organic electroluminescent devices

Abstract

An organic electroluminescent device comprising: a first electrode, a second electrode, and an emission layer between the first electrode and the second electrode, wherein the emission layer comprises a compound represented by Formula 1 to achieve high efficiency and improved efficiency droop in a deep blue emission wavelength region: Formula 1

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2019-0133199, filed on October 24, 2019, which is hereby incorporated by reference in its entirety. Technical Field

[0003] One or more aspects of the embodiments of the present disclosure relate to organic electroluminescent devices and compounds for organic electroluminescent devices. Background Art

[0004] Recently, development of organic electroluminescent displays (ELDs) as image display devices has been actively underway. Unlike liquid crystal displays (LCDs), ELDs are self-luminous displays in which holes and electrons injected from a first electrode and a second electrode recombine in an emissive layer. Consequently, the luminescent material (including an organic compound) in the emissive layer emits light, displaying an image.

[0005] When organic electroluminescent devices are applied to display devices, organic electroluminescent devices having low driving voltage, high luminous efficiency and long life are required (or expected), and there is a continuous need (or expectation) to develop materials for organic electroluminescent devices that can stably achieve such characteristics.

[0006] In recent years, in particular, in order to implement efficient organic electroluminescent devices, technologies related to phosphorescent emission using triplet energy or technologies using delayed fluorescence using triplet-triplet annihilation (TTA) in which singlet excitons are generated by collision of triplet excitons are being developed, and thermally activated delayed fluorescence (TADF) materials using the delayed fluorescence phenomenon are being developed. Summary of the Invention

[0007] One or more aspects of the embodiments of the present disclosure are directed to an organic electroluminescent device having improved efficiency droop.

[0008] One or more aspects of the embodiments of the present disclosure also relate to compounds for organic electroluminescent devices having high efficiency characteristics.

[0009] An embodiment of the present disclosure provides a compound represented by Formula 1.

[0010] Formula 1

[0011]

[0012] In Formula 1, any one selected from Ar1 and Ar2 may be a substituted or unsubstituted adamantyl group, the remaining one selected from Ar1 and Ar2 may be a substituted or unsubstituted adamantyl group or a substituted or unsubstituted phenyl group, a may be an integer selected from 1 to 5, R1 may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 ring carbon atoms, and at least one R1 may be represented by Formula 2.

[0013] Formula 2

[0014]

[0015] In Formula 2, R2 to R9 may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 ring-forming carbon atoms, and at least one pair selected from R6 and R7 and R8 and R9 may be combined with each other to form a condensed heterocyclic ring, and -* indicates a position to be connected.

[0016] Formula 1 can be represented by Formula 1-1 or Formula 1-2.

[0017] Formula 1-1

[0018]

[0019] Formula 1-2

[0020]

[0021] In Formula 1-1 and Formula 1-2, b may be an integer selected from 0 to 5, R 11 It may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 ring carbon atoms, and a and R1 are the same as defined in Formula 1.

[0022] Formula 1-1 can be represented by Formula 1-1A or Formula 1-1B.

[0023] Formula 1-1A

[0024]

[0025] Formula 1-1B

[0026]

[0027] In Formula 1-1A and Formula 1-1B, b and R 11 The same as defined in formula 1-1, and R 21 and R 22 can be independently represented by Formula 2.

[0028] Formula 1-2 can be represented by Formula 1-2A or Formula 1-2B.

[0029] Formula 1-2A

[0030]

[0031] Formula 1-2B

[0032]

[0033] In Formula 1-2A and Formula 1-2B, R 23 and R 24 can be independently represented by Formula 2.

[0034] Formula 2 can be expressed by any one of Formula 2-1 to Formula 2-3.

[0035] Formula 2-1

[0036]

[0037] Formula 2-2

[0038]

[0039] Formula 2-3

[0040]

[0041] In Formula 2-1 to Formula 2-3, X1 and X2 can each independently be NR 13 , O or S, R 13 It can be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, an unsubstituted aryl group having 6 to 20 ring carbon atoms, or an unsubstituted heteroaryl group having 2 to 20 ring carbon atoms, c and d can each independently be an integer selected from 0 to 4, R6, R7, R 31 and R 32 Each of them may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 ring carbon atoms, and R2 to R5 are the same as defined in Formula 2.

[0042] Formula 2-1 can be represented by any one of Formula 2-1A to Formula 2-1C.

[0043] Formula 2-1A

[0044]

[0045] Formula 2-1B

[0046]

[0047] Formula 2-1C

[0048]

[0049] In Formula 2-1A to Formula 2-1C, R2 to R7, R 13 、R 31 and c are the same as defined in Formula 2-1.

[0050] Formula 2-2 can be represented by any one of Formula 2-2A to Formula 2-2C.

[0051] Formula 2-2A

[0052]

[0053] Formula 2-2B

[0054]

[0055] Formula 2-2C

[0056]

[0057] In Formula 2-2A to Formula 2-2C, R2 to R5, R 13 、R 31 、R 32 , c, d and X2 are the same as defined in Formula 2-2.

[0058] Formula 2-3 can be represented by any one of Formula 2-3A to Formula 2-3C.

[0059] Formula 2-3A

[0060]

[0061] Formula 2-3B

[0062]

[0063] Formula 2-3C

[0064]

[0065] In Formula 2-3A to Formula 2-3C, R2 to R5, R 13 、R 31 、R 32 , c, d and X2 are the same as defined in Formula 2-3.

[0066] The compound represented by Formula 1 may be a thermally activated delayed fluorescent material.

[0067] In other embodiments of the present disclosure, the organic electroluminescent device includes a first electrode, a second electrode on the first electrode, and an emission layer between the first electrode and the second electrode, wherein the first electrode and the second electrode each independently include: at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, In, Sn and Zn; or a compound selected from two or more thereof; a mixture of two or more thereof; or its oxide, and contains the compound of the above embodiment.

