WO2013094921A1 - Azaindeno anthracene derivative and organic electroluminescent element using same - Google Patents

Abstract

The present invention relates to an azaindeno anthracene derivative and an organic electroluminescent element using same. In the present invention, the azaindeno anthracene derivative is applied to a luminescent layer of the organic electroluminescent element to provide better efficiency, driving voltage, and service life.

Description

Azaindenoanthracene derivatives and organic electroluminescent devices using the same

The present invention relates to an azaindenoanthracene derivative and an organic electroluminescent device using the same, and more particularly to an organic electroluminescent device exhibiting excellent efficiency, driving voltage, life, etc. by applying azaindenoanthracene derivative to the light emitting layer will be.

In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic light emitting device using such an organic light emitting phenomenon usually has a structure including an anode, a cathode and an organic material layer therebetween. In this case, the organic material layer is often composed of a multilayer structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, a hole injection layer, a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL), electrons Injection layer and the like.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected from the anode, and electrons are injected into the organic material layer from the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine. In this case, the material used as the organic material layer may be classified into a light emitting material, a charge transport material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.

The luminescent material may be classified into blue, green, and red luminescent materials and yellow and orange luminescent materials required to achieve better natural colors according to the emission color. In addition, in order to increase luminous efficiency through increase in color purity and energy transfer, a host / dopant system may be used as the light emitting material. The principle is that when a small amount of dopant having a smaller energy band gap than the host mainly constituting the light emitting layer and excellent luminous efficiency is mixed in the light emitting layer, excitons generated in the host are transported to the dopant to give high efficiency light. In this case, since the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.

In order to fully exhibit the excellent characteristics of the above-described organic light emitting device, a material constituting the organic material layer in the device, that is, a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc. Must be preceded. For example, Korean Patent Publication No. 10-2011-0024695 discloses an organic electroluminescent device using an anthracene derivative and an amine derivative. However, the development of a stable and efficient organic material layer for an organic light emitting device has not yet been made sufficiently, and therefore, development of new materials is continuously required.

The present invention has been made to solve the above problems, to provide a novel material that can be used as a light emitting layer to improve the luminous efficiency, brightness, power efficiency, thermal stability and device life of the device and to provide an organic electroluminescent device using the same The purpose.

In addition, other technical problems to be achieved by the present invention are not limited to the above-mentioned technical problems, and other technical problems not mentioned above are clearly understood by those skilled in the art from the following description. Could be.

The present invention provides a compound represented by the following formula (1), preferably an azaindenoanthracene-based compound.

Formula 1

In the above formula,

Each X is independently carbon or nitrogen, wherein at least one of X is nitrogen,

R ₁ to R ₁₂ are the same or different, each independently represent hydrogen, deuterium, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₆ ~ C ₄₀ aryl group, C ₅ ~ C ₄₀ of a heteroaryl group, C ₆ ~ C ₄₀ of the aryloxy group, C ₆ ~ C ₄₀ aryl group, C ₆ ~ C ₄₀ of the diarylamino group, C aryl group of _{6 ~ C 40, C 6 ~} C 40 of the arylalkenyl Nyl group, C ₃ ~ C ₄₀ cycloalkyl group and C ₃ ~ C ₄₀ heterocycloalkyl group, each of which are adjacent groups and condensed aliphatic ring, condensed aromatic ring, condensed heteroaliphatic ring or condensed heteroaromatic ring Form or not form

In the above R ₁ to R ₁₂ , C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ Alkenyl group, C ₆ ~ C ₄₀ aryl group, C ₅ ~ C ₄₀ Heteroaryl group, C ₆ ~ C ₄₀ Aryloxy group, C ₆ ~ C ₄₀ arylamino group, C ₆ ~ C ₄₀ diarylamino group, C ₆ ~ C ₄₀ arylalkyl group, C ₆ ~ C ₄₀ aryl alkenyl group, C ₃ ~ C ₄₀ cycloalkyl group Or C ₃ to C ₄₀ heterocycloalkyl group are each independently deuterium, halogen, nitrile group, nitro group, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₁ to C ₄₀ Alkoxy group, C ₁ -C ₄₀ amino group, C ₃ -C ₄₀ cycloalkyl group, C ₃ -C ₄₀ heterocycloalkyl group, C ₆ -C ₄₀ aryl group and C ₅ -C ₄₀ heteroaryl group Substituted or substituted with one or more selected from.

