Organic electroluminescent compound and organic electroluminescent device comprising same

Abstract

The present application relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. The present disclosure relates to an organic electroluminescent compound represented by Formula 1 and an organic electroluminescent device comprising the same. By comprising the organic electroluminescent compound of the present disclosure, it is possible to provide an organic electroluminescent device having improved driving voltage, luminous efficiency, lifespan characteristics, and / or power efficiency.

Description

Technical Field

[0001] This disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. Background Technology

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

[0003] The most important factor determining the luminescence efficiency in organic electroluminescent devices (OLEDs) is the luminescent material. Fluorescent materials have been widely used as luminescent materials to date. However, given the electroluminescence mechanism, phosphorescent materials have been extensively studied because they theoretically enhance luminescence efficiency by four (4) times compared to fluorescent materials. To date, iridium (III) complexes have been well-known as phosphorescent materials, including bis(2-(2'-benzothiophene)-pyridine-N,C-3')(acetylacetone)iridium[(acac)Ir(btp)2], tris(2-phenylpyridine)iridium[Ir(ppy)3], and bis(4,6-difluorophenylpyridine-N,C2)pyridinecarboxyiridium (Firpic), which are luminescent in red, green, and blue, respectively.

[0004] Among existing technologies, 4,4'-N,N'-dicarbazole-biphenyl (CBP) is the most well-known phosphorescent host material. Recently, Pioneer Corporation (Japan) and others have developed high-performance OLEDs using copper bath (BCP), a hole-blocking material, and aluminum (III) bis(2-methyl-8-quinoline salt)(4-phenylphenol salt) (BAlq) as host materials.

[0005] However, while conventional materials offer good luminescence characteristics, they have the following drawbacks: (1) Due to their low glass transition temperature and poor thermal stability, they may degrade during high-temperature deposition processes in a vacuum, potentially shortening the device's lifespan. (2) The power efficiency of an OLED is derived from [(π / voltage) × current efficiency], and power efficiency is inversely proportional to voltage. Although OLEDs containing phosphorescent host materials offer higher current efficiency (cd / A) than OLEDs containing fluorescent materials, they require considerably higher driving voltages. Therefore, there is no advantage in terms of power efficiency (lm / W). (3) Furthermore, OLEDs have short operating lifetimes, and there is still a need to improve luminescence efficiency.

[0006] Various materials or concepts for organic layers in organic electroluminescent devices have been proposed to enhance luminous efficiency, driving voltage, and / or lifetime characteristics. However, they have not been satisfactory in practical applications.

[0007] Korean Patent Application Publication Nos. 2014-0055137 and 2015-0126340 disclose fused carbazole derivatives. However, there is a continued need for developing organic electroluminescent materials to improve OLED performance. Summary of the Invention

[0008] Technical issues

[0009] The purpose of this disclosure is to provide an organic electroluminescent compound that is effective in producing organic electroluminescent devices with improved driving voltage, luminous efficiency, lifetime characteristics, and / or power efficiency. Another purpose of this disclosure is to provide an organic electroluminescent device comprising the said organic electroluminescent compound.

[0010] Solution to the problem

[0011] Compounds containing an aryl moiety exhibit high stability when used in electrical devices. The inventors of this invention have discovered that phenanthrene-based compounds possess higher HOMO, LUMO, and triplet band gaps (E0) than anthracene-based compounds. T Therefore, phenanthrene-based compounds were introduced into organic electroluminescent devices. As a result, higher stability was demonstrated compared to the introduction of anthracene-based compounds. This can also be explained by Clar's rule. That is, this higher stability appears to be due to the effect of the phenanthrene structure, which has lower bridging conjugation and steric hindrance compared to the anthracene structure. More specifically, the inventors of this invention have discovered that the above objectives can be achieved by organic electroluminescent compounds represented by the following formula 1:

[0012]

[0013] in

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

[0015]

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

[0017] R1 can be independently represented by hydrogen, deuterium, halogen, or cyano;

[0018] R 11It 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.

[0019] R 12 and R 13 Each of these elements 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 they may be linked together to form a ring.

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

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

[0022] Ar1 can independently represent 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, b represents an integer from 1 to 10, where if a and b are integers of 2 or greater, then each R1 and each R 21 They can be the same or different;

[0024] * indicates a site that is fused with a 5-membered ring containing X;

[0025] The premise is that X is NR 11 Then ring A is not

[0026] Beneficial effects of the present invention

[0027] By using the organic electroluminescent compounds disclosed herein, organic electroluminescent devices with low driving voltage, high luminous efficiency, excellent lifetime characteristics, and / or high power efficiency can be produced. Detailed Implementation

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

[0029] The term "organic electroluminescent compound" in this disclosure refers to a compound that can be used in an organic electroluminescent device. If desired, the organic electroluminescent compound can be included in any layer constituting the organic electroluminescent device.

[0030] The term "organic electroluminescent material" in this disclosure refers to a material that can be used in an organic electroluminescent device and may contain at least one compound. If desired, the organic electroluminescent material may be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole assist material, a light-emitting assist material, an electron blocking material, a light-emitting material (including a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0031] The organic electroluminescent material disclosed herein may comprise at least one compound represented by Formula 1. The compound represented by Formula 1 may be included in, but is not limited to, a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and / or an electron injection layer. The compound represented by Formula 1 may be included in at least one layer constituting the hole transport region, but is not limited to this. When included in the hole transport layer, hole auxiliary layer, or light-emitting auxiliary layer of the hole transport region, the compound represented by Formula 1 may be included as a hole transport material, a hole auxiliary material, or a light-emitting auxiliary material. Furthermore, when included in the light-emitting layer, the compound represented by Formula 1 may be included as a host material, but is not limited to this. In this document, the host material may be the host material of a blue, green, or red organic electroluminescent device.

[0032] The compounds represented by Formula 1 will be described in more detail below.

