WO2015099406A1 - Organic electroluminescent device - Google Patents

Abstract

The present invention relates to an organic electroluminescent device and may provide an organic electroluminescent device having improved characteristics of luminous efficiency, driving voltage, life, and the like by comprising an asymmetric anthracene derivative as an organic layer material, preferably a luminescent layer material, or more preferably a fluorescent host material of the organic electroluminescent device.

Description

Organic electroluminescent element

The present invention relates to an organic electroluminescent device having improved characteristics such as driving voltage, luminous efficiency and lifetime.

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.

When voltage is applied between two electrodes of the organic light emitting device, 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. When a small amount of dopant having a smaller energy band gap than the host 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 produce 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, it is necessary to use a stable and efficient material as a material forming 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, or an electron injection material. It must be preceded. 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.

An object of the present invention is to provide an organic electroluminescent device having improved luminescence efficiency, driving voltage, lifespan, etc. by introducing a compound which is excellent in fluorescence ability and can be used as a light emitting layer material to an organic electroluminescent device.

In order to achieve the above object, the present invention is an anode; cathode; And one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers includes a compound represented by Formula 1 below. .

[Formula 1]

In Chemical Formula 1,

A plurality of R ₁ are the same or different from each other,

R ₁ is phenyl or naphthyl,

Ar ₁ is a substituent represented by any one of the formulas A-1 to A-6,

However, Ar ₁ is

Except in the same case.

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

Hereinafter, the present invention will be described in detail.

The present invention is characterized in that at least one of the one or more organic material layers interposed between the anode and the cathode of the organic electroluminescent device comprises a compound represented by the formula (1).

The compound represented by Formula 1 has an asymmetric anthracene-based skeleton having excellent device characteristics, and at least one specific aromatic ring is introduced at a specific position of the skeleton.

Specifically, the compound represented by the formula (1) of the present invention, while a phenyl group or biphenyl group substituted with naphthyl at position 9 of the anthracene basic skeleton is introduced, biphenyl, terphenyl, By introducing an aromatic ring such as naphthyl, phenanthrene, pyrene, triphenylene, or phenylnaphthyl, stacking can be relatively suppressed to prevent shifting or crystallization of the emission wavelength band due to intermolecular interaction, Therefore, compared to the anthracene compound having a conventional symmetrical structure, characteristics such as luminous efficiency, driving voltage, and lifetime may be improved. