KR102191779B1 - Aromatic compound and organoelectro luminescent device comprising the compound - Google Patents

Abstract

The present invention relates to an aromatic compound represented by the following [Chemical Formula 1] and an organic electroluminescent device including the same. The organic electroluminescent device including the aromatic compound according to the present invention has a low driving voltage and excellent luminous efficiency.
[Formula 1]

Description

Aromatic compound and organoelectro luminescent device comprising the compound

The present invention relates to an aromatic compound and an organic electroluminescent device comprising the same.

An organic electroluminescent device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls back to the ground. These organic electroluminescent devices are known to have characteristics such as self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high-speed response.

Materials used as the organic material layer in the organic electroluminescent device can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, electron injection materials, and the like, according to their functions. The light-emitting material may be classified into a high-molecular-type and a low-molecular-type according to its molecular weight, and may be classified into a fluorescent material derived from the singlet excited state of the electron and a phosphorescent material derived from the triplet excited state of the electron according to the light emitting mechanism. . In addition, the light-emitting material may be classified into blue, green, and red light-emitting materials and yellow and orange light-emitting materials necessary for realizing a better natural color according to the light-emitting color.

On the other hand, when only one material is used as a light-emitting material, the maximum emission wavelength shifts to a long wavelength due to intermolecular interactions, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect.Therefore, the increase in color purity and energy transfer A host-dopant system may be used as a light-emitting material in order to increase the luminous efficiency through.

The principle is that when a small amount of a dopant having an energy band gap smaller than that of the host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant used.

Organic light-emitting devices are gradually expanding their application fields to the display and lighting fields of various electronic products, but efficiency and lifespan characteristics are limiting the expansion of the application field, and materials as well as devices are used to improve efficiency and lifespan characteristics. On the side, many studies are being conducted. In terms of materials, a host-dopant system is mainly used as a method for maximizing luminous efficiency, and a phosphorescent material is used for the dopant as a luminescent material, and CBP (4,4'-N, N'-dicarbazolbiphenyl) and carbazole have various substituents introduced therein, but further improvement is required in terms of efficiency and lifespan characteristics.

[Prior technical literature]

[Patent Literature]

Japanese Patent Publication 2008-214244

Japanese Patent Publication 2003-133075

The problem to be solved by the present invention is to provide a novel aromatic compound and an organic electroluminescent device including the same and low driving voltage and excellent luminous efficiency.

The present invention provides an aromatic compound represented by the following [Chemical Formula 1] in order to solve the above problems.

[Formula 1]

In addition, the present invention provides an organic electroluminescent device having a first electrode, a second electrode, and an organic material layer interposed between the first electrode and the second electrode, and including an aromatic compound represented by [Chemical Formula 1]. .

A specific substituent of the above [Formula 1] will be described later.

When the aromatic compound according to the present invention is used in the organic material layer of an organic light emitting device, low voltage driving is possible, so that power efficiency is excellent and brightness is improved, so that a very economical organic light emitting device can be implemented.

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

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

The aromatic compound according to the present invention is characterized by being represented by the following [Chemical Formula 1].

[Formula 1]

In the above [Formula 1],

Q is selected from a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 60 carbon atoms, and a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms.

L is a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynylene group having 2 to 60 carbon atoms, or substituted or unsubstituted A substituted or unsubstituted heterocycloalkylene group having 2 to 6 carbon atoms, including at least one selected from N, O and S, a cycloalkylene group having 3 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms And a substituted or unsubstituted divalent linking group selected from the group consisting of a heteroarylene group having 3 to 50 carbon atoms, l and m are integers of 0 to 3, when l and m are 2 or more, a plurality of L is the same or different, respectively can do.

X is selected from the group consisting of CR ₁₁ R ₁₂ , NR ₁₃ , O, Se, P, S and SiR ₁₄ R ₁₅ .

R ₁ to R ₁₅ 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 40 carbon atoms, a substituted or unsubstituted carbon number 2 to 30 alkenyl group, substituted or unsubstituted C 2 to C 20 alkynyl group, substituted or unsubstituted C 3 to C 30 cycloalkyl group, substituted or unsubstituted C 5 to C 30 cycloalkenyl group, substituted or unsubstituted A ringed heteroaryl group having 2 to 40 carbon atoms having O, N, S or P as hetero 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 an unsubstituted C1-C30 alkylthioxy group, a substituted or unsubstituted C5-C30 arylthioxy group, a substituted or unsubstituted C1-C30 alkylamine group, a substituted or unsubstituted C5-C30 Is any one selected from an arylamine group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a cyano group, a hydroxyl group, a nitro group and a halogen group. .

The Q, L, X, R ₁ to R ₁₅ , and their substituents may be bonded to each other or adjacent substituents to form a saturated or unsaturated ring, or may be attached or fused together in a pendant manner.

According to an embodiment of the present invention, the Q, L, X and R ₁ to R ₁₅ are each independently a deuterium atom, a cyano group, a halogen atom, a hydroxy group, a nitro group, an alkyl group having 1 to 40 carbon atoms, and 3 to 40 carbon atoms. Cycloalkyl group, C2-C30 alkenyl group, C2-C40 alkynyl group, C1-C40 alkoxy group, C1-C40 alkylamino group, C6-C40 arylamino group, C3-C40 hetero Arylamino group, alkylsilyl group having 1 to 40 carbon atoms, arylsilyl group having 6 to 40 carbon atoms, aryl group having 6 to 40 carbon atoms, aryloxy group having 3 to 40 carbon atoms, heteroaryl group having 3 to 40 carbon atoms, germanium group, It may be substituted with one or more selected from the group consisting of phosphorus and boron.

In the present invention, the term "substituted" means to be substituted with the above one or more substituents.

In addition, the range of carbon atoms of the alkyl group or aryl group in the "substituted or unsubstituted alkyl group having 1 to 30 carbon atoms", "substituted or unsubstituted aryl group having 5 to 40 carbon atoms", etc. considers the portion where the substituent is substituted It does not mean the total number of carbon atoms constituting the alkyl moiety or the aryl moiety when viewed as unsubstituted. For example, a phenyl group in which a butyl group is substituted in the para position corresponds to an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

In addition, according to a preferred embodiment of the present invention, when l and m are each 1, the L may be a single bond or any one selected from the following [Structural Formula A1] to [Structure A8].

[Structural Formula A1] [Structural Formula A2] [Structural Formula A3] [Structural Formula A4]

[Structural Formula A5] [Structural Formula A6] [Structural Formula A7] [Structural Formula A8]

In the [Structural Formulas A1] to [Structural Formulas A8], hydrogen or deuterium may be bonded to the carbon of the aromatic ring in each of the structural formulas.

