Organic electroluminescent compounds, materials and light emitting devices comprising same

Abstract

Organic electroluminescent compounds, materials and light emitting devices comprising the same. The present disclosure relates to an organic electroluminescent compound represented by Formula 1, an organic electroluminescent material comprising compounds represented by Formula 1 and Formula 2, an organic electroluminescent material comprising compounds represented by Formula 1 and Formula 3, and an organic electroluminescent device comprising the same. An organic electroluminescent device having improved driving voltage, luminous efficiency, and / or lifespan characteristics can be provided by comprising an organic electroluminescent compound or an organic electroluminescent material according to the present disclosure.

Description

Technical Field

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

[0002] Small molecule green organic electroluminescent device (OLED) was first developed by Tang et al. of Eastman Kodak in 1987 using a TPD / ALq3 double layer consisting of a light-emitting layer and a charge transport layer. Since then, OLED development has progressed rapidly and achieved commercialization. At present, OLED mainly uses phosphorescent materials with excellent luminous efficiency in panel implementation. However, in various applications such as TV and lighting equipment, the life of OLED is often insufficient, and OLED with higher efficiency is still needed. Generally, the life of OLED shortens as its brightness increases. Therefore, OLED with high luminous efficiency and / or extended life is essential for long-term use and high-resolution displays.

[0003] In order to improve luminous efficiency, driving voltage and / or lifespan, various materials or concepts for organic layers of organic electroluminescent devices have been proposed, but these have not proven to be satisfactory in actual use. In addition, there is a continuing need to develop organic electroluminescent materials having enhanced properties, such as improved driving voltage, luminous efficiency, power efficiency and / or lifespan characteristics compared to previously disclosed combinations of specific compounds.

[0004] Meanwhile, Korean Patent Application Publication No. 10-2023-0001569, Chinese Patent Application Publication No. 111423390A, Korean Patent Application Publication No. 10-2022-0123495, and Korean Patent Application Publication No. 10-2021-0062293 disclose fluoranthene derivatives and the like as organic electroluminescent compounds. However, the aforementioned references do not specifically disclose compounds having specific structures as claimed in the present disclosure and organic electroluminescent materials comprising the same. In addition, there is a continuing need to develop organic electroluminescent materials having enhanced performance, such as improved driving voltage, luminous efficiency, and / or life characteristics compared to the combination of previously disclosed specific compounds. Summary of the invention

[0005] Technical issues

[0006] The object of the present disclosure is to provide an organic electroluminescent compound having a novel structure suitable for application in an organic electroluminescent device. Another object of the present disclosure is to provide an organic electroluminescent compound and an organic electroluminescent material capable of providing an organic electroluminescent device having improved driving voltage, luminous efficiency and / or life characteristics.

[0007] Solution to the problem

[0008] As a result of intensive studies to solve the technical problem, the inventors of the present invention have found that the above object can be achieved by the following: an organic electroluminescent compound represented by the following Formula 1.

[0009]

[0010] In formula 1,

[0011] R 1 and R 2 are linked to each other to form one or more substituted or unsubstituted fused rings;

[0012] R 3 To R 10 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- to 30-membered)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or substituted or unsubstituted tri(C6-C30)arylsilyl; and

[0013] The one or more fused rings and R 3 To R 10 At least one of the one or more substituents represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group containing at least one N.

[0014] Furthermore, the inventors of the present invention have found that the above object can be achieved by an organic electroluminescent material comprising a compound represented by the above formula 1 and a compound represented by the following formula 2 or a compound represented by the above formula 1 and a compound represented by the following formula 3.

[0015]

[0016] In formula 2,

[0017] Y 1 and Y 2 Each independently represents -N=, -NR 16 -, -O- or -S-, provided that Y 1 and Y 2 Any one of -N=, and Y 1 and Y 2 Another representation in -NR 16-, -O-, or -S-;

[0018] R 12 represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group;

[0019] R 13 To R 16 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C 30 )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) 30 )alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted condensed ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or -L 1 -N-(Ar 1 )(Ar 2 ); or may be linked to one or more adjacent substituents to form one or more rings; provided that R 13 To R 15 At least one of them is -L 1 -N-(Ar 1 )(Ar 2 );

[0020] Ar 1 and Ar 2 Each independently represents a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, or a substituted or unsubstituted condensed ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings;

[0021] L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group; and

[0022] a and b each independently represent an integer of 1 or 2, and c represents an integer of 1 to 4, wherein if a to c are integers of 2 or more, each R 13 To each R 15 May be the same as or different from each other.

[0023]

[0024] In formula 3,

[0025] X stands for O, S, CR 21 R 22 NR 23 or Se;

[0026] R 21 To R 23 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C 30 )alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3- to 30-membered)heteroaryl; or may be linked to one or more adjacent substituents to form one or more rings;

[0027] R 17 To R 20 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl,

[0028] The premise is R 17 To R 20 At least one of

[0029] L 2 and L 3 each independently represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, a substituted or unsubstituted (C3-C30)cycloalkylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group;

[0030] Ar 3 To Ar 7 each independently represents a substituted or unsubstituted (C6-C30)aryl group or a substituted or unsubstituted (3- to 30-membered) heteroaryl group;

[0031] d and g represent integers of 1 to 4, and e and f represent integers of 1 or 2, wherein if d to g are integers of 2 or more, each R 17 To each R 20 may be the same as or different from each other; and

[0032] * indicates the site of connection with Formula 3.

[0033] Beneficial effects of the present invention

[0034] An organic electroluminescent device having improved driving voltage, luminous efficiency, and / or lifespan characteristics may be provided by including the organic electroluminescent compound according to the present disclosure and an organic electroluminescent material. BRIEF DESCRIPTION OF THE DRAWINGS

[0035] Figure 1 Representative formulas of organic electroluminescent compounds according to the present disclosure are shown. DETAILED DESCRIPTION

[0036] Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present disclosure and is not intended to limit the scope of the present disclosure.

[0037] The term "organic electroluminescent compound" in the present disclosure refers to a compound that can be used in an organic electroluminescent device and can be incorporated into any layer constituting the organic electroluminescent device as necessary.

[0038] The term "organic electroluminescent material" in the present disclosure refers to a material that can be used in an organic electroluminescent device and can contain at least one compound. If necessary, the organic electroluminescent material can be incorporated into any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material can be any of the following: a hole injection material, a hole transport material, a hole auxiliary material, a luminescence auxiliary material, an electron blocking material, a luminescent material (including a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0039] The term "multiple host materials" in the present disclosure means a host material comprising a combination of at least two compounds, which may be included in any light-emitting layer constituting an organic electroluminescent device. It may mean both a material before being included in an organic electroluminescent device (e.g., before vapor deposition) and a material after being included in an organic electroluminescent device (e.g., after vapor deposition). For example, the multiple host materials of the present disclosure are a combination of at least two host materials, and may selectively further include conventional materials contained in organic electroluminescent materials. At least two compounds contained in the multiple host materials of the present disclosure may be contained together in one light-emitting layer, or may be contained in different light-emitting layers, respectively. For example, at least two host materials may be mixed evaporated or co-evaporated, or may be evaporated individually.

[0040] The term "hole transport zone" in the present disclosure means a zone in which holes move between the first electrode and the light-emitting layer, and may include, for example, one or more of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, and an electron blocking layer. The hole injection layer, the hole transport layer, the hole auxiliary layer, the light-emitting auxiliary layer, and the electron blocking layer may each be a single layer, two or more layers, or a multilayer in which three or more layers are laminated. According to one embodiment of the present disclosure, the hole transport zone may include a first hole transport layer and a second hole transport layer, and may further include a third hole transport layer. The second hole transport layer and the third hole transport layer may be at least one of a plurality of hole transport layers, and may include at least one of a hole auxiliary layer, a light-emitting auxiliary layer, and an electron blocking layer. In addition, according to another embodiment of the present disclosure, the hole transport region includes a first hole transport layer and a second hole transport layer, the first hole transport layer may be located between the first electrode and the light-emitting layer, the second hole transport layer may be located between the first hole transport layer and the light-emitting layer, and the second hole transport layer may be a layer that acts as a hole transport layer, a light-emitting auxiliary layer, a hole auxiliary layer and / or an electron blocking layer. According to another embodiment of the present disclosure, the hole transport region includes a first hole transport layer, a second hole transport layer, and a third hole transport layer, wherein the first hole transport layer may be located between the first electrode and the light-emitting layer, the second hole transport layer may be located between the first hole transport layer and the light-emitting layer, the third hole transport layer may be located between the second hole transport layer and the light-emitting layer, and the third hole transport layer may be a layer that acts as a hole transport layer, a light-emitting auxiliary layer, a hole auxiliary layer, and / or an electron blocking layer.

