KR102243624B1 - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to an organic light-emitting compound represented by the following [Chemical Formula 1] and an organic light-emitting device comprising the same, wherein the organic light-emitting compound according to the present invention is used as a host material in the light emitting layer of the device, or holes in the hole injection layer and the hole transport layer The organic electroluminescent device employed as a transport material has improved luminous efficiency and long life characteristics compared to conventional host compounds or hole transport materials, and is capable of low voltage driving.
[Formula 1]

Description

An electroluminescent compound and an electroluminescent device comprising the same}

The present invention relates to an organic light emitting compound, and more particularly, to a compound employed as a host compound of a light emitting layer or a hole transport material of a hole injection layer or a hole transport layer, and an organic light emitting device including the same.

Organic electroluminescent devices not only can form devices on a transparent substrate, but can drive a low voltage of 10 V or less compared to plasma display panels or inorganic electroluminescent (EL) displays, and consume relatively little power. In addition, it has the advantage of excellent color sense, and can display three colors of green, blue, and red, which has recently been a subject of much interest as a next-generation display device.

However, in order for such an organic light emitting device to exhibit the above characteristics, a material that forms an organic layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material. However, the development of an organic material layer material for a stable and efficient organic electroluminescent device has not been sufficiently developed until now. Accordingly, the development of new materials having low voltage driving, high efficiency and long life is still required.

In particular, as conventional hole transport materials, copper phthalocyanine (CuPc), MTDATA, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-diphenyl- N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine (TPD), etc., are known, but there is a problem that the efficiency and lifespan decrease when employing it in a device. However, in order to improve this, arylamine-based compounds having various substituents are being developed, but still have a problem that is not sufficient to satisfy the efficiency and long life at the same time.

In addition, the most important factor determining luminous efficiency in an organic light emitting device is a light emitting material. Currently, a fluorescent material is widely used as a light emitting material, but the development of a phosphorescent material is one of the methods that can theoretically improve luminous efficiency more due to the light emitting mechanism, and accordingly, various phosphorescent materials have been developed up to now. In particular, as a phosphorescent host material, CBP is the most widely known until now, and an organic light emitting device using a BALq derivative as a host is known.

However, an organic light emitting device using a phosphorescent material has a significantly higher current efficiency than a device using a fluorescent light emitting material, but when a material such as BAlq or CBP is used as a host of the phosphorescent material, the driving voltage is higher than that of the device using the fluorescent material. Due to this high power efficiency, there is no great advantage in terms of power efficiency, and the lifespan of the device is not satisfactory. Therefore, development of a more stable and high-performance host material is required.

Accordingly, the present invention has been devised to solve the above problems, and is to provide an organic light emitting compound having improved efficiency and lifetime characteristics at the same time compared to a conventional light emitting layer host material or a hole transport material.

In addition, the present invention is to provide an organic electroluminescent device having very excellent luminous efficiency and lifetime characteristics by employing such an organic light emitting compound.

In order to solve the above problems, the present invention is to provide an organic light-emitting compound represented by the following [Chemical Formula 1] and an organic light-emitting device including the same.

[Formula 1]

Specific characteristics of the organic light-emitting compound according to [Chemical Formula 1] and each substituent will be described later.

The organic light-emitting compound according to the present invention is capable of improved luminous efficiency, long life characteristics, and low voltage driving compared to a conventional phosphorescent host material or hole transport material, and thus an organic light-emitting device employing the same can be usefully used in various display devices.

1 is a cross-sectional view illustrating a structure of an organic light emitting diode according to an embodiment of the present invention.

Hereinafter, the present invention will be described in more detail.

The present invention relates to an organic light-emitting compound employed in an organic layer of an organic light-emitting device, represented by the following [Chemical Formula 1], and is used as a light-emitting host material or a hole transport material depending on the substituent introduced into the core skeleton, thereby luminous efficiency of the device. And improving life characteristics and enabling low voltage driving.

[Formula 1]

Each substituent in [Chemical Formula 1] is as follows.

R ₁ and R ₂ are selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms do.

Z is a substituted or unsubstituted aromatic ring or heteroaromatic ring having 10 or more carbon atoms, and may be preferably any one selected from the following [Structural Formula C1] to [Structural Formula C8].

In the [Structural Formula C1] to [Structural Formula C8],

R'is selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, and m Is an integer of 1 to 8, and when m is 2 or more, each R'may be the same as or different from each other, and * means a site bonded to [Chemical Formula 1].

X ₁ to X ₈ are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted carbon number 2 to 30 alkenyl group, substituted or unsubstituted C 2 to C 30 alkynyl group, substituted or unsubstituted C 3 to C 30 cycloalkyl group, substituted or unsubstituted and selected from O, N, S, and P as heteroatoms A heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 1 to 30 carbon atoms. 30 alkylamine group, substituted or unsubstituted C5 to C30 arylamine group, substituted or unsubstituted C1 to C30 alkylsilyl group, substituted or unsubstituted C5 to C30 arylsilyl group, cyano group And a halogen group.

In addition, _{at least one of X 1} to X ₈ is bonded to the following [Structural Formula A] or is bonded to the following [Structural Formula B].

In the [Structural Formula A] and [Structural Formula B], * means a site bonding to X _{1 to X 8 of the [Chemical Formula 1].}

In the [Structural Formula A] and [Structural Formula B],

L ₁ and L ₂ are each independently a substituted or unsubstituted C1-C30 alkylene group, a substituted or unsubstituted C2-C30 alkylene group. Alkenylene group, substituted or unsubstituted C2 to C30 alkynylene group, substituted or unsubstituted C3 to C30 A cycloalkylene group, a substituted or unsubstituted arylene group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms, a substituted or unsubstituted substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms fused to one or more It is selected from a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms in which one or more substituted or unsubstituted C3 to C30 cycloalkyl groups are fused, and n and m are 0 Is an integer of 2, and when n and m are 2, a plurality of L ₁ and L ₂ may be the same or different from each other.

Ar ₁ to Ar ₃ are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted C 5 to 50 It is selected from an aryl group and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having any one or more selected from O, N, S, and P as hetero atoms.

In the [Chemical Formula 1], [Structural Formula A] and [Structural Formula B], Z, X ₁ to X ₈ , R ₁ and R ₂ , L ₁ and L ₂ , Ar ₁ to Ar ₃ may each be connected with a substituent adjacent to each other to form a substituted or aromatic monocyclic or polycyclic ring, and the carbon atoms of the formed alicyclic, aromatic monocyclic or polycyclic ring are N, S and O It may be substituted with one or more heteroatoms selected from among.

In addition,'substituted'in'substituted or unsubstituted' in [Chemical Formula 1] means that it is further substituted with one or more substituents, and the one or more substituents are deuterium, cyano group, halogen group, hydroxy group, Nitro group, C1-C24 alkyl group, C1-C24 halogenated alkyl group, C1-C24 alkenyl group, C1-C24 alkynyl group, C1-C24 heteroalkyl group, C6-C24 aryl group , C6-C24 arylalkyl group, C2-C24 heteroaryl group, C2-C24 heteroarylalkyl group, C1-C24 alkoxy group, C1-C24 alkylamino group, C1-C24 aryl It is selected from the group consisting of an amino group, a C1-C24 heteroarylamino group, a C1-C24 alkylsilyl group, a C1-C24 arylsilyl group, and a C1-C24 aryloxy group.

According to a preferred embodiment of the present invention, Ar ₃ of [Structural Formula B] may be any one selected from the following [Structural Formula D1] to [Structural Formula D6].

In the [Structural Formula D1] to [Structural Formula D6],

X is O, S, NR or CRR (R is the _{same as the definition of R 1} and R ₂ in [Chemical Formula 1]), and R" is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted C5 to C50 aryl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C3 to C30 cyclo Alkyl group, substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted 1 carbon number To 30 alkylthio groups, substituted or unsubstituted arylthioxy groups having 5 to 30 carbon atoms, substituted or unsubstituted alkylamine groups having 1 to 30 carbon atoms, substituted or unsubstituted arylamine groups having 5 to 30 carbon atoms, substituted Or an unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having O, N or S as a hetero atom, a cyano group, a nitro group, and a halogen group, n is 1 It is an integer of 8, and when n is 2 or more, a plurality of R" may be the same as or different from each other.

