Organic electroluminescent compound, plurality of host materials, and organic electroluminescent device comprising the same

Abstract

The present disclosure relates to organic electroluminescent compounds, a plurality of host materials, and an organic electroluminescent device comprising the same. By comprising the organic electroluminescent compound and / or the plurality of host materials according to the present disclosure, an organic electroluminescent device having a low driving voltage and / or high luminous efficiency and / or long lifespan can be provided.

Description

Technical Field

[0001] This disclosure relates to organic electroluminescent compounds, various host materials, and organic electroluminescent devices comprising the same. Background Technology

[0002] Electroluminescent devices (EL devices) are self-emissive display devices that offer advantages such as a wider viewing angle, a higher contrast ratio, and a faster response time. Organic electroluminescent devices (OLEDs) were first developed by Eastman Kodak in 1987 using small aromatic diamine molecules and aluminum complexes as materials for forming the light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].

[0003] The most important factor determining the luminous efficiency of OLEDs is the luminescent material used. Functionally, luminescent materials are divided into host materials and dopant materials. Luminescent materials can be used as a combination of host and dopant to improve color purity, luminous efficiency, and stability. Typically, devices with excellent electroluminescence (EL) characteristics have a structure comprising a luminescent layer formed by doping dopant into the host. When using such a dopant / host material system as the luminescent material, the selection of the host material is crucial because it significantly affects the efficiency and lifetime of the luminescent device.

[0004] Recently, the urgent task is to develop OLEDs with high efficiency and long lifespan. In particular, considering the EL characteristics required for medium and large OLED panels, there is an urgent need to develop highly superior luminescent materials that outperform conventional luminescent materials.

[0005] US 2013 / 0175519 A1 discloses organic light-emitting elements using fused polycyclic compounds, specifically fused benzo[a]phenanthrene compounds, as the host. However, there is still a need to develop light-emitting materials with improved performance, such as improved driving voltage, luminous efficiency, and / or lifetime characteristics. Summary of the Invention

[0006] Problems to be solved

[0007] The purpose of this disclosure is firstly to provide an organic electroluminescent compound (which is capable of producing an organic electroluminescent device with low driving voltage and / or high luminous efficiency and / or long lifetime characteristics) and / or a variety of host materials comprising the same, and secondly to provide an organic electroluminescent device comprising the organic electroluminescent compound and / or the variety of host materials.

[0008] Solution to the problem

[0009] As a result of in-depth research into solving the above-mentioned technical problems, the inventors of this invention have discovered that the above-mentioned objectives can be achieved by an organic electroluminescent compound represented by Formula 1 and a variety of host materials comprising a compound represented by Formula 1 as a first host material and a compound represented by Formula 2 as a second host material, thereby completing this invention.

[0010]

[0011] In Equation 1,

[0012] X represents N-L1-Ar1, O, S, or CR1R2;

[0013] Y1 to Y 10 Each can be represented independently as CR3 or N;

[0014] R1 and R2 each independently represent a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, or a substituted or unsubstituted (C3-C30) cycloalkyl; or they may be connected to each other to form one or more rings;

[0015] R3 represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, or -L2-Ar2; or adjacent R3s may be linked together to form one or more rings;

[0016] L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C1-C30) alkylene, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3- to 30-membered) heteroarylene, or a substituted or unsubstituted (C3-C30) cycloalkylene.

[0017] Ar1 and Ar2 represent substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted fused rings of (C3-C30) aliphatic and (C6-C30) aromatic rings, -Si-(R'1)(R'2) or -N-(R'3)(R'4); and

[0018] R'1 to R'4 each independently represent a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C2-C30) alkenyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3- to 30-membered) heteroaryl.

[0019]

[0020] In Equation 2,

[0021] T5 and T6 are connected to each other to form a loop as shown in Equation 3; or

[0022] T7 and T8 are connected to each other to form a loop as shown in Equation 3; or

[0023] T5 and T6 are connected to each other to form a loop of Equation 3, and T7 and T8 are connected to each other to form a loop of Equation 3.

[0024]

[0025] In equations 2 and 3,

[0026] T1 to T4 and T9 to T3 do not form a ring 14 T5 to T8 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, Substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted fused rings of (C3-C30) aliphatic rings and (C6-C30) aromatic rings, substituted or unsubstituted mono- or di-(C1-C30)arylsilyl, 0) Alkylamino, substituted or unsubstituted mono- or di-(C2-C30) alkenylamino, substituted or unsubstituted (C1-C30) alkyl(C2-C30) alkenylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, substituted or unsubstituted mono- or di-(3- to 30-membered) heteroarylamino The following are substituted or unsubstituted (C1-C30) alkyl (3- to 30-membered) heteroarylamino, substituted or unsubstituted (C2-C30) alkenyl (C6-C30) arylamino, substituted or unsubstituted (C2-C30) alkenyl (3- to 30-membered) heteroarylamino, substituted or unsubstituted (C6-C30) aryl (3- to 30-membered) heteroarylamino, or -L2-Ar2; provided that T1 to T 14 At least one of them is -L2-Ar2;

[0027] L2 represents a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene;

[0028] Ar2 represents substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (3- to 30-membered) heteroaryl;

[0029] --- indicates the site fused to Equation 2; and

[0030] The heteroaryl group contains at least one heteroatom selected from B, N, O, S, Si, and P.

[0031] Beneficial effects of the present invention

[0032] By incorporating the organic electroluminescent compound according to the present disclosure and / or a variety of host materials, an organic electroluminescent device with low driving voltage and / or high luminous efficiency and / or long lifetime characteristics can be provided. Detailed Implementation

[0033] This disclosure will now be described in detail. However, the following description is intended to explain the invention and is not intended to limit the scope of the invention in any way.

[0034] This disclosure relates to an organic electroluminescent compound represented by Formula 1, an organic electroluminescent material comprising the organic electroluminescent compound, and an organic electroluminescent device comprising the organic electroluminescent compound and / or the organic electroluminescent material.

[0035] This disclosure relates to a variety of host materials and organic electroluminescent devices comprising the host materials, the variety of host materials including a first host material and a second host material, the first host material comprising a compound represented by Formula 1, and the second host material comprising a compound represented by Formula 2.

[0036] The term "organic electroluminescent compound" in this disclosure means a compound that can be used in an organic electroluminescent device and can be included, as needed, in any material layer constituting the organic electroluminescent device.

[0037] In this document, "organic electroluminescent material" refers to a material that can be used in an organic electroluminescent device and may contain at least one compound. As needed, the organic electroluminescent material may be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole assist material, a light-emitting assist material, an electron blocking material, a light-emitting material (containing a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material, etc.

[0038] The term "multiple organic electroluminescent materials" in this disclosure refers to an organic electroluminescent material comprising a combination of at least two compounds, which may be contained in any layer constituting an organic electroluminescent device. It can mean both materials contained before (e.g., before vapor deposition) and materials contained after (e.g., after vapor deposition) the organic electroluminescent device. For example, multiple organic electroluminescent materials may be a combination of at least two compounds, which may be contained in at least one of the following layers: a hole injection layer, a hole transport layer, a hole assist layer, a light-emitting assist layer, an electron blocking layer, a light-emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. Such at least two compounds may be contained in the same layer or different layers and may be mixed-evaporated or co-evaporated, or may be evaporated individually.

[0039] In this document, "multiple host materials" means an organic electroluminescent material comprising a combination of at least two host materials. It can mean both materials included before being incorporated into an organic electroluminescent device (e.g., before vapor deposition) and materials included after being incorporated into the organic electroluminescent device (e.g., after vapor deposition). The multiple host materials of this disclosure can be included in any light-emitting layer constituting an organic electroluminescent device. These at least two compounds included in the multiple host materials can be included together in a single light-emitting layer, or they can each be included in a separate light-emitting layer. When at least two host materials are included in a layer, these at least two host materials can be mixed-evaporated to form a layer, or they can be co-evaporated individually and simultaneously to form a layer.