In addition, the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer is a compound represented by the formula (1) It provides an organic electroluminescent device comprising a.

Here, the organic material layer including the compound represented by Formula 1 is preferably a light emitting layer.

When the compound represented by Formula 1 according to the present invention is adopted as the light emitting layer material of the organic electroluminescent device, it may exhibit an increase in efficiency and an improvement in life compared to conventional light emitting materials.

Therefore, the organic electroluminescent device of the present invention including the compound represented by Formula 1 exhibits excellent characteristics in terms of luminous efficiency, brightness, power efficiency, driving voltage and lifetime, thereby maximizing performance and improving lifetime in full color organic EL panels. It can be effective.

Hereinafter, the present invention will be described in detail.

The present invention is characterized by introducing an aromatic ring or a heteroaromatic ring at a specific position of the basic skeleton while having an azaindenoanthracene-based basic skeleton having excellent device characteristics.

The azaindenonoanthracene compound contains a 5-membered ring structure. Here, the five-membered ring structure has excellent electron withdrawing properties, thereby exhibiting electron injection properties. Therefore, the organic light emitting device using the azaindenoanthracene compound is effective to transport electrons generated from the cathode, and the low driving voltage that can be generated contributes to the improvement of efficiency and lifetime.

Since the specific position of the azaindenoanthracene compound described above, particularly the 9 position, is the most reactive substitution position, introduction of an electronically stable substituent may constitute a more stable compound. In one example, when an aryl group, a heteroaryl group, an alkylaryl group or the like is introduced into the 9-position, as so be able to control the band gap depending on the substituents, as well as the light emitting layer by the introduction of various substituents hole transport layer, an electron transport layer, or a host application Can be.

In addition, due to the wide bandgap derived from the azaindenoanthracene backbone, it can exhibit excellent properties as a host material.

In addition, by introducing various aromatic ring substituents into the azaindenoanthracene skeleton, the molecular weight of the compound is significantly increased, thereby increasing the glass transition temperature and thereby having high thermal stability. Therefore, the device containing the azaindenoanthracene compound of this invention can exhibit the durability and lifetime improvement.

In the compound represented by Formula 1 according to the present invention, except for R ₁ , R ₂ , R ₃ , R ₄ , R ₉ , R ₅ to R ₈ , and R ₁₀ to R ₁₂ are all preferably hydrogen or deuterium. Do. More specifically, since the R ₉ position of the azaindenoanthracene is the most reactive substitution position, a more stable compound can be constituted by introducing an electronically stable substituent. Therefore, in the present invention, it is more preferable that all of R ₁ to R ₈ and R ₁₀ to R ₁₂ except for R ₉ are hydrogen or deuterium.

When R ₁ to R ₈ and R ₁₀ to R ₁₂ are all hydrogen or deuterium as described above, R ₉ is a C ₆ to C ₄₀ aryl group or a C ₅ to C ₄₀ heteroaryl group, each of which is adjacent to each other. Form or not form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring with a group; The aryl group or heteroaryl group is each independently deuterium, halogen, nitrile group, nitro group, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C _{One selected} from the group consisting of ₁ to C ₄₀ amino group, C ₃ to C ₄₀ cycloalkyl group, C ₃ to C ₄₀ heterocycloalkyl group, C ₆ to C ₄₀ aryl group and C ₅ to C ₄₀ heteroaryl group It may be substituted or unsubstituted above.

In the present invention, the aryl group is preferably phenyl, naphthalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, benzofluoranthene, perylene, fluorene, the heteroaryl group is pyridine, pyri Preferred is a case of midine, triazine, carbazole, acridine, dibenzothiophene, dibenzofuran, thianthrene.

Meanwhile, the compound represented by Chemical Formula 1 of the present invention should be introduced with at least one nitrogen as X, of which one nitrogen atom is preferably introduced as X. As such, when nitrogen having a relatively higher electronegativity than carbon is introduced, the electron recruitment of the five-membered ring structure can be enhanced.

