Organic electroluminescent compound, plurality of host materials, and organic

Abstract

The present disclosure relates to an organic electroluminescent compound, a plurality of host materials, and an organic electroluminescent device comprising the same. By comprising a compound according to the present disclosure or by comprising a specific combination of compounds according to the present disclosure as various host materials, it is possible to provide an organic electroluminescent device having improved luminous efficiency and / or lifespan characteristics.

Description

Technical Field

[0001] The present disclosure relates to an organic electroluminescent compound, a plurality of host materials, 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 more efficient OLED 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 the luminous efficiency, driving voltage and / or lifespan, various materials or concepts for the organic layer 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 luminescent materials having enhanced properties, such as improved driving voltage, luminous efficiency, power efficiency and / or lifespan characteristics compared to the combination of previously disclosed specific compounds.

[0004] In contrast, Korean Patent Application Publication No. 10-2020-0013600 discloses phenanthroline derivatives as compounds contained in a variety of host materials. However, the aforementioned references do not specifically disclose compounds with specific structures as claimed in the present disclosure and a variety of host materials containing them. In addition, there is a continuing need to develop luminescent 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 improved multiple host materials capable of providing an organic electroluminescent device having improved luminous efficiency and / or life characteristics. Further, another object of the present disclosure is to provide an organic electroluminescent device having improved luminous efficiency and / or life characteristics by comprising a compound of the present disclosure or a specific combination of compounds of the present disclosure.

[0007] Solution to the problem

[0008] As a result of in-depth research to solve the technical problem, the inventors of the present invention found that the above-mentioned purpose can be achieved by the following items: an organic electroluminescent compound represented by the following formula 1; or a plurality of host materials, which include at least one first host material comprising an organic electroluminescent compound according to the following formula 1 and at least one second host material different from the first host material.

[0009]

[0010] In formula 1,

[0011] X represents NR1, O, S, Se, CR2R3 or SiR4R5;

[0012] R1 to R5 each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-membered to 30-membered) heteroaryl group;

[0013] Y represents O, S, Se or Te;

[0014] Z1 to Z6 each independently represent N or CR 11 ;

[0015] R 11 Represents hydrogen, deuterium or -L1-R 13 ;

[0016] R 12 Indicates -L2-R 14 ;

[0017] L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group;

[0018] R 13 and R 14 Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, -L'1-SiR'1R'2R'3, -L'2-GeR'4R'5R'6, -L'3-NR'7R'8, -L'4(NR'9R' 10 )(NR' 11 R' 12 ),-L'5-NR' 13 R' 14 , or -L'6-(NR' 15 )-L'7(NR' 16 R' 17 );

[0019] L'1 to L'7 each independently represent a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3-membered to 30-membered)heteroarylene group; and

[0020] R'1 to R' 17 Each independently represents a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted (3- to 30-membered)heteroaryl group, or a substituted or unsubstituted (C3-C30)cycloalkyl group.

[0021] Beneficial Effects of the Invention

[0022] The organic electroluminescent compound according to the present disclosure exhibits properties suitable for using it in an organic electroluminescent device. In addition, an organic electroluminescent device having improved driving voltage, luminous efficiency and / or life characteristics compared to a conventional organic electroluminescent device is provided by including the compound according to the present disclosure as a single host material or by including multiple compounds as host materials, and a display system or a lighting system can be produced using the organic electroluminescent device. BRIEF DESCRIPTION OF THE DRAWINGS

[0023] Figure 1 Representative formulas for organic electroluminescent compounds according to the present disclosure are shown. DETAILED DESCRIPTION

[0024] Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present disclosure and is not intended to limit the scope of the present disclosure in any way.

[0025] The term "organic electroluminescent compound" in the present disclosure means a compound that can be used in an organic electroluminescent device and, if necessary, can be contained in any layer constituting the organic electroluminescent device.

[0026] The term "organic electroluminescent material" in the present disclosure means 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 contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole 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.

[0027] 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 included in organic electroluminescent materials. At least two compounds included in the multiple host materials of the present disclosure may be included in one light-emitting layer together, or may be included 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.

[0028] The term "hole transport zone" in the present disclosure means a region where holes move between the first electrode and the light-emitting layer, and may include, for example, at least one 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 or a plurality of layers in which two or more layers or three or more layers are stacked. 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, wherein the first hole transport layer can be placed between the first electrode and the light-emitting layer, the second hole transport layer can be placed between the first hole transport layer and the light-emitting layer, and wherein the second hole transport layer can 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 can be placed between the first electrode and the light-emitting layer, the second hole transport layer can be placed between the first hole transport layer and the light-emitting layer, the third hole transport layer can be placed between the second hole transport layer and the light-emitting layer, and wherein the third hole transport layer can 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.

[0029] 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 hydrocarbon or polycyclic hydrocarbon having 3 to 30 ring skeleton carbon atoms, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The above-mentioned cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, and the like. The term "(3-membered to 7-membered) heterocycloalkyl" means a cycloalkyl group having 3 to 7 ring skeleton atoms and including at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, and preferably the group consisting of O, S, and N. The above-mentioned heterocycloalkyl can include tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc. The terms "(C6-C30) aryl", "(C6-C30) arylene", 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, arylene 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-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 9-phenanthrenyl, naphthacetyl, pyrenyl, 1- Base, 2- Base, 3- Base, 4- Base, 5- Base, 6- Benzo[c]phenanthrenyl, benzo[g] 1-triphenylene, 2-triphenylene, 3-triphenylene, 4-triphenylene, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo[a]fluorenyl, benzo[b]fluorenyl, benzo[c]fluorenyl, dibenzofluorenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl -yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 3-fluoranthene, 4-fluoranthene, 8-fluoranthene, 9-fluoranthene, benzofluoranthene, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumyl, m-cumyl, p-cumyl, p-tert-butylphenyl, 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-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9 ,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, 11,11-dimethyl-1-benzo[a]fluorenyl, 11,11-dimethyl-2-benzo[a]fluorenyl, 11,11-dimethyl-3-benzo[a]fluorenyl, 11,11-dimethyl-4-benzo[a]fluorenyl, 11,11-dimethyl-1-benzo[a]fluorenyl methyl-5-benzo[a]fluorenyl, 11,11-dimethyl-6-benzo[a]fluorenyl, 11,11-dimethyl-7-benzo[a]fluorenyl, 11,11-dimethyl-8-benzo[a]fluorenyl, 11,11-dimethyl-9-benzo[a]fluorenyl, 11,11-dimethyl-10-benzo[a]fluorenyl, 11,11-dimethyl- 1-Benzo[b]fluorenyl, 11,11-dimethyl-2-benzo[b]fluorenyl, 11,11-dimethyl-3-benzo[b]fluorenyl, 11,11-dimethyl-4-benzo[b]fluorenyl, 11,11-dimethyl-5-benzo[b]fluorenyl, 11,11-dimethyl-6-benzo[b]fluorenyl, 11,11-dimethyl-7-benzo[ b]fluorenyl, 11,11-dimethyl-8-benzo[b]fluorenyl, 11,11-dimethyl-9-benzo[b]fluorenyl, 11,11-dimethyl-10-benzo[b]fluorenyl, 11,11-dimethyl-1-benzo[c]fluorenyl, 11,11-dimethyl-2-benzo[c]fluorenyl, 11,11-dimethyl-3-benzo[c]fluorenyl 11,11-dimethyl-4-benzo[c]fluorenyl, 11,11-dimethyl-5-benzo[c]fluorenyl, 11,11-dimethyl-6-benzo[c]fluorenyl, 11,11-dimethyl-7-benzo[c]fluorenyl, 11,11-dimethyl-8-benzo[c]fluorenyl, 11,11-dimethyl-9-benzo[c]fluorenyl, 11,11-dimethyl-11-dimethyl-10-benzo[c]fluorenyl, 11,11-diphenyl-1-benzo[a]fluorenyl, 11,11-diphenyl-2-benzo[a]fluorenyl, 11,11-diphenyl-3-benzo[a]fluorenyl, 11,11-diphenyl-4-benzo[a]fluorenyl, 11,11-diphenyl-5-benzo[a]fluorenyl, 11,11-diphenyl-6-benzo[a]fluorenyl, 11,11-diphenyl-7-benzo[a]fluorenyl, 11,11-diphenyl-8-benzo[a]fluorenyl, 11,1 1-diphenyl-9-benzo[a]fluorenyl, 11,11-diphenyl-10-benzo[a]fluorenyl, 11,11-diphenyl-1-benzo[b]fluorenyl, 11,11-diphenyl-2-benzo[b]fluorenyl, 11,11-diphenyl-3-benzo[b]fluorenyl, 11,11-diphenyl-4-benzo[b]fluorenyl, 11,11-diphenyl-5-benzo[b]fluorenyl, 11,11-diphenyl-6-benzo[b]fluorenyl, 11,11-diphenyl-7-benzo[b]fluorenyl, 11,11- diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9-benzo[b]fluorenyl, 11,11-diphenyl-10-benzo[b]fluorenyl, 11,11-diphenyl-1-benzo[c]fluorenyl, 11,11-diphenyl-2-benzo[c]fluorenyl, 11,11-diphenyl-3-benzo[c]fluorenyl, 11,11-diphenyl-4-benzo[c]fluorenyl, 11,11-diphenyl-5-benzo[c]fluorenyl, 11,11-diphenyl-6-benzo[c]fluorenyl, 11,11-diphenyl- Phenyl-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.

