Organic electro-luminescent compound, and plural host materials and organic electro-luminescent device including the same

Abstract

To provide an organic electro-luminescent compound, and plural host materials and an organic electro-luminescent device including the organic electro-luminescent compound.SOLUTION: The present disclosure relates to an organic electro-luminescent compound, and a plurality of host materials and an organic electro-luminescent device including the organic electro-luminescent compound. A long-life organic electro-luminescent device can be manufactured by using the host materials of the present disclosure as materials of the electro-luminescent device.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present disclosure relates to organic electroluminescent compounds, a number of host materials and organic electroluminescent devices containing same. [Background technology]

[0002] Electroluminescent devices (EL devices) are self-emitting display devices, and have the advantages of wide viewing angle, excellent contrast, and fast response speed. In 1987, Eastman Kodak first developed an organic EL device using small aromatic diamine molecules and aluminum complexes as materials for forming the light-emitting layer (see Non-Patent Document 1).

[0003] The light-emitting material of an organic electroluminescent device is the most important factor that determines the luminous efficiency of the device, and the light-emitting material must have high quantum efficiency and high electron and hole mobility, and the light-emitting material layer formed must be uniform and stable. Light-emitting materials can be divided into host materials and dopant materials in terms of functionality, and may be used by mixing a host and a dopant to improve color purity, luminous efficiency, and stability. The desired properties of a host material that functions as a solid-state solvent and energy carrier are that it must have high purity and appropriate molecular weight to enable vacuum deposition. In addition, thermal stability must be ensured based on high glass transition temperature and thermal decomposition temperature, high electrochemical stability is required for long life, amorphous thin films must be easily formed, and it is preferable that the adhesion with other adjacent layer materials is good but no interlayer migration occurs. When using such a dopant / host material system, the selection of the host material is important because it has a large effect on the efficiency and life of the light-emitting device.

[0004] Although various compounds are known as such host materials, new materials are required due to the high driving voltage, low efficiency, and short lifespan of organic electroluminescent devices using known materials. Therefore, there is a need to develop host materials that can realize organic electroluminescent devices with excellent lifespan characteristics even when driven at low voltages and with high luminance.

[0005] Patent Document 1 discloses an organic optoelectronic device that uses, as a host in an emission layer, a compound having a carbazole-carbazole moiety and a compound having a benzonaphtho-based heteroaryl moiety as a basic skeleton. However, it does not disclose multiple host materials that use, as in the present invention, a compound having a carbazole-based heteroaryl moiety as a basic skeleton and a compound in which a five-membered heteroaryl is condensed to a side benzene ring of a phenanthrene skeleton. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Korean Patent Application Publication No. 10-2019-0013353 [Patent Document 2] Korean Patent Application Publication No. 2017-0022865 [Patent Document 3] Korean Patent Application Publication No. 2021-0124018 [Patent Document 4] Korean Patent Application Publication No. 2021-0006283 [Non-patent literature]

[0007] [Non-Patent Document 1] Appl. Phys. Lett. 51, 913, 1987 Summary of the Invention [Problem to be solved by the invention]

[0008] An object of the present disclosure is to provide an organic electroluminescent compound capable of producing an organic electroluminescent device having long life characteristics, and an organic electroluminescent device containing the same.

[0009] Another object of the present disclosure is to provide host materials and organic electroluminescent devices containing the host materials that can produce organic electroluminescent devices with long life characteristics. [Means for solving the problem]

[0010] As a result of intensive research to solve the above technical problems, the present inventors have found that a compound represented by the following formula 1, and a plurality of host materials including a first host material containing a compound represented by the following formula 1 and a second host material containing a compound represented by the following formula 2, can achieve the above object, thereby completing the present invention. [ka]

[0011] In formula 1, X1 and Y1 each independently represent -N=, -NR5-, -O-, or -S-, provided that one of X1 and Y1 is -N=, and the other of X1 and Y1 is -NR5-, -O-, or -S-; R1 represents a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 membered) heteroaryl, or the following formula 1-a; and R2 to R5 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or the following formula 1-a, or may be linked to adjacent substituents to form a ring, and at least one of R1 to R5 represents the following formula 1-a: [ka] This is subject to the condition that:

[0012] In formula 1-a, L1 represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; Ar1 represents a substituted or unsubstituted (C6 to C30) aryl or a substituted or unsubstituted (3 to 30 membered) heteroaryl; Ar2 represents a substituted or unsubstituted (3 to 30 membered) heteroaryl; R6 is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6- represents a substituted or unsubstituted (C30)arylsilyl, a substituted or unsubstituted fused ring of a (C3-C30)aliphatic ring and a (C6-C30)aromatic ring, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, a substituted or unsubstituted mono- or di-(3-30 membered)heteroarylamino, or a substituted or unsubstituted (C6-C30)aryl(3-30 membered)heteroarylamino, or may be linked to adjacent substituents to form a ring; a and b each independently represent an integer of 1 or 2, and c and d each independently represent an integer of 1 to 4; When a to d are integers of 2 or more, each of R2 to R4 and each of R6 may be the same or different.

[0013] [ka] In formula 2, X2 is -O- or -S-; Ring A is benzene or naphthalene; R 21 and R 22each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, or substituted or unsubstituted tri(C6-C30) arylsilyl, or may be linked to adjacent substituents to form a ring; L2 represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; HAr represents a substituted or unsubstituted (3-30 membered) heteroaryl containing at least one nitrogen atom; n is an integer from 1 to 5, and m is an integer from 1 to 4; When n and m are integers of 2 or more, R 21 and R 22 Each of may be the same or different.

[0014] Advantageous Effects of the Invention By using the organic electroluminescent compounds according to the present disclosure and a number of host materials containing the same, organic electroluminescent devices with long life characteristics can be fabricated. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0015] The present disclosure is described in detail below, which is for illustrative purposes and should not be construed as a way of limiting the scope of the present disclosure.

[0016] The present disclosure relates to an organic electroluminescent compound represented by Formula 1 and an organic electroluminescent device comprising the organic electroluminescent compound.

[0017] Furthermore, the present disclosure relates to a plurality of host materials including one or more first host materials comprising a compound represented by Formula 1 and one or more second host materials comprising a compound represented by Formula 2, and organic electroluminescent devices comprising these host materials.

[0018] As used herein, the term "organic electroluminescent compound" in the present disclosure refers to a compound that can be used in an organic electroluminescent device and can be included in any layer that constitutes the organic electroluminescent device as needed.

[0019] In this specification, the term "organic electroluminescent material" in the present disclosure refers to a material that can be used in organic electroluminescent device, can contain one or more compounds, and can be included in any layer that constitutes organic electroluminescent device as needed.For example, organic electroluminescent material can be hole injection material, hole transport material, hole auxiliary material, light-emitting auxiliary material, electron blocking material, light-emitting material (including host material and dopant material), electron buffer material, hole blocking material, electron transport material, electron injection material, etc.

[0020] In this specification, the term "multiple host materials" in the present disclosure refers to a host material that includes a combination of two or more compounds that can be included in any light-emitting layer that constitutes an organic electroluminescent device, and may refer to both the material before (e.g., before deposition) and after (e.g., after deposition) that is included in an organic electroluminescent device. For example, the multiple host materials of the present disclosure may be a combination of two or more host materials, and may optionally further include conventional materials that are included in organic electroluminescent materials. The two or more compounds included in the multiple host materials of the present disclosure may be included together in one light-emitting layer or in different light-emitting layers according to the method used in the art. For example, two or more types of compounds may be mixed-deposited, co-deposited, or deposited separately.