[0033] In this document, the term "(C1-C30)alkyl" refers to a straight-chain or branched 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 aforementioned alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, etc. The term "(C2-C30)alkenyl" refers to a straight-chain or branched 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 aforementioned alkenyl group may include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc. The term "(C2-C30) ynyl" refers to a straight-chain or branched ynyl 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 aforementioned ynyl group may include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpentan-2-ynyl, etc. The term "(C3-C30) cycloalkyl" refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 carbon atoms in the cyclic skeleton, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The aforementioned cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, etc. The term "(3- to 7-membered) heterocyclic alkyl" refers to a cycloalkyl group having 3 to 7, preferably 5 to 7, cyclic skeleton atoms and containing at least one heteroatom, wherein the heteroatom is selected from the group consisting of B, N, O, S, Si, and P, and preferably from the group consisting of O, S, and N. The aforementioned heterocyclic alkyl group may include tetrahydrofuran, pyrrolidine, tetrahydrothiophene, tetrahydropyran, etc. The term "(C6-C30)(aryl)alkyl" refers to a monocyclic or fused-ring group derived from an aromatic hydrocarbon having 6 to 30 cyclic skeleton carbon atoms, wherein the number of cyclic skeleton carbon atoms is preferably 6 to 25, and more preferably 6 to 18. The aforementioned (aryl)alkyl group may be partially saturated and may contain a spirostructure. The aforementioned aryl groups may include phenyl, biphenyl, terphenyl, naphthyl, binatyl, phenylnaphthyl, naphthylphenyl, phenyl terphenyl, fluorenyl, phenylfluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, phenylphenanthryl, anthracene, indene, triphenylene, pyrene, tetraphenyl, perylene, etc. Aryl, naphthyl, fluoranthyl, spirodifluorenyl, azulel, tetramethyldihydrophenanthryl, etc. More specifically, the above-mentioned aryl groups may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthrayl, 2-anthrayl, 9-anthrayl, benzanthyl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthyl, pyrene, 1- basal, 2- basal, 3- basal, 4- Base, 5- Base, 6- Benzyl, benzo[c]phenanthrene, 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, dibenzo[a]fluorenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, o-triphenyl, m-triphenyl-4-yl, m-triphenyl-3-yl, m-triphenyl-2-yl, p-triphenyl-4-yl, p-triphenyl-3-yl, p-triphenyl-2-yl, m-tetraphenyl, 3-fluoranthyl, 4-fluoranthyl, 8-fluoranthyl, 9-fluoranthyl, benzo[a]fluoranthyl, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl 4'-methylbiphenyl, 4'-tert-butyl-p-triphenyl-4'-yl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9, 9-Diphenyl-1-fluorenyl, 9,9-Diphenyl-2-fluorenyl, 9,9-Diphenyl-3-fluorenyl, 9,9-Diphenyl-4-fluorenyl, 11,11-Dimethyl-1-benzo[a]fluorenyl, 11,11-Dimethyl-2-benzo[a]fluorenyl, 11,11-Dimethyl-3-benzo[a]fluorenyl, 11,11-Dimethyl-4-benzene [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 a]fluorenyl, 11,11-dimethyl-1-benzo[b]fluorenyl, 11,11-dimethyl-2-benzo[b]fluorenyl, 11,11-dimethyl-3-benzo[b]fluorenyl, 11,11-dimethyl-4-benzo[b]fluorenyl, 11,11-dimethyl-5-benzo[b]fluorenyl, 11,11-dimethyl-6-benzo[b]fluorenyl 11,11-dimethyl-7-benzo[b]fluorenyl, 11,11-dimethyl-8-benzo[b]fluorenyl, 11,11-dimethyl-9-benzo[b]fluorenyl, 11,11-dimethyl-10-benzo[b]fluorenyl, 11,11-dimethyl-1-benzo[c]fluorenyl, 11,11-dimethyl-2-benzo[c]fluorenyl 11,11-Dimethyl-3-benzo[c]fluorenyl, 11,11-Dimethyl-4-benzo[c]fluorenyl, 11,11-Dimethyl-5-benzo[c]fluorenyl, 11,11-Dimethyl-6-benzo[c]fluorenyl, 11,11-Dimethyl-7-benzo[c]fluorenyl, 11,11-Dimethyl-8-benzo[c]fluorenyl, 11,11-Dimethyl-9-benzo[c]fluorenyl, 11,11-dimethyl-10-benzo[c]fluorenyl, 11,11-diphenyl-1-benzo[a]fluorenyl, 11,11-diphenyl-2-benzo[a]fluorenyl, 11,11-diphenyl-3-benzo[a]fluorenyl, 11,11-diphenyl-4-benzo[a]fluorenyl, 11,11-diphenyl-5-benzo[a]fluorenyl, 11,11-diphenyl-6-benzo[a]fluorenyl, 11,11-diphenyl-7-benzo[a]fluorenyl, 11,11-diphenyl -8-benzo[a]fluorenyl, 11,11-diphenyl-9-benzo[a]fluorenyl, 11,11-diphenyl-10-benzo[a]fluorenyl, 11,11-diphenyl-1-benzo[b]fluorenyl, 11,11-diphenyl-2-benzo[b]fluorenyl, 11,11-diphenyl-3-benzo[b]fluorenyl, 11,11-diphenyl-4-benzo[b]fluorenyl, 11,11-diphenyl-5-benzo[b]fluorenyl, 11,11-diphenyl-6-benzo[b]fluorenyl, 11,11-diphenyl-7-benzo[b]fluorenyl ]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-phenanthyl, 9,9,10,10-tetramethyl-9,10-dihydro-2-phenanthyl, 9,9,10,10-tetramethyl-9,10-dihydro-3-phenanthyl, 9,9,10,10-tetramethyl-9,10-dihydro-4-phenanthyl, etc.

[0034] The term "(3- to 30-)-heteroaryl" refers to 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 aforementioned heteroaryl group can be monocyclic or a fused ring condensed with at least one benzene ring; it can be partially saturated; it can be a heteroaryl group formed by linking at least one heteroaryl group or an aryl group to another heteroaryl group via one or more single bonds; and it can contain a spirostructure. The aforementioned heteroaryl group can include monocyclic heteroaryl groups such as furanyl, thiophene, pyrrole, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetraazinyl, triazolyl, tetraazolyl, furazonyl, pyridinyl, pyrazinyl, pyrimidinyl, and pyridazinyl, and fused ring heteroaryl groups such as benzofuranyl, benzothiophene, isobenzofuranyl, diphenyl benzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, benzofuran-quinolinyl, benzofuran-quinazolinyl, benzofuran-naphthidyl, benzofuran-pyrimidyl, naphthofuran-pyrimidyl, benzothiophene-quinolinyl, benzothiophene-quinazolinyl, benzothiophene-naphthidyl, benzothiophene-pyrimidyl, naphthothiophene-pyrimidyl, pyrimidylindolyl Benzopyrimidindolyl, benzofuranopyrazinyl, naphthofuranopyrazinyl, benzothiophenopyrazinyl, naphthothiophenopyrazinyl, pyrazindolyl, benzopyrazindolyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisooxazolyl, benzooxazolyl, isoindolyl, indolyl, benzoindolyl, indazole, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quin Azolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphridinyl, carbazole, benzocarbazole, dibenzocarbazole, phenoxazinyl, phenthiazinyl, phenanthidyl, benzodioxacyclopentenyl, dihydroacridinyl, benzotriazolephenazinyl, imidazopyridinyl, benzopyranoquinazolinyl, thiobenzopyranoquinazolinyl, dimethylbenzopyrimidinyl, indolocarbazole, indenecarbazole, etc. More specifically, the aforementioned heteroaryl groups may include 1-pyrrolithyl, 2-pyrrolithyl, 3-pyrrolithyl, pyrazinyl, 2-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indololinyl, 2-indololinyl, 3-indololinyl, 5-indololinyl, 6-indololinyl, etc. Dolinyl, 7-indolinyl, 8-indolinyl, 2-imidazopyridyl, 3-imidazopyridyl, 5-imidazopyridyl, 6-imidazopyridyl, 7-imidazopyridyl, 8-imidazopyridyl, 3-pyridyl, 4-pyridyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl5-Isoindolyl, 6-Isoindolyl, 7-Isoindolyl, 2-furanyl, 3-furanyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl 1-Isobenzofuranyl, 7-Isobenzofuranyl, 2-quinolinyl, 3-quinolinyl, 4-quinolinyl, 5-quinolinyl, 6-quinolinyl, 7-quinolinyl, 8-quinolinyl, 1-isoquinolinyl, 3-isoquinolinyl, 4-isoquinolinyl, 5-isoquinolinyl, 6-isoquinolinyl, 7-isoquinolinyl, 8-isoquinolinyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1 -Carbazole, 2-Carbazole, 3-Carbazole, 4-Carbazole, 9-Carbazole, azacarbazole-1-yl, azacarbazole-2-yl, azacarbazole-3-yl, azacarbazole-4-yl, azacarbazole-5-yl, azacarbazole-6-yl, azacarbazole-7-yl, azacarbazole-8-yl, azacarbazole-9-yl, 1-Phenyridyl 2-Phenyridyl, 3-Phenyridyl, 4-Phenyridyl, 6-Phenyridyl, 7-Phenyridyl, 8-Phenyridyl, 9-Phenyridyl, 10-Phenyridyl, 1-Acridineyl, 2-Acridineyl, 3-Acridineyl, 4-Acridineyl, 9-Acridineyl, 2-Oxazolyl, 4-Oxazolyl, 5-Oxazolyl, 2-Oxadiazolyl, 5-Oxadiazolyl, 3-Furazonyl, 2-Thiophenyl 3-Thienyl, 2-methylpyrrolo-1-yl, 2-methylpyrrolo-3-yl, 2-methylpyrrolo-4-yl, 2-methylpyrrolo-5-yl, 3-methylpyrrolo-1-yl, 3-methylpyrrolo-2-yl, 3-methylpyrrolo-4-yl, 3-methylpyrrolo-5-yl, 2-tert-butylpyrrolo-4-yl, 3-(2-phenylpropyl)pyrrolo-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4-tert-butyl-1-indolyl, 2-tert-butyl-3-indolyl, 4-tert-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl 1-Dibenzothiophene, 2-Dibenzothiophene, 3-Dibenzothiophene, 4-Dibenzothiophene, 1-Naphtho-[1,2-b]-benzofuranyl, 2-Naphtho-[1,2-b]-benzofuranyl, 3-Naphtho-[1,2-b]-benzofuranyl, 4-Naphtho-[1,2-b]-benzofuranyl, 5-Naphtho-[1,2-b]-benzofuranyl [-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 -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]-benzofuran 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 Thiophene, 8-naphtho-[1,2-b]-benzothiophene, 9-naphtho-[1,2-b]-benzothiophene, 10-naphtho-[1,2-b]-benzothiophene, 1-naphtho-[2,3-b]-benzothiophene, 2-naphtho-[2,3-b]-benzothiophene, 3-naphtho-[2,3-b]-benzothiophene, 4-naphtho- -[2,3-b]-benzothiophene, 5-naphtho-[2,3-b]-benzothiophene, 1-naphtho-[2,1-b]-benzothiophene, 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-benzyl benzofuran[3,2-d]pyrimidinyl, 7-benzofuran[3,2-d]pyrimidinyl, 8-benzofuran[3,2-d]pyrimidinyl, 9-benzofuran[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-Benzofurano[3,2-d]pyrazinyl, 6-Benzofurano[3,2-d]pyrazinyl, 7-Benzofurano[3,2-d]pyrazinyl, 8-Benzofurano[3,2-d]pyrazinyl, 9-Benzofurano[3,2-d]pyrazinyl, 2-Benzothieno[3,2-d]pyrazinyl, 6-Benzothieno[3,2-d]pyrazinyl, 7-Benzothieno[3,2-d]pyrazinyl The compounds include benzothieno[3,2-d]pyrazinyl, 8-benzothieno[3,2-d]pyrazinyl, 9-benzothieno[3,2-d]pyrazinyl, 1-siliconfluorenyl, 2-siliconfluorenyl, 3-siliconfluorenyl, 4-siliconfluorenyl, 1-germaniumfluorenyl, 2-germaniumfluorenyl, 3-germaniumfluorenyl, 4-germaniumfluorenyl, 1-dibenzo[2,2-d]benzenelenyl, 2-dibenzo[2,2-d]benzenelenyl, 3-dibenzo[2,2-d]benzenelenyl, and 4-dibenzo[2,2-d]benzenelenyl. In addition, "halogens" include F, Cl, Br, and I.

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

[0036] In this document, "substituted" in the phrase "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), and is replaced by a substituent group in which two or more substituents are attached. For example, "a substituent in which two or more substituents are attached" could be pyridine-triazine. That is, pyridine-triazine could be a heteroaryl group or could be interpreted as a substituent in which two heteroaryl groups are attached. In the formula disclosed herein, the substituents of the substituted alkyl, substituted cycloalkyl, substituted heterocycloalkyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted silyl, and substituted amino groups are each independently selected from at least one of the following groups: 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)heterocyclic alkyl; (C6-C30)aryloxy; (C6-C30)arylthio; unsubstituted or (3- to 30-membered)heteroaryl substituted with one or more (C6-C30)aryl groups; unsubstituted or (C6-C30)aryl substituted with at least one of one or more (C1-C30) alkyl 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 Silyl; (C1-C30)alkylbis(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) heteroarylamino; (C6-C30) aryl (3 to 30) heteroarylamino; (C1-C30) alkyl carbonyl; (C1-C30) alkoxy carbonyl; (C6-C30) aryl carbonyl; (C6-C30) arylphosphine; di(C6-C30) arylboron carbonyl; di(C1-C30) alkylboron carbonyl; (C1-C30) alkyl(C6-C30) arylboron carbonyl; (C6-C30) aryl(C1-C30) alkyl; and (C1-C30) alkyl(C6-C30) aryl.According to one embodiment of this disclosure, each substituent is independently at least one selected from the group consisting of: (C1-C6)alkyl, (C6-C20)aryl, unsubstituted or substituted (C6-C15) aryl (5- to 15-membered) heteroaryl, di(C6-C12)arylamino, and (C1-C6)alkyl(C6-C15)aryl. Specifically, each substituent may be independently at least one selected from the group consisting of: methyl, phenyl, naphthyl, biphenyl, phenanthrene, benzo[a]phenanthrene, dimethylfluorenyl, dibenzofuranyl, dibenzothiopheneyl, diphenyltriazinyl, phenylnaphthyltriazinyl, phenylcarbazoyl, and diphenylamino.

[0037] In Equation 1, ring A is selected from the following equation.

[0038]

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

[0040]

[0041] According to another embodiment of this disclosure, ring A is selected from the following formula.

[0042]

[0043] According to yet another embodiment of this disclosure, ring A is selected from the following formula.

