KR20150114658A - An organoelectro luminescent compounds and organoelectro luminescent device using the same - Google Patents

Abstract

The present invention relates to an organic light emitting compound represented by the chemical formula 1 and an organic electroluminescent device comprising the same. According to the present invention, an organic light emitting compound is capable of performing an organic electroluminescent device with improved various light emitting properties such as a driving voltage, light emitting efficiency, brightness, thermal stability, device durability, etc., by reducing a band gap of HOMO and LUMO and effectively performing light manifested in a dopant.

Description

[0001] The present invention relates to an organic electroluminescent compound and an organic electroluminescent device using the same,

More particularly, the present invention relates to a bipolar compound containing a benzocarbazole-based compound and an organic electroluminescent compound capable of being driven at a low voltage and having excellent luminous efficiency, luminance, thermal stability, Emitting device.

In recent years, organic light emitting devices capable of being driven by a low voltage in a self-emission type are superior in viewing angle and contrast ratio compared to a liquid crystal display, which is a mainstream of a flat panel display device, require no backlighting and are lightweight and thin, And has been attracting attention as a next generation display device.

An organic electroluminescent device is a device that injects electric charge into an organic light emitting layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode) to form an electron and a hole.

The organic electroluminescent device can be formed on a transparent substrate that can be made of plastic and can be driven at a voltage as low as 10 V or less as compared with a plasma display panel or an inorganic electroluminescent display and has a relatively low power consumption , And has an advantage of excellent color. In addition, organic electroluminescent devices are capable of displaying three colors of green, blue, and red, and thus are attracting much attention as next-generation rich color display devices.

The most important factor determining the luminous efficiency in an organic electroluminescent device is a light emitting material. However, the development of a phosphorescent material on a light-emitting mechanism is one of the ways that the luminous efficiency can be improved more theoretically. Accordingly, a variety of phosphorescent materials have been developed to date, Particularly, CBP (4,4'-N, N'-dicarbazolbiphenyl) is the most widely known phosphorescent host material, and materials in which various substituents are introduced into carbazole are disclosed in Japanese Patent Laid-Open Publication No. 2008-214244 2003-133075) or an organic electroluminescent device using a BALq derivative as a host.

However, an organic electroluminescent device using a phosphorescent material has a significantly higher current efficiency than a device using a fluorescent material. However, when a material such as BAlq or CBP is used as a host of a phosphorescent material, There is no great advantage in terms of power efficiency because the voltage is high and the recombination of excitons in the light emitting layer is uneven when the transport of electrons or holes is shifted to either side, It is required to develop a high-performance host material which is more stable in driving voltage, lifetime characteristics, and the like.

Further, the inventors of the present invention succeeded in uniformizing the recombination of the exciton using the benzocarbazole-based bipolar compound (Korean Patent Application No. 10-2013-0042687) filed before the present invention, but the band of HOMO and LUMO It has been difficult to efficiently realize the light emitted from the dopant because the band gap is large.

Therefore, further improvement is required in terms of efficiency and lifetime in order to realize a more stable organic electroluminescent device and high efficiency, long life, and large size of the device.

Accordingly, it is an object of the present invention to solve the above-mentioned problems, and it is an object of the present invention to provide a method for forming a hole transporting layer by additionally introducing a p-type substituent into a substituent having the property of a hole transporting layer of a bipolar compound to reduce bandgap between HOMO and LUMO, To provide an organic light emitting compound capable of further improving various light emitting properties such as a driving voltage, a light emitting efficiency, a luminance, a thermal stability, and a device life.

Also, the present invention is to provide an organic electroluminescent device which can be driven at a low voltage by employing the organic electroluminescent compound as a light emitting material, and which has high efficiency, brightness, and lifetime characteristics.

In order to solve the above-described problems, the present invention provides an organic luminescent compound represented by the following formula (1).

[Chemical Formula 1]

Further, the present invention is a liquid crystal display device comprising a first electrode, a second electrode facing the first electrode, and at least one organic layer interposed between the first electrode and the second electrode, The organic electroluminescent device includes at least one organic electroluminescent compound to be displayed.