[0021] In the present specification, the term "hole transport zone" in the present disclosure means a region where holes move between the first electrode and the light-emitting layer, and may include, for example, one or more of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, and an electron blocking layer. Each of the hole injection layer, the hole transport layer, the hole auxiliary layer, the light-emitting auxiliary layer, and the electron blocking layer may be a single layer, or may be two or more layers, or may be a plurality of layers in which three or more layers are stacked. According to one embodiment of the present disclosure, the hole transport zone may include a first hole transport layer and a second hole transport layer, and may further include a third hole transport layer. The second hole transport layer and the third hole transport layer may be one or more layers of a plurality of hole transport layers, which may include one or more of a hole auxiliary layer, a light-emitting auxiliary layer, and an electron blocking layer. In addition, according to another embodiment of the present application, the hole transport zone may include a first hole transport layer and a second hole transport layer, the first hole transport layer may be disposed between the first electrode and the light emitting layer, the second hole transport layer may be disposed between the first hole transport layer and the light emitting layer, and the second hole transport layer may serve as a hole transport layer, a light emitting auxiliary layer, a hole auxiliary layer, and / or an electron blocking layer. The hole transport zone may include a first hole transport layer, a second hole transport layer, and a third hole transport layer, the first hole transport layer may be disposed between the first electrode and the light emitting layer, the second hole transport layer may be disposed between the first hole transport layer and the light emitting layer, and the third hole transport layer may be disposed between the second hole transport layer and the light emitting layer, and the third hole transport layer may serve as a hole transport layer, a light emitting auxiliary layer, a hole auxiliary layer, and / or an electron blocking layer.

[0022] As used herein, the term "(C1-C30) alkyl(ene)" in the present disclosure refers to a straight or branched alkyl(ene) having 1 to 30 carbon atoms constituting the chain, and the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10. Specific examples of alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and tert-butyl.

[0023] As used herein, the term "(C3-C30)cycloalkyl(ene)" refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 ring skeletal carbon atoms, preferably 3 to 20 carbon atoms, more preferably 3 to 7 carbon atoms. Examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like.

[0024] As used herein, the term "(C3-C30)cycloalkenyl" refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 ring carbon atoms, preferably 3 to 20 carbon atoms, more preferably 3 to 7 carbon atoms, and containing a double bond in the ring skeleton. Examples of cycloalkenyl include cyclopropenyl, cyclobutenyl, and cyclopentenyl.

[0025] As used herein, the term "(3- to 7-membered)heterocycloalkyl" in the present disclosure refers to a cycloalkyl having 3 to 7, preferably 5 to 7, ring skeletal atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably from the group consisting of O, S, and N, such as tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, etc.

[0026] As used herein, "(C6-C30)aryl(ene)" in the present disclosure refers to a radical based on a single ring or fused rings derived from an aromatic hydrocarbon having 6 to 30 ring skeletal carbon atoms, which may be partially saturated and also includes those having a spiro structure. The number of ring skeletal carbon atoms is preferably 6 to 20, more preferably 6 to 15. Specific examples of aryl include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthrenyl, benzophenanthrenyl, phenylphenanthrenyl, anthracenyl, benzanthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, benzochrysenyl, naphthacenyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, mesityl, cumenyl, spiro[fluorene-fluorenyl]yl (spirobifluorenyl), spiro[fluorene-benzofluorenyl]yl, azulenyl, and the like.More specifically, aryl includes o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, pt-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-t-butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-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, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl , 1-chrysenyl, 2-chrysenyl, 3-chrysenyl, 4-chrysenyl, 5-chrysenyl, 6-chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, and the like.

[0027] In the present disclosure, the term "(3-30 membered)heteroaryl(ene)" refers to an aryl group having 3-30 ring skeletal atoms, preferably 5-25 ring skeletal atoms, and containing one or more heteroatoms selected from the group consisting of B, N, O, S, Si, P, Se, and Ge. The number of heteroatoms is preferably 1-4, and the ring may be a monocyclic ring or a fused ring system fused with one or more benzene rings, and may be partially saturated. Furthermore, the heteroaryl in the present specification also includes a form in which at least one heteroaryl group or aryl group is bonded to a heteroaryl group by a single bond. Specific examples of heteroaryl include monocyclic heteroaryls such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl; and benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzyl, and benzophenyl. and fused ring type heteroaryls such as benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, indolizidinyl, acridinyl, silafluorenyl, and germafluorenyl. More specifically, heteroaryl is 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolizidinyl, 2-indolizidinyl, 3-indolizidinyl, 5-indolizidinyl, 6-indolizidinyl, 7-indolizidinyl, 8-indolizidinyl,2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 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 azacarbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazol-1-yl, azacarbazol-2-yl, azacarbazolyl-3-yl, azacarbazolyl-4-yl, azacarbazolyl-5-yl, azacarbazolyl-6-yl, azacarbazolyl-7-yl, azacarbazolyl-8-yl, azacarbazolyl-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl , 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl,2-t-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-t-butyl-1-indolyl, 4-t-butyl-1-indolyl, 2-t-butyl-3-indolyl, 4-t-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-germafluorenyl, and 4-germafluorenyl. Furthermore, "heteroaryl(ene)" can be classified into heteroaryl(ene) having electronic properties and heteroaryl(ene) having hole properties. Heteroaryl(ene) having electronic properties is a substituent having relatively abundant electrons in the mother nucleus, and may be, for example, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinolyl, etc. Heteroaryl(ene) having hole properties is a substituent having relatively insufficient electrons in the mother nucleus, and may be, for example, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.

[0028] In the present specification, the term "a fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring" refers to a ring functional group in which at least one aliphatic ring having 3 to 30, preferably 3 to 25, more preferably 3 to 18 ring skeletal carbon atoms is fused with at least one aromatic ring having 6 to 30, preferably 6 to 25, more preferably 6 to 18 ring skeletal carbon atoms. For example, a fused ring of at least one benzene and at least one cyclohexane, or a fused ring of at least one naphthalene and at least one cyclopentane can be mentioned.

[0029] A carbon atom in the condensed ring of the (C3-C30) aliphatic ring and the (C6-C30) aromatic ring may be substituted with at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S. As used herein, "halogen" in the present disclosure includes F, Cl, Br, and I atoms.

[0030] Furthermore, "ortho (o-)", "meta (m-)", and "para (p-)" refer to the substitution positions of all substituents, with the ortho position referring to the position of the substituent immediately adjacent thereto, such as the 1st or 2nd position in the case of benzene, the meta position referring to the position next to the adjacent substitution position, such as the 1st or 3rd position in the case of benzene, and the para position referring to the position next to the meta position, such as the 1st or 4th position in the case of benzene.

[0031] In the present specification, the term "ring formed by linking adjacent substituents" in the present disclosure means a substituted or unsubstituted (3-30 membered) monocyclic or polycyclic aliphatic ring, aromatic ring, or combination thereof formed by linking or condensing two or more adjacent substituents, and may be a substituted or unsubstituted (3-26 membered) monocyclic or polycyclic aliphatic ring, aromatic ring, or combination thereof. In addition, the formed ring may contain at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S. According to one embodiment of the present disclosure, the number of ring skeletal atoms is (5-20 members), and according to another embodiment of the present disclosure, the number of ring skeletal atoms is (5-15 members).

[0032] In addition, in the description of "substituted or unsubstituted" in this specification, "substituted" means that a hydrogen atom in a specific functional group is replaced with another atom or another functional group (i.e., a substituent). Unless otherwise specified, the substituent may replace a hydrogen atom at a position that can be substituted, and when two or more hydrogen atoms in a specific functional group are replaced with each substituent, each substituent may be the same as or different from each other. The maximum number of substituents that can be substituted with a specific functional group can be the total number of substituted valence atoms of each atom that constitutes the functional group. In the present disclosure, R1 to R6 and R 21 , R 22In Ar1, Ar2, and HAr, the substituted alkyl, substituted aryl(ene), substituted heteroaryl, substituted cycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, a condensed ring of a substituted aliphatic ring and an aromatic ring, substituted mono- or di-alkylamino, substituted mono- or di-arylamino, substituted alkylarylamino, substituted mono- or di-heteroarylamino, and substituted arylheteroarylamino are each independently deuterium, halo, aryl, cyano, carboxyl, nitro, hydroxy, (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, (3-7 membered) heterocycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio, unsubstituted or (C6-C30) aryl-substituted (5-30 membered) heteroaryl, unsubstituted or (5-30 membered ... (C6-C30)aryl substituted with heteroaryl, tri(C1-C30)alkylsilyl, tri(C6-C30)arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C1-C30)alkyldi(C6-C30)arylsilyl, condensed ring of (C3-C30)aliphatic ring and (C6-C30)aromatic ring, amino, mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, (C1-C30)alkyl(C6-C30)arylamino, mono- or di-(C6-C30)arylamino, or di-(3-30 membered)heteroarylamino, (C1-C30)alkyl(3-30 membered)heteroarylamino, (C6-C30)aryl(3-30 membered)heteroarylamino, (C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30)arylcarbonyl, (C6-C30)arylphosphinyl, di(C6-C30)arylboronyl, di(C1-C30)alkylboronyl, (C1-C30)alkyl(C6-C30)arylboronyl, (C6-C30)ar(C1-C30)alkyl,and (C1 to C30) alkyl (C6 to C30) aryl. For example, the substituent may be deuterium, substituted or unsubstituted methyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracenyl, substituted or unsubstituted chrysenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted norbornenyl, substituted or unsubstituted adamantenyl, substituted or unsubstituted carbazolyl, unsubstituted or phenyl-substituted carbazolyl, substituted or unsubstituted dibenzofuranyl, unsubstituted or deuterium-substituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzonaphthofuranyl, or substituted or unsubstituted phenanthrooxazolyl.

