KR20160000284A - Novel aromatic amine compounds for organic light-emitting diode and organic light-emitting diode including the same - Google Patents

Abstract

The present invention relates to an organic light emitting compound represented by chemical formula A, and an organic light emitting device comprising the same.

Description

TECHNICAL FIELD [0001] The present invention relates to novel aromatic organic light-emitting compounds and organic light-

The present invention relates to a novel aromatic organic light emitting compound and an organic light emitting device comprising the same, and more particularly, to a compound for an organic light emitting device exhibiting excellent device characteristics when used as a light emitting material and an organic light emitting device .

The organic light emitting diode (OLED) is a display using a self-luminous phenomenon. The organic light emitting diode (OLED) has a wide viewing angle and is thinner and lighter than a liquid crystal display and has a fast response speed. ) Applications for display or illumination are expected.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in order to enhance the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layered structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out. Such an organic light emitting device is known to have characteristics such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

A material used as an organic material layer in an organic light emitting device can be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions. The light emitting material may be classified into a polymer type and a low molecular type depending on the molecular weight and may be classified into a fluorescent material derived from singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons according to an emission mechanism . Further, the light emitting material can be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural color depending on the luminescent color.

On the other hand, when only one material is used as the light emitting material, there arises a problem that the maximum light emitting wavelength shifts to a long wavelength due to intermolecular interaction, the color purity drops, or the efficiency of the device decreases due to the light emission attenuating effect. A host-dopant system can be used as a light emitting material to increase the efficiency of light emission through the transition.

When the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with a small amount of the light emitting layer, the 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 is shifted to the wavelength band of the dopant, the light of the desired wavelength can be obtained according to the type of the dopant used.

 As a prior art related to the host compound in such a light emitting layer, Japanese Patent Registration No. 10-1092006 (Dec. 12, 2011) discloses an organic light emitting device comprising an anthracene derivative in which a phenyl group having a substituent is bonded at both ends of an anthracene structure, And Patent Document 10-2006-0113954 (Nov. 3, 2006) discloses a technique relating to an organic light emitting device including an asymmetric anthracene derivative of a specific structure in a light emitting medium layer.

However, despite the fact that various kinds of compounds for use in the light emitting medium layer have been prepared including the above-mentioned conventional arts, there is a continuing need to develop stable, efficient and long-life organic compound layer materials for organic light emitting devices It is true.

Patent Registration No. 10-1092006 (December, 2011)

Patent Document 10-2006-0113954 (November 3, 2006)

Accordingly, the first technical object of the present invention is to provide a compound for an organic light emitting device which can be used for an organic light emitting layer and has excellent device characteristics such as a low driving voltage and improved color purity.

A second object of the present invention is to provide an organic light emitting device comprising the compound.

In order to achieve the first technical object, the present invention provides an organic light emitting compound represented by the following formula (A).

(A)

In the above formula (A)

Any one of R ₁ to R ₈ is a single bond which bonds with the linking group L;

The substituents R ₁ to R ₁₉ are the same or different from each other and each independently represent 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 C2-C20 alkynyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, A substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having at least one heteroatom selected from O, N, S and Si, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon number A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, A substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, 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 nitro group, and a halogen group, and may be connected to adjacent substituents to form a monocyclic or polycyclic ring of an alicyclic or aromatic group, and a monocyclic or polycyclic ring of the formed alicyclic or aromatic group The carbon atom may be substituted with any one or more heteroatoms selected from N, S, and O;

The linking group L is a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted group having 2 to 60 carbon atoms Substituted or unsubstituted C2-C60 alkynylene groups, substituted or unsubstituted C3-C60 alkynylene groups, substituted or unsubstituted C2- A substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;

Wherein n is an integer of 1 to 3, and when n is 2 or more, each L may be the same or different.

According to another aspect of the present invention, there is provided a plasma display panel comprising 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 light emitting device including at least one organic light emitting compound of the present invention is provided.

According to the present invention, the organic electroluminescent compound represented by the formula (A) has excellent device characteristics such as low driving voltage and improved color purity as compared with existing materials, and can be used for the production of stable and excellent devices.

1 is a schematic view of an organic light emitting device according to an embodiment of the present invention.

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

The present invention provides a compound represented by the following formula (A) as an organic compound that can be used in a light emitting layer of an organic light emitting device.

(A)

In the above formula (A)

Any one of R ₁ to R ₈ is a single bond which bonds with the linking group L;

The substituents R ₁ to R ₁₉ are the same or different from each other and each independently represent 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 C2-C20 alkynyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, A substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having at least one heteroatom selected from O, N, S and Si, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon number A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, A substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, 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 nitro group, and a halogen group, and may be connected to adjacent substituents to form a monocyclic or polycyclic ring of an alicyclic or aromatic group, and a monocyclic or polycyclic ring of the formed alicyclic or aromatic group The carbon atom may be substituted with any one or more heteroatoms selected from N, S, and O;

The linking group L is a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted group having 2 to 60 carbon atoms Substituted or unsubstituted C2-C60 alkynylene groups, substituted or unsubstituted C3-C60 alkynylene groups, substituted or unsubstituted C2- A substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;

Wherein n is an integer of 1 to 3, and when n is 2 or more, each L may be the same or different,

The "substituted" in the "substituted or unsubstituted" in the above [Formula A] is a substituent selected from the group consisting of deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group having 1 to 24 carbon atoms, 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, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, An alkylamino group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, An arylsilyl group having 1 to 24 carbon atoms, and an aryloxy group having 1 to 24 carbon atoms.

In consideration of the range of the alkyl or aryl group in the above "substituted or unsubstituted alkyl group having 1 to 24 carbon atoms" and "substituted or unsubstituted aryl group having 6 to 24 carbon atoms", it is preferable that the number of carbon atoms is 1 to 24 And the number of carbon atoms in the aryl group of 6 to 24 carbon atoms means the total number of carbon atoms constituting the alkyl moiety or aryl moiety when it is considered that the substituent is not substituted without considering the substituted moiety. For example, a phenyl group substituted with a butyl group at the para position should be considered to correspond to an aryl group having 6 carbon atoms substituted with a butyl group having a carbon number of 4.

An aryl group, which is a substituent used in the compound of the present invention, refers to an aromatic system composed of a hydrocarbon containing at least one ring, and when the aryl group has a substituent, it is fused with neighboring substituents to further form a ring .

Specific examples of the aryl group include 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, An aromatic group such as a phenyl group, an indenyl group, a fluorenyl group, a tetrahydronaphthyl group, a perylenyle group, a crycenyl group, a naphthacenyl group and a fluoranthenyl group, and at least one hydrogen atom of the aryl group may be substituted with a deuterium atom, a halogen atom (-NH ₂₎ , -NH (R), -N (R ') (R "), R' and R" are independently of each other an alkyl group having 1 to 10 carbon atoms 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, a halogenated alkyl group having 1 to 24 carbon atoms, an alkyl group having 1 to 24 carbon atoms An alkenyl 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, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, or a heteroarylalkyl group having 2 to 24 carbon atoms.

The heteroaryl group, which is a substituent used in the compounds of the present invention, refers to a C 2 -C 24 ring aromatic system containing 1, 2 or 3 heteroatoms selected from N, O, P or S and the remaining ring atoms are carbon, The rings may be fused to form a ring. And at least one hydrogen atom of the heteroaryl group may be substituted with the same substituent as the aryl group.

Specific examples of the alkyl group as a substituent used in the present invention include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl and the like. The atom may be substituted with the same substituent as in the case of the aryl group.

Specific examples of the alkoxy group used as the substituent in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, isoamyloxy, hexyloxy, At least one hydrogen atom in the alkoxy group may be substituted with the same substituent as in the case of the aryl group.

Specific examples of the silyl group used as the substituent in the compound of the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, silyl, diphenylvinylsilyl, Butylsilyl, dimethylpurylsilyl and the like, and at least one hydrogen atom of the silyl group may be substituted with the same substituent as the aryl group.

In the present invention, the linking group L of the organic electroluminescent compound represented by the formula (A) is a single bond or any one selected from the following structural formulas 1 to 9,

n may be 1 or 2.

[Structural Formula 1] [Structural Formula 2] [Structural Formula 3] [Structural Formula 4]

[Structural formula 5] [Structural formula 6] [Structural formula 7]

[Structural formula 8] [Structural formula 9]

In the substituent L, the carbon of the aromatic ring may be bonded to hydrogen or deuterium.

The substituent R ₁₉ in the formula (A) of the present invention may be a substituted or unsubstituted aryl group having 6 to 24 carbon atoms.

More specifically, the Wherein L is a single bond or may be the following [structural formula 11] or [structural formula 12] and n may be 1. [

[Structural formula 11] [Structural formula 12]

The substituent R ₁₉ in the above formula (A) is a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, which may include deuterium in the aromatic ring.

In one embodiment, the present invention provides an organic luminescent compound represented by any one of the following formulas (1) to (48).

≪ Formula 1 >    (2) (3)   

≪ Formula 4 >    ≪ Formula 5 > (6)   

&Lt; Formula 7 >    &Lt; Formula 8 > < EMI ID =    

&Lt; Formula 10 >    &Lt; Formula 11 > &Lt; Formula 12 >

&Lt; Formula 13 >    &Lt; Formula 14 >  &Lt; Formula 15 >

&Lt; Formula 16 >    &Lt; Formula 17 >  &Lt; Formula 18 >  

(19)    (20)  (21)

(22)    &Lt; Formula 23 >  &Lt; EMI ID =    

&Lt; Formula 25 >    (26)  &Lt; Formula 27 >        

(28)   (29)  (30)

(31)   (32)  &Lt; Formula 33 >   

(34)    &Lt; Formula 35 >  &Lt; EMI ID =    

(37)    &Lt; Formula 38 >  &Lt; EMI ID =    

&Lt; EMI ID =    &Lt; EMI ID =  (42)    

&Lt; Formula 43 >    &Lt; Formula 44 >  <Formula 45>    

&Lt; EMI ID =    &Lt; EMI ID =  (48)    

The present invention relates to a plasma display panel comprising a first electrode; A second electrode facing the first electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer contains at least one of the anthracene derivatives of the present invention.