[0030] 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 include 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, 8-imidazopyridinyl oxazolopyridinyl, 3-pyridinyl, 4-pyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furanyl, 3-furanyl, 2-phenylindole benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6- -quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, 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- 3-Methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2-tert-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4-tert-butyl-1-indolyl, 2-tert-butyl-3-indolyl, 4-tert-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophene, 2-dibenzothiophene, 3-dibenzothiophene, 4-dibenzothiophene, 1-naphtho-[1,2-b]-benzofuranyl, 2-naphtho-[1,2-b]-benzofuranyl, 3-naphtho-[1,2-b]-benzofuranyl, 4-naphtho-[1,2-b]-benzofuranyl, 5-naphtho-[1,2-b]-benzofuranyl, 6-naphtho-[1,2-b]-benzofuranyl, 7-naphtho-[1,2-b]-benzofuranyl , 8-naphtho-[1,2-b]-benzofuranyl, 9-naphtho-[1,2-b]-benzofuranyl, 10-naphtho-[1,2-b]-benzofuranyl, 1-naphtho-[2,3-b]-benzofuranyl, 2-naphtho-[2,3-b]-benzofuranyl, 3-naphtho-[2,3-b]-benzofuranyl, 4-naphtho-[2, 3-b]-benzofuranyl, 5-naphtho-[2,3-b]-benzofuranyl, 6-naphtho-[2,3-b]-benzofuranyl, 7-naphtho-[2,3-b]-benzofuranyl, 8-naphtho-[2,3-b]-benzofuranyl, 9-naphtho-[2,3-b]-benzofuranyl, 10-naphtho-[2,3-b]-benzofuranyl 1-naphtho-[2,1-b]-benzofuranyl, 2-naphtho-[2,1-b]-benzofuranyl, 3-naphtho-[2,1-b]-benzofuranyl, 4-naphtho-[2,1-b]-benzofuranyl, 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” may be classified into a heteroaryl (sub) group having an electron characteristic and a heteroaryl (sub) group having a hole characteristic. The (sub)heteroaryl group with electron characteristics is a relatively electron-rich substituent in the parent nucleus, such as substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazine, substituted or unsubstituted quinazoline, substituted or unsubstituted quinoxaline, or substituted or unsubstituted quinolyl, etc. The (sub)heteroaryl group with hole characteristics is a relatively electron-poor substituent in the parent nucleus, such as substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, etc. In addition, "halogen" includes F, Cl, Br, and I. ,

[0031] In addition, "ortho (o-)", "meta (m-)", and "para (p-)" are prefixes that indicate the relative positions of substituents, respectively. Ortho means that two substituents are adjacent to each other, and for example, when two substituents in a benzene derivative occupy positions 1 and 2 or positions 2 and 3, it is referred to as ortho. Meta means that two substituents are at positions 1 and 3, and for example, when two substituents in a benzene derivative occupy positions 1 and 3, it is referred to as meta. Para means that two substituents are at positions 1 and 4, and for example, when two substituents in a benzene derivative occupy positions 1 and 4, it is referred to as para.

[0032] In this article, the expression "substituted or unsubstituted" in "substituted" means that the hydrogen atom in a functional group is replaced by another atom or another functional group (i.e., a substituent). Unless otherwise specified, a substituent can replace the hydrogen at the position where the substituent can be replaced, without limitation, and when two or more hydrogen atoms in a functional group are each replaced by a substituent, each substituent can be the same or different from each other. The maximum number of substituents that can be replaced in a functional group can be the total number of valences that can be replaced for each atom forming the functional group. Herein, substituted alkyl, substituted aryl, substituted heteroaryl, substituted arylene, substituted heteroarylene and substituted cycloalkyl are each independently substituted by at least one selected from the group consisting of: deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; (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-membered to 7-membered)heterocycloalkyl; (C (C6-C30)aryloxy; (C6-C30)arylthio; (3- to 30-membered)heteroaryl, unsubstituted or substituted by at least one of one or more (C6-C30)aryl groups; (C6-C30)aryl, unsubstituted or substituted by at least one of one or more (C1-C30)alkyl groups and one or more (3- to 30-membered)heteroaryl groups; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)alkyl C30)arylsilyl; amino; mono- or di-(C1-C30)alkylamino; mono- or di-(C2-C30)alkenylamino; mono- or di-(C6-C30)arylamino unsubstituted or substituted by one or more (C1-C30)alkyl; mono- or di-(3- to 30-membered)heteroarylamino; (C1-C30)alkyl(C2-C30)alkenylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkyl(3- to 30-membered)heteroarylamino; (C2-C30)alkenyl(C6-C30) (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 alkyl group and the like may each independently be substituted by at least one selected from the group consisting of: deuterium; substituted or unsubstituted (3- to 30-membered) heteroaryl; substituted or unsubstituted (C6-C30) aryl; amino; mono- or di-(C6-C30) arylamino; (C1-C30) alkyl (C2-C30) alkenylamino; (C1-C30) alkyl (C6-C30) arylamino; (C1-C30) alkyl (3- to 30-membered) heteroarylamino; (C2-C30) alkenyl (C6-C30) arylamino; (C2-C30) alkenyl (3- to 30-membered) heteroarylamino. According to another embodiment of the present disclosure, the substituted alkyl group, etc., can be substituted independently by at least one selected from the group consisting of: substituted or unsubstituted (3-20-membered) heteroaryl; substituted or unsubstituted (C6-C20) aryl; mono- or di-(C6-C25) arylamino. For example, the substituted alkyl group, etc. can be substituted independently by phenyl, naphthyl, dibenzofuranyl, diphenylamino or phenylnaphthylamino, and these can be further substituted by deuterium.

