Organic electroluminescent compounds, organic electroluminescent materials containing the same, and organic electroluminescent devices

Abstract

To provide: a specific organic electroluminescent compound including a triazine skeleton and carbazole skeleton; an organic electroluminescent material comprising the compound; and an organic electroluminescent device.SOLUTION: The present disclosure relates to: a specific organic electroluminescent compound including a triazine skeleton and carbazole skeleton; an organic electroluminescent material comprising the compound; and an organic electroluminescent device. By comprising the specific organic electroluminescent compound including a triazine skeleton and carbazole skeleton, an organic electroluminescent device can be provided which has improved driving voltage and / or luminous efficiency and / or lifespan characteristics compared with organic electroluminescent devices comprising a conventional organic electroluminescent compound.SELECTED DRAWING: None

Description

[Technical Field]

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

[0002] Electroluminescent devices (EL devices) are self-emissive display devices that offer advantages such as wider viewing angles, higher contrast ratios, and faster response times. The first organic EL device was developed in 1987 by Eastman Kodak by using small aromatic diamine molecules and aluminum complexes as materials to form the light-emitting layer (Non-Patent Literature 1).

[0003] The most important factor in determining the luminescence efficiency of organic electroluminescent devices is the luminescent material. Until now, fluorescent materials have been widely used as luminescent materials. However, from the perspective of the electroluminescent mechanism, phosphorescent luminescent materials theoretically increase the luminescence efficiency by four times compared to fluorescent luminescent materials, so phosphorescent luminescent materials are being widely studied. Iridium(III) complexes are widely known as phosphorescent luminescent materials, such as bis(2-(2'-benzothienyl)-pyridinate-N,C-3')iridium(acetylacetonate)[(acac)Ir(btp)2], tris(2-phenylpyridine)iridium[Ir(ppy)3], and bis(4,6-difluorophenylpyridinate-N,C2)picolinatoiridium (Firpic), which emit red, green, and blue light, respectively.

[0004] In prior art, 4,4'-N,N'-dicarbazole-biphenyl (CBP) is the most widely known phosphorescent host material. Recently, Pioneer et al. (Japan) developed high-performance organic electroluminescent devices using bathocuproine (BCP) and aluminum(III) bis(2-methyl-8-quinolinate)(4-phenylphenolate)(BAlq) as host materials, which were known as hole-blocking materials.

[0005] However, while conventional materials offer excellent luminescence properties, they have the following drawbacks: (1) Due to their low glass transition temperature and insufficient thermal stability, degradation can occur during high-temperature deposition processes in vacuum, potentially reducing the device's lifespan. (2) The power efficiency of organic electroluminescent devices is determined by [(π / voltage) × current efficiency], where power efficiency is inversely proportional to voltage. Organic electroluminescent devices containing phosphorescent host materials offer higher current efficiency (cd / A) than those containing fluorescent materials, but require significantly higher drive voltages. Therefore, they offer no advantage in terms of power efficiency (lm / W). (3) Furthermore, organic electroluminescent devices have a short operating life, and further improvements in luminescence efficiency are needed.

[0006] Various materials and concepts have been proposed for the organic layer of organic electroluminescent devices to improve luminous efficiency, drive voltage, and / or lifespan, but these have not been satisfactory in practical applications. [Prior art documents] [Non-patent literature]

[0007] [Non-Patent Document 1] Appl.Phys.Lett.51,913,1987 [Overview of the Initiative] [Problems that the invention aims to solve]

[0008] The object of this disclosure is, firstly, to provide an organic electroluminescent compound and an organic electroluminescent material containing the same that is effective for manufacturing an organic electroluminescent device having a low drive voltage and / or high luminescence efficiency and / or long life; and secondly, to provide an organic electroluminescent device containing the organic electroluminescent compound. [Means for solving the problem]

[0009] Specifically, the inventors discovered that the aforementioned objectives can be achieved by an organic electroluminescent compound represented by the following formula 1, and thus completed the present invention. [ka] (In the formula, X represents either O or S; Ar1 and Ar2 independently represent substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted 9,9'-spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted 9-phenylcarbazolyl, substituted or unsubstituted 2-phenylbenzoxazolyl, or substituted or unsubstituted 2-phenylbenzothiazolyl; L1 and L2 independently represent a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted dibenzothiophenylene, a substituted or unsubstituted 9-phenylcarbazolylene, a substituted or unsubstituted 9,9-dimethylfluorenylene, a substituted or unsubstituted 9,9-diphenylfluorenylene, or a substituted or unsubstituted 9,9'-spirobifluorenylene; R1-R4, R', and R'' each independently represent hydrogen or deuterium; a and d each independently represent an integer from 1 to 4, b represents an integer from 1 to 3, and c represents the integer 1; When a, b, and d are integers greater than or equal to 2, R1, R2, and R4 may be the same or different respectively).

[0010] Advantageous effects of the invention By including the organic electroluminescent compound and the organic electroluminescent material containing the same according to the present disclosure, an organic electroluminescent device having a low driving voltage and / or a high luminous efficiency and / or a long lifespan can be manufactured.

Modes for carrying out the invention

[0011] Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present invention and does not mean to limit the scope of the present invention in any way.

[0012] The term "organic electroluminescent compound" in the present disclosure means a compound that can be used in an organic electroluminescent device and can be included in any layer constituting the organic electroluminescent device as needed.

[0013] In this specification, "organic electroluminescent material" means a material that can be used in an organic electroluminescent device and can contain at least one compound. The organic electroluminescent material can be included in any layer constituting the organic electroluminescent device as needed. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole auxiliary material, a light emission auxiliary material, an electron blocking material, a light emitting material, an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material, etc.

[0014] In this specification, “multiple host materials” means an organic electroluminescent material comprising a combination of at least two host materials. This may mean both materials before (e.g., before deposition) and materials after (e.g., after deposition) the organic electroluminescent device is included. The multiple host materials of this disclosure may be included in any light-emitting layer constituting an organic electroluminescent device. Two or more compounds included in the multiple host materials of this disclosure may be included in one light-emitting layer or each may be included in different light-emitting layers. If at least two host materials are included in one layer, the at least two host materials may be mixed and evaporated to form the layer, or they may be co-evaporated simultaneously and individually to form the layer.

[0015] In this disclosure, the term "electron transport band" means a band in which electrons move between the cathode and the light-emitting layer. For example, the electron transport band may include at least one of an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer, preferably at least one of a hole blocking layer, an electron transport layer, and an electron injection layer. The hole blocking layer has the function of preventing holes from entering the cathode through the light-emitting layer in the operation of an organic electroluminescent device.

