Organic electroluminescent compound, organic electroluminescent material containing the same, and organic electroluminescent device

Abstract

To provide an organic electroluminescent device having a low driving voltage and / or high luminous efficiency and / or long lifetime.SOLUTION: The organic electroluminescent device includes an organic electroluminescent material according to the following formula.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present disclosure relates to organic electroluminescent compounds, organic electroluminescent materials containing the compounds, and organic electroluminescent devices. [Background technology]

[0002] Among display devices, electroluminescent devices (EL devices) are self-emitting display devices that have the advantages of providing a wider viewing angle, a larger contrast ratio, and a faster response time. In 1987, Eastman Kodak developed the first organic EL device by using small aromatic diamine molecules and aluminum complexes as materials for forming the light-emitting layer (Non-Patent Document 1).

[0003] An organic electroluminescent device (OLED) has a multilayer structure including a hole injection layer, a hole transport layer, an emitting layer, an electron transport layer, an electron injection layer, etc., in order to improve its efficiency and stability. In this case, the selection of compounds contained in the hole transport layer, etc., is recognized as one of the means for improving device properties such as hole transport efficiency to the emitting layer, luminous efficiency, and lifespan.

[0004] In this regard, compounds such as copper phthalocyanine (CuPc), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine (TPD), and 4,4',4''-tris(3-methylphenylphenylamino)triphenylamine (MTDATA) have been used as hole-injection and transport materials in OLEDs. However, OLEDs fabricated using these materials suffer from reduced quantum efficiency and lifetime. This is due to the thermal stress that occurs between the anode and the hole-injection layer when the OLED is driven under high current, which significantly reduces the device lifetime. Furthermore, the organic materials used in the hole-injection layer have very high hole mobility, which disrupts the charge balance between holes and electrons, resulting in reduced quantum efficiency (cd / A).

[0005] Therefore, there remains a need to develop materials for the hole transport layer to improve the performance of OLEDs.

[0006] Patent Document 1 discloses an example of a host material in which tetramethylphenanthrene is used as a linking group for a carbazole-carbazole compound. However, the reference does not disclose specific device examples or a method for synthesizing the compound. In addition, the compound in the reference is not used as a material for a hole transport layer. [Prior art documents] [Patent documents]

[0007] [Patent Document 1] U.S. Patent No. 8,343,637 B2 [Non-patent literature]

[0008] [Non-Patent Document 1] Appl.Phys.Lett.51,913,1987 Summary of the Invention [Problem to be solved by the invention]

[0009] The object of the present disclosure is, first, to provide an organic electroluminescent compound that can be used to manufacture an organic electroluminescent device having a low driving voltage and / or high luminous efficiency and / or long life, and, second, to provide an organic electroluminescent device comprising the organic electroluminescent compound. [Means for solving the problem]

[0010] As a result of intensive research to solve the above technical problems, the present inventors have discovered that a compound represented by the following formula 1 having a dihydrophenanthrene moiety exhibits improved degradation properties, and have completed the present invention. [ka]

[0011] In Equation 1, R1 to R4 are each independently *-(L1) a -(Ar1) b , hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl, or may be linked to adjacent substituents to form a ring; R5~R 12 are each independently *-(L1) a -(Ar1) b, hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, or substituted or unsubstituted tri(C6-C30) arylsilyl, or may be linked to adjacent substituents to form a ring; R1~R 12 At least one of the following is *-(L1) a -(Ar1) b Provided that it represents; L1 represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30-membered) heteroarylene; Ar1 represents a substituted or unsubstituted (C6 to C30) aryl, a substituted or unsubstituted (3 to 30-membered) heteroaryl, or -N-(Ar2)(Ar3); Ar2 and Ar3 each independently represent a substituted or unsubstituted (C1 to C30) alkyl, a substituted or unsubstituted (C2 to C30) alkenyl, a substituted or unsubstituted fused ring of a (C3 to C30) aliphatic ring and a (C6 to C30) aromatic ring, a substituted or unsubstituted (C6 to C30) aryl, or a substituted or unsubstituted (3 to 30-membered) heteroaryl; a represents an integer of 1 or 2, b represents an integer of 1 to 4, and when a and b are 2 or more, each L1 and each Ar1 may be the same or different; R5~R 10 and R 12 is hydrogen and R 11 with the proviso that compounds of formula 1 containing a substituted amino group are excluded.

[0012] Advantageous Effects of the Invention By including the organic electroluminescent compound according to the present disclosure and the organic electroluminescent material containing the same, an organic electroluminescent device having a low driving voltage and / or high luminous efficiency and / or long life can be manufactured. DETAILED DESCRIPTION OF THE INVENTION

[0013] The present disclosure will be described in detail below. However, the following description is intended to illustrate the present invention and is not intended to limit the scope of the present invention in any way.

[0014] The present disclosure relates to an organic electroluminescent compound represented by Formula 1 above, an organic electroluminescent material comprising the organic electroluminescent compound, and an organic electroluminescent device comprising the organic electroluminescent material.

[0015] Furthermore, the present disclosure relates to an organic electroluminescent compound represented by Formula 2 and an organic electroluminescent device comprising the organic electroluminescent compound.

[0016] The present disclosure further relates to an organic electroluminescent compound represented by Formula 3 and an organic electroluminescent device comprising the organic electroluminescent compound.

[0017] The term "organic electroluminescent compound" in the present disclosure means a compound that can be used in an organic electroluminescent device and can be included in any layer that constitutes the organic electroluminescent device as needed.

[0018] 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 at least one compound. The organic electroluminescent material can be included in any layer that constitutes an organic electroluminescent device as needed. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole auxiliary material, an emitting auxiliary material, an electron blocking material, an emitting material (including a host and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material.

[0019] The term "multiple host materials" in the present disclosure refers to an organic electroluminescent material comprising a combination of at least two host materials. It can refer to both the material before being included in an organic electroluminescent device (for example, before vapor deposition) and the material after being included in an organic electroluminescent device (for example, after vapor deposition). The multiple host materials of the present disclosure can be included in any light-emitting layer constituting an organic electroluminescent device. Two or more compounds included in the multiple host materials of the present disclosure can be included in one light-emitting layer, or can be included in different light-emitting layers. When at least two host materials are included in one layer, the at least two host materials can be mixed and vapor-deposited to form a layer, or can be simultaneously and separately vapor-deposited to form a layer.

[0020] In the present disclosure, the term "(C1-C30) alkyl" refers to a straight-chain or branched alkyl having 1 to 30 carbon atoms constituting the chain, preferably 1 to 20, and more preferably 1 to 10. Examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and sec-butyl. In the present disclosure, the term "(C2-C30) alkenyl" refers to a straight-chain or branched alkenyl having 2 to 30 carbon atoms constituting the chain, preferably 2 to 20, and more preferably 2 to 10. Examples of the alkenyl include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, and 2-methylbut-2-enyl. In the present disclosure, the term "(C3-C30)cycloalkyl" refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 ring skeletal carbon atoms, preferably 3 to 20, more preferably 3 to 7. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, and cyclohexylmethyl. In the present disclosure, the term "(3- to 7-membered)heterocycloalkyl" refers to a cycloalkyl having 3 to 7 ring skeletal atoms, preferably 5 to 7 ring skeletal atoms, and at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably O, S, and N, and examples thereof include tetrahydrofuran, pyrrolidine, thiolane, and tetrahydropyran. In the present disclosure, "(C6-C30)aryl(ene)" refers to a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring skeletal carbon atoms, the number of which is preferably 6 to 20, more preferably 6 to 15, and may be partially saturated or may contain a spiro structure. Specific examples of aryl include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl,Examples include diphenylbenzofluorenyl, dibenzofluorenyl, phenanthrenyl, benzophenanthrenyl, phenylphenanthrenyl, anthracenyl, benzanthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, benzochrysenyl, naphthacenyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, mesityl, cumenyl, spiro[fluorene-fluoren]yl, spiro[fluorene-benzofluoren]yl, azulenyl, and tetramethyl-dihydrophenanthrenyl. More specifically, aryl is o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, p-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-t-butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-Terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2- Fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-chrysenyl, 2-chrysenyl, 3-chrysenyl, 4-chrysenyl, 5-chrysenyl, 6-chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl,11,11-dimethyl-1-benzo[a]fluorenyl, 11,11-dimethyl-2-benzo[a]fluorenyl, 11,11-dimethyl-3-benzo[a]fluorenyl, 11,11-dimethyl-4-benzo[a]fluorenyl, 11,11-dimethyl-5-benzo[a]fluorenyl, 11,11-dimethyl-6-benzo[a]fluorenyl, 11,11-dimethyl-7-benzo[a]fluorenyl, 11,11-dimethyl-8-benzo[a]fluorenyl, 11,11-dimethyl-9-benzo[a]fluorenyl, 11,11-dimethyl-10-benzo[a]fluorenyl benzo[a]fluorenyl, 11,11-dimethyl-1-benzo[b]fluorenyl, 11,11-dimethyl-2-benzo[b]fluorenyl, 11,11-dimethyl-3-benzo[b]fluorenyl, 11,11-dimethyl-4-benzo[b]fluorenyl, 11,11-dimethyl-5-benzo[b]fluorenyl, 11,11-dimethyl-6-benzo[b]fluorenyl, 11,11-dimethyl-7-benzo[b]fluorenyl, 11,11-dimethyl-8-benzo[b]fluorenyl, 11,11-dimethyl-9-benzo[b]fluorenyl, 11,1 1-dimethyl-10-benzo[b]fluorenyl, 11,11-dimethyl-1-benzo[c]fluorenyl, 11,11-dimethyl-2-benzo[c]fluorenyl, 11,11-dimethyl-3-benzo[c]fluorenyl, 11,11-dimethyl-4-benzo[c]fluorenyl, 11,11-dimethyl-5-benzo[c]fluorenyl, 11,11-dimethyl-6-benzo[c]fluorenyl, 11,11-dimethyl-7-benzo[c]fluorenyl, 11,11-dimethyl-8-benzo[c]fluorenyl, 11,11-dimethyl-9-benzo[c] fluorenyl, 11,11-dimethyl-10-benzo[c]fluorenyl, 11,11-diphenyl-1-benzo[a]fluorenyl, 11,11-diphenyl-2-benzo[a]fluorenyl, 11,11-diphenyl-3-benzo[a]fluorenyl, 11,11-diphenyl-4-benzo[a]fluorenyl, 11,11-diphenyl-5-benzo[a]fluorenyl, 11,11-diphenyl-6-benzo[a]fluorenyl, 11,11-diphenyl-7-benzo[a]fluorenyl, 11,11-diphenyl-8-benzo[a]fluorenyl,11,11-diphenyl-9-benzo[a]fluorenyl, 11,11-diphenyl-10-benzo[a]fluorenyl, 11,11-diphenyl-1-benzo[b]fluorenyl, 11,11-diphenyl-2-benzo[b]fluorenyl, 11,11-diphenyl-3-benzo[b]fluorenyl, 11,11-diphenyl-4-benzo[b]fluorenyl, 11,11-diphenyl-5-benzo[b]fluorenyl 11,11-diphenyl-6-benzo[b]fluorenyl, 11,11-diphenyl-7-benzo[b]fluorenyl, 11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9-benzo[b]fluorenyl, 11,11-diphenyl-10-benzo[b]fluorenyl, 11,11-diphenyl-1-benzo[c]fluorenyl, 11,11-diphenyl-2-benzo[c]fluorenyl 11,11-diphenyl-3-benzo[c]fluorenyl, 11,11-diphenyl-4-benzo[c]fluorenyl, 11,11-diphenyl-5-benzo[c]fluorenyl, 11,11-diphenyl-6-benzo[c]fluorenyl, 11,11-diphenyl-7-benzo[c]fluorenyl, 11,11-diphenyl-8-benzo[c]fluorenyl, 11,11-diphenyl-9-benzo[c]fluorenyl Examples of such heteroaryls include 11,11-diphenyl-10-benzo[c]fluorenyl, 9,9,10,10-tetramethyl-9,10-dihydro-1-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-2-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-3-phenanthrenyl, and 9,9,10,10-tetramethyl-9,10-dihydro-4-phenanthrenyl. In the present disclosure, a "(3- to 30-membered)heteroaryl(ene)" refers to an aryl having 3 to 30 skeletal ring atoms, including at least one heteroatom selected from the group consisting of B, N, O, S, Si, P, Se, and Ge, preferably at least one heteroatom selected from N, O, and S. The number of skeletal ring carbon atoms is preferably 5 to 25. The number of heteroatoms in the heteroaryl is preferably 1 to 4. The heteroaryl may be a monocyclic ring,Alternatively, it may be a fused ring fused with at least one benzene ring; or it may be partially saturated. Furthermore, the heteroaryl described above in this specification may be formed by bonding at least one heteroaryl group or aryl group to a heteroaryl group via a single bond. Specific examples of heteroaryl include monocyclic heteroaryls such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl; and benzofuranyl, benzothiophenyl, isobenzofuranyl, Dibenzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, benzofuroquinolinyl, benzofuroquinazolinyl, benzofuronaphthyridinyl, benzofuropyrimidinyl, naphthofuropyrimidinyl, benzothienoquinolinyl, benzothienoquinazolinyl, benzothienonaphthyridinyl, benzothienopyrimidinyl, naphthothienopyrimidinyl, pyrimidoindolyl, benzopyrimidoindolyl, benzofuropyrazinyl, naphthofuropyradizinyl nyl, benzothienopyrazinyl, naphthothienopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl Examples of fused ring heteroaryls include aryl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, indolizidinyl, acridinyl, silafluorenyl, germafluorenyl, benzotriazolyl, phenazinyl, imidazopyridinyl, chromenoquinazolinyl, thiochromenoquinazolinyl, dimethylbenzoperimidinyl, indolocarbazolyl, and indenocarbazolyl. More specifically, heteroaryls include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl,2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolizidinyl, 2-indolizidinyl, 3-indolizidinyl, 5-indolizidinyl, 6-indolizidinyl, 7-indolizidinyl, 8-indolizidinyl, inyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazo aryl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazol-1-yl, azacarbazol-2-yl, azacarbazol-3-yl, azacarbazol-4-yl, azacarbazol-5-yl, azacarbazol-6-yl, azacarbazol-7-yl, azacarbazol-8-yl, azacarbazol-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl yl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl,3-methylpyrrol-5-yl, 2-t-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-t-butyl-1-indolyl, 4-t-butyl-1-indolyl, 2-t-butyl-3-indolyl, 4-t-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl , 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-naphtho-[1,2-b]-benzofuranyl, 2-naphtho-[1,2-b]-benzofuranyl, 3-naphtho-[1,2-b]-benzofuranyl, 4-naphtho-[1,2-b]-benzofuranyl, 5-naphtho-[1,2-b]-benzofuranyl, 6-naphtho-[1,2-b]-benzofuranyl, 7-naphtho-[1,2-b]-benzofuranyl, 8-naphtho-[1,2-b]-benzofuranyl, 9-naphtho-[1,2-b]-benzofuranyl, 10-naphtho-[1,2-b]-benzofuranyl 1-naphtho-[2,3-b]-benzofuranyl, 2-naphtho-[2,3-b]-benzofuranyl, 3-naphtho-[2,3-b]-benzofuranyl, 4-naphtho-[2,3-b]-benzofuranyl, 5-naphtho-[2,3-b]-benzofuranyl, 6-naphtho-[2,3-b]-benzofuranyl, 7-naphtho-[2,3-b]-benzofuranyl, 8-naphtho-[2,3-b]-benzofuranyl, 9-naphtho-[2,3-b]-benzofuranyl, 10-naphtho-[2,3-b]-benzofuranyl, 1-naphtho-[2,1-b]-benzofuranyl, 2 -naphtho-[2,1-b]-benzofuranyl, 3-naphtho-[2,1-b]-benzofuranyl, 4-naphtho-[2,1-b]-benzofuranyl, 5-naphtho-[2,1-b]-benzofuranyl, 6-naphtho-[2,1-b]-benzofuranyl, 7-naphtho-[2,1-b]-benzofuranyl, 8-naphtho-[2,1-b]-benzofuranyl, 9-naphtho-[2,1-b]-benzofuranyl, 10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b]-benzothiophenyl, 2-naphtho-[1,2-b]-benzothiophenyl,3-naphtho-[1,2-b]-benzothiophenyl, 4-naphtho-[1,2-b]-benzothiophenyl, 5-naphtho-[1,2-b]-benzothiophenyl, 6-naphtho-[1,2-b]-benzothiophenyl, 7-naphtho-[1,2-b]-benzothiophenyl, 8-naphtho-[1,2-b]-benzothiophenyl, 9-naphtho-[1,2-b]-benzothiophenyl, 10-naphtho-[1,2-b]-benzothiophenyl, 1-naphtho-[2,3-b]-benzothiophenyl, 2-naphtho-[2,3-b]-benzothiophenyl, 3-naphtho-[2 ,3-b]-benzothiophenyl, 4-naphtho-[2,3-b]-benzothiophenyl, 5-naphtho-[2,3-b]-benzothiophenyl, 1-naphtho-[2,1-b]-benzothiophenyl, 2-naphtho-[2,1-b]-benzothiophenyl, 3-naphtho-[2,1-b]-benzothiophenyl, 4-naphtho-[2,1-b]-benzothiophenyl, 5-naphtho-[2,1-b]-benzothiophenyl, 6-naphtho-[2,1-b]-benzothiophenyl, 7-naphtho-[2,1-b]-benzothiophenyl, 8-naphtho-[2,1-b]-benzo Thiophenyl, 9-naphtho-[2,1-b]-benzothiophenyl, 10-naphtho-[2,1-b]-benzothiophenyl, 2-benzofuro[3,2-d]pyrimidinyl, 6-benzofuro[3,2-d]pyrimidinyl, 7-benzofuro[3,2-d]pyrimidinyl, 8-benzofuro[3,2-d]pyrimidinyl, 9-benzofuro[3,2-d]pyrimidinyl, 2-benzothio[3,2-d]pyrimidinyl, 6-benzothio[3,2-d]pyrimidinyl, 7-benzothio[3,2-d]pyrimidinyl, 8-benzothio[3,2-d]pyrimidinyl, 9-benzofuro[3,2-d]pyrimidinyl benzothio[3,2-d]pyrimidinyl, 2-benzofuro[3,2-d]pyrazinyl, 6-benzofuro[3,2-d]pyrazinyl, 7-benzofuro[3,2-d]pyrazinyl, 8-benzofuro[3,2-d]pyrazinyl, 9-benzofuro[3,2-d]pyrazinyl, 2-benzothio[3,2-d]pyrazinyl, 6-benzothio[3,2-d]pyrazinyl, 7-benzothio[3,2-d]pyrazinyl, 8-benzothio[3,2-d]pyrazinyl, 9-benzothio[3,2-d]pyrazinyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl,The ring may be 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-germafluorenyl, 4-germafluorenyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, etc. In the present disclosure, the term "fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring" refers to a ring formed by fusing at least one aliphatic ring having 3 to 30 ring skeletal carbon atoms (preferably 3 to 25, more preferably 3 to 18, carbon atoms) with at least one aromatic ring having 6 to 30 ring skeletal carbon atoms (preferably 6 to 25, more preferably 6 to 18, carbon atoms). For example, the fused ring may be a fused ring of at least one benzene and at least one cyclohexane, or a fused ring of at least one naphthalene and at least one cyclopentane. In this specification, a carbon atom of a fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring may be replaced with at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S. In the present disclosure, the term "halogen" includes F, Cl, Br, and I.