In the present invention, "(organic layer) includes one or more compounds "," (organic layer) may include one kind of compound belonging to the scope of the present invention or two or more different compounds belonging to the category of the above compound Can be interpreted as "exist".

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

Also, in the present invention, the organic layer interposed between the first electrode and the second electrode may be a light emitting layer, and in this case, the light emitting layer may be composed of a host and a dopant.

In the present invention, the compound of formula (A) may be used as a host.

Specific examples of the dopant substance used in the light emitting layer include a pyrene-based compound, a deuterium-substituted pyrene-based compound, an arylamine, a deuterium-substituted arylamine, a peryl-based compound, a deuterium-substituted peryl- Substituted carbazole-based compounds, stilbene-based compounds, deuterated substituted stilbene-based compounds, starburst-based compounds, deuterium-substituted starburst-based compounds, deuterium- An oxadiazole-based compound, a deuterium-substituted oxadiazole-based compound, coumarine, deuterium-substituted coumarine, and the like, but the present invention is not limited thereto.

When the light emitting layer includes a host and a dopant, the dopant may be selected from the range of about 0.01 to about 20 parts by weight based on 100 parts by weight of the host, but is not limited thereto.

In the present invention, at least one layer selected from the hole injecting layer, the hole transporting layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transporting layer and the electron injecting layer may be formed by a single molecular deposition method or a solution process. Here, the deposition method refers to a method of forming a thin film by evaporating a material used as a material for forming each of the layers through heating or the like under vacuum or low pressure, Refers to a method of mixing a material used as a material with a solvent and forming the thin film by a method such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating or the like.

Further, the organic light emitting device of the present invention may be a flat panel display device; A flexible display device; Monochrome or white flat panel illumination devices; And a single-color or white-colored flexible lighting device.

As a specific example of the present invention, a hole transport layer (HTL) is further stacked between the anode and the organic emission layer, and an electron transport layer (ETL) is added between the cathode and the organic emission layer The hole transport layer is laminated in order to facilitate injection of holes from the anode. As the material of the hole transport layer, an electron donor molecule having a low ionization potential is used, and mainly triphenylamine is used as a basic skeleton Triamine or tetraamine derivatives are widely used.

In the present invention, 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'- , 1-biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine (a-NPD).

A hole injection layer (HIL) may be additionally formed on the lower portion of the hole transport layer. The material for the hole injection layer is not particularly limited as long as it is commonly used in the art. For example, (4,4 ', 4 "-tri (N-carbazolyl) triphenylamine), m-MTDATA (4,4', 4" -tris- (3-methylphenylphenyl amino) triphenylamine) can be used.

In addition, the electron transport layer used in the organic light emitting device according to the present invention has an opportunity to recombine in the light emitting layer by smoothly transporting electrons supplied from the cathode to the organic light emitting layer and suppressing the movement of holes which are not bonded in the organic light emitting layer .

The material of the electron transport layer is not particularly limited as long as it is commonly used in the art. For example, it is possible to use an oxadiazole derivative such as PBD, BMD, BND or Alq ₃ as described above .

Meanwhile, an electron injection layer (EIL) may be further formed on the electron transport layer to facilitate injection of electrons from the cathode to ultimately improve power efficiency. The electron injection layer material As long as it is commonly used in the related art, it can be used without any particular limitation. For example, materials such as LiF, NaCl, CsF, Li ₂ O, and BaO can be used.

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

1 is a cross-sectional view showing the structure of an organic light emitting device of the present invention. The organic light emitting 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, An injection layer 70 may be further formed. In addition, one or two intermediate layers may be further formed, or a hole blocking layer or an electron blocking layer may be further formed.

Referring to FIG. 1, the organic light emitting device of the present invention and a method of manufacturing the same will be described below. First, an anode electrode material is coated on the substrate 10 to form an anode 20. Here, as the substrate 10, an organic substrate or a transparent plastic substrate which is excellent in transparency, surface smoothness, ease of handling, and waterproofness is used as a substrate used in a conventional organic EL device. As the 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 excellent in conductivity are used.

A hole injection layer 30 is formed on the anode 20 by vacuum thermal deposition or spin coating. Subsequently, a hole transport layer 40 is formed by vacuum thermal deposition or spin coating on the hole transport layer 30 above the hole injection layer 30.

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 to form a thin film on the organic light emitting layer 50 can do. In the case where holes are injected into the cathode through the organic light-emitting layer, the lifetime and the efficiency of the device are reduced, and thus 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 . In this case, the hole blocking material to be used is not particularly limited, but it is required to have an ionization potential higher than that of the light emitting compound while having electron transporting ability. Typically, BAlq, BCP, TPBI and the like can be used.