[0016] In this specification, "(C1-C30) alkyl" means a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, where the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10. Examples of the alkyls mentioned above include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, etc. In this specification, the term "(C2-C30) alkenyl" means a linear or branched alkenyl having 2 to 30 carbon atoms constituting the chain, where the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10. Examples of the alkenyls mentioned above include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbuta-2-enyl, etc. In this specification, the term "(C2-C30) alkynyl" means a linear or branched alkynyl having 2 to 30 carbon atoms constituting the chain, where the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10. Examples of the above alkynyl include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpenta-2-inyl, etc. In this specification, the term "(C3-C30) cycloalkyl" means a monocyclic or polycyclic hydrocarbon having 3 to 30 carbon atoms in the ring skeleton, where the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7. Examples of the above cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, etc. In this specification, "(C6-C30)aryl(ene)" is a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring skeleton carbon atoms (preferably 6 to 25, more preferably 6 to 18), and may be partially saturated. Examples of aryls include, specifically, phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl,Examples include dibenzofluorenyl, phenantrenyl, benzophenantrenyl, phenylphenantrenyl, anthracenyl, benzanthracenyl, indenyl, triphenylenyl, pyrenyl, tetracerenyl, perilenyl, crisenyl, benzocrisenyl, naphthacenyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, mesityl, cumenyl, spiro[fluoren-fluoren]yl, spiro[fluoren-benzofluoren]yl, azlenyl, tetramethyl-dihydrophenantrenyl, and others. More specifically, aryls include o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, pt-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-t-butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl Nyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl- Tyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-crisenyl, 2- Crisenyl, 3-crisenyl, 4-crisenyl, 5-crisenyl, 6-crisenyl, benzo[c]phenanthryl, benzo[g]crisenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, 11,11-dimethyl-1-benzo[a]fluorenyl,11,11-dimethyl-2-benzo[a]fluorenyl, 11,11-dimethyl-3-benzo[a]fluorenyl, 11,11-dimethyl-4-benzo[a]fluorenyl, 11,11-dimethyl-5-benzo[a]fluorenyl, 11,11-dimethyl-6-benzo[a]fluorenyl, 11,11-dimethyl-7-benzo[a]fluorenyl, 11,11-dimethyl-8-benzo[a]fluorenyl, 11,11-dimethyl-9-benzo[a]fluorenyl, 11,11-dimethyl-10-benzo[a]fluorenyl, 11,11-dimethyl-1-benzo[a]fluorenyl Zo[b]fluorenyl, 11,11-dimethyl-2-benzo[b]fluorenyl, 11,11-dimethyl-3-benzo[b]fluorenyl, 11,11-dimethyl-4-benzo[b]fluorenyl, 11,11-dimethyl-5-benzo[b]fluorenyl, 11,11-dimethyl-6-benzo[b]fluorenyl, 11,11-dimethyl-7-benzo[b]fluorenyl, 11,11-dimethyl-8-benzo[b]fluorenyl, 11,11-dimethyl-9-benzo[b]fluorenyl, 11,11-dimethyl-10-benzo[b]fluorenyl, 11,1 1-dimethyl-1-benzo[c]fluorenyl, 11,11-dimethyl-2-benzo[c]fluorenyl, 11,11-dimethyl-3-benzo[c]fluorenyl, 11,11-dimethyl-4-benzo[c]fluorenyl, 11,11-dimethyl-5-benzo[c]fluorenyl, 11,11-dimethyl-6-benzo[c]fluorenyl, 11,11-dimethyl-7-benzo[c]fluorenyl, 11,11-dimethyl-8-benzo[c]fluorenyl, 11,11-dimethyl-9-benzo[c]fluorenyl, 11,11-dimethyl-10-benzo[c] Fluorenyl, 11,11-diphenyl-1-benzo[a]fluorenyl, 11,11-diphenyl-2-benzo[a]fluorenyl, 11,11-diphenyl-3-benzo[a]fluorenyl, 11,11-diphenyl-4-benzo[a]fluorenyl, 11,11-diphenyl-5-benzo[a]fluorenyl, 11,11-diphenyl-6-benzo[a]fluorenyl, 11,11-diphenyl-7-benzo[a]fluorenyl, 11,11-diphenyl-8-benzo[a]fluorenyl, 11,11-diphenyl-9-benzo[a]fluorenyl,11,11-diphenyl-10-benzo[a]fluorenyl, 11,11-diphenyl-1-benzo[b]fluorenyl, 11,11-diphenyl-2-benzo[b]fluorenyl, 11,11-diphenyl-3-benzo[b]fluorenyl, 11,11-diphenyl-4-benzo[b]fluorenyl, 11,11-diphenyl-5-benzo[b]fluorenyl, 11,11-diphenyl-6-benzo[b Fluorenyl, 11,11-diphenyl-7-benzo[b]fluorenyl, 11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9-benzo[b]fluorenyl, 11,11-diphenyl-10-benzo[b]fluorenyl, 11,11-diphenyl-1-benzo[c]fluorenyl, 11,11-diphenyl-2-benzo[c]fluorenyl, 11,11-diphenyl- 3-benzo[c]fluorenyl, 11,11-diphenyl-4-benzo[c]fluorenyl, 11,11-diphenyl-5-benzo[c]fluorenyl, 11,11-diphenyl-6-benzo[c]fluorenyl, 11,11-diphenyl-7-benzo[c]fluorenyl, 11,11-diphenyl-8-benzo[c]fluorenyl, 11,11-diphenyl-9-benzo[c]fluorenyl, 11,11 -Diphenyl-10-benzo[c]fluorenyl, 9,9,10,10-tetramethyl-9,10-dihydro-1-phenantrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-2-phenantrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-3-phenantrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-4-phenantrenyl, etc. In this specification, "(3-30 membered) heteroaryl" is an aryl having 3 to 30 ring skeleton atoms, including at least one, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, Si, P, Se, and Ge. The above heteroaryl may be a monoring, a fused ring fused with at least one benzene ring, or partially saturated. Furthermore, the heteroaryls described herein may be formed by bonding at least one heteroaryl or aryl group to a heteroaryl group via a single bond.They may also contain spiro structures. Examples of heteroaryls include, specifically, monocyclic heteroaryls