KR101779915B1 - Fused arylamine compound and organic electroluminescent devices comprising the same - Google Patents

Abstract

The present invention relates to a novel condensed arylamine-based compound and an organic electroluminescent device including the same, wherein the organic electroluminescent device comprising the condensed arylamine compound according to the present invention has an excellent effect on luminance, color purity and lifetime .

Description

TECHNICAL FIELD [0001] The present invention relates to a condensed arylamine-based compound and an organic electroluminescent device including the same.

The present invention relates to a condensed arylamine-based compound and an organic electroluminescent device including the same. More particularly, the present invention relates to a condensed arylamine-based compound having excellent brightness, color purity and lifetime, and an organic electroluminescent device including the same.

In recent years, the demand for a flat display device having a small space occupation has been increasing due to the enlargement of a display device. The liquid crystal display, which is a typical flat display device, has an advantage of being lighter than a conventional CRT (cathode ray tube) angle is limited and a back light is necessarily required. On the other hand, an organic light emitting diode (OLED), which is a new flat display device, is a display using a self-luminous phenomenon, has a large viewing angle, is slimmer and smaller than a liquid crystal display, And in recent years, application to a full-color display or illumination is 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 electroluminescent device using an organic light emitting phenomenon usually has a structure including an anode, an anode, and an organic material layer therebetween. Here, in order to enhance the efficiency and stability of the organic electroluminescent device, the organic material layer may have a multi-layer 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 the organic electroluminescent device, holes are injected into the anode, electrons are injected into the organic layer, and excitons are formed when injected holes and electrons meet. When it falls back to the ground state, the light comes out. Such an organic electroluminescent device is known to have properties 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 electroluminescent 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 necessary for realizing better natural color depending on the luminescent color.

On the other hand, when only one material is used as a light emitting material, there arises a problem that the maximum light emission wavelength shifts to a long wavelength due to intermolecular interaction, the color purity decreases, or the efficiency of the device decreases due to the light emission attenuating effect. A host / dopant system may be used as the light emitting material in order to increase the light emitting efficiency through the light emitting layer. 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, light of a desired wavelength can be obtained depending on the type of dopant used.

In order for the organic electroluminescent device to sufficiently exhibit the above-described excellent characteristics, materials constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, and an electron injecting material are supported by a stable and efficient material However, the development of a stable and efficient organic material layer material for an organic electroluminescence device has not been sufficiently developed yet. Therefore, there is a continuing need in the art for the development of new materials.

SUMMARY OF THE INVENTION The present invention provides a condensed arylamine compound having excellent light emission luminance and color purity and long life.

A second object of the present invention is to provide an organic electroluminescent device including the condensed arylamine compound.

In order to accomplish the first technical object, the present invention provides a condensed arylamine compound represented by the following general formula (1).

In Formula 1,

R 1 to R 6 each independently represent hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted group having 3 to 24 carbon atoms A substituted or unsubstituted alkoxy group having 1 to 24 carbon atoms, a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 6 to 24 carbon atoms A substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, and a substituted or unsubstituted silyl group having 1 to 24 carbon atoms,

Each independently represent a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 24 carbon atoms, a substituted or unsubstituted An aryl group having 6 to 24 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 24 carbon atoms,

L is selected from the group consisting of a direct bond, a substituted or unsubstituted arylene group having 6 to 24 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 24 carbon atoms,

Ar is selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 40 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms,

p is 1 or 2;

In order to solve the second technical problem, the present invention provides a semiconductor device comprising: an anode; Cathode; And a layer comprising a condensed arylamine compound represented by the general formula (1), which is interposed between the anode and the cathode.

The organic electroluminescent device containing the condensed arylamine compound represented by the formula (1) in the organic material layer according to the present invention has excellent brightness, color purity and lifetime characteristics, and thus can be used for display and illumination.

1 is a schematic view of an organic electroluminescent device according to one embodiment of the present invention.
FIG. 2 is a diagram showing a change in relative brightness (T80) according to luminance and time according to the current density among the evaluation results of Examples 1 to 3 and Comparative Example 1 according to one embodiment of the present invention.
FIG. 3 is a graph showing the relative luminance change (T80) according to luminance and time according to the current density among the evaluation results of Examples 4 to 6 and Comparative Example 2 according to one embodiment of the present invention.
Description of the Related Art
10: substrate 20: anode
30: Hole injection layer 40: Hole transport layer
50: organic light emitting layer 60: electron transporting layer
70: electron injection layer 80: cathode

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

The condensed arylamine compound according to the present invention is characterized by being represented by the above formula (1).

