Organic electroluminescent device and compound for organic electroluminescent device

Abstract

The present application relates to an organic electroluminescent device, which includes a first electrode, a second electrode, and an emission layer between the first electrode and the second electrode, wherein the emission layer contains a compound represented by the following Formula 1. Embodiments of the present disclosure exhibit improved emission efficiency and long life characteristics. [Formula 1]

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2019-0074027, filed on Jun. 21, 2019, which is hereby incorporated by reference in its entirety. Technical Field

[0003] One or more aspects of the exemplary embodiments of the present disclosure relate to an organic electroluminescent device and a compound used in the organic electroluminescent device, and for example, to a compound used as a light-emitting material and an organic electroluminescent device including the compound. Background Art

[0004] Recently, development of organic electroluminescent display devices as image display devices is being actively carried out. The organic electroluminescent display device is different from the liquid crystal display device in that it is a so-called self-luminous display device in which holes and electrons injected from the first electrode and the second electrode, respectively, are recombined in the emission layer, and the light emitting material including organic compounds in the emission layer emits light to achieve display.

[0005] When an organic electroluminescent device is applied to a display device, a reduced driving voltage, increased luminous efficiency, and a long service life of the organic electroluminescent device are desired. Further development of organic electroluminescent device materials that can stably achieve the requirements is also desired.

[0006] Recent research has focused on phosphorescence emission using triplet energy or delayed fluorescence emission using triplet-triplet annihilation (TTA) in which singlet excitons are generated by collision of triplet excitons, including development of materials for thermally activated delayed fluorescence (TADF) using delayed fluorescence emission. Summary of the invention

[0007] One or more aspects of embodiments of the present disclosure relate to an organic electroluminescent device showing good lifespan characteristics and excellent emission efficiency.

[0008] One or more aspects of embodiments of the present disclosure relate to compounds that are materials for organic electroluminescent devices having high efficiency and long life characteristics.

[0009] One or more exemplary embodiments of the present disclosure provide a compound represented by Formula 1:

[0010] [Formula 1]

[0011]

[0012] In formula 1, M1 and M 2 Each is independently a substituted or unsubstituted hydrocarbon ring having 5 to 30 carbon atoms to form a ring, or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms to form a ring. a R is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted silyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted boryl group, a substituted or unsubstituted phosphino group, a substituted or unsubstituted phosphinooxy group, a substituted or unsubstituted phosphine sulfide group, a substituted or unsubstituted sulfonyl group, or a substituted or unsubstituted sulfinyl group. b is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, or a substituted or unsubstituted amino group, and in some embodiments, R a and / or R b can be optionally (e.g., optionally) with M 1 or M 2 Combine to form a ring. M 1 and M 2 The (eg, one) substituent is a polycyclic hetero group represented by Formula 2:

[0013] [Formula 2]

[0014]

[0015] In Formula 2, X is Si or Ge, and M 3 and M 4 Each is independently a substituted or unsubstituted hydrocarbon ring having 5 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms for forming a ring. L is a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms for forming a ring, and R c and Rd each independently represents a substituted or unsubstituted alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, or a substituted or unsubstituted amino group, or R c and R d Combined with each other to form a substituted or unsubstituted hydrocarbon ring having 5 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms for forming a ring. * indicates a connection site with Formula 1.

[0016] In an embodiment, Formula 1 may be represented by Formula 1-1 or Formula 1-2:

[0017] [Formula 1-1]

[0018]

[0019] [Formula 1-2]

[0020]

[0021] In formula 1-2, Y 1 is B and Y 2 NR a , or Y 1 N and Y 2 For BR b , Z is a direct bond, O, S, C=O, BR e NR f , CR g R h 、SiR i R j ,GeR k R l 、POR m 、PSR n , SO or SO 2 , and R e To R nEach is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring. In Formula 1-1 and Formula 1-2, R 11 To R 18 and R 21 To R 31 Each of the substituents is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted oxy group, or a substituted or unsubstituted thiol group, or combines with an adjacent group to form a condensed ring. 11 To R 18 Any one of them, or by R 11 To R 18 The substituents of the formed fused ring are polycyclic hetero groups represented by Formula 2, R 21 To R 31 Any one of them, or by R 21 To R 31 The substituent of the formed condensed ring is a polycyclic hetero group represented by Formula 2, and R a and R b Same as defined in Formula 1.

[0022] In an embodiment, Formula 2 may be represented by Formula 2-1 or Formula 2-2:

[0023] [Formula 2-1]

[0024]

[0025] [Formula 2-2]

[0026]

[0027] In formula 2-1 and formula 2-2, R 41 To R 48each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted oxy group, or a substituted or unsubstituted thiol group, and L, R c , R d and * are the same as defined in Formula 2.

[0028] In an embodiment, Formula 1-1 may be represented by Formula 1-1A or Formula 1-1B:

[0029] [Formula 1-1A]

[0030]

[0031] [Formula 1-1B]

[0032]

[0033] In formula 1-1B, M 5 is a substituted or unsubstituted hydrocarbon ring having 5 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms for forming a ring, and in Formula 1-1A and Formula 1-1B, R a and R b Same as defined in Formula 1, and X, L, M 3 、M 4 , R c and R d Same as defined in Equation 2.

[0034] In an embodiment, Formula 1-2 may be represented by one selected from Formula 1-2A to Formula 1-2C:

[0035] [Formula 1-2A]

[0036]

[0037] [Formula 1-2B]

[0038]

[0039] [Formula 1-2C]

[0040]

[0041] In formula 1-2C, Q is a direct bond, O, S, C=O, BR g or NR h , R g and R h are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, and in Formulae 1-2A to 1-2C, R a , R b , Y 1 , Y 2 , Z and R 21 To R 31 The same as defined in Formula 1-2.

[0042] In an embodiment, Formula 1-2 may be represented by one selected from Formula 1-2D to Formula 1-2F:

[0043] [Formula 1-2D]

[0044]

[0045] [Formula 1-2E]

[0046]

[0047] [Formula 1-2F]

[0048]

[0049] In formula 1-2F, M 6 is a substituted or unsubstituted hydrocarbon ring having 5 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms for forming a ring, and in Formula 1-2D to Formula 1-2F, R 21 To R 31 , Y 1 , Y 2 and Z are the same as those defined in Formula 1-2, and X, L, M 3 、M 4 , R c and R d Same as defined in Equation 2.

[0050] In the embodiment, M 1 and M 2Each independently may be a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted dibenzothiophene ring.

[0051] In the embodiment, M 3 and M 4 The benzene ring may be substituted or unsubstituted.

[0052] The emission layer is a delayed fluorescence emission layer including a host and a dopant, and the dopant includes the compound represented by Formula 1.

[0053] In an embodiment, the compound represented by Formula 1 may be a material emitting thermally activated delayed fluorescence.

[0054] One or more exemplary embodiments of the present disclosure provide an organic electroluminescent device including a first electrode; a second electrode disposed on the first electrode; and an emission layer disposed between the first electrode and the second electrode, wherein the emission layer includes the compound of the embodiment.

[0055] In an embodiment, the first electrode and the second electrode may each independently comprise: one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, In, Sn and Zn, a compound of two or more selected therefrom, a mixture of two or more selected therefrom, or an oxide thereof.

[0056] In an embodiment, the emitting layer may be designed to emit delayed fluorescence.

[0057] In the embodiment, the emission layer may be a delayed fluorescence emission layer including a host and a dopant, and the dopant may include the compound of the embodiment.

[0058] In an embodiment, the emissive layer may be designed to emit blue light having a central wavelength of about 430 nm to about 490 nm. BRIEF DESCRIPTION OF THE DRAWINGS

[0059] The accompanying drawings are included to provide a further understanding of the present disclosure and are incorporated in and constitute a part of this specification. The accompanying drawings illustrate exemplary embodiments of the present disclosure and together with the description serve to explain the principles of the present disclosure. In the drawings:

[0060] Figure 1 is a cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present disclosure;

[0061] Figure 2is a cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present disclosure;

[0062] Figure 3 is a cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present disclosure; and

[0063] Figure 4 is a cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present disclosure. DETAILED DESCRIPTION

[0064] The present invention may have various modifications and may be implemented in different forms, and the exemplary embodiments will be explained in more detail with reference to the accompanying drawings. However, the present invention may be implemented in different forms and should not be construed as being limited to the embodiments described herein. On the contrary, all modifications, equivalents and substitutions included in the gist and technical scope of the present invention should be included in this disclosure.

[0065] It should also be understood that when an element (or region, layer, component, etc.) is referred to as being "on," "connected to," or "combined with" another element, it can be directly on / connected to / combined with another element, or a third element can be present therebetween. In contrast, when an element is referred to as being "directly on" another element, there are no intervening elements.

[0066] The same reference numerals denote the same elements throughout, and repeated descriptions thereof may not be provided. In the accompanying drawings, the thickness, ratio, and size of elements may be exaggerated to effectively explain technical features.

[0067] The term "and / or" includes one or more than one combinations that can be limited by the relevant elements. Expressions such as "at least one of...", "one of...", "selected from", "at least one of..." and "one of...", when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list.

[0068] It should be understood that although the terms "first", "second", etc. can be used in this article to describe different elements, the elements mentioned are not limited to these terms. These terms are only used to distinguish one element from another element. Therefore, without departing from the teachings of the present invention, the first element can be referred to as the second element. Similarly, the second element can be referred to as the first element. As used herein, the singular form is intended to also include the plural form, unless the context clearly indicates otherwise.

[0069] In addition, the terms "lower", "below", "above", "upper", etc. are used to explain the relationship among the elements shown in the drawings. These terms are relative concepts and will be explained and further interpreted and understood based on the directions indicated in the drawings.

[0070] It should be understood that, unless otherwise defined, the terms (including technical terms and scientific terms) used in this disclosure have the same meanings as those generally understood by those skilled in the art. In addition, the terms defined in commonly used dictionaries should be interpreted as having a meaning consistent with their meaning in the context of the relevant technical concepts, unless otherwise interpreted as having an ideal or overly formal meaning.

[0071] It should also be understood that the terms “comprises” and / or “comprising”, when used in the present specification, specify the presence of the described features, numbers, steps, operations, elements, parts or their combinations, but do not exclude the presence or addition of one or more other features, numbers, steps, operations, elements, parts or their combinations.