such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetradinyl, triazolyl, tetrazolyl, flazanil, pyridyl, pyrazinyl, pyrimidinyl, pyridadinyl; as well as benzofuranil, benzothiophenyl, isobenzofuranil, Dibenzofuranil, dibenzothiophenyl, dibenzoselenophenyl, benzofloxinolinil, benzofloxinazolinil, benzoflonaphtylidinil, benzoflopyrimidinil, naphthoflopyrimidinil, benzothienocinolyl, benzothienonaphtylidinil, benzothienopyrimidinil, naphthienopyrimidinil, pyrimidoindolyl, benzopyrimidoindolyl, benzoflopyrazinil, naphthoflopyrimidinil Nyl, benzothienopyrazinyl, naphthienopyrazinyl, pyrazinoindolyl, benzopyradinoindolyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacal Examples of condensed ring heteroaryls include bazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxadinyl, phenantridinyl, benzodioxolyl, indolinyl, acridinyl, silafluorenyl, germafluorenyl, benzotriazolyl, phenadinyl, imidazopyridinyl, clomenoquinazolinyl, thioclomenoquinazolinyl, dimethylbenzopyrimidinyl, indolocarbazolyl, and indenocarbazolyl. More specifically, heteroaryls include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazine-4-yl, 1,2,4-triazine-3-yl, 1,3,5-triazine-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolinyl, 2-indolinyl,3-Indolinyl, 5-Indolinyl, 6-Indolinyl, 7-Indolinyl, 8-Indolinyl, 2-Imidazopyridinyl, 3-Imidazopyridinyl, 5-Imidazopyridinyl, 6-Imidazopyridinyl, 7-Imidazopyridinyl, 8-Imidazopyridinyl, 1-Indolyl, 2-Indolyl, 3-Indolyl Drill, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl Nyl, 2-Quinolyl, 3-Quinolyl, 4-Quinolyl, 5-Quinolyl, 6-Quinolyl, 7-Quinolyl, 8-Quinolyl, 1-Isoquinolyl, 3-Isoquinolyl, 4-Isoquinolyl, 5-Isoquinolyl, 6-Isoquinolyl, 7-Isoquinolyl, 8-Isoquinolyl, 2-Quinoxalinyl, 5-Quinoxalinyl, 6-Quinoxalinyl, 1-Carbazolyl, 2-Carbazolyl, 3-Carbazolyl, 4-Carbazolyl, 9-Carbazolyl, Azacarbazole-1-yl, Azacarbazole-2-yl, Azacarbazole-3-yl, Azacarbazole-4-yl, Aza Carbazole-5-yl, azacarbazole-6-yl, azacarbazole-7-yl, azacarbazole-8-yl, azacarbazole-9-yl, 1-phenanthridine, 2-phenanthridine, 3-phenanthridine, 4-phenanthridine, 6-phenanthridine, 7-phenanthridine, 8-phenanthridine, 9-phenanthridine, 10-phenanthridine, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl , 2-oxadiazolyl, 5-oxadiazolyl, 3-flazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrole-1-yl, 2-methylpyrrole-3-yl, 2-methylpyrrole-4-yl, 2-methylpyrrole-5-yl, 3-methylpyrrole-1-yl, 3-methylpyrrole-2-yl, 3-methylpyrrole-4-yl, 3-methylpyrrole-5-yl, 2-t-butylpyrrole-4-yl, 3-(2-phenylpropyl)pyrrole-1-yl, 2-methyl-1-indolly, 4-methyl-1-indolly, 2-methyl-3-indolly,4-methyl-3-indolyl, 2-t-butyl-1-indolyl, 4-t-butyl-1-indolyl, 2-t-butyl-3-indolyl, 4-t-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-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 Lanyl, 7-naphtho-[1,2-b]-benzofuranil, 8-naphtho-[1,2-b]-benzofuranil, 9-naphtho-[1,2-b]-benzofuranil, 10-naphtho-[1,2-b]-benzofuranil, 1-naphtho-[2,3-b]-benzofuranil, 2-naphtho-[2,3-b]-benzofuranil, 3-naphtho-[2,3-b]-benzofuranil, 4-naphtho-[2,3-b]-benzofuranil, 5-naphtho-[2,3-b]-benzofuranil, 6-naphtho-[2,3-b]-benzofuranil, 7-naphtho-[2,3-b]-benzofuranil, 8-naphtho-[2,3-b]-benzofuranil Naphtho-[2,3-b]-benzofuranil, 9-naphtho-[2,3-b]-benzofuranil, 10-naphtho-[2,3-b]-benzofuranil, 1-naphtho-[2,1-b]-benzofuranil, 2-naphtho-[2,1-b]-benzofuranil, 3-naphtho-[2,1-b]-benzofuranil, 4-naphtho-[2,1-b]-benzofuranil, 5-naphtho-[2,1-b]-benzofuranil, 6-naphtho-[2,1-b]-benzofuranil, 7-naphtho-[2,1-b]-benzofuranil, 8-naphtho-[2,1-b]-benzofuranil, 9-naphtho-[2,1 -b]-benzofuranyl, 10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b]-benzothiophenyl, 2-naphtho-[1,2-b]-benzothiophenyl, 3-naphtho-[1,2-b]-benzothiophenyl, 4-naphtho-[1,2-b]-benzothiophenyl, 5-naphtho-[1,2-b]-benzothiophenyl, 6-naphtho-[1,2-b]-benzothiophenyl, 7-naphtho-[1,2-b]-benzothiophenyl, 8-naphtho-[1,2-b]-benzothiophenyl, 9-naphtho-[1,2-b]-benzothiophenyl,10-Naphtho-[1,2-b]-benzothiophenyl, 1-Naphtho-[2,3-b]-benzothiophenyl, 2-Naphtho-[2,3-b]-benzothiophenyl, 3-Naphtho-[2,3-b]-benzothiophenyl, 4-Naphtho-[2,3-b]-benzothiophenyl, 5-Naphtho-[2,3-b]-benzothiophenyl, 1-Naphtho-[2,1-b]-benzothiophenyl, 2-Naphtho-[2,1-b]-benzothiophenyl, 3-Naphtho-[2,1-b]-benzothiophenyl, 4-Naphtho-[2,1-b]-benzothiophenyl, 5-Naphtho To-[2,1-b]-benzothiophenyl, 6-naphtho-[2,1-b]-benzothiophenyl, 7-naphtho-[2,1-b]-benzothiophenyl, 8-naphtho-[2,1-b]-benzothiophenyl, 9-naphtho-[2,1-b]-benzothiophenyl, 10-naphtho-[2,1-b]-benzothiophenyl, 2-benzoflo[3,2-d]pyrimidinyl, 6-benzoflo[3,2-d]pyrimidinyl, 7-benzoflo[3,2-d]pyrimidinyl, 8-benzoflo[3,2-d]pyrimidinyl, 9-benzoflo[3,2-d]pyrimidinyl, 2-Benzothio[3,2-d]pyrimidinyl, 6-Benzothio[3,2-d]pyrimidinyl, 7-Benzothio[3,2-d]pyrimidinyl, 8-Benzothio[3,2-d]pyrimidinyl, 9-Benzothio[3,2-d]pyrimidinyl, 2-Benzoflo[3,2-d]pyrazinyl, 6-Benzoflo[3,2-d]pyrazinyl, 7-Benzoflo[3,2-d]pyrazinyl, 8-Benzoflo[3,2-d]pyrazinyl, 9-Benzoflo[3,2-d]pyrazinyl, 2-Benzothio[3,2-d]pyrazinyl, 6-Benzothio[3,2-d]pyrazinyl, 7-Benzothio[3,2-d]pyrazinyl, 8-Benzothio[3,2-d]pyrazinyl, 9-Benzothio[3,2-d]pyrazinyl, 1-Dibenzothiophenyl, 2-Dibenzothiophenyl, 3-Dibenzothiophenyl, 4-Dibenzothiophenyl, 1-Silafluorenyl, 2-Silafluorenyl, 3-Silafluorenyl, 4-Silafluorenyl, 1-Germafluorenyl, 2-Germafluorenyl, 3-Germafluorenyl, 4-Germafluorenyl, 1-Dibenzoselenophenyl, 2-Dibenzoselenophenyl, 3-Dibenzoselenophenyl,It may also be 4-dibenzoselenophenyl, etc. In this specification, "halogen" includes F, Cl, Br, and I.

