Organic electroluminescent compound, plurality of host materials, and organic

Abstract

The present disclosure relates to an organic electroluminescent compound, a plurality of host materials, and an organic electroluminescent device comprising the same. By including the organic electroluminescent compound according to the present disclosure, an organic electroluminescent device having long lifespan characteristics can be prepared, and by including a plurality of host materials according to the present disclosure, an organic electroluminescent device having long lifespan characteristics can be prepared.

Description

Technical Field

[0001] The present disclosure relates to an organic electroluminescent compound, a plurality of host materials, and an organic electroluminescent device comprising the same. Background Art

[0002] Organic electroluminescent devices (EL devices) are self-luminous 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 low molecular weight aromatic diamines and aluminum complexes as materials for forming a light-emitting layer (see: Appl. Phys. Lett. [Applied Physics Letters] 51, 913, 1987).

[0003] The luminescent material of organic electroluminescent device is the most important factor that determines the luminous efficiency of the device, and the luminescent material should have high quantum efficiency and high electron and hole mobility, and the luminescent material layer formed should be uniform and stable. The luminescent material can be divided into a host material and a dopant material in terms of function, and can be used by mixing a host and a dopant to improve color purity, luminous efficiency and stability. The desired characteristics of the solvent in the solid state and the host material acting as an energy carrier should be high purity and have an appropriate molecular weight so that vacuum deposition can be performed. In addition, thermal stability should be ensured based on high glass transition temperature and thermal decomposition temperature, high electrochemical stability is required for long life, amorphous films should be easily formed, and the adhesion with the materials of other adjacent layers is good, but interlayer movement is preferably not performed. When using this dopant / host material system, the host material has a great influence on the efficiency and life of the light-emitting device, and therefore its selection is important.

[0004] Various compounds are known as such host materials, but in the case of an organic electroluminescent device using known materials, due to high driving voltage, low efficiency and short life, new materials are required. Therefore, it is necessary to develop such a host material that enables an organic electroluminescent device having excellent life characteristics even at low voltage driving and high brightness.

[0005] Korean Patent Publication No. 10-2019-0013353 discloses an organic optoelectronic device that uses a compound having a benzonaphtho-based heteroaryl portion as a base skeleton together with a compound having a carbazole-carbazole portion as a host of a light-emitting layer, but does not disclose a variety of host materials as in the present invention, which uses a compound in which a 5-membered heteroaryl group is condensed with a side benzene ring of a phenanthrene skeleton together with a compound having a carbazole-based heteroaryl portion as a base skeleton. Summary of the invention

[0006] Issues to be resolved

[0007] An object of the present disclosure is to provide an organic electroluminescent compound capable of producing an organic electroluminescent device having a long life characteristic, and an organic electroluminescent device including the same.

[0008] Another object of the present disclosure is to provide a variety of host materials capable of producing an organic electroluminescent device having a long life characteristic, and an organic electroluminescent device including the plurality of host materials.

[0009] Solution to the problem

[0010] As a result of in-depth research to solve the above-mentioned technical problems, the inventors of the present invention found that the compound represented by the following formula 1 and a plurality of host materials comprising a first host material and a second host material achieved the above-mentioned purpose, thereby completing the present invention. The first host material comprises the compound represented by the following formula 1, and the second host material comprises the compound represented by the following formula 2.

[0011]

[0012] In formula 1,

[0013] X1 and Y1 each independently represent -N=, -NR5, -O- or -S-, provided that either one of X1 and Y1 is -N= and the other of X1 and Y1 is -NR5-, -O- or -S-;

[0014] R1 represents a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, or the following formula 1-a: and

[0015] 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- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) Alkyl (C6-C30) aryl silyl, substituted or unsubstituted (C1-C30) alkyl di (C6-C30) aryl silyl, substituted or unsubstituted tri (C6-C30) aryl silyl, a substituted or unsubstituted condensed ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or the following formula 1-a; or may be connected with adjacent substituents to form a ring, provided that at least one of R1 to R5 is the following formula 1-a.

[0016]

[0017] In formula 1-a,

[0018] L1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group;

[0019] Ar1 represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group;

[0020] Ar2 represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group;

[0021] R6 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted condensed ring 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- to 30-membered)heteroarylamino, or a substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino; or may be connected to an adjacent substituent to form a ring;

[0022] 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; and

[0023] When a to d are integers of 2 or more, each of R2 to R4, and each R6 may be the same or different.

[0024]

[0025] In formula 2,

[0026] X2 is -O- or -S-;

[0027] Ring A is benzene or naphthalene;

[0028] 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- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, or substituted or unsubstituted tri(C6-C30) arylsilyl; or may be linked to an adjacent substituent to form a ring;

[0029] L2 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group;

[0030] HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group containing at least one nitrogen atom;

[0031] n is an integer from 1 to 5, and m is an integer from 1 to 4; and

[0032] When n and m are integers of 2 or greater, each R 21 and each R 22 Can be the same or different.

[0033] Beneficial effects of the present invention

[0034] By using the organic electroluminescent compound according to the present disclosure and various host materials including the same, an organic electroluminescent device having a long lifespan characteristic may be prepared. BRIEF DESCRIPTION OF THE DRAWINGS

[0035] Figure 1 A compound according to one example of the present invention is shown. DETAILED DESCRIPTION

[0036] Hereinafter, the present disclosure will be described in detail. However, this is for the purpose of description and should not be construed as a method of limiting the scope of the present disclosure.

[0037] The present disclosure relates to an organic electroluminescent compound represented by Formula 1 and an organic electroluminescent device including the organic electroluminescent compound.

[0038] In addition, the present disclosure relates to a variety of host materials and organic electroluminescent devices comprising these host materials, wherein the plurality of host materials include one or more first host materials and one or more second host materials, wherein the first host material includes a compound represented by Formula 1, and the second host material includes a compound represented by Formula 2.

[0039] 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 constituting the organic electroluminescent device as necessary.

[0040] In this article, the term "organic electroluminescent material" in the present disclosure refers to a material that can be used in an organic electroluminescent device, and can include one or more compounds, and can be included in any layer constituting the organic electroluminescent device as required. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole auxiliary material, a luminescence auxiliary material, an electron blocking material, a luminescent material (including a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0041] In this article, the term "multiple host materials" in the present disclosure refers to a host material comprising a combination of two or more compounds, which may be included in any light-emitting layer constituting an organic electroluminescent device, and may refer to both materials before (e.g., before deposition) and after (e.g., after deposition) being included in the 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 included in the organic electroluminescent material. Two or more compounds included in the multiple host materials of the present disclosure may be included together in one light-emitting layer by methods used in the art, or may be included in different light-emitting layers. For example, two or more compounds may be mixed deposited, co-deposited, or deposited separately.

[0042] In this article, the term "hole transport zone" in the present disclosure refers to a region in which holes move between the first electrode and the light-emitting layer, and may include, for example, one or more of a hole injection layer, a hole transport layer, a hole auxiliary layer, a luminescence auxiliary layer, and an electron blocking layer. The hole injection layer, the hole transport layer, the hole auxiliary layer, the luminescence auxiliary layer, and the electron blocking layer may each be a single layer, two or more layers, or a plurality of layers in which three or more layers are stacked. According to an example of the present disclosure, the hole transport belt 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, and may include a hole auxiliary layer, a luminescence auxiliary layer, and one or more of an electron blocking layer. In addition, according to another example of the present disclosure, the hole transport band may include a first hole transport layer and a second hole transport layer, the first hole transport layer may be placed between the first electrode and the light-emitting layer, the second hole transport layer may be placed between the first hole transport layer and the light-emitting layer, and the second hole transport layer may act as a hole transport layer, a light-emitting auxiliary layer, a hole auxiliary layer, and / or an electron blocking layer. The hole transport band may include a first hole transport layer, a second hole transport layer, and a third hole transport layer, wherein 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, 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 act as a hole transport layer, a light-emitting auxiliary layer, a hole auxiliary layer, and / or an electron blocking layer.