In the condensed arylamine compound according to the present invention, the substituents of the above formula (1) will be described in more detail as follows.

delete

Specific examples of the alkyl group as the substituent used in the present invention include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isoamyl group, a hexyl group, a heptyl group, A halogen atom, a hydroxyl group, a nitro group, a cyano group, a trifluoromethyl group, a silyl group (in this case, a " alkylsilyl group "hereinafter), a substituted or unsubstituted amino group _{(-NH 2, -NH (R)} , -N (R ') (R''), where R, R' and R" are each independently a carbon number 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 (for example, an alkyl group having 1 to 24 carbon atoms , An alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, An aryl group having from 5 to 24 carbon atoms, an aryl group having from 5 to 24 carbon atoms, an arylalkyl group having from 6 to 24 carbon atoms, a heteroaryl group having from 3 to 24 carbon atoms, or a heteroarylalkyl group having from 3 to 24 carbon atoms.

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, And can be substituted with substituents similar to those in the case of the alkyl group.

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

Specific examples of the aryl group as the substituent group used in the compound of the present invention include a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 4-ethylphenyl group, Examples of the aryl group include phenyl group, 4-methylbiphenyl group, 4-ethylbiphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, 1-naphthyl group, , Anthryl group, phenanthryl group, pyrenyl group, fluorenyl group, perylenyl group, tetrahydronaphthyl group and the like, which may be substituted with the same substituents as those of the alkyl group.

Specific examples of the heteroaryl group used as the substituent in the compound of the present invention include pyridinyl, pyrimidinyl, triazinyl, indolinyl, quinolinyl, pyrrolidinyl, piperidinyl, An oxazolyl group, an oxadiazolyl group, a benzoxazolyl group, a thiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a triazolyl group, an imidazolyl group, a benzoimidazole group, And at least one of the hydrogen atoms of the heteroaryl group may be substituted with the same substituent as the alkyl group.

In the present invention, the term "substituted or unsubstituted" refers to a group selected from the group consisting of deuterium, halogen, alkyl, alkenyl, alkoxy, aryl, arylalkyl, arylalkenyl, heteroaryl, Substituted or unsubstituted with at least one substituent selected from the group consisting of an acetylene group, a nitrile group and an acetylene group.

In the condensed arylamine compound according to the present invention, Ar of Formula 1 is a substituted or unsubstituted pyrene group, a substituted or unsubstituted anthracene group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluorene group , A substituted or unsubstituted biphenyl group, and a substituted or unsubstituted naphthalene group, but is not limited thereto.

Specifically, the condensed arylamine compound according to the present invention may be any one of compounds represented by the following formulas (2) to (45).

The method for producing the condensed arylamine compound according to the present invention is specifically shown in the following Examples.

The present invention also relates to a fuel cell comprising an anode; Cathode; And a layer comprising a condensed arylamine compound represented by the general formula (1), which is interposed between the anode and the cathode.

In this case, the layer containing the condensed arylamine compound is preferably a light emitting layer between the anode and the cathode, and a hole injecting layer, a hole transporting layer, an electron blocking layer, a hole blocking layer, an electron transporting layer, And at least one layer selected from the group consisting of injection layers.

In addition, according to another embodiment of the present invention, the thickness of the light emitting layer is preferably 0.5 nm to 500 nm, and the light emitting layer may further include an anthracene compound represented by the following Chemical Formula 46.

(46)

As a specific example, a hole transport layer (HTL) may be additionally stacked, and an electron transport layer (ETL) may be further stacked between the cathode and the organic emission layer. An electron donor molecule having a low ionization potential is used as the material of the hole transport layer. A diamine, triamine or tetraamine derivative having a basic skeleton of triphenylamine is used as the hole transport layer. It is 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 HIL (Hole Injection Layer) may be additionally deposited 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-methylphenylphenylamino) triphenylamine).

In addition, the electron transport layer used in the organic electroluminescent device according to the present invention can transport electrons supplied from the cathode smoothly to the organic luminescent layer and inhibit the movement of holes which are not bonded in the organic luminescent layer, . The material of the electron transport layer is not particularly limited as long as it is commonly used in the art. For example, oxadiazole derivative PBD, BMD, BND or Alq ₃ can be used.

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 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.

The organic electroluminescent device according to the present invention can be used for a display device, a display device, an element for a single color or a white light, and the like.

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.

Referring to FIG. 1, the organic electroluminescent device of the present invention and its manufacturing method will be described as follows. 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.

According to another embodiment of 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 is formed by a single molecular deposition method or a solution process And the organic electroluminescent device according to the present invention can be used for a display device, a display device, and a monochromatic or white illumination device.

