Plurality of organic electroluminescent materials and organic electroluminescent device comprising the same

Abstract

To provide a plurality of organic electroluminescent materials and an organic electroluminescent device including the same.SOLUTION: The present disclosure relates to a plurality of organic electroluminescent materials comprising at least one first compound and at least one second compound, and an organic electroluminescent device comprising the same. By comprising a specific combination of compounds, in which the first compound is represented by formula 1 and the second compound is represented by formula 2, it is possible to provide an organic electroluminescent device having improved lifespan characteristics.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present disclosure relates to a number of organic electroluminescent materials and organic electroluminescent devices including the same. [Background technology]

[0002] Electroluminescent devices (EL devices) are self-emissive display devices that have the advantages of providing wider viewing angles, greater contrast ratios, and faster response times. The first organic electroluminescent device was developed by Eastman Kodak in 1987 by using small aromatic diamine molecules and aluminum complexes as materials for forming the light-emitting layer. (See Non-Patent Document 1).

[0003] Organic electroluminescent devices (OLEDs) convert electrical energy into light by applying electricity to organic electroluminescent materials and typically include an anode, a cathode, and an organic layer formed between the two electrodes. The organic layers of an OLED may include a hole injection layer, a hole transport layer, an electron blocking layer, an emissive layer, an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. Materials used in the organic layers can be classified according to their functions: hole injection materials, hole transport materials, electron blocking materials, emissive materials, electron buffer materials, hole blocking materials, electron transport materials, electron injection materials, etc. In OLEDs, holes from the anode and electrons from the cathode are injected into the emissive layer by applying a voltage, and high-energy excitons are generated by the recombination of the holes and electrons. Organic light-emitting compounds transition to an excited state using the energy generated when the organic light-emitting compound returns to its ground state, and emit light from this energy.

[0004] The selection of compounds contained in the hole transport layer, etc., is recognized as a means to improve device properties such as hole transport efficiency to the light-emitting layer, light-emitting efficiency, and lifetime. In addition, the most important factor determining the light-emitting efficiency of an OLED is the light-emitting material. The light-emitting material must have high quantum efficiency and high electron and hole mobility, and the formed light-emitting layer must be uniform and stable. Light-emitting materials can be classified into blue, green, and red light-emitting materials depending on the emission color, and may also include yellow or orange light-emitting materials. Light-emitting materials can be used by mixing a host and a dopant to improve color purity, light-emitting efficiency, and stability. Generally, devices with excellent EL properties have a structure that includes an light-emitting layer fabricated by doping a dopant into a host. When using such a dopant / host material system, the selection of the host material is important because it has a significant impact on the efficiency and lifetime of the organic electroluminescent device.

[0005] Patent Document 1 (published January 26, 2017) discloses phenanthrenes substituted with arylamines. In addition, Patent Document 2 (published November 28, 2017) discloses organic electroluminescent devices containing anthracene derivative compounds and boron derivative compounds. However, the aforementioned references do not specifically disclose that the performance of organic electroluminescent devices can be improved by combining phenanthrene derivative compounds with boron derivative compounds. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] US Patent Application Publication No. 2017 / 0025609 A1 [Patent Document 2] Korean Patent Application Publication No. 2017-0130434 A [Patent Document 3] Japanese Patent No. 3915256 [Patent Document 4] Korean Patent No. 0817380 B1 Specification [Patent Document 5] Japanese Patent No. 4377783 [Patent Document 6] Korean Patent Application Publication No. 2017-0080432 A [Patent Document 7] Korean Patent No. 1876763 B1 Specification [Patent Document 8] Japanese Patent No. 5935199 [Non-patent literature]

[0007] [Non-Patent Document 1] Appl.Phys.Lett.51,913,1987 Summary of the Invention [Problem to be solved by the invention]

[0008] It is an object of the present disclosure to provide an organic electroluminescent device having longer life characteristics compared to conventional organic electroluminescent devices by including a specific combination of compounds in the organic layers of the organic electroluminescent device. [Means for solving the problem]

[0009] As a result of inventive research to solve the above technical problems, the present inventors have found that the above object can be achieved by a plurality of organic electroluminescent materials, comprising at least one first compound and at least one second compound, wherein the first compound is represented by the following formula 1, and the second compound is represented by the following formula 2: [ka]

[0010] In Equation 1, R1~R 10are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, or [ka] where R1 to R 10 At least one of [ka] and; L1 represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30-membered) heteroarylene; Ar1 and Ar2 each independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl; or Ar1 and Ar2 may be bonded to each other to form a fused ring; * indicates the point of attachment to the phenanthrene. [ka]

[0011] In Equation 2, Ring A, ring B, and ring C each independently represent a substituted or unsubstituted monocyclic or polycyclic (3 to 50 membered) alicyclic or aromatic ring, or a combination thereof, which may contain at least one heteroatom selected from B, N, O, S, Si, and P; ring B and ring C may be bonded to each other to form a fused ring; Y1 represents B; X1 and X2 each independently represent NR or O; R each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 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 mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C2-C30) alkenylamino, represents a substituted or unsubstituted mono- or di-(C6-C30)arylamino, a substituted or unsubstituted mono- or di-(3-30 membered)heteroarylamino, a substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, a substituted or unsubstituted (C1-C30)alkyl(3-30 membered)heteroarylamino, a substituted or unsubstituted (C2-C30)alkenyl(C6-C30)arylamino, a substituted or unsubstituted (C2-C30)alkenyl(3-30 membered)heteroarylamino, or a substituted or unsubstituted (3-30 membered)heteroaryl(C6-C30)arylamino; or may be bonded to at least one of ring A, ring B, and ring C to form a fused ring.

[0012] Advantageous Effects of the Invention By including a specific combination of compounds according to the present disclosure in an organic layer, it is possible to provide an organic electroluminescent device having a longer life span and / or higher luminous efficiency compared to conventional organic electroluminescent devices, and to use the same to manufacture a display system or a lighting system.In addition, with or alternatively, it is possible to provide an organic electroluminescent device that emits light with a deeper blue color than conventional organic electroluminescent devices. DETAILED DESCRIPTION OF THE INVENTION

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

[0014] The term "organic electroluminescent material" in this disclosure refers to a material that can be used in an organic electroluminescent device and can include at least one compound. The organic electroluminescent material can be included in any layer that constitutes an organic electroluminescent device, as needed. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole auxiliary material, an emitting auxiliary material, an electron blocking material, an emitting material (including a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0015] The term "multiple organic electroluminescent materials" in the present disclosure refers to an organic electroluminescent material containing a combination of at least two compounds that can be included in any layer constituting an organic electroluminescent device. It can refer to both the material before being included in the organic electroluminescent device (e.g., before deposition) and the material after being included in the organic electroluminescent device (e.g., after deposition). Specifically, the multiple organic electroluminescent materials can be a combination of at least two compounds that can be included in at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary 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. For example, the multiple organic electroluminescent materials of the present disclosure can be a combination of at least one dopant material and at least one hole transport material, and can optionally further include conventional materials that are included in organic electroluminescent materials. The at least two compounds can be included in the same layer or different layers by methods used in the art, and can be mixed, evaporated simultaneously, or evaporated separately.

[0016] Hereinafter, the organic electroluminescent devices of the present disclosure will be described in more detail.

[0017] As used herein, the term "(C1-C30) alkyl" refers to a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, preferably 1 to 20, more preferably 1 to 10. Examples of alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and the like. The term "(C2-C30) alkenyl" refers to a linear or branched alkenyl having 2 to 30 carbon atoms constituting the chain, preferably 2 to 20, more preferably 2 to 10. Examples of the alkenyl include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, and the like. The term "(C2-C30)alkynyl" refers to a linear or branched alkynyl having 2 to 30 carbon atoms constituting the chain, preferably 2 to 20, more preferably 2 to 10. The alkynyl may include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, and the like. The term "(C3-C30)cycloalkyl" refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 ring skeletal carbon atoms, preferably 3 to 20, more preferably 3 to 7. The cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like. The term "(3- to 7-membered)heterocycloalkyl" refers to a cycloalkyl having 3 to 7, preferably 5 to 7, skeletal ring atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably O, S, and N. The heterocycloalkyl may include tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, etc. The term "(C6-C30)aryl(ene)" refers to a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 skeletal ring carbon atoms. The aryl(ene) may be partially saturated or may include a spiro structure.The number of ring skeleton carbon atoms is preferably 6 to 25, more preferably 6 to 18. Aryl may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, azulenyl, and the like.More specifically, aryl includes phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, 1-chrysenyl, 2-chrysenyl, 3-chrysenyl, 4-chrysenyl, 5-chrysenyl, 6-chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, fluorenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzofluorenyl, dibenzofluorenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl -4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, p-tert-butylphenyl, p-(2-phenylpropyl) )phenyl, 4'-methylbiphenylyl, 4"-tert-butyl-p-terphenyl-4-yl, 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, and the like.

[0018] The term "(3- to 30-membered)heteroaryl(ene)" refers to an aryl(ene) having 3 to 30 skeletal ring atoms and containing at least one, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, Si, and P. The heteroaryl(ene) may be a monocyclic ring or a fused ring fused with at least one benzene ring; may be partially saturated; may be formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond; or may include a spiro structure. Heteroaryl includes monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and the like, as well as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzimidazolyl, benzothiazolyl, benzo and fused-ring heteroaryls such as diisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, and the like. More specifically, heteroaryl includes 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolizinyl, 2-indolizinyl, 3-indolizinyl, 5-indolizinyl, 6-indolizinyl, 7-indolizinyl, 8-indolizinyl, 2-imidazopyridyl, 3-imidazopyridyl, 5-imidazopyridyl, 6-imidazopyridyl, 7-imidazopyridyl,8-Imidazopyridyl, 3-pyridyl, 4-pyridyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4- Isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazolyl-1-yl, aza Carbazolyl-2-yl, azacarbazolyl-3-yl, azacarbazolyl-4-yl, azacarbazolyl-5-yl, azacarbazolyl-6-yl, azacarbazolyl-7-yl, azacarbazolyl-8-yl, azacarbazolyl-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2-tert-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl,Examples of "halogen" include 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-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-germafluorenyl, 4-germafluorenyl, and the like. "Halogen" includes F, Cl, Br, and I.

[0019] In addition, "ortho (o-)", "meta (m-)", and "para (p-)" are prefixes that respectively indicate the relative positions of substituents. Ortho indicates that two substituents are adjacent to each other; for example, when two substituents in a benzene derivative occupy the 1st and 2nd positions, it is called the ortho position. Meta indicates that two substituents are at the 1st and 3rd positions; for example, when two substituents in a benzene derivative occupy the 1st and 3rd positions, it is called the meta position. Para indicates that two substituents are at the 1st and 4th positions; for example, when two substituents in a benzene derivative occupy the 1st and 4th positions, it is called the para position.

[0020] Additionally, the term "substituted" in the phrase "substituted or unsubstituted" means that a hydrogen atom in a particular functional group has been replaced with another atom or another functional group, ie, a substituent. In the present disclosure, the substituents of substituted alkyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted cycloalkyl, substituted heterocycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted mono- or di-alkylamino, substituted mono- or di-alkenylamino, substituted mono- or di-arylamino, substituted mono- or di-heteroarylamino, substituted alkylalkenylamino, substituted alkylarylamino, substituted alkylheteroarylamino, substituted alkenylarylamino, substituted alkenylheteroarylamino, substituted heteroarylarylamino, and substituted rings are each independently selected from the group consisting of deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, unsubstituted or at least one deuterium-substituted (C1-C30)alkyl, halo(C1-C30)alkyl, (C2-C30)alkenyl, (C2-C3 0)alkynyl; (C1-C30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl; (3-7 membered)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (3-30 membered)heteroaryl substituted with at least one of unsubstituted or deuterium, (C1-C30)alkyl, (C6-C30)aryl, and di(C6-C30)arylamino; unsubstituted or deuterium, (C1 (C6-C30)aryl substituted with at least one of (C6-C30)alkyl, (3-30 membered)heteroaryl, and di(C6-C30)arylamino; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; amino; mono- or di-(C1-C30)alkylamino; mono- or di-(C2-C30)alkenylamino;Mono- or di-(C6-C30)arylamino unsubstituted or substituted with at least one of deuterium, (C1-C30)alkyl, (3-30 membered)heteroaryl, and di(C6-C30)arylamino; mono- or di-(3-30 membered)heteroarylamino; (C1-C30)alkyl(C2-C30)alkenylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkyl(3-30 membered)heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30)alkenyl(3-30 membered)heteroarylamino; non At least one selected from the group consisting of (3-30 membered)heteroaryl(C6-C30)arylamino substituted with or substituted with at least one of (C1-C30)alkyl and (C6-C30)aryl; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl. According to one embodiment of the present disclosure, the substituents are each independently at least one selected from the group consisting of deuterium; unsubstituted or deuterium-substituted (C1-C20) alkyl; (5-25 membered) heteroaryl unsubstituted or substituted with at least one of deuterium, (C1-C20) alkyl, and (C6-C18) aryl; (C6-C25) aryl unsubstituted or substituted with at least one of deuterium, (C1-C20) alkyl, (5-25 membered) heteroaryl, and di(C6-C18) arylamino; mono- or di-(C6-C25) arylamino unsubstituted or substituted with at least one of deuterium, (C1-C20) alkyl, and di(C6-C18) arylamino; and (5-25 membered) heteroaryl(C6-C18) arylamino unsubstituted or substituted with at least one of (C1-C20) alkyl and (C6-C18) aryl. According to another embodiment of the present disclosure, the substituents are each independently selected from the group consisting of deuterium;at least one selected from the group consisting of (C1-C10) alkyl unsubstituted or substituted with at least one deuterium; (5-25 membered) heteroaryl unsubstituted or substituted with at least one of deuterium and (C1-C10) alkyl; (C6-C18) aryl unsubstituted or substituted with at least one of deuterium, (C1-C10) alkyl, (5-20 membered) heteroaryl, and di(C6-C18) arylamino; di(C6-C18) arylamino unsubstituted or substituted with at least one of deuterium, (C1-C10) alkyl, and di(C6-C18) arylamino; and (5-20 membered) heteroaryl(C6-C18) arylamino unsubstituted or substituted with at least one of (C1-C10) alkyl and (C6-C18) aryl. For example, the substituents may each independently be at least one selected from the group consisting of deuterium; unsubstituted or at least one deuterium-substituted methyl; tert-butyl; unsubstituted or at least one substituted phenyl with deuterium, methyl, carbazolyl, dibenzofuranyl, phenoxazinyl, phenothiazinyl, 9,9-dimethyl-dihydroacridinyl, and diphenylamino; naphthyl; biphenyl; terphenyl; triphenylenyl; carbazolyl; phenoxazinyl; phenothiazinyl; 9,9-dimethyl-dihydroacridinyl; unsubstituted or at least one substituted diphenylamino with deuterium, methyl, tert-butyl, and diphenylamino; dinaphthylamino; phenylnaphthylamino; phenylnaphthylamino substituted with tert-butyl; dibiphenylamino; carbazolylphenylamino substituted with phenyl; dibenzofuranylphenylamino; and tetrahydroacridinylphenylamino substituted with at least one methyl.

[0021] In the formula of the present disclosure, when adjacent substituents are bonded to each other to form a ring, the ring may be a substituted or unsubstituted monocyclic or polycyclic (3 to 50-membered) alicyclic ring or aromatic ring, or a combination thereof; preferably a substituted or unsubstituted monocyclic or polycyclic (5 to 40-membered) alicyclic ring or aromatic ring, or a combination thereof; more preferably an unsubstituted monocyclic or polycyclic (5 to 35-membered) aromatic ring. In addition, the formed ring may contain at least one heteroatom selected from N, O, and S. Furthermore, the ring may be a spiro ring formed by a skeletal structure. For example, the ring can be 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 benzoxazine ring, a substituted or unsubstituted benzothiazine ring, a substituted or unsubstituted dihydroquinoline ring, or the like.

[0022] In the formulas of the present disclosure, heteroaryl(ene)s and heterocycloalkyls can each independently contain at least one heteroatom selected from B, N, O, S, Si, and P. In addition, the heteroatom can be selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 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) It can be bonded to at least one selected from the group consisting of arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, and substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino.

[0023] The compounds represented by formula 1 or 2 are described in more detail herein below.

[0024] In formula 1, R1 to R 10 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, or [ka] represents; However, R1~R10 At least one of [ka] and; * indicates the point of attachment to the phenanthrene. According to one embodiment of the present disclosure, R to R 10 are each independently hydrogen, deuterium, a substituted or unsubstituted (C1-C10) alkyl, a substituted or unsubstituted (C6-C25) aryl, a substituted or unsubstituted (5-25 membered) heteroaryl, or [ka] represents; However, R1~R 10 At least one of [ka] is. According to another embodiment of the present disclosure, R to R 10 are each independently hydrogen, deuterium, or [ka] represents; However, R1~R 10 One of the following is [ka] is. For example, R1~R 10 One of the following is [ka] It can be, The others may each independently be hydrogen or deuterium.

[0025] L1 represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene. According to one embodiment of the present disclosure, L1 represents a single bond or a substituted or unsubstituted (C6-C25) arylene. According to another embodiment of the present disclosure, L1 represents a single bond or an unsubstituted (C6-C18) arylene. For example, L1 can be a single bond, phenylene, or naphthylene.

[0026] Ar1 and Ar2 each independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl, or Ar1 and Ar2 may be bonded to each other to form a fused ring. Ar1 and Ar2 may be the same or different. According to one embodiment of the present disclosure, Ar1 and Ar2 each independently represent substituted or unsubstituted (C6-C25) aryl or substituted or unsubstituted (5-25 membered) heteroaryl. According to another embodiment of the present disclosure, Ar1 and Ar2 each independently represent unsubstituted or (C1-C10) alkyl-substituted (C6-C25) aryl, or unsubstituted or (C6-C18) aryl-substituted (5-25 membered) heteroaryl. For example, Ar1 and Ar2 can each independently be phenyl, biphenyl, naphthylphenyl, phenylnaphthyl, terphenyl, dimethylfluorenyl, diphenylfluorenyl, 9,9'-spirobifluorenyl, dibenzothiophenyl, dibenzofuranyl, or carbazolyl substituted with phenyl.

[0027] Equation 1 can be expressed as the following Equation 1-1. [ka]

[0028] In Formula 1-1, L1, Ar1, Ar2, R1 to R4, and R6 to R 10is as defined in Equation 1.

