Organic electroluminescent device and amine compound for use in organic electroluminescent device

Abstract

The present application provides an amine compound represented by the following formula 1 and an organic electroluminescent device. The organic electroluminescent device includes a first electrode; a hole transport region on the first electrode and containing the amine compound represented by formula 1; 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, [Formula 1]

Description

[0001] Cross - reference to related applications

[0002] Korean Patent Application No. 10 - 2018 - 0108393, filed with the Korean Intellectual Property Office on September 11, 2018 and entitled "Organic Electroluminescent Device and Amine Compound for Organic Electroluminescent Device", is incorporated herein by reference in its entirety. Technical field

[0003] Embodiments relate to an amine compound and an organic electroluminescent device including the amine compound. Background art

[0004] The development of organic electroluminescent displays for image display is being actively carried out. Organic electroluminescent displays are different from liquid crystal displays and are called self - emissive displays, which achieve display by recombining holes and electrons injected from a first electrode and a second electrode in an emission layer and emitting light from a light - emitting material containing an organic compound in the emission layer.

[0005] In the application of using organic electroluminescent devices for displays, a reduction in the driving voltage of organic electroluminescent devices, an improvement in emission efficiency, and an extension of lifetime are required, and there is also an ongoing need to develop materials that can stably achieve these requirements in organic electroluminescent devices. Summary of the invention

[0006] Embodiments relate to an amine compound represented by the following formula 1,

[0007] [Formula 1]

[0008]

[0009] In Formula 1, R1 may be a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, R2 and R3 may each independently be a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 40 ring carbon atoms, and R4 to R 11Each independently may be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 40 ring carbon atoms, or may combine with adjacent groups to form a ring. In Formula 1, Ar1 and Ar2 each independently may be a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 40 ring carbon atoms, L may be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, and n may be an integer from 0 to 4.

[0010] In an exemplary embodiment, Formula 1 may be represented by the following Formula 1-1 or Formula 1-2,

[0011] [Formula 1-1]

[0012]

[0013] [Formula 1-2]

[0014]

[0015] In Formula 1-1 and Formula 1-2, R1 to R 11 , Ar1, Ar2, L and n are the same as defined in Formula 1.

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

[0017] [Formula 2-1]

[0018]

[0019] [Formula 2-2]

[0020]

[0021] In Formula 2-1 and Formula 2-2, X and Y each independently may be a hydrocarbon ring having 6 to 40 ring carbon atoms, or a heterocycle having 2 to 40 ring carbon atoms, R 12 and R 13Each may independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 40 ring carbon atoms, p and q may each independently be an integer from 0 to 3, and R1 to R 11 , Ar1, Ar2, L and n are the same as defined in Formula 1.

[0022] In an exemplary embodiment, Formula 2-1 and Formula 2-2 may be represented by the following Formula 2-1A and Formula 2-2A, respectively,

[0023] [Formula 2-1A]

[0024]

[0025] [Formula 2-2A]

[0026]

[0027] In Formula 2-1A and Formula 2-2A, R 12 and p are the same as defined in Formula 2-1, R 13 and q are the same as defined in Formula 2-2, and R1 to R 11 , Ar1, Ar2, L and n are the same as defined in Formula 1.

[0028] In an exemplary embodiment, in Formula 1, R1 may be an unsubstituted phenyl group.

[0029] In an exemplary embodiment, in Formula 1, R2 and R3 may each independently be an unsubstituted phenyl group, an unsubstituted dibenzofuranyl group, or an unsubstituted dibenzothiophenyl group.

[0030] In an exemplary embodiment, in Formula 1, R2 and R3 may be the same as each other.

[0031] In an exemplary embodiment, in Formula 1, Ar1 and Ar2 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolinyl group, or a substituted or unsubstituted fluorenyl group.

[0032] In an exemplary embodiment, in Formula 1, L may be a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted divalent dibenzofuran group.

[0033] In an exemplary embodiment, an organic electroluminescent device may include a first electrode; a hole transport region on the first electrode and including an amine compound according to the exemplary embodiment; 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.

[0034] In an exemplary embodiment, the hole transport region may include a hole injection layer disposed between the first electrode and the emission layer and a hole transport layer disposed between the hole injection layer and the emission layer, and the hole transport layer may include an amine compound according to the exemplary embodiment.

[0035] In an exemplary embodiment, the emission layer may include an anthracene derivative represented by the following Formula 3,

[0036] [Formula 3]

[0037]

[0038] In Formula 3, R 21 to R 30 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, or may form a ring by bonding to each other through adjacent groups, and c and d may each independently be an integer from 0 to 5. [[ID=P25]]BRIEF DESCRIPTION OF THE DRAWINGS

[0039] Features will become apparent to those skilled in the art by describing exemplary embodiments in detail with reference to the accompanying drawings, in which:

[0040] Figure 1 A schematic cross-sectional view of an organic electroluminescent device according to the exemplary embodiment is illustrated;

[0041] Figure 2 A schematic cross-sectional view of an organic electroluminescent device according to the exemplary embodiment is illustrated; and

[0042] Figure 3 A schematic cross-sectional view of an organic electroluminescent device according to the exemplary embodiment is illustrated. DETAILED DESCRIPTION

[0043] Exemplary embodiments will now be described more fully hereinafter with reference to the accompanying drawings; however, they may be embodied in different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the exemplary implementations to those skilled in the art. The same reference numerals refer to the same elements throughout.

[0044] It should be understood that although the terms first, second, etc. may be used herein to describe different elements, these elements should not be limited by these terms. These terms are only used to distinguish one element from another. For example, the first element discussed below may be referred to as the second element, and similarly, the second element may be referred to as the first element. As used herein, the singular forms are also intended to include the plural forms unless the context clearly indicates otherwise.

[0045] It will be further understood that when used in this specification, the terms "comprising" or "having" specify the presence of the stated features, numbers, steps, operations, elements, components, or combinations thereof, but do not preclude the presence or addition of one or more other features, numbers, steps, operations, elements, components, or combinations thereof. It should also be understood that when a layer, film, region, plate, etc. is referred to as being "on" another component, it can be "directly" on the other component, or there can also be an intervening layer.

[0046] In the present disclosure, "*" means the position to be connected.

[0047] In the present disclosure, "substituted or unsubstituted" may mean unsubstituted or substituted with at least one substituent selected from deuterium, halogen, cyano, nitro, amino, silyl, boron, phosphine oxide, phosphine sulfide, alkyl, alkenyl, alkoxy, aryloxy, alkylthio, arylthio, hydrocarbon ring, aryl, and heterocyclic groups. In addition, each of the substituents exemplified above may be substituted or unsubstituted. For example, biphenyl may be interpreted as an aryl or phenyl substituted with a phenyl group.

[0048] In the present disclosure, examples of halogen atoms are fluorine atoms, chlorine atoms, bromine atoms, or iodine atoms.

[0049] In the present disclosure, an alkyl group may have a straight-chain, branched-chain, or cyclic form. The number of carbon atoms in the alkyl group may be from 1 to 50, from 1 to 30, from 1 to 20, from 1 to 10, or from 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-butyl octyl, 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-butyldecyl, 2-hexyldecyl, 2-octyldecyl, 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.

[0050] In the present disclosure, a hydrocarbon ring may mean an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The hydrocarbon ring does not contain a heteroatom and may be a ring containing 5 to 60 ring carbon atoms. The hydrocarbon ring may be a monocyclic or polycyclic ring.