[0068] The emission layer can emit delayed fluorescence. BRIEF DESCRIPTION OF THE DRAWINGS

[0069] The accompanying drawings are included to provide a further understanding of the present disclosure and are incorporated into and constitute a part of this specification. The drawings illustrate example embodiments of the present disclosure and, together with the description, serve to explain the principles of the present disclosure. In the drawings:

[0070] Figure 1 is a cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present disclosure;

[0071] Figure 2 is a cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present disclosure;

[0072] Figure 3 is a cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present disclosure; and

[0073] Figure 4 FIG. 1 is a cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present disclosure. DETAILED DESCRIPTION

[0074] The present disclosure may have various modifications and may be embodied in different forms, and example embodiments will be explained in more detail with reference to the accompanying drawings. However, the present disclosure may be embodied in different forms and should not be construed as being limited to the embodiments set forth herein. On the contrary, all modifications, equivalents, and replacements within the spirit and technical scope of the present disclosure should be included in the present disclosure.

[0075] It will be understood that when an element or layer is referred to as being “on,” “connected to” or “coupled to” another element or layer, it can be directly on, directly connected or directly coupled to the other element or layer without any intervening elements or layers, or intervening elements or layers may be present.

[0076] The same reference numerals refer to the same elements throughout the text. Moreover, in the accompanying drawings, the thickness, proportion and size of the elements are exaggerated in order to effectively describe the technical content.

[0077] The term "and / or" includes all combinations of one or more that can be defined in the associated configuration. For example, expressions such as "at least one of," "one of," and "selected from," when preceding a list of elements, modify the entire list of elements and do not modify the individual elements in that list. In addition, when describing embodiments of the present disclosure, the use of "may" refers to "one or more embodiments of the present disclosure."

[0078] It will be understood that although the terms "first," "second," etc. may be used herein to describe various elements, these elements should not be limited by these terms. These terms are only used to distinguish one element from another. For example, a first element may be referred to as a second element, and similarly, a second element may be referred to as a first element, without departing from the scope of the exemplary embodiments of the present disclosure. Unless the context clearly indicates otherwise, terms in the singular may include plural forms.

[0079] In addition, terms such as "below," "lower," "above," and "upper" are used to describe the relationship of the configurations shown in the drawings. These terms are used as relative concepts and are described with reference to directions indicated in the drawings.

[0080] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which the present disclosure belongs. It should also be understood that terms defined in commonly used dictionaries should be interpreted as having a meaning consistent with their meaning in the context of the prior art and not in an ideal or overly formal sense unless they are explicitly defined herein.

[0081] It should be understood that the terms “include,” “comprising,” and “having” are intended to indicate the presence of the stated features, integers, steps, operations, elements, components, or combinations thereof in the present disclosure, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.

[0082] Hereinafter, an organic electroluminescent device according to an embodiment of the present disclosure and a compound of an embodiment included therein will be described with reference to the accompanying drawings.

[0083] Figures 1 to 4Schematically shows a cross-sectional view of an organic electroluminescent device according to an 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 positioned to face each other, and the emission layer EML may be provided between the first electrode EL1 and the second electrode EL2.

[0084] In addition to the emission layer EML, the organic electroluminescent device 10 of the embodiment further includes multiple functional layers between the first electrode EL1 and the second electrode EL2. The multiple functional layers may include a hole transport region HTR and an electron transport region ETR. For example, the organic electroluminescent device 10 according to the embodiment may include the first electrode EL1, the hole transport region HTR, the emission layer EML, the electron transport region ETR, and the second electrode EL2, which are stacked in this order. In some embodiments, the organic electroluminescent device 10 may include a capping layer CPL on the second electrode EL2.

[0085] The organic electroluminescent device 10 of the embodiment includes a compound of the embodiment, which will be described in more detail later, in the emission layer EML between the first electrode EL1 and the second electrode EL2.

[0086] and Figure 1 compared to, Figure 2 1 shows a cross-sectional view of an organic electroluminescent device 10 according to an embodiment, wherein the hole transport region HTR includes a hole injection layer HIL and a hole transport layer HTL, and the electron transport region ETR includes an electron injection layer EIL and an electron transport layer ETL. Figure 1 compared to, Figure 3 1 shows a cross-sectional view of an organic electroluminescent device 10 according to an embodiment, wherein the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL, and an electron blocking layer EBL, and the 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 is shown, illustrating an embodiment including a capping layer CPL on the second electrode EL2 .

[0087] The first electrode EL1 is conductive. The first electrode EL1 may be formed of a metal alloy or any suitable conductive compound. The first electrode EL1 may be an anode. Furthermore, the first electrode EL1 may be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a transflective electrode, or a reflective electrode. When the first electrode EL1 is a transmissive electrode, the first electrode EL1 may include a transparent metal oxide, such as 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 transflective electrode or a reflective electrode, the first electrode EL1 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, compounds thereof, or mixtures thereof (e.g., a mixture of Ag and Mg). In some embodiments, the first electrode EL1 may have a multilayer structure including a reflective layer or a transflective layer and a transmissive layer formed of indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), or the like. For example, the first electrode EL1 may have a three-layer structure of ITO / Ag / ITO, but is not limited thereto. The thickness of the first electrode EL1 may be about 100 Å. to about For example, about to about

[0088] The hole transport region HTR may be provided on the first electrode EL1. The hole transport region HTR may include at least one of 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

[0089] The hole transport region HTR may have a single layer formed of a single material, a single layer formed of a plurality of different materials, or a multi-layered structure including a plurality of layers formed of a plurality of different materials.

[0090] For example, the hole transport region HTR may have a single-layer structure of a hole injection layer HIL or a hole transport layer HTL, or may have a single-layer structure formed of a hole injection material and a hole transport material. In some embodiments, the hole transport region HTR may have a single-layer structure formed of a plurality of different materials, or a structure in which hole injection layer HIL / hole transport layer HTL, hole injection layer HIL / hole transport layer HTL / hole buffer layer, hole injection layer HIL / hole buffer layer, hole transport layer HTL / hole buffer layer, or hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL are stacked in sequence from the first electrode EL1, but embodiments are not limited thereto.

