Nitrogen-containing compound and organic electroluminescent device comprising the same

Abstract

The present invention provides a nitrogen-containing compound and an organic electroluminescent device including the nitrogen-containing compound. The nitrogen-containing compound according to an embodiment of the present disclosure is represented by Formula 1. In Formula 1, "n" is 0 or 1, and M 1 and M 2 Each is independently represented by Formula 2 or Formula 3: #imgabs0#

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2017-0178632, filed on Dec. 22, 2017, which is hereby incorporated by reference herein in its entirety. Technical Field

[0003] One or more embodiments of the present disclosure relate to an organic electroluminescent device and a nitrogen-containing compound for an organic electroluminescent device. Background Art

[0004] Recently, development of organic electroluminescent devices as image display devices is being actively carried out. Unlike liquid crystal display devices, organic electroluminescent display devices are self-luminous display devices in which holes and electrons injected by a first electrode and a second electrode are recombined in an emission layer, and a light-emitting material including an organic compound in the emission layer emits light to realize display (e.g., realize display of an image).

[0005] When an organic electroluminescent device is applied to a display device, it is desired to reduce a driving voltage and to improve emission efficiency and lifespan, and development of a material for stably achieving improved characteristics of the organic electroluminescent device continues to be desired. Summary of the invention

[0006] One or more embodiments of the present disclosure relate to an organic electroluminescent device and a nitrogen-containing compound for an organic electroluminescent device.

[0007] Embodiments of the present disclosure provide an organic electroluminescent device comprising a first electrode, a hole transport region on the first electrode, an emission layer on the hole transport region, an electron transport region on the emission layer, and a second electrode on the electron transport region, wherein the emission layer comprises a nitrogen-containing compound represented by the following Formula 1:

[0008] Formula 1

[0009]

[0010] In formula 1, Q 1 NAr 1 , O or S, Ar 1 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation, R 1 and R 2each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted phosphinooxy group, a substituted or unsubstituted phosphinothio group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation, wherein the adjacent R 1 and R 2 Each of them can independently combine with adjacent groups to form a ring, "a" and "b" are each independently an integer from 0 to 4, "n" is 0 or 1, and M 1 and M 2 Each is independently represented by the following formula 2 or formula 3:

[0011]

[0012] In formula 2 and formula 3, X 1 To X 6 Each independently is CR 3 or N, X 1 To X 4 At least one of N, R 3 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation, and R 3 One or more of them can combine with adjacent groups to form a ring, W is O, NAr 3 or CAr 4 Ar 5 ,Ar 2 To Ar 5 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation, and Ar 2 To Ar 5 They can independently combine with adjacent groups to form a ring.

[0013] In one embodiment, Formula 2 may be represented by one of the following Formulas 2-1 to 2-3:

[0014]

[0015]

[0016] In Formula 2-1 to Formula 2-3, X 1 and X 2 Each independently is CR 3 or N, where X 1 or X 2 At least one of N, X 7 To X 10 Each independently is CR 6 or N, where X 7 To X 10 At least one of them is N, and R 3 To R 6 Each is independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation.

[0017] In one embodiment, Formula 3 may be represented by one of the following Formulas 3-1 to 3-4:

[0018]

[0019] In formulas 3-1, 3-3 and 3-4, Ar 2 and Ar 5 Each is independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation.

[0020] In one embodiment, Q 1 Can be NAr 1 , and Ar 1 It may be a substituted or unsubstituted phenyl group.

[0021] In one embodiment, Formula 1 may be represented by the following Formula 1-1 or Formula 1-2:

[0022]

[0023]

[0024] In formulas 1-1 and 1-2, Q 1 , R 1 , R 2 、M 1 、M 2 , “n”, “a” and “b” are the same as defined above.

[0025] In one embodiment, "a" may be zero.

[0026] In one embodiment, Formula 1 can be represented by the following Formula 1-3:

[0027]

[0028] In formula 1-3, Q 1 , R 1 , R 2 , "a" and "b" are the same as defined above, Q 2 Definition and Q 1 The definition of Q is the same as 1 and Q 2 Can be the same or different, R 7 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation, "c" is an integer from 0 to 5, and M 3 It is represented by the following formula 4:

[0029]

[0030] In formula 4, X 11 C=O or CR 8 , and R 8 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation.

[0031] In one embodiment, "b" can be 0 or 1, and if "b" is 1, then R 2 Can be used with M 1 same.

[0032] In one embodiment, the nitrogen-containing compound represented by Formula 1 may have a lowest triplet energy level of about 3.0 eV or more.

[0033] In an implementation, the emission layer may include a host and a dopant, and the host may include the nitrogen-containing compound represented by Formula 1 above.

[0034] In one embodiment, the dopant may be a phosphorescent dopant.

[0035] Embodiments of the present disclosure provide a nitrogen-containing compound represented by Formula 1. BRIEF DESCRIPTION OF THE DRAWINGS

[0036] The accompanying drawings are included to provide a further understanding of the present disclosure, and are incorporated into and constitute a part of the specification. The accompanying drawings, together with the specification, illustrate exemplary embodiments of the present disclosure and are used to explain the principles of the present disclosure. In the drawings:

[0037] Figure 1 A cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present disclosure;

[0038] Figure 2 A cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present disclosure; and

[0039] Figure 3 FIG. 1 is a cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present disclosure. DETAILED DESCRIPTION

[0040] With reference to the accompanying drawings, the above-mentioned objects, other objects, features and advantages of the present disclosure will be easily understood according to the exemplary embodiments. However, the present disclosure can be embodied in different forms and should not be interpreted as being limited to the embodiments described herein. On the contrary, exemplary embodiments are provided so that the contents disclosed herein are thorough and complete, and those skilled in the art fully understand the spirit of the present disclosure.

[0041] The same reference numerals indicate the same elements to illustrate each of the accompanying drawings. In the accompanying drawings, the size of the elements may be magnified to make the disclosure clear. It should be understood that although the terms first, second, etc. may be used to describe various elements in this article, these elements should not be limited by these terms. These terms are only used to distinguish one element from another element. For example, the first element discussed below may be referred to as the second element, and similarly, the second element may also be referred to as the first element. As used herein, the singular form is also intended to include the plural form, unless the context clearly indicates otherwise.

[0042] It will be further understood that the terms "comprising" or "including" when used in this specification refer to the presence of the described features, values, steps, operations, elements, components or combinations thereof, but do not exclude the presence or addition of one or more other features, values, steps, operations, elements, components or combinations thereof. It will also be understood that when a layer, film, region, plate, etc. is referred to as being "on" another component, it can be "directly" "on" another component, or there can be intermediate components. In addition, when a layer, film, region, plate, etc. is referred to as being "under" another component, it can be "directly" "under" another component, or there can be intermediate components.

[0043] Expressions such as "at least one of...", "one of..." and "selected from...", when preceding a list of elements, modify the entire list of elements rather than the individual elements in the list. In addition, when describing embodiments of the present invention, the use of "may" refers to "one or more embodiments of the present invention."

[0044] First, refer to Figures 1 to 3 An organic electroluminescent device according to an exemplary embodiment of the present disclosure is explained.

[0045] Figure 1 FIG. 1 is a cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present disclosure. Figure 2 FIG. 1 is a cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present disclosure. Figure 3 FIG. 1 is a cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present disclosure.

[0046] refer to Figures 1 to 3 , the organic electroluminescent device according to the exemplary embodiment of the present disclosure 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 .

[0047] The emission layer EML may include a nitrogen-containing compound according to an embodiment of the present disclosure. However, the embodiments of the present disclosure are not limited thereto. At least one of the one or more organic layers disposed (e.g., placed) between the first electrode EL1 and the second electrode EL2 may include a nitrogen-containing compound according to an embodiment of the present disclosure. For example, the hole transport region HTR may include a nitrogen-containing compound according to an embodiment of the present disclosure.

[0048] Hereinafter, the nitrogen-containing compound according to an embodiment of the present disclosure will be explained in more detail, and then, each layer of the organic electroluminescent device 10 will be explained.

[0049] The nitrogen-containing compound according to an embodiment of the present disclosure may be represented by the following Formula 1:

[0050]

[0051] In formula 1, Q 1 Can be NAr 1 , O or S, Ar 1 may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation, R 1 and R 2and R are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted phosphinooxy group (e.g., a phosphine oxide group), a substituted or unsubstituted phosphinothio group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation, wherein R 1 and R 2 can be independently combined with adjacent groups to form a ring, "a" and "b" can be independently an integer from 0 to 4, "n" is 0 or 1, and M 1 and M 2 They can be independently represented by the following formula 2 or formula 3:

[0052]

[0053] In formula 2, X 1 To X 4 Can be independently CR 3 or N, where X 1 To X 4 At least one of them can be N, R 3 may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation, and R 3 It can combine with adjacent groups to form a ring.

[0054] In formula 3, X 5 and X 6 Can be independently CR 3 or N, R 3 may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation, and R 3 Can combine with adjacent groups to form a ring, W can be O, NAr 3 or CAr 4 Ar 5 ,Ar 2 To Ar 5may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation, and Ar 2 To Ar 5 They can independently combine with adjacent groups to form a ring.

[0055] In this disclosure, Can refer to the moiety to be linked (eg, a binding site).

[0056] In the present disclosure, "substituted or unsubstituted" may refer to an unsubstituted group or a group substituted by at least one substituent selected from the following: a deuterium atom, a halide, 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, an arylamine group, a phosphine oxide group, a phosphinethio group, an alkyl group, an alkenyl group, an aryl group, and a heterocyclic group. In addition, each of the substituents described above may be substituted or unsubstituted. For example, a biphenyl group may be described as an aryl group or a phenyl group substituted by a phenyl group.

[0057] In the present disclosure, the term "forming a ring by combining with an adjacent group" may refer to forming a substituted or unsubstituted hydrocarbon ring, or forming a substituted or unsubstituted heterocyclic ring by combining one group with an adjacent group. The hydrocarbon ring may include an aliphatic hydrocarbon ring and an aromatic hydrocarbon ring. The heterocyclic ring may include an aliphatic heterocyclic ring and an aromatic heterocyclic ring. The hydrocarbon ring and the heterocyclic ring may each independently be a monocyclic ring or a polycyclic ring. In addition, the ring formed by combining with an adjacent group may combine with other rings to form a spiro structure.

[0058] In the present disclosure, the term "adjacent groups" may refer to a pair of substituent groups in which a first substituent is attached to an atom that is directly attached to another atom substituted by a second substituent, a pair of substituent groups attached to the same atom, or a pair of substituent groups in which the first substituent is spatially located closest to the second substituent. For example, in 1,2-dimethylbenzene, two methyl groups may be interpreted as "adjacent groups" to each other, and in 1,1-diethylcyclopentene, two ethyl groups may be interpreted as "adjacent groups" to each other.

[0059] In the present disclosure, the halogen atom may include a fluorine atom, a chlorine atom, a bromine atom and / or an iodine atom, but is not limited thereto.

[0060] In the present disclosure, the alkyl group may be a linear, branched or cyclic group. The carbon number of the alkyl group may be 1 to 30, 1 to 20, 1 to 10 or 1 to 4. The alkyl group may include, but is not limited to, 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.

[0061] In the present disclosure, aryl may refer to a functional group or a substituent derived from an aromatic hydrocarbon ring. The aryl may be a monocyclic aryl or a polycyclic aryl. The number of carbon atoms in the aryl used for ring formation may be 6 to 30, 6 to 20, or 6 to 15. Non-limiting examples of aryl may include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, pentaphenyl, hexaphenyl, biphenylenyl, triphenylenyl, pyrenyl, benzofluoranthenyl, Ji et al.