[0021] Additionally, "ortho (o)," "meta (m)," and "para (p)" are meant to indicate the substitution positions of all substituents. The ortho position refers to compounds where the substituents are adjacent to each other, i.e., at the 1st and 2nd positions on the benzene. The meta position refers to the substitution position next to the immediately adjacent substitution position, i.e., compounds with substituents at the 1st and 3rd positions on the benzene. The para position refers to the substitution position next to the meta position, i.e., compounds with substituents at the 1st and 4th positions on the benzene.

[0022] The term "ring formed by linking adjacent substituents" in the present disclosure refers to a substituted or unsubstituted (3- to 30-membered) monocyclic or polycyclic aliphatic ring, aromatic ring, or combination thereof, formed by linking or condensing two or more adjacent substituents. Preferably, the ring formed includes a substituted or unsubstituted (3- to 26-membered) monocyclic or polycyclic aliphatic ring, aromatic ring, or combination thereof. Furthermore, the ring may include at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably at least one heteroatom selected from the group consisting of N, O, and S. According to one embodiment of the present disclosure, the number of atoms in the ring skeleton is 5 to 20; according to another embodiment of the present disclosure, the number of atoms in the ring skeleton is 5 to 15. The bond or fused ring may be, for example, a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted benzene ring, or a substituted or unsubstituted carbazole ring.

[0023] Furthermore, the term "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a specific functional group is replaced with another atom or another functional group, i.e., a substituent. Preferably, in the present disclosure, the substituted (C1-C30) alkyl, substituted (C2-C30) alkenyl, substituted (C6-C30) aryl(ene), substituted (3-30 membered) heteroaryl(ene), substituted (C3-C30) cycloalkyl, substituted (3-7 membered) heterocycloalkyl, substituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, substituted tri(C1-C30) alkylsilyl, substituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted (C1-C30) alkyldi(C6-C30) The substituents of the (C30)arylsilyl and substituted tri(C6-C30)arylsilyl are each independently deuterium, halogen, cyano, carboxyl, nitro, hydroxy, (C1-C30)alkyl, halo(C1-C30)alkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C1-C30)alkoxy, (C1-C30)alkylthio, (C3-C30)cycloalkyl, (C3-C30)cycloalkenyl, (3- to 7-membered)heterocycloalkyl, (C6-C30)arylthio, oxy, (C6-C30)arylthio, unsubstituted or (5-30 membered) heteroaryl substituted with (C6-C30)aryl, unsubstituted or (5-30 membered) heteroaryl substituted with (C6-C30)aryl, tri(C1-C30)alkylsilyl, tri(C6-C30)arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C1-C30)alkyldi(C6-C30)arylsilyl, fused rings of (C3-C30)aliphatic rings and (C6-C30)aromatic rings, amino, mono - or di-(C1 to C30) alkylamino, mono- or di-(C2 to C30) alkenylamino, (C1 to C30) alkyl(C2 to C30) alkenylamino, substituted or unsubstituted mono- or di-(C6 to C30) arylamino, (C1 to C30) alkyl(C6 to C30) arylamino, mono- or di-(3 to 30 membered) heteroarylamino, (C1 to C30) alkyl(3 to 30 membered) heteroarylamino, (C2 to C30) alkenyl(C6 to C30) arylamino,The substituent represents at least one selected from the group consisting of (C2-C30)alkenyl(3-30 membered)heteroarylamino, (C6-C30)aryl(3-30 membered)heteroarylamino, (C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30)arylcarbonyl, di(C6-C30)arylboronyl, di(C1-C30)alkylboronyl, (C1-C30)alkyl(C6-C30)arylboronyl, (C6-C30)ar(C1-C30)alkyl, and (C1-C30)alkyl(C6-C30)aryl. For example, the substituent may be methyl, phenyl, naphthyl, p-biphenyl, m-biphenyl, m-terphenyl, fluorenyl, phenanthrenyl, pyridyl, dibenzothiophenyl, or dibenzofuranyl.

[0024] In the following, an organic electroluminescent compound according to one embodiment is described.

[0025] The organic electroluminescent compound according to one embodiment is represented by Formula 1 below: [ka]

[0026] In Equation 1, R1 to R4 are each independently *-(L1) a -(Ar1) b , hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl, or may be linked to adjacent substituents to form a ring; R5~R 12 are each independently *-(L1) a -(Ar1) b, hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, or substituted or unsubstituted tri(C6-C30) arylsilyl, or may be linked to adjacent substituents to form a ring; R1~R 12 At least one of the following is *-(L1) a -(Ar1) b Provided that it represents; L1 represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30-membered) heteroarylene; Ar1 represents a substituted or unsubstituted (C6 to C30) aryl, a substituted or unsubstituted (3 to 30-membered) heteroaryl, or -N-(Ar2)(Ar3); Ar2 and Ar3 each independently represent a substituted or unsubstituted (C1 to C30) alkyl, a substituted or unsubstituted (C2 to C30) alkenyl, a substituted or unsubstituted fused ring of a (C3 to C30) aliphatic ring and a (C6 to C30) aromatic ring, a substituted or unsubstituted (C6 to C30) aryl, or a substituted or unsubstituted (3 to 30-membered) heteroaryl; a represents an integer of 1 or 2, b represents an integer of 1 to 4, and when a and b are 2 or more, each L1 and each Ar1 may be the same or different; R5~R 10 and R 12 represents hydrogen, and R 11 with the proviso that compounds of formula 1 containing a substituted amino group are excluded.

[0027] In one embodiment, R1 to R4 are each independently *-(L1) a -(Ar1) b , substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl, and preferably *-(L1) a -(Ar1) b , substituted or unsubstituted (C1-C10) alkyl, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5-25 membered) heteroaryl, more preferably *-(L1) a -(Ar1) b , substituted or unsubstituted (C1-C4) alkyl, substituted or unsubstituted (C6-C18) aryl, or substituted or unsubstituted (5-18 membered) heteroaryl. For example, R1 to R4 may each independently be substituted or unsubstituted methyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, or *-(L1) a -(Ar1) b may be.

[0028] In one embodiment, R to R 12 are each independently *-(L1) a -(Ar1) b , hydrogen, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl; or it may be linked to adjacent substituents to form a ring, preferably *-(L1) a -(Ar1) b , hydrogen, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5-25 membered) heteroaryl; or may be linked with adjacent substituents to form a substituted or unsubstituted (5-30 membered) monocyclic or polycyclic aliphatic ring, aromatic ring, or a combination thereof, more preferably *-(L1) a -(Ar1)b , hydrogen, substituted or unsubstituted (C6-C18) aryl, or substituted or unsubstituted (5-18 membered) heteroaryl; or may be linked with adjacent substituents to form a substituted or unsubstituted (5-30 membered) monocyclic or polycyclic aromatic ring.

[0029] In the above equation 1, R1 to R 12 At least one of the is *-(L1) a -(Ar1) b For example, at least one of R1 to R4, at least one of R5 to R8, or at least one of R9 to R 12 At least one of the is *-(L1) a -(Ar1) b For example, *-(L1) among R1 to R4 may be used. a -(Ar1) b R1 to R4 other than the above may each independently be substituted or unsubstituted methyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl. 12 Of *-(L1) a -(Ar1) b Other than R5~R 12 may each independently be hydrogen, unsubstituted or (C6-C30)aryl or deuterium-substituted phenyl, substituted or unsubstituted m-biphenyl, or substituted or unsubstituted pyridyl, or R5 to R 12 or R to R 12 Adjacent substituents may be linked to each other to form a benzene ring, a naphthalene ring, or a phenanthrene ring.

[0030] According to one embodiment, Formula 1 may be an organic electroluminescent compound in which Ar1 represents a substituted or unsubstituted (3-30 membered) heteroaryl containing at least one N or -N-(Ar2)(Ar3); and L1 represents a single bond or a substituted or unsubstituted (C6-C30) arylene.

[0031] According to one embodiment, the organic electroluminescent compound represented by Formula 1 can be represented by any one of the following Formulas 1-1 to 1-4. [ka]

[0032] In formulas 1-1 to 1-4, R1~R 12 , L1, Ar1, a, and b are as defined in Formula 1 above.

[0033] According to another embodiment, the organic electroluminescent compound represented by Formula 1 can be represented by any one of the following Formulas 1-5 to 1-13. [ka] [ka] [ka]

[0034] In formulas 1-5 to 1-13, R1~R 12 is as defined in Equation 1 above; R 13 ~R 18 are each independently *-(L1) a -(Ar1) b, hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, or substituted or unsubstituted tri(C6-C30) arylsilyl, or may be linked to adjacent substituents to form a ring; R1 to R in formulas 1-5 to 1-7 14 At least one of R1 to R2 in formulas 1-8 to 1-10 16 and at least one of R1 to R2 in formulas 1-11 to 1-13. 18 At least one of the following is *-(L1) a -(Ar1) b Provided that it represents; L1, Ar1, a, and b are as defined in Formula 1.