[0043] Herein, the term "(C1-C30) (ene) alkyl" in the present disclosure refers to a straight or branched chain (ene) alkyl group having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10. Specific examples of the alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl and the like.

[0044] In this article, the term "(C3-C30) (sub) cycloalkyl" in the present disclosure refers to a monocyclic hydrocarbon or polycyclic hydrocarbon having 3 to 30 ring backbone carbon atoms, preferably 3 to 20 carbon atoms, and more preferably 3 to 7 carbon atoms. Examples of cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.

[0045] Herein, the term "(C3-C30)cycloalkenyl" in the present disclosure refers to a monocyclic hydrocarbon or polycyclic hydrocarbon having 3 to 30 ring backbone carbon atoms and containing double bonds on the ring backbone, preferably having 3 to 20 carbon atoms, and more preferably having 3 to 7 carbon atoms. Examples of cycloalkenyl may include cyclopropenyl, cyclobutenyl, cyclopentenyl, etc.

[0046] As used herein, the term "(3- to 7-membered) heterocycloalkyl" in the present disclosure refers to a cycloalkyl group having 3 to 7, preferably 5 to 7 ring backbone atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably O, S, and N, for example, tetrahydrofuran, pyrrolidine, tetrahydrothiophene (thiolane), tetrahydropyran, etc.

[0047] In this article, "(C6-C30) (sub)aryl" in the present disclosure refers to a monocyclic or condensed ring-based group derived from an aromatic hydrocarbon having 6 to 30 ring skeleton carbon atoms, and may be partially saturated, and includes those having a spiro structure. The number of ring skeleton carbon atoms is preferably 6 to 20, more preferably 6 to 15. Examples of aryl groups specifically include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthrenyl, triphenylenyl, phenylphenanthrenyl, anthracenyl, benzanthryl, indenyl, triphenylene, pyrenyl, naphthyl, perylene, Benzo The aryl group may include an aryl group, a cyclopentyl ... biphenyl-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, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 9-phenanthrenyl, 1- Base, 2- Base, 3- Base, 4- Base, 5- Base, 6- Benzo[c]phenanthrenyl, benzo[g] 1-triphenylene, 2-triphenylene, 3-triphenylene, 4-triphenylene, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl and the like.

[0048] In this article, the term "(3 yuan to 30 yuan) (sub) heteroaryl" in the present disclosure refers to an aryl group having 3 to 30 ring backbone atoms and including one or more heteroatomic groups selected from B, N, O, S, Si, P, Se and Ge, and preferably having 5 to 25 ring backbone atoms. The number of heteroatoms is preferably 1 to 4, and can be a monocyclic system or a fused ring system fused with one or more benzene rings, and can be partially saturated. In addition, heteroaryl herein also includes a form in which at least one heteroaryl or aryl is connected to a heteroaryl group by a single bond. Examples of heteroaryl groups specifically include monocyclic heteroaryl groups such as furanyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, and the like; and fused ring heteroaryl groups such as benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothienyl, benzo imidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, imidazopyridyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, indolizinyl, acridinyl, silafluorenyl, germaniumfluorenyl, etc. More specifically, the heteroaryl group is 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidyl, 4-pyrimidyl, 5-pyrimidyl, 6-pyrimidyl, 1,2,3-triazine-4-yl, 1,2,4-triazine-3-yl, 1,3,5-triazine-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1 -indolizinyl, 2-indolizinyl, 3-indolizinyl, 5-indolizinyl, 6-indolizinyl, 7-indolizinyl, 8-indolizinyl, 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-furanyl, 3-furanyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isoindolyl, benzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl,7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazolyl-1-yl, azacarbazolyl-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, -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-tert-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4 -tert-butyl-1-indolyl, 2-tert-butyl-3-indolyl, 4-tert-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophene, 2-dibenzothiophene, 3-dibenzothiophene, 4-dibenzothiophene, 1-silicon fluorenyl, 2-silicon fluorenyl, 3-silicon fluorenyl, 4-silicon fluorenyl, 1-germanium fluorenyl, 2-germanium fluorenyl, 3-germanium fluorenyl, 4-germanium fluorenyl. In addition, "(sub) heteroaryl" can be classified into (sub) heteroaryl with electronic characteristics and (sub) heteroaryl with hole characteristics. The (sub)heteroaryl group having an electron characteristic is a substituent having relatively abundant electrons in the parent nucleus, and may be, for example, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazine group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinolyl group, etc. The (sub)heteroaryl group having a hole characteristic is a substituent having relatively deficient electrons in the parent nucleus, and may be, for example, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophene group.

[0049] Herein, the term "condensed ring of (C3-C30) aliphatic ring and (C6-C30) aromatic ring" in the present disclosure refers to a functional group of such rings, wherein at least one aliphatic ring having 3 to 30, preferably 3 to 25, more preferably 3 to 18 ring backbone carbon atoms and at least one aromatic ring having 6 to 30, preferably 6 to 25, more preferably 6 to 18 ring backbone carbon atoms are condensed. For example, the condensed ring of at least one benzene and at least one cyclohexane, or the condensed ring of at least one naphthalene and at least one cyclopentane can be mentioned.

[0050] The carbon atoms of the fused ring of the (C3-C30) aliphatic ring and the (C6-C30) aromatic ring may be replaced by at least one heteroatom selected from B, N, O, S, Si and P, preferably at least one heteroatom selected from N, O and S. Herein, the "halogen" in the present disclosure includes F, Cl, Br and I atoms.

[0051] In addition, "ortho (ortho-)", "meta (meta-)" and "para (para-)" mean the substitution positions of all substituents, the ortho position means the compound in which the position of the substituent is directly adjacent to it, for example, in the case of benzene, it means the 1 or 2 position; the meta position means the position next to the directly adjacent substitution position, for example, in the case of benzene, it means the 1 or 3 position; and the para position means the position adjacent to the meta position, for example, in the case of benzene, it means the 1 or 4 position.

[0052] In this article, the term "ring formed by connecting to adjacent substituents" in the present disclosure refers to a substituted or unsubstituted (3- to 30-membered) monocyclic or polycyclic alicyclic ring or aromatic ring, or a combination thereof, formed by connecting or fusing two or more adjacent substituents, and preferably, a substituted or unsubstituted (3- to 26-membered) monocyclic or polycyclic alicyclic ring or aromatic ring, or a combination thereof. In addition, the formed ring may contain at least one heteroatom selected from B, N, O, S, Si and P, preferably at least one heteroatom selected from N, O and S. According to one embodiment of the present disclosure, the number of ring skeleton atoms is (5- to 20-membered), and according to another embodiment of the present disclosure, the number of ring skeleton atoms is (5- to 15-membered).