[0017] Furthermore, "ortho (o)", "meta (m)", and "para (p)" indicate the substitution positions of all substituents. The ortho position is, for example, a compound with substituents adjacent to each other at positions 1 and 2 of benzene. The meta position is the substitution position immediately following the directly adjacent substitution position, for example, a compound with substituents at positions 1 and 3 of benzene. The para position is the substitution position immediately following the meta position, for example, a compound with substituents at positions 1 and 4 of benzene.

[0018] In this specification, “a ring formed by bonding to adjacent substituents” means a substituted or unsubstituted (3 to 30 member) monocyclic or polycyclic alicyclic, aromatic ring, or a combination thereof, formed by linking or fusing two or more adjacent substituents, and preferably a substituted or unsubstituted (3 to 26 member) monocyclic or polycyclic alicyclic, aromatic ring, or a 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, and according to another embodiment of this disclosure, the number of atoms in the ring skeleton is 5 to 15. In one embodiment, the condensed ring may be, for example, a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted benzene ring, a substituted or unsubstituted carbazole ring, a substituted or unsubstituted benzocarbazole ring, and the like.

[0019] Furthermore, in the expression "substituted or unsubstituted," "substituted" means that a hydrogen atom in a functional group is replaced by another atom or functional group, i.e., a substituent, and that the substitution is by a group in which two or more substituents are bonded to each other. For example, a "substituent in which two or more substituents are bonded" may be a pyridine-triazine. That is, a pyridine-triazine may be a heteroaryl group, or it may be interpreted as a single substituent in which two heteroaryl groups are bonded.Preferably, the formulas of the present disclosure include substituted (C1-C30) alkyl, substituted (C2-C30) alkenyl, substituted (C2-C30) alkynyl, substituted (C3-C30) cycloalkyl, substituted (C6-C30) aryl(ene), substituted (3-30 member) heteroaryl, substituted tri(C1-C30) alkylsilyl, substituted tri(C6-C30) arylsilyl, substituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted mono- or di-(C1-C30) alkylamino, and The substituents of the substituted mono- or di-(C6-C30)arylamino are, independently, deuterium, halogen, cyano, carboxyl, nitro, hydroxy, phosphine oxide, (C1-C30) alkyl, halo(C1-C30) alkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C1-C30) alkoxy, (C1-C30) alkylthio, (C3-C30) cycloalkyl, (C3-C30) cycloalkenyl, (3-7 member) heterocycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio, and non- (C6-C30) substituted or (C6-C30) aryl-substituted (5-30 member) heteroaryls, (C6-C30) aryls unsubstituted or (C6-C30) substituted with (5-30 member) heteroaryls, tri(C1-C30) alkylsilyls, tri(C6-C30) arylsilyls, di(C1-C30) alkyl(C6-C30) arylsilyls, (C1-C30) alkyldi(C6-C30) arylsilyls, aminos, mono- or di-(C1-C30) alkylaminos, unsubstituted or (C1-C30) alkyl-substituted mono- or di-(C6-C30) It is at least one selected from the group consisting of arylamino, (C1-C30)alkyl(C6-C30)arylamino, (C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30)arylcarbonyl, (C6-C30)arylphosphinyl, di(C6-C30)arylboronyl, di(C1-C30)alkylboronyl, (C1-C30)alkyl(C6-C30)arylboronyl, (C6-C30)aryl(C1-C30)alkyl, and (C1-C30)alkyl(C6-C30)aryl.More preferably, the substituent may be at least one selected from the group consisting of deuterium, cyano, (C1-C5) alkyl, (C6-C12) aryl, (5-15 member) heteroaryl, and tri(C6-C12) arylsilyl. For example, the substituent may be deuterium, cyano, methyl, tert-butyl, phenyl, biphenyl, naphthyl, unsubstituted or phenyl-substituted pyridyl, carbazolyl, or triphenylsilyl.

[0020] The following describes an organic electroluminescent compound according to one embodiment.

[0021] An organic electroluminescent compound according to one embodiment is represented by the following formula 1. [ka]

[0022] In Equation 1, X represents either O or S; Ar1 and Ar2 independently represent substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted 9,9'-spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted 9-phenylcarbazolyl, substituted or unsubstituted 2-phenylbenzoxazolyl, or substituted or unsubstituted 2-phenylbenzothiazolyl; L1 and L2 independently represent a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted dibenzothiophenylene, a substituted or unsubstituted 9-phenylcarbazolylene, a substituted or unsubstituted 9,9-dimethylfluorenylene, a substituted or unsubstituted 9,9-diphenylfluorenylene, or a substituted or unsubstituted 9,9'-spirobifluorenylene; R1-R4, R', and R'' each independently represent hydrogen or deuterium; a and d each independently represent integers from 1 to 4, b represents an integer from 1 to 3, and c represents an integer of 1; If a, b, and d are integers greater than or equal to 2, then R1, R2, and R4 may be the same or different.

[0023] According to one embodiment, the organic electroluminescent compound represented by formula 1 can be represented by the following formulas 1-1 or 1-2. [ka]

[0024] In equations 1-1 to 1-2, X, Ar1, Ar2, L1, L2, R1~R4, R', R'', a, b, and d are defined as in Equation 1.

[0025] In one embodiment, Ar1 and Ar2 independently represent substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted 9,9'-spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted 9-phenylcarbazolyl, substituted or unsubstituted 2-phenylbenzoxazolyl, or substituted or unsubstituted 2-phenylbenzothiazolyl, preferably substituted or unsubstituted phenyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted m-terphenyl, or substituted or unsubstituted 9,9-dimethylfluorenyl This represents nyl, substituted or unsubstituted 9,9'-spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted 9-phenyl-carbazolyl, more preferably unsubstituted or substituted with one or more elements selected from the group consisting of deuterium, cyano, (C1-C5) alkyl, (C6-C12) aryl, and (5-15 member) heteroaryl, substituted or unsubstituted p-biphenyl, unsubstituted or substituted m-biphenyl with (C6-C12) aryl, substituted or unsubstituted naphthyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9'-spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted 9-phenyl-carbazolyl. For example, Ar1 and Ar2 may each independently be unsubstituted or phenyl substituted with one or more elements selected from the group consisting of cyano, tert-butyl, phenyl, naphthyl, and carbazolyl, unsubstituted p-biphenyl, unsubstituted or phenyl-substituted m-biphenyl, unsubstituted naphthyl, unsubstituted m-terphenyl, unsubstituted 9,9-dimethylfluorenyl, unsubstituted 9,9'-spirobifluorenyl, unsubstituted dibenzofuranyl, unsubstituted dibenzothiophenyl, or unsubstituted 9-phenyl-carbazolyl.

[0026] In one embodiment, L1 and L2 each independently represent a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted dibenzothiophenylene, a substituted or unsubstituted 9-phenylcarbazolylene, a substituted or unsubstituted 9,9-dimethylfluorenylene, a substituted or unsubstituted 9,9-diphenylfluorenylene, or a substituted or unsubstituted 9,9'-spirobifluorenylene, and preferably, L1 and L2 each independently represent a single bond, a substituted or unsubstituted phenylene, a substituted or L1 and L2 may be unsubstituted p-biphenylene, substituted or unsubstituted m-biphenylene, substituted or unsubstituted o-biphenylene, substituted or unsubstituted naphthylene, or substituted or unsubstituted dibenzofuranylene, more preferably a single bond, unsubstituted or substituted with one or more elements selected from the group consisting of deuterium, cyano, (C1-C5)alkyl, (C6-C12)aryl, and (5-15 member) heteroaryl, phenylene, substituted or unsubstituted p-biphenylene, substituted or unsubstituted m-biphenylene, substituted or unsubstituted o-biphenylene, substituted or unsubstituted naphthylene, or substituted or unsubstituted dibenzofuranylene. For example, L1 and L2 may each independently be a single bond, or an unsubstituted or phenyl-substituted phenylene, unsubstituted p-biphenylene, unsubstituted m-biphenylene, unsubstituted o-biphenylene, unsubstituted naphthylene, or unsubstituted dibenzofuranylene.