[0035] In one embodiment, Ar1 may be a substituted or unsubstituted (C6 to C30) aryl, a substituted or unsubstituted (5 to 30-membered) heteroaryl, or -N-(Ar2)(Ar3), preferably a substituted or unsubstituted (5 to 25-membered) heteroaryl containing at least one N, or -N-(Ar2)(Ar3), more preferably a substituted or unsubstituted (5 to 25-membered) heteroaryl containing at least one N, or -N-(Ar2)(Ar3). Here, Ar2 and Ar3 may each independently represent a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30-membered) heteroaryl, preferably a substituted or unsubstituted fused ring of a (C3-C20) aliphatic ring and a (C6-C25) aromatic ring, a substituted or unsubstituted (C6-C25) aryl, or a substituted or unsubstituted (5-25-membered) heteroaryl, and more preferably a substituted or unsubstituted fused ring of a (C3-C10) aliphatic ring and a (C6-C18) aromatic ring, a substituted or unsubstituted (C6-C18) aryl, or a substituted or unsubstituted (5-18-membered) heteroaryl. For example, Ar2 and Ar3 may each independently be substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted chrysenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzofluorenyl, or substituted or unsubstituted dihydrophenanthrenyl.

[0036] In one embodiment, the substituted or unsubstituted (C6 to C30) aryl in Ar1 may be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylenyl, or substituted or unsubstituted phenanthrenyl, and preferably phenyl that is unsubstituted or substituted with deuterium or a (5 to 30-membered)heteroaryl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted m-terphenyl, or substituted or unsubstituted naphthyl.

[0037] In one embodiment, the substituted or unsubstituted (C3-C30)heteroaryl in Ar1 is substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted dibenzoquinolinyl, substituted or unsubstituted dibenzoquinazolinyl, substituted or unsubstituted dibenzoquinoxalinyl, substituted or unsubstituted indenopyridyl, substituted or unsubstituted indenopyrimidinyl, substituted or unsubstituted indenopyrazinyl, substituted or unsubstituted benzofuropyridyl, substituted or unsubstituted benzofuropyrimidinyl, substituted or unsubstituted benzofuropyrazinyl, substituted or unsubstituted benzothiopyridyl, substituted or unsubstituted benzothiopyrimidinyl, and quinazolinyl unsubstituted or substituted with (C6-C30) aryl and / or (5-30-membered) heteroaryl, quinoxalinyl unsubstituted or substituted with (C6-C30) aryl and / or (5-30-membered) heteroaryl, benzoquinoxalinyl unsubstituted or substituted with (C6-C30) aryl, benzoquinoxalinyl unsubstituted or substituted with (C6-C30) aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or triazinyl unsubstituted or substituted with (C6-C30) aryl and / or (5-30-membered) heteroaryl.

[0038] In one embodiment, L1 may be a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (5 to 30-membered) heteroarylene, preferably a single bond, a substituted or unsubstituted (C6 to C25) arylene, or a substituted or unsubstituted (5 to 25-membered) heteroarylene, and more preferably a single bond, a substituted or unsubstituted (C6 to C18) arylene, or a substituted or unsubstituted (5 to 18-membered) heteroarylene. For example, L1 is a single bond, or a substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthrenylene, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted triazinylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted quinoxalinylene, substituted or unsubstituted quinazolinylene, substituted or unsubstituted dibenzofuranylene, or substituted or unsubstituted and may be a substituted or unsubstituted benzoquinoxalinylene, and preferably may be a substituted or unsubstituted phenylene, substituted or unsubstituted p-biphenylene, substituted or unsubstituted m-biphenylene, substituted or unsubstituted o-biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted pyridylene, substituted or unsubstituted triazinylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted quinoxalinylene, substituted or unsubstituted quinazolinylene, substituted or unsubstituted dibenzofuranylene, or substituted or unsubstituted benzoquinoxalinylene.

[0039] In one embodiment, a may be an integer of 1 or 2, b may be an integer of 1 or 2, and when a and b are 2, each L1 and each Ar1 may be the same or different.

[0040] According to one embodiment, the organic electroluminescent compounds represented by the above formula 1 can be more specifically exemplified by, but not limited to, the following compounds: [ka]

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[0041] The organic electroluminescent compound of formula 1 according to the present disclosure can be prepared as shown in the following reaction schemes 1 to 3, but is not limited thereto. Furthermore, it can be prepared by synthetic methods known to those skilled in the art. [ka] [ka]

[0042] In the above reaction schemes 1 to 3, R1 to R 12 , L1, and Ar1 are as defined in Equation 1 above, and R 13 ~R 16 is R5~R in the above equation 1. 12 It is as defined above.

[0043] As described above, illustrative synthetic examples of compounds represented by Formula 1 according to the present disclosure are described, and these are based on Suzuki cross-coupling reactions, Buchwald-Hartwig cross-coupling reactions, N-arylation reactions, H-mont-mediated etherification reactions, Miyaura borylation reactions, intramolecular acid-induced cyclization reactions, Pd(II)-catalyzed oxidative cyclization reactions, Grignard reactions, Heck reactions, cyclodehydration reactions, SN1 substitution reactions, SN2 substitution reactions, and phosphine-mediated reductive cyclization reactions, etc. It will be understood by those skilled in the art that the above reactions will also proceed when other substituents defined in Formula 1 other than those described in the specific synthetic examples are bonded.

[0044] The organic electroluminescent compound according to another embodiment can be represented by Formula 2 below: [ka]

[0045] In Equation 2, R'1 to R'4 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C3 to C30) cycloalkyl, substituted or unsubstituted (3 to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6 to C30) aryl, or substituted or unsubstituted (3 to 30-membered) heteroaryl, or may be linked to adjacent substituents to form a ring; R'5 and R'6 each independently represent hydrogen or deuterium; L'1 to L'3 each independently represent a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30-membered) heteroarylene; Ar' represents a substituted or unsubstituted (C6 to C30) aryl or a substituted or unsubstituted (3 to 30-membered) heteroaryl; BFL represents substituted or unsubstituted benzo[a]fluorenyl, substituted or unsubstituted benzo[b]fluorenyl, or substituted or unsubstituted benzo[c]fluorenyl; m represents an integer of 1 to 4, n represents an integer of 1 to 3, and when m and n are 2 or greater, each R'5 and each R'6 may be the same or different.

[0046] In one embodiment, R'1 to R'4 may each independently represent hydrogen, deuterium, substituted or unsubstituted (C1 to C30) alkyl, or substituted or unsubstituted (C6 to C30) aryl, preferably substituted or unsubstituted (C1 to C10) alkyl, or substituted or unsubstituted (C6 to C25) aryl, more preferably substituted or unsubstituted (C1 to C4) alkyl. For example, all of R'1 to R'4 may be methyl.

[0047] In one embodiment, all of R'5 and R'6 can be hydrogen, or all of R'5 and R'6 can be deuterium.

[0048] In one embodiment, L'1 to L'3 may each independently represent a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (5 to 30-membered) heteroarylene, preferably a single bond, a substituted or unsubstituted (C6 to C25) arylene, or a substituted or unsubstituted (5 to 25-membered) heteroarylene, and more preferably a single bond, a substituted or unsubstituted (C6 to C18) arylene, or a substituted or unsubstituted (5 to 18-membered) heteroarylene. For example, L'1 to L'3 may each independently represent a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted carbazolylene.

[0049] In one embodiment, Ar' may be substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (5-30-membered) heteroaryl, preferably substituted or unsubstituted (C6-C25) aryl or substituted or unsubstituted (5-25-membered) heteroaryl, and more preferably substituted or unsubstituted (C6-C18) aryl or substituted or unsubstituted (5-18-membered) heteroaryl. For example, Ar' may be substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, unsubstituted or deuterated p-biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted dibenzofuranyl.

[0050] In one embodiment, BFL may be a substituted or unsubstituted benzo[a]fluorenyl, a substituted or unsubstituted benzo[b]fluorenyl, or a substituted or unsubstituted benzo[c]fluorenyl, and the substituents of these substituted benzo[a]fluorenyl, substituted benzo[b]fluorenyl, or substituted benzo[c]fluorenyl may be deuterium, (C1-C10) alkyl, or (C6-C18) aryl, such as deuterium, methyl, or phenyl.

[0051] According to one embodiment, the organic electroluminescent compounds represented by the above formula 2 can be more specifically exemplified by, but not limited to, the following compounds: [ka] [ka] [ka] [ka]

[0052] The organic electroluminescent compound of formula 2 according to the present disclosure can be prepared by referring to, but not limited to, the reactions shown in the above reaction schemes 1 to 3. Furthermore, it can be prepared by synthetic methods known to those skilled in the art.

[0053] The organic electroluminescent compound according to another embodiment can be represented by the following formula 3: [ka]

[0054] In Equation 3, R' 11 ~R' 14 each independently represents a substituted or unsubstituted methyl; R' 15 and R' 16 each independently represents hydrogen or deuterium; Ar' 11 and Ar' 12 each independently represent an unsubstituted or deuterium-substituted phenyl, an unsubstituted or deuterium-substituted biphenyl, an unsubstituted or deuterium-substituted terphenyl, an unsubstituted or deuterium-substituted naphthyl, an unsubstituted or deuterium-substituted group of formula (a) below, or a combination thereof: [ka] (x represents an integer of 1 to 4, y represents an integer of 1 to 3, and when x and y are 2 or more, each R' 15 and each R' 16 may be the same or different).

[0055] In one embodiment, R' 11 ~R' 14 All of these may be unsubstituted methyl.

[0056] In one embodiment, R' 15 and R' 16may all be hydrogen, or R' 15 and R' 16 may all be deuterium.

[0057] In one embodiment, Ar' 11 and Ar' 12 may each independently be unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted biphenyl, unsubstituted or deuterium-substituted terphenyl, unsubstituted or deuterium-substituted naphthyl, unsubstituted or deuterium-substituted group of the above formula (a), or a combination thereof, and preferably be unsubstituted phenyl, unsubstituted o-biphenyl, unsubstituted m-biphenyl, unsubstituted or deuterium-substituted p-biphenyl, unsubstituted o-terphenyl, unsubstituted m-terphenyl, unsubstituted p-biphenyl, unsubstituted group of the above formula (a), or a combination thereof.

[0058] According to one embodiment, the organic electroluminescent compounds represented by the above formula 3 can be more specifically exemplified by, but not limited to, the following compounds: [ka] [ka]

[0059] The organic electroluminescent compound of formula 3 according to the present disclosure can be prepared by referring to, but not limited to, the reactions shown in the above reaction schemes 1 to 3. Furthermore, it can be prepared by synthetic methods known to those skilled in the art.

[0060] The present disclosure relates to an organic electroluminescent material comprising an organic electroluminescent compound of Formula 1 and an organic electroluminescent device comprising the organic electroluminescent material. We can provide services.

[0061] Furthermore, the present disclosure can provide an organic electroluminescent compound of Formula 2, and an organic electroluminescent device including the same.

[0062] Furthermore, the present disclosure can provide an organic electroluminescent compound of Formula 3, and an organic electroluminescent device including the same.

[0063] According to one embodiment of the present disclosure, the organic electroluminescent material of the present disclosure may contain only the organic electroluminescent compound of Formula 1, or may further contain conventional materials contained in organic electroluminescent materials. In one embodiment, the compound of Formula 1 may be contained in a hole transporting zone as a hole transporting material. The hole transporting zone may be composed of one or more layers selected from the group consisting of a hole transporting layer, a hole injection layer, an electron blocking layer, and a hole auxiliary layer, and each of the layers may be composed of one or more layers. In another embodiment, the compound of Formula 1 may be contained in an electron transporting zone as an electron transporting material. The electron transporting zone may be composed of one or more layers selected from the group consisting of an electron transporting layer, an electron injection layer, a hole blocking layer, and an electron auxiliary layer, and each of the layers may be composed of one or more layers. In another embodiment, the compound of Formula 1 may be contained in an emitting layer as a host material.

[0064] According to another embodiment of the present disclosure, the organic electroluminescent compound represented by Formula 2 and / or the organic electroluminescent compound represented by Formula 3 may be included in the hole transporting zone as a hole transporting material.

[0065] The organic electroluminescent material of the present disclosure may further include, in addition to the organic electroluminescent compound of Formula 1 above, at least one host compound and at least one dopant.

[0066] The host material included in the organic electroluminescent material of the present disclosure may further include an organic electroluminescent compound different from the organic electroluminescent compound of Formula 1 (first host material) as a second host material. That is, the organic electroluminescent material according to one embodiment of the present disclosure may include multiple host materials. Specifically, the multiple host materials according to one embodiment may include at least one compound of Formula 1 as a first host material and at least one second host material different from the first host material. The weight ratio between the first host material and the second host material is 1:99 to 99:1, preferably 10:90 to 90:10, and more preferably 30:70 to 70:30.

[0067] The second host material according to one embodiment comprises a compound represented by Formula 11: [ka]

[0068] In Equation 11, L a represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30-membered) heteroarylene; Ar a represents a substituted or unsubstituted (C6 to C30) aryl or a substituted or unsubstituted (3 to 30-membered) heteroaryl, R9 and R 10are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-50 membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C2-C30) alkenylamino , a substituted or unsubstituted (C1-C30) alkyl(C2-C30) alkenylamino, a substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, a substituted or unsubstituted (C1-C30) alkyl(3-30 membered) heteroarylamino, a substituted or unsubstituted (C2-C30) alkenyl(C6-C30) arylamino, a substituted or unsubstituted (C2-C30) alkenyl(3-30 membered) heteroarylamino, a substituted or unsubstituted mono- or di-(C6-C30) arylamino, a substituted or unsubstituted mono- or di-(3-30 membered) heteroarylamino, or a substituted or unsubstituted (C6-C30) aryl(3-30 membered) arylamino, or adjacent substituents may be bonded to each other to form a ring; f and g each independently represent an integer of 1 to 4, and when f and g are 2 or more, each of R9 and R 10 may be the same or different.

[0069] The second host material represented by Formula 11 according to one embodiment can be represented by Formula 12 or 13 below. [ka]

[0070] In equations 12 and 13, L a, Ar a , R9, R 10 , and f are as defined in Equation 11 above; T1 and T2 each independently represent a single bond, O, or S; L b is the above equation 11. a as defined above; Ar b is the above equation 11, Ar a as defined above; R 11 ~R 14 are each independently as defined for R9 in Formula 11 above; X1 is O, S, or NR a represents; R a represents a substituted or unsubstituted (C6-C30) aryl; g' and h each independently represent an integer of 1 to 3, i and k each independently represent an integer of 1 to 4, j represents an integer of 1 or 2, and when g', h, i, j, and k are 2 or more, R 10 Each of R 11 Each of R 12 Each of R 13 and R 14 may be the same or different.