[0053] In addition, in the description of "substituted or unsubstituted" in this article, "substituted" means that a hydrogen atom in a functional group is replaced by another atom or another functional group (i.e., a substituent). Unless otherwise specified, a substituent may, but is not limited to, replace hydrogen at a position where a substituent may be substituted, and when two or more hydrogen atoms are replaced by each substituent in a functional group, each substituent may be the same or different from each other. The maximum number of substituents that can be substituted for a functional group may be the total number of substituted valence atoms of each atom constituting the functional group. Preferably, in the present disclosure, R1 to R6, R21 , R 22 In Ar1, Ar2 and HAr, substituted alkyl, substituted (sub)aryl, substituted heteroaryl, substituted cycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted condensed ring of aliphatic ring and 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 substituted by one or more selected from the group consisting of: deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C30) alkyl, halogenated (C1-C30) alkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C1-C30) alkoxy, (C1-C30) alkylthio, (C3-C30) cycloalkyl, (C3-C30) cycloalkenyl, (3- to 7-membered) heterocycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio, (5- to 30-membered) heteroaryl which is unsubstituted or substituted by (C6-C30) aryl, (C6-C30) alkylthio which is unsubstituted or substituted by (5- to 30-membered) heteroaryl 0) aryl, 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) heteroaromatic The invention also includes but is not limited to the following: a (C1-C30)alkylamino, (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)arylborylcarbonyl, di(C1-C30)alkylborylcarbonyl, (C1-C30)alkyl(C6-C30)arylborylcarbonyl, (C6-C30)aryl(C1-C30)alkyl, and (C1-C30)alkyl(C6-C30)aryl. For example, the substituents 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 phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted substituted or unsubstituted triphenylene, substituted or unsubstituted fluoranthene, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted norbornenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted carbazolyl, unsubstituted or phenyl-substituted carbazolyl, substituted or unsubstituted dibenzofuranyl, unsubstituted or deuterium-substituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted benzonaphthofuranyl, or substituted or unsubstituted phenanthroxazolyl.

[0054] In the present disclosure, when no substituent is shown in a formula or compound structure, this may mean that all positions that can appear as a substituent are hydrogen or deuterium. That is, in the case of deuterium (isotope of hydrogen), some hydrogen atoms may be deuterium, which is an isotope; and in this case, the content of deuterium may be 0% to 100%. In the case where no substituent is shown in a formula or compound structure, when deuterium is not explicitly excluded (such as when the content of deuterium is 0%, the content of hydrogen is 100%, and all substituents are hydrogen), hydrogen and deuterium can be mixed and used in the compound. Deuterium is one of the isotopes of hydrogen and is an element with a deuteron as its core, which is composed of one proton and one neutron. It can be expressed as hydrogen-2, and the element symbol can be written as D or 2H. Isotopes refer to atoms with the same atomic number (Z) but different mass numbers (A). It can also be interpreted as elements with the same number of protons but different numbers of neutrons.

[0055] As used herein, "combinations thereof" in the present disclosure means that one or more components of the corresponding list are combined to form known or chemically stable arrangements that can be imagined by a person skilled in the art from the corresponding list. For example, alkyl and deuterium can be combined to form partially or fully deuterated alkyl; halogen and alkyl can be combined to form haloalkyl substituents; and halogen, alkyl and aryl can be combined to form haloarylalkyl. For example, preferred combinations of substituents can include up to 50 atoms other than hydrogen and deuterium, or up to 40 atoms other than hydrogen and deuterium, or up to 30 atoms other than hydrogen and deuterium, or in many cases, preferred combinations of substituents can include up to 20 atoms other than hydrogen and deuterium.

[0056] In the formulae of the present disclosure, when a plurality of substituents are represented by the same symbol, each of these substituents represented by the same symbol may be the same as or different from each other.

[0057] Hereinafter, a host material according to one embodiment is described.

[0058] The plurality of host materials according to one embodiment may include a first host material including a compound represented by Formula 1 and a second host material including a compound represented by Formula 2, and may be included in at least one light emitting layer of the organic electroluminescent device according to one embodiment.

[0059] The first host material as a host material according to one embodiment may include a compound represented by Formula 1 below.

[0060]

[0061] In formula 1,

[0062] X1 and Y1 each independently represent -N=, -NR5, -O- or -S-, provided that either one of X1 and Y1 is -N= and the other of X1 and Y1 is -NR5-, -O- or -S-;

[0063] R1 represents a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, or the following formula 1-a: and

[0064] 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- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) Alkyl (C6-C30) aryl silyl, substituted or unsubstituted (C1-C30) alkyl di (C6-C30) aryl silyl, substituted or unsubstituted tri (C6-C30) aryl silyl, a substituted or unsubstituted condensed ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or the following formula 1-a; or may be connected with an adjacent substituent to form a ring, provided that at least one of R1 to R5 is the following formula 1-a:

[0065]

[0066] In formula 1-a,

[0067] L1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group;

[0068] Ar1 represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group;

[0069] Ar2 represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group;

[0070] R6 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted condensed ring 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- to 30-membered)heteroarylamino, or a substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino; or may be connected to an adjacent substituent to form a ring;

[0071] 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; and

[0072] When a to d are integers of 2 or more, each of R2 to R4, and each R6 may be the same or different.

[0073] 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-.

[0074] In one embodiment, R1 may represent a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, or Formula 1-a, and preferably, R1 may represent a substituted or unsubstituted (C6-C25) aryl, a substituted or unsubstituted (3- to 25-membered) heteroaryl, or Formula 1-a. For example, R1 may be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, or Formula 1-a.

[0075] In one embodiment, R2 to R5 may each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, or formula 1-a, and preferably, R2 to R5 may each independently represent hydrogen, deuterium, halogen, cyano, or formula 1-a. For example, R2 to R5 may each independently represent hydrogen or formula 1-a.

[0076] In one embodiment, L1 may represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene, and preferably, L1 may represent a single bond, a substituted or unsubstituted (C6-C25)arylene, or a substituted or unsubstituted (3- to 25-membered)heteroarylene. For example, L1 may be a single bond or a substituted or unsubstituted phenylene.

[0077] In one embodiment, Ar1 may represent a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3- to 30-membered) heteroaryl, and preferably, Ar1 may represent a substituted or unsubstituted (C6-C25) aryl, or a substituted or unsubstituted (5- to 25-membered) heteroaryl. For example, Ar1 may be a substituted or unsubstituted 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 dimethylfluorenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothienyl, or a substituted or unsubstituted carbazole. The substituent of the substituted phenyl may be deuterium or methyl, and the substituent of the substituted carbazole may be phenyl.

[0078] In one embodiment, Ar2 may represent a substituted or unsubstituted (3 to 30 yuan) heteroaryl, and preferably, Ar2 may represent a substituted or unsubstituted (5 to 25 yuan) heteroaryl. For example, Ar2 may be a substituted or unsubstituted dibenzofuranyl or a substituted or unsubstituted dibenzothienyl. The substituent of the substituted dibenzofuran may be deuterium, methyl or phenyl.

[0079] In one embodiment, R6 can represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C6-C30) aryl, and 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.

[0080] In one embodiment, a and b may each independently be an integer of 1 or 2, c and d may each independently be an integer of 1 to 4, and when a to d are integers of 2 or greater, each of R2 to R4 and each R6 may be the same or different.

[0081] The compound represented by Formula 1 may be represented by any one of the following Formulae 1-1 to 1-4.

[0082]

[0083] In formulas 1-1 to 1-4,

[0084] c′ is an integer from 1 to 3;

[0085] When c' is an integer of 2 or greater, each R4 may be the same or different;

[0086] X1, Y1, R1 to R4, R6, L1, Ar1, Ar2, and a to d are the same as defined in Formula 1.

