KR101724303B1 - Pyrene compound and organic electroluminescent devices comprising the same - Google Patents

Abstract

The present invention relates to a pyrene-based compound represented by the formula (1) and an organic electroluminescent device including the same, and more particularly to a pyrene-based compound having excellent luminance, color purity and lifetime characteristics and an organic electroluminescent device will be.
(1)

Description

FIELD OF THE INVENTION The present invention relates to a pyrene-based compound and an organic electroluminescent device including the same.

The present invention relates to a pyrene-based compound and an organic electroluminescent device including the same, and more particularly, to a pyrene-based compound having excellent luminance, color purity, and lifetime characteristics, and an organic electroluminescent device including the same.

In recent years, the demand for a flat display device having a small space occupancy has been increased 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, And a back light is necessarily required. On the contrary, an organic light emitting diode (OLED), which is a new flat display device, is a display using a self-luminescent phenomenon, has a large viewing angle, is thinner and thinner than a liquid crystal display, And in recent years, application to a full-color display or illumination is expected. For this purpose, there is a growing need for high luminance, high efficiency and high color purity blue light emitting materials.

As a blue light emitting material, US Pat. No. 7053255 discloses a blue light emitting compound having a diphenyl anthracene structure and an aryl group substituted at the terminal thereof, and an organic electroluminescent device using the blue light emitting compound. However, there was.

On the other hand, US Pat. No. 7233019 and Korean Patent Laid-Open Publication No. 2006-0006760 disclose an organic electroluminescent device using a substituted pyrene compound. However, since the color purity of blue is low, a deep blue It is difficult to realize a full-color full-color display.

SUMMARY OF THE INVENTION The present invention provides a pyrene-based compound having excellent brightness and color purity of blue and long life.

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

In order to accomplish the first technical object, the present invention provides a pyrene-based compound represented by the following formula (1).

(1)

In this formula,

A is selected from a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms,

B and C represent a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 24 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 24 carbon atoms, a substituted or unsubstituted alkoxy group, A substituted or unsubstituted aryloxy group, 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, boron, a cyano group, a halogen group, a trifluoromethyl group , Deuterium, and hydrogen,

m and n are integers of 1 to 4,

x is an integer of 1 to 4, y is an integer of 1 to 7,

When B or C is 2 or more, they may be the same or different from each other.

According to one embodiment of the present invention, the substituent of A, B or C is a substituted or unsubstituted C6-C24 aryl group, a substituted or unsubstituted C2-C24 heteroaryl group, a substituted or unsubstituted A substituted or unsubstituted C1 to C24 alkyl group, 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 A substituted or unsubstituted aryloxy group having 6 to 24 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, Hydrogen, deuterium, and hydrogen,

And B is preferably selected from the group consisting of a cyano group, a halogen group, and a trifluoromethyl group.

According to another embodiment of the present invention, A is selected from a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, and B is a cyano group , A halogen group, a trifluoromethyl group,

x is an integer of 1 to 4, and when x is 2 or more, each B may be the same or different from each other, and y is preferably a compound.

According to another embodiment of the present invention, it may be any one compound selected from the group consisting of BD1 to BD68 described in the following examples.

In order to solve the second technical problem,

The present invention relates to an anode; Cathode; And a layer including a pyrene compound of the formula (1) interposed between the anode and the cathode.

The layer containing the pyrene 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 an electron injecting layer are provided between the anode and the cathode Lt; RTI ID = 0.0 > a < / RTI >

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 at least one compound selected from compounds represented by the following formulas BH1 to BH39 can do.

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.

As described above, the organic electroluminescent device comprising the compound of formula (1) according to the present invention in the organic material layer is excellent in blue brightness, color purity, and lifetime characteristics, and thus can be used for display and illumination.