In addition, when l and m are each 2, L may be any one selected from the following [Structural Formula B].

[Structural Formula B]

In the [Structural Formula B], hydrogen or deuterium may be bonded to the carbon of the aromatic ring in each structural formula. In addition, in the case of a substituent other than hydrogen, a saturated or unsaturated ring may be formed by bonding with adjacent substituents.

According to a preferred embodiment of the present invention, the aromatic compound according to [Chemical Formula 1] is not limited by the following specific examples, but more specifically compounds represented by the following [Chemical Formula 1-1] to [Chemical Formula 1-3] It can be any one of.

[Formula 1-1] [Formula 1-2] [Formula 1-3]

In the [Chemical Formula 1-1] to [Chemical Formula 1-3], L, l, m, X and R ₁ to R ₁₄ are the same as defined in [Chemical Formula 1].

On the other hand, the aryl group contained in the organic light-emitting compound according to the present invention is an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen, and a single or fused ring system containing 5 to 7 members, preferably 5 or 6 members. In addition, when the aryl group has a substituent, it may be fused with neighboring substituents to further form a ring.

Specific examples of such aryl are phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-ethylphenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, 4-methylbiphenyl group, 4- Ethylbiphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, 1-naphthyl group, 2-naphthyl group, 1-methylnaphthyl group, 2-methylnaphthyl group, anthryl group, phenanthryl group, pyre And aromatic groups such as anyl group, indenyl, fluorenyl group, tetrahydronaphthyl group, pyrenyl, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl, and the like.

In addition, 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, and in this case, referred to as an "alkylamino group"), an amidino group, a hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, a C1-C24 group Alkyl group, halogenated alkyl group having 1 to 24 carbon atoms, alkenyl group having 1 to 24 carbon atoms, alkynyl group having 1 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 6 to 24 carbon atoms , It may be substituted with a C2-C24 heteroaryl group or a C2-C24 heteroarylalkyl group.

The heteroaryl group, which is a substituent used in the present invention, may be any one selected from the following [Structural Formula 1] to [Structural Formula 6] when R ₁ and R ₆ are heteroaryl groups.

[Structural Formula 1] [Structural Formula 2] [Structural Formula 3]

[Structural Formula 4] [Structural Formula 5] [Structural Formula 6]

In the [Structural Formula 1] to [Structural Formula 6],

T ₁ to T ₈ 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 , The R ₃₁ to R ₄₄ are the same 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 cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted The aryl group having 5 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms having O, NS and P as heteroatoms may be any one selected from [Structural Formulas 1] to [Structural Formulas] 6] in the above R ₃₁ to R ₄₄ One of them may be combined with the [Chemical Formula 1-1] to [Chemical Formula 1-3] to form a single bond.

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 ₅ and R ₃₃ and R ₃₄ are the same as defined above.

Further, according to a preferred embodiment of the present invention, the heteroaryl group may be selected from [Structural Formula 1] to [Structural Formula 6] below [Structural Formula 7].

[Structural Formula 7]

In [Structural Formula 7],

X is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 2 to 20 alkynyl group, substituted or unsubstituted C 3 to C 30 cycloalkyl group, substituted or unsubstituted C 5 to C 30 cycloalkenyl group, substituted or unsubstituted C 1 to C 30 alkoxy group, substituted or unsubstituted A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyl thioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted alkyl having 1 to 30 carbon atoms The group consisting of an amine group, a substituted or unsubstituted aryl group having 5 to carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms having O, N, S or P as a hetero atom, a cyano group, a nitro group, a halogen group It may be any one selected from among.

m is an integer of 1 to 11, and when m is 2 or more, a plurality of Xs are the same as or different from each other, and any one of the at least one X is a single bond with the [Formula 1-1] to [Formula 1-3] It can be achieved.

Specific examples of the alkyl group as a substituent 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 , Octyl group, stearyl group, trichloromethyl group, trifluoromethyl group, etc., and at least one hydrogen atom of 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 (In this case, referred to as "alkylsilyl group"), a substituted or unsubstituted amino group (-NH ₂ , -NH(R), -N(R')(R"), wherein R, R'and R" are each It is independently an alkyl group having 1 to 24 carbon atoms (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, an alkyl group having 1 to 24 carbon atoms, and having 1 to 24 carbon atoms 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 hetero It may be substituted with an aryl group or a heteroarylalkyl group having 3 to 24 carbon atoms.

Specific examples of the alkoxy group as a substituent used in the compound of the present invention include methoxy group, ethoxy group, propoxy group, isobutyloxy group, sec-butyloxy group, pentyloxy group, iso-amyloxy group, hexyloxy group, etc. And the same substituents as in the case of the above alkyl group.

Specific examples of the halogen group that is a substituent used in the compound of the present invention include fluorine (F), chlorine (Cl), bromine (Br), and the like.

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 as a substituent used in the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, silyl, diphenylvinylsilyl, methylcyclobutylsilyl And dimethylfurylsilyl.

Specific examples of the alkenyl group used in the present invention represent a linear or branched alkenyl group, 3-pentenyl group, 4-hexenyl group, 5-heptenyl group, 4-methyl-3-pentenyl group, 2,4 -Dimethyl-pentenyl group, 6-methyl-5-heptenyl group, 2,6-dimethyl-5-heptenyl group, etc. are mentioned.

Specific examples of the aromatic compound according to the present invention may include any one compound selected from the group consisting of compounds represented by the following [Chemical Formula 2] to [Chemical Formula 242], but the present invention is not limited thereto.

[화학식 218] [화학식 219] [화학식 220] [화학식 221]

[Formula 218] [Formula 219] [Formula 220] [Formula 221]

[화학식 222] [화학식 223] [화학식 224] [화학식 225]

[Formula 222] [Formula 223] [Formula 224] [Formula 225]

[화학식 226] [화학식 227] [화학식 228] [화학식 229]

[Formula 226] [Formula 227] [Formula 228] [Formula 229]

[화학식 230] [화학식 231] [화학식 232] [화학식 233]

[Formula 230] [Formula 231] [Formula 232] [Formula 233]

[화학식 234] [화학식 235] [화학식 236] [화학식 237]

[Formula 234] [Formula 235] [Formula 236] [Formula 237]

[Formula 238] [Formula 239] [Formula 240] [Formula 241]

[Formula 242]

In addition, the present invention includes a first electrode, a second electrode opposite to the first electrode, and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer is the [Chemical Formula 1] in the present invention. It may contain one or more types of aromatic compounds represented by.

In addition, the organic layer containing the aromatic 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, an emission 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 aromatic compound of the present invention may be used as a host.

Meanwhile, in the present invention, a dopant material may be used in addition to a host for the emission layer. When the emission 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.