[0091] The hole transport region HTR may be formed using one or more suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Brockett (LB) method, inkjet printing, laser printing, and / or laser induced thermal imaging (LITI).

[0092] The hole injection layer HIL may include, for example, a phthalocyanine compound (such as copper phthalocyanine), N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine (DNTPD), 4,4',4"-[tris(3-methylphenyl)phenylamino]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)

[0014] The present invention relates to polyaniline / poly (4-styrene sulfonate) (PANI / PSS), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly (4-styrenesulfonate) (PANI / PSS), N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine (NPD), 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-hexanitrile (HAT-CN), etc.

[0093] The hole transport layer HTL may further include, for example, carbazole derivatives (such as N-phenylcarbazole and / or polyvinylcarbazole), fluorine derivatives, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD), triphenylamine derivatives (such as 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA)), N,N'-di(1-naphth-1-yl)-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-carbazolyl)benzene (mCP), and the like.

[0094] 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 satisfy the above ranges, satisfactory (or appropriate) hole transport properties may be achieved without a significant increase in driving voltage.

[0095] In addition to the above materials, the hole transport region HTR may further include a charge generating material to increase 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 one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. Non-limiting examples of p-dopants may include quinone derivatives (such as tetracyanoquinodimethane (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ)) and metal oxides (such as tungsten oxide and / or molybdenum oxide).

[0096] 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 can compensate for the optical resonance distance according to the wavelength of light emitted from the emission layer EML and can increase light emission efficiency. The materials that can be included in the hole transport region HTR can be used as the materials that can be included in the hole buffer layer. The electron blocking layer EBL is a layer used to prevent or reduce the injection of electrons from the electron transport region ETR into the hole transport region HTR.

[0097] An emission layer EML may be provided on the hole transport region HTR. The thickness of the emission layer EML may be, for example, about to about or about to about The emission layer EML may have a single layer formed of a single material, a single layer formed of a plurality of different materials, or a multi-layered structure having a plurality of layers formed of a plurality of different materials.

[0098] The emission layer EML in the organic electroluminescent device 10 of the embodiment may include the compound according to the embodiment of the present disclosure.

[0099] In this description, the term "substituted or unsubstituted" may refer to an unsubstituted group or a group 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 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 group, an aryl group, and a heterocyclic group (e.g., a heterocycle). In addition, each of the above substituents may itself be substituted or unsubstituted. For example, a biphenyl group may be interpreted as an aryl group, or a phenyl group substituted by a phenyl group.

[0100] In the present description, examples of the halogen atom may include a fluorine atom, a chlorine atom, a bromine atom, and / or an iodine atom.

[0101] In the present description, the alkyl group may be a linear, branched, or cyclic alkyl group. The number of carbon atoms in the alkyl group is 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of the alkyl group may 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-butyldecyl, 2-Hexyldecyl, 2-octyldecyl, 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, etc., but are not limited thereto.

[0102] In this description, an aryl group may refer to a functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. The number of ring carbon atoms in the aryl group may be 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, pentyl, hexaphenyl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, chrysene, and the like.

[0103] In the present description, the heteroaryl group may include at least one of B, O, N, P, Si, and S as a ring-forming heteroatom. When the heteroaryl group contains two or more heteroatoms, the two or more heteroatoms may be the same as or different from each other. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. The number of ring-forming carbon atoms in the heteroaryl group may be 2 to 30, 2 to 20, or 2 to 10. Examples of heteroaryl groups may include, but are not limited to, thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazolopyrazinyl, isoquinolyl, indolyl, carbazolyl, N-arylcarbazolyl, N-heteroarylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothiphenyl, benzofuranyl, phenanthrolinyl, isothiazolyl, isoxazolyl, thiadiazolyl, phenothiazinyl, dibenzothiazolyl, dibenzofuranyl, and the like.

[0104] In the present description, the thio group may include an alkylthio group and an arylthio group.

[0105] In the present description, the alkyl group in the alkylthio group is the same as described herein.

[0106] In this description, oxy groups may include alkoxy groups and aryloxy groups. Alkoxy groups may be straight, branched, or cyclic. The number of carbon atoms in the alkoxy group may be, for example, 1 to 20 or 1 to 10, but is not particularly limited thereto. Furthermore, the number of carbon atoms in the aryloxy group may be, for example, 6 to 20 or 6 to 10, but is not particularly limited thereto. Examples of oxy groups may include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, benzyloxy, etc.

[0107] In the present description, the aryl group in the aryloxy group and the arylthio group is the same as described herein.

[0108] In the present description, "-*" refers to a position to be linked (eg, a binding site).

[0109] The compound according to an embodiment of the present disclosure may be represented by Formula 1.

[0110] Formula 1

[0111]

[0112] In Formula 1, any one selected from Ar1 and Ar2 may be a substituted or unsubstituted adamantyl group, and the other selected from Ar1 and Ar2 may be a substituted or unsubstituted adamantyl group or a substituted or unsubstituted phenyl group. a may be an integer selected from 1 to 5.

[0113] When a is an integer of 2 or greater, a plurality of R1s may be the same as or different from each other.

[0114] R1 may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 ring-forming carbon atoms, and at least one R1 may be represented by Formula 2.

[0115] Formula 2

[0116]

[0117] In Formula 2, R2 to R9 may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 ring carbon atoms. At least one pair selected from R6 and R7 and R8 and R9 is combined with each other to form a fused heterocyclic ring.

[0118] The compound of the embodiment may be a triazine derivative, wherein the three N (nitrogen) and three C (carbon) included in the aromatic ring are arranged alternately, wherein the triazine derivative includes an adamantyl group directly bonded to at least one of the three C groups. Substituted or unsubstituted phenyl groups may be bonded to a C atom that is not bonded to an adamantyl group. The phenyl group bonded to the C atom may include at least one fused heterocycle (e.g., may be substituted by at least one fused heterocycle). The fused heterocycle has a structure in which 5 to 7 membered aromatic rings are fused, and may include two or three heteroatoms. At least one of the two or three heteroatoms is a nitrogen atom, and the other heteroatoms may each independently be a nitrogen atom, an oxygen atom, or a sulfur atom.