[0072] Hereinafter, an organic electroluminescent device according to an embodiment of the present disclosure and a compound according to an embodiment of the present disclosure included therein will be explained with reference to the accompanying drawings.

[0073] Figures 1 to 4 is a cross-sectional view schematically illustrating an organic electroluminescent device according to an exemplary embodiment of the present disclosure. Figures 1 to 4 In the organic electroluminescent device 10 according to the embodiment, the first electrode EL1 and the second electrode EL2 are disposed opposite to each other (eg, face each other), and the emission layer EML is between the first electrode EL1 and the second electrode EL2.

[0074] The organic electroluminescent device 10 according to the embodiment may further include a plurality of functional layers other than the emission layer EML between the first electrode EL1 and the second electrode EL2. The plurality of functional layers may include a hole transport region HTR and an electron transport region ETR. That is, the organic electroluminescent device 10 according to the embodiment may include a first electrode EL1, a hole transport region HTR, an emission layer EML, an electron transport region ETR, and a second electrode EL2 laminated in sequence. In addition, the organic electroluminescent device 10 according to the embodiment may include a capping layer CPL disposed on the second electrode EL2.

[0075] The organic electroluminescent device 10 according to the embodiment may include a compound according to the embodiment (described below) in the emission layer EML disposed between the first electrode EL1 and the second electrode EL2. However, the embodiments of the present disclosure are not limited thereto, and for example, the organic electroluminescent device 10 according to the embodiment may include a compound in a hole transport region HTR and / or in an electron transport region ETR, which are a plurality of functional layers disposed between the first electrode EL1 and the second electrode EL2 other than the emission layer EML. In some embodiments, the compound may be included in a capping layer CPL disposed on the second electrode EL2.

[0076] and Figure 1 compared to, Figure 2 A cross-sectional view of an organic electroluminescent device 10 according to an embodiment is shown, in which a hole transport region HTR includes a hole injection layer HIL and a hole transport layer HTL, and an electron transport region ETR includes an electron injection layer EIL and an electron transport layer ETL. Figure 1 compared to, Figure 3 A cross-sectional view of an embodiment of an organic electroluminescent device 10 is shown, in which a hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL, and an electron blocking layer EBL, and an electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL, and a hole blocking layer HBL. Figure 2 compared to, Figure 4 A cross-sectional view of an organic electroluminescent device 10 according to an embodiment including a cover layer CPL disposed on the second electrode EL2 is shown.

[0077] The first electrode EL1 has conductivity. The first electrode EL1 can be formed using a metal alloy and / or a conductive compound. The first electrode EL1 can be an anode. In some embodiments, the first electrode EL1 can be a pixel electrode. The first electrode EL1 can be a transmissive electrode, a semi-transmissive reflective electrode, or a reflective electrode. When the first electrode EL1 is a transmissive electrode, the first electrode EL1 can include a transparent metal oxide (e.g., indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), and / or indium tin zinc oxide (ITZO)). When the first electrode EL1 is a semi-transmissive reflective electrode or a reflective electrode, the first electrode EL1 can include silver (Ag), magnesium (Mg), copper (Cu), aluminum (Al), platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), neodymium (Nd), iridium (Ir), chromium (Cr), lithium (Li), calcium (Ca), LiF / Ca, LiF / Al, molybdenum (Mo), titanium (Ti), compounds thereof, and / or mixtures thereof (e.g., mixtures of Ag and Mg). In some embodiments, the first electrode EL1 may have a structure including a plurality of layers including, in addition to a transmissive conductive layer formed using ITO, IZO, ZnO, and / or ITZO, a reflective layer or a semi-transmissive reflective layer formed using the above materials. In some embodiments, for example, the first electrode EL1 may include a three-layer structure of ITO / Ag / ITO. However, the embodiments of the present disclosure are not limited thereto. The thickness of the first electrode EL1 may be about 1000 Å. to about For example, about to about

[0078] A hole transport region HTR is provided on the first electrode EL1. The hole transport region HTR may include at least one selected from a hole injection layer HIL, a hole transport layer HTL, a hole buffer layer, and an electron blocking layer EBL. The thickness of the hole transport region HTR may be, for example, about 100 Å. to about

[0079] The hole transport region HTR may be a single layer formed using a single material, a single layer formed using a plurality of different materials, or a multi-layered structure including a plurality of layers formed using a plurality of different materials.

[0080] For example, the hole transport region HTR may have a single-layer structure (e.g., a hole injection layer HIL or a hole transport layer HTL), and in some embodiments, may have a structure of a single layer formed using a hole injection material and a hole transport material (e.g., simultaneously). In some embodiments, the hole transport region HTR may have a structure of a single layer formed using a plurality of different materials, or a structure including a plurality of layers, such as a hole injection layer HIL / hole transport layer HTL, a hole injection layer HIL / hole transport layer HTL / hole buffer layer, a hole injection layer HIL / hole buffer layer, a hole transport layer HTL / hole buffer layer, or a hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL, each of which is laminated on or from the first electrode EL1, without limitation.

[0081] The hole transport region HTR may be formed using any suitable method such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing and / or laser induced thermal imaging (LITI) method.

[0082] The hole injection layer HTL may include, for example, a phthalocyanine compound (e.g., copper phthalocyanine); N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine (DNTPD), 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tris{N-(2-naphthyl)-N-phenylamino}triphenylamine (2-TNATA), poly(3,4-ethylenedioxythiophene) / poly(4-phenylethylenedioxythiophene) / triphenylamine (TDATA). The products include poly(4-styrene sulfonate) (PANI / PSS), polyaniline / dodecylbenzenesulfonate (PANI / DBSA), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine (NPB), triphenylamine-containing polyether ketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium tetrakis(pentafluorophenyl)borate, dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN), etc.

[0083] The hole transport layer HTL may further include, for example, carbazole derivatives (e.g., N-phenylcarbazole and / or polyvinylcarbazole), fluorene-based derivatives, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD), triphenylamine-based derivatives (e.g., 4,4',4"-tri(N-carbazol-9-yl)triphenylamine (TCTA)), N,N'-di(naphthyl)-N,N'-diphenyl-benzidine (NPB), 4,4'-cyclohexylenebis[N,N-bis(4-methylphenyl)]aniline (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), 1,3-bis(N-carbazyl)benzene (mCP), and the like.

[0084] The thickness of the hole transport region HTR may be about to about For example, about to about The thickness of the hole injection layer HIL may be, for example, about to about And the thickness of the hole transport layer HTL may be about to about For example, the thickness of the electron blocking layer EBL may be about to about When the thicknesses of the hole transport region HTR, the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL each satisfy the above-described range, satisfactory hole transport properties may be achieved without a significant increase in driving voltage.

[0085] In addition to the materials described above (e.g., simultaneously with the materials described above), the hole transport region HTR may further include a charge generating material to improve conductivity. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region HTR. The charge generating material may be, for example, a p-dopant. The p-dopant may be selected from quinone derivatives, metal oxides, and compounds containing cyano groups, without limitation. Non-limiting examples of p-dopants may include quinone derivatives (e.g., tetracyanoquinodimethane (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ)) and metal oxides (e.g., tungsten oxide and / or molybdenum oxide), without limitation.

[0086] As described above, in addition to the hole injection layer HIL and the hole transport layer HTL, the hole transport region HTR may further include at least one of a hole buffer layer and an electron blocking layer EBL. The hole buffer layer may compensate for the resonance distance according to the wavelength of light emitted from the emission layer EML and may thereby increase the light emission efficiency. The material contained in the hole transport region HTR may (for example, may also) be used as the material contained in the hole buffer layer. The electron blocking layer EBL may block or reduce the electron injection from the electron transport region ETR to the hole transport region HTR.

[0087] An emission layer EML is provided on the hole transport region HTR. The emission layer EML may have, for example, about to about or about to about The emission layer EML may have a single layer formed using a single material, a single layer formed using a plurality of different materials, or a multilayer structure having a plurality of layers formed using a plurality of different materials.

[0088] In the organic electroluminescent device 10 of the embodiment, the emission layer EML may include the compound according to the embodiment.

[0089] In the description, the term "substituted or unsubstituted" refers to a formula structure that is unsubstituted or substituted by at least one substituent selected from the group consisting of a deuterium atom, a halogen atom, a cyano group, a nitro group, an amino group, a silyl group, an oxy group, a sulfenyl group, a sulfinyl group, a sulfonyl group, a carbonyl group, a boron group, a phosphine oxide group, a phosphine sulfide group, an alkyl group, an alkenyl group, an alkoxy group, a hydrocarbon ring, an aryl group, and a heterocyclic group. In addition, each of the substituents may further be substituted or unsubstituted. For example, a biphenyl group may be interpreted as an aryl group or as a phenyl group substituted by a phenyl group.

[0090] In the description, the term "forming a ring by combining adjacent groups with each other" may refer to forming a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle by combining adjacent groups with each other. The hydrocarbon ring may include an aliphatic hydrocarbon ring and an aromatic hydrocarbon ring. The heterocycle may include an aliphatic heterocycle and an aromatic heterocycle. The ring formed by combining adjacent groups with each other may be a monocyclic ring or a polycyclic ring. In addition, the ring formed by combining adjacent groups may be connected to another ring to form a spiro structure.

[0091] In the description, the term "adjacent groups" may refer to a substituent group at an atom directly connected to a second atom having a corresponding substituent, a substituent group at a (e.g., identical) atom having a corresponding substituent, or a substituent group that is sterically disposed (stereochemically positioned) at the closest position (e.g., within a distance associated with bonding or another intramolecular contact) to the corresponding substituent. For example, the two methyl groups in 1,2-dimethylbenzene may be interpreted as "adjacent groups," and the two ethyl groups in 1,2-diethylcyclopentene may be interpreted as "adjacent groups."

[0092] In the description, non-limiting examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0093] In the description, the term "alkyl group" may refer to a linear, branched or cyclic alkyl group. The carbon number of the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyl decyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, and the like.