[0040] In this document, "(C1-C30)alkyl" refers to a straight-chain or branched alkyl group having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10. The aforementioned alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, etc. In this document, the term "(C3-C30)cycloalkyl" refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 carbon atoms in the cyclic skeleton, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The aforementioned cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, etc. In this document, "(C6-C30)(aryl)" refers to a monocyclic or fused-ring group derived from an aromatic hydrocarbon having 6 to 30 carbon atoms in its ring skeleton, wherein the number of carbon atoms in the ring skeleton is preferably 6 to 20, more preferably 6 to 15, and may be partially saturated and may contain a spirostructure. Specific examples of aryl groups include phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, binatyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzo[a]fluorenyl, diphenylbenzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthrene, benzo[a]phenanthrene, phenylphenanthrene, anthracene, benzo[a]anthrene, indene, triphenylene, pyrene, tetraphenyl, floryl, etc. Benzyl, benzo[ Naphthacenyl, fluoranyl, benzofluoranyl, tolyl, xylyl, mesityl, cumenel, spiro[fluorene-fluorene]yl, spiro[fluorene-benzofluorene]yl, azulenyl, tetramethyldihydrophenanthrene, etc. More specifically, the aryl group may be o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesitylelel, o-cumenel, m-cumenel, p-cumenel, p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4'-tert-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 ... Biphenyl-2-yl, meta-tetraphenyl, 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-anthrayl, 2-anthrayl, 9-anthrayl, 1-phenanthyl, 2-phenanthyl, 3-phenanthyl, 4-phenanthyl, 9-phenanthyl, 1- basal, 2- basal, 3- basal, 4- Base, 5- Base, 6- Benzyl, benzo[c]phenanthrene, benzo[g] 1-Triphenylene, 2-Triphenylene, 3-Triphenylene, 4-Triphenylene, 3-Fluoranthryl, 4-Fluoranthryl, 8-Fluoranthryl, 9-Fluoranthryl, benzo[a]fluorenyl, 11,11-Dimethyl-1-benzo[a]fluorenyl, 11,11-Dimethyl-2-benzo[a]fluorenyl, 11,11-Dimethyl-3-benzo[a]fluorenyl, 11, 11-Dimethyl-4-benzo[a]fluorenyl, 11,11-dimethyl-5-benzo[a]fluorenyl, 11,11-dimethyl-6-benzo[a]fluorenyl, 11,11-dimethyl-7-benzo[a]fluorenyl, 11,11-dimethyl-8-benzo[a]fluorenyl, 11,11-dimethyl-9-benzo[a]fluorenyl, 11,11- Dimethyl-10-benzo[a]fluorenyl, 11,11-dimethyl-1-benzo[b]fluorenyl, 11,11-dimethyl-2-benzo[b]fluorenyl, 11,11-dimethyl-3-benzo[b]fluorenyl, 11,11-dimethyl-4-benzo[b]fluorenyl, 11,11-dimethyl-5-benzo[b]fluorenyl, 11,11-dimethyl 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 [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 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-phenanthyl, 9,9,10,10-tetramethyl-9,10-dihydro-2-phenanthyl, 9,9,10,10-tetramethyl-9,10-dihydro-3-phenanthyl, 9,9,10,10-tetramethyl-9,10-dihydro-4-phenanthyl, etc. In this document, "(3- to 30-membered) (hypo)aryl" refers to an aryl group having 3 to 30 ring skeleton atoms, comprising at least one, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, Si, P, Se, and Ge, wherein the number of carbon atoms in the ring skeleton is preferably 5 to 25. The aforementioned (hypo)aryl can be a monocyclic ring or a fused ring condensed with at least one benzene ring; and can be partially saturated. Furthermore, the aforementioned heteroaryl or hypoaryl can be a heteroaryl or hypoaryl formed by attaching at least one heteroaryl or aryl group to a heteroaryl group via one or more single bonds. Specific examples of heteroaryl groups can be monocyclic heteroaryl groups, including furanyl, thiopheneyl, pyrroleyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetraazinyl, triazolyl, tetraazolyl, furazanyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc.; and fused-ring heteroaryl groups.Including benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, benzofuran-quinolinyl, benzofuran-quinazolinyl, benzofuran-naphthidyl, benzofuran-pyrimidyl, naphthofuran-pyrimidyl, benzothiophene-quinolinyl, benzothiophene-quinazolinyl, benzothiophene-naphthidyl, benzothiophene-pyrimidyl, naphthophene-pyrimidyl, pyrimidyl-indolyl, benzopyrimidyl-indolyl, benzofuran-pyrazinyl, naphthophene-pyrazinyl, naphthophene-pyrazinyl, pyrazinyl-indolyl, benzopyrazinyl-indolyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisooxazolyl Benzooxazolyl, imidazopyridyl, isoindolyl, indolyl, benzoindolyl, indazole, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxolinyl, carbazoleyl, azacarbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl, phenoxazinyl, phenanthidyl, benzodioxacyclopentenyl, indolizidinyl, acridineyl, silafluorenyl, germanfluorenyl, benzotriazolyl, phenazinyl, imidazopyridyl, chromenoquinazolinyl, thiochromenoquinazolinyl, dimethylbenzopyrimidinyl, indolocarbazoleyl, indenecarbazoleyl, etc. More specifically, the heteroaryl group can be 1-pyrrolithyl, 2-pyrrolithyl, 3-pyrrolithyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-Triazine-2-yl, 1-Imidazolyl, 2-Imidazolyl, 1-Pyrazolyl, 1-Indolithidyl, 2-Indolithidyl, 3-Indolithidyl, 5-Indolithidyl, 6-Indolithidyl, 7-Indolithidyl, 8-Indolithidyl, 2-Imidazolopyridyl, 3-Imidazolopyridyl, 5-Imidazolopyridyl, 6-Imidazolopyridyl 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-Furfuryl, 3-Furfuryl, 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-quinolinyl, 3-quinolinyl, 4-quinolinyl, 5-quinolinyl 6-Quinolinyl, 7-Quinolinyl, 8-Quinolinyl, 1-Isoquinolinyl, 3-Isoquinolinyl, 4-Isoquinolinyl, 5-Isoquinolinyl, 6-Isoquinolinyl, 7-Isoquinolinyl, 8-Isoquinolinyl, 2-Quinoxolinyl, 5-Quinoxolinyl, 6-Quinoxolinyl, 1-Carbazoleyl, 2-Carbazoleyl, 3-Carbazoleyl, 4-Carbazoleyl, 9-Carbazoleyl, Azacarbazole-1- 1-Phenyridyl, 2-Phenyridyl, 3-Phenyridyl, 4-Phenyridyl, 5-Phenyridyl, 6-Phenyridyl, 7-Phenyridyl, 8-Phenyridyl, 9-Phenyridyl, 1-Phenyridyl, 2-Phenyridyl, 3-Phenyridyl, 4-Phenyridyl, 6-Phenyridyl, 7-Phenyridyl, 8-Phenyridyl, 9-Phenyridyl, 10-Phenyridyl -Phenyridyl, 1-Acridinel, 2-Acridinel, 3-Acridinel, 4-Acridinel, 9-Acridinel, 2-Oxazolyl, 4-Oxazolyl, 5-Oxazolyl, 2-Oxadiazolyl, 5-Oxadiazolyl, 3-Furazonyl, 2-Thienyl, 3-Thienyl, 2-Methylpyrrolo-1-yl, 2-Methylpyrrolo-3-yl, 2-Methylpyrrolo-4-yl, 2-Methylpyrrolo- 5-yl, 3-methylpyrrolo-1-yl, 3-methylpyrrolo-2-yl, 3-methylpyrrolo-4-yl, 3-methylpyrrolo-5-yl, 2-tert-butylpyrrolo-4-yl, 3-(2-phenylpropyl)pyrrolo-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4-tert-butyl-1-indolyl, 2-tert-butyl-3-indolyl, 4-tert-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-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 [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]-benzofuran 1-Naphtho-[2,1-b]-benzofuranyl, 2-Naphtho-[2,1-b]-benzofuranyl, 3-Naphtho-[2,1-b]-benzofuranyl, 4-Naphtho-[2,1-b]-benzofuranyl, 5-Naphtho-[2,1-b]-benzofuranyl, 6-Naphtho-[2,1-b]-benzofuranyl, 7-Naphtho-[2,1-b]-benzofuranyl 1-b]-benzofuranyl, 8-naphtho-[2,1-b]-benzofuranyl, 9-naphtho-[2,1-b]-benzofuranyl, 10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b]-benzothiophenyl, 2-naphtho-[1,2-b]-benzothiophenyl, 3-naphtho-[1,2-b]-benzothiophene 4-Naphtho-[1,2-b]-benzothiophene, 5-Naphtho-[1,2-b]-benzothiophene, 6-Naphtho-[1,2-b]-benzothiophene, 7-Naphtho-[1,2-b]-benzothiophene, 8-Naphtho-[1,2-b]-benzothiophene, 9-Naphtho-[1,2-b]-benzothiophene, 10-Naphtho-[1 [2,3-b]-benzothiophene, 1-naphtho-[2,3-b]-benzothiophene, 2-naphtho-[2,3-b]-benzothiophene, 3-naphtho-[2,3-b]-benzothiophene, 4-naphtho-[2,3-b]-benzothiophene, 5-naphtho-[2,3-b]-benzothiophene, 1-naphtho-[2,1-b]-benzothiophene 2-Naphtho-[2,1-b]-benzothiophene, 3-Naphtho-[2,1-b]-benzothiophene, 4-Naphtho-[2,1-b]-benzothiophene, 5-Naphtho-[2,1-b]-benzothiophene, 6-Naphtho-[2,1-b]-benzothiophene, 7-Naphtho-[2,1-b]-benzothiophene, 8-Naphtho-[2,1-b]-benzothiophene1-b]-benzothiophene, 9-naphtho-[2,1-b]-benzothiophene, 10-naphtho-[2,1-b]-benzothiophene, 2-benzofurano[3,2-d]pyrimidinyl, 6-benzofurano[3,2-d]pyrimidinyl, 7-benzofurano[3,2-d]pyrimidinyl, 8-benzofurano[3,2-d]pyrimidinyl, 9 -Benzofurano[3,2-d]pyrimidinyl, 2-benzothieno[3,2-d]pyrimidinyl, 6-benzothieno[3,2-d]pyrimidinyl, 7-benzothieno[3,2-d]pyrimidinyl, 8-benzothieno[3,2-d]pyrimidinyl, 9-benzothieno[3,2-d]pyrimidinyl, 2-benzofuran[3,2-d]pyrazinyl 6-Benzofurano[3,2-d]pyrazinyl, 7-Benzofurano[3,2-d]pyrazinyl, 8-Benzofurano[3,2-d]pyrazinyl, 9-Benzofurano[3,2-d]pyrazinyl, 2-Benzothieno[3,2-d]pyrazinyl, 6-Benzothieno[3,2-d]pyrazinyl, 7-Benzothieno[3,2-d]pyrazinyl Zincazine, 8-benzothieno[3,2-d]pyrazine, 9-benzothieno[3,2-d]pyrazine, 1-siliconfluorenyl, 2-siliconfluorenyl, 3-siliconfluorenyl, 4-siliconfluorenyl, 1-germaniumfluorenyl, 2-germaniumfluorenyl, 3-germaniumfluorenyl, 4-germaniumfluorenyl, 1-dibenzoselenenyl, 2-dibenzoselenenyl, 3-dibenzoselenenyl, 4-dibenzoselenenyl, etc. In this document, the term "fused ring of (C3-C30) aliphatic ring and (C6-C30) aromatic ring" refers to a ring formed by fusion of at least one aliphatic ring having 3 to 30 carbon atoms in its ring skeleton (preferably 3 to 25, more preferably 3 to 18) with at least one aromatic ring having 6 to 30 carbon atoms in its ring skeleton (preferably 6 to 25, more preferably 6 to 18). For example, the fused ring can 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 this document, the carbon atoms in the fused ring of (C3-C30) aliphatic ring and (C6-C30) aromatic ring can be replaced by at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S. The term "halogen" in this disclosure includes F, Cl, Br, and I.

[0041] Furthermore, "ortho (o)," "meta (m)," and "para (p)" indicate the substitution positions of all substituents. The ortho position is a compound with substituents adjacent to each other, such as at positions 1 and 2 on benzene. The meta position is the next substitution position after the immediately adjacent substitution position; for example, a compound with substituents at positions 1 and 3 on benzene. The para position is the next substitution position after the meta position; for example, a compound with substituents at positions 1 and 4 on benzene.