[0044]

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

[0046] In this article, R 11 This indicates 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. According to one embodiment of this disclosure, R 11 This refers to a substituted or unsubstituted (C6-C15) aryl group, or a substituted or unsubstituted heteroaryl group containing one or more nitrogen atoms (5-membered to 15-membered). According to another embodiment of this disclosure, R... 11This refers to a (C6-C15) aryl group substituted with 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 with 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 this disclosure, R 11 To R 13 The substituted or unsubstituted (3- to 30-membered) heteroaryl groups are each independently represented by substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazine, substituted or unsubstituted pyrazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted dibenzoquinolinyl, substituted or unsubstituted dibenzoquinoxalinyl, substituted or unsubstituted... Dibenzoquinoxalinyl, substituted or unsubstituted indopyridyl, substituted or unsubstituted indopyrimidyl, substituted or unsubstituted indopyrazinyl, substituted or unsubstituted benzofuranopyridyl, substituted or unsubstituted benzofuranopyrimidyl, substituted or unsubstituted benzofuranopyrazinyl, substituted or unsubstituted benzothiophenopyridyl, substituted or unsubstituted benzothiophenopyrimidyl, substituted or unsubstituted benzothiophenopyrazinyl, substituted or unsubstituted carbazoleyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl. Specifically, R 11 It can represent a phenyl group substituted with diphenyltriazine or diphenylamino; a naphthyl group substituted with diphenyltriazine or phenylnaphthyltriazine; a triazine, quinazolinyl, quinoxalinyl, or benzoquinoxalinyl group substituted with at least one of one or more phenyl groups, one or more naphthyl groups, one or more biphenyl groups, one or more phenanthryl groups, one or more benzophenanthryl groups, one or more dibenzofuranyl groups, one or more dibenzothiophenyl groups, and one or more phenylcarbazoyl groups; etc.

[0047] In addition, R 12 and R 13 Each of these elements 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 they may be linked together to form a ring. According to one embodiment of this disclosure, R 12 and R 13 Each can be independently represented as methyl, ethyl, or propyl.

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

[0049] In this document, L1 independently represents a single-bonded, substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group. According to one embodiment of this disclosure, L1 independently represents a single-bonded, substituted or unsubstituted (C6-C15) aryl group, or a substituted or unsubstituted (5- to 15-membered) heteroaryl group. According to another embodiment of this disclosure, L1 independently represents a single-bonded, unsubstituted, or (C6-C15) aryl group substituted with one or more (C6-C15) aryl groups, or an unsubstituted (5- to 15-membered) heteroaryl group. According to another embodiment of this disclosure, L1 can independently represent a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted phenanthylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted fluorene, or a substituted or unsubstituted pyridylene. Specifically, L1 can independently represent a single bond, a phenylene, a naphthylene, a biphenylene, a phenylene substituted with a phenyl group, a pyridylene, etc.

[0050] Furthermore, Ar1 can independently represent 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. According to one embodiment of this disclosure, Ar1 can independently represent hydrogen, substituted or unsubstituted (5- to 15-membered) heteroaryl containing one or more nitrogen atoms, or substituted or unsubstituted amino. According to another embodiment of this disclosure, Ar1 independently represents hydrogen; a (5- to 15-membered) heteroaryl group substituted with 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 with 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 another embodiment of this disclosure, the substituted or unsubstituted (3-membered to 30-membered) heteroaryl groups of Ar1 each independently represent substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazine, substituted or unsubstituted pyrazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted dibenzoquinolinyl, substituted or unsubstituted dibenzoquinoxalinyl Substituted or unsubstituted dibenzoquinoxalinyl, substituted or unsubstituted indopyridyl, substituted or unsubstituted indopyrimidinyl, substituted or unsubstituted indopyrazinyl, substituted or unsubstituted benzofuranopyridyl, substituted or unsubstituted benzofuranopyrimidinyl, substituted or unsubstituted benzofuranopyrazinyl, substituted or unsubstituted benzothiophenopyridyl, substituted or unsubstituted benzothiophenopyrimidinyl, substituted or unsubstituted benzothiophenopyrazinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiopheninyl. Specifically, Ar1 can independently represent hydrogen; triazinyl, quinazolinyl, quinoxalinyl, or benzoquinoxalinyl, which is substituted by at least one of one or more phenyl, one or more naphthyl, one or more biphenyl, one or more phenanthryl, one or more dimethylfluorenyl, one or more dibenzofuranyl, and one or more dibenzothiopheneyl; amino, which is substituted by at least one of one or more phenyl, one or more naphthyl, one or more biphenyl, one or more dimethylfluorenyl, one or more dibenzofuranyl, one or more dibenzothiopheneyl, and one or more phenylcarbazoyl.

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

[0052] According to one embodiment of this disclosure, R 11 L1 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 independently represents a single bond, a substituted or unsubstituted (C6-C15) arylene group, or a substituted or unsubstituted (5- to 15-membered) heteroaryl group; and Ar1 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 this disclosure, R 11 L1 represents an unsubstituted (C6-C15) aryl group, or a (C6-C15) aryl group substituted with 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 with at least one of one or more (C6-C20) aryl groups and one or more (5- to 15-membered) heteroaryl groups; L1 independently represents a single bond, an unsubstituted (C6-C15) aryl group, or a (C6-C15) aryl group substituted with one or more (C6-C15) aryl groups. A arylene, or an unsubstituted (5- to 15-membered) heteroarylene; Ar1, each independently representing hydrogen; a (5- to 15-membered) heteroarylene substituted with at least one of one or more (C6-C15) aryl, one or more (5- to 15-membered) heteroaryl and one or more (C1-C6) alkyl (C6-C15) aryl; or an amino group substituted with at least one of one or more (C6-C15) aryl, one or more (5- to 15-membered) heteroaryl and one or more (C1-C6) alkyl (C6-C15) aryl.

[0054] In the formulas of this 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 may be a substituted or unsubstituted monocyclic or polycyclic (3-membered to 30-membered) aliphatic or aromatic ring, or a combination thereof. Furthermore, the formed ring may 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 this disclosure, the number of ring skeleton atoms is 5 to 20. According to another embodiment of this disclosure, the number of ring skeleton atoms is 5 to 15. For example, the fused ring may 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 formulas disclosed herein, the heterocyclic alkyl and (heteroaryl) groups may each independently contain at least one heteroatom selected from B, N, O, S, Si, and P. Furthermore, 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 selected from, but is not limited to, one of the following compounds.

[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 compounds represented by Formula 1 of this disclosure can be produced by synthetic methods 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 synthetic examples of compounds represented by Formula 1 have been described above, those skilled in the art will readily understand that they are all based on Suzuki cross-coupling reactions, Wittig reactions, Miyaura borylation reactions, Ullmann reactions, Buchwald-Hartwig cross-coupling reactions, N-arylation reactions, H-mont-mediated etherification reactions, intramolecular acid-induced cyclization reactions, Pd(II)-catalyzed oxidative cyclization reactions, Grignard reactions, Heck reactions, dehydration cyclization reactions, SN1 substitution reactions, SN2 substitution reactions, phosphine-mediated reductive cyclization reactions, etc., and that these reactions continue even if substituents defined in Formula 1 above but not specified in the specific synthetic examples are bonded.