[0071] In one embodiment, L a and L b may each independently represent a single bond or a substituted or unsubstituted (C6 to C30) arylene, preferably a single bond or a substituted or unsubstituted (C6 to C25) arylene, and more preferably a single bond or a substituted or unsubstituted (C6 to C18) arylene. For example, L a and L b may each independently be a single bond, phenylene, or biphenylene.

[0072] In one embodiment, Ar a and Ar bmay each independently be a substituted or unsubstituted (C6-C30) aryl, preferably a substituted or unsubstituted (C6-C25) aryl, more preferably an unsubstituted (C6-C30) aryl or a (C6-C25) aryl substituted with a (5- to 30-membered) heteroaryl. For example, Ar a and Ar b may each independently be unsubstituted phenyl or substituted with at least one of methyl, cyano, triphenylsilane, phenyl, biphenyl, and naphthyl, unsubstituted or phenyl-substituted carbazolyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted fluorenyl, unsubstituted or phenyl-substituted naphthyl, or substituted or unsubstituted triphenylenyl.

[0073] In one embodiment, R a may be a substituted or unsubstituted (C6-C30) aryl, preferably a substituted or unsubstituted (C6-C25) aryl, and more preferably a (C6-C25) aryl that is unsubstituted or substituted with a (C6-C30) aryl or a (5-30 membered) heteroaryl. For example, R a may be unsubstituted or phenyl substituted with at least one of phenyl, biphenyl, and naphthyl, unsubstituted or phenyl-substituted carbazolyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, unsubstituted or phenyl-substituted naphthyl, or substituted or unsubstituted triphenylenyl.

[0074] In one embodiment, R to R 14may each independently represent hydrogen, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl, preferably hydrogen, a substituted or unsubstituted (C1-C10) alkyl, a substituted or unsubstituted (C6-C25) aryl, or a substituted or unsubstituted (5-25 membered) heteroaryl, more preferably hydrogen, a substituted or unsubstituted (C1-C4) alkyl, a substituted or unsubstituted (C6-C18) aryl, or a substituted or unsubstituted (5-18 membered) heteroaryl. For example, R9 to R 14 may each independently be hydrogen, substituted or unsubstituted methyl, substituted or unsubstituted phenyl, or substituted or unsubstituted carbazolyl.

[0075] According to one embodiment, the compound represented by formula 11 can be more specifically exemplified by, but not limited to, the following compounds: [ka] [ka] [ka] [ka] [ka]

[0076] Compounds of formula 11 according to the present disclosure can be prepared by synthetic methods known to those skilled in the art.

[0077] The dopant contained in the organic electroluminescent material of the present disclosure can be at least one phosphorescent or fluorescent dopant, preferably a phosphorescent dopant.The phosphorescent dopant material applied to the present disclosure is not particularly limited, but preferably can be a metal complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), optionally, a metal complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), more preferably an ortho-metal complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and even more preferably an ortho-metal iridium complex compound.

[0078] The dopant included in the organic electroluminescent device of the present disclosure may be, but is not limited to, a compound represented by the following formula 101: [ka]

[0079] In Equation 101, L is the following structure 1 to 3: [ka] is selected from In structures 1 to 3, R 100 ~R 103each independently represent hydrogen, deuterium, halogen, unsubstituted or deuterium and / or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (3-30 membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; or adjacent substituents may be bonded to each other to form a ring, for example, a ring with pyridine, such as substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted benzofuropyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuroquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indenoquinoline; R 104 ~R 107 each independently represent hydrogen, deuterium, halogen, unsubstituted or deuterium and / or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; or adjacent substituents may be bonded to each other to form a ring, for example, a ring together with benzene, such as substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuropyridine, or substituted or unsubstituted benzothienopyridine; R 201 ~R 220 each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium and / or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C6-C30) aryl; or adjacent substituents can be linked to each other to form a ring; s represents an integer of 1 to 3.

[0080] In particular, specific examples of dopant compounds include, but are not limited to, the following: [ka] [ka] [ka] [ka] [ka] [ka]

[0081] In the following, organic electroluminescent devices to which the above-mentioned organic electroluminescent compounds and / or organic electroluminescent materials are applied will be described.

[0082] An organic electroluminescent device according to one embodiment includes a first electrode, a second electrode, and at least one organic layer sandwiched between the first and second electrodes. The organic layer may include at least one layer selected from a hole transport layer, a hole injection layer, an electron blocking layer, a hole auxiliary layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron auxiliary layer, and each layer may be further composed of multiple layers. The organic layer may further include at least one compound selected from the group consisting of arylamine compounds and styrylarylamine compounds, and may further include at least one metal selected from the group consisting of Group 1 metals, Group 2 metals, Period 4 transition metals, Period 5 transition metals, lanthanides, and organometallic d-transition elements of the periodic table, or at least one complex compound containing such a metal.

[0083] The compound represented by Formula 1 and / or the compound represented by Formula 2 in the present disclosure can be included in one or more layers constituting an organic electroluminescent device. According to one embodiment, the organic layer includes a hole transporting zone and / or an electron transporting zone, and / or an emitting layer comprising the organic electroluminescent compound according to the present disclosure, such as a hole transporting layer and / or a hole assisting layer and / or a hole blocking layer and / or an electronic assisting layer and / or an emitting layer. For example, when the compound of Formula 1 is included in the hole transporting layer and / or the hole assisting layer and / or the hole blocking layer and / or the electronic assisting layer and / or the emitting layer, the compound of Formula 1 can be included as a hole transporting material and / or a hole assisting material and / or a hole blocking material and / or an electronic assisting material and / or a host material, respectively. The hole transport layer and / or the hole auxiliary layer and / or the hole blocking layer and / or the electron auxiliary layer and / or the light-emitting layer may, for example, contain the organic electroluminescent compound of the present disclosure alone or a mixture of at least two organic electroluminescent compounds, and may further contain conventional materials contained in organic electroluminescent materials.

[0084] According to one embodiment, the hole transport layer may comprise at least one organic electroluminescent compound represented by Formula 1, for example, the hole transport layer may comprise at least one compound selected from compounds C-1 to C-700 represented by Formula 1. According to another embodiment, the hole transport layer may comprise at least one organic electroluminescent compound represented by Formula 2, for example, the hole transport layer may comprise at least one compound selected from compounds C1-1 to C1-69 represented by Formula 2. According to another embodiment, the hole transport layer may comprise at least one organic electroluminescent compound represented by Formula 3, for example, the hole transport layer may comprise at least one compound selected from compounds C2-1 to C2-38 represented by Formula 3.

[0085] An emitting layer according to one embodiment may include multiple host materials including at least one first host material represented by Formula 1 and at least one second host material represented by Formula 11. According to one embodiment, the emitting layer may include at least one compound selected from compounds C-1 to C-700 as the first host material represented by Formula 1, and at least one compound selected from compounds H-1 to H-85 as the second host material represented by Formula 11. According to another embodiment, the emitting layer may include an organic electroluminescent compound represented by Formula 2. For example, the emitting layer may include at least one compound selected from compounds C1-1 to C1-69 represented by Formula 2.

[0086] According to another embodiment, the hole-blocking layer may include at least one organic electroluminescent compound represented by Formula 1, for example, the hole-blocking layer may include at least one of compounds C-1 to C-700 represented by Formula 1.

[0087] The organic electroluminescent material according to one embodiment can be used as a material for the organic layer of a white organic light-emitting device. White organic light-emitting devices have suggested various structures, such as a parallel side-by-side arrangement method, a stacked arrangement method, or a color conversion material (CCM) method, depending on the arrangement of R (red), G (green), YG (yellow-green), or B (blue) light-emitting units. In addition, the organic electroluminescent material according to one embodiment can also be applied to an organic electroluminescent device containing QDs (quantum dots).

[0088] One of the first electrode and the second electrode can be an anode, and the other can be a cathode. In this case, the first electrode and the second electrode can be formed as a transparent conductive material, a semi-transparent conductive material, or a reflective conductive material, respectively. The organic electroluminescent device can be a top-emitting type, a bottom-emitting type, or a dual-side emitting type depending on the type of material forming the first electrode and the second electrode.

[0089] 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. The hole injection layer may be a multilayer to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, and each of the multilayers can simultaneously use two types of compounds. The hole injection layer can be doped with a p-type dopant. An electron blocking layer can also be disposed between the hole transport layer (or hole injection layer) and the light-emitting layer, preventing electrons from overflowing from the light-emitting layer, thereby confining excitons within the light-emitting layer and preventing light leakage. The hole transport layer or electron blocking layer can be a multilayer, in which case each layer can use multiple compounds.

[0090] An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof can be used between the light-emitting layer and the cathode. The electron buffer layer can be multi-layered to control electron injection and improve the interface characteristics between the light-emitting layer and the electron injection layer, and each layer can use two different compounds simultaneously. The hole blocking layer or the electron transport layer can be multi-layered, and each layer can use multiple compounds. The electron injection layer can also be doped with an n-type dopant.

[0091] The light-emitting auxiliary layer can be disposed between the anode and the light-emitting layer or between the cathode and the light-emitting layer. When the light-emitting auxiliary layer is disposed between the anode and the light-emitting layer, it can be used to promote hole injection and / or hole transport or prevent electron overflow. When the light-emitting auxiliary layer is disposed between the cathode and the light-emitting layer, it can be used to promote electron injection and / or electron transport or prevent hole overflow. In addition, the hole auxiliary layer can be disposed between the hole transport layer (or hole injection layer) and the light-emitting layer and can be effective in promoting or blocking the hole transport rate (or hole injection rate), thereby allowing the charge balance to be controlled. When an organic electroluminescent device includes two or more hole transport layers, the additional hole transport layer can be used as a hole auxiliary layer or an electron blocking layer. The light-emitting auxiliary layer, hole auxiliary layer, or electron blocking layer can have the effect of improving the efficiency and / or life of the organic electroluminescent device.

[0092] In the organic electroluminescent device of the present disclosure, at least one layer (hereinafter referred to as "surface layer") selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer may be disposed on the inner surface of one or both electrodes. Specifically, a silicon and aluminum chalcogenide (including oxide) layer is preferably disposed on the anode side of the electroluminescent medium layer, and a metal halide or metal oxide layer is preferably disposed on the cathode side of the electroluminescent medium layer. The surface layer may provide operational stability for the organic electroluminescent device. Preferably, the chalcogenide is SiO X (1≦X≦2), AlO X (1≦X≦1.5), SiON, SiAlON, etc., metal halides include LiF, MgF2, CaF2, rare earth metal fluorides, etc., and metal oxides include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0093] Furthermore, in the organic electroluminescent device of the present disclosure, a mixed region of an electron transport compound and a reductive dopant or a mixed region of a hole transport compound and an oxidative dopant can be preferably disposed on the surface of at least one of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, which facilitates the injection and transport of electrons from the mixed region to the electroluminescent medium. Furthermore, the hole transport compound is oxidized to a cation, which facilitates the injection and transport of holes from the mixed region to the electroluminescent medium. Preferably, the oxidative dopant includes various Lewis acids and acceptor compounds, and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. Using the reductive dopant layer as a charge generation layer, an organic electroluminescent device having two or more light-emitting layers and emitting white light can be fabricated.

[0094] To form each layer of the organic electroluminescent device of the present disclosure, dry film formation methods such as vacuum evaporation, sputtering, plasma, ion plating, etc., or wet film formation methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating, etc. can be used.

[0095] When using a wet film-forming method, a thin film can be formed by dissolving or dispersing the materials that form each layer in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent can be any solvent in which the materials that form each layer can be dissolved or dispersed and which has no problem with film-forming ability.

[0096] According to one embodiment, when organic electroluminescent compound is used to form a layer, the layer can be formed by the method listed above, and in many cases can be formed by co-evaporation or mixed deposition.Co-evaporation is the mixed deposition method that two or more materials are put into each separate crucible source, and current is passed through both cells at the same time to evaporate material, and mixed deposition is performed;Mixed deposition is the mixed deposition method that two or more materials are mixed in one crucible source before deposition, and then current is passed through one cell to evaporate material.

[0097] According to one embodiment, the organic electroluminescent device of the present disclosure can be used for manufacturing display devices such as smartphones, tablets, notebooks, PCs, TVs, or display devices for vehicles, or lighting devices such as outdoor or indoor lighting.

[0098] In order to provide a detailed understanding of the present disclosure, methods for preparing compounds according to the present disclosure are described below with reference to representative compounds or intermediate compounds. [Example]

[0099] [Example 1] Synthesis of Compound C1-14 [ka] 1) Synthesis of Compound 1 Phenanthrene-9,10-dione (100.0 g, 480 mmol) was placed in a flask and dissolved in THF. Next, while filling with nitrogen, methylmagnesium bromide (MeMgBr) (3 M in THF) solution (480 mL, 1,440 mmol) was added dropwise at 0 °C, followed by stirring for 2 hours. After the reaction was complete, the mixture was neutralized with aqueous ammonium chloride (NH4Cl), extracted with methyl chloride (MC), and then dried over magnesium sulfate (MgSO4). The solid was then separated by column chromatography, followed by the addition of methanol (MeOH). The resulting solid was then filtered under reduced pressure to obtain compound 1 (43.0 g, yield: 36%).

[0100] 2) Synthesis of Compound 2 Compound 1 (60.0 g, 250 mmol), H2SO4 (202 mL, 375 mmol), and 500 mL of benzene were placed in a flask and stirred under reflux at 120 °C for 2 hours. After the reaction was completed, the mixture was neutralized with sodium bicarbonate (NaHCO3), extracted with MC, and then dried with MgSO4. It was then separated by column chromatography, and MeOH was added to it. The resulting solid was then filtered under reduced pressure to obtain compound 2 (50.0 g, yield: 90%).

[0101] 3) Synthesis of Compound 3 Compound 2 (20.0 g, 90.0 mmol) was placed in a flask and dissolved in THF. Then, while filling with nitrogen, MeMgBr (3 M in THF) solution (45 mL, 135 mmol) was added dropwise at 0 °C, followed by stirring for 2 hours. After the reaction was completed, the mixture was neutralized with isopropyl alcohol (IPA) and aqueous NH4Cl solution, then extracted with MC, and then dried with MgSO4. It was then separated by column chromatography, and MeOH was added to it. The resulting solid was then filtered under reduced pressure to obtain compound 3 (23.0 g, yield: 107%).