[0051] In the present disclosure, a heterocyclic ring includes an aliphatic heterocyclic ring and an aromatic heterocyclic ring. The heterocyclic ring may be a monocyclic or polycyclic ring. The heterocyclic ring contains at least one heteroatom for forming the ring, and the number of carbon atoms for forming the ring in the heterocyclic ring may be from 2 to 60 and the number of heteroatoms in the heterocyclic ring may be from 1 to 20, from 1 to 10, or from 1 to 5, such as 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0052] In the present disclosure, an aryl group means any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl or a polycyclic aryl. The number of carbon atoms for forming the ring in the aryl group may be from 6 to 40, from 6 to 30, from 6 to 20, or from 6 to 15. Examples of the aryl group may include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, quaterphenyl, quinquephenyl, sexiphenyl, benzophenanthryl, pyrenyl, benzo[a]pyrenyl, Base etc.

[0053] In the present disclosure, the fluorenyl group may be substituted, and two substituents may combine with each other to form a spiro structure. Examples of the substituted fluorenyl group may include the following groups.

[0054]

[0055] In the present disclosure, the heteroaryl group may be a heteroaryl containing at least one of O, N, P, Si, and S as a heteroatom. The number of carbon atoms for forming the ring of the heteroaryl group may be 2 to 40, 2 to 30, or 2 to 20, and the number of heteroatoms of the heteroaryl group may be 1 to 20, 1 to 10, or 1 to 5, such as 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. The heteroaryl group may be a monocyclic heteroaryl or a polycyclic heteroaryl. The polycyclic heteroaryl may have, for example, a bicyclic or tricyclic structure. Examples of the heteroaryl group may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, N-arylcarbazolyl, N-heteroarylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuryl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, dibenzothiolyl, dibenzofuryl, etc.

[0056] In the present disclosure, the silyl group includes alkylsilyl and arylsilyl. Examples of the silyl group may include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc.

[0057] In the present disclosure, the oxy group may include alkoxy and aryloxy. The alkoxy group may have a straight-chain, branched-chain, or cyclic form. The number of carbon atoms of the alkoxy group is not particularly limited and may be, for example, 1 to 20, or 1 to 10. Examples of the alkoxy group may include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, etc.

[0058] In the present disclosure, the above examples of the aryl group can be applied to the aryl group in the aryloxy. The number of carbon atoms for forming the ring of the aryloxy group is not particularly limited and may be, for example, 6 to 30. For example, the aryloxy group may be a benzyloxy group.

[0059] In the present disclosure, the term "forming a ring by binding adjacent groups to each other" may mean forming a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring by binding adjacent groups to each other. The hydrocarbon ring includes an aliphatic hydrocarbon ring and an aromatic hydrocarbon ring. The heterocyclic ring includes an aliphatic heterocyclic ring and an aromatic heterocyclic ring. The ring formed by binding adjacent groups may be a monocyclic or polycyclic ring. In addition, the ring formed by binding adjacent groups may be connected to another ring to form a spiro structure.

[0060] In the present disclosure, the term "adjacent group" may mean a substituent on an atom directly bonded to another atom substituted with a corresponding substituent, another substituent on an atom substituted with a corresponding substituent, or a substituent spatially arranged at the position closest to the corresponding substituent. For example, the two methyl groups in 1,2-dimethylbenzene may be interpreted as "adjacent groups", and the two ethyl groups in 1,1-diethylcyclopentene may be interpreted as "adjacent groups".

[0061] Hereinafter, an organic electroluminescent device according to an exemplary embodiment and an amine compound according to an exemplary embodiment included therein will be described with reference to the accompanying drawings.

[0062] Figures 1 to 3 Each of [the figures] is a schematic cross-sectional view illustrating an organic electroluminescent device according to an exemplary embodiment.

[0063] Referring to Figures 1 to 3 , an organic electroluminescent device 10 according to an exemplary embodiment may include a first electrode EL1, a hole transport region HTR, an emission layer EML, an electron transport region ETR, and a second electrode EL2 laminated in order.

[0064] The first electrode EL1 and the second electrode EL2 are disposed opposite to each other, and a plurality of organic layers may be disposed between the first electrode EL1 and the second electrode EL2. The plurality of organic layers may include a hole transport region HTR, an emission layer EML, and an electron transport region ETR.

[0065] The organic electroluminescent device 10 according to an exemplary embodiment may contain an amine compound according to an exemplary embodiment in the hole transport region HTR disposed between the first electrode EL1 and the second electrode EL2.

[0066] Compared with Figure 1 , Figure 2 shows a schematic cross-sectional view illustrating an organic electroluminescent device 10 according to an exemplary embodiment, in which 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. In addition, compared with Figure 1 , Figure 3The drawing shows a schematic cross-sectional view of an organic electroluminescent device 10 according to an exemplary embodiment, in which a hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL, and an electron blocking layer EBL, and an electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL, and a hole blocking layer HBL. In the organic electroluminescent device 10 according to the exemplary embodiment, the hole transport layer HTL may contain an amine compound according to the exemplary embodiment described below.

[0067] Although not shown, in the organic electroluminescent device 10 according to the exemplary embodiment, the hole transport layer HTL may include a plurality of sub-layers (not shown) for hole transport, and a sub-layer (not shown) adjacent to the emission layer EML among the plurality of sub-layers for hole transport may contain an amine compound according to the exemplary embodiment described below.

[0068] The first electrode EL1 has conductivity. The first electrode EL1 may be formed of a metal alloy or a conductive compound. The first electrode EL1 may be an anode. The first electrode EL1 may also be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a semi-transmissive reflective electrode, or a reflective electrode. If the first electrode EL1 is a transmissive electrode, the first electrode EL1 may contain a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO). If the first electrode EL1 is a semi-transmissive reflective electrode or a reflective electrode, the first electrode EL1 may contain 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 (for example, a mixture of Ag and Mg). Additionally, the first electrode EL1 may have a structure including a plurality of layers, the plurality of layers including a reflective layer or a semi-transmissive reflective layer formed using the above materials, and a transparent conductive layer formed using ITO, IZO, ZnO, or ITZO. For example, the first electrode EL1 may have a three-layer structure of ITO / Ag / ITO. The thickness of the first electrode EL1 may be about to about For example, about to about

[0069] The hole transport region HTR is 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 (not shown), and an electron blocking layer EBL.

[0070] The hole transport region HTR may have a single-layer structure formed of a single material, a single-layer structure formed of a plurality of different materials, or a multi-layer structure including a plurality of layers formed of a plurality of different materials.

[0071] 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 using a hole injection material and a hole transport material. In addition, the hole transport region HTR may have a single-layer structure formed using a variety of different materials, or a laminated structure of a hole injection layer HIL / hole transport layer HTL, a hole injection layer HIL / hole transport layer HTL / hole buffer layer (not shown), a hole injection layer HIL / hole buffer layer (not shown), a hole transport layer HTL / hole buffer layer, or a hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL laminated in order from the first electrode EL1.

[0072] The hole transport region HTR can be formed using various methods (e.g., vacuum deposition method, spin coating method, casting method, Langmuir-Blodgett (LB) method, inkjet printing method, laser printing method, and laser-induced thermal imaging (LITI) method).

[0073] In the organic electroluminescent device 10 according to an exemplary embodiment, the hole transport region HTR may contain an amine compound represented by the following formula 1.

[0074] [Formula 1]

[0075]

[0076] The amine compound according to an exemplary embodiment may include a phenazasiline moiety and an arylamine moiety

[0077] In Formula 1, R1 may be a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, and R2 and R3 may each independently be a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 40 ring carbon atoms.

