Organic electroluminescent compound, plurality of host materials, and organic

Abstract

An organic electroluminescent compound, a plurality of host materials, and an organic electroluminescent device comprising the same. Provided is an organic electroluminescent compound represented by the following formula 2-1-1: # imgabs0 #

Description

[0001] This invention patent application is a divisional application of the invention patent application with application number 202311333320.4, application date October 16, 2023, and name “Organic electroluminescent compounds, multiple host materials and organic electroluminescent devices containing the same”. Technical Field

[0002] The present disclosure relates to an organic electroluminescent compound, a plurality of host materials, and an organic electroluminescent device comprising the same. Background Art

[0003] Small molecule green organic electroluminescent device (OLED) was first developed by Tang et al. of Eastman Kodak in 1987 by using a TPD / ALq3 double layer consisting of a light-emitting layer and a charge transport layer. Since then, the development of OLED has been completed rapidly and OLED has been commercialized. At present, OLED mainly uses phosphorescent materials with excellent luminous efficiency in panel implementation. However, in many applications such as TV and lighting equipment, the life of OLED is insufficient, and more efficient OLED is still needed. Typically, the higher the brightness of OLED, the shorter the life of OLED. Therefore, for long-term use and high resolution of display, OLED with high luminous efficiency and / or long life characteristics is needed.

[0004] In order to improve luminous efficiency, driving voltage and / or life span, various materials or concepts for organic layers of OLEDs have been proposed. However, they are not satisfactory in practical use. In addition, it has been necessary to develop organic electroluminescent materials with more improved performance (e.g., improved driving voltage, luminous efficiency, power efficiency and / or life span characteristics) compared to the combination of previously disclosed specific compounds.

[0005] Meanwhile, Korean Patent Application Publication No. 2017-0022865 discloses an organic electroluminescent device using phenanthroxazole and phenanthrothiazole compounds as a host. However, the aforementioned references do not specifically disclose an organic electroluminescent device using a specific compound claimed herein or a specific combination of multiple host materials, and there is still a need to develop host materials to improve OLED performance. Summary of the invention

[0006] Technical issues

[0007] The present invention provides an organic electroluminescent compound having a novel structure suitable for application in an organic electroluminescent device. Another object of the present invention is to provide an organic electroluminescent device having higher luminous efficiency and / or improved lifespan characteristics by including a plurality of host materials containing a specific combination of compounds.

[0008] Solution to the problem

[0009] The inventors of the present invention have noticed that a compound having a core (such as phenanthroxazole, phenanthrothiazole, etc.) has a uniquely lower LUMO (lowest unoccupied molecular orbital) energy level compared to a typical hole-type host, and have studied a hole-type host capable of forming an appropriate energy gap with the compound. As a result, when a combination of a compound represented by the following formula 1 and a compound represented by the following formula 2 is used in a light-emitting layer, hole and electron properties are balanced by appropriate HOMO and LUMO energy levels, and an organic electroluminescent device having higher luminous efficiency and / or longer life than a conventional organic electroluminescent device can be provided.

[0010] Specifically, the inventors of the present invention have found that the above-mentioned purpose can be achieved by a compound represented by the following formula 1' and containing at least one deuterium. In addition, as a result of in-depth research to solve these technical problems, the inventors of the present invention have found that the above-mentioned purpose can be achieved by a plurality of host materials, the plurality of host materials comprising a first host material and a second host material, the first host material comprising at least one compound represented by the following formula 1, the second host material comprising at least one compound represented by the following formula 2, wherein at least one of the first host material and the second host material comprises deuterium.

[0011] Furthermore, among various host materials, the inventors of the present invention have found that the above-mentioned object can be achieved by various host materials further comprising a third host material.

[0012] For example, among a plurality of host materials further comprising a third host material, the inventors of the present invention have found that the above-mentioned object can be achieved by a plurality of host materials, wherein the third host material comprises a compound represented by at least one of Formula 3 below.

[0013]

[0014] In formula 1',

[0015] X1 and Y1 each independently represent -N=, -NR7-, -O- or -S-, provided that one of X1 and Y1 represents -N=, and the other of X1 and Y1 represents -NR7-, -O- or -S-;

[0016] R1 represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group;

[0017] R2 to R7 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkylsilyl, (C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstitutedtri(C6-C30)arylsilyl, substituted or unsubstitutedcondensed ring group of one or more (C3-C30)aliphatic rings and one or more (C6-C30)aromatic rings, substituted or unsubstituted mono- or di-(C1-C3 0)alkylamino, substituted or unsubstituted mono- or di-(C2-C30)alkenylamino, substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, substituted or unsubstituted mono- or di-(3- to 30-membered)heteroarylamino, substituted or unsubstituted substituted (C1-C30)alkyl (3- to 30-membered) heteroarylamino, substituted or unsubstituted (C2-C30)alkenyl (C6-C30) arylamino, substituted or unsubstituted (C2-C30)alkenyl (3- to 30-membered) heteroarylamino, or substituted or unsubstituted (C6-C30)aryl (3- to 30-membered) heteroarylamino, or may be connected to one or more adjacent substituents to form one or more rings;

[0018] L1, U1 and U2 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;

[0019] b and c each independently represent an integer of 1 or 2, and d represents an integer of 1 to 4, wherein if b to d represent an integer of 2 or greater, each R2 to each R4 may be the same as or different from each other; and

[0020] In Formula 1', at least one deuterium is included.

[0021]

[0022] In formula 1,

[0023] X1 and Y1 each independently represent -N=, -NR7-, -O- or -S-, provided that one of X1 and Y1 represents -N=, and the other of X1 and Y1 represents -NR7-, -O- or -S-;

[0024] R1 represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group;

[0025] R2 to R7 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkylsilyl, (C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstitutedtri(C6-C30)arylsilyl, substituted or unsubstitutedcondensed ring group of one or more (C3-C30)aliphatic rings and one or more (C6-C30)aromatic rings, substituted or unsubstituted mono- or di-(C1-C3 0)alkylamino, substituted or unsubstituted mono- or di-(C2-C30)alkenylamino, substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, substituted or unsubstituted mono- or di-(3- to 30-membered)heteroarylamino, substituted or unsubstituted substituted (C1-C30)alkyl (3- to 30-membered) heteroarylamino, substituted or unsubstituted (C2-C30)alkenyl (C6-C30) arylamino, substituted or unsubstituted (C2-C30)alkenyl (3- to 30-membered) heteroarylamino, or substituted or unsubstituted (C6-C30)aryl (3- to 30-membered) heteroarylamino, or may be connected to one or more adjacent substituents to form one or more rings;

[0026] L1, U1 and U2 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; and

[0027] b and c each independently represent an integer of 1 or 2, and d represents an integer of 1 to 4, wherein if b to d represent an integer of 2 or more, each R2 to each R4 may be the same as or different from each other.

[0028]

[0029] In formula 2,

[0030] X represents O or S;

[0031] HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group containing at least one nitrogen atom;

[0032] L represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group;

[0033] R8 and R9 each independently represent hydrogen, deuterium, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, or -SiR 21 R 22 R 23 ;

[0034] R 21 To R 23 each independently represents 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; and

[0035] e represents an integer of 1 to 4, and f represents an integer of 1 to 3, wherein if e and f represent an integer of 2 or more, each R8 and each R9 may be the same as or different from each other.

[0036]

[0037] In formula 3,

[0038] X stands for O, S, CR 31 R 32 NR 33 or Se;

[0039] R 31 To R 33 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 to one or more adjacent substituents to form one or more rings;

[0040] A represents a substituted or unsubstituted phenanthrene ring represented by the following formula 3-1;

[0041]

[0042] In equations 3 and 3-1,

[0043] R 21 To R 24 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, The premise is R 21 To R 24 At least one of the

[0044] 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;

[0045] Ar1 to Ar5 each independently represent a substituted or unsubstituted (C6-C30)aryl group or a substituted or unsubstituted (3-membered to 30-membered) heteroaryl group;

[0046] g and j represent integers of 1 to 4, and h and i represent integers of 1 or 2, wherein if g to h represent integers of 2 or more, each R 21 To each R 24 can be the same as or different from one another;

[0047] The * in Formula 3-1 represents the site of connection with Formula 3; and

[0048] R 21 To R 24 The * in the formula represents the site of connection with Formula 3 or 3-1.