When the substituent R" is not bonded to the carbon of the aromatic ring in the heteroaryl group of [Structural Formula D1] to [Structural Formula D6], hydrogen or deuterium may be bonded, and one of the plurality of R″ is bonded to a nitrogen atom. It may be a single bond.

The organic light-emitting compound of [Chemical Formula 1] according to the present invention may be any one compound selected from the group represented by the following [Chemical Formula 2] to [Chemical Formula 65]. However, the scope of [Chemical Formula 1] is not limited thereby.

According to a preferred embodiment of the present invention _{, only one of the X 1} to X ₈ is bonded to the [Structural Formula A], and n is 1 or 2, and L ₁ is a single bond, or the following [Structural Formula 1] to It may be any one selected from [Structural Formula 8]. Hydrogen or deuterium may be bonded to the carbon site of the aromatic ring of the following [Structural Formula 1] to [Structural Formula 8].

_{In addition, Ar 1} and Ar ₂ of [Structural Formula A] may be the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 24 carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 24 carbon atoms have.

The organic light-emitting compound of [Chemical Formula 1] according to the present invention may be any one compound selected from the group represented by the following [Chemical Formula 66] to [Chemical Formula 113]. However, the scope of [Chemical Formula 1] is not limited thereby.

Specific examples of the alkyl group used in the present invention include methyl group, ethyl group, propyl group, isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, iso-amyl group, hexyl group, heptyl group, oxy And a butyl group, a stearyl group, a trichloromethyl group, a trifluoromethyl group, and the like, and at least one hydrogen atom in the alkyl group is a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a trifluoromethyl group, a silyl group (this In the case of "alkylsilyl group"), a substituted or unsubstituted amino group (-NH ₂ , -NH(R), -N(R')(R"), wherein R, R'and R" are each independently It is a C1-C24 alkyl group (referred to as an "alkylamino group" in this case)), an amidino group, a hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, a C1-C24 alkyl group, a C1-C24 halogenated Alkyl group, C2-C24 alkenyl group, C2-C24 alkynyl group, C1-C24 heteroalkyl group, C5-C24 aryl group, C6-C24 arylalkyl group, C3-C24 heteroaryl group Or it may be substituted with a C3-C24 heteroarylalkyl group.

The aryl group used in the present invention is an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen, and includes a single or fused ring system containing 5 to 7 members, preferably 5 or 6 members, and the aryl group If there is a substituent, it may be fused with neighboring substituents to further form a ring.

As a specific example of the aryl group, a phenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, naphthyl group, anthryl group, phenanthryl group And aromatic groups such as pyrenyl group, indenyl, fluorenyl group, tetrahydronaphthyl group, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl, and the like.

In addition, the aryl group may also be further substituted with one or more substituents, and more specifically, at least one hydrogen atom in the aryl group is a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a silyl group, an amino group (-NH ₂ , -NH(R), -N(R')(R"), R'and R" are each independently an alkyl group having 1 to 10 carbon atoms, in this case referred to as an "alkylamino group"), an amidino group, a hydrazine Group, hydrazone group, carboxyl group, sulfonic acid group, phosphoric acid group, C1-C24 alkyl group, C1-C24 halogenated alkyl group, C1-C24 alkenyl group, C1-C24 alkynyl group, C1-C24 hetero It may be substituted with an alkyl group, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, a heteroarylalkyl group having 2 to 24 carbon atoms, and the like.

Specific examples of the alkoxy group used in the present invention include methoxy group, ethoxy group, propoxy group, isobutyloxy group, sec-butyloxy group, pentyloxy group, iso-amyloxy group, hexyloxy group, and the like. , It can be substituted with the same substituent as in the case of the above alkyl group.

Specific examples of the halogen group used in the present invention include fluorine (F), chlorine (Cl), and bromine (Br).

The aryloxy group used in the present invention refers to an -O- aryl radical, wherein the aryl group is as defined above, and specific examples include phenoxy, naphthoxy, anthracenyloxy, phenanthrenyloxy, fluorenyloxy, Indenyloxy, etc., and one or more hydrogen atoms contained in the aryloxy group may be further substituted.

Specific examples of the silyl group used in the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, silyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethyl Furylsilyl, etc. are mentioned.

The heteroaryl group used in the present invention may be any one selected from the following [Structural Formula 1] to [Structural Formula 10].

In the [Structural Formula 1] to [Structural Formula 10],

T ₁ to T ₁₂ are the same as or different from each other, and each independently, may be any one selected from _{C (R 41} ), C (R ₄₂ ) (R ₄₃ ), N, N (R _{44 ), O and S} And T ₁ to T ₁₂ are not all carbon atoms at the same time, and R ₄₁ to R ₄₄ are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted Or an unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C5-C30 aryl group, and a substituted or unsubstituted C2-C30 heteroaryl group having O, N, S or P as a hetero atom. Is selected.

In addition, the [Structural Formula 3] may include a compound represented by the following [Structural Formula 3-1] by a resonance structure according to the movement of electrons.

[Structural Formula 3-1]

In the [Structural Formula 3-1], T ₁ to T ₇ are the same as defined in [Structural Formula 5] to [Structural Formula 14].

According to a preferred embodiment of the present invention, the [Structural Formula 1] to [Structural Formula 10] may be selected from the following [Structural Formula 11].

[Structural Formula 11]

In the [Structural Formula 11],

_{X is the same as the definition of X 1} to X ₈ in [Chemical Formula 1], m is an integer of 1 to 11, and when m is 2 or more, a plurality of Xs are the same or different from each other, and in [Chemical Formula 1] It may be connected with a substituent.

In addition, another aspect of the present invention relates to an organic electroluminescent device comprising a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layer includes the [Formula 1] It may contain at least one or more organic light-emitting compounds according to the present invention represented by ].

In addition, the organic layer containing the organic light emitting compound of the present invention may include at least one of a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function at the same time, a light emitting layer, an electron transport layer, and an electron injection layer. .

At this time, the organic layer interposed between the first electrode and the second electrode may include a light emitting layer, the light emitting layer is made of a host and a dopant, and the organic light emitting compound according to [Formula 1] of the present invention is used as a host. I can. Meanwhile, in the present invention, a dopant material may be used in addition to the host for the light emitting layer. When the light emitting layer includes a host and a dopant, the content of the dopant may be generally selected from about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host.

In addition, the organic layer interposed between the first electrode and the second electrode may include a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function at the same time, the hole injection layer, the hole transport layer, The organic light-emitting compound according to [Chemical Formula 1] of the present invention may be included in a functional layer having a hole injection function and a hole transport function at the same time.

Hereinafter, an embodiment of an organic light emitting diode according to the present invention will be described in more detail with reference to FIG. 1 below.

1 is a cross-sectional view showing the structure of an organic electroluminescent device of the present invention. The organic electroluminescent device according to the present invention includes an anode 20, a hole transport layer 40, an organic light emitting layer 50, an electron transport layer 60, and a cathode. It includes (80), and may further include a hole injection layer 30 and an electron injection layer 70 if necessary, and in addition to that, it is possible to further form an intermediate layer of one or two layers, and a hole blocking layer Alternatively, an electron blocking layer may be further formed, and an organic layer having various functions may be further included according to the characteristics of the device.

Referring to FIG. 1, an organic light emitting device of the present invention and a method of manufacturing the same will be described as follows.

First, an anode 20 is formed by coating a material for an anode electrode on the substrate 10. Here, as the substrate 10, a substrate used in a typical organic electroluminescent device is used, and an organic substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling and waterproofness is preferable. In addition, as a material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), and the like, which are transparent and have excellent conductivity, are used.

The hole injection layer 30 is formed by vacuum thermal evaporation or spin coating of a hole injection layer material on the anode 20 electrode. Thereafter, a hole transport layer material is vacuum thermally evaporated or spin coated on the hole injection layer 30 to form the hole transport layer 40.

The hole injection layer material may be used without particular limitation as long as it is commonly used in the art, and as a specific example, 2-TNATA[4,4',4"-tris(2-naphthylphenyl-phenylamino)-triphenylamine] , NPD[N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine)], TPD[N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'- biphenyl-4,4'-diamine], DNTPD[N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine ] And the like, and the [Chemical Formula 1] compound according to the present invention may be used.