[0033] In the present disclosure, when a substituent is not shown in a formula or a compound structure, it may mean that all positions that may exist as a substituent may be hydrogen or deuterium. That is, in the case of deuterium, which is an isotope of hydrogen, some of the hydrogen atoms may be deuterium, which is an isotope, in which case the content of deuterium may be 0% to 100%. When a substituent is not shown in a formula or a compound structure, if deuterium is not explicitly excluded, a mixture of hydrogen and deuterium may be used in the compound, for example, when the content of deuterium is 0%, the content of hydrogen is 100%, and all the substituents are hydrogen. Deuterium is one of the isotopes of hydrogen, and is an element having a deuteron, which consists of one proton and one neutron as its atomic nucleus. It can be represented as hydrogen-2, and its element symbol can be written as D or 2H. Isotopes refer to atoms that have the same atomic number (Z) but different mass numbers (A). They can also be interpreted as elements that have the same number of protons but different numbers of neutrons.

[0034] As used herein, "combinations thereof" in the present disclosure refer to one or more members of the corresponding list being combined to form a known or chemically stable configuration that one skilled in the art can conceive of from the corresponding list. For example, alkyl and deuterium can be combined to form a partially or fully deuterated alkyl group; halogen and alkyl can be combined to form a halogenated alkyl substituent; halogen, alkyl and aryl can be combined to form a halogenated aryl alkyl. For example, a preferred combination of substituents may contain up to 50 atoms excluding hydrogen and deuterium, or may contain up to 40 atoms excluding hydrogen and deuterium, or may contain up to 30 atoms excluding hydrogen and deuterium, or in many cases, a preferred combination of substituents may contain up to 20 atoms excluding hydrogen and deuterium.

[0035] In the formulae of the present disclosure, when multiple substituents are represented by the same symbol, each of those substituents represented by the same symbol can be the same or different from one another.

[0036] The host material according to one embodiment will be described below.

[0037] The multiple host materials according to one embodiment include a first host material comprising a compound represented by Formula 1 and a second host material comprising a compound represented by Formula 2, which may be included in at least one light-emitting layer of an organic electroluminescent device according to one embodiment.

[0038] The first host material, which is a host material according to one embodiment, may include a compound represented by Formula 1 below: [ka]

[0039] In formula 1, X1 and Y1 each independently represent -N=, -NR5-, -O-, or -S-, provided that one of X1 and Y1 is -N=, and the other of X1 and Y1 is -NR5-, -O-, or -S-; R1 represents a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 membered) heteroaryl, or the following formula 1-a; and R2 to R5 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or the following formula 1-a, or may be linked to adjacent substituents to form a ring, and at least one of R1 to R5 represents the following formula 1-a: [ka] This is subject to the condition that:

[0040] In formula 1-a, L1 represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; Ar1 represents a substituted or unsubstituted (C6 to C30) aryl or a substituted or unsubstituted (3 to 30 membered) heteroaryl; Ar2 represents a substituted or unsubstituted (3 to 30 membered) heteroaryl; R6 is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6- represents a substituted or unsubstituted (C30)arylsilyl, a substituted or unsubstituted fused ring of a (C3-C30)aliphatic ring and a (C6-C30)aromatic ring, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, a substituted or unsubstituted mono- or di-(3-30 membered)heteroarylamino, or a substituted or unsubstituted (C6-C30)aryl(3-30 membered)heteroarylamino, or may be linked to adjacent substituents to form a ring; a and b each independently represent an integer of 1 or 2, and c and d each independently represent an integer of 1 to 4; When a to d are integers of 2 or more, each of R2 to R4 and each of R6 may be the same or different.

[0041] In one embodiment, X1 and Y1 may each independently represent N, O, or S, provided that either one of X1 and Y1 may be -N= and the other may be -O- or -S-.

[0042] In one embodiment, R1 may represent substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-membered to 30-membered) heteroaryl, or formula 1-a, preferably, R1 may represent substituted or unsubstituted (C6-C25) aryl, substituted or unsubstituted (3-membered to 25-membered) heteroaryl, or formula 1-a. For example, R1 may be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, or formula 1-a.

[0043] In one embodiment, R2 to R5 can each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, or formula 1-a, and preferably R2 to R5 can each independently represent hydrogen, deuterium, halogen, cyano, or formula 1-a. For example, R2 to R5 can each independently represent hydrogen or formula 1-a.

[0044] In one embodiment, L1 may represent a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene, and preferably L1 may represent a single bond, an unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (3-25 membered) heteroarylene. For example, L1 may be a single bond or a substituted or unsubstituted phenylene.

[0045] In one embodiment, Ar1 may represent substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (3-30 membered) heteroaryl, preferably, Ar1 may represent substituted or unsubstituted (C6-C25) aryl or substituted or unsubstituted (5-25 membered) heteroaryl. For example, Ar1 may be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted naphthalenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazolyl. Here, the substituent of the substituted phenyl may be deuterium or methyl, and the substituent of the substituted carbazole may be phenyl.

[0046] In one embodiment, Ar2 may be a substituted or unsubstituted (3-30 membered) heteroaryl, preferably Ar2 may be a substituted or unsubstituted (5-25 membered) heteroaryl. For example, Ar2 may be a substituted or unsubstituted dibenzofuranyl or a substituted or unsubstituted dibenzothiophenyl. Here, the substituent of the substituted dibenzofuran may be deuterium, methyl, or phenyl.

[0047] In one embodiment, R6 can represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C6-C30) aryl, preferably R6 can represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C25) alkyl, or substituted or unsubstituted (C6-C25) aryl. For example, R6 can be hydrogen, deuterium, methyl, or phenyl.

[0048] In one embodiment, a and b each independently represent an integer of 1 or 2, c and d each independently represent an integer of 1 to 4, and when a to d each represent an integer of 2 or more, each of R2 to R4 and each of R6 may be the same or different.

[0049] The compound represented by formula 1 can be represented by any one of the following formulas 1-1 to 1-4. [ka]

[0050] In formulas 1-1 to 1-4, c' is an integer from 1 to 3; When c' is an integer of 2 or greater, each R4 may be the same or different; X1, Y1, R1 to R4, R6, L1, Ar1, Ar2, and a to d are the same as defined in formula 1.

[0051] In one embodiment, c' represents an integer from 1 to 3, and when c' is an integer of 2 or greater, each R4 may be the same or different.

[0052] According to one embodiment, Ar2 in formula 1-a may be represented by any one of the following formulas R-1 to R-4. [ka] (In formulas R-1 to R-4, X is O, S, Se, or N; R 11 ~R 18 may each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl, or a substituted or unsubstituted (C6-C30) aryl.

[0053] In one embodiment, X can be O, Se, or S.

[0054] In one embodiment, R 11 ~R 18 may each independently represent hydrogen, deuterium, or a substituted or unsubstituted (C1-C10) alkyl, preferably R 11 ~R 18 may each independently represent hydrogen or deuterium. For example, R11 ~R 18 may all be hydrogen.

[0055] According to one embodiment, the first host material may be exemplified by, but is not limited to, the following compounds: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0056] The compound represented by formula 1 according to the present disclosure can be prepared by a synthesis method known to those skilled in the art, and in particular can use the synthesis methods disclosed in a number of patent documents.For example, it can be synthesized with reference to, but not limited to, the method disclosed in (Patent Document 2) (March 2, 2017).