1 is a schematic view showing an organic electroluminescent device according to an embodiment of the present invention.
FIG. 2 is a graph showing changes in relative brightness over time of the organic electroluminescent device according to Examples 1 to 4 and Comparative Example 1. FIG.
FIG. 3 is a graph showing a change in relative luminance over time of the organic electroluminescent device according to Examples 5 to 8 and Comparative Example 2. FIG.
4 is a graph showing the current efficiency according to the luminance of the organic electroluminescent device according to Examples 1 to 4 and Comparative Example 1. FIG.
5 is a graph showing the current efficiency according to the luminance of the organic electroluminescent device according to Examples 1 to 4 and Comparative Example 2. FIG.

Hereinafter, the present invention will be described in more detail with reference to Examples.

The pyrene compound according to the present invention is characterized by being represented by the following formula.

(1)

In this formula,

A is selected from a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms,

B and C represent a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 24 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 24 carbon atoms, a substituted or unsubstituted alkoxy group, A substituted or unsubstituted aryloxy group, 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, boron, deuterium, and hydrogen ,

m and n are integers of 1 to 4,

x is an integer of 1 to 4, y is an integer of 1 to 7,

When B or C is 2 or more, they may be the same or different from each other.

According to one embodiment of the present invention, the substituent of A, B or C is a substituted or unsubstituted C6-C24 aryl group, a substituted or unsubstituted C2-C24 heteroaryl group, a substituted or unsubstituted A substituted or unsubstituted C1 to C24 alkyl group, 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 A substituted or unsubstituted aryloxy group having 6 to 24 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, Hydrogen, deuterium, and hydrogen,

And B is preferably selected from the group consisting of a cyano group, a halogen group, and a trifluoromethyl group.

According to another embodiment of the present invention, A is selected from a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms,

B is selected from the group consisting of a cyano group, a halogen group, a trifluoromethyl group,

x is an integer of 1 to 4, and when x is 2 or more, each B may be the same or different from each other, and y is preferably a compound.

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 " Substituted or unsubstituted amino group (-NH2, -NH (R), -N (R ') (R "), R' and R" each independently represent an alkyl group having 1 to 24 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, 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 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.

Specific examples of the cycloalkyl group used as the substituent in the compound of the present invention include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, and the like, ≪ / RTI >

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, tetrahydronaphthyl group and the like, which may be substituted with the same substituents as those in the case 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, or 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.

Specifically, the pyrene compound according to the present invention may be any one of the following compounds represented by BD1 to BD68.

(BD1) (BD2) (BD3) (BD4)

(BD5) (BD6) (BD7) (BD8)

(BD9) (BD10) (BD11) (BD12)

(BD13) (BD14) (BD15) (BD16)

(BD17) (BD18) (BD19) (BD20)

(BD21) (BD22) (BD23) (BD24)

(BD25) (BD26) (BD27) (BD28)

(BD29) (BD30) (BD31) (BD32)

(BD33) (BD34) (BD35) (BD36)

(BD37) (BD38) (BD39) (BD40)

(BD41) (BD42) (BD43) (BD44)

(BD45) (BD46) (BD47) (BD48)

(BD49) (BD50) (BD51) (BD52)

(BD53) (BD54) (BD55) (BD56)

(BD57) (BD58) (BD59) (BD60)

(BD61) (BD62) (BD63) (BD64)

(BD65) (BD66) (BD67) (BD68)

The organic electroluminescent device according to the present invention includes an anode; Cathode; And a layer containing a pyrene compound according to the above formula (1) interposed between the anode and the cathode.

At this time, it is preferable that the pyrene compound according to an embodiment of the present invention is included in the light emitting layer between the anode and the cathode, and a hole injecting layer, a hole transporting layer, a hole blocking layer, a light emitting layer, An electron injection layer, and an electron blocking layer.

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 at least one compound selected from compounds represented by the following formulas BH1 to BH39 can do.

