]

[0103]

[0104] [Reaction Scheme 7]

[0105]

[0106] In Reaction Schemes 1 to 7, X, R1, L1, Ar1, and a are as defined in Formula 1, and Hal represents a halogen.

[0107] Although illustrative synthesis examples of the compounds represented by Formula 1 are described above, those skilled in the art will be able to easily understand that they are all based on Suzuki cross-coupling reaction, Wittig reaction, Miyaura borylation reaction, Ullmann reaction, Buchwald-Hartwig cross-coupling reaction, N-arylation reaction, H-mont-mediated etherification reaction, intramolecular acid-induced cyclization reaction, Pd(II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, dehydration cyclization reaction, SN1 substitution reaction, SN2 substitution reaction, phosphine-mediated reductive cyclization reaction, etc., and the above reactions proceed even if a substituent defined in Formula 1 above but not specified in the specific synthesis example is bonded.

[0108] The hole transport region of the present disclosure may be composed of one or more layers selected from the group consisting of a hole transport layer, a hole injection layer, an electron blocking layer, and a hole auxiliary layer. Each layer may be composed of one or more layers.

[0109] According to one embodiment of the present disclosure, the hole transport region may include a hole transport layer. In addition, the hole transport region may include a hole transport layer and further include one or more layers of a hole injection layer, an electron blocking layer, and a hole auxiliary layer.

[0110] The present disclosure provides an organic electroluminescent material including a compound represented by Formula 1, and an organic electroluminescent device including the organic electroluminescent material.

[0111] The organic electroluminescent material may consist of only the compound according to the present disclosure, or may further contain conventional materials included in organic electroluminescent materials.

[0112] The organic electroluminescent compound of formula 1 disclosed herein may be included in one or more layers of a light-emitting layer, a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer; preferably, it is included in a light-emitting layer. When used in a light-emitting layer, the organic electroluminescent compound of formula 1 disclosed herein may be included as a host material. Preferably, the light-emitting layer may further include one or more dopants. If necessary, the organic electroluminescent compound of the present disclosure may be used as a co-host material. That is, the light-emitting layer may further include an organic electroluminescent compound other than the organic electroluminescent compound represented by formula 1 of the present disclosure (first host material) as a second host material. In this case, the weight ratio between the first host material and the second host material is 1:99 to 99:1. When two or more materials are included in a layer, mixed deposition can be performed to form a layer, or co-deposition can be performed separately at the same time to form a layer.

[0113] According to one embodiment of the present disclosure, when the organic electroluminescent compound having Formula 1 of the present disclosure is included in a light-emitting layer, the light-emitting layer may further include a compound represented by the following Formula 2:

[0114]

[0115] in

[0116] X1 and Y1 each independently represent -N=, -NR7-, -O-, or -S-, provided that either one of X1 and Y1 represents -N=, and the other of X1 and Y1 represents -NR7-, -O-, or -S-;

[0117] R' represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group;

[0118] R2 to R7 each independently represent 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 fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, substituted or unsubstituted mono- or di-(C1- C30)alkylamino, substituted or unsubstituted mono- or di-(C2-C30)alkenylamino, substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, substituted or unsubstituted mono- or di-(3- to 30-membered)heteroarylamino, substituted or unsubstituted (C1-C30)alkyl (3- to 30-membered)heteroarylamino, substituted or unsubstituted (C2-C30)alkenyl (C6-C30)arylamino, substituted or unsubstituted (C2-C30)alkenyl (3- to 30-membered)heteroarylamino, or substituted or unsubstituted (C6-C30)aryl (3- to 30-membered)heteroarylamino; or may be linked to adjacent substituents to form one or more rings;

[0119] L' represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group; and

[0120] f represents 1, g and h each independently represent 1 or 2, and i represents an integer of 1 to 4, wherein if each of g to i is an integer of 2 or greater, each R2 to each R4 may be the same or different.

[0121] In Formula 2, X1 and Y1 each independently represent -N=, -NR7-, -O-, or -S-, provided that either one of X1 and Y1 represents -N=, and the other of X1 and Y1 represents -NR7-, -O-, or -S-. According to one embodiment, either one of X1 and Y1 represents -N=, and the other represents -O- or -S-. For example, X1 represents -N=, and Y1 represents -O-; X1 represents -O-, and Y1 represents -N=; or X1 represents -S-, and Y1 represents -N=. In Formula 2, R' represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group. According to one embodiment, R' represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (5- to 25-membered) heteroaryl group. According to another embodiment, R' represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5-20 membered) heteroaryl group. For example, R' represents an unsubstituted phenyl group, an unsubstituted biphenyl group, an unsubstituted naphthyl group, a fluorenyl group substituted with one or more methyl groups, a benzofluorenyl group substituted with one or more methyl groups, an unsubstituted dibenzofuranyl group, an unsubstituted dibenzothiophenyl group, a spiro[fluorene-fluorenyl] group, a spiro[fluorene-benzofluorenyl] group, or an unsubstituted pyridyl group.