[0087] In one embodiment, c′ may be an integer from 1 to 3, and when c′ is an integer of 2 or more, each R4 may be the same or different.

[0088] According to one embodiment, Ar2 in Formula 1-a may be represented by any one of the following formulae R-1 to R-4.

[0089]

[0090]

[0091] In formulae R-1 to R-4,

[0092] X is O, S, Se or N; and

[0093] R 11 To R 18 Each independently may represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl group, or a substituted or unsubstituted (C6-C30) aryl group.

[0094] In one embodiment, X may be O, Se or S.

[0095] In one embodiment, R 11 To R 18 can each independently represent hydrogen, deuterium, or substituted or unsubstituted (C1-C10) alkyl. Preferably, R 11 To R 18 can each independently represent hydrogen or deuterium. For example, all R 11 To R 18 It can all be hydrogen.

[0096] According to one embodiment, the first host material may be exemplified by the following compounds, but is not limited thereto.

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105] 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, a synthesis method disclosed in many patent documents can be used. For example, it can be synthesized with reference to the method disclosed in Korean Patent Publication No. 2017-0022865 (March 2, 2017), but is not limited thereto.

[0106] As another host material according to one embodiment, the second host material may include a compound represented by Formula 2 below.

[0107]

[0108] In formula 2,

[0109] X2 is -O- or -S-;

[0110] Ring A is a benzene ring or a naphthalene ring;

[0111] 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- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, or substituted or unsubstituted tri(C6-C30) arylsilyl; or may be linked to an adjacent substituent to form a ring;

[0112] L2 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group;

[0113] HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group containing at least one nitrogen atom;

[0114] n is an integer from 1 to 5, and m is an integer from 1 to 4; and

[0115] When n and m are integers of 2 or greater, each R 21 and each R 22 Can be the same or different.

[0116] In one embodiment, R 21 and R 22 Each may independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl, or substituted or unsubstituted tri(C6-C30)arylsilyl; or may be connected to an adjacent substituent to form a ring; preferably, R 21 and R 22 Each may independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C25) alkyl, substituted or unsubstituted (C6-C25) aryl, substituted or unsubstituted (3- 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 an adjacent substituent to form a ring. For example, R 21 and R 22 and 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.

[0117] In one embodiment, L2 may represent a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3- to 30-membered) heteroarylene group. Preferably, L2 may represent a single bond, a substituted or unsubstituted (C6-C25) arylene group, or a substituted or unsubstituted (3- to 30-membered) heteroarylene group. For example, L2 may be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted phenylnaphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted naphthylphenylene group.

[0118] In one embodiment, HAr may represent a substituted or unsubstituted (3- to 30-membered) heteroaryl group containing at least one nitrogen atom, and preferably, HAr may represent a substituted or unsubstituted (5- to 25-membered) heteroaryl group containing at least two nitrogen atoms. For example, HAr may represent a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazine group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted benzoquinazolinyl group, or a substituted or unsubstituted naphthoquinoxalinyl group. The substituent of the substituted pyrimidine group may be a phenyl group or a pyridinyl group substituted by a phenyl group. The substituent of the substituted quinoxaline group may be phenyl, biphenyl, naphthyl, dimethylfluorenyl, diphenylfluorenyl, dibenzothienyl, or a carbazolyl substituted with a phenyl group, the substituent of the substituted quinazolinyl group may be phenyl, biphenyl, naphthyl, dimethylfluorenyl, or dibenzothienyl, the substituent of the substituted benzoquinoxaline group may be phenyl or naphthyl, the substituent of the substituted benzoquinazolinyl group may be phenyl, and the substituent of the substituted naphthoquinazolinyl group may be phenyl.

[0119] In one embodiment, the compound represented by Formula 2 may be represented by any one of Formulae 2-1 to 2-16.

[0120]

[0121]

[0122] In formulas 2-1 to 2-16,

[0123] L3 and L4 may each independently represent a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group;

[0124] Ar3 and Ar4 each independently represent a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group;

[0125] X2, R 21 , R 22 , L2, n and m are the same as defined in Formula 2;

[0126] n′ is an integer from 1 to 3; and

[0127] When n' is an integer of 2 or greater, each R 21 May be the same as or different from each other.

[0128] In one embodiment, L3 and L4 may each independently represent a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3- to 30-membered) heteroarylene group; preferably, L3 and L4 may each independently represent a single bond, a substituted or unsubstituted (C6-C25) arylene group, or a substituted or unsubstituted (3- to 25-membered) heteroarylene group. For example, L3 and L4 may each independently represent a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted phenanthrenyl group.

[0129] In one embodiment, Ar3 and Ar4 can each independently represent a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5- to 30-membered) heteroaryl group; preferably, Ar3 and Ar4 can each independently represent a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5- to 25-membered) heteroaryl group. For example, Ar3 and Ar4 can each independently represent a substituted or unsubstituted phenyl group, an unsubstituted or methyl-substituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted naphthylphenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted The invention also includes a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted carbazolyl group, an unsubstituted or phenyl-substituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, an unsubstituted or deuterium-substituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted phenanthroxazolyl group, and the substituent of the substituted phenyl group, the substituted biphenyl group, the dibenzofuranyl group, or the substituted benzonaphthofuranyl group may be at least one selected from deuterium, norbornene group and adamantyl group, and the substituent of the substituted naphthyl group may be at least one selected from deuterium, biphenyl group and naphthyl group.

[0130] According to one embodiment, the second host material may be exemplified by the following compounds, but is not limited thereto.

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163] The compound represented by Formula 2 according to the present disclosure can also be prepared by a synthetic method known to those skilled in the art, and in particular, a synthetic method disclosed in many patent documents can be used. For example, Korean Patent Publication Nos. 2021-0124018 (2021.10.14.) and 2021-0006283 (2021.01.18.) can be synthesized with reference to the method disclosed in the present disclosure, but are not limited thereto.

[0164] Hereinafter, an organic electroluminescent device to which an organic electroluminescent compound, various host materials, and the organic electroluminescent compound are applied will be described.

[0165] Figure 1 A compound according to one example of the present invention is shown.

[0166] According to one embodiment, an organic electroluminescent device includes a first electrode; a second electrode; and one or more organic layers inserted between the first electrode and the second electrode, and according to one example, a first host material including a compound represented by Formula 1 and a second host material including a compound represented by Formula 2 may be included in the same organic layer, or may be included in different organic layers.

[0167] 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, the plurality of host materials including one or more first host materials and one or more second host materials, the first host material including a compound represented by Formula 1, and the second host material including a compound represented by Formula 2. According to one embodiment, the light-emitting layer may include at least one compound of compounds H1-1 to H1-171 (which is the first host material represented by Formula 1) and at least one compound of H2-1 to H2-795 (which is the second host material represented by Formula 2).

[0168] The organic electroluminescent device according to one embodiment may include a hole transport band between the first electrode and the light emitting layer. According to one embodiment, the hole transport band may include at least two layers, for example, may include three layers.

[0169] 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-transmissive reflective or reflective conductive material. In addition to the light-emitting layer, the organic layer may further include one or more layers selected from the following: a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron injection layer, an intermediate layer, a hole blocking layer, an electron blocking layer, and an electron buffer layer.