Specific substituents of the organic luminescent compound represented by the formula (1) according to the present invention will be described later.

The organic luminescent compound according to the present invention reduces the bandgap between HOMO and LUMO to realize light efficiently in a dopant to improve light emitting properties such as a driving voltage, a luminous efficiency, a luminance, a thermal stability and a device life An organic electroluminescent device can be realized.

1 is a conceptual view illustrating a structure of an organic electroluminescent device according to an embodiment of the present invention.

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

The present invention is an organic luminescent compound employed in an organic layer of an organic electroluminescent device, characterized by being represented by the following formula (1) and being a bipolar compound having a hole transporting unit and an electron transporting unit simultaneously in the molecule.

[Chemical Formula 1]

In the above formula (1)

Z ₁ , Z ₂ and Z ₃ are each independently CH or N, and at least one of Z ₁ to Z ₃ is N.

X and Y each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms.

L is a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarylene group having 6 to 30 carbon atoms, n is an integer of 0 to 3, 2 or more, the plural Ls may be the same or different from each other.

-HTU ₁ (Hole Transportation Unit) is a benzocarbazole-based hole transporting unit and is characterized by being represented by the following formula (2).

(2)

In the above formula (2)

R ₁ , R ₂ , R ₃ and R ₄ are the same or different and each independently represents hydrogen, deuterium, halogen, a nitro group, a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, A substituted or unsubstituted C1-C40 alkenyl group, a substituted or unsubstituted C1-C40 alkoxy group, a substituted or unsubstituted C1-C40 amino group, a substituted or unsubstituted C3-C40 cycloalkyl group, a substituted or unsubstituted C3- A substituted or unsubstituted aryl group having 6 to 40 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 40 carbon atoms.

The adjacent two of R ₁ to R ₄ may combine with each other to form at least one fused ring.

Q is selected from the group consisting of hydrogen, deuterium, halogen, nitro, substituted or unsubstituted alkyl having 1 to 40 carbon atoms, substituted or unsubstituted alkenyl having 2 to 40 carbon atoms, substituted or unsubstituted alkoxy having 1 to 40 carbon atoms, Or an unsubstituted or substituted amino group having 1 to 40 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 40 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms And a substituted or unsubstituted heteroaryl group having 5 to 40 carbon atoms, m is an integer of 1 to 5, and when m is 2 or more, the plurality of Qs may be the same or different from each other.

The Q may also be bonded to adjacent substituents to form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring.

* HTU ₂ (Hole Transportation Unit) is a diarylamine or carbazole-based positive-working air vent, and is characterized by being represented by the following formula 3.

(3)

In the above formula 3,

R ₅ , R ₆ , R ₇ , R ₈ , R ₉ and R ₁₀ are the same or different and each independently represents hydrogen, deuterium, a halogen, a nitro group, a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 40 carbon atoms, a substituted or unsubstituted amino group having 1 to 40 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 40 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 40 carbon atoms, Or a substituted or unsubstituted C6-C40 aryl group and a substituted or unsubstituted C6-C40 heteroaryl group, or a substituted or unsubstituted C6-C40 heteroaryl group.

R ₉ and R ₁₀ may combine with each other to form a fused ring.

Q is selected from the group consisting of hydrogen, deuterium, halogen, nitro, substituted or unsubstituted alkyl having 1 to 40 carbon atoms, substituted or unsubstituted alkenyl having 2 to 40 carbon atoms, substituted or unsubstituted alkoxy having 1 to 40 carbon atoms, Or an unsubstituted or substituted amino group having 1 to 40 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 40 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms And a substituted or unsubstituted heteroaryl group having 5 to 40 carbon atoms, m is an integer of 1 to 5, and when m is 2 or more, the plurality of Qs may be the same or different from each other.

The Q may also be bonded to adjacent substituents to form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring.

