KR101661591B1 - triazolyl substituted pyrene derivatives and organic electroluminescent device including the same - Google Patents

Abstract

[상기 화학식 1에서 각 치환기들의 정의는 발명의 상세한 설명에서 정의한 바와 같다.]There is provided a pyrene derivative substituted with a triazole group represented by the following formula (1).
[Chemical Formula 1]

[Wherein the definition of each substituent in Formula 1 is as defined in the description of the invention]

Description

(Triazole-substituted pyrene derivatives and organic electroluminescent devices including the same)

TECHNICAL FIELD The present invention relates to a pyrene derivative substituted with a triazole group and an organic electroluminescent device including the same. More particularly, the present invention relates to an organic electroluminescent device having high luminous efficiency, ≪ / RTI >

The organic light emitting diode (OLED) display is composed of a multilayer thin film, and exciters are formed by electrons and holes injected through two thin film electrodes, and display using a phenomenon in which light of a specific wavelength is generated from the formed excitons.

This OLED was first attempted in 1963 by Pope et al. To study the carrier injection type electroluminescence (EL) using an anthracene aromatic hydrocarbon single crystal of an organic material. From these studies, it was found that charge injection, recombination, , Basic mechanisms such as luminescence, electroluminescence characteristics, and so on.

In addition, in 1987, Tang and Van Slyke reported a high efficiency using a multilayer thin film structure of an organic light emitting diode (OLED) [Tang, C. W., Van Slyke, S. A. Appl. Phys. Lett. 51, 913 (1987)], OLEDs have been widely studied for their excellent potential as a next generation display, as well as for their potential to be used for LCD backlighting and illumination [Kido, J., Kimura, M., and Nagai, K., Science 267,1332 (1995)]. Especially, in order to increase the luminous efficiency, various approaches such as structural change and material development have been performed [Sun, S., Forrest, S. R., Appl. Phys. Lett. 91, 263503 (2007) / Ken-Tsung Wong, Org. Lett., 7, 2005, 5361-5364].

In the organic electroluminescent device, the light emitting material is largely divided into fluorescence and phosphorescence. The method of forming the light emitting layer includes a method of doping a fluorescent host with phosphorescence, a method of doping a fluorescent dopant into a fluorescent host, and a method of implementing a long wavelength using a dopant Method.

In the case of the blue material in terms of the light emitting material, the blue material system (DPVBi) of Idemitsu-Gosan, the anthracene (9,10-di (2-naphthyl) anthracene of KODAK, tetra (t-butyl) perlyene) system.

Common requirements that light emitting materials must have in a display include color coordinates, low driving voltage of the device, high luminous efficiency, and high glass transition temperature.

However, the blue material has not reached the level satisfying the demand of the display industry, which is progressively increasing in size. Therefore, a lot of research and development on blue materials is required, and research on organic EL materials is continuously required.

Korean Patent Publication No. 2010-0075101

The object of the present invention is to provide a novel pyrene derivative excellent in luminous efficiency and durability as compared with conventional materials, and furthermore, the above-mentioned pyrene derivative is contained in an organic film to lower the driving voltage of the device, And to provide an electroluminescent device.

[상기 화학식 1에서,
Ar₁은

또는

이며,
(X는 각각 독립적으로 CH 또는 N이고, Z는 O 또는 S임),
L₁은

또는

이다.]According to one aspect of the present invention, there is provided a pyrene derivative substituted with a triazole group represented by the following formula (1).
[Chemical Formula 1]

[In the above formula (1)
Ar ₁ is

or

Lt;
(X is each independently CH or N and Z is O or S)
L ₁ is

or

to be.]

delete

delete

delete

delete

delete

delete

delete

delete

delete

delete

According to another aspect of the present invention, there is provided an organic electroluminescent device comprising the pyrene derivative substituted with the triazole group.

According to another aspect of the present invention, there is provided an organic electroluminescent device comprising a first electrode, a second electrode, and at least one organic film disposed between the electrodes, wherein the organic film includes an organic field including a pyrene derivative substituted with the triazole group A light emitting element is provided.

The triazole-substituted pyrene derivative according to an embodiment of the present invention may be included in an organic layer of an organic electroluminescence device, preferably a hole injection layer or a hole transport layer, thereby lowering the driving voltage of the device and improving the luminous efficiency . Further, the lifetime of the organic electroluminescent device can be improved by the thermal stability of the pyrene derivative substituted with the triazole group of the present invention.