[0108] The hole transport region disclosed herein may consist of one or more layers, wherein the one or more layers are 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 consist of one or more layers.

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

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

[0111] The organic electroluminescent material may consist solely of compounds according to this disclosure, or may further include conventional materials included in organic electroluminescent materials.

[0112] The organic electroluminescent compound of Formula 1 disclosed herein may be contained in one or more layers selected from the following: 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 contained in the light-emitting layer. When used in the light-emitting layer, the organic electroluminescent compound of Formula 1 disclosed herein may be contained as a host material. Preferably, the light-emitting layer may further contain one or more dopants. If desired, the organic electroluminescent compound of this disclosure may be used as a co-host material. That is, the light-emitting layer may further contain an organic electroluminescent compound other than the organic electroluminescent compound of Formula 1 of this disclosure (the 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 a layer contains two or more materials, a mixed deposition may be performed to form the layer, or co-deposition may be performed simultaneously or separately to form the layer.

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

[0114]

[0115] in

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

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

[0118] R2 to R7 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, fused ring groups 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, The amino group may contain 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.

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

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

[0121] In Formula 2, X1 and Y1 independently represent -N=, -NR7-, -O-, or -S-, provided that either X1 or Y1 represents -N= and the other represents -NR7-, -O-, or -S-. According to one embodiment, either X1 or 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-membered to 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]yl group, a spiro[fluorene-benzofluorenyl]yl 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- 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 groups of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, substituted or unsubstituted mono- or di-(C6-C30)arylsilyl groups. 1-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 The 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, a substituted or unsubstituted (C6-C25) aryl, a substituted or unsubstituted (3- to 25-membered) heteroaryl, or a 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 or aromatic rings, wherein one or more carbon atoms of the alicyclic or aromatic ring 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- to 25-membered) heteroaryl, substituted or unsubstituted di(C6-C18) arylamino, substituted or unsubstituted mono- or di-(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 substituted or unsubstituted, monocyclic or polycyclic (C3-C25) alicyclic or aromatic rings, wherein one or more carbon atoms of the alicyclic or aromatic ring may be replaced by at least one heteroatom selected from nitrogen and sulfur, and the heteroaryl 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 substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted triazine, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted Quinazolinyl, substituted or unsubstituted quinoxolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted benzoquinoxolinyl, substituted or unsubstituted benzofuranopyrimidinyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted naphridinyl, substituted or unsubstituted benzonaphthofuranyl, or substituted or unsubstituted benzonaphthothiopheneyl. For example, at least one of R5 and R6 independently represents a substituted or unsubstituted phenyl, a substituted or unsubstituted o-phenyl, a substituted or unsubstituted meta-phenyl, a substituted or unsubstituted para-phenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, or a substituted or unsubstituted benzofluorenyl.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, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, naphthylphenyl, phenylnaphthyl, dimethylbenzofluorenyl, terphenyl, spirodifluorenyl, benzofuranyl, benzothiopheneyl, dibenzothiopheneyl, unsubstituted or substituted dibenzofuranyl, carbazoyl substituted with one or more phenyl groups, or benzonaphthylfuranyl; and the one or more substituents of the substituted phenyl 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; anthraceneyl; fluoranthyl; phenylfluorenyl; cyclohexyl; pyridyl substituted with one or more phenyl groups; phenoxazinyl; and benzimidazolyl substituted with one or more phenyl groups.

[0123] In Equation 2, f represents 1 or 2, preferably 1; g and h each independently represent 1 or 2, preferably 1; 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, then each R2 to each R4 can be the same or different.

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

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

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132] According to another embodiment of this disclosure, when the organic electroluminescent compound of formula 1 of this disclosure is included in the luminescent layer, the luminescent layer may further include a compound represented by formula 3:

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

[0134] in

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

[0136] L2 independently represents substituted or unsubstituted (C6-C30) aryl groups;

[0137] Ar2 can independently represent substituted or unsubstituted (C6-C30) aryl groups, or formula 4 below, provided that at least one of Ar2 is a 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 They can be connected to form a ring;

[0141] R 31 To R 38 Each independently represents a site linked 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) alkylsilyl, etc. 0) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyl di(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, 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 independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene;

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

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

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

[0146] * indicates a site connected to L2.

[0147] In Formula 3, HAr represents a substituted or unsubstituted heteroaryl group containing one or more nitrogen atoms (3-membered to 20-membered). According to one embodiment of this disclosure, HAr represents a substituted or unsubstituted heteroaryl group containing one or more nitrogen atoms (3-membered to 15-membered). According to another embodiment of this disclosure, HAr represents an unsubstituted heteroaryl group containing one or more nitrogen atoms (5-membered to 15-membered). Specifically, HAr can be pyridinyl, pyrimidinyl, triazinyl, quinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, pyridopyrazinyl, benzoquinazolinyl, benzoquinoxalinyl, benzofuranopyrimidinyl, etc.

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

[0149] In Formula 3, Ar2 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 this disclosure, Ar2 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 can independently be phenyl, naphthyl, phenylnaphthyl, naphthylphenyl, biphenyl, terphenyl, phenanthrene, triphenylene, etc. The phenyl group, unsubstituted or substituted with one or more phenyl groups, phenyl group substituted with one or more phenylquinoxalinyl groups, phenyl group substituted with one or more diphenylamino groups, etc., or Formula 4.

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

[0151] In Equation 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 They can be connected to each other to form a ring. According to one embodiment of this 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 They can be connected to each other to form a ring. According to another embodiment of this 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 They can be connected to each other to form a loop. Specifically, R 41 To R 43 Each can independently represent methyl, phenyl, etc., or R 41 and R 42 They can connect with each other to form fluorene rings.

[0152] In Equation 4, R 31 To R 38Each independently represents a site linked 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) alkylsilyl, etc. 0) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyl di(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, fused ring groups of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or -L4-N(Ar3)(Ar4); or may be linked with adjacent substituents to form one or more rings. According to one embodiment of this disclosure, R 31 To R 38 Each can independently represent a site linked to L2; or represent hydrogen, or a substituted or unsubstituted (C6-C20) aryl group; or can be linked with adjacent substituents to form one or more rings. According to another embodiment of this disclosure, R 31 To R 38 Each can independently represent a site linked to L2; or represent hydrogen, or an unsubstituted (C6-C18) aryl group; or can be linked with adjacent substituents to form one or more rings. For example, R 31 To R 38 Each can be an independent site connected to L2; or it can be hydrogen, phenyl, naphthyl, biphenyl, naphthylphenyl, phenylnaphthyl, etc.; or it can be connected to an adjacent substituent to form a benzene ring.