[0122] In Formula 2, R2 to R7 each independently represent 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 fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, substituted or unsubstituted mono- or di-(C substituted or unsubstituted (C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C2-C30)alkenylamino, substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, substituted or unsubstituted mono- or di-(3- to 30-membered)heteroarylamino , substituted or unsubstituted (C1-C30)alkyl (3- to 30-membered)heteroarylamino, substituted or unsubstituted (C2-C30)alkenyl (C6-C30)arylamino, substituted or unsubstituted (C2-C30)alkenyl (3- to 30-membered)heteroarylamino, or substituted or unsubstituted (C6-C30)aryl (3- to 30-membered)heteroarylamino; or may be connected with adjacent substituents to form one or more rings. According to one embodiment, R2 to R7 each independently represent hydrogen, substituted or unsubstituted (C6-C25)aryl, substituted or unsubstituted (3-25 membered)heteroaryl, or substituted or unsubstituted mono- or di-(C6-C25)arylamino; or may be connected with adjacent substituents to form one or more substituted or unsubstituted, monocyclic or polycyclic (C3-C30) alicyclic rings or aromatic rings, one or more carbon atoms of the alicyclic rings or aromatic rings may be replaced by at least one heteroatom selected from nitrogen, oxygen and sulfur.According to another embodiment, R2 to R7 each independently represent hydrogen, substituted or unsubstituted (C6-C25)aryl, substituted or unsubstituted (5-membered to 25-membered)heteroaryl, substituted or unsubstituted di(C6-C18)arylamino, substituted or unsubstituted mono- or di-(3-membered to 30-membered)heteroarylamino, or substituted or unsubstituted (C6-C30)aryl (3-membered to 30-membered)heteroarylamino; or may be connected with adjacent substituents to form one or more substituted or unsubstituted, monocyclic or polycyclic (C3-C25)alicyclic rings or aromatic rings, one or more carbon atoms of the alicyclic rings or aromatic rings may be replaced by at least one heteroatom selected from nitrogen and sulfur, and the heteroaryl group may contain at least one heteroatom selected from the group consisting of B, N, O, S, Si and P. Specifically, R', R5 and R6 each independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted benzofuranopyrimidinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzonaphthofuranyl, or substituted or unsubstituted benzonaphthothiophenyl. For example, at least one of R5 and R6 each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted o-biphenyl group, a substituted or unsubstituted m-biphenyl group, a substituted or unsubstituted p-biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted benzofluorenyl group.For example, R' can be phenyl, biphenyl, or pyridyl; R2 and R3 can be hydrogen; R4 can be hydrogen or phenyl; R5 and R6 can each independently be substituted phenyl, naphthyl, biphenyl, phenanthrenyl, dimethylfluorenyl, diphenylfluorenyl, naphthylphenyl, phenylnaphthyl, dimethylbenzofluorenyl, terphenyl, spirobifluorenyl, benzofuranyl, benzothienyl, dibenzothienyl, unsubstituted or dibenzofuranyl substituted with one or more phenyl groups, carbazolyl substituted with one or more phenyl groups, or benzonaphthofuranyl; and the one or more substituents of the substituted phenyl group can be at least one selected from the group consisting of: phenyl substituted with at least one of deuterium, one or more methyl groups and one or more tert-butyl groups; anthracenyl; fluoranthenyl; phenylfluorenyl; cyclohexyl; pyridyl substituted with one or more phenyl groups; phenoxazinyl; and benzimidazolyl substituted with one or more phenyl groups.

[0123] In Formula 2, f represents 1 or 2, preferably 1; g and h each independently represent 1 or 2, preferably 1; and i represents an integer from 1 to 4, preferably 1 or 2. If each of g to i is an integer of 2 or greater, each R2 to each R4 may be the same or different.

[0124] In Formula 2, L' represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group. According to one embodiment of the present disclosure, L' represents a single bond, or a substituted or unsubstituted (C6-C18)arylene group. According to another embodiment of the present disclosure, L' represents a single bond, or an unsubstituted (C6-C12)arylene group. For example, L' represents a single bond, or an unsubstituted phenylene group.

[0125] The compound represented by Formula 2 may be one selected from the following compounds, but is not limited thereto.

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132] According to another embodiment of the present disclosure, when the organic electroluminescent compound having Formula 1 of the present disclosure is included in a light-emitting layer, the light-emitting layer may further include a compound represented by the following Formula 3:

[0133] HAr-((L2)e-Ar2)d-----(3)

[0134] in

[0135] HAr represents a substituted or unsubstituted (3- to 20-membered) heteroaryl group containing one or more nitrogen atoms;

[0136] L2 each independently represents a substituted or unsubstituted (C6-C30)arylene group;

[0137] Ar2 each independently represents a substituted or unsubstituted (C6-C30)aryl group, or the following formula 4, provided that at least one of Ar2 represents formula 4;

[0138]

[0139] Y represents O, S, CR 41 R 42 , N-*, or NR 43 ;

[0140] R 41 to R 43 Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, or a substituted or unsubstituted (C6-C30) aryl group, or R 41 and R 42 Can be connected to each other to form a ring;

[0141] R 31 to R 38 Each independently represents a site of attachment to L2; or represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) 0) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or -L4-N (Ar3) (Ar4); or may be connected with adjacent substituents to form one or more rings;

[0142] L4 each independently represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group;

[0143] Ar3 and Ar4 each independently represent hydrogen, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group;

[0144] d represents an integer from 1 to 3, wherein if d is an integer of 2 or greater, each ((L2) e -Ar2) may be the same or different;

[0145] e represents an integer from 0 to 2, wherein if e is 2, each L2 may be the same or different; and

[0146] * indicates the site of attachment to L2.

[0147] In Formula 3, HAr represents a substituted or unsubstituted (3- to 20-membered) heteroaryl group containing one or more nitrogen atoms. According to one embodiment of the present disclosure, HAr represents a substituted or unsubstituted (3- to 15-membered) heteroaryl group containing one or more nitrogen atoms. According to another embodiment of the present disclosure, HAr represents an unsubstituted (5- to 15-membered) heteroaryl group containing one or more nitrogen atoms. Specifically, HAr can be a pyridyl group, a pyrimidyl group, a triazine group, a quinolyl group, a quinazolinyl group, a quinoxalinyl group, a naphthyridinyl group, a pyridopyrazinyl group, a benzoquinazolinyl group, a benzoquinoxalinyl group, a benzofuranopyrimidinyl group, or the like.

[0148] In Formula 3, L2 each independently represents a substituted or unsubstituted (C6-C30)arylene group. According to one embodiment of the present disclosure, L2 each independently represents a substituted or unsubstituted (C6-C20)arylene group. According to another embodiment, L2 each independently represents an unsubstituted (C6-C20)arylene group. Specifically, L2 each independently can be a phenylene group, a naphthylene group, a biphenylene group, a triphenylene group, etc.

[0149] In Formula 3, Ar2 each independently represents a substituted or unsubstituted (C6-C30)aryl group, or Formula 4, provided that at least one of Ar2 represents Formula 4. According to one embodiment of the present disclosure, Ar2 each independently represents a (C6-C30)aryl group substituted with a (5- to 15-membered) heteroaryl group, wherein the (5- to 15-membered) heteroaryl group is substituted with one or more (C6-C12)aryl groups; a (C6-C30)aryl group substituted with one or more di(C6-C12)arylamino groups; an unsubstituted (C6-C30)aryl group; or Formula 4. Specifically, Ar2 each independently can be phenyl, naphthyl, phenylnaphthyl, naphthylphenyl, biphenyl, terphenyl, phenanthrenyl, triphenylene, phenyl, unsubstituted or triphenylene group substituted with one or more phenyl groups, phenyl substituted with one or more phenylquinoxalinyl groups, phenyl substituted with one or more diphenylamino groups, etc., or Formula 4.