[0042] In this document, "a ring formed by connection with adjacent substituents" means a substituted or unsubstituted (3-membered to 30-membered) monocyclic or polycyclic alicyclic ring, aromatic ring, or combination thereof formed by connecting or fused two or more adjacent substituents; preferably, it can be a substituted or unsubstituted (3-membered to 26-membered) monocyclic or polycyclic alicyclic 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 this disclosure, the number of atoms in the ring skeleton is 5 to 20; according to another embodiment of this 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 naphthyl 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, etc.

[0043] Furthermore, the term "substituted" in the phrase "substituted or unsubstituted" means that a hydrogen atom in a functional group is replaced by another atom or functional group (i.e., a substituent), or by a group in which two or more substituents are attached. For example, "a substituent in which two or more substituents are attached" could be pyridine-triazine. That is, pyridine-triazine could be a heteroaryl group, or it could be interpreted as a substituent in which two heteroaryl groups are attached. In the formulas disclosed herein, substituted ()alkylene), substituted alkenyl, substituted ()aryl), substituted ()heteroaryl), substituted ()cycloalkylene), substituted alkoxy, and substituents of substituted aliphatic and aromatic fused rings each independently represent at least one selected from the group consisting of: deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, phosphine oxide, (C1-C30)alkyl, halo(C1-C30)alkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C1-C30)alkoxy, (C1-C30)alkylthio, (C3-C30)cycloalkyl, ( (C3-C30)cycloalkenyl, (3- to 7-membered)heterocyclic alkyl, (C6-C30)aryloxy, (C6-C30)arylthio, unsubstituted or substituted with at least one of deuterium and (C6-C30)aryl, unsubstituted or substituted with at least one of deuterium and (C6- to 30)heterocyclic aryl, tri(C1-C30)alkylsilyl, tri(C6-C30)arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C1-C30)alkyldi(C6-C30)aryl Silyl, fused rings of (C3-C30) aliphatic and (C6-C30) aromatic rings, amino, mono- or di-(C1-C30)alkylamino, mono- or di-(C2-C30)alkenylamino, (C1-C30)alkyl(C2-C30)alkenylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, (C1-C30)alkyl(C6-C30)arylamino, mono- or di-(3- to 30-membered)heteroarylamino, (C1-C30)alkyl(3- to 30-membered)heteroarylamino, (C2-C30)alkenyl(C6-C30)arylamino alkylamino, (C2-C30)alkenyl(3- to 30-membered)heteroarylamino, (C6-C30)aryl(3- to 30-membered)heteroarylamino, (C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30)arylcarbonyl, (C6-C30)aryloxyphosphinyl, di(C6-C30)arylboroncarbonyl, di(C1-C30)alkylboroncarbonyl, (C1-C30)alkyl(C6-C30)arylboroncarbonyl, (C6-C30)aryl(C1-C30)alkyl, and (C1-C30)alkyl(C6-C30)aryl.

[0044] The organic electroluminescent compound according to one embodiment will be described below.

[0045] According to one embodiment, the organic electroluminescent compound is represented by the following formula 1.

[0046]

[0047] In Equation 1,

[0048] X represents N-L1-Ar1, O, S, or CR1R2;

[0049] Y1 to Y 10 Each can be represented independently as CR3 or N;

[0050] R1 and R2 each independently represent a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, or a substituted or unsubstituted (C3-C30) cycloalkyl; or they may be connected to each other to form one or more rings;

[0051] R3 represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, or -L2-Ar2; or adjacent R3s may be linked together to form one or more rings;

[0052] L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C1-C30) alkylene, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3- to 30-membered) heteroarylene, or a substituted or unsubstituted (C3-C30) cycloalkylene.

[0053] Ar1 and Ar2 independently represent substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted fused rings of (C3-C30) aliphatic and (C6-C30) aromatic rings, -Si-(R'1)(R'2) or -N-(R'3)(R'4); and

[0054] R'1 to R'4 each independently represent a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C2-C30) alkenyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3- to 30-membered) heteroaryl.

[0055] In one embodiment, X can be N-L1-Ar1.

[0056] In one embodiment, L1 can be a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5- to 30-membered) heteroarylene, preferably a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (5- to 25-membered) heteroarylene, more preferably a single bond, a substituted or unsubstituted (C6-C18) arylene, or a substituted or unsubstituted (5- to 18-membered) heteroarylene. For example, L1 can be a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted o-biphenylene, a substituted or unsubstituted meta-biphenylene, a substituted or unsubstituted para-biphenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted pyridylene. For example, the substituent of the substituted group can be deuterium.

[0057] In one embodiment, Ar1 can be a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (5- to 30-membered) heteroaryl, preferably a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (5- to 25-membered) heteroaryl, more preferably a substituted or unsubstituted (C6-C18) aryl or a substituted or unsubstituted (5- to 18-membered) heteroaryl. For example, Ar1 can be a substituted or unsubstituted phenyl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted o-terphenyl, a substituted or unsubstituted meta-terphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted triazine, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted benzoquinoxalinyl, or a substituted or unsubstituted dibenzoquinoxalinyl. For example, the substituent of the substituted group can be at least one selected from the group consisting of: deuterium, methyl, unsubstituted or deuterated phenyl, biphenyl, naphthyl, fluorenyl, unsubstituted or phenyl-substituted pyridyl, dibenzofuranyl and dibenzothiopheneyl.

[0058] In one embodiment, Ar1 can be -N-(R'3)(R'4). R'3 and R'4 can each independently be a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (5- to 30-membered) heteroaryl, preferably a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (5- to 25-membered) heteroaryl, more preferably a substituted or unsubstituted (C6-C18) aryl or a substituted or unsubstituted (5- to 18-membered) heteroaryl. For example, R'3 and R'4 can each independently be a substituted or unsubstituted phenyl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted meta-biphenyl, a substituted or unsubstituted fluorenyl, or a substituted or unsubstituted dibenzofuranyl. For example, the substituent of the substituted group can be at least one selected from the group consisting of deuterium, methyl, and naphthyl.

[0059] In one embodiment, X can be O, S, or CR1R2.

[0060] In one embodiment, R1 and R2 can each independently be a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5- to 30-membered) heteroaryl, preferably a substituted or unsubstituted (C1-C10) alkyl, a substituted or unsubstituted (C6-C25) aryl, or a substituted or unsubstituted (5- to 25-membered) heteroaryl, more preferably a substituted or unsubstituted (C1-C4) alkyl, a substituted or unsubstituted (C6-C18) aryl, or a substituted or unsubstituted (5- to 18-membered) heteroaryl. For example, R1 and R2 can each independently be methyl, a substituted or unsubstituted phenyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted triazine, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiopheneyl. For example, the substituent of the substituted group can be at least one selected from the group consisting of: phenyl, p-phenyl, meta-phenyl, naphthyl, dimethylfluorenyl, unsubstituted or phenyl-substituted pyridyl, dibenzofuranyl and dibenzothiopheneyl.

[0061] In one embodiment, Y1 to Y 10 Each can be independently either CR3 or N, for example, Y1 to Y. 10 Both can be CR3.

[0062] In one embodiment, R3 may be hydrogen, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5- to 30-membered) heteroaryl; or adjacent R3 may be connected to each other to form one or more rings, preferably hydrogen, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5- to 25-membered) heteroaryl; or adjacent R3 may be connected to each other to form substituted or unsubstituted (5- to 30-membered) monocyclic or polycyclic alicyclic rings or aromatic rings, or combinations thereof, more preferably hydrogen, substituted or unsubstituted (C6-C18) aryl, or substituted or unsubstituted (5- to 18-membered) heteroaryl; or adjacent R3 may be connected to each other to form substituted or unsubstituted (5- to 25-membered) monocyclic or polycyclic aromatic rings. For example, R3 can be hydrogen, a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, or a substituted or unsubstituted triazine group; or adjacent R3 groups can be linked or fused together to form a substituted or unsubstituted indole ring or a substituted or unsubstituted benzofuran ring. For example, the substituent of the substituted group can be a phenyl group or a substituted or unsubstituted triazine group.

[0063] In one embodiment, R3 can be -L2-Ar2.

[0064] In one embodiment, L2 may be a single-bonded or substituted or unsubstituted (C6-C30) arylene, preferably a single-bonded or substituted or unsubstituted (C6-C25) arylene, and more preferably a single-bonded or substituted or unsubstituted (C6-C18) arylene. For example, L2 may be a single-bonded, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, or substituted or unsubstituted anthracene. For example, the substituent of the substituted group may be deuterium.

[0065] In one embodiment, Ar2 can be a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (5- to 30-membered) heteroaryl, preferably a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (5- to 25-membered) heteroaryl, more preferably a substituted or unsubstituted (C6-C18) aryl or a substituted or unsubstituted (5- to 18-membered) heteroaryl. For example, Ar2 can be a substituted or unsubstituted phenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted triazine, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinoxalinyl, or a substituted or unsubstituted benzoquinoxalinyl. For example, the substituent of the substituted group can be at least one selected from the group consisting of: deuterium, methyl, unsubstituted or deuterated or naphthyl phenyl, unsubstituted or deuterated biphenyl, naphthyl, fluorenyl, unsubstituted or phenyl pyridyl, dibenzofuranyl and dibenzothiopheneyl.

[0066] In one embodiment, Ar2 can be -N-(R'3)(R'4). R'3 and R'4 can each independently be a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (5- to 30-membered) heteroaryl, preferably a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (5- to 25-membered) heteroaryl, more preferably a substituted or unsubstituted (C6-C18) aryl or a substituted or unsubstituted (5- to 18-membered) heteroaryl. For example, R'3 and R'4 can each independently be a substituted or unsubstituted phenyl, a substituted or unsubstituted para-phenyl, a substituted or unsubstituted meta-phenyl, a substituted or unsubstituted fluorenyl, or a substituted or unsubstituted dibenzofuranyl. For example, the substituent of the substituted group can be at least one selected from the group consisting of deuterium, methyl, and naphthyl.

[0067] An organic electroluminescent compound represented by Formula 1 according to one embodiment can be represented by any one of Formulas 1-1 to 1-8 below.