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

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

[0155] In Equation 3, d represents an integer from 1 to 3, where if d is an integer of 2 or greater, then 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 Equation 3, e represents an integer from 0 to 2, where if e is 2, then each L2 can be the same or different.

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

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170] The dopant included in the organic electroluminescent device of this disclosure can be at least one phosphorescent dopant or fluorescent dopant, and preferably a phosphorescent dopant. The phosphorescent dopant material used in the organic electroluminescent device of this disclosure is not particularly limited, but can preferably be selected from metallized iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt) complexes, more preferably from ortho-metallized iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt) complexes, and even more preferably from ortho-metallized iridium complexes.

[0171] The dopants included in the organic electroluminescent devices of this disclosure may include, but are not limited to, compounds represented by the following formula 101.

[0172]

[0173] In Equation 101, L is selected from the following structures 1 to 3.

[0174]

[0175] R 100 To R 103 Each can independently represent 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 can be linked with adjacent substituents to form one or more rings with pyridine, such as substituted or unsubstituted quinoline, isoquinoline, benzofuranopyridine, benzothienopyridine, indoxpyridine, benzofuranoquinoline, benzothienoquinoline, or indoxpyridine;

[0176] R 104 To R 107 Each can independently represent 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 can be linked with adjacent substituents to form one or more rings with benzene, such as substituted or unsubstituted naphthalene, fluorene, dibenzothiophene, dibenzofuran, indenepyridine, benzofuranopyridine, or benzothiophenepyridine;

[0177] R 201 To R 220 Each of these groups independently represents hydrogen, deuterium, halogen, unsubstituted or deuterated and / or one or more halogenated (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

[0178] s represents an integer from 1 to 3.

[0179] Specific examples of dopant compounds are shown below, but are not limited to.

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186] The organic electroluminescent device according to this 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 and second electrodes can be an anode, and the other can be a cathode. The organic layer includes a light-emitting layer and may further include at least one layer selected from the following: 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. Furthermore, each layer may consist of multiple layers.

[0188] The first and second electrodes can each be formed from a transmissive conductive material, a semi-transmissive reflective conductive material, or a reflective conductive material. Depending on the types of materials used to form the first and second electrodes, the organic electroluminescent device can be a top-emitting, bottom-emitting, or side-emitting type. Furthermore, 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 this disclosure, the organic electroluminescent device of this disclosure may further include, in addition to the organic electroluminescent compound of this disclosure, at least one of an azazine-based compound as an electron transport material, an electron injection material, an electron buffer material, and a hole blocking material.

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

[0191] Furthermore, in the organic electroluminescent device disclosed herein, the organic layer may further comprise at least one metal selected from the group consisting of: metals of Group 1, Group 2, transition metals of Period 4, transition metals of Period 5, organometals of lanthanides and d-transition elements, or at least one complex compound comprising said metal.

[0192] In addition to the compounds disclosed herein, the organic electroluminescent device of this disclosure may emit white light by further comprising at least one light-emitting layer containing a compound known in the art that emits blue, red, or green light. Furthermore, if desired, it may further comprise a layer that emits yellow or orange light.

[0193] In the organic electroluminescent device disclosed herein, at least one layer selected from chalcogenide layers, metal halide layers, and metal oxide layers (hereinafter, "surface layer") is preferably placed on one or more inner surfaces of one or two electrodes. Specifically, a silicon or aluminum chalcogenide (including oxide) layer is preferably placed on the anode surface of the electroluminescent dielectric layer, and a metal halide layer or metal oxide layer is preferably placed on the cathode surface of the electroluminescent dielectric layer. The surface layer can provide operational stability to the organic electroluminescent device. Preferably, the chalcogenide includes SiO₂. 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, can be used between the anode and the light-emitting layer. The hole injection layer can be multilayered to reduce the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or electron blocking layer, wherein each of the multilayers can use two compounds simultaneously. The hole transport layer or electron blocking layer can also be multilayered.

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

[0196] A light-emitting auxiliary layer can be placed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer. When placed between the anode and the light-emitting layer, it can promote hole injection and / or hole transport, or prevent electron overflow. When placed between the cathode and the light-emitting layer, it can promote electron injection and / or electron transport, or prevent hole overflow. Furthermore, a hole auxiliary layer can be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, effectively promoting or limiting the hole transport rate (or hole injection rate), thereby enabling charge balance control. Additionally, an electron blocking layer can be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, blocking overflowing electrons from the light-emitting layer and confining excitons within the light-emitting layer to prevent light leakage. When an organic electroluminescent device includes two or more hole transport layers, the further included hole transport layers can serve as hole auxiliary layers or electron blocking layers. Hole auxiliary layers and electron blocking layers can improve the efficiency and / or lifetime of the organic electroluminescent device.

[0197] In the organic electroluminescent device of this disclosure, it is preferable to place a mixed region of electron transport compound and reducing dopant, or a mixed region of hole transport compound and oxidizing dopant, on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to anion, and thus it becomes easier to inject and transport electrons from the mixed region into the electroluminescent medium. Furthermore, the hole transport compound is oxidized to cation, and thus it becomes easier to inject and transport holes from the mixed region into the electroluminescent medium. Preferably, the oxidizing dopant includes various Lewis acids and acceptor compounds; and the reducing dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. The reducing dopant layer can be used as a charge-generating layer to produce an organic electroluminescent device having two or more light-emitting layers that emit white light.

[0198] According to one embodiment of this disclosure, organic electroluminescent materials can be used as luminescent materials for white organic light-emitting devices. Various structures for white organic light-emitting devices have been proposed, such as parallel arrangement (side-by-side) methods, stacking methods, or color conversion material (CCM) methods, depending on the arrangement of R (red), G (green), B (blue), or YG (yellow-green) luminescent units. Furthermore, according to one embodiment of this disclosure, the organic electroluminescent material can also be applied to organic electroluminescent devices containing quantum dots (QDs).

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

[0200] When using a wet film-forming method, a thin film can be formed by dissolving or dispersing the materials forming each layer in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. There are no particular restrictions on the solvent, as long as the materials constituting each layer are soluble or dispersible in the solvent, which will not cause any problems during film formation.

[0201] Display systems, such as those for smartphones, tablets, laptops, PCs, TVs, or automobiles, can be produced using the organic electroluminescent devices disclosed herein; or lighting systems, such as outdoor or indoor lighting systems.

[0202] The preparation methods of the compounds of this disclosure and the properties of the compounds will be explained in detail below with reference to representative compounds of this disclosure. However, this 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-dioxapentoboran-2-yl)-9H-carbazole (26.2 g, 51.5 mmol), tetra(triphenylphosphine)palladium(0) (2.95 g, 2.55 mmol), NaOH (4.12 g, 255 mmol), 360 mL tetrahydrofuran (THF), and 90 mL H2O were introduced into a flask, and the mixture was stirred under reflux at 90 °C for 1.5 h. After the reaction was complete, the reaction mixture was neutralized with aqueous NH4Cl 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 Compounds 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. The mixture was stirred for 3 hours, neutralized with NH4Cl, extracted with 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 1-2 (20.0 g, yield: 97%).