[0078] For example, in Formula 1, R1 may be a substituted or unsubstituted phenyl group. For example, R1 may be an unsubstituted phenyl group.

[0079] In the amine compound according to an exemplary embodiment represented by Formula 1, R2 and R3 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group. For example, R₂ and R₃ may each independently be an unsubstituted phenyl group, an unsubstituted dibenzofuranyl group, or an unsubstituted dibenzothiophenyl group.

[0080] In the amine compound according to an exemplary embodiment, R2 and R3 may be the same as each other. For example, both R2 and R3 may be unsubstituted phenyl groups, both R2 and R3 may be unsubstituted dibenzofuranyl groups, or both R2 and R3 may be unsubstituted dibenzothiophenyl groups. R2 and R3 may be different from each other.

[0081] In Formula 1, R4 to R 11 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 40 ring carbon atoms, or may combine with adjacent groups to form a ring.

[0082] For example, in Formula 1, R4 to R 11 the adjacent groups among them may combine with each other to form a hydrocarbon ring or a heterocyclic ring. R4 to R 11 the adjacent groups among them may combine with the phenazasiline moiety to form a fused ring.

[0083] In an exemplary embodiment, for example, except at the positions of the arylamine moiety, R4 to R 11 in Formula 1 may be hydrogen atoms.

[0084] In the amine compound represented by Formula 1, Ar1 and Ar2 may each independently be a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 40 ring carbon atoms. In the amine compound according to an exemplary embodiment, Ar1 and Ar2 may be the same as or different from each other.

[0085] For example, in the amine compound according to an exemplary embodiment, Ar1 and Ar2 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolinyl group, or a substituted or unsubstituted fluorenyl group.

[0086] For example, Ar1 and Ar2 can each independently be an unsubstituted phenyl group, a phenyl group substituted with a halogen atom, a phenyl group substituted with a naphthyl group, a phenyl group substituted with a carbazole group, an unsubstituted naphthyl group, an unsubstituted phenanthryl group, an unsubstituted biphenyl group, a biphenyl group substituted with a phenyl group, an unsubstituted terphenyl group, an unsubstituted dibenzofuranyl group, an unsubstituted dibenzothiophenyl group, or a fluorenyl group substituted with a phenyl group.

[0087] In Formula 1, L can be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, and n can be an integer from 0 to 4, for example an integer from 1 to 4. In an exemplary embodiment, L can be a direct bond. In the present disclosure, a direct bond can be a single bond.

[0088] For example, L can be a substituted or unsubstituted phenylene group, or a substituted or unsubstituted divalent dibenzofuran group. For example, L can be a direct bond, an unsubstituted phenylene group, or an unsubstituted divalent dibenzofuran group.

[0089] In Formula 1, n can be 0 or 1, for example 1. If n is an integer of 2 or greater than 2, then multiple Ls can be the same as or different from each other.

[0090] In an exemplary embodiment, the amine compound can be represented by a combination of the following formulas (the phenazasiline moiety and the amine moiety are illustrated separately), where the amine moiety –(L) n * in NAr1Ar2 is a bond that is connected to a ring carbon atom of the phenazasiline moiety at one of R8, R9, R 10 or R 11 :

[0091] and the other three of R8 to R 11 each independently are a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 40 ring carbon atoms, or form a ring by bonding with adjacent groups to each other.

[0092] The amine compound according to the exemplary embodiment represented by Formula 1 can be represented by the following Formula 1-1 or Formula 1-2.

[0093] [Formula 1-1]

[0094]

[0095] [Formula 1-2]

[0096]

[0097] The positions where Formula 1-1 and Formula 1-2 bind to the amine moiety in the phenazasiline moiety are different from each other. Formula 1-1 shows the case where the amine moiety binds to phenazasiline at the position of R 10 in Formula 1. Formula 1-2 shows the case where the amine moiety binds to phenazasiline at the position of R9 in Formula 1.

[0098] The above description of Formula 1 can be applied to R1 to R 11 、Ar1, Ar2, L, and n in Formula 1-1 and Formula 1-2.

[0099] Formula 1 can also be represented by the following Formula 2-1 or Formula 2-2.

[0100] [Formula 2-1]

[0101]

[0102] [Formula 2-2]

[0103]

[0104] Formula 2-1 and Formula 2-2 show the case where adjacent groups among R4 to R 11 bind to each other to form a ring. For example, in Formula 2-1 and Formula 2-2, adjacent groups among R4 to R 11 bind to each other to form a fused ring with phenazasiline.

[0105] Formula 2-1 shows the case where R9 and R 10 of Formula 1 bind to each other to form a fused ring with phenazasiline. Formula 2-2 shows the case where R5 and R6 of Formula 1 bind to each other to form a fused ring with phenazasiline.

[0106] In Formula 2-1, X can be a hydrocarbon ring having 6 to 40 ring carbon atoms, or a heterocyclic ring having 2 to 40 ring carbon atoms. For example, X can be an aryl group having 6 to 40 ring carbon atoms, or a heteroaryl group having 2 to 40 ring carbon atoms.

[0107] In Formula 2-1, R 12It may be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 40 ring carbon atoms. In addition, in Formula 2-1, p may be an integer from 0 to 3.

[0108] In Formula 2-1, if p is an integer of 2 or greater than 2, then multiple Rs 12 may be the same as or different from each other.

[0109] The above description regarding Formula 1 can be applied to R1 to R8, R 11 , Ar1, Ar2, L, and n in Formula 2-1.

[0110] Formula 2-1 can be represented by the following Formula 2-1A.

[0111] [Formula 2-1A]

[0112]

[0113] Formula 2-1A shows the case where X in Formula 2-1 forms a heterocycle. X in Formula 2-1 may be a hydrocarbon ring bonded to phenazasiline.

[0114] In Formula 2-2, Y may be a hydrocarbon ring having 6 to 40 ring carbon atoms, or a heterocycle having 2 to 40 ring carbon atoms. For example, Y may be an aryl group having 6 to 40 ring carbon atoms, or a heteroaryl group having 2 to 40 ring carbon atoms.

[0115] In Formula 2-2, R 13 may be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 40 ring carbon atoms. In addition, in Formula 2-2, q may be an integer from 0 to 3.

[0116] In Formula 2-2, if q is an integer of 2 or greater than 2, then multiple Rs 13 may be the same as or different from each other.

[0117] The above description regarding Formula 1 can be applied to R1 to R4, R7 to R11 , Ar1, Ar2, L, and n.

[0118] Formula 2-2 can be represented by the following Formula 2-2A.

[0119] [Formula 2-2A]

[0120]

[0121] Formula 2-2A shows the case where Y in Formula 2-2 forms a hydrocarbon ring. Y in Formula 2-2 can be a heterocyclic ring bonded to phenazasiline.

[0122] The amine compound according to an exemplary embodiment may include a phenazasiline moiety. The amine compound according to an exemplary embodiment may be a monoamine compound having a fused ring including a phenazasiline moiety as a substituent.

[0123] The amine compound according to an exemplary embodiment includes both a phenazasiline moiety and an arylamine moiety. The amine compound may exhibit a long lifetime and provide enhanced efficiency to a device using the amine compound.