[0068]

[0069]

[0070] In equations 1-1 to 1-8,

[0071] X, Y1 to Y 10 L1, L2, Ar1, and Ar2 are defined as in Equation 1;

[0072] Y 11 To Y 18 and Y'1 to Y' 12 It is defined as Y1 in Equation 1;

[0073] L3 and L4 are defined in the same way as L1 in Equation 1;

[0074] Ar3 and Ar4 are defined in the same way as Ar1 in Equation 1;

[0075] X' represents O or S;

[0076] "X" represents O, S, CR 11 R 12 or NR 13 ;and

[0077] R 11 To R 13Each of these can independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- to 30-membered)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C1-C30)alkylsilyl, etc. The 6-C30) arylsilyl, a substituted or unsubstituted fused ring of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, a substituted or unsubstituted mono- or di-(C1-C30) alkylamino, a substituted or unsubstituted mono- or di-(C6-C30) arylamino, a substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered) heteroarylamino, or a substituted or unsubstituted (C6-C30) aryl(3- to 30-membered) heteroarylamino; or may be attached to an adjacent substituent to form one or more rings.

[0078] In one embodiment, L3 and L4 in Formulas 1-4 can each independently be a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5- to 30-membered) heteroarylene, preferably a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (5- to 25-membered) heteroarylene, more preferably a single bond, a substituted or unsubstituted (C6-C18) arylene, or a substituted or unsubstituted (5- to 18-membered) heteroarylene. For example, L3 and L4 can each independently be a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted dibenzofuranyl.

[0079] In one embodiment, Ar3 and Ar4 in Formulas 1-4 can each independently be a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5- to 30-membered) heteroaryl, preferably a substituted or unsubstituted (C1-C10) alkyl, a substituted or unsubstituted (C6-C25) aryl, or a substituted or unsubstituted (5- to 25-membered) heteroaryl, more preferably a substituted or unsubstituted (C1-C4) alkyl, a substituted or unsubstituted (C6-C18) aryl, or a substituted or unsubstituted (5- to 18-membered) heteroaryl. For example, Ar3 and Ar4 can each independently be methyl, a substituted or unsubstituted phenyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted triazine, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiopheneyl. For example, the substituent of the substituted group can be at least one selected from the group consisting of: phenyl, p-phenyl, meta-phenyl, naphthyl, dimethylfluorenyl, unsubstituted or phenyl-substituted pyridyl, and dibenzofuranyl.

[0080] In one embodiment, Y in Equations 1-5 11 To Y 18 Each can be CR3 or N independently, preferably Y. 11 To Y 18 All of them can be CR3. R3 can be hydrogen, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5-membered to 30-membered) heteroaryl group, preferably hydrogen, a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5-membered to 25-membered) heteroaryl group, more preferably hydrogen, a substituted or unsubstituted (C6-C18) aryl group, or a substituted or unsubstituted (5-membered to 18-membered) heteroaryl group. For example, R3 can be a substituted or unsubstituted biphenyl, a substituted or unsubstituted pyridyl, or a substituted or unsubstituted triazine. For example, the substituent of the substituted group can be at least one selected from the group consisting of phenyl, p-biphenyl, meta-phenyl, and naphthyl.

[0081] Furthermore, in Equation 1-5, R3 can be -L2-Ar2.

[0082] In one embodiment, L2 in Formulas 1-5 can be a single bond, or a substituted or unsubstituted (C6-C30) arylene, preferably a single bond or a substituted or unsubstituted (C6-C25) arylene, more preferably a single bond or a substituted or unsubstituted (C6-C18) arylene. For example, L2 can be a single bond or a phenylene.

[0083] In one embodiment, Ar2 in Formulas 1-5 can be -N-(R'3)(R'4). R'3 and R'4 can each independently be a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (5- to 30-membered) heteroaryl, preferably a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (5- to 25-membered) heteroaryl, more preferably a substituted or unsubstituted (C6-C18) aryl or a substituted or unsubstituted (5- to 18-membered) heteroaryl. For example, R'3 and R'4 can each independently be a substituted or unsubstituted phenyl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted meta-biphenyl, a substituted or unsubstituted fluorenyl, or a substituted or unsubstituted dibenzofuranyl. For example, the substituent of the substituted group can be methyl.

[0084] In one embodiment, X in Equations 1-6 can be N-L1-Ar1.

[0085] In one embodiment, L1 in Formulas 1-6 can be a single bond, or a substituted or unsubstituted (C6-C30) arylene, preferably a single bond or a substituted or unsubstituted (C6-C25) arylene, more preferably a single bond or a substituted or unsubstituted (C6-C18) arylene. For example, L1 can be a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, or a substituted or unsubstituted naphthylene. For example, the substituent of the substituted group can be deuterium.

[0086] In one embodiment, Ar1 in Formulas 1-6 can be a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (5- to 30-membered) heteroaryl, preferably a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (5- to 25-membered) heteroaryl, more preferably a substituted or unsubstituted (C6-C18) aryl or a substituted or unsubstituted (5- to 18-membered) heteroaryl. For example, Ar1 can be a substituted or unsubstituted phenyl, a substituted or unsubstituted o-biphenyl, a substituted or unsubstituted para-biphenyl, a substituted or unsubstituted o-terphenyl, a substituted or unsubstituted meta-terphenyl, a substituted or unsubstituted para-terphenyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted triazine, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted benzoquinoxalinyl, or a substituted or unsubstituted dibenzoquinoxalinyl. For example, the substituent of the substituted group can be at least one selected from the group consisting of: unsubstituted or deuterated phenyl, unsubstituted or deuterated biphenyl, naphthyl, dimethylfluorenyl, unsubstituted or phenyl-substituted pyridyl and dibenzofuranyl.

[0087] In one embodiment, Ar1 in Formulas 1-6 can be -N-(R'3)(R'4). R'3 and R'4 can each independently be a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (5- to 30-membered) heteroaryl, preferably a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (5- to 25-membered) heteroaryl, more preferably a substituted or unsubstituted (C6-C18) aryl or a substituted or unsubstituted (5- to 18-membered) heteroaryl. For example, R'3 and R'4 can each independently be a substituted or unsubstituted phenyl, a substituted or unsubstituted para-phenyl, a substituted or unsubstituted meta-phenyl, a substituted or unsubstituted fluorenyl, or a substituted or unsubstituted dibenzofuranyl. For example, the substituent of the substituted group can be methyl.

[0088] In one embodiment, Y'5 to Y'8 in Formulas 1-7 can each independently be CR3 or N, where R3 can be hydrogen.

[0089] In one embodiment, X” in Equations 1-8 can be O or NR. 13 , where R 13 It can be phenyl.

[0090] In one embodiment, Y'9 to Y' in Equations 1-8 12 Each can be CR3 independently, where R3 can be hydrogen.

[0091] According to one embodiment, the organic electroluminescent compound represented by Formula 1 can be further illustrated by the following compounds, but is not limited thereto.

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106] The compounds represented by Formula 1 according to this disclosure can be prepared as represented by, but not limited to, the following reaction schemes 1 to 3; they can be further produced by synthetic methods known to those skilled in the art.

[0107] [Reaction Scheme 1]

[0108]

[0109] [Reaction Scheme 2]

[0110]

[0111] [Reaction Scheme 3]

[0112]

[0113]

[0114] In reaction schemes 1 to 3 above, each substituent is defined as in Formula 1, and R can be defined as -L3-Ar3 and / or -L4-Ar4 in Formulas 1-4.

[0115] As described above, exemplary synthetic examples of compounds represented by Formula 1 according to this disclosure are presented, but they are based on Sandmeyer reaction, Buchwald-Hartwig cross-coupling reaction, N-arylation reaction, H-montmorillonite-mediated etherification reaction, Miyaura borylation reaction, Suzuki cross-coupling reaction, intramolecular acid-induced cyclization reaction, Pd(II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, dehydration cyclization reaction, SN1 substitution reaction, SN2 substitution reaction, and phosphine-mediated reductive cyclization reaction, etc. Those skilled in the art will understand that the above reactions will continue even if other substituents defined in Formula 1 are bonded besides those described in the specific synthetic examples.

[0116] According to another embodiment, this disclosure provides a variety of body materials, including a first body material and a second body material.

[0117] According to one embodiment, multiple host materials include a first host material comprising a compound represented by Formula 1 and a second host material comprising a compound represented by Formula 2 below, and may be included in the light-emitting layer of an organic electroluminescent device according to one embodiment.

[0118] According to one embodiment, the second body material may comprise a compound represented by Formula 2.

[0119]

[0120] In Equation 2,

[0121] T5 and T6 are connected to each other to form a loop of the following formula 3; or T7 and T8 are connected to each other to form a loop of the following formula 3; or T5 and T6 are connected to each other to form a loop of the following formula 3, and T7 and T8 are connected to each other to form a loop of the following formula 3;

[0122]

[0123] In equations 2 and 3,

[0124] T1 to T4 and T9 to T3 do not form a ring 14T5 to T8 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, Substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted fused rings of (C3-C30) aliphatic rings and (C6-C30) aromatic rings, substituted or unsubstituted mono- or di-(C1-C30)arylsilyl, 0) Alkylamino, substituted or unsubstituted mono- or di-(C2-C30) alkenylamino, substituted or unsubstituted (C1-C30) alkyl(C2-C30) alkenylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, substituted or unsubstituted mono- or di-(3- to 30-membered) heteroarylamino The following are substituted or unsubstituted (C1-C30) alkyl (3- to 30-membered) heteroarylamino, substituted or unsubstituted (C2-C30) alkenyl (C6-C30) arylamino, substituted or unsubstituted (C2-C30) alkenyl (3- to 30-membered) heteroarylamino, substituted or unsubstituted (C6-C30) aryl (3- to 30-membered) heteroarylamino, or -L2-Ar2, provided that T1 to T 14 At least one of them is -L2-Ar2;

[0125] L2 represents a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene;

[0126] Ar2 represents substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl;

[0127] --- indicates the site fused to Equation 2; and

[0128] The heteroaryl group contains at least one heteroatom selected from B, N, O, S, Si, and P.

[0129] In one embodiment, T5 and T6 may be connected to each other to form a loop of Formula 3, and / or T7 and T8 may be connected to each other to form a loop of Formula 3.

[0130] In one embodiment, T1 to T 14Each can independently be hydrogen, substituted or unsubstituted (C6-C30) aryl, or -L2-Ar2, preferably hydrogen, substituted or unsubstituted (C6-C25) aryl, or -L2-Ar2, more preferably hydrogen, substituted or unsubstituted (C6-C18) aryl, or -L2-Ar2. For example, T1 to T 14 Each can be hydrogen, phenyl, naphthyl, biphenyl, or -L2-Ar2 independently.

[0131] In one embodiment, T1 to T4, T does not form a ring 11 To T 14 And at least one of T5 to T8 can be -L2-Ar2.