1 is a schematic cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
Fig. 2 is an EL (electroluminescence) spectrum obtained by measuring an OLED device manufactured for the compound (3-4) of the present invention.
3 shows the results of LC-MS analysis of the compound (3-4) of the present invention.

As used herein, the term "alkyl" includes straight chain, branched chain hydrocarbon groups or combinations thereof and includes alkenyl or alkynyl.

The term "heteroalkyl ", unless otherwise specified, means a stable straight or branched chain hydrocarbon group consisting of at least one carbon atom and at least one heteroatom selected from the group consisting of O, N, P, Si and S , The N, P and S atoms can optionally be oxidized and the N heteroatoms can be quaternized as the case may be.

The terms "cycloalkyl" and "heterocycloalkyl" refer to a cyclic version of "alkyl" and "heteroalkyl ", respectively,

The term "aryl" means a polyunsaturated aromatic hydrocarbon substituent, which may be a single ring or a multiple ring (one to three rings) fused or covalently bonded unless otherwise specified.

The aryl includes a single or fused ring system, suitably containing from 4 to 7, preferably 5 or 6, ring atoms in each ring. Also included are structures in which one or more aryls are attached through a chemical bond. Specific examples of the aryl include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, It is not limited.

The term "heteroaryl" means an aryl group (or a ring) comprising one to four heteroatoms selected from N, O and S (in each ring in the case of multiple rings) and N and S atoms Are optionally oxidized and the N atom (s) are quaternized, as the case may be. Heteroaryl groups can be attached to the remainder of the molecule through carbon or heteroatoms.

The heteroaryl includes 5- to 6-membered monocyclic heteroaryl and polycyclic heteroaryl fused with one or more benzene rings, and may be partially saturated. Also included are structures in which one or more heteroaryls are attached via a chemical bond. The heteroaryl groups include divalent aryl groups in which the heteroatoms in the ring are oxidized or trisubstituted to form, for example, an N-oxide or a quaternary salt.

Specific examples of the heteroaryl include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, Monocyclic heteroaryl such as pyridyl, pyridyl, pyrazinyl, pyridazinyl and the like, benzofuranyl, benzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl , Benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, (Such as pyridyl N-oxide, quinolyl N-oxide), quaternary salts thereof, and the like, but are not limited thereto. But is not limited thereto.

The term "aralkyl" refers to an alkyl group substituted with aryl, wherein the alkyl and aryl moieties are independently optionally substituted.

The term "heteroaralkyl" refers to an alkyl group substituted with heteroaryl, wherein the alkyl and heteroaryl moieties are independently optionally substituted.

"Substituted" in the expression " substituted or unsubstituted ", as used herein, means that at least one hydrogen atom in the hydrocarbon is each independently replaced with the same or different substituents. Useful substituents include, but are not limited to:

Such substituents include, but are not limited to, -F; -Cl; -Br; -CN; -NO ₂ ; -OH; A C ₁ -C ₂₀ alkyl group which is unsubstituted or substituted by -F, -Cl, -Br, -CN, -NO ₂ or -OH; A C ₁ -C ₂₀ alkoxy group unsubstituted or substituted by -F, -Cl, -Br, -CN, -NO ₂ or -OH; C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, -F, -Cl, -Br, -CN , -NO _2, or substituted by -OH or unsubstituted C ₆ ~ C ₃₀ aryl group; C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, -F, -Cl, -Br, -CN , -NO 2 or -OH-substituted or unsubstituted C ₆ ~ C ₃₀ heteroaryl group, a; C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, -F, -Cl, -Br, -CN , -NO 2 , or substituted by -OH or unsubstituted C ₅ ~ C ₂₀ cycloalkyl group; C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, -F, -Cl, -Br, -CN , -NO 2 , or substituted or unsubstituted by -OH unsubstituted C ₅ ~ C ₃₀ heterocycloalkyl group; And a group represented by -N (G ₁ ) (G ₂ ). Wherein G ₁ and G ₂ are each independently selected from the group consisting of hydrogen; A C ₁ -C ₁₀ alkyl group; Or a C ₆ -C ₃₀ aryl group substituted or unsubstituted with a C ₁ -C ₁₀ alkyl group.

Among the terms indicating the number of carbon atoms, for example, "C _n to C ₃₀ " means that the carbon number may have n to 30 carbon atoms.

Hereinafter, the present invention will be described in detail.