[0124] Without being bound by theory, it is believed that by introducing a phenazasiline moiety having excellent heat resistance and charge resistance into an arylamine moiety having an extended lifetime property, the amine compound according to an exemplary embodiment has enhanced high-temperature resistance and charge resistance, and thus, it can be used as a material for an organic electroluminescent device having a further extended lifetime. In addition, it is believed that the nitrogen atom contained in the phenazasiline moiety enhances the hole transport ability of the entire molecule of the amine compound, thereby increasing the chance of recombination of holes and electrons in the emission layer of the organic electroluminescent device, which enables the organic electroluminescent device using the amine compound according to an exemplary embodiment to have improved emission efficiency.

[0125] The amine compound according to an exemplary embodiment represented by Formula 1 can be any of the compounds represented by the following Compound Group A and Compound Group B. Accordingly, the organic electroluminescent device according to an exemplary embodiment may include at least one of the compounds represented by the following Compound Group A and Compound Group B in the hole transport region HTR.

[0126] In Compound Group A, the amine moiety is connected at the R 10 position of Formula 1. In Compound Group B, the amine moiety is connected at the R9 position of Formula 1.

[0127] [Compound Group A]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136] [Group B of Compounds]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143] In Figures 1 to 3 organic electroluminescent device 10 according to an exemplary embodiment shown therein, the hole transport region HTR may include one or more than one of the amine compounds represented in Group A of Compounds and Group B of Compounds. In addition to the amine compounds represented in Group A of Compounds and Group B of Compounds, the hole transport region HTR may further include suitable materials.

[0144] If the organic electroluminescent device 10 according to an exemplary embodiment includes multiple layers in the hole transport region HTR, at least one layer of the multiple layers included in the hole transport region HTR may include the amine compound according to an exemplary embodiment described above. For example, the amine compound according to an exemplary embodiment described above may be included in a layer adjacent to the emission layer EML among the multiple layers included in the hole transport region HTR. A layer that does not include the amine compound according to an exemplary embodiment among the multiple layers may include a suitable hole injection material or a suitable hole transport material. In addition, a layer that includes the amine compound according to an exemplary embodiment may further include a suitable hole injection material or a suitable hole transport material.

[0145] For example, an amine compound according to an exemplary embodiment may be included in a hole transport layer HTL of a hole transport region HTR. Further, if the hole transport layer HTL includes a plurality of organic layers, the amine compound according to the exemplary embodiment may be included in a layer adjacent to an emission layer EML among the plurality of organic layers.

[0146] For example, if an organic electroluminescent device 10 according to an exemplary embodiment includes a hole injection layer HIL and a hole transport layer HTL in a hole transport region HTR, the amine compound according to the exemplary embodiment may be included in the hole transport layer HTL. If the organic electroluminescent device 10 according to the exemplary embodiment includes a hole injection layer HIL, a hole transport layer HTL, and an electron blocking layer EBL in a hole transport region HTR, the amine compound according to the exemplary embodiment may be included in the electron blocking layer EBL.

[0147] In the organic electroluminescent device 10 according to the exemplary embodiment, if the hole transport layer HTL contains the amine compound according to the exemplary embodiment, the hole injection layer HIL may contain a suitable hole injection material. For example, the hole injection layer HIL may contain triphenylamine-containing polyether ketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium tetrakis(pentafluorophenyl)borate (PPBI), N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine (DNTPD), a phthalocyanine compound (such as copper phthalocyanine), 4,4',4''-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPB), N,N'-bis(1-naphthyl)-N,N'-diphenyl-4,4'-diamine (α-NPD), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4''-tris(N,N-2-naphthylphenylamino)-triphenylamine (2-TNATA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN), 4,4',4''-tris(N-(1-naphthyl)-N-phenylamino)-triphenylamine (1-TNATA), etc.

[0148] In the organic electroluminescent device 10 according to an exemplary embodiment, in addition to the amine compound according to the exemplary embodiment, the hole transport layer HTL may further include a suitable hole transport material. For example, the hole transport layer HTL may include 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC); carbazole derivatives such as N-phenylcarbazole, polyvinylcarbazole; fluorine-based derivatives; N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD); triphenylamine-based derivatives such as 4,4',4''-tris(N-carbazolyl)triphenylamine (TCTA); N,N'-di(naphthalen-1-yl)-N,N'-diphenyl-benzidine (NPB); 4,4'-cyclohexylidenebis[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), etc.

[0149] As described above, in the organic electroluminescent device 10 according to an exemplary embodiment, in addition to the hole injection layer HIL and the hole transport layer HTL, the hole transport region HTR may further include at least one of a hole buffer layer and an electron blocking layer EBL. The hole buffer layer may compensate for the optical resonance distance according to the wavelength of the light emitted from the emission layer EML and enhance the light emission efficiency. The material included in the hole transport region HTR may be used as the material included in the hole buffer layer.

[0150] If the hole transport region HTR further includes an electron blocking layer EBL disposed between the hole transport layer HTL and the emission layer EML, the electron blocking layer EBL may prevent electrons from being injected from the electron transport region ETR into the hole transport region HTR.

[0151] In the organic electroluminescent device 10 according to an exemplary embodiment, if the hole transport region HTR includes an electron blocking layer EBL, the electron blocking layer EBL may include an amine compound according to an exemplary embodiment. In addition to the amine compound according to an exemplary embodiment, the electron blocking layer EBL may further include suitable materials in the art. The electron blocking layer EBL may include, for example, carbazole derivatives such as N-phenylcarbazole, polyvinylcarbazole; fluorine-based derivatives; N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD); triphenylamine-based derivatives such as 4,4',4''-tris(N-carbazolyl)triphenylamine (TCTA); N,N'-di(naphthalen-1-yl)-N,N'-diphenyl-benzidine (NPD); 4,4'-cyclohexylidenebis[N,N-bis(4-methylphenyl)aniline] (TAPC); 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD); or mCP, etc.

[0152] In the organic electroluminescent device 10 according to an exemplary embodiment, if the hole transport region HTR has a single layer, the hole transport region HTR may include an amine compound according to an exemplary embodiment. In this case, the hole transport region HTR may further include a suitable hole injection material or a suitable hole transport material.

[0153] 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 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 hole transport properties can be obtained without a significant increase in the driving voltage.

[0154] In addition to the materials described above, the hole transport region HTR may further include a charge generation material to improve conductivity. The charge generation material may be uniformly or non-uniformly dispersed in the hole transport region HTR. The charge generation material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, or a cyanide group-containing compound. For example, non-limiting examples of the p-dopant may include quinone derivatives (such as tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ)), metal oxides (such as tungsten oxide and molybdenum oxide).

[0155] The emission layer EML is on the hole transport region HTR. The thickness of the emission layer EML may be, for example, about to about The emission layer EML may have a single-layer structure formed of a single material, a single-layer structure formed of multiple different materials, or a multi-layer structure having multiple layers formed of multiple different materials.

[0156] The emission layer EML may emit one of red light, green light, blue light, white light, yellow light, or cyan light. The emission layer EML may include a fluorescent material or a phosphorescent material.

[0157] In the organic electroluminescent device 10 according to an exemplary embodiment, the emission layer EML may include an anthracene derivative, a pyrene derivative, a fluoranthene derivative, a derivative, a dihydrobenzanthracene derivative, or a benzophenanthrene derivative. For example, the emission layer EML may include an anthracene derivative or a pyrene derivative.

[0158] The emission layer EML may include an anthracene derivative represented by the following formula 3.

[0159] [Formula 3]

[0160]

[0161] In formula 3, R 21 to R 30 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, or may be combined with adjacent groups to form a ring. At the same time, R 21 to R 30 may be combined with adjacent groups to form a saturated hydrocarbon ring or an unsaturated hydrocarbon ring.