[0033] In the present disclosure, if there is no indication of a substituent in a chemical formula or compound structure, this may mean that all possible positions of the substituent are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be isotope deuterium, and in this case, the content of deuterium may be 0% to 100%. In the present disclosure, in the case of no indication of a substituent in a chemical formula or compound structure, if deuterium is not explicitly excluded, such as 0% deuterium, 100% hydrogen, and all substituents are hydrogen, hydrogen and deuterium may be mixed in the compound. Deuterium is one of the isotopes of hydrogen and is an element having a deuteron as its core, which is composed of one proton and one neutron. It can be represented as hydrogen-2, and its element symbol may also be written as D or 2H. Isotopes are atoms with the same atomic number (Z) but different mass numbers (A), which may also be interpreted as elements with the same number of protons but different numbers of neutrons.

[0034] 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 contain up to 50 atoms that are not hydrogen or deuterium, or up to 40 atoms that are not hydrogen or deuterium, or up to 30 atoms that are not hydrogen or deuterium, or in many cases, preferred combinations of substituents can contain up to 20 atoms that are not hydrogen or deuterium.

[0035] In the formula of the present disclosure, when the ring is formed by the connection of adjacent substituents, the ring can be a substituted or unsubstituted, monocyclic or polycyclic (3 to 30 yuan) alicyclic ring or aromatic ring, or a combination thereof, and the ring is formed by the connection of at least two adjacent substituents. 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, and according to another embodiment of the present disclosure, the number of ring skeleton atoms is 5 to 15.

[0036] The present disclosure provides an organic electroluminescent compound represented by Formula 1.

[0037] Hereinafter, the compound represented by Formula 1 will be described in more detail.

[0038] In Formula 1, X represents NR1, O, S, Se, CR2R3 or SiR4R5. According to one embodiment of the present disclosure, X represents O or S. For example, X may represent O.

[0039] In Formula 1, R1 to R5 each independently represent a substituted or unsubstituted (C1-C30) alkyl group, 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, R1 to R5 each independently represent a substituted or unsubstituted (C1-C30) alkyl group, or a substituted or unsubstituted (C6-C30) aryl group.

[0040] In Formula 1, Y represents O, S, Se or Te. According to one embodiment of the present disclosure, Y represents O, S or Se. For example, Y may represent O or S.

[0041] In Formula 1, Z1 to Z6 each independently represent N or CR 11 For example, Z1 to Z6 can each independently represent CR 11 .

[0042] In formula 1, R 11 Represents hydrogen, deuterium or -L1-R 13 For example, R 11 Can represent hydrogen or -L1-R 13 .

[0043] In formula 1, R 12 Indicates -L2-R 14 .

[0044] In Formula 1, L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3- to 30-membered) heteroarylene group. According to one embodiment of the present disclosure, L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6-C20) arylene group, or a substituted or unsubstituted (3- to 20-membered) heteroarylene group. According to another embodiment of the present disclosure, L1 and L2 each independently represent a single bond, or a substituted or unsubstituted (C6-C20) arylene group. For example, L1 and L2 each independently may be a single bond or a phenylene group.

[0045] In formula 1, R 13 and R 14 Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, -L'1-SiR'1R'2R'3, -L'2-GeR'4R'5R'6, -L'3-NR'7R'8, -L'4(NR'9R' 10 )(NR' 11 R' 12 ),-L'5-NR' 13 R' 14 , or -L'6-(NR' 15 )-L'7(NR' 16 R' 17 ). According to one embodiment of the present disclosure, R 13 and R 14 Each independently represents a substituted or unsubstituted (C1-C20) alkyl group, a substituted or unsubstituted (C6-C20) aryl group, a substituted or unsubstituted (3- to 20-membered) heteroaryl group, a substituted or unsubstituted (C3-C20) cycloalkyl group, -L'3-NR'7R'8, -L'4(NR'9R' 10 )(NR' 11 R' 12 ),-L'5-NR' 13 R' 14 , or -L'6-(NR' 15 )-L'7(NR' 16 R' 17 ). According to another embodiment of the present disclosure, R 13 and R 14 Each independently represents a substituted or unsubstituted (C6-C20)aryl group, a substituted or unsubstituted (3- to 20-membered) heteroaryl group, -L'3-NR'7R'8, -L'4(NR'9R' 10 )(NR' 11 R' 12),-L'5-NR' 13 R' 14 , or -L'6-(NR' 15 )-L'7(NR' 16 R' 17 ). For example, R 13 and R 14 Each independently can be phenyl, -L'3-NR'7R'8, -L'4(NR'9R' 10 )(NR' 11 R' 12 ),-L'5-NR' 13 R' 14 , or -L'6-(NR' 15 )-L'7(NR' 16 R' 17 ).

[0046] In Formula 1, L'1 to L'7 each independently represent 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 to L'7 each independently represent a single bond, or a substituted or unsubstituted (C6-C30)arylene group. According to another embodiment of the present disclosure, L'1 to L'7 each independently represent a single bond, or a substituted or unsubstituted (C6-C25)arylene group. For example, L'1 to L'7 each independently may be a single bond, a phenylene group, or a dimethylfluorenyl group, etc.

[0047] In Formula 1, R'1 to R' 17 Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, or a substituted or unsubstituted (C3-C30) cycloalkyl group. According to one embodiment of the present disclosure, R'1 to R' 17 Each independently represents a substituted or unsubstituted (C1-C25) alkyl group, a substituted or unsubstituted (C6-C25) aryl group, a substituted or unsubstituted (3- to 25-membered) heteroaryl group, or a substituted or unsubstituted (C3-C25) cycloalkyl group. 17 Each independently may be a phenyl group which is unsubstituted or substituted by one or more naphthyl groups, one or more diphenylamino groups, or one or more phenylnaphthylamino groups; a biphenyl group; a dibenzofuranyl group; a dibenzothienyl group; a dimethylfluorenyl group which is unsubstituted or substituted by one or more diphenylamino groups; a phenanthrenyl group; a terphenyl group; a naphthyl group; or a carbazolyl group which is substituted by one or more phenyl groups.

[0048] According to one embodiment of the present disclosure, Formula 1 may be represented by one of the following Formulas 1-1 to 1-3.

[0049]

[0050] In formulas 1-1 to 1-3,

[0051] R 21 and R 22 Each independently represents hydrogen, deuterium, or an unsubstituted or deuterium-substituted (C6-C30) aryl group. According to one embodiment of the present disclosure, R 21 and R 22 Each independently represents hydrogen, deuterium, or unsubstituted or deuterium-substituted (C6-C25) aryl. 21 and R 22 It may be hydrogen.

[0052] n and m each independently represent an integer of 3, l and o each independently represent an integer of 2, and each R 21 and each R 22 May be the same as or different from each other.