[상기 화학식 1에서,
Ar₁은

또는

이며,
(X는 각각 독립적으로 CH 또는 N이고, Z는 O 또는 S임),
L₁은

또는

이다.]The triazole-substituted pyrene derivative according to an embodiment of the present invention may be represented by the following formula (1).
[Chemical Formula 1]

[In the above formula (1)
Ar ₁ is

or

Lt;
(X is each independently CH or N and Z is O or S)
L ₁ is

or

to be.]

delete

delete

delete

delete

delete

delete

delete

delete

delete

Specific examples of the triazole-substituted pyrene derivative represented by the formula (1) according to an embodiment of the present invention may be represented by the following formula (2), and examples of various structures other than the triazine- The solubilization may be included in the substituted pyrene derivative.

(2)

In Formula 2, X and Z are the same as defined in Formula 1 above.

More specifically, the compound represented by Formula 1 may be selected from among the compounds represented by Formula 3, but is not limited thereto.

delete

(3)

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delete

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The pyrene derivative represented by the above formula (1) can be synthesized using a known organic synthesis method. The method for synthesizing the pyrene derivative can be easily recognized by those skilled in the art with reference to the following production examples.

Also, according to the present invention, there is provided an organic electroluminescent device comprising the pyrene derivative represented by the above formula (1).

The pyrene derivative of Formula 1 is useful as a light emitting layer material, preferably a blue fluorescent dopant material, and can be used as a host or dopant material for green or red phosphorescent devices, or as a hole injecting or hole transporting material.

The organic electroluminescent device according to the present invention includes a first electrode, a second electrode, and at least one organic film disposed between the electrodes. The organic film contains at least one pyrene derivative represented by the above formula (1).

The organic layer includes a hole injecting layer, a hole transporting layer, a functional layer having both a hole injecting function and a hole transporting function, a buffer layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transporting layer, And at least one layer selected from the group consisting of functional layers having at the same time.

For example, the pyrene derivative may be contained in at least one selected from the group consisting of a light emitting layer, an organic layer disposed between the anode and the light emitting layer, and an organic layer disposed between the light emitting layer and the cathode. Preferably, the pyrene derivative may be contained in at least one layer selected from the group consisting of a light emitting layer, a hole injecting layer, a hole transporting layer, and a functional layer having both a hole injecting function and a hole transporting function. The pyrene derivative may be included in the organic film as a single substance or a combination of different substances. Alternatively, the pyrene derivative may be used in combination with a conventionally known compound such as a hole transport layer and a hole injection layer.

The organic electroluminescent device according to the present invention can be applied to an organic electroluminescent device including a positive electrode / a light emitting layer / a cathode, a positive electrode / a hole injecting layer / a light emitting layer / a negative electrode, an anode / a hole injecting layer / a hole transporting layer / a light emitting layer / an electron transporting layer / / Light emitting layer / electron transporting layer / electron injecting layer / cathode structure. Alternatively, the organic electroluminescent device may include a functional layer / a light emitting layer / an electron transporting layer / a cathode having both an anode / hole injecting function and a hole transporting function, a functional layer / a light emitting layer / an electron transporting layer / Electron injecting layer / cathode structure, but the present invention is not limited thereto.

1 is a schematic cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.

The organic electroluminescent device may be manufactured using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. For example, an anode is formed by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate, and an organic film including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer is formed thereon And then depositing a material which can be used as a cathode thereon. In addition to such a method, an organic electroluminescent device may be formed by sequentially depositing a cathode material, an organic film, and a cathode material on a substrate.

Meanwhile, the organic layer may be prepared by a wet process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer by using various polymer materials instead of a vapor deposition method.

The organic electroluminescent device according to the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.

Hereinafter, the present invention will be described in more detail with reference to the following examples. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the present invention.

Example  1: Synthesis of compound (3-1)

The synthesis route of the compound (3-1) is shown below.

(Synthesis of Intermediate (1)

14.03 g (0.039 mol) of 1,6-dibromopyrene, 3,4-diphenyl-5- (4- (4,4,5,5,5- Tetramethyl-1,3,2-dioxabororan-2-yl) phenyl) -4H-1,2,4-triazole (3,4-diphenyl-5- (4- , 11.0 g (0.026 mol) of Pd (dppf) Cl _{2 and} 0.64 g (0.78 mmol) of Pd (dppf) Cl _{2 were added to a} solution of 5-tetramethyl-1,3,2-dioxaborolan- K ₂ CO ₃ 6.10 g (0.044 mol) of triethylamine were added to THF / H ₂ O (10 / 1,550 mL) and the reaction temperature was stirred at 90 ° C for 2 hours under nitrogen. After lowering the temperature to room temperature, stir for one hour. After the reaction was completed, the solvent was removed by vacuum distillation. This compound was purified to obtain intermediate (1), and the yield was 5.8 g (yield: 38%).