In addition, as long as the material for the hole transport layer is not particularly limited as long as it is commonly used in the art, for example, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1 -Biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine (α-NPD), etc. can be used, and the present invention The compound of [Chemical Formula 1] may be used.

Subsequently, an organic light-emitting layer 50 is stacked on the hole transport layer 40 and a hole blocking layer (not shown) is selectively formed on the organic light-emitting layer 50 by a vacuum deposition method or a spin coating method. can do. The hole blocking layer serves to prevent this problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level because when holes pass through the organic light emitting layer and flow into the cathode, the life and efficiency of the device are reduced. . In this case, the hole blocking material to be used is not particularly limited, but must have an electron transport ability and an ionization potential higher than that of a light-emitting compound, and representatively, BAlq, BCP, TPBI, and the like may be used.

As the material used for the hole blocking layer, any one selected from BAlq, BCP, Bphen, TPBI, NTAZ, BeBq ₂ , OXD-7, Liq, and [Formula 501] to [Formula 507] may be used, but limited thereto. It does not become.

BAlq BCP Bphen

TPBI NTAZ BeBq ₂

OXD-7 Liq

[Chemical Formula 501] [Chemical Formula 502] [Chemical Formula 503]

[Chemical Formula 504] [Chemical Formula 505] [Chemical Formula 506]

[Chemical Formula 507]

After depositing the electron transport layer 60 on the hole blocking layer through a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed, and a cathode-forming metal is vacuum-heated on the electron injection layer 70. The organic EL device is completed by vapor deposition to form the cathode 80 electrode. Here, the cathode-forming metals include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-ridium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver ( Mg-Ag) or the like can be used, and in order to obtain a top light emitting device, a transmissive cathode using ITO or IZO can be used.

As the material for the electron transport layer, a known electron transport material may be used as it has a function of stably transporting electrons injected from an electron injection electrode (Cathode). Examples of known electron transport materials include quinoline derivatives, in particular tris (8-quinolinorate) aluminum (Alq3), TAZ, Balq, beryllium bis (benzoquinolin-10-noate) (beryllium bis (benzoquinolin-10- olate: Bebq2), ADN, [Chemical Formula 401], [Chemical Formula 402], and oxadiazole derivatives such as PBD, BMD, BND, and the like may be used.

TAZ BAlq

[Compound 401] [Compound 402] BCP

In addition, as for the electron transport layer used in the present invention, an organometallic compound represented by the following [Chemical Formula C] may be used alone or in combination with the electron transport layer material.

[Formula C]

In [Chemical Formula C],

Y is a portion in which any one selected from C, N, O, and S is directly bonded to the M to form a single bond, and a portion in which any one selected from C, N, O, and S forms a coordination bond to the M. It includes, and is a ligand chelated by the single bond and the coordination bond. M is an alkali metal, alkaline earth metal, aluminum (Al) or boron (B) atom.

OA is a monovalent ligand capable of a single bond or coordination bond with M, wherein O is oxygen, and A is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, A substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C5-C30 cyclo Any one selected from an alkenyl group and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having O, N or S as a hetero atom.

In addition, when M is one metal selected from alkali metals, m=1, n=0, and when M is one metal selected from alkaline earth metals, m=1, n=1, or m =2, n=0, and when M is boron or aluminum, m=1 to 3, and n is any one of 0 to 2, which satisfies m+n=3.

'Substituted' in the'substituted or unsubstituted' is deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group, alkoxy group, alkylamino group, arylamino group, hetero arylamino group, alkylsilyl group, arylsilyl group, It means substituted with one or more substituents selected from the group consisting of aryloxy group, aryl group, heteroaryl group, germanium, phosphorus and boron.

In addition, each of the Y's is the same or different, and may be any one independently selected from the following [Structural Formula C1] to [Structural Formula C39], but is not limited thereto.

[Structural Formula C1] [Structural Formula C2] [Structural Formula C3]

[Structural Formula C4] [Structural Formula C5] [Structural Formula C6]

[Structural Formula C7] [Structural Formula C8] [Structural Formula C9] [Structural Formula C10]

[Structural Formula C11] [Structural Formula C12] [Structural Formula C13]

[Structural Formula C14] [Structural Formula C15] [Structural Formula C16]

[Structural Formula C17] [Structural Formula C18] [Structural Formula C19] [Structural Formula C20]

[Structural Formula C21] [Structural Formula C22] [Structural Formula C23]

[Structural Formula C24] [Structural Formula C25] [Structural Formula C26]

[Structural Formula C27] [Structural Formula C28] [Structural Formula C29] [Structural Formula C30]

[Structural Formula C31] [Structural Formula C32] [Structural Formula C33]

[Structural Formula C34] [Structural Formula C35] [Structural Formula C36]

[Structural Formula C37] [Structural Formula C38] [Structural Formula C39]

In the [Structural Formula C1] to [Structural Formula C39],

R is the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted A C3-C30 heteroaryl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or Unsubstituted C1-C30 alkylamino group, substituted or unsubstituted C1-C30 alkylsilyl group, substituted or unsubstituted C6-C30 arylamino group, and substituted or unsubstituted C6-C30 arylsilyl It is selected from groups, and may be connected to an adjacent substituent with alkylene or alkenylene to form a spiro ring or a fused ring.

L is a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C5-C30 alkyl group. It is selected from a heteroaryl group and a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms, wherein L is an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, and 3 to 20 carbon atoms It is further substituted with one or more substituents selected from a heteroaryl group, a cyano group, a halogen group, deuterium and hydrogen, and may be connected to an adjacent substituent by alkylene or alkenylene to form a spiro ring or a fused ring.

In addition, the organic electroluminescent device according to the present invention is characterized in that the organic layer includes an emission layer, and the emission layer further includes at least one phosphorescent dopant in addition to the at least one organic emission compound represented by [Chemical Formula 1], The light-emitting dopant applied to the organic electroluminescent device of the present invention is not particularly limited, but may be one or more compounds selected from compounds represented by the following [General Formula A-1] to [General Formula J-1].

[General Formula A-1]

The M is selected from the group consisting of metals of groups 7, 8, 9, 10, 11, 13, 14, 15 and 16, preferably Ir, Pt, Pd, Rh, Re , Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au and Ag. In addition, the L ₁ , L ₂ and L ₃ may be the same as or different from each other as a ligand, and may each independently include any one selected from the following [Structural Formula D], but is not limited thereto. In addition, * in the following [Structural Formula D] represents a site that binds to the metal ion M.

[Structural Formula D]

In the [Structural Formula D],

R is different from each other or the same, and each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted A heteroaryl group having 5 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or Unsubstituted C1-C30 alkylamino group, substituted or unsubstituted C1-C30 alkylsilyl group, substituted or unsubstituted C6-C30 arylamino group, and substituted or unsubstituted C6-C30 arylsilyl It may be any one selected from the group.

Each of R is independently selected from an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a cyano group, a halogen group, deuterium and hydrogen. It may be further substituted with one or more substituents.

In addition, R may be connected to each of the adjacent substituents by alkylene or alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring.

The L may be connected to an adjacent substituent with alkylene or alkenylene to form a spiro ring or a fused ring.

As an example, the dopant represented by [General Formula A-1] may be any one selected from the following compounds, but is not limited thereto.

[General Formula B-1]

In the above [general formula B-1],

M ^A1 represents the same metal ion as defined in [General Formula A-1], and Y ^A11 , Y ^A14 , Y ^A15 and Y ^A18 Each independently represents a carbon atom or a nitrogen atom, Y ^A12 , Y ^A13 , Y ^A16 and Y ^A17 each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom, and a sulfur atom, L ^A11 , L ^A12 , L ^A13 , and L ^A14 each represent a linking group as defined above, and Q ^A11 and Q ^A12 represent a partial structure containing an atom bonded to M ^A1.

An exemplary structure of the compound represented by [General Formula B-1] is as follows, but is not limited thereto.

[General Formula C-1]

In the above [general formula C-1],

M ^B1 represents the same metal ion as defined in [General Formula A-1], Y ^B11 , Y ^B14 , Y ^B15 and Y ^B18 each independently represent a carbon atom or a nitrogen atom, and Y ^B12 , Y ^B13 , Y ^B16 And Y ^B17 each independently represents a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom, and a sulfur atom, L ^B11 , L ^B12 , L ^B13 , L ^B14 represent a linking group, and Q ^B11 , Q ^B12 are It shows a partial structure containing an atom bonded to ^{M B1.}

An exemplary structure of the compound represented by [General Formula C-1] is as follows, but is not limited thereto.

[General Formula D-1]

In the above [general formula D-1],

M ^C1 represents the same metal ion as defined in [General Formula A-1], and R ^C11 and R ^C12 are each independently a hydrogen atom, a substituent that connects to each other to form a five-membered ring, and does not have any linking to each other. Represents a substituent, and R ^C13 and R ^C14 are each independently a hydrogen atom, a substituent that connects to each other to form a five-membered ring, and represents a substituent that does not have anything connected to each other, and G ^C11 and G ^C12 are each independently a nitrogen atom, substituted Or it represents an unsubstituted carbon atom, L ^C11 and L ^C12 represent a linking group, and Q ^C11 and Q ^C12 represent a partial structure containing an atom bonded to M ^C1.

An exemplary structure of the compound represented by [General Formula D-1] is as follows, but is not limited thereto.

[General Formula E-1]

In the above [general formula E-1],

M ^D1 represents the same metal ion as defined in [General Formula A-1], G ^D11 and G ^D12 each independently represent a nitrogen atom, a substituted or unsubstituted carbon atom, and J ^D11 , J ^D12 , J ^D13 and Each of J ^D14 represents an atomic group required to form a five-membered ring independently, and L ^D11 and L ^D12 represent a linking group.

An exemplary structure of the compound represented by [General Formula E-1] is as follows, but is not limited thereto.

[General Formula F-1]

In the above [general formula F-1],

M ^E1 represents the same metal ion as defined in [General Formula A-1], and J ^E11 and J ^E12 each independently represent an atomic group required to form a 5-membered ring, and G ^E11 , G ^E12 , G ^E13 and G ^E14 each independently represents a nitrogen atom, a substituted or unsubstituted carbon atom, and Y ^E11 , Y ^E12 , Y ^E13 and Y ^E14 each independently represent a nitrogen atom, a substituted or unsubstituted carbon atom.

An exemplary structure of the compound represented by [General Formula F-1] is as follows, but is not limited thereto.

[General Formula G-1]

In the above [general formula G-1],

M ^F1 represents the same metal ion as defined in [General Formula A-1].

L ^F11 , L ^F12 and L ^F13 represent a linking group, R ^F11 , R ^F12 , R ^F13 and R ^F14 represent a substituent, and R ^F11 and R ^F12 , R ^F12 And R ^F13 , R ^F13 and R ^F14 may be linked to each other to form a ring, wherein the ring formed by R ^F1 and R ^F12 , R ^F13 and R ^F14 is a 5-membered ring. In addition, Q ^F11 and Q ^F12 represent a partial structure containing an atom bonded to M ^F1.

An exemplary structure of the compound represented by [General Formula G-1] is as follows, but is not limited thereto.

[General Formula H-1] [General Formula H-2] [General Formula H-3]

In the above [General Formula H-1] to [General Formula H-3],

R ¹¹ , R ¹² are substituents of alkyl, aryl or heteroaryl; In addition, a fused ring may be formed with a substituent adjacent to each other, and q11 and q12 are integers of 0 to 4, preferably 0 to 2.

In addition, when q11 and q12 are 2 to 4, a plurality of R11 and R12 may be the same or different, respectively.

L ¹ is a ligand that binds to platinum, and is preferably a ligand capable of forming an ortho metalized platinum complex, a nitrogen-containing heterocyclic ligand, a diketone ligand, a halogen ligand, and more preferably an ortho metal. It is a ligand, a bipyridyl ligand, or a phenanthroline ligand that forms a )-plated platinum complex.

n ¹ is an integer of 0 to 3, preferably 0, and m ¹ is 1 or 2, preferably 2.

In addition, ^{it is preferable that n 1} and m ¹ make the metal complex represented by the general formula H-1 become a neutral complex.

In the above [General Formula H-2],

R ²¹ , R ²² , n ² , m ² , q ²² , L ² are the same as R ¹¹ , R ¹² , n ¹ , m ¹ , q ¹² and L ¹ , respectively, and q ²¹ is an integer of 0 to 2 , 0 is preferred.

In the above [General Formula H-3],

R ³¹ , n ³ , m ³ , L ³ are the same as R ¹¹ , n ¹ , m ¹ , and L ¹ , respectively, and q ³¹ represents an integer of 0 to 8, preferably 0 to 2, and more than 0 desirable.

Examples of specific compounds of the [General Formula H-1] to [General Formula H-3] are as follows, but are not limited thereto.

[General Formula I-1]

In the above [general formula I-1],

Ring A, Ring B, Ring C, and Ring D represent a nitrogen-containing heterocycle in which any two rings of the rings A to D may have a substituent, and the other two rings are an aryl ring or a hetero ring that may have a substituent. Represents and represents an aryl ring, and a condensed ring can be formed by ring A and ring B, ring A and ring C, and/or ring B and ring D. X ¹ , X ² , X ³ and X ⁴ represent a nitrogen atom in which any two of them are coordinated to a platinum atom, and the other two represent a carbon atom or a nitrogen atom. Q ¹ , Q ² and Q ³ each independently represent a divalent atom (term) or a bond, but Q ¹ , Q ² and Q ³ do not represent a bond at the same time. Z ¹ , Z ² , Z ³ and Z ⁴ are any two representing a coordination bond, and the other two represent a covalent bond, an oxygen atom, or a sulfur atom.

Examples of specific compounds of the [General Formula I-1] are as follows, but are not limited thereto.

[General Formula J-1]

In the above [general formula J-1],

M represents the same metal ion as defined in [General Formula A-1], Ar1 represents a substituted or unsubstituted cyclic structure, and two azomethine bonds bonded to M (-C=N-) In this case, the nitrogen atom (N) is each bonded to the M, and as a whole, forms a tridentate ligand that is bonded to the M at three loci.

In addition, in Ar1, C represents a carbon atom constituting the ring structure represented by Ar1. In addition, R1 and R2 may be the same as or different from each other, and each represents a substituted or unsubstituted alkyl group or aryl group, and L represents a monodentate ligand.

In the above [general formula J-1], it is preferable that M is Pt. Moreover, it is preferable that Ar1 is selected from a 5-membered ring, a 6-membered ring, and a condensed ring group thereof.

Examples of specific compounds of the [General Formula J-1] are as follows, but are not limited thereto.

In addition, the emission layer may further include various hosts and various dopant materials in addition to the dopant and host.

In addition, at least one layer selected from the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer may be formed by a monomolecular deposition method or a solution process, wherein the deposition method Refers to a method of forming a thin film by evaporating a material used as a material for forming each layer through heating in a vacuum or low pressure state, and the solution process is used as a material for forming each layer It refers to a method of forming a thin film through a method such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating, and the like by mixing the material to be formed with a solvent.

In addition, the organic electroluminescent device according to the present invention may be used in a device selected from a flat panel display device, a flexible display device, a monochromatic or white flat lighting device, and a monochromatic or white flexible lighting device.

Hereinafter, the present invention will be described in more detail with reference to preferred examples. However, these examples are intended to describe the present invention in more detail, and it will be apparent to those of ordinary skill in the art that the scope of the present invention is not limited thereto.

Synthesis example 1. Synthesis of Formula 2

Synthesis example 1-1. Synthesis of <1-a>

<1-a> was synthesized according to the following Scheme 1.

[Scheme 1]

<1-a>

In a 2 L reactor, 90 g (446 mmol) of 2-bromonitrobenzene, 92 g (535 mmol) of 1-naphthalene boronic acid, 123.2 g (891 mmol) of potassium carbonate, 17.2 g (9 mmol) of tetrakistriphenylphosphine palladium ), H ₂ O 180 mL, toluene 450 mL, and 1,4-dioxane 450 mL were added and stirred under reflux for 24 hours. After completion of the reaction, the mixture was concentrated under reduced pressure and separated by column chromatography to obtain 103 g of <1-a>. (Yield 87%)

Synthesis example 1-2. Synthesis of <1-b>

<1-b> was synthesized according to Scheme 2 below.