[0094] In the description, the term "alkenyl group" may refer to a hydrocarbon group containing one or more carbon-carbon double bonds in the middle or at the end of an alkyl group having 2 or more carbon atoms. The alkenyl group may be straight chain or branched. The carbon number is not particularly limited, and may be, for example, 2 to 30, 2 to 20, or 2 to 10. Non-limiting examples of alkenyl groups may include vinyl groups, 1-butenyl groups, 1-pentenyl groups, 1,3-butadienyl aryl groups, styryl groups, styryl vinyl groups, etc.

[0095] In the description, the term "alkynyl group" may refer to a hydrocarbon group containing one or more carbon-carbon triple bonds in the middle or at the end of an alkyl group having 2 or more carbon atoms. The alkynyl group may be straight chain or branched. The carbon number is not particularly limited, but may be 2 to 30, 2 to 20, or 2 to 10. Non-limiting examples of alkynyl groups include ethynyl groups, propynyl groups, etc.

[0096] In the description, the term "hydrocarbon ring" may refer to a functional group or substituent derived from an aliphatic hydrocarbon ring, or a functional group or substituent derived from an aromatic hydrocarbon ring. The carbon number of the hydrocarbon ring used to form the ring may be 5 to 60, 5 to 30, or 5 to 20.

[0097] In the description, the term "aryl group" refers to a functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group can be a monocyclic aryl group or a polycyclic aryl group. The number of carbon atoms used to form the ring in the aryl group can be 6 to 30, 6 to 20, or 6 to 15. Non-limiting examples of aryl groups include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, pentaphenyl (quinqphenyl), hexaphenyl, triphenylenyl, pyrenyl, benzofluoranthenyl, Ji et al.

[0098] In the description, the term "heterocycle" refers to a functional group or substituent derived from a ring containing one or more heteroatoms selected from boron (B), oxygen (O), nitrogen (N), phosphorus (P), silicon (Si) and sulfur (S). The heterocycle can be an aliphatic heterocycle or an aromatic heterocycle. The aromatic heterocycle can be a heteroaryl group. The aliphatic heterocycle and the aromatic heterocycle can each be monocyclic or polycyclic.

[0099] In the description, the heterocycle may contain one or more heteroatoms selected from B, O, N, P, Si and S. In the case where the heterocycle contains two or more heteroatoms, the two or more heteroatoms may be the same or different. The heterocycle may be a monocyclic heterocycle or a polycyclic heterocycle, and may have the concept of including a heteroaryl group. The carbon number of the heterocycle used to form the ring may be 2 to 30, 2 to 20 or 2 to 10.

[0100] In the description, the aliphatic heterocycle may contain one or more heteroatoms selected from B, O, N, P, Si and S. The carbon number of the aliphatic heterocycle used to form the ring may be 2 to 30, 2 to 20 or 2 to 10. Non-limiting examples of the aliphatic heterocycle include an oxirane group, an oxirane group, a pyrrolidine group, a piperidine group, a tetrahydrofuran group, a tetrahydrothiophene group, a thiolane group, a tetrahydropyran group, a 1,4-dioxane group and the like.

[0101] In the description, the heteroaryl group may contain one or more than one selected from B, O, N, P, Si and S as a heteroatom. If the heteroaryl group includes two or more heteroatoms, the two or more heteroatoms may be the same or different. The heteroaryl group may be a monocyclic heterocycle or a polycyclic heterocycle. The number of carbon atoms in the heteroaryl group for forming the ring may be 2 to 30, 2 to 20 or 2 to 10. Non-limiting examples of heteroaryl groups can include thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, N-arylcarbazolyl, N-heteroarylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothiphenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, dibenzosilolyl, dibenzofuranyl, and the like.

[0102] In the present description, the description of the aryl group may be the same as that of the arylene group, but the arylene group is divalent. The description of the heteroaryl group may be the same as that of the heteroarylene group, but the heteroarylene group is divalent.

[0103] In the description, silyl groups include alkylsilyl groups and arylsilyl groups. Non-limiting examples of silyl groups include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc. However, the embodiments of the present disclosure are not limited thereto.

[0104] In the description, the boryl group includes an alkyl boryl group and an aryl boryl group. Non-limiting examples of the boryl group include a trimethyl boryl group, a triethyl boryl group, a tert-butyl dimethyl boryl group, a triphenyl boryl group, a diphenyl boryl group, a phenyl boryl group, and the like.

[0105] In the description, the carbon number of the amino group is not particularly limited, but can be 1 to 30. The amino group can include an alkylamino group, an arylamino group or a heteroarylamino group. Non-limiting examples of the amino group include a methylamino group, a dimethylamino group, a phenylamino group, a diphenylamino group, a naphthylamino group, a 9-methyl-anthrylamino group, a triphenylamino group, etc.

[0106] In the description, the carbon number of the carbonyl group is not particularly limited, and may be, for example, 1 to 40, 1 to 30, or 1 to 20. For example, the carbonyl group may have the following structure without limitation:

[0107]

[0108] In the description, the carbon number of the sulfinyl group and the sulfonyl group is not particularly limited, and may be, for example, 1 to 30. The sulfinyl group may include an alkylsulfinyl group and an arylsulfinyl group. The sulfonyl group may include an alkylsulfonyl group and an arylsulfonyl group.

[0109] In the description, the thio group may be an alkylthio group or an arylthio group.

[0110] In the description, the oxy group can be an alkoxy group or an aryloxy group. The alkoxy group can be a straight chain, a branched chain or a cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited, and can be, for example, 1 to 20 or 1 to 10. The non-limiting examples of the oxy group include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, benzyloxy etc.

[0111] In the description, the alkyl group in the alkoxy group, alkylthio group, alkylsulfinyl group, alkylsulfonyl group, alkylamino group, alkylboryl group, and alkylsilyl group may be the same as the alkyl group (including examples thereof) described above.

[0112] In the description, the aryl group in the aryloxy group, arylthio group, arylsulfinyl group, arylsulfonyl group, arylamino group, arylboryl group and arylsilyl group may be the same as the aryl group (including examples thereof) described above.

[0113] In the description, a direct bond may mean a single bond.

[0114] At the same time, in the description, Or “—*” refers to the connection position.

[0115] The emission layer EML of the organic electroluminescent device 10 of the embodiment may include a compound represented by Formula 1:

[0116] [Formula 1]

[0117]

[0118] In formula 1, M 1 and M 2 Each may independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 carbon atoms to form a ring, or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms to form a ring.

[0119] In formula 1, R a It may be a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted silyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted boronyl group, a substituted or unsubstituted phosphino group, a substituted or unsubstituted phosphinooxy group, a substituted or unsubstituted phosphine sulfide group, a substituted or unsubstituted sulfonyl group, or a substituted or unsubstituted sulfinyl group.

[0120] In addition, R b It may be a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, or a substituted or unsubstituted amino group.

[0121] R a and R b Can optionally be used with M 1 or M 2 Combine to form a ring. For example, R a and R b Can optionally be used with M 1 or M 2 Combine to form a fused ring.

[0122] In formula 1, M 1 and M 2 Any of the substituents is a polycyclic hetero group represented by Formula 2 (e.g., M 1 and M 2is substituted once or at least once by a polycyclic hetero group represented by Formula 2):

[0123] [Formula 2]

[0124]

[0125] In Formula 2, X is Si or Ge. In Formula 2, M 3 and M 4 Each may independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 carbon atoms to form a ring, or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms to form a ring.

[0126] L may be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms for forming a ring.

[0127] R c and R d Each of them may be independently a substituted or unsubstituted alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, or a substituted or unsubstituted amino group. In some embodiments, R c and R d They may be combined with each other to form a substituted or unsubstituted hydrocarbon ring having 5 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms.

[0128] For example, in the polycyclic heterocyclic group represented by Formula 2, R c and R d It can be an isopropyl group (iPr-*) or a phenyl group (Ph-*, In some embodiments, R c and R d May combine with each other to form a heterocyclic ring having Si as a ring-constituting atom.

[0129] The compound of the embodiment may include: a core part represented by Formula 1 including an azaborane moiety, and an azasilane group or an azagermine group represented by Formula 2 as a substituent of the core part in the form of a polycyclic hetero group. When compared with the case where only the azaborane moiety is included by including a polycyclic hetero group having a heavy atom as a substituent, or the case where it is substituted by a substituent not including a heavy atom, the compound of the embodiment may show excellent life characteristics and improved efficiency properties.

[0130] For example, in the compound of the embodiment represented by Formula 1, M 1 and M 2 Each independently may be a substituted or unsubstituted benzene 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 dibenzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring, a substituted or unsubstituted pyridine ring. However, the embodiments of the present disclosure are not limited thereto.

[0131] For example, in Formula 2, M 3 and M 4 Each independently may be a substituted or unsubstituted benzene 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 dibenzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring, or a substituted or unsubstituted pyridine ring. However, the embodiments of the present disclosure are not limited thereto.

[0132] Formula 1 can be expressed by Formula 1-1 or Formula 1-2:

[0133] [Formula 1-1]

[0134]

[0135] [Formula 1-2]

[0136]

[0137] In formula 1-1, R 11 To R 18Each may independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted oxy group, or a substituted or unsubstituted thiol group, or may combine with an adjacent group to form a condensed ring.

[0138] In formula 1-1, R 11 To R 18 Either or through R 11 To R 18 The substituent of any condensed ring formed by combining with adjacent groups may be a polycyclic hetero group represented by Formula 2.

[0139] In formula 1-1, R a and R b It can be the same as in Formula 1.

[0140] In formula 1-2, Y 1 Can be B and Y 2 Can be NR a , or Y 1 Can be N and Y 2 Can be BR b .

[0141] In formula 1-2, Z can be a direct bond, O, S, C=O, BR e NR f , CR g R h 、SiR i R j ,GeR k R l 、POR m 、PSR n , SO or SO 2 .

[0142] R e To R nEach may independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring.

[0143] In formula 1-2, R 21 To R 31 The substituents may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted oxy group, or a substituted or unsubstituted thiol group, or may combine with an adjacent group to form a condensed ring.

[0144] R 21 To R 31 Either or through R 21 To R 31 The substituent of the condensed ring formed by combining with the adjacent group may be a polycyclic hetero group represented by Formula 2.