[0029] The compound represented by formula 1 can be at least one selected from the group consisting of the following compounds, but is not limited thereto: [ka] [ka] [ka] [ka] [ka]

[0030] In the above compound, D n represents that n hydrogen atoms are replaced with deuterium atoms, and n represents an integer of 1 or more. The upper limit of n is determined by the number of hydrogen atoms that can be substituted in each compound. According to one embodiment of the present disclosure, each n independently represents an integer of preferably 10 or more, more preferably 15 or more. When deuteration is performed to a number equal to or greater than the lower limit, the bond dissociation energy associated with deuteration may increase, thereby exhibiting improved lifetime characteristics.

[0031] In Formula 2, ring A, ring B, and ring C each independently represent a substituted or unsubstituted monocyclic or polycyclic (3-50 membered) alicyclic ring or aromatic ring, or a combination thereof, which may contain at least one heteroatom selected from B, N, O, S, Si, and P; ring B and ring C may be bonded to each other to form a fused ring. According to one embodiment of the present disclosure, ring A, ring B, and ring C each independently represent a substituted or unsubstituted monocyclic or polycyclic (5-40 membered) alicyclic ring or aromatic ring, or a combination thereof, which may contain at least one heteroatom selected from B, N, O, and S; ring B and ring C may be bonded to each other to form a fused ring. According to another embodiment of the present disclosure, ring A represents a substituted or unsubstituted monocyclic or polycyclic (6-30 membered) aromatic ring; ring B and ring C each independently represent a substituted or unsubstituted monocyclic or polycyclic (6-40 membered) aromatic ring, and the ring may contain at least one heteroatom selected from B, N, O, and S. Rings B and C may be bonded to each other by a single bond or by using -O- as a linker to form a fused ring. For example, ring A may be a substituted or unsubstituted benzene ring, an unsubstituted naphthalene ring, or a (21-membered) heterocycle substituted with methyl. The substituent of the substituted benzene ring may be at least one selected from the group consisting of deuterium, unsubstituted or deuterium-substituted methyl, tert-butyl, unsubstituted or substituted with at least one of deuterium, methyl, and tert-butyl diphenylamino, phenylnaphthylamino, unsubstituted or tert-butyl-substituted phenylbiphenylamino, dinaphthylamino, dibiphenylamino, phenyldibenzofuranylamino, substituted or unsubstituted phenyl, naphthyl, biphenyl, terphenyl, triphenylenyl, carbazolyl, phenoxazinyl, phenothiazinyl, 9,9-dimethyl-dihydroacridinyl, and dimethylxanthenyl. The substituent of the substituted phenyl may be at least one selected from the group consisting of methyl, carbazolyl, dibenzofuranyl, diphenylamino, phenoxazinyl, phenothiazinyl, and 9,9-dimethyl-dihydroacridinyl.For example, ring B and ring C may each independently be a substituted or unsubstituted benzene ring, an unsubstituted naphthalene ring, an unsubstituted dibenzothiophene ring, an unsubstituted dibenzofuran ring, a carbazole ring substituted with at least one of phenyl and diphenylamino, a (21-membered) heterocycle containing B and N and substituted with at least one of methyl and phenyl, a (25-membered) heterocycle containing B and N and substituted with phenyl, or a (36-membered) heterocycle containing B and N and substituted with methyl; the substituent of the substituted benzene ring may be at least one of deuterium, methyl, tert-butyl, phenyl, naphthyl, substituted or unsubstituted diphenylamino, phenylnaphthylamino, dibiphenylamino, dinaphthylamino, phenyldibenzofuranylamino, carbazolylphenylamino substituted with phenyl, and dihydroacridinylphenylamino substituted with methyl; the substituent of the substituted diphenylamino may be at least one of methyl and diphenylamino.

[0032] In formula 2, Y1 represents B; X1 and X2 each independently represent NR or O, where R each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 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 mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C2-C30)alkenylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, substituted or unsubstituted mono- or di-(3-30 membered)heteroarylamino, substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, substituted or unsubstituted (C1-C30)alkyl(3-30 membered)heteroarylamino, substituted or unsubstituted (C2-C30)alkenyl(C6-C30)arylamino, substituted or unsubstituted (C2-C30)alkenyl(3-30 membered)heteroarylamino, or substituted or unsubstituted (3-30 membered)heteroaryl(C6-C30)arylamino; or it may be bonded to at least one of ring A, ring B, and ring C to form a fused ring. According to one embodiment of the present disclosure, each R independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (3-25 membered) heteroaryl; or may combine with at least one of ring A, ring B, and ring C to form a ring.According to another embodiment of the present disclosure, each R independently represents hydrogen, deuterium, unsubstituted (C1-C10) alkyl, (C6-C18) aryl unsubstituted or substituted with at least one of deuterium, (C1-C10) alkyl, and di(C6-C18) arylamino, or (5-20 membered) heteroaryl substituted with (C6-C18) aryl, or may be bonded to at least one of ring A, ring B, and ring C to form a ring. For example, each R independently may be hydrogen, deuterium, unsubstituted phenyl substituted with at least one of deuterium, methyl, and tert-butyl, naphthyl, unsubstituted biphenyl or substituted with diphenylamino, triphenylenyl, or carbazolyl substituted with phenyl, or may be bonded to at least one of ring A, ring B, and ring C via a single bond or O, S, B, or isopropylene as a linker to form a ring.

[0033] According to one embodiment of the present disclosure, Equation 2 can be represented by the following Equation 2-1: [ka]

[0034] In formula 2-1, Y1, X1, and X2 are each independently as defined in formula 2.

