Organic electroluminescent compounds and organic electroluminescent devices containing the same

Abstract

To provide an organic electroluminescent compound that can achieve an organic electroluminescent device with characteristics of low driving voltage and / or high luminous efficiency.SOLUTION: An organic electroluminescent compound represented by the following formula.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present disclosure relates to organic electroluminescent compounds and organic electroluminescent devices containing the same. [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 a compound 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 examples in which spiro[fluorene-9,9'-xanthene] derivative compounds and spiro[fluorene-9,9'-thioxanthene] derivative compounds are used as materials for an electron buffer layer or an electron transport layer, but the compounds in this document are not used as materials for a hole transport layer. [Prior art documents] [Patent documents]

[0007] [Patent Document 1] International Publication No. 2016 / 021989A1 Brochure [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 capable of fabricating an organic electroluminescent device characterized by low driving voltage and / or high luminous efficiency, 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 found that the above-mentioned object can be achieved by an organic electroluminescent compound represented by the following formula 1, and have completed the present invention. [ka]

[0011] In Equation 1, X and Y each independently represent O or S; L1 represents a single bond, a substituted or unsubstituted (C1 to C30) alkylene, a substituted or unsubstituted (C6 to C30) arylene, a substituted or unsubstituted (3 to 30-membered) heteroarylene, or a substituted or unsubstituted (C3 to C30) cycloalkylene; Ar1 and Ar2 each independently represent a substituted or unsubstituted (C6 to C30) aryl, a substituted or unsubstituted (3 to 30-membered) heteroaryl, a substituted or unsubstituted (C3 to C30) cycloalkyl, a substituted or unsubstituted fused ring of a (C3 to C30) aliphatic ring and a (C6 to C30) aromatic ring, or -L2-N-(Ar3)(Ar4), or may be linked to adjacent substituents to form a ring; R1 to R4 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C30) aryl, substituted or unsubstituted (3 to 30-membered) heteroaryl, substituted or unsubstituted (C3 to C30) cycloalkyl, substituted or unsubstituted (C1 to C30) alkoxy, 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, or -L3-N-(Ar5)(Ar6), or can be linked to adjacent substituents to form a ring; L2 and L3 each independently represent a single bond, a substituted or unsubstituted (C1 to C30) alkylene, a substituted or unsubstituted (C6 to C30) arylene, a substituted or unsubstituted (3 to 30-membered) heteroarylene, or a substituted or unsubstituted (C3 to C30) cycloalkylene; Ar3 to Ar6 each independently represent a substituted or unsubstituted (C1 to C30) alkyl, a substituted or unsubstituted (C2 to C30) alkenyl, a substituted or unsubstituted (C6 to C30) aryl, a substituted or unsubstituted fused ring of a (C3 to C30) aliphatic ring and a (C6 to C30) aromatic ring, or a substituted or unsubstituted (3 to 30-membered) heteroaryl; a to c each independently represent an integer of 1 to 4, and d represents an integer of 1 to 3; When a to d are each independently an integer of 2 or more, R1 to R4 may be the same or different.

[0012] Advantageous Effects of the Invention Organic electroluminescent devices with low driving voltage and / or high luminous efficiency properties can be fabricated by incorporating the organic electroluminescent compounds according to the present disclosure. 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 organic electroluminescent compounds represented by the above formula 1, organic electroluminescent materials comprising the organic electroluminescent compounds, and organic electroluminescent devices comprising the organic electroluminescent compounds.

[0015] 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.

[0016] 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.

[0017] The term "hole transport zone" in the present disclosure refers to a zone through which holes travel between the first electrode and the light-emitting layer. For example, the hole transport zone may include at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, an emission auxiliary layer, and an electron blocking layer. Each of the hole injection layer, the hole transport layer, the hole auxiliary layer, the emission auxiliary layer, and the electron blocking layer may be a single layer or a multilayer structure in which two or more layers are stacked. According to one embodiment of the present application, the hole transport zone may include a first hole transport layer and a second hole transport layer. The second hole transport layer may be at least one layer of the multiple hole transport layers, and may include at least one of the hole auxiliary layer, the emission auxiliary layer, and the electron blocking layer. Additionally, according to another embodiment of the present application, the hole transport zone may include a first hole transport layer and a second hole transport layer, the first hole transport layer may be disposed between the first electrode and the light-emitting layer, the second hole transport layer may be disposed between the first hole transport layer and the light-emitting layer, and the second hole transport layer may be a layer that serves as a hole transport layer, a light-emitting auxiliary layer, a hole auxiliary layer, and / or an electron blocking layer.