Hereinafter, the organic electroluminescent device of the present invention will be described with reference to FIG. 1.

1 is a cross-sectional view showing the structure of an organic light emitting 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 80, and if necessary, the hole injection layer 30 and An electron injection layer 70 may be further included, and in addition to that, a first or second intermediate layer may be further formed, and a hole blocking layer or an electron blocking layer may be further formed.

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, the 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 conventional organic EL device is used, and an organic substrate or a transparent plastic substrate excellent in 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), etc., which are transparent and have excellent conductivity, are used.

The hole injection layer 30 is formed by vacuum thermal evaporation or spin coating on the anode 20 electrode. Then, 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 is not particularly limited as long as it is commonly used in the art, and may be used, for 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 ], etc. can be used.

In addition, as the material of the hole transport layer is not particularly limited as long as it is commonly used in the art, and 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), and the like can 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 vacuum deposition or spin coating to form a thin film. can do. The hole blocking layer plays a role of preventing such a 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. . At this time, the hole blocking material used is not particularly limited, but it must have an electron transport ability and have a higher ionization potential than the light-emitting compound, and representatively, BAlq, BCP, TPBI, and the like may be used.

As a material used for the hole blocking layer, any one selected from BAlq, BCP, Bphen, TPBI, NTAZ, BeBq ₂ , OXD-7, Liq, and [Formula 101] to [Formula 107] may be used, but limited thereto It does not become.

BAlq BCP Bphen

TPBI NTAZ BeBq ₂

OXD-7 Liq

Formula 101 Formula 102 Formula 103

Formula 104 Formula 105 Formula 106

Chemical Formula 107

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 metal is lithium (Li), magnesium (Mg), aluminum (Al), aluminum-ridium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver ( Mg-Ag) or the like may be used, and in order to obtain a top light emitting device, a transmissive cathode using ITO or IZO may 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, [Compound 201], [Compound 202], and oxadiazole derivatives such as PBD, BMD, BND, and the like may be used.

TAZ BAlq

[Compound 201] [Compound 202] 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 alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms 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 is any one of 1 to 3, and n is any one of 0 to 2, satisfying 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 Y is the same or different, and may be any one selected from the following [Structural Formula C1] to [Structural Formula C39] independently of each other.

[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 heteroaryl group having 3 to 30 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 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 alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted C 5 to 30 carbon atom 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.

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 at least one aromatic compound represented by [Chemical Formula 1]. The light-emitting dopant applied to the electroluminescent device 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]

mL ₁ L ₂ L ₃

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 [Structure D], but is not limited thereto.

In addition, * in the following [Structural Formula D] represents a site coordinated with 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, the 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.

[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 represents 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 5-membered ring, and does not have any 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 that connects to each other, and G ^C11 and G ^C12 are each independently a nitrogen atom, substituted Or 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],

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. ) A ligand that forms a platinum complex, a bipyridyl ligand, or a phenanthroline ligand.

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 general formula H-2, R ²¹ , R ²² , n ² , m ² , q ²² , L ² are the same as the R ¹¹ , R ¹² , n ¹ , m ¹ , q ¹² , L ¹ , respectively, and q ²¹ is an integer of 0-2, and 0 is preferable.

In the 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, and 0 to 2 is preferable and 0 is more preferable.

Examples of specific compounds of the general formulas H-1 to 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 ring A to ring D may have a substituent, and the other two rings are an aryl ring that may have a substituent or Represents and represents a heteroaryl ring, and a condensed ring may 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 ring structure, and two azomethine bonds (-C=N-) bound to the M 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. In addition, 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, one or more layers 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 single molecule deposition method or a solution process, wherein the deposition method Means 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 a 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 monochrome or white flat lighting device, and a single color or white flexible lighting device.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are for explaining 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]

In a 5L round bottom flask, 91.0 g (0.410 mol) of 1-bromo-4-aminonaphthalene, 514.2 ml of water, and 1028.3 ml of 12N hydrochloric acid were added, and the internal temperature was lowered to 0°C under a nitrogen atmosphere. After lowering to 0℃, 28.3g (0.410mol) of sodium nitrite (NaNO2) was dissolved in 282.7ml of water, and then slowly added dropwise to the reaction solution. After the dropwise addition, after stirring for 30 minutes, 388.5 g (2.049 mol) of tin chloride (SnCl2) was dissolved in 350 ml of 12N hydrochloric acid and slowly added dropwise. When the dropwise addition was completed, the temperature of the reaction solution was raised to room temperature, stirred for 3 hours, cooled to 5° C. after 3 hours, and filtered to give <1-a> 110.0 g (yield 98.1%).

Synthesis Example 1-2 Synthesis of <1-b>

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

[Scheme 2]

In a 2L round-bottom flask, <1-a> 110.0g (0.402mol) synthesized in [Scheme 1], 39.45g (0.402mol) cyclohexanone, and 1100.0ml of ethanol were added and refluxed for 10 hours. When the reaction was completed, the reaction solution was concentrated and then <1-b>128.6g (yield 95.7%) was obtained by column chromatography.

Synthesis Example 1-3 Synthesis of <1-c>

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

[Scheme 3]

In a 2L round bottom flask, <1-b> 128.6g (0.428mol) synthesized in [Scheme 2], iodobenzene 131.1g (0.643mol), cupperiodide (CuI) 4.08g (0.021mol), tripotassium Phosphate (K ₃ PO ₄ ) 190.99 g (0.900 mol), trans-1,2-cyclohexanediamine 97.85 g (0.857 mol), and 1,4-dioxane 643.0 ml were added and refluxed for 12 hours. When the reaction was completed, the mixture was cooled to room temperature, extracted with 1L of water, and the organic layer was anhydrous, concentrated under reduced pressure, and <1-c> 142.9g (yield 88.6%) was obtained using adsorption column chromatography.

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

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

[Scheme 4]

<1-c> 100g (0.266mol) methylanthranyrate 48.2g (0.319mol), palladium acetate (Pd(OAc) ₂ ) 1.19g (0.005mol) synthesized in [Scheme 3] in a 2L round bottom flask under nitrogen ), Xantphos 5.54g (0.010mol), cesium carbonate 120.9g (0.371mol), and toluene 1000mL were added and refluxed for 6 hours. When the reaction was completed, the reaction product was separated into layers to remove an aqueous layer, and the organic layer was separated and concentrated under reduced pressure, and then <1-d> 86.6 g (yield 70.4%) was obtained through column chromatography.