[0150] In formula 4, Y represents O, S, CR 41 R 42 , N-*, or NR 43 ; and * indicates the site of attachment to L2.

[0151] In formula 4, R 41 to R 43 Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, or a substituted or unsubstituted (C6-C30) aryl group, or R 41 and R 42 Can be connected to each other to form a ring. According to one embodiment of the present disclosure, R 41 to R 43 Each independently represents a substituted or unsubstituted (C1-C6) alkyl group, or a substituted or unsubstituted (C6-C12) aryl group, or R 41 and R 42 Can be connected to each other to form a ring. According to another embodiment of the present disclosure, R 41 to R 43 Each independently represents an unsubstituted (C1-C6) alkyl group, or an unsubstituted (C6-C12) aryl group, or R 41 and R 42 can be connected to each other to form a ring. 41 to R 43 Each independently represents a methyl group, a phenyl group, or R 41 and R 42 They can be linked to each other to form a fluorene ring.

[0152] In formula 4, R 31 to R 38Each independently represents a site of attachment to L2; or represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) 0) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or -L4-N (Ar3) (Ar4); or it may be connected with adjacent substituents to form one or more rings. According to one embodiment of the present disclosure, R 31 to R 38 Each independently represents a site of attachment to L2; or represents hydrogen, or a substituted or unsubstituted (C6-C20) aryl group; or may be connected with adjacent substituents to form one or more rings. According to another embodiment of the present disclosure, R 31 to R 38 Each independently represents a site for connection to L2; or represents hydrogen, or an unsubstituted (C6-C18) aryl group; or can be connected with adjacent substituents to form one or more rings. For example, R 31 to R 38 Each independently may be a site for connection to L2; or may be hydrogen, phenyl, naphthyl, biphenyl, naphthylphenyl, phenylnaphthyl, etc.; or may be connected to an adjacent substituent to form a benzene ring.

[0153] L4 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group.

[0154] Ar3 and Ar4 each independently represent hydrogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted fused ring group of one or more (C3-C30)aliphatic rings and one or more (C6-C30)aromatic rings, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered)heteroaryl group.

[0155] In Formula 3, d represents an integer from 1 to 3, wherein if d is an integer of 2 or greater, each ((L2) e -Ar2) can be the same or different. For example, d can be an integer of 2 or 3, and each ((L2) e -Ar2) can be the same or different.

[0156] In Formula 3, e represents an integer from 0 to 2, wherein if e is 2, each L2 may be the same or different.

[0157] The compound represented by Formula 3 may be one selected from the following compounds, but is not limited thereto.

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171] The dopant contained in the organic electroluminescent device of the present disclosure may be at least one phosphorescent dopant or fluorescent dopant, and is preferably a phosphorescent dopant. The phosphorescent dopant material used in the organic electroluminescent device of the present disclosure is not particularly limited, but may be preferably selected from metallized iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt) complex compounds, more preferably selected from ortho-metallized iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt) complex compounds, and even more preferably ortho-metallized iridium complex compounds.

[0172] The dopant included in the organic electroluminescent device of the present disclosure may include a compound represented by the following Formula 101, but is not limited thereto.

[0173]

[0174] In Formula 101, L is selected from the following Structures 1 to 3.

[0175]

[0176] R 100 to R 103 each independently represents hydrogen, deuterium, halogen, unsubstituted or substituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C6-C30)aryl, cyano, substituted or unsubstituted (3- to 30-membered)heteroaryl, or substituted or unsubstituted (C1-C30)alkoxy; or may be linked to adjacent substituents to form one or more rings together with pyridine, for example, substituted or unsubstituted quinoline, isoquinoline, benzofuropyridine, benzothienopyridine, indenopyridine, benzofuranoquinoline, benzothienoquinoline, or indenoquinoline;

[0177] R 104 to R 107 Each independently represents hydrogen, deuterium, halogen, unsubstituted or substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; or may be linked to adjacent substituents to form one or more rings together with benzene, such as substituted or unsubstituted naphthalene, fluorene, dibenzothiophene, dibenzofuran, indenopyridine, benzofuropyridine, or benzothienopyridine;

[0178] R 201 to R 220 Each independently represents hydrogen, deuterium, halogen, unsubstituted or substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C6-C30) aryl; or may be linked with adjacent substituents to form one or more rings; and

[0179] s represents an integer from 1 to 3.

[0180] Specific examples of the dopant compound are as follows, but are not limited thereto.

[0181]

[0182]

[0183]

[0184]

[0185]

[0186] An organic electroluminescent device according to the present disclosure has a first electrode, a second electrode, and at least one organic layer between the first electrode and the second electrode.

[0187] One of the first electrode and the second electrode may be an anode, and the other may be a cathode. The organic layer includes a light-emitting layer and may further include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer. In addition, each layer may be composed of multiple layers.

[0188] The first electrode and the second electrode can each be formed of a transmissive conductive material, a semi-transmissive reflective conductive material, or a reflective conductive material. Depending on the type of material forming the first electrode and the second electrode, the organic electroluminescent device can be a top-emitting type, a bottom-emitting type, or a double-sided emitting type. In addition, the hole injection layer can be further doped with a p-type dopant, and the electron injection layer can be further doped with an n-type dopant.

[0189] According to one embodiment of the present disclosure, the organic electroluminescent device of the present disclosure may further include an azine-based compound as at least one of an electron transport material, an electron injection material, an electron buffer material, and a hole blocking material in addition to the organic electroluminescent compound of the present disclosure.

[0190] In the organic electroluminescent device according to the present disclosure, the organic layer may further include at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.

[0191] In addition, in the organic electroluminescent device of the present disclosure, the organic layer may further contain at least one metal selected from the group consisting of: metals of Group 1 of the periodic table, metals of Group 2, transition metals of Period 4, transition metals of Period 5, lanthanide elements, and organometallics of d-transition elements, or at least one complex compound containing the metal.

[0192] In addition to the compounds of the present invention, the organic electroluminescent device of the present invention can emit white light by further comprising at least one light-emitting layer containing a compound known in the art that emits blue light, red light, or green light. In addition, if desired, it can further include a layer that emits yellow light or orange light.