[0057] As another host material according to an embodiment, the second host material may include a compound represented by Formula 2 below. [ka]

[0058] In formula 2, X2 is -O- or -S-; Ring A is a benzene ring or a naphthalene ring; R 21 and R 22 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, or substituted or unsubstituted tri(C6-C30) arylsilyl, or may be linked to adjacent substituents to form a ring; L2 represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; HAr represents a substituted or unsubstituted (3-30 membered) heteroaryl containing at least one nitrogen atom; n is an integer from 1 to 5, and m is an integer from 1 to 4; When n and m are integers of 2 or more, R 21 and R 22 Each of may be the same or different.

[0059] In one embodiment, R 21 and R 22each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, or substituted or unsubstituted tri(C6-C30) arylsilyl, or may be linked to adjacent substituents to form a ring; preferably, R 21 and R 22 may each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C25) alkyl, substituted or unsubstituted (C6-C25) aryl, substituted or unsubstituted (3-membered to 25-membered) heteroaryl, substituted or unsubstituted (C3-C25) cycloalkyl, substituted or unsubstituted (C1-C25) alkoxy, substituted or unsubstituted tri(C1-C25) alkylsilyl, substituted or unsubstituted di(C1-C25) alkyl(C6-C25) arylsilyl, substituted or unsubstituted (C1-C25) alkyldi(C6-C25) arylsilyl, or substituted or unsubstituted tri(C6-C25) arylsilyl, or may be linked to adjacent substituents to form a ring. For example, R 21 and R 22 may each independently be hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted naphthylphenyl, substituted or unsubstituted phenanthrenyl, or substituted or unsubstituted benzoxazolyl.

[0060] In one embodiment, L2 may represent a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene, and preferably, L2 may represent a single bond, an unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene. For example, L2 may be a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted phenylnaphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted naphthylphenylene.

[0061] In one embodiment, HAr may represent a substituted or unsubstituted (3-membered to 30-membered) heteroaryl containing at least one nitrogen atom, and preferably, HAr may represent a substituted or unsubstituted (5-membered to 25-membered) heteroaryl containing at least two nitrogen atoms. For example, HAr may represent a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted benzoquinoxalinyl, a substituted or unsubstituted benzoquinazolinyl, or a substituted or unsubstituted naphthoquinoxalinyl. The substituent of the substituted pyrimidine may be phenyl or phenyl-substituted pyridinyl. The substituent of the substituted quinoxalinyl may be phenyl, biphenyl, naphthyl, dimethylfluorenyl, diphenylfluorenyl, dibenzothiophenyl, or phenyl-substituted carbazolyl; the substituent of the substituted quinazolinyl may be phenyl, biphenyl, naphthyl, dimethylfluorenyl, or dibenzothiophenyl; the substituent of the substituted benzoquinoxalinyl may be phenyl or naphthyl; the substituent of the substituted benzoquinazolinyl may be phenyl; and the substituent of the substituted naphthoquinazolinyl may be phenyl.

[0062] In one embodiment, the compound represented by formula 2 can be represented by any one of formulas 2-1 to 2-16. [ka] [ka] [ka]

[0063] In formulas 2-1 to 2-16, L3 and L4 each independently represent a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; Ar3 and Ar4 each independently represent a substituted or unsubstituted (C6 to C30) aryl or a substituted or unsubstituted (3 to 30 membered) heteroaryl; X2, R 21 , R 22 , L2, n, and m are the same as defined in Equation 2; n' is an integer from 1 to 3; When n' is 2 or more, R 21 may be the same or different from one another.

[0064] In one embodiment, L3 and L4 may each independently represent a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene, and preferably, L3 and L4 may each independently represent a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (3-25 membered) heteroarylene. For example, L3 and L4 may each independently represent a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted phenanthrylene.

[0065] In one embodiment, Ar3 and Ar4 may each independently represent a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (5-30 membered) heteroaryl, and preferably, Ar3 and Ar4 may each independently represent a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (5-25 membered) heteroaryl. For example, Ar3 and Ar4 may each independently represent a substituted or unsubstituted phenyl, an unsubstituted or methyl-substituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted o-terphenyl, a substituted or unsubstituted m-terphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted naphthylphenyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted chrysenyl, a substituted or unsubstituted triphenylenyl, a substituted or unsubstituted fluoranthenyl, a substituted or unsubstituted dimethylfluorenyl, a substituted or unsubstituted diphenylfluorenyl, a substituted or unsubstituted spinyl, a substituted or unsubstituted phenyl ... The substituted phenyl, substituted biphenyl, dibenzofuranyl, or substituted benzonaphthofuranyl may be at least one selected from deuterium, norbornenyl, and adamantenyl, and the substituted naphthyl may be at least one selected from deuterium, biphenyl, and naphthyl.

[0066] According to one embodiment, the second host material may be exemplified by, but is not limited to, the following compounds: [ka] [ka] [ka]

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[0067] The compound represented by formula 2 according to the present disclosure can also be prepared by a synthesis method known to those skilled in the art, and in particular, the synthesis methods disclosed in many patent documents can be used. For example, the synthesis of (Patent Document 3) (October 14, 2021) and (Patent Document 4) (January 18, 2021) can be performed with reference to the methods disclosed in the present disclosure, but is not limited thereto.

[0068] Hereinafter, an organic electroluminescent compound, a number of host materials, and an organic electroluminescent device to which the organic electroluminescent compound is applied will be described.

[0069] FIG. 1 shows a compound according to one embodiment of the present invention.

[0070] An organic electroluminescent device according to one embodiment includes a first electrode; a second electrode; and one or more organic layers sandwiched between the first electrode and the second electrode, and according to one example, a first host material comprising a compound represented by Formula 1 and a second host material comprising a compound represented by Formula 2 may be included in the same organic layer or may be included in different organic layers.

[0071] The organic layer may include at least one light-emitting layer, and the at least one light-emitting layer may include a plurality of host materials including one or more first host materials including a compound represented by Formula 1 and one or more second host materials including a compound represented by Formula 2. According to one embodiment, the light-emitting layer may include at least one compound selected from compounds H1-1 to H1-171, which are the first host materials represented by Formula 1, and at least one compound selected from compounds H2-1 to H2-795, which are the second host materials represented by Formula 2.

[0072] An organic electroluminescent device according to an embodiment may include a hole transport zone between the first electrode and the light emitting layer. According to an embodiment, the hole transport zone may include at least two layers, for example, three layers.

[0073] One of the first electrode and the second electrode may be a positive electrode (anode), and the other may be a negative electrode (cathode). In this case, the first electrode and the second electrode may be formed of a transparent conductive material, or may be formed of a semi-transparent conductive material or a reflective conductive material. In addition to the light-emitting layer, the organic layer may further include one or more layers selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron injection layer, an intermediate layer, a hole blocking layer, an electron blocking layer, and an electron buffer layer.

[0074] The organic layer may further include an amine-based compound and / or an azine-based compound in addition to the light-emitting material of the present disclosure. Specifically, the hole injection layer, the hole transport layer, the hole auxiliary layer, the light-emitting layer, the light-emitting auxiliary layer, or the electron blocking layer may include an amine-based compound, such as an arylamine-based compound or a styrylarylamine-based compound, as a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting material, a light-emitting auxiliary material, and an electron blocking material. Furthermore, the electron transport layer, the electron injection layer, the electron buffer layer, and the hole blocking layer may include an azine-based compound as an electron transport material, an electron injection material, an electron buffer material, and a hole blocking material. In addition, the organic layer may further include one or more metals selected from the group consisting of organometallic compounds of Group 1, Group 2, fourth-period transition metals, fifth-period transition metals, lanthanide metals, and d-transition metals, or one or more complex compounds containing these metals.

[0075] The host materials according to one embodiment can be used as the emitting material for white organic light-emitting devices.For white organic electroluminescent devices, various structures have been proposed, such as side-by-side, stacking, or color conversion material (CCM), depending on the arrangement of R (red), G (green), YG (yellow green) and B (blue) emitting units.In addition, the host materials according to one embodiment can also be used in organic electroluminescent devices that contain quantum dots (QDs).

[0076] 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. In the hole injection layer, multiple layers may be used for the purpose of lowering the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, and two types of compounds may be used simultaneously in each layer. The hole injection layer may be doped as a p-type dopant. The electron blocking layer may be disposed between the hole transport layer (or the hole injection layer) and the light emitting layer, and may prevent the overflow of electrons from the light emitting layer and confine excitons in the light emitting layer, thereby preventing light emission leakage. As the hole transport layer or the electron blocking layer, multiple layers may be used, and multiple compounds may be used in each layer.