The 'substituted' in the 'substituted or unsubstituted' may be a hydrogen, a deuterium, a halogen, a nitro group, an alkyl group having 1 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an alkoxy group having 1 to 40 carbon atoms, Substituted with at least one substituent selected from the group consisting of an amino group having 1 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, a heterocycloalkyl group having 3 to 40 carbon atoms, an aryl group having 6 to 40 carbon atoms, and a heteroaryl group having 5 to 40 carbon atoms as the X, Y, L, R ₁ to R _60, and Q may be further substituted with the substituents independently of each other.

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 is a single or fused ring system containing 5 to 7 atoms, preferably 5 or 6 atoms And when a substituent is present in the aryl group, it may be fused with an adjacent substituent to further form a ring.

Specific examples of the aryl group include a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 4-ethylphenyl group, an o- Naphthyl group, 1-methylnaphthyl group, 2-methylnaphthyl group, anthryl group, phenanthryl group, naphthyl group, An aromatic group such as a fluorenyl group, a pyrenyl group, an indenyl group, a fluorenyl group, a tetrahydronaphthyl group, a pyrenyl group, a perylene group, a crycenyl group, a naphthacenyl group and a fluoranthenyl group.

The at least one hydrogen atom in the aryl group may be substituted with at least one substituent selected from the group consisting of a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a silyl group, an amino group (-NH2, -NH (R) R 'and R "are independently an alkyl group having 1 to 10 carbon atoms, and in this case, they are referred to as" alkylamino group "), amidino group, hydrazine group, hydrazone group, carboxyl group, sulfonic acid group, phosphoric acid group, , A halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, 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.

On the other hand, the heteroaryl group contained in the organic light emitting compound according to the present invention is a heteroaromatic group having 2 to 24 carbon atoms which may contain 1 to 4 hetero atoms selected from N, O, P or S in each ring in the aryl group Refers to an organic radical, which rings can 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.

When X and Y are each independently an aryl group or a heteroaryl group, they may be more specifically selected from the group consisting of the following structural formula (1).

[Structural formula 1]

In the above formula 1,

Q ₁ is the same as the definition of Q in the above formula 2, 1 is an integer of 1 to 9, and when 1 is 2 or more, the plurality of Qs are the same or different from each other and combine with adjacent substituents to form a condensed aliphatic ring , Condensed aromatic rings, condensed heteroaliphatic rings or condensed heteroaromatic rings.

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 in the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy and hexyloxy. May be substituted with the same substituent as in the case of the aryl group.

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

Specific examples of the alkenyl group used in the present invention include straight or branched chain alkenyl groups, and examples thereof include a 3-pentenyl group, a 4-hexenyl group, a 5-heptenyl group, a 4-methyl- Dimethyl-pentenyl group, 6-methyl-5-heptenyl group and 2,6-dimethyl-5-heptenyl group.

According to a preferred embodiment of the present invention, the organic luminescent compound represented by the above formula (1) may be more specifically selected from the following compounds [compound 1] to [compound 175].

Further, the present invention provides an organic electroluminescent device comprising a first electrode, a second electrode facing the first electrode, and an organic layer interposed between the first electrode and the second electrode, May contain one or more kinds of luminescent compounds.

The organic layer containing the organic luminescent compound of the present invention may include 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, have.

When the compound represented by Formula 1 is included in the organic electroluminescent device as the material of the electron injecting layer, the electron transporting layer, the hole injecting layer, and the hole transporting layer, the electron injecting / transporting ability of the organic electroluminescent device, / Transport capacity can be maximized.

In addition, the organic layer interposed between the first electrode and the second electrode may include a light emitting layer, and the light emitting layer may specifically include a host and a dopant, and the organic light emitting compound of the present invention may be used as a host, The luminous efficiency and lifetime characteristics of the organic electroluminescent device are maximized.

In addition, in the present invention, a dopant material may be used for the light emitting layer, in addition to the host. When the light emitting layer comprises a host and a dopant, the content of 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, A dopant compound can be used.