[0018] 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, more preferably 1 to 10 carbon atoms. The alkyl may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, etc. 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 carbon atoms. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, etc. 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 skeletal ring carbon atoms (preferably 6 to 20, more preferably 6 to 15 skeletal ring carbon atoms), which may be partially saturated. The aryl may include a spiro structure. Specific examples of aryl include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthrenyl, benzophenanthrenyl, phenylphenanthrenyl, anthracenyl, benzanthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, benzochrysenyl, naphthacenyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, mesityl, cumenyl, spiro[fluorene-fluoren]yl, spiro[fluorene-benzofluoren]yl, azulenyl, tetramethyl-dihydrophenanthrenyl, and the like. 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, 11,11-dimethyl-1-benzo[b]fluorenyl, 11,11-dimethyl-2-benzo[b]fluorenyl, 11,11-dimethyl-3-benzo[b]fluorenyl, 11,11-dimethyl-4-benzo[b]fluorenyl, 11,11-dimethyl-5-benzo[b]fluorenyl,11,11-dimethyl-6-benzo[b]fluorenyl, 11,11-dimethyl-7-benzo[b]fluorenyl, 11,11-dimethyl-8-benzo[b]fluorenyl, 11,11-dimethyl-9-benzo[b]fluorenyl, 11,11-dimethyl-10-benzo[b]fluorenyl, 11,11-dimethyl-1-benzo[c]fluorenyl, 11,11-dimethyl-2-benzo[c]fluorenyl, 11,11-dimethyl-3-benzo[c]fluorenyl, 11,11-dimethyl-4-benzo[c]fluorenyl, 11,11-dimethyl-5 -benzo[c]fluorenyl, 11,11-dimethyl-6-benzo[c]fluorenyl, 11,11-dimethyl-7-benzo[c]fluorenyl, 11,11-dimethyl-8-benzo[c]fluorenyl, 11,11-dimethyl-9-benzo[c]fluorenyl, 11,11-dimethyl-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 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 nyl, 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 , 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, 9,9,10,10-tetramethyl-9,10-dihydro-4-phenanthrenyl, etc. In the present disclosure, the term "(3- to 30-membered)heteroaryl(ene)" refers to an aryl having 3 to 30 skeletal ring atoms containing at least one, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, Si, P, Se, and Ge, and the number of skeletal ring carbon atoms is preferably 5 to 25. The heteroaryl or heteroarylene may be a monocyclic ring or a fused ring fused with at least one benzene ring; and may be partially saturated. The heteroaryl in the present disclosure may also be formed by attaching at least one heteroaryl or aryl group to a heteroaryl group via a single bond. Specific examples of heteroaryl include monocyclic heteroaryl 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, and benzothienoquinazolinyl.benzothienonaphthyridinyl, benzothienopyrimidinyl, naphthothienopyrimidinyl, pyrimidoindolyl, benzopyrimidindolyl, benzofuropyrazinyl, naphthofuropyrazinyl, benzothienopyrazinyl, naphthothienopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, Examples of fused ring heteroaryls include isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, indolizidinyl, acridinyl, silafluorenyl, germafluorenyl, benzotriazolyl, phenazinyl, imidazopyridinyl, chromenoquinazolinyl, thiochromenoquinazolinyl, dimethylbenzoperimidinyl, indolocarbazolyl, and indenocarbazolyl. More specifically, heteroaryl is selected from the group consisting of 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolizidinyl, 2-indolizidinyl, 3-indolizidinyl, 5-indolizidinyl, 6-indolizidinyl, 7-indolizidinyl, 8-indolizidinyl, 2-imidazopyridinyl, nyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl,1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-Isoquinolyl, 5-Isoquinolyl, 6-Isoquinolyl, 7-Isoquinolyl, 8-Isoquinolyl, 2-Quinoxalinyl, 5-Quinoxalinyl, 6-Quinoxalinyl, 1-Carbazolyl, 2-Carbazolyl, 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, 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-1-yl pyrrol-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 thyl-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]-benzo Furanyl, 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]-benzothiophenyl, 9-naphtho-[2,1-b]-benzothiophenyl, 10-naphtho-[2,1-b]-benzothiophenyl, 2-benzofuro[3,2-d]pyrimidinyl, 6-benzofuro[3,2-d]pyrimidinyl Nyl, 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-benzothio[3,2-d]pyrimidinyl, 2-benzo Furo[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, The ring may be 9-benzothio[3,2-d]pyrazinyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 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 skeletal carbon atoms (preferably 3 to 25, more preferably 3 to 18, carbon atoms) with at least one aromatic ring having 6 to 30 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, etc. In the present disclosure, a carbon atom of the 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.