[0077] 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. In the electron buffer layer, multiple layers may be used for the purpose of adjusting the amount of electron injection and improving the interface properties between the light emitting layer and the electron injection layer, and two kinds of compounds may be used simultaneously in each layer. Multiple layers may be used for the hole blocking layer or the electron transport layer, and multiple compounds may be used in each layer. The electron injection layer may be doped with an n-dopant.

[0078] The light-emitting auxiliary layer is disposed between the anode and the light-emitting layer or between the cathode and the light-emitting layer. When the light-emitting auxiliary layer is disposed between the anode and the light-emitting layer, the light-emitting auxiliary layer can be used to promote hole injection and / or transport or to block electron overflow, and when the light-emitting auxiliary layer is disposed between the cathode and the light-emitting layer, the light-emitting auxiliary layer can be used to promote electron injection and / or transport or to block hole overflow. In addition, the hole auxiliary layer can be disposed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can exhibit the effect of promoting or blocking the transport rate (or injection rate) of holes, thereby adjusting the charge balance. When the organic electroluminescent device includes two or more hole transport layers, the additionally included hole transport layer can be used as a hole auxiliary layer or an electron blocking layer. The light-emitting 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.

[0079] In the organic electroluminescent device of the present disclosure, it is preferable that one or more layers selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter referred to as a "surface layer") are disposed on the inner surface of at least one of a pair of electrodes. Specifically, it is preferable that a chalcogenide (including oxide) layer of silicon and aluminum is disposed on the surface of the anode on the light-emitting medium layer side, and a metal halide layer or a metal oxide layer is disposed on the surface of the cathode on the light-emitting medium layer side. Driving stabilization in the organic electroluminescent device can be obtained by the surface layer. A preferable example of the chalcogenide is SiO X (1≦X≦2), AlO X (1≦X≦1.5), SiON, SiAlON, etc.; preferred examples of metal halides include LiF, MgF2, CaF2, rare earth metal fluorides, etc., and preferred examples of metal oxides include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0080] The organic electroluminescent device according to an embodiment of the present disclosure may be an organic electroluminescent device having a tandem structure. In the case of the tandem organic electroluminescent device according to an embodiment, two or more single light-emitting units may be connected by a charge generating layer. The organic electroluminescent device may include two or more light-emitting units, for example, three or more light-emitting units, each of which has a first electrode and a second electrode facing each other on a substrate, and a light-emitting layer stacked between the first electrode and the second electrode and emitting light of a specific wavelength band, each light-emitting unit may include a hole transport zone, a light-emitting layer, and an electron transport zone, the hole transport zone may include a hole injection layer and a hole transport layer, the electron transport zone may include an electron transport layer and an electron injection layer, and according to an embodiment, the light-emitting unit may include three or more light-emitting layers. The multiple light-emitting units may emit the same color or different colors. In addition, one light-emitting unit may include one or more light-emitting layers, and the multiple light-emitting layers may be light-emitting layers of the same color or different colors. One or more charge generation layers may be included between each light-emitting unit. The charge generation layer refers to a layer in which holes and electrons are generated when a voltage is applied. When there are three or more light-emitting units, a charge generation layer may be disposed between the light-emitting units. In this case, the charge generation layers may be the same as or different from each other. Since the charge generation layer is disposed between the light-emitting units, the current efficiency in each light-emitting unit can be improved and the charge can be smoothly distributed. Specifically, the charge generation layer is disposed between two adjacent stacks and can function to drive the tandem organic electroluminescent device using only an anode and cathode pair without a separate internal electrode disposed between the stacks.

[0081] An organic electroluminescent device according to an embodiment may include two or more organic layers, and may further include one or more charge generating layers, which may be disposed between the organic layers, and when two or more organic layers are included, the charge generating layers may be the same or different. Because the charge generating layer is disposed between the organic layers, the organic electroluminescent device can be driven by only a pair of anode and cathode, without disposing another separate internal electrode between the organic layers.

[0082] The charge generation layer can include an n-type charge generation layer and a p-type charge generation layer, and the n-type charge generation layer can be doped with an alkali metal, an alkaline earth metal, or a compound of an alkali metal and an alkaline earth metal. The alkali metals can include those selected from the group consisting of Li, Na, K, Rb, Cs, Fr, Yb, and combinations thereof, and the alkaline earth metals can include those selected from the group consisting of Be, Mg, Ca, Sr, Ba, Ra, and combinations thereof.

[0083] Furthermore, in the organic electroluminescent device of the present disclosure, it is also preferred to arrange 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 on the surface of at least one of the pair of electrodes. In this manner, the electron transport compound is reduced to an anion, so that it is easier to inject and transport electrons from the mixed region to the light-emitting medium. Furthermore, the hole transport compound is oxidized to a cation, so that it is easier to inject and transport holes from the mixed region to the light-emitting medium. Preferred oxidative dopants include various Lewis acids and acceptor compounds, and preferred reductive dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, by using a reductive dopant layer as a charge generation layer, a white light-emitting organic electroluminescent device having two or more light-emitting layers can be manufactured.

[0084] The light-emitting layer of the organic electroluminescent device according to one embodiment can be a single layer on which light is emitted, or can be a multi-layer structure of two or more layers stacked together.The light-emitting layer can further comprise one or more dopants, and the doping concentration of the dopant compound relative to the host compound of the light-emitting layer can be less than 20% by weight, preferably less than 10% by weight.

[0085] As the dopant contained in the organic electroluminescent device of the present disclosure, one or more phosphorescent or fluorescent dopants can be used, and fluorescent dopants are preferred.The phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particularly limited, but can be a complex compound of metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and in some cases can be an ortho-metallized complex compound of metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and in some cases can be more preferably an ortho-metallized iridium complex compound.

[0086] As a dopant contained in the organic electroluminescent device of the present disclosure, a compound represented by the following formula 101 can be used, but the present disclosure is not limited thereto. [ka]

[0087] In formula 101, L is the following structure 1 to 3: [ka] represented by any one selected from: R 100 ~R 103each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium and / or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (3-membered to 30-membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy, or may be linked with adjacent substituents to form a ring, such as unsubstituted or pyridine-substituted quinoline, substituted or unsubstituted benzofuropyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuroquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indenoquinoline; R 104 ~R 107 may each independently represent hydrogen, deuterium, halogen, unsubstituted or deuterium and / or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy, or may be linked with adjacent substituents to form a substituted or unsubstituted ring, such as unsubstituted or benzene-substituted naphthyl, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuropyridine, or substituted or unsubstituted benzothienopyridine; R 201 ~R 220 each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium and / or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C6-C30) aryl, or may be linked to adjacent substituents to form a substituted or unsubstituted ring; s represents an integer of 1 to 3.

[0088] Specifically, specific examples of dopant compounds are as follows, but are not limited to these. [ka] [ka] [ka] [ka] [ka] [ka]

[0089] Each layer of the organic electroluminescent device of the present disclosure can be formed using any of dry film-forming methods such as vacuum deposition, sputtering, plasma, ion plating, etc., and wet film-forming methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating, etc. In the wet film-forming method, a thin film is formed by dissolving or dispersing the material forming each layer in a suitable solvent such as ethanol, chloroform, tetrahydrofuran, or dioxane, and the solvent may be any solvent in which the material forming each layer can be dissolved or dispersed and which has no problem in film-forming properties.

[0090] When forming the first host material and the second host material according to an embodiment, the film can be formed by the above-mentioned method, but preferably, the film can be formed by co-evaporation or mixed deposition. Co-evaporation is a method in which two or more isomeric materials are put into respective crucible sources, and the materials are evaporated and mixed simultaneously by passing electric current through two cells, while mixed deposition is a method in which two or more isomeric materials are mixed and evaporated in one crucible source before deposition, and then the materials are evaporated and mixed by passing electric current through one cell.

[0091] According to one embodiment, when the first host material and the second host material are present in the same layer or different layers of an organic electroluminescent device, the two host materials can be vapor-deposited separately. For example, the second host material can be vapor-deposited after the first host material is vapor-deposited.

[0092] According to one embodiment, the present disclosure can provide a compound obtained by depositing an organic layer in a manufacturing process of an organic electroluminescent device, and then recovering and purifying the material of the organic layer attached to the deposition apparatus. The recovered compound can be subjected to a purification process and / or a recrystallization process, and the purity of the purified and / or recrystallized compound obtained therefrom can be 99.9% or more.