Hereinafter, preferred embodiments of the present invention will be described in order to facilitate understanding of the present invention. However, the following examples are provided only for the purpose of easier understanding of the present invention, and the present invention is not limited thereto.

< Example >

< Synthetic example  1> Preparation of the compound represented by the formula (2)

1) Synthesis of the compound represented by the formula 1-a

The compound represented by the formula (1-a) was synthesized by the following Reaction Scheme 1.

[Reaction Scheme 1]

(1.92mol) of methyl-2-aminobenzoate, 1,300g (4.99mol) of methyl-2-iodobenzoate, 24.4g (0.38mol) of copper and 36.5g (0.19mol) of iodogel were placed in a 500ml round- 2.4 L of diphenylether was added to 610 g (4.4 mol) of potassium carbonate, and the mixture was stirred at 190 캜 for 48 hours. After completion of the reaction, the reaction mixture was filtered, and the residue was purified by column chromatography using hexane and ethyl acetate as eluent. The solid was dried to obtain 375 g (46.6%) of a compound represented by the formula (I-a).

2) Synthesis of the compound represented by the formula 1-b

A compound represented by the formula 1-b was synthesized by the following Reaction Scheme 2.

[Reaction Scheme 2]

In a 5 L round bottom flask, 81 g of magnesium, a small amount of iodine, and 400 ml of ethyl ether were added. 220 ml (3.53 mol) of iodomethane in 2 L of ethyl ether was slowly added dropwise and refluxed for 1 hour. 80 g (19 mmol) of the compound represented by the formula 1-a contained in 2.4 L of toluene was slowly added dropwise and refluxed for 24 hours. After the temperature was lowered, 360 ml of sulfuric acid was slowly dropped in 10 L of ice water. The mixture was extracted twice with methylene chloride and water, and the organic layer was separated by vacuum distillation and column chromatography. To obtain 21.5 g (yield: 26.9%) of the compound represented by the formula (1-b) as a white solid.

3) Synthesis of the compound represented by the formula 1-c

The compound represented by the formula 1-c was synthesized by the following Reaction Scheme 3.

[Reaction Scheme 3]

21.5 g (51 mmol) of the compound represented by the formula (1-b) and 215 ml (85%) of phosphoric acid were placed in a 500 ml round bottom flask. After stirring for 2 hours at room temperature, the mixture was neutralized with aqueous sodium hydroxide (2M), extracted with methylene chloride and water, and the organic layer was distilled off under reduced pressure. Separation of the compound represented by the formula (1-c) using methylene chloride and hexane as a developing solvent gave 9.6 g (yield: 51.3%) of a white solid.

4) Synthesis of the compound represented by the formula (1-d)

The compound represented by the formula 1-d was synthesized by the following Reaction Scheme 4.

[Reaction Scheme 4]

9.6 g (26.3 mmol) of the compound represented by the formula 1-c obtained from the reaction formula 3 was dissolved in 5 L of chloroform, and 4.7 g (26.3 mmol) of N-bromosuccinimide was slowly added to a 10 L round bottom flask And stirred at room temperature for 5 hours. When the reaction was completed, the solution was separated from the organic layer at room temperature, concentrated under reduced pressure, and then subjected to column chromatography using hexane and methylene chloride as eluent to obtain a solid. The resulting solid was dried to obtain 9.2 g (yield: : 78.8%) as a white solid.

5) Synthesis of the compound represented by the formula 1-e

The compound represented by the formula 1-e was synthesized according to the following Reaction Scheme 5.

[Reaction Scheme 5]

9.2 g (20.7 mmol) of the compound represented by the formula 1-d obtained from the reaction formula 4, 6.3 g (24.8 mmol) of bis (pinacolato) diboron and 0.254 g (0.3 mmol) of PdCl ₂ (dppf) were placed in a 500 ml round- , 4.1 g (41.4 mmol) of potassium acetate and 100 ml of toluene were added and refluxed for 12 hours. When the reaction was completed, the temperature was lowered to room temperature and extracted with toluene and water. The organic layer was concentrated under reduced pressure, and then subjected to column chromatography using hexane and methylene chloride as eluent to obtain 7.6 g (yield: 74.7%) of a compound represented by the formula (1-e) as a white solid.

6) Synthesis of Compound Represented by Chemical Formula 2

The compound represented by the general formula (2) was synthesized by the following Reaction Scheme (6).