[0162] In formula 3, c and d may each independently be an integer from 0 to 5.

[0163] The compound represented by Formula 3 can be any one of the compounds represented by the following Formula 3-1 to Formula 3-12.

[0164]

[0165] In Figures 1 to 3 in the organic electroluminescent device 10 according to an exemplary embodiment shown, the emission layer EML may include a host and a dopant, and the emission layer EML may include the compound represented by Formula 3 described above as a host material.

[0166] The emission layer EML may further include a suitable material as a host material. For example, the emission layer EML may include at least one of bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 4,4'-bis(carbazol-9-yl)biphenyl (CBP), 1,3-bis(carbazol-9-yl)benzene (mCP), 2,8-bis(diphenylphosphoryl)dibenzofuran (PPF), 4,4',4''-tris(carbazol-9-yl)-triphenylamine (TCTA), and 1,3,5-tris(N-phenylbenzimidazol-zo-2-yl)benzene (TPBi) as a host material. For example, tris(8-hydroxyquinolinato)aluminum (Alq3), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), poly(N-vinylcarbazole) (PVK), 9,10-bis(naphthalen-2-yl)anthracene (ADN), 4,4',4''-tris(carbazol-9-yl)-triphenylamine (TCTA), 1,3,5-tris(N-phenylbenzimidazol-zo-2-yl)benzene (TPBi), 3-tert-butyl-9,10-bis(naphthalen-2-yl)anthracene (TBADN), stilbene-substituted arylide (DSA), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH2), hexaphenylcyclotrisiloxane (DPSiO3), octaphenylcyclotetrasiloxane (DPSiO4), 2,8-bis(diphenylphosphoryl)dibenzofuran (PPF), etc. can be used as host materials.

[0167] In an exemplary embodiment, the emission layer EML may contain styryl derivatives (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2-yl)vinyl)phenyl)-N-phenylaniline (N-BDAVBi)), perylene and its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)), pyrene and its derivatives (e.g., 1,1-dipyrene, 1,4-dipyrenylbenzene, 1,4-bis(N,N-diphenylamino)pyrene), etc. as suitable dopant materials.

[0168] When the emission layer EML emits red light, the emission layer EML may further contain, for example, tris(dibenzoylmethane)europium(III) phenanthroline (PBD:Eu(DBM)3(Phen)), or a fluorescent material containing perylene. If the emission layer EML emits red light, the dopants contained in the emission layer EML may be selected from metal complexes or organometallic complexes, such as bis(1-phenylisoquinoline)iridium(III) acetylacetonate (PIQIr(acac)), bis(1-phenylquinoline)iridium(III) acetylacetonate (PQIr(acac)), tris(1-phenylquinoline)iridium(III) (PQIr), and platinum octaethylporphyrin (PtOEP), rubrene and its derivatives, and 4-dicyanomethylene-2-(p-dimethylaminostyryl)-6-methyl-4H-pyran (DCM) and its derivatives.

[0169] When the emission layer EML emits green light, the emission layer EML may further contain a fluorescent material, including, for example, tris(8-hydroxyquinoline)aluminum (Alq3). If the emission layer EML emits green light, the dopants contained in the emission layer EML may be selected from metal complexes or organometallic complexes, such as fac-tris(2-phenylpyridine)iridium(III) (Ir(ppy)3), or coumarin and its derivatives.

[0170] When the emission layer EML emits blue light, the emission layer EML may further contain a fluorescent material, including at least one selected from the group consisting of, for example, spiro-DPVBi, spiro-6P, biphenylvinyl-benzene (DSB), biphenylvinyl-arylide (DSA), polyfluorene (PFO)-based polymers, and poly(p-phenylene vinylene) (PPV)-based polymers. If the emission layer EML emits blue light, the dopants contained in the emission layer EML may be selected from metal complexes or organometallic complexes, such as (4,6-F2ppy)2Irpic, or perylene and its derivatives.

[0171] In the organic electroluminescent device 10 according to an exemplary embodiment, the emission layer EML may emit blue light or green light. The emission layer EML may emit blue light having a wavelength range of 450 nm to 480 nm, or green light having a wavelength range of 490 nm to 560 nm.

[0172] In the organic electroluminescent device 10 according to an exemplary embodiment, an electron transport region ETR may be provided over 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.

[0173] 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 multilayer structure having a plurality of layers formed of a plurality of different materials.

[0174] 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 of an electron injection material and an electron transport material. Further, the electron transport region ETR may have a single layer structure containing a plurality of different materials, or a laminated structure of an electron transport layer ETL / electron injection layer EIL, or a hole blocking layer HBL / electron transport layer ETL / electron injection layer EIL laminated in order from the emission layer EML. The thickness of the electron transport region ETR may be, for example, about to about

[0175] The electron transport region ETR may be formed using various methods (e.g., vacuum deposition method, spin coating method, casting method, Langmuir-Blodgett (LB) method, inkjet printing method, laser printing method, and laser induced thermal imaging (LITI) method).

[0176] If the electron transport region (ETR) includes an electron transport layer (ETL), the ETR may comprise tris(8-hydroxyquinolinato)aluminum (Alq3), 1,3,5-tris[(3-pyridinyl)-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-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalen-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-hydroxyquinolinato-N1,O8)-(1,1'-biphenyl-4-yl)aluminum (BAlq), bis(benzoquinolinato-10)beryllium (Bebq2), 9,10-bis(naphthalen-2-yl)anthracene (ADN), and mixtures thereof.

[0177] If the electron transport region (ETR) includes an electron transport layer (ETL), the thickness of the ETL may be about to about For example, about to about If the thickness of the ETL satisfies the above range, satisfactory electron transport properties can be obtained without a significant increase in the driving voltage.

[0178] When the electron transport region (ETR) includes an electron injection layer (EIL), the ETR may use LiF, lithium 8-hydroxyquinolate (LiQ), Li2O, BaO, NaCl, CsF, lanthanide metals (such as Yb), or metal halides (such as RbCl, RbI, and KI). The EIL may also be formed using a mixture material of an electron transport material and an insulating organometallic salt. The organometallic salt may be a material having a band gap of about 4 eV or greater than 4 eV. In particular, the organometallic salt may include, for example, metal acetates, metal benzoates, metal acetoacetates, metal acetylacetonates, or metal stearates.

[0179] If the electron transport region (ETR) includes an electron injection layer (EIL), the thickness of the EIL may be about to about For example, about to about If the thickness of the electron injection layer EIL satisfies the above range, satisfactory electron injection properties can be obtained without causing a significant increase in the driving voltage.

[0180] The electron transport region ETR may include a hole blocking layer HBL as described above. The hole blocking layer HBL may contain at least one of, for example, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) and 4,7-diphenyl-1,10-phenanthroline (Bphen).

[0181] The second electrode EL2 is on the electron transport region ETR. The second electrode EL2 has conductivity. The second electrode EL2 may be formed of a metal alloy or a conductive compound. The second electrode EL2 may be a cathode. The second electrode EL2 may be a transmissive electrode, a semi-transmissive reflective electrode, or a reflective electrode. If the second electrode EL2 is a transmissive electrode, the second electrode EL2 may be formed using a transparent metal oxide (such as ITO, IZO, ZnO, ITZO, etc.).

[0182] If the second electrode EL2 is a semi-transmissive reflective electrode or a reflective electrode, the second electrode EL2 may contain Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, compounds thereof, or mixtures thereof (for example, a mixture of Ag and Mg). The second electrode EL2 may have a multilayer structure including a reflective layer or a semi-transmissive reflective layer formed using the materials described above and a transparent conductive layer formed using ITO, IZO, ZnO, ITZO, etc.