[0062] In the present disclosure, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure. Non-limiting examples of substituted fluorenyl groups are shown below. However, embodiments of the present disclosure are not limited thereto:

[0063]

[0064] In the present disclosure, the alkyl group in the haloalkyl group, the alkoxy group, the aralkyl group and the alkylthio group may be the same as the alkyl group described above.

[0065] In the present disclosure, the aryl group in the aryloxy group, the arylalkyl group and the arylthio group may be the same as the aryl group described above.

[0066] In the present disclosure, the heteroaryl group may be a heteroaryl group (e.g., a cycloaromatic group) including at least one of O, N, P, Si, or S as a heteroatom. If the heteroaryl group includes two heteroatoms, the two heteroatoms may be the same or different. The carbon number of the ring used to form the heteroaryl group may be 2 to 30 or 2 to 20. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. Examples of polycyclic heteroaryl groups may have a two-ring structure or a three-ring structure. 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, pyrazolopyrazinyl, 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.

[0067] In the present disclosure, silyl groups may include, without limitation, alkylsilyl groups and arylsilyl groups. Examples of silyl groups may include trimethylsilyl groups, triethylsilyl groups, tert-butyldimethylsilyl groups, vinyldimethylsilyl groups, propyldimethylsilyl groups, triphenylsilyl groups, diphenylsilyl groups, phenylsilyl groups, etc. However, embodiments of the present disclosure are not limited thereto.

[0068] In the present disclosure, boryl (boryl group) may include, but is not limited to, alkyl boryl and aryl boryl. Non-limiting examples of boryl may include trimethyl boryl, triethyl boryl, tert-butyl dimethyl boryl, triphenyl boryl, diphenyl boryl, phenyl boryl, and the like.

[0069] In the present disclosure, the alkenyl group may have a straight chain or a branched chain. The carbon number of the alkenyl group is not specifically limited and may be 2 to 30, 2 to 20, or 2 to 10. Non-limiting examples of the alkenyl group may include vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienyl aryl, styryl, styryl vinyl, etc.

[0070] In the present disclosure, the carbon number of the amino group is not specifically limited, but may be 1 to 30. The amino group may include, without limitation, an alkylamino group and an arylamino group. Non-limiting examples of the amino group may include methylamino, dimethylamino, phenylamino, diphenylamino, naphthylamino, 9-methyl-anthrylamino, triphenylamino, and the like.

[0071] In the present disclosure, the phosphinooxy group (eg, phosphine oxide group) may be substituted, for example, with at least one of an alkyl group or an aryl group.

[0072] In the present disclosure, the phosphinothio group may be substituted, for example, with at least one of an alkyl group or an aryl group.

[0073] In formula 1, if "a" is 1, then R 1 may not be a hydrogen atom, and if "b" is 1, then R 2 If "a" is 2 or more, then multiple R 1 The groups may be the same or different, and if "b" is 2 or more, then multiple R 2 The groups may be the same or different.

[0074] In formula 1, if R 1 The group is plural (for example, if there are two or more R 1 group), then two adjacent R 1 The groups may be combined with each other to form a ring, for example, a heterocycle.

[0075] In equations 2 and 3, if R 3 If there are multiple groups, then two adjacent R 3 The groups may be combined with each other to form a ring.

[0076] In formula 2, X 1 To X 4 The number of N in can be 1, 2 or 3 (e.g., 1 To X 4 1, 2 or 3 of them may be nitrogen).

[0077] Formula 2 can be expressed by one of the following Formulas 2-1 to 2-3:

[0078]

[0079] In formula 2-1, X 1 and X 2 Can be independently CR 3 or N, and X 1 or X 2 At least one of them can be N, and R 3 It may be a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation.

[0080] In formula 2-1, R 3 It may be a hydrogen atom, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted nitrogen-containing heteroaryl group. The nitrogen-containing heteroaryl group may be, for example, a substituted or unsubstituted pyridyl group or a substituted or unsubstituted pyrimidyl group, without limitation.

[0081] In formula 2-2, X 1 and X 2 Can be independently CR3 or N, and X 1 or X 2 At least one of N, X 7 To X 10 Can be independently CR 6 or N, and X 7 To X 10 At least one of them can be N, and R 3 and R 6 Each may independently be a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation.

[0082] In formula 2-3, X 1 and X 2 Can be independently CR 3 or N, and X 1 or X 2 At least one of them can be N, and R 3 To R 5 Each may independently be a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation.

[0083] Formula 2-1 can be expressed by one of the following Formulas 2-1-1 to 2-1-3:

[0084]

[0085]

[0086] Formula 2-2 can be represented by, for example, the following formula 2-2-1:

[0087]

[0088] Formula 2-3 can be expressed by one of the following Formulas 2-3-1 to 2-3-4:

[0089]

[0090] In Formula 3, W may be O. However, the embodiments of the present disclosure are not limited thereto, and W may be NAr 3 , and Ar 3 Can be used with Ar 2 In another embodiment, in Formula 2, W can be CAr 4 Ar 5 , and Ar 4 and Ar 5 One of them can be combined with Ar 2 Combine to form a ring.

[0091] Formula 3 can be expressed by one of the following Formulas 3-1 to 3-4:

[0092]

[0093]

[0094] In formula 3-1, Ar 2 It may be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation. 2 For example, it may be substituted or unsubstituted phenyl.

[0095] In formula 3-3, Ar 5 It may be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation. 5 For example, it may be substituted or unsubstituted phenyl.

[0096] In formula 3-4, Ar 5 It may be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation. 5 For example, it may be substituted or unsubstituted phenyl.