[0041] Herein, the term "(C1-C30) alkyl" means a straight or branched alkyl group having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 10, and more preferably 1 to 6. The above-mentioned alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, and the like. The term "(C3-C30) cycloalkyl" means a monocyclic or polycyclic hydrocarbon having 3 to 30 ring skeleton carbon atoms, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The above-mentioned cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, and the like. The term "(3- to 7-membered) heterocycloalkyl" means a cycloalkyl group having 3 to 7 ring skeleton atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, and preferably the group consisting of O, S, and N. The above-mentioned heterocycloalkyl can include tetrahydrofuran, pyrrolidine, tetrahydrothiophene (thiolan), tetrahydropyran and the like. The terms "(C6-C30) aryl", "(C6-C30) arylidene", and "(C6-C30) arene triyl" mean a monocyclic or condensed ring group derived from an aromatic hydrocarbon having 6 to 30 ring skeleton carbon atoms. The above-mentioned aryl, arylidene and arene triyl can be partially saturated and can contain a spiro structure. The above-mentioned aryl can include phenyl, biphenyl, terphenyl, pentyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, triphenylenyl, anthracenyl, indenyl, triphenylene, pyrenyl, naphthyl, perylene, The aryl groups include phenyl, 1-naphthyl, 2-naphthyl, 1-anthracenyl, 2-anthracenyl, 9-anthracenyl, benzanthracenyl, 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 9-phenanthrenyl, tetraphenyl, pyrenyl, 1- Base, 2- Base, 3- Base, 4- Base, 5- Base, 6- Benzo[c]phenanthrenyl, benzo[g] 1-triphenylene, 2-triphenylene, 3-triphenylene, 4-triphenylene, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo[a]fluorenyl, benzo[b]fluorenyl, benzo[c]fluorenyl, dibenzofluorenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-5-yl, m-terphenyl-6-yl, m-terphenyl-7-yl, m-terphenyl-8-yl, m-terphenyl-9-yl, m-terphenyl-10-yl, m-terphenyl-11-yl, m-terphenyl-12-yl, m-terphenyl-13-yl, m-terphenyl-14-yl, m-terphenyl-15-yl phenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, p-tert-butylbutylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, 11,11-dimethyl-1-benzo[a]fluorenyl, 11,11-dimethyl-2-benzo[a]fluorenyl, 11,11-dimethyl-3-benzo[a]fluorenyl, 11,11- dimethyl-4-benzo[a]fluorenyl, 11,11-dimethyl-5-benzo[a]fluorenyl, 11,11-dimethyl-6-benzo[a]fluorenyl, 11,11-dimethyl-7-benzo[a]fluorenyl, 11,11-dimethyl-8-benzo[a]fluorenyl, 11,11-dimethyl-9-benzo[a]fluorenyl, 11,11-dimethyl- 10-benzo[a]fluorenyl, 11,11-dimethyl-1-benzo[b]fluorenyl, 11,11-dimethyl-2-benzo[b]fluorenyl, 11,11-dimethyl-3-benzo[b]fluorenyl, 11,11-dimethyl-4-benzo[b]fluorenyl, 11,11-dimethyl-5-benzo[b]fluorenyl, 11,11-dimethyl-6-benzo[b]fluorenyl [b]fluorenyl, 11,11-dimethyl-7-benzo[b]fluorenyl, 11,11-dimethyl-8-benzo[b]fluorenyl, 11,11-dimethyl-9-benzo[b]fluorenyl, 11,11-dimethyl-10-benzo[b]fluorenyl, 11,11-dimethyl-1-benzo[c]fluorenyl, 11,11-dimethyl-2-benzo[c]fluorenyl 11,11-dimethyl-3-benzo[c]fluorenyl, 11,11-dimethyl-4-benzo[c]fluorenyl, 11,11-dimethyl-5-benzo[c]fluorenyl, 11,11-dimethyl-6-benzo[c]fluorenyl, 11,11-dimethyl-7-benzo[c]fluorenyl, 11,11-dimethyl-8-benzo[c]fluorenyl, 11,11-dimethyl-11-dimethyl-9-benzo[c]fluorenyl, 11,11-dimethyl-10-benzo[c]fluorenyl, 11,11-diphenyl-1-benzo[a]fluorenyl, 11,11-diphenyl-2-benzo[a]fluorenyl, 11,11-diphenyl-3-benzo[a]fluorenyl, 11,11-diphenyl-4-benzo[a]fluorenyl, 11,11-diphenyl-5-benzo[a]fluorenyl, 11,11-diphenyl-6-benzo[a]fluorenyl, 11,11-diphenyl-7-benzo[a]fluorenyl, 11,11-diphenyl 11,11-diphenyl-9-benzo[a]fluorenyl, 11,11-diphenyl-10-benzo[a]fluorenyl, 11,11-diphenyl-1-benzo[b]fluorenyl, 11,11-diphenyl-2-benzo[b]fluorenyl, 11,11-diphenyl-3-benzo[b]fluorenyl, 11,11-diphenyl-4-benzo[b]fluorenyl, 11,11-diphenyl-5-benzo[b]fluorenyl, 11,11-diphenyl-6-benzo[b]fluorenyl, 11,11-diphenyl-7-benzo[b]fluorenyl ] fluorenyl, 11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9-benzo[b]fluorenyl, 11,11-diphenyl-10-benzo[b]fluorenyl, 11,11-diphenyl-1-benzo[c]fluorenyl, 11,11-diphenyl-2-benzo[c]fluorenyl, 11,11-diphenyl-3-benzo[c]fluorenyl, 11,11-diphenyl-4-benzo[c]fluorenyl, 11,11-diphenyl-5-benzo[c]fluorenyl, 11,11-diphenyl-6-benzo[c]fluorenyl, 11 ,11-diphenyl-7-benzo[c]fluorenyl, 11,11-diphenyl-8-benzo[c]fluorenyl, 11,11-diphenyl-9-benzo[c]fluorenyl, 11,11-diphenyl-10-benzo[c]fluorenyl, 9,9,10,10-tetramethyl-9,10-dihydro-1-phenanthryl, 9,9,10,10-tetramethyl-9,10-dihydro-2-phenanthryl, 9,9,10,10-tetramethyl-9,10-dihydro-3-phenanthryl, 9,9,10,10-tetramethyl-9,10-dihydro-4-phenanthryl, etc. ,

[0042] The terms "(3- to 30-membered) heteroaryl", "(3- to 30-membered) heteroarylene" and "(3- to 30-membered) heteroarenetriyl" mean 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, P, Se, Te and Ge. The above heteroaryl group may be a monocyclic ring or a condensed ring condensed with at least one benzene ring; may be partially saturated; may be a heteroaryl group formed by connecting at least one heteroaryl group or aryl group to a heteroaryl group via one or more single bonds; and may contain a spiro structure. The above heteroaryl groups may include monocyclic heteroaryl groups, such as furanyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl and pyridazinyl, and fused ring heteroaryl groups, such as benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothienyl, dibenzo benzothiophene, naphthobenzofuranyl, naphthobenzothiophene, naphthooxazolyl, benzofuranoquinolyl, benzofuranoquinazolinyl, benzofuranonaphthyridinyl, benzofuranopyrimidinyl, naphthofuranopyrimidinyl, benzothiophenoquinolyl, benzothiophenoquinazolinyl, naphthyridinyl, benzothiophenonaphthyridinyl, benzothiophenopyrimidinyl, naphthyphenopyrimidinyl, pyrimidoindolyl, benzofuranopyrazine yl, naphthofuranopyrazinyl, benzothiophenopyrazinyl, naphthothiophenopyrazinyl, phenanthroxazolyl, phenanthrothiazolyl, phenanthrobenzofuranyl, benzophenanthrothienyl, pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, benzoquinolinyl, The heteroaryl groups may include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazine-4-yl, 1,2,4-triazine-3-yl, 1,3,5-triazine-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolyl, 2-indolyl, 3-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 8-indolyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, pyridyl, 8-imidazopyridyl, 3-pyridyl, 4-pyridyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furanyl, 3-furanyl benzofuranyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, 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-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 2-methylpyrrol-6-yl, 2-methylpyrrol-7-yl, 2-methylpyrrol-8-yl, 2-methylpyrrol-9-yl, 2-methylpyrrol-1-yl, 2-methylpyrrol-2-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4 ...5-yl, 2-methylpyrrol-6-yl, 2-methylpyrrol-7-yl, 2-methylpyrrol-8-yl, 2-methylpyrrol-9-yl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, pyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2-tert-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4-tert-butyl-1-indolyl, 2-tert-butyl-3-indolyl, 4-tert-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-naphtho-[1,2-b]-benzofuranyl, 2-naphtho-[1,2-b]-benzofuranyl, 3-naphtho-[1,2-b]-benzofuranyl, 4-naphtho-[1,2-b]-benzofuranyl, 5-naphtho-[1,2-b]-benzofuranyl, 6-naphtho-[1,2-b]-benzofuranyl, 7-naphtho-[1,2-b]-benzofuranyl , 8-naphtho-[1,2-b]-benzofuranyl, 9-naphtho-[1,2-b]-benzofuranyl, 10-naphtho-[1,2-b]-benzofuranyl, 1-naphtho-[2,3-b]-benzofuranyl, 2-naphtho-[2,3-b]-benzofuranyl, 3-naphtho-[2,3-b]-benzofuranyl, 4-naphtho-[2, 3-b]-benzofuranyl, 5-naphtho-[2,3-b]-benzofuranyl, 6-naphtho-[2,3-b]-benzofuranyl, 7-naphtho-[2,3-b]-benzofuranyl, 8-naphtho-[2,3-b]-benzofuranyl, 9-naphtho-[2,3-b]-benzofuranyl, 10-naphtho-[2,3-b]-benzofuranyl 1-naphtho-[2,1-b]-benzofuranyl, 2-naphtho-[2,1-b]-benzofuranyl, 3-naphtho-[2,1-b]-benzofuranyl, 4-naphtho-[2,1-b]-benzofuranyl, 5-naphtho-[2,1-b]-benzofuranyl, 6-naphtho-[2,1-b]-benzofuranyl, 7-naphtho-[2,1-b]-benzofuranyl, 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]-benzothiophenyl, 5-naphtho-[1,2-b]-benzothiophenyl, 6-naphtho-[1,2-b]-benzothiophenyl, 7-naphtho-[1,2-b]-benzothiophenyl, 8-naphtho-[1,2-b]-benzothiophenyl, 9-naphtho-[1,2-b]-benzothiophenyl, 10-naphtho-[1 ,2-b]-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 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,1-b]-benzothiophenyl, 9-naphtho-[2,1-b]-benzothiophenyl, 10-naphtho-[2,1-b]-benzothiophenyl, 2-benzofurano[3,2-d]pyrimidinyl, 6-benzofurano[3,2-d]pyrimidinyl, 7-benzofurano[3,2-d]pyrimidinyl, 8-benzofurano[3,2-d]pyrimidinyl, 9-benzofurano[3,2-d]pyrimidinyl, 2-benzothio[3,2-d]pyrimidinyl, 6-benzothio[3,2-d]pyrimidinyl, 7-benzothio[3,2-d]pyrimidinyl, 8-benzothio[3,2-d]pyrimidinyl, 9-benzothio[3,2-d]pyrimidinyl, 2-benzofurano[3,2-d]pyrimidinyl, , 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-benzothio[3,2-d]pyrazinyl, 6-benzothio[3,2-d]pyrazinyl, 7-benzothio[3,2-d]pyrazinyl