[0183] Although not shown, the second electrode EL2 may be connected to an auxiliary electrode. If the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.

[0184] In the organic electroluminescent device 10, according to the voltage applied to each of the first electrode EL1 and the second electrode EL2, the holes injected from the first electrode EL1 may move to the emission layer EML via the hole transport region HTR, and the electrons injected from the second electrode EL2 may move to the emission layer EML via the electron transport region ETR. The electrons and holes recombine in the emission layer EML to generate excitons, and light may be emitted via the transition of the excitons from the excited state to the ground state.

[0185] If the organic electroluminescent device 10 is a top emission type, the first electrode EL1 may be a reflective electrode, and the second electrode EL2 may be a transmissive electrode or a semi-transmissive reflective electrode. If the organic electroluminescent device 10 is a bottom emission type, the first electrode EL1 may be a transmissive electrode or a semi-transmissive reflective electrode, and the second electrode EL2 may be a reflective electrode.

[0186] The organic electroluminescent device 10 according to an exemplary embodiment may include a cover layer (not shown) on the second electrode EL2. The cover layer (not shown) 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(naphthalen-1-yl), etc.

[0187] The amine compound according to the exemplary embodiment described above may be included in an organic layer other than the hole transport region HTR as a material for the organic electroluminescent device 10. The organic electroluminescent device 10 according to the exemplary embodiment may include the amine compound described above in at least one of the organic layers disposed between the first electrode EL1 and the second electrode EL2, or in a cover layer (not shown) on the second electrode EL2.

[0188] The organic electroluminescent device 10 according to the exemplary embodiment includes the amine compound described above in the hole transport region HTR, and may provide high emission efficiency and improved device lifetime.

[0189] For example, the organic electroluminescent device 10 according to the exemplary embodiment includes the amine compound according to the exemplary embodiment in an organic layer adjacent to the emission layer among a plurality of organic layers in the hole transport region, which may help the hole transport region to maintain a high hole transport ability and block electron transport to ensure improved emission efficiency.

[0190] The amine compound according to the exemplary embodiment includes both a phenazasiline moiety and an arylamine moiety, which may provide excellent reliability. The organic electroluminescent device according to the exemplary embodiment includes an amine compound having both a phenazasiline moiety and an arylamine moiety in the hole transport region, which may provide an extended device lifetime. Without being bound by theory, it is believed that the nitrogen atom contained in the phenazasiline moiety enhances the hole transport ability of the entire molecule of the amine compound to increase the chance of recombining holes and electrons in the emission layer of the organic electroluminescent device, which may enable the organic electroluminescent device according to the exemplary embodiment to have improved emission efficiency and a low driving voltage.

[0191] The following examples and comparative examples are provided to highlight the characteristics of one or more embodiments, but it should be understood that the examples and comparative examples are not to be construed as limiting the scope of the embodiments, nor are the comparative examples to be construed as outside the scope of the embodiments. In addition, it should be understood that the embodiments are not limited to the specific details described in the examples and comparative examples.

[0192] [Example]

[0193] 1. Synthesis of amine compounds

[0194] The exemplary synthesis methods of compounds A4, A15, A45, and A53 in reference compound group A and compounds B4, B15, and B53 in compound group B will be described in detail for the synthesis of amine compounds according to the exemplary embodiments.

[0195] (Synthesis of compound A4)

[0196] Compound A4 (amine compound according to the exemplary embodiment) can be synthesized, for example, as shown in the following Reaction Scheme 1.

[0197] [Reaction Scheme 1]

[0198]

[0199] (Synthesis of intermediate A-1)

[0200] Under an argon (Ar) atmosphere, 2,5-dibromoaniline (25.1 g, 100 mmol), t-BuONa (14.4 g, 150 mmol), and toluene (250 mL) were added to a 500 mL three-necked flask, and the mixture was stirred at room temperature for about 30 minutes. After sequentially adding 2-iodobenzene (28.3 g, 100 mmol), Pd2(dba)3 (0.46 g, 0.5 mmol), and 1,1'-bis(diphenylphosphino)ferrocene (dppf, 0.54 g, 1.0 mmol) to the reaction solution, the mixture was stirred and heated to reflux for about 6 hours. After cooling to room temperature in air, the reaction solution was filtered through Celite to remove insoluble residues, and the filtrate was concentrated. The crude product thus obtained was purified by silica gel column chromatography (developing solvent: hexane / CH2Cl2 = 9:1) to obtain intermediate A-1 (33.3 g, yield 82%) as a white solid. Intermediate A-1 was identified by measuring FAB-MS, in which a molecular ion peak was observed at mass m / z = 406.

[0201] (Synthesis of intermediate A-2)

[0202] Under an argon atmosphere, intermediate A-1 (30.8 g, 75.8 mmol), iodobenzene (77.3 g, 379 mmol), CuI (14.4 g, 75.8 mmol) and K2CO3 (21.0 g, 151.6 mmol) were added to a 500 mL three-necked flask in sequence, and the mixture was stirred and heated at about 190 °C for about 72 hours. After cooling to room temperature in air, the reaction solvent was evaporated. The crude product thus obtained was purified by silica gel column chromatography (developing solvent: hexane / CH2Cl2 = 9:1) to obtain intermediate A-2 (39 g, yield 80%) as a white solid. Intermediate A-2 was identified by measuring FAB-MS, in which a molecular ion peak was observed at a mass m / z = 482.

[0203] <Synthesis of Intermediate A-3>

[0204] Under an argon atmosphere, intermediate A-2 (28.00 g, 58.0 mmol) and THF (290 mL) were added to a 500 mL three-necked flask, and the mixture was cooled to about -78 °C. Then, n-butyllithium (1.6 M, 72.5 mL, 31.8 mmol) was added dropwise thereto, and the mixture was stirred at about -78 °C for about 30 minutes. Dichlorodiphenylsilane dissolved in THF (30 mL) was added dropwise thereto, and the mixture was stirred for about 1 hour. After cooling to room temperature in air, the mixture was stirred for an additional about 2 hours, and then stirred and heated to reflux for about 1 hour. After cooling to room temperature in air, water was added to the reaction solution, and the organic layer was separated and taken out. Toluene was added to the remaining aqueous layer, and then the aqueous layer was extracted to obtain another organic layer. The organic layers were combined and then dried over MgSO4. MgSO4 was filtered off and the organic layer was concentrated. The crude product thus obtained was purified by silica gel column chromatography (developing solvent: hexane / CH2Cl2 = 9:1) to obtain intermediate A-3 (16.10 g, yield 55%) as a white solid. Intermediate A-3 was identified by measuring FAB-MS, in which a molecular ion peak was observed at a mass m / z = 504.

[0205] <Synthesis of Compound A4>

[0206] Under an argon atmosphere, intermediate A-3 (8.02 g, 15.9 mmol), Pd(dba)2 (0.27 g, 0.03 equivalent, 0.5 mmol), NaOtBu (3.05 g, 2 equivalents, 31.8 mmol), toluene (80 mL), bis(4-biphenyl)amine (5.62 g, 1.1 equivalents, 17.5 mmol), and tBu3P (0.32 g, 0.1 equivalent, 1.6 mmol) were added to a 500 mL three-necked flask in sequence, and the mixture was stirred and heated to reflux for about 6 hours. After cooling to room temperature in air, water was added to the reaction solution, and the organic layer was separated and taken out. Toluene was added to the remaining aqueous layer, and then the aqueous layer was extracted to obtain another organic layer. The organic layers were combined, washed with brine, and then dried over MgSO4. The MgSO4 was filtered off and the organic layer was concentrated. The crude product thus obtained was purified by silica gel column chromatography (using a mixture of hexane and toluene as the eluent) to obtain compound A4 (9.48 g, yield 80%) as a white solid. Compound A4 was identified by measuring FAB-MS, in which a molecular ion peak was observed at a mass m / z = 745.