[0193] In the organic electroluminescent device disclosed herein, at least one layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter, "surface layer") may be preferably placed on one or more inner surfaces of one or both electrodes. Specifically, a silicon or aluminum chalcogenide (including oxide) layer is preferably placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or a metal oxide layer is preferably placed on the cathode surface of the electroluminescent medium layer. The surface layer can provide operational stability for the organic electroluminescent device. Preferably, the chalcogenide comprises SiO X (1≤X≤2), AlO X (1≤X≤1.5), SiON, SiAlON, etc.; metal halides include LiF, MgF2, CaF2, rare earth metal fluorides, etc.; and metal oxides include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0194] A hole injection layer, a hole transport layer, or an electron blocking layer, or a combination thereof, may be used between the anode and the light-emitting layer. The hole injection layer may be a multilayer layer in order to reduce the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, wherein each of the multilayer layers may use two compounds simultaneously. The hole transport layer or the electron blocking layer may also be a multilayer layer.

[0195] An electron buffer layer, hole blocking layer, electron transport layer, electron injection layer, or a combination thereof may be used between the light-emitting layer and the cathode. The electron buffer layer may be multilayered to control electron injection and improve the interface properties between the light-emitting layer and the electron injection layer, wherein each of the multilayers may use two compounds simultaneously. The hole blocking layer or electron transport layer may also be multilayered, wherein each of the multilayers may use multiple compounds.

[0196] The luminescence auxiliary layer can be placed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer. When the luminescence auxiliary layer is placed between the anode and the light-emitting layer, it can be used to promote hole injection and / or hole transport, or to prevent electron overflow. When the luminescence auxiliary layer is placed between the cathode and the light-emitting layer, it can be used to promote electron injection and / or electron transport, or to prevent hole overflow. In addition, the hole auxiliary layer can be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can effectively promote or limit the hole transport rate (or hole injection rate), thereby enabling control of charge balance. In addition, the electron blocking layer can be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can block the overflow electrons from the light-emitting layer and confine the excitons in the light-emitting layer to prevent light leakage. 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 hole auxiliary layer and the electron blocking layer can have the effect of improving the efficiency and / or life of the organic electroluminescent device.

[0197] In the organic electroluminescent device disclosed herein, a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant is preferably placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to anions, and thus it becomes easier to inject and transport electrons from the mixed region to the electroluminescent medium. In addition, the hole transport compound is oxidized to cations, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium. Preferably, the oxidative dopant includes various Lewis acids and acceptor compounds; and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. The reductive dopant layer can be used as a charge generation layer to produce an organic electroluminescent device having two or more light-emitting layers that emit white light.

[0198] According to one embodiment of the present disclosure, an organic electroluminescent material can be used as a light-emitting material for a white organic light-emitting device. Depending on the arrangement of R (red), G (green), B (blue), or YG (yellow-green) light-emitting units, white organic light-emitting devices have various structures, such as a parallel arrangement (side-by-side) method, a stacking method, or a color conversion material (CCM) method. In addition, according to one embodiment of the present disclosure, the organic electroluminescent material can also be applied to an organic electroluminescent device containing quantum dots (QDs).

[0199] To form each layer of the organic electroluminescent device of the present disclosure, a dry film-forming method such as vacuum evaporation, sputtering, plasma, ion plating, etc., or a wet film-forming method such as inkjet printing, spin coating, dip coating, flow coating, etc. can be used. The first and second host compounds of the present disclosure can be co-evaporated or mixed to form a film.

[0200] When a wet film-forming method is used, a thin film can be formed by dissolving or dispersing the material constituting each layer in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. There is no particular limitation on the solvent as long as the material constituting each layer is soluble or dispersible in the solvent, which does not cause any problem in forming a film.

[0201] A display system, such as a display system for a smartphone, tablet computer, notebook computer, PC, TV, or automobile; or a lighting system, such as an outdoor or indoor lighting system, can be produced by using the organic electroluminescent device of the present disclosure.

[0202] Hereinafter, the preparation method of the compound of the present disclosure and the characteristics of the compound will be explained in detail with reference to the representative compounds of the present disclosure. However, the present disclosure is not limited to the following examples.

[0203] Example 1: Preparation of Compound C-686

[0204]

[0205] Synthesis of compound 1-1

[0206] 1-Bromo-2-naphthaldehyde (20.0 g, 85.1 mmol), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (26.2 g, 51.5 mmol), tetrakis(triphenylphosphine)palladium(0) (2.95 g, 2.55 mmol), NaOH (4.12 g, 255 mmol), 360 mL of tetrahydrofuran (THF), and 90 mL of H2O were introduced into a flask, and the mixture was stirred at 90 ° C. for 1.5 hours under reflux. After the reaction was completed, the reaction mixture was neutralized with NH4Cl aqueous solution, extracted with dichloromethane (MC), and dried over MgSO4. The residue was separated by column chromatography, and the solid obtained by adding MeOH was filtered under reduced pressure to obtain compound 1-1 (20.0 g, yield: 73%).

[0207] Synthesis of compound 1-2

[0208] Compound 1-1 (19.0 g, 59.1 mmol), (methoxymethyl) triphenylphosphonium chloride (30.4 g, 88.7 mmol) and 300 mL of THF were introduced into a flask, and while stirring at 0° C., 33.3 mL of a 1 M K-Ot-Bu solution dissolved in THF was added dropwise thereto. The mixture was stirred for 3 hours, neutralized with NH 4 Cl, extracted with MC, and dried over MgSO 4 . The residue was separated by column chromatography, and the solid obtained by adding MeOH was filtered under reduced pressure to obtain compound 1-2 (20.0 g, yield: 97%).

[0209] Synthesis of compounds 1-3

[0210] Compound 1-2 (66.3 g, 191 mmol), 34 mL of Eaton's reagent, and 950 mL of chlorobenzene were introduced into a flask, and the mixture was stirred at 180° C. under reflux overnight. After the reaction was completed, the reaction mixture was neutralized with NaHCO 3 , extracted with MC, and dried over MgSO 4 . The residue was separated by column chromatography, and the solid obtained by adding MeOH was filtered under reduced pressure to obtain compound 1-3 (27 g, yield: 45%).