[0019] Additionally, in this disclosure, "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.

[0020] In the present disclosure, the term "ring formed by linking adjacent substituents" 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, and is preferably a substituted or unsubstituted (3- to 26-membered) monocyclic or polycyclic aliphatic ring, aromatic ring, or combination thereof. Furthermore, the formed ring may contain at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably 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. In one embodiment, the 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.

[0021] Furthermore, in the present disclosure, the term "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a functional group is replaced with another atom or functional group, i.e., a substituent, and two or more substituents are connected by a group connecting the substituents. For example, a "substituent having two or more substituents bonded thereto" may be pyridine-triazine. That is, pyridine-triazine may be a heteroaryl, or may be interpreted as one substituent bonded to two heteroaryls. Preferably, the substituents of the substituted alkyl, substituted alkylene, substituted alkenyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted cycloalkyl, substituted cycloalkylene, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, and the substituted fused ring of an aliphatic ring and an aromatic ring in the formula of the present disclosure are each independently deuterium; halogen; cyano; carboxyl; nitro; hydroxy; phosphine oxide; (C1-C30) alkyl; halo(C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3- to 7-membered) hetero cycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (5-50 membered) heteroaryl unsubstituted or substituted with at least one of (C1-C30)alkyl, (C6-C30)aryl, and di(C6-C30)arylamino; (C6-C30)aryl unsubstituted or substituted with at least one of (C1-C30)alkyl, (3-50 membered)heteroaryl, and mono- or di-(C6-C30)arylamino; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; amino; mono- or di-(C1-C30)alkylamino; mono- or di-(C2-C30)alkenylamino;Mono- or di-(C6-C30)arylamino which is unsubstituted or substituted with at least one of (C1-C30)alkyl, (5-30 membered)heteroaryl, and di(C6-C30)arylamino; mono- or di-(3-30 membered)heteroarylamino; (C1-C30)alkyl(C2-C30)alkenylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkyl(3-30 membered)heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30)alkenyl(3-30 membered) The group represents at least one selected from the group consisting of heteroarylamino, (C6-C30)aryl(3-30 membered)heteroarylamino, (C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30)arylcarbonyl, (C6-C30)arylphosphinyl, di(C6-C30)arylboronyl, di(C1-C30)alkylboronyl, (C1-C30)alkyl(C6-C30)arylboronyl, (C6-C30)aryl(C1-C30)alkyl, and (C1-C30)alkyl(C6-C30)aryl. For example, the substituent may be unsubstituted methyl, unsubstituted phenyl, or unsubstituted naphthyl.

[0022] In the following, an organic electroluminescent compound according to one embodiment is described.

[0023] The organic electroluminescent compound according to one embodiment is represented by Formula 1 below: [ka]

[0024] In Equation 1, X and Y each independently represent O or S; L1 represents a single bond, a substituted or unsubstituted (C1 to C30) alkylene, a substituted or unsubstituted (C6 to C30) arylene, a substituted or unsubstituted (3 to 30-membered) heteroarylene, or a substituted or unsubstituted (C3 to C30) cycloalkylene; Ar1 and Ar2 each independently represent a substituted or unsubstituted (C6 to C30) aryl, a substituted or unsubstituted (3 to 30-membered) heteroaryl, a substituted or unsubstituted (C3 to C30) cycloalkyl, a substituted or unsubstituted fused ring of a (C3 to C30) aliphatic ring and a (C6 to C30) aromatic ring, or -L2-N-(Ar3)(Ar4), or may be linked to adjacent substituents to form a ring; R1 to R4 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C30) aryl, substituted or unsubstituted (3 to 30-membered) heteroaryl, substituted or unsubstituted (C3 to C30) cycloalkyl, substituted or unsubstituted (C1 to C30) alkoxy, 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, or -L3-N-(Ar5)(Ar6), or can be linked to adjacent substituents to form a ring; L2 and L3 each independently represent a single bond, a substituted or unsubstituted (C1 to C30) alkylene, a substituted or unsubstituted (C6 to C30) arylene, a substituted or unsubstituted (3 to 30-membered) heteroarylene, or a substituted or unsubstituted (C3 to C30) cycloalkylene; Ar3 to Ar6 each independently represent a substituted or unsubstituted (C1 to C30) alkyl, a substituted or unsubstituted (C2 to C30) alkenyl, a substituted or unsubstituted (C6 to C30) aryl, a substituted or unsubstituted fused ring of a (C3 to C30) aliphatic ring and a (C6 to C30) aromatic ring, or a substituted or unsubstituted (3 to 30-membered) heteroaryl; a to c each independently represent an integer of 1 to 4, and d represents an integer of 1 to 3; When a to d are each independently an integer of 2 or greater, R1 to R4 may be the same or different.