[0119] The compound represented by Formula 1 may be represented by Formula 1-1 or Formula 1-2.

[0120] Formula 1-1

[0121]

[0122] Formula 1-2

[0123]

[0124] Formula 1-1 represents a case where one of Ar1 and Ar2 is an adamantyl group, and Formula 1-2 represents a case where both Ar1 and Ar2 are adamantyl groups. a and R1 may be the same as described in Formula 1.

[0125] In Formula 1-1 and Formula 1-2, b is an integer selected from 0 to 5, and when b is an integer of 2 or greater, a plurality of R 11 They may be the same as or different from each other.

[0126] R 11 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 ring carbon atoms.

[0127] The compound represented by Formula 1-1 may be represented by Formula 1-1A or Formula 1-1B.

[0128] Formula 1-1A

[0129]

[0130] Formula 1-1B

[0131]

[0132] Formula 1-1A has a triazine derivative and R 21 The structure is bonded at the meta position relative to the middle phenyl group, and Formula 1-1B has a structure in which the triazine derivative and R 22 The structure is bonded at the para position relative to the middle phenyl group.

[0133] In Formula 1-1A and Formula 1-1B, R 21 and R 22 Each of them can be independently represented by Formula 2. For example, the compound of this embodiment can be represented by Formula 1-1AA or Formula 1-1BB. However, the embodiments of the present disclosure are not limited thereto.

[0134] Formula 1-1AA

[0135]

[0136] Formula 1-1BB

[0137]

[0138] b and R 11R2 to R9 may be the same as those described in Formula 1-1. In some embodiments, the compound represented by Formula 1-2 may be represented by Formula 1-2A or Formula 1-2B.

[0139] Formula 1-2A

[0140]

[0141] Formula 1-2B

[0142]

[0143] Formula 1-2A has a triazine derivative and R 23 The structure is bonded at the meta position relative to the middle phenyl group, and Formula 1-2B has a structure in which the triazine derivative and R 24 The structure is bonded at the para position relative to the middle phenyl group.

[0144] In Formula 1-2A and Formula 1-2B, R 23 and R 24 Each is independently represented by Formula 2. For example, Formula 1-2A or Formula 1-2B can be represented by Formula 1-2AA or Formula 1-2BB. However, the embodiments of the present disclosure are not limited thereto.

[0145] Formula 1-2AA

[0146]

[0147] Formula 1-2BB

[0148]

[0149] R2 to R9 may be the same as described in Formula 2.

[0150] Formula 2 can be expressed by any one of Formula 2-1 to Formula 2-3.

[0151] Formula 2-1

[0152]

[0153] Formula 2-2

[0154]

[0155] Formula 2-3

[0156]

[0157] In Formula 2-1, R8 and R9 of Formula 2 form a condensed heterocyclic ring, and in Formula 2-2 and Formula 2-3, R6 and R7 and R8 and R9 of Formula 2 each form a condensed heterocyclic ring.

[0158] In Formula 2-1 to Formula 2-3, X1 and X2 can each independently be NR 13 , O or S. R2 to R5 may be the same as described in Formula 2.

[0159] R 13 It may be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, an unsubstituted aryl group having 6 to 20 ring carbon atoms, or an unsubstituted heteroaryl group having 2 to 20 ring carbon atoms.

[0160] c and d may each independently be an integer selected from 0 to 4. When c and / or d is an integer of 2 or greater, a plurality of R 31 or multiple R 32 They may be the same as or different from each other.

[0161] R6, R7, R 31 and R 32 Each of them may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 ring carbon atoms.

[0162] Formula 2-1 can be represented by any one of Formula 2-1A to Formula 2-1C.

[0163] Formula 2-1A

[0164]

[0165] Formula 2-1B

[0166]

[0167] Formula 2-1C

[0168]

[0169] Formula 2-1A represents that X1 is NR 13 , Formula 2-1B represents the case where X1 is O, and Formula 2-1C represents the case where X1 is S.

[0170] In Formula 2-1A to Formula 2-1C, R2 to R7, R 13 、R 31 and c may be the same as described in Formula 2-1.

[0171] Formula 2-2 can be represented by any one of the described Formulas 2-2A to 2-2C.

[0172] Formula 2-2A

[0173]

[0174] Formula 2-2B

[0175]

[0176] Formula 2-2C

[0177]

[0178] Formula 2-2A represents that X1 is NR 13 , Formula 2-2B represents the case where X1 is O, and Formula 2-2C represents the case where X1 is S.

[0179] In Formula 2-2A to Formula 2-2C, R2 to R5, R 13 、R 31 、R 32 , c, d and X2 may be the same as described in Formula 2-2.

[0180] Formula 2-3 can be represented by any one of Formula 2-3A to Formula 2-3C.

[0181] Formula 2-3A

[0182]

[0183] Formula 2-3B

[0184]

[0185] Formula 2-3C

[0186]

[0187] Formula 2-3A represents that X1 is NR 13 , Formula 2-3B represents the case where X1 is O, and Formula 2-3C represents the case where X1 is S.

[0188] In Formula 2-3A to Formula 2-3C, R2 to R5, R 13 、R 31 、R 32 , c, d and X2 may be the same as described in Formula 2-3.

[0189] The compound of the embodiment may have a structure in which one or two of the three phenyl groups connected to the three carbon atoms in the triazine group included in the triazine derivative are replaced by an unsubstituted adamantyl group. At least one of the phenyl groups connected to the triazine derivative in the triazine derivative may have one or more heterocycles as substituents. The compound according to the embodiment may be used as an emitting material for emitting deep blue light having an emission center wavelength in a wavelength region of about 430 nm to 470 nm. For example, the compound of the embodiment represented by Formula 1 may be an emitting material having an emission center wavelength in a wavelength region of about 430 nm to about 490 nm.