[0097] In formula 1, Q 1 Can be NAr 1 , and Ar 1 It can be a substituted or unsubstituted phenyl group. For example, Q 1 Can be NAr 1 , and Ar 1 Q may be a phenyl group substituted with a silyl group or an unsubstituted phenyl group. 1 Can be NAr 1 , and Ar 1 It may be a phenyl group substituted by a triphenylsilyl group or an unsubstituted phenyl group. However, the embodiments of the present disclosure are not limited thereto. In Formula 1, Q 1 Can be O or S.

[0098] Formula 1 can be represented by, for example, the following formula 1-1 or formula 1-2:

[0099]

[0100] In formula 1-1 and formula 1-2, Q 1 , R 1 , R 2 、M 1 、M2 , “n”, “a” and “b” are the same as defined above.

[0101] In formula 1-1 and formula 1-2, if "n" is 1, then M 1 and M 2 However, the embodiments of the present disclosure are not limited thereto.

[0102] For example, "n" can be 1, and M 1 and M 2 It can be represented by the above formula 2-2-1. In another embodiment, "n" can be 1, and M 1 and M 2 It can be expressed by the above formula 3-2.

[0103] Formula 1 can be represented by, for example, the following formula 1-3:

[0104]

[0105] In formula 1-3, Q 1 , R 1 , R 2 , "a" and "b" are the same as defined above, Q 2 Definition and Q 1 The definition of Q is the same as 1 and Q 2 Can be the same or different, R 7 It may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation, and "c" is an integer of 0 to 5.

[0106] In formula 1-3, if "c" is 1, then R 7 may not be a hydrogen atom, and if "c" is 2 or greater, multiple R 7 The groups may be the same or different. "c" may be 0, but the embodiments of the present disclosure are not limited thereto.

[0107] In formula 1-3, M 3 It can be expressed by the following formula 4:

[0108]

[0109] In formula 4, X 11 Can be C=O or CR 8 , and R 8It may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for ring formation.

[0110] In formula 4, if X 11 For C=O, then X 11 and the two N atoms are connected by a single bond, and if X 11 CR 8 , then one of the two N atoms is bound to CR via a double bond 8 connect.

[0111] In formula 4, R 8 It may be a hydrogen atom or a substituted or unsubstituted phenyl group.

[0112] In Formula 1, "a" can be 0. For example, it can be 2 The substituted benzene ring may be 2 Monosubstituted or unsubstituted. "a" may be 1 or greater, and R 1 may be a substituent instead of a hydrogen atom. However, the embodiments of the present disclosure are not limited thereto. For example, R 1 The group may be, but is not limited to, an arylamine group, an arylsilyl group, a phosphinooxy group, a phosphinothio group, an arylboron group, a halogen atom and / or a halogenated alkyl group.

[0113] Formula 1 can be represented by the following formula 1-4:

[0114]

[0115] In formula 1-4, Q 3 Can be O, S or NR 11 , R 9 To R 11 may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, and Q 1 、M 1 , R 2 and "b" are the same as above.

[0116] In Formula 1, "b" may be 0. "b" may be 1, but the embodiments of the present disclosure are not limited thereto. If "b" is 1, then R 2 and M 1 For example, "b" can be 1, and R 2 and M 1 It can be represented by Formula 2-2-1. In another embodiment, "b" can be 1, and R 2 and M 1 It can be expressed by formula 3-2.

[0117] In another embodiment, "b" may be 1 or greater, and R 2 may be a substituent other than a hydrogen atom. For example, R 1 The group may be, but is not limited to, an arylamine group, an arylsilyl group, a phosphinooxy group, a phosphinothio group, an arylboron group, a halogen atom and / or a halogenated alkyl group.

[0118] The nitrogen-containing compound represented by Formula 1 may be at least one selected from the compounds represented in Compound Group 1. However, embodiments of the present disclosure are not limited thereto.

[0119] Compound Group 1

[0120]

[0121]

[0122]

[0123] In the above structures, Ph may refer to a phenyl group.

[0124] The nitrogen-containing compound according to an embodiment of the present disclosure has a triazole, oxadiazole or thiadiazole skeleton (e.g., part), and has a structure in which the electron-withdrawing substituent is substituted with the skeleton (e.g., the above-mentioned part) at an ortho position on the benzene ring. By replacing two types of nitrogen-containing five-membered rings at an ortho position on the benzene ring, the resulting molecular structure can be distorted and the lowest triplet energy level can be increased. Therefore, the nitrogen-containing compound according to an embodiment of the present disclosure can be easily applied as a phosphorescent host material. If the nitrogen-containing compound according to an embodiment of the present disclosure is used as a phosphorescent host material, a high charge mobility can be obtained, and at the same time, the capture of the lowest triplet energy level of the dopant can become possible.

[0125] The nitrogen-containing compound according to an embodiment of the present disclosure may have a lowest triplet energy level (T1) of about 3.0 eV or more.

[0126] Reference again Figures 1 to 3 , an organic electroluminescent device according to an embodiment of the present disclosure will be explained.

[0127] Hereinafter, the above-described nitrogen-containing compound according to an embodiment of the present disclosure will be explained mainly with respect to different features, and the unexplained portion will follow the above explanation in conjunction with the nitrogen-containing compound according to an embodiment of the present disclosure.

[0128] The first electrode EL1 has conductivity. The first electrode EL1 may be a pixel electrode or an anode. The first electrode EL1 may be a transmissive electrode, a semi-transmissive electrode or a reflective electrode. If the first electrode EL1 is a transmissive electrode, the first electrode EL1 may be formed using a transparent metal oxide such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO) and / or indium tin zinc oxide (ITZO). If the first electrode EL1 is a semi-transmissive 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 / Ca, LiF / Al, Mo, Ti, a compound thereof or a mixture thereof (e.g., a mixture of Ag and Mg). Moreover, the first electrode EL1 may include a plurality of layers, including a reflective layer and / or a semi-transmissive layer formed using any of the above materials, or a transparent layer formed using ITO, IZO, ZnO and / or ITZO. For example, the first electrode EL1 may have a triple-layer structure of ITO / Ag / ITO, but embodiments of the present disclosure are not limited thereto.