[0025] In one embodiment, both X and Y may be O, or both X and Y may be S. For example, X may be O and Y may be S. As a further example, X may be S and Y may be O.

[0026] In one embodiment, L1 may be a single bond or a substituted or unsubstituted (C6-C30) arylene, preferably a single bond or a substituted or unsubstituted (C6-C25) arylene, and more preferably a single bond or a substituted or unsubstituted (C6-C18) arylene. For example, L1 may be a single bond or unsubstituted phenylene.

[0027] In one embodiment, Ar1 and Ar2 may each independently represent a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 membered) heteroaryl, or a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, preferably a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (5-30 membered) heteroaryl, or a substituted or unsubstituted fused ring of a (C3-C20) aliphatic ring and a (C6-C25) aromatic ring, more preferably a substituted or unsubstituted (C6-C25) aryl, a substituted or unsubstituted (5-25 membered) heteroaryl, or a substituted or unsubstituted fused ring of a (C3-C10) aliphatic ring and a (C6-C18) aromatic ring. For example, Ar1 and Ar2 may each independently be unsubstituted or naphthyl-substituted phenyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted dihydrotetramethylphenanthrenyl.

[0028] In one embodiment, R1 to R4 may all be hydrogen.

[0029] According to one embodiment, the organic electroluminescent compound of Formula 1 can be represented by any one of the following Formulas 1-1 to 1-4: [ka]

[0030] In formulas 1-1 to 1-4, R1 to R4, X, Y, L1, Ar1, Ar2, and a to d are 、 each independently as defined in Equation 1 above.

[0031] In one embodiment, the organic electroluminescent compounds represented by formulas 1-1 to 1-4 may be those in which X and Y each independently represent O or S; L1 represents a single bond or a substituted or unsubstituted (C6 to C30) arylene; Ar1 ​​and Ar2 each independently represent a substituted or unsubstituted (C6 to C30) aryl, a substituted or unsubstituted (3 to 30-membered) heteroaryl, or a substituted or unsubstituted fused ring of a (C3 to C30) aliphatic ring and a (C6 to C30) aromatic ring; and all of R1 to R4 are hydrogen.

[0032] 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] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0033] The compound of formula 1 according to the present disclosure can be prepared as depicted in, but not limited to, the following reaction schemes 1-3. Furthermore, it can be prepared by synthetic methods known to those skilled in the art. [ka] [ka]

[0034] In the above reaction schemes 1 to 3, the definition of each substituent is as defined in formula 1 above.

[0035] As described above, illustrative synthetic examples of compounds represented by Formula 1 according to the present disclosure are described, and these are based on Buchwald-Hartwig cross-coupling reactions, N-arylation reactions, H-mont-mediated etherification reactions, Miyaura borylation reactions, Suzuki cross-coupling 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.

[0036] According to an embodiment, the present disclosure may provide an organic electroluminescent material comprising the organic electroluminescent compound of Formula 1, and an organic electroluminescent device comprising the organic electroluminescent material.

[0037] The organic electroluminescent material may consist solely of the organic electroluminescent compound of Formula 1 of the present disclosure, or may further contain conventional materials contained in organic electroluminescent materials.

[0038] An organic electroluminescent material according to one embodiment may include at least one compound represented by Formula 1. The organic electroluminescent compound of Formula 1 of the present disclosure may preferably be included as a hole transport material in the hole transport zone of an organic electroluminescent device. The hole transport zone includes a hole transport layer. Furthermore, the hole transport zone may further include at least one of a hole injection layer, a hole auxiliary layer, a light-emitting auxiliary layer, and an electron blocking layer in addition to the hole transport layer.