[0190] The compound of the embodiment may be any one of the compounds represented by compound group 1. The organic electroluminescent device 10 of the embodiment may include at least one of the compounds represented by compound group 1 in the emission layer EML.

[0191] Compound Group 1

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198] In the organic electroluminescent device 10 of the embodiment, the emission layer EML may emit delayed fluorescence. For example, the emission layer EML may emit thermally activated delayed fluorescence (TADF).

[0199] In some embodiments, the organic electroluminescent device 10 may include a plurality of emission layers EML. When the organic electroluminescent device 10 includes a plurality of emission layers EML, at least one emission layer EML may include the compound of this embodiment.

[0200] In an embodiment, the emission layer EML includes a host and a dopant, and may include the compound of the embodiment as the dopant. For example, in the organic electroluminescent device 10 of the embodiment, the emission layer EML may include a host for delayed fluorescence and a dopant for delayed fluorescence, and the compound of the embodiment may be the dopant for delayed fluorescence. The emission layer EML may include at least one of the compounds represented by compound group 1 as a thermally activated delayed fluorescence dopant.

[0201] In embodiments, the emission layer EML may be a delayed fluorescent emission layer, and the emission layer EML may include any suitable host material and the compound of the present embodiment. For example, in embodiments, the compound may be used as a TADF dopant.

[0202] 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-hydroxyquinoline)aluminum (Alq3), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), poly(N-vinylcarbazole) (PVK), 9,10-di(naphthalene-2-yl)anthracene (ADN), 4,4',4"-tris(carbazol-9-yl)-triphenylamine (TCTA), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBi), 3-tert-butyl-9,10-di(naphthalene-2-yl)anthracene (TBADN), distyrylarene (DSA), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), 2-methyl-9, 10-bis(naphthalene-2-yl)anthracene (MADN), bis[2-(diphenylphosphine)phenyl]ether oxide (DPEPO), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH2), hexaphenylcyclotrisiloxane (DPSiO3), octaphenylcyclotetrasiloxane (DPSiO4), 2,8-bis(diphenylphosphoryl)dibenzofuran (PPF), 3,3'-bis(N-carbazolyl)-1,1'-biphenyl (mCBP) and / or 1,3-bis(N-carbazolyl)benzene (mCP) as host materials, but the embodiments of the present disclosure are not limited thereto. For example, in addition to the host materials proposed, a suitable delayed fluorescence host material may be included.

[0203] 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 a styryl derivative (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4″-[(di-p-tolylamino)styryl]stilbene (DPAVB) and / or N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2-yl)vinyl)phenyl)-N-phenylaniline (N-BDAVBi)), perylene and / or its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)), pyrene and / or its derivatives (e.g., 1,1-dipyrene, 1,4-dipyrenylbenzene, 1,4-bis(N,N-diphenylamino)pyrene, etc.) as a dopant.

[0204] exist Figures 1 to 4In the organic electroluminescent device 10 of the embodiment shown in FIG, an electron transport region ETR may be 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, but the embodiment is not limited thereto.

[0205] The electron transport region ETR may have a single layer formed of a single material, a single layer formed of a plurality of different materials, or a multi-layered structure including a plurality of layers formed of a plurality of different materials.

[0206] 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, and may have a single-layer structure formed of an electron injection material and an electron transport material. In some embodiments, the electron transport region ETR may have a single-layer structure formed of a plurality of different materials, or may have a structure in which an electron transport layer ETL / electron injection layer EIL or a hole blocking layer HBL / electron transport layer ETL / electron injection layer EIL are stacked in sequence from the emission layer EML, but is not limited thereto. The thickness of the electron transport region ETR may be, for example, about 1000Å. to about

[0207] The electron transport region ETR can be formed using one or more suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Brockett (LB) method, inkjet printing, laser printing, laser induced thermal imaging (LITI), etc.

[0208] When the electron transport region ETR includes an electron transport layer ETL, the electron transport region ETR may include an anthracene compound. However, the present disclosure is not limited thereto, and the electron transport region ETR may include, for example, tris(8-hydroxyquinoline)aluminum (Alq3), 1,3,5-tris[(3-pyridyl)-phenyl-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, 1,3,5-tris(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- The electron transport layer ETL may be made of a material selected from the group consisting of 2-(4-biphenyl)-5-(4-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-hydroxyquinolinolato-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), bis(benzoquinolinolato-10-hydroxy)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. The thickness of the electron transport layer ETL may be about 1000 nm. to about and can be, for example, about to about If the thickness of the electron transport layer ETL satisfies the above range, satisfactory electron transport properties may be obtained without a significant increase in driving voltage.

[0209] When the electron transport region ETR includes an electron injection layer EIL, the electron transport region ETR may include a metal halide (such as LiF, NaCl, CsF, RbCl and / or RbI), a lanthanide metal (such as Yb), a metal oxide (such as Li2O and / or BaO) and / or 8-hydroxyquinoline lithium (LiQ), but is not limited thereto. The electron injection layer EIL may also be formed of a mixture material of an electron transport material and an insulating organic metal salt. The insulating organic metal salt may be a material having an energy band gap of about 4 eV or greater. For example, the insulating organic metal salt may include a metal acetate, a metal benzoate, a metal acetoacetate, a metal acetylacetonate and / or a metal stearate. The thickness of the electron injection layer EIL may be about 100 nm. to about or about to about When the thickness of the electron injection layer EIL satisfies the above range, satisfactory (or appropriate) electron injection properties may be obtained without a significant increase in driving voltage.

[0210] As described above, the electron transport region ETR may include a hole blocking layer HBL. 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), but is not limited thereto.

[0211] The second electrode EL2 may be provided on the electron transport region ETR. The second electrode EL2 may be a common electrode and / or a cathode. The second electrode EL2 may be a transmissive electrode, a transflective electrode, or a reflective electrode. If the second electrode EL2 is a transmissive electrode, the second electrode EL2 may include a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), and / or indium tin zinc oxide (ITZO).