[0102] 4) Synthesis of Compound 4 Compound 3 (18.6 g, 78 mmol) and 78 mL of thionyl chloride (1 M in MC) solution were placed in a flask and stirred at 0 °C for 2 hours. After the temperature was lowered to -78 °C, 78 mL of trimethylaluminum (AlMe) (2 M in toluene) solution was added, followed by stirring for 3 hours and then reacting at room temperature overnight. After the reaction was complete, IPA and HO were added to quench the solution, and the layers were separated using MC. This was then separated by column chromatography, and MeOH was added to it. The resulting solid was then filtered under reduced pressure to obtain compound 4 (18.7 g, yield: 101%).

[0103] 5) Synthesis of Compound 5 Compound 4 (19.2 g, 81 mmol) and 200 mL of DMF were placed in a flask. While filling with nitrogen, N-bromosuccinimide (NBS) (26.0 g, 146 mmol) dissolved in 100 mL of DMF was added dropwise, followed by overnight reaction with stirring. After the reaction was completed, ethyl acetate (EA) and HO were added thereto, and the organic layer was separated to remove the organic solvent. This was then separated by column chromatography, and MeOH was added thereto. The resulting solid was then filtered under reduced pressure to obtain compound 5 (23.2 g, yield: 90%).

[0104] 6) Synthesis of Compound C1-14 Compound 5 (5.59 g, 24.8 mmol), N-([1,1'-biphenyl]-4-yl)-11,11-dimethyl-11H-benzo[b]fluoren-2-amine (10.2 g, 24.8 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (0.81 g, 0.89 mmol), tri-tert-butylphosphine (P(t-Bu)3) (0.359 g, 1.77 mmol), sodium tert-butoxide (NaOt-Bu) (3.41 g, 35.5 mmol), and 60 mL of toluene were placed in a flask and stirred at 120 °C for 1.5 h. After the reaction was completed, the organic solvent was removed, and the resulting solid was then separated by column chromatography. Next, MeOH was added thereto, and the resulting solid was then filtered under reduced pressure to give compound C1-14 (1.3 g, yield: 11%).

[0105] [Table 1]

[0106] [Example 2] Synthesis of Compound C-14 [ka] Compound 5 (6.0 g, 19.0 mmol), 2,4-diphenyl-6-(3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-3-yl)-1,3,5-triazine (11.7 g, 22.8 mmol), Pd(PPh3)4 (1.10 g, 0.95 mmol), K2CO3 (7.9 g, 57 mmol), 50 mL of toluene, 25 mL of EtOH, and 25 mL of HO were placed in a flask and stirred under reflux at 140 °C. After the reaction was completed, the organic solvent was removed and the resulting solid was separated by column chromatography. Next, MeOH was added to the mixture, and the resulting solid was filtered under reduced pressure to obtain compound C-14 (2.4 g, yield: 20.3%).

[0107] [Table 2]

[0108] [Example 3] Synthesis of Compound C-578 [ka]

[0109] 1) Synthesis of Compound 1-1 9,9,10,10-Tetramethyl-9,10-dihydrophenanthrene (34.0 g, 144 mmol), iodine (I2) (18.3 g, 71.9 mmol), iodic acid (12.7 g, 71.9 mmol), 280 mL of acetic acid (AcOH), 36 mL of H2SO4, 36 mL of water (HO), and 15 mL of CHCl3 were placed in a flask and stirred at 65 °C. After the reaction was completed, the solvent was removed and then separated by column chromatography. Next, MeOH was added thereto, and the resulting solid was filtered under reduced pressure to obtain compound 1-1 (56.0 g, yield: 107%).

[0110] 2) Synthesis of Compound 1-2 Compound 1-1 (35.0 g, 96.6 mmol), 5-chloro-2-formyl-phenyl)boronic acid (21.4 g, 116 mmol), Pd(PPh3)4 (5.58 g, 4.83 mmol), K2CO3 (33.4 g, 242 mmol), 300 mL of toluene, 100 mL of EtOH, and 100 mL of HO were added to a flask and stirred at 140 °C. After the reaction was completed, EA and HO were added to the reaction mixture to separate the layers, and then the organic layer was separated. The solvent was removed by vacuum filtration, followed by separation using column chromatography. Next, MeOH was added to the mixture, and the resulting solid was filtered under vacuum to give compound C1-2 (36.0 g, yield: 99.4%).

[0111] 3) Synthesis of Compounds 1-3 Compound 1-2 (30.0 g, 80.0 mmol), chloro-(methoxymethyl)-triphenyl-λ5-phosphane (38.4 g, 112 mmol), and 370 mL of THF were dissolved in a flask. Then, 112 mL of KOt-Bu (1 M in THF) solution was added dropwise with stirring. After the reaction was completed, EA and HO were added to the reaction mixture to separate the layers, and then the organic layer was separated. The solvent was removed by vacuum filtration, followed by separation using column chromatography. Next, MeOH was added to the mixture, and the resulting solid was filtered under vacuum to obtain compound 1-3 (20.0 g, yield: 62.0%).

[0112] 4) Synthesis of Compounds 1-4 Compound 1-3 (19.0 g, 47.2 mmol) and 250 mL of MC were dissolved in a flask. Then, 17.8 mL of BF3·EtOEt solution was added dropwise to the mixture while stirring at 0 °C. After the reaction was completed, MC and NaHCO3(aq) were added to the mixture, and the layers were separated. The organic layer was then isolated. The solvent was removed by vacuum filtration, followed by separation using column chromatography. Next, MeOH was added to the mixture, and the resulting solid was filtered under vacuum to obtain compound 1-4 (16.0 g, yield: 91.5%).

[0113] 5) Synthesis of Compound C-578 Compound 1-4 (6.0 g, 16.2 mmol), N-phenyldibenzofuran-3-amine (4.40 g, 17.0 mmol), Pd2(dba)3 (0.741 g, 0.809 mmol), sphos (0.664 g, 1.62 mmol), NaOt-Bu (3.11 g, 32.4 mmol), and 80 mL of o-xylene were placed in a flask and stirred under reflux at 180 °C. After the reaction was completed, the solvent was removed by vacuum filtration and then separated by column chromatography. Next, MeOH was added to it, and the resulting solid was filtered under vacuum to give compound C-578 (2.3 g, yield: 23.9%).

[0114] [Table 3]

[0115] [Example 4] Synthesis of Compound C-470 [ka]

[0116] 1) Synthesis of Compound 2-1 3-Bromo-9,9,10,10-tetramethyl-9,10-dihydrophenanthrene (30.0 g, 95.2 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaneborolane) (29.0 g, 114.1 mmol), PdCl2(PPh3)2 (3.34 g, 4.76 mmol), KOAc (23.3 g, 237.9 mmol), and 500 mL of 1,4-dioxane were placed in a flask and stirred at 140 °C for 3 h. After the reaction was completed, the organic solvent was removed, and the resulting solid was separated by column chromatography. Next, MeOH was added to the mixture, and the resulting solid was filtered under reduced pressure to obtain compound 2-1 (31 g, yield: 90%).

[0117] 2) Synthesis of Compound C-470 Compound 2-1 (6.0 g, 16.6 mmol), 2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (7.94 g, 18.2 mmol), Pd(PPh3)4 (0.960 g, 0.83 mmol), K2CO3 (6.88 g, 49.8 mmol), 40 mL of toluene, 20 mL of EtOH, and 20 mL of HO were added to a flask and stirred at 140 °C for 2 h. After the reaction was completed, the organic solvent was removed, and the resulting solid was separated by column chromatography. Next, MeOH was added to the mixture, and the resulting solid was filtered under reduced pressure to obtain compound C-470 (4.5 g, yield: 44%).

[0118] [Table 4]

[0119] [Example 5] Synthesis of Compound C-77 [ka]

[0120] Compound 2-1 (4.5 g, 12.4 mmol), 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (4.65 g, 13.0 mmol), Pd(PPh3)4 (0.716 g, 0.62 mmol), K2CO3 (6.88 g, 31.0 mmol), 30 mL of toluene, 15 mL of EtOH, and 15 mL of HO were added to a flask and stirred at 140 °C for 2 h. After the reaction was completed, the organic solvent was removed, and the resulting solid was separated by column chromatography. Next, MeOH was added to the mixture, and the resulting solid was filtered under reduced pressure to obtain compound C-77 (4.5 g, yield: 44%).

[0121] [Table 5]

[0122] [Example 6] Synthesis of Compound C-652 [ka]

[0123] 1) Synthesis of Compound 3-1 10,10-Dimethylphenanthren-9(10H)-one (10.0 g, 45.0 mmol) was placed in a flask and dissolved in THF. Then, under nitrogen, phenylmagnesium bromide (PhMgBr) (3 M in THF) solution (22.5 mL, 67.5 mmol) was added dropwise at 0 °C and stirred for 2 h. After the reaction was completed, the mixture was neutralized with aqueous NH4Cl, extracted with MC, and then dried with MgSO4. It was then separated by column chromatography. MeOH was added to the mixture, and the resulting solid was filtered under reduced pressure to obtain compound 3-1 (12.5 g, yield: 92%).

[0124] 2) Synthesis of Compound C-652 Compound 3-1 (12.4 g, 41.3 mmol), N-([1,1'-biphenyl]-4-yl)-N-phenyl-[1,1'-biphenyl]-4-amine (65.6 g, 165 mmol), and 200 mL of MC were placed in a flask and stirred at 0 °C. 6.7 mL of H2SO4 was added dropwise, followed by reaction for 1 day. After the reaction was completed, the mixture was neutralized with K2CO3, extracted with MC, and then dried with MgSO4. It was then separated by column chromatography. MeOH was then added to it, and the resulting solid was filtered under reduced pressure to obtain compound C-652 (8.6 g, yield: 31%).

[0125] [Table 6]

[0126] [Example 7] Synthesis of Compound C-469 [ka]

[0127] 1) Synthesis of Compound 4-1 3-Bromophenanthrene-9,10-dione (60.0 g, 209 mmol) was placed in a flask and dissolved in THF solution (1 L). Next, while filling with nitrogen, MeMgBr (3 M in THF) solution (209 mL, 627 mmol) was added dropwise at 0 °C and then stirred for 1 h. After the reaction was completed, MeMgBr was quenched with IPA, MeOH, and HO, and then neutralized with aqueous NH Cl solution. The organic layer was then extracted with EA and subsequently dried with MgSO . It was then separated on a Celite filter, and MeOH was added to it. The resulting solid was then filtered under reduced pressure to obtain compound 4-1 (74.0 g, yield: 110%).

[0128] 2) Synthesis of Compounds 4-2 and 4-3 Compound 4-1 (74.0 g, 232 mmol), H2SO4 (18.9 mL, 348 mmol), and 1,000 mL of MC were placed in a flask and stirred under reflux at 80 °C for 1 hour. After the reaction was completed, H2O was added to the mixture to dilute the H2SO4, and the mixture was then neutralized with NaHCO3. It was then extracted with MC and dried with MgSO4. It was then separated by column chromatography, and MeOH was added to it. The resulting solid was then filtered under reduced pressure to give compounds 4-2 and 4-3 (60.0 g, yield: 85%).

[0129] 3) Synthesis of Compounds 4-4 and 4-5 Compounds 4-2 and 4-3 (60.0 g, 199 mmol) were placed in a flask and dissolved in THF solution (1 L). Then, while filling with nitrogen, MeMgBr (3 M in THF) solution (99.6 mL, 299 mmol) was added dropwise at 0 °C and stirred for 3 h. After the reaction was completed, the mixture was neutralized with IPA and aqueous NH4Cl solution, then extracted with MC, followed by drying with MgSO4. This was then separated by column chromatography, and MeOH was added to it. The resulting solid was then filtered under reduced pressure to give compounds 4-4 and 4-5 (63.2 g, yield: 100%).

[0130] 4) Synthesis of Compounds 4-6 Compounds 4-4 and 4-5 (63.2 g, 199.2 mmol) and 183 mL of thionyl chloride (SOCl2) (1 M in MC) solution were placed in a flask and stirred at 0 °C for 2 h. After the temperature was lowered to -78 °C, 183 mL of AlMe3 (2 M in toluene) solution was added and stirred for 3 h, followed by overnight reaction at room temperature. After the reaction was completed, IPA and HO were added to quench the solution, and the layers were separated using MC. This was then separated by column chromatography, and MeOH was added to it. The resulting solid was then filtered under reduced pressure to obtain compound 4-6 (59.0 g, yield: 94%).

[0131] 5) Synthesis of Compound C-469 Compound 4-6 (5.0 g, 15.7 mmol), N-([1,1'-biphenyl]-4-yl)-11,11-dimethyl-11H-benzo[b]fluoren-2-amine (8.45 g, 17.4 mmol), Pd2(dba)3 (0.719 g, 0.785 mmol), P(t-Bu)3 (0.318 g, 1.57 mmol), NaOt-Bu (3.02 g, 31.4 mmol), and 60 mL of toluene were added to a flask and stirred at 130 °C for 1 h. After the reaction was completed, the organic solvent was removed, and the resulting solid was separated by column chromatography. MeOH was then added to the mixture, and the resulting solid was filtered under reduced pressure to give compound C-469 (2.1 g, 19% yield).

[0132] [Table 7]

[0133] [Example 8] Synthesis of Compound C-317 [ka] Compound A (2.6 g, 6.64 mmol), di([1,1'-biphenyl]-4-yl)amine (2.1 g, 6.64 mmol), Pd(dba) (0.3 g, 0.33 mmol), P(t-Bu) (0.3 mL, 0.66 mmol), NaOt-Bu (1.0 g, 9.96 mmol), and 33 mL of toluene were added to a reaction vessel and stirred under reflux for 1 h. After the reaction was complete, the reaction mixture was cooled to room temperature, and the solid was filtered and subsequently washed with ethyl acetate. The filtrate was then distilled under reduced pressure and purified by column chromatography to give compound C-317 (2.5 g, 59% yield).