[0170] In addition to the luminescent material of the present disclosure, the organic layer may further include amine-based compounds and / or azine-based compounds. Specifically, the hole injection layer, the hole transport layer, the hole auxiliary layer, the luminescent layer, the luminescent auxiliary layer, or the electron blocking layer may include amine-based compounds (e.g., arylamine-based compounds, styryl arylamine-based compounds, etc.) as hole injection materials, hole transport materials, hole auxiliary materials, luminescent materials, luminescent auxiliary materials, and electron blocking materials. In addition, the electron transport layer, the electron injection layer, the electron buffer layer, and the hole blocking layer may include azine-based compounds as electron transport materials, electron injection materials, electron buffer materials, and hole blocking materials. In addition, the organic layer may further include one or more metals selected from the group consisting of: organic metals of the 1st group, the 2nd group, the 4th period transition metals, the 5th period transition metals, lanthanide metals, and d-transition metals, or one or more complex compounds containing these metals.

[0171] A variety of host materials according to an embodiment can be used as a light-emitting material for a white organic light-emitting device. According to the arrangement type of R (red), G (green), YG (yellow-green) or B (blue) light-emitting units, various structures such as a side-by-side type, a stacked type or a color conversion material (CCM) type have been proposed as a white organic electroluminescent device. In addition, a variety of host materials according to an embodiment can also be used in an organic electroluminescent device containing quantum dots (QDs).

[0172] A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof can be used between the anode and the light-emitting layer. In the hole injection layer, for the purpose of reducing the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, multiple layers can be used, and in each layer, two compounds can be used simultaneously. The hole injection layer can be doped with a p-type dopant. The electron blocking layer can be arranged between the hole transport layer (or hole injection layer) and the light-emitting layer, and can block the electron overflow from the light-emitting layer to confine the excitons in the light-emitting layer, thereby preventing light leakage. As a hole transport layer or an electron blocking layer, multiple layers can be used, and a variety of compounds can be used in each layer.

[0173] 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 regulating electron injection and improving the interface characteristics between the light-emitting layer and the electron injection layer, and two compounds may be used for each layer at the same time. Multiple layers may be used for the hole blocking layer or the electron transport layer, and multiple compounds may be used for each layer. The electron injection layer may be doped with an n-type dopant.

[0174] The luminescent auxiliary layer is placed between the anode and the luminescent layer or between the cathode and the luminescent layer, and when the luminescent auxiliary layer is placed between the anode and the luminescent layer, it can be used to promote the injection and / or transfer of holes or block the overflow of electrons, and when the luminescent auxiliary layer is placed between the cathode and the luminescent layer, it can be used to promote the injection and / or transfer of electrons or block the overflow of holes. In addition, the hole auxiliary layer can be arranged between the hole transport layer (or hole injection layer) and the luminescent layer, and can show the effect of smoothing or blocking the transfer speed (or injection speed) 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 luminescent auxiliary layer, the hole auxiliary layer, or the electron blocking layer can have the effect of improving the efficiency and / or life of the organic electroluminescent device.

[0175] In the organic electroluminescent device of the present disclosure, it is preferred 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 arranged on at least one inner surface of a pair of electrodes. Specifically, it is preferred that a chalcogenide (including oxide) layer of silicon and aluminum is arranged on the surface of the anode on one side of the light-emitting medium layer, and a metal halide layer or a metal oxide layer is arranged on the surface of the cathode on one side of the light-emitting medium layer. Driving stabilization of the organic electroluminescent device can be obtained by the surface layer. Preferred examples of chalcogenides include SiO X (1≤X≤2), AlO X (1≤X≤1.5), SiON, SiAlON, etc.; preferred examples of metal halides include LiF, MgF2, CaF2, rare earth metal fluorides, etc.; and preferred examples of metal oxides include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0176] The organic electroluminescent device according to one embodiment of the present disclosure may be an organic electroluminescent device having a tandem structure. In the case of a tandem organic electroluminescent device according to one embodiment, two or more single light-emitting units may be connected by a charge generation 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, wherein each light-emitting unit may include a hole transport band, a light-emitting layer, and an electron transport band, wherein the hole transport band may include a hole injection layer and a hole transport layer, wherein the electron transport band may include an electron transport layer and an electron injection layer, and according to one embodiment, one or more light-emitting layers included in the light-emitting unit may be three or more. Multiple light-emitting units may emit the same color or emit different colors. In addition, a light-emitting unit may also 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 placed between each light-emitting unit may be included. The charge generation layer refers to a layer that generates holes and electrons when a voltage is applied. When there are three or more light-emitting units, the charge generation layer may be placed between the light-emitting units. In this case, the plurality of charge generation layers may be identical to each other, and may be different from each other. Because the charge generation layer is placed between the light-emitting units, the current efficiency in each light-emitting unit may be increased, and the charge may be uniformly distributed. Specifically, the charge generation layer may be disposed between two adjacent stacks for connecting an organic electroluminescent device in series with only a pair of anodes and cathodes, without requiring a separate internal electrode placed between the stacks.

[0177] An organic electroluminescent device according to an embodiment may include two or more organic layers, and may further include one or more charge generation layers, wherein the charge generation layer may be disposed between the organic layers, and when two or more organic layers are included, the charge generation layers may be the same or different. Since the charge generation layer is disposed between the organic layers, the organic electroluminescent device may be driven by only a pair of anodes and cathodes without a separate internal electrode disposed between the organic layers.

[0178] The charge generation layer may include an n-type charge generation layer and a p-type charge generation layer, the n-type charge generation layer may be doped with an alkali metal, an alkaline earth metal, or a compound of an alkali metal and an alkaline earth metal, the alkali metal may include one selected from the group consisting of Li, Na, K, Rb, Cs, Fr, Yb and a combination thereof, and the alkaline earth metal may include one selected from the group consisting of Be, Mg, Ca, Sr, Ba, Ra and a combination thereof.

[0179] In addition, 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 reducing dopant, or a mixed region of a hole transport compound and an oxidizing dopant on at least one surface of a pair of electrodes. Since the electron transport compound is reduced to anions by this method, it is easy to inject and transport electrons from the mixed region to the luminescent medium. In addition, the hole transport compound is oxidized to a cation, and it is therefore easy to inject and transport holes from the mixed region to the luminescent medium. Preferred oxidizable dopants include various Lewis acids and acceptor compounds, and preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, an organic electroluminescent device emitting white light having two or more luminescent layers can be manufactured by using a reducing dopant layer as a charge generating layer.

[0180] The light-emitting layer of the organic electroluminescent device according to one embodiment may be a single layer as a layer on which light is emitted, and may be a plurality of layers in which two or more layers are stacked. The light-emitting layer may further contain one or more dopants, and the doping concentration of the dopant compound relative to the host compound of the light-emitting layer may be less than 20% by weight, preferably less than 10% by weight.

[0181] As the dopant included in the organic electroluminescent device of the present disclosure, one or more phosphorescent or fluorescent dopants can be used, and the fluorescent dopant is 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 a metal atom selected from the following: iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and in some cases, it can be preferably an ortho-metallated complex compound of a metal atom selected from the following: iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and in some cases, it can be more preferably an ortho-metallated iridium complex compound.

[0182] As a dopant included in the organic electroluminescent device of the present disclosure, a compound represented by the following Formula 101 may be used, but the present disclosure is not limited thereto.