[0049] Beneficial Effects of the Invention

[0050] The organic electroluminescent compound according to the present disclosure exhibits properties suitable for use in an organic electroluminescent device. In addition, an organic electroluminescent device having higher luminous efficiency and / or improved 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 host materials according to the present disclosure, and a display system or a lighting system can be manufactured using the organic electroluminescent device. DETAILED DESCRIPTION

[0051] 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.

[0052] 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.

[0053] 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.

[0054] 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 together in one light-emitting layer, 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 separately.

[0055] Herein, the term "(C1-C30) alkyl" means a straight or branched chain alkyl 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 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 may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, and the like. The term "(3- to 7-membered) heterocycloalkyl" means a cycloalkyl having 3 to 7 ring skeleton atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, and preferably the group consisting of O, S, and N. The above-mentioned heterocycloalkyl group can include tetrahydrofuran, pyrrolidine, tetrahydrothiophene (thiolane), tetrahydropyran and the like. The term "(C6-C30) aryl" or "(C6-C30) arylene" means a monocyclic or condensed ring group derived from an aromatic hydrocarbon having 6 to 30 ring skeleton carbon atoms. The above-mentioned aryl group can be partially saturated and can include a spiro structure. The above-mentioned aryl group can include phenyl, biphenyl, terphenyl, pentaphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, triphenylene, 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, naphthacetyl, pyrenyl, 1- Base, 2- Base, 3- Base, 4- Base, 5- Base, 6- Benzo[c]phenanthrenyl, benzo[g] 1-triphenylene, 2-triphenylene, 3-triphenylene, 4-triphenylene, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo[a]fluorenyl, benzo[b]fluorenyl, benzo[c]fluorenyl, dibenzofluorenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl phenyl, 4'-methylbiphenyl, 4"-tert-butyl-4-p-terphenyl-4-yl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4 ... 9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, 11,11-dimethyl-1-benzo[a]fluorenyl, 11,11-dimethyl-2-benzo[a]fluorenyl, 11,11-dimethyl-3-benzo[a]fluorenyl, 11,11-dimethyl-4-benzo[a]fluorenyl 11,11-dimethyl-5-benzo[a]fluorenyl, 11,11-dimethyl-6-benzo[a]fluorenyl, 11,11-dimethyl-7-benzo[a]fluorenyl, 11,11-dimethyl-8-benzo[a]fluorenyl, 11,11-dimethyl-9-benzo[a]fluorenyl, 11,11-dimethyl-10-benzo[ a] fluorenyl, 11,11-dimethyl-1-benzo[b]fluorenyl, 11,11-dimethyl-2-benzo[b]fluorenyl, 11,11-dimethyl-3-benzo[b]fluorenyl, 11,11-dimethyl-4-benzo[b]fluorenyl, 11,11-dimethyl-5-benzo[b]fluorenyl, 11,11-dimethyl-6-benzo[b]fluorenyl 11,11-dimethyl-7-benzo[b]fluorenyl, 11,11-dimethyl-8-benzo[b]fluorenyl, 11,11-dimethyl-9-benzo[b]fluorenyl, 11,11-dimethyl-10-benzo[b]fluorenyl, 11,11-dimethyl-1-benzo[c]fluorenyl, 11,11-dimethyl-2-benzo[c]fluorenyl, 11,11-dimethyl-3-benzo[c]fluorenyl, 11,11-dimethyl-4-benzo[c]fluorenyl, 11,11-dimethyl-5-benzo[c]fluorenyl, 11,11-dimethyl-6-benzo[c]fluorenyl, 11,11-dimethyl-7-benzo[c]fluorenyl, 11,11-dimethyl-8-benzo[c]fluorenyl, 11,11-dimethyl-11-dimethyl-9-benzo[c]fluorenyl, 11,11-dimethyl-10-benzo[c]fluorenyl, 11,11-diphenyl-1-benzo[a]fluorenyl, 11,11-diphenyl-2-benzo[a]fluorenyl, 11,11-diphenyl-3-benzo[a]fluorenyl, 11,11-diphenyl-4-benzo[a]fluorenyl, 11,11-diphenyl-5-benzo[a]fluorenyl, 11,11-diphenyl-6-benzo[a]fluorenyl, 11,11-diphenyl-7-benzo[a]fluorenyl, 11,11-diphenyl 11,11-diphenyl-9-benzo[a]fluorenyl, 11,11-diphenyl-10-benzo[a]fluorenyl, 11,11-diphenyl-1-benzo[b]fluorenyl, 11,11-diphenyl-2-benzo[b]fluorenyl, 11,11-diphenyl-3-benzo[b]fluorenyl, 11,11-diphenyl-4-benzo[b]fluorenyl, 11,11-diphenyl-5-benzo[b]fluorenyl, 11,11-diphenyl-6-benzo[b]fluorenyl, 11,11-diphenyl-7-benzo[b]fluorenyl ] fluorenyl, 11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9-benzo[b]fluorenyl, 11,11-diphenyl-10-benzo[b]fluorenyl, 11,11-diphenyl-1-benzo[c]fluorenyl, 11,11-diphenyl-2-benzo[c]fluorenyl, 11,11-diphenyl-3-benzo[c]fluorenyl, 11,11-diphenyl-4-benzo[c]fluorenyl, 11,11-diphenyl-5-benzo[c]fluorenyl, 11,11-diphenyl-6-benzo[c]fluorenyl, 11 ,11-diphenyl-7-benzo[c]fluorenyl, 11,11-diphenyl-8-benzo[c]fluorenyl, 11,11-diphenyl-9-benzo[c]fluorenyl, 11,11-diphenyl-10-benzo[c]fluorenyl, 9,9,10,10-tetramethyl-9,10-dihydro-1-phenanthryl, 9,9,10,10-tetramethyl-9,10-dihydro-2-phenanthryl, 9,9,10,10-tetramethyl-9,10-dihydro-3-phenanthryl, 9,9,10,10-tetramethyl-9,10-dihydro-4-phenanthryl, etc. ,

[0056] The term "(3- to 30-membered) heteroaryl" or "(3- to 30-membered) heteroarylene" means an aryl group having 3 to 30 ring skeleton atoms and including at least one, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, Si and P. The above 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 an 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, di ... triazinyl, triazinyl, triazinyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl and pyridazinyl, and fused ring heteroaryl groups, such as furanyl, thienyl, benzothienyl, dibenzoselenophene, naphthobenzofuranyl, naphthobenzothienyl, naphthooxazolyl, benzofuranoquinolyl, benzofuranoquinazolinyl, benzofuranonaphthyridinyl, benzofuranopyrimidinyl, naphthofuranopyrimidinyl, benzothienoquinolyl, benzothienoquinazolinyl, naphthyridinyl, benzothienonaphthyridinyl, benzothienopyrimidinyl, naphthienopyrimidinyl, pyrimidoindolyl, benzopyrimidindolyl, benzofuranopyrazinyl, naphthofuranopyrazinyl, benzothienopyrazinyl, naphthienopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, Quinoxaline, benzoquinoxaline, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, benzotriazolyl, phenazinyl, imidazopyridinyl, chromenoquinazolinyl, thiochromenoquinazolinyl, dimethylbenzoperimidinyl, indolecarbazolyl, indenocarbazolyl, etc. More specifically, the above-mentioned 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 The term "heteroaryl" includes 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, etc. "(sub)heteroaryl" can be divided into (sub)heteroaryl having electron characteristics and (sub)heteroaryl having hole characteristics. The (sub)heteroaryl 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 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. ,

[0057] In addition, "ortho (o-)", "meta (m-)", and "para (p-)" are prefixes that indicate the relative positions of substituents, respectively. The ortho position indicates 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 the ortho position. The meta position indicates that two substituents are at positions 1 and 3, and for example, when two substituents in a benzene derivative occupy positions 1 and 3, it is referred to as the meta position. The para position indicates that two substituents are at positions 1 and 4, and for example, when two substituents in a benzene derivative occupy positions 1 and 4, it is referred to as the para position.