[0035] In formula 2-1, R 21 ~R 31are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 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 mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-( or R represents (C2-C30)alkenylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, substituted or unsubstituted mono- or di-(3-30 membered)heteroarylamino, substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, substituted or unsubstituted (C1-C30)alkyl(3-30 membered)heteroarylamino, substituted or unsubstituted (C2-C30)alkenyl(C6-C30)arylamino, substituted or unsubstituted (C2-C30)alkenyl(3-30 membered)heteroarylamino, or substituted or unsubstituted (3-30 membered)heteroaryl(C6-C30)arylamino; or R 21 ~R 31 According to one embodiment of the present disclosure, adjacent ones of R 21 ~R 31 each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C25) aryl, substituted or unsubstituted (5-20 membered) heteroaryl, substituted or unsubstituted mono- or di-(C6-C25) arylamino, or substituted or unsubstituted (5-20 membered) heteroaryl(C6-C25) arylamino; or R 21 ~R 31 According to another embodiment of the present disclosure, adjacent ones of R 21 ~R31 each independently represents hydrogen; deuterium; unsubstituted or deuterium-substituted (C1-C10) alkyl; (C6-C18) aryl unsubstituted or substituted with at least one of deuterium, (C1-C10) alkyl, (13-18 membered) heteroaryl, and di(C6-C18) arylamino; (5-18 membered) heteroaryl unsubstituted or substituted with at least one of deuterium and (C1-C10) alkyl; mono- or di-(C6-C18) arylamino unsubstituted or substituted with at least one of deuterium, (C1-C10) alkyl, di(C6-C18) arylamino, and (13-20 membered) heteroaryl; or (5-20 membered) heteroaryl(C6-C25) arylamino unsubstituted or substituted with at least one of (C1-C10) alkyl and (C6-C18) aryl; or R 21 ~R 31 Adjacent groups may be bonded to each other to form a ring. For example, R 21 ~R 31 are each independently hydrogen; deuterium; unsubstituted or deuterium-substituted methyl; tert-butyl; substituted or unsubstituted phenyl; naphthyl; biphenyl; terphenyl; triphenylenyl; carbazolyl; phenoxazinyl; phenothiazinyl; 9,9-dimethyl-dihydroacridinyl; dimethylxanthenyl; diphenylamino unsubstituted or substituted with at least one of deuterium, methyl, tert-butyl, and diphenylamino; phenylnaphthylamino; unsubstituted or tert-butyl-substituted phenylbiphenylamino; dinaphthylamino; dibiphenylamino; phenyl-substituted carbazolylphenylamino; dibenzofuranylphenylamino; methyl-substituted dihydroacridinylphenylamino; or (17-21 membered)heteroaryl substituted with at least one of methyl and phenyl; or R 21 ~R 31Adjacent rings of may be bonded to each other to form a benzene ring, an indole ring substituted with at least one of phenyl and diphenylamino, a benzofuran ring, a benzothiophene ring, a (17-32 membered) heterocycle containing B and N and substituted with at least one of methyl and phenyl. 24 and R 25 can be attached via -O- as a linker. The substituent of the substituted phenyl can be at least one of methyl, carbazolyl, dibenzofuranyl, diphenylamino, phenoxazinyl, phenothiazinyl, and 9,9-dimethyl-dihydroacridinyl.

[0036] The compound represented by formula 2 can be at least one selected from the group consisting of the following compounds, but is not limited thereto: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0037] In the above compounds, D2 to D5 respectively represent that 2 to 5 hydrogen atoms have been replaced with deuterium atoms, for example, D5 represents that 5 hydrogen atoms have been replaced with deuterium atoms.

[0038] The organic electroluminescent materials according to an embodiment of the present disclosure may include a compound represented by Formula 1 of the present disclosure as a hole transporting zone material and a compound represented by Formula 2 of the present disclosure as a dopant material. The hole transporting zone material may be at least one selected from the group consisting of a hole transporting material, a hole injection material, an electron blocking material, and a hole assisting material.

[0039] The compound represented by Formula 1 according to the present disclosure can be prepared by a synthetic method known to those skilled in the art. For example, the compound represented by Formula 1 can be prepared by referring to, but not limited to, Patent Document 3 (registered February 16, 2007), Patent Document 4 (registered March 20, 2008), Patent Document 5 (registered September 18, 2009), Patent Document 1 (published January 26, 2017), and Patent Document 6 (published July 10, 2017).

[0040] The compound represented by formula 2 according to the present disclosure can be prepared by a synthetic method known to those skilled in the art. For example, the compound represented by formula 2 can be prepared by referring to, but not limited to, Patent Document 7 (registered July 11, 2018), Patent Document 8 (registered May 20, 2016), and Patent Document 2 (published November 28, 2017).

[0041] Deuterated compounds of the present disclosure can be prepared in a similar manner by using deuterated precursor raw materials, or more commonly, by treating non-deuterated compounds with a deuterated solvent, i.e., D6-benzene, in the presence of a Lewis acid, e.g., an H / D exchange catalyst, such as aluminum trichloride or ethylaluminum chloride. In addition, the degree of deuteration can be controlled by varying reaction conditions, such as reaction temperature. For example, the number of deuterium atoms in the formulas of the present disclosure can be controlled by adjusting the reaction temperature, time, acid equivalents, etc.

[0042] The organic electroluminescent device according to the present disclosure comprises a first electrode, a second electrode facing the first electrode, and an organic layer between the first electrode and the second electrode. The organic layer comprises at least one layer of a hole transport zone and at least one layer of an emitting layer; the at least one layer of the hole transport zone comprises a compound represented by Formula 1; the at least one layer of the emitting layer comprises at least one dopant compound and at least one host compound; and the at least one dopant compound comprises a compound represented by Formula 2.

[0043] In addition to the light-emitting layer and the hole-transporting layer, the organic layer may further include at least one layer selected from a light-emitting auxiliary layer, an electron-transporting layer, an electron buffer layer, an electron-injecting layer, an intermediate layer, and a hole-blocking layer.

[0044] The hole transport zone of the present disclosure may be composed of one or more layers selected from the group consisting of a hole transport layer, a hole injection layer, an electron blocking layer, and a hole auxiliary layer, and each of these layers may be composed of one or more layers. Preferably, the hole transport zone may include a hole transport layer. Additionally, the hole transport zone may include a hole transport layer and further include at least one of a hole injection layer, an electron blocking layer, and a hole auxiliary layer.

[0045] In this specification, the hole auxiliary layer or the light emitting auxiliary layer is disposed between the hole transport layer and the light emitting layer to control the hole transport rate, and provides the effect of improving the efficiency and lifespan of the organic electroluminescent device.

[0046] According to one embodiment of the present disclosure, the hole transport layer may consist of a single layer and may include a hole transport material including a compound represented by formula 1 of the present disclosure.