[0063] In some embodiments, the present invention includes 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, etc. The “heteroaryl (sub) group” can be classified into a heteroaryl (sub) group having an electron characteristic and a heteroaryl (sub) group having a hole characteristic. The (sub)heteroaryl with electron characteristics is a relatively electron-rich substituent in the parent core, such as substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazine, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinolinyl, etc. The (sub)heteroaryl with hole characteristics is a relatively electron-deficient substituent in the parent core, such as substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, etc. In the present disclosure, the term "halogen" includes F, Cl, Br and I. ,

[0043] In addition, "ortho-", "(o-)", "meta-", "(m-), and "para-", "(p-)" are prefixes, each of which indicates the relative position of a substituent. The prefix "ortho-" means that two substituents are adjacent to each other, and for example, when two substituents in a benzene derivative occupy positions 1 and 2 or positions 2 and 3, this is referred to as the "ortho-" configuration. The prefix "meta-" means that two substituents are at positions 1 and 3, and for example, when two substituents in a benzene derivative occupy positions 1 and 3, this is referred to as the "meta-" configuration. The prefix "para-" means that two substituents are at positions 1 and 4, and for example, when two substituents in a benzene derivative occupy positions 1 and 4, this is referred to as the "para-" configuration. Unless otherwise indicated, a substituent may replace a hydrogen at a position where a substituent may be substituted, without limitation, and when two or more hydrogen atoms in a functional group are each replaced by a substituent, each substituent may be the same or different from one another. The maximum number of substituents that can be substituted for a functional group may be the total number of valences that can be substituted for each atom forming the functional group.Here, in the formula of the present disclosure, the substituted alkyl, substituted cycloalkyl, substituted (ene)aryl, substituted (ene)heteroaryl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted condensed ring, substituted condensed ring group of one or more aliphatic rings and one or more aromatic rings are each independently substituted by at least one selected from the group consisting of: deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; phosphine oxide; (C1-C30)alkyl; halogenated (C1-C30)alkyl; (C2-C30)alkenyl; (C2-C30)alkynyl; (C1-C 30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl; (3- to 7-membered)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (C6-C30)aryl, unsubstituted or substituted with at least one of one or more (C1-C30)alkyl and one or more di(C6-C30)arylamino; (3- to 30-membered)heteroaryl, unsubstituted or substituted with one or more (C6-C30)aryl; tri(C1-C30)alkylsilyl; one or more tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C 30) arylsilyl; (C1-C30) alkyldi(C6-C30) arylsilyl; a fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings; amino; mono- or di-(C1-C30) alkylamino; mono- or di-(C2-C30) alkenylamino; mono- or di-(C6-C30) arylamino which is unsubstituted or substituted by one or more (C1-C30) alkyl; mono- or di-(3- to 30-membered) heteroarylamino; (C1-C30) alkyl(C2-C30) alkenylamino; (C1-C30) alkyl(C6-C30) arylamino; (C1-C30) (C2-C30)alkyl(3- to 30-membered)heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30)alkenyl(3- to 30-membered)heteroarylamino; (C6-C30)aryl(3- to 30-membered)heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylborylcarbonyl; di(C1-C30)alkylborylcarbonyl; (C1-C30)alkyl(C6-C30)arylborylcarbonyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl.According to one embodiment of the present disclosure, the substituted compounds are each independently substituted by at least one selected from the group consisting of: deuterium; halogen; (C1-C30) alkyl; halogenated (C1-C30) alkyl; (C2-C30) alkenyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3- to 7-membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (C6-C30) aryl which is unsubstituted or substituted by at least one of one or more (C1-C30) alkyl and one or more di(C6-C30) arylamino groups; unsubstituted or substituted by one or more (C6-C30)aryl (3- to 30-membered) heteroaryl; a fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings; an amino group; a mono- or di-(C1-C30) alkylamino group; a mono- or di-(C2-C30) alkenylamino group; a mono- or di-(C6-C30) arylamino group unsubstituted or substituted by one or more (C1-C30) alkyl group; a mono- or di-(3- to 30-membered) heteroarylamino group; a (C1-C30) alkyl (C2-C30) alkenylamino group; a (C1-C30) alkyl (C6-C30) arylamino group; a (C. 1 -C30)alkyl (3- to 30-membered) heteroarylamino; (C 2-C30)alkenyl(C6-C30)arylamino; (C2-C30)alkenyl(3- to 30-membered)heteroarylamino; (C6-C30)aryl(3- to 30-membered)heteroarylamino; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl. According to another embodiment of the present disclosure, the substituted compounds are each independently substituted by at least one selected from the group consisting of: deuterium; halogen; (C1-C30) alkyl; halogenated (C1-C30) alkyl; (C2-C30) alkenyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (3- to 7-membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (C6-C30) aryl which is unsubstituted or substituted with at least one of one or more (C1-C30) alkyl and one or more di(C6-C30) arylamino; (3- to 30-membered) heteroaryl which is unsubstituted or substituted with one or more (C6-C30) aryl. a fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings; an amino group; a mono- or di-(C6-C30)arylamino group which is unsubstituted or substituted by one or more (C1-C30)alkyl groups; a (C1-C30)alkyl(C6-C30)arylamino group; a (C1-C30)alkyl(3- to 30-membered)heteroarylamino group; a (C2-C30)alkenyl(C6-C30)arylamino group; a (C2-C30)alkenyl(3- to 30-membered)heteroarylamino group; a (C6-C30)aryl(3- to 30-membered)heteroarylamino group; a (C6-C30)aryl(C1-C30)alkyl group; and a (C1-C30)alkyl(C6-C30)aryl group. For example, the substituted compounds can each independently be substituted by at least one selected from the group consisting of deuterium, methyl, cyclohexyl, fluoranthene, phenoxazinyl, tert-butylphenyl, phenyl, phenyl substituted by deuterium, phenyl substituted by naphthyl, biphenyl, terphenyl, naphthyl, naphthyl substituted by phenyl, dinaphthyl, dibenzofuranyl, dibenzofuranyl substituted by phenyl, triazine substituted by diphenyl, dibenzothiophenyl, carbazolyl substituted by phenyl, carbazolyl, benzothiazolyl, phenanthryl, dibenzoselenophene, isothiophene, substituted by phenyl, pyridyl, dimethylbenzene, dimethylfluorenyl, naphthotriazolyl, benzonaphthofuranyl, dimethylbenzofluorenyl, benzonaphthofuranyl and diphenylamino.

[0044] In the present disclosure, if there is no indication of substituents in the formula or compound structure, this may mean that all possible positions of the substituent are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms can be isotope deuterium, and in this case, the content of deuterium can be 0% to 100%. In the present disclosure, in the case of no indication of substituents in the formula or compound structure, if substituents are not explicitly excluded, such as 0% deuterium, 100% hydrogen, and all substituents are hydrogen, then hydrogen and deuterium can be mixed in the compound. Deuterium is one of the isotopes of hydrogen and is an element with a deuteron as its core, which is composed of a proton and a neutron. It can be expressed as hydrogen-2, and its element symbol can be written as D or 2H. Isotopes are atoms with the same atomic number (Z) but different mass numbers (A), and can also be interpreted as elements with the same number of protons but different numbers of neutrons.

[0045] In the present disclosure, "combinations thereof" refers to combinations of one or more elements from the corresponding list to form known or chemically stable arrangements that can be envisioned by a person skilled in the art from the corresponding list. For example, alkyl and deuterium can be combined to form partially or fully deuterated alkyl; halogen and alkyl can be combined to form haloalkyl substituents; halogen, alkyl and aryl can be combined to form haloarylalkyl. For example, preferred combinations of substituents include up to 50 atoms other than hydrogen or deuterium, up to 40 atoms other than hydrogen or deuterium, up to 30 atoms other than hydrogen or deuterium, or in many cases, preferred combinations of substituents can include up to 20 atoms other than hydrogen or deuterium.

[0046] In the formula of the present disclosure, when there are a plurality of substituents represented by the same symbol, each substituent represented by the same symbol may be the same as or different from each other.