[0145] Formula 2 can be expressed by Formula 2-1 or Formula 2-2:

[0146] [Formula 2-1]

[0147]

[0148] [Formula 2-2]

[0149]

[0150] In formula 2-1 and formula 2-2, R 41 To R 48Each of them may independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted oxy group, or a substituted or unsubstituted thiol group.

[0151] In formula 2-1 and formula 2-2, L, R c and R d It can be the same as defined in Formula 2.

[0152] For example, R 41 To R 48 Each of them independently may be a hydrogen atom, an alkyl group or a substituted or unsubstituted phenyl group. L may be a direct bond or a substituted or unsubstituted phenylene group.

[0153] In the compound of the embodiment represented by Formula 1-1, R 11 To R 18 7 of them can be hydrogen atoms, and R 11 To R 18 Any one of may be a polycyclic hetero group represented by the above formula 2. In addition, in formula 1-1, R 11 To R 18 Two adjacent substituents in may be combined with each other to form a condensed ring, and the condensed ring may be substituted with the polycyclic hetero group represented by Formula 2 above.

[0154] Formula 1-1 can be represented by Formula 1-1A or Formula 1-1B:

[0155] [Formula 1-1A]

[0156]

[0157] [Formula 1-1B]

[0158]

[0159] In Formula 1-1A and Formula 1-1B, R a and R b It may be the same as described in Formula 1. In addition, in Formula 1-1A and Formula 1-1B, M 3 、M 4 ,X,R c and R d It can be the same as described in Formula 2.

[0160] In formula 1-1B, M 5 It may be a substituted or unsubstituted hydrocarbon ring having 5 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms.

[0161] For example, in Formula 1-1B, M 5 It may be a substituted or unsubstituted benzene 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 dibenzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring, or a substituted or unsubstituted pyridine ring. However, the embodiments of the present disclosure are not limited thereto.

[0162] The compound of the embodiment represented by Formula 1-2 may be represented by any one selected from Formula 1-2A to Formula 1-2C:

[0163] [Formula 1-2A]

[0164]

[0165] [Formula 1-2B]

[0166]

[0167] [Formula 1-2C]

[0168]

[0169] In Formula 1-2A to Formula 1-2C, Y 1 , Y 2 , Z and R 21 To R 31 It may be the same as described in Formula 1-2.

[0170] In formula 1-2C, Q can be a direct bond, O, S, C=O, BR g or NR h In addition, R g and R h Each may independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring.

[0171] Formula 1-2 may be represented by any one selected from Formula 1-2D to Formula 1-2F:

[0172] [Formula 1-2D]

[0173]

[0174] [Formula 1-2E]

[0175]

[0176] [Formula 1-2F]

[0177]

[0178] In formula 1-2F, M 6 It may be a substituted or unsubstituted hydrocarbon ring having 5 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms.

[0179] For example, in Formula 1-2F, M 6 It may be a substituted or unsubstituted benzene 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 dibenzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring, or a substituted or unsubstituted pyridine ring. However, the embodiments of the present disclosure are not limited thereto.

[0180] In Formula 1-2D to Formula 1-2F, R 21 To R 31 , Y 1 , Y 2 and Z may be the same as described in Formula 1-2. In addition, in Formula 1-2D to Formula 1-2F, X, L, M 3 、M 4 , R c and R d It can be the same as described in Formula 2.

[0181] The compound of the embodiment may be any one selected from the compounds represented in Compound Group 1. The organic electroluminescent device 10 of the embodiment may include at least one compound among the compounds represented in Compound Group 1 in the emission layer EML.

[0182] In compound group 1, i Pr represents an isopropyl group, and Ph represents a phenyl group:

[0183] [Compound Group 1]

[0184]

[0185]

[0186]

[0187]

[0188] The compound of the embodiment may be a material that emits thermally activated delayed fluorescence. The compound of the embodiment may include an electron acceptor represented by Formula 1 and an electron donor represented by Formula 2.

[0189] In the compound of the embodiment, the electron acceptor represented by Formula 1 may include an azaborane moiety having both a boron atom (B) and a nitrogen atom (N) as ring-forming atoms, and may exhibit excellent emission efficiency and long life characteristics.

[0190] In addition, the compound of the embodiment includes the polycyclic hetero group represented by Formula 2 as an electron donor and may exhibit excellent emission efficiency and improved lifespan characteristics.

[0191] The compound of the embodiment may have a difference (ΔE) between the lowest triplet excitation energy level (T1 level) and the lowest singlet excitation energy level (S1 level) of about 0.25 eV or less. ST ) is a thermally activated delayed fluorescent dopant. However, the embodiments of the present disclosure are not limited thereto.

[0192] The compound of the embodiment represented by Formula 1 may have a light emitting center wavelength in a wavelength region of about 490 nm or less. For example, the compound of the embodiment represented by Formula 1 may be a light-emitting material having a light-emitting center wavelength in a wavelength region of about 430 nm to about 490 nm. The compound of the embodiment represented by Formula 1 may be a blue thermally activated delayed fluorescence dopant.

[0193] In the organic electroluminescent device 10 of the embodiment, the emission layer EML may be designed to emit delayed fluorescence. For example, the emission layer EML may be designed to emit thermally activated delayed fluorescence (TADF).

[0194] The organic electroluminescent device 10 of the embodiment may include a plurality of emission layers. The plurality of emission layers may be laminated one by one and provided in the organic electroluminescent device in a prescribed order. For example, the organic electroluminescent device 10 including a plurality of emission layers may be intended to emit white light. The organic electroluminescent device including a plurality of emission layers may be an organic electroluminescent device having a tandem structure. When the organic electroluminescent device 10 includes a plurality of emission layers, at least one emission layer EML may include the compound represented by Formula 1 described above.

[0195] In the embodiment, the emission layer EML includes a host and a dopant, and may include the compound of the embodiment as a dopant. For example, in the organic electroluminescent device 10 of the embodiment, the emission layer EML may include a host that emits delayed fluorescence and a dopant that emits delayed fluorescence, and may include the compound of the embodiment as a dopant that emits delayed fluorescence. The emission layer EML may include at least one of the compounds represented in compound group 1 as a thermally activated delayed fluorescence dopant.

[0196] In an embodiment, the emission layer EML is a delayed fluorescent emission layer, and the emission layer EML may include any suitable host material and the compound of the embodiment described above. For example, in an embodiment, the compound of the embodiment may be used as a TADF dopant.

[0197] In an embodiment, the emission layer EML may include any suitable host material. For example, in an embodiment, the emission layer EML may include tris(8-hydroxyquinolinolato)aluminum (Alq 3 )、4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), poly(N-vinylcarbazole) (PVK), 9,10-di(naphthalene-2-yl)anthracene (ADN), 4,4',4"-tri(carbazol-9-yl)-triphenylamine (TCTA), 1,3,5-tri(N-phenylbenzimidazol-2-yl)benzene (TPBi), 3-tert-butyl-9,10-di(naphthalene-2-yl)anthracene (TBADN) , distyryl arylide (DSA), 4,4'-bis(9-carbazolyl)-2,2"-dimethyl-biphenyl (CDBP), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH2), hexaphenylcyclotrisiloxane (DPSiO 3 ), octaphenylcyclotetrasiloxane (DPSiO 4 ), 2,8-bis(diphenylphosphoryl)dibenzo[b,d]furan (PPF), 3,3'-bis(N-carbazolyl)-1,1'-biphenyl (mCBP), 1,3-bis(N-carbazolyl)benzene (mCP), etc. However, the embodiments of the present disclosure are not limited thereto, and any suitable host material emitting delayed fluorescence may be included in addition to the suggested host material.

[0198] In the organic electroluminescent device 10 of the embodiment, the emission layer EML may further include any suitable dopant material. In the embodiment, the emission layer EML may further include styryl derivatives (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB) and N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalene-2-yl)vinyl)phenyl)-N-phenylaniline (N-BDAVBi)), perylene and its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)), pyrene and its derivatives (e.g., 1,1-dipyrene, 1,4-dipyrenylbenzene and 1,4-bis(N,N-diphenylamino)pyrene), etc. as dopants.

[0199] exist Figures 1 to 3 In the organic electroluminescent device 10 of the exemplary embodiment shown in FIG, an electron transport region ETR is provided on the emission layer EML. The electron transport region ETR may include at least one of a hole blocking layer HBL, an electron transport layer ETL, and an electron injection layer EIL. However, embodiments of the present disclosure are not limited thereto.

[0200] The electron transport region ETR may have a single layer formed using a single material, a single layer formed using a plurality of different materials, or a multi-layered structure having a plurality of layers formed using a plurality of different materials.

[0201] For example, the electron transport region ETR may have a single-layer structure of an electron injection layer EIL or an electron transport layer ETL, or a single-layer structure formed using an electron injection material and an electron transport material. In addition, the electron transport region ETR may have a single-layer structure including a plurality of different materials, or a structure including an electron transport layer ETL / electron injection layer EIL, or a hole blocking layer HBL / electron transport layer ETL / electron injection layer EIL laminated from the emission layer EML, without limitation. The thickness of the electron transport region ETR may be, for example, about 100 Å. to about

[0202] The electron transport region ETR may be formed using any suitable method such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB), inkjet printing, laser printing, and / or laser induced thermal imaging (LITI).

[0203] When the electron transport region ETR includes an electron transport layer ETL, the electron transport layer ETL may include an anthracene-based compound. The electron transport layer ETL may include, for example, tris(8-hydroxyquinolinolato)aluminum (Alq 3)、1,3,5-tri[(3-pyridyl)-phenyl-3-yl]benzene, 2,4,6-tri(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4- triazole (TAZ), 4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (tBu-PBD), bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-biphenyl-4-ato)aluminum (BAlq), bis(benzoquinolin-10-ato)beryllium (Bebq2), 9,10-di(naphthalene-2-yl)anthracene (ADN), 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB), or a mixture thereof without limitation. The thickness of the electron transport layer ETL may be about 1000 nm. to about For example, about to about When the thickness of the electron transport layer ETL satisfies the above-described range, satisfactory electron transport properties may be obtained without a significant increase in driving voltage.