[0047] According to another embodiment of the present disclosure, the hole transport zone includes a hole transport layer, which may be composed of two or more layers, and at least one layer of the multilayer may include a hole transport material including the compound represented by Formula 1 of the present disclosure. The hole transport layer or other layer including the compound represented by Formula 1 may include any compound used in conventional hole transport materials. For example, it may include a compound represented by the following Formula 10. [ka]

[0048] In Equation 10, L 11 represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30-membered) heteroarylene; Ar 11 and Ar 12 each independently represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 membered) heteroaryl, or Ar 11 and Ar 12 can form a nitrogen-containing (3- to 30-membered) heteroaryl together with the nitrogen to which they are attached; R 11 ~R 13 each independently represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, -NR 41 R 42 , -SiR 43 R 44 R 45 , -SR 46 , -OR 47 , -COR 48 , or -B(OR 49 )(OR 50 ), or combine with adjacent substituents to form a monocyclic or polycyclic (3 to 30 membered) alicyclic or aromatic ring, or a combination thereof, whose carbon atoms may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur; R 41 ~R50 each independently represent hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl; or combine with adjacent substituents to form a monocyclic or polycyclic (3-30 membered) alicyclic or aromatic ring, or a combination thereof, in which a carbon atom may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur; x represents an integer of 1 to 4, and when x is an integer of 2 or more, R 11 each of which may be the same or different; y represents an integer of 1 to 3, and when y is an integer of 2 or more, R 12 each of which may be the same or different; Heteroaryl(ene) contains at least one heteroatom selected from B, N, O, S, Si, and P; Heterocycloalkyl contains at least one heteroatom selected from O, S, and N.

[0049] The compound represented by formula 2 of the present disclosure can be included in the light-emitting layer. When used in the light-emitting layer, the organic electroluminescent compound represented by formula 2 of the present disclosure can be included as a dopant material. Preferably, the light-emitting layer can further include one or more host materials.

[0050] The host material can be any known host, preferably any known phosphorescent host, but more preferably one selected from Formula 11 below: [ka]

[0051] In Equation 11, L 11 and L 12 each independently represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30-membered) heteroarylene; Ar 11 and Ar 12 each independently represents a substituted or unsubstituted (C6 to C30) aryl or a substituted or unsubstituted (3 to 30-membered) heteroaryl; R 21 ~R 28 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 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 mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di- -(C2-C30)alkenylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, substituted or unsubstituted mono- or di-(3-30 membered)heteroarylamino, substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, substituted or unsubstituted (C1-C30)alkyl(3-30 membered)heteroarylamino, substituted or unsubstituted (C2-C30)alkenyl(C6-C30)arylamino, substituted or unsubstituted (C2-C30)alkenyl(3-30 membered)heteroarylamino, or substituted or unsubstituted (3-30 membered)heteroaryl(C6-C30)arylamino.

[0052] The light-emitting layer is a light-emitting layer containing a host and a dopant, and may be a single layer or a multilayer structure consisting of two or more stacked layers. Here, the host primarily functions to promote the recombination of electrons and holes and to confine excitons in the light-emitting layer, while the dopant primarily functions to allow the excitons obtained by recombination to efficiently emit light. The dopant compound in the light-emitting layer may be doped in an amount of less than 25 wt %, preferably less than 17 wt %, based on the total amount of the host compound and the dopant compound.

[0053] One of the first and second electrodes can be an anode and the other can be a cathode. The second electrode can be a semi-transparent or reflective electrode, and can be top-, bottom-, or dual-emitting, depending on the material.

[0054] The organic layer may further contain an amine-based compound and / or an azine-based compound in addition to the light-emitting material of the present disclosure. Specifically, the hole injection layer, hole transport layer, hole auxiliary layer, light-emitting layer, light-emitting auxiliary layer, and / or electron blocking layer may contain an amine-based compound, such as an arylamine-based compound or a styrylarylamine-based compound, as the hole injection material, hole transport material, hole auxiliary material, light-emitting material, light-emitting auxiliary material, and / or electron blocking material. In addition, the electron transport layer, electron injection layer, electron buffer layer, and / or hole blocking layer may contain an azine-based compound as the electron transport material, electron injection material, electron buffer material, and / or hole blocking material.

[0055] Additionally, the organic layer may further comprise at least one metal selected from the group consisting of metals from Group 1, metals from Group 2, metals from Periodic Table transition period 4, metals from Period 5, organometallics of the lanthanides and d-transition elements, or at least one complex compound containing said metals.

[0056] A hole injection layer, a hole transport layer, or an electron blocking layer, or a combination thereof, may be used between the anode and the light-emitting layer. The hole injection layer may be a multilayer to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, where each of the multilayers may use two compounds simultaneously. The electron blocking layer may be disposed between the hole transport layer (or hole injection layer) and the light-emitting layer, and may prevent electron overflow from the light-emitting layer and trap excitons in the light-emitting layer to prevent light leakage. The hole transport layer or the electron blocking layer may be a multilayer, where each of the multilayers may use multiple compounds.

[0057] An electron buffer layer, a hole blocking layer, an electron transport layer, or 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 interfacial properties between the light-emitting layer and the electron injection layer, where each layer can use two compounds simultaneously. The hole blocking layer or the electron transport layer can also be multilayered, where each layer can use multiple compounds.

[0058] The light-emitting auxiliary layer can be disposed between the anode and the light-emitting layer or between the cathode and the light-emitting layer. When the light-emitting auxiliary layer is disposed between the anode and the light-emitting layer, it can be used to promote hole injection and / or hole transport or to prevent electron overflow. When the light-emitting auxiliary layer is disposed between the cathode and the light-emitting layer, it can be used to promote electron injection and / or electron transport or to prevent hole overflow.

[0059] In addition, a hole-assisting layer may be disposed between the hole-transporting layer (or hole-injecting layer) and the light-emitting layer, and may be effective in promoting or blocking the hole transport rate (or hole injection rate), thereby enabling charge balance to be controlled. When an organic electroluminescent device includes two or more hole-transporting layers, the additional hole-transporting layer may be used as a hole-assisting layer or an electron-blocking layer. The light-emitting assisting layer, hole-assisting layer, or electron-blocking layer may have the effect of improving the efficiency and / or life of the organic electroluminescent device.