[0212] If the second electrode EL2 is a transflective 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, Mo, Ti, compounds thereof, or mixtures thereof (e.g., a mixture of Ag and Mg). In some embodiments, the second electrode EL2 may have a multilayer structure including a reflective layer or a transflective layer formed of any of the above materials and a transparent conductive layer formed of indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), or the like.

[0213] In some embodiments, the second electrode EL2 may be connected to the auxiliary electrode. When the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.

[0214] The organic electroluminescent device 10 of the embodiment may further include a capping layer CPL on the second electrode EL2. The capping layer CPL may include, for example, α-NPD, NPB, TPD, m-MTDATA, Alq3, 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), and the like.

[0215] The organic electroluminescent device 10 according to an embodiment of the present disclosure includes the compound of the embodiment in the emission layer EML between the first electrode EL1 and the second electrode EL2, and can obtain excellent luminous efficiency and improved efficiency drop in the deep blue emission wavelength region. In addition, the compound according to the embodiment can be a thermally activated delayed fluorescence dopant, and the emission layer EML including the compound of the embodiment can emit thermally activated delayed fluorescence, thereby obtaining reasonable luminous efficiency characteristics.

[0216] Hereinafter, referring to Examples and Comparative Examples, the compounds according to the embodiments of the present disclosure and the organic electroluminescent devices of the embodiments will be described in more detail. In addition, the examples shown below are only for explanation of the present disclosure, and the scope of the present disclosure is not limited thereto.

[0217] Example

[0218] 1. Synthesis of the compounds of the examples

[0219] First, the synthesis method of the compound according to the present embodiment will be described in more detail by showing an exemplary method for synthesizing Compound 1, Compound 8, Compound 15, Compound 16, Compound 18, Compound 20, Compound 29, Compound 43, Compound 57, and Compound 63. In addition, the synthesis method of the compound described below is merely an example, and the synthesis method of the compound according to the embodiment of the present disclosure is not limited to the examples given.

[0220] (1) Synthesis of Compound 1

[0221] For example, Compound 1 according to the embodiment can be synthesized through Reaction Formula 1.

[0222] Reaction 1

[0223]

[0224] To the reactant 1-A (4.0 g, 8.04 mmol), the reactant 1-B (4.26 g, 8.44 mmol), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.15 g, 0.16 mmol), tri-tert-butylphosphine tetrafluoroborate (P(t-Bu)3HBF4, 0.19 g, 0.64 mmol) and sodium tert-butoxide (NaOt-Bu, 0.77 g, 12.1 mmol), toluene (200 ml) was added, and heated and stirred at about 80°C for about 2 hours. Water was added to the reaction solution, and the resulting product was subjected to diatomaceous earth filtration and liquid separation to concentrate the organic layer. The concentrated solid was purified by silica gel column chromatography to obtain compound 1 (6.30 g, yield 85%). The molecular weight of compound 1 was m / z=921 (M as measured by fast atom bombardment mass spectrometry (FAB-MS) measurement.+ +1).

[0225] (2) Synthesis of Compound 8

[0226]

[0227] Compound 8 (5.06 g, yield 73%) was synthesized in substantially the same manner as for compound 1, except that reactant 1-D was used instead of reactant 1-B. The molecular weight of compound 8 as measured by FAB-MS was m / z = 921 (M + +1).

[0228] (3) Synthesis of compound 15

[0229]

[0230] Compound 15 (5.13 g, yield 74%) was synthesized in substantially the same manner as for compound 1, except that reactant 1-C was used instead of reactant 1-B. The molecular weight of compound 15 as measured by FAB-MS was m / z=863 (M + +1).

[0231]

[0232] Compound 16 (5.22 g, 70% yield) was synthesized in substantially the same manner as for compound 1, except that reactant 1-E was used instead of reactant 1-A, and reactant 1-C was used instead of reactant 1-B. The molecular weight of compound 16 as measured by FAB-MS was m / z=788 (M + +1).

[0233] (5) Synthesis of Compound 18

[0234]

[0235] Compound 18 (4.77 g, 65% yield) was synthesized in substantially the same manner as for compound 1, except that reactant 1-F was used instead of reactant 1-A, and reactant 1-C was used instead of reactant 1-B. The molecular weight of compound 18 as measured by FAB-MS was m / z=804 (M + +1).

[0236] (6) Synthesis of Compound 20

[0237]

[0238] Compound 20 (5.21 g, 65% yield) was synthesized in substantially the same manner as for compound 1, except that reactant 1-G was used instead of reactant 1-A, and reactant 1-C was used instead of reactant 1-B. The molecular weight of compound 20 as measured by FAB-MS method S was m / z = 729 (M + +1).

[0239] (7) Synthesis of Compound 29

[0240]

[0241] Compound 29 (5.11 g, 69% yield) was synthesized in substantially the same manner as for compound 1, except that reactant 1-H was used instead of reactant 1-A. The molecular weight of compound 29 as measured by FAB-MS was m / z = 921 (M + +1).

[0242] (8) Synthesis of Compound 43

[0243]

[0244] Compound 43 (4.54 g, 61% yield) was synthesized in substantially the same manner as for compound 1, except that reactant 1-H was used instead of reactant 1-A, and reactant 1-C was used instead of reactant 1-B. The molecular weight of compound 43 as measured by FAB-MS was m / z=863 (M + +1).

[0245] (9) Synthesis of Compound 57

[0246]

[0247] Compound 57 (7.28 g, yield 80%) was synthesized in substantially the same manner as for compound 1, except that reactant 1-I was used instead of reactant 1-A. The molecular weight of compound 57 as measured by FAB-MS was m / z=756 (M + +1).

[0248] (10) Synthesis of Compound 63

[0249]

[0250] Compound 63 (6.80 g, yield 81%) was synthesized in substantially the same manner as for compound 1, except that reactant 1-I was used instead of reactant 1-A, and reactant 1-C was used instead of reactant 1-B. The molecular weight of compound 63 as measured by FAB-MS was m / z=698 (M + +1).