[0204] When the electron transport region ETR includes the electron injection layer EIL, the electron injection layer EIL may include a metal halide such as LiF, NaCl, CsF, RbCl, and RbI, a lanthanide metal such as Yb, or a lanthanide metal such as Li 2 O and BaO metal oxide, or lithium quinoline (LiQ). However, the embodiments of the present disclosure are not limited thereto. A mixture material of an electron injection material and an insulating organic metal salt can also be used to form the electron injection layer EIL. The organic metal salt can be a material having an energy band gap of about 4 eV or greater than 4 eV. For example, the organic metal salt can include, for example, metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate, or metal stearate. The thickness of the electron injection layer EIL can be about to about or about to about When the thickness of the electron injection layer EIL satisfies the above-described range, satisfactory electron injection properties may be obtained without causing a significant increase in driving voltage.

[0205] The electron transport region ETR may include a hole blocking layer HBL as described above. The hole blocking layer HBL may include, for example, at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) and 4,7-diphenyl-1,10-phenanthroline (Bphen). However, embodiments of the present disclosure are not limited thereto.

[0206] A second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 may be a common electrode or a cathode. The second electrode EL2 may be a transmissive electrode, a semi-transmissive reflective electrode or a reflective electrode. When the second electrode EL2 is a transmissive electrode, the second electrode EL2 may include a transparent metal oxide, for example, ITO, IZO, ZnO, ITZO, etc.

[0207] When the second electrode EL2 is a semi-transmissive reflective electrode or a reflective electrode, the second electrode EL2 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, a compound thereof, or a mixture thereof (e.g., a mixture of Ag and Mg). The second electrode EL2 may have a multilayer structure including a reflective layer or a semi-transmissive reflective layer formed using the materials described above and a transparent conductive layer formed using ITO, IZO, ZnO, ITZO, etc.

[0208] In some embodiments, the second electrode EL2 may be connected to an auxiliary electrode. When the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.

[0209] In some embodiments, a capping layer CPL may be further disposed on the second electrode EL2 of the organic electroluminescent device 10 of the embodiment. The capping layer CPL may include, for example, α-NPD, NPB, TPD, m-MTDATA, Alq 3 , CuPc, N4,N4,N4',N4'-tetrakis(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15), 4,4',4"-tris(carbazol-9-yl)triphenylamine (TCTA), N,N'-bis(naphthalene-1-yl), etc.

[0210] The organic electroluminescent device 10 according to the embodiment of the present disclosure may include the compound according to the embodiment in the emission layer EML disposed between the first electrode EL1 and the second electrode EL2, and may show improved life characteristics and excellent emission efficiency. In addition, the compound according to the embodiment may be a thermally activated delayed fluorescence dopant, and the emission layer EML may include the compound of the embodiment to emit thermally activated delayed fluorescence to provide excellent emission efficiency properties in the blue wavelength region.

[0211] The compound of the embodiment may be included in an organic layer other than the emission layer EML as a material for the organic electroluminescent device 10. For example, the organic electroluminescent device 10 according to the embodiment of the present disclosure may include the compound in at least one functional layer disposed between the first electrode EL1 and the second electrode EL2 or a cover layer CPL disposed on the second electrode EL2.

[0212] The compound of the embodiment includes an azaborane moiety containing both N and B as ring-forming heteroatoms, and an azasilane group or an azagermane group substituted on the azaborane moiety and having a heavy atom, and therefore, if used as a material for an organic electroluminescent device, the efficiency and lifespan characteristics of the organic electroluminescent device can be even further improved.

[0213] Hereinafter, the compound according to the embodiment of the present disclosure and the organic electroluminescent device of the embodiment will be explained in more detail by referring to specific embodiments and comparative embodiments.In addition, the following embodiments are only examples to help understanding of the present disclosure, and the scope of the present disclosure is not limited thereto.

[0214] [Example]

[0215] 1. Synthesis of Compounds of Embodiments

[0216] First, the synthesis method of the compound according to the embodiment will be explained by referring to the synthesis methods of Compound 1, Compound 9, Compound 12, Compound 30, Compound 31, Compound 65, and Compound 67. In addition, the synthesis method of the following compound is only an embodiment, and the synthesis method of the compound according to the embodiment of the present disclosure is not limited thereto.

[0217] (1) Synthesis of Compound 1

[0218] Compound 1 according to the embodiment can be synthesized, for example, by reaction 1:

[0219] [Reaction 1]

[0220]

[0221] Synthesis of intermediate compound A

[0222] Under an argon (Ar) atmosphere, 16.9 g (100 mmol) of diphenylamine, 15.2 g (50 mmol) of 1,3-dibromo-2,5-dichlorobenzene, 1.42 g (2.0 mmol) of (Amphos)PdCl 2 and 10.6 g (110 mmol) of NaO tBu was added to a 1,000 mL three-necked flask and stirred at about 100 ° C in 500 mL of toluene solvent for about 2 hours. After cooling in air, water was added, the organic layer was separated, and the solvent was removed by distillation. The crude product thus obtained was separated by column chromatography (silica gel) to obtain 20.46 g (yield 85%) of intermediate compound A in the form of a white solid. The molecular weight of intermediate compound A measured by FAB-MS was 481.

[0223] Synthesis of intermediate compound B

[0224] Under argon atmosphere, 200mL of dehydrated tert-butylbenzene solution of 20.22g (42mmol) of intermediate compound A was added to a 500mL three-necked flask and stirred at about -78°C. 44mL (84mmol) of pentane solution of 1.9M t-BuLi was added dropwise thereto. After completion of the dropwise addition, the temperature was raised to about 60°C and stirred for about 2 hours. Then, components with a lower boiling point than tert-butylbenzene were removed by distillation. The temperature was lowered to about -30°C, and 8.0mL (84mmol) of BBr was added to the flask. 3 Add dropwise thereto. After completion of dropwise addition, the temperature is raised to room temperature and stirred for about 2 hours. Then, the temperature is lowered to about 0 ° C, and 15mL (84mmol) of N, N-diisopropylethylamine is added dropwise. After completion of dropwise addition, the temperature is raised to room temperature and stirred for about 1 hour, and then, the temperature is raised to about 120 ° C and stirred and heated for about 8 hours. The reaction solution is cooled to room temperature, and the NaOAc aqueous solution and toluene cooled in an ice bath are added, and the solution is separated. Then, the solution thus obtained is separated by short column chromatography, and recrystallized by toluene / hexane solvent, to obtain 5.54g (yield 29%) of intermediate compound B in the shape of a yellow solid. The molecular weight of intermediate compound B measured by FAB-MS is 454.

[0225] Synthesis of compound 1

[0226] Under an argon atmosphere, 2.73 g (6.0 mmol) of the intermediate compound B, 2.10 g (6.0 mmol) of 10,10-diphenyl-5,10-dihydrodibenzo[b,e][1,4]azasilane, 0.055 g (0.06 mmol) of Pd 2 (dba) 3 , 0.11 g (0.24 mmol) of Ruphos and 3.82 g (18.0 mmol) of K 2 PO 4Add to a 100 mL three-necked flask and stir in 30 mL of toluene solvent at about 110° C. for about 8 hours. After cooling in air, water is added, the organic layer is separated, and the solvent is removed by distillation. The crude product thus obtained is separated by silica gel column chromatography to obtain 3.32 g (yield 72%) of compound 1 in the form of a yellow solid. The molecular weight of compound 1 measured by FAB-MS is 767. In addition, by 1 H-NMR (CDCl 3 ) measured the δ (chemical shift value) of compound 1 to be [7.71 (2H), 7.50-7.16 (24H), 7.10-6.98 (10H), 6.49 (2H)].

[0227] (2) Synthesis of Compound 9

[0228] Compound 9 according to the embodiment can be synthesized by, for example, reaction 2:

[0229] [Reaction 2]

[0230]

[0231] Synthesis of intermediate compound C

[0232] Under an argon atmosphere, 7.86 g (25 mmol) of 2,3-dichloro-N,N-diphenyl-1,3-aniline, 3.8 mL (27 mmol) of 2,4,6-trimethylaniline, 0.35 g (0.5 mmol) of (Amphos)PdCl 2 and 2.59 g (27 mmol) of NaO t Bu was added to a 200 mL three-necked flask and stirred for about 8 hours in 50 mL of xylene solvent at about 120 ° C. After cooling in air, water was added, the organic layer was separated, and the solvent was removed by distillation. The crude product thus obtained was separated by silica gel column chromatography to obtain 9.09 g (yield 88%) of intermediate compound C in the form of a white solid. The molecular weight of intermediate compound C measured by FAB-MS was 412.

[0233] Synthesis of intermediate compound D

[0234] Under an argon atmosphere, 5.97 g (22 mmol) of intermediate compound C, 2.8 mL (24 mmol) of 1-bromo-3-chlorobenzene, 0.20 g (0.22 mmol) of Pd 2 (dba) 3 , 0.18 g (0.88 mmol) of P t Bu 3 and 2.31 g (24 mmol) of NaO tBu was added to a 200 mL three-necked flask and stirred at about 100 ° C for about 2 hours in 50 mL of toluene solvent. After cooling in air, water was added, the organic layer was separated, and the solvent was removed by distillation. The crude product thus obtained was separated by silica gel column chromatography to obtain 10.6 g (yield 92%) of intermediate compound D in the form of a white solid. The molecular weight of the intermediate compound D measured by FAB-MS was 523.

[0235] Synthesis of intermediate compound E

[0236] Under argon atmosphere, 100mL dehydrated tert-butylbenzene solution of 6.78g (20mmol) of intermediate compound D was added to a 300mL three-necked flask and stirred at about -78°C. 21mL (40mmol) pentane solution of 1.9M t-BuLi was added dropwise thereto. After completion of the dropwise addition, the temperature was raised to about 60°C and stirred for about 2 hours. Then, components with a lower boiling point than tert-butylbenzene were removed by distillation. The temperature was lowered to about -30°C, and 3.8mL (40mmol) of BBr was added. 3 Add dropwise thereto. After completion of dropwise addition, the temperature is raised to room temperature and stirred for about 2 hours. Then, the temperature is lowered to about 0 ° C again, and 7.0 mL (40 mmol) of N, N-diisopropylethylamine is added dropwise thereto. After completion of dropwise addition, the temperature is raised to room temperature and stirred for about 1 hour, and then, the temperature is raised to about 120 ° C and stirred and heated for about 8 hours. The reaction solution is cooled to room temperature, and an aqueous NaOAc solution and toluene cooled in an ice bath are added, and a separation solution is separated. Then, the solution thus obtained is separated by short column chromatography, and recrystallized by toluene / hexane solvent to obtain 3.18 g (yield 32%) of intermediate compound E in the form of a yellow solid. The molecular weight of intermediate compound E measured by FAB-MS is 496.