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

1 is a cross-sectional view showing the structure of an organic electroluminescent device of the present invention. The organic electroluminescent device according to the present invention includes an anode 20, a hole transport layer 40, an organic emission layer 50, an electron transport layer 60 and a cathode 80, The electron injecting 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.

Hereinafter, an organic electroluminescent device and a method of manufacturing the same will be described with reference to FIG.

First, an anode electrode material is coated on the substrate 10 to form an anode 20. Here, as the substrate 10, a substrate used in a typical organic electroluminescent device is used, and an organic substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness is preferable. 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.

The hole injection layer material is not particularly limited as long as it is conventionally used in the art. For example, 2-TNATA [4,4 ', 4 "-tris (2-naphthylphenyl-phenylamino) -triphenylamine] , NPD [N, N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'- biphenyl-4,4'-diamine], DNTPD [N, N'-diphenyl-N, N'-bis- [4- ] Can be used.

The material for the hole transport layer is not particularly limited as long as it is commonly used in the art and includes, for example, N, N'-bis (3-methylphenyl) -N, N'- -Biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine (? -NPD).

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 the present invention, as the electron transporting layer material, a known electron transporting material can be used, which functions to stably transport electrons injected from an electron injection electrode (cathode). Examples of electron transport materials are known, a quinoline derivative, in particular tris (8-quinolinolato) aluminum (Alq _3), TAZ, Balq, beryllium bis (benzo-10-quinolinyl furnace benzoate) (beryllium bis (10-benzoquinolin -olate: Bebq2), ADN, oxadiazole derivative PBD, BMD, BND, and the like may be used, but the present invention is not limited thereto.

In addition, the light emitting layer may be made of a host and a dopant. According to a specific example of the present invention, the thickness of the light emitting layer is preferably 50 to 2,000 ANGSTROM.

In addition, the organic electroluminescent device according to the present invention may have an insulating layer or an adhesive layer interposed between the electrode and the organic layer, as well as the structure in which the anode, one or more organic layers and the cathode are sequentially stacked, as described above.

In the organic electroluminescent device according to the present invention, the organic material layer containing the compound represented by Formula 1 may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

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, Refers to a method of forming a thin film by evaporating a material used as a material for forming each layer through heating or the like under a vacuum or a low pressure state, Refers to a method of forming a thin film by mixing with a solvent and then subjecting it to a method such as ink jet printing, roll to roll coating, screen printing, spray coating, dip coating, spin coating and the like.

The organic electroluminescent device according to the present invention may be formed by using materials and methods known in the art, except that at least one layer of one or more organic layers is formed to include an organic light emitting compound represented by Formula 1 of the present invention Thereby forming an organic layer and an electrode.

Further, the organic electroluminescent device according to the present invention can be used in a device selected from a flat panel display device, a flexible display device, a monochromatic or white flat panel illumination device, and a single color or white flexible illumination device.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the appended claims. It will be clear to those who have knowledge.

<Examples>

Synthesis Example 1 Synthesis of Compound Represented by Compound 1

Synthesis Example 1-1 Synthesis of Compound a

[Reaction Scheme 1-1]

At room temperature, 20 g of compound (1) is dissolved in 100 mL of chloroform, and then 7.12 g of N-bromosuccinamide (NBS) is added. The mixture was further stirred at room temperature for 2 hours, and the precipitated solid was collected by filtration and washed with 100 mL of methanol to obtain 17.08 g (yield: 74%) of a white solid.

Synthesis Example 1-2 Synthesis of Compound 1

[Reaction Scheme 1-2]

0.1 g of bis (dibenzylidene acetone) palladium (0), 0.04 g of tri- t- butylphosphine and 1.24 g of sodium tertbutoxide were placed in 40 mL of toluene, and the mixture was refluxed The mixture was stirred at room temperature for 15 hours, cooled to room temperature, 40 mL of water was added, stirred for 10 minutes, and the organic layer was separated. The separated organic layer was concentrated and purified by column chromatography (n-hexane / dichloromethane = 4/1) to obtain 3.89 g (yield: 85%) of a compound represented by Compound 1 as a white solid.

_{1H NMR (500MHz, CDCl 3)} 6.48 (d, 1H), 7.01 (t, 2H), 7.07 (d, 4H), 7.24-7.27 (m, 4H), 7.48-7.53 (m, 6H), 7.57-7.67 (m, 2H), 8.34 (d, 4H), 7.72 (d, 1H), 7.90 ), 8.49 (d, 1 H)

Synthesis Example 2 Synthesis of Compound 11

[Reaction Scheme 2]

The [Synthesis Example 1-1] Compound a 4 g, N -phenyl-1 -naphthaleneamine 1.53 g, bis (dibenzylideneacetone) palladium (0) 0.11 g, tri- t -butylphosphine 0.04 g and 1.24 g sodium tertbutoxide obtained in toluene And the mixture is stirred at reflux for 15 hours. After cooling to room temperature, 40 mL of water is added, stirring is continued for 10 minutes, and the organic layer is separated. The separated organic layer was concentrated and purified by column chromatography (n-hexane / dichloromethane = 4/1) to obtain 4.07 g (yield: 83%) of a compound represented by Compound 11 as a white solid.

_{1H NMR (500MHz, CDCl 3)} 6.48 (d, 1H), 7.01 (t, 1H), 7.10 (d, 2H), 7.24 (t, 2H), 7.48-7.52 (m, 8H), 7.57-7.63 (m (M, 3H), 8.22-8.25 (m, 3H), 7.80 (d, ), 8.36 (dd, 4H), 8.52 (d, 1 H)

Synthesis Example 3 Synthesis of Compound Represented by Compound 16

[Reaction Scheme 3]

0.1 g of bis (dibenzylideneacetone) palladium (0), 0.04 g of tri- t- butylphosphine and 1.24 g of sodium tertbutoxide were placed in 40 ml of toluene, and the mixture was stirred under reflux conditions For 15 hours, cooled to room temperature, 40 mL of water is added, stirred for 10 minutes, and the organic layer is separated. The separated organic layer was concentrated and purified by column chromatography (n-hexane / dichloromethane = 4/1) to obtain 3.93 g (yield 86%) of a compound represented by Compound 16 as a white solid.

_{1H NMR (500MHz, CDCl 3)} 7.16-7.20 (m, 2H), 7.31 (t, 1H), 7.47-7.51 (m, 7H), 7.54-7.60 (m, 3H), 7.68-7.73 (m, 5H) , 7.91 (d, IH), 8.07 (d, IH), 8.11-8.12 (m, 2H), 8.21-8.24 (m, 3H), 8.34 , 1H)

Synthesis Example 4 Synthesis of Compound Represented by Compound 89

Synthesis Example 4-1 Synthesis of Compound b

[Reaction Scheme 4-1]

At room temperature, 20 g of compound (1) is dissolved in 100 ml of chloroform and 14.24 g of NBS is added. The mixture was further stirred at room temperature for 12 hours, and the precipitated solid was collected by filtration and washed with 100 mL of methanol to obtain 16.13 g (yield: 62%) of white solid.

Synthesis Example 4-2 Synthesis of Compound Represented by Formula 89

[Reaction Scheme 4-2]

0.25 g of diphenylamine, 0.22 g of bis (dibenzylidene acetone) palladium (0), 0.08 g of tri- t- butylphosphine and 2.48 g of sodium tertbutoxide were placed in 40 mL of toluene, and the mixture was refluxed The mixture was stirred at room temperature for 24 hours, cooled to room temperature, and 40 mL of water was added. The mixture was stirred for 10 minutes, and the organic layer was separated. The separated organic layer was concentrated and purified by column chromatography (n-hexane / dichloromethane = 4/1) to obtain 3.28 g (yield 65%) of a compound represented by Compound 89 as a white solid.

_{1H NMR (500MHz, CDCl 3)} 6.48 (d, 1H), 6.98-7.02 (m, 4H), 7.07 (d, 8H), 7.24 (t, 8H), 7.32 (s, 1H), 7.50-7.52 (m 2H), 7.20 (d, IH), 7.90 (d, IH), 7.51-7.61 8.24 (dd, 1 H), 8.34-8.37 (m, 4 H)

Synthesis Example 5 Synthesis of Compound Represented by Compound 99

[Reaction Scheme 5]

The [Synthesis Example 4-1] Compound b 4 g, N -phenyl-1 -naphthaleneamine 2.70 g, bis (dibenzylideneacetone) palladium (0) 0.22 g, tri- t -butylphosphine 0.08 g and 2.48 g sodium tertbutoxide obtained in toluene 40 mL, and the mixture is stirred at reflux for 24 hours. After cooling to room temperature, 40 mL of water is added and stirred for 10 minutes, and the organic layer is separated. The separated organic layer was concentrated and purified by column chromatography (n-hexane / dichloromethane = 4/1) to obtain 3.26 g (yield: 58%) of a compound represented by Compound 99 as a white solid.

_{1H NMR (500MHz, CDCl 3)} 6.48 (d, 1H), 6.97-7.01 (m, 2H), 7.08 (d, 4H), 7.22-7.26 (m, 4H), 7.32 (s, 1H), 7.48-7.52 (m, 1H), 7.59-7.66 (m, 7H), 7.82 (d, 2H), 7.90 , &Lt; / RTI &gt; 4H), 8.34-8.37 (m, 4H)

Synthesis Example 6 Synthesis of Compound Represented by Compound 104

[Reaction Scheme 6]

0.22 g of bis (dibenzylideneacetone) palladium (0), 0.08 g of tri- t- butylphosphine and 2.48 g of sodium tertbutoxide were added to 40 mL of toluene, and the mixture was stirred under reflux conditions For 24 hours, then cooled to room temperature, add 40 mL of water, stir for 10 minutes, and separate the organic layer. The separated organic layer was concentrated and purified by column chromatography (n-hexane / dichloromethane = 4/1) to obtain 3.26 g (yield: 58%) of a compound represented by Chemical Formula 107 as a white solid.

_{1H NMR (500MHz, CDCl 3)} 7.15-7.21 (m, 4H), 7.35 (t, 2H), 7.47-7.51 (m, 8H), 7.57-7.61 (m, 5H), 7.68-7.70 (m, 3H) , 7.75 (d, IH), 7.92 (d, 2H), 8.08 (d, IH), 8.10-8.12 (m, 2H), 8.20-8.23 (m, 4H), 8.36 , 2H)

Examples 1 to 6 Fabrication of Organic Electroluminescent Device

OLED devices were fabricated using the organic light emitting compounds according to the present invention. The transparent electrode ITO thin film (1500 Å) was ultrasonically washed with trichlorethylene, acetone, ethanol, and distilled water sequentially, and stored in isopropanol before use. Next, an ITO substrate was placed on a substrate folder of a vacuum deposition apparatus, and NPB [ N , N- di (naphthalene-1-yl) -N , N- diphenylbenzidine] The transport layer was deposited.

Subsequently, organic light emitting compounds according to the present invention synthesized in Synthesis Examples 1 to 6 were used as hosts, and (piq) ₂ Ir (acac) [bis- (1-phenylisoquinolyl) iridium III) acetylacetonate] was doped to a thickness of 30 nm to form a light emitting layer.

Subsequently, BPhen [bathophenanthroline] was deposited as an electron transport layer on the light emitting layer to a thickness of 30 nm, lithium fluoride was deposited to a thickness of 1 nm as an electron injection layer, and an Al cathode was deposited to a thickness of 100 nm to form an OLED device .

&Lt; Comparative Example 1 &

An organic luminescent device was prepared in the same manner as in Example 1, except that the following [Comparative Compound] was used as a host instead of the compound represented by Compound 1 as a host material in forming the luminescent layer in Example 1 above.

[Comparative compound]

<Experimental Example 1>

The driving voltage and the current efficiency were measured for each of the organic light emitting devices manufactured in Examples 1 to 6 and Comparative Example 1, and the results are shown in Table 1 below.

Claims (8)

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

In the above formula (1)
Z ₁ , Z ₂ and Z ₃ are each independently CH or N, and at least one of Z ₁ to Z ₃ is N,
X and Y are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms,
L is a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarylene group having 6 to 30 carbon atoms, n is an integer of 0 to 3, and n is 2 or more The plurality of L's may be the same or different from each other,
* -HTU ₁ of the above formula (1) is represented by the following formula (2)
(2)

In the above formula (2)
R ₁ , R ₂ , R ₃ and R ₄ are the same or different and each independently represents hydrogen, deuterium, halogen, a nitro group, a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, A substituted or unsubstituted C1-C40 alkenyl group, a substituted or unsubstituted C1-C40 alkoxy group, a substituted or unsubstituted C1-C40 amino group, a substituted or unsubstituted C3-C40 cycloalkyl group, a substituted or unsubstituted C3- A substituted or unsubstituted aryl group having 6 to 40 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 40 carbon atoms,
The adjacent two of R ₁ to R ₄ may combine with each other to form at least one fused ring,
Q is selected from the group consisting of hydrogen, deuterium, halogen, nitro, substituted or unsubstituted alkyl having 1 to 40 carbon atoms, substituted or unsubstituted alkenyl having 2 to 40 carbon atoms, substituted or unsubstituted alkoxy having 1 to 40 carbon atoms, Or an unsubstituted or substituted amino group having 1 to 40 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 40 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms And a substituted or unsubstituted heteroaryl group having 5 to 40 carbon atoms, m is an integer of 1 to 5, and when m is 2 or more, plural Qs are the same or different,
The Q may be bonded to adjacent substituents to form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring,
* -HTU ₂ of the above formula (1) is represented by the formula (3)
(3)

In the above formula 3,
R ₅ , R ₆ , R ₇ , R ₈ , R ₉ and R ₁₀ are the same as defined for R ₁ to R ₄ in Formula 2, and R ₉ and R ₁₀ are bonded to each other to form a fused ring Maybe,
Q and m are the same as defined in the above formula (2)
The Q may combine with adjacent substituents to form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring. The method according to claim 1,
Wherein X, Y, L, R ₁ to R ₁₀ and Q is hydrogen, deuterium, a halogen, a nitro group, a C 1 -C 40 alkyl group, a C2 to 40 alkenyl group, having 1 to 40 carbon atoms in the alkoxy group, a C 1 -C Is further substituted with at least one substituent selected from the group consisting of an amino group having 1 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, a heterocycloalkyl group having 3 to 40 carbon atoms, an aryl group having 6 to 40 carbon atoms, and a heteroaryl group having 5 to 40 carbon atoms . &Lt; / RTI &gt; The method according to claim 1,
And X and Y are each independently any one selected from the group consisting of the following structural formula 1:
[Structural formula 1]
[Structural formula 1]

In the above formula 1,
Q ₁ is the same as the definition of Q in the above formulas (2) to (3), 1 is an integer of 1 to 9,
When l is 2 or more, the plurality of Qs may be the same or different from each other and may combine with adjacent substituents to form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, or a condensed heteroaromatic ring. The method according to claim 1,
The organic luminescent compound according to claim 1, wherein the compound represented by Formula 1 is selected from the following compounds 1 to 175:

A first electrode; A second electrode facing the first electrode; And at least one organic layer interposed between the first electrode and the second electrode,
Wherein the organic layer comprises at least one organic electroluminescent compound represented by Formula 1 according to Claim 1. 6. The method of claim 5,
Wherein the organic layer comprises one or more layers selected from the group consisting 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. The method according to claim 6,
Wherein the light emitting layer comprises at least one host compound and at least one dopant compound, and the host compound is an organic light emitting compound represented by the following formula (1). 6. The method of claim 5,
Wherein the organic layer further comprises one or more organic light emitting layers emitting red, green, or blue light to emit white light.

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