[Scheme 2]

<1-b>

In a 2 L reactor, <1-a> 103 g (413 mmol) and triphenylphosphine 325.2 g (1240 mmol) were added to 1000 mL of dichlorobenzene and stirred under reflux for 24 hours. After completion of the reaction, the mixture was concentrated and separated by column chromatography to obtain 70 g of <1-b>. (Yield 57%)

Synthesis example 1-3. Synthesis of <1-c>

<1-c> was synthesized according to Scheme 3 below.

[Scheme 3]

<1-c>

In a 500 mL reactor <1-b> 19 g (87 mmol), methyl 5-bromo-2-iodobenzoate 32.8 g (96 mmol), copper powder 5.6 g (83 mmol), 18-crown-6 -Ether 4.6 g (82 mmol) and potassium carbonate 24.2 g (175 mmol) were added, dichlorobenzene was added, and the mixture was stirred under reflux for 24 hours. After completion of the reaction, dichlorobenzene was removed and separated by column chromatography to obtain 15 g of <1-c>. (Yield 52%)

Synthesis example 1-4. Synthesis of <1-d>

<1-d> was synthesized according to Scheme 4 below.

[Scheme 4]

<1-d>

In a dried 1000 mL reactor, <1-c> 39 g (336 mmol) and 400 mL of tetrahydrofuran were added under nitrogen, and 91 mL (336 mmol) of methylmagnesium bromide was added dropwise at 0 °C. After the dropwise addition is completed, the mixture is stirred at room temperature for 3 hours. After completion of the reaction, 100 mL of 2 N-HCl aqueous solution was added at 0° C. and stirred for 30 minutes. Concentrate the organic layer, immediately add 400 mL of acetic acid and 20 mL of hydrochloric acid, and stir under reflux for 3 hours. After completion of the reaction, an excess of water was added, stirred for 30 minutes, filtered, and separated by column chromatography to obtain 14 g of <1-d>. (Yield 47%)

Synthesis example 1-5. Synthesis of <1-e>

<1-e> was synthesized according to Scheme 5 below.

[Scheme 5]

<1-e>

In a 500 mL reactor <1-d> 14 g (34 mmol), bispinacolatodiboron 10.4 g (41 mmol), palladium (II) chloride-1,1'-bis (diphenylphosphino) ferrocene 1.4 g ( 1 mmol), potassium acetate 6.7 g (68 mmol), and 140 mL of toluene are added and stirred under reflux for 10 hours. After completion of the reaction, the solid is filtered off, and the filtrate is concentrated under reduced pressure. Separated by column chromatography to obtain <1-g> 10.5 g. (Yield 61%)

Synthesis example 1-6. Synthesis of <Formula 2>

<Chemical Formula 2> was synthesized by the following Scheme 6.

[Scheme 6]

<Formula 2>

In Synthesis Example 1-1, 2-bromonitrobenzene and 1-naphthalene boronic acid were synthesized in the same manner, except that 2-chloro-4-phenyl-quinazoline and <1-e> were used instead of <Chemical Formula 2> 4.1 g was obtained. (Yield 32%)

MS [M] ⁺ 537.22

Synthesis example 2. Synthesis of Formula 9

Synthesis example 2-1. Synthesis of <2-a>

<2-a> was synthesized according to Scheme 7 below.

[Scheme 7]

<2-a>

Except for using 2-bromobenzoate instead of 5-bromo-2-iodobenzoate in Synthesis Example 1-3, it was synthesized in the same manner and <2-a> 25.6 g was obtained. (Yield 71%)

Synthesis example 2-2. Synthesis of <2-b>

<2-b> was synthesized according to Reaction Scheme 8 below.

[Scheme 8]

<2-b>

In Synthesis Example 1-4, <2-b> was synthesized in the same manner except that <2-a> was used instead of <1-c> to obtain 28.6 g of <2-b>. (Yield 71%)

Synthesis example 2-3. Synthesis of <2-c>

<2-c> was synthesized according to Scheme 9 below.

[Scheme 9]

<2-c>

After filling the dried 500 mL reactor with nitrogen, <2-b> 28.6 g (97 mmol) and 300 mL of dimethylformamide were added and stirred. Then, 28.4 g (97 mmol) of N-bromosuccinimide was slowly added to the reactor. Stir at room temperature for 4 hours. When the reaction was completed, distilled water was added dropwise at room temperature, and when brown crystals were formed, filtered and separated by column chromatography to obtain 27.8 g of <2-c>. (Yield 91%)

Synthesis example 2-4. Synthesis of <2-d>

<2-d> was synthesized according to Scheme 10 below.

[Scheme 10]

<2-d>

In Synthesis Example 1-5, <2-d> was synthesized in the same manner except that <2-c> was used instead of <1-d> to obtain 32.4 g of <2-d>. (Yield 82%)

Synthesis example 2-5. Synthesis of <Formula 9>

<Chemical Formula 9> was synthesized by the following Scheme 11.

[Scheme 11]

<Formula 9>

In Synthesis Example 1-1, 2-bromonitrobenzene and 1-naphthalene boronic acid were synthesized in the same manner except that 2-chloro-4-phenyl-quinazoline and <2-d> were used instead of <Chemical Formula 9> 3.5 g was obtained. (Yield 26%)

MS [M] ⁺ 537.22

Synthesis example 3. Synthesis of Formula 10

Synthesis example 3-1. Synthesis of <3-a>

<3-a> was synthesized according to Scheme 12 below.

[Scheme 12]

<3-a>

In Synthesis Example 1-1, <3-a> 31.2 g was obtained by synthesizing in the same manner except that 9-phenanthrene bronic acid was used instead of 1-naphthalene bronic acid. (Yield 87%)

Synthesis example 3-2. Synthesis of <3-b>

<3-b> was synthesized according to Scheme 13 below.

[Scheme 13]

<3-b>

In Synthesis Example 1-2, <3-b> was synthesized in the same manner except that <3-a> was used instead of <1-a> to obtain 28.4 g of <3-b>. (Yield 67%)

Synthesis example 3-3. Synthesis of <3-c>

<3-c> was synthesized according to Scheme 14 below.

[Scheme 14]

<3-c>

Except for using <3-b> instead of <1-b> in Synthesis Example 1-3, it was synthesized in the same manner to obtain 20.7 g of <3-c>. (Yield 62%)

Synthesis example 3-4. Synthesis of <3-d>

<3-d> was synthesized according to Scheme 15 below.

[Scheme 15]

<3-d>

In Synthesis Example 1-4, <3-d> was synthesized in the same manner except that <3-c> was used instead of <1-c> to obtain 32.4 g of <3-d>. (Yield 57%)

Synthesis example 3-5. Synthesis of <3-e>

<3-e> was synthesized according to Scheme 16 below.

[Scheme 16]

<3-e>

In Synthesis Example 1-5, <3-e> was synthesized in the same manner, except that <3-d> was used instead of <1-e> to obtain 27.4 g of <3-e>. (Yield 84%)

Synthesis example 3-6. Synthesis of <Formula 10>

<Chemical Formula 10> was synthesized by the following Scheme 17.

[Scheme 17]

<Formula 10>

In Synthesis Example 1-1, except for using 2-chloro-4-phenyl-quinazoline and <3-e> instead of 2-bromonnitrobenzene and 1-naphthalene boronic acid, it was synthesized in the same manner and <Chemical Formula 10> 2.8 g was obtained. (Yield 22%)

MS [M] ⁺ 587.24

Synthesis example 4. Synthesis of Formula 21

Synthesis example 4-1. Synthesis of <4-a>

<4-a> was synthesized according to Scheme 18 below.

[Scheme 18]

<4-a>

In Synthesis Example 1-3, <1-b> and 5-bromo-2-iodobenzoate were synthesized in the same manner except that <3-b> and 2-bromobenzoate were used instead of <4- a> 20.7 g was obtained. (Yield 62%)

Synthesis example 4-2. Synthesis of <4-b>

<4-b> was synthesized according to Scheme 19 below.

[Scheme 19]

<4-b>

In Synthesis Example 1-4, <4-b> 31.5 g was obtained by synthesizing in the same manner except that <4-a> was used instead of <1-c>. (Yield 65%)

Synthesis example 4-3. Synthesis of <4-c>

<4-c> was synthesized according to Scheme 20 below.

[Scheme 20]

<4-c>

In Synthesis Example 2-3, <4-b> was synthesized in the same manner, except that <4-b> was used instead of <2-b> to obtain 24.3 g of <4-c>. (Yield 83%)

Synthesis example 4-4. Synthesis of <4-d>

<4-d> was synthesized according to Scheme 21 below.