[0132] In one embodiment, L2 may be a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5- to 30-arylene) heteroarylene, preferably a single bond or a substituted or unsubstituted (C6-C25) arylene, more preferably a single bond or an unsubstituted or (C6-C18) arylene substituted with a (C6-C18) arylene. For example, L2 can be a single bond, an unsubstituted or phenyl-substituted phenylene, naphthylene, or biphenylene, such as 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, 1,2-biphenylene, 1,3-biphenylene, 1,4-biphenylene, 1,2-naphthylene, 1,3-naphthylene, 1,4-naphthylene, 1,5-naphthylene, 1,6-naphthylene, 1,7-naphthylene, 1,8-naphthylene, 2,3-naphthylene, 2,6-naphthylene, or 2,7-naphthylene.

[0133] In one embodiment, Ar2 may be a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (5- to 30-aryl) heteroaryl, preferably a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (5- to 25-aryl) heteroaryl, more preferably an unsubstituted or (C6-C30) aryl substituted (5- to 25-aryl) heteroaryl or (5- to 30-aryl) heteroaryl, or even more preferably an unsubstituted or (C6-C30) aryl substituted nitrogen-containing (5- to 25-aryl) heteroaryl or (5- to 30-aryl) heteroaryl. For example, Ar2 can be substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazine, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted dibenzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted dibenzoquinoxalinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted naphridyl, substituted or unsubstituted benzoisoquinoxalinyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted phenanthemiimidazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted phenanthemizothiazolyl, substituted or unsubstituted oxazolyl, substituted... Or unsubstituted benzoxazolyl, substituted or unsubstituted phenanthoxazolyl, substituted or unsubstituted naphthoxazolyl, substituted or unsubstituted naphthothiazolyl, substituted or unsubstituted benzothiophenepyrimidinyl, substituted or unsubstituted benzothiophenepyrazinyl, substituted or unsubstituted benzofuranpyrimidinyl, substituted or unsubstituted benzofuranpyrazinyl, substituted or unsubstituted benzothiophenequinolinyl, substituted or unsubstituted benzofuranquinolinyl, substituted or unsubstituted acenaphthopyrimidinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted dibenzocarbazolyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted benzopyrimidinyl, substituted or unsubstituted 17-membered heteroaryl containing at least two nitrogen atoms, or substituted or unsubstituted 25-membered heteroaryl having at least one nitrogen atom. For example, the substituent of the substituted group can be at least one of the following: methyl; phenyl; fluorinated phenyl; tert-butyl phenyl; trimethylsilyl phenyl; triphenylsilyl phenyl; carbazolyl phenyl; cyclohexyl phenyl; cyano phenyl; naphthyl; biphenyl; terphenyl; naphthylphenyl; phenylnaphthyl; phenanthryl; anthraceneyl; ; benzophenanthryl; dimethylfluorenyl; diphenylfluorenyl; spirodifluorenyl; phenyl-substituted pyridyl; dibenzothiopheneyl; dibenzofuranyl; phenyl-substituted dibenzofuranyl; biphenyl-substituted dibenzofuranyl; unsubstituted or phenyl-substituted carbazoyl; phenoxazinyl; benzothiopheneyl; and phenyl-substituted naphthooxazolinyl.

[0134] According to one embodiment, the compound represented by Formula 2 can be represented by Formula 2-1 or 2-2.

[0135]

[0136] In equations 2-1 and 2-2,

[0137] T1 to T 14 It is as defined in Equation 2.

[0138] According to one embodiment, the compound represented by Formula 2 can be represented by any of the following formulas.

[0139]

[0140]

[0141] In the formula,

[0142] T1 to T 14 Each of these elements independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted fused rings of (C3-C30) aliphatic rings and (C6-C30) aromatic rings, substituted or unsubstituted mono- or di-(C1- C30) alkylamino, substituted or unsubstituted mono- or di-(C2-C30) alkenylamino, substituted or unsubstituted (C1-C30) alkyl(C2-C30) alkenylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, substituted or unsubstituted mono- or di-(3- to 30-membered) heteroarylamino, substituted or unsubstituted (C1-C30) alkyl(3- to 30-membered) heteroarylamino, substituted or unsubstituted (C2-C30) alkenyl(C6-C30) arylamino, substituted or unsubstituted (C2-C30) alkenyl(3- to 30-membered) heteroarylamino, or substituted or unsubstituted (C6-C30) aryl(3- to 30-membered) heteroarylamino; and

[0143] L2 and Ar2 are defined as in Equation 2.

[0144] In one embodiment, the compound represented by Formula 2 can be further described by, but is not limited to, the following compounds.

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158] The compounds represented by Formula 2 according to this disclosure can be produced by synthetic methods known to those skilled in the art, for example, they can be prepared as represented by the following reaction schemes 4 and 5.

[0159] [Reaction Scheme 4]

[0160]

[0161] [Reaction Scheme 5]

[0162]

[0163] In reaction schemes 4 and 5 above, T and T′ are each independently T1 to T in equation 2. 14 As defined, x represents an integer from 1 to 7, z represents an integer from 1 to 4, and when x and z are integers of 2 or greater, each in T and each in T′ can be the same or different.

[0164] As described above, exemplary synthetic examples of compounds represented by Formula 2 according to this disclosure are presented, but they are based on Buchwald-Hartwig cross-coupling reactions, N-arylation reactions, H-montmorillonite-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, dehydration cyclization reactions, SN1 substitution reactions, SN2 substitution reactions, and phosphine-mediated reductive cyclization reactions, etc. Those skilled in the art will understand that the above reactions will continue even if other substituents defined in Formula 2 are bonded besides those described in the specific synthetic examples.

[0165] According to one embodiment, this disclosure may provide an organic electroluminescent material comprising an organic electroluminescent compound having Formula 1, and an organic electroluminescent device comprising the organic electroluminescent material.

[0166] According to another embodiment, this disclosure can provide a variety of host materials and an organic electroluminescent device comprising the variety of host materials, the variety of host materials comprising a first host material having a compound having Formula 1 and a second host material having a compound having Formula 2.

[0167] The organic electroluminescent material may be made solely of the organic electroluminescent compounds of this disclosure, or may further include conventional materials included in organic electroluminescent materials. When two or more materials are included in a layer, the at least two host materials may be mixed and evaporated to form a layer, or they may be co-evaporated individually and simultaneously to form a layer. The organic electroluminescent material according to one embodiment may contain at least one compound represented by Formula 1 above. The organic electroluminescent compound of Formula 1 of this disclosure may preferably be included in the hole transport layer, the light-emitting layer, the buffer layer, and / or the electron transport layer of the organic electroluminescent device, and more preferably in the light-emitting layer or the electron buffer layer. When included in the light-emitting layer, the compound of Formula 1 may be included as a host, and more specifically as a phosphorescent red host. According to another embodiment, the organic electroluminescent material may include a first host material and a second host material. The first host material includes a compound represented by Formula 1, and the second host material includes a compound represented by Formula 2. Specifically, at least one compound selected from C-1 to C-320 serves as the first host material including a compound represented by Formula 1, and at least one compound selected from H2-1 to H2-281 serves as the second host material including a compound represented by Formula 2. Multiple host materials may be included in the same organic layer, such as in a light-emitting layer, or may be included in different light-emitting layers.

[0168] In addition to the organic electroluminescent compound represented by Formula 1 and various host materials containing thereto, the organic electroluminescent material according to this disclosure may also contain at least one dopant.

[0169] The dopant included in the organic electroluminescent material of this disclosure may be at least one phosphorescent dopant or fluorescent dopant, preferably a phosphorescent dopant. There are no particular limitations on the phosphorescent dopant material used in this disclosure, but it may preferably be one or more metallized complexes of one or more metal atoms selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt) (if desired); more preferably, one or more ortho-metallized complexes of one or more metal atoms selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt) (if desired); and even more preferably, one or more ortho-metallized iridium complexes (if desired).

[0170] The dopants according to this disclosure may be compounds represented by formula 101, but are not limited thereto.

[0171]

[0172] In Equation 101,

[0173] L is selected from any one of the following structures 1 to 3:

[0174]

[0175] R 100 To R 103 Each can independently represent hydrogen, deuterium, halogen, unsubstituted or deuterated and / or halogenated (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (3- to 30-membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; or can be attached to an adjacent substituent to form one or more rings with pyridine, such as substituted or unsubstituted quinoline, substituted or unsubstituted benzofuranopyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted indopyridine, substituted or unsubstituted benzofuranoquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indoquinoline;

[0176] R 104 To R 107 Each of these can independently represent hydrogen, deuterium, halogen, unsubstituted or deuterated and / or halogenated (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; or can be attached to an adjacent substituent to form one or more substituted or unsubstituted rings with benzene, for example, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indopyridine, substituted or unsubstituted benzofuran-pyridine, or substituted or unsubstituted benzothiophene-pyridine;

[0177] R 201 To R 220 Each can independently represent hydrogen, deuterium, halogen, unsubstituted or deuterated and / or halogenated (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C6-C30) aryl; or can be attached to adjacent substituents to form one or more substituted or unsubstituted rings; and

[0178] s represents an integer from 1 to 3.

[0179] Specifically, examples of dopant compounds include, but are not limited to, the following.

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186] The following will describe an organic electroluminescent device that uses the above-mentioned organic electroluminescent compound or organic electroluminescent material.

[0187] An organic electroluminescent device according to one embodiment includes a first electrode; a second electrode; and at least one organic layer inserted between the first electrode and the second electrode. In one embodiment, the organic layer includes a hole transport layer, a light-emitting layer, a buffer layer, and / or an electron transport layer, preferably a light-emitting layer or an electron buffer layer, which contains an organic electroluminescent compound according to the present disclosure. For example, the light-emitting layer may contain only the organic electroluminescent compound of the present disclosure, or a mixture of at least two of the organic electroluminescent compounds, and may further contain conventional materials included in organic electroluminescent materials. In addition to the hole transport layer, the light-emitting layer, the buffer layer, and the electron transport layer, the organic layer may further contain at least one layer selected from a hole injection layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron injection layer, a sandwich layer, a hole blocking layer, and an electron blocking layer, and each layer may further consist of multiple layers.