[Reaction Scheme 6]

(15.5 mmol) of the compound represented by the formula 1-e prepared in the above reaction formula 5, 2.3 g (6.4 mmol) of 1,6-dibromopyrene, 0.1 g of tetrakistriphenylphosphine palladium { Pd (PPh ₃ ) ₄ }, 3.6 g (25.8 mmol) of potassium carbonate, 20 ml of water, 50 ml of toluene and 50 ml of 1,4-dioxane were fed into a flask and the mixture was reacted at 80 ° C. for 24 hours . After the completion of the reaction, the reaction product was separated to remove the aqueous layer. The organic layer was separated, concentrated under reduced pressure, and recrystallized from toluene and hexane to obtain 1.4 g (yield: 23.4%) of a pale yellow solid.

MS (MALDI-TOF): m / z 928 [M] ^&lt; ^{+ &}

< Synthetic example  2> Preparation of the compound represented by the formula (3)

Except that 9,10-dibromoanthracene was used instead of 1,6-dibromopyrene in Synthesis Example 1, 6), 2.8 g (Yield: 53.4 %) Of a pale yellow solid.

MS (MALDI-TOF): m / z 904 [M] ^&lt; ⁺ & gt ^;

< Synthetic example  3> Preparation of the compound represented by the formula (4)

Except that 3,7-dibromophorylene was used instead of 1,6-dibromopyrrene in Synthesis Example 1, 6), 0.7 g (yield: 25.7%) of the compound represented by Formula (4) ) Of a pale yellow solid.

MS (MALDI-TOF): m / z 978 [M] ^&lt; ⁺ & gt ^;

< Synthetic example  4> Preparation of the compound represented by the formula (5)

Except that 2,7-dibromo-9,9'-dimethylfluorene was used instead of 1,6-dibromopyrene in Synthesis Example 1, 6) (Yield: 42.8%) of the title compound as a yellow solid.

MS (MALDI-TOF): m / z 920 [M] ^&lt; ⁺ & gt ^;

< Synthetic example  5> To 28  Preparation of indicated compounds

Except that p-tolyl iodide and 1-phenyl-6-bromopyrene were used instead of 1,6-dibromopyrene in iodomethane and 6) in Synthesis Example 1, 2) To obtain 1.6 g (yield: 13.6%) of a compound represented by the formula (28) as a pale yellow solid.

MS (MALDI-TOF): m / z 1097 [M] ^&lt; ^{+ &}

< Synthetic example  6> Preparation of the compound represented by the formula (29)

Except that p-tolyl iodide and 9-bromo-10- (1-naphthyl) anthracene were used instead of 1,6-dibromoprene in iodomethane and 6) in Synthesis Example 1, 2) Were synthesized in the same manner to give a pale yellow solid of 2.9 g (Yield: 36.1%) of the compound represented by the formula (29).

MS (MALDI-TOF): m / z 1123 [M] ^&lt; ^{+ &}

< Example  1> The organic electroluminescent device  Produce

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the ITO glass was mounted in a vacuum chamber, the base pressure was adjusted to 1 × 10 ^-7 torr. Subsequently, CuPc (800 Å) and α-NPD (300 Å) were sequentially deposited on the ITO, Alq ₃ (350 ANGSTROM), LiF (5 ANGSTROM), and Al (500 ANGSTROM) were deposited in this order to form an organic electroluminescent device. The luminescent characteristics of the organic electroluminescent device were measured at 0.4 mA.

[CuPc]

[? -NPD]

[Alq ₃ ]

< Example  2> The organic electroluminescent device  Produce

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the ITO glass was mounted in a vacuum chamber, the base pressure was adjusted to 1 × 10 ^-7 torr. Subsequently, CuPc (800 Å) and α-NPD (300 Å) were sequentially deposited on the ITO, Alq ₃ (350 ANGSTROM), LiF (5 ANGSTROM) and Al (500 ANGSTROM) were deposited in this order to form an organic electroluminescent device. The luminescent characteristics of the organic electroluminescent device were measured at 0.4 mA.

< Example  3> The organic electroluminescent device  Produce

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the ITO glass was mounted in a vacuum chamber, the base pressure was adjusted to 1 × 10 ^-7 torr. Subsequently, CuPc (800 Å) and α-NPD (300 Å) were sequentially deposited on the ITO, Alq ₃ (350 ANGSTROM), LiF (5 ANGSTROM) and Al (500 ANGSTROM) were deposited in this order to form an organic electroluminescent device. The luminescent characteristics of the organic electroluminescent device were measured at 0.4 mA.