[0134] [Table 8]

[0135] [Example 9] Synthesis of Compound C-400 [ka] Compound A (3.5 g, 8.94 mmol), N-([1,1'-biphenyl]-4-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)phenyl)-[1,1'-biphenyl]-4-amine (4.7 g, 8.94 mmol), PPh3)4 (0.5 g, 0.45 mmol), Na2CO3 (2.4 g, 22.35 mmol), 45 mL of toluene, 11 mL of ethanol, and 11 mL of HO were added to a reaction vessel and stirred at 120 °C for 4 hours. After completion of the reaction, the mixture was washed with distilled water, and the organic layer was extracted with ethyl acetate. The extracted organic layer was then dried over magnesium sulfate. The solvent was then removed using a rotary evaporator, and the product was purified by column chromatography to obtain compound C-400 (2.0 g, yield: 32%).

[0136] [Table 9]

[0137] [Example 10] Synthesis of Compound C2-31 [ka] Compound 5 (6.5 g, 20.6 mmol), compound 10 (10.0 g, 20.6 mmol), Pd(dba) (943 mg, 1.03 mmol), P(t-Bu) (1.0 mL, 2.06 mmol, 50% toluene solution), NaOt-Bu (3.0 g, 30.9 mmol), and 103 mL of toluene were placed in a flask and refluxed for 3 h. After the reaction was complete, the reaction mixture was cooled to room temperature, and the solvent was removed using a rotary evaporator. The mixture was then purified by column chromatography to give compound C2-31 (5.3 g, 36% yield) as a white solid.

[0138] [Table 10]

[0139] [Example 11] Synthesis of Compound 2-8 [ka] Compound 1-1 (9.0 g, 24.8 mmol), di([1,1'-biphenyl]-4-yl)amine (9.6 g, 29.8 mmol), Pd2(dba)3 (1.1 g, 1.24 mmol), P(t-Bu)3 (1.2 mL, 2.48 mmol, 50% toluene solution), NaOt-Bu (4.8 g, 49.6 mmol), and 130 mL of toluene were placed in a flask and refluxed for 4 h. After the reaction was complete, the reaction mixture was cooled to room temperature, and the solvent was removed using a rotary evaporator. The mixture was then purified by column chromatography to give compound C2-8 (4.1 g, 30% yield) as a white solid.

[0140] [Table 11]

[0141] [Example 12] Synthesis of Compound C2-32 [ka]

[0142] 1) Synthesis of Compound 12-1 Compound 1-1 (30.0 g, 82.8 mmol), 4-chloroaniline (21.7 g, 169.8 mmol), palladium(II) acetate (Pd(OAC)2) (1.3 g, 5.68 mmol), S-Phos (4.6 g, 11.3 mmol), NaOt-Bu (16.3 g, 169.8 mmol), and 566 mL of o-xylene were placed in a flask and refluxed for 3 h. After the reaction was complete, the reaction mixture was cooled to room temperature, and the solvent was removed using a rotary evaporator. The residue was purified by column chromatography to give compound 12-1 (18 g, 60% yield).

[0143] 2) Synthesis of Compound 12-2 Compound 12-1 (18.0 g, 49.7 mmol), phenylboronic acid (13.2 g, 74.6 mmol), Pd(OAC) (559 mg, 2.49 mmol), S-Phos (2.0 g, 4.97 mmol), NaOt-Bu (12 g, 124.4 mmol), 250 mL of o-xylene, 60 mL of 1,4-dioxane, and 60 mL of distilled water were placed in a flask and refluxed for 4 h. After the reaction was complete, the reaction mixture was cooled to room temperature, and the solvent was removed by rotary evaporation. The resulting mixture was purified by column chromatography to give compound 12-2 (18.1 g, 90% yield).

[0144] 3) Synthesis of compound C2-32 Compound 12-2 (10.2 g, 25.2 mmol), compound 12-3 (10.0 g, 25.2 mmol), Pd(dba) (1.2 g, 1.26 mmol), P(t-Bu) (1.24 mL, 2.52 mmol, 50% toluene solution), NaOt-Bu (3.6 g, 37.8 mmol), and 126 mL of toluene were added to a flask and refluxed for 4 h. After the reaction was complete, the reaction mixture was cooled to room temperature, and the solvent was removed by rotary evaporation. The mixture was then purified by column chromatography to give compound C2-32 (5.9 g, 33% yield) as a white solid.

[0145] [Table 12]

[0146] [Example 13] Synthesis of Compound C-696 [ka] 3-Bromo-9,9,10,10-tetramethyl-9,10-dihydrophenanthrene (5.5 g, 10.4 mmol), 2,4-diphenyl-6-(8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-1-yl)-1,3,5-triazine (4.3 g, 13.5 mmol), Pd(PPh3)4 (0.6 g, 0.52 mmol), K2CO3 (2.8 g, 20.8 mmol), 100 mL of toluene, 20 mL of HO, and 20 mL of EtOH were placed in a flask and stirred at 150 °C. After the reaction was complete, EA and HO were added to the reaction mixture to separate the layers, and then the organic layer was separated. The solvent was then removed by vacuum filtration, followed by separation using column chromatography. Next, MeOH was added thereto, and the resulting solid was then filtered under reduced pressure to obtain compound C-696 (5.4 g, yield: 83%).

[0147] [Table 13]

[0148] [Example 14] Synthesis of Compound C-697 [ka]

[0149] 1) Synthesis of Compound 11 3-Bromo-9,9,10,10-tetramethyl-9,10-dihydrophenanthrene (13.3 g, 42.1 mmol), (9H-carbazol-2-yl)boronic acid (13.3 g, 63.1 mmol), Pd(PPh3)4 (2.43 g, 2.1 mmol), K2CO3 (11.6 g, 84.2 mmol), 210 mL of toluene, 40 mL of HO, and 20 mL of EtOH were added to a flask and stirred at 150 °C. After the reaction was completed, the organic layer was separated by adding EA and HO, and the solvent was removed by filtration under reduced pressure. This was then separated by column chromatography, and MeOH was added to it. The resulting solid was then filtered under reduced pressure to give compound 11 (6.9 g, yield: 40.8%).

[0150] 2) Synthesis of Compound C-697 Compound 11 (6.9 g (15.9 mmol), 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (6.8 g, 17.5 mmol), Pd(OAC) (0.18 g, 0.8 mmol), S-Phos (0.65 g, 1.59 mmol), NaOt-Bu (3.0 g, 31.8 mmol), and 160 mL of o-xylene were placed in a flask and stirred at 180 °C. After the reaction was completed, the organic layer was separated by adding EA and HO, and the solvent was removed by filtration under reduced pressure. This was then separated by column chromatography, and MeOH was added to it. The resulting solid was then filtered under reduced pressure to give compound C-697 (4.8 g, yield: 42.8%).

[0151] [Table 14]

[0152] [Example 15] Synthesis of Compound C-572 [ka]

[0153] 1) Synthesis of Compound 12 9-Chloro-5,5,6,6-tetramethyl-5,6-dihydrobenzo[k]tetraphene (7.5 g, 20.2 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaneborolane) (10.3 g, 40.4 mmol), Pd(dba) (0.92 g, 1.01 mmol), S-Phos (0.83 g, 2.02 mmol), KOAC (4.95 g, 50.5 mmol), and 100 mL of 1,4-dioxane were placed in a flask and stirred at 180 °C. After the reaction was complete, the organic layer was separated by adding EA and HO, and the solvent was removed by vacuum filtration. This was then separated by column chromatography, followed by the addition of MeOH. The resulting solid was then filtered under reduced pressure to give Compound 12 (9.6 g, yield: 95%).

[0154] 2) Synthesis of Compound C-572 Compound 12 (9.6 g, 20.7 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.3 g, 19.7 mmol), Pd(pph3)4 (1.13 g, 0.98 mmol), K2CO3 (5.4 g, 39.4 mmol), 200 mL of toluene, 40 mL of EtOH, and 40 mL of HO were added to a flask and stirred at 160 °C. After the reaction was completed, the organic layer was separated by adding EA and HO, and the solvent was removed by vacuum filtration. This was then separated by column chromatography, and MeOH was added to it. The resulting solid was then vacuum filtered to give compound C-572 (8.5 g, yield: 80%).

[0155] [Table 15]

[0156] Hereinafter, the light-emitting characteristics of the organic electroluminescent device including the organic electroluminescent compound of the present disclosure will be described in order to understand the present disclosure in detail.

[0157] [Device Example 1-1] Fabrication of an OLED Containing an Organic Electroluminescent Compound According to the Present Disclosure The organic electroluminescent compound of the present disclosure was used to fabricate an OLED. First, a transparent electrode indium tin oxide (ITO) thin film (10 Ω / sq) (Geomatec Co., Ltd., Japan) on a glass substrate for the OLED was subjected to ultrasonic cleaning in acetone, ethanol, and distilled water, and then stored in isopropanol. The vacuum in the chamber was adjusted to 10 -6 After evacuating the chamber to 3000 rpm, the ITO substrate was mounted on a substrate holder in a vacuum evaporation system. Compound HT-1 was then introduced into one cell of the vacuum evaporation system, and compound HI-1 was introduced into another cell. The two materials were evaporated at different rates, each with a doping amount of 3 wt. % to form a hole injection layer with a thickness of 10 nm on the ITO substrate. Compound HT-1 was then introduced into one cell of the vacuum evaporation system, and a current was passed through the cell to evaporate it, thereby forming a first hole transport layer with a thickness of 90 nm on the hole injection layer. Compound C1-14, listed in Table 1 below, was then introduced into another cell of the vacuum evaporation system, and a current was passed through the cell to evaporate it, thereby forming a second hole transport layer with a thickness of 60 nm on the first hole transport layer. After forming the hole injection layer and hole transport layer, an emissive layer was formed thereon as follows: compound RH was placed in one cell of the vacuum evaporation system as a host, and compound D-39 was placed in another cell as a dopant. The two materials were evaporated, and the dopant was deposited at a doping amount of 2 wt% based on the total amount of the host and dopant to form a 40 nm-thick light-emitting layer on the second hole-transporting layer. Next, in two other cells, compound ET and compound EI were evaporated in a 1:1 ratio to deposit a 35 nm-thick electron-transporting layer on the light-emitting layer. Next, compound EI was deposited as a 2 nm-thick electron-injecting layer, and then an 80 nm-thick Al cathode was deposited on the electron-injecting layer using a separate vacuum deposition system. Thus, an OLED was fabricated.

[0158] [Comparative Example 1-1] Fabrication of OLED containing conventional compounds An OLED was fabricated in the same manner as in Device Example 1-1, except that the compound NPB was used as the material of the second hole transport layer.

[0159] The OLEDs according to Device Example 1-1 and Comparative Example 1-1 prepared as described above were measured for the driving voltage, luminous efficiency, and color coordinates at a luminance of 1,000 nits, as well as the time required for the luminance to decrease from 100% to 95% (lifetime; T95) at a luminance of 10,000 nits, and the results are shown in Table 1-1 below:

[0160] [Table 16]

[0161] [Device Examples 1-2 to 1-4] Fabrication of OLEDs Containing Organic Electroluminescent Compounds According to the Present Disclosure An OLED was fabricated in the same manner as in Device Example 1-1, except that compound RH-2 was used as the host in the light-emitting layer and the compound listed in Table 1-2 below was used as the material in the second hole-transporting layer.

[0162] [Comparative Examples 1-2] Fabrication of OLEDs containing conventional compounds An OLED was fabricated in the same manner as in Device Example 1-1, except that compound RH-2 was used as the host in the light-emitting layer and the compound listed in Table 1-2 below was used as the material in the second hole-transporting layer.

[0163] The time required for the light emission to decrease from 100% to 95% (lifetime; T95) at a brightness of 10,000 nits for the OLEDs of the device Examples 1-2 to 1-4 and Comparative Example 1-2 manufactured as described above was measured, and the results are shown in Table 1-2 below.

[0164] [Table 17]

[0165] By incorporating the organic electroluminescent compound according to the present disclosure into the hole transporting zone, an organic electroluminescent device having low driving voltage, high luminous efficiency, and long life characteristics can be provided.

[0166] Device Examples 2-1 and 2-2: Fabrication of OLEDs Containing Organic Electroluminescent Compounds According to the Present Disclosure An OLED according to the present disclosure was fabricated. First, an indium tin oxide (ITO) thin film (10 Ω / sq) (Geomatec Co., Ltd., Japan), a transparent electrode on a glass substrate for the OLED, was subjected to ultrasonic cleaning in acetone and isopropyl alcohol, and then stored in isopropanol before use. Next, the ITO substrate was attached to a substrate holder in a vacuum evaporation system. Compound HI-1 was then introduced into one cell of the vacuum evaporation system, and compound HT-1 was introduced into another cell of the vacuum evaporation system. The two materials were evaporated at different rates, and compound HI-1 was deposited with a doping amount of 3 wt.% based on the total amount of the two materials to form a hole injection layer with a thickness of 10 nm. Next, compound HT-1 was deposited on the hole injection layer as a first hole transport layer with a thickness of 80 nm. Compound HT-2 was then introduced into another cell of the vacuum evaporation system, and evaporated by passing a current through the cell, thereby forming a second hole transport layer with a thickness of 30 nm on the first hole transport layer. After forming the hole injection layer and hole transport layer, an emitting layer was formed thereon as follows: the compound shown in Table 2 below was introduced as a host into one cell of a vacuum evaporation system, and compound D-50 was introduced as a dopant into another cell. Simultaneously, the dopant material was evaporated at different rates and deposited at a doping amount of 10 wt. % based on the total amount of host and dopant to form a 40 nm-thick emitting layer on the hole transport layer. Next, compound ET and compound EI were deposited in a weight ratio of 40:60 as electron transport layer materials to form a 35 nm-thick electron transport layer on the emitting layer. Compound EI was then deposited as an electron injection layer material with a thickness of 2 nm on the electron transport layer, and an 80 nm-thick Al cathode was deposited on the electron injection layer using a separate vacuum evaporation system. Thus, an OLED was fabricated. Each compound used in all materials was 10 -6It was purified by vacuum sublimation in torr.

[0167] Device Examples 2-3 and 2-4: Fabrication of OLEDs Containing Multiple Host Materials According to the Present Disclosure An OLED was fabricated in the same manner as in Device Example 2-1, except that the compounds shown in Table 2 below were used as host materials, and the light-emitting layer was deposited by evaporating the two host materials at different rates of 1:2.