[0047] In the formula of the present disclosure, when a ring is formed by connecting with an adjacent substituent, the ring can be connected with two or more adjacent substituents to form a substituted or unsubstituted, monocyclic or polycyclic (3 to 30 yuan) alicyclic or aromatic ring, or a combination thereof. In addition, 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 the present disclosure, the number of ring skeleton atoms is (5 to 20 yuan), and according to another embodiment of the present disclosure, the number of ring skeleton atoms is (5 to 15 yuan).

[0048] Hereinafter, a compound according to one embodiment will be described in more detail.

[0049] The compound according to one embodiment of the present disclosure is represented by Formula 1 below.

[0050]

[0051] In formula 1,

[0052] R 1 and R 2 are linked to each other to form one or more substituted or unsubstituted condensed rings.

[0053] R 3 To R 10 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, or substituted or unsubstituted tri(C6-C30) arylsilyl. The above condensed ring or R 3 To R 10 At least one of the substituents is a substituted or unsubstituted (3- to 30-membered) heteroaryl group containing nitrogen. According to one embodiment of the present disclosure, R 3 To R 10 Each independently may represent hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C1-C30) alkoxy. According to another embodiment of the present disclosure, R 3 To R 10 Each independently may represent hydrogen, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C1-C30) alkoxy. 3 To R 10The triazine radicals are independently hydrogen, triazine radicals substituted by one or more diphenyl radicals, triazine radicals substituted by phenyl and biphenyl radicals, triazine radicals substituted by phenyl and naphthyl radicals, triazine radicals substituted by one or more dinaphthyl radicals, triazine radicals substituted by phenyl and dibenzofuranyl radicals, triazine radicals substituted by dibenzothienyl and phenyl radicals, triazine radicals substituted by phenyl and carbazolyl radicals substituted by one or more phenyl radicals, triazine radicals substituted by one or more diphenyl radicals substituted by deuterium, phenyl radicals substituted by one or more triazine radicals substituted by one or more diphenyl radicals, triazine radicals substituted by one or more diphenyl radicals, substituted naphthyl, pyrimidinyl substituted with one or more diphenyl groups, quinazolinyl substituted with one or more phenyl groups, quinoxalinyl substituted with one or more phenyl groups, benzotriazolyl substituted with one or more phenyl groups, phenyl substituted with one or more benzotriazolyl groups, triazinyl substituted with phenyl and naphthyl substituted with one or more phenyl groups, triazinyl substituted with phenyl and phenyl substituted with one or more naphthyl groups, triazinyl substituted with naphthyl and phenanthryl, unsubstituted or substituted triazinyl substituted with phenyl and dibenzoselenophene, unsubstituted or substituted triazinyl substituted with phenanthryl and dibenzofuranyl, unsubstituted or substituted triazinyl substituted with isocyanate, The invention also comprises a triazinyl group substituted with a dibenzofuranyl group and a dibenzofuranyl group, a triazinyl group substituted with a dimethylfluorenyl group and a dibenzofuranyl group, a phenyl group substituted with one or more naphthotriazolyl groups, a naphthotriazolyl group substituted with one or more phenyl groups, a triazinyl group substituted with a dibenzofuranyl group and a carbazolyl group substituted with one or more phenyl groups, a triazinyl group substituted with a phenyl group and a dibenzofuranyl group substituted with one or more phenyl groups, a triazinyl group substituted with a phenyl group and a dibenzofuranyl group substituted with one or more phenyl groups, a triazinyl group substituted with a phenyl group and a benzonaphthofuranyl group, a triazinyl group substituted with a phenyl group and a terphenyl group, a triazinyl group substituted with a phenyl group and a dimethylbenzofluorenyl group, or a triazinyl group substituted with a phenyl group and a benzonaphthofuranyl group.

[0054] According to one embodiment of the present disclosure, Formula 1 may be represented by any one of the following Formulas 1-1 to 1-4.

[0055]

[0056] In formulas 1-1 to 1-4,

[0057] R 3 To R 10 is defined as in Equation 1.

[0058] A 1 To A 9Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, or substituted or unsubstituted tri(C6-C30) arylsilyl. According to one embodiment of the present disclosure, A 1 To A 9 Each independently represents hydrogen, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C1-C30) alkoxy. According to another embodiment of the present disclosure, A 1 To A 9 Each independently represents hydrogen, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (3- to 25-membered) heteroaryl. 1 To A 9 Each independently represents hydrogen, a triazinyl substituted by one or more diphenyl groups, a triazinyl substituted by phenyl and biphenyl groups, a triazinyl substituted by phenyl and naphthyl groups, a triazinyl substituted by one or more dinaphthyl groups, a triazinyl substituted by phenyl and dibenzofuranyl groups, a triazinyl substituted by dibenzothienyl and phenyl groups, a triazinyl substituted by phenyl and a carbazolyl substituted by one or more phenyl groups, a triazinyl substituted by one or more diphenyl groups substituted by deuterium, a phenyl substituted by one or more triazinyl substituted by one or more diphenyl groups, a naphthyl substituted by a triazinyl substituted by one or more diphenyl groups, a pyrimidinyl substituted by one or more diphenyl groups, a quinazolinyl substituted by one or more phenyl groups, or a quinoxalinyl substituted by one or more phenyl groups.

[0059] X 1 means -N=; and X 2 Indicates -NR 11 , -O-, or -S-.

[0060] R 11represents 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, or substituted or unsubstituted tri(C6-C30) arylsilyl. According to one embodiment of the present disclosure, R 11 represents hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, or substituted or unsubstituted (C3-C30) cycloalkyl. According to another embodiment of the present disclosure, R 11 represents hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C6-C30) aryl.

[0061] For example, R 11 represents hydrogen or phenyl.

[0062] R 3 To R 11 and A 1 To A 9 At least one of represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group containing at least one N.

[0063] The compound represented by Formula 1 may be selected from the following compounds, but is not limited thereto.

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076] The present disclosure provides an organic electroluminescent device including an organic electroluminescent compound represented by Formula 1.

[0077] The organic electroluminescent compound represented by Formula 1 of the present disclosure may be contained in at least one layer selected from 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, and may preferably be contained in a light-emitting layer (host material), an electron transport layer or an electron buffer layer.

[0078] According to another embodiment of the present disclosure, an organic electroluminescent material including a compound represented by the above Formula 1 and a compound represented by the following Formula 2 is provided.

[0079]

[0080] In formula 2,

[0081] Y 1 and Y 2 Each independently represents -N=, -NR 16 -, -O- or -S-, provided that Y 1 and Y 2 Any one of -N=, and Y 1 and Y 2 Another representation in -NR 16 -, -O-, or -S-. For example, Y 1 or Y 2 Can be -N=, and Y 1 or Y 2 The other one in can be -O- or -S-.

[0082] R 12 represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group. According to one embodiment of the present disclosure, R 12 represents a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (3- to 25-membered) heteroaryl group. According to another embodiment of the present disclosure, R 12 Indicates substituted or unsubstituted (C6-C 25 ) aryl. For example, R 12 It may represent phenyl, biphenyl, naphthyl or phenanthryl.

[0083] R 13 To R 16 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted condensed ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or -L 1 -N-(Ar 1 )(Ar 2 ); or may be linked to one or more adjacent substituents to form one or more rings; provided that R 13 To R 15 At least one of them is -L 1 -N-(Ar 1 )(Ar 2 ). According to one embodiment of the present disclosure, R 13 To R 16 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted condensed ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or -L 1 -N(Ar 1 )(Ar 2 ); or may be linked to one or more adjacent substituents to form one or more rings; provided that R 13 To R 15 At least one of them is -L 1 -N-(Ar 1 )(Ar 2 ). According to another embodiment of the present disclosure, R 13 To R 16 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C20) aryl, substituted or unsubstituted (3-20-membered) heteroaryl, a substituted or unsubstituted fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or -L 1 -N(Ar1 )(Ar 2 ); or may be linked to one or more adjacent substituents to form one or more rings; provided that R 13 To R 15 At least one of them is -L 1 -N-(Ar 1 )(Ar 2 ). For example, R 13 To R 16 Each independently represents hydrogen, phenyl, or -L 1 -N(Ar 1 )(Ar 2 ), or may be connected with one or more adjacent substituents to form one or more benzene rings; provided that R 13 To R 15 At least one of them is -L 1 -N-(Ar 1 )(Ar 2 ).

[0084] Ar 1 and Ar 2 Each independently represents a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, or a substituted or unsubstituted condensed ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings. According to one embodiment of the present disclosure, Ar 1 and Ar 2 Each independently represents a substituted or unsubstituted (C6-C25) aryl group, a substituted or unsubstituted (3- to 25-membered) heteroaryl group, or a substituted or unsubstituted condensed ring group of one or more (C3-C25) aliphatic rings and one or more (C6-C25) aromatic rings. For example, Ar 1 and Ar 2Each of the following may be independently benzonaphthofuranyl, benzothienyl, dibenzofuranyl, dibenzofuranyl substituted with one or more phenyl groups, dibenzothienyl, dimethylbenzofluorenyl, dimethylfluorenyl, diphenylfluorenyl, naphthyl, naphthyl substituted with one or more phenyl groups, phenyl, phenyl substituted with one or more anthracene groups, phenyl substituted with one or more benzimidazolyl groups substituted with one or more phenyl groups, phenyl substituted with one or more naphthyl groups, phenyl substituted with one or more pyridyl groups substituted with one or more phenyl groups, phenyl substituted with one or more phenyl groups, Phenyl substituted with multiple diphenylamino groups, phenyl substituted with one or more xylenes, phenyl substituted with one or more deuterium substituted phenyl, phenyl substituted with one or more cyclohexanes, phenyl substituted with one or more fluoranthene groups, phenyl substituted with one or more phenoxazine groups, phenyl substituted with one or more tert-butylphenyl groups, biphenyl groups, terphenyl groups, quaterphenyl groups, benzonaphthothienyl groups, carbazolyl groups substituted with one or more phenyl groups, phenanthrenyl groups, spirobifluorenyl groups, dihydrophenanthrenyl groups substituted with one or more methyl groups, or (C22)aryl groups.