[0058] 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 may be substituted for a functional group may be the total number of valences that may be substituted for each atom that forms the functional group.Herein, substituted aryl, substituted heteroaryl, substituted arylene, substituted heteroarylene, substituted alkyl, substituted cycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted condensed ring group of one or more aliphatic rings and one or more aromatic rings, substituted mono- or di-alkylamino, substituted mono- or di-alkenylamino, substituted alkylalkenylamino, substituted mono- or di-arylamino, substituted alkylarylamino, substituted mono- or di-heteroarylamino, substituted alkylheteroarylamino, substituted alkenylarylamino, substituted alkenylheteroarylamino and substituted arylheteroarylamino are each independently The present invention is independently substituted by at least one selected from the group consisting of: deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; phosphine oxide; (C1-C30) alkyl; halo (C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3- to 7-membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (3- to 30-membered) heteroaryl, which is unsubstituted or substituted by at least one of deuterium and (C6-C30) aryl; (C6-C30) aryl, which is unsubstituted or substituted by at least one of deuterium and (C6-C30) aryl. alkyl; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; a condensed 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; (C1-C30)alkyl(C2-C30)alkenylamino; mono- or di-(C6-C30)arylamino; (C1-C30)alkyl(C6-C30)arylamino; mono- or di-(3- to 30-membered)heteroarylamino alkyl; (C1-C30)alkyl(3- to 30-membered)heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30)alkenyl(3- to 30-membered)heteroarylamino; (C6-C30)aryl(3- to 30-membered)heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; (C6-C30)arylphosphine; di(C6-C30)arylborylcarbonyl; di(C1-C30)alkylborylcarbonyl; (C1-C30)alkyl(C6-C30)arylborylcarbonyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl.According to one embodiment of the present disclosure, the substituted alkyl group and the like are each independently substituted by at least one selected from the group consisting of: deuterium; unsubstituted or deuterium-substituted (C1-C10) alkyl; unsubstituted or (C6-C22) aryl substituted by at least one of deuterium and (C6-C18) aryl; unsubstituted or deuterium-substituted (6- to 20-membered) heteroaryl; and unsubstituted or deuterium-substituted tri(C6-C15) arylsilyl. According to another embodiment of the present disclosure, the substituted alkyl group, etc. are each independently substituted by at least one selected from the group consisting of: deuterium; unsubstituted or deuterium-substituted (C1-C6) alkyl; unsubstituted or (C6-C18) aryl substituted by at least one of deuterium and (C6-C18) aryl; unsubstituted or deuterium-substituted (6-15-membered) heteroaryl; and unsubstituted or deuterium-substituted tri(C6-C10) arylsilyl. For example, the substituted alkyl group, etc. may be substituted by deuterium or by at least one selected from the group consisting of: methyl, tetramethyl, phenyl, biphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, terphenyl, naphthyl substituted by one or more biphenyls, phenanthrenyl, benzo[c]phenanthrenyl,. The invention also includes 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67,

[0059] If there is no indication substituent in the chemical formula or compound structure of this article, this may mean that all positions where the substituent can be substituted 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 case of no indication substituent in the chemical formula or compound structure of this article, if deuterium is not explicitly excluded (such as the content of deuterium is 0%, the content of hydrogen is 100%), all substituents are hydrogen, and hydrogen and deuterium can be used together 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. Isotope refers to an atom with the same atomic number (Z) but different mass number (A), and can also be interpreted as an element with the same number of protons but different numbers of neutrons.

[0060] In the present disclosure, the term "combination thereof" refers to a combination of one or more elements from the corresponding list to form a known or chemically stable arrangement that a person skilled in the art can envision from the corresponding list. For example, an alkyl group and a deuterium group can be combined to form a partially or fully deuterated alkyl group; a halogen group and an alkyl group can be combined to form a haloalkyl substituent; a halogen group, an alkyl group, and an aryl group can be combined to form a haloarylalkyl group. For example, a preferred combination of substituents contains 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. Alternatively, in many cases, a preferred combination of substituents can contain up to 20 atoms that are not hydrogen or deuterium.

[0061] 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.

[0062] In the formula of the present disclosure, the heteroaryl group or the heteroarylene group may each independently contain at least one heteroatom selected from B, N, O, S, Si and P. In addition, the heteroatom may be bonded to at least one selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl, (C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, and substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino.

[0063] Hereinafter, an organic electroluminescent compound according to one embodiment of the present disclosure will be described.

[0064] The organic electroluminescent compound according to one embodiment of the present disclosure is represented by the following Formula 1' and contains one or more deuteriums.

[0065]

[0066] In formula 1',

[0067] X1 and Y1 each independently represent -N=, -NR7-, -O- or -S-, provided that one of X1 and Y1 represents -N=, and the other of X1 and Y1 represents -NR7-, -O- or -S-;

[0068] R1 represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group;

[0069] R2 to R7 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkylsilyl, (C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstitutedtri(C6-C30)arylsilyl, substituted or unsubstitutedcondensed ring group of one or more (C3-C30)aliphatic rings and one or more (C6-C30)aromatic rings, substituted or unsubstituted mono- or di-(C1-C3 0)alkylamino, substituted or unsubstituted mono- or di-(C2-C30)alkenylamino, substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, substituted or unsubstituted mono- or di-(3- to 30-membered)heteroarylamino, substituted or unsubstituted substituted (C1-C30)alkyl (3- to 30-membered) heteroarylamino, substituted or unsubstituted (C2-C30)alkenyl (C6-C30) arylamino, substituted or unsubstituted (C2-C30)alkenyl (3- to 30-membered) heteroarylamino, or substituted or unsubstituted (C6-C30)aryl (3- to 30-membered) heteroarylamino, or may be connected to one or more adjacent substituents to form one or more rings;

[0070] L1, U1 and U2 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;

[0071] b and c each independently represent an integer of 1 or 2, and d represents an integer of 1 to 4, wherein if b to d represent an integer of 2 or greater, each R2 to each R4 may be the same as or different from each other; and

[0072] In Formula 1', at least one deuterium is included.

[0073] The compound represented by Formula 1' may be selected from the group consisting of the following compounds, but is not limited thereto.

[0074]

[0075]

[0076]

[0077]

[0078]

[0079] Hereinafter, various host materials according to the present disclosure will be described.

[0080] The plurality of host materials according to the present disclosure include a first host material and a second host material, the first host material includes at least one compound represented by the above formula 1, the second host material includes at least one compound represented by the above formula 2, wherein at least one of the first host material and the second host material includes deuterium. In addition, the plurality of host materials further include a third host material, wherein as an example, the third host material includes a plurality of host materials including the following formula 3.

[0081] Hereinafter, the compound represented by Formula 1 will be described in more detail.

[0082] In Formula 1, X1 and Y1 each independently represent -N=, -NR7-, -O- or -S-, provided that one of X1 and Y1 represents -N=, and the other of X1 and Y1 represents -NR7-, -O- or -S-. According to one embodiment of the present disclosure, one of X1 and Y1 represents -N=, and the other of X1 and Y1 represents -O- or -S-.

[0083] In Formula 1, R1 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, R1 represents an unsubstituted or deuterated (C6-C15) aryl group, or an unsubstituted or deuterated (5- to 15-membered) heteroaryl group. According to another embodiment of the present disclosure, R1 represents an unsubstituted or deuterated (C6-C15) aryl group, or an unsubstituted or deuterated (6- to 13-membered) heteroaryl group. Specifically, R1 can be a phenyl group, a biphenyl group, a naphthyl group, or a pyridyl group, etc., which can be further substituted with deuterium.

[0084] In Formula 1, R2 to R7 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, substituted or unsubstituted mono- or di-(C1-C30) alkyldi(C6-C30) arylsilyl, C30)alkylamino, substituted or unsubstituted mono- or di-(C2-C30)alkenylamino, substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, substituted or unsubstituted mono- or di-(3- to 30-membered)heteroarylamino, substituted or unsubstituted (C1-C30)alkyl(3- to 30-membered)heteroarylamino, substituted or unsubstituted (C2-C30)alkenyl(C6-C30)arylamino, substituted or unsubstituted (C2-C30)alkenyl(3- to 30-membered)heteroarylamino, or substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino, may be connected to one or more adjacent substituents to form one or more rings.