[0129] The thickness of the first electrode EL1 may be about to about or, for example, about to about

[0130] A hole transport region HTR is 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, or an electron blocking layer.

[0131] The hole transport region HTR may have a single layer formed using a single material, a single layer formed using a plurality of different materials, or a multi-layer structure including a plurality of layers formed using a plurality of different materials.

[0132] For example, the hole transport region HTR may have a single-layer structure such as a hole injection layer HIL or a hole transport layer HTL, and may have a single-layer structure formed using a hole injection material and a hole transport material. In one embodiment, the hole transport region HTR may have a single-layer structure formed using a plurality of different materials, or the following structure laminated from the first electrode EL1: 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.

[0133] The hole transport region HTR may be formed using various methods such as a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Brokett (LB) method, an inkjet printing method, a laser printing method, and / or a laser induced thermal imaging (LITI) method.

[0134] The hole injection layer HIL may include, for example, non-limitingly, phthalocyanine compounds (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-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-styrene sulfonate) (PEDOT / PSS), polyaniline / dodecylbenzene sulfonic acid (PANI / DBSA), polyaniline / camphor sulfonic acid (PANI / CSA), polyaniline / poly(4-styrene sulfonate) (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, tetrakis(pentafluorophenyl)borate, 1,4,5,8,9,12-hexaazatriphenylene hexanitrile (HAT-CN), etc.

[0135] The hole transport layer HTL may include, for example, without limitation, 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"-tri(N-carbazolyl)triphenylamine (TCTA)), N,N'-di(1-naphth-1-yl)-N,N'-diphenylbenzidine (NPB), 4,4'-cyclohexylenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), and the like.

[0136] The electron blocking layer EBL may include, for example, materials known in the art. The electron blocking layer EBL may 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'-diphenylbenzidine (NPD), 4,4'-cyclohexylenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), mCP, etc. In addition, as described above, the electron blocking layer EBL may include a nitrogen-containing compound according to an embodiment of the present disclosure.

[0137] The thickness of the hole transport region HTR may be about to about or, for example, about to about The thickness of the hole injection layer HIL may be 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 If 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 obtained without significantly increasing the driving voltage.

[0138] In addition to the above materials, 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-type dopant. The p-type dopant may be one of a quinone derivative, a metal oxide, or a cyano-containing compound without limitation. Non-limiting examples of p-type dopants may include quinone derivatives (such as tetracyanoquinodimethane (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ)), metal oxides (such as tungsten oxide and / or molybdenum oxide).

[0139] As described above, the hole transport region HTR may further include at least one of a hole buffer layer or an electron blocking layer. The hole buffer layer may compensate for the resonance distance according to the wavelength of light emitted by the emission layer EML and may improve the emission efficiency. Any material included in the hole transport region HTR may be used as the material included in the hole buffer layer. The electron blocking layer is a layer that prevents (or reduces) electron injection from the electron transport region ETR to the hole transport region HTR.

[0140] An emission layer EML may be provided on the hole transport region HTR. The emission layer EML may have, for example, approximately 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.

[0141] The emission layer EML may include the nitrogen-containing compound according to an embodiment of the present disclosure.

[0142] The emission layer EML may include one, two or more nitrogen-containing compounds represented by Formula 1. In addition to the nitrogen-containing compounds represented by Formula 1, the emission layer EML may further include known materials. For example, the emission layer EML may further include a material selected from any one of spiro-DPVBi, 2,2',7,7'-tetra(biphenyl-4-yl)-9,9'-spirobifluorene (spiro-hexaphenyl) (spiro-6P), distyryl-benzene (DSB), distyryl-arene (DSA), polyfluorene (PFO)-based polymers, and poly(p-phenylene vinylene) (PPV)-based polymers. However, embodiments of the present disclosure are not limited thereto.

[0143] The emission layer EML may include a host and a dopant. The host may include a nitrogen-containing compound according to an embodiment of the present disclosure, and the dopant may be a phosphorescent dopant. For example, the nitrogen-containing compound according to an embodiment of the present disclosure may be used as a phosphorescent host material. However, the embodiments of the present disclosure are not limited thereto. For example, the nitrogen-containing compound according to an embodiment of the present disclosure may be used as a material for thermally activated delayed fluorescence.

[0144] The emission layer EML may be, for example, a blue emission layer emitting blue light, However, the embodiments of the present disclosure are not limited thereto, and the EML may be a layer emitting red light or green light.

[0145] In addition to the nitrogen-containing compound according to the embodiment of the present disclosure, the host may further include a host material known in the art. For example, it may further include tris(8-hydroxyquinoline)aluminum (Alq 3), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), poly(N-vinylcarbazole) (PVK), 9,10-di(naphthalene-2-yl)anthracene (AND), 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), distyrylarene (DSA), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), 2-methyl-9,10-bis(naphthalene-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)dibenzofuran (PPF), etc.

[0146] The dopant may include materials known in the art. For example, a metal complex may be included, which includes at least one of iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh) or thulium (Tm). For example, bis[2-(4,6-difluorophenyl)pyridine-C2,N](picolinato)iridium (III) (FIrpic) may be included. The dopant may be a fluorescent dopant. The fluorescent dopant may include, for example, an arylamine compound or a styrylamine compound.

[0147] The electron transport region ETR may be provided on the emission layer EML. The electron transport region ETR may include, without limitation, at least one of a hole blocking layer HBL, an electron transport layer ETL, or an electron injection layer EIL.

[0148] 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 multilayer structure having a plurality of layers formed using a plurality of different materials.