Compounds of the present invention in which one nitrogen atom is introduced as X may be more specified as in Chemical Formula 2 below.

Formula 2

Wherein R ₁ to R ₃ and R ₅ to R ₁₂ are as defined in Chemical Formula 1.

In the compound represented by Formula 2, R ₅ to R ₈ , and R ₁₀ to R ₁₂ , except R ₁ , R ₂ , R ₃ , and R ₉ , are all preferably hydrogen or deuterium, and particularly, except R ₉ . More preferably, R ₁ to R ₃ , R ₅ to R ₈ and R ₁₀ to R ₁₂ are all hydrogen or deuterium.

When R ₁ to R ₃ , R ₅ to R ₈ and R ₁₀ to R ₁₂ are all hydrogen or deuterium as described above, R ₉ is a C ₆ to C ₄₀ aryl group or a C ₅ to C ₄₀ heteroaryl group Wherein they each form or do not form condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings or condensed heteroaromatic rings with adjacent groups; The aryl group or heteroaryl group is each independently deuterium, halogen, nitrile group, nitro group, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C _{One selected} from the group consisting of ₁ to C ₄₀ amino group, C ₃ to C ₄₀ cycloalkyl group, C ₃ to C ₄₀ heterocycloalkyl group, C ₆ to C ₄₀ aryl group and C ₅ to C ₄₀ heteroaryl group It may be substituted or unsubstituted above.

The azaindenoanthracene-based compound represented by the general formula (1) according to the present invention may be more specified by the chemical formulas illustrated below. However, the compound represented by Formula 1 of the present invention is not limited to those illustrated below.

According to the present invention, the compound represented by Chemical Formula 1 may be synthesized according to a general synthesis method, and their detailed synthesis process will be described in detail in the synthesis examples described below.

<Organic EL device>

On the other hand, another aspect of the present invention relates to an organic electroluminescent device comprising a compound represented by the formula (1) according to the present invention.

Specifically, the organic electroluminescent device according to the present invention comprises (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode, wherein the at least one organic layer At least one of them is characterized in that it comprises a compound represented by the formula (1) of the present invention.

Herein, the organic material layer including the compound represented by Chemical Formula 1 may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. Preferably, the compound represented by Formula 1 may be included in the organic electroluminescent device as a light emitting layer material. In this case, the organic EL device may improve luminous efficiency, brightness, power efficiency, thermal stability, and device life.

In particular, the compound represented by Formula 1 according to the present invention may be included as a phosphorescent or fluorescent host material or a dopant material thereof. Preferably, the compound represented by Formula 1 may be included in the organic light emitting device as a phosphorescent host, a fluorescent host, or a dopant material of blue, green, and / or red.

In addition, in the organic electroluminescent device according to the present invention, other organic material layers other than the organic material layer containing the compound of Formula 1 may be a hole injection layer, a hole transport layer, a light emitting layer, and / or an electron transport layer.

For example, a substrate, an anode, a hole injection layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode may be sequentially stacked, and the light emitting layer may be represented by Formula 1 according to the present invention. It may include a compound represented by. An electron injection layer may be positioned on the electron transport layer.

In addition, as described above, the organic EL device according to the present invention may not only have a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked, but an insulating layer or an adhesive layer may be inserted between the electrode and the organic material layer interface.

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

The organic electroluminescent device according to the present invention forms an organic material layer and an electrode using materials and methods known in the art, except that at least one layer of the organic material layer is formed to include the compound represented by Chemical Formula 1. It can be manufactured by.

For example, a silicon wafer, quartz or glass plate, metal plate, plastic film or sheet may be used as the substrate.

The anode material may be a metal such as vanadium, chromium, copper, zinc, gold or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but is not limited thereto.

The negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; Multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like, but are not limited thereto.

In addition, materials such as a hole injection layer, a hole transport layer, and an electron transport layer are not particularly limited, and conventional materials known in the art may be used without limitation.

Hereinafter, the present invention will be described in detail with reference to the following Examples. However, the following examples are merely to illustrate the present invention and the present invention is not limited by the following examples.