[0085] L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group. According to one embodiment of the present disclosure, L 1 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene group. According to another embodiment of the present disclosure, L 1 represents a single bond, or a substituted or unsubstituted (C6-C20)arylene group. 1 It may be a single bond or a phenylene group.

[0086] In Formula 2, a and b each independently represent an integer of 1 or 2, and c represents an integer of 1 to 4, wherein if a to c are integers of 2 or more, each R 13 To each R 15 May be the same as or different from each other.

[0087] According to one embodiment of the present disclosure, the compound represented by Formula 2 may be more specifically exemplified as the following compounds, but is not limited thereto.

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094] According to another embodiment of the present disclosure, there is provided a compound represented by Formula 1 and

[0095] An organic electroluminescent material of the compound represented by formula 3.

[0096]

[0097] In formula 3,

[0098] X stands for O, S, CR 21 R 22 NR 23 According to one embodiment of the present disclosure, X represents O or S. For example, X may be O.

[0099] R 21 To R 23 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; or may be connected with one or more adjacent substituents to form one or more rings. According to one embodiment of the present disclosure, R 21 To R 23 Each independently may be hydrogen, deuterium, halogen, or substituted or unsubstituted (C1-C30) alkyl.

[0100] R 17 To R 20 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, The premise is R 17 To R 20 At least one of According to one embodiment of the present disclosure, R 17 To R 20 Each independently represents hydrogen, deuterium, The premise is R 17 To R 20 At least one of For example, R 17 To R 20 Each independently can be hydrogen, The condition is R 17 To R 20 At least one of

[0101] L 2 and L 3Each independently represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, a substituted or unsubstituted (C3-C30)cycloalkylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group. According to one embodiment of the present disclosure, L 2 and L 3 Each independently represents a single bond, or a substituted or unsubstituted (C6-C30)arylene group. 2 and L 3 Each independently may be a single bond or a phenylene group.

[0102] Ar 3 To Ar 7 Each independently represents a substituted or unsubstituted (C6-C30) aryl group or a substituted or unsubstituted (3- to 30-membered) heteroaryl group. According to one embodiment of the present disclosure, Ar 3 To Ar 7 Each independently represents a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (3- to 25-membered) heteroaryl group. 3 To Ar 7 Each independently can be phenyl, phenyl substituted by one or more phenylpropyl groups, biphenyl, terphenyl, naphthyl, phenanthryl, pyridyl substituted by one or more phenyl groups, dibenzofuranyl, naphthyl substituted by one or more phenyl groups, phenylcarbazolyl, or dihydrophenanthryl substituted by one or more methyl groups.

[0103] d and g represent integers of 1 to 4, and e and f represent integers of 1 or 2, wherein if d to g are integers of 2 or more, each R 17 To each R 20 May be the same as or different from each other.

[0104] * indicates the site of connection with Formula 3.

[0105] According to one embodiment of the present disclosure, the compound represented by Formula 3 may be more specifically exemplified as the following compounds, but is not limited thereto.

[0106]

[0107]

[0108]

[0109] At least one of the compound represented by Formula 1 and compounds H1-1 to H1-131 may be used in an organic electroluminescent material. According to one embodiment of the present disclosure, the present disclosure provides an organic electroluminescent device including an organic electroluminescent material.

[0110] At least one of the compound represented by Formula 1 and compounds H1-132 to H1-204 may be used in an organic electroluminescent material. According to one embodiment of the present disclosure, the present disclosure provides an organic electroluminescent device including an organic electroluminescent material.

[0111] The compound represented by Formula 1 according to the present disclosure may be produced by referring to the following Reaction Scheme 1, but is not limited thereto.

[0112] [Reaction Scheme 1]

[0113]

[0114] In reaction scheme 1, R 1 To R 10 is as defined for Eq. 1.

[0115] The compound represented by Formula 2 according to the present disclosure can be synthesized by referring to a synthesis method known to those skilled in the art, and in particular, a synthesis method disclosed in many patent documents can be used. For example, it can be synthesized by referring to the synthesis method disclosed in Korean Patent Application Publication No. 2017-0022865 (published on June 24, 2032), but is not limited thereto.

[0116] The compound represented by Formula 3 according to the present disclosure may be produced by referring to the following Reaction Scheme 2, but is not limited thereto, and it may also be produced by a synthesis method known to those skilled in the art.

[0117] [Reaction Scheme 2]

[0118]

[0119] Although illustrative synthesis examples of the compounds represented by Formulae 1 to 3 are described above, those skilled in the art will be able to easily understand that they are all based on Buchwald-Hartwig cross-coupling reaction, N-arylation reaction, H-mont mediated etherification reaction, Miyaura borylation reaction, Suzuki cross-coupling reaction, intramolecular acid-induced cyclization reaction, Pd(II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, dehydration cyclization reaction, SN1 substitution reaction, SN2 substitution reaction, phosphine-mediated reductive cyclization reaction, and Wittig reaction, etc., and that the above reactions proceed even when substituents defined in Formulae 1 to 3 other than the substituents specified in the specific synthesis examples are bonded.

[0120] Hereinafter, an organic electroluminescent device using the compound and an organic electroluminescent material including the compound will be described.

[0121] According to one embodiment of the present disclosure, the organic electroluminescent device of the present disclosure includes a first electrode; a second electrode; and at least one organic layer between the first electrode and the second electrode, wherein the organic layer includes a hole transport layer and a light-emitting layer. According to one example, the hole transport layer may include a compound represented by Formula 1. According to another example, the light-emitting layer may include a compound represented by Formula 1 as a first host compound and a compound represented by Formula 2 as a second host compound. Here, the weight ratio of the first host compound to the second host compound contained in the light-emitting layer may be in the range of about 1:99 to about 99:1, preferably about 10:90 to about 90:10, more preferably about 30:70 to about 70:30, more preferably about 40:60 to about 60:40, and even more preferably about 50:50. According to another example, the light-emitting layer may include a compound represented by Formula 1 as a first host compound and a compound represented by Formula 3 as a second host compound. Here, a weight ratio of the first host compound to the second host compound contained in the light emitting layer may be in the range of about 1:99 to about 99:1, preferably about 10:90 to about 90:10, more preferably about 30:70 to about 70:30, more preferably about 40:60 to about 60:40, and even more preferably about 50:50.

[0122] According to one example, the organic electroluminescent material of the present disclosure includes at least one compound of compounds H2-1 to H2-305 and at least one compound of compounds H1-1 to H1-131, and these organic electroluminescent materials may be included in the same organic layer (e.g., light-emitting layer), or may be included in different light-emitting layers, respectively. In addition, according to another example, the organic electroluminescent material of the present disclosure includes at least one compound of compounds H2-1 to H2-305 and at least one compound of compounds H1-132 to H1-204, and these organic electroluminescent materials may be included in the same organic layer (e.g., light-emitting layer), or may be included in different light-emitting layers, respectively.

[0123] In addition to the hole transport layer and the light-emitting layer, the organic layer may further include at least one layer selected from a hole injection layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron injection layer, an intermediate layer, a hole blocking layer, an electron blocking layer and an electron buffer layer. In addition to the light-emitting material of the present disclosure, the organic layer may further include an amine-based compound and / or an azine-based compound. Specifically, the hole injection layer, the hole transport layer, the hole auxiliary layer, the light-emitting layer, the light-emitting auxiliary layer, or the electron blocking layer may include an amine-based compound (e.g., an arylamine-based compound, a styryl arylamine-based compound, etc.) as a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting material, a light-emitting auxiliary material, or an electron blocking material. In addition, the electron transport layer, the electron injection layer, the electron buffer layer, and the hole blocking layer may include an azine-based compound as an electron transport material, an electron injection material, an electron buffer material, or a hole blocking material. In addition, the organic layer may further contain at least one metal selected from the group consisting of metals of Group 1 of the periodic table, metals of Group 2, transition metals of Period 4, transition metals of Period 5, lanthanoids and organometallics of d-transition elements, or at least one complex compound containing a metal therein.

[0124] According to one embodiment of the present disclosure, the organic electroluminescent material can be used as a light-emitting material for a white organic light-emitting device. It has been proposed that the white organic light-emitting device has various structures, such as a side-by-side structure or a stacked structure, depending on the arrangement of R (red), G (green) or YG (yellow-green) and B (blue) light-emitting parts, or a color conversion material (CCM) method, etc. In addition, the compound or organic electroluminescent material according to one embodiment of the present disclosure can also be used in an organic electroluminescent device containing quantum dots (QDs).

[0125] One of the first electrode and the second electrode may be an anode, and the other may be a cathode. At this time, the first electrode and the second electrode may each be formed of a transparent conductive material, or a semi-transparent or reflective conductive material. Depending on the type of material forming the first electrode and the second electrode, the organic electroluminescent device may be a front emission type, a rear emission type, or a double-side emission type.

[0126] A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof can be used between the anode and the light-emitting layer. For the purpose of reducing the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, the hole injection layer can be composed of multiple layers, and each layer can use two compounds at the same time. In addition, the hole injection layer can be doped with a p-type dopant. The electron blocking layer can be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can block the overflow of electrons from the light-emitting layer and confine the excitons in the light-emitting layer to prevent light leakage. The hole transport layer or the electron blocking layer can use multiple layers, and a variety of compounds can be used in each layer.

[0127] An electron buffer layer, a hole blocking layer, an electron transport layer, 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 a multilayer to control the injection of electrons and improve the interface characteristics between the light-emitting layer and the electron injection layer, wherein each of the multilayers can use two compounds at the same time. The hole blocking layer is located between the electron transport layer (or electron injection layer) and the light-emitting layer, and is a layer that blocks holes from reaching the cathode, thereby improving the recombination probability of electrons and holes in the light-emitting layer. The hole blocking layer or the electron transport layer can also be a multilayer, and a variety of compounds can be used in each layer. In addition, the electron injection layer can be doped with an n-type dopant.

[0128] The luminescence auxiliary layer may be a layer placed between the anode and the luminescent layer or between the cathode and the luminescent layer. When the luminescence auxiliary layer is placed between the anode and the luminescent layer, the luminescence auxiliary layer may be used to promote hole injection and / or hole transport or block the overflow of electrons. When the luminescence auxiliary layer is placed between the cathode and the luminescent layer, the luminescence auxiliary layer may be used to promote electron injection and / or electron transport or block the overflow of holes. In addition, the hole auxiliary layer may be placed between the hole transport layer (or hole injection layer) and the luminescent layer, and may exhibit the effect of promoting or blocking the hole transport rate (or hole injection rate), and thus may adjust the charge balance. When the organic electroluminescent device includes two or more hole transport layers, the further included hole transport layer may be used as a hole auxiliary layer or an electron blocking layer. The luminescence auxiliary layer, the hole auxiliary layer or the electron blocking layer may have the effect of improving the efficiency and / or life of the organic electroluminescent device.

[0129] In the organic electroluminescent device of the present disclosure, at least one layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter referred to as a "surface layer") is preferably placed on at least one inner surface of a pair of electrodes. Specifically, a chalcogenide (including oxide) layer of silicon and aluminum is preferably placed on the anode surface on the electroluminescent medium layer side, and a metal halide layer or a metal oxide layer is preferably placed on the cathode surface on the electroluminescent medium layer side. The driving stability of the organic electroluminescent device can be obtained by the surface layer. Preferred examples of chalcogenides include SiO X (1≤X≤2), AlO X (1≤X≤1.5), SiON, SiAlON, etc. Preferred examples of metal halides include LiF, MgF 2 , CaF 2 , rare earth metal fluorides, etc., and preferred examples of metal oxides include Cs 2 O. Li 2 O, MgO, SrO, BaO, CaO, etc.

[0130] In addition, in the organic electroluminescent device of the present disclosure, a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant can be placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to anions, and thus it becomes easier to inject and transport electrons from the mixed region to the luminescent medium. In addition, the hole transport compound is oxidized to cations, and thus it becomes easier to inject and transport holes from the mixed region to the luminescent medium. Preferred oxidative dopants include various Lewis acids and acceptor compounds, and preferred reductive dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, an organic electroluminescent device having at least two light-emitting layers and emitting white light can be manufactured by using a reductive dopant layer as a charge generation layer.

[0131] The organic electroluminescent device according to the present disclosure may be an organic electroluminescent device having a series structure. In the case of a series organic electroluminescent device according to one embodiment, a single light-emitting unit (light-emitting part) may be formed into a structure in which two or more units are connected by a charge generation layer. The organic electroluminescent device may include a plurality of two or more light-emitting units, for example, a plurality of three or more light-emitting units, the light-emitting unit having a first electrode and a second electrode opposite to each other on a substrate and a light-emitting layer stacked between the first electrode and the second electrode and emitting light within a specific wavelength range. The organic electroluminescent device may include a plurality of light-emitting units, and each of these light-emitting units may include a hole transport region, a light-emitting layer, and an electron transport region, and the hole transport region may include a hole injection layer and a hole transport layer, and the electron transport region may include an electron transport layer and an electron injection layer. According to one embodiment of the present disclosure, three or more light-emitting layers may be included in the light-emitting unit. Multiple light-emitting units may emit the same color or different colors. In addition, a light-emitting unit may include one or more light-emitting layers, and multiple light-emitting layers may be light-emitting layers of the same or different colors. It may include one or more charge generation layers located between each light-emitting unit. The charge generation layer refers to a layer that generates holes and electrons when a voltage is applied. When there are three or more light-emitting units, the charge generation layer may be located between the light-emitting units. In this case, the multiple charge generation layers may be the same as or different from each other. By arranging the charge generation layer between the light-emitting units, the current efficiency in each light-emitting unit is increased, and the charge can be evenly distributed. Specifically, the charge generation layer is arranged between two adjacent stacks, and can be used to drive a tandem organic electroluminescent device using only a pair of anodes and cathodes, without the need for a separate internal electrode located between the stacks.

[0132] The charge generation layer may be composed of an N-type charge generation layer and a P-type charge generation layer, and the N-type charge generation layer may be doped with an alkali metal, an alkaline earth metal, or a compound of an alkali metal and an alkaline earth metal. The alkali metal may include one selected from the group consisting of Li, Na, K, Rb, Cs, Fr, Yb, and combinations thereof, and the alkaline earth metal may include one selected from the group consisting of Be, Mg, Ca, Sr, Ba, Ra, and combinations thereof. The P-type charge generation layer may be made of a metal or an organic material doped with a P-type dopant. For example, the metal may be made of one or two or more alloys selected from the group consisting of: Al, Cu, Fe, Pb, Zn, Au, Pt, W, In, Mo, Ni, and Ti. In addition, commonly used materials may be used as P-type dopants and host materials used in P-type doped organic materials.

[0133] The manufacturing method of the organic electroluminescent device disclosed in the present invention is not limited, and the manufacturing method of the device example described below is only an example and is not limited thereto. A person skilled in the art can reasonably modify the manufacturing method of the device example described below by relying on the prior art. For example, there is no particular restriction on the mixing ratio of the first compound and the second compound, and therefore a person skilled in the art can reasonably select within a certain range according to the prior art. For example, based on the total weight of the light-emitting layer material, the total weight of the first compound and the second compound accounts for 99.5%-80.0% of the total weight of the light-emitting layer, the weight ratio of the first compound to the second compound is 1:99 to 99:1, the weight ratio of the first compound to the second compound can be 20:80 to 99:1, or the weight ratio of the first compound to the second compound can be 50:50 to 90:10. In the manufacture of the device, when the light-emitting layer is formed by co-depositing two or more host materials and light-emitting materials, the two or more host materials and the light-emitting materials can be placed in different evaporation sources and co-deposited to form a light-emitting layer, or a pre-mixed mixture of two or more host materials can be placed on the same evaporation source and then co-deposited with the light-emitting material placed on another evaporation source to form a light-emitting layer. This premixing method can further save evaporation sources. According to one embodiment, the first compound, the second compound, and the light-emitting material of the present disclosure can be placed in different evaporation sources and co-deposited to form a light-emitting layer, or the premixed mixture of the first compound and the second compound can be placed in the same evaporation source and then co-deposited with the light-emitting material placed in another evaporation source to form a light-emitting layer.

[0134] The organic electroluminescent device according to one embodiment may further include one or more dopants in the light emitting layer.

[0135] The dopant included in the organic electroluminescent device of the present disclosure may be at least one phosphorescent dopant or fluorescent dopant, and is preferably a phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particularly limited, but may preferably be selected from the group consisting of metallized iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt) complex compounds, more preferably selected from the group consisting of ortho-metallized iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt) complex compounds, and even more preferably ortho-metallized iridium complex compounds.

[0136] The dopant included in the organic electroluminescent device of the present disclosure may be a compound represented by the following Formula 101, but is not limited thereto.

[0137]

[0138] In formula 101,

[0139] L is selected from any one of the following structures 1 to 3;

[0140]

[0141] R 100 To R 103 Each independently represents hydrogen, deuterium, halogen, unsubstituted or substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (3- to 30-membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; or may be linked to one or more adjacent substituents to form one or more rings together with pyridine, such as substituted or unsubstituted quinoline, benzofuranopyridine, benzothienopyridine, indenopyridine, benzofuranoquinoline, benzothienoquinoline, or indenoquinoline;

[0142] R 104 To R 107 Each independently represents hydrogen, deuterium, halogen, unsubstituted or substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; or may be linked to one or more adjacent substituents to form one or more substituted or unsubstituted rings with benzene, such as substituted or unsubstituted naphthalene, fluorene, dibenzothiophene, dibenzofuran, indenopyridine, benzofuranopyridine, or benzothienopyridine;

[0143] R 201 To R 220 Each independently represents hydrogen, deuterium, halogen, unsubstituted or substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C6-C30) aryl; or may be connected with one or more adjacent substituents to form one or more substituted or unsubstituted rings; and

[0144] s represents an integer of 1 to 3.

[0145] Specific examples of the dopant compound are as follows, but are not limited thereto.