[0188] Furthermore, the organic layer may further comprise at least one selected from arylamine-based compounds and styrylarylamine-based compounds. Additionally, the organic layer may further comprise at least one metal selected from the group consisting of: metals of Group 1, Group 2, transition metals of Period 4, transition metals of Period 5, lanthanides, and organometallic compounds of d-transition elements, or at least one complex compound comprising such metal.

[0189] According to one embodiment, the organic electroluminescent material can be used as a luminescent material for a white organic light-emitting device. Various structures have been proposed for white organic electroluminescent devices, such as parallel side-by-side arrangements, stacked arrangements, or color conversion material (CCM) methods, depending on the arrangement of R (red), G (green), YG (yellow-green), or B (blue) luminescent units. Furthermore, according to one embodiment, the organic electroluminescent material can also be applied to organic electroluminescent devices containing QDs (quantum dots).

[0190] One of the first electrode and the second electrode can be an anode, and the other can be a cathode. The first electrode and the second electrode can each be formed of a transmissive conductive material, a semi-transmissive reflective conductive material, or a reflective conductive material. Depending on the types of materials forming the first electrode and the second electrode, the organic electroluminescent device can be a top-emitting type, a bottom-emitting type, or a side-emitting type.

[0191] A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof can be used between the anode and the emissive layer. The hole injection layer can be multilayered to reduce the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or electron blocking layer, wherein each of the multilayers can use two compounds simultaneously. Furthermore, the hole injection layer can be doped with a p-type dopant. Additionally, an electron blocking layer can be placed between the hole transport layer (or hole injection layer) and the emissive layer, and can confine excitons within the emissive layer by blocking electrons from escaping from the emissive layer to prevent light leakage. The hole transport layer or electron blocking layer can be multilayered, wherein each layer can use multiple compounds.

[0192] 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 properties between the light-emitting layer and the electron injection layer, wherein each of the multilayers can use two compounds simultaneously. The hole blocking layer or electron transport layer can also be multilayered, wherein each layer can use multiple compounds. Furthermore, the electron injection layer can be doped with an n-type dopant.

[0193] An auxiliary light-emitting layer can be placed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer. When placed between the anode and the light-emitting layer, it can promote hole injection and / or hole transport, or prevent electron overflow. When placed between the cathode and the light-emitting layer, it can promote electron injection and / or electron transport, or prevent hole overflow. Furthermore, a hole auxiliary layer can be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can effectively promote or limit the hole transport rate (or hole injection rate), thereby enabling charge balance control. When an organic electroluminescent device includes two or more hole transport layers, the further included hole transport layers can serve as hole auxiliary layers or electron blocking layers. The auxiliary light-emitting layer, hole auxiliary layer, or electron blocking layer can improve the efficiency and / or lifetime of the organic electroluminescent device.

[0194] In the organic electroluminescent device disclosed herein, at least one layer selected from chalcogenide layers, metal halide layers, and metal oxide layers (hereinafter, "surface layer") is preferably placed on one or more inner surfaces of one or two electrodes. Specifically, silicon and aluminum chalcogenide (including oxide) layers are preferably placed on the anode surface of the electroluminescent dielectric layer, and metal halide layers or metal oxide layers are preferably placed on the cathode surface of the electroluminescent dielectric layer. The operational stability of the organic electroluminescent device can be achieved through the surface layer. Preferably, the chalcogenide includes SiO₂. 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.

[0195] Furthermore, in the organic electroluminescent device of this disclosure, preferably, a mixed region of electron transport compound and reducing dopant, or a mixed region of hole transport compound and oxidizing dopant, can be placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to anion, and thus it becomes easier to inject and transport electrons from the mixed region into the electroluminescent medium. Furthermore, the hole transport compound is oxidized to cation, and thus it becomes easier to inject and transport holes from the mixed region into the electroluminescent medium. Preferably, the oxidizing dopant includes various Lewis acids and acceptor compounds, and the reducing dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. The reducing dopant layer can be used as a charge-generating layer to prepare an organic electroluminescent device having two or more light-emitting layers and emitting white light.

[0196] To form each layer of the organic electroluminescent device of this disclosure, dry film-forming methods such as vacuum evaporation, sputtering, plasma, ion plating, etc., or wet film-forming methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating, etc., can be used.

[0197] When using a wet film-forming method, a thin film can be formed by dissolving or diffusing the material forming each layer into any suitable solvent (such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.). The solvent can be any solvent in which the material forming each layer can dissolve or diffuse and in which there are no problems with film-forming ability.

[0198] When a layer is formed from a host compound and a dopant compound according to one embodiment, the layer can be formed by co-deposition or hybrid deposition, but is not limited thereto. Co-deposition is a hybrid deposition method in which two or more materials are placed in respective single crucible sources and current is applied to two chambers simultaneously to evaporate the materials; and hybrid deposition is a method in which two or more materials are mixed in a crucible source before being deposited and then current is applied to a chamber to evaporate the materials.

[0199] According to one embodiment, this disclosure can provide a display device comprising an organic electroluminescent compound represented by Formula 1 and / or a variety of host materials including thereof. Furthermore, by using the organic electroluminescent device of this disclosure, display devices such as smartphones, tablets, laptops, PCs, TVs, or display devices for vehicles, or lighting devices such as outdoor or indoor lighting, can be fabricated.

[0200] In the following, the preparation methods of compounds according to this disclosure will be explained with reference to the synthesis methods of representative compounds or intermediate compounds in order to provide a detailed understanding of this disclosure.

[0201] [Example 1] Preparation of compound C-32

[0202]

[0203] 1) Synthesis of compound 1-1

[0204] 2-Bromo-1-chloro-3-nitrobenzene (60 g, 253.75 mmol), 2-bromophenylboronic acid (51 g, 253.75 mmol), tetrakis(triphenylphosphine)palladium(0)(Pd(PPh3)4) (20.5 g, 17.76 mmol), sodium hydroxide (25.4 g, 634.40 mmol), 1,200 mL of tetrahydrofuran, and 300 mL of H2O were added to a reaction vessel, and the mixture was then refluxed for 12 hours. After the reaction was complete, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. The mixture was then purified by column chromatography to obtain compound 1-1 (44 g, yield: 56%).

[0205] 2) Synthesis of compounds 1-2

[0206] Compound 1-1 (44 g, 141.51 mmol), 2-formylphenylboronic acid (53 g, 353.78 mmol), Pd(PPh3)4 (11.4 g, 9.91 mmol), potassium hydroxide (17.4 g, 311.32 mmol), 440 mL of o-xylene, 88 mL of acetonitrile, and 176 mL of H2O were added to a reaction vessel, and the mixture was then refluxed for 12 hours. After the reaction was complete, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. Next, it was purified by column chromatography to obtain compound 1-2 (28.3 g, yield: 59%).

[0207] 3) Synthesis of compounds 1-3

[0208] Compounds 1-2 (28.3 g, 83.79 mmol), (methoxymethyl)triphenylphosphine chloride (43 g, 125.68 mmol), and 380 mL of tetrahydrofuran were added to the reaction vessel and stirred for 5 minutes. Next, potassium tert-butoxide (1 M in THF, 126 mL) was slowly added dropwise to the reaction mixture at 0 °C. The temperature was slowly raised to room temperature and stirred for 4 hours. Distilled water was added to the reaction solution to terminate the reaction, and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. It was then purified by column chromatography to obtain compounds 1-3 (23 g, yield: 75%).

[0209] 4) Synthesis of compounds 1-4

[0210] Compounds 1-3 (23 g, 62.87 mmol), palladium(II) acetate (710 mg, 3.14 mmol), tricyclohexylphosphine tetrafluoroborate (2.3 g, 6.29 mmol), cesium carbonate (61.4 g, 188.61 mmol), and 320 mL of o-xylene were added to a reaction vessel, and the mixture was then refluxed for 12 hours. After the reaction was complete, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. The mixture was then purified by column chromatography to obtain compounds 1-4 (13.6 g, yield: 66%).

[0211] 5) Synthesis of compounds 1-5

[0212] Compounds 1-4 (13.6 g, 41.29 mmol) and 200 mL of dichloromethane were added to a reaction vessel at 0 °C and stirred for 5 min. Next, boron trifluoride diethyl ether (15.6 mL, 123.88 mmol) was slowly added dropwise to the reaction mixture at 0 °C. The temperature was slowly raised to room temperature and stirred for 3 h. Distilled water was added to the reaction solution to terminate the reaction. After neutralization with aqueous sodium bicarbonate solution, the organic layer was extracted with dichloromethane. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. It was then purified by column chromatography to obtain compounds 1-5 (10.2 g, yield: 83%).

[0213] 6) Synthesis of compounds 1-6

[0214] Compounds 1-5 (10.2 g, 34.48 mmol), triphenylphosphine (27.1 g, 103.43 mmol), and 170 mL of o-dichlorobenzene were added to the reaction vessel, and the mixture was then refluxed for 12 hours. After the reaction was complete, the mixture was cooled to room temperature. Next, it was purified by column chromatography to obtain compounds 1-6 (6.7 g, yield: 74%). 1 H NMR (400MHz, CDCl3)8.86-8.84 (d, 1H), 8.40 (s, 1H), 8.33-8.31 (d, 1H), 8.21-8.17 (t, 2H), 8.11-8.09 (d, 1H), 8.05-8.01 (t, 1H), 7.95-7.94 (d, 1H), 7.93-7.92 (d, 1H), 7.87-7.83 (t, 1H), 7.67-7.65 (d, 1H)

[0215] 7) Synthesis of compound C-32

[0216] Compounds 1-6 (3.8 g, 14.32 mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (6.1 g, 15.76 mmol), palladium(II) acetate (160 mg, 0.72 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (590 mg, 1.43 mmol), sodium tert-butoxide (3.4 g, 35.80 mmol), and 72 mL of o-xylene were added to a reaction vessel, and the mixture was then refluxed for 4 hours. After the reaction was complete, the mixture was cooled to room temperature, and the reaction mixture was poured into methanol to precipitate a solid. The precipitated solid was filtered and dried. It was then purified by column chromatography to obtain compound C-32 (4.9 g, yield: 60%).

[0217] MW MP C-32 572.67 344℃

[0218] [Example 2] Preparation of compound C-53

[0219]

[0220] Compounds 1-6 (3 g, 11.61 mmol), 2-chloro-3-phenylquinoxaline (4.54 g, 18.86 mmol), cesium carbonate (7.5 g, 23.01 mmol), 4-dimethylaminopyridine (715 mg, 5.85 mmol), and 60 mL of dimethyl sulfoxide were added to a reaction vessel, and the mixture was then refluxed for 4 hours. After the reaction was complete, the mixture was cooled to room temperature, and the reaction mixture was poured into distilled water to precipitate a solid. The precipitated solid was filtered and dried. It was then purified by column chromatography to obtain compound C-53 (2.8 g, yield: 52%).