[0149] 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. Further, the electron transport region ETR may have a single-layer structure without limitation, which has a plurality of different materials, or has a structure in which the following are laminated from the emission layer EML: electron transport layer ETL / electron injection layer EIL or hole blocking layer HBL / electron transport layer ETL / electron injection layer EIL. The thickness of the electron transport region ETR may be, for example, about 100 Å. to about

[0150] The electron transport region ETR may be formed using various methods such as a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Brokett (LB) method, an inkjet printing method, a laser printing method, and / or a laser induced thermal imaging (LITI) method.

[0151] If the electron transport region ETR includes an electron transport layer ETL, the electron transport region ETR may include tris(8-hydroxyquinoline)aluminum (Alq 3 ), 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, bis[2-(diphenylphosphine)phenyl]ether oxide (DPEPO), 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-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-hydroxyquinolinol-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), bis(benzoquinolinol-10-hydroxy)beryllium (Bebq 2 ), 9,10-di(naphthalene-2-yl)anthracene (ADN), or a mixture thereof. However, the embodiments of the present disclosure are not limited thereto. The thickness of the electron transport layer ETL may be about to about For example, about to about If the thickness of the electron transport layer ETL satisfies the above range, satisfactory (or appropriate) electron transport characteristics may be obtained without significantly increasing the driving voltage.

[0152] If the electron transport region ETR includes an electron injection layer EIL, the electron transport region ETR may be formed using LiF, 8-hydroxyquinoline lithium (LiQ), Li 2O, BaO, NaCl, CsF, lanthanide metals (such as Yb) or metal halides (such as RbCl and / or RbI). However, the embodiments of the present disclosure are not limited thereto. The electron injection layer EIL may also be formed using a mixture material of an electron transport material and an insulating organic metal salt. The organic metal salt may be a material having an energy band gap of about 4 eV or greater. For example, the 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 1000 nm. to about about to about If the thickness of the electron injection layer EIL satisfies the above range, satisfactory (or appropriate) electron transport characteristics may be obtained without significantly increasing the driving voltage.

[0153] The electron transport region ETR may include a hole blocking layer HBL, as described above. For example, the hole blocking layer HBL may include 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen) and / or bis[2-(diphenylphosphine)phenyl]ether oxide (DPEPO). However, embodiments of the present disclosure are not limited thereto.

[0154] The second electrode EL2 may be 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 electrode or a reflective electrode. If 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., without limitation.

[0155] If the second electrode EL2 is a semi-transmissive electrode or a reflective electrode, the second electrode EL2 may include, for example, Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, a compound containing them, or a mixture thereof (for example, a mixture of Ag and Mg). The second electrode EL2 may have a multi-layer structure including a reflective layer or a semi-transmissive layer formed using any of the above materials and a transparent conductive layer formed using ITO, IZO, ZnO, ITZO, etc.

[0156] Although not shown, the second electrode EL2 may be connected to the auxiliary electrode. If the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.

[0157] In the organic electroluminescent device 10, holes injected by the first electrode EL1 may move to the emission layer EML via the hole transport region HTR, and electrons injected by the second electrode EL2 may move to the emission layer EML via the electron transport region ETR, according to a voltage applied to each of the first electrode EL1 and the second electrode EL2. The electrons and holes are recombined in the emission layer EML to generate excitons, and the excitons may emit light by transitioning from an excited state to a ground state.

[0158] If the organic electroluminescent device 10 is a top emission device, the first electrode EL1 may be a reflective electrode, and the second electrode EL2 may be a transmissive electrode or a semi-transmissive electrode. If the organic electroluminescent device 10 is a bottom emission device, the first electrode EL1 may be a transmissive electrode or a semi-transmissive electrode, and the second electrode EL2 may be a reflective electrode.

[0159] When the organic electroluminescent device 10 according to an embodiment of the present disclosure includes the nitrogen-containing compound represented by Formula 1, high emission efficiency may be achieved.

[0160] Hereinafter, the present disclosure will be explained in more detail with reference to specific preparation methods, embodiments and comparative embodiments. The following embodiments are merely illustrative to help understand the present disclosure, and the scope of the present disclosure is not limited thereto.

[0161] (synthesis example)

[0162] For example, the nitrogen-containing compound according to an exemplary embodiment of the present disclosure may be synthesized as follows. However, the embodiments of the present disclosure are not limited thereto.

[0163] 1. Synthesis of Compound 1

[0164] For example, the nitrogen-containing compound according to an embodiment of the present disclosure, Compound 1, can be synthesized by the following reaction.

[0165]

[0166] In a 200 ml three-necked flask under an argon (Ar) atmosphere, 4.62 g (14.6 mmol) of 3-(2-fluorophenyl)-4,5-diphenyl-4H-1,2,4-triazole, 1.73 g (14.6 mmol) of benzimidazole, 9.54 g (29.3 mmol) of Cs 2 CO 3 and 44 ml of dimethyl sulfoxide (DMSO) and stirred at about 160° C. for about 2 hours. After the resulting mixture was cooled in air, water was added thereto, and the resulting white precipitate was filtered and extracted. The crude product thus obtained was separated by silica gel column chromatography to obtain 5.36 g (yield 89%) of compound 1 as a white solid.

[0167] The molecular weight of compound 1 was determined to be 413 by fast atom bombardment mass spectrometry (FAB-MS). 1 H-NMR (CDCl 3 )The chemical shift (δ) values ​​of compound 1 measured by HPLC were 8.04 (1H), 7.70-7.60 (3H), 7.48 (1H), 7.38 (1H), 7.29 (1H), 7.23-7.16 (5H), 7.06 (1H), 6.97 (1H), 6.82-6.73 (3H), and 6.19 (2H).

[0168] 2. Synthesis of Compound 7

[0169] For example, the nitrogen-containing compound according to an embodiment of the present disclosure, Compound 7, can be synthesized by the following reaction.