[0093] According to one embodiment, the present disclosure provides a method of recovering a plurality of host materials, the method including vapor-depositing a plurality of host materials comprising at least one first host material comprising a compound represented by Formula 1 and at least one second host material comprising a compound represented by Formula 2, recovering the plurality of host materials attached to the vapor-deposition apparatus, and purifying and / or recrystallizing the recovered plurality of host materials to obtain the plurality of host materials having a purity of 99.9% or greater.

[0094] According to one embodiment, the present disclosure can provide a display device, such as a smartphone, tablet, laptop, PC, TV, or vehicle display device, or a lighting device, such as an outdoor or indoor light, using a plurality of host materials including a compound represented by Formula 1 and a compound represented by Formula 2.

[0095] In the following, for a detailed understanding of the present disclosure, the preparation methods of the compounds according to the present disclosure are illustrated using the synthesis methods of representative compounds or intermediate compounds of the present disclosure as examples. EXAMPLES

[0096] Example 1: Synthesis of Compound H1-3 [ka] Compound CPPO (4 g, 12.1 mmol), compound 1 (4.4 g, 13.3 mol), Pd2(dba)3 (553 mg, 0.6 mmol), 2-dichlorohexylphosphine-2',6'-dimethoxybiphenyl ("S-Phos") (397 mg, 0.968 mmol), and sodium tert-butoxide ("NaOt-Bu") (2.3 g, 24.2 mmol) were dissolved in 60 mL of xylene, and the mixture was stirred at 160° C. for 4 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered through Celite to obtain a solid, which was then separated by column chromatography to obtain compound H1-3 (4.0 g, yield: 52.5%).

[0097] [Table 1]

[0098] Example 2: Synthesis of Compound H1-14 [ka] Compound CPPO (7.0 g, 21.22 mmol), compound 2 (7.8 g, 23.34 mmol), tris(dibenzylideneacetone)dipalladium ("Pd2(dba)3") (0.97 g, 1.061 mmol), NaOt-Bu (5.0 g, 53.05 mmol), and S-Phos (0.87 g, 2.12 mmol) were dissolved in 106 mL of o-xylene, and the mixture was stirred at reflux at 160° C. for 1 hour. After completion of the reaction, the mixture was cooled to room temperature and filtered through Celite to obtain a solid, which was then separated by column chromatography to obtain compound H1-14 (4.3 g, yield: 33%).

[0099] [Table 2]

[0100] Example 3: Synthesis of Compound H1-1 [ka] 5.1g of compound A (15.6mmol), 6g of compound B (15.5mmol), 0.71g of Pd2(dba)3 (0.776mmol), 0.64g of S-phos (1.55mmol), and 3.7g of NaOt-Bu (38.8mmol) were dissolved in 80mL of o-xylene in a reaction vessel, and the mixture was stirred for 2 hours under reflux at 160°C. After completion of the reaction, the mixture was cooled to room temperature, methanol was added thereto, stirred for 30 minutes, filtered, dried, and separated by column chromatography to obtain compound H1-1 (6g, yield: 62%).

[0101] [Table 3]

[0102] Example 4: Synthesis of compound H1-2 [ka] (1) Synthesis of Compound D Compound C (15 g, 61 mmol), (4-chlorophenyl)boronic acid (12 g, 73.2 mmol), potassium carbonate (21 g, 153 mmol), Pd(PPh3)4 (3.6 g, 3.1 mmol), and 200 mL of THF were dissolved in 70 mL of water in a reaction vessel, and the mixture was refluxed at 130° C. for 5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate, and the residual water was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound D (15 g, yield: 88%).

[0103] (2) Synthesis of compound H1-2 Compound D (7 g, 25.1 mmol), N,2-diphenylphenanthro[3,4-d]oxazol-10-amine (11 g, 27 mmol), Pd2(dba)3 (1.2 g, 1.3 mmol), [2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl] ("X-Phos") (1.1 g, 2.5 mmol), and NaOt-Bu (6.0 g, 63 mmol) were dissolved in 150 mL of xylene in a reaction vessel, and the mixture was stirred at reflux at 160° C. for 1 hour. After the reaction was completed, the reaction mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate, magnesium sulfate was used to remove residual water, dried, and separated by column chromatography to obtain compound H1-2 (7 g, yield: 45%).

[0104] [Table 4]

[0105] Example 5: Synthesis of Compound H1-6 [ka] Compound E (5.5 g, 9.69 mmol), bromobenzene (3 g, 19.3 mmol), Pd2(dba)3 (443 mg, 0.48 mmol), X-Phos (318 mg, 0.775 mmol), and NaOt-Bu (1.4 g, 14.5 mmol) were dissolved in 50 mL of xylene in a reaction vessel and refluxed at 160 °C for 2 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate, magnesium sulfate was used to remove residual water, dried, and separated by column chromatography to obtain compound H1-6 (2.8 g, yield: 44%).

[0106] [Table 5]

[0107] Example 6: Synthesis of Compound H1-56 [ka] (1) Synthesis of compound G In a reaction vessel, compound F (30 g, 121.41 mmol), (4-chlorophenyl)boronic acid (20.88 g, 133.55 mmol), Pd(PPh3)4 (4.21 g, 3.64 mmol), and K2CO3 (41.95 g, 303.53 mmol) were dissolved in 607 ml of toluene, 152 ml of ethanol, and 152 ml of water, and refluxed at 130° C. for 24 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered through Celite to obtain a solid, which was then separated by column chromatography to obtain compound G (26.3 g, yield: 77.7%).

[0108] (2) Synthesis of Compound I Compound G (26.3 g, 94.35 mmol), [1,1'-biphenyl]-2-amine (15.97 g, 94.35 mmol), Pd2(dba)3 (4.32 g, 4.72 mmol), S-Phos (3.87 g, 9.44 mmol), and NaOt-Bu (13.60 g, 141.53 mmol) were dissolved in 472 ml of xylene in a reaction vessel and refluxed at 130° C. for 4 hours. After the reaction was completed, the mixture was cooled to room temperature and filtered through Celite to obtain a solid, which was then separated by column chromatography to obtain compound I (30 g, yield: 77.2%).

[0109] (3) Synthesis of compound H1-56 In a reaction vessel, compound H (8 g, 24.26 mmol), compound I (9.98 g, 24.26 mmol), Pd2(dba)3 (1.11 g, 1.21 mmol), S-phos (1 g, 2.43 mmol), and NaOt-Bu (3.50 g, 36.39 mmol) were dissolved in 122 ml of xylene and refluxed at 130° C. for 4 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered through Celite to obtain a solid, which was then separated by column chromatography to obtain compound H1-56 (6 g, yield: 35.09%).

[0110] [Table 6]

[0111] In the following, for a detailed understanding of the present disclosure, the fabrication method and features of the organic electroluminescent device comprising multiple host materials according to the present disclosure are described.

[0112] Device Examples 1-3: Fabrication of OLEDs with co-deposited first and second host compounds according to the present disclosure An OLED according to the present disclosure was fabricated. First, a transparent electrode indium tin oxide (ITO) thin film (10 Ω / sq) on a glass substrate for an OLED (Geomatec Co., Ltd., Japan) was subjected to ultrasonic cleaning in acetone and isopropyl alcohol, successively, and then stored in isopropyl alcohol. The ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus. Compound HI-1 in Table 7 was placed in one cell of the vacuum deposition apparatus, and compound HT-1 was placed in another cell. The two materials were evaporated at different rates, and compound HI-1 was deposited with a doping amount of 3 wt % based on the total amount of compound HI-1 and compound HT-1 to form a first hole injection layer with a thickness of 10 nm. Compound HT-1 was then deposited on the first hole injection layer to form a first hole transport layer with a thickness of 80 nm. Next, the compound HT-2 was introduced into another cell of the vacuum deposition apparatus and evaporated by passing a current through the cell, thereby depositing a second hole transport layer having a thickness of 55 nm on the first hole transport layer. Thereafter, the compound HT-3 was introduced into another cell of the vacuum deposition apparatus and evaporated by passing a current through the cell, thereby depositing a third hole transport layer having a thickness of 5 nm on the second hole transport layer.