(BH01) (BH02) (BH03) (BH04)

(BH05) (BH06) (BH07) (BH08)

(BH09) (BH10) (BH11) (BH12)

(BH13) (BH14) (BH15) (BH16)

(BH17) (BH18) (BH19) (BH20)

(BH21) (BH22) (BH23) (BH24)

(BH25) (BH26) (BH27) (BH28)

(BH29) (BH30) (BH31) (BH32)

(BH33) (BH34) (BH35) (BH36)

(BH37) (BH38) (BH39)

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 material of 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, CuPc or starburst type amines such as TCTA and m-MTDATA may be used.

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 for 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.

On the other hand, 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. 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 synthesis example of 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 light emitting diode according to the present invention includes an anode 20, a hole transporting layer 40, an organic light emitting layer 50, an electron transporting 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 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), and zinc oxide (ZnO), 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. When the holes pass through the organic light emitting layer and enter the cathode, the lifetime and efficiency of the hole blocking layer are reduced. Therefore, the hole blocking layer plays a role of preventing such a problem by using a material having a very low HOMO level.

The hole blocking material used herein is not particularly limited, but it is required to have an ionization potential higher than that of a light emitting compound while having an 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, the present invention will be described in more detail with reference to the following Synthesis Examples, but the following Synthesis Examples are for illustrative purposes only and are not intended to limit the present invention.

Synthesis Example 1. Synthesis of Compound BD1

Synthesis Example 1- (1): Synthesis of 3-bromo-5- (naphthalen-1-yl) benzonitrile

To a round bottom flask was added 3,5-dibromo-benzonitrile 20.0 g (77 mmol) and 1-naphthalene boronic acid 13.2 g (77 mmol), tetrakis (triphenylphosphine) palladium _{{Pd (PPh 3) 4}} 1.8 g ( 2 mmol), potassium carbonate (21.2 g, 153 mmol), water (30 mL), toluene (100 mL) and tetrahydrofuran (100 mL) and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction product was separated, and the organic layer was concentrated under reduced pressure. The organic layer was recrystallized from hexane and dried to obtain 13.1 g of a white solid having a yield of 55.5%.

Synthesis Example 1- (2): Synthesis of 3- (naphthalen-1-yl) -5- (phenylamino) benzonitrile

13.1 g (43 mmol) of 3-bromo-5- (naphthalen-1-yl) benzonitrile prepared in Example 1- (2), 3.6 g (43 mmol) of aniline, 0.14 g (0.6 mmol) of 2,2-bisdiphenylphosphino-1,1'-binaphthyl, 8.2 g (0.6 mmol) of sodium tertiary butoxide and 130 ml of toluene were added, Lt; / RTI > After the temperature was lowered, the organic layer was concentrated and separated by column chromatography. Recrystallization from dichloromethane and hexane followed by filtration and drying gave 7.9 g of a white solid with a yield of 58%.

Synthesis Example 1- (3): Synthesis of BD1

7.9 g (25 mmol) of 3- (naphthalene-1-yl) -5- (phenylamino) benzonitrile prepared in Example 1- (2), 3.7 g (10 mmol) of dibromo- 0.09 g (0.4 mmol) of palladium acetate {Pd (OAc) ₂ }, 3.95 g (41 mmol) of sodium tertiary butoxide, 0.08 g (0.4 mmol) of triturated butylphosphine and 80 ml of toluene, Lt; / RTI > for 2 hours. When the reaction was terminated, the temperature was lowered to room temperature. When crystals were formed, the crystals were separated by filtration and then column chromatography. And recrystallized with toluene and ethanol. The resulting solid was filtered and dried to obtain 1.8 g (yield: 19.7%) of pale yellow solid.

MS (MALDI-TOF): m / z 838 [M] ^< ^{+ &}

Synthesis Example 2. Synthesis of Compound BD3

Synthesis was conducted in the same manner as in Synthesis Example 1- (1), except that 2-naphthalene boronic acid was used instead of 1-naphthalene boronic acid in place of aniline in 1- (2), and the yield was 63.1% A yellow solid was obtained.