[0060] In the organic electroluminescent device of the present disclosure, at least one layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter referred to as a "surface layer") may be preferably disposed on the inner surface of one or both electrodes. Specifically, a silicon or aluminum chalcogenide (including oxide) layer is preferably disposed on the anode side of the electroluminescent medium layer, and a metal halide or metal oxide layer is preferably disposed on the cathode side of the electroluminescent medium layer. Such a surface layer may provide operational stability to the organic electroluminescent device. Preferably, the chalcogenide includes SiO X (1≦X≦2), AlO X (1≦X≦1.5), SiON, SiAlON, etc.; metal halides include LiF, MgF2, CaF2, rare earth metal fluorides, etc.; metal oxides include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0061] In the organic electroluminescent device of the present disclosure, a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant, is preferably disposed on the surface of at least one of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, thereby making it easier to inject and transport electrons from the mixed region into the electroluminescent medium. Furthermore, the hole transport compound is oxidized to a cation, thereby making it easier to inject and transport holes from the mixed region into the electroluminescent medium. Preferably, the oxidative dopant includes various Lewis acids and acceptor compounds; the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. The reductive dopant layer can be used as a charge generation layer to prepare an organic electroluminescent device having two or more light-emitting layers and emitting white light.

[0062] Various structures have been proposed for white organic electroluminescent devices, such as the arrangement of R (red), G (green) or YG (yellow-green) and B (blue) light-emitting components, or side-by-side structures or stacked structures according to the method of color conversion materials (CCM), etc. The organic electroluminescent materials of the present disclosure can also be applied to such white organic electroluminescent devices.

[0063] The organic electroluminescent materials according to an embodiment of the present disclosure can also be applied to organic electroluminescent devices including QDs (quantum dots).

[0064] In addition, the present disclosure may provide a display system by using a plurality of organic electroluminescent materials according to an embodiment of the present disclosure. That is, a display system or a lighting system can be manufactured by using the compound of the present disclosure. Specifically, a display system, such as a display system for a smartphone, tablet, notebook, PC, TV, or automobile, or a lighting system, such as an outdoor or indoor lighting system, can be manufactured by using the compound of the present disclosure.

[0065] To form each layer of the organic electroluminescent device of the present disclosure, dry film forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film forming methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating and flow coating methods can be used.When using wet film forming methods, thin films can be formed by dissolving or diffusing the materials that form each layer in any suitable solvent, such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.The solvent can be any solvent as long as the materials that form each layer can be dissolved or diffused therein and there is no problem with film forming ability.

[0066] The host and dopant compounds of the present disclosure can be co-evaporated or mixed-evaporated. Co-evaporation is a mixed vapor deposition method in which two or more isomeric materials are placed in their respective crucible sources, and current is passed through both cells at the same time to evaporate the materials. Mixed vapor deposition is a mixed vapor deposition method in which two or more isomeric materials are mixed in one crucible source before evaporating, and current is passed through the cells to evaporate the materials.

[0067] Hereinafter, the preparation methods of the compounds of the present disclosure and their properties will be described in detail with reference to representative compounds of the present disclosure. However, the present disclosure is not limited by the following examples. [Example]

[0068] Example 1: Preparation of Compound C-2 [ka]

[0069] Synthesis of Compound 1-1 15 g of 9-phenanthrenyl-boronic acid (0.068 mol), 28.7 g of 1-bromo-3-iodobenzene (0.10 mol), 3.9 g of Pd(PPh3)4 (0.003 mol), 18.7 g of K2CO3 (0.135 mol), 510 mL of toluene, 65 mL of ethanol, and 65 mL of distilled water were added to a flask, and the mixture was stirred at 100 °C for 5 hours. The reaction mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. Residual water was removed with magnesium sulfate, and the organic layer was dried and separated by column chromatography to obtain 13.9 g of compound 1-1 (yield: 61.7%).

[0070] Synthesis of compound C-2 40.6 g of compound 1-1 (0.122 mol), 53.3 g of N-([1,1'-biphenyl]-4-yl)-[1,1':3',1''-terphenyl]-4-amine (0.134 mol), 1.4 g of Pd(OAc)2 (0.006 mol), 5 g of S-Phos (0.012 mol), 23.4 g of NaOt-Bu (0.244 mmol), and 610 mL of toluene were added to a flask, and the mixture was stirred under reflux at 150 °C for 2 hours. The reaction mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. Residual water was removed with magnesium sulfate, the organic layer was dried, and the extract was separated by column chromatography to obtain 54.7 g of compound C-2 (yield: 69.07%).

[0071] Example 2: Preparation of Compound C-50 [ka] In a flask, 23.0 g of compound C-2 (0.035 mol) was dissolved in 442 mL of benzene-D6, and 18.8 mL of triflic acid (0.212 mol) was added thereto. The mixture was then stirred at room temperature for 23 hours. 400 mL of 2.0 M Na3PO4 aqueous solution was slowly added to the reaction mixture. The organic layer was then extracted with ethyl acetate. Residual water was removed with magnesium sulfate, the organic layer was dried, and the mixture was separated by column chromatography to obtain 17.4 g of compound C-50 (yield: 71.9%).

[0072] Hereinafter, the present disclosure will be described in detail with respect to the preparation method of an organic electroluminescent device (OLED) comprising the compound of the present disclosure and its characteristics. However, the following examples only serve to describe in detail the characteristics of the OLED of the present disclosure, and the present disclosure is not limited to the following examples.

[0073] Device Example 1: Fabrication of an OLED using compounds according to the present disclosure An OLED was fabricated using the organic electroluminescent compound according to the present disclosure as follows: A transparent electrode indium tin oxide (ITO) thin film (10 Ω / sq) (Geomatec Co., Ltd., Japan) on a glass substrate for the OLED was subjected to ultrasonic cleaning in acetone, ethanol, and distilled water, successively, and then stored in isopropanol. -6After evacuating the chamber to 3000 rpm, the ITO substrate was mounted on a substrate holder in a vacuum evaporation system. Compound HT-1 was introduced into one cell of the vacuum evaporation system, and compound HI-1 was introduced into another cell of the vacuum evaporation system. The two materials were evaporated, and compound HI-1 was deposited at a doping amount of 3 wt.% based on the total amount of compounds HI-1 and HT-1 to form a hole injection layer with a thickness of 10 nm on the ITO substrate. Compound HT-1 was then deposited on the hole injection layer to form a first hole transport layer with a thickness of 75 nm. Compound C-2 was then introduced into another cell of the vacuum evaporation system and evaporated by passing a current through the cell, thereby forming a second hole transport layer with a thickness of 5 nm on the first hole transport layer. After forming the hole injection layer and hole transport layer, an emissive layer was formed thereon as follows: compound BH-1 was introduced into one cell of the vacuum evaporation system as the emissive layer host, and compound BD-2 was introduced into another cell as the dopant. The two materials were evaporated, and the dopant was deposited at a doping amount of 2 wt% based on the total amount of the host and dopant to form an emissive layer with a thickness of 20 nm on the second hole-transporting layer. Next, compound ET-1 was evaporated to form a hole-blocking layer with a thickness of 5 nm on the emissive layer. Compounds ET-2 and EI-1 were evaporated in a 1:1 ratio in two other cells to form an electron-transporting layer with a thickness of 30 nm on the hole-blocking layer. Compound EI-1 was then evaporated as an electron-injection layer with a thickness of 2 nm, followed by deposition of an 80 nm Al cathode using a separate vacuum deposition system. In this way, an OLED was fabricated.