[0053] L1, L2, X, Y, and R 12 To R 14 is defined as in Equation 1.

[0054] According to one embodiment of the present disclosure, Formula 1 may be represented by one of the following Formulas 1-11 to 1-21.

[0055]

[0056]

[0057]

[0058] In formulas 1-11 to 1-21,

[0059] R 21 and R 22 Each independently represents hydrogen, deuterium, or an unsubstituted or deuterium-substituted (C6-C30) aryl group. According to one embodiment of the present disclosure, R 21 and R 22 Each independently represents hydrogen, deuterium, or unsubstituted or deuterium-substituted (C6-C25) aryl. 21 and R 22 It may be hydrogen.

[0060] n and m each independently represent an integer of 3, l and o each independently represent an integer of 2, and each R 21 and each R 22 May be the same as or different from each other.

[0061] X, Y, L'3 to L'7, R'7 to R'17 , and R 12 is defined as in Equation 1.

[0062] According to one embodiment of the present disclosure, R'7 to R' 17 Each independently can be selected from phenyl, biphenyl, terphenyl, p-pentaphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, The invention may be substituted with deuterium or a combination thereof, and the selected substituent may be partially or completely substituted with deuterium.

[0063] According to one embodiment of the present disclosure, Formula 1 may be represented by one of the following Formulas 1-31 to 1-33.

[0064]

[0065] In formulas 1-31 to 1-33,

[0066] X1 to X3 each independently represent N, CH or CD, and at least one of these is N. For example, X1 to X3 each independently may be N.

[0067] R 23 and R 24 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, R 23 and R 24 Each independently 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 23 and R 24 Each independently selected from phenyl, biphenyl, terphenyl, p-pentaphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, , fluorenyl, dimethylfluorenyl, methylphenylfluorenyl, diphenylfluorenyl, phenanthrenyl, dibenzofuranyl, dibenzothienyl, pyridyl, carbazolyl, or a combination thereof, and the selected substituent may be partially or completely substituted with deuterium. 23 and R 24 Each independently can be phenyl, biphenyl, naphthyl, phenanthryl, yl, dibenzofuranyl or dibenzothiophenyl.

[0068] R 21 and R 22 Each independently represents hydrogen, deuterium, or (C6-C30)aryl. According to one embodiment of the present disclosure, R 21 and R22 Each independently represents hydrogen, deuterium, or (C6-C25)aryl. 21 and R 22 It may be hydrogen.

[0069] n and m each independently represent an integer of 3, l and o each independently represent an integer of 2, and each R 21 and each R 22 May be the same as or different from each other.

[0070] X, Y, L1, L2, and R 12 is defined as in Equation 1.

[0071] The compound represented by Formula 1 may be selected from the group consisting of the following compounds, but is not limited thereto.

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079] The present disclosure provides an organic electroluminescent material including an organic electroluminescent compound represented by Formula 1, and an organic electroluminescent device including the same.

[0080] The organic electroluminescent material may consist of only the organic electroluminescent compound disclosed herein, and may further contain conventional materials included in organic electroluminescent materials.

[0081] The organic electroluminescent compound represented by Formula 1 may be contained in at least one layer selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer, and is preferably contained in at least one layer of a light-emitting layer (host material), a hole transport region, and an electron transport region.

[0082] In addition, the present disclosure provides a plurality of host materials, which include at least one first host material including the organic electroluminescent compound according to claim 1 and at least one second host material different from the first host material. According to one embodiment of the present disclosure, the second host material may include an organic electroluminescent compound represented by the following Formula 2.

[0083] In formula 2, X 11 To X 13 Each independently represents N, CH or CD. According to one embodiment of the present disclosure, X 11 To X 13 Each independently represents N or CH. For example, X 11 To X 13 Each independently represents N.

[0084] In formula 2, L 21 To L 23 Each independently represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group. According to one embodiment of the present disclosure, L 21 To L 23 Each independently represents a single bond, a substituted or unsubstituted (C6-C25)arylene group, or a substituted or unsubstituted (3- to 25-membered)heteroarylene group. According to another embodiment of the present disclosure, L 21 To L 23 Each independently represents a single bond, a substituted or unsubstituted (C6-C20)arylene group, or a substituted or unsubstituted (3- to 20-membered)heteroarylene group. 21 To L 23 Each independently may be a single bond, a phenylene group, a biphenylene group, a naphthylene group, or a dibenzofuranylene group.

[0085] In formula 2, Ar 21 To Ar 23 Each independently represents a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tri(C1-C30) alkylsilyl group, a substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl group, a substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tri(C6-C30) arylsilyl 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 21 To Ar 23Each independently represents a substituted or unsubstituted (C6-C25) aryl group, a substituted or unsubstituted (3- to 25-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C25) alkoxy group, a substituted or unsubstituted tri(C1-C30) alkylsilyl 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 another embodiment of the present disclosure, Ar 21 To Ar 23 Each independently represents a substituted or unsubstituted (C6-C25) aryl group, a substituted or unsubstituted (3- to 25-membered) heteroaryl group, a substituted or unsubstituted (C3-C25) cycloalkyl group, a substituted or unsubstituted (C1-C20) alkoxy 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. According to another embodiment of the present disclosure, Ar 21 To Ar 23 and each independently represents a substituted or unsubstituted phenylnaphthyl, a substituted or unsubstituted naphthylphenyl, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted dimethylbenzofluorenyl, a substituted or unsubstituted dimethylfluorenyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted benzonaphthofuranyl, a substituted or unsubstituted substituted or unsubstituted diphenylbenzofluorenyl, substituted or unsubstituted binaphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, or substituted or unsubstituted dibenzothiophene. 21 To Ar 23 Each independently may be phenyl, biphenyl, terphenyl, triphenylene, dibenzofuranyl, dibenzothiophenyl, dimethylbenzofluorenyl, dimethylfluorenyl, naphthyl, phenanthryl, benzonaphthofuranyl, which are unsubstituted or substituted with one or more naphthyl or one or more dibenzofuranyl groups, which are unsubstituted or substituted with one or more phenyl groups, yl, or diphenylbenzofluorenyl.

[0086] The compound represented by Formula 2 may be selected from the group consisting of the following compounds, but is not limited thereto.

[0087]

[0088]

[0089]

[0090] A combination of at least one of Compounds C-1 to C-150 and at least one of Compounds H2-1 to H2-85 can be used in an organic electroluminescent device.

[0091] The compound represented by Formula 1 according to the present disclosure may be produced by referring to the following Reaction Schemes 1 to 10, but is not limited thereto.

[0092] [Reaction Scheme 1]

[0093]

[0094] [Reaction Scheme 2]

[0095]

[0096] [Reaction Scheme 3]

[0097]

[0098] [Reaction Scheme 4]

[0099]

[0100] [Reaction Scheme 5]

[0101]

[0102] [Reaction Scheme 6]

[0103]

[0104] [Reaction Scheme 7]

[0105]

[0106] [Reaction Scheme 8]

[0107]

[0108] [Reaction Scheme 9]

[0109]

[0110] [Reaction Scheme 10]

[0111]

[0112] In reaction formulas 1 to 10, X is as defined in formula 1, and R is R'7 to R' 17 or R of formula 1-31 to 1-33 23 or R 24 As defined in .