[0209] Synthesis of compounds 1-3

[0210] Compounds 1-2 (66.3 g, 191 mmol), 34 mL Eaton reagent, and 950 mL chlorobenzene were introduced into a flask, and the mixture was stirred overnight at 180 °C under reflux. After the reaction was complete, the reaction mixture was neutralized with NaHCO3, extracted with 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 compounds 1-3 (27 g, yield: 45%).

[0211] Synthesis of compound C-686

[0212] Compounds 1-3 (10.0 g, 11 mmol), 2-chloro-3-phenyl-quinoxaline (7.6 g, 31.5 mmol), Cs₂CO₃ (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 complete, the solid obtained by adding H₂O 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] Compounds 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 overnight at 180 °C under reflux. After the reaction was complete, 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'-bis(1,3,2-dioxane) (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 under reflux at 130 °C for 2 hours. After the reaction was complete, 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-chlorobenzaldehyde (25.8 g, 117 mmol), tetrakis(triphenylphosphine)palladium(0) (3.88 g, 3.36 mmol), NaOH (13.4 g, 336 mmol), 450 mL THF, and 150 mL H2O were introduced into a flask, and the mixture was stirred under reflux at 130 °C for 2 hours. After the reaction was complete, the reaction mixture was neutralized with aqueous HCl, 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 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. The mixture was stirred for 3 hours, neutralized with NH4Cl, extracted with 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 3-3 (37.0 g, yield: 138%).

[0226] Synthesis of compounds 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 BF3·EtOEt was added dropwise while stirring at 0 °C. After the reaction was complete, the reaction mixture was neutralized with NaHCO3, extracted with 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 3-4 (18.7 g, yield: 56.5%).

[0228] Synthesis of compound C-589

[0229] Compounds 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] Compounds 3-4 (9.0 g, 24.4 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxane) (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 under reflux at 130 °C for 2 hours. After the reaction was complete, 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 toluene, 25.0 mL EtOH, and 25.0 mL H₂O were introduced into a flask, and the mixture was stirred under reflux at 140 °C for 2 hours. After the reaction was complete, the reaction mixture was diluted with 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-Chloronaphtho[1,2-b]benzofuran (50.0 g, 198 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxacyclopentaborane) (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 under reflux at 130 °C for 3 hours. After the reaction was complete, 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-chlorobenzaldehyde (33.6 g, 153 mmol), tetrakis(triphenylphosphine)palladium(0) (5.06 g, 4.38 mmol), NaOH (17.5 g, 438 mmol), 500 mL THF, and 250 mL H2O were introduced into a flask, and the mixture was stirred under reflux at 130 °C for 2 hours. After the reaction was complete, the reaction mixture was neutralized with aqueous NH4Cl 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 1 M K-Ot-Bu solution dissolved in THF was added dropwise. The mixture was stirred for 3 hours, neutralized with NH4Cl, 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 5-3 (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 BF3·EtOEt was added dropwise while stirring at 0 °C. After the reaction was complete, the reaction mixture was neutralized with NaHCO3, extracted with 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 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 h. 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-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-dioxane) (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 under reflux at 130 °C for 3 hours. After the reaction was complete, 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 toluene, 10 mL EtOH, and 10 mL H₂O were introduced into a flask, and the mixture was stirred under reflux at 130 °C for 2 hours. After the reaction was complete, 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), tetra(triphenylphosphine)palladium(0) (0.589 g, 0.51 mmol), K₂CO₃ (3.52 g, 25.5 mmol), 30.0 mL toluene, 10.0 mL EtOH, and 10.0 mL H₂O were introduced into a flask, and the mixture was stirred under reflux at 140 °C for 2 hours. After the reaction was complete, the reaction mixture was diluted with 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]

[0262]

[0263] Device Example 1: Production of an OLED emitting red light according to this disclosure

[0264] OLEDs containing compounds according to this disclosure are produced. A transparent electrode indium tin oxide (ITO) film (10 Ω / sq) (GEOMATEC CO.,LTD., Japan) on a glass substrate for the OLED is sequentially ultrasonically washed with acetone and isopropanol, and then stored in isopropanol. The ITO substrate is then mounted on a substrate holder in a vacuum vapor deposition apparatus. Compound HI-1 is introduced into one chamber of the vacuum vapor deposition apparatus, and compound HT-1 is introduced into another chamber. The two materials are evaporated at different rates, and compound HI-1 is deposited at a doping amount of 3 wt% based on the total amount of compounds HI-1 and HT-1 to form a hole injection layer with a thickness of 10 nm on the ITO substrate. Next, compound HT-1 is introduced into one chamber of the vacuum vapor deposition apparatus and evaporated by applying a current to the chamber, thereby forming a first hole transport layer with a thickness of 80 nm on the hole injection layer. Compound HT-2 was then introduced into another chamber of a vacuum vapor deposition apparatus and evaporated by applying current to the chamber, thereby 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 the hole transport layer, a light-emitting layer was formed thereon as follows: Compound C-686 was introduced as the host into one chamber of the vacuum vapor deposition apparatus, and Compound D-39 was introduced as the 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 the host and the dopant to form a light-emitting layer with a thickness of 40 nm on the second hole transport layer. Compounds ETL-1 and EIL-1 were evaporated at a weight ratio of 50:50 as electron transport materials to form an electron transport layer with a thickness of 35 nm on the light-emitting layer. After depositing 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 using another vacuum vapor deposition apparatus. Thus, an OLED was produced. All compounds used as materials are in 10 -6 Purification is achieved through vacuum sublimation.

[0265] Device Example 2: Production of an OLED emitting red light according to this disclosure

[0266] The OLED was produced in the same manner as in Device Example 1, except that compound C-700 was used as the main body of the light-emitting layer.

[0267] Comparative Example: Production of OLEDs Containing Comparative Compounds as the Main Body

[0268] The OLED is produced in the same manner as in Device Example 1, except that the compound CBP is used as the main body of the light-emitting layer.

[0269] Table 1 below provides the driving voltage, luminous efficiency, and emission color of the OLEDs produced in Device Examples 1 and 2 and the Comparative Examples at a brightness of 1,000 nits, as well as the time (lifetime; T95) taken for the brightness to decrease from 100% to 95% at a brightness of 5,000 nits.

[0270] [Table 1]

[0271]

[0272] Compared to OLEDs using compounds from comparative examples, OLEDs containing organic electroluminescent compounds according to this disclosure as the main body exhibit lower driving voltage, higher luminous efficiency, and superior lifetime characteristics.

[0273] Device Examples 3 to 6: Production of Red-Emitting OLEDs According to This Disclosure

[0274] OLEDs are produced according to this disclosure. A transparent electrode indium tin oxide (ITO) film (10 Ω / sq) (Geoma Ltd., Japan) on a glass substrate for the OLED is sequentially ultrasonically washed with acetone and isopropanol, and then stored in isopropanol. The ITO substrate is then mounted on a substrate holder in a vacuum vapor deposition apparatus. Compound HI-1 is introduced into one chamber of the vacuum vapor deposition apparatus, and compound HT-1 is introduced into another chamber. The two materials are evaporated at different rates, and compound HI-1 is deposited at a doping amount of 3 wt% based on the total amount of compounds HI-1 and HT-1 to form a hole injection layer with a thickness of 10 nm on the ITO substrate. Next, compound HT-1 is introduced into one chamber of the vacuum vapor deposition apparatus and evaporated by applying a current to the chamber, thereby forming a first hole transport layer with a thickness of 80 nm on the hole injection layer. Compound HT-2 was then introduced into another chamber of the vacuum vapor deposition apparatus, and the compound was evaporated by applying an electric current to the chamber, thereby 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 the hole transport layer, a light-emitting layer was formed thereon as follows: The first and second host materials shown in Table 2 were introduced as hosts into two chambers of the 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 1:1 rate, and the dopant material was evaporated simultaneously at different rates. The dopant was deposited at a doping amount of 3 wt% based on the total amount of the host and dopant to form a light-emitting layer with a thickness of 40 nm on the second hole transport layer. Compounds ETL-1 and EIL-1 were evaporated at a 50:50 weight ratio as electron transport materials to form an electron transport layer with a thickness of 35 nm on the light-emitting layer. After depositing compound EIL-1 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 phase deposition apparatus. This produced an OLED. All compounds used as materials were selected at 10... -6 Purification is achieved through vacuum sublimation.

[0275] Table 2 below provides the driving voltage, luminous efficiency, and emission color of the OLEDs produced in device examples 3 to 6 at a brightness of 1,000 nits, as well as the time (lifetime; T95) taken for the brightness to decrease from 100% to 95% at a brightness of 5,000 nits.

[0276] [Table 2]

[0277]

[0278] The OLED disclosed herein exhibits low driving voltage, high luminous efficiency, and remarkably superior lifetime characteristics.

[0279] [Table 3]

[0280]

Claims

1. An organic electroluminescent compound, represented by formula 1: in Ring A is selected from the following formula: X represents NR 11 or CR 12 R 13 ; R1 can be independently represented by hydrogen, deuterium, halogen, or cyano; R 11 It 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. R 12 and R 13 Each of these elements 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 they may be linked together to form a ring. R 21 Represents -L1-Ar1, where if R 21 If there are multiple R, then each R 21 They can be the same or different; L1 independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene; Ar1 can independently represent 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. a represents an integer from 1 to 4, b represents an integer from 1 to 10, where if a and b are integers of 2 or greater, then each R1 and each R 21 They can be the same or different; * indicates a site that is fused with a 5-membered ring containing X; The premise is that X is NR 11 Then ring A is not 2. The organic electroluminescent compound according to claim 1, wherein, In R11 to R13, 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 groups are each independently selected from at least one of the following groups: 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; (C30)alkylthio; (C30)alkylthio; (C2- ... -C30)cycloalkyl; (C3-C30)cycloalkenyl; (3- to 7-membered)heteroalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; unsubstituted or (3- to 30-membered)heteroaryl substituted with one or more (C6-C30)aryl groups; unsubstituted or (C6-C30)aryl substituted with at least one of one or more (C1-C30)alkyl 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)aryl Amino; (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)arylboroncarbonyl; di(C1-C30)alkylboroncarbonyl; (C1-C30)alkyl(C6-C30)arylboroncarbonyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl.

3. The organic electroluminescent compound according to claim 1, wherein, Ring A is selected from the following formula:

4. The organic electroluminescent compound according to claim 1, wherein, Ring A is selected from the following formula:

5. The organic electroluminescent compound according to claim 1, wherein, Ring A is selected from the following formula:

6. The organic electroluminescent compound according to claim 1, wherein, L1 independently represents a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted phenanthylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted fluorene, or a substituted or unsubstituted pyridylene.

7. The organic electroluminescent compound according to claim 1, wherein, R 11 To R 13 The substituted or unsubstituted (3- to 30-membered) heteroaryl groups of Ar1 are each independently represented by substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazine, substituted or unsubstituted pyrazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted dibenzoquinolinyl, substituted or unsubstituted dibenzoquinoxalinyl, substituted or unsubstituted Substituted dibenzoquinoxalinyl, substituted or unsubstituted indopyridyl, substituted or unsubstituted indopyrimidinyl, substituted or unsubstituted indopyrazinyl, substituted or unsubstituted benzofuranopyridyl, substituted or unsubstituted benzofuranopyrimidinyl, substituted or unsubstituted benzofuranopyrazinyl, substituted or unsubstituted benzothiophenopyridyl, substituted or unsubstituted benzothiophenopyrimidinyl, substituted or unsubstituted benzothiophenopyrazinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiopheninyl.

8. The organic electroluminescent compound according to claim 1, wherein, The compound represented by Formula 1 is selected from the following compounds:

9. An organic electroluminescent material comprising the organic electroluminescent compound according to claim 1.

10. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1.

11. The organic electroluminescent device according to claim 10, wherein, The organic electroluminescent compound is contained in the light-emitting layer or hole transport region.

12. The organic electroluminescent device according to claim 11, 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 can each independently represent -N=, -NR7-, -O-, or -S-, provided that either X1 or Y1 represents -N=, and the other X1 or Y1 represents -NR7-, -O-, or -S-. R' indicates a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; R2 to R7 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, fused ring groups 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, The amino group may contain 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. L' represents a single-bonded, substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; and f represents 1, g and h each independently represent 1 or 2, and i represents an integer from 1 to 4, where each R2 to each R4 can be the same or different if each of g to i is an integer of 2 or greater.

13. The organic electroluminescent device according to claim 12, wherein, The compound represented by Formula 2 is selected from the following compounds:

14. The organic electroluminescent device according to claim 11, wherein, When the organic electroluminescent compound is contained in the light-emitting layer, the light-emitting layer further contains a compound represented by Formula 3: HAr-((L2) e -Ar2) d -----(3) in HAr represents a substituted or unsubstituted heteroaryl group containing one or more nitrogen atoms (3-membered to 20-membered); L2 independently represents substituted or unsubstituted (C6-C30) aryl groups; Ar2 can independently represent substituted or unsubstituted (C6-C30) aryl groups, or formula 4 below, provided that at least one of Ar2 is a 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 They can be connected to form a ring; R 31 To R 38 Each independently represents a site linked 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) alkylsilyl, etc. 0) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyl di(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, 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 independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene; Ar3 and Ar4 each independently represent hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-membered to 30-membered) heteroaryl; d represents an integer from 1 to 3, where if d is an integer of 2 or greater, then each ((L2)) e -Ar2) can be the same or different; e represents an integer from 0 to 2, where if e is 2, then each L2 can be the same or different; and * indicates a site connected to L2.

15. The organic electroluminescent device according to claim 14, wherein, The compound represented by Formula 3 is selected from the following compounds:

Images