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

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

[Scheme 5]

In a 2L round bottom flask, <1-d> 86.6g (0.194mol) obtained from [Reaction Scheme 4] and 1299ml of diisopropyl ether were added to a 2L round bottom flask, and after stirring, 226.3ml of methylmagnesium bromide was slowly added dropwise. After dropwise addition, the mixture was stirred at 50 degrees. When the reaction was completed, the reaction product was separated into layers to remove the aqueous layer, and the organic layer was separated and concentrated under reduced pressure, and then <1-e> 82.4g (yield 95.1%) was obtained through column chromatography.

Synthesis Example 1-6. Synthesis of <1-f>

<1-f> was synthesized according to Scheme 6 below.

[Scheme 6]

In a 1L round bottom flask, <1-e> 35.7g (0.080mol) obtained from [Scheme 5] and 500ml of phosphoric acid were added and stirred at 60°C. When the reaction was complete, water was added to the reaction product and stirred. After stirring, it was filtered and washed with water and methanol. <1-f> 31.5g (yield 91.9%) was obtained through column chromatography.

Synthesis Example 1-7 Synthesis of <1-g>

<1-g> was synthesized according to Scheme 7 below.

[Scheme 7]

After creating a nitrogen atmosphere in a 100 ml reactor, magnesium (3.36 g, 0.1384 mol), 40 ml of dry tetrahydrofuran and a small amount of iodine were added and stirred for 30 minutes. To this mixed pressure solution, 20 ml of a dry tetrahydrofuran solution of bromobenzene (19.2 g, 0.1216 mol) was added dropwise at Yeongdo. After the dropwise addition, the mixture was heated and stirred at 65° C. for 2 hours. After dissolving 2-diphenylamino-4,6-dichloro-1,3,5-triazine (18 g, 0.0568 mol) in 100 ml of dry tetrahydrofuran in a 250 ml reactor, the mixture of 100 ml reactor was added dropwise at Yeongdo. After dropwise addition, the mixture is stirred at room temperature for 12 hours. When the reaction is complete, add 200 ml of 2N HCl, add ethyl acetate and water, and extract. The organic layer was subjected to anhydrous treatment and then concentrated under reduced pressure to obtain <1-f> 9.8g (yield 64.5%) using column chromatography.

Synthesis Example 1-8 Synthesis of [Formula 2]

[Chemical Formula 2] was synthesized by the following Scheme 8.

[Scheme 8]

In a 500 ml round bottom flask, sodium hydride (60% mineral oil) (NaH), 0.9 g (0.023 mol), and 66.0 ml of N,N-dimethylformamide were put in a nitrogen atmosphere, and the reaction solution was cooled to 0°C. At 0℃, a solution of <1-f> 6.6g (0.015mol) synthesized in [Scheme 6] dissolved in 66.0ml of N,N-dimethylformamide was slowly added dropwise and stirred at 0℃ for 1 hour. . After 1 hour, a solution of <1-g> 6.7 g (0.018 mol) synthesized in [Scheme 7] dissolved in 150 ml of N,N-dimethylformamide is slowly added dropwise. When the dropwise addition is complete, the reaction solution is raised to room temperature and stirred. When the reaction is complete, the reaction solution is poured into 1 L of water to precipitate a solid and then filtered. The solid was recrystallized using monochlorobenzene to obtain 6.0 g (yield 59.0%) of [Chemical Formula 2].

MS(MALDI-TOF): m/z 659.30[M] ⁺

Anal. Calc. for C ₄₆ H ₃₇ N ₅ C, 83.73; H,5.65; N, 10.61. Found C, 83.74; H, 5.64; N, 10.61.

Synthesis example 2. Synthesis of [Formula 9]

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

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

[Scheme 9]

Except for using bromobenzene-D5 instead of bromobenzene used in Scheme 6, <2-a> 30.1g (yield 69.1%) was obtained.

Synthesis Example 2-2. Synthesis of [Formula 9]

[Chemical Formula 9] was synthesized by the following Scheme 10.

[Scheme 10]

Except for using <2-a> synthesized in Scheme 9 instead of <1-g> used in Scheme 8, [Chemical Formula 9] 7.2g (yield 63.0%) was obtained.

MS(MALDI-TOF): m/z 669.37[M] ⁺

Anal. Calc. for C ₄₆ H ₂₇ D ₁₀ N ₅ C, 82.48; H,7.07; N, 10.45. Found C, 82.48; H, 7.08; N, 10.44.

Synthesis example 3. Synthesis of [Formula 11]

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

<3-a> was synthesized according to Scheme 11 below.

[Scheme 11]

Except for using 4-fluoro-bromobenzene instead of bromobenzene used in Scheme 6, it was synthesized in the same manner to give <3-a> 31.2g (yield 60.4%).

Synthesis Example 3-2. Synthesis of [Formula 11]

[Chemical Formula 11] was synthesized by the following Scheme 12.

[Scheme 12]

Except for using <3-a> synthesized in Scheme 11 instead of <1-g> used in Scheme 8, [Chemical Formula 9] 6.7g (yield 83.0%) was obtained.

MS(MALDI-TOF): m/z 695.29[M] ⁺

Anal. Calc. for C ₄₆ H ₃₅ F ₂ N ₅ C, 79.40; H,5.07; F, 5.46; N, 10.07. Found C, 79.40; H, 5.07; F, 5.46; N, 10.07.

Synthesis example 4. Synthesis of [Formula 38]

Synthesis Example 4-1 Synthesis of <4-a>

<4-a> was synthesized according to Scheme 13 below.

[Scheme 13]

Except for using 4-phenylcyclohexanone instead of the cyclohexanone used in Scheme 2, it was synthesized in the same manner to obtain 80.0 g (yield 92.3%).

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

<4-b> was synthesized according to Scheme 14 below.

[Scheme 14]

Except for using <4-a> synthesized in Scheme 13 instead of <1-b> used in Scheme 3, <4-b> 96.2 g (yield 89.4%) was obtained.

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

<4-c> was synthesized according to Scheme 15 below.

[Scheme 15]

Except for using <4-b> synthesized in Scheme 14 instead of <1-c> used in Scheme 4, <4-c> 81.3g (yield 69.9%) was obtained.

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

<4-d> was synthesized according to Scheme 16 below.

[Scheme 16]

<1-d> used in Scheme 5 was synthesized in the same manner, except that <4-c> synthesized in Scheme 15 was used, and <4-d> 78.2g (yield 95.1%) was obtained.

Synthesis Example 4-5. Synthesis of <4-e>

<4-e> was synthesized according to Scheme 17 below.

[Scheme 17]

Except for using <4-d> synthesized in Scheme 16 instead of <1-e> used in Scheme 6, <4-e> 48.3g (yield 90.3%) was obtained.

Synthesis Example 4-6. Synthesis of [Formula 38]

[Chemical Formula 38] was synthesized by the following Scheme 18.

[Scheme 18]

Except for using <4-d> synthesized in Scheme 17 instead of <1-f> used in Scheme 8, [Formula 38] 7.9g (yield 83.0%) was obtained.