After the electron transport layer 60 is deposited on the hole blocking layer by a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed, and a cathode forming metal is deposited on the electron injection layer 70 in a vacuum heat- And the cathode 80 is formed by vapor deposition to complete the organic EL device. Here, as the metal for forming the cathode, lithium, magnesium, aluminum, aluminum-lithium, calcium, magnesium-magnesium, Mg-Ag), and a transmissive cathode using ITO or IZO can be used to obtain a top light-emitting device.

In addition, according to a specific example of the present invention, the thickness of the light emitting layer is preferably 50 to 2,000 ANGSTROM, and the light emitting layer may be composed of a host and a dopant, and the compound of the present invention may be used as a host.

In this case, the dopant may be a compound represented by the following Chemical Formula 1 or Chemical Formula 2. At this time, the light emitting layer may further include various dopant materials.

[Chemical Formula 1] &lt; EMI ID =

Among the above-mentioned formulas (1) and (2)

A is a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S as a hetero atom, an optionally substituted arylene group having 6 to 60 carbon atoms , A substituted or unsubstituted heteroarylene group having 3 to 50 carbon atoms having a hetero atom O, N or S, and the like.

More specifically, A is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms or a single bond, preferably an anthracene, pyrene, phenanthrene, indenophenanthrene, klysene, naphthacene, Perylene, pentacene, and more particularly, the A may be a substituent represented by any one of the following formulas (A1) to (A10).

[Formula A1] [Formula A2] [Formula A3]

[Chemical Formula A4] [Chemical Formula A5] [Chemical Formula A6]

[Chemical formula A7] [Chemical formula A8] [Chemical formula A9]

(A10)

Wherein Z ₁ to Z ₂ in the formula [A3] are each independently selected from the group consisting of hydrogen, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted Or an unsubstituted or substituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted aryl group having 2 to 60 carbon atoms (Substituted or unsubstituted C1-C60 alkyl) amino group, or a substituted or unsubstituted C6-C60 aryl) amino group, a substituted or unsubstituted C1-C60 alkylamino group, , (Substituted or unsubstituted aryl group having 6 to 60 carbon atoms) amino group, and Z ₁ to Z ₂ are the same or different from each other and can form a condensed ring with adjacent groups.

In the above formula (1)

X ₁ and X ₂ are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a single bond, X ₁ and X ₂ may be bonded to each other,

Y ₁ and Y ₂ are each independently a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted Or a substituted or unsubstituted C1 to C24 heteroalkyl group, a substituted or unsubstituted C3 to C24 cycloalkyl group, a substituted or unsubstituted C1 to C24 alkoxy group, a cyano group, a halogen group, a substituted or unsubstituted carbon number A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, boron, deuterium, and hydrogen. more selected species and, Y ₁ to Y ₂ each are the same or different each other, may form a fused ring group of the aliphatic, aromatic, aliphatic hetero, or aromatic heterocyclic group which are adjacent to each other It was.

Each of l and m is an integer of 1 to 20, and n is an integer of 1 to 4.

In the above formula (2)

C _y is a substituted or unsubstituted cycloalkyl having 3 to 8 carbon atoms, b is an integer of 1 to 4, and when b is 2 or more, each cycloalkane may be in a fused form, Each of which may be substituted with deuterium or alkyl, and may be the same as or different from each other.

In addition, Is a single bond or - [C (R ₅ ) (R ₆ )] _p -, and p is an integer of 1 to 3; when p is 2 or more, R ₅ and R ₆ are the same or different from each other;

Wherein _{R 1, R 2, R 3} , R 5 and R ₆ are, each independently, hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms , A substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted carbon number A substituted or unsubstituted aryloxy group having 6 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, Or beach (Substituted or unsubstituted alkyl group having 1 to 60 carbon atoms), a di (substituted or unsubstituted alkyl group having 1 to 60 carbon atoms) amino group, a substituted or unsubstituted amino group having 6 to 60 carbon atoms, An aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, boron,

a is an integer of 1 to 4, and when a is 2 or more, R ₃ of 2 or more are the same or different, and when R ₃ is plural, each R ₃ may be in fused form, and n is 1 to 4 It is an integer.

The amine group bonded to A in the formulas (1) and (2) may be represented by any one selected from the group consisting of the following [substituents 1] to [52], but is not limited thereto.

[Substituent 1]  [Substituent 2]    [Substituent 3]   

  [Substituent group 4] [Substituent group 5] [Substituent group 6]

[Substituent group 7]     [Substituent group 8] [Substituent group 9]

 [Substituent 10]      [Substituent group 11]   [Substituent group 12]

 [Substituent group 13] [Substituent group 14] [Substituent 15]

 [Substituent group 16] [Substituent group 17] [Substituent 18]

 [Substituent group 19] [Substituent group 20] [Substituent group 21]

 [Substituent 22]   [Substituent group 23] [Substituent group 24]

[Substituent 25] [Substituent 26] [Substituent 27]

[Substituent 28]     [Substituent group 29] [Substituent group 30]

[Substituent 31]  [Substituent group 32]     [Substituent group 33]

[Substituent 34] [Substituent 35]      [Substituent 36]

[Substituent group 37]    [Substituent group 38] [Substituent group 39]

[Substituent 40]  [Substituent 41]  [Substituent 42]

[Substituent 43]   [Substituent 44] [Substituent 45]

[Substituent group 46] [Substituent group 47]  [Substituent group 48]

[Substituent group 49] [Substituent group 50] [Substituent group 51]

[Substituent 52]

In the above substituents, R may be the same or different from each other and is selected from the group consisting of hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted C1- A substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted C1 to C60 alkoxy group, A substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, (Substituted or unsubstituted alkyl having 1 to 60 carbon atoms) amino group, or a substituted or unsubstituted aryl (having 6 to 60 carbon atoms) amino group, di (substituted or unsubstituted A substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, and boron, and each has 1 To 12 carbon atoms, and each of the substituents may form a condensed ring with adjacent groups.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. It will be apparent, however, to those skilled in the art that these embodiments are for further explanation of the present invention and that the scope of the present invention is not limited thereby.

(Example)

Synthesis Example 1: Synthesis of Formula 2

Synthesis Example 1- (1): Synthesis of Intermediate 1-a

Intermediate 1-a was synthesized according to Scheme 1 below:

<Reaction Scheme 1>

                                       <Intermediate 1-a>

(53.0 g, 0.381 mol), 2-bromobenzyl bromide (100 g, 0.400 mol), potassium carbonate (131.64 g, 0.952 mol) and acetonitrile (740 ml) were added to a 2L round bottom flask reactor under nitrogen atmosphere And the mixture was refluxed overnight. After completion of the reaction, the temperature was lowered to room temperature and 1 L of water was added and stirred. The reaction solution was extracted with ethyl acetate and the organic layer was separated. After removing water with magnesium sulfate, the mixture was filtered and concentrated under reduced pressure. 200 ml of dichloromethane was added, and the mixture was stirred, and 500 ml of heptane was added to crystallize. The resulting solid was filtered and washed with 500 ml of heptane. <Intermediate 1-a> (112 g, 96%) was obtained as a white solid.

Synthesis Example 1- (2): Synthesis of Intermediate 1-b

Intermediate 1-b was synthesized according to Scheme 2 below:

<Reaction Scheme 2>

<Intermediate 1-a> <Intermediate 1-b>

(37.0 g, 0.12 mol), palladium acetate (1.4 g, 0.006 mol), potassium acetate (76.8 g, 0.783 mol), tetrabutylammonium bromide (1.94 g, , 1100 ml of N, N-dimethylacetamide and 110 ml of water were added and the mixture was heated and stirred at 110 DEG C for about 1 hour. After confirming completion of the reaction, the temperature was cooled to room temperature. The reaction solution was extracted with water and ethyl acetate. The organic layer was separated, and water was removed with magnesium sulfate, followed by filtration and concentration under reduced pressure. Recrystallization from dichloromethane and methanol gave <Intermediate 1-b> (23.6 g, 86.5%).

Synthesis Example 1- (3): Synthesis of Intermediate 1-c

Intermediate 1-c was synthesized according to scheme 3 below:

<Reaction Scheme 3>

<Intermediate 1-b> <Intermediate 1-c>

<Intermediate 1-b> (71.0 g, 0.31 mol) was dissolved in 710 ml of ethyl acetate and stirred in a 1 L round bottom flask under a nitrogen atmosphere. To the reaction solution, 350 ml of ethanol was added, tin (III) chloride dihydrate (282.0 g, 1.25 mol) was added little by little, and the mixture was stirred at room temperature overnight. After completion of the reaction, the reaction solution was transferred into a 5 L flask, and 2 L of water was added thereto. 600 g of potassium carbonate and 1 L of EA were added and stirred. The organic layer was separated, concentrated under reduced pressure, and recrystallized from dichloromethane and methanol to obtain Intermediate 1-c (43 g, 70%).

Synthesis Example 1- (4): Synthesis of Intermediate 1-d

Intermediate 1-d was synthesized according to Scheme 4 below:

<Reaction Scheme 4>

<Intermediate 1-c> <Intermediate 1-d>

<Intermediate 1-c> (17 g, 0.086 mol), 100 ml of water and 20 ml of hydrochloric acid (con.) Were added to a 1 L round bottom flask reactor and stirred at 0 ° C. Sodium nitrite (7.1 g, 0.103 mol) was dissolved in 50 ml of water and added dropwise to the reaction solution, followed by stirring at the same temperature for 1 hour. Potassium iodide (28.6 g, 0.172 mol) was dissolved in 50 ml of water and added dropwise to the reaction solution. Note that the temperature of the reaction solution should not exceed 5 ° C. After completion of dropwise addition, the mixture was stirred overnight at room temperature. After completion of the reaction, 50 ml of sodium cyanosulfate pentahydrate aqueous solution was added and stirred for 10 minutes. The reaction mixture was extracted with ethyl acetate and water. The organic layer was separated, concentrated under reduced pressure, and then subjected to column separation to obtain <Intermediate 1-d> (15 g, 56.5%).