(Synthesis of final compound)

2 intermediate to obtain 100ml flask (1) 0.3 g (0.52 mol ) and diphenylamine (diphenylamine) 0.10 g (0.61 mmol ), Pd (dba) 2 8.4 mg (0.015 mmol), P (t-Bu) 3 0.024 ml _{(0.052 mmol), Cs 2 CO} 3 504 mg (1.54 mmol) was added to toluene (toluene) and refluxed under nitrogen for 18 hours. After the reaction was completed, the solvent was removed by vacuum distillation. This compound was subjected to column chromatography (Column Chromatography) to give compound (3-1), and the yield was 0.09 g (yield: 26%).

Example  2: Synthesis of compound (3-2)

The synthesis route of the compound (3-2) is shown below.

(Synthesis of final compound)

In two 100ml flasks intermediate (1) 0.3 g (0.52 mol ) and 4-aminobenzonitrile (4-phenylaminobenzonitrile) 0.12 g ( 0.61 mmol), Pd (dba) 2 8.4 mg (0.015 mmol), P (t- _{Bu) 3 0.024 ml (0.052 mmol} ), Cs 2 CO 3 504 mg (1.54 mmol) of triethylamine are added to toluene under nitrogen and refluxed for 18 hours. After the reaction was completed, the solvent was removed by vacuum distillation. This compound was subjected to column chromatography to obtain compound (3-2), and the yield was 0.06 g (yield: 10%).

Example  3: Synthesis of compound (3-3)

The synthesis route of the compound (3-3) is shown below.

(Synthesis of final compound)

In a two-necked 100 ml flask, 0.3 g (0.52 mol) of Intermediate (1) and 0.5 g of 5- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- ) -5H-pyrido [3,2-b] indole (5- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-b] indole and 504 mg (1.54 mmol) of Cs ₂ CO _{3 were added to a} solution of 0.28 g (0.75 mmol), Pd (PPh ₃ ) ₄ 18 mg (0.015 mmol) TBAB 5 mg (0.015 mmol) After the reaction was completed, the solvent was removed by distillation under reduced pressure. This compound was subjected to column chromatography to obtain the compound (3-3), and the yield was 0.16 g (Yield: 42%).

Example  4: Synthesis of compound (3-4)

The synthesis route of the compound (3-4) is shown below.

(Synthesis of final compound)

In a two-necked 100 ml flask, 0.3 g (0.52 mol) of Intermediate (1) and 0.5 g of 5- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 5H-pyrido [3,2-b] indole (5- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-b] indole and Pd (PPh ₃ ) ₄ 18 mg (0.015 mmol), TBAB 5 mg (0.015 mmol) and Cs ₂ CO ₃ 504 mg (1.54 mmol) were dissolved in toluene After the reaction was completed, the solvent was removed by distillation under reduced pressure. This compound was subjected to column chromatography to obtain the compound (3-4), and the yield was 0.10 g (yield: 26%).

Example  5: Synthesis of compound (3-5)

The synthesis route of the compound (3-5) is shown below.

(Synthesis of final compound)

In a two-necked 100 ml flask, 0.3 g (0.52 mol) of Intermediate (1) and 9- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- ) -9H-carbazole (0.23 g, 0.61 mmol), Pd < RTI ID = 0.0 > _{(PPh 3) 4 18 mg (} 0.015 mmol), TBAB 5 mg (0.015 mmol), Cs 2 CO 3 504 mg (1.54 mmol) was added to toluene under nitrogen and refluxed for 30 hours. After the reaction was completed, the solvent was removed by vacuum distillation. This compound was subjected to column chromatography to obtain compound (3-5), and the yield was 0.09 g (yield: 23%).

Example  6: Synthesis of compound (3-6)

The synthesis route of the compound (3-6) is shown below.

(Synthesis of final compound)

In a two-necked 100 ml flask, 0.3 g (0.52 mol) of intermediate (1) and 9- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- ) -9H-carbazole (0.23 g, 0.61 mmol), Pd _{(PPh 3) 4 18 mg (} 0.015 mmol), TBAB 5 mg (0.015 mmol), Cs 2 CO 3 504 mg (1.54 mmol) was added to toluene under nitrogen and refluxed for 30 hours. After the reaction was completed, the solvent was removed by vacuum distillation. Compound (3-6) was obtained using this compound by column chromatography, and the yield was 0.10 g (yield: 38%).