Preparation Example 1. Preparation of 2- (anthracen-9-yl) -3-bromopyridine of Scheme 1>

[Scheme 1]

2,3-dibromopyridine 10g (42.21mmol), anthracen-9-ylboronic acid 9.37g (42.21mmol), Pd (PPh ₃ ) ₄ 2.44g (0.05 equiv), K ₂ CO ₃ 16.23g (3 equiv) 140 ml toluene , 63 ml of water and 35 ml of ethanol were added to a mixed solvent, and the mixture was heated and stirred at 100 to 110 ° C for 3 hours. After completion of the reaction, the reaction solution was filtered through Celite, and 8.5 g (yield: 60%) of 2- (anthracen-9-yl) -3-bromopyridine of Scheme 1 was obtained through column chromatography.

HRMS [M] ⁺ : 333

Preparation Example 2 Preparation of Compound azaindenoanthracene of Scheme 2

[Scheme 2]

8.5 g (25.43 mmol) of 2- (anthracen-9-yl) -3-bromopyridine, 0.9 g (0.05 equiv) of Pd (PPh ₃ ) Cl ₂ and 11.6 g ( ₃ equiv) of diazabicycloundecene obtained in Preparation Example 1 were added to 130 ml of DMF. It was put in to and stirred with heating at 140 ℃ for 6 hours. After completion of the reaction, the reaction solution was filtered through Celite, and then 3.2g of azaindenoanthracene compound of Scheme 2 (yield: 50%) was obtained through column chromatography.

HRMS [M] ⁺ : 252

Preparation Example 3 Preparation of Compound 9-bromo azaindenoanthracene of Scheme 3

Scheme 3

3.2 g (12.6 mmol) of azaindenoanthracene obtained in Preparation Example 2 was prepared in a 160 ml solution of dichloromethane at 0 ° C. under a nitrogen atmosphere. A mixture of bromine 2g (1 equivalent) and dichloromethane 32ml was added thereto, followed by stirring for 5 hours. After the reaction was completed, the reaction solution was filtered and washed with methanol to obtain 2.9 g (yield: 70%) of 9-bromo azaindenoanthracene.

HRMS [M] ⁺ : 331

Synthesis Example 1. Preparation of compound Mat-1 of Scheme 4>

Scheme 4

14 g (42.21 mmol) of 9-bromo azaindenoanthracene obtained in Preparation Example 3, 9.37 g (42.21 mmol) of anthracen-2-ylboronic acid, 2.44 g (0.05 equivalent) of Pd (PPh ₃ ) ₄ , 16.23 g of K ₂ CO ₃ (3) Equivalent weight) was added to a mixed solvent of 140 ml of toluene, 63 ml of water, and 35 ml of ethanol, followed by heating and stirring at 100 to 110 ° C. for 3 hours. After completion of the reaction, the reaction solution was filtered through Celite, and then 14.5 g (yield: 80%) of the Mat-1 compound of Scheme 4 was obtained through column chromatography.

Elemental Analysis: C, 92.28; H, 4. 46; N, 3.26 / HRMS [M] ⁺ : 428

Synthesis Example 2. Preparation of Compound Mat-3

Compound Mat-3 was prepared by following the same procedure as in Synthesis Example 1, except that pyren-1-ylboronic acid was used instead of anthracen-2-ylboronic acid.

Elemental Analysis: C, 92.69; H, 4. 22; N, 3.09 / HRMS [M] ⁺ : 452

Synthesis Example 3. Preparation of Compound Mat-4

Compound Mat-4 was prepared by the same procedure as in Synthesis Example 1, except that 9,9-dimethyl-9H-fluoren-2-ylboronic acid was used instead of anthracen-2-ylboronic acid.

Elemental Analysis: C, 91.65; H, 5.20; N, 3.14 / HRMS [M] ⁺ : 444

Synthesis Example 4. Preparation of Compound Mat-9

Except for using triphenylen-2-ylboronic acid instead of anthracen-2-ylboronic acid, Compound Mat-9 was prepared in the same manner as in Synthesis Example 1.