[0237] Synthesis of compound 9

[0238] Under an argon atmosphere, 3.13 g (6.3 mmol) of the intermediate compound E, 2.30 g (6.3 mmol) of 10,10-diphenyl-5,10-dihydrodibenzo[b,e][1,4]azasilane, and 0.060 g (0.06 mmol) of Pd 2 (dba) 3 , 0.12 g (0.13 mmol) of Ruphos and 4.01 g (18.9 mmol) of K 2 PO 4Add to a 200 mL three-necked flask and stir in 30 mL of toluene solvent at about 110° C. for about 8 hours. After cooling in air, water was added, the organic layer was separated, and the solvent was removed by distillation. The crude product thus obtained was separated by silica gel column chromatography to obtain 3.52 g (yield 69%) of compound 9 in the form of a yellow solid. The molecular weight of compound 9 measured by FAB-MS was 809. In addition, by 1 H-NMR (CDCl 3 ) measured δ (chemical shift values) of compound 9 were [7.73-7.65 (2H), 7.48-7.16 (21H), 7.10-6.98 (6H), 6.86-6.81 (4H), 6.77 (2H), 2.26 (3H), 2.12 (6H)].

[0239] (3) Synthesis of Compound 30

[0240] Compound 30 according to the embodiment can be synthesized by, for example, reaction 3:

[0241] [Reaction 3]

[0242]

[0243] Synthesis of intermediate compound F

[0244] Under an argon atmosphere, 9.86 g (50 mmol) of N-phenyl-3-dibenzothiopheneamine, 10.65 g (25 mmol) of 1,3-dibromo-2,5-dichlorobenzene, 0.71 g (1.0 mmol) of (Amphos)PdCl 2 and 5.29 g (55 mmol) of NaO t Bu was added to a 500 mL three-necked flask and stirred at about 100 ° C for about 2 hours in 250 mL of toluene solvent. After cooling in air, water was added, the organic layer was separated, and the solvent was removed by distillation. The crude product thus obtained was separated by silica gel column chromatography to obtain 16.13 g (yield 93%) of intermediate compound F in the form of a white solid. The molecular weight of the intermediate compound F measured by FAB-MS was 693.

[0245] Synthesis of intermediate compound G

[0246] Under argon atmosphere, 120mL dehydrated tert-butylbenzene solution of 16.0g (23mmol) of intermediate compound F was added to a 300mL three-necked flask and stirred at about -78°C. A pentane solution of 24mL (46mmol) of 1.9M t-BuLi was added dropwise thereto. After completion of the dropwise addition, the temperature was raised to about 60°C and stirred for about 2 hours. Then, components with a lower boiling point than tert-butylbenzene were removed by distillation under reduced pressure. The temperature was lowered to about -30°C, and 4.4mL (46mmol) of BBr was added. 3 Add dropwise thereto. After completion of dropwise addition, the temperature is raised to room temperature and stirred for about 2 hours. Then, the temperature is lowered to about 0 ° C again, and 8.0mL (46mmol) of N, N-diisopropylethylamine is added dropwise thereto. After completion of dropwise addition, the temperature is raised to room temperature and stirred for about 1 hour. Then, the temperature is raised to about 120 ° C and stirred and heated for about 8 hours. The reaction solution is cooled to room temperature, and the NaOAc aqueous solution and toluene cooled in an ice bath are added, and the solution is separated. Then, the solution thus obtained is separated by short column chromatography, and recrystallized by toluene / hexane solvent to obtain 3.38g (yield 22%) of intermediate compound G in the shape of a yellow solid. The molecular weight of intermediate compound G measured by FAB-MS is 667.

[0247] Synthesis of compound 30

[0248] Under an argon atmosphere, 3.34 g (5.0 mmol) of the intermediate compound G, 1.89 g (5.0 mmol) of 10,10-diphenyl-3,6-dimethyl-5,10-dihydrodibenzo[b,e][1,4]azasilane, and 0.055 g (0.05 mmol) of Pd 2 (dba) 3 , 0.093 g (0.20 mmol) of Ruphos and 3.18 g (15.0 mmol) of K 2 PO 4 Add to a 200 mL three-necked flask and stir in 25 mL of toluene solvent at about 110° C. for about 8 hours. After cooling in air, water is added, the organic layer is separated, and the solvent is removed by distillation. The crude product thus obtained is separated by silica gel column chromatography to obtain 2.97 g (yield 59%) of compound 30 in the form of a yellow solid. The molecular weight of compound 30 measured by FAB-MS is 1008. In addition, by 1 H-NMR (CDCl 3) measured the δ value of compound 30 as [8.45 (2H), 7.95-7.85 (4H), 7.77 (2H), 7.58-7.36 (16H), 7.27-7.21 (8H), 7.10-6.98 (6H), 6.49 (2H), 2.36 (2H)].

[0249] (4) Synthesis of Compound 31

[0250] Compound 31 according to the embodiment can be synthesized by, for example, reaction 4:

[0251] [Reaction 4]

[0252]

[0253] Synthesis of intermediate compound H

[0254] Under an argon atmosphere, 8.26 g (30 mmol) of N-phenyl-3-dibenzothiopheneamine, 6.78 g (30 mmol) of 1-bromo-2,3-dichlorobenzene, 0.27 g (0.30 mmol) of Pd 2 (dba) 2 , 0.69 g (1.2 mmol) of Xanphos and 3.17 g (33 mmol) of NaO t Bu was added to a 300 mL three-necked flask and stirred at about 100 ° C for about 2 hours in 150 mL of toluene solvent. After cooling in air, water was added, the organic layer was separated, and the solvent was removed by distillation. The crude product thus obtained was separated by silica gel column chromatography to obtain 11.35 g (yield 90%) of intermediate compound H in the form of a white solid. The molecular weight of the intermediate compound H measured by FAB-MS was 420.

[0255] Synthesis of intermediate compound I

[0256] Under an argon atmosphere, 11.24 g (27 mmol) of intermediate compound H, 4.2 mL (30 mmol) of 2,4,6-trimethylaniline, 0.38 g (0.54 mmol) of (Amphos)PdCl 2 and 2.88 g (30 mmol) of NaO t Bu was added to a 300 mL three-necked flask and stirred for about 8 hours at about 120 ° C in 55 mL of xylene solvent. After cooling in air, water was added, the organic layer was separated, and the solvent was removed by distillation. The crude product thus obtained was separated by silica gel column chromatography to obtain 11.35 g (yield 81%) of intermediate compound I in the form of a white solid. The molecular weight of the intermediate compound I measured by FAB-MS was 519.

[0257] Synthesis of intermediate compound J

[0258] Under an argon atmosphere, 11.0 g (21 mmol) of intermediate compound I, 2.6 mL (22 mmol) of 1-bromo-3-chlorobenzene, 0.19 g (0.21 mmol) of Pd 2 (dba) 3 , 0.17 g (0.84 mmol) of P t Bu 3 and 2.12 g (22 mmol) of NaO t Bu was added to a 300 mL three-necked flask and stirred at about 100 ° C in 85 mL of toluene solvent for about 3 hours. After cooling in air, water was added, the organic layer was separated, and the solvent was removed by distillation. The crude product thus obtained was separated by silica gel column chromatography to obtain 10.31 g (yield 78%) of intermediate compound J in the form of a white solid. The molecular weight of intermediate compound J measured by FAB-MS was 629.

[0259] Synthesis of intermediate compound K

[0260] Under argon atmosphere, 80mL of dehydrated tert-butylbenzene solution of 10.08g (16mmol) of intermediate compound J was added to a 300mL three-necked flask and stirred at about -78°C. 17mL (32mmol) of pentane solution of 1.9M t-BuLi was added dropwise thereto. After completion of the dropwise addition, the temperature was raised to about 60°C and stirred for about 2 hours. Then, components with a lower boiling point than tert-butylbenzene were removed by distillation under reduced pressure. The temperature was lowered to about -30°C, and 3.0mL (32mmol) of BBr was added. 3 Add dropwise thereto. After completion of dropwise addition, the temperature is raised to room temperature and stirred for about 2 hours. Then, the temperature is lowered to about 0 ° C again, and 5.6mL (32mmol) of N, N-diisopropylethylamine is added dropwise thereto. After completion of dropwise addition, the temperature is raised to room temperature and stirred for about 1 hour. Then, the temperature is raised to about 120 ° C and stirred and heated for about 8 hours. The reaction solution is cooled to room temperature, and the NaOAc aqueous solution and toluene cooled in an ice bath are added, and the solution is separated. Then, the solution thus obtained is separated by short column chromatography, and recrystallized by toluene / hexane solvent to obtain 3.76g (yield 39%) of intermediate compound K in the shape of a yellow solid. The molecular weight of intermediate compound K measured by FAB-MS is 602.

[0261] Synthesis of compound 31

[0262] Under an argon atmosphere, 3.74 g (6.2 mmol) of the intermediate compound K, 2.57 g (6.8 mmol) of 10,10-diphenyl-3,6-dimethyl-5,10-dihydrodibenzo[b,e][1,4]azasilane, and 0.060 g (0.06 mmol) of Pd 2 (dba) 3 , 0.12 g (0.13 mmol) of Ruphos and 3.95 g (18.6 mmol) of K 2 PO 4 Add to a 200 mL three-necked flask and stir in 70 mL of toluene solvent at about 110° C. for about 8 hours. After cooling in air, water is added, the organic layer is separated, and the solvent is removed by distillation. The crude product thus obtained is separated by silica gel column chromatography to obtain 3.34 g (yield 57%) of compound 31 in the form of a yellow solid. The molecular weight of compound 31 measured by FAB-MS is 944. In addition, by 1 H-NMR (CDCl 3 ) measured the δ value of compound 31 as [8.45 (1H), 7.93 (1H), 7.87 (1H), 7.77 (1H), 7.67 (1H), 7.58-7.36 (14H), 7.29-7.21 (7H), 7.10-6.98 (3H), 6.86-6.81 (4H), 6.77 (2H), 2.36 (2H), 2.26 (3H), 2.12 (6H)].