[0074] Device Example 2: Fabrication of an OLED Using Compounds According to the Present Disclosure An OLED was fabricated in the same manner as in Device Example 1, except that compound C-50 was used in the second hole transport layer.

[0075] Comparative Example 1: OLED Fabrication Using Conventional Compounds An OLED was fabricated in the same manner as in Device Example 1, except that compound BD-1 was used as the dopant in the emissive layer.

[0076] Table 1 shows the CIE color coordinates, electroluminescence wavelength, and full width at half maximum (FWHM) based on a luminance of 1,000 nits of the OLEDs fabricated in the above device examples and comparative examples, as well as the minimum time required for the luminance to decrease from 100% to 95% (lifetime; T95) based on a luminance of 2,000 nits.

[0077] [Table 1]

[0078] From the above device examples and comparative examples, it can be seen that organic electroluminescent devices containing specific combinations of compounds according to the present disclosure as hole transport materials for the hole transport layer and dopants for the light-emitting layer exhibit a deeper blue light emission than conventional organic electroluminescent devices. Blue-emitting OLEDs can enable a wider range of color expression in display implementations than conventional blue-emitting OLEDs. In addition, it can be seen that organic electroluminescent devices containing multiple organic electroluminescent materials according to the present disclosure exhibit longer lifetime characteristics than organic electroluminescent devices using conventional materials. That is, by including multiple organic electroluminescent materials according to the present disclosure, it is possible to provide a blue OLED with a longer lifetime.

[0079] The compounds used in the device examples and comparative examples are listed below. [ka]

Claims

1. Formula 1 below: 【Chemistry 1】 [In the formula, R １ ~R １０ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, or 【Chemistry 2】 where R １ ~R １０ At least one of 【Transformation 3】 and L １ represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene; Ar １ and Ar ２ each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl, or Ar １ and Ar ２ may be linked to each other to form a fused ring; * indicates the point of attachment to phenanthrene. The organic electroluminescent material is represented by

2. The substituents of the substituted alkyl, the substituted aryl(ene), the substituted heteroaryl(ene), the substituted cycloalkyl, the substituted heterocycloalkyl, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, and the substituted triarylsilyl are each independently selected from the group consisting of deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, unsubstituted or at least one deuterium-substituted (C1-C30)alkyl, halo(C1-C30)alkyl, and (C2-C30)alkane. (C6-C30)arylthio; (3- to 30-membered)heteroaryl unsubstituted or substituted with at least one of deuterium, (C1-C30)alkyl, (C6-C30)aryl, and di(C6-C30)arylamino; (C1-C30)alkyl, (C6-C30)aryl, (C6-C30)aryl, (C6-C30)aryl, (C6-C30)aryl, (C6-C30)aryl, and (C6-C30)arylamino; (C6-C30)aryl, ... (C6-C30)aryl substituted with at least one of (C6-C30) heteroaryl and di(C6-C30)arylamino; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; amino; mono- or di-(C1-C30)alkylamino; mono- or di-(C2-C30)alkenylamino; unsubstituted or deuterium, (C1-C30)alkyl, (3- to 30-membered) Mono- or di-(C6-C30)arylamino substituted with at least one of heteroaryl and di(C6-C30)arylamino; mono- or di-(3- to 30-membered)heteroarylamino; (C1-C30)alkyl(C2-C30)alkenylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkyl(3- to 30-membered)heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30)alkenyl(3- to 30-membered)heteroarylamino;2. The organic electroluminescent material according to claim 1, which is at least one selected from the group consisting of unsubstituted or (3-30 membered)heteroaryl(C6-C30)arylamino substituted with at least one of (C1-C30) alkyl and (C6-C30) aryl; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; di(C6-C30) arylboronyl; di(C1-C30) alkylboronyl; (C1-C30) alkyl(C6-C30) arylboronyl; (C6-C30) aryl(C1-C30) alkyl; and (C1-C30) alkyl(C6-C30) aryl.

3. Formula 1 is the following formula 1-1: 【Chemistry 4】 (In the formula, L １ , Ar １ , Ar ２ , R １ ~R ４ , and R ６ ~R １０ is as defined in claim 1) 2. The organic electroluminescent material according to claim 1, wherein

4. R １ ~R １０ are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C10) alkyl, substituted or unsubstituted (C6-C25) aryl, substituted or unsubstituted (5-25 membered) heteroaryl, or 【Transformation 5】 where R １ ~R １０ At least one of 【Transformation 6】 and 2. The organic electroluminescent material of claim 1, wherein * represents the point of attachment to the phenanthrene.

5. R １ ~R １０ are each independently hydrogen, deuterium, or 【Transformation 7】 where R １ ~R １０ At least one of 【Transformation 8】 and 2. The organic electroluminescent material of claim 1, wherein * represents the point of attachment to the phenanthrene.

6. The compound of formula 1 is the following compound: 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 (In the formula, D ｎ represents that n hydrogen atoms have been replaced with deuterium atoms; n represents an integer of 1 or greater.

2. The organic electroluminescent material according to claim 1, wherein the organic electroluminescent material is at least one selected from:

7. 2. The organic electroluminescent material according to claim 1, wherein the organic electroluminescent material represented by Formula 1 is included as a hole transporting zone material.

8. 10. An organic electroluminescent device comprising a first electrode, a second electrode facing the first electrode, and an organic layer between the first electrode and the second electrode, wherein the organic layer comprises the organic electroluminescent material described in claim 1.

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