Elemental Analysis: C, 92.67; H, 4.41; N, 2.92 / HRMS [M] ⁺ : 478

Synthesis Example 5. Preparation of Compound Mat-12

Compound Mat-12 was prepared by following the same procedure as in Synthesis Example 1, except that 9,10-di (naphthalen-2-yl) anthracen-2-ylboronic acid was used instead of anthracen-2-ylboronic acid. .

Elemental Analysis: C, 93.36; H, 4.58; N, 2.05 / HRMS [M] ⁺ : 680

Synthesis Example 6. Preparation of Compound Mat-13

Compound Mat-13 was prepared by the same procedure as in Synthesis Example 1, except that fluoranthen-3-ylboronic acid was used instead of anthracen-2-ylboronic acid.

Elemental Analysis: C, 92.69; H, 4. 22; N, 3.09 / HRMS [M] ⁺ : 452

Synthesis Example 7. Preparation of Compound Mat-14

Compound Mat-14 was prepared in the same manner as in Synthesis Example 1, except that 7,12-diphenylbenzo [k] fluoranthen-3-ylboronic acid was used instead of anthracen-2-ylboronic acid.

Elemental Analysis: C, 93.41; H, 4. 46; N, 2.14 / HRMS [M] ⁺ : 654

Synthesis Example 8. Preparation of Compound Mat-16

Compound Mat-16 was prepared by the same procedure as in Synthesis Example 1, except that 4- (phenanthren-9-yl) phenylboronic acid was used instead of anthracen-2-ylboronic acid.

Elemental Analysis: C, 92.64; H, 4.59; N, 2.77 / HRMS [M] ⁺ : 504

Synthesis Example 9. Preparation of Compound Mat-25

Except for using 9,9,9 ', 9'-tetramethyl-9H, 9'H-2,2'-bifluoren-7-ylboronic acid instead of anthracen-2-ylboronic acid, the same as in Synthesis Example 1 The procedure was carried out to prepare compound Mat-25.

Elemental Analysis: C, 92.27; H, 5.53; N, 2.20 / HRMS [M] ⁺ : 636

Synthesis Example 10 Preparation of Compound Mat-38

Compound Mat-38 was prepared in the same manner as in Synthesis Example 1, except that 9-phenyl-9H-carbazol-3-ylboronic acid was used instead of anthracen-2-ylboronic acid.

Elemental Analysis: C, 89.85; H, 4. 48; N, 5.66 / HRMS [M] ⁺ : 493

Synthesis Example 11. Preparation of Compound Mat-44

Compound Mat-44 was prepared in the same manner as in Synthesis Example 1, except that 4- (naphthalen-1-yl) phenylboronic acid was used instead of anthracen-2-ylboronic acid.

Elemental Analysis: C, 92.28; H, 4.65; N, 3.07 / HRMS [M] ⁺ : 454

Synthesis Example 12 Preparation of Compound Mat-52

Compound Mat-52 was prepared by the same procedure as in Synthesis Example 1, except that 4- (9-phenyl-9H-carbazol-3-yl) phenylboronic acid was used instead of anthracen-2-ylboronic acid.

Elemental Analysis: C, 90.50; H, 4.59; N, 4.91 / HRMS [M] ⁺ : 569

Synthesis Example 13. Preparation of Compound Mat-53

8.26 g (12.6 mmol) of the Mat-14 compound prepared in Synthesis Example 7 was prepared in a 160 ml solution of 0 ° C. dichloromethane under a nitrogen atmosphere. 2 g (1 equivalent) of bromine and 32 ml of dichloromethane were added thereto, followed by stirring for 5 hours. After completion of the reaction, the reaction solution was filtered and washed with methanol, 6.4 g of 2-bromo-8- (7,12-diphenylbenzo [k] fluoranthen-3-yl) aceanthryleno [1,2-b] pyridine (yield: 70% )

2-bromo-8- (7,12-diphenylbenzo [k] fluoranthen-3-yl) aceanthryleno [1,2-b] pyridine 5g (6.8mmol), phenylboronic acid 0.83g (6.8mmol), Pd (PPh ₃ ) ₄ 0.4 g (0.05 equiv) and 2.8 g ( ₃ equiv) of K ₂ CO ₃ were added to a mixed solvent of 25 ml of toluene, 11 ml of water and 6.5 ml of ethanol, followed by heating and stirring at 100 to 110 ° C. for 3 hours. . After completion of the reaction, the reaction solution was filtered through Celite, and then 4 g of Mat-53 compound (yield: 80%) was obtained through column chromatography.