[0085] According to one embodiment of the present disclosure, R5 and R6 each independently represent a substituted or unsubstituted (C6-C28)aryl group, a substituted or unsubstituted (6- to 25-membered) heteroaryl group. According to another embodiment of the present disclosure, R5 and R6 each independently represent deuterium, an unsubstituted or (C6-C28)aryl group substituted with at least one of deuterium, (C1-C10)alkyl, (C6-C12)aryl and tri(C6-C10)arylsilyl, or an unsubstituted or (6- to 20-membered) heteroaryl group substituted with at least one of deuterium, (C6-C10)aryl and (6- to 10-membered) heteroaryl group. Specifically, R2 to R4 can each independently be hydrogen or deuterium; R5 and R6 can each independently be phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, triphenylene, dimethylfluorenyl, diphenylfluorenyl, pyridyl, unsubstituted or substituted with one or more phenyls, dibenzofuranyl, dibenzothienyl, carbazolyl, benzofuranopyridyl, benzonaphthofuranyl, benzonaphthothienyl, or triphenylsilyl, which can be further substituted with deuterium.

[0086] According to another embodiment of the present disclosure, R5 and R6 can independently be substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted triazine, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinazoline, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted quinazoline, substituted or unsubstituted pyrimidinyl ... substituted quinoxalyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted benzofuranopyridyl, substituted or unsubstituted benzofuranopyrimidinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophenyl, or triphenylsilyl.

[0087] L1, U1 and U2 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, U1 and U2 each independently represent 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, L1, U1 and U2 each independently represent a single bond, an unsubstituted or deuterated (C6-C15) arylene group, or an unsubstituted or deuterated (3- to 25-membered) heteroarylene group. Specifically, L1, U1 and U2 each independently represent a single bond, a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, a dibenzofuranyl group, a pyridylene group, a carbazolyl group, etc., which may be further substituted with deuterium.

[0088] In Formula 1, b and c each independently represent an integer of 1 or 2, and d represents an integer of 1 to 4, wherein if b to d represent an integer of 2 or more, each R1 to each R4 may be the same as or different from each other.

[0089] According to one embodiment of the present disclosure, Formula 1 may be represented by at least one of the following Formulas 1-1 to 1-4.

[0090]

[0091]

[0092] In Formulae 1-1 to 1-4, R1 to R6, L1, U1, U2, and b to d are as defined in Formula 1.

[0093] According to one embodiment of the present disclosure, when the compound represented by Formula 1 contains deuterium, the deuterium substitution rate may be about 0.1% to 100%, about 10% to about 95% according to one embodiment, about 20% to about 90% according to another embodiment, about 30% to about 85% according to another embodiment, about 40% to about 80% according to another embodiment, and about 50% to about 75% according to another embodiment. The compound having Formula 1 substituted with the deuterium substitution rate can increase the stability of the compound by increasing the bond dissociation energy due to deuteration, and the organic electroluminescent device including the compound can exhibit improved life characteristics.

[0094] Hereinafter, the compound represented by Formula 2 will be described in more detail.

[0095] In Formula 2, X represents O or S.

[0096] In Formula 2, HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group containing at least one nitrogen atom. According to one embodiment of the present disclosure, HAr represents a substituted or unsubstituted (6- to 15-membered) heteroaryl group containing at least two nitrogen atoms. According to another embodiment of the present disclosure, HAr represents a substituted or unsubstituted (6-membered) heteroaryl group containing at least two nitrogen atoms, and the substituent of the heteroaryl group is deuterium; a (C6-C20) aryl group that is unsubstituted or substituted with at least one of deuterium and a (C6-C12) aryl group; or a (6- to 15-membered) heteroaryl group that is unsubstituted or substituted with deuterium. Specifically, HAr is a substituted triazinyl group, and the substituent of the triazinyl group is a phenyl group, a biphenyl group, a terphenyl group, a phenylnaphthyl group, a naphthylphenyl group, a naphthyl group substituted with one or more biphenyl groups, a phenanthrenyl group, a benzo[c]phenanthrenyl group, At least one of a benzofuranyl group and a dibenzofuranyl group, which may be further substituted with deuterium.

[0097] In Formula 2, L represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3-membered to 30-membered)heteroarylene group. Specifically, L may be a single bond.

[0098] In Formula 2, R8 and R9 each independently represent hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, or -SiR 21 R 22 R 23 . According to one embodiment of the present disclosure, R8 and R9 each independently represent hydrogen, deuterium, or substituted or unsubstituted (C6-C20)aryl. According to another embodiment of the present disclosure, R8 and R9 each independently represent hydrogen, deuterium, or unsubstituted or (C6-C15)aryl substituted by at least one of deuterium and (C6-C12)aryl. Specifically, R8 and R9 each independently can be hydrogen, deuterium, phenyl, biphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, or phenanthryl, which can be further substituted by deuterium.

[0099] R 21 To R 23 Each independently represents 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.

[0100] In Formula 2, e represents an integer of 1 to 4, and f represents an integer of 1 to 3, wherein if e and f represent an integer of 2 or more, each R8 and each R9 may be the same as or different from each other.

[0101] According to one embodiment of the present disclosure, Formula 2 may be represented by the following Formula 2-1.

[0102]

[0103] In Formula 2-1, X'1 to X'3 each independently represent CR' or N, provided that at least two of X'1 to X'3 represent N. Specifically, X'1 to X'3 may all be N.

[0104] R' represents hydrogen or deuterium.

[0105] In formula 2-1, R 10 and R 11 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 10 and R 11 Each independently represents a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (6- to 20-membered) heteroaryl group. According to another embodiment of the present disclosure, R 10 and R 11 Each independently represents an unsubstituted or (C6-C20)aryl group substituted with at least one of deuterium and (C6-C18)aryl group; or an unsubstituted or (6- to 15-membered) heteroaryl group substituted with at least one of deuterium and (C6-C18)aryl group. Specifically, R 10 and R 11 Each independently may be phenyl which is unsubstituted or substituted with naphthyl (substituted with one or more phenyl groups or one or more phenanthryl groups), biphenyl, terphenyl, quaterphenyl, phenylnaphthyl, naphthylphenyl, naphthyl which is unsubstituted or substituted with one or more biphenyl groups or one or more naphthyl groups, phenanthryl which is unsubstituted or substituted with one or more phenyl groups or one or more naphthyl groups, benzo[c]phenanthryl, The invention further comprises a dibenzofuranyl group, a terphenylene group, a fluoranthenyl group, or a dibenzofuranyl group which is unsubstituted or substituted with one or more phenyl groups and which may be further substituted with deuterium.

[0106] In Formula 2-1, X, L, R8, R9, e and f are as defined in Formula 2.

[0107] According to one embodiment of the present disclosure, Formula 2 may be represented by at least one of the following Formulas 2-1-1 to 2-1-4.

[0108]

[0109]

[0110] In formulas 2-1-1 to 2-1-4,

[0111] X, X'1 to X'3, R8 to R 11 , L, e and f are defined as in Formula 2-1.

[0112] According to one embodiment of the present disclosure, when the compound represented by Formula 2 contains deuterium, the deuterium substitution rate may be about 0.1% to 100%, about 10% to about 95% according to one embodiment, about 20% to about 90% according to another embodiment, about 30% to about 85% according to another embodiment, about 40% to about 80% according to another embodiment, and about 50% to about 75% according to another embodiment. The compound having Formula 2 substituted with the deuterium substitution rate can increase the stability of the compound by increasing the bond dissociation energy due to deuteration, and the organic electroluminescent device including the compound can exhibit improved life characteristics.

[0113] Hereinafter, the compound represented by Formula 3 will be described in more detail.

[0114]

[0115] In formula 3,

[0116] X stands for O, S, CR 31 R 32 NR 33 According to one embodiment of the present disclosure, X represents O, S, CR 31 R 32 or NR 33 Specifically, X may be O or S.

[0117] R 31 To R 33 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 to one or more adjacent substituents to form one or more rings. According to one embodiment of the present disclosure, R 31 To R 33 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C3-C12) alkyl, or substituted or unsubstituted (C6-C15) aryl. According to another embodiment of the present disclosure, R 31 To R 33 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C3-C12) alkyl, or substituted or unsubstituted (C6-C15) aryl. 31 To R 33 Each independently can be hydrogen or deuterium.

[0118] A represents a substituted or unsubstituted phenanthrene ring represented by the following formula 3-1.