[0251] 2. Evaluation of compounds and fabrication and evaluation of organic electroluminescent devices

[0252] The light emitting characteristics of the compounds of the synthesis examples and the organic electroluminescent devices of the examples including the compounds in the emission layer were evaluated as follows: The method for manufacturing the organic electroluminescent devices used for the evaluation is described below.

[0253] The organic electroluminescent devices of Examples 1 to 10 were manufactured using Compound 1, Compound 8, Compound 15, Compound 16, Compound 18, Compound 20, Compound 29, Compound 43, Compound 57, and Compound 63 as dopants for the emission layer. Comparative Examples 1 to 4 were organic electroluminescent devices manufactured using Comparative Compound C1, Comparative Compound C2, Comparative Compound C3, and Comparative Compound C4, respectively, as dopants for the emission layer.

[0254] Table 1 shows the compounds used in Examples 1 to 10 and Comparative Examples 1 to 4.

[0255] Table 1

[0256]

[0257]

[0258] Evaluation of the luminescence properties of compounds

[0259] Toluene (5.0 mM) solution was prepared to evaluate the luminescent properties of the Example compounds and the Comparative Example compounds, and JASCO V-670 spectrometer was used to evaluate the luminescent properties. The emission spectra at room temperature and 77 K were measured. Table 2 shows the maximum emission wavelength λ in the emission spectra measured at room temperature. max and full width at half maximum (FWHM). In addition, the PLQY (photoluminescence quantum yield) of a 5.0 mM toluene solution for each compound was measured using HAMAMATSU Quantaurus-QY.

[0260] Table 2

[0261] Compound <![CDATA[λ max (nm)]]> FWHM(nm) PLQY (%) Compound 1 459 62 85 Compound 8 453 61 65 Compound 15 463 63 79 Compound 16 451 61 60 Compound 18 456 65 63 Compound 20 443 61 65 Compound 29 454 56 82 Compound 43 460 63 83 Compound 57 445 62 76 Compound 63 449 63 74 Comparative Compound C1 522 78 89 Comparative Compound C2 461 61 60 Comparative Compound C3 440 58 30 Comparative Compound C4 630 82 80

[0262] Referring to the results of Table 2, it can be seen that Compound 1, Compound 8, Compound 15, Compound 16, Compound 18, Compound 20, Compound 29, Compound 43, Compound 57 and Compound 63 of the Examples exhibited a maximum emission wavelength of 465 nm or less, and emitted deep blue light therefrom.

[0263] In addition, it can be seen that compared with comparative compound C1 and comparative compound C4, compound 1, compound 8, compound 15, compound 16, compound 18, compound 20, compound 29, compound 43, compound 57 and compound 63 of the examples have narrower full width at half maximum (FWHM) in the emission spectra.

[0264] It can be seen that compared with comparative compound C2 and comparative compound C3, compound 1, compound 8, compound 15, compound 16, compound 18, compound 20, compound 29, compound 43, compound 57 and compound 63 of the examples have larger PLQY values, thereby providing superior luminous efficiency.

[0265] It can be seen that Comparative Compounds C1 and C4 emit light with lower color purity than the Example Compounds by emitting light of a long wavelength and having a wide full width at half maximum. Although Comparative Compounds C2 and C3 have short wavelengths and narrow full width at half maximum, their PLQY is lower than that of the Example Compounds.

[0266] The example compounds containing one or two adamantyl groups had a weaker acceptor portion of the triazine derivative to emit short-wavelength light compared to Comparative Compounds C1 and C4, and achieved superior luminous efficiency compared to Comparative Compounds C2 and C3.

[0267] Fabrication of organic electroluminescent devices

[0268] As the first electrode, ITO was patterned to approximately The HAT-CN was deposited to a thickness of , and washed with ultrapure water, cleaned with ultrasound, irradiated with UV for 30 minutes, and then ozone treated. The thickness of α-NPD was deposited to The thickness of the mCP is deposited to to form a hole transport region.

[0269] Next, when forming each emission layer, the Example compound or the Comparative Example compound and mCBP were co-deposited at a ratio of 1:99 to form a That is, the emission layers formed by co-deposition in Examples 1 to 10 were deposited by mixing Compound 1, Compound 8, Compound 15, Compound 16, Compound 18, Compound 20, Compound 29, Compound 43, Compound 57, and Compound 63 with mCBP, respectively, and the emission layers in Comparative Examples 1 to 4 were deposited by mixing Comparative Compound C1, Comparative Compound C2, Comparative Compound C3, and Comparative Compound C4 with mCBP, respectively.

[0270] Afterwards, a TPBi layer with A layer of thickness of , and formed thereon by LiF having Then, a layer having a thickness of 1000 nm is formed by aluminum (Al) to form an electron transport region. The thickness of the second electrode is .

[0271] In an embodiment, the hole transport region, the emission layer, the electron transport region, and the second electrode are formed using a vacuum deposition apparatus.

[0272] Evaluation of organic electroluminescent device characteristics

[0273] Table 3 shows the evaluation results of the organic electroluminescent devices of Examples 1 to 10 and Comparative Examples 1 to 4. Table 3 shows the maximum emission wavelength (λ) of the manufactured organic electroluminescent devices by comparison. max ) and external quantum efficiency (EQE max In the characteristic evaluation results of the examples and comparative examples shown in Table 3, the maximum emission wavelength (λ max ) indicates the wavelength representing the maximum value in the emission spectrum, and at 1000 cd / m 2 The external quantum efficiency (EQE max , 1000尼特 ).

[0274] Table 3

[0275]

[0276]

[0277] Referring to the results in Table 3, the organic electroluminescent devices of Examples 1 to 3 and Examples 7 to 10 emitted short, deep blue light with high efficiency compared to the organic electroluminescent devices of Comparative Examples 1 to 4. It was confirmed that the organic electroluminescent devices of Examples 4 to 6 emitted short, deep blue light while having similar levels of luminous efficiency compared to the organic electroluminescent devices of Comparative Examples 1 and 2. Furthermore, it was confirmed that Examples 4 to 6 exhibited improved luminous efficiency values ​​compared to Comparative Examples 3 and 4.