[0146]

[0147]

[0148]

[0149]

[0150]

[0151] In order to form each layer of the organic electroluminescent device of the present disclosure, a dry film-forming method such as vacuum evaporation, sputtering, plasma, ion plating method, etc., or a wet film-forming method such as spin coating, dip coating, flow coating method, etc. can be used. When a wet film-forming method is used, a thin film can be formed by dissolving or diffusing the material forming each layer in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent can be any solvent in which the material forming each layer can be dissolved or diffused and there is no problem in film-forming ability.

[0152] When forming a film of an organic electroluminescent material according to an embodiment, the film can be formed by the methods listed above, and can be generally formed by a co-deposition or a mixed deposition process. Co-deposition is a method of mixing and depositing two or more materials by placing them in separate crucible sources and applying current to two chambers at the same time to evaporate the materials, and mixed deposition is a method of mixing two or more materials in one crucible source before deposition and then applying current to one chamber to evaporate the materials.

[0153] According to one embodiment of the present disclosure, the present disclosure may provide a display device comprising a compound represented by Formula 1, a display device comprising an organic electroluminescent material comprising a first host compound represented by Formula 1 and a second host compound represented by Formula 2, and / or a display device comprising an organic electroluminescent material comprising a first host compound represented by Formula 1 and a second host compound represented by Formula 3. In addition, the organic electroluminescent device of the present disclosure may be used to produce a display system, such as a display system for a smartphone, a tablet computer, a notebook, a PC, a TV, or a car; or a lighting system, such as an outdoor or indoor lighting system.

[0154] Hereinafter, for a detailed understanding of the present disclosure, a method for preparing a compound according to the present disclosure will be described using the synthesis of a representative compound or an intermediate compound of the present disclosure as an example.

[0155] Example 1: Preparation of Compound H2-5

[0156]

[0157] 1) Synthesis of Compound 1-1

[0158] In a flask, 10-bromo-2-chlorophenanthrene (20 g, 68 mmol), 2-bromophenylboronic acid (15 g, 75 mmol), Pd(PPh 3 ) 4(4 g, 3.4 mmol) and K 2 CO 3 (23.7 g, 171 mmol) was dissolved in 340 mL of toluene, 85 mL of ethanol and 85 mL of water, and then refluxed at 120 ° C for 4 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the remaining moisture was removed with magnesium sulfate. Thereafter, the organic layer was dried and separated by column chromatography to obtain compound 1-1 (21 g, yield: 83%).

[0159] 2) Synthesis of Compound 1-2

[0160] In a flask, compound 1-1 (21 g, 57 mmol), Pd(PPh 3 ) 2 Cl 2 (2g, 2.8mmol) and 1,8-diazabicyclo[5,4,0]undec-7-ene (25.6mL, 171mmol) were dissolved in 190mL of dimethylformamide (DMF), and then refluxed at 165°C for 4 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the remaining moisture was removed with magnesium sulfate. Thereafter, the organic layer was dried and separated by column chromatography to obtain compound 1-2 (12.2g, yield: 63%).

[0161] 3) Synthesis of Compound 1-3

[0162] In a flask, compound 1-2 (5 g, 17 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bis(1,3,2-dioxaborolane) (22 g, 87 mmol), Pd 2 dba 3 (798 mg, 0.8 mmol), SPhos (715 mg, 1.7 mmol) and KOAc (4.3 g, 43 mmol) were dissolved in 113 mL of 1,4-dioxane, followed by reflux at 100 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the remaining moisture was removed with magnesium sulfate. Thereafter, the organic layer was dried and separated by column chromatography to obtain compound 1-3 (6.5 g, yield: 82%).

[0163] 4) Synthesis of Compound H2-5

[0164] In a flask, compound 1-3 (6 g, 15.8 mmol), 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (5.6 g, 15.8 mmol), Pd(PPh 3 ) 4 (916 mg, 0.8 mmol) and K2 CO 3 (5.5g, 40mmol) was dissolved in 80mL toluene, 20mL ethanol and 20mL water, and then stirred for 4 hours under reflux. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the remaining moisture was removed with magnesium sulfate. Thereafter, the organic layer was dried and separated by column chromatography to obtain compound H2-5 (3.6g, yield: 40%).

[0165] MW MP <![CDATA[T g ]]> H2-5 573.65 294.7℃ 123℃

[0166] Example 2: Preparation of Compound H2-35

[0167]

[0168] 1) Synthesis of compound 2-1

[0169] In a flask, 9-bromo-2-chlorophenanthrene (50 g, 171 mmol), 2-bromophenylboronic acid (38 g, 188 mmol), Pd(PPh 3 ) 4 (9.9 g, 8.5 mmol) and K 2 CO 3 (59 g, 428 mmol) was dissolved in 860 mL of toluene, 215 mL of ethanol and 215 mL of water, and then refluxed at 120 ° C for 4 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the remaining moisture was removed with magnesium sulfate. Thereafter, the organic layer was dried and separated by column chromatography to obtain compound 2-1 (56.7 g, yield: 90%).

[0170] 2) Synthesis of Compound 2-2

[0171] In a flask, compound 2-1 (26.7 g, 72 mmol), Pd(PPh 3 ) 2 Cl 2 (2.5 g, 3.6 mmol) and 1,8-diazabicyclo[5,4,0]undec-7-ene (32.5 mL, 217 mmol) were dissolved in 240 mL of dimethylformamide (DMF), followed by reflux at 165 ° C for 4 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the remaining moisture was removed with magnesium sulfate. Thereafter, the organic layer was dried and separated by column chromatography to obtain compound 2-2 (16.5 g, yield: 79%).

[0172] 3) Synthesis of Compound 2-3

[0173] In a flask, compound 2-2 (7.6 g, 26 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bis(1,3,2-dioxaborolane) (13.4 g, 53 mmol), Pd 2 dba 3 (1.2 g, 1.3 mmol), SPhos (1.1 g, 2.6 mmol) and KOAc (6.5 g, 66 mmol) were dissolved in 173 mL of 1,4-dioxane, followed by reflux at 100 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the remaining moisture was removed with magnesium sulfate. Thereafter, the organic layer was dried and separated by column chromatography to obtain compound 2-3 (8.1 g, yield: 81%).

[0174] 4) Synthesis of Compound H2-35

[0175] In a flask, compound 2-3 (4 g, 10 mmol), 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (3.78 g, 10 mmol), Pd(PPh 3 ) 4 (610 mg, 0.5 mmol) and K 2 CO 3 (3.6 g, 26 mmol) was dissolved in 52 mL toluene, 13 mL ethanol and 13 mL water, and then stirred for 5 hours under reflux. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the remaining moisture was removed with magnesium sulfate. Thereafter, the organic layer was dried and separated by column chromatography to obtain compound H2-35 (3.1 g, yield: 51%).

[0176] MW MP <![CDATA[T g ]]> H2-35 573.65 329.6℃ 128℃

[0177] Example 3: Preparation of Compound H2-33

[0178]

[0179] In a flask, compound 2-3 (4 g, 10.5 mmol), 2-chloro-4-(2-naphthyl)-6-phenyl-1,3,5-triazine (3.7 g, 11 mmol), Pd(PPh 3 ) 4 (610 mg, 0.5 mmol) and K 2 CO 3(3.6 g, 26 mmol) was dissolved in 52 mL toluene, 13 mL ethanol and 13 mL water, and then stirred for 8 hours under reflux. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the remaining moisture was removed with magnesium sulfate. Thereafter, the organic layer was dried and separated by column chromatography to obtain compound H2-33 (2 g, yield: 35%).

[0180] MW MP <![CDATA[T g ]]> H2-33 533.63 303.6℃ 103℃

[0181] Device Examples 1 to 3: Production of OLEDs containing organic electroluminescent materials according to the present disclosure

[0182] Produce an OLED according to the present disclosure. First, a transparent electrode indium tin oxide (ITO) film (10Ω / sq) on a glass substrate for OLED (GEOMATEC CO., LTD., Japan) is ultrasonically washed with acetone and isopropanol in sequence, and then stored in isopropanol. The ITO substrate is mounted on a substrate holder of a vacuum vapor deposition device. The compound HI-1 shown in Table 3 is introduced into a chamber of the vacuum vapor deposition device, and the compound HT-1 is introduced into another chamber. The two materials are evaporated at different rates, and the compound HI-1 is deposited at a doping amount of 3wt% based on the total amount of the compound HI-1 and the compound HT-1 to form a first hole injection layer with a thickness of 10nm. Subsequently, the compound HT-1 is deposited on the first hole injection layer to form a first hole transport layer with a thickness of 80nm. Next, the compound HT-2 is introduced into another chamber of the vacuum vapor deposition device, and the compound is evaporated by applying an electric current to the chamber, thereby depositing a second hole transport layer with a thickness of 60nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, the light-emitting layer was deposited thereon as follows: Each of the first host compound and the second host compound shown in Table 1 below was introduced as a host into two chambers of a vacuum vapor deposition device, and compound D-39 was introduced as a dopant into another chamber. The two host materials were evaporated at a rate of 1:1, the dopant materials were evaporated simultaneously at different rates, and the dopant was deposited in a doping amount of 3wt% based on the total amount of the host and the dopant to form a light-emitting layer with a thickness of 40nm on the second hole transport layer. Then, compound ET-1 and compound EI-1 were evaporated as electron transport materials at a weight ratio of 50:50 to form an electron transport layer with a thickness of 35nm on the light-emitting layer. After compound EI-1 was deposited as an electron injection layer with a thickness of 2nm on the electron transport layer, an Al cathode with a thickness of 80nm was deposited on the electron injection layer using another vacuum vapor deposition device to produce an OLED. All materials used to produce OLEDs were heated to 10 -6 Purify by vacuum sublimation under vacuum.