Synthesis Example 1- (5): Synthesis of Intermediate 1-e

Intermediate 1-e was synthesized according to Scheme 5 below:

<Reaction Scheme 5>

                                  <Intermediate 1-e>

To a 500 mL round bottom flask reactor were added 1-bromo-4-iodobenzene (15 g, 0.053 mol), 10-phenylanthracene-9-boronic acid (17.4 g, 0.058 mol), tetrakis (triphenylphosphine) palladium 1.23 g, 1.1 mmol) and potassium carbonate (14.6 g, 0.106 mol) were placed, and 75 mL of toluene, 75 mL of tetrahydrofuran and 30 mL of water were added. The temperature of the reactor was raised to 90 ° C and stirred overnight. When the reaction was completed, the temperature of the reactor was lowered to room temperature, extracted with ethyl acetate, and the organic layer was separated. The organic layer was concentrated under reduced pressure, dissolved in toluene, and filtered on a silica gel pad. The filtrate was concentrated under reduced pressure and then recrystallized with methanol to obtain <Intermediate 1-e> (16.5 g, 76%).

Synthesis Example 1- (6): Synthesis of Intermediate 1-f

Intermediate 1-f was synthesized according to Scheme 6 below:

<Reaction Scheme 6>

<Intermediate 1-e> <Intermediate 1-f>

(16.5 g, 0.04 mol), bis (dipinacoleato) diboron (13.1 g, 0.052 mol), PdCl2 (dppf) (0.7 g, 1 mmol), potassium acetate 9.8 g, 0.1 mol) was added, 165 ml of toluene was added, and the mixture was refluxed overnight. After completion of the reaction, the reaction mixture was subjected to hot filtration and the filtrate was concentrated under reduced pressure and purified by column chromatography to obtain <Intermediate 1-f> (12.5 g, 68%

Synthesis Example 1- (7): Synthesis of Compound (2)

Formula 2 was synthesized according to Scheme 7 below:

<Reaction Scheme 7>

&Lt; Intermediate 1-d > < Intermediate 1-f &

<Intermediate 1-d> (5.0 g, 0.016 mol), <Intermediate 1-f> (8.2 g, 0.018 mol), tetrakis (triphenylphosphine) palladium (0.38 g, 0.3 mmol) in a 100 mL round bottom flask reactor, , Potassium carbonate (4.5 g, 0.032 mol) were placed, and 25 mL of toluene, 25 mL of tetrahydrofuran, and 10 mL of water were added. The temperature of the reactor was raised to 90 ° C and stirred overnight. When the reaction was completed, the temperature of the reactor was lowered to room temperature, 40 ml of methanol was added to the reactor, and the mixture was stirred for 1 hour. The resulting solid was filtered and washed with methanol. The solid was dissolved in toluene and filtered through silica gel. The filtrate was concentrated and acetone was added to crystallize. Recrystallization from toluene and acetone gave 5.2 g (62%).

MS (MALDI-TOF): m / z 515.23 [M ^&lt; ⁺ &^gt;].

Synthesis Example 2: Synthesis of Compound (8)

Synthesis Example 2- (1): Synthesis of Compound (8)

Intermediate 2-a was synthesized according to Scheme 8 below:

<Reaction Scheme 8>

                                           <Intermediate 2-a>

<Intermediate 2-a> (40 g, 90.3%) was obtained in the same manner as in Synthesis Example 1- (1), except that 3-nitrophenol was used instead of 2-nitrophenol.

Synthesis Example 2- (2): Synthesis of Intermediate 2-b

Intermediate 2-b was synthesized according to Scheme 9 below:

<Reaction Scheme 9>

&Lt; Intermediate 2-a > < Intermediate 2-b &

<Intermediate 2-b> (18 g, 81%) was obtained using the same method except that <Intermediate 2-a> was used in place of <Intermediate 1-a> in Synthesis Example 1- (2).

Synthesis Example 2- (3): Synthesis of Intermediate 2-c

Intermediate 2-c was synthesized according to Scheme 10 below:

<Reaction formula 10>

<Intermediate 2-b> <Intermediate 2-c>

<Intermediate 2-c> (11.3 g, 72.3%) was obtained using the same method as in Synthesis Example 1- (3), except that <Intermediate 2-b> was used instead of <Intermediate 1-b>.

Synthesis Example 2- (4): Synthesis of Intermediate 2-d

Intermediate 2-d was synthesized according to Scheme 11 below:

<Reaction Scheme 11>

<Intermediate 2-c> <Intermediate 2-d>

<Intermediate 2-d> (10.5 g, 59.5%) was obtained using the same method except that <Intermediate 2-c> was used in place of <Intermediate 1-c> in Synthesis Example 1- (4).