MS(MALDI-TOF): m/z 735.34[M] ⁺

Anal. Calc. for C ₅₂ H ₄₁ N ₅ C, 84.87; H,5.62; N, 9.52. Found C, 84.87; H, 5.62; N, 9.52.

Synthesis example 5. Synthesis of [Formula 39]

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

<5-a> was synthesized according to Scheme 19 below.

[Scheme 19]

In a 1L round bottom flask, 26.4 g (0.112 mol) of 1,4-dibromobenzene was dissolved in 300.0 ml of tetrahydrofuran, cooled to -70°C, and 74.0 ml (0.118 mol) of 1.6M n-butyllithium was slowly added dropwise thereto. After the dropwise addition, the mixture was stirred at -70°C for 1 hour, and then <1-g> 30.0g (0.112mol) synthesized in Scheme 6 was dissolved in 200ml of tetrahydrofuran and slowly added dropwise. After the dropwise addition, the reaction solution was heated to room temperature. When the reaction is complete, 200 ml of water and 200 ml of ethyl acetate are added to the reaction solution and extracted. The organic layer was subjected to anhydrous treatment, concentrated under reduced pressure, and then <5-a> 14.8g (yield 34%) was obtained by column chromatography.

Synthesis Example 5-2 Synthesis of [Formula 39]

[Chemical Formula 39] was synthesized by the following Scheme 20.

[Scheme 20]

In a 500ml round bottom flask, <4-d> 10.0g (0.020mol) synthesized in Scheme 17, <5-a> 9.2g (0.024mol) synthesized in Scheme 19, Cooper 0.8g (0.013mol), 18-crown -6-ether 1.7 g (0.007 mol), potassium carbonate 11.0 g (0.079 mol), and dimethyl sulfoxide 200.0 ml were added and refluxed for 12 hours. When the reaction was completed, the reaction solution was cooled to room temperature, extracted with ethyl acetate and water, anhydrous treatment, concentrated under reduced pressure, and then subjected to column chromatography to obtain 14.2 g (yield 88.3%).

MS(MALDI-TOF): m/z 811.37[M] ⁺

Anal. Calc. for C ₅₈ H ₄₅ N ₅ C, 85.79; H,5.59; N, 8.62. Found C, 85.80; H, 5.60; N, 8.60.

Synthesis example 6. Synthesis of [Formula 47]

Synthesis Example 6-1. Synthesis of [Formula 47]

[Chemical Formula 47] was synthesized by the following Scheme 21.

[Scheme 21]

Except for using <4-d> synthesized in Scheme 17 instead of <1-f> used in Scheme 12, [Formula 47] 5.4g (yield 68.1%) was obtained.

MS(MALDI-TOF): m/z 771.32[M] ⁺

Anal. Calc. for C ₅₂ H ₃₉ F ₂ N ₅ C, 80.91; H,5.09; F, 4.92 N, 9.07. Found C, 80.90; H, 5.10; F, 4.91 N, 9.08.

Synthesis example 7. Synthesis of [Formula 45]

Synthesis Example 7-1 Synthesis of [Formula 45]

[Chemical Formula 45] was synthesized by the following Scheme 22.

[Scheme 22]

Except for using <4-d> synthesized in Scheme 17 instead of <1-f> used in Scheme 10, [Formula 47] 6.7g (yield 69.1%) was obtained.

MS(MALDI-TOF): m/z 745.40[M] ⁺

Anal. Calc. for C ₅₂ H ₃₁ D ₁₀ N ₅ C, 83.72; H,6.89; N, 9.39. Found C, 83.70; H, 6.90; N, 9.40.

Synthesis example 8. Synthesis of [Formula 110]

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

<8-a> was synthesized according to Scheme 23 below.

[Scheme 23]

Except that phenyl magnesium bromide was used instead of methyl magnesium bromide used in Scheme 5, the synthesis was carried out in the same manner to obtain <8-a> 40.2 g (yield 96.8%).

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

<8-b> was synthesized according to Scheme 24 below.

[Scheme 24]

<1-e> used in Scheme 6 was synthesized in the same manner except that <8-a> synthesized in Scheme 23 was used, and <8-b> 36.3g (yield 92.0%) was obtained.

Synthesis Example 8-3. Synthesis of [Formula 110]

[Chemical Formula 110] was synthesized by the following Scheme 25.

[Scheme 25]

[Chemical Formula 110] 7.9g (yield 74.0%) was obtained by synthesizing in the same manner except for using <8-b> synthesized in Scheme 24 instead of <1-f> used in Scheme 8.

MS(MALDI-TOF): m/z 783.34[M] ⁺

Anal. Calc. for C ₅₆ H ₄₁ N ₅ C, 85.80; H,5.27; N, 8.93. Found C, 85.82; H, 5.26; N, 8.92.

Synthesis example 9, synthesis of [Chemical Formula 115]

Synthesis Example 9-1. Synthesis of [Formula 115]

[Chemical Formula 115] was synthesized by the following Scheme 26.

[Scheme 26]

[Chemical Formula 115] 6.7g (yield 68.1%) was obtained by synthesizing in the same manner except for using <1-f> synthesized in Scheme 23 instead of <1-f> used in Scheme 12.

MS(MALDI-TOF): m/z 819.32[M] ⁺

Anal. Calc. for C ₅₆ H ₃₉ F ₂ N ₅ C, 82.03; H,4.79; F, 4.63 N, 8.54. Found C, 82.01; H, 4.81; F, 4.63 N, 8.54.

Synthesis example 10, Synthesis of [Formula 182]

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

<10-a> was synthesized according to Scheme 27 below.

[Scheme 27]

In a 1 L round bottom flask, sodium hydride (60% mineral oil) (NaH), 1.9 g (0.040 mol), and 100.0 ml of N,N-dimethylformamide were added in a nitrogen atmosphere, and the reaction solution was cooled to 0°C. A solution of <1-b> 10.0g (0.033mol) synthesized in Scheme 2 at 0°C was slowly added dropwise to 100.0ml of N,N-dimethylformamide, and stirred at 0°C for 1 hour. After 1 hour, a solution of <1-g> 10.7 g (0.040 mol) synthesized in Scheme 7 in 150 ml of N,N-dimethylformamide was slowly added dropwise. When the dropwise addition is complete, the reaction solution is raised to room temperature and stirred. When the reaction is complete, the reaction solution is poured into 1 L of water to precipitate a solid and then filtered. The solid was recrystallized using monochlorobenzene to give <10-a> 14.7 g (83.0% yield).

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

<10-b> was synthesized according to Scheme 28 below.