[0278] It is believed that in the case of the example compounds, the inclusion of one or two adamantyl groups as substituents in the triazine derivative reduces conjugation and weakens the acceptor moiety, thereby emitting light of a short wavelength.

[0279] Comparative Compound C1 used in the organic electroluminescent device of Comparative Example 1 includes a triazine derivative whose acceptor moiety is not substituted with an adamantyl group, and thus has a longer emission wavelength than that of the Example compounds.

[0280] Comparative Example 3 showed a low external quantum efficiency value. Due to the steric hindrance of two adjacent phenyl groups in Comparative Compound C3, a large torsion angle was generated in the donor portion and the acceptor portion, and the oscillation angle became smaller, resulting in low external quantum efficiency.

[0281] In Comparative Example 4, since the ΔE between the lowest singlet excitation energy level (S1) and the lowest triplet excitation energy level (T1) of the comparative compound C4 is ST Therefore, no TADF emission is exhibited, resulting in a low external quantum efficiency value.

[0282] The compound of the embodiment includes one or two unsubstituted adamantyl groups and a fused heterocycle centered on a triazine derivative (connected to the triazine derivative), thereby emitting short blue light with high efficiency. In addition, the organic electroluminescent device of the embodiment includes the compound of the embodiment in the emission layer to obtain improved efficiency drop in the deep blue emission wavelength region.

[0283] The organic electroluminescent device of the embodiment may have improved device characteristics with high efficiency in a deep blue wavelength region.

[0284] The compound of the embodiment may be included in an emission layer of an organic electroluminescent device to contribute to high efficiency of the organic electroluminescent device.

[0285] As used herein, the terms "use," "using," and "used" may be considered synonymous with the terms "utilize," "utilizing," and "utilized," respectively.

[0286] Additionally, the terms "substantially," "about," and similar terms are used as terms of approximation rather than terms of degree, and are intended to account for the inherent variations in measurements or calculations that those skilled in the art would recognize.

[0287] Moreover, any numerical range listed herein is intended to include all subranges of the same numerical precision included in the listed range. For example, the range of "1.0 to 10.0" is intended to include all subranges between the listed minimum value of 1.0 and the listed maximum value of 10.0 (and including the end values), that is, a subrange with a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limit listed herein is intended to include all lower numerical limits included therein, and any minimum numerical limit listed in this specification is intended to include all higher numerical limits included therein. Therefore, the applicant reserves the right to amend this specification (including the claims) to explicitly list any subranges included in the range explicitly listed herein.

[0288] Although the present disclosure has been described with reference to example embodiments thereof, it will be understood that the present disclosure should not be limited to these example embodiments, but various changes and modifications may be made by those skilled in the art without departing from the spirit and scope of the present disclosure.

[0289] Therefore, the technical scope of the present disclosure is not intended to be limited to the contents set forth in the detailed description of the specification, but is intended to be defined by the appended 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: at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, In, Sn and Zn; or a compound selected from two or more thereof; or a mixture selected from two or more thereof; or an oxide thereof, The emission layer comprises a compound represented by Formula 1: Formula 1 In formula 1, Any one selected from Ar1 and Ar2 is a substituted or unsubstituted adamantyl group, and the other selected from Ar1 and Ar2 is a substituted or unsubstituted adamantyl group or a substituted or unsubstituted phenyl group, a is an integer selected from 1 to 5, R1 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 ring carbon atoms, and At least one R1 is represented by any one of Formula 2-1 to Formula 2-3: Formula 2-1 Formula 2-2 Formula 2-3 Among them, in formula 2-1, X1 is O or S, In formula 2-2 and formula 2-3, X1 and X2 are each independently NR 13 , O or S, R 13 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, an unsubstituted aryl group having 6 to 20 ring carbon atoms, or an unsubstituted heteroaryl group having 2 to 20 ring carbon atoms, In formula 2-1 to formula 2-3, c and d are each independently an integer selected from 0 to 4, R2 to R9, R 31 and R 32 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 ring carbon atoms, and, -* indicates the location to connect to.

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, In formula 1-1 and formula 1-2, b is an integer selected from 0 to 5, R 11 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 ring carbon atoms, and a and R1 are the same as defined in Formula 1.

3. 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 in, In Formula 1-1A and Formula 1-1B, b and R 11 is the same as defined in formula 1-1, and R 21 and R 22 Each is independently represented by any one of Formula 2-1 to Formula 2-3.

4. The organic electroluminescent device according to claim 2, wherein Formula 1-2 is represented by Formula 1-2A or Formula 1-2B: Formula 1-2A Formula 1-2B in, In Formula 1-2A and Formula 1-2B, R 23 and R 24 Each is independently represented by any one of Formula 2-1 to Formula 2-3.

5. The organic electroluminescent device according to claim 1 , wherein Formula 2-1 is represented by any one of Formula 2-1B and Formula 2-1C: Formula 2-1B Formula 2-1C in, In Formula 2-1B and Formula 2-1C, R2 to R7, R 31 and c are the same as defined in Formula 2-1.

6. The organic electroluminescent device according to claim 1, wherein Formula 2-2 is represented by any one of Formula 2-2A to Formula 2-2C: Formula 2-2A Formula 2-2B Formula 2-2C in, In Formula 2-2A to Formula 2-2C, R2 to R5, R 13 、R 31 、R 32 , c, d and X2 are the same as defined in Formula 2-2.

7. The organic electroluminescent device according to claim 1, wherein Formula 2-3 is represented by any one of Formula 2-3A to Formula 2-3C: Formula 2-3A Formula 2-3B Formula 2-3C in, In Formula 2-3A to Formula 2-3C, R2 to R5, R 13 、R 31 、R 32 , c, d and X2 are the same as defined in Formula 2-3. The organic electroluminescent device according to claim 1 , wherein the emission layer is configured to emit delayed fluorescence.

9. The organic electroluminescent device according to claim 1, wherein the emission layer comprises at least one of the compounds of compound group 1: Compound Group 1

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