[0221] MW MP C-53 469.55 275℃

[0222] [Example 3] Preparation of compound C-4

[0223]

[0224] Compounds 1-6 (3.35 g, 12.63 mmol), 3-bromo-1,1':2',1”-terphenyl (4.3 g, 13.89 mmol), palladium(II) acetate (141 mg, 0.63 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (520 mg, 1.26 mmol), sodium tert-butoxide (3 g, 31.58 mmol), and 80 mL of o-xylene were added to a reaction vessel, and the mixture was then refluxed for 12 hours. After the reaction was complete, the mixture was cooled to room temperature and then purified by column chromatography to obtain compound C-4 (2.58 g, yield: 41%).

[0225] MW MP C-4 493.61 157℃

[0226] [Example 4] Preparation of compound C-7

[0227]

[0228] Compounds 1-6 (3.35 g, 12.63 mmol), N-(3-bromophenyl)-N-phenyl-[1,1'-biphenyl]-4-amine (5.56 g, 13.89 mmol), tris(dibenzylacetone)dipalladium(0) (580 mg, 0.63 mmol), tri-tert-butylphosphine (50 wt% in toluene, 0.62 mL), sodium tert-butoxide (3 g, 31.58 mmol), and 80 mL of toluene were added to a reaction vessel, and the mixture was then refluxed for 12 hours. After the reaction was complete, the mixture was cooled to room temperature and then purified by column chromatography to obtain compound C-7 (4.36 g, yield: 59%).

[0229] MW MP C-7 584.72 199℃

[0230] [Example 5] Preparation of compound H2-29

[0231]

[0232] 1) Synthesis of compound 5-1

[0233] Naphthalene-2-ylboronic acid (50 g, 291 mmol), 2-bromo-4-chlorobenzaldehyde (63 g, 291 mmol), tetrakis(triphenylphosphine)palladium (16.8 g, 14.5 mmol), sodium carbonate (77 g, 727 mmol), toluene (1,080 mL), ethanol (240 mL), and distilled water (360 mL) were added to a reaction vessel, and the mixture was stirred at 140 °C for 5 hours. After the reaction was complete, the precipitated solid was washed with distilled water and methanol. The solid was then purified by column chromatography to obtain compound 5-1 (71 g, yield: 92%).

[0234] 2) Synthesis of compound 5-2

[0235] Compound 5-1 (71 g, 268 mmol), (methoxymethyl)triphenylphosphine chloride (110 g, 321 mmol), and tetrahydrofuran (1,300 mL) were added to a reaction vessel, and the reaction mixture was stirred for 10 minutes. Then, potassium tert-butoxide (1 M, 300 mL in THF) was slowly added dropwise at 0 °C. The temperature was slowly increased, and the mixture was stirred at room temperature for 3 hours. Distilled water was added to the reaction solution to terminate the reaction, and the mixture was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. Next, it was purified by column chromatography to obtain compound 5-2 (71 g, yield: 90%).

[0236] 3) Synthesis of compound 5-3

[0237] Compound 5-2 (70 g, 238 mmol), Eaton reagent (7 mL), and chlorobenzene (1,180 mL) were added to the reaction vessel and refluxed for 1 hour. After the reaction was complete, the mixture was cooled to room temperature and extracted with dichloromethane (MC). The extracted organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. Next, it was purified by column chromatography to obtain compound 5-3 (60 g, yield: 96%).

[0238] 4) Synthesis of compound 5-4

[0239] Compound 5-3 (35 g, 133.2 mmol), bis(pinacolyl)diborane (44 g, 173 mmol), tris(dibenzylacetone)dipalladium (6.1 g, 6.66 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (s-phos) (5.5 g, 13.3 mmol), potassium acetate (39.2 g, 400 mmol), and 1,4-dioxane (666 mL) were added to a reaction vessel, and the mixture was stirred at 150 °C for 3 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by a rotary evaporator. The resulting solution was then purified by column chromatography to obtain compound 5-4 (38 g, yield: 81%).

[0240] 5) Synthesis of compound H2-29

[0241] Compound 5-4 (5 g, 14.1 mmol), 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (6.6 g, 18.3 mmol), tetra(triphenylphosphine)palladium (0.8 g, 0.7 mmol), potassium carbonate (3.9 g, 28.2 mmol), toluene (42 mL), ethanol (10 mL), and distilled water (14 mL) were added to a reaction vessel, and the mixture was stirred at 140 °C for 8 hours. After the reaction was complete, the mixture was added dropwise to methanol, and the resulting solid was filtered off. The solid was purified by column chromatography to obtain compound H2-29 (6.8 g, yield: 88%).

[0242] MW MP H2-29 549.6 267℃

[0243] The following will explain the preparation method and device characteristics of an organic electroluminescent device comprising the organic electroluminescent compound and / or multiple host materials disclosed herein, in order to provide a detailed understanding of this disclosure.

[0244] [Apparatus Examples 1 and 2] Preparation of OLEDs deposited using compounds according to this disclosure as the host material

[0245] The OLED is produced according to this disclosure. First, a transparent electrode indium tin oxide (ITO) thin film (10 Ω / sq) (GEOMATEC CO., LTD., Japan) on a glass substrate used for the OLED is subjected to ultrasonic washing sequentially with acetone and isopropanol, and then stored in isopropanol for use. Subsequently, the ITO substrate is mounted on a substrate support in a vacuum vapor deposition apparatus. Then, compound HI-1 is introduced as a first hole injection compound into one chamber of the vacuum vapor deposition apparatus, and compound HT-1 is introduced as a first hole transport compound into another chamber. The two materials are evaporated at different rates, and the first hole injection compound is deposited at a doping amount of 3 wt% based on the total amount of the first hole injection compound and the first hole transport compound to form a first hole injection layer with a thickness of 10 nm. Next, compound HT-1 is deposited on the first hole injection layer as a first hole transport layer with a thickness of 80 nm. Compound HT-2 was then introduced into another chamber of a vacuum vapor deposition apparatus, and evaporated by applying current to the chamber, 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 the hole transport layer, the light-emitting layer was formed thereon as follows: the host material described in Table 1 was introduced as the host into one chamber of the vacuum vapor deposition apparatus, and compound D-39 was introduced as the dopant into another chamber. The two materials were evaporated at different rates, and the dopant was deposited at a doping amount of 3 wt% based on the total amount of the host and the dopant to form a light-emitting layer with a thickness of 40 nm on the second hole transport layer. Next, compounds ETL-1 and EIL-1 were deposited as materials for the electron transport layer in a 50:50 weight ratio to form an electron transport layer with a thickness of 35 nm on the light-emitting layer. After depositing compound EIL-1 as an electron injection layer with a thickness of 2 nm on the electron transport layer, an Al cathode with a thickness of 80 nm was deposited on the electron injection layer using another vacuum vapor deposition apparatus. Thus, an OLED was produced. Each compound used in all materials will be in 10 -6 Purification is achieved through vacuum sublimation.

[0246] [Device Comparison Example 1] Fabrication of an OLED Containing Conventional Compounds as the Main Body

[0247] The OLED is produced in the same manner as in Device Example 1, except that the compound CBP is used as the main body of the light-emitting layer.

[0248] The driving voltage, luminous efficiency, and emission color of the OLEDs manufactured as described above according to Device Examples 1 and 2 and Comparative Example 1 were measured at a brightness of 1,000 nits, as well as the time (lifetime; T95) taken for the brightness to decrease from 100% to 95% at a brightness of 5,000 nits, and the results are shown in Table 1 below:

[0249] Table 1

[0250]

[0251] As can be seen from Table 1 above, compared with organic electroluminescent devices using conventional host materials, organic electroluminescent devices containing organic electroluminescent compounds according to the present disclosure as host materials have low driving voltage, high luminous efficiency and significantly improved lifetime characteristics.

[0252] [Device Examples 3 and 4] Fabrication of OLEDs Incorporating Multiple Host Materials

[0253] The OLED is produced in the same manner as in Device Example 1, except that: the first host material and the second host material, which are shown in Table 2 below, are introduced into two chambers of a vacuum vapor deposition apparatus, respectively, and compound D-39 is introduced into another chamber as a dopant. The two host materials are evaporated at a rate of 1:1, and the dopant material is evaporated simultaneously at different rates. The dopant material is deposited with a doping amount of 3 wt% based on the total amount of the host and the dopant to form a light-emitting layer with a thickness of 40 nm on the hole transport layer.

[0254] The driving voltage, luminous efficiency, and emission color of the OLEDs manufactured as described above according to device examples 3 and 4 were measured at a brightness of 1,000 nits, as well as the time (lifetime; T95) taken for the brightness to decrease from 100% to 95% at a brightness of 5,000 nits, and the results are shown in Table 2 below:

[0255] Table 2

[0256]

[0257] Table 2 above confirms that a specific combination of the host materials according to this disclosure can improve driving, luminous efficiency, and lifetime characteristics at low voltage.

[0258] The compounds used in the above apparatus examples 1 to 4 and apparatus comparative example 1 are specifically shown in Table 3 below.