[0119]

[0120] In equations 3 and 3-1,

[0121] R 21 To R 24 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, The premise is R 21 To R 24 At least one of the According to one embodiment of the present disclosure, R 21 To R 24 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C15) alkyl, substituted or unsubstituted (C6-C15) aryl, According to another embodiment of the present disclosure, R 21 To R 24 Each independently represents hydrogen, deuterium, halogen, unsubstituted (C1-C15) alkyl, unsubstituted (C6-C15) aryl, Specifically, R 21 To R 24 Each independently can be hydrogen, deuterium, phenyl, biphenyl, naphthyl,

[0122] 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 (3-30-membered) heteroarylene group. According to one embodiment of the present disclosure, L2 and L3 each independently represent a single bond, a substituted or unsubstituted (C6-C12) arylene group, or a substituted or unsubstituted (C6-C25) cycloalkylene group. Specifically, L2 and L3 each independently can be a single bond, a phenylene group, a phenylene group substituted by one or more diphenylamino groups, a phenylene group substituted by one or more naphthyl groups, or a naphthyl group substituted by one or more phenyl groups.

[0123] Ar1 to Ar5 each independently represent a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3- to 30-membered) heteroaryl. According to one embodiment of the present disclosure, Ar1 to Ar5 each independently represent an unsubstituted (C6-C12) aryl substituted with at least one of deuterium, (C5-C15) aryl and (3- to 30-membered) heteroaryl; an unsubstituted (C6-C25) aryl substituted with one or more (C6-C18) aryl, one or more (5- to 15-membered) heteroaryl, or one or more (C1-C6) arylene; an unsubstituted (5- to 25-membered) heteroaryl, a terphenyl or a quaterphenyl substituted with deuterium or one or more (C6-C18) aryl. Specifically, Ar1 to Ar5 can each independently be a phenyl group which is unsubstituted or substituted with at least one of deuterium, naphthyl, carbazolyl, phenylcarbazolyl, dibenzofuranyl, dibenzothiophenyl, phenanthryl, fluorenyl substituted with one or more methyl groups, pyridyl and adamantyl; a biphenyl group which is unsubstituted or substituted with deuterium; a phenanthryl group substituted with one or more tetramethyl groups, a propylenediphenyl group, a carbazolyl group which is unsubstituted or substituted with one or more phenyl groups, substituted by one or more phenyl groups, one or more biphenyl groups or one or more pyridyl groups; pyridyl groups unsubstituted or substituted by one or more phenyl groups or one or more naphthyl groups; triphenylsilyl, dibenzothiophenyl groups unsubstituted or substituted by one or more phenyl groups, terphenyl groups unsubstituted or substituted by one or more cyano groups, quaterphenyl groups and phenanthroline groups substituted by one or more phenyl groups.

[0124] g and j represent integers of 1 to 4, and h and i represent integers of 1 or 2, wherein if g to h represent integers of 2 or more, each R 21 and each R 24 May be the same as or different from each other.

[0125] The * in Formula 3-1 indicates the site of connection with Formula 3, and R 21 To R 24 The * in the formula represents the site of connection with Formula 3 or 3-1.

[0126] According to one embodiment of the present disclosure, Formula 3 may be represented by the following Formula 3-2 or 3-3.

[0127]

[0128] In formulas 3-2 and 3-3, X, R 21 To R 24, and g to j are as defined in Formula 3. The compound represented by Formula 1 may be selected from the group consisting of the following compounds, but is not limited thereto.

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139] The compound represented by Formula 2 may be selected from the group consisting of the following compounds, but is not limited thereto.

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150] The compound represented by Formula 3 may be selected from the group consisting of the following compounds, but is not limited thereto.

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175] A combination of at least one of compounds H1-1 to H1-315 and at least one of compounds H2-1 to H2-276 can be used in an organic electroluminescent device.

[0176] Furthermore, a combination of at least one of compounds H1-1 to H1-315, at least one of compounds H2-1 to H2-276, and at least one of compounds H3-1 to H3-771 can be used in an organic electroluminescent device.

[0177] The compound represented by Formula 1 according to the present disclosure can be produced by a synthesis method known to those skilled in the art, and in particular, by using a synthesis method disclosed in many patent documents, for example, by referring to the methods disclosed in Korean Patent Application Publication No. 2018-0099487 (published on September 5, 2018), Korean Patent Application Publication No. 2021-0098316 (published on August 10, 2021), Korean Patent Application Publication No. 2022-0051794 (published on April 26, 2022), and Korean Patent Application Publication No. 2021-0109436 (published on September 6, 2021), etc., but is not limited thereto.

[0178] The compound represented by Formula 2 according to the present disclosure can be produced by a synthesis method known to those skilled in the art, and in particular, by using a synthesis method disclosed in many patent documents, for example, by referring to the methods disclosed in Korean Patent Application Publication No. 2022-0051794 (published on April 26, 2022), Korean Patent Application Publication No. 2021-0124018 (published on October 14, 2021), and Korean Patent Application Publication No. 2021-0109436 (published on September 6, 2021), etc., but is not limited thereto.

[0179] The compound represented by Formula 3 according to the present disclosure may be produced by referring to the following Reaction Scheme 1, but is not limited thereto, and may be produced by a synthesis method known to those skilled in the art.

[0180] [Reaction Scheme 1]

[0181]

[0182] Although the illustrative synthesis examples of the compounds represented by Formulae 1 to 3 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, etc., and the above reactions proceed even when substituents defined in Formulae 1 to 3 above but not specified in the specific synthesis examples are bonded.

[0183] In addition, the deuterated compounds of formula 1 to 3 can be prepared in a similar manner using deuterated precursor materials, or more generally, can be prepared by treating undeuterated compounds with deuterated solvents or D6-benzene in the presence of H / D exchange catalysts (such as Lewis acids, such as aluminum chloride or ethylaluminum chloride). In addition, the degree of deuteration can be controlled by changing reaction conditions such as reaction temperature. For example, the number of deuterium in formula 1 to 3 can be controlled by adjusting the reaction temperature and time, the equivalent of acid, etc.

[0184] The present disclosure provides an organic electroluminescent device, which includes the organic electroluminescent compound according to the present disclosure having a specific formula 1'.

[0185] 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 or the first host material to the third host material according to the present disclosure may be contained in one light-emitting layer, or may be contained in different light-emitting layers, respectively. In the various host materials of the present disclosure, for example, 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, or the compound represented by Formulas 1 to 3 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.

[0186] Herein, the first host material in the various host materials of the present disclosure can be about 5 to about 90 weight %, preferably about 10 to about 90 weight %, more preferably about 10 to about 80 weight %, even more preferably about 15 to about 70 weight %, further more preferably about 30 to about 70 weight %, and further more preferably about 30 to about 60 weight %. In the various host materials of the present disclosure, the second host material can be about 5 to about 90 weight %, preferably about 10 to about 90 weight %, more preferably about 10 to about 80 weight %, even more preferably about 15 to about 70 weight %, further more preferably about 30 to about 70 weight %, and further more preferably about 30 to about 60 weight %. In the various host materials of the present disclosure, the third host material can be about 5 to about 90 weight %, preferably about 10 to about 90 weight %, more preferably about 10 to about 80 weight %, even more preferably about 15 to about 70 weight %, further more preferably about 30 to about 70 weight %, and further more preferably about 30 to about 60 weight %. For example, the plurality of host materials includes about 5 to about 70 weight percent of a first host material, about 5 to about 70 weight percent of a second host material, and about 10 to about 90 weight percent of a third host material.

[0187] 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.

[0188] 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.

[0189]

[0190] In formula 101,

[0191] L' is selected from the following structures 1 to 3:

[0192]

[0193] R 100 To R 103Each 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;

[0194] 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;

[0195] 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

[0196] s represents an integer of 1 to 3.

[0197] Specific examples of the dopant compound are as follows, but are not limited thereto.

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204] 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.

[0205] The anode and cathode may each be formed of a transparent conductive material, or a semi-transmissive reflective 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.

[0206] 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.

[0207] 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.

[0208] 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.

[0209] 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.

[0210] 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.

[0211] 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.

[0212] 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.