MS (MALDI-TOF): m / z 866 [M] ^< ^{+ &}

Synthesis Example 3. Synthesis of Compound BD21

Except that 2-fluoro-4- (naphthalen-2-yl) aniline was used instead of bromobenzene and aniline in place of 3-bromo-5- (naphthalen-1-yl) benzonitrile in Synthesis Example 1- (2) , The title compound was synthesized in the same manner as in Example 1 to give a pale yellow solid having a yield of 4.1 g (51%).

MS (MALDI-TOF): m / z 824 [M] ^< ⁺ & gt ^;

Synthesis Example 4: Synthesis of compound BD30

Bromo-3-fluoro-5- (naphthalen-1-yl) benzene instead of 3-bromo-5- (naphthalen-1-yl) benzonitrile in Synthesis Example 1- (2) , 2.7 g of a pale yellow solid with a yield of 28% was obtained.

MS (MALDI-TOF): m / z 852 [M] ^< ^{+ &}

Synthesis Example 5. Synthesis of Compound BD45

Bromo-3-fluoro-5- (naphthalen-2-yl) benzene instead of 3-bromo-5- (naphthalen-1-yl) benzonitrile in Synthesis Example 1- (2) -Butylaniline, the title compound was obtained in the form of a pale yellow solid having a yield of 4.1 g (38%).

MS (MALDI-TOF): m / z 936 [M] ^< ⁺ & gt ^;

Synthesis Example 6. Synthesis of Compound BD53

(3-trifluoromethyl-5- (naphthalen-1-yl) aniline was used instead of bromobenzene and aniline in place of 3-bromo-5- (naphthalen-1-yl) benzonitrile in Synthesis Example 1- , The title compound was synthesized by the same method to obtain a pale yellow solid having a yield of 47% at 3.9 g.

MS (MALDI-TOF): m / z 924 [M] ^< ^{+ &}

Synthesis Example 7: Synthesis of compound BD54

3-trifluoromethyl-5- (naphthalen-1-yl) aniline was used instead of 4-bromotoluene and aniline in place of 3-bromo-5- (naphthalen-1-yl) benzonitrile in Synthesis Example 1- (2) Was synthesized in the same way to obtain 3.3 g (41%) of a pale yellow solid.

MS (MALDI-TOF): m / z 1036 [M] ^< ^{+ &}

Synthesis Example 8. Synthesis of Compound BD35

Bromo-3-fluoro-5- (naphthalen-1-yl) benzene instead of 3-bromo-5- (naphthalen-1-yl) benzonitrile in Synthesis Example 1- (2) Benzonitrile, the same procedure was repeated to obtain 2.3 g of a pale yellow solid with a yield of 22%.

MS (MALDI-TOF): m / z 874 [M] ^< ^{+ &}

Examples 1 to 8: Preparation of 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. Subsequently, CuPc (800 Å) and α-NPD (300 Å) (350 Å), LiF (5 Å), and Al (500 Å) in this order to form an organic electroluminescent device. The luminescent characteristics of the organic electroluminescent device were measured at 0.4 mA.

ET01

In Examples 2 to 8, an organic electroluminescent device was fabricated in the same manner as described in [Table 1], except that BD1 was used. The luminescent characteristics of the organic electroluminescent device were measured at 0.4 mA.

Comparative Examples 1 to 2

An organic electroluminescent device was fabricated in the same manner as in Example 1 except that BD69 and BD70 were used instead of BD1, and the luminescent characteristics of the organic electroluminescent device were measured at 0.4 mA. The structure of the BD 69 and the BD 70 is as follows.