[0207] (Synthesis of Compound A15)

[0208] Compound A15 (amine compound according to an exemplary embodiment) can be synthesized, for example, as shown in the following Reaction Scheme 2.

[0209] [Reaction Scheme 2]

[0210]

[0211] Under an argon atmosphere, intermediate A-3 (8.02 g, 15.9 mmol), Pd(dba)2 (0.27 g, 0.03 equiv, 0.5 mmol), NaOtBu (3.05 g, 2 equiv, 31.8 mmol), toluene (80 mL), N-(4-(naphthalen-1-yl)phenyl)-[1,1'-biphenyl]-4-amine (6.50 g, 1.1 equiv, 17.5 mmol), and tBu3P (0.32 g, 0.1 equiv, 1.6 mmol) were added to a 500 mL three-necked flask in sequence, and the mixture was stirred and heated to reflux for about 6 hours. After cooling to room temperature in air, water was added to the reaction solution, and the organic layer was separated and taken out. Toluene was added to the remaining aqueous layer, and then the aqueous layer was extracted to obtain another organic layer. The organic layers were combined, washed with brine, and then dried over MgSO4. The MgSO4 was filtered off and the organic layer was concentrated. The crude product thus obtained was purified by silica gel column chromatography (using a mixture of hexane and toluene as the eluent) to obtain compound A15 (10.75 g, yield 85%) as a white solid. Compound A15 was identified by measuring FAB-MS, in which the molecular ion peak was observed at a mass m / z = 795.

[0212] (Synthesis of Compound A45)

[0213] Compound A45 (an amine compound according to an exemplary embodiment) can be synthesized, for example, as shown in the following Reaction Scheme 3.

[0214] [Reaction Scheme 3]

[0215]

[0216] Under an argon atmosphere, intermediate A-3 (6.91 g, 13.7 mmol), Pd(dba)2 (0.24 g, 0.03 eq, 0.4 mmol), NaOtBu (2.63 g, 2 eq, 27.4 mmol), toluene (69 mL), N-[4-(1-naphthyl)phenyl]-4-dibenzothiophenyl-4-amine (6.05 g, 1.1 eq, 15.1 mmol) and tBu3P (0.28 g, 0.1 eq, 1.4 mmol) were added to a 500 mL three-necked flask in sequence, and the mixture was stirred and heated to reflux for about 6 hours. After cooling to room temperature in air, water was added to the reaction solution, and the organic layer was separated and taken out. Toluene was added to the remaining aqueous layer, and then the aqueous layer was extracted to obtain another organic layer. The organic layers were combined, washed with brine, and then dried over MgSO4. The MgSO4 was filtered off and the organic layer was concentrated. The crude product thus obtained was purified by silica gel column chromatography (using a mixture of hexane and toluene as the eluent) to obtain compound A45 (8.93 g, yield 79%) as a white solid. Compound A45 was identified by measuring FAB-MS, in which the molecular ion peak was observed at a mass m / z = 825.

[0217] (Synthesis of Compound A53)

[0218] Compound A53 (the amine compound according to the exemplary embodiment) can be synthesized, for example, as shown in the following Reaction Scheme 4.

[0219] [Reaction Scheme 4]

[0220]

[0221] Under an argon atmosphere, intermediate A-3 (8.02 g, 15.9 mmol), N,N-bis(4-biphenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (9.15 g, 1.1 equivalents, 17.5 mmol), K2CO3 (6.59 g, 3 equivalents, 47.7 mmol), Pd(PPh3)4 (0.92 g, 0.05 equivalents, 0.8 mmol) and a mixed solution of toluene / EtOH / water (4 / 2 / 1) (110 mL) were added successively to a 300 mL three-necked flask, and the mixture was stirred and heated at about 80 °C for about 5 hours. After cooling to room temperature in air, the reaction solution was extracted with toluene. After removing the aqueous layer, the organic layer was washed with brine and then dried over MgSO4. The MgSO4 was filtered off and the organic layer was concentrated. The crude product thus obtained was purified by silica gel column chromatography (using a mixture of hexane and toluene as the eluent) to obtain compound A53 (11.3 g, yield 87%) as a white solid. Compound A53 was identified by measuring FAB-MS, in which a molecular ion peak was observed at mass m / z = 821.

[0222] (Synthesis of Compound B4)

[0223] Compound B4 (amine compound according to the exemplary embodiment) can be synthesized, for example, as shown in the following Reaction Scheme 5.

[0224] [Reaction Scheme 5]

[0225]

[0226] Compound B4 was synthesized by carrying out the same synthesis method as that for compound A4, except that 2,4-dibromoaniline was used instead of 2,5-dibromoaniline in the synthesis method of compound A4. Compound B4 was identified by measuring FAB-MS, in which a molecular ion peak was observed at mass m / z = 745.

[0227] (Synthesis of Compound B15)

[0228] Compound B15 (amine compound according to the exemplary embodiment) can be synthesized, for example, as shown in the following Reaction Scheme 6.

[0229] [Reaction Scheme 6]

[0230]

[0231] Compound B15 was synthesized by carrying out the same synthetic method as that for compound A15, except that intermediate B-3 was used in place of intermediate A-3 in the synthetic method of compound A15. Compound B15 was identified by measuring FAB-MS, in which a molecular ion peak was observed at a mass m / z = 795.

[0232] (Synthesis of Compound B53)

[0233] Compound B53 (an amine compound according to an exemplary embodiment) can be synthesized, for example, as shown in the following Reaction Scheme 7.

[0234] [Reaction Scheme 7]

[0235]

[0236] Compound B53 was synthesized by carrying out the same synthetic method as that for compound A53, except that intermediate B-3 was used in place of intermediate A-3 in the synthetic method of compound A53. Compound B53 was identified by measuring FAB-MS, in which a molecular ion peak was observed at a mass m / z = 821.

[0237] 2. Fabrication and Evaluation of an Organic Electroluminescent Device Containing an Amine Compound

[0238] (Fabrication of an Organic Electroluminescent Device)

[0239] An organic electroluminescent device according to an exemplary embodiment containing an amine compound according to an exemplary embodiment in the hole transport layer was fabricated by the following method. Organic electroluminescent devices of Examples 1 to 7 were fabricated by using the above-described compounds A4, A15, A45, A53, B4, B15, and B53 as materials for the hole transport layer. Organic electroluminescent devices of Comparative Examples 1 to 5 were fabricated by using the following comparative compounds R1 to R5 as materials for the hole transport layer.

[0240] Table 1 shows the compounds used in the hole transport layer for Examples 1 to 7 and Comparative Examples 1 to 5.

[0241] [Table 1]

[0242]

[0243]

[0244] The ITO was patterned on a glass substrate to a thickness of about and then washed with ultrapure water and subjected to UV ozone treatment for about 10 minutes. A hole injection layer was formed using 1-TNATA to a thickness of about The thickness. Thereafter, an embodiment compound or a comparative compound is used to form a hole transport layer to about The thickness.