Synthesis Example 2- (5): Synthesis of Compound (8)

(8) was synthesized according to Scheme 12 below:

<Reaction Scheme 12>

&Lt; Intermediate 2-d > < Intermediate 1-f &

(4.8 g, 57.4%) was obtained using the same method except that <Intermediate 2-d> was used in place of <Intermediate 1-d> in Synthesis Example 1- (7).

MS (MALDI-TOF): m / z 515.23 [M ^&lt; ⁺ &^gt;].

Synthesis Example 3: Synthesis of Formula 24

Synthesis Example 3- (1): Synthesis of Intermediate 3-a

Intermediate 3-a was synthesized according to Scheme 13 below:

<Reaction Scheme 13>

                         <Intermediate 3-a>

2-bromomethylbenzoate (113 g, 0.525 mol) and 900 ml of tetrahydrofuran were placed in a 2 L round bottom flask under a nitrogen atmosphere and then cooled to 0 ° C. Add methylmagnesium bromide (3M) (525.5 ml, 1.576 mol) dropwise at the same temperature and take care not to exceed 15 degrees. After completion of the dropwise addition, the temperature was gradually raised and stirred at room temperature overnight. The reaction solution was poured into 2 L of ice water and stirred. 300 ml of concentrated hydrochloric acid was slowly added and extracted with ethyl acetate. The organic layer was separated, washed with an aqueous solution of sodium hydrogencarbonate, and then water was removed with magnesium sulfate, followed by filtration and concentration under reduced pressure. The material was separated and purified by column chromatography to obtain <Intermediate 3-a> (89 g, 78.7%).

Synthesis Example 3- (2): Synthesis of Intermediate 3-b

Intermediate 3-b was synthesized according to Scheme 14 below:

<Reaction Scheme 14>

&Lt; Intermediate 3-a > < Intermediate 3-b &

(85.3 g, 0.397 mol), palladium acetate (4.5 g, 0.05 mol), triphenylphosphine (10.4 g, 0.04 mol), cesium carbonate (261 g, 0.8 ml) and N, N-dimethylformamide (1000 ml) were added, and the mixture was stirred at 80 ° C for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and 1000 ml of ammonium chloride was added to the reaction solution. The reaction solution was extracted with dichloromethane and the organic layer was separated and concentrated under reduced pressure. The material was separated and purified by column chromatography to obtain <Intermediate 3-b> (58 g, 69%).

Synthesis Example 3- (3): Synthesis of Intermediate 3-c

Intermediate 3-c was synthesized according to Scheme 15 below:

<Reaction Scheme 15>

<Intermediate 3-b> <Intermediate 3-c>

<Intermediate 3-b> (28.0 g, 0.133 mol) and 180 ml of tetrahydrofuran were dissolved in a 500 ml round-bottomed flask under a nitrogen atmosphere and then cooled to -78 ° C. N-butyl lithium (1.6 m) (87.4 ml, 0.14 mol) was added dropwise to the cooled reaction solution. After dropwise addition, the temperature was raised to room temperature and then stirred. After stirring for 20 hours, the temperature was further cooled to -78 ° C, iodine (35.5 g, 0.140 mol) was added in small portions, and the mixture was stirred at room temperature. After completion of the reaction, the reaction mixture was washed with an aqueous solution of sodium cyanosulfate, followed by extraction with ethyl acetate and water. The organic layer was separated, and water was removed with magnesium sulfate, followed by concentration under reduced pressure. The material was separated and purified by column chromatography to obtain <Intermediate 3-c> (21.3 g, 47%).

Synthesis Example 3- (4): Synthesis of Formula 24

24 was synthesized according to Scheme 16 below:

<Reaction Scheme 16>

&Lt; Intermediate 3-c > < Intermediate 1-f &

(4.8 g, 59.4%) was obtained by using the same method as in Synthesis Example 1- (7), except that <Intermediate 3-c> was used instead of <Intermediate 1-d>.

MS (MALDI-TOF): m / z 543.26 [M ^&lt; ⁺ &^gt;].

Example

1 to 5. Preparation of Organic Light Emitting Diode

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the substrate was mounted in a vacuum chamber, the substrate was pressurized to a pressure of 1 x 10 ^-6 torr. Then, an organic substance was injected onto the ITO using DNTPD (700 ANGSTROM), NPD (300 ANGSTROM), the compound prepared by the present invention + BD1 (5% (E-1): [Formula E-2] = 1: 1, Formula E-1 (5 Å) and Al (1,000 Å). The structures of [DNTPD], [? -NPD], [E-1], [E-2] and [BD 1]

<DNTPD> <α-NPD>

<Formula E-1><FormulaE-2><BD1>

Comparative Example

The organic light emitting diode device for the comparative example was fabricated in the same manner except that BH1 and BH2, which are commonly used as fluorescent host materials, were used instead of the compound prepared by the invention in the device structure of the above embodiment, and the structures of BH1 and BH2 Is as follows

<BH1><BH2>

Voltage, luminance, and color coordinates were measured for the organic electroluminescent device manufactured according to Examples 1 to 5 and Comparative Examples 1 and 2, and the results are shown in Table 1 below.