[0027] According to one embodiment, the organic electroluminescent compound represented by Formula 1 above can be more specifically exemplified by, but is not limited to, the following compounds. [ka] [ka] [ka] [ka] [ka] [ka]

[0028] The compounds of Formula 1 according to this disclosure can be prepared by synthetic methods known to those skilled in the art. For example, they can be prepared as shown by the following reaction scheme 1 or 2.

[0029] [Reaction Scheme 1] [ka]

[0030] [Reaction Scheme 2] [ka]

[0031] In reaction schemes 1 and 2 described above, the definitions of each substituent are as defined in Equation 1.

[0032] As described above, exemplary synthetic examples of compounds represented by Formula 1 in this disclosure are described, which are based on the Ullmann reaction, Miyaura borylation reaction, Suzuki cross-coupling reaction, Buchwald-Hartwig cross-coupling reaction, N-arylation reaction, H-mont-mediated etherification reaction, intramolecular acid-induced cyclization reaction, Pd(II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, cyclic dehydration reaction, SN1 substitution reaction, SN2 substitution reaction, and phosphine-mediated reductive cyclization reaction, etc. It will be understood by those skilled in the art that the above reactions proceed even when other substituents defined in Formula 1 other than those described in the specific synthetic examples are attached.

[0033] According to one embodiment, the present disclosure provides an organic electroluminescent material comprising an organic electroluminescent compound of Formula 1, and an organic electroluminescent device comprising the organic electroluminescent material.

[0034] According to one embodiment of the present disclosure, the organic electroluminescent material of the present disclosure may comprise only the organic electroluminescent compound of Formula 1, or may further comprise conventional materials included in the organic electroluminescent material. Specifically, the organic electroluminescent material of the present disclosure may comprise at least one compound represented by Formula 1 above. For example, the compound of Formula 1 may be included in the light-emitting layer, and if the compound of Formula 1 is included in the light-emitting layer, the compound of Formula 1 may be included as a host, more specifically as a phosphorescent green host.

[0035] According to another embodiment of the present disclosure, the organic electroluminescent material of the present disclosure may further include an organic electroluminescent compound different from the organic electroluminescent compound of formula 1 (first host material) as a second host material. That is, the organic electroluminescent material according to one embodiment of the present disclosure may include a plurality of host materials. Specifically, the plurality of host materials according to one embodiment may include at least one compound of formula 1 as the first host material, and may include at least one second host material different from the first host material. The weight ratio between the first host material and the second host material is 1:99 to 99:1, preferably 10:90 to 90:10, and more preferably 30:70 to 70:30.

[0036] A second host material according to one embodiment comprises a compound represented by the following formula 11. [ka]

[0037] In Equation 11, A1 and A2 each independently represent a substituted or unsubstituted (C6-C30) aryl; L 23 , 11 , 26 , 14 , represents a single bond or a substituted or unsubstituted (C6-C30) arylene; X’, X”, X 11 ~X 14 and X 23 ~X 26 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, or substituted or unsubstituted mono- or di-(C6-C30) arylamino, or adjacent substituents may be linked to each other to form a ring; m and n each independently represent an integer from 1 to 3; When m and n are integers of 2 or more, each of X’ and X” may be the same or different.

[0038] The second host material represented by Formula 11 according to one embodiment can be represented by any one of Formulas 12 to 14 below.

Chemical formula

[0039] In Formulas 12 to 14, A1, A2, X 11 ~X 14 and X 23 ~X 26 are as defined in Formula 11; X15 ~X 22 These are, independently, the same as those defined by X' in Equation 11.

[0040] In one embodiment, A1 and A2 preferably each independently represent a substituted or unsubstituted (C6-C18) aryl, and more preferably each independently represent an unsubstituted (C6-C18) aryl or a (C6-C18) aryl substituted with one or more selected from the group consisting of (C1-C6) alkyl, (C6-C18) aryl, (5-20 member) heteroaryl, and tri(C6-C12) arylsilyl. Specifically, A1 and A2 may each be independently unsubstituted or phenyl substituted with one or more selected from the group consisting of methyl, phenyl, naphthyl, triphenylsilyl, and unsubstituted or phenyl-substituted pyridyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, unsubstituted or substituted fluorenyl with at least one of methyl and phenyl, unsubstituted or substituted benzofluorenyl with at least one of methyl and phenyl, substituted or unsubstituted phenantrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted indenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted tetracenyl, substituted or unsubstituted perilennyl, substituted or unsubstituted crisenyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted naphthylphenyl, or substituted or unsubstituted fluoranthenyl.

[0041] In one embodiment, L 11 This preferably represents a single bond, or a substituted or unsubstituted (C6-C18) arylene, more preferably a single bond, or an unsubstituted (C6-C18) arylene. Specifically, L 11 This may be a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted biphenylene.

[0042] In one embodiment, X 11 ~X 26Preferably, each atom independently represents hydrogen or a substituted or unsubstituted (5-20 membered) heteroaryl ring, or adjacent substituents may be linked to each other to form a substituted or unsubstituted (C6-C12) monocyclic or polycyclic aliphatic or aromatic ring, and more preferably, each atom independently represents hydrogen or an unsubstituted (5-20 membered) heteroaryl ring, or adjacent substituents may be linked to each other to form an unsubstituted (C6-C12) monocyclic or polycyclic aromatic ring. Specifically, X 11 ~X 26 Each of these independently represents hydrogen, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted dibenzofuranyl, or X 11 ~X 14 The adjacent one or X 23 ~X 26 Adjacent elements among them may be linked to each other to form a benzene ring.

[0043] According to one embodiment, the compound represented by formula 11 can be more specifically exemplified by, but is not limited to, the following compounds. [ka] [ka]

[0044] The compounds of formula 11 according to this disclosure can be prepared by synthetic methods known to those skilled in the art.

[0045] The following describes organic electroluminescent devices to which the organic electroluminescent material, which includes the aforementioned organic electroluminescent compound and / or multiple host materials, is applied.

[0046] An organic electroluminescent device according to one embodiment may include a first electrode, a second electrode, and at least one organic layer between the first electrode and the second electrode. The organic layer includes a light-emitting layer. The light-emitting layer may include a plurality of host materials, including at least one first host material represented by formula 1 and at least one second host material represented by formula 11.

[0047] According to one embodiment, the organic electroluminescent material of the present disclosure comprises at least one of compounds H1-1 to H1-144 as a first host material represented by formula 1, and at least one of compounds H2-1 to H2-34 as a second host material represented by formula 11. The multiple host materials may be contained in the same organic layer, such as an emissive layer, or they may be contained in different emissive layers. In addition to the emissive layer, the organic layer may further include at least one layer selected from hole injection layers, hole transport layers, hole auxiliary layers, emissive layer, electron transport layers, electron injection layers, intermediate layers, hole blocking layers, electron blocking layers, and electron buffer layers.

[0048] According to another embodiment, at least one of the organic electroluminescent compounds H1-1 to H1-144 represented by Formula 1 may be included in the electron transport band. For example, the organic electroluminescent compound represented by Formula 1 according to this disclosure may be included in the hole blocking layer.

[0049] The organic layer may further contain amine compounds and / or azine compounds in addition to the light-emitting material of this disclosure. Specifically, the hole injection layer, hole transport layer, hole auxiliary layer, light-emitting layer, light-emitting auxiliary layer, or electron blocking layer may contain amine compounds, such as arylamine compounds and styrylarylamine compounds, as hole injection material, hole transport material, hole auxiliary material, light-emitting material, light-emitting auxiliary material, or electron blocking material. In addition, the electron transport layer, electron injection layer, electron buffer layer, and hole blocking layer may contain azine compounds as electron transport material, electron injection material, electron buffer material, and hole blocking material.

[0050] Furthermore, the organic layer further comprises 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 d-transition elements, or at least one complex compound containing such a metal.

[0051] An organic electroluminescent material according to one embodiment can be used as a light-emitting material for white organic light-emitting devices. Various structures have been proposed for white organic light-emitting 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) light-emitting units. In addition, the organic electroluminescent material according to one embodiment can also be applied to organic electroluminescent devices containing QDs (quantum dots).

[0052] One of the first and second electrodes may be an anode, and the other may be a cathode. Here, the first and second electrodes may be formed as a permeable conductive material, a semi-permeable conductive material, or a reflective conductive material, respectively. The organic electroluminescent device may be top-emission, bottom-emission, or double-sided emission type depending on the type of material forming the first and second electrodes.

[0053] A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof can be used between the anode and the light-emitting layer. The hole injection layer may be multilayered to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or electron blocking layer, where each layer may use two compounds simultaneously. The hole injection layer may also be doped as a p-dopant. An electron blocking layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer to prevent light leakage by confining excitons within the light-emitting layer by preventing electron overflow from the light-emitting layer. The hole transport layer or electron blocking layer may be multilayered, where each layer may use multiple compounds.

[0054] Electron buffer layers, hole blocking layers, electron transport layers, electron injection layers, or combinations thereof can be used between the light-emitting layer and the cathode. The electron buffer layer may be multilayered to control electron injection and improve the interfacial properties between the light-emitting layer and the electron injection layer, where each layer may use two compounds simultaneously. The hole blocking layer can be placed between the electron transport layer (or electron injection layer) and the light-emitting layer, which prevents holes from arriving at the cathode, thereby improving the probability of electron-hole recombination in the light-emitting layer. The hole blocking layer or electron transport layer may also be multilayered, where each layer may use multiple compounds. The electron injection layer may also be doped as an n-type dopant.

[0055] A luminescence auxiliary layer may be placed between the anode and the luminescence layer, or between the cathode and the luminescence layer. When the luminescence auxiliary layer is placed between the anode and the luminescence layer, it can be used to facilitate hole injection and / or hole transport, or to prevent electron overflow. When the luminescence auxiliary layer is placed between the cathode and the luminescence layer, it can be used to facilitate electron injection and / or electron transport, or to prevent hole overflow. In addition, a hole auxiliary layer may be placed between a hole transport layer (or hole injection layer) and the luminescence layer, and can be effective in facilitating or blocking the hole transport rate (or hole injection rate), thereby allowing the charge balance to be controlled. If the organic electroluminescent device includes two or more hole transport layers, any additionally included hole transport layers can be used as hole auxiliary layers or electron blocking layers. Luminescence auxiliary layers, hole auxiliary layers, or electron blocking layers may have the effect of improving the efficiency and / or lifetime of the organic electroluminescent device.

[0056] In the organic electroluminescent device of this disclosure, at least one layer (hereinafter referred to as the "surface layer") preferably selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer may be disposed on the inner surface of one or both electrodes. Specifically, silicon and aluminum chalcogenide (including oxide) layers are preferably disposed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer is preferably disposed on the cathode surface of the electroluminescent medium layer. Operational stability for the organic electroluminescent device can be obtained by the surface layer. Preferably, the chalcogenide is SiO X (1≦X≦2), AlO X Examples of metal halides (1≦X≦1.5) include SiON and SiAlON; examples of metal halides include LiF, MgF2, CaF2, and rare earth metal fluorides; and examples of metal oxides include Cs2O, Li2O, MgO, SrO, BaO, and CaO.

[0057] Furthermore, in the organic electroluminescent device of this disclosure, preferably, a mixed region of an electron transport compound and a reducing dopant or a mixed region of a hole transport compound and an oxidizing dopant may be located on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to anion, thus facilitating the injection and transport of electrons from the mixed region into the electroluminescent medium. Furthermore, the hole transport compound is oxidized to a cation, thus facilitating the injection and transport of 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. An organic electroluminescent device having two or more light-emitting layers and emitting white light can be prepared by using the reducing dopant layer as a charge-generating layer.

[0058] An organic electroluminescent device according to one embodiment may further include at least one dopant in the light-emitting layer.

[0059] The dopants included in the organic electroluminescent devices of this disclosure may be at least one phosphorescent or fluorescent dopant, preferably a phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent devices of this disclosure is not particularly limited, but is preferably a metallized complex compound of a metal atom selected as necessary from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably an orthometallated complex compound of a metal atom selected as necessary from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably an orthometallated iridium complex compound.

[0060] The dopants included in the organic electroluminescent devices of this disclosure may be, but are not limited to, compounds represented by the following formula 101. [ka]

[0061] In Equation 101, L has the following structure 1-3: [ka] Selected from; In structures 1-3, R 100 ~R 103Each of these independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium and / or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (3-30 member) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; or adjacent substituents can bond to each other to form a ring with pyridine, for example, a substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted benzoflopyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzoflopyrinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indenoquinoline ring; R 104 ~R 107 Each of these independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium and / or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; or adjacent substituents can bond to each other to form a ring with benzene, such as a substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzoflopyridine, or substituted or unsubstituted benzothienopyridine ring; R 201 ~R 220 Each of these independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium and / or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C6-C30) aryl; or adjacent substituents can be linked to each other to form a substituted or unsubstituted ring; s represents an integer between 1 and 3.

[0062] In particular, specific examples of dopant compounds include, but are not limited to, the following. [ka] [ka] [ka] [ka] [ka] [ka]

[0063] To form each layer of the organic electroluminescent device of this disclosure, dry deposition methods such as vacuum deposition, sputtering, plasma deposition, and ion plating, or wet deposition methods such as spin coating, dip coating, and flow coating can be used. When using wet deposition methods, thin films can be formed by dissolving or diffusing the material forming each layer in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, or dioxane. Any solvent can be used as long as the material forming each layer can be dissolved or diffused and there are no problems with film formation ability.

[0064] In one embodiment, when a layer is formed by a first host material and a second host material, the layer can be formed by the method described above, and in many cases, by co-evaporation or mixed evaporation. Co-evaporation is a mixed evaporation method in which two or more isomer materials are placed in separate crucible sources and an electric current is passed through both cells simultaneously to evaporate the materials and perform mixed evaporation; mixed evaporation is a mixed evaporation method in which two or more isomer materials are mixed in one crucible source before evaporation, and then an electric current is passed through one cell to evaporate the materials.