[0263] (5) Synthesis of Compound 12

[0264] Compound 12 according to the embodiment can be synthesized by, for example, reaction 5:

[0265] [Reaction 5]

[0266]

[0267] Under an argon atmosphere, 1.36 g (3.0 mmol) of the intermediate compound B, 1.18 g (3.0 mmol) of 10,10-diphenyl-5,10-dihydrodibenzo[b,e][1,4]azasilane, 0.14 g (0.15 mmol) of Pd 2 (dba) 3 , 0.28 g (0.6 mmol) of Ruphos and 1.91 g (9.0 mmol) of K 3 PO 4Add to a 100 mL three-necked flask and stir in 15 mL of toluene solvent at about 80° C. for about 24 hours. After cooling in air, water is added, the organic layer is separated, and the solvent is removed by distillation. The crude product thus obtained is separated by silica gel column chromatography to obtain 1.57 g (yield 75%) of compound 12 in the form of a yellow solid. The molecular weight of compound 12 measured by FAB-MS is 699. In addition, by 1 H-NMR (CDCl 3 ) measured the δ value of compound 12 to be [7.71 (2H), 7.44-7.37 (4H), 7.31-7.16 (10H), 7.10-6.98 (10H), 6.49 (2H), 1.45 (2H), 0.97 (12H)].

[0268] (6) Synthesis of Compound 65

[0269] Compound 65 according to the embodiment can be synthesized by, for example, reaction 6:

[0270] [Reaction 6]

[0271]

[0272] Under an argon atmosphere, 1.36 g (3.0 mmol) of the intermediate compound B, 1.18 g (3.0 mmol) of 10,10-diphenyl-5,10-dihydrodibenzo[b,e][1,4]azagermane, and 0.14 g (0.15 mmol) of Pd 2 (dba) 3 , 0.28 g (0.6 mmol) of Ruphos and 1.91 g (9.0 mmol) of K 3 PO 4 Add to a 100 mL three-necked flask and stir in 15 mL of toluene solvent at about 80° C. for about 24 hours. After cooling in air, water is added, the organic layer is separated, and the solvent is removed by distillation. The crude product thus obtained is separated by silica gel column chromatography to obtain 1.25 g (yield 51%) of compound 65 in the form of a yellow solid. The molecular weight of compound 65 measured by FAB-MS is 812. In addition, by 1 H-NMR (CDCl 3 ) measured the δ value of compound 65 to be [7.71 (2H), 7.38-7.16 (24H), 7.10-6.98 (10H), 6.49 (2H)].

[0273] (7) Synthesis of Compound 67

[0274] Compound 67 according to the embodiment can be synthesized by, for example, reaction 7:

[0275] [Reaction 7]

[0276]

[0277] Under an argon atmosphere, 2.68 g (5.0 mmol) of 3-bromo-5,10-dihydro-5-phenyl-10-[2,4,6-tri(1-methylethyl)phenyl]benzaborane, 1.75 g (5.0 mmol) of 10,10-diphenyl-5,10-dihydrodibenzo[b,e][1,4]azasilane, 0.046 g (0.05 mmol) of Pd 2 (dba) 3 , 0.040 g (0.20 mmol) of P t Bu 3 and 0.48 g (5.0 mmol) of NaO t Bu was added to a 100 mL three-necked flask and stirred at about 100° C. in 25 mL of toluene solvent for about 2 hours. After cooling in air, water was added, the organic layer was separated, and the solvent was removed by distillation. The crude product thus obtained was separated by silica gel column chromatography to obtain 3.10 g (yield 77%) of compound 67 in the form of a yellow solid. The molecular weight of compound 67 measured by FAB-MS was 804. In addition, by 1 H-NMR (CDCl 3 ) measured the δ value of compound 67 [7.73-7.65 (2H), 7.48-7.36 (14H), 7.31-7.16 (8H), 7.10-6.98 (6H), 6.86-6.81 (2H), 2.90-2.85 (3H), 1.22-1.16 (18H)].

[0278] 2. Fabrication and evaluation of organic electroluminescent devices

[0279] 2-1. Example A of organic electroluminescent device

[0280] The organic electroluminescent device of the embodiment containing the compound of the embodiment in the emission layer is manufactured according to the method described below. The organic electroluminescent devices of Examples 1 to 6 are manufactured using Compound 1, Compound 9, Compound 30, Compound 31, Compound 12 and Compound 65 as dopant materials of the emission layer, respectively. The organic electroluminescent devices of Comparative Examples 1 and 2 are manufactured using Comparative Compounds C1 and C2 as dopant materials of the emission layer, respectively.

[0281] The compounds used in Examples 1 to 6 and Comparative Examples 1 and 2 are shown in Table 1:

[0282] [Table 1]

[0283]

[0284] (Manufacturing of Organic Electroluminescent Device A)

[0285] Will be about ITO with a thickness of 1000 nm was patterned on a glass substrate, and then, washed with ultrapure water, cleaned with ultrasonic waves, exposed to UV for about 30 minutes, and then, treated with ozone. Then, HAT-CN was deposited to about The thickness of α-NPD was deposited to about The thickness of the mCP was about to form a hole transport region.

[0286] Then, the exemplary compound or comparative compound was co-deposited with mCBP at a ratio of 1:99 to form a For example, the emission layer is formed by mixing Compound 1, Compound 9, Compound 30, Compound 31, Compound 12, and Compound 65 with mCBP in Examples 1 to 6, respectively, and mixing Comparative Compound C1 and Comparative Compound C2 with mCBP in Comparative Examples 1 and 2, respectively, and depositing the mixture into a layer, thereby obtaining an emission layer formed by co-deposition.

[0287] Thereafter, on the emission layer, a BmPyPhB layer with a thickness of about A layer of thickness of about A layer with a thickness of about Then, a layer with a thickness of about 1000 nm was formed using aluminum (Al). The thickness of the second electrode is .

[0288] In the embodiment, the hole transport region, the emission layer, the electron transport region, and the second electrode are formed using a vacuum deposition apparatus.

[0289] (Evaluation of Properties of Organic Electroluminescent Device A)

[0290] The evaluation results of the organic electroluminescent devices of Examples 1 to 6 and Comparative Examples 1 and 2 are shown in Table 2. In Table 2, the emission efficiency and half-life of the organic electroluminescent devices thus manufactured are compared and shown. In the evaluation results of the properties of the Examples and Comparative Examples shown in Table 2, the emission efficiency is shown at about 5 mA / cm 2 The current efficiency value at a current density of , and the half-life indicates that the brightness increases from about 100 cd / m 2 The time required for the initial brightness to decrease by half.

[0291] [Table 2]

[0292] Classification Dopant materials Emission efficiency (EQE) (%) Half-life (hours) Example 1 Compound 1 10.8 6.9 Example 2 Compound 9 10.2 16.5 Example 3 Compound 30 18.4 33.4 Example 4 Compound 31 15.6 39.8 Example 5 Compound 12 11.6 4.2 Example 6 Compound 65 12.6 4.4 Comparative Example 1 Comparative Compound C1 4.8 2.2 Comparative Example 2 Comparative Compound C2 9.8 0.8

[0293] Referring to the results of Table 2, when compared with the organic electroluminescent devices of Comparative Examples 1 and 2, it was found that the organic electroluminescent devices of Examples 1 to 6 showed higher efficiency and longer life characteristics.

[0294] When compared to the compounds used in the examples, comparison compound C1 does not include an azasilane group substituent, and when examples 1 to 6 are compared with comparison example 1, improved emission efficiency and lifetime characteristics are observed in examples 1 to 6, which include a polycyclic hetero group such as azasilane as a substituent in a compound used as a material for an emission layer.

[0295] Comparative compound C2 includes an azasilane group substituent (like the compounds used in the examples), but Si is substituted with a methyl group, whereas the compounds used in Examples 1 to 6 are substituted with a phenyl group or an isopropyl group at Si. Since the diphenylsilylene group (or isopropyl group) is stable (e.g., more stable) when compared to the dimethylsilylene group, the service life of Examples 1 to 6 is increased compared to Comparative Example 2.

[0296] As shown in the examples, when a heavy atom is included in the substituent substituted at the polycyclic hetero group in the compound used in the light-emitting layer, a reverse intersystem crossing (RISC) phenomenon between the triplet energy state and the singlet energy state can be promoted, and then the luminous efficiency can be improved. In addition, due to the substituent having a heavy atom, the lifespan characteristics are improved.

[0297] 2-2. Example B of organic electroluminescent device

[0298] An embodiment of an organic electroluminescent device comprising a compound of the embodiment in an emission layer was manufactured by the method described below. The organic electroluminescent device of Example 7 was manufactured using Compound 67 as a dopant material for the emission layer. The organic electroluminescent devices of Comparative Examples 3 to 6 were manufactured using Comparative Compounds C3 to C6 as dopant materials for the emission layer.

[0299] The compounds used in Example 7 and Comparative Examples 3 to 6 are shown in Table 3:

[0300] [Table 3]

[0301]

[0302]

[0303] (Manufacturing of Organic Electroluminescent Device B)

[0304] Will be about ITO with a thickness of 1000 nm was patterned on a glass substrate, and then, washed with ultrapure water, cleaned with ultrasonic waves, exposed to UV for about 30 minutes, and then, treated with ozone. Then, HAT-CN was deposited to about The thickness of α-NPD was deposited to about The thickness of the mCP was about to form a hole transport region.

[0305] Then, the exemplary compound or the comparative compound was co-deposited with DPEPO at a ratio of 20:80 to form a That is, the emission layer was formed by mixing Compound 67 with DPEPO in Example 7 and mixing Comparative Compounds C3 to C6 with DPEPO in Comparative Examples 3 to 6, respectively, and depositing the mixtures as layers, thereby obtaining the emission layer formed by co-deposition.

[0306] Thereafter, DPEPO was used to form a layer having a thickness of about A layer of thickness of about A layer with a thickness of about Then, a layer with a thickness of about 1000 nm was formed using aluminum (Al). The thickness of the second electrode is .