[0211] Synthesis of compound C-686

[0212] Compound 1-3 (10.0 g, 11 mmol), 2-chloro-3-phenyl-quinoxaline (7.6 g, 31.5 mmol), Cs CO (10.3 g, 31.5 mmol), dimethylaminopyridine (DMAP) (1.92 g, 0.0158 mmol), and 60 mL of dimethyl sulfoxide (DMSO) were introduced into a flask, and the mixture was stirred at 100° C. for 4 hours. After the reaction was completed, the solid obtained by adding H O to the mixture was separated by column chromatography, and the solid obtained by adding MeOH was filtered under reduced pressure to obtain compound C-686 (1.3 g, yield: 8%).

[0213] Compound MW Melting point C-686 521.61 269℃

[0214] Example 2: Preparation of Compound C-700

[0215]

[0216] Compound 1-3 (5.0 g, 15.8 mmol), 2- (2- bromophenyl) -4,6- diphenyl -1,3,5- triazine (6.71 g, 17.3 mmol), CuSO4 (1.0 g, 6.30 mmol), K2CO3 (4.35 g, 31.5 mmol) and 80 mL of o-dichlorobenzene (o-DCB) were introduced into a flask, and the mixture was stirred at 180 ° C. overnight under reflux. After the reaction was completed, a solid was obtained by adding MeOH to the mixture, and the solid was dissolved in CHCl3. The residue was separated by column chromatography, and the solid obtained by adding MeOH was filtered under reduced pressure to obtain compound C-700 (2.0 g, yield: 20%).

[0217] Compound MW Melting point C-700 624.73 236℃

[0218] Example 3: Preparation of Compound C-589

[0219]

[0220] Synthesis of compound 3-1

[0221] 5-Bromobenzo[b]naphtho[1,2-d]thiophene (50.0 g, 160 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-di(1,3,2-dioxaborolane) (48.6 g, 192 mmol), PdCl2(PPh3)2 (5.60 g, 7.98 mmol), KOAc (39.2 g, 399 mmol), and 800 mL of 1,4-dioxane were introduced into a flask, and the mixture was stirred at 130° C. under reflux for 2 hours. After the reaction was completed, the reaction mixture was separated by column chromatography, and the solid obtained by adding MeOH was filtered under reduced pressure to obtain compound 3-1 (41.3 g, yield: 72%).

[0222] Synthesis of compound 3-2

[0223] Compound 3-1 (40.3 g, 112 mmol), 2-bromo-5-chloro-benzaldehyde (25.8 g, 117 mmol), tetrakis(triphenylphosphine)palladium(0) (3.88 g, 3.36 mmol), NaOH (13.4 g, 336 mmol), 450 mL of THF, and 150 mL of H O were introduced into a flask, and the mixture was stirred at 130 ° C for 2 hours under reflux. After the reaction was completed, the reaction mixture was neutralized with an aqueous HCl solution, extracted with EA, and dried over MgSO. The residue was separated by column chromatography, and the solid obtained by adding MeOH was filtered under reduced pressure to obtain compound 3-2 (26.0 g, yield: 62.3%).

[0224] Synthesis of compound 3-3

[0225] Compound 3-2 (25.0 g, 67.0 mmol), (methoxymethyl) triphenylphosphonium chloride (34.6 g, 101 mmol), and 340 mL of THF were introduced into a flask, and while stirring at 0° C., 101 mL of a 1 M K-Ot-Bu solution dissolved in THF was added dropwise thereto. The mixture was stirred for 3 hours, neutralized with NH 4 Cl, extracted with MC, and dried over MgSO 4 . The residue was separated by column chromatography, and the solid obtained by adding MeOH was filtered under reduced pressure to obtain compound 3-3 (37.0 g, yield: 138%).

[0226] Synthesis of compound 3-4

[0227] Compound 3-3 (36.0 g, 89.8 mmol) was dissolved in 450 mL of MC in a flask, and 34 mL of BF 3 · EtOEt was added dropwise thereto while stirring at 0° C. After the reaction was completed, the reaction mixture was neutralized with NaHCO 3 , extracted with MC, and dried over MgSO 4 . The residue was separated by column chromatography, and the solid obtained by adding MeOH was filtered under reduced pressure to obtain compound 3-4 (18.7 g, yield: 56.5%).

[0228] Synthesis of compound C-589

[0229] Compound 3-4 (4.50 g, 12.2 mmol), N-phenyldibenzofuran-3-amine (3.32 g, 12.8 mmol), Pd2(dba)3 (0.559 g, 0.610 mmol), s-phos (0.501 g, 1.22 mmol), NaOt-Bu (2.34 g, 24.4 mmol), and 60 mL of toluene were introduced into a flask, and the mixture was stirred at 140° C. for 2 hours. After the reaction was complete, the mixture was cooled to room temperature and separated by column chromatography. The solid obtained by adding MeOH was then filtered under reduced pressure to obtain compound C-589 (2.5 g, yield: 34.6%).

[0230] Compound MW Melting point C-589 591.72 122.6℃

[0231] Example 4: Preparation of Compound C-101

[0232]

[0233] Synthesis of compound 4-1

[0234] Compound 3-4 (9.0 g, 24.4 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (8.05 g, 31.7 mmol), Pd2(dba)3 (1.12 g, 1.22 mmol), s-phos (1.00 g, 2.44 mmol), KOAc (7.18 g, 73.2 mmol), and 110 mL of 1,4-dioxane were introduced into a flask, and the mixture was stirred at 130° C. under reflux for 2 hours. After the reaction was completed, the reaction mixture was separated by column chromatography, and the solid obtained by adding MeOH was filtered under reduced pressure to obtain compound 4-1 (10.0 g, yield: 89%).

[0235] Synthesis of compound C-101

[0236] Compound 4-1 (5.0 g, 10.9 mmol), 2- (2- bromophenyl) -4,6- diphenyl -1,3,5- triazine (4.22 g, 10.9 mmol), tetrakis (triphenylphosphine) palladium (0) (0.627 g, 0.543 mmol), K2CO3 (3.75 g, 27.2 mmol), 50.0 mL of toluene, 25.0 mL of EtOH, and 25.0 mL of H2O were introduced into a flask, and the mixture was stirred at 140 ° C for 2 hours under reflux. After the reaction was completed, the reaction mixture was diluted by adding water, extracted with EA, and dried over MgSO4. The residue was separated by column chromatography, and the solid obtained by adding MeOH was filtered under reduced pressure to obtain compound C-101 (3.0 g, yield: 43.0%).