[0183]

[0184] In formula 101,

[0185] L is represented by any one selected from the following structures 1 to 3;

[0186]

[0187] R 100 To R 103Each independently represents hydrogen, deuterium, halogen, unsubstituted or substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (3- to 30-membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; or may be linked to an adjacent substituent to form a ring, for example, unsubstituted or quinoline substituted with pyridine, substituted or unsubstituted benzofuranopyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuranoquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indenoquinoline;

[0188] R 104 To R 107 Each may independently represent hydrogen, deuterium, halogen, unsubstituted or (C1-C30) alkyl substituted by deuterium and / or one or more halogens, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; or may be connected with one or more adjacent substituents to form a substituted or unsubstituted ring, for example, unsubstituted or benzene-substituted naphthyl, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuranopyridine, or substituted or unsubstituted benzothienopyridine;

[0189] R 201 To R 220 Each independently represents hydrogen, deuterium, halogen, unsubstituted or substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C6-C30) aryl; or may be connected with one or more adjacent substituents to form a substituted or unsubstituted ring; and

[0190] s is an integer from 1 to 3.

[0191] Specifically, specific examples of the dopant compound are as follows, but are not limited thereto.

[0192]

[0193]

[0194]

[0195]

[0196]

[0197] The various layers of the organic electroluminescent device of the present disclosure can be formed by using any of the following: dry film forming methods such as vacuum deposition, sputtering, plasma, ion plating, etc., and wet film forming methods such as inkjet printing, nozzle printing, slit coating, spin coating, dip coating, flow coating, etc. For the wet film method, the material forming each layer is dissolved or dispersed in a suitable solvent (such as ethanol, chloroform, tetrahydrofuran or dioxane) to form a thin film, and the solvent can be any solvent in which the material forming each layer can be dissolved or dispersed, and there is no problem of film forming property.

[0198] When forming the first host material and the second host material according to one embodiment, the film can be formed by the above method, and preferably, the film can be formed by a co-deposition or a mixed deposition process. Co-deposition is a method of putting two or more isomer materials into each crucible source and evaporating and mixing the materials by applying current to two chambers at the same time, and mixed deposition is a method of mixing and depositing two or more isomer materials in one crucible source before deposition, and then evaporating and mixing the materials by applying current to one chamber.

[0199] According to one embodiment, when the first host material and the second host material exist in the same layer or different layers in the organic electroluminescent device, the two host materials can be deposited separately. For example, the second host material can be deposited after the first host material is deposited.

[0200] According to one embodiment, the present disclosure can provide a compound obtained by depositing an organic layer in a process for manufacturing an organic electroluminescent device, and then recovering and purifying the material of the organic layer attached to the deposition device. The recovered compound can be subjected to a purification and / or recrystallization process, and the purity of the purified and / or recrystallized compound obtained thereby can be 99.9% or higher.

[0201] According to one embodiment, the present disclosure provides a method for recovering multiple host materials, wherein the method includes: depositing multiple host materials, which include at least one first host material and at least one second host material, the first host material includes a compound represented by Formula 1, and the second host material includes a compound represented by Formula 2; recovering the multiple host materials attached to the deposition equipment; and purifying and / or recrystallizing the recovered multiple host materials to obtain multiple host materials with a purity of 99.9% or higher.

[0202] According to one embodiment, using a plurality of host materials including a compound represented by Formula 1 and a compound represented by Formula 2, the present disclosure can provide a display device such as a display device of a smartphone, a tablet computer, a notebook computer, a PC, a TV, or a vehicle, or a lighting device such as an outdoor or indoor lighting device.

[0203] Hereinafter, for a detailed understanding of the present disclosure, a method for preparing a compound according to the present disclosure will be explained using a synthesis method of a representative compound or an intermediate compound of the present disclosure as an example.

[0204] Example 1: Synthesis of Compound H1-3

[0205]

[0206] 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 the reaction was completed, the mixture was cooled to room temperature, filtered with diatomaceous earth to obtain a solid, and separated by column chromatography to obtain compound H1-3 (4.0 g, yield: 52.5%).

[0207] MW MP H1-3 628.72 251.2℃

[0208] Example 2: Synthesis of Compound H1-14

[0209]

[0210] 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 160° C. under reflux for 1 hour. After the reaction was completed, the mixture was cooled to room temperature, filtered with diatomaceous earth to obtain a solid, and separated by column chromatography to obtain compound H1-14 (4.3 g, yield: 33%).

[0211] MW MP H1-14 628.72 215.2℃

[0212] Example 3: Synthesis of Compound H1-1

[0213]

[0214] In a reaction vessel, 5.1 g of compound A (15.6 mmol), 6 g of compound B (15.5 mmol), 0.71 g of Pd2(dba)3 (0.776 mmol), 0.64 g of S-phos (1.55 mmol), and 3.7 g of NaOt-Bu (38.8 mmol) were dissolved in 80 mL of o-xylene, and the mixture was stirred at 160° C. under reflux for 2 hours. After the reaction was completed, 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 (6 g, yield: 62%).

[0215] MW MP H1-1 628.73 250℃

[0216] Example 4: Synthesis of Compound H1-2

[0217]

[0218] (1) Synthesis of Compound D

[0219] In a reaction vessel, compound C (15 g, 61 mmol), (4-chlorophenyl) boronic acid (12 g, 73.2 mmol), potassium carbonate (21 g, 153 mmol), Pd (PPh 3 ) 4 (3.6 g, 3.1 mmol), and 200 mL of THF were dissolved in 70 mL of water, and the mixture was refluxed at 130° C. for 5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, the organic layer was extracted with ethyl acetate, magnesium sulfate was used to remove residual moisture, dried, and separated by column chromatography to obtain compound D (15 g, yield: 88%).

[0220] (2) Synthesis of Compound H1-2

[0221] In a reaction vessel, 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, and the mixture was stirred at 160° C. under reflux for 1 hour. After the reaction was completed, the reaction mixture was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound H1-2 (7 g, yield: 45%).

[0222] MW MP H1-2 628.73 258℃

[0223] Example 5: Synthesis of Compound H1-6

[0224]

[0225] In a reaction vessel, 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 and refluxed at 160° C. for 2 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound H1-6 (2.8 g, yield: 44%).

[0226] MW MP H1-6 644.78 272.2℃

[0227] Example 6: Synthesis of Compound H1-56

[0228]

[0229] (1) Synthesis of Compound G

[0230] In a reaction vessel, compound F (30 g, 121.41 mmol), (4-chlorophenyl) boronic acid (20.88 g, 133.55 mmol), Pd(PPh 3 ) 4 (4.21 g, 3.64 mmol), and K 2 CO 3 (41.95 g, 303.53 mmol) were dissolved in 607 ml of toluene, 152 ml of ethanol, and 152 ml of water, and the mixture was refluxed at 130° C. for 24 hours. After the reaction was completed, the mixture was cooled to room temperature and filtered with celite to obtain a solid, which was separated by column chromatography to obtain compound G (26.3 g, yield: 77.7%).

[0231] (2) Synthesis of Compound I

[0232] In a reaction vessel, 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 and refluxed at 130° C. for 4 hours. After the reaction was completed, the mixture was cooled to room temperature and filtered with celite to obtain a solid, which was separated by column chromatography to obtain compound I (30 g, yield: 77.2%).

[0233] (3) Synthesis of Compound H1-56

[0234] 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 the reaction was completed, the mixture was cooled to room temperature and filtered with celite to obtain a solid, which was separated by column chromatography to obtain compound H1-56 (6 g, yield: 35.09%).

[0235] MW MP H1-56 704.8 208.6℃

[0236] Hereinafter, for a detailed understanding of the present disclosure, a method for manufacturing an organic electroluminescent device including a plurality of host materials according to the present disclosure and features thereof will be described.