(BD69) (BD70)

The voltage, current, luminance, color coordinates, and lifetime of the organic electroluminescent device manufactured according to Examples 1 to 8 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.

division Voltage (V) Current density
(MA / cm2) External quantum efficiency Luminance
(cd / m 2) CIEx CIEy T80 Example 1 4.3 10 6.3 522 0.140 0.094 105 Example 2 4.2 10 6.9 663 0.133 0.119 210 Example 3 4.1 10 6.7 579 0.135 0.102 120 Example 4 4.1 10 7.1 671 0.131 0.117 195 Example 5 4.1 10 7.4 819 0.129 0.145 45 Example 6 4.0 10 7.2 627 0.137 0.099 245 Example 7 4.3 10 6.9 710 0.133 0.131 100 Example 8 4.0 10 6.1 453 0.140 0.079 145 Comparative Example 1 4.5 10 4.0 421 0.133 0.138 95 Comparative Example 2 4.6 10 4.2 452 0.139 0.135 35

As can be seen from the results of the above Table 1, the organic electroluminescent device according to the present invention exhibits superior luminance and color purity than conventional blue luminescent compounds and has a long life.

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

Claims (12)

A pyrene-based derivative represented by the following formula (1)
(1)

In this formula,
A is a substituted or unsubstituted aryl group having 6 to 24 carbon atoms,
B and C are each independently selected from the group consisting of hydrogen, a cyano group, a halogen group, a trifluoromethyl group and an alkyl group having 1 to 6 carbon atoms (except when B and C are both hydrogen)
When A is a substituted aryl group, A is an aryl group substituted with at least one member selected from deuterium, cyano, alkyl group having 1 to 6 carbon atoms, alkoxy group having 1 to 6 carbon atoms, and aryl group having 6 to 12 carbon atoms Or a substituted heteroaryl group,
m and n are integers of 1 to 2, x is an integer of 1 to 4, y is an integer of 1 to 4 (provided that when x is 2 or more, each B may be the same or different and y is 0)
When B or C is 2 or more, each is the same or different from each other. delete delete delete The method according to claim 1,
Wherein the pyrene-based derivative represented by Formula 1 is any one selected from the group consisting of the following compounds represented by BD1 to BD68:
(BD1) (BD2) (BD3) (BD4)

(BD5) (BD6) (BD7) (BD8)

(BD9) (BD10) (BD11) (BD12)

(BD13) (BD14) (BD15) (BD16)

(BD17) (BD18) (BD19) (BD20)

(BD21) (BD22) (BD23) (BD24)

(BD25) (BD26) (BD27) (BD28)

(BD29) (BD30) (BD31) (BD32)

(BD33) (BD34) (BD35) (BD36)

(BD37) (BD38) (BD39) (BD40)

(BD41) (BD42) (BD43) (BD44)

(BD45) (BD46) (BD47) (BD48)

(BD49) (BD50) (BD51) (BD52)

(BD53) (BD54) (BD55) (BD56)

(BD57) (BD58) (BD59) (BD60)

(BD61) (BD62) (BD63) (BD64)

(BD65) (BD66) (BD67) (BD68)

Anode;
Cathode; And
The organic electroluminescent device according to claim 1, wherein the layer comprises a pyrene-based derivative interposed between the anode and the cathode. The method according to claim 6,
Wherein the layer containing the pyrene-based derivative is a light emitting layer between the anode and the cathode. 8. The method of claim 7,
Wherein 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. 8. The method of claim 7,
Wherein the thickness of the light emitting layer is 0.5 nm to 500 nm. 8. The method of claim 7,
Wherein the light emitting layer further comprises at least one compound selected from compounds represented by the following formulas BH1 to BH39.
(BH01) (BH02) (BH03) (BH04)

(BH05) (BH06) (BH07) (BH08)

(BH09) (BH10) (BH11) (BH12)

(BH13) (BH14) (BH15) (BH16)

(BH17) (BH18) (BH19) (BH20)

(BH21) (BH22) (BH23) (BH24)

(BH25) (BH26) (BH27) (BH28)

(BH29) (BH30) (BH31) (BH32)

(BH33) (BH34) (BH35) (BH36)

(BH37) (BH38) (BH39)

9. The method of claim 8,
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. The method according to claim 6,
Wherein the organic electroluminescent device is used in one of a display device, a display device, and a monochromatic or white illumination device.

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