[Scheme 21]

<4-d>

In Synthesis Example 1-5, <4-d> was synthesized in the same manner except that <4-c> was used instead of <1-d> to obtain 30.4 g of <4-d>. (Yield 82%)

Synthesis example 4-5. Synthesis of <Formula 21>

<Chemical Formula 21> was synthesized by the following Scheme 22.

[Scheme 22]

<Formula 21>

In Synthesis Example 1-1, 2-bromonitrobenzene and 1-naphthalene boronic acid were synthesized in the same manner, except that 2-chloro-4-phenyl-quinazoline and <4-d> were used instead of <Chemical Formula 21> 2.6 g was obtained. (Yield 31%)

MS [M] ⁺ 587.24

Synthesis example 5. Synthesis of Formula 24

Synthesis example 5-1. Synthesis of <5-a>

<5-a> was synthesized according to Reaction Scheme 23 below.

[Scheme 23]

<5-a>

To a dried 2 L reactor, magnesium 6.8 g (282 mmol), a small amount of iodine, and 200 mL of tetrahydrofuran were added and stirred under nitrogen for 15 minutes. 2-bromo-9,9-dimethyl-9H-fluorene 70 g (256 mmol) is dissolved in tetrahydrofuran and added dropwise at 0°C. After stirring under reflux for about 2 hours, 15.4 g (128 mmol) of 2-aminobenzonitrile was dissolved in tetrahydrofuran at 0° C. and added dropwise, followed by reflux stirring for 2 hours. After completion of the reaction, 6 N-HCl aqueous solution was added dropwise at 0° C., and the mixture was stirred under reflux for 2 hours. At 0 ℃ 6 N-NaOH aqueous solution was added dropwise to neutralize, followed by extraction, and the organic layer was concentrated. Separated by column chromatography to obtain 20 g of <5-a>. (Yield 52%)

Synthesis example 5-2. Synthesis of <5-b>

<5-b> was synthesized according to Reaction Scheme 24 below.

[Scheme 24]

<5-b>

In a 500 mL reactor, <5-a> 34 g (108 mmol), urea 26 g (434 mmol), and 340 mL of acetic acid were added and stirred under reflux for 12 hours. After completion of the reaction, the reactant was added to water in excess, precipitated, and filtered. The slurry was hot with methanol, filtered, and then hot slurry with toluene was filtered and dried to obtain 15 g of <5-b>. (Yield 66%)

Synthesis example 5-3. Synthesis of <5-c>

<5-c> was synthesized according to Scheme 25 below.

[Scheme 25]

<5-c>

In a 300 mL reactor, <5-b> 15 g (44 mmol) and 150 mL of phosphorus oxychloride were added and stirred under reflux for 3 hours. After completion of the reaction, the reactant was slowly added to an excess of water at 0° C. to precipitate and then filtered. Separated by column chromatography to obtain 12 g of <5-c>. (Yield 62%)

Synthesis example 5-4. Synthesis of <Formula 24>

<Chemical Formula 24> was synthesized according to Reaction Scheme 26 below.

[Scheme 26]

<Formula 24>

In Synthesis Example 1-1, <1-e> and <5-c> were used instead of 2-bromontrobenzene and 1-naphthalene boronic acid, and 2.9 g of <Chemical Formula 24> was obtained. (Yield 29%)

MS [M] ⁺ 653.28

Synthesis example 6. Synthesis of Formula 39

Synthesis example 6-1. Synthesis of <6-a>

<6-a> was synthesized according to Scheme 27 below.

[Scheme 27]

<6-a>

After filling the dried 2 L reactor with nitrogen, it was dissolved in ethyl cyanoacetate 139.8 g (1.236 mol), potassium cyanide 29.5 g (0.453 mol), potassium hydroxide 46.2 g (0.824 mol), and 920 mL of dimethylformamide. Stir at 10° C. for 20 minutes. Then, 1-nitronaphthalene 92 g (412 mol) was added and stirred at 60° C. for 4 hours. After completion of the reaction, the solvent was concentrated, 600 mL of a 10% sodium hydroxide aqueous solution was added, and the mixture was stirred under reflux for 1 hour. The solid was filtered and separated by column chromatography to obtain 50 g of <6-a>. (Yield 60%)

Synthesis example 6-2. Synthesis of <6-b>

<6-b> was synthesized according to Scheme 28 below.

[Scheme 28]

<6-b>

After filling the dried 1 L reactor with nitrogen, <6-a> 50.0 g (297 mmol) and 500 mL of dimethylformamide were stirred. Then, 55.56 g (312 mmol) of N-bromosuccinimide was slowly added to the reactor. Stir at room temperature for 4 hours. When the reaction was completed, distilled water was added dropwise at room temperature to form brown crystals. The crystals were filtered and separated by column chromatography to obtain 68 g of <6-b>. (Yield 93%)

Synthesis example 6-3. Synthesis of <6-c>

<6-c> was synthesized according to Scheme 29 below.

[Scheme 29]

<6-c>

In Synthesis Example 1-1, <6-b> and phenyl boronic acid were used instead of 2-bromonitrobenzene and 1-naphthalene boronic acid, and <6-c> 35.1 g was obtained. (Yield 81%)

Synthesis example 6-4. Synthesis of <6-d>

<6-d> was synthesized according to Scheme 30 below.

[Scheme 30]

<6-d>

After filling the dried 2 L reactor with nitrogen, 45.0 g (381 mmol) of 2-aminobenzonitrile and 450 mL of tetrahydrofuran were added, and 250 mL (430 mmol) of phenylmagnesium bromide was slowly added dropwise at 0 °C, followed by reflux stirring for 3 hours. do. After dissolving 30 g (225 mmol) of ethyl chloroformate in 200 mL of tetrahydrofuran, it was slowly added dropwise and stirred under reflux for 2 hours. After completion of the reaction, extraction was performed, and the organic layer was concentrated under reduced pressure and separated by column chromatography to obtain 51 g of <6-d>. (Yield 78%)

Synthesis example 6-5. Synthesis of <6-e>

<6-e> was synthesized according to Reaction Scheme 31 below.

[Scheme 31]

<6-e>

Synthesis was performed in the same manner as <6-e>, except that <6-d> obtained in Scheme 30 was used instead of <5-b> used in Scheme 25 of Synthesis Example 5-3 to obtain 37 g of <6-e>. (Yield 72%)

Synthesis example 6-5. Synthesis of <Formula 39>

<Chemical Formula 39> was synthesized according to Reaction Scheme 32 below.

[Scheme 32]

<Formula 39>

In Synthesis Example 1-1, <2-d> and <6-e> were used instead of 2-bromonnitrobenzene and 1-naphthalene boronic acid, and 3.4 g of <Chemical Formula 39> was obtained. (Yield 27%)

MS [M] ⁺ 663.27

Synthesis example 7. Synthesis of Formula 66

Synthesis example 7-1. Synthesis of <7-a>

<7-a> was synthesized according to Reaction Scheme 33 below.

[Scheme 33]

<7-a>

In a 2 L reactor, biphenyl-4-amine 50.0 g (330 mmol), 2-bromo-9,9-dimethyl-9H-fluorene 43.2 g (276 mmol), palladium acetate 1.2 g (5.6 mmol), xantphos 6.4 g (11.02 mmol), 126 g (386 mmol) of cesium carbonate, and 1000 mL of toluene were added and stirred under reflux for 24 hours. After completion of the reaction, the mixture was cooled to room temperature, filtered, and toluene was concentrated under reduced pressure. Separated by column chromatography to obtain 57 g of <1-d>. (Yield 91%)

Synthesis example 7-2. Synthesis of <Formula 66>

<Chemical Formula 66> was synthesized according to Reaction Scheme 34 below.

[Scheme 34]

<Formula 66>

In a 250 mL reactor, <1-d> 7.9 g (24.6 mmol), <7-a> 8.3 g (30 mmol), palladium acetate 0.4 g (0.3 mmol), sodium tertiary butoxide 4.2 g (43 mmol), tri Add 0.1 g (0.3 mmol) tertiary butylphosphine and 100 mL of toluene, and stir under reflux for 13 hours. After completion of the reaction, it was concentrated. Separated by column chromatography and recrystallized with methylene chloride and methanol to obtain 4.0 g of <Chemical Formula 66>. (Yield 45%)

MS [M] ⁺ 692.32

Synthesis example 8. Synthesis of Formula 74

Synthesis example 8-1. Synthesis of <8-a>

<8-a> was synthesized according to Scheme 35 below.