[0237] Device Examples 1 to 3: OLEDs Co-deposited with a First Host Compound and a Second Host Compound According to the Disclosure Preparation

[0238] Prepare an OLED according to the present disclosure. First, a transparent electrode indium tin oxide (ITO) film (10Ω / □) on a glass substrate for OLED (GEOMATEC CO., LTD., Japan) was ultrasonically washed with acetone and isopropanol in sequence, and then stored in isopropanol. The ITO substrate was mounted on a substrate holder of a vacuum vapor deposition device. Compound HI-1 of Table 7 was introduced into a chamber of a vacuum vapor deposition device and compound HT-1 was introduced into another chamber. The two materials were evaporated at different rates, and compound HI-1 was deposited at a doping amount of 3wt% based on the total amount of compound HI-1 and compound HT-1 to form a first hole injection layer having a thickness of 10nm. Subsequently, compound HT-1 was deposited on the first hole injection layer to form a first hole transport layer having a thickness of 80nm. Next, compound HT-2 was introduced into another chamber of a vacuum vapor deposition device, and the compound was evaporated by applying an electric current to the chamber, thereby depositing a second hole transport layer having a thickness of 55nm on the first hole transport layer. Then, compound HT-3 was introduced into another chamber of the vacuum vapor deposition apparatus, and the compound was evaporated by applying electric current to the chamber, thereby depositing a third hole transport layer having a thickness of 5 nm on the second hole transport layer.

[0239] After forming the hole injection layer and the hole transport layer, the light-emitting layer was deposited thereon as follows: After placing each of the first host compound and the second host compound listed in Table 1 as the host in two chambers of a vacuum deposition device, and placing compound D-39 as a dopant in another chamber, the two host materials were evaporated at a rate of 1:1, and at the same time, the dopant material was evaporated at different rates to dope the dopant in an amount of 3wt% based on the total amount of the host and the dopant, thereby depositing a light-emitting layer having a thickness of 40nm on the second hole transport layer. Next, compound ET-1 and compound EI-1 were deposited on the light-emitting layer as electron transport materials at a weight ratio of 50:50 to form an electron transport layer having a thickness of 35nm. Subsequently, compound EI-1 was deposited on the electron transport layer as an electron injection layer to a thickness of 2nm, and then an Al cathode was deposited on the electron injection layer to a thickness of 80nm by using another vacuum deposition device, thereby completing the preparation of the OLED. For each material, by 10 -6 Each compound was purified by vacuum sublimation under vacuum.

[0240] Device Comparative Example 1: Preparation of OLEDs containing comparative compounds as hosts

[0241] An OLED was prepared in the same manner as in Device Example 1, except that the compound in the following Table 1 was used as the first host compound.

[0242] The driving voltage based on a luminance of 1,000 nits, the luminous color, and the time taken until the light intensity dropped from 100% to 95% based on a luminance of 10,000 nits (lifetime; T95) of the organic electroluminescent devices of Device Comparative Example 1 and Device Examples 1 to 3 manufactured as described above were measured, and the results are shown in Table 1 below.

[0243] Table 1

[0244]

[0245]

[0246] As can be confirmed from Table 1, the organic electroluminescent device including the compound according to the specific combination of the present disclosure as a host material has significantly better lifespan characteristics compared to the organic electroluminescent device used as a host material in combination with a conventional host compound.

[0247] Device Examples 4 to 6: OLEDs Co-deposited with a First Host Compound and a Second Host Compound According to the Disclosure Preparation

[0248] An OLED was prepared in the same manner as in Device Example 1, except that the first host compound and the second host compound in the following Table 2 were used as hosts for the light-emitting layer.

[0249] Device Comparative Example 2: Preparation of OLEDs containing comparative compounds as hosts

[0250] An OLED was prepared in the same manner as in Device Example 4, except that the first host compound in the following Table 2 was used as a host of the light-emitting layer.

[0251] The driving voltage based on a luminance of 1,000 nits, the luminous color, and the time taken until the light intensity dropped from 100% to 95% based on a luminance of 10,000 nits (lifetime; T95) of the organic electroluminescent devices of Device Comparative Example 2 and Device Examples 4 to 6 manufactured as described above were measured, and the results are shown in Table 2 below.

[0252] Table 2

[0253]

[0254] As can be confirmed from Table 2, the organic electroluminescent device including the compound according to the specific combination of the present disclosure as a host material has significantly better lifespan characteristics compared to the organic electroluminescent device used as a host material in combination with a conventional host compound.

[0255] Device Examples 7 to 9: OLEDs Co-deposited with a First Host Compound and a Second Host Compound According to the Disclosure Preparation

[0256] An OLED was prepared in the same manner as in Device Example 1, except that the first host compound and the second host compound in the following Table 3 were used as hosts for the light-emitting layer.

[0257] Device Comparative Example 3: Preparation of OLEDs containing comparative compounds as hosts

[0258] An OLED was prepared in the same manner as in Device Example 7, except that the first host compound in the following Table 3 was used as a host of the light-emitting layer.

[0259] The driving voltage based on a luminance of 1,000 nits, the luminous color, and the time taken until the light intensity dropped from 100% to 95% based on a luminance of 10,000 nits (lifetime; T95) of the organic electroluminescent devices of Device Comparative Example 3 and Device Examples 7 to 9 manufactured as described above were measured, and the results are shown in Table 3 below.

[0260] Table 3

[0261]

[0262] From the above, it can be confirmed that an organic electroluminescent device including the compound according to the specific combination of the present disclosure as a host material has significantly better lifespan characteristics compared to an organic electroluminescent device used as a host material in combination with a conventional host compound.

[0263] In addition, as a result of measuring the luminous efficiency of the produced organic electroluminescent device based on the brightness of 1,000 nits, the device comparative example 3 was 30.4 cd / A, and the device examples 8 and 9 were 30.9 and 30.7 cd / A, respectively. Thus, it can be confirmed that the organic electroluminescent device according to the present disclosure has improved efficiency compared to the organic electroluminescent device using the conventional host compound combination.

[0264] Device Examples 10 to 12: Co-deposited with a first host compound and a second host compound according to the present disclosure Preparation of OLED

[0265] An OLED was prepared in the same manner as in Device Example 1, except that the first host compound and the second host compound in the following Table 4 were used as hosts for the light-emitting layer.

[0266] Device Comparative Example 4: Preparation of OLEDs containing comparative compounds as hosts

[0267] An OLED was prepared in the same manner as in Device Example 10, except that the first host compound in the following Table 4 was used as a host of the light-emitting layer.

[0268] The driving voltage based on a luminance of 1,000 nits, the luminous color, and the time taken until the light intensity dropped from 100% to 95% (lifetime; T95) based on a luminance of 10,000 nits of the organic electroluminescent devices of Device Comparative Example 4 and Device Examples 10 to 12 manufactured as described above were measured, and the results are shown in Table 4 below.

[0269] Table 4

[0270]

[0271] As can be confirmed from Table 4, the organic electroluminescent device including the compound according to the specific combination of the present disclosure as a host material has significantly better lifespan characteristics compared to the organic electroluminescent device used as a host material in combination with a conventional host compound.

[0272] Device Example 13: OLED Co-Deposited with the First and Second Host Compounds According to the Disclosure preparation

[0273] An OLED was prepared in the same manner as in Device Example 1, except that the first host compound and the second host compound in the following Table 5 were used as hosts for the light-emitting layer.

[0274] Device Comparative Example 5: Preparation of OLEDs containing comparative compounds as hosts

[0275] An OLED was prepared in the same manner as in Device Example 13, except that the first host compound in the following Table 5 was used as a host of the light-emitting layer.