[0065] According to one embodiment, when the first host material and the second host material are present in the same or different layers of an organic electroluminescent device, the layers of the two host compounds may be formed separately. For example, the second host material may be deposited after the first host material has been deposited.

[0066] According to one embodiment, the present disclosure can provide a display device comprising a plurality of host materials, including a first host material represented by formula 1 and a second host material represented by formula 11. Furthermore, by using the organic electroluminescent device of the present disclosure, it can be used for the manufacture of display devices such as smartphones, tablets, notebooks, PCs, and TVs, or display devices for automobiles, or lighting devices such as outdoor or indoor lighting.

[0067] In the following sections, in order to understand this disclosure in detail, we will describe the method of preparing compounds according to this disclosure and their properties, referring to the synthesis methods of representative compounds. [Examples]

[0068] [Example 1] Preparation of compound H1-1 [ka] Compound H1-1-1 (4.0 g, 11.99 mmol), compound H1-1-2 (6.05 g, 15.59 mmol), Pd(OAc)2 (0.13 g, 0.59 mmol), S-Phos (0.49 g, 1.19 mmol), NaOt-Bu (2.88 g, 29.99 mmol), and 150 mL of o-xylene were placed in a flask and stirred at 160 °C for 3 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual water was removed, and the mixture was dried over magnesium sulfate. Compound H1-1 was then separated by column chromatography (5.2 g, yield: 67.70%).

[0069] [Table 1]

[0070] [Example 2] Preparation of compound H1-16 [ka] Compound H1-1-1 (4.0 g, 11.99 mmol), compound H1-16-1 (5.6 g, 14.39 mmol), Pd(OAc)2 (0.13 g, 0.59 mmol), S-Phos (0.49 g, 1.19 mmol), NaOt-Bu (2.88 g, 29.99 mmol), and 150 mL of o-xylene were placed in a flask and stirred at 160 °C for 4 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual water was removed, and the mixture was dried over magnesium sulfate. Compound H1-16 was then separated by column chromatography (3.5 g, yield: 45.57%).

[0071] [Table 2]

[0072] [Example 3] Preparation of compound H1-81 [ka] Compound H1-81-1 (3.0 g, 9.0 mmol), compound H1-1-2 (4.2 g, 10.8 mmol), Pd(OAc)2 (0.1 g, 0.45 mmol), S-Phos (0.37 g, 0.9 mmol), NaOt-Bu (1.73 g, 18.0 mmol), and 45 mL of o-xylene were placed in a flask and stirred at 180°C for 4.5 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, and the resulting solid was filtered under reduced pressure by adding methanol. After dissolving the solid in chloroform, the mixture was separated by column chromatography to obtain compound H1-81 (2.3 g, yield: 40.35%).

[0073] [Table 3]

[0074] [Device Examples 1 and 2] Manufacturing of OLEDs containing the compound according to the present disclosure as a host A thin film of indium tin oxide (ITO) (10Ω / sq) (Geomatec Co., Ltd., Japan), which is a transparent electrode on a glass substrate for OLEDs, was sequentially subjected to ultrasonic cleaning with acetone and isopropyl alcohol, then stored in isopropanol, and subsequently used. Next, the ITO substrate was mounted in the substrate holder of a vacuum deposition apparatus. Then, compound HI-1 as the first hole injection compound was introduced into the cell of the vacuum deposition apparatus, and compound HT-1 as the first hole transport compound was introduced into another cell of the vacuum deposition apparatus. The two materials were evaporated at different rates, and the first hole injection compound was deposited with 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 was deposited on the first hole injection layer as a first hole transport layer with a thickness of 80 nm. Next, compound HT-2 was introduced into another cell of the vacuum deposition apparatus and evaporated by passing an electric current through the cell, thereby forming a second hole transport layer with a thickness of 30 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, an emissive layer was formed on top of it as follows: Each of the hosts shown in Table 1 below was introduced as a host into two cells of the vacuum deposition apparatus, and compound D-50 was introduced as a dopant into another cell. The two host materials were evaporated in different ratios of 2:1, and the dopant materials were evaporated simultaneously in different ratios. The dopant was deposited with a doping amount of 10 wt% based on the total amount of host and dopant to form an emissive layer with a thickness of 40 nm on the hole transport layer. Next, compounds ET-1 and EI-1 were deposited as electron transport materials in a weight ratio of 40:60 to form an electron transport layer with a thickness of 35 nm on the emissive layer. After depositing compound EI-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 a separate vacuum deposition apparatus. In this way, an OLED was fabricated. Each compound used in all materials was 10 -6It was purified by vacuum sublimation using a Thor device.

[0075] [Device Example 3] Manufacturing of an OLED containing the compound according to the present disclosure as a host An OLED was fabricated in the same manner as in Device Example 1, except that compound HT-3 was used as the second hole transport material and compound H1-2 was used as the first host for the light-emitting layer.

[0076] [Device Example 4] Manufacturing of an OLED containing the compound according to the present disclosure as a host An OLED was fabricated in the same manner as in Device Example 1, except that compound HT-3 was used as the second hole transport material and compound H1-31 was used as the first host for the light-emitting layer.

[0077] [Comparative Example 1] Production of OLEDs containing a conventional compound as a host The OLED was manufactured in the same manner as in Device Example 1, except that compound C-1 was used as the first host for the light-emitting layer.

[0078] [Comparative Example 2] Production of OLEDs containing a conventional compound as a host An OLED was manufactured using the same method as in Comparative Example 1, except that compound HT-3 was used as the second hole transport material.

[0079] The driving voltage, luminous efficiency, and luminous color at a brightness of 1,000 nits, as well as the time required for the luminescence to decrease from 100% to 95% (lifetime; T95) at a brightness of 20,000 nits, were measured for the organic electroluminescent devices manufactured as described above in Device Examples 1 to 4 and Comparative Examples 1 and 2. The results are shown in Table 1 below.

[0080] [Table 4]

[0081] Table 1 above confirms that the organic electroluminescent device containing the organic electroluminescent compound of this disclosure as a host material not only has excellent luminescence efficiency, but also significantly improves lifetime characteristics compared to conventional organic electroluminescent devices containing host materials.

[0082] Table 2 below shows the compounds used in the above device examples 1 to 4 and comparative examples 1 and 2.