[0113] The compound represented by Formula 2 according to the present disclosure may be produced by a synthesis method known to those skilled in the art, and specifically by using a synthesis method disclosed in many patent documents, for example, by referring to the method disclosed in Korean Patent Application Publication No. 2020-0011884 and Korean Patent Application Publication No. 2020-0026083, etc., but is not limited thereto.

[0114] Although the illustrative synthesis examples of the compounds represented by Formulae 1 and 2 of the present disclosure 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, acidified montmorillonite (H-mont)-mediated etherification reaction, Miyaura borylation reaction, Suzuki cross-coupling reaction, intramolecular acid-induced cyclization reaction, Pd(II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, dehydration cyclization reaction, SN1 substitution reaction, SN2 substitution reaction, and phosphine-mediated reductive cyclization reaction, Wittig reaction, etc., and the above reactions proceed even when substituents defined in Formulae 1 and 2 above but not specified in the specific synthesis examples are bonded.

[0115] The present disclosure provides an organic electroluminescent device, comprising an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein at least one light-emitting layer comprises a plurality of host materials according to the present disclosure. The first host material and the second host material according to the present disclosure may be contained in one light-emitting layer, or may each be contained in a different light-emitting layer. In the various host materials of the present disclosure, the ratio of the compound represented by Formula 1 and the compound represented by Formula 2 is about 1:99 to about 99:1, preferably about 10:90 to about 90:10, more preferably about 30:70 to about 70:30. In addition, the compound represented by Formula 1 and the compound represented by Formula 2 in the desired ratio can be combined by mixing them in an oscillator, by dissolving them in a glass tube by heating, or by dissolving them in a solvent, etc.

[0116] According to one embodiment of the present disclosure, the doping concentration of the dopant compound relative to the host compound in the light-emitting layer can be less than 20wt%. The dopant included in the organic electroluminescent device of the present disclosure can be at least one phosphorescent dopant or a 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 can be preferably 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.

[0117] 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.

[0118]

[0119] In formula 101,

[0120] L is selected from the following structures 1 to 3:

[0121]

[0122] 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 connected to an adjacent substituent to form one or more rings with pyridine, such as substituted or unsubstituted quinoline, benzofuranopyridine, benzothienopyridine, indenopyridine, benzofuranoquinoline, benzothienoquinoline, or indenoquinoline;

[0123] 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 connected to an adjacent substituent to form one or more substituted or unsubstituted rings with benzene, such as substituted or unsubstituted naphthalene, fluorene, dibenzothiophene, dibenzofuran, indenopyridine, benzofuranopyridine, or benzothienopyridine;

[0124] 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 to adjacent substituents to form one or more substituted or unsubstituted rings; and

[0125] s represents an integer of 1 to 3.

[0126] Specific examples of the dopant compound are as follows, but are not limited thereto.

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133] The organic electroluminescent device according to the present disclosure has an anode, a cathode, and at least one organic layer between the anode and the cathode. The organic layer includes a light-emitting layer and may further include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer. Each of these layers may be further configured into a plurality of layers.

[0134] The anode and cathode may each be formed of a transparent conductive material, or a transflective or reflective conductive material. Depending on the materials forming the anode and cathode, the organic electroluminescent device may be a top emission type, a bottom emission type, or a two-side emission type. In addition, the hole injection layer may be further doped with a p-type dopant, and the electron injection layer may be further doped with an n-type dopant.

[0135] The organic layer may further include at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds. In addition, the organic layer may further include 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 the metal.

[0136] In addition, the organic electroluminescent device of the present disclosure can emit white light by further comprising at least one light-emitting layer, which, in addition to the compounds of the present disclosure, also comprises a blue, red or green electroluminescent compound known in the art. If necessary, it can further comprise a yellow or orange light-emitting layer.

[0137] In the organic electroluminescent device of the present disclosure, preferably, at least one layer selected from the group consisting of a chalcogenide layer, a metal halide layer and a metal oxide layer (hereinafter, "surface layer") can be placed on one or more inner surfaces of one or both electrodes. Specifically, it is preferred to place a chalcogenide (including oxide) layer of silicon or aluminum on the anode surface of the electroluminescent medium layer, and it is preferred to place a metal halide layer or a metal oxide layer on the cathode surface of the electroluminescent medium layer. Such a surface layer provides operational stability for the organic electroluminescent device. Preferably, the chalcogenide comprises SiO X (1≤X≤2), AlO X (1≤X≤1.5), SiON, SiAlON, etc.; metal halides include LiF, MgF2, CaF2, rare earth metal fluorides, etc.; and metal oxides include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0138] A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof may be used between the anode and the light emitting layer. The hole injection layer may be a multilayer to reduce the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, wherein each of the multilayers may use two compounds simultaneously. The hole transport layer or the electron blocking layer may also be a multilayer.

[0139] An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be used between the light-emitting layer and the cathode. The electron buffer layer may 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 may use two compounds at the same time. The hole blocking layer or the electron transport layer may also be a multilayer, wherein each of the multilayers may use a plurality of compounds.

[0140] The luminescent auxiliary layer can be placed between the anode and the luminescent layer, or between the cathode and the luminescent layer. When the luminescent auxiliary layer is placed between the anode and the luminescent layer, it can be used to promote hole injection and / or hole transport, or to prevent electron overflow. When the luminescent auxiliary layer is placed between the cathode and the luminescent layer, it can be used to promote electron injection and / or electron transport, or to prevent hole overflow. In addition, the hole auxiliary layer can be placed between the hole transport layer (or hole injection layer) and the luminescent layer, and the hole transport rate (or hole injection rate) can be effectively promoted or limited, so that the charge balance can be controlled. In addition, the electron blocking layer can be placed between the hole transport layer (or hole injection layer) and the luminescent layer, and the excitons can be confined in the luminescent layer by blocking the electrons from overflowing from the luminescent layer to prevent luminescent leakage. When the organic electroluminescent device includes two or more hole transport layers, the hole transport layer further included can be used as a hole auxiliary layer or an electron blocking layer. The luminescent auxiliary layer, the hole auxiliary layer or the electron blocking layer can have the effect of improving the efficiency and / or life of the organic electroluminescent device.

[0141] 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. Preferably, the oxidative dopant includes various Lewis acids and acceptor compounds; and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. The reductive dopant layer can be used as a charge generation layer to produce an organic electroluminescent device having two or more light-emitting layers and emitting white light.

[0142] The organic electroluminescent device according to the present disclosure may be an organic electroluminescent device having a tandem structure. In the case of a tandem organic electroluminescent device according to one embodiment, a single light-emitting unit (light-emitting 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.

[0143] 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 a combination thereof, and the alkaline earth metal may include one selected from the group consisting of Be, Mg, Ca, Sr, Ba, Ra and a combination 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.

[0144] According to one embodiment of the present disclosure, an organic electroluminescent material may be used as a light-emitting material for a white organic light-emitting device. According to the arrangement of R (red), G (green) or YG (yellow-green), and B (blue) light-emitting units, a white organic light-emitting device having various structures has been proposed, such as a side-by-side arrangement method, a stacked arrangement method, or a color conversion material (CCM) method, etc. In addition, according to one embodiment of the present disclosure, the organic electroluminescent material may also be used in an organic electroluminescent device including quantum dots (QDs).

[0145] 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 inkjet printing, nozzle printing, slit coating, spin coating, dip coating, flow coating method, etc. can be used. When forming a film of the first host compound and the second host compound of the present disclosure, co-deposition or mixed deposition is performed.