[0237] Compound MW Melting point C-101 641.79 254.6℃

[0238] Example 5: Preparation of Compound C-715

[0239]

[0240] Synthesis of compound 5-1

[0241] 4-Chloro-naphtho[1,2-b]benzofuran (50.0 g, 198 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (65.3 g, 257 mmol), Pd2(dba)3 (9.06 g, 9.89 mmol), s-phos (8.13 g, 19.8 mmol), KOAc (58.3 g, 399 mmol), and 1000 mL of 1,4-dioxane were introduced into a flask, and the mixture was stirred at 130° C. under reflux for 3 hours. After the reaction was completed, the reaction mixture was separated by column chromatography, and the solid obtained by adding MeOH was filtered under reduced pressure to obtain compound 5-1 (51.2 g, yield: 75%).

[0242] Synthesis of compound 5-2

[0243] Compound 5-1 (50.2 g, 146 mmol), 2-bromo-5-chloro-benzaldehyde (33.6 g, 153 mmol), tetrakis(triphenylphosphine)palladium(0) (5.06 g, 4.38 mmol), NaOH (17.5 g, 438 mmol), 500 mL of THF, and 250 mL of H O were introduced into a flask, and the mixture was stirred at 130 ° C. for 2 hours under reflux. After the reaction was completed, the reaction mixture was neutralized with an NH4Cl aqueous solution, extracted with EA, and dried over MgSO4. The residue was separated by column chromatography, and the solid obtained by adding MeOH was filtered under reduced pressure to obtain compound 5-2 (36.0 g, yield: 69.1%).

[0244] Synthesis of compound 5-3

[0245] Compound 5-2 (36.0 g, 100.9 mmol), (methoxymethyl) triphenylphosphonium chloride (51.9 g, 151.3 mmol) and 500 mL of THF were introduced into a flask, and while stirring at 0° C., 151.3 mL of a 1M K-Ot-Bu solution dissolved in THF was added dropwise thereto. The mixture was stirred for 3 hours, neutralized with NH 4 Cl, extracted with EA, and dried over MgSO 4 . The residue was separated by column chromatography, and the solid obtained by adding MeOH was filtered under reduced pressure to obtain compound 5-3 (38.0 g, yield: 98%).

[0246] Synthesis of compound 5-4

[0247] Compound 5-3 (37.0 g, 96.1 mmol) was dissolved in 550 mL of MC in a flask, and 251 mL of BF 3 · EtOEt was added dropwise thereto while stirring at 0° C. After the reaction was completed, the reaction mixture was neutralized with NaHCO 3 , extracted with MC, and dried over MgSO 4 . The residue was separated by column chromatography, and the solid obtained by adding MeOH was filtered under reduced pressure to obtain compound 5-4 (13.6 g, yield: 40.1%).

[0248] Synthesis of compound C-715

[0249] Compound 5-4 (4.80 g, 13.6 mmol), N-phenyldibenzofuran-3-amine (3.7 g, 14.3 mmol), Pd2(dba)3 (0.559 g, 0.680 mmol), s-phos (0.501 g, 1.36 mmol), NaOt-Bu (2.61 g, 27.2 mmol) and 70 mL of o-xylene were introduced into a flask, and the mixture was stirred at 190 ° C for 1.5 hours. After the reaction was completed, the mixture was cooled to room temperature and separated by column chromatography. The solid obtained by adding MeOH was then filtered under reduced pressure to obtain compound C-715 (3.9 g, yield: 49.8%).

[0250] Compound MW Melting point C-715 575.67 258.9℃

[0251] Example 6: Preparation of Compound C-13

[0252]

[0253] Synthesis of compound 6-1

[0254] Compound 5-4 (9.0 g, 25.5 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (8.43 g, 33.2 mmol), Pd2(dba)3 (1.17 g, 1.28 mmol), s-phos (1.05 g, 2.55 mmol), KOAc (7.50 g, 76.5 mmol), and 130 mL of 1,4-dioxane were introduced into a flask, and the mixture was stirred at 130° C. under reflux for 3 hours. After the reaction was completed, the reaction mixture was separated by column chromatography, and the solid obtained by adding MeOH was filtered under reduced pressure to obtain compound 6-1 (10.5 g, yield: 92.7%).

[0255] Synthesis of compound C-13

[0256] Compound 6-1 (5.0 g, 11.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (3.03 g, 11.3 mmol), tetrakis(triphenylphosphine)palladium(0) (0.650 g, 0.563 mmol), K2CO3 (3.88 g, 28.1 mmol), 30 mL of toluene, 10 mL of EtOH, and 10 mL of H2O were introduced into a flask, and the mixture was stirred at 130 ° C for 2 hours under reflux. After the reaction was completed, the reaction mixture was filtered and dried. The residue was separated by column chromatography, and the solid obtained by adding MeOH was filtered under reduced pressure to obtain compound C-13 (2.5 g, yield: 40.3%).

[0257] Compound MW Melting point C-13 549.63 297.4℃

[0258] Example 7: Preparation of Compound C-220

[0259]

[0260] Compound 4-1 (4.7 g, 10.2 mmol), 2-chloro-4-(dibenzo[b, d]furan-1-yl)-6-phenyl-1,3,5-triazine (3.84 g, 10.7 mmol), tetrakis(triphenylphosphine)palladium(0) (0.589 g, 0.51 mmol), K2CO3 (3.52 g, 25.5 mmol), 30.0 mL of toluene, 10.0 mL of EtOH, and 10.0 mL of H2O were introduced into a flask, and the mixture was stirred at 140°C for 2 hours under reflux. After the reaction was completed, the reaction mixture was diluted by adding water, extracted with EA, and dried over MgSO4. The residue was separated by column chromatography, and the solid obtained by adding MeOH was filtered under reduced pressure to obtain compound C-220 (3.6 g, yield: 53.8%).