[0276] The driving voltage based on a brightness of 1,000 nits, the luminous color, and the time taken until the light intensity dropped from 100% to 95% (lifetime; T95) based on a brightness of 10,000 nits of the organic electroluminescent devices of Device Comparative Example 5 and Device Example 13 manufactured as described above were measured, and the results are shown in Table 5 below.

[0277] Table 5

[0278]

[0279] As can be confirmed from Table 5, the organic electroluminescent device including the compound according to the specific combination of the present disclosure as a host material has significantly better lifespan characteristics compared to the organic electroluminescent device used as a host material in combination with a conventional host compound.

[0280] Device Examples 14 and 15: Preparation of OLEDs with Deposition of Second Hole Transport Layer Compounds According to the Disclosure

[0281] An OLED was prepared in the same manner as in Device Example 1, except that compound HT-4 of Table 7 was used as the first hole injection layer and the first hole transport layer, the compound of the following Table 6 was deposited thereon to a thickness of 60 nm as the second hole transport layer, and compound ET-2 was used as the electron transport layer material.

[0282] Comparative Example 6: Preparation of an OLED comprising a comparative compound as a second hole transport layer

[0283] An OLED was prepared in the same manner as in Device Example 14, except that the compound of the following Table 6 was used as the second hole transport layer.

[0284] The driving voltage based on a brightness of 1,000 nits, the luminous color, and the time taken until the light intensity drops from 100% to 95% (lifetime; T95) based on a brightness of 10,000 nits of the organic electroluminescent devices of Device Comparative Example 6 and Device Examples 14 and 15 manufactured as described above were measured, and the results are shown in Table 6 below.

[0285] Table 6

[0286]

[0287] It can be confirmed from Table 6 that the organic electroluminescent device including the compound according to the present disclosure as the second hole transport layer material has significantly better lifespan characteristics compared to the organic electroluminescent device using a conventional hole transport material.

[0288] The compounds used in the device examples and the device comparative examples are shown in Table 7 below.

[0289] Table 7

[0290]

[0291]

Claims

1. A variety of main materials, including: A first host material, wherein the first host material comprises a compound represented by the following Formula 1: in, X1 and Y1 each independently represent -N=, -NR5, -O- or -S-, provided that either 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 group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, or the following formula 1-a: in, L1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group; Ar1 represents a substituted or unsubstituted (C6-C30) aryl group or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; Ar2 represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group; and R6 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted condensed ring 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- to 30-membered)heteroarylamino, or a substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino; or may be linked to an adjacent substituent to form a ring; 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- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) Alkyl (C6-C30) aryl silyl, substituted or unsubstituted (C1-C30) alkyl di (C6-C30) aryl silyl, substituted or unsubstituted tri (C6-C30) aryl silyl, a substituted or unsubstituted condensed ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or Formula 1-a; or may be connected with an adjacent substituent to form a ring, provided that at least one of R1 to R5 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; and When a to d are integers of 2 or more, each of R2 to R4, and each R6 may be the same or different, and A second host material, the second host material comprising a compound represented by the following Formula 2: in, 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- to 30-membered)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or substituted or unsubstituted tri(C6-C30)arylsilyl, or may be linked to an adjacent substituent to form a ring; L2 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group; HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group containing at least one nitrogen atom; n is an integer from 1 to 5, and m is an integer from 1 to 4; and When n and m are integers of 2 or greater, each R 21 and each R 22 Can be the same or different.

2. The plurality of host materials according to claim 1, wherein: The substituted alkyl, the substituted (ene)aryl, 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 an 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 selected from the group consisting of: one or more of: deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C30) alkyl, halogenated (C1-C30) alkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C1-C30) alkoxy, (C1-C30) alkylthio, (C3-C30) cycloalkyl, (C3-C30) cycloalkenyl, (3- to 7-membered) heterocycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio, (5- to 30-membered) heteroaryl, unsubstituted or substituted by (C6-C30) aryl, substituted (C6-C30)aryl, 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, an amino group, a mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, a (C1-C30)alkyl(C6-C30)arylamino group, a mono- or di-(3- to 30-membered) The invention also includes the following: (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)arylborylcarbonyl, di(C1-C30)alkylborylcarbonyl, (C1-C30)alkyl(C6-C30)arylborylcarbonyl, (C6-C30)aryl(C1-C30)alkyl, and (C1-C30)alkyl(C6-C30)aryl.

3. The 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: in, 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; and X1, Y1, R1 to R4, R6, L1, Ar1, Ar2, and a to d are the same as defined in claim 1.

4. The plurality of host materials according to claim 1, wherein: Ar2 of the formula 1-a represents any one of the following formulas R-1 to R-4: in, X is O, S, Se or N; and R 11 To R 18 Each independently may represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl group, or a substituted or unsubstituted (C6-C30) aryl group.

5. The plurality of host materials according to claim 1, wherein: Formula 2 is represented by any one of the following formulas 2-1 to 2-16: in, L3 and L4 may each independently represent a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group; Ar3 and Ar4 each independently represent a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; X2, R 21 , R 22 , L2, n and m are the same as defined in claim 1; n′ is an integer from 1 to 3; and When n' is an integer of 2 or greater, each R 21 May be the same as or different from each other.

6. The plurality of host materials according to claim 1, wherein: The compound represented by Formula 1 is selected from the following compounds:

7. The plurality of host materials according to claim 1, wherein: The compound represented by Formula 2 is selected from the following compounds: 8 . An organic electroluminescent device comprising a first electrode; a second electrode; and at least one light-emitting layer between the first electrode and the second electrode, wherein the at least one light-emitting layer comprises a plurality of host materials according to claim 1 . 9 . The organic electroluminescent device according to claim 8 , further comprising a hole transport band interposed between the first electrode and the light emitting layer, wherein the hole transport band comprises at least two layers.

10. An organic electroluminescent compound represented by the following formula 1: in, X1 and Y1 each independently represent -N=, -NR5, -O- or -S-, provided that either 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 group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, or the following formula 1-a: in, L1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group; Ar1 represents a substituted or unsubstituted (C6-C30) aryl group or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; Ar2 represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group; and R6 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted condensed ring 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- to 30-membered)heteroarylamino, or a substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino; or may be linked to an adjacent substituent to form a ring; 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- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) Alkyl (C6-C30) aryl silyl, substituted or unsubstituted (C1-C30) alkyl di (C6-C30) aryl silyl, substituted or unsubstituted tri (C6-C30) aryl silyl, a substituted or unsubstituted condensed ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or the following formula 1-a; or may be connected with an adjacent substituent to form a ring, provided that at least one of R1 to R5 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; and When a to d are integers of 2 or more, each of R2 to R4, and each R6 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: in, 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; and X1, Y1, R1 to R4, R6, L1, Ar1, Ar2, and a to d are the same as defined in claim 10.

12. The organic electroluminescent compound according to claim 10, wherein Ar2 in the formula 1-a represents any one of the following formulas R-1 to R-4: in, X is O, S, Se or N; and R 11 To R 18 Each independently may represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl group, or a substituted or unsubstituted (C6-C30) aryl group.

13. The organic electroluminescent compound according to claim 10, wherein The compound represented by Formula 1 is selected from the following compounds: 14 . An organic electroluminescent material comprising the organic electroluminescent compound according to claim 10 . 15 . An organic electroluminescent device comprising the organic electroluminescent compound according to claim 10 .

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