[0146] When a wet film-forming method is used, a thin film can be formed by dissolving or diffusing a material forming each layer in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent may be any solvent in which the material forming each layer can be dissolved or diffused and which has no problem in film-forming ability.

[0147] 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.

[0148] Furthermore, a display system such as a display system for a smartphone, a tablet computer, a notebook computer, a PC, a TV, or a car; or a lighting system such as an outdoor or indoor lighting system can be produced by using the organic electroluminescent device of the present disclosure.

[0149] Hereinafter, the preparation method of the compound according to the present disclosure and its characteristics, as well as the driving voltage and luminous efficiency of the organic electroluminescent device (OLED) containing various host materials according to the present disclosure will be explained in detail with reference to the representative compounds of the present disclosure. However, the following examples only describe the characteristics of the compound according to the present disclosure and the OLED containing it, and the present disclosure is not limited to the following examples.

[0150] Example 1: Preparation of Compound C-10

[0151]

[0152] 1) Synthesis of Compound 1-2

[0153] Compound A (12 g, 44.28 mmol), compound 1-1 (7.58 g, 48.71 mmol), Pd2dba3 (2.84 g, 3.10 mmol), x-phos (2.96 g, 6.20 mmol), K3PO4 (18.8 g, 88.56 mmol) and 220 mL of toluene were added to a flask and stirred at 140° C. for 2 hours. After the reaction was completed, the reactant was cooled to room temperature and separated by column chromatography to obtain compound 1-2 (15 g, yield: 98%).

[0154] 2) Synthesis of Compound 1-3

[0155] Compound 1-2 (9 g, 26.03 mmol), Cu(OTf)2 (14.1 g, 39.04 mmol) and 330 mL of 1,2-DCB were added to a flask and stirred at 160° C. for 12 hours. After the reaction was completed, the mixture was distilled to concentrate the organic matter and separated by column chromatography to obtain compound 1-3 (1.5 g, yield: 16%).

[0156] 3) Synthesis of Compound C-10

[0157] Compound 1-3 (2 g, 3.5 mmol), N-phenyldibenzo [b, d] furan-2-amine (1.1 g, 4.22 mmol), Pd2dba3 (193 mg, 0.21 mmol), s-phos (173 mg, 0.42 mmol), NaOtBu (1.0 g, 10.55 mmol) and 30 mL of o-xylene were added to a flask and stirred at 150° C. for 4 hours. After the reaction was completed, the reactant was cooled to room temperature and separated by column chromatography to obtain compound C-10 (1.3 g, yield: 54%).

[0158] MW MP C-10 566.62 231℃

[0159] Example 2: Preparation of Compound C-15

[0160]

[0161] Compound 1-3 (1.74 g, 5.06 mmol), N-phenyldibenzo [b, d] furan-2-amine (1.31 g, 5.06 mmol), Pd2dba3 (230 mg, 0.25 mmol), s-phos (207 mg, 0.51 mmol), NaOtBu (1.21 g, 12.65 mmol) and 35 mL of o-xylene were added to a flask and stirred at 150° C. for 2 hours. After the reaction was completed, the mixture was cooled to room temperature and purified by column chromatography to obtain compound C-15 (1.8 g, yield: 63%).

[0162] MW MP C-15 566.62 304℃

[0163] Example 3: Preparation of Compound C-13

[0164]

[0165] Compound 1-3 (1.3 g, 3.78 mmol), N-([1,1'-biphenyl]-2-yl)dibenzo[b,d]furan-2-amine (1.33 g, 3.97 mmol), Pd2dba3 (173 mg, 0.19 mmol), s-phos (155 mg, 0.38 mmol), NaOtBu (908 mg, 9.45 mmol) and 25 mL of o-xylene were added to a flask and stirred at 160° C. for 2 hours. After the reaction was completed, the reactant was cooled to room temperature and separated by column chromatography to obtain compound C-13 (1.4 g, yield: 58%).

[0166] MW MP C-13 642.71 275℃

[0167] Example 4: Preparation of Compound C-3

[0168]

[0169] Compound 1-3 (1.55 g, 4.51 mmol), N-phenyl-[1,1'-biphenyl]-2-amine (1.55 g, 4.51 mmol), Pd2dba3 (206 mg, 0.23 mmol), s-phos (185 mg, 0.45 mmol), NaOtBu (1.08 g, 11.28 mmol) and 30 mL of o-xylene were added to a flask and stirred at 160° C. for 3 hours. After the reaction was completed, the mixture was cooled to room temperature and purified by column chromatography to obtain compound C-3 (1.37 g, yield: 55%).

[0170] MW MP C-3 552.63 178℃

[0171] Example 5: Preparation of Compound C-63

[0172]

[0173] 1) Synthesis of compound 2-1

[0174] Compound B (50 g, 163.6 mmol), benzamide (21.8 g, 180.0 mmol), Pd2dba3 (10.5 g, 11.45 mmol), x-phos (10.7 g, 22.9 mmol), K3PO4 (69.4 g, 327.3 mmol) and 820 mL of toluene were added to a flask and stirred at 140° C. for 2 hours. After the reaction was completed, the reactant was cooled to room temperature and separated by column chromatography to obtain compound 2-1 (25 g, yield: 41%).

[0175] 2) Synthesis of Compound 2-2

[0176] Compound 2-1 (25 g, 72.3 mmol), Cu(OTf)2 (78.4 g, 216.9 mmol) and 900 mL of o-DCB were added to a flask and stirred at 160° C. for 48 hours. After the reaction was completed, the mixture was distilled to concentrate the organic matter and separated by column chromatography to obtain compound 2-2 (5.7 g, yield: 23%).

[0177] 3) Synthesis of Compound C-63

[0178] Compound 2-2 (2.83 g, 8.23 ​​mmol), N-phenyldibenzo [b, d] furan-3-amine (2.13 g, 8.23 ​​mmol), Pd2dba3 (377 mg, 0.41 mmol), s-phos (337 mg, 0.82 mmol), NaOtBu (1.98 g, 20.58 mmol) and 55 mL of o-xylene were added to a flask and stirred at 150° C. for 4 hours. After the reaction was completed, the reactant was cooled to room temperature and separated by column chromatography to obtain compound C-63 (1.9 g, yield: 41%).

[0179] MW MP C-63 566.62 284℃

[0180] Example 6: Preparation of Compound C-125

[0181]

[0182] 1) Synthesis of Compound 2-3

[0183] Compound 2-2 (2.0 g, 5.82 mmol), bis(pinacolato)diboron (2.91 g, 11.40 mmol), Pd2dba3 (520 mg, 0.57 mmol), s-phos (470 mg, 1.14 mmol), KOAc (1.7 g, 17.1 mmol) and 40 mL of 1,4-dioxane were added to a flask and stirred at 130° C. for 4 hours. After the reaction was completed, the reactant was cooled to room temperature and separated by column chromatography to obtain compound 2-3 (2.2 g, yield: 87%).