[0113] After forming the hole injection layer and the hole transport layer, the light-emitting layer was deposited thereon as follows: the first host compound and the second host compound shown in Table 1 were placed in two cells of a vacuum deposition apparatus as hosts, and the compound D-39 was placed in another cell as a dopant, and then the two host materials were evaporated in a 1:1 ratio, and at the same time, the dopant material was evaporated in a different ratio to dope the dopant at 3 wt % based on the total amount of the host and the dopant, thereby depositing a light-emitting layer having a thickness of 40 nm on the second hole transport layer. Next, the compounds ET-1 and EI-1 were deposited on the light-emitting layer as electron transport materials in a weight ratio of 50:50 to form an electron transport layer with a thickness of 35 nm. After that, the compound EI-1 was deposited on the electron transport layer as an electron injection layer to a thickness of 2 nm, and then another vacuum deposition apparatus was used to deposit an Al cathode on the electron injection layer to a thickness of 80 nm, thereby completing the manufacture of the OLED. For each material, 10 -6 Each compound was purified by vacuum sublimation at 1000 torr.

[0114] Comparative Device Example 1: Fabrication of an OLED Containing a Comparative Compound as a Host An OLED was fabricated in the same manner as in Device Example 1, except that the compound in Table 1 below was used as the first host compound.

[0115] The organic electroluminescent devices of Comparative Device 1 and Examples 1 to 3 prepared as described above were measured for the driving voltage based on the luminance of 1,000 nit, the emission color, and the time required for the light intensity based on the luminance of 10,000 nit to decrease from 100% to 95% (lifetime; T95). The results are shown in Table 1 below.

[0116] [Table 7]

[0117] From Table 1, it can be seen that the organic electroluminescent device comprising the specific combination of compounds according to the present disclosure as a host material has significantly better life characteristics than the organic electroluminescent device in which a conventional host compound is used in combination as a host material.

[0118] Device Examples 4-6: Fabrication of OLEDs with co-deposited first and second host compounds according to the present disclosure An OLED was fabricated in the same manner as Device Example 1, except that the first host compound and the second host compound in Table 2 below were used as hosts in the emissive layer.

[0119] Comparative Device Example 2: Fabrication of an OLED Containing a Comparative Compound as a Host An OLED was fabricated in the same manner as Device Example 4, except that the first host compound in Table 2 below was used as the host in the emissive layer.

[0120] The organic electroluminescent devices of Comparative Device 2 and Examples 4 to 6 prepared as described above were measured for the driving voltage based on the luminance of 1,000 nit, the emission color, and the time required for the light intensity based on the luminance of 10,000 nit to decrease from 100% to 95% (lifetime; T95). The results are shown in Table 2 below.

[0121] [Table 8]

[0122] From Table 2, it can be seen that the organic electroluminescent device comprising the specific combination of compounds according to the present disclosure as a host material has significantly better life characteristics than the organic electroluminescent device in which a conventional host compound is used in combination as a host material.

[0123] Device Examples 7-9: Fabrication of OLEDs with co-deposited first and second host compounds according to the present disclosure An OLED was fabricated in the same manner as Device Example 1, except that the first host compound and the second host compound in Table 3 below were used as hosts in the emissive layer.

[0124] Comparative Device Example 3: Fabrication of an OLED Containing a Comparative Compound as a Host An OLED was fabricated in the same manner as Device Example 7, except that the first host compound in Table 3 below was used as the host in the emissive layer.

[0125] The organic electroluminescent devices of Comparative Example 3 and Examples 7 to 9 prepared as described above were measured for the driving voltage based on the luminance of 1,000 nit, the emission color, and the time required for the light intensity based on the luminance of 10,000 nit to decrease from 100% to 95% (lifetime; T95). The results are shown in Table 3 below.

[0126] [Table 9]

[0127] From the above, it can be seen that an organic electroluminescent device comprising a specific combination of compounds according to the present disclosure as a host material has significantly better life characteristics than an organic electroluminescent device in which a conventional host compound is used in combination as a host material.

[0128] In addition, the luminous efficiency of the prepared organic electroluminescent device was measured based on the brightness of 1000 nit, and the luminous efficiency was 30.4 cd / A for device comparative example 3, and 30.9 cd / A and 30.7 cd / A for device examples 8 and 9, respectively. This confirms that the organic electroluminescent device according to the present disclosure has improved efficiency compared to the organic electroluminescent device using the conventional combination of host compounds.

[0129] Device Examples 10-12: Fabrication of OLEDs with co-deposited first and second host compounds according to the present disclosure An OLED was fabricated in the same manner as Device Example 1, except that the first host compound and the second host compound in Table 4 below were used as hosts in the emissive layer.

[0130] Comparative Device Example 4: Preparation of an OLED Containing a Comparative Compound as a Host An OLED was fabricated in the same manner as Device Example 10, except that the first host compound in Table 4 below was used as the host in the emissive layer.

[0131] The organic electroluminescent devices of Comparative Example 4 and Examples 10 to 12 prepared as described above were measured for the driving voltage based on the luminance of 1,000 nit, the emission color, and the time required for the light intensity based on the luminance of 10,000 nit to decrease from 100% to 95% (lifetime; T95).The results are shown in Table 4 below.

[0132] [Table 10]

[0133] From Table 4, it can be seen that the organic electroluminescent device comprising the specific combination of compounds according to the present disclosure as a host material has significantly better life characteristics than the organic electroluminescent device using a combination of conventional host compounds as a host material.

[0134] Device Example 13: Fabrication of an OLED with co-deposited first and second host compounds according to the present disclosure An OLED was fabricated in the same manner as in Device Example 1, except that the first host compound and the second host compound in Table 5 below were used as hosts in the emissive layer.

[0135] Comparative Device Example 5: Fabrication of an OLED Containing a Comparative Compound as a Host An OLED was fabricated in the same manner as Device Example 13, except that the first host compound in Table 5 below was used as the host in the emissive layer.

[0136] The organic electroluminescent devices of Comparative Example 5 and Example 13 are prepared as described above, and the driving voltage, emission color, and the time required for the light intensity to decrease from 100% to 95% at a brightness of 10,000 nit (lifetime; T95) are measured.The results are shown in Table 5 below.

[0137] [Table 11]

[0138] From Table 5, it can be seen that the organic electroluminescent device comprising the specific combination of compounds according to the present disclosure as a host material has significantly better life characteristics than the organic electroluminescent device using a combination of conventional host compounds as a host material.

[0139] Device Examples 14 and 15: Fabrication of OLEDs Deposited with Second Hole Transport Layer Compounds According to the Present Disclosure An OLED was fabricated in the same manner as in Device Example 1, except that the compound HT-4 in Table 7 was used as the first hole injection layer and the first hole transport layer, the compound in Table 6 below was evaporated thereon to a thickness of 60 nm as the second hole transport layer, and the compound ET-2 was used as the electron transport layer material.

[0140] Comparative Example 6: Preparation of an OLED containing a comparative compound as a second hole transport layer An OLED was fabricated in the same manner as Device Example 14, except that a compound in Table 6 below was used as the second hole transport layer.

[0141] The organic electroluminescent devices of Comparative Example 6 and Examples 14 and 15 are prepared as described above, and the driving voltage, emission color, and the time (lifetime; T95) that is required for the light intensity to decrease from 100% to 95% at a brightness of 10,000 nit are measured.The results are shown in Table 6 below.

[0142] [Table 12]

[0143] From Table 6, it can be seen that the organic electroluminescent device comprising the compound according to the present disclosure as the second hole transport layer material has significantly better life characteristics than the organic electroluminescent device using the conventional hole transport material.

[0144] The compounds used in the device examples and comparative device examples are shown in Table 7 below.