[Scheme 35]

<8-a>

In a 500 mL reactor, tribromobenzene 25 g (79 mmol), phenylbronic acid 23.3 g (191 mmol), potassium carbonate 32.9 g (238 mmol), tetrakistriphenylphosphine palladium 6.12 g (3 mmol), distilled water 50 mL, 125 mL of toluene, and 125 mL of 1,4-dioxane were added and stirred under reflux for 24 hours. After completion of the reaction, the reaction product was separated into layers, and the organic layer was concentrated under reduced pressure. Recrystallized from toluene and methanol to obtain 21 g of <8-a>. (Yield 85%)

Synthesis example 8-2. Synthesis of <8-b>

<8-b> was synthesized according to Scheme 36 below.

[Scheme 36]

<8-b>

In Synthesis Example 7-1, <8-b> was synthesized in the same manner, except that <8-a> was used instead of 2-bromo-9,9-dimethyl-9H-fluorene to obtain 14 g of <8-b>. (Yield 72%)

Synthesis example 8-3. Synthesis of <Formula 74>

<Chemical Formula 74> was synthesized according to Reaction Scheme 37 below.

[Scheme 37]

<Formula 74>

Except for using <3-d> and <8-b> instead of <1-d> and <7-a> in Synthesis Example 7-2, it was synthesized in the same manner to obtain 3.2 g of <Chemical Formula 74>. (Yield 19%)

MS [M] ⁺ 778.33

Synthesis example 9. Synthesis of Formula 98

Synthesis example 9-1. Synthesis of <9-a>

<9-a> was synthesized according to Scheme 38 below.

[Scheme 38]

<9-a>

Synthesis was performed in the same manner as in Synthesis Example 7-1, except that 2-aminonaphthalene was used instead of 4-aminobiphenyl to obtain 17 g of <9-a>. (Yield 62%)

Synthesis example 9-2. Synthesis of <Formula 98>

<Chemical Formula 98> was synthesized according to Reaction Scheme 39 below.

[Scheme 39]

<Formula 98>

In Synthesis Example 7-2, except that <9-a> was used instead of <7-a>, it was synthesized in the same manner to obtain 3.1 g of <Chemical Formula 98>. (Yield 28%)

MS [M] ⁺ 666.30

Synthesis example 10. Synthesis of Formula 106

Synthesis example 10-1. Synthesis of <10-a>

<10-a> was synthesized according to Scheme 40 below.

[Scheme 40]

<10-a>

Synthesis was performed in the same manner except that 1-bromo-5-methoxynaphthalene was used instead of <1-d> used in Scheme 5 of Synthesis Example 1-5 to obtain 63 g of <10-a>. (Yield 82%)

Synthesis example 10-2. Synthesis of <10-b>

<10-b> was synthesized according to Scheme 41 below.

[Scheme 41]

<10-b>

Synthesis was carried out in the same manner except that <10-a> obtained in Scheme 40 was used instead of 1-naphthalene boronic acid used in Scheme 1 of Synthesis Example 1-1, and <10-b> 58.3 g was obtained. (Yield 86%)

Synthesis example 10-3. Synthesis of <10-c>

<10-c> was synthesized according to Scheme 42 below.

[Scheme 42]

<10-c>

Synthesis was performed in the same manner except that <10-b> obtained in Scheme 41 was used instead of <1-a> used in Scheme 2 of Synthesis Example 1-2 to obtain 31 g of <10-c>. (Yield 64%)

Synthesis example 10-4. Synthesis of <10-d>

<10-d> was synthesized according to Scheme 43 below.

[Scheme 43]

<10-d>

Except for using <10-c> obtained in Scheme 42 instead of <1-b> used in Scheme 3 of Synthesis Example 1-3, it was synthesized in the same manner to obtain 24.6 g of <10-d>. (Yield 62%)

Synthesis example 10-5. Synthesis of <10-e>

<10-e> was synthesized according to Scheme 44 below.

[Scheme 44]

<10-e>

Except for using <10-d> obtained in Scheme 43 instead of <1-c> used in Scheme 4 of Synthesis Example 1-4, <10-e> 20.4 g was obtained. (Yield 72%)

Synthesis example 10-6. Synthesis of <10-f>

<10-f> was synthesized according to Scheme 45 below.

[Scheme 45]

<10-f>

In a 500 mL reactor, <10-f> 20.4 g (320 mmol), hydrogen bromide 20 g (276 mmol), and 200 mL of acetic acid were added and stirred under reflux for 15 hours. After completion of the reaction, extraction was performed and the organic layer was concentrated. Separated by column chromatography to obtain 18 g of <10-f>. (Yield 91%)

Synthesis example 10-7. Synthesis of <10-g>

<10-g> was synthesized according to Scheme 46 below.

[Scheme 46]

<10-g>

In a 500 mL reactor, <10-f> 18 g (52 mmol), trifluoromethanesulfonic anhydride 17.5 g (62 mmol), pyridine 4.9 g (62 mmol), and methylene chloride 180 mL were added and stirred at room temperature for 5 hours. . After completion of the reaction, extraction was performed and the organic layer was concentrated. Separated by column chromatography, <10-g> 22.8 g was obtained. (Yield 94%)

Synthesis example 10-8. Synthesis of <Formula 106>

<Chemical Formula 106> was synthesized by the following Scheme 47.

[Scheme 47]

<Formula 106>

Except for using <10-g> instead of <1-d> in Synthesis Example 7-2, it was synthesized in the same manner to obtain 2.1 g of <Chemical Formula 106>. (Yield 18%)

MS [M] ⁺ 692.32

Example 1 to 6: Preparation of organic light emitting diode

The ITO glass was patterned so that the light emitting area had a size of 2 mm×2 mm, and then washed. After mounting the substrate in the vacuum chamber, the base pressure is 1 × 10 ^-6 torr, and then the organic material is placed on the ITO DNTPD (700 Å), NPD (300 Å), the compound prepared by the present invention + RD-1 ( 10%) (300 Å), Alq ₃ (350 Å), LiF (5 Å), and Al (1,000 Å) were formed in the order, and the measurement was performed at 0.4 mA.

<DNTPD> <α-NPB>

<RD-1><CompoundE><Liq>

Comparative example 1 to 2

The organic light-emitting diode device for Comparative Example 1 was manufactured in the same manner, except that BAlq and RH1, which are commonly used as phosphorescent host materials, were used instead of the compound prepared by the invention in the device structure of the above example. The structure is as follows.

<BAlq> <RH1>

For the organic electroluminescent devices manufactured according to Examples 1 to 6 and Comparative Examples 1 to 2, voltage, current density, luminance, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. T95 refers to the time it takes for the luminance to decrease from the initial luminance (3000 cd/m2) to 95%.

division Host Doping concentration% V Cd/㎡ CIEx CIEy T ₉₅ (Hr) Comparative Example 1 BAlq 10 6.2 1470 0.665 0.334 40 Comparative Example 2 RH1 10 4.3 2100 0.665 0.334 110 Example 1 2 10 4.0 2310 0.665 0.335 224 Example 2 9 10 4.2 2350 0.664 0.335 185 Example 3 10 10 4.1 2230 0.665 0.334 187 Example 4 21 10 4.2 2360 0.665 0.334 216 Example 5 24 10 4.0 2300 0.666 0.333 191 Example 6 39 10 4.2 2390 0.665 0.334 220

As shown in [Table 1], the organic compound secured by the present invention has higher efficiency and lower driving voltage than BAlq among host materials commonly used as phosphorescent host materials, and has more improved lifespan than RH1.

Example 7: Preparation of organic light-emitting diode

The ITO glass was patterned so that the light emitting area had a size of 2 mm×2 mm, and then washed. After the substrate is mounted in a vacuum chamber, the base pressure is set to 1 × 10 ^-6 torr, and then an organic material is deposited on the ITO in the order of DNTPD (700 Å), compound 66 (300 Å) prepared by the present invention. , After mixing the host BH1 and 3% of the dopant BD1 to form a film (250 Å), the compound E1: Liq = 1:1 (250 Å), Liq (10 Å), Al (1,000 Å) was formed in the order, and 0.4 Measurements were made in mA.