[Scheme 28]

<1-c> used in Scheme 4 was synthesized in the same manner, except that <10-a> synthesized in Scheme 27 was used, and <10-b> 12.8g (77.1% yield) was obtained.

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

<10-c> was synthesized according to Scheme 29 below.

[Scheme 29]

<1-d> used in Scheme 23 was synthesized in the same manner, except that <10-b> synthesized in Scheme 28 was used, and <10-c> 14.9g (yield 96.7%) was obtained.

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

<10-d> was synthesized according to Reaction Scheme 30 below.

[Scheme 30]

Except for using <10-c> synthesized in Scheme 29 instead of <1-e> used in Scheme 6, <10-d> 13.0g (yield 89.6%) was obtained.

Synthesis Example 10-5. Synthesis of [Formula 182]

[Chemical Formula 182] was synthesized by the following Scheme 31.

[Scheme 31]

In a 500 ml round bottom flask, <10-d> 13.0 g (0.018 mol) synthesized in Scheme 30, iodobenzene 4.5 g (0.022 mol), Cooper 0.8 g (0.012 mol), 18-crown-6-ether 1.6 g ( 0.006 mol), potassium carbonate 10.2 g (0.073 mol), and dimethyl sulfoxide 260.0 ml were added and refluxed for 24 hours. When the reaction was completed, the reaction solution was cooled to room temperature, extracted with chloroform and water, and the organic layer was anhydrous, concentrated under reduced pressure, and then 5.9 g (yield 41.0%) was obtained by column chromatography.

MS(MALDI-TOF): m/z 783.34[M] ⁺

Anal. Calc. for C ₅₆ H ₄₁ N ₅ C, 85.80; H,5.27; N, 8.93. Found C, 85.78; H, 5.28; N, 8.94.

Synthesis example 11. Synthesis of [Formula 219]

Synthesis Example 11-1. Synthesis of <11-a>

<11-a> was synthesized according to Scheme 32 below.

[Scheme 32]

<11-a>

1-nitronaphthalene 97g (0.56mol), methyl cyanoacetate 166.5g (1.68mol), potassium cyanide 40.1g (0.62mol), potassium hydroxide 62.9g (1.12mol) were added and stirred. Then, 970 mL of dimethylformamide was added and stirred at 60°C overnight. After removing the solvent by concentrating under reduced pressure at room temperature, 500 mL of a 10% aqueous sodium hydroxide solution was added and refluxed for about 1 hour. After extraction with ethyl acetate, separation by column chromatography and recrystallization from toluene and heptane gave <11-a> 50.8 g (yield 54%).

Synthesis Example 11-2 Synthesis of <11-b>

<11-b> was synthesized according to Reaction Scheme 33 below.

[Scheme 33]

<11-b>

<11-a> 25.0g (149mmol) obtained from Scheme 32 was added to 200 mL of tetrahydrofuran and stirred. Phenyl magnesium bromide (3.0 M in Et ₂ O) 87.4 mL (297 mmol) was added dropwise and refluxed at 0° C. for about 1 hour. After dropping 19.4 g (179 mmol) of ethyl chloroformate, it was refluxed for about 1 hour. An aqueous ammonium chloride solution was added until it became weakly acidic, and washed with water and heptane to give 32.4 g (yield 80%) of <11-b>.

Synthesis Example 11-3 Synthesis of <11-c>

<11-c> was synthesized according to Scheme 34 below.

[Scheme 34]

<11-c>

<11-b> 30g (110mmol) obtained from Scheme 33 was added to about 80 mL of phosphorus oxychloride and refluxed overnight. After cooling the temperature to -20 °C, about 400 mL of distilled water was slowly added. Washed with water, methanol and heptane, and recrystallized from toluene and heptane to give <11-c> 14.1 g (yield 44%).

Synthesis Example 11-4 Synthesis of <11-d>

<11-d> was synthesized according to Scheme 35 below.

[Scheme 35]

<11-d>

Except for using 1-bromo-3,5-diphenylbenzene instead of iodobenzene used in Scheme 3, it was synthesized in the same manner to obtain <11-d> (yield 86%).

Synthesis Example 11-5 Synthesis of <11-e>

<11-e> was synthesized according to Scheme 36 below.

[Scheme 36]

<11-e>

In the same manner as in Scheme 4 to Scheme 6, except for using <11-d> synthesized in Scheme 35 instead of <1-c> used in Scheme 4, <11-e> (yield 86%) was obtained.

Synthesis Example 11-5 Synthesis of [Chemical Formula 219]

[Chemical Formula 219] was synthesized by the following Scheme 37.

[Scheme 37]

[Chemical Formula 219]

Synthesized in the same manner except that <11-e> synthesized in Scheme 36 was used instead of <1-f> used in Scheme 8, and <11-c> synthesized in Scheme 34 was used instead of <1-g>. Thus, [Chemical Formula 219] (yield 60%) was obtained.

MS(MALDI-TOF): m/z 834.37[M] ⁺

Anal. Calc. for C ₆₁ H ₄₆ N ₄ C, 87.74; H, 5.55; N, 6.71. Found C, 87.77; H, 5.53; N, 6.70.

Synthesis example 12. Synthesis of [Chemical Formula 220]

Synthesis Example 12-1 Synthesis of <12-a>

<12-a> was synthesized according to Scheme 38 below.

[Scheme 38]

<12-a>

Except for using 9-nitrophenanthrene instead of 1-nitronaphthalene used in Scheme 32, it was synthesized in the same manner as Scheme 32 to Scheme 34 to obtain <12-a> (yield 56%).

Synthesis Example 12-2 Synthesis of <12-b>

<12-b> was synthesized according to Scheme 39 below.

[Scheme 39]

<12-b>

Except for using 4-bromo-9,9-dimethyl-9H-fluorene instead of iodobenzene used in Scheme 3, it was synthesized in the same manner to obtain <12-b> (yield 85%).

Synthesis Example 12-3 Synthesis of <12-c>

<12-c> was synthesized according to Scheme 40 below.

[Scheme 40]

<12-c>

In the same manner as in Scheme 4 to Scheme 6, except that <12-b> synthesized in Scheme 39 was used instead of <1-c> used in Scheme 4, and phenyl magnesium bromide was used instead of methyl magnesium bromide used in Scheme 5. It synthesized to give <12-c> (yield 90%).

Synthesis of Synthesis Example 12-4 [Chemical Formula 220]

[Chemical Formula 220] was synthesized by the following Scheme 41.

[Scheme 41]

[Chemical Formula 220]

Synthesized in the same manner except that <12-c> synthesized in Scheme 40 was used instead of <1-f> used in Scheme 8, and <12-a> synthesized in Scheme 38 was used instead of <1-g>. Thus, [Chemical Formula 219] (yield 65%) was obtained.