[0039] The organic electroluminescent material according to one embodiment may be a hole transport material, a hole injection material, a hole assisting material, an emitting assisting material, or an electron blocking material, and preferably may be a hole transport material, a hole assisting material, or an emitting assisting material for a green light-emitting organic electroluminescent device. When the hole transport layer is a multi-layer structure, the hole transport material (hole assisting material) may be included in the hole transport layer adjacent to the emitting layer.

[0040] The organic electroluminescent material of the present disclosure may include, in addition to the organic electroluminescent compound of Formula 1 above, at least one host compound and at least one dopant.

[0041] The host contained in the organic electroluminescent material of the present disclosure can be any known phosphorescent host, for example, multiple host compounds (co-hosts) can be used as host materials. In this case, they can be contained in the organic electroluminescent material in a weight ratio of the first host material to the second host material of 1:9 to 9:1, for example, 2:8 to 8:2, 3:7 to 7:3, 4:6 to 6:4, and 5:5. When two or more materials are contained in one layer, these materials can be mixed and vapor-deposited to form a layer, or can be simultaneously and separately vapor-deposited to form a layer.

[0042] The dopant contained in the organic electroluminescent material of the present disclosure can be at least one phosphorescent or fluorescent dopant, preferably phosphorescent dopant.The phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particularly limited, but can be preferably a metal complex compound of a metal atom optionally selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), more preferably an ortho-metal complex compound of a metal atom optionally selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and even more preferably an ortho-metal iridium complex compound optionally.

[0043] The dopant contained in the organic electroluminescent device of the present disclosure can be, but is not limited to, a compound represented by the following formula 101: [ka]

[0044] In Equation 101, L is any one of the following structures 1 to 3: [ka] is selected from R 100 ~R 103 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, cyano, substituted or unsubstituted (3-30 membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy, or can be bonded to adjacent substituents to form a ring together with the pyridine, such as a substituted or unsubstituted quinoline, substituted or unsubstituted benzofuropyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuroquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indenoquinoline ring; R 104 ~R 107each 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 can be combined with adjacent substituents to form a ring together with benzene, such as a 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 ring; R 201 ~R 220 each independently represent 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 together to form a substituted or unsubstituted ring; s represents an integer of 1 to 3.

[0045] In particular, specific examples of dopant compounds include, but are not limited to, the following: [ka] [ka] [ka] [ka] [ka] [ka]

[0046] In the following, an organic electroluminescent device to which the above-mentioned organic electroluminescent compounds or organic electroluminescent materials are applied will be described.

[0047] 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.

[0048] In one embodiment, the organic layer comprises a hole transporting zone comprising the organic electroluminescent compound of the present disclosure. The hole transporting zone may comprise at least one layer selected from the group consisting of a hole injection layer, a hole transporting layer, a hole auxiliary layer, a light-emitting auxiliary layer, and an electron blocking layer, for example, a hole transporting layer, a hole injection layer, a hole auxiliary layer, and an electron blocking layer. For example, it may comprise only the organic electroluminescent compound of the present disclosure, or may comprise a mixture of at least two organic electroluminescent compounds, or may further comprise conventional materials contained in organic electroluminescent materials.

[0049] In addition to the hole-transporting zone, the organic layer may further include at least one layer selected from the group consisting of an emitting layer, an electron-transporting layer, an electron-injecting layer, an intermediate layer, a hole-blocking layer, and an electron buffer layer, and each layer may further include multiple layers. The organic layer may further include at least one compound selected from an arylamine compound and a styrylarylamine compound. The organic layer 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.

[0050] The organic electroluminescent material according to one embodiment can be used as a light-emitting material for a white organic light-emitting device. Various structures of the white organic electroluminescent device have been proposed, 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 the 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).

[0051] 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.

[0052] 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, where each of the multiple layers can simultaneously use two types of compounds. The hole injection layer can also be doped as a p-dopant. The electron blocking layer can also be disposed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can confine excitons within the light-emitting layer by preventing electron overflow from the light-emitting layer, thereby preventing light leakage. The hole transport layer or electron blocking layer can be a multilayer, in which case each layer can use multiple compounds.

[0053] 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 multilayered to control electron injection and improve the interface characteristics between the light-emitting layer and the electron injection layer, where each layer can simultaneously use two different compounds. The hole blocking layer or the electron transport layer can also be multilayered, where each layer can use multiple compounds. The electron injection layer can also be doped with an n-type dopant.

[0054] 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.

[0055] 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.

[0056] 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 prepared.