Example 8 to 10: Preparation of an organic light emitting diode

An organic electroluminescent device was manufactured in the same manner as in Example 7, except that the compound 66 prepared by the present invention used in Example 7 was used instead of the one described in [Table 2]. Was measured at 0.4 mA.

<BH1><BD1>

Comparative example 3 to 4

In the device structures of Examples 7 to 10, except for the fact that α-NPB and HT1, which are commonly used as hole transport layer materials, were used instead of the compounds prepared by the invention, the structures of α-NPB and HT1 were It is as follows.

<α-NPB> <HT1>

For the organic electroluminescent devices prepared in Examples 7 to 10 and Comparative Examples 3 to 4, voltage, current, luminance, color coordinates, and lifetime were measured, and the results are shown in Table 2 below. T80 refers to the time it takes for the luminance to decrease to 80% compared to the initial luminance (3000 cd/㎡).

division Hole transport compound V Cd/㎡ CIEx CIEy T ₈₀ (Hrs) 3000 cd/㎡ Comparative Example 3 α-NPB 4.4 650 0.133 0.129 85 Comparative Example 4 HT1 4.2 730 0.150 0.150 110 Example 7 Formula 66 4.1 810 0.133 0.128 175 Example 8 Formula 74 4.2 790 0.132 0.126 180 Example 9 Formula 98 4.3 795 0.132 0.127 185 Example 10 Formula 106 4.3 770 0.132 0.127 170

As shown in [Table 2], the organic light-emitting compound according to the present invention has higher luminous efficiency and long life than α-NPB and HT1 among transport layer materials commonly used as hole transport layer materials.

Claims (13)

Organic light-emitting compound represented by the following [Chemical Formula 1]:
[Formula 1]

In the above [Formula 1],
Z is any one selected from the following [Structural Formula C1] to [Structural Formula C8],

In the [Structural Formula C1] to [Structural Formula C8],
Each R'is independently selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms. Become,
m is an integer of 1 to 8, and when m is 2 or more, each R'may be the same as or different from each other, and * means a site bonded to [Formula 1],
X ₁ to X ₈ are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted carbon number 2 to 30 alkenyl group, substituted or unsubstituted C 2 to C 30 alkynyl group, substituted or unsubstituted C 3 to C 30 cycloalkyl group, substituted or unsubstituted and selected from O, N, S, and P as heteroatoms A heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 1 to 30 carbon atoms. 30 alkylamine group, substituted or unsubstituted C5 to C30 arylamine group, substituted or unsubstituted C1 to C30 alkylsilyl group, substituted or unsubstituted C5 to C30 arylsilyl group, cyano group And a halogen group,
At least one of the X ₁ to X ₈ is bonded to the following [Structural Formula A], or is bonded to the following [Structural Formula B],

In the [Structural Formula A] and [Structural Formula B],
* Means a site bonding to X _{1 to X 8} of the [Chemical Formula 1],
L ₁ and L ₂ are each independently a substituted or unsubstituted C1-C30 alkylene group, a substituted or unsubstituted C2-C30 alkylene group. Alkenylene group, substituted or unsubstituted C2 to C30 alkynylene group, substituted or unsubstituted C3 to C30 A cycloalkylene group, a substituted or unsubstituted arylene group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms, a substituted or unsubstituted substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms fused to one or more It is selected from a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms in which one or more substituted or unsubstituted C3 to C30 cycloalkyl groups are fused, and n and m are 0 Is an integer of 2, and when n and m are 2, a plurality of L ₁ and L ₂ are the same as or different from each other,
Ar ₁ to Ar ₃ are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted C 5 to 50 It is selected from an aryl group and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having any one or more selected from O, N, S, and P as a hetero atom,
R ₁ and R ₂ are selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms Become,
R ₁ and R ₂ , L ₁ and L ₂ , Ar ₁ to Ar ₃ may each be connected with a substituent adjacent to each other to form a substituted or aromatic monocyclic or polycyclic ring, and the carbon atoms of the formed alicyclic, aromatic monocyclic or polycyclic ring are N, S and O It may be substituted with any one or more heteroatoms selected from,
'Substituted'in'substituted or unsubstituted' in [Chemical Formula 1] means to be further substituted with one or more substituents, and the one or more substituents are deuterium, cyano group, halogen group, hydroxy group, nitro group , An alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, 6 to 24 arylalkyl group, C 2 to C 24 heteroaryl group, or C 2 to C 24 heteroarylalkyl group, C 1 to C 24 alkoxy group, C 1 to C 24 alkylamino group, C 1 to C 24 arylamino group, It is selected from the group consisting of a C1-C24 heteroarylamino group, a C1-C24 alkylsilyl group, a C1-C24 arylsilyl group, and a C1-C24 aryloxy group. delete The method of claim 1,
_{Ar 3} of the [Structural Formula B] is an organic light-emitting compound, characterized in that any one selected from the following [Structural Formula D1] to [Structural Formula D6]:

In the [Structural Formula D1] to [Structural Formula D6],
X is O, S, NR or CRR (R is the same as the definition _{of R 1} and R _{2 in [Chemical Formula 1]),}
R" is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or Unsubstituted C6-C30 aryloxy group, substituted or unsubstituted C1-C30 alkylthioxy group, substituted or unsubstituted C5-C30 arylthioxy group, substituted or unsubstituted C1-C30 aryloxy group Alkylamine group, substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, substituted or unsubstituted aryl group having 5 to 50 carbon atoms, substituted or unsubstituted and having 2 to 50 carbon atoms having O, N or S as a hetero atom It is selected from a heteroaryl group, a cyano group, a nitro group and a halogen group,
n is an integer of 1 to 8, and when n is 2 or more, a plurality of R"s are the same as or different from each other,
When the substituent R" is not bonded to the carbon of the aromatic ring in the heteroaryl group of [Structural Formula D1] to [Structural Formula D6], hydrogen or deuterium may be bonded,
One of the plurality of R" may be a single bond bonded to a nitrogen atom. The method of claim 1,
[Chemical Formula 1] is an organic light-emitting compound, characterized in that any one compound selected from the group represented by the following [Chemical Formula 2] to [Chemical Formula 65]:

The method of claim 1,
Only one of X ₁ to X ₈ is bonded to the [Structural Formula A], and n is an integer of 0 to 2, and L ₁ is a single bond, or selected from the following [Structural Formula 1] to [Structural Formula 8] Which one,
An organic light-emitting compound, characterized in that hydrogen or deuterium may be bonded to the carbon site of the aromatic ring of the following [Structural Formula 1] to [Structural Formula 8]:

The method of claim 1,
_{Ar 1} and Ar ₂ of the [Structural Formula A] are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 24 carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 24 carbon atoms. Organic light-emitting compounds. The method of claim 1,
[Chemical Formula 1] is an organic light-emitting compound, characterized in that any one compound selected from the group represented by the following [Chemical Formula 66] to [Chemical Formula 113].

A first electrode; A second electrode facing the first electrode; And an organic layer interposed between the first electrode and the second electrode,
An organic electroluminescent device, characterized in that the organic layer includes at least one organic light-emitting compound according to any one of claims 1 and 3 to 7. The method of claim 8,
The organic layer includes at least one of a hole injection layer, a hole transport layer, an emission layer, a hole blocking layer, an electron transport layer, and an electron injection layer. The method of claim 8,
An organic layer interposed between the first electrode and the second electrode includes an emission layer, and the emission layer includes a host and a dopant,
An organic electroluminescent device, characterized in that the organic light-emitting compound according to any one of claims 1 and 3 to 7 is used as a host. The method of claim 8,
The organic layer interposed between the first electrode and the second electrode includes at least one of a hole injection layer and a hole transport layer,
An organic electroluminescent device, characterized in that the organic light-emitting compound according to any one of claims 1 and 3 to 7 is used for a hole injection layer or a hole transport layer. The method of claim 9,
The organic electroluminescent device, characterized in that the organic layer is formed by a deposition process or a solution process. The method of claim 8,
The organic light-emitting device is an organic light-emitting device, characterized in that used in any one device selected from a flat panel display device, a flexible display device, a single-color or white flat-panel lighting device, and a single-color or white flexible lighting device.

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