[0261] Compound MW Melting point C-220 655.78 346.5℃

[0262] Device Example 1: Production of a Red-Emitting OLED According to the Disclosure

[0263] An OLED comprising a compound according to the present disclosure is produced. A transparent electrode indium tin oxide (ITO) film (10Ω / sq) on a glass substrate for OLED (GEOMATEC CO., LTD., Japan) is ultrasonically washed with acetone and isopropyl alcohol in sequence, and then stored in isopropyl alcohol. The ITO substrate is then mounted on a substrate holder of a vacuum vapor deposition device. Compound HI-1 is introduced into a chamber of a vacuum vapor deposition device, and compound HT-1 is introduced into another chamber. The two materials are evaporated at different rates, and compound HI-1 is deposited in an amount of 3wt% based on the total amount of compound HI-1 and compound HT-1 to form a hole injection layer with a thickness of 10nm on the ITO substrate. Next, compound HT-1 is introduced into a chamber of a vacuum vapor deposition device and the compound is evaporated by applying an electric current to the chamber, thereby forming a first hole transport layer with a thickness of 80nm on the hole injection layer. Compound HT-2 was then introduced into another chamber of a vacuum vapor deposition apparatus and evaporated by applying an electric current to the chamber, forming a second hole transport layer with a thickness of 60 nm on the first hole transport layer. After forming the hole injection layer and hole transport layer, a light-emitting layer was formed thereon as follows: Compound C-686 was introduced as a host into one chamber of a vacuum vapor deposition apparatus, and compound D-39 was introduced as a dopant into another chamber. The two materials were evaporated at different rates, and the dopant was deposited at a doping amount of 3 wt% based on the total amount of host and dopant, forming a light-emitting layer with a thickness of 40 nm on the second hole transport layer. Compound ETL-1 and compound EIL-1 were evaporated as electron transport materials in a 50:50 weight ratio to form a 35 nm thick electron transport layer on the light-emitting layer. After compound EIL-1 was deposited as a 2 nm thick electron injection layer on the electron transport layer, an 80 nm thick Al cathode was deposited on the electron injection layer using another vacuum vapor deposition apparatus. Thus, an OLED was produced. All compounds used as materials were -6 Purify by vacuum sublimation under vacuum.

[0264] Device Example 2: Production of a Red-Emitting OLED According to the Disclosure

[0265] An OLED was produced in the same manner as in Device Example 1, except that Compound C-700 was used as a host of the light-emitting layer.

[0266] Comparative Example: Production of OLEDs containing comparative compounds as hosts

[0267] An OLED was produced in the same manner as in Device Example 1, except that compound CBP was used as a host of the light-emitting layer.

[0268] Table 1 below provides the driving voltage, luminous efficiency, and luminescent color of the OLEDs produced in Device Examples 1 and 2 and Comparative Example at a luminance of 1,000 nits, and the time it takes for the luminance to decrease from 100% to 95% at a luminance of 5,000 nits (lifetime; T95).

[0269] [Table 1]

[0270]

[0271] The OLED including the organic electroluminescent compound according to the present disclosure as a host exhibits lower driving voltage, higher luminous efficiency, and excellent lifespan characteristics compared to the OLED using the compound of the comparative example.

[0272] Device Examples 3 to 6: Production of Red-Emitting OLEDs According to the Disclosure

[0273] An OLED according to the present disclosure was produced. A transparent electrode indium tin oxide (ITO) film (10Ω / sq) on a glass substrate for OLED (Japan Gioma Co., Ltd.) was ultrasonically washed with acetone and isopropyl alcohol in sequence, and then stored in isopropyl alcohol. The ITO substrate was then mounted on a substrate holder of a vacuum vapor deposition device. Compound HI-1 was introduced into a chamber of a vacuum vapor deposition device, and compound HT-1 was introduced into another chamber. The two materials were evaporated at different rates, and compound HI-1 was deposited in an amount of 3wt% based on the total amount of compound HI-1 and compound HT-1 to form a hole injection layer with a thickness of 10nm on the ITO substrate. Next, compound HT-1 was introduced into a chamber of a vacuum vapor deposition device and the compound was evaporated by applying an electric current to the chamber, thereby forming a first hole transport layer with a thickness of 80nm on the hole injection layer. Compound HT-2 was then introduced into another chamber of a vacuum vapor deposition apparatus and evaporated by applying an electric current to the chamber, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light-emitting layer was formed thereon as follows: the first host material and the second host material shown in Table 2 below were introduced as hosts into two chambers of a vacuum vapor deposition apparatus, respectively, and compound D-39 was introduced as a dopant into another chamber. The two host materials were evaporated at a rate of 1:1 and the dopant material was evaporated simultaneously at different rates, and the dopant was deposited at a doping amount of 3 wt% based on the total amount of host and dopant to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer. Compounds ETL-1 and EIL-1 were evaporated as electron transport materials at a weight ratio of 50:50 to form an electron transport layer having a thickness of 35 nm on the light-emitting layer. After depositing the compound EIL-1 as an electron injection layer with a thickness of 2 nm on the electron transport layer, an Al cathode with a thickness of 80 nm was deposited on the electron injection layer by another vacuum vapor deposition device. Thus, an OLED was produced. All the compounds used as materials were -6 Purify by vacuum sublimation under vacuum.

[0274] The driving voltage, luminous efficiency, and luminescent color of the OLEDs produced in Device Examples 3 to 6 at a luminance of 1,000 nits, and the time taken for the luminance to decrease from 100% to 95% at a luminance of 5,000 nits (lifetime; T95) are provided in Table 2 below.

[0275] [Table 2]

[0276]

[0277] The OLED according to the present disclosure exhibits low driving voltage, high luminous efficiency, and remarkably excellent lifespan characteristics.