[0184] 2) Synthesis of Compound C-125

[0185] Compound 2-3 (2.2 g, 5.05 mmol), 2-chloro-4-(dibenzo[b, d]furan-1-yl)-6-phenyl-1,3,5-triazine (1.81 g, 5.05 mmol), Pd(PPh3)4 (290 mg, 0.25 mmol), Cs2CO3 (4.1 g, 12.63 mmol), 24 mL of toluene, 6 mL of ethanol and 6 mL of H2O were added to a flask and stirred at 140°C for 2 hours. After the reaction was completed, the reactant was cooled to room temperature and separated by column chromatography to obtain compound C-125 (2.1 g, yield: 66%).

[0186] MW MP C-125 630.66 342℃

[0187] Device Example 1: Production of OLED using the second hole transport layer compound according to the present disclosure

[0188] An OLED according to the present disclosure is produced. 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. Compound HI-1 shown in Table 4 is introduced into a chamber of the vacuum vapor deposition device, and compound HT-1 is introduced into another chamber. The two materials are evaporated at different rates, and compound HI-1 is deposited in an amount of 3wt% based on the total amount of compound HI-1 and compound HT-1 to form a first hole injection layer having a thickness of 10nm. Subsequently, compound HT-1 is deposited on the first hole injection layer to form a first hole transport layer having a thickness of 80nm. Next, compound C-15 is introduced into another chamber of a vacuum vapor deposition device, and the compound is evaporated by applying an electric current to the chamber, thereby depositing a second hole transport layer having a thickness of 60nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light-emitting layer is deposited thereon as follows: each of the first host compound H1 and the second host compound H2-76 is introduced as a host into two chambers of a vacuum vapor deposition device, and compound D-39 is introduced as a dopant into another chamber. The two host materials are evaporated at a rate of 1:1, the dopant materials are evaporated at different rates simultaneously, and the dopant is deposited at a doping amount of 3wt% based on the total amount of the host and the dopant to form a light-emitting layer having a thickness of 40nm on the second hole transport layer. Then, compound ET-2 and compound EI-1 are evaporated as electron transport materials at a weight ratio of 50:50 to form an electron transport layer having a thickness of 35nm on the light-emitting layer. After depositing compound EI-1 as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 80 nm was deposited on the electron injection layer using another vacuum vapor deposition apparatus, thereby producing an OLED. All materials used to produce OLEDs were prepared at 10 -6 Purify by vacuum sublimation under vacuum.

[0189] Comparative Example 1: Production of an OLED containing a comparative compound as a host

[0190] An OLED was produced in the same manner as in Device Example 1, except that the materials in the following Table 1 were used as the second hole transport layer material.

[0191] Table 1 below shows the driving voltage, luminous efficiency, luminous color, and the time taken for the luminance to decrease from 100% to 95% (lifetime: T95) at a luminance of 10,000 nits for the OLEDs of device example 1 and comparative example 1 produced as described above.

[0192]

Table 1

[0193]

[0194] As can be confirmed from the above Table 1, the OLED (Device Example 1) including the compound according to the present disclosure in the second hole transport layer exhibits significantly improved luminous efficiency and lifespan characteristics compared to the OLED (Comparative Example 1) not including the compound according to the present disclosure.

[0195] Device Example 2: Production of OLEDs Comprising Various Host Materials According to the Disclosure

[0196] An OLED according to the present disclosure is produced. A transparent electrode indium tin oxide (ITO) film (10Ω / sq) (GEOMATEC CO., LTD., Japan) on a glass substrate for OLED is subjected to ultrasonic washing with acetone and isopropanol in sequence, and then stored in isopropanol. The ITO substrate is then mounted on a substrate holder of a vacuum vapor deposition device. Compound HI-1 shown in Table 4 below is introduced into a chamber of the vacuum vapor deposition device, and compound HT-1 is introduced into another chamber of the vacuum vapor deposition device. The two materials are evaporated at different rates, and compound HI-1 is deposited at a doping amount of 3wt% based on the total amount of compound HI-1 and compound HT-1 to form a first hole injection layer having a thickness of 10nm on the ITO substrate. Next, compound HT-1 is deposited on the first hole injection layer to form a first hole transport layer having a thickness of 80nm. Compound HT-2 is then introduced into another chamber of a vacuum vapor deposition apparatus, and the compound is evaporated by applying an electric current to the chamber, thereby forming a second hole transport layer having a thickness of 60nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light-emitting layer is deposited thereon as follows: each of the first host compound and the second host compound shown in Table 2 below is introduced as a host into two chambers of a vacuum vapor deposition apparatus, and compound D-39 is introduced into another chamber as a dopant. The two host materials are evaporated at a rate of 1:1, the dopant materials are evaporated at different rates simultaneously, and the dopant is deposited in a doping amount of 3wt% based on the total amount of the host and the dopant to form a light-emitting layer having a thickness of 40nm on the second hole transport layer. Then, compound ET-1 and compound EI-1 are evaporated as electron transport materials at a weight ratio of 50:50 to form an electron transport layer having a thickness of 35nm on the light-emitting layer. After depositing compound EI-1 as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 80 nm was deposited on the electron injection layer using another vacuum vapor deposition apparatus, thereby producing an OLED. All materials used to produce OLEDs were prepared at 10-6 Purify by vacuum sublimation under vacuum.

[0197] Device Examples 3-5: Production of OLEDs Comprising Various Host Materials According to the Disclosure

[0198] In Device Examples 3 to 5, OLEDs were produced in the same manner as in Device Example 2, except that Compounds C-15, C-13, and C-63 described in Table 2 below were used as the first host compound instead of Compound C-10.

[0199] Comparative Example 2: Production of an OLED containing a comparative compound as a host

[0200] An OLED was produced in the same manner as in Device Example 2, except that only the second host compound of the following Table 2 was used as a host for the light-emitting layer.

[0201] Table 2 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 2 to 5 and comparative example 2 produced as described above.

[0202]

Table 2

[0203]

[0204] It can be confirmed from Table 2 above that, compared with the OLED containing a single host material (Comparative Example 2), the OLED containing multiple host materials according to the present disclosure (Device Examples 2 to 5) exhibits equivalent levels of driving voltage and luminous efficiency characteristics, as well as significantly improved lifespan characteristics.

[0205] Device Example 6: Production of an OLED Comprising a Single Host Compound According to the Disclosure

[0206] 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 4 is introduced into a chamber of the vacuum vapor deposition device, and the compound HT-3 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-3 to form a first hole injection layer with a thickness of 10nm. Subsequently, the compound HT-3 is deposited on the first hole injection layer to form a first hole transport layer with a thickness of 80nm. Next, the compound HT-4 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 55nm on the first hole transport layer. Next, compound HT-5 is introduced into another chamber of a vacuum vapor deposition apparatus, and the compound is evaporated by applying an electric current to the chamber, thereby depositing a third hole transport layer having a thickness of 5nm on the second hole transport layer. After forming the hole injection layer and the hole transport layer, a light-emitting layer is deposited thereon as follows: the host compound shown in Table 3 below is introduced as the host into a chamber of a vacuum vapor deposition apparatus, and compound D-39 is introduced as a dopant into another chamber. The host material and the dopant material are evaporated at different rates, and the dopant is deposited in an amount of 3wt% based on the total amount of the host and the dopant to form a light-emitting layer having a thickness of 40nm on the third hole transport layer. Then, compound ET-2 and compound EI-1 are evaporated as electron transport materials at a weight ratio of 50:50 to form an electron transport layer having a thickness of 35nm on the light-emitting layer. After depositing compound EI-1 as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 80 nm was deposited on the electron injection layer using another vacuum vapor deposition apparatus, thereby producing an OLED. All materials used to produce OLEDs were prepared at 10 -6 Purify by vacuum sublimation under vacuum.