[0083] [Table 5]

[0084] [Table 6]

[0085] [Device Example 5] Production of an OLED containing an organic electroluminescent compound according to the present disclosure An OLED was manufactured using the organic electroluminescent compounds described herein. First, a transparent electrode indium tin (ITO) thin film (10 Ω / sq) (Geomatec Co., Ltd., Japan) on a glass substrate for the OLED was sequentially ultrasonically cleaned with acetone, ethanol, and distilled water, then stored in isopropanol, and subsequently used. Next, the ITO substrate was mounted in the substrate holder of a vacuum deposition apparatus. Compound HT-1 was introduced into the cell of the vacuum deposition apparatus, and compound HI-1 was introduced into another cell of the vacuum deposition apparatus. Next, the pressure in the chamber of the apparatus was set to 10 -6The vacuum was controlled to Thor. Subsequently, the two materials were evaporated, and compound HI-1 was deposited at a doping rate of 3 wt% based on the total amount of compound HT-1 and compound HI-1 to form a 10 nm thick hole injection layer on the ITO substrate. Next, compound HT-1 was introduced into the cell of the vacuum deposition apparatus, and an electric current was passed through the cell to evaporate the introduced material, thereby forming a 75 nm thick first hole transport layer on top of the hole injection layer. Next, compound HT-4 was introduced into another cell of the vacuum deposition apparatus. Subsequently, an electric current was passed through the cell to evaporate the introduced material, thereby forming a 5 nm thick second hole transport layer on top of the first hole transport layer. After forming the hole injection layer and the hole transport layer, an emissive layer was deposited on top of it as follows: Compound BH-1 was introduced as the host into one cell of the vacuum deposition apparatus, and compound BD-1 was introduced as the dopant into the other cell. Simultaneously, the dopant materials were evaporated at different rates. A dopant was doped at a doping rate of 2% by weight relative to the total amount of host and dopant to form a light-emitting layer with a thickness of 20 nm on the second hole transport layer. Next, compound H1-1 was deposited to a thickness of 5 nm as a hole blocking layer. Compounds ET-1 and EI-1 were introduced into two other cells, evaporated and deposited in a ratio of 4:6, respectively, to form an electron transport layer with a thickness of 30 nm on the hole blocking layer. Subsequently, compound EI-1 with a thickness of 2 nm was deposited as an electron injection layer, and an Al cathode with a thickness of 80 nm was deposited using a separate vacuum deposition apparatus. In this way, an OLED was manufactured.

[0086] [Device Example 6] Production of an OLED containing an organic electroluminescent compound according to the present disclosure The OLED was manufactured in the same manner as in Device Example 5, except that compound H1-16 was used as a hole-blocking material.

[0087] [Device Example 7] Production of an OLED containing an organic electroluminescent compound according to the present disclosure The OLED was manufactured in the same manner as in Device Example 5, except that compound H1-81 was used as a hole-blocking material.

[0088] [Comparative Example 3] Manufacturing of OLEDs containing conventional organic electroluminescent compounds The OLED was manufactured in the same manner as in Device Example 5, except that compound C-1 was used as a hole-blocking material.

[0089] The driving voltage, luminous efficiency, and emitted color of the organic electroluminescent devices manufactured as described above, according to Device Examples 5-7 and Comparative Example 3, were measured at a brightness of 1,000 nits. Furthermore, the time required for the emission to decrease from 100% to 95% (lifetime; T95) of the organic electroluminescent devices according to Device Example 7 and Comparative Example 3 at a brightness of 2,500 nits was measured. The results are shown in Tables 3 and 4 below.

[0090] [Table 7]

[0091] Table 3 above confirms that the organic electroluminescent device containing the organic electroluminescent compound of this disclosure as a hole-blocking material has a lower drive voltage and higher luminescence efficiency compared to conventional organic electroluminescent devices containing hole-blocking materials.

[0092] [Table 8]

[0093] From Table 4 above, it can be confirmed that organic electroluminescent devices containing the organic electroluminescent compound of this disclosure as a hole-blocking material exhibit luminescence efficiency equivalent to or higher than that of conventional organic electroluminescent devices containing hole-blocking materials, and in particular, significantly improve lifetime characteristics compared to conventional organic electroluminescent devices containing hole-blocking materials. Furthermore, the organic electroluminescent devices of this disclosure can be used to manufacture long-life blue organic electroluminescent devices, and thus a lifetime balance between organic electroluminescent devices according to this disclosure and red or green organic electroluminescent devices can be maintained.

[0094] Table 5 below shows the compounds used in the above device examples 5 to 7 and comparative example 3.

[0095] [Table 9]

[0096] [Table 10]

Claims

1. The following equation 1: 【Chemistry 1】 (In the formula, X represents O or S; Ar １ and Ar ２ Each of these independently represents a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted 9,9-dimethylfluorenyl, a substituted or unsubstituted 9,9-diphenylfluorenyl, a substituted or unsubstituted 9,9'-spirobifluorenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted 9-phenylcarbazolyl, a substituted or unsubstituted 2-phenylbenzoxazolyl, or a substituted or unsubstituted 2-phenylbenzothiazolyl; L １ and L ２ Each of these independently represents a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted dibenzothiophenylene, a substituted or unsubstituted 9-phenylcarbazolylene, a substituted or unsubstituted 9,9-dimethylfluorenylene, a substituted or unsubstituted 9,9-diphenylfluorenylene, or a substituted or unsubstituted 9,9'-spirobifluorenylene; R １ ~R ４ R' and R'' each independently represent hydrogen or deuterium; a and d each independently represent integers from 1 to 4, b represents an integer from 1 to 3, and c represents an integer of 1; When a, b, and d are integers greater than or equal to 2, R １ , R ２ , and R ４ may be the same or different, respectively) An organic electroluminescent compound represented by, The following compounds: 【Chemistry 2】 Organic electroluminescent compounds, excluding those mentioned above.

2. Equation 1 is the following Equation 1-1 or 1-2: 【Transformation 3】 (In the formula, X, Ar １ Ar ２ , L １ , L ２ , R １ ~R ４ (R', R'', a, b, and d are as defined in claim 1) The organic electroluminescent compound according to claim 1, represented as shown in the image.

3. The Ar １ Ar ２ , L １ , and L ２ The organic electroluminescent compound according to claim 1, wherein each substituent in the substituted substituent represents at least one selected from the group consisting of deuterium, cyano, (C1-C5) alkyl, (C6-C12) aryl, and (5-15 membered) heteroaryl.

4. The Ar １ and Ar ２ However, each is independent of the following group 1: [Group 1] 【Chemistry 4】 【Transformation 5】 The organic electroluminescent compound according to claim 1, wherein one substituent is selected from any of the substituents listed above.

5. The compound represented by formula 1 is the following compound: 【Transformation 6】 【Transformation 7】 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 An organic electroluminescent compound according to claim 1, selected from the above.

6. An organic electroluminescent material comprising the organic electroluminescent compound described in claim 1.

7. A plurality of host materials comprising at least one of the organic electroluminescent materials described in claim 6 as a first host material, and at least one of a second host material different from the first host material.

8. The second host material is given by the following formula 11: 【Chemistry 13】 (In the formula, A １ and A ２ Each of these independently represents a substituted or unsubstituted (C6-C30) aryl; L １１ This represents a single bond, or a substituted or unsubstituted (C6-C30) arylene; X', X'', X １１ ~X １４ , and X ２３ ~X ２６ Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C60) aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted This represents a substituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or adjacent substituents may be linked to each other to form a ring; m and n each represent an integer between 1 and 3 independently; (If m and n are integers greater than or equal to 2, X' and X'' may be the same or different.) A plurality of host materials according to claim 7, comprising a compound represented by [the specified compound].

9. The compound represented by formula 11 is the following compound: 【Chemistry 14】 【Chemistry 15】 A plurality of host materials according to claim 8, selected from the above.

10. An organic electroluminescent device comprising the organic electroluminescent compound described in claim 1.

11. The organic electroluminescent device according to claim 10, wherein the organic electroluminescent compound is included in the light-emitting layer and / or electron transport band.

12. An organic electroluminescent device comprising an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein the at least one light-emitting layer comprises a plurality of host materials as described in claim 7.

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