[0168] [Comparative Example 2] Fabrication of an OLED containing a conventional compound as a host An OLED was fabricated in the same manner as in Device Example 2-1, except that only the compound CBP was used as a host material for depositing the light-emitting layer, the compound BAlq was used as a hole-blocking layer material for depositing a 5-nm-thick hole-blocking layer on the light-emitting layer, and then the compounds ET and EI were deposited in a weight ratio of 40:60 as electron-transporting layer materials to form a 30-nm-thick electron-transporting layer on the hole-blocking layer.

[0169] The OLEDs according to the device examples 2-1 to 2-4 and comparative example 2 manufactured as described above were measured for the driving voltage, luminous efficiency, power efficiency, and luminous color at a brightness of 1,000 nits, as well as the time required for the luminance to decrease from 100% to 95% (lifetime; T95) at a brightness of 20,000 nits, and the results are shown in Table 2 below.

[0170] [Table 18]

[0171] By including the organic electroluminescent compound according to the present disclosure and a plurality of host materials containing the same in the light-emitting layer, it is possible to provide a long-life organic electroluminescent device that not only has low driving voltage and excellent light-emitting properties, but also has a significantly improved lifetime compared to OLEDs containing conventional host materials.

[0172] [Device Example 3-1] Fabrication of an OLED containing a compound according to the present disclosure An OLED was fabricated using the organic electroluminescent compound of the present disclosure. First, an indium tin oxide (ITO) thin film (10 Ω / sq) (Geomatec Co., Ltd., Japan), which is a transparent electrode on a glass substrate for an OLED, was subjected to ultrasonic cleaning in acetone, ethanol, and isopropyl alcohol, and then stored in isopropanol before use. The vacuum in the chamber was adjusted to 10 -6 After evacuating the system to 3000 Torr, the ITO substrate was mounted on a substrate holder in a vacuum evaporation system. Compound HT-1 was then introduced into one cell of the vacuum evaporation system, and compound HI-1 was introduced into another cell of the vacuum evaporation system. The two materials were evaporated at different rates, and each compound was deposited with a doping amount of 3 wt% to form a hole injection layer with a thickness of 10 nm on the ITO substrate. Compound HT-1 was then introduced into one cell of the vacuum evaporation system and evaporated by passing a current through the cell, thereby forming a first hole transport layer with a thickness of 75 nm on the hole injection layer. Compound HT-3 was then introduced into another cell of the vacuum evaporation system and evaporated by passing a current through the cell, thereby forming a second hole transport layer with a thickness of 5 nm on the first hole transport layer. After forming the hole injection layer and hole transport layer, an emissive layer was formed thereon as follows: compound BH-1 was introduced into one cell of the vacuum evaporation system as a host, and compound BD was introduced into the other cell as a dopant. The two materials were then evaporated, and the dopant was deposited at a doping amount of 2 wt% based on the total amount of host and dopant to form a 20 nm-thick light-emitting layer on the second hole-transporting layer. Next, compound C-14 was deposited as a hole-blocking material to form a 5 nm-thick hole-blocking layer. In another two cells, compound ET and compound EI were evaporated at a 1:1 ratio to form a 30 nm-thick electron-transporting layer on the hole-blocking layer. After compound EI was deposited as a 2 nm-thick electron-injection layer, an 80 nm-thick Al cathode was deposited using a separate vacuum deposition system. OLEDs were thus fabricated.

[0173] [Comparative Example 3-1] Fabrication of OLED containing conventional compounds An OLED was fabricated in the same manner as in Device Example 3-1, except that no hole-blocking layer was deposited, and a 33-nm-thick electron-transporting layer was deposited on the light-emitting layer by evaporating compound ET and compound EI at a ratio of 1:1.

[0174] The driving voltage, current efficiency and CIE color coordinates at a luminance of 1,000 nits of the OLEDs according to Device Example 3-1 and Comparative Example 3-1 prepared as above were measured, and the results are shown in Table 3-1 below.

[0175] [Table 19]

[0176] Device Examples 3-2 and 3-3: Fabrication of OLEDs Containing Compounds According to the Present Disclosure An OLED was fabricated in the same manner as in Device Example 3-1, except that compound BD-1 was used as the dopant material and the compounds shown in Table 3-2 below were used as materials for the hole-blocking layer.

[0177] [Comparative Example 3-2] Fabrication of OLED containing conventional compounds An OLED was fabricated in the same manner as in Device Example 3-1, except that no hole-blocking layer was deposited, compound BD-1 was used as a dopant material, and a 35-nm-thick electron-transporting layer was deposited on the light-emitting layer by evaporating compounds ET and EI at a ratio of 1:1.

[0178] The driving voltage, current efficiency and CIE color coordinates at a luminance of 1,000 nits of the OLEDs according to the device Examples 3-2 and 3-3 and Comparative Example 3-2 prepared as above were measured, and the results are shown in Table 3-2 below.

[0179] [Table 20]

[0180] By including the organic electroluminescent compound according to the present disclosure in the hole-blocking layer, an organic electroluminescent device having low driving voltage and / or high luminous efficiency characteristics can be provided.

[0181] Device Example 4: Fabrication of a Red-Emitting OLED According to the Present Disclosure An OLED according to the present disclosure was fabricated as follows: First, an indium tin oxide (ITO) thin film (10 Ω / sq) (Geomatec Co., Ltd., Japan), a transparent electrode on a glass substrate for an OLED, was subjected to ultrasonic cleaning in acetone and isopropyl alcohol, and then stored in isopropanol before use. Next, the ITO substrate was attached to a substrate holder in a vacuum evaporation system. Compound HI-1 was then introduced into one cell of the vacuum evaporation system, and compound HT-1 was introduced into another cell of the vacuum evaporation system. The two materials were evaporated at different rates, and compound HI-1 was deposited with a doping amount of 3 wt. % based on the total amount of the two materials to form a hole injection layer with a thickness of 10 nm. Next, compound HT-1 was deposited on the first hole injection layer as a first hole transport layer with a thickness of 80 nm. Compound HT-4 was then introduced into another cell of the vacuum evaporation system and evaporated by passing a current through the cell, thereby forming a second hole transport layer with a thickness of 60 nm on the first hole transport layer. After forming the hole injection layer and hole transport layer, an emitting layer was formed thereon as follows: the first and second host compounds shown in Table 4 below were introduced into two cells of a vacuum evaporation system as hosts, and compound D-39 was introduced into another cell as a dopant. The two host materials were evaporated in a 1:1 ratio, and simultaneously, the dopant was evaporated at a different rate. The dopant was evaporated at a doping amount of 3 wt % based on the total amount of host and dopant to form a 40 nm-thick emitting layer on the second hole transport layer. Next, compound ET and compound EI were evaporated in a 50:50 weight ratio as materials for the electron transport material layer to form a 35 nm-thick electron transport layer on the emitting layer. Compound EI was evaporated on the electron transport layer as a 2 nm-thick electron injection layer, and then an 80 nm-thick Al cathode was evaporated on the electron injection layer using a separate vacuum evaporation system. An OLED was fabricated in this manner. All compounds used in the materials were purified by vacuum sublimation at 10-6 Torr.

[0182] [Comparative Example 4] Fabrication of an OLED containing a conventional compound as a host An OLED was fabricated in the same manner as in Device Example 4, except that the compound CBP was used alone as the host in the emissive layer.

[0183] The OLEDs according to Device Example 4 and Comparative Example 4 prepared as described above were measured for driving voltage, luminous efficiency, and luminous color at a luminance of 1,000 nits, as well as the time required for the luminance to decrease from 100% to 95% (lifetime; T95) at a luminance of 5,000 nits, and the results are shown in Table 4 below.

[0184] [Table 21]

[0185] The compounds used in the above device examples and comparative examples are shown in Table 5 below.

[0186] [Table 22]

[0187] [Table 23]

[0188] [Table 24]

[0189] Furthermore, in the organic electroluminescent compound represented by formula 1 according to the present disclosure, R to R 12 The LUMO (lowest unoccupied molecular orbital) energy level, HOMO (highest unoccupied molecular orbital) energy level, and triplet energy level of compounds in which is linked to adjacent substituents to form a benzene ring or a naphthalene ring were measured, and the results are shown in Table 6 below.

[0190] [Table 25]

[0191] *The structure was optimized using the Gaussian quantum chemistry calculation program Gaussian 16 by applying hybrid density functional theory (hybrid DFT) (B3LYP) and the 6-31G(d) basis set. The triplet state was calculated using time-dependent DFT (TD-DFT).

[0192] Referring to Table 6 above, in the organic electroluminescent compound represented by Formula 1 according to the present disclosure, R5 to R8 and / or R9 to R 12 It can be seen that even when is bonded to adjacent substituents to form a benzene ring or naphthalene, it has a main core energy level that can be used as a material for an OLED according to the present disclosure. The present invention may include the following aspects. [Aspect 1] Formula 1 below: [ka] (In the formula, R1 to R4 are each independently *-(L1) a -(Ar1) b , hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl, or may be linked to adjacent substituents to form a ring; R5~R 12 are each independently *-(L1) a -(Ar1) b, hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, or substituted or unsubstituted tri(C6-C30) arylsilyl, or may be linked to adjacent substituents to form a ring; R1~R 12 At least one of the following is *-(L1) a -(Ar1) b Provided that it represents; L1 represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30-membered) heteroarylene; Ar1 represents a substituted or unsubstituted (C6 to C30) aryl, a substituted or unsubstituted (3 to 30-membered) heteroaryl, or -N-(Ar2)(Ar3); Ar2 and Ar3 each independently represent a substituted or unsubstituted (C1 to C30) alkyl, a substituted or unsubstituted (C2 to C30) alkenyl, a substituted or unsubstituted fused ring of a (C3 to C30) aliphatic ring and a (C6 to C30) aromatic ring, a substituted or unsubstituted (C6 to C30) aryl, or a substituted or unsubstituted (3 to 30-membered) heteroaryl; a represents an integer of 1 or 2, b represents an integer of 1 to 4, and when a and b are 2 or more, each L1 and each Ar1 may be the same or different; R5~R 10 and R 12 represents hydrogen and R 11 provided that compounds of formula 1 containing a substituted amino group are excluded. 1. An organic electroluminescent compound represented by the formula: [Aspect 2] Ar1 represents a substituted or unsubstituted (3 to 30-membered) heteroaryl containing at least one N, or -N-(Ar2)(Ar3); L1 represents a single bond or a substituted or unsubstituted (C6 to C30) arylene; 2. The organic electroluminescent compound according to embodiment 1. [Aspect 3] The compound represented by formula 1 is represented by the following formulae 1-1 to 1-4: [ka] (In the formula, R1~R 12 , L1, Ar1, a, and b are as defined in embodiment 1). 2. The organic electroluminescent compound according to embodiment 1, represented by any one of: [Aspect 4] The compound represented by formula 1 is a compound represented by the following formulas 1-5 to 1-13: [ka] [ka] [ka] (In the formula, R1~R 12 is as defined in aspect 1; R 13 ~R 18 are each independently *-(L1) a -(Ar1) b, hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, or substituted or unsubstituted tri(C6-C30) arylsilyl, or may be linked to adjacent substituents to form a ring; R1 to R in formulas 1-5 to 1-7 14 At least one of R1 to R2 in formulas 1-8 to 1-10 16 and at least one of R1 to R2 in formulas 1-11 to 1-13. 18 At least one of the following is *-(L1) a -(Ar1) b Provided that it represents; L1, Ar1, a, and b are as defined in embodiment 1. 2. The organic electroluminescent compound according to embodiment 1, represented by any one of: [Aspect 5] 2. The organic electroluminescent compound of embodiment 1, wherein L1 represents a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthrenylene, substituted or unsubstituted triphenylenylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted triazinylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted quinoxalinylene, substituted or unsubstituted quinazolinylene, substituted or unsubstituted dibenzofuranylene, or substituted or unsubstituted benzoquinoxalinylene. [Aspect 6] The substituted or unsubstituted (3-30 membered) heteroaryl of Ar1 is substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted dibenzoquinolinyl, substituted or unsubstituted dibenzoquinazolinyl, substituted or unsubstituted dibenzoquinoxalinyl, substituted or unsubstituted indole, 2. The organic electroluminescent compound of embodiment 1, wherein the benzothiopyridyl, substituted or unsubstituted indenopyrimidinyl, substituted or unsubstituted indenopyrazinyl, substituted or unsubstituted benzofuropyridyl, substituted or unsubstituted benzofuropyrimidinyl, substituted or unsubstituted benzofuropyrazinyl, substituted or unsubstituted benzothiopyridyl, substituted or unsubstituted benzothiopyrimidinyl, substituted or unsubstituted benzothiopyrazinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl. [Aspect 7] 2. The organic electroluminescent compound according to claim 1, wherein the substituted or unsubstituted (C6-C30)aryl in Ar1 represents substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylenyl, or substituted or unsubstituted phenanthrenyl. [Aspect 8] The organic electroluminescent compound according to embodiment 1, wherein Ar2 and Ar3 each independently represent substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted chrysenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzofluorenyl, or substituted or unsubstituted dihydrophenanthrenyl. [Aspect 9] The compound of formula 1 is a compound: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] 2. The organic electroluminescent compound according to embodiment 1, selected from: [Aspect 10] An organic electroluminescent material comprising the organic electroluminescent compound according to embodiment 1. [Aspect 11] A plurality of host materials comprising at least one organic electroluminescent material according to embodiment 10 as a first host material and at least one second host material different from the first host material. [Aspect 12] The second host material has the following formula 11: [ka] (In the formula, L a represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30-membered) heteroarylene; Ar a represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 membered) heteroaryl; R9 and R 10are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-50 membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C2-C30) alkenylamino , a substituted or unsubstituted (C1-C30) alkyl(C2-C30) alkenylamino, a substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, a substituted or unsubstituted (C1-C30) alkyl(3-30 membered) heteroarylamino, a substituted or unsubstituted (C2-C30) alkenyl(C6-C30) arylamino, a substituted or unsubstituted (C2-C30) alkenyl(3-30 membered) heteroarylamino, a substituted or unsubstituted mono- or di-(C6-C30) arylamino, a substituted or unsubstituted mono- or di-(3-30 membered) heteroarylamino, or a substituted or unsubstituted (C6-C30) aryl(3-30 membered) heteroarylamino, or may be linked to adjacent substituents to form a ring; f and g each independently represent an integer of 1 to 4, and when f and g are 2 or more, each of R9 and R 10 may be the same or different) 12. The plurality of host materials of embodiment 11, comprising a compound represented by: [Aspect 13] The compound represented by formula 11 is represented by the following formula 12 or 13: [ka] (In the formula, L a , Ar a , R9, R10 and f is as defined in aspect 12; T1 and T2 each independently represent a single bond, O, or S; L b In aspect 12, L a is as defined as; Ar b In aspect 12, Ar a is as defined as; R 11 ~R 14 are each independently as defined as R9 in embodiment 12; X1 is O, S, or NR a represents; R a represents a substituted or unsubstituted (C6-C30) aryl; g' and h each independently represent an integer of 1 to 3, i and k each independently represent an integer of 1 to 4, j represents an integer of 1 or 2, and when g', h, i, j, and k are 2 or more, R 10 Each of R 11 Each of R 12 Each of R 13 and R 14 may be the same or different) 13. The plurality of host materials of embodiment 12, represented by: [Aspect 14] The compound of formula 11 is a compound: [ka] [ka] [ka] [ka] 13. The plurality of host materials of embodiment 12, selected from: [Aspect 15] An organic electroluminescent device comprising the organic electroluminescent compound according to embodiment 1. [Aspect 16] 16. The organic electroluminescent device of embodiment 15, wherein the organic electroluminescent compound is included in the hole-transporting zone and / or the electron-transporting zone and / or the light-emitting layer. [Aspect 17] 12. An organic electroluminescent device comprising: an anode; a cathode; and at least one light-emitting layer between the anode and the cathode, wherein the at least one light-emitting layer comprises a plurality of host materials according to embodiment 11. [Aspect 18] An organic electroluminescent compound represented by the following formula 2: [ka] (In the formula, R'1 to R'4 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C3 to C30) cycloalkyl, substituted or unsubstituted (3 to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6 to C30) aryl, or substituted or unsubstituted (3 to 30-membered) heteroaryl, or may be linked to adjacent substituents to form a ring; R'5 and R'6 each independently represent hydrogen or deuterium; L'1 to L'3 each independently represent a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30-membered) heteroarylene; Ar' represents a substituted or unsubstituted (C6 to C30) aryl or a substituted or unsubstituted (3 to 30-membered) heteroaryl; BFL represents substituted or unsubstituted benzo[a]fluorenyl, substituted or unsubstituted benzo[b]fluorenyl, or substituted or unsubstituted benzo[c]fluorenyl; m represents an integer of 1 to 4, n represents an integer of 1 to 3, and when m and n are 2 or greater, each R'5 and each R'6 may be the same or different. An organic electroluminescent compound represented by the formula: [Aspect 19] The compound of formula 2 is a compound: [ka] [ka] [ka] 19. The organic electroluminescent compound according to embodiment 18, selected from: [Aspect 20] An organic electroluminescent device comprising the organic electroluminescent compound according to embodiment 18. [Aspect 21] Equation 3 below: [ka] (In the formula, R' 11 ~R' 14 each independently represents a substituted or unsubstituted methyl; R' 15 and R' 16 each independently represents hydrogen or deuterium; Ar' 11 and Ar' 12 are each independently an unsubstituted or deuterium-substituted phenyl, an unsubstituted or deuterium-substituted biphenyl, an unsubstituted or deuterium-substituted terphenyl, an unsubstituted or deuterium-substituted naphthyl, or an unsubstituted or deuterium-substituted group of the following formula (a): [ka] or a combination thereof, x represents an integer of 1 to 4, y represents an integer of 1 to 3, and when x and y are 2 or more, each R' 15 and each R' 16 may be the same or different) An organic electroluminescent compound represented by the formula: [Aspect 22] The compound of formula 3 is a compound: [ka] [ka] 22. The organic electroluminescent compound according to embodiment 21, selected from:

Claims

1. Formula 1 below: 【Chemical 1】 (In the formula, R １ ~R ４ are each independently *-(L １ ) ａ -(Ar １ ) ｂ , hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C3 to C30) cycloalkyl, substituted or unsubstituted (3 to 7 membered) heterocycloalkyl, substituted or unsubstituted (C6 to C30) aryl, or substituted or unsubstituted (3 to 30 membered) heteroaryl, or may be linked to adjacent substituents to form a ring; R ５ ~R １２ are each independently *-(L １ ) ａ -(Ar １ ) ｂ , hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C3 to C30) cycloalkyl, substituted or unsubstituted (3 to 7-membered) heterocycloalkyl, a substituted or unsubstituted fused ring of a (C3 to C30) aliphatic ring and a (C6 to C30) aromatic ring, substituted or unsubstituted (C6 to C30) aryl, substituted or unsubstituted (3 to 30-membered) heteroaryl, substituted or unsubstituted tri(C1 to C30) alkylsilyl, substituted or unsubstituted di(C1 to C30) alkyl(C6 to C30) arylsilyl, substituted or unsubstituted (C1 to C30) alkyldi(C6 to C30) arylsilyl, or substituted or unsubstituted tri(C6 to C30) arylsilyl, or may be linked to adjacent substituents to form a ring; R １ ~R １２ At least one of *-(L １ ) ａ -(Ar １ ) ｂ provided that it represents; L １ represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; Ar １ is a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 membered) heteroaryl, or —N—(Ar ２ ) (Ar ３ ) represents; Ar ２ and Ar ３ each independently represents a substituted or unsubstituted (C1 to C30) alkyl, a substituted or unsubstituted (C2 to C30) alkenyl, a substituted or unsubstituted fused ring of a (C3 to C30) aliphatic ring and a (C6 to C30) aromatic ring, a substituted or unsubstituted (C6 to C30) aryl, or a substituted or unsubstituted (3 to 30-membered) heteroaryl; a represents an integer of 1 or 2, b represents an integer of 1 to 4, and when a and b are 2 or more, each L １ and each Ar １ may be the same or different; R ５ ~R １０ and R １２ is hydrogen and R １１ with the proviso that compounds of Formula 1 containing a substituted amino group are excluded) 1. An organic electroluminescent compound represented by the formula:

2. Ar １ is a substituted or unsubstituted (3 to 30 membered) heteroaryl containing at least one N, or —N—(Ar ２ ) (Ar ３ ) represents; L １ 2. The organic electroluminescent compound according to claim 1, wherein represents a single bond or a substituted or unsubstituted (C6-C30) arylene.

3. The compound represented by formula 1 is represented by the following formulas 1-1 to 1-4: 【Chemistry 2】 (In the formula, R １ ~R １２ , L １ , Ar １ , a, and b are as defined in claim 1.

2. The organic electroluminescent compound according to claim 1, wherein the compound is represented by any one of the following formulas:

4. The compound represented by formula 1 is a compound represented by the following formulas 1-5 to 1-13: 【Chemistry 3】 【Chemistry 4】 【Chemistry 5】 (In the formula, R １ ~R １２ is as defined in claim 1; R １３ ~R １８ are each independently *-(L １ ) ａ -(Ar １ ) ｂ , hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C3 to C30) cycloalkyl, substituted or unsubstituted (3 to 7-membered) heterocycloalkyl, a substituted or unsubstituted fused ring of a (C3 to C30) aliphatic ring and a (C6 to C30) aromatic ring, substituted or unsubstituted (C6 to C30) aryl, substituted or unsubstituted (3 to 30-membered) heteroaryl, substituted or unsubstituted tri(C1 to C30) alkylsilyl, substituted or unsubstituted di(C1 to C30) alkyl(C6 to C30) arylsilyl, substituted or unsubstituted (C1 to C30) alkyldi(C6 to C30) arylsilyl, or substituted or unsubstituted tri(C6 to C30) arylsilyl, or may be linked to adjacent substituents to form a ring; R in formulas 1-5 to 1-7 １ ~R １４ At least one of R in formulas 1-8 to 1-10 １ ~R １６ and at least one of R in formulas 1-11 to 1-13. １ ~R １８ At least one of *-(L １ ) ａ -(Ar １ ) ｂ provided that it represents; L １ , Ar １ , a, and b are as defined in claim 1.

2. The organic electroluminescent compound according to claim 1, wherein the compound is represented by any one of the following formulas:

5. L １ 2. The organic electroluminescent compound according to claim 1, wherein R represents a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthrenylene, substituted or unsubstituted triphenylenylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted triazinylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted quinoxalinylene, substituted or unsubstituted quinazolinylene, substituted or unsubstituted dibenzofuranylene, or substituted or unsubstituted benzoquinoxalinylene.

6. Ar １ The substituted or unsubstituted (3- to 30-membered) heteroaryl may be substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted dibenzoquinolinyl, substituted or unsubstituted dibenzoquinazolinyl, substituted or unsubstituted dibenzoquinoxalinyl, substituted or unsubstituted indeno 2. The organic electroluminescent compound according to claim 1, wherein the substituted or unsubstituted benzothiopyridyl is substituted or unsubstituted indenopyrimidinyl, substituted or unsubstituted indenopyrazinyl, substituted or unsubstituted benzofuropyridyl, substituted or unsubstituted benzofuropyrimidinyl, substituted or unsubstituted benzofuropyrazinyl, substituted or unsubstituted benzothiopyridyl, substituted or unsubstituted benzothiopyrimidinyl, substituted or unsubstituted benzothiopyrazinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.

7. Ar １ 2. The organic electroluminescent compound according to claim 1, wherein the substituted or unsubstituted (C6-C30) aryl represents a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted triphenylenyl, or a substituted or unsubstituted phenanthrenyl.

8. Ar ２ and Ar ３ are each independently substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted chrysenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzofluorenyl, or substituted or unsubstituted dihydrophenanthrenyl.

9. The compound represented by formula 1 is the following compound: 【Chemistry 6】 【Chemistry 7】 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】 【Chemical 21】 【Chemical 22】 【Chemical 23】 【Chemistry 24】 【Chemistry 25】 【Chemical 26】 【Chemical 27】 【Chemical 28】 【Chemical 29】 【Chemistry 30】 【Chemical 31】 【Chemical 32】 2. The organic electroluminescent compound according to claim 1, selected from:

10. An organic electroluminescent material comprising the organic electroluminescent compound of claim 1.

11. 11. A plurality of host materials, comprising at least one organic electroluminescent material according to claim 10 as a first host material and at least one second host material different from the first host material.

12. The second host material has the following formula 11: 【Chemical Formula 33】 (In the formula, L ａ represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; Ar ａ represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 membered) heteroaryl; R ９ and R １０ each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C30) aryl, substituted or unsubstituted (3 to 50-membered) heteroaryl, substituted or unsubstituted tri(C1 to C30) alkylsilyl, substituted or unsubstituted di(C1 to C30) alkyl(C6 to C30) arylsilyl, substituted or unsubstituted (C1 to C30) alkyldi(C6 to C30) arylsilyl, substituted or unsubstituted tri(C6 to C30) arylsilyl, a substituted or unsubstituted fused ring of a (C3 to C30) aliphatic ring and a (C6 to C30) aromatic ring, substituted or unsubstituted mono- or di-(C1 to C30) alkylamino, substituted or unsubstituted mono- or di-(C2 to C30) alkenylamino , a substituted or unsubstituted (C1 to C30) alkyl(C2 to C30) alkenylamino, a substituted or unsubstituted (C1 to C30) alkyl(C6 to C30) arylamino, a substituted or unsubstituted (C1 to C30) alkyl(3 to 30 membered) heteroarylamino, a substituted or unsubstituted (C2 to C30) alkenyl(C6 to C30) arylamino, a substituted or unsubstituted (C2 to C30) alkenyl(3 to 30 membered) heteroarylamino, a substituted or unsubstituted mono- or di-(C6 to C30) arylamino, a substituted or unsubstituted mono- or di-(3 to 30 membered) heteroarylamino, or a substituted or unsubstituted (C6 to C30) aryl(3 to 30 membered) heteroarylamino, or it may be linked to adjacent substituents to form a ring; f and g each independently represent an integer of 1 to 4, and when f and g are 2 or more, R ９ and R １０ may be the same or different) 12. The plurality of host materials of claim 11, comprising a compound represented by:

13. The compound represented by formula 11 is a compound represented by the following formula 12 or 13: 【Chemical 34】 (In the formula, L ａ , Ar ａ , R ９ , R １０ and f is as defined in claim 12; T １ and T ２ each independently represents a single bond, O, or S; L ｂ is in claim 12 ａ as defined as: Ar ｂ is Ar in claim 12 ａ as defined as: R １１ ~R １４ are each independently R in claim 12. ９ as defined as: X １ is O, S, or NR ａ represents; R ａ represents a substituted or unsubstituted (C6-C30) aryl; g' and h each independently represent an integer of 1 to 3, i and k each independently represent an integer of 1 to 4, j represents an integer of 1 or 2, and when g', h, i, j, and k are 2 or more, R １０ Each of R １１ Each of R １２ Each of R １３ and R １４ may be the same or different) 13. The plurality of host materials of claim 12, represented by:

14. The compound represented by formula 11 is the following compound: 【Chemical 35】 【Chemical 36】 【Chemical 37】 【Chemical Formula 38】 13. The plurality of host materials of claim 12 selected from:

15. An organic electroluminescent device comprising the organic electroluminescent compound of claim 1.

16. 16. The organic electroluminescent device according to claim 15, wherein the organic electroluminescent compound is comprised in the hole transporting zone and / or the electron transporting zone and / or the light-emitting layer.

17. 12. An organic electroluminescent device comprising an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein the at least one light-emitting layer comprises a plurality of host materials according to claim 11.

18. Formula 3 below: 【Chemical 39】 (In the formula, R' １１ ~R' １４ each independently represents a substituted or unsubstituted methyl; R' １５ and R' １６ each independently represents hydrogen or deuterium; Ar' １１ and Ar' １２ are each independently an unsubstituted or deuterium-substituted phenyl, an unsubstituted or deuterium-substituted biphenyl, an unsubstituted or deuterium-substituted terphenyl, an unsubstituted or deuterium-substituted naphthyl, or an unsubstituted or deuterium-substituted alkyl group of the following formula (a): 【Chemistry 40】 or a combination thereof, x represents an integer of 1 to 4, y represents an integer of 1 to 3, and when x and y are 2 or more, each R' １５ and each R' １６ may be the same or different) An organic electroluminescent compound represented by the formula:

19. The compound represented by formula 3 is the following compound: 【Chemistry 41】 【Chemistry 42】 19. The organic electroluminescent compound according to claim 18, selected from:

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