[0170]

[0171] Under argon (Ar) atmosphere, 3.64g (11.5mmol) of 3- (2-fluorophenyl) -4,5-diphenyl -4H-1,2,4-triazole, 2.38g (11.5mmol) of 5H-benzimidazole [1,2-a] benzimidazole, 0.703g (29.3mmol) of NaH and 58ml of N- (2-hydroxypropyl) methacrylamide (HPMA) were added to a 200ml three-necked flask and stirred for about 12 hours at about 200°C. After the resulting mixture was cooled in air, water was added thereto, and the resulting white precipitate was filtered and extracted. The crude product thus obtained was separated by silica gel column chromatography to obtain 2.83g (yield 49%) of compound 7 as a white solid.

[0172] The molecular weight of compound 7 was determined to be 502 by FAB-MS. 1 H-NMR (CDCl 3 )The chemical shift (δ) values ​​of compound 7 measured by HPLC were 8.58-8.54 (3H), 8.28 (2H), 7.82-7.75 (2H), 7.68-7.46 (9H), 7.38 (2H), and 7.30-7.19 (4H).

[0173] 3. Synthesis of Compound 9

[0174] For example, the nitrogen-containing compound according to an embodiment of the present disclosure, Compound 9, can be synthesized by the following reaction.

[0175]

[0176] In a 200 ml three-necked flask under an argon (Ar) atmosphere, 3.34 g (10.0 mmol) of 3,5-bis(2-fluorophenyl)-4-phenyl-4H-1,2,4-triazole, 2.36 g (20.0 mmol) of benzimidazole, and 13.03 g (40.0 mmol) of Cs 2 CO 3 and 60 ml of DMSO, and stirred at about 160° C. for about 2 hours. After the resulting mixture was cooled in air, water was added thereto, and a white precipitate was produced thereby. The crude product thus obtained was separated by silica gel column chromatography to obtain 4.29 g (yield 81%) of compound 9 as a white solid.

[0177] The molecular weight of compound 9 was determined to be 529 by FAB-MS. 1 H-NMR (CDCl 3 )The chemical shift (δ) values ​​of compound 9 measured by HPLC were 8.56 (2H), 8.08 (2H), 7.82-7.75 (4H), and 7.68-7.19 (15H).

[0178] 4. Synthesis of Compound 12

[0179] For example, the nitrogen-containing compound according to an embodiment of the present disclosure, Compound 12, can be synthesized by the following reaction.

[0180]

[0181] In a 200 ml three-necked flask under an argon (Ar) atmosphere, 3.34 g (10.0 mmol) of 3,5-bis(2-fluorophenyl)-4-phenyl-4H-1,2,4-triazole, 3.88 g (20.0 mmol) of 2-phenylbenzimidazole, and 13.03 g (40.0 mmol) of Cs 2 CO 3 and 60 ml of DMSO, and stirred at about 160° C. for about 2 hours. After the resulting mixture was cooled in air, water was added thereto, and the resulting white precipitate was filtered and extracted. The crude product thus obtained was separated by silica gel column chromatography to obtain 6.27 g (yield 92%) of compound 12 as a white solid.

[0182] The molecular weight of compound 12 was determined to be 681 by FAB-MS. 1 H-NMR (CDCl 3 )The chemical shift (δ) values ​​of compound 12 measured by HPLC were 8.56 (2H), 8.28 (4H), 7.83-7.75 (6H), 7.68-7.46 (15H), 7.38 (2H), and 7.28 (2H).

[0183] 5. Synthesis of Compound 21

[0184] For example, the nitrogen-containing compound according to an embodiment of the present disclosure, Compound 21, can be synthesized by the following reaction.

[0185]

[0186] In a 200 ml three-necked flask under an argon (Ar) atmosphere, 3.11 g (11.4 mmol) of 2-(2-chlorophenyl)-5-phenyl-1,3,4-thiadiazole, 2.21 g (11.4 mmol) of 2-phenylbenzimidazole, 7.43 g (22.8 mmol) of Cs 2 CO 3 And 23ml of DMSO, and stirred at about 180°C for about 12 hours. After the resulting mixture was cooled in air, water was added thereto, and the resulting white precipitate was filtered and extracted. The crude product thus obtained was separated by silica gel column chromatography to obtain 3.53g (yield 72%) of compound 21 as a white solid.

[0187] The molecular weight of compound 21 was determined to be 430 by FAB-MS. 1 H-NMR (CDCl 3 )The chemical shift (δ) values ​​of compound 21 measured by HPLC were 8.56 (1H), 8.28 (2H), 8.03 (2H), 7.83-7.75 (3H), 7.66 (1H), 7.55-7.48 (8H), 7.28 (1H).

[0188] The above-mentioned synthesis examples are exemplary embodiments, and the reaction conditions can be changed as needed. In addition, the compounds according to the embodiments of the present disclosure can be synthesized using known methods and materials so as to have various substituents. By introducing various substituents into the core structure represented by Formula 1, suitable properties of the organic electroluminescent device can be obtained.

[0189] (Device Manufacturing Example)

[0190] The organic electroluminescent devices of Examples 1 to 5 were manufactured using each of Compounds 1, 7, 9, 12, and 21 as a host material of an emission layer.

[0191] Example compounds

[0192]

[0193] The organic electroluminescent devices of Comparative Examples 1 to 7 were manufactured using each of the comparative compounds c1 to c7 as a host material of an emission layer.