[0145] [Table 13]

[0146] [Table 14]

Claims

1. Formula 1 below: 【Chemistry 1】 (In the formula, X １ and Y １ are each independently -N=, -NR ５ represents -, -O-, or -S-, provided that X １ and Y １ Either one of the above is -N=, and X １ and Y １ The other is -NR ５ -, -O-, or -S-; R １ is a substituted or unsubstituted (C6 to C30) aryl, a substituted or unsubstituted (3 to 30 membered) heteroaryl, or a group represented by the following formula 1-a: 【Chemistry 2】 represents; L １ represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; Ar １ represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 membered) heteroaryl; Ar ２ represents a substituted or unsubstituted (3 to 30 membered) heteroaryl; R ６ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C3 0) arylsilyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted mono- or di-(C1-C30) alkylamino, a substituted or unsubstituted mono- or di-(C6-C30) arylamino, a substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, a substituted or unsubstituted mono- or di-(3-30 membered) heteroarylamino, or a substituted or unsubstituted (C6-C30) aryl(3-30 membered) heteroarylamino, or may be linked to adjacent substituents to form a ring; R ２ ~R ５ each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or the following formula 1-a, or may be linked to adjacent substituents to form a ring, but R １ ~R ５ is represented by formula 1-a; a and b each independently represent an integer of 1 or 2, and c and d each independently represent an integer of 1 to 4; When a to d are integers of 2 or more, R ２ ~R ４ Each of and R ６ may be the same or different) and a first host material represented by: Formula 2 below: 【Chemistry 3】 (In the formula, X ２ is -O- or -S-; Ring A represents a benzene ring or a naphthalene ring; R ２１ and R ２２ each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, or substituted or unsubstituted tri(C6-C30) arylsilyl, or may be linked to adjacent substituents to form a ring; L ２ represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; HAr represents a substituted or unsubstituted (3-30 membered) heteroaryl containing at least one nitrogen atom; n is an integer from 1 to 5, and m is an integer from 1 to 4; When n and m are integers of 2 or more, R ２１ and R ２２ may be the same or different) and a second host material represented by: A plurality of host materials including:

2. the substituted alkyl, the substituted aryl(ene), the substituted heteroaryl, the substituted cycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, the fused ring of a substituted aliphatic ring and a substituted aromatic ring, the substituted mono- or di-alkylamino, the substituted mono- or di-arylamino, the substituted alkylarylamino, the substituted mono- or di-heteroarylamino, and the substituted arylheteroarylamino are each independently In particular, deuterium, halogen, cyano, carboxyl, nitro, hydroxy, (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, (3-7 membered) heterocycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio, (5-30 membered) heteroaryl unsubstituted or substituted with (C6-C30) aryl, unsubstituted or substituted with (C6-C30) aryl, (C6-C30)aryl substituted with (5-30-membered) heteroaryl, tri(C1-C30)alkylsilyl, tri(C6-C30)arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C1-C30)alkyldi(C6-C30)arylsilyl, a condensed ring of a (C3-C30)aliphatic ring and a (C6-C30)aromatic ring, amino, mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, (C1-C30)alkyl(C6-C30)arylamino, mono- or di-(3- to 30-membered)heteroarylamino, (C1-C30)alkyl(3- to 30-membered)heteroarylamino, (C6-C30)aryl(3- to 30-membered)heteroarylamino, (C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30)arylcarbonyl, (C6-C30)arylphosphinyl, di(C6-C30)arylboronyl, di(C1-C30)alkylboronyl, (C1-C30)alkyl(C6-C30)arylboronyl, (C6-C30)ar(C1-C30)alkyl,10. The host materials of claim 1, wherein the host materials are substituted with at least one selected from the group consisting of (C1-C30) alkyl, (C6-C30) aryl,

3. The plurality of host materials according to claim 1, wherein the formula 1 is represented by any one of the following formulas 1-1 to 1-4: 【Chemistry 4】 (In the formula, c' is an integer from 1 to 3; When c′ is an integer of 2 or more, R ４ each of may be the same or different; X １ , Y １ , R １ ~R ４ , R ６ , L １ , Ar １ , Ar ２ , and a to d are the same as defined in formula 1).

4. Ar in the above formula 1-a ２ The plurality of host materials of claim 1 , wherein R represents any one of the following formulas R-1 to R-4: 【Chemistry 5】 (In the formula, X is O, S, Se, or N; R １１ ~R １８ each independently represents hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl, or a substituted or unsubstituted (C6-C30) aryl.

5. The host material according to claim 1, wherein the formula 2 is represented by any one of the following formulas 2-1 to 2-16: 【Chemistry 6】 【Chemistry 7】 (In the formula, L ３ and L ４ each independently can represent a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene; Ar ３ and Ar ４ each independently represents a substituted or unsubstituted (C6 to C30) aryl, or a substituted or unsubstituted (3 to 30 membered) heteroaryl; X ２ , R ２１ , R ２２ , L ２ , n, and m are as defined in claim 1; n' is an integer from 1 to 3; When n′ is 2 or more, R ２１ may be the same or different from each other).

6. The compound represented by formula 1 is the following compound: 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 2. The host material of claim 1 , wherein the host material is selected from:

7. The compound represented by formula 2 is the following compound: 【Chemistry 17】 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemical 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemical 27】 【Chemistry 28】 【Chemical 29】 【Chemistry 30】 【Chemistry 31】 【Chemistry 32】 【Chemical 33】 【Chemical 34】 【Chemistry 35】 【Chemical 36】 【Chemical 37】 【Chemical Formula 38】 【Chemical Formula 39】 【Chemistry 40】 【Chemistry 41】 【Chemistry 42】 【Chemistry 43】 【Chemistry 44】 【Chemistry 45】 【Chemistry 46】 【Chemistry 47】 【Chemistry 48】 【Chemistry 49】 【Chemistry 50】 【Chemistry 51】 【Chemistry 52】 【Chemistry 53】 【Chemical 54】 2. The host material of claim 1 , wherein the host material is selected from:

8. 13. An organic electroluminescent device comprising: a first electrode; a second electrode; and one or more emissive layers sandwiched between the first electrode and the second electrode, wherein at least one emissive layer comprises a plurality of host materials according to claim 1.

9. 9. The organic electroluminescent device of claim 8, further comprising a hole transport zone sandwiched between the first electrode and the light-emitting layer, the hole transport zone comprising at least two layers.

10. An organic electroluminescent compound represented by the following formula 1: 【Chemistry 55】 (In the formula, X １ and Y １ are each independently -N=, -NR ５ represents -, -O-, or -S-, provided that X １ and Y １ Either one of the above is -N=, and X １ and Y １ The other is -NR ５ -, -O-, or -S-; R １ is a substituted or unsubstituted (C6 to C30) aryl, a substituted or unsubstituted (3 to 30 membered) heteroaryl, or a group represented by the following formula 1-a: 【Chemistry 56】 represents L １ represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; Ar １ represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 membered) heteroaryl; Ar ２ represents a substituted or unsubstituted (3 to 30 membered) heteroaryl; R ６ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C3 0) arylsilyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted mono- or di-(C1-C30) alkylamino, a substituted or unsubstituted mono- or di-(C6-C30) arylamino, a substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, a substituted or unsubstituted mono- or di-(3-30 membered) heteroarylamino, or a substituted or unsubstituted (C6-C30) aryl(3-30 membered) heteroarylamino, or may be linked to adjacent substituents to form a ring; R ２ ~R ５ each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or the following formula 1-a, or may be linked to adjacent substituents to form a ring, but R １ ~R ５ is represented by formula 1-a; a and b each independently represent an integer of 1 or 2, and c and d each independently represent an integer of 1 to 4; When a to d are integers of 2 or more, R ２ ~R ４ Each of and R ６ may be the same or different).

11. The organic electroluminescent compound according to claim 10, wherein the formula 1 is represented by any one of the following formulas 1-1 to 1-4: 【Chemistry 57】 (In the formula, c' is an integer from 1 to 3; When c′ is an integer of 2 or more, R ４ each of may be the same or different; X １ , Y １ , R １ ~R ４ , R ６ , L １ , Ar １ , Ar ２ , and a to d are the same as defined in formula 1).

12. Ar in the above formula 1-a ２ The organic electroluminescent compound according to claim 10, wherein R-1 represents one of the following formulae R-1 to R-4: 【Chemistry 58】 (In the formula, X is O, S, Se, or N; R １１ ~R １８ each independently represents hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl, or a substituted or unsubstituted (C6-C30) aryl.

13. The compound represented by formula 1 is the following compound: 【Chemistry 59】 【Chemistry 60】 【Chemistry 61】 【Chemistry 62】 【Chemistry 63】 【Chemistry 64】 【Chemistry 65】 【Chemistry 66】 【Chemistry 67】 The organic electroluminescent compound according to claim 10, wherein the organic electroluminescent compound is selected from the group consisting of

14. An organic electroluminescent material comprising the organic electroluminescent compound according to claim 10.

15. An organic electroluminescent device comprising the organic electroluminescent compound of claim 10.

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