MS(MALDI-TOF): m/z 972.42 [M] ⁺

Anal. Calc. for C ₇₂ H ₅₂ N ₄ C, 88.86; H, 5.39; N, 5.76. Found C, 88.87; H, 5.38; N, 5.76.

Synthesis example 13. Synthesis of [Formula 221]

Synthesis Example 13-1 Synthesis of <13-a>

<13-a> was synthesized according to Scheme 42 below.

[Scheme 42]

<13-a>

1,3-dibromonaphthalene 34.9g (122mmol), 2-nitrobenzeneboronic acid 24.4g (146mmol), tetrakis (triphenylphosphine) palladium 7g (6mmol), potassium carbonate 33.7g (244mmol) 1, It was added to 150 mL of 4-dioxane, 150 mL of toluene, and 60 mL of distilled water and refluxed overnight. After extraction with ethyl acetate, it was recrystallized from dichloromethane and acetone to give <13-a> 25.6g (64% yield).

Synthesis Example 13-2 Synthesis of <13-b>

<13-b> was synthesized according to Scheme 43 below.

[Scheme 43]

<13-b>

<13-a> 16.4g (50mmol) synthesized in Scheme 42 was added to 200 mL of 1,2-dichlorobenzene, 200 mL of triethylphosphite, and refluxed at 150° C. for 12 hours. Cooled to room temperature and separated by column chromatography to give 11.1 g (75% yield) of <13-b>.

Synthesis Example 13-3 Synthesis of <13-c>

<13-c> was synthesized according to Scheme 44 below.

[Scheme 44]

<13-c>

<13-c> was synthesized in the same manner except that <13-b> synthesized in Scheme 43 was used instead of <1-b> used in Scheme 3, and pentadeutereobromobenzene was used instead of iodobenzene. (Yield 88%) was obtained.

Synthesis Example 13-4 Synthesis of <13-d>

<13-d> was synthesized according to Scheme 45 below.

[Scheme 45]

<13-d>

Except for using <13-c> synthesized in Scheme 44 instead of <1-c> used in Scheme 4, <13-d> (yield 88%) was obtained by synthesizing in the same manner as in Scheme 4 to Scheme 6.

Synthesis Example 13-5 Synthesis of <13-e>

<13-e> was synthesized according to Scheme 46 below.

[Scheme 46]

<13-e>

Except for using 3-aminonaphthalene-2-carbonitrile instead of <11-a> used in Scheme 33, it was synthesized in the same manner as Scheme 33 to Scheme 34 to obtain <13-e> (yield 71%).

Synthesis Example 13-6 Synthesis of [Chemical Formula 221]

[Chemical Formula 221] was synthesized by the following Scheme 47.

[Scheme 47]

<Formula 221>

Synthesized in the same manner except that <13-d> synthesized in Scheme 45 was used instead of <1-f> used in Scheme 8, and <13-e> synthesized in Scheme 46 was used instead of <1-g>. To obtain [Chemical Formula 221] (66% yield).

MS(MALDI-TOF): m/z 683.31 [M] ⁺

Anal. Calc. for C ₄₉ H ₂₉ D ₅ N ₄ C, 86.06; H, 5.75; N, 8.19. Found C, 86.07; H, 5.74; N, 8.19.

Synthesis example 14. Synthesis of [Formula 223]

Synthesis Example 14-1 Synthesis of <14-a>

<14-a> was synthesized according to Scheme 48 below.

[Scheme 48]

<14-a>

Synthesized in the same manner except that 3-bromo-4-iodopyridine was used instead of <1-c> used in Scheme 4, and 1-amino-4-bromonaphthalene was used instead of methylanthranyrate. <14-a> (yield 72%) was obtained.

Synthesis Example 14-2 Synthesis of <14-b>

<14-b> was synthesized according to Scheme 49 below.

[Scheme 49]

<14-b>

<14-a> 11.3g (0.03mol) synthesized in Scheme 48, potassium acetate 4.0g (0.04mol), tetrakistriphenylphosphine palladium 0.8g (0.001mol) was added to 125mL of dimethylformamide and 24 at 150 ℃. Stir for hours. Separated by column chromatography and recrystallized with hexane to give <14-b> 2.7 g (30% yield).

Synthesis Example 14-3 Synthesis of <14-c>

<14-c> was synthesized according to the following Scheme 50.

[Scheme 50]

<14-c>

Except for using <14-b> synthesized in Scheme 49 instead of <1-b> used in Scheme 3, <14-c> (yield 87%) was obtained.

Synthesis Example 14-4 Synthesis of <14-d>

<14-d> was synthesized according to Scheme 51 below.

[Scheme 51]

<14-d>

Except for using <14-c> synthesized in Scheme 50 instead of <1-c> used in Scheme 4, it was synthesized in the same manner as Scheme 4 to Scheme 6 to obtain <14-d> (yield 87%).

Synthesis Example 14-5 Synthesis of <14-e>

<14-e> was synthesized according to Scheme 52 below.

[Scheme 52]

<14-e>

The same method except that <12-a> synthesized in Scheme 38 was used instead of 1,3-dibromonaphthalene used in Scheme 42, and 4-iodophenylboronic acid was used instead of 2-nitrobenzeneboronic acid. Synthesis was performed to give <14-e> (yield 77%).

Synthesis Example 14-6 Synthesis of [Formula 223]

[Chemical Formula 223] was synthesized by the following Scheme 53.

[Scheme 53]

[Chemical Formula 223]

Synthesized by the same method except that <14-d> synthesized in Scheme 51 was used instead of <1-f> used in Scheme 8, and <14-e> synthesized in Scheme 52 was used instead of <1-g>. This gave [Chemical Formula 223] (yield 68%).

MS(MALDI-TOF): m/z 805.32 [M] ⁺

Anal. Calc. for C ₅₈ H ₃₅ N ₅ C, 86.43; H, 4.88; N, 8.69. Found C, 86.43; H, 4.86; N, 8.71.

Examples 1 to 10: Preparation of organic light emitting diode

The ITO glass was patterned so that the light emitting area was 2 mm × 2 mm in size and 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 in the synthesis example + Ir (ppy) ₃ ( 10%) (300 Å), Alq ₃ (350 Å), LiF (5 Å), Al (1,000 Å) were formed in the order, and the measurement was performed at 0.4 mA.

Comparative example One

The organic light emitting diode device for Comparative Example 1 was fabricated in the same manner, except that CBP, which is commonly used as a phosphorescent host material, was used instead of the compound prepared by the invention in the device structure of the above example. same.