Elemental Analysis: C, 93.54; H, 4.54; N, 1.91 / HRMS [M] ⁺ : 730

Synthesis Example 14. Preparation of Compound Mat-56

The same procedure as in Synthesis Example 1 was performed except that 10- (biphenyl-4-yl) -9- (naphthalen-2-yl) anthracen-2-ylboronic acid was used instead of anthracen-2-ylboronic acid. Compound Mat-56 was prepared.

Elemental Analysis: C, 93.32; H, 4. 70; N, 1.98 / HRMS [M] ⁺ : 706

Synthesis Example 15 Preparation of Compound Mat-63

A compound was prepared in the same manner as in Synthesis Example 1, except that 9,9'-diphenyl-9H, 9'H-3,3'-bicarbazol-7-ylboronic acid was used instead of anthracen-2-ylboronic acid. Mat-63 was prepared.

Elemental Analysis: C, 89.77; H, 4.52; N, 5.71 / HRMS [M] ⁺ : 734

Synthesis Example 16 Preparation of Compound Mat-76

Except for using phenylboronic acid instead of anthracen-2-ylboronic acid, Compound Mat-76 was prepared in the same manner as in Synthesis Example 1.

Elemental Analysis: C, 91.16; H, 4.59; N, 4.25 / HRMS [M] ⁺ : 328

Synthesis Example 17 Preparation of Compound Mat-77

Compound Mat-77 was prepared by the same procedure as in Synthesis Example 1, except that naphthalen-2-ylboronic acid was used instead of anthracen-2-ylboronic acid.

Elemental Analysis: C, 91.79; H, 4.52; N, 3.69 / HRMS [M] ⁺ : 378

Example 1 Fabrication of Organic Electroluminescent Light Emitting Device

An organic electroluminescent device was manufactured by the following method.

The glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol and the like was dried and then transferred to a plasma cleaner, and then the substrate was cleaned for 5 minutes using an oxygen plasma and the substrate was transferred to a vacuum evaporator.

DS-205 (Doosan Co., Ltd.) was vacuum-deposited to a thickness of 800 kPa on the prepared ITO (anode) to form a hole injection layer, and α-NPB ( N , N- , a hole transporting material, on the hole injection layer). di (naphthalene-1-yl) -N , N- diphenylbenzidine) was vacuum deposited to a thickness of 150 kPa to form a hole transport layer.

Using the compound Mat-1 prepared in Synthesis Example 1 as a green host material thereon, by doping 5% of C-545T as a dopant to vacuum deposition to a thickness of 300Å to form a light emitting layer. An electron transport layer was formed by vacuum depositing Alq3, which is an electron transport material, on the light emitting layer to a thickness of 250 kPa. Thereafter, LiF, which is an electron injection material, was deposited to a thickness of 10 kW to form an electron injection layer, and aluminum was vacuum deposited to a thickness of 2000 kW thereon to form a cathode to fabricate an organic EL device.

Example 2-3 Fabrication of Organic Electroluminescent Green Light Emitting Device

An organic electroluminescent device of Examples 2 and 3 was manufactured by the same method as Example 1, except that Compound Mat-3 and Mat-4 were used instead of Compound Mat-1 when forming the emission layer.

Examples 4 to 9 Fabrication of Organic Electroluminescent Green Light-Emitting Element

In the light emitting layer, DS-H522 (Doosan Co., Ltd.) was used as a green host, and as a green dopant, compounds Mat-9 (Example 4), Mat-12 (Example 5), Mat-13 (Example 6), Mat- The organic electric field of Examples 4-9 was carried out in the same manner as in Example 1, except that 14 (Example 7), Mat-25 (Example 8), and Mat-53 (Example 9) were used, respectively. A green light emitting device was manufactured.