< Example  4> The organic electroluminescent device  Produce

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the ITO glass was mounted in a vacuum chamber, the base pressure was adjusted to 1 × 10 ^-7 torr. Subsequently, CuPc (800 Å) and α-NPD (300 Å) were sequentially deposited on the ITO, Alq ₃ (350 Å), LiF (5 Å) and Al (500 Å) were deposited in this order to form an organic electroluminescent device. The luminescent characteristics of the organic electroluminescent device were measured at 0.4 mA.

< Example  5> The organic electroluminescent device  Produce

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the ITO glass was mounted in a vacuum chamber, the base pressure was adjusted to 1 × 10 ^-7 torr. Subsequently, CuPc (800 Å) and α-NPD (300 Å) were sequentially deposited on the ITO, for manufactured by 5 mixing the compound 3% of the formula 28 by a film forming (250Å), and then _{Alq 3 (350Å), LiF (} 5Å), the order of film formation by the Al (500Å) to prepare an organic electroluminescent device. The luminescent characteristics of the organic electroluminescent device were measured at 0.4 mA.

< Example  6> The organic electroluminescent device  Produce

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the ITO glass was mounted in a vacuum chamber, the base pressure was adjusted to 1 × 10 ^-7 torr. Subsequently, CuPc (800 Å) and α-NPD (300 Å) were sequentially deposited on the ITO, Alq ₃ (350 ANGSTROM), LiF (5 ANGSTROM), and Al (500 ANGSTROM) were deposited in this order to form an organic electroluminescent device. The luminescent characteristics of the organic electroluminescent device were measured at 0.4 mA.

< Comparative Example  1> Compounds containing a compound represented by the formula (47) Organic electroluminescent device

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the ITO glass was mounted in a vacuum chamber, the base pressure was adjusted to 1 × 10 ^-7 torr, and then CuPc (800 Å) and α-NPD (300 Å) were sequentially deposited on the ITO. 47 was mixed to form a film (250 ANGSTROM) Next, Alq ₃ (350 Å), LiF (5 Å) and Al (500 Å) were deposited in this order to produce an organic electroluminescent device.

(47)

< Comparative Example  2 > The compound represented by the formula (48) Organic electroluminescent device

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the ITO glass was mounted in a vacuum chamber, the base pressure was adjusted to 1 × 10 ^-7 torr, and then CuPc (800 Å) and α-NPD (300 Å) were sequentially deposited on the ITO. 48 (3%) were mixed to form a film (250 ANGSTROM) Next, Alq ₃ (350 Å), LiF (5 Å) and Al (500 Å) were deposited in this order to produce an organic electroluminescent device.

(48)

The voltage, current, luminance, color coordinates, and lifetime of the organic electroluminescent device manufactured according to Examples 1 to 6 and Comparative Examples 1 and 2 were measured, and the results are shown in Table 1 below. T80 means the time required for the luminance to be reduced to 80% of the initial luminance.

From the results of Examples 1 to 6, Comparative Examples 1 and 2 and Table 1, the compound represented by the formula (1) according to the present invention has excellent luminescence properties and can be used for display devices, display devices, .

Claims (11)

A condensed arylamine compound represented by the following formula (1)
[Chemical Formula 1]

In Formula 1,
Gt; to R &lt; 6 &gt; are each hydrogen,
Each of A1 to A6 is independently selected from the group consisting of an alkyl group having 1 to 24 carbon atoms and an aryl group having 6 to 24 carbon atoms,
L is a direct bond or a substituted or unsubstituted arylene group having 6 to 24 carbon atoms and a substituted or unsubstituted heteroarylene group having 3 to 24 carbon atoms,
Ar is selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 40 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms,
p is 2. The method according to claim 1,
L and Ar in Formula 1 are each independently substituted with at least one member selected from the group consisting of an alkyl group having 1 to 40 carbon atoms and an aryl group having 6 to 40 carbon atoms. delete delete Anode;
Cathode; And
And a layer containing the condensed arylamine compound according to claim 1 interposed between the anode and the cathode. 6. The method of claim 5,
Wherein the layer containing the condensed arylamine compound is a light emitting layer between the anode and the cathode. The method according to claim 6,
And at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, an electron blocking layer, a hole blocking layer, an electron transporting layer and an electron injecting layer is further interposed between the anode and the cathode. The method according to claim 6,
Wherein the thickness of the light emitting layer is 0.5 nm to 500 nm. The method according to claim 6,
Wherein the light emitting layer further comprises a compound represented by Formula 46:
(46)

8. The method of claim 7,
Wherein at least one layer selected from the group consisting of the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer is formed by a single molecular deposition method or a solution process. 6. The method of claim 5,
Wherein the organic electroluminescent device is used in a display device, a display device, or a device for monochromatic or white illumination.

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