[0278] [Table 3]

[0279]

Claims

1. An organic electroluminescent compound, which is represented by the following formula 1: in Ring A is selected from the following formulae: X represents O or S; R1 each independently represents hydrogen, deuterium, halogen, or cyano; R 21 represents -L1-Ar1; L1 each independently represents a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted 3- to 30-membered heteroarylene group; Ar1 each independently represents a cyano group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted silyl group, or a substituted or unsubstituted amino group; a represents an integer from 1 to 4, and b represents an integer of 1, wherein if a is an integer of 2 or greater, each R1 may be the same or different; * indicates the site of fusion with the 5-membered ring containing X, wherein In L1 and Ar1, the substituents of the substituted alkyl, substituted cycloalkyl, substituted heterocycloalkyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted silyl, and substituted amino are each independently at least one selected from the group consisting of: deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; phosphine oxide; C1-C30 alkyl; halo(C1-C30)alkyl; C2-C30 alkenyl; C2-C30 alkynyl; C1-C30 alkoxy; C1-C30 alkylthio; C3-C30 cycloalkyl; C3-C30 cycloalkenyl; 3- to 7-membered heterocycloalkyl; C6-C30 aryloxy; C6-C30 arylthio; 3- to 30-membered heteroaryl, which is unsubstituted or substituted with one or more C6-C30 aryl groups; C6-C30 aryl, which is unsubstituted or substituted with at least one of one or more C1-C30 alkyl groups and one or more 3- to 30-membered heteroaryl groups; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30 )alkyldi(C6-C30)arylsilyl; amino; mono- or di-(C1-C30)alkylamino; mono- or di-(C2-C30)alkenylamino; mono- or di-(C6-C30)arylamino; mono- or di-(3- to 30-membered)heteroarylamino; (C1-C30)alkyl(C2-C30)alkenylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkyl(3- to 30-membered)heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; ( (C2-C30)alkenyl(3- to 30-membered)heteroarylamino; (C6-C30)aryl(3- to 30-membered)heteroarylamino; C1-C30 alkylcarbonyl; C1-C30 alkoxycarbonyl; C6-C30 arylcarbonyl; C6-C30 arylphosphine; di(C6-C30)arylborylcarbonyl; di(C1-C30)alkylborylcarbonyl; (C1-C30)alkyl(C6-C30)arylborylcarbonyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl.

2. The organic electroluminescent compound according to claim 1, wherein L1 each independently represents a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenylene group, or a substituted or unsubstituted pyridylene group.

3. The organic electroluminescent compound according to claim 1, wherein The substituted or unsubstituted 3- to 30-membered heteroaryl groups of Ar1 each independently represent a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinolyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted dibenzoquinolyl group, a substituted or unsubstituted dibenzoquinazolinyl group, a substituted or unsubstituted dibenzoquinoxalinyl, substituted or unsubstituted indenopyridinyl, substituted or unsubstituted indenopyrimidinyl, substituted or unsubstituted indenopyrazinyl, substituted or unsubstituted benzofuranopyridinyl, substituted or unsubstituted benzofuranopyrimidinyl, substituted or unsubstituted benzofuranopyrazinyl, substituted or unsubstituted benzothienopyridinyl, substituted or unsubstituted benzothienopyrimidinyl, substituted or unsubstituted benzothienopyrazinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothienyl.

4. The organic electroluminescent compound according to claim 1, wherein The compound represented by Formula 1 is selected from the following compounds: An organic electroluminescent material comprising the organic electroluminescent compound according to claim 1 . An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1 .

7. The organic electroluminescent device according to claim 6, wherein: The organic electroluminescent compound is contained in the light emitting layer or the hole transporting zone.

8. The organic electroluminescent device according to claim 7, wherein: When the organic electroluminescent compound is contained in the light-emitting layer, the light-emitting layer further contains a compound represented by the following Formula 2: in X1 and Y1 each independently represent -N=, -NR7-, -O-, or -S-, provided that either one of X1 and Y1 represents -N=, and the other of X1 and Y1 represents -NR7-, -O-, or -S-; R' represents a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted 3- to 30-membered heteroaryl group; R2 to R7 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3- to 30-membered heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted fused ring group of one or more C3-C30 aliphatic rings and one or more C6-C30 aromatic rings, substituted or unsubstituted mono- or di-(C1-C30)alkylamino or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, substituted or unsubstituted mono- or di-(3- to 30-membered)heteroarylamino, substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, substituted or unsubstituted mono- or di-(3- to 30-membered)heteroarylamino, substituted or unsubstituted (C2-C30)alkenyl(C6-C30)arylamino, substituted or unsubstituted (C2-C30)alkenyl(3- to 30-membered)heteroarylamino, or substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino; or may be linked to adjacent substituents to form one or more rings; L' represents a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted 3- to 30-membered heteroarylene group; and f represents 1, g and h each independently represent 1 or 2, and i represents an integer of 1 to 4, wherein if each of g to i is an integer of 2 or greater, each R2 to each R4 may be the same or different.

9. The organic electroluminescent device according to claim 8, wherein: The compound represented by Formula 2 is selected from the following compounds:

10. The organic electroluminescent device according to claim 7, wherein: When the organic electroluminescent compound is contained in the light-emitting layer, the light-emitting layer further contains a compound represented by the following Formula 3: <h2 style=";text-align:left;direction:ltr">HAr-((L2)<h2 style=";text-align:left;direction:ltr"> e <h2 style=";text-align:left;direction:ltr"> -Ar2)<h2 style=";text-align:left;direction:ltr"> d <h2 style=";text-align:left;direction:ltr"> -----(3) in HAr represents a substituted or unsubstituted 3- to 20-membered heteroaryl group containing one or more nitrogen atoms; L2 each independently represents a substituted or unsubstituted C6-C30 arylene group; Ar2 each independently represents a substituted or unsubstituted C6-C30 aryl group, or the following formula 4, provided that at least one of Ar2 represents formula 4; Y represents O, S, CR 41 R 42 , N-*, or NR 43 ; R 41 to R 43 Each independently represents a substituted or unsubstituted C1-C30 alkyl group, or a substituted or unsubstituted C6-C30 aryl group, or R 41 and R 42 Can be connected to each other to form a ring; R 31 to R 38 Each independently represents a site for attachment to L2; or represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3- to 30-membered heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkane alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted fused ring group of one or more C3-C30 aliphatic rings and one or more C6-C30 aromatic rings, or -L4-N(Ar3)(Ar4); or may be connected with adjacent substituents to form one or more rings; L4 each independently represents a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted 3- to 30-membered heteroarylene group; Ar3 and Ar4 each independently represent hydrogen, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted fused ring group of one or more C3-C30 aliphatic rings and one or more C6-C30 aromatic rings, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted 3- to 30-membered heteroaryl group; d represents an integer from 1 to 3, wherein if d is an integer of 2 or greater, each ((L2) e -Ar2) may be the same or different; e represents an integer from 0 to 2, wherein if e is 2, each L2 may be the same or different; and * indicates the site of attachment to L2. The organic electroluminescent device according to claim 10 , wherein: The compound represented by Formula 3 is selected from the following compounds:

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