<CBP>

division Host Dopant Doping concentration% V Cd/m ² CIEx CIEy T ₈₀ (Hr) Comparative Example 1 CBP Ir(ppy) ₃ 10 7.93 3801 0.297 0.624 68 Example 1 2 Ir(ppy) ₃ 10 4.13 5248 0.288 0.624 251 Example 2 9 Ir(ppy) ₃ 10 4.17 5318 0.294 0.623 192 Example 3 11 Ir(ppy) ₃ 10 4.25 5289 0.299 0.631 182 Example 4 38 Ir(ppy) ₃ 10 4.30 4698 0.304 0.625 165 Example 5 39 Ir(ppy) ₃ 10 4.62 4925 0.302 0.622 192 Example 6 45 Ir(ppy) ₃ 10 4.14 5098 0.312 0.619 223 Example 7 47 Ir(ppy) ₃ 10 4.55 5157 0.303 0.624 242 Example 8 110 Ir(ppy) ₃ 10 4.44 5126 0.298 0.627 125 Example 9 115 Ir(ppy) ₃ 10 4.65 5140 0.296 0.628 191 Example 10 182 Ir(ppy) ₃ 10 4.16 4948 0.309 0.632 99

In order to measure the band gap of Formulas 2, 9, 11, 38, 39, 45, 47, 110, 115, and 182 of the present invention, an absorption spectrometer (UV/Vis absorption spectrometer) and a voltage ammeter (Cyclic voltammetry) were used. Measured.

division UV (λmax) PL (λmax) HOMO(eV) LUMO(eV) Band Gap(ev) Formula 2 292, 316, 341 474 6.1 2.9 3.2 Formula 9 294, 318, 342 474 6.0 3.0 3.0 Formula 11 290, 318, 342 473 6.1 2.8 3.3 Formula 38 291, 317, 343 474 6.0 2.8 3.2 Formula 39 295, 318, 341 475 6.2 2.9 3.3 Formula 45 294, 315, 342 476 6.0 2.7 3.3 Formula 47 290, 318, 342 473 6.2 2.8 3.4 Formula 110 294, 318, 342 474 6.1 3.0 3.1 Chemical Formula 115 291, 317, 343 474 6.2 2.9 3.3 Chemical Formula 182 291.319, 343 476 6.1 2.8 3.3

Example 11 to 14

Organic light-emitting diode devices for Examples 11 to 14 used [Chemical Formula 219] to [Chemical Formula 221] and [Chemical Formula 223] for the light emitting layer in the device structures of Examples 1 to 10, and instead of [Ir(ppy) ₃ ] Except for the use of [(piq) ₂ Ir(acac)], it was manufactured in the same way, and the structure of [(pic) ₂ Ir(acac)] is as follows.

[(pic) ₂ Ir(acac)]

Comparative example 2

The organic light emitting diode device for Comparative Example 2 was manufactured in the same manner as in Comparative Example 1, except that [(piq) ₂ Ir(acac)] was used instead of [Ir(ppy) ₃ ] for the light emitting layer in the device structure of Comparative Example 1. I did.

division Host Dopant Doping concentration (%) V Cd/㎡ CIEx CIEy T ₈₀ (Hr) Example 11 Chemical Formula 219 [(pic) ₂ Ir(acac)] 10 3.99 5005 0.675 0.332 206 Example 12 Formula 220 [(pic) ₂ Ir(acac)] 10 3.86 4987 0.671 0.328 171 Example 13 Chemical Formula 221 [(pic) ₂ Ir(acac)] 10 4.06 4982 0.673 0.331 189 Example 14 Formula 223 [(pic) ₂ Ir(acac)] 10 3.98 4838 0.669 0.330 193 Comparative Example 2 CBP [(pic) ₂ Ir(acac)] 10 7.91 3655 0.667 0.324 50

As shown in Tables 1 and 3, the organic compound secured by the present invention has a lower driving voltage, higher luminous efficiency, and a longer life than CBP among host materials commonly used as phosphorescent host materials.

Claims (12)

Aromatic compound represented by the following [Chemical Formula 1]:
[Formula 1]

In the above [Formula 1],
Q is selected from a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 60 carbon atoms, and a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms,
L is a single bond or a divalent linking group selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 carbon atoms and a substituted or unsubstituted heteroarylene group having 3 to 50 carbon atoms,
l and m are integers of 0 to 3, and when l and m are 2 or more, a plurality of L may be the same or different,
X is selected from the group consisting of CR ₁₁ R ₁₂ , NR ₁₃ , O, S and SiR ₁₄ R ₁₅ (however, when X is CR ₁₁ R ₁₂ or NR ₁₃ , the case where Q is phenyl is excluded) ,
R ₁ to R ₁₅ 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 6 to 40 carbon atoms, a substituted or unsubstituted carbon number A 3 to 30 cycloalkyl group, a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms having O, N, S or P as a hetero atom, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted Aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkyl thioxy group having 1 to 30 carbon atoms, substituted or unsubstituted arylthioxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms , A substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a hydroxyl group, It is any one selected from a nitro group and a halogen group,
The Q, L, R ₁ to R ₁₅ and their substituents may be combined with each other or with adjacent substituents to form a saturated or unsaturated ring. The method of claim 1,
The Q, L and R ₁ to R ₁₅ are each independently a deuterium atom, a cyano group, a halogen atom, a hydroxy group, a nitro group, an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, an alkenyl group having 2 to 30 carbon atoms , C2-C40 alkynyl group, C1-C40 alkoxy group, C1-C40 alkylamino group, C6-C40 arylamino group, C3-C40 heteroarylamino group, C1-C40 alkylsilyl group , One selected from the group consisting of arylsilyl group having 6 to 40 carbon atoms, aryl group having 6 to 40 carbon atoms, aryloxy group having 6 to 40 carbon atoms, heteroaryl group having 3 to 40 carbon atoms, germanium group, phosphorus and boron An aromatic compound, characterized in that the above-described substitution. delete delete delete delete delete The method of claim 1,
[Formula 1] is an aromatic compound, characterized in that any one selected from the group of compounds represented by the following formula:

[Chemical Formula 218] [Chemical Formula 219] [Chemical Formula 220]

[Formula 223] [Formula 224] [Formula 225]

[Formula 226] [Formula 227] [Formula 228] [Formula 229]

[Formula 230] [Formula 231] [Formula 232] [Formula 233]

[Chemical Formula 234] [Chemical Formula 236] [Chemical Formula 237] A first electrode; A second electrode; And an organic material layer comprising the aromatic compound according to claim 1 between the first electrode and the second electrode. The method of claim 9,
The aromatic compound is an organic electroluminescent device, characterized in that included in the emission layer between the first electrode and the second electrode. The method of claim 9,
The organic material layer further comprises one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer. The method of claim 9,
An organic electroluminescent device, characterized in that used for a display device, a display device, and a single color or white lighting device.

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