[0183] Comparative Example 1: Production of an OLED containing a comparative compound as a host

[0184] An OLED was produced in the same manner as in Device Example 1, except that the second host compound shown in the following Table 1 was used.

[0185] Table 1 below shows the driving voltage, luminous efficiency, luminous color at a luminance of 1,000 nits, and the time it takes for the luminance to decrease from 100% to 95% at a luminance of 10,000 nits (lifetime: T95) for the OLEDs of device examples 1 to 3 and comparative example 1 produced as described above.

[0186] [Table 1]

[0187]

[0188]

[0189] As can be confirmed from the above Table 1, the OLED according to the present disclosure exhibits lower driving voltage and significantly higher luminous efficiency and lifespan characteristics compared to Comparative Example 1 using a conventional compound as the second host.

[0190] Device Examples 4 and 5: Production of OLEDs Comprising Organic Electroluminescent Compounds According to the Disclosure

[0191] An OLED was produced in the same manner as in Device Example 1, except that only the host compounds in Table 2 below were used as the host of the light-emitting layer.

[0192] Comparative Example 2: Production of an OLED containing a comparative compound as a host

[0193] An OLED was produced in the same manner as in Device Example 4, except that only the host compounds in the following Table 2 were used as the host for the light-emitting layer.

[0194] Table 2 below shows the driving voltage, luminous efficiency, luminous color at a luminance of 1,000 nits, and the time taken for the luminance to decrease from 100% to 95% at a luminance of 10,000 nits (lifetime: T95) of the OLEDs of device examples 4, 5 and comparative example 2 produced as described above.

[0195] [Table 2]

[0196]

[0197] As can be confirmed from the above Table 2, the OLED according to the present disclosure exhibits lower driving voltage and significantly higher luminous efficiency and lifespan characteristics compared to Comparative Example 2 using a conventional compound as a host.

[0198] [Table 3]

[0199]

Claims

1. An organic electroluminescent compound, which is represented by the following formula 1: In formula 1, R1 and R2 are linked to each other to form one or more substituted or unsubstituted condensed rings; R3 to R 10 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- to 30-membered)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or substituted or unsubstituted tri(C6-C30)arylsilyl; and The one or more fused rings and R3 to R 10 At least one of the one or more substituents represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group containing at least one N.

2. The organic electroluminescent compound according to claim 1, wherein The substituted alkyl, the substituted cycloalkyl, the substituted aryl, the substituted heteroaryl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, and the substituted condensed ring are each independently substituted by at least one selected from the group consisting of: deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; phosphine oxide; (C1-C30)alkyl; halogenated (C1-C30)alkyl; (C2-C30)alkenyl; (C2-C30)alkynyl; (C1-C30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl; (3- to 7-membered)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (C6-C30)aryl, unsubstituted or substituted by at least one of one or more (C1-C30)alkyl and one or more di(C6-C30)arylamino; (3- to 30-membered)heteroaryl, unsubstituted or substituted by at least one of one or more (C6-C30)aryl; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C 1-C30)alkyldi(C6-C30)arylsilyl; a fused ring group of one or more (C3-C30)aliphatic rings and one or more (C6-C30)aromatic rings; an amino group; a mono- or di-(C1-C30)alkylamino group; a mono- or di-(C2-C30)alkenylamino group; a mono- or di-(C6-C30)arylamino group which is unsubstituted or substituted by one or more (C1-C30)alkyl groups; a mono- or di-(3- to 30-membered)heteroarylamino group; a (C1-C30)alkyl(C2-C30)alkenylamino group; a (C1-C30)alkyl(C6-C30)arylamino group; a (C1-C30)alkyl(C2-C30)alkenylamino group; a (C1-C30)alkyl(C6-C30)arylamino group; a (C1-C30)alkyl( (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30)alkenyl(3- to 30-membered)heteroarylamino; (C6-C30)aryl(3- to 30-membered)heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylborylcarbonyl; di(C1-C30)alkylborylcarbonyl; (C1-C30)alkyl(C6-C30)arylborylcarbonyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl.

3. The organic electroluminescent compound according to claim 1, wherein Formula 1 is represented by any one of the following formulas 1-1 to 1-4: In formulas 1-1 to 1-4, R3 to R 10 is as defined in claim 1; A1 to A9 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, or substituted or unsubstituted tri(C6-C30)arylsilyl; X1 means -N=; X2 stands for -NR 11 , -O- or -S-; R 11 represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- to 30-membered)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or substituted or unsubstituted tri(C6-C30)arylsilyl; and R3 to R 11 and at least one of A1 to A9 represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group containing at least one N.

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

5. An organic electroluminescent material comprising a compound represented by the following formula 1 and a compound represented by the following formula 2: In formula 1, R1 and R2 are linked to each other to form one or more substituted or unsubstituted condensed rings; R3 to R 10 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- to 30-membered)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or substituted or unsubstituted tri(C6-C30)arylsilyl; and The one or more fused rings and R3 to R 10 At least one of the one or more substituents represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group containing at least one N, and In Formula 2, Y1 and Y2 each independently represent -N=, -NR 16 -, -O- or -S-, provided that either one of Y1 and Y2 represents -N= and the other of Y1 and Y2 represents -NR 16 -, -O-, or -S-; R 12 represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; R 13 To R 16 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) Arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, a substituted or unsubstituted condensed ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or -L1-N-(Ar1)(Ar2); or may be connected with one or more adjacent substituents to form one or more rings; provided that R 13 To R 15 At least one of them is -L1-N-(Ar1)(Ar2); Ar1 and Ar2 each independently represent a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, or a substituted or unsubstituted condensed ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings; L1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group; and a and b each independently represent an integer of 1 or 2, and c represents an integer of 1 to 4, wherein if a to c are integers of 2 or more, each R 13 To each R 15 May be the same as or different from each other.

6. The organic electroluminescent material according to claim 5, wherein The substituted alkyl, substituted cycloalkyl, substituted (ene)aryl, substituted (ene)heteroaryl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted fused ring, and substituted fused ring group of one or more aliphatic rings and one or more aromatic rings are substituted by at least one selected from the group consisting of: deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; phosphine oxide; (C1-C30)alkyl; halogenated (C1-C30)alkyl; (C2-C30)alkenyl; (C2-C30)alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3- to 7-membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (C6-C30) aryl which is unsubstituted or substituted by at least one of one or more (C1-C30) alkyl and one or more di(C6-C30) arylamino groups; (3- to 30-membered) heteroaryl which is unsubstituted or substituted by one or more (C6-C30) aryl groups; tri(C1-C30) alkylsilyl; one or more tri(C6-C30) arylsilyl; di(C1-C30) alkyl(C (C1-C30)alkyldi(C6-C30)arylsilyl; a fused ring group of one or more (C3-C30)aliphatic rings and one or more (C6-C30)aromatic rings; an amino group; a mono- or di-(C1-C30)alkylamino group; a mono- or di-(C2-C30)alkenylamino group; a mono- or di-(C6-C30)arylamino group which is unsubstituted or substituted by one or more (C1-C30)alkyl groups; a mono- or di-(3- to 30-membered)heteroarylamino group; a (C1-C30)alkyl(C2-C30)alkenylamino group; a (C1-C30)alkyl(C6-C30)arylamino group; a (C1-C30)alkyl(C2-C30)alkenylamino group; a (C1-C30)alkyl(C6-C30)arylamino group; a (C1-C30)alkyl -C30)alkyl(3- to 30-membered)heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30)alkenyl(3- to 30-membered)heteroarylamino; (C6-C30)aryl(3- to 30-membered)heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylborylcarbonyl; di(C1-C30)alkylborylcarbonyl; (C1-C30)alkyl(C6-C30)arylborylcarbonyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl.

7. The organic electroluminescent material according to claim 5, wherein The compound represented by Formula 2 is at least one of the following formulae:

8. An organic electroluminescent material comprising a compound represented by the following formula 1 and a compound represented by the following formula 3: In formula 1, R1 and R2 are linked to each other to form one or more substituted or unsubstituted condensed rings; R3 to R 10 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- to 30-membered)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or substituted or unsubstituted tri(C6-C30)arylsilyl; and The one or more fused rings and R3 to R 10 At least one of the one or more substituents represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group containing at least one N, and In formula 3, X stands for O, S, CR 21 R 22 NR 23 or Se; R 21 To R 23 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; or may be linked to one or more adjacent substituents to form one or more rings; R 17 To R 20 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, The premise is R 17 To R 20 At least one of L2 and L3 each independently represent a single bond, a substituted or unsubstituted (C6-C30)arylene group, a substituted or unsubstituted (C3-C30)cycloalkylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group; Ar3 to Ar7 each independently represent a substituted or unsubstituted (C6-C30)aryl group or a substituted or unsubstituted (3-membered to 30-membered) heteroaryl group; d and g represent integers of 1 to 4, and e and f represent integers of 1 or 2, wherein if d to g are integers of 2 or more, each R 17 To each R 20 may be the same as or different from each other; and * indicates the site of connection with Formula 3.

9. The organic electroluminescent compound according to claim 8, wherein The compound represented by Formula 3 is selected from the following compounds: 10 . An organic electroluminescent device comprising the compound according to claim 1 . 11 . An organic electroluminescent device comprising the organic electroluminescent material according to claim 5 . 12 . An organic electroluminescent device comprising the organic electroluminescent material according to claim 8 .

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