division Host Dopant V Cd / m ² CIEx CIEy Comparative Example 1 BH1 BD1 4.3 550 0.14 0.12 Comparative Example 2 BH2 BD1 4.2 530 0.14 0.11 Example 1 2 BD1 3.6 505 0.131 0.10 Example 2 8 BD1 3.6 680 0.132 0.11 Example 3 24 BD1 3.6 480 0.134 0.10 Example 4 31 BD1 3.6     510 0.131 0.10 Example 5 32 BD1 3.6 489 0.130 0.10

As shown in the evaluation results of Table 1, the organic electroluminescent device using the compound of the new structure according to the embodiment of the present invention has a lower driving voltage and better color purity than the comparative example due to the structural characteristic of the formula (A) .

Claims (11)

An organic light-emitting compound represented by the following formula (A).
(A)

In the above formula (A)
Any one of R ₁ to R ₈ is a single bond which bonds with the linking group L;
The substituents R ₁ to R ₁₉ are the same or different from each other and each independently represent 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 C2-C20 alkynyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, A substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having at least one heteroatom selected from O, N, S and Si, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon number A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, A substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, 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 nitro group, and a halogen group, and may be connected to adjacent substituents to form a monocyclic or polycyclic ring of an alicyclic or aromatic group, and a monocyclic or polycyclic ring of the formed alicyclic or aromatic group The carbon atom may be substituted with any one or more heteroatoms selected from N, S, and O;
The linking group L is a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted group having 2 to 60 carbon atoms Substituted or unsubstituted C2-C60 alkynylene groups, substituted or unsubstituted C3-C60 alkynylene groups, substituted or unsubstituted C2- A substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;
Wherein n is an integer of 1 to 3, and when n is 2 or more, each L may be the same or different,
The "substituted" in the "substituted or unsubstituted" in the above [Formula A] is a substituent selected from the group consisting of deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group having 1 to 24 carbon atoms, 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, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, An alkylamino group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, An arylsilyl group having 1 to 24 carbon atoms, and an aryloxy group having 1 to 24 carbon atoms. The method according to claim 1,
The linking group L may be a single bond or any one selected from the following Structural Formulas 1 to 9,
and n is 1 or 2.
[Structural Formula 1] [Structural Formula 2] [Structural Formula 3] [Structural Formula 4]

[Structural formula 5] [Structural formula 6] [Structural formula 7]

[Structural formula 8] [Structural formula 9]

In the substituent L, the carbon of the aromatic ring may be bonded to hydrogen or deuterium. The method according to claim 1,
Wherein the substituent R &lt; ₁₉ &gt; in the formula (A) is a substituted or unsubstituted aryl group having 6 to 24 carbon atoms. The method according to claim 1,
Wherein L is a single bond or is represented by the following formula [11] or [12]
and n is 1.
[Structural formula 11] [Structural formula 12]

The method according to claim 1,
The substituent R &lt; ₁₉ &gt; in the formula (A) is a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, and includes deuterium in an aromatic ring. The method according to claim 1,
Wherein the organic luminescent compound is any one selected from the group consisting of the following chemical formulas (1) to (48).

&Lt; Formula 1 >< EMI ID =

&Lt; Formula 4 &gt;&lt; EMI ID =

&Lt; Formula 7 >< EMI ID =

&Lt; Formula 10 &gt;&lt; EMI ID =

&Lt; Formula 13 >< EMI ID =

&Lt; Formula 16 &gt;&lt; EMI ID =

&Lt; Formula 19 >< EMI ID =

&Lt; Formula 22 &gt;&lt; EMI ID =

&Lt; Formula 25 >< EMI ID = 26.0 >

&Lt; Formula 28 >< EMI ID = 29.0 >

&Lt; Formula 31 >< EMI ID =

&Lt; Formula 34 &gt;&lt; EMI ID =

&Lt; Formula 37 >< EMI ID = 38.0 >

&Lt; Formula 40 >< EMI ID =

&Lt; General Formula 43 &gt;

&Lt; Formula 46 &gt;&lt; EMI ID = A first electrode;
A second electrode facing the first electrode; And
And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer contains at least one compound selected from the group consisting of the compounds of claims 1 to 6. 8. The method of claim 7,
Wherein the organic layer comprises at least one of a hole injecting layer, a hole transporting layer, a functional layer having both a hole injecting function and a hole transporting function, a light emitting layer, an electron transporting layer, and an electron injecting layer. 9. The method of claim 8,
Wherein the organic layer interposed between the first electrode and the second electrode is a light emitting layer, and the light emitting layer comprises a host and a dopant, and the organic light emitting compound is used as a host. 9. The method of claim 8,
Wherein at least one layer selected from the respective layers is formed by a deposition process or a solution process. 8. The method of claim 7,
The organic light emitting device includes a flat panel display device; A flexible display device; Monochrome or white flat panel illumination devices; And a device for flexible illumination of a single color or a white color.

Images