[0207] Comparative Example 3: Production of an OLED containing a comparative compound as a host

[0208] An OLED was produced in the same manner as in Device Example 6, except that the host compound of the following Table 3 was used as a host of the light-emitting layer.

[0209] Table 3 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 Example 6 and Comparative Example 3 produced as described above.

[0210]

Table 3

[0211]

[0212] As can be confirmed from Table 3 above, the OLED (Device Example 6) comprising the compound according to the present disclosure in the light-emitting layer exhibits a lower driving voltage, and significantly improved luminous efficiency and lifespan characteristics compared to the OLED (Comparative Example 3) not comprising the compound according to the present disclosure.

[0213] The compounds used in the device examples and comparative examples are shown in Table 4 below.

[0214]

Table 4

[0215]

[0216]

Claims

1. An organic electroluminescent compound, which is represented by the following formula 1: In formula 1, X represents NR1, O, S, Se, CR2R3 or SiR4R5; R1 to R5 each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-membered to 30-membered) heteroaryl group; Y represents O, S, Se or Te; Z1 to Z6 each independently represent N or CR 11 ; R 11 Represents hydrogen, deuterium or -L1-R 13 ; R 12 Indicates -L2-R 14 ; L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group; R 13 and R 14 Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, -L'1-SiR'1R'2R'3, -L'2-GeR'4R'5R'6, -L'3-NR'7R'8, -L'4(NR'9R' 10 )(NR' 11 R' 12 ),-L'5-NR' 13 R' 14 , or -L'6-(NR' 15 )-L'7(NR' 16 R' 17 ); L'1 to L'7 each independently represent a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3-membered to 30-membered)heteroarylene group; and R'1 to R' 17 Each independently represents a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted (3- to 30-membered)heteroaryl group, or a substituted or unsubstituted (C3-C30)cycloalkyl group.

2. The organic electroluminescent compound according to claim 1, wherein Formula 1 is represented by one of the following formulas 1-1 to 1-3: In the formula, R 21 and R 22 Each independently represents hydrogen, deuterium, or unsubstituted or deuterium-substituted (C6-C30)aryl; n and m each independently represent an integer of 3, l and o each independently represent an integer of 2, and each R 21 and each R 22 may be the same as or different from each other; and L1, L2, X, Y, and R 12 To R 14 As defined in claim 1.

3. The organic electroluminescent compound according to claim 1, wherein X and Y each independently represent O or S.

4. The organic electroluminescent compound according to claim 1, wherein Formula 1 is represented by one of the following formulas 1-11 to 1-21: In the formula, R 21 and R 22 Each independently represents hydrogen, deuterium, or unsubstituted or deuterium-substituted (C6-C30)aryl; n and m each independently represent an integer of 3, l and o each independently represent an integer of 2, and each R 21 and each R 22 may be the same as or different from each other; and X, Y, L'3 to L'7, R'7 to R' 17 , and R 12 As defined in claim 1.

5. The organic electroluminescent compound according to claim 4, wherein R'7 to R' 17 Each independently selected from phenyl, biphenyl, terphenyl, p-pentaphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, The invention may be substituted with deuterium or a combination thereof, and the selected substituent may be partially or completely substituted with deuterium.

6. The organic electroluminescent compound according to claim 1, wherein Formula 1 is represented by one of the following formulas 1-31 to 1-33: In the formula, X1 to X3 each independently represent N, CH or CD, and at least one of these is N; R 23 and R 24 Each independently represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; R 21 and R 22 Each independently represents hydrogen, deuterium, or (C6-C30)aryl; n and m each independently represent an integer of 3, l and o each independently represent an integer of 2, and each R 21 and each R 22 may be the same as or different from each other; and X, Y, L1, L2, and R 12 As defined in claim 1.

7. The organic electroluminescent compound according to claim 6, wherein R 23 and R 24 Each independently selected from phenyl, biphenyl, terphenyl, p-pentaphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, The substituents may be substituted with deuterium in part or in whole.

8. The organic electroluminescent compound according to claim 1, wherein The one or more substituents of the substituted alkyl, substituted aryl, substituted heteroaryl, substituted arylene, substituted heteroarylene, and substituted cycloalkyl are each independently at least one selected from the group consisting of: deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; (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-membered (C6-C30) arylsilyl; (C6-C30) alkyl (C6-C30) arylsilyl; (C1 ...aryl (C6-C30) arylsilyl; (C1-C30) alkyl (C6-C30) arylsilyl; (C1-C30) aryl (C6-C30) arylsilyl; (C1-C30) alkyl (C6-C30) arylsilyl; (C1-C30) aryl (C6-C30) arylsilyl; (C1-C30) aryl (C6-C30) arylsilyl; (C1-C30) aryl (C6-C30) arylsilyl; (C1-C30) aryl (C6-C30) aryl (C6-C30) aryl (C6-C30) aryl (C6-C30) aryl (C6-C30) aryl (C6-C30) aryl (C6-C30) aryl (C6-C30) aryl (C6-C30) aryl (C6-C30) aryl (C6-C30) aryl Alkyldi(C6-C30)arylsilyl; amino; mono- or di-(C1-C30)alkylamino; mono- or di-(C2-C30)alkenylamino; mono- or di-(C6-C30)arylamino unsubstituted or substituted by one or more (C1-C30)alkyl; mono- or di-(3- to 30-membered)heteroarylamino; (C1-C30)alkyl(C2-C30)alkenylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkyl(3- to 30-membered)heteroarylamino; (C2-C30)alkenyl (C6-C30)arylamino; (C2-C30)alkenyl(3- to 30-membered)heteroarylamino; (C6-C30)aryl(3- to 30-membered)heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylborylcarbonyl; di(C1-C30)alkylborylcarbonyl; (C1-C30)alkyl(C6-C30)arylborylcarbonyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl.

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

10. A plurality of host materials comprising at least one first host material comprising the organic electroluminescent compound according to claim 1 and at least one second host material different from the first host material.

11. The plurality of host materials according to claim 10, wherein: The second host material includes an organic electroluminescent compound represented by the following Formula 2: In formula 2, X 11 To X 13 Each independently represents N, CH or CD; L 21 To L 23 each independently represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group; Ar 21 To Ar 23 Each independently represents a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl 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.

12. The plurality of host materials according to claim 11, wherein: Ar 21 To Ar 23 and each independently represents a substituted or unsubstituted phenylnaphthyl, a substituted or unsubstituted naphthylphenyl, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted dimethylbenzofluorenyl, a substituted or unsubstituted dimethylfluorenyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted benzonaphthofuranyl, a substituted or unsubstituted a substituted or unsubstituted diphenylbenzofluorenyl group, a substituted or unsubstituted binaphthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzocarbazolyl group, or a substituted or unsubstituted dibenzothiophene group.

13. The plurality of host materials of claim 11, wherein: The compound represented by Formula 2 is at least one selected from the following compounds. 14 . An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1 .

15. An organic electroluminescent device, comprising: anode; cathode; and at least one light-emitting layer between the anode and the cathode, wherein the at least one light-emitting layer comprises a plurality of host materials according to claim 10.

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