[0194] Comparative compounds

[0195]

[0196] The organic electroluminescent devices according to Examples 1 to 5 and Comparative Examples 1 to 7 were manufactured as follows: a first electrode having a thickness of about 150 nm was formed using ITO, a hole injection layer having a thickness of about 10 nm was formed using HAT-CN, a hole transport layer having a thickness of about 40 nm was formed using NPB, an electron blocking layer having a thickness of about 10 nm was formed using mCP, an emission layer having a thickness of about 20 nm was formed using each example compound or comparative compound doped with 8% FIrpic, a hole blocking layer having a thickness of about 10 nm was formed using DPEPO, an electron transport layer having a thickness of about 30 nm was formed using TPBi, an electron injection layer having a thickness of about 2 nm was formed using LiF, and a second electrode having a thickness of about 120 nm was formed using Al. Each layer was formed by a deposition method under vacuum.

[0197] Table 1

[0198] Main material of the emission layer Maximum transmission efficiency Example 1 Example Compound 1 130％ Example 2 Example Compound 7 120％ Example 3 Example Compound 9 130％ Example 4 Example Compound 12 110％ Example 5 Example Compound 21 110％ Comparative Example 1 Comparative compound c1 100％ Comparative Example 2 Comparative compound c2 105％ Comparative Example 3 Comparative compound c3 80％ Comparative Example 4 Comparative compound c4 70％ Comparative Example 5 Comparative compound c5 50％ Comparative Example 6 Comparative compound c6 80％ Comparative Example 7 Comparative compound c7 60％

[0199] The maximum emission efficiency is based on Comparative Example 1 and is expressed in %.

[0200] Referring to Table 1, Examples 1 to 5 have improved emission efficiency when compared with Comparative Examples 1 to 7. In Comparative Examples 1 and 2, since carbazole or carboline is substituted at the ortho position of the phenyl group substituted by triazole or oxadiazole, the lowest triplet energy level is lowered and the emission efficiency is lowered. In addition, in Comparative Examples 3 to 6, since the substitution position of benzimidazole is meta or para, the distortion of the molecule is reduced, and the triplet energy level is lowered and the emission efficiency is lowered. At the same time, in Comparative Examples 5 and 7, a biphenyl group is included in the molecule, and the lowest triplet energy level is lowered, and as a result, the emission efficiency is lowered.

[0201] The nitrogen-containing compound according to an embodiment of the present disclosure may be used in an emission layer and may improve emission efficiency of an organic electroluminescent device.

[0202] The nitrogen-containing compound according to an embodiment of the present disclosure may be used in an emission layer and may improve the lifespan of an organic electroluminescent device.

[0203] The organic electroluminescent device according to an embodiment of the present disclosure has excellent emission efficiency.

[0204] The nitrogen-containing compound according to an embodiment of the present disclosure may be applied to an organic electroluminescent device and may contribute to improvement of emission efficiency.

[0205] As used herein, the terms "substantially," "about," and similar terms are used as terms of approximation rather than terms of degree, and are intended to take into account the inherent variations in measurements or calculations recognized by those of ordinary skill in the art.

[0206] Moreover, any numerical range described herein is intended to include all sub-ranges of the same numerical precision covered within the range. For example, the range of "1.0 to 10.0" is intended to include all sub-ranges between (and including) the minimum value 1.0 and the maximum value 10.0, that is, having a minimum value greater than or equal to 1.0 and a maximum value less than or equal to 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limit described herein is intended to include all smaller numerical limits covered herein, and any minimum numerical limit described in this specification is intended to include all larger numerical limits covered herein. Therefore, the applicant reserves the right to amend this specification, including the claims, to explicitly state any sub-ranges covered within the range explicitly described herein.

[0207] 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 a person skilled in the art may make various changes and modifications within the spirit and scope of the present invention as defined by the claims and their equivalents.

Claims

1. A nitrogen-containing compound represented by Formula 1: Formula 1 in, In formula 1, Q1 is NAr1, O or S, Ar1 is an unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, R1 and R2 are each independently a hydrogen atom or a deuterium atom, "a" and "b" are each independently an integer from 0 to 4, "n" is 0 or 1, and M1 and M2 are each independently represented by Formula 2-1 or Formula 3-2: Formula 2-1 Among them, in formula 2-1, X1 is CR3, X2 is N, R3 is a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for ring formation, Formula 3-2 and Substituted or unsubstituted refers to an unsubstituted group or a group substituted with at least one substituent selected from the group consisting of a deuterium atom, an alkyl group and an aryl group, wherein the number of carbon atoms in the alkyl group is 1 to 30 and the number of carbon atoms in the aryl group for ring formation is 6 to 30.

2. The nitrogen-containing compound according to claim 1, wherein Formula 1 is represented by Formula 1-1 or Formula 1-2: Formula 1-1 Formula 1-2 Among them, in formula 1-1 and formula 1-2, Q1, R1, R2, M1, M2, "n", "a" and "b" are the same as defined in Formula 1.

3. The nitrogen-containing compound according to claim 1, wherein The nitrogen-containing compound has a lowest triplet energy level of 3.0 eV or greater.

4. The nitrogen-containing compound according to claim 1, wherein The nitrogen-containing compound represented by Formula 1 is at least one compound selected from the following compound group 1: Compound Group 1 Wherein Ph refers to phenyl.

5. An organic electroluminescent device, comprising: a first electrode; a hole transport region on the first electrode; an emission layer on the hole transport region, wherein the emission layer comprises a nitrogen-containing compound according to any one of claims 1 to 4; An electron transport region on the emissive layer; and a second electrode on the electron transport region, The first electrode and the second electrode are each independently a transmissive electrode, a semi-reflective electrode or a reflective electrode, and wherein: The transmissive electrode comprises at least one selected from the group consisting of indium tin oxide, indium zinc oxide, zinc oxide, and indium tin zinc oxide; and The semi-transmissive electrode and the reflective electrode each independently include: selected from: Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, their compounds or their mixtures.

6. The organic electroluminescent device according to claim 5, wherein: The emission layer includes a host and a dopant, and The host comprises the nitrogen-containing compound according to any one of claims 1 to 4.

7. The organic electroluminescent device according to claim 6, wherein: The dopant is a phosphorescent dopant.

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