[0245] Then, ADN doped with 3% TBP is used to form an emission layer to about The thickness. Thereafter, Alq3 is used to form an electron transport layer to about The thickness, and LiF is used to form an electron injection layer to about The thickness.

[0246] Then, Al is used to form a second electrode to about The thickness.

[0247] The hole injection layer, hole transport layer, emission layer, electron transport layer, electron injection layer, and second electrode are formed by using a vacuum deposition apparatus.

[0248] (Performance Evaluation of Organic Electroluminescent Device)

[0249] The performance evaluation results of the organic electroluminescent devices fabricated in Examples 1 to 7 and Comparative Examples 1 to 5 are shown in Table 2 below. Table 2 shows a comparison of the driving voltage, emission efficiency, and device lifetime of the organic electroluminescent devices. As shown in the performance evaluation results of the organic electroluminescent devices shown in Table 2, the emission efficiency is the measured value at a current density of about 10 mA / cm 2 , and the device lifetime means the time required for the initial luminance of 1,000 cd / m 2 to decrease to half the luminance.

[0250] The current density, voltage, and emission efficiency of the organic electroluminescent devices fabricated in the examples and comparative examples are measured in a dark room by using a source meter 2400 series (Keithley Instruments), a colorimeter CS-200 (Konica Minolta, Inc.), and a computer program LabVIEW 2.0 (Japan National Instruments Corporation).

[0251] [Table 2]

[0252]

[0253] Referring to the results in Table 2, it can be seen that the organic electroluminescent device of the example using the amine compound according to the exemplary embodiment as the material for the hole transport layer has a reduced driving voltage, improved efficiency, and extended device lifetime. It can be seen that when compared with the organic electroluminescent devices of Comparative Examples 1 to 5, the organic electroluminescent devices of Examples 1 to 7 exhibit a reduced driving voltage, improved emission efficiency, and significantly improved half-life.

[0254] The amine compound used in the example contains a phenazasiline moiety having both Si and N atoms in the fused ring, and provides improved efficiency and extended lifetime for the device using the compound. Further, without being bound by theory, it is believed that due to the suppression of crystallinity caused by the introduction of the amine group in one side of the phenazasiline moiety, the amine compound used in the example has enhanced amorphous properties; when compared with, for example, the comparative compound R4, the asymmetry of the entire molecule of the amine compound according to the exemplary embodiment can provide improved emission efficiency and extended device lifetime. Further, without being bound by theory, it is believed that the amine compound used in the example (which contains a nitrogen atom in the phenazasiline fused ring) further improves the hole transport ability and increases the chance of recombination of holes and electrons in the emission layer, thereby further improving the emission efficiency of the organic electroluminescent device using the amine compound.

[0255] Compared with the amine compound used in the example, the comparative compounds used in Comparative Examples 1 to 3 (which are amine compounds having a fused ring containing Si as a heteroatom) do not have a nitrogen atom in the fused ring. When compared with the organic electroluminescent device of the example, the organic electroluminescent devices of Comparative Examples 1 to 3 exhibit reduced emission efficiency and short device lifetime. Without being bound by theory, it is believed that in the amine compound used in the example, the nitrogen atom contained in the fused ring contributes to improving the hole transport ability.

[0256] The comparative compounds used in Comparative Examples 4 and 5 have a phenazasiline moiety substituted with a heteroaryl group (such as carbazole or benzothienopyridine). When compared with the organic electroluminescent device of the example, the organic electroluminescent devices of Comparative Examples 4 and 5 exhibit low emission efficiency and short device lifetime.

[0257] Referring to the results in Table 2, it can be seen that when compared with an organic electroluminescent device of a comparative example using a comparative compound as a material for the hole transport layer, the organic electroluminescent device of an example using an amine compound according to an exemplary embodiment as a material for the hole transport layer has an extended device lifetime and improved efficiency. The amine compound according to the exemplary embodiment includes both a phenazasiline moiety and an arylamine moiety, and can improve the quality of the layer via improved electron resistance and thermal stability caused by the phenazasiline moiety while maintaining the amine properties, and thus, it can contribute to improving the efficiency and lifetime of the organic electroluminescent device.

[0258] Through summary and review, the development of materials for the hole transport layer is being studied, which suppresses the dispersion of exciton energy in the emission layer to achieve an organic electroluminescent device with high efficiency.

[0259] As described above, the embodiment relates to an amine compound that can be used in the hole transport region and an organic electroluminescent device including the amine compound.

[0260] The amine compound according to the exemplary embodiment includes both a phenazasiline moiety and an arylamine moiety. The amine compound can exhibit a long lifetime and provide improved efficiency for a device using the amine compound.

[0261] Without being bound by theory, it is considered that since the phenazasiline moiety has excellent heat resistance and charge resistance and the arylamine moiety has a long lifetime property, the amine compound according to the exemplary embodiment has enhanced high temperature resistance and charge resistance, and thus, it can be used as a material for an organic electroluminescent device with a further extended lifetime. In addition, it is considered that the nitrogen atom contained in the phenazasiline moiety enhances the hole transport ability of the entire molecule of the amine compound to increase the chance of recombination of holes and electrons in the emission layer of the organic electroluminescent device, which enables the organic electroluminescent device including the amine compound according to the exemplary embodiment in the hole transport region to have improved emission efficiency.

[0262] The amine compound according to the exemplary embodiment can improve the emission efficiency and lifetime of the organic electroluminescent device.

[0263] The organic electroluminescent device according to the exemplary embodiment can include the amine compound according to the exemplary embodiment and can exhibit improved emission efficiency and an extended lifetime.

[0264] Exemplary embodiments have been disclosed herein, and although specific terms are employed, they are used and interpreted in a general and descriptive sense only and not for purposes of limitation. In some instances, as would be apparent to one of ordinary skill in the art prior to the filing of the present application, features, characteristics, and / or elements described with respect to a particular embodiment may be used alone or in combination with those described with respect to other embodiments, unless otherwise expressly indicated. Accordingly, those skilled in the art will appreciate that various changes in form and detail may be made without departing from the spirit and scope of the invention as set forth in the claims.

Claims

1. An amine compound represented by the following formula 1: [Formula 1] In formula 1, R1 is a substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms, R2 and R3 are each independently a substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms, R4 to R 11 each independently represents a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothiophenyl group, or a substituted or unsubstituted dibenzothiophenyl group, L is a direct bond, or a substituted or unsubstituted phenylene group, and n is 1, wherein "substituted" means substituted by at least one substituent selected from deuterium, halogen, and an alkyl group having 1 to 10 carbon atoms.

2. The amine compound according to claim 1, wherein formula 1 is represented by the following formula 1-1 or formula 1-2: [Formula 1-1] [Formula 1-2] In Formula 1-1 and Formula 1-2, R1 to R 11 , Ar1, Ar2, L and n are the same as those defined in Formula 1.

3. The amine compound according to claim 1, wherein R1 is an unsubstituted phenyl group.

4. The amine compound according to claim 1, wherein R2 and R3 are each independently an unsubstituted phenyl group.

5. The amine compound according to claim 1, wherein R2 and R3 are the same as each other.

6. The amine compound according to claim 1, wherein Ar1 and Ar2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted fluorenyl group, wherein "substituted" is defined as in claim 1.

7. An amine compound, wherein the amine compound is any one of the compounds represented in the following compound group A and compound group B: [Compound group A] [Compound group B] 8. An organic electroluminescent device, comprising: a first electrode; a hole transport region on the first electrode and containing the amine compound according to any one of claims 1 to 7; 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.

Images