[0307] In each embodiment, the hole transport region, the emission layer, the electron transport region, and the second electrode are each formed using a vacuum deposition apparatus.

[0308] (Evaluation of Properties of Organic Electroluminescent Device B)

[0309] The evaluation results of the organic electroluminescent devices in Example 7 and Comparative Examples 3 to 6 are shown in Table 4. In Table 4, the emission efficiency and half-life of the organic electroluminescent devices thus manufactured are compared and shown. In the evaluation results of the properties of the Examples and Comparative Examples shown in Table 4, the emission efficiency is shown at about 5 mA / cm 2 The current efficiency value at a current density of , and the half-life indicates that the brightness increases from about 100 cd / m 2 The time required for the initial brightness to decrease by half.

[0310] [Table 4]

[0311] Classification Dopant materials Emission efficiency (EQE) (%) Half-life (hours) Example 7 Compound 67 19.6 3.9 Comparative Example 3 Comparative Compound C3 11.4 0.2 Comparative Example 4 Comparative Compound C4 16.8 2.9 Comparative Example 5 Comparative Compound C5 16.2 0.6 Comparative Example 6 Comparative Compound C6 18.5 0.9

[0312] Referring to the results of Table 4, when compared with the organic electroluminescent devices of Comparative Examples 3 to 6, it was found that the organic electroluminescent device of Example 7 showed higher efficiency and longer life characteristics.

[0313] Comparative Compound C3 includes an acridan group instead of an azasilane group as a polycyclic hetero group compound when compared with Compound 67 used in Examples, and shows improved emission efficiency and lifetime characteristics when Example 7 is compared with Comparative Example 3.

[0314] Furthermore, Comparative Compounds C4 to C6 include azasilane group substituents as in the compound used in Example 7, but differ in that the nitrogen atom in the azaborane portion corresponding to the core portion is substituted with O, Si, B, etc. Referring to the results of Example 7 and Comparative Examples 4 to 6, in the case where the azaborane portion is included in the core portion corresponding to the electron donor, the lifespan characteristics are improved when compared with the case where O, Si, B, etc. are substituted for N as a heteroatom.

[0315] The compound of the embodiment can show excellent emission efficiency and improved life characteristics by having a core part including an azaborane part and an azasilane group or an azagermane group having a large molecular weight as a substituent, and easily generating reverse intersystem crossing. The organic electroluminescent device of the embodiment includes the compound of the embodiment in the emission layer so as to have a narrow half width in the emission wavelength region, and shows excellent color characteristics, high emission efficiency and long life characteristics.

[0316] The organic electroluminescent device of the embodiment may show improved device properties of long life and high efficiency.

[0317] The compound of the embodiment is contained in an emission layer of an organic electroluminescent device and can contribute to an increase in the life span and efficiency of the organic electroluminescent device.

[0318] As used herein, the term "about" and similar terms are used as terms of approximation rather than as terms of degree, and are intended to account for the inherent deviations in measured or calculated values ​​that would be recognized by one of ordinary skill in the art. In addition, when describing embodiments of the present disclosure, the use of "may" refers to "one or more than one embodiment of the present disclosure."

[0319] In addition, any numerical range listed herein is intended to include all sub-ranges of the same numerical precision within the scope of the listing. For example, the range of "1.0 to 10.0" is intended to include all sub-ranges between the listed minimum value 1.0 and the listed maximum value 10.0 (and including the end value), that is, having a minimum value equal to 1.0 or greater than 1.0 and a maximum value equal to 10.0 or less than 10.0, such as 2.4 to 7.6. Any maximum numerical value listed herein is intended to include all lower numerical limits included therein, and any minimum numerical value listed in this specification is intended to include all higher numerical limits included therein. Therefore, the applicant reserves the right to modify this specification (including claims) to clearly list any sub-ranges included in the scope clearly listed herein.

[0320] Although exemplary embodiments of the present invention have been described, it should be understood that the present invention should not be limited to these exemplary embodiments, but that various changes and modifications may be made by those skilled in the art within the spirit and scope of the present invention as defined by the claims and their equivalents.

Claims

1. An organic electroluminescent device, comprising: a first electrode; a second electrode on the first electrode; as well as an emitting layer between the first electrode and the second electrode, wherein the first electrode and the second electrode each independently comprise: one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, In, Sn and Zn, a compound of two or more selected therefrom, a mixture of two or more selected therefrom, or an oxide thereof; and The emission layer comprises a compound represented by Formula 1: [Formula 1] In formula 1, M1 is a substituted or unsubstituted hydrocarbon ring having 5 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms, and M2 is a substituted hydrocarbon ring having 5 to 30 carbon atoms, or a substituted heterocyclic ring having 2 to 30 carbon atoms, R a is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted silyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted boronyl group, a substituted or unsubstituted phosphino group, a substituted or unsubstituted phosphinooxy group, a substituted or unsubstituted phosphine sulfide group, a substituted or unsubstituted sulfonyl group, or a substituted or unsubstituted sulfinyl group, R b is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, or a substituted or unsubstituted amino group, R a and / or R b optionally combines with M1 or M2 to form a ring, and Any one of the substituents of M1 and M2 is a polycyclic hetero group represented by Formula 2: [Formula 2] In Formula 2, X is Si or Ge, M3 and M4 are each independently a substituted or unsubstituted hydrocarbon ring having 5 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms, L is a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, and R c and R d are each independently a substituted or unsubstituted alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, or R c and R d are combined with each other to form a substituted or unsubstituted hydrocarbon ring having 5 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms, * indicates the connection site with Formula 1, "Substituted" means substituted with at least one substituent selected from the group consisting of a deuterium atom, a halogen atom, an amino group, a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms for forming a ring, and a heterocyclic group having 2 to 20 carbon atoms for forming a ring.

2. The organic electroluminescent device according to claim 1, wherein Formula 1 is represented by Formula 1-1 or Formula 1-2: [Formula 1-1] [Formula 1-2] In formula 1-2, Y1 is B and Y2 is NR a , or Y1 is N and Y2 is BR b , Z is a direct bond, O, S, C=O, BR e NR f , CR g R h 、SiR i R j ,GeR k R l , POR m 、PSR n , SO or SO2, and R e To R n each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, In Formula 1-1 and Formula 1-2, R 11 To R 18 and R 21 To R 31 each independently a hydrogen atom, a deuterium atom, a halogen atom, a straight-chain alkyl group having 1 to 10 carbon atoms, a branched-chain alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms for forming a ring, a heteroaryl group having 2 to 20 carbon atoms for forming a ring, or a substituent of an amino group, or combines with an adjacent group to form a condensed ring, R 11 To R 18 One or more of 11 To R 18 The substituent of the formed condensed ring is the polycyclic hetero group represented by Formula 2, R 21 To R 31 One or more of 21 To R 31 The substituent of the formed condensed ring is the polycyclic hetero group represented by Formula 2, and R a and R b Same as defined in Equation 1, "Substitution" is the same as defined in claim 1.

3. The organic electroluminescent device according to claim 1, wherein Formula 2 is represented by Formula 2-1 or Formula 2-2: [Formula 2-1] [Formula 2-2] In Formula 2-1 and Formula 2-2, R 41 To R 48 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms for forming a ring, a heteroaryl group having 2 to 20 carbon atoms for forming a ring, or an amino group, and L, R c , R d and * are the same as defined in Formula 2, "Substitution" is the same as defined in claim 1.

4. The organic electroluminescent device according to claim 2, wherein Formula 1-1 is represented by Formula 1-1A or Formula 1-1B: [Formula 1-1A] [Formula 1-1B] Wherein in Formula 1-1B, M5 is a substituted or unsubstituted hydrocarbon ring having 5 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms, and In Formula 1-1A and Formula 1-1B, R a and R b The same as defined in Formula 1, and X, L, M3, M4, R c and R d Same as defined in Equation 2, "Substitution" is the same as defined in claim 1.

5. The organic electroluminescent device according to claim 2, wherein Formula 1-2 is represented by one selected from Formula 1-2A to Formula 1-2C: [Formula 1-2A] [Formula 1-2B] [Formula 1-2C] Wherein in Formula 1-2C, Q is a direct bond, O, S, C=O, BR g or NR h ,as well as R g and R h each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, Wherein in Formula 1-2A to Formula 1-2C, R a , R b , Y1, Y2, Z and R 21 To R 31 Same as defined in formula 1-2, "Substitution" is the same as defined in claim 1.

6. The organic electroluminescent device according to claim 2, wherein Formula 1-2 is represented by one selected from Formula 1-2D to Formula 1-2F: [Formula 1-2D] [Formula 1-2E] [Formula 1-2F] Wherein in Formula 1-2F, M6 is a substituted or unsubstituted hydrocarbon ring having 5 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms, and In Formula 1-2D to Formula 1-2F, R 21 To R 31 , Y1, Y2 and Z are the same as those defined in Formula 1-2, and X, L, M3, M4, R c and R d Same as defined in Equation 2, "Substitution" is the same as defined in claim 1.

7. The organic electroluminescent device according to claim 1, wherein M1 is a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted dibenzothiophene ring, and M2 is a substituted benzene ring, a substituted naphthalene ring, or a substituted dibenzothiophene ring, "Substitution" is the same as defined in claim 1.

8. The organic electroluminescent device according to claim 1, wherein M3 and M4 are substituted or unsubstituted benzene rings, "Substitution" is the same as defined in claim 1. 9 . The organic electroluminescent device as claimed in claim 1 , wherein the compound represented by Formula 1 is a material emitting thermally activated delayed fluorescence.

10. The organic electroluminescent device according to claim 1, wherein Formula 1 is at least one selected from Compound Group 1: [Compound Group 1] 11 . The organic electroluminescent device as claimed in claim 1 , further comprising a capping layer on the second electrode.

12. The organic electroluminescent device of claim 1, wherein the emission layer is intended to emit delayed fluorescence.

13. The organic electroluminescent device according to claim 1, wherein the emission layer is a delayed fluorescent emission layer comprising a host and a dopant, and The dopant includes the compound represented by Formula 1. 14 . The organic electroluminescent device of claim 1 , wherein the emission layer is intended to emit blue light having a central wavelength of 430 nm to 490 nm, wherein the central wavelength is a wavelength at the center of an emission peak of the blue light.

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