[0259] Table 3

[0260]

[0261] [Device Example 5] Fabrication of a blue light-emitting OLED according to the present disclosure

[0262] The OLED is produced according to this disclosure. First, a transparent electrode indium tin oxide (ITO) thin film (10 Ω / sq) (GEOMATEC CO., LTD., Japan) on a glass substrate used for the OLED is subjected to ultrasonic washing sequentially with acetone and isopropanol, and then stored in isopropanol for use. Subsequently, the ITO substrate is mounted on a substrate support in a vacuum vapor deposition apparatus. Then, compound HI-1 is introduced as a hole injection compound into one chamber of the vacuum vapor deposition apparatus, and hole transport compound HT-3 is introduced into another chamber. The two materials are evaporated at different rates, and the hole injection compound is deposited with a doping amount of 7 wt% based on the total amount of the hole injection compound and the hole transport compound to form a hole injection layer with a thickness of 10 nm. Next, compound HT-1 is deposited on the hole injection layer as a first hole transport layer with a thickness of 75 nm. Next, compound C-4 was introduced as a material for the second hole transport layer into another chamber of the vacuum vapor deposition apparatus, and the compound was evaporated by applying an electric current to the chamber, 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 the hole transport layer, a light-emitting layer was formed thereon as follows: compound BH was introduced as a host into two chambers of the vacuum deposition apparatus, and compound BD was introduced as a dopant into another chamber. The two materials were evaporated at different rates and the dopant material was deposited with a dopant amount of 2 wt% based on the total amount of the host and dopant to form a light-emitting layer with a thickness of 20 nm on the second hole transport layer. Next, compound HBL was deposited as an electron buffer layer on the light-emitting layer to form an electron buffer layer with a thickness of 5 nm. Next, compounds ETL-1 and EIL-1 were deposited as electron transport layers in a 5:5 ratio to form an electron transport layer with a thickness of 30 nm on the electron buffer layer. After depositing compound EIL-1 as a 2 nm thick electron injection layer on the electron transport layer, an 80 nm thick Al cathode was deposited on the electron injection layer using another vacuum vapor deposition apparatus. This produced an OLED.

[0263] [Device Example 6] Fabrication of a Blue Light Emitting OLED according to the present disclosure

[0264] The OLED was produced in the same manner as in Device Example 5, except that compound C-7 was used as the second hole transport layer.

[0265] [Comparative Example 2] Fabrication of a Blue Light Emitting OLED Not Based on This Disclosure

[0266] The OLED is produced in the same manner as in Device Example 5, except that the first hole transport layer is deposited to a thickness of 80 nm without a second hole transport layer.

[0267] The driving voltage, luminous efficacy, and CIE color coordinates of the OLEDs manufactured as described above according to device examples 5 and 6 and comparative example 2 were measured at a brightness of 1,000 nits, and the results are shown in Table 4 below:

[0268] Table 4

[0269]

[0270] As can be seen from Table 4 above, organic electroluminescent devices incorporating organic electroluminescent compounds according to the present disclosure as hole transport materials exhibit excellent efficiency characteristics.

[0271] The compounds used in apparatus examples 5 and 6 and apparatus comparative example 2 are specifically shown in Table 5 below:

[0272] Table 5

[0273]

[0274] [Device Comparison Example 3] Fabrication of a Blue Light Emitting OLED Without an Electron Buffer Layer

[0275] The production of OLEDs is not based on this disclosure. First, a transparent electrode indium tin oxide (ITO) film (10 Ω / sq) (GEOMATEC CO., LTD., Japan) on a glass substrate used for the OLED is subjected to ultrasonic washing with isopropanol, and then stored in isopropanol for use. Subsequently, the ITO substrate is mounted on a substrate support in a vacuum vapor deposition apparatus. Then, compound HI-1 is introduced as a first hole injection compound into one chamber of the vacuum vapor deposition apparatus, and a first hole transport compound HT-4 is introduced into another chamber. The two materials are evaporated at different rates, and the first hole injection compound is deposited at a doping amount of 3 wt% based on the total amount of the first hole injection compound and the first hole transport compound to form a first hole injection layer with a thickness of 10 nm. Next, compound HT-1 is deposited on the first hole injection layer as a first hole transport layer with a thickness of 80 nm. Next, compound HT-4 was introduced into another chamber of a vacuum vapor deposition apparatus, and the compound was evaporated by applying current to the chamber, 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 the hole transport layer, the light-emitting layer was formed thereon as follows: compound BH-1 was introduced as the host into one chamber of the vacuum vapor deposition apparatus, and compound BD-1 was introduced as the dopant into another chamber. The two materials were evaporated at different rates, and the dopant material was deposited with a dopant content of 2 wt% based on the total amount of the host and the dopant to form a light-emitting layer with a thickness of 20 nm on the second hole transport layer. Next, compounds ETL-1 and EIL-1 were deposited as electron transport materials in a 50:50 weight ratio to form an electron transport layer with a thickness of 35 nm on the light-emitting layer. After depositing compound EIL-1 as an electron injection layer with a thickness of 2 nm on the electron transport layer, an Al cathode with a thickness of 80 nm was deposited on the electron injection layer using another vacuum vapor deposition apparatus. Thus, an OLED was produced.

[0276] [Apparatus Example 7] Preparation of an OLED emitting blue light comprising a compound according to the present disclosure as an electron buffer material

[0277] The OLED was produced in the same manner as in Comparative Example 3, except that the electron transport layer was deposited to a thickness of 30 nm and compound C-32 was deposited between the light-emitting layer and the electron transport layer to form an electron buffer layer with a thickness of 5 nm.

[0278] The driving voltage, luminous efficiency, CIE color coordinates, and external quantum efficiency of the OLEDs manufactured as described above according to Comparative Examples 3 and 7 were measured at a brightness of 1,000 nits, as well as the time (lifetime; T50) taken for the brightness to decrease from 100% to 50% at a constant current of 2,750 nits. The results are shown in Table 6 below:

[0279] Table 6

[0280]

[0281] As can be seen from Table 6 above, due to the rapid electronic current characteristics of the electronic buffer material of this disclosure, device example 7 has superior lifetime characteristics compared with comparative example 3 without electronic buffer material.

[0282] The compounds used in apparatus comparative example 3 and apparatus example 7 are specifically shown in Table 7 below:

[0283] Table 7

[0284]

[0285] In the organic electroluminescent compounds represented by Formula 1 according to this disclosure, the LUMO (lowest unoccupied molecular orbital) level, HOMO (highest occupied molecular orbital) level and triplet energy of compounds in which X represents N-L1-Ar1 (where L1 represents a single bond and Ar1 represents a phenyl), O, S and CR1R2 (where R1 and R2 are both methyl) were measured, and the results are shown in Table 8 below.

[0286] Table 8

[0287]

[0288] *The structure was optimized using the Gaussian16 quantum chemistry calculation program, with hybrid density functional theory (hybrid DFT) (B3LYP) and 6-31G(d) basis sets applied, and the triplet state was calculated using TD-DFT (time-dependent DFT).

[0289] Referring to Table 8 above, in the organic electroluminescent compounds represented by Formula 1 according to this disclosure, when X represents N-L1-Ar1, O, S, and CR1R2, it can be confirmed that all parent nuclei have similar energy levels. Therefore, even when O, S, or CR1R2 instead of N-L1-Ar1 is introduced into the parent nucleus, device characteristics similar to those of the device examples 1 and 2 above are expected.

Claims

1. An organic electroluminescent compound, represented by the following formula 1-1: --- (1-1) in, Y1 to Y 10 Each can be represented independently as CR3; R3 represents hydrogen, deuterium, a C6-C30 aryl group substituted or unsubstituted with at least one selected from deuterium, C6-C30 aryl and 3- to 30-membered heteroaryl, or a 3- to 30-membered heteroaryl group substituted or unsubstituted with at least one selected from deuterium and C6-C30 aryl. L1 represents a single bond, a deuterated or unsubstituted C6-C30 arylene, or a deuterated or unsubstituted 5- to 18-membered heteroarylene; Ar1 represents a deuterated or unsubstituted C6-C30 aryl group, selected from at least one substituted or unsubstituted 3- to 30-membered heteroaryl group selected from deuterium, C1-C30 alkyl, C6-C30 aryl, and 3- to 30-membered heteroaryl groups, or -N-R'3R'4; and R'3 and R'4 each independently represent a C6-C30 aryl group that is substituted or unsubstituted with at least one of deuterium and C1-C30 alkyl groups, or a 3- to 30-membered heteroaryl group that is deuterated or unsubstituted.

2. An organic electroluminescent compound, wherein, The organic electroluminescent compound is selected from the following compounds: 。 3. An organic electroluminescent material comprising the organic electroluminescent compound according to claim 1.

4. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1.

5. The organic electroluminescent device according to claim 4, wherein, The organic electroluminescent compound is contained in at least one of a hole transport layer, a light-emitting layer, a buffer layer, and an electron transport layer.

6. A plurality of host materials comprising a first host material and a second host material, wherein the first host material comprises an organic electroluminescent compound according to claim 1, and the second host material comprises an organic electroluminescent compound represented by formula 2: --- (2) in, T5 and T6 are connected to each other to form a loop of the following formula 3; or T7 and T8 are connected to each other to form a loop of the following formula 3; or T5 and T6 are connected to each other to form a loop of the following formula 3, and T7 and T8 are connected to each other to form a loop of the following formula 3; --- (3) T1 to T4 and T9 to T3 do not form a ring 14 T5 to T8 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3- to 30-membered heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted tri-C1-C30 alkylsilyl, substituted or unsubstituted di-C1-C30 alkylC6-C30 arylsilyl, substituted or unsubstituted C1-C30 alkyldi-C6-C30 arylsilyl, substituted or unsubstituted tri-C6-C30 arylsilyl, substituted or unsubstituted fused rings of C3-C30 aliphatic rings and C6-C30 aromatic rings, substituted or unsubstituted mono- or di-C 1-C30 alkylamino, substituted or unsubstituted mono- or di-C2-C30 alkenylamino, substituted or unsubstituted C1-C30 alkyl C2-C30 alkenylamino, substituted or unsubstituted mono- or di-C6-C30 arylamino, substituted or unsubstituted C1-C30 alkyl C6-C30 arylamino, substituted or unsubstituted mono- or di-3- to 30-membered heteroarylamino, substituted or unsubstituted C1-C30 alkyl 3- to 30-membered heteroarylamino, substituted or unsubstituted C2-C30 alkenyl C6-C30 arylamino, substituted or unsubstituted C2-C30 alkenyl 3- to 30-membered heteroarylamino, substituted or unsubstituted C6-C30 aryl 3- to 30-membered heteroarylamino, or -L2-Ar2, provided that T1 to T 14 At least one of them is -L2-Ar2; L2 represents a single bond, a substituted or unsubstituted C6-C30 arylene, or a substituted or unsubstituted 3- to 30-membered heteroarylene; Ar2 represents substituted or unsubstituted C6-C30 aryl groups, or substituted or unsubstituted 3- to 30-membered heteroaryl groups; --- indicates the site fused to Equation 2; and The heteroaryl group contains at least one heteroatom selected from B, N, O, S, Si, and P.

7. The various main body materials according to claim 6, wherein, The compound represented by Formula 2 is selected from the following compounds: and .

8. An organic electroluminescent device comprising a plurality of host materials as described in claim 6.

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