[0057] To form each layer of the organic electroluminescent device of the present disclosure, dry film formation methods such as vacuum evaporation, sputtering, plasma, and ion plating, or wet film formation methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, and flow coating can be used.

[0058] 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.

[0059] When forming a layer by using at least one organic electroluminescent compound according to an embodiment, the layer can be formed by, but not limited to, 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 the 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 the material.

[0060] According to one embodiment, the organic electroluminescent device of the present disclosure can be used to manufacture a display device, such as a smartphone, tablet, laptop, PC, TV, or vehicle display device, or a lighting device, such as an outdoor or indoor light.

[0061] To provide a detailed understanding of the present disclosure, methods for preparing compounds according to the present disclosure are described below with reference to synthetic methods for representative compounds or intermediate compounds. [Example]

[0062] [Example 1] Preparation of Compound C-1 [ka]

[0063] 1) Synthesis of Compound 1-2 Compound 1-1 (141 g, 375 mmol) was dissolved in 1.4 L of toluene in a flask, and then 700 mL of 30% hydrogen peroxide (HO) was slowly added dropwise at room temperature. Next, 200 mL of 35% aqueous sodium bisulfite solution was slowly added dropwise. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the remaining water was removed with magnesium sulfate and then dried. Compound 1-2 (90 g, yield: 69%) was then obtained by column chromatography.

[0064] 2) Synthesis of Compounds 1-3 Compound 1-2 (90 g, 258 mmol), 2-bromo-1-chloro-3-fluorobenzene (54 g, 258 mmol), potassium carbonate (53 g, 387 mmol), and 900 mL of N-methylpyrrolidone (NMP) were added to a flask and refluxed at 160 °C for 4 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and residual water was removed with magnesium sulfate and then dried. This was then separated by column chromatography to obtain compound 1-3 (97 g, yield: 70%).

[0065] 3) Synthesis of Compounds 1-4 Compound 1-3 (100 g, 186 mmol), palladium acetate (Pd(OAc)2) (2 g, 9.3 mmol), tricyclohexylphosphine (PCy3) (5.2 g, 18 mmol), potassium carbonate (77 g, 558 mmol), and 1.5 L of dimethylacetamide (DMAc) were added to a flask and refluxed at 150 °C for 10 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the residual water was removed with magnesium sulfate and then dried. This was then separated by column chromatography to give compound 1-4 (43 g, 50% yield).

[0066] 4) Synthesis of Compound C-1 Compound 1-4 (8.0 g, 17.5 mmol), compound 1-5 (5.2 g, 21.0 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2dba3) (0.80 g, 0.88 mmol), tri-tert-butylphosphine (P(tBu)3) (0.86 mL, 1.75 mmol in 50% toluene solution), sodium t-butoxide (NaOtBu) (3.4 g, 35 mmol), and 90 mL of toluene were placed in a flask and refluxed at 110 °C for 18 h. After the reaction was completed, the reaction mixture was cooled to room temperature, and the solvent was removed using a rotary evaporator. This was then purified by column chromatography to give compound C-1 as a white solid (8.8 g, yield: 76%).

[0067] [Table 1]

[0068] [Example 2] Preparation of Compound C-2 [ka] Compound 1-4 (8.0 g, 17.5 mmol), compound 1-6 (6.0 g, 21.0 mmol), Pd2dba3 (0.80 g, 0.88 mmol), P(tBu)3 (0.86 mL, 1.75 mmol, 50% toluene solution), NaOtBu (3.4 g, 35 mmol), and 90 mL of toluene were added to a flask and refluxed at 110 °C for 18 h. After the reaction was complete, the reaction mixture was cooled to room temperature, and the solvent was removed using a rotary evaporator. This was then purified by column chromatography to give compound C-2 as a white solid (6.6 g, yield: 53%).

[0069] [Table 2]

[0070] [Example 3] Preparation of Compound C-3 [ka] Compound 1-4 (10.0 g, 21.9 mmol), compound 1-7 (9.49 g, 26.3 mmol), Pd2dba3 (1.00 g, 1.09 mmol), P(tBu)3 (1.08 mL, 2.19 mmol, 50% toluene solution), NaOtBu (4.21 g, 43.8 mmol), and 90 mL of toluene were added to a flask and refluxed at 110 °C for 18 h. After the reaction was complete, the reaction mixture was cooled to room temperature, and the solvent was removed using a rotary evaporator. This was then purified by column chromatography to give compound C-3 as a white solid (8.7 g, yield: 51%).