Example 10-11 Fabrication of Organic Electroluminescent Blue Light Emitting Device

The same method as in Example 1, except that DS-405 (Doosan Co., Ltd.), blue dopant compound Mat-76 (Example 10), and Mat-77 (Example 11) were used as the blue host to form the emission layer. To perform the organic electroluminescent blue light emitting device was manufactured.

Comparative Example 1 Fabrication of Organic Light Emitting Diode

The organic light emitting layer was organically formed in the same manner as in Example 1, except that Alq3 and C-545T, which are systems represented by green devices, were used instead of the compound and DS-H522 (Doosan Co., Ltd.). An electroluminescent device was produced.

Comparative Example 2 Fabrication of Organic Electroluminescent Blue Light Emitting Device

An organic electroluminescent device was manufactured in the same manner as in Example 1, except for using the blue device system ADN and DS-405 instead of the compound and DS-405 (Doosan Co., Ltd.) used to fabricate the light emitting layer in the present invention. Produced.

Table 1

	Examples of the organic electroluminescent device of Examples 1 to 11 and Comparative Examples 1 to 2
Hole Injection Layer (HIL)	DS-205
Hole Transport Layer (HTL)	a-NPB
Organic Light Emitting Layer (EML)	See Table 2
Electron Transport Layer (ETL)	Alq3
Electron Injection Layer (EIL)	LiF
Cathode	Al

TABLE 2

	Organic Light Emitting Layer (EML)
	Green host	Green dopant
Example 1	Mat-1	C-545
Example 2	Mat-3	C-545
Example 3	Mat-4	C-545
Example 4	DS-H522	Mat-9
Example 5	DS-H522	Mat-12
Example 6	DS-H522	Mat-13
Example 7	DS-H522	Mat-14
Example 8	DS-H522	Mat-25
Example 9	DS-H522	Mat-53
Comparative Example 1	Alq3	C-545
	Blue host	Blue dopant
Example 10	Mat-76	DS-405
Example 11	Mat-77	DS-405
Comparative Example 2	ADN	DS-405

At this time, the structure of NPB, C-545T, ADN is as follows.

Experimental Example 1. Performance Evaluation of Organic Light Emitting Diode

For each of the organic electroluminescent devices manufactured in Examples 1 to 9 and Comparative Example 1, the luminous efficiency and driving voltage at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 3 below.

TABLE 3

compound	Voltage (V)	Efficiency (cd / A)
Mat-1 (Example 1)	6.0	11.5
Mat-3 (Example 2)	6.8	10.2
Mat-4 (Example 3)	6.2	11.0
Mat-9 (Example 4)	6.2	12.0
Mat-12 (Example 5)	5.5	12.9
Mat-13 (Example 6)	5.3	12.3
Mat-14 (Example 7)	5.0	13.0
Mat-25 (Example 8)	6.0	11.9
Mat-53 (Example 9)	5.3	12.9
Comparative Example 1	6.9	9.5

As shown in the table, the organic EL device of Examples 1 to 3 using the compound according to the present invention as a green host was able to confirm slightly improved performance in terms of driving voltage and efficiency.

In addition, the organic EL device of Examples 4 to 9 using the compound according to the present invention as a green dopant was able to confirm a significantly improved performance in terms of driving voltage and efficiency.

[ Experimental Example 2. Performance Evaluation of Organic Electroluminescent Blue Light Emitting Device]

 For each organic electroluminescent blue light emitting device manufactured in Example 10-11 and Comparative Example 2, the luminous efficiency and driving voltage at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 4 below.

Table 4

compound	Voltage (V)	Efficiency (cd / A)
Mat-76 (Example 10)	5.4	5.1
Mat-77 (Example 11)	5.2	5.2
Comparative Example 2	5.6	4.8

As shown in Table 4, it was confirmed that the organic EL device using the compound according to the present invention as a blue host shows improved performance in terms of driving voltage and efficiency.