Example  7: Synthesis of compound (3-7)

The synthesis route of the compound (3-7) is shown below.

(Synthesis of final compound)

In a two-necked 100 ml flask, 0.3 g (0.52 mol) of intermediate (1) and 9- (6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 3-yl) -9H-carbazole (9,6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl) pyridin- (0.62 mmol), Pd (PPh 3) 4 18 mg (0.015 mmol), TBAB 5 mg (0.015 mmol), Cs 2 CO 3 504 mg (1.54 mmol) was added to toluene under nitrogen and refluxed for 30 hours. After the reaction was completed, the solvent was removed by vacuum distillation. The compound (3-7) was obtained by column chromatography, and the yield was 0.27 g (yield: 70%).

Example  8: Synthesis of compound (3-8)

The synthesis route of the compound (3-8) is shown below.

(Synthesis of final compound)

In a two-necked 100 ml flask, 0.3 g (0.52 mol) of Intermediate (1) and 9- (5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 3-yl) -9H-carbazole (9-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridin- 184 mg (0.015 mmol) of Pd (PPh ₃ ) ₄ , 5 mg (0.015 mmol) of TBAB and 504 mg (1.54 mmol) of Cs ₂ CO ₃ were added to toluene under nitrogen, Reflux. After the reaction was completed, the solvent was removed by vacuum distillation. This compound was subjected to column chromatography to give compound (3-8), and the yield was 0.12 g (yield: 31%).

Example  9: Synthesis of compound (3-9)

The synthesis route of the compound (3-9) is shown below.

(Synthesis of final compound)

In a two-necked 100 ml flask, 0.3 g (0.52 mol) of Intermediate (1) and 0.5 g of 5- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- ) -5H-benzofuro [2,3-e] pyrido [3,4-b] indole 5- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- A solution of 0.29 g (0.62 mmol) of Pd (PPh3) ₄ 18 mg (0.015 mmol) of TBAB 5 mg (0.015 mmol) of _3- mmol), Cs ₂ CO ₃ 504 mg (1.54 mmol) was added to toluene under nitrogen and refluxed for 30 hours. After the reaction was completed, the solvent was removed by vacuum distillation. Compound (3-9) was obtained by column chromatography using this compound, and the yield was 0.15 g (yield: 35%).

Test Example  One

LC-MS was measured using a Waters Acquity UPLC H-Class / SQD2 system instrument for the compounds of the examples of the present invention, and the results are shown in Table 1 below.

Classification (compound) MS Calcd. LC-MS Found [M + 1] < + > Example 1 (Compound 3-1) 664.26 665.55 Example 2 (Compound 3-2) 689.26 690.56 Example 3 (Compound 3-3) 739.27 740.65 Example 4 (Compound 3-4) 739.27 740.65 Example 5 (Compound 3-5) 738.28 739.66 Example 6 (Compound 3-6) 738.28 739.72 Example 7 (Compound 3-7) 739.27 740.65 Example 8 (Compound 3-8) 739.27 740.72 Example 9 (Compound 3-9) 829.28 830.59

Test Example 2

The UV / VIS spectra of the OLED compounds of the present invention were measured using a Jasco V-630 instrument and PL (photoluminescence) spectra were measured using a Jasco FP-8500 instrument and are shown in Table 2 below.

Classification (compound) UV / VIS (nm) * 1 PL (nm, room temperature) * 2 Example 1 (Compound 3-1) 246, 281, 337, 400, 408 495.5 Example 2 (Compound 3-2) 244, 281, 333, 381 460.5 Example 3 (Compound 3-3) 245, 289, 364 424.5 Example 4 (Compound 3-4) 243, 288, 362 418 Example 5 (Compound 3-5) 243, 288, 366 431 Example 6 (Compound 3-6) 243, 288, 363 419 Example 7 (Compound 3-7) 243, 288, 368 428 Example 8 (Compound 3-8) 242, 289, 365 416.5 Example 9 (Compound 3-9) 247, 290, 382 433.5 * 1: 1.0 x 10 ^-5 M in Methylene Chloride
* 2: 5.0 x 10 ^-6 M in Methylene Chloride

Device fabrication Test Example

2-TNATA is a hole injection layer, NPB is a hole transport layer, αβ-ADN is a host of a light emitting layer, Bphen is an electron transport layer, Liq is an electron injection layer, Al is a cathode, Respectively. The structures of these compounds are shown below.

Comparative test example  : ITO  / 2- TNATA  / NPB  / αβ- ADN , 9,9- diethyl -2,7- bis ((E) -4- tritylstyryl ) -9H-fluorene / Bphen  / Liq  / Al

A blue fluorescent organic light-emitting device was prepared in the same manner as in Example 1 except that ITO (180 nm) / 2-TNATA (60 nm) / NPB (20 nm) / αβ-ADN: 9,9-diethyl- -9H-fluorene was deposited in the order of 10% (30 nm) / Bphen (40 nm) / Liq (2 nm) / Al (100 nm). Before deposition of the organic material, the ITO electrode was subjected to oxygen plasma treatment at 125 W for 2 minutes at 2 × 10 ^-2 Torr. Organic matters were deposited at a vacuum of 9 × 10 ^-7 Torr. The blue fluorescent dopant was simultaneously deposited at 0.02 Å / sec on the basis of Liq and 0.18 Å / sec for αβ-ADN. / sec. < / RTI > The blue fluorescent dopant used in the experiment was 9,9-diethyl-2,7-bis ((E) -4-tritylstyryl) -9H-fluorene and the concentration of the dopant was fixed at 10%. After fabricating the device, it was sealed in a glove box filled with nitrogen gas to prevent air and moisture contact of the device. Barium oxide (Barium Oxide), which is a hygroscopic agent capable of removing moisture and so on, was put into a glass plate after 3M's adhesive tape was formed.

Test Example  One : ITO  / 2- TNATA  / NPB  / αβ- ADN , Compound (3-4) / Bphen   / Liq  / Al

A device was prepared in the same manner as in the Comparative Test Example except that the compound (3-4) prepared in Example 4 was used as a material for the light emitting layer instead of the blue fluorescent dopant substance used in the above Comparative Test Example.

Table 3 shows the electroluminescent characteristics of the organic light emitting device fabricated in the comparative test example and the test example 1.

Color coordinates
(x, y) EL Peak
(nm) Luminous efficiency
(cd / A,
@ 20 mA / cm 2) External quantum efficiency
(%,
@ 20 mA / cm 2) Comparative test example (0.17, 0.19) 456 1.89 1.20 Test Example 1
(Compound (3-4)) (0.15, 0.18) 479 3.35 2.57

(result)

As can be seen from Table 3 and FIG. 2, the device fabricated using the compound of the present invention as a light emitting layer material emits light in the blue wavelength region, and the device of Test Example 1 has a higher luminous efficiency than the device of Comparative Test Example, And the efficiency characteristics are all improved. The improvement of the luminous efficiency and the external quantum efficiency characteristic can provide an organic electroluminescent device with improved driving voltage and luminous efficiency.

Claims (11)

A pyrene derivative substituted with a triazole group represented by the following formula (1).
[Chemical Formula 1]

[In the above formula (1)
Ar ₁ is

or

Lt;
(X is each independently CH or N and Z is O or S)
L ₁ is

or

to be.] delete The method according to claim 1,
The compound represented by Formula 1 is a pyrene derivative substituted with a triazole group selected from the structures of Formula 2 below.
(2)

[In the formula 2, X and Z are as defined in the formula 1.] The method according to claim 1,
The pyrene derivative substituted with a triazole group is characterized in that the compound of the formula (1) is selected from the group consisting of the following formula (3).
(3)

An organic electroluminescent device comprising a pyrene derivative substituted with a triazole group according to any one of claims 1, 3, and 4. 6. The method of claim 5,
Wherein the triazole-substituted pyrene derivative is used as a hole injecting material or a hole transporting material. 6. The method of claim 5,
Wherein the triazole-substituted pyrene derivative is used as a host or dopant material of a blue fluorescent device. A first electrode, a second electrode, and at least one organic film disposed between the electrodes,
Wherein the organic layer comprises a pyrene derivative substituted with a triazole group according to any one of claims 1, 3, and 4. 9. The method of claim 8,
The organic layer includes a hole injecting layer, a hole transporting layer, a functional layer having both a hole injecting function and a hole transporting function, a buffer layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transporting layer, And at least one functional layer having at least one functional group at the same time. 9. The method of claim 8,
The triazole-substituted pyrene derivative is contained in at least one selected from the group consisting of a light emitting layer, an organic film disposed between the anode and the light emitting layer, and an organic film disposed between the light emitting layer and the cathode. 9. The method of claim 8,
The triazole-substituted pyrene derivative is contained in at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, and a functional layer having both a hole injection function and a hole transport function.

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