[0071] [Table 3]

[0072] [Example 4] Synthesis of Compound C-6 [ka] Compound 1-4 (5.0 g, 10.9 mmol), compound 1-8 (2.95 g, 12.0 mmol), Pd2dba3 (0.50 g, 0.55 mmol), P(tBu)3 (0.54 mL, 1.09 mmol, 50% toluene solution), NaOtBu (2.10 g, 21.9 mmol), and 55 mL of toluene were added to a flask and refluxed for 18 h. After the reaction was complete, the reaction mixture was cooled to room temperature and the solvent was removed using a rotary evaporator. This was then purified by column chromatography to give compound C-6 as a white solid (3.4 g, yield: 47%).

[0073] [Table 4]

[0074] [Example 5] Synthesis of Compound C-281 [ka] Compound 1-4 (10.0 g, 21.9 mmol), compound 1-9 (6.46 g, 21.9 mmol), Pd2dba3 (1.00 g, 1.09 mmol), P(tBu)3 (1.08 mL, 2.19 mmol, 50% toluene solution), NaOtBu (4.21 g, 43.8 mmol), and 110 mL of toluene were added to a flask and refluxed for 18 h. After the reaction was complete, the reaction mixture was cooled to room temperature and the solvent was removed using a rotary evaporator. This was then purified by column chromatography to give compound C-281 as a white solid (9.0 g, 57% yield).

[0075] [Table 5]

[0076] 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.

[0077] Device Example 1: Fabrication of a Green-Emitting OLED 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 first 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. Next, compound C-1 was introduced into another cell of the vacuum evaporation system, and a current was passed through the cell to evaporate the compound, 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. Compounds H-1 and H-2 were introduced as hosts into two cells of a vacuum evaporation system, respectively, and compound D-130 was introduced as a dopant into another cell. The two host materials were evaporated in different ratios of 2:1, and the dopant materials were co-evaporated in different ratios. The dopant materials were deposited at a doping amount of 10 wt% based on the total amount of host and dopant to form an emitting layer with a thickness of 40 nm on the second hole transport layer. Next, compounds ETL-1 and EIL-1 were evaporated as electron transport materials in a weight ratio of 40:60 to form a 35 nm electron transport layer on the emitting layer. Compound EIL-1 was evaporated as a 2 nm-thick electron injection layer on the electron transport 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 thus fabricated.

[0078] Device Example 2: Fabrication of a Green-Emitting OLED According to the Present Disclosure An OLED was fabricated in the same manner as in Device Example 1, except that Compound C-2 was used as the material of the second hole transport layer.

[0079] Device Example 3: Fabrication of a Green-Emitting OLED According to the Present Disclosure An OLED was fabricated in the same manner as in Device Example 1, except that Compound C-3 was used as the material of the second hole transport layer.

[0080] Device Example 4: Fabrication of a Green-Emitting OLED According to the Present Disclosure An OLED was fabricated in the same manner as in Device Example 1, except that Compound C-6 was used as the material of the second hole transport layer.

[0081] Comparative Example 1: Fabrication of a green-emitting OLED not according to the present disclosure An OLED was fabricated in the same manner as in Device Example 1, except that compound HT-1 was used as the material of the second hole transport layer.

[0082] Comparative Example 2: Fabrication of a green-emitting OLED not according to the present disclosure An OLED was fabricated in the same manner as in Device Example 1, except that compound HT-2 was used as the material of the second hole transport layer.

[0083] The driving voltage, luminous efficiency, and CIE color coordinates at a luminance of 1,000 nits of the OLEDs according to the device examples and comparative examples prepared as described above were measured, and the results are shown in Table 1 below:

[0084] [Table 6]

[0085] From Table 1 above, it can be seen that the organic electroluminescent device that comprises the organic electroluminescent compound of the present disclosure as a hole transport material exhibits the characteristics of lower driving voltage and higher luminous efficiency compared with the organic electroluminescent device that comprises conventional hole transport material.

[0086] The compounds used in the device examples and comparative examples are specifically shown in Table 2 below:

[0087]

Table 7

[0088]

Table 8

Claims

1. An organic electroluminescent compound represented by the following formula 1: 【Chemical 1】 (In the formula, X and Y each independently represent O or S; L １ represents a single bond, a substituted or unsubstituted (C1 to C30) alkylene, a substituted or unsubstituted (C6 to C30) arylene, a substituted or unsubstituted (3 to 30-membered) heteroarylene, or a substituted or unsubstituted (C3 to C30) cycloalkylene; Ar １ and Ar ２ each independently represents a substituted or unsubstituted (C6 to C30) aryl, a substituted or unsubstituted (3 to 30-membered) heteroaryl, a substituted or unsubstituted (C3 to C30) cycloalkyl, a substituted or unsubstituted fused ring of a (C3 to C30) aliphatic ring and a (C6 to C30) aromatic ring, or -L ２ -N-(Ar ３ ) (Ar ４ ) or may be linked to adjacent substituents to form a ring; R １ ~R ４ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C30) aryl, substituted or unsubstituted (3 to 30 membered) heteroaryl, substituted or unsubstituted (C3 to C30) cycloalkyl, substituted or unsubstituted (C1 to C30) alkoxy, 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, or -L ３ -N(Ar ５ ) (Ar ６ ) or can be linked to adjacent substituents to form a ring; L ２ and L ３ each independently represents a single bond, a substituted or unsubstituted (C1 to C30) alkylene, a substituted or unsubstituted (C6 to C30) arylene, a substituted or unsubstituted (3 to 30-membered) heteroarylene, or a substituted or unsubstituted (C3 to C30) cycloalkylene; Ar ３ ~Ar ６ each independently represent a substituted or unsubstituted (C1 to C30) alkyl, a substituted or unsubstituted (C2 to C30) alkenyl, a substituted or unsubstituted (C6 to C30) aryl, a substituted or unsubstituted fused ring of a (C3 to C30) aliphatic ring and a (C6 to C30) aromatic ring, or a substituted or unsubstituted (3 to 30-membered) heteroaryl; a to c each independently represent an integer of 1 to 4, and d represents an integer of 1 to 3; When a to d are each independently an integer of 2 or more, R １ ~R ４ may be the same or different).

2. 2. The organic electroluminescent compound according to claim 1, wherein the formula 1 is represented by any one of the following formulas 1-1 to 1-4: 【Chemistry 2】 (In the formula, R １ ~R ４ , X, Y, L １ , Ar １ , Ar ２ , and a to d are each independently as defined in claim 1).

3. L １ represents a single bond or a substituted or unsubstituted (C6 to C30) arylene; Ar １ and Ar ２ each independently represents a substituted or unsubstituted (C6 to C30) aryl, a substituted or unsubstituted (3 to 30-membered) heteroaryl, or a substituted or unsubstituted fused ring of a (C3 to C30) aliphatic ring and a (C6 to C30) aromatic ring; The organic electroluminescent compound according to claim 2 .

4. The substituted alkyl, the substituted alkylene, the substituted alkenyl, the substituted aryl, the substituted arylene, the substituted heteroaryl, the substituted heteroarylene, the substituted cycloalkyl, the substituted cycloalkylene, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, and the substituents of the substituted fused ring of the aliphatic ring and the aromatic ring are each independently deuterium; halogen; cyano; carboxyl; nitro; hydroxy; phosphine oxide; (C1 (C6-C30)arylthio; (5-50 membered)heteroaryl that is unsubstituted or substituted with at least one of (C1-C30)alkyl, (C6-C30)aryl, and di(C6-C30)arylamino; and unsubstituted. or (C6-C30)aryl substituted with at least one of (C1-C30)alkyl, (3- to 50-membered)heteroaryl, and mono- or di-(C6-C30)arylamino; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; amino; mono- or di-(C1-C30)alkylamino; mono- or di-(C2-C30)alkenylamino; unsubstituted or (C1-C30)alkenyl mono- or di-(C6-C30)arylamino substituted with at least one of alkyl, (5-30 membered)heteroaryl, and di(C6-C30)arylamino; mono- or di-(3-30 membered)heteroarylamino; (C1-C30)alkyl(C2-C30)alkenylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkyl(3-30 membered)heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30)alkenyl(3-30 membered)heteroarylamino;2. The organic electroluminescent compound according to claim 1, which is at least one selected from the group consisting of (C6-C30)aryl(3-30 membered)heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; (C6-C30)arylphosphinyl; di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl.

5. 2. The organic electroluminescent compound according to claim 1, wherein the compound represented by formula 1 is selected from the following compounds: 【Chemistry 3】 【Chemistry 4】 【Chemistry 5】 【Chemistry 6】 【Chemistry 7】 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 。

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

7. 7. The organic electroluminescent device according to claim 6, wherein the organic electroluminescent compound is contained in a hole transport zone.

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