Claims (10)

1. Compound represented by the following formula (1):

   [Formula 1]

   

   In the above formula,

   Each X is independently carbon or nitrogen, wherein at least one of X is nitrogen;

   R ₁ to R ₁₂ are the same or different, each independently represent hydrogen, deuterium, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₆ ~ C ₄₀ aryl group, C ₅ ~ C ₄₀ of a heteroaryl group, C ₆ ~ C ₄₀ of the aryloxy group, C ₆ ~ C ₄₀ aryl group, C ₆ ~ C ₄₀ of the diarylamino group, C aryl group of _{6 ~ C 40, C 6 ~} C 40 of the arylalkenyl Nyl group, C ₃ ~ C ₄₀ cycloalkyl group and C ₃ ~ C ₄₀ heterocycloalkyl group, each of which are adjacent groups and condensed aliphatic ring, condensed aromatic ring, condensed heteroaliphatic ring or condensed heteroaromatic ring Form or not form;

   In the above R ₁ to R ₁₂ , C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ Alkenyl group, C ₆ ~ C ₄₀ aryl group, C ₅ ~ C ₄₀ Heteroaryl group, C ₆ ~ C ₄₀ Aryloxy group, C ₆ ~ C ₄₀ arylamino group, C ₆ ~ C ₄₀ diarylamino group, C ₆ ~ C ₄₀ arylalkyl group, C ₆ ~ C ₄₀ aryl alkenyl group, C ₃ ~ C ₄₀ cycloalkyl group Or C ₃ to C ₄₀ heterocycloalkyl group are each independently deuterium, halogen, nitrile group, nitro group, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₁ to C ₄₀ Alkoxy group, C ₁ -C ₄₀ amino group, C ₃ -C ₄₀ cycloalkyl group, C ₃ -C ₄₀ heterocycloalkyl group, C ₆ -C ₄₀ aryl group and C ₅ -C ₄₀ heteroaryl group Substituted or substituted with one or more selected from.
2. The compound of claim 1, wherein R ₅ to R ₈ , and R ₁₀ to R ₁₂ are each independently hydrogen or deuterium.
3. The compound of claim 1, wherein R ₁ to R ₈ and R ₁₀ to R ₁₂ are each independently hydrogen or deuterium.
4. The compound of claim 1, wherein R ₉ is a C ₆ -C ₄₀ aryl group or a C ₅ -C ₄₀ heteroaryl group, each of which is an adjacent group and a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, or a condensed group. Forming or not forming a heteroaromatic ring;

   The aryl group or heteroaryl group is each independently deuterium, halogen, nitrile group, nitro group, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C _{One selected} from the group consisting of ₁ to C ₄₀ amino group, C ₃ to C ₄₀ cycloalkyl group, C ₃ to C ₄₀ heterocycloalkyl group, C ₆ to C ₄₀ aryl group and C ₅ to C ₄₀ heteroaryl group It is substituted or unsubstituted above.
5. The compound of claim 1, wherein the nitrogen in X is one.
6. The compound of claim 5, wherein R ₅ to R ₈ , and R ₁₀ to R ₁₂ are all hydrogen or deuterium.
7. The compound according to claim 5, wherein R ₁ to R ₈ and R ₁₀ to R ₁₂ are all hydrogen or deuterium.
8. 8. A compound according to claim 7, wherein R ₉ is a C ₆ -C ₄₀ aryl group or a C ₅ -C ₄₀ heteroaryl group, each of which is an adjacent group and a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or condensed Forming or not forming a heteroaromatic ring;

   The aryl group or heteroaryl group is each independently deuterium, halogen, nitrile group, nitro group, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C _{One selected} from the group consisting of ₁ to C ₄₀ amino group, C ₃ to C ₄₀ cycloalkyl group, C ₃ to C ₄₀ heterocycloalkyl group, C ₆ to C ₄₀ aryl group and C ₅ to C ₄₀ heteroaryl group It is substituted or unsubstituted above.
9. An organic electroluminescent device comprising an anode, a cathode, and at least one organic material layer interposed between the anode and the cathode.

   At least one of the one or more organic material layers comprises an compound represented by the formula (1) according to any one of claims 1 to 8.
10. The organic electroluminescent device according to claim 9, wherein the organic material layer including the compound represented by Chemical Formula 1 is a light emitting layer.