[0213] The organic electroluminescent material according to the present disclosure can be used as a light-emitting material for a white organic light-emitting device. White organic light-emitting devices have been proposed to have 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 components, or a color conversion material (CCM) method, etc. The organic electroluminescent material according to the present disclosure can also be used in an organic electroluminescent device containing quantum dots (QDs).

[0214] 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 the first to third host compounds of the present disclosure are used to form a film, a co-evaporation process or a mixed evaporation process is performed.

[0215] 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 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.

[0216] The organic electroluminescent device according to one embodiment of the present disclosure may be an organic electroluminescent device having a tandem structure. According to one embodiment of the tandem organic electroluminescent device, a single light-emitting unit (light-emitting unit) may be formed into a structure in which two or more light-emitting units are connected by a charge generation layer. The organic electroluminescent device may include a plurality of two 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, for example, it may include a plurality of three or more light-emitting units. The organic electroluminescent device may include a plurality of light-emitting units, and each light-emitting unit may include a hole transport region, a light-emitting layer, and an electron transport band, and the hole transport region may include a hole injection layer and a hole transport layer. The transport band may include an electron transport layer and an electron injection layer, and according to one example, the light-emitting unit may include three or more light-emitting layers. According to one embodiment, the light-emitting layers constituting the light-emitting unit may be three or more. A plurality of 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 the plurality of light-emitting layers may have the same or different colors. The light-emitting unit 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 can be located between each light-emitting unit. At this time, the multiple charge generation layers can 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 series organic electroluminescent device using only a pair of anodes and cathodes without the need for a separate internal electrode located between the stacks.

[0217] 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 composed of a metal or an organic material doped with a P-type dopant. For example, the metal may be made of one 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 can be used as P-type dopants and host materials used in P-type doped organic materials.

[0218] The manufacturing method of the organic electroluminescent device of the present disclosure is not limited, and the manufacturing method of the following device example is only an example and is not limited thereto. Those skilled in the art can reasonably describe the manufacturing method of the following device example based on the prior art.

[0219] For example, there is no particular restriction on the mixing ratio of the first compound and the second compound, and those 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, two or more types of host materials and light-emitting materials can be placed in different evaporation sources and co-deposited to form a light-emitting layer, and a pre-mixed mixture of two or more host materials can be placed on the same evaporation source and then co-deposited with a light-emitting material placed on another evaporation source to form a light-emitting layer. This pre-mixing method can further save evaporation sources. According to one embodiment, the first compound, the second compound, and the light-emitting material of the present disclosure may be placed in different evaporation sources and co-deposited to form a light-emitting layer, or a premixed mixture of the first compound and the second compound may 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.

[0220] 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.

[0221] 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.

[0222] Example 1: Preparation of compound H1-27-D14

[0223]

[0224] Compound H1-152 (35.0 g, 55.6 mmol), benzene-D6 and 1.4 L dichlorobenzene were added to a flask, and 70 mL trifluoromethanesulfonic acid was added at 40 ° C. After 3 hours, the mixture was cooled to room temperature, 35 mL heavy water was added and stirred for 10 minutes. The mixture was neutralized with K3PO4 aqueous solution and the organic layer was extracted with dichloromethane. After removing the remaining moisture using magnesium sulfate, the filtrate was distilled under reduced pressure and separated by column chromatography to obtain compound H1-27-D14 (wherein n is 14) (32.3 g, yield: 92.2%).

[0225] Example 2: Preparation of Compound H1-121-D18

[0226]

[0227] Compound H1-246 (35.0 g, 49.7 mmol), benzene-D6 and 1.4 L dichlorobenzene were added to a flask, and 70 mL trifluoromethanesulfonic acid was added at 40 ° C. After 3 hours, the mixture was cooled to room temperature, 35 mL heavy water was added and stirred for 10 minutes. The mixture was neutralized with K3PO4 aqueous solution and the organic layer was extracted with dichloromethane. After removing the remaining moisture using magnesium sulfate, the filtrate was distilled under reduced pressure and separated by column chromatography to obtain compound H1-121-D18 (wherein n is 18) (31 g, yield: 88.5%).

[0228] Example 3: Preparation of Compound H1-33-D15

[0229]

[0230] Compound H1-158 (35.0 g, 54.2 mmol), benzene-D6 and 1.4 L dichlorobenzene were added to a flask, and 70 mL trifluoromethanesulfonic acid was added at 40 ° C. After 3 hours, the mixture was cooled to room temperature, 35 mL heavy water was added and stirred for 10 minutes. The mixture was neutralized with K3PO4 aqueous solution and the organic layer was extracted with dichloromethane. After removing the remaining moisture using magnesium sulfate, the filtrate was distilled under reduced pressure and separated by column chromatography to obtain compound H1-33-D15 (wherein n is 15) (31 g, yield: 88.5%).

[0231] Example 4: Preparation of Compound H2-1-D11

[0232]

[0233] Compound H2-51 (35.0 g, 54.2 mmol), benzene-D6 and 1.4 L dichlorobenzene were added to a flask, and 60 mL trifluoromethanesulfonic acid was added at 40 ° C. After 3 hours, the mixture was cooled to room temperature, 30 mL heavy water was added and stirred for 10 minutes. The mixture was neutralized with K3PO4 aqueous solution and the organic layer was extracted with dichloromethane. After removing the remaining moisture using magnesium sulfate, the filtrate was distilled under reduced pressure and separated by column chromatography to obtain compound H2-1-D11 (wherein n is 11) (15 g, yield: 49%).

[0234] Example 5: Preparation of Compound H2-1

[0235]

[0236] 1) Synthesis of compound 5-1

[0237] 2-Chloro-6-phenylnaphthalene (44.5 g, 186.3 mmol), benzene-D6 and 0.9 L dichlorobenzene were added to a flask, and 60 mL trifluoromethanesulfonic acid was added at 60 ° C. After 12 hours, the mixture was cooled to room temperature, 45 mL heavy water was added and stirred for 10 minutes. The mixture was neutralized with K3PO4 aqueous solution and the organic layer was extracted with dichloromethane. After removing the remaining moisture using magnesium sulfate, the filtrate was distilled under reduced pressure and separated by column chromatography to obtain compound 5-1 (32.6 g, yield: 73%).

[0238] 2) Synthesis of compound 5-2

[0239] Compound 5-1 (30g, 122mmol), bis(pinacol)diboron (46.5g, 183mmol), tris(dibenzylideneacetone)dipalladium (5.6g, 6.1mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (s-phos) (5.0g, 12.2mmol), potassium acetate (36.0g, 366mmol) and 610mL of 1,4-dioxane were added to the reaction vessel and stirred at 150°C for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. After the organic layer was dried over magnesium sulfate, the solvent was removed by a rotary evaporator. The residue was purified by column chromatography to obtain compound 5-2 (34g, yield: 82%).

[0240] 3 ) Compound H2-1 Synthesis

[0241] Compound 5-2 (34 g, 103 mmol), 2-chloro-4-(dibenzo[b, d]furan-1 base)-6-(naphthalene-2-yl)-1,3,5-triazine (42 g, 103 mmol), tetrakis(triphenylphosphine)palladium (5.9 g, 5.2 mmol), calcium carbonate (28.4 g, 206 mmol), 515 mL toluene, 129 mL ethanol, 129 mL distilled water were added to a reaction vessel and stirred at 120 ° C for 8 hours. After the reaction was completed, the mixture was added dropwise to methanol, and the resulting solid was filtered. Thereafter, the product was purified by column chromatography to obtain compound H2-1 (42 g, yield: 70%).

[0242] Example 6: Preparation of Compound H2-38

[0243]

[0244] 1) Synthesis of compound 6-1

[0245] 3-Chloro (30g, 114mmol), benzene-D6 and 0.7L dichlorobenzene were added to a flask, and 9mL trifluoromethanesulfonic acid was added at 50°C. After 12 hours, the mixture was cooled to room temperature, 30mL heavy water was added and stirred for 10 minutes. The mixture was neutralized with K3PO4 aqueous solution and the organic layer was extracted with dichloromethane. After removing the remaining moisture using magnesium sulfate, the filtrate was distilled under reduced pressure and separated by column chromatography to obtain compound 6-1 (24g, yield: 80%).

[0246] 2) Synthesis of compound 6-2

[0247] Compound 6-1 (24g, 93mmol), bis(pinacol)diboron (35.7g, 140mmol), tris(dibenzylideneacetone)dipalladium (4.3g, 4.6mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (s-phos) (3.8g, 9.4mmol), potassium acetate (27.5g, 280mmol) and 460mL of 1,4-dioxane were added to the reaction vessel and stirred at 150°C for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. After the organic layer was dried over magnesium sulfate, the solvent was removed by a rotary evaporator. The residue was purified by column chromatography to obtain compound 6-2 (25g, yield: 73%).

[0248] 3 ) Compound H2-38 Synthesis

[0249] Compound 6-2 (10 g, 28 mmol), 2-chloro-4-(dibenzo[b, d]furan-1 base)-6-phenyl-1,3,5-triazine (12 g, 34 mmol), tetrakis(triphenylphosphine)palladium (1.6 g, 1.4 mmol), calcium carbonate (7.8 g, 56 mmol), 141 mL toluene, 20 mL ethanol, 30 mL distilled water were added to a reaction vessel and stirred at 120 ° C for 8 hours. After the reaction was completed, the mixture was added dropwise to methanol, and the resulting solid was filtered. Thereafter, the product was purified by column chromatography to obtain compound H2-38 (12 g, yield: 70%).

[0250] Example 7: Preparation of Compound H2-36

[0251]

[0252] 1) Synthesis of compound 7-1

[0253] 1-Chloro (28g, 107mmol), benzene-D6 and 2.1L dichlorobenzene were added to a flask, and 9mL trifluoromethanesulfonic acid was added at 50°C. After 12 hours, the mixture was cooled to room temperature, 30mL heavy water was added and stirred for 10 minutes. The mixture was neutralized with K3PO4 aqueous solution and the organic layer was extracted with dichloromethane. After removing the remaining moisture using magnesium sulfate, the filtrate was distilled under reduced pressure and separated by column chromatography to obtain compound 7-1 (24g, yield: 85%).

[0254] 2) Synthesis of Compound 7-2

[0255] Compound 7-1 (22.5g, 86mmol), bis(pinacol)diboron (32.6g, 128mmol), tris(dibenzylideneacetone)dipalladium (3.9g, 4.3mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (s-phos) (3.5g, 8.6mmol), potassium acetate (25.2g, 257mmol) and 430mL of 1,4-dioxane were added to the reaction vessel and stirred at 150°C for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. After the organic layer was dried over magnesium sulfate, the solvent was removed by a rotary evaporator. The residue was purified by column chromatography to obtain compound 7-2 (23.5g, yield: 78%).

[0256] 3 ) Compound H2-36 Synthesis

[0257] Compound 7-2 (10 g, 28 mmol), 2-chloro-4-(dibenzo[b, d]furan-1 base)-6-phenyl-1,3,5-triazine (12 g, 34 mmol), tetrakis(triphenylphosphine)palladium (1.6 g, 1.4 mmol), calcium carbonate (7.8 g, 56 mmol), 141 mL toluene, 20 mL ethanol, 30 mL distilled water were added to a reaction vessel and stirred at 120 ° C for 8 hours. After the reaction was completed, the mixture was added dropwise to methanol, and the resulting solid was filtered. Thereafter, the product was purified by column chromatography to obtain compound H2-36 (12 g, yield: 70%).

[0258] Example 8: Preparation of Compound H1-35

[0259]

[0260] Compound H1-160 was synthesized by selecting one of the deuteration methods disclosed in Korean Patent Publication Nos. 10-2283849, 10-1427457, etc. to obtain Compound H1-35 (1.9 g, yield: 18%).

[0261] Example 9: Preparation of Compound H3-88

[0262]

[0263] Compound 9-1 (5.7 g, 18.95 mmol), compound 9-2 (6 g, 14.58 mmol), Pd2(dba)3 (0.66 g, 0.729 mmol), NaOt-Bu (2.1 g, 21.87 mmol), P(t-bu)3 (50%) (0.7 mL, 1.458 mmol) and 75 mL of toluene were added to a reaction vessel and stirred under reflux for 1 hour. After the reaction was completed, the mixture was cooled to room temperature, filtered through diatomaceous earth, and the filtrate was then distilled under reduced pressure and separated by column chromatography to obtain compound H3-88 (4 g, yield: 40%).

[0264] MW Melting point H3-88 677.7 256.5℃

[0265] Example 10: Preparation of Compound H3-744

[0266]

[0267] Compound H3-88 was synthesized by selecting one of the deuteration methods disclosed in Korean Patent Publication Nos. 10-2283849, 10-1427457, etc. to obtain compound H3-744 (4.0 g, yield: 35%, MS: [M+H] + =694.2).

[0268] Example 11: Preparation of Compound H3-66

[0269]

[0270] Compound 9-1 (5.9 g, 19.8 mmol), compound 11-1 (7 g, 21.7 mmol), Pd2(dba)3 (906 mg, 0.99 mmol), S-Phos (650 mg, 1.58 mmol) and NaOtBu (2.85 g, 29.7 mmol) were dissolved in 100 mL of xylene and stirred at 160° C. under reflux for 30 minutes. After the reaction was completed, the mixture was cooled to room temperature, filtered through celite to obtain a solid, and purified by column chromatography to obtain compound H3-66 (2.4 g, yield: 20.6%).

[0271] MW Melting point H3-66 587.72 253.3℃

[0272] Example 12: Preparation of Compound H3-746

[0273]

[0274] Compound 9-1 (6.3 g, 21 mmol), compound 12-1 (8 g, 23.1 mmol), Pd2(dba)3 (956 mg, 1.05 mmol), S-Phos (689 mg, 1.68 mmol) and NaOtBu (3.03 g, 31.5 mmol) were dissolved in 105 mL of xylene and stirred at 160° C. under reflux for 30 minutes. After the reaction was completed, the mixture was cooled to room temperature, filtered through celite to obtain a solid, and purified by column chromatography to obtain compound H3-746 (3.5 g, yield: 27%).

[0275] MW Melting point H3-746 611.74 149℃

[0276] Example 13: Preparation of Compound H3-42

[0277]

[0278] Compound 9-1 (5.08 g, 16.77 mmol), compound 13-1 (7.0 g, 17.66 mmol), Pd2(dba)3 (0.77 g, 0.84 mmol), S-phos (0.7 g, 1.68 mmol) and NaOtBu (2.42 g, 25.15 mmol) were dissolved in 84 mL of o-xylene and stirred at 160 ° C for 4 hours under reflux. After the reaction was completed, the mixture was cooled to room temperature, the layers were separated (EA / H2O), filtered through diatomaceous earth, and then filtered through silica to obtain a solid. Then, the solid was filtered to obtain compound H3-42 (4.7 g, yield: 40%).

[0279] MW Melting point H3-42 663.8 257℃

[0280] Example 14: Preparation of Compound H3-700

[0281]

[0282] Compound 14-1 (7.4 g, 14.48 mmol), compound 14-2 (1.68 mL, 12.07 mmol), tris (dibenzylideneacetone) dipalladium (0) (0.55 g, 0.603 mmol), NaOtBu (1.74 g, 18.10 mmol), s-phos (0.5 g, 1.207 mmol) were dissolved in 60 mL of o-xylene and stirred at 160° C. under reflux for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered through celite, and the filtrate was distilled under reduced pressure and separated by column chromatography to obtain compound H3-700 (4.5 g, yield: 58%).

[0283] MW Melting point H3-700 637.7 197℃

[0284] Example 15: Preparation of Compound H3-724

[0285]

[0286] Compound 15-1 (5 g, 13.91 mmol), compound 15-2 (6.65 mL, 16.69 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.63 g, 0.695 mmol), NaOt-Bu (2 g, 20.86 mmol) and s-phos (0.57 g, 1.391 mmol) were dissolved in 70 mL of o-xylene and stirred at 160° C. under reflux for 24 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered through celite, and the filtrate was distilled under reduced pressure and separated by column chromatography to obtain compound H3-724 (4 g, yield: 42%).

[0287] MW Melting point H3-724 676.8 218.3℃

[0288] Device Examples 1 and 2: Production of OLEDs Comprising Various Host Materials According to the Disclosure

[0289] 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 6 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 in an amount of 3wt% based on the total amount of compound HI-1 and compound HT-1 to form a hole injection layer having a thickness of 10nm on the ITO substrate. Next, compound HT-1 is deposited on the hole injection layer to form a first hole transport layer having a thickness of 80nm. Compound HT-2 was then introduced into another chamber of a vacuum vapor deposition apparatus, and the compound was evaporated by applying an electric current to the chamber, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light-emitting layer was formed thereon as follows: each of the first host compound and the second host compound disclosed in Table 1 below was introduced as a host into two chambers of a vacuum vapor deposition apparatus, and compound D-150 was introduced as a dopant into another chamber. The two host materials were evaporated at different rates of 1:1, and the dopant materials were evaporated at different rates simultaneously, 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 having a thickness of 40 nm on the second hole transport layer. Compound ET-1 and compound EI-1 were evaporated at a weight ratio of 50:50 to form an electron transport layer having a thickness of 35 nm on the light-emitting layer. After compound EI-1 was deposited as an electron injection layer with a thickness of 2 nm on the electron transport layer, an Al cathode with a thickness of 80 nm was deposited on the electron injection layer by another vacuum vapor deposition device. Thus, an OLED was produced. All materials used to produce OLED were prepared at 10 -6 Purify by vacuum sublimation under vacuum.

[0290] Comparative Example 1: Production of an OLED containing a comparative compound as a host

[0291] An OLED was produced in the same manner as in Device Example 1, except that the second host compound in the following Table 1 was used as a host for the light-emitting layer.

[0292] The emission colors of the OLEDs produced in Device Examples 1 and 2 and Comparative Example 1 at a luminance of 15,000 nits and the time taken for the luminance to decrease from 100% to 90% (lifetime; T90) are shown in Table 1 below.

[0293]

Table 1

[0294]

[0295] As can be confirmed from the above Table 1, the lifespan of the organic electroluminescent device including a plurality of host materials including a specific combination of the compounds according to the present disclosure is significantly improved compared to the conventional organic electroluminescent device including a host material not containing deuterium.

[0296] Device Example 3: Production of OLEDs Comprising Various Host Materials According to the Disclosure

[0297] An OLED was produced in the same manner as in Device Example 2, except that after compound HT-3 in Table 7 below was formed into a second hole transport layer with a thickness of 45 nm, compound HT-4 in Table 7 below was deposited thereon as a third hole transport layer with a thickness of 15 nm, the thickness of the electron transport layer was reduced to 30 nm, and compound BF-1 in Table 7 was deposited to a thickness of 5 nm between the light-emitting layer and the electron transport layer to form an electron buffer layer, and compound ET-2 was used in the electron transport layer.

[0298] Comparative Example 2: Production of an OLED containing a comparative compound as a host

[0299] An OLED was produced in the same manner as in Device Example 3, except that the first host and the second host in the following Table 2 were used as the host of the light-emitting layer.

[0300] The emission colors of the OLEDs produced in Device Example 3 and Comparative Example 2 at a luminance of 10,000 nits and the time taken for the luminance to decrease from 100% to 95% (lifetime: T95) are shown in Table 2 below.

[0301]

Table 2

[0302]

[0303] As can be confirmed from the above Table 2, the organic electroluminescent devices including various host materials according to the present disclosure exhibit longer lifetime characteristics compared to conventional organic electroluminescent devices including a host material not containing deuterium.

[0304] Device Examples 4-6: Production of OLEDs Comprising Various Host Materials According to the Disclosure

[0305] An OLED was produced in the same manner as in Device Example 1, except that Compound HT-5 in the following Table 7 was used as a second hole transport layer and Compound D-39 was used as a dopant.

[0306] Comparative Examples 3 to 5: Production of OLEDs containing comparative compounds as hosts

[0307] An OLED was produced in the same manner as in Device Example 4, except that the first host and the second host in the following Table 3 were used as the host of the light-emitting layer.

[0308] The emission colors of the OLEDs produced in Device Examples 4 to 6 and Comparative Examples 3 to 5 at a luminance of 10,000 nits and the time taken for the luminance to decrease from 100% to 95% (lifetime: T95) are shown in Table 3 below.

[0309]

Table 3

[0310]

[0311] As can be confirmed from the above Table 3, the lifespan of the organic electroluminescent device including the various host materials according to the present disclosure exhibits a longer lifespan characteristic compared to the conventional organic electroluminescent device including the host material not containing deuterium.

[0312] Device Examples 7 and 8: Production of OLEDs Comprising Various Host Materials According to the Disclosure

[0313] An OLED was produced in the same manner as in Device Example 1, except that the ratio of the first host to the second host of the light-emitting layer host material was deposited at a ratio of 4:6 and Compound D-39 in the following Table 7 was used as a dopant.

[0314] Comparative Example 6: Production of an OLED containing a comparative compound as a host

[0315] An OLED was produced in the same manner as in Device Example 7, except that the first host and the second host in the following Table 4 were used as the host of the light-emitting layer.

[0316] The emission colors of the OLEDs produced in Device Examples 7 and 8 and Comparative Example 6 at a luminance of 10,000 nits and the time taken for the luminance to decrease from 100% to 95% (lifetime: T95) are shown in Table 4 below.

[0317]

Table 4

[0318]

[0319] As can be confirmed from the above Table 4, the organic electroluminescent devices including various host materials according to the present disclosure exhibited longer lifetime characteristics compared to conventional organic electroluminescent devices including a host material not containing deuterium.

[0320] Device Examples 9-11: Production of OLEDs Comprising Various Host Materials According to the Disclosure

[0321] An OLED was produced in the same manner as in Device Example 7, except that the ratio of the first host, the second host, and the third host of the light-emitting layer host materials were deposited in a ratio of 2:6:2.

[0322] Comparative Example 7: Production of an OLED containing a comparative compound as a host

[0323] An OLED was produced in the same manner as in Device Example 9, except that the first host, the second host, and the third host in the following Table 5 were used as the host of the light-emitting layer.

[0324] The emission colors of the OLEDs produced in Device Examples 9 to 11 and Comparative Example 7 at a luminance of 10,000 nits and the time taken for the luminance to decrease from 100% to 95% (lifetime: T95) are shown in Table 5 below.

[0325]

Table 5

[0326]

[0327]

[0328] As can be confirmed from the above Table 5, the organic electroluminescent device including various host materials according to the present disclosure exhibits a longer lifetime characteristic compared to a conventional organic electroluminescent device including a host material not containing deuterium.

[0329] Device Examples 12 and 13: Production of OLEDs Comprising Various Host Materials According to the Disclosure

[0330] An OLED was produced in the same manner as in Device Example 7, except that Compound D-151 in the following Table 7 was used as a dopant.

[0331] Comparative Examples 8 and 9: Production of OLEDs containing comparative compounds as hosts

[0332] An OLED was produced in the same manner as in Device Example 7, except that the first host and the second host in the following Table 6 were used as the host of the light-emitting layer.

[0333] The emission colors of the OLEDs produced in Device Examples 12 and 13 and Comparative Examples 8 and 9 at a luminance of 10,000 nits and the time taken for the luminance to decrease from 100% to 95% (lifetime: T95) are shown in Table 6 below.

[0334]

Table 6

[0335]

[0336] As can be confirmed from the above Table 6, the organic electroluminescent devices including various host materials according to the present disclosure exhibited longer lifetime characteristics compared to conventional organic electroluminescent devices including a host material not containing deuterium.

[0337] The compounds used in the device examples and comparative examples are shown in Table 7 below.

[0338]

Table 7

[0339]

[0340]

[0341]

Claims

1. An organic electroluminescent compound represented by the following formula 2-1-1: In formula 2-1-1, X represents O or S; X'1 to X'3 each independently represent CR' or N, provided that at least two of X'1 to X'3 represent N; R' represents hydrogen or deuterium; R8 and R9 each independently represent hydrogen or deuterium; R 10 represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group, which may be further substituted by deuterium; R 11 represents phenyl substituted naphthyl substituted phenyl, which may be further substituted with deuterium; e represents an integer of 1 to 4, and f represents an integer of 1 to 3, wherein if e and f represent an integer of 2 or more, each R8 and each R9 may be the same as or different from each other.

2. The organic electroluminescent compound according to claim 1, wherein The organic electroluminescent compound represented by formula 2-1-1 is selected from the following compounds:

3. An organic electroluminescent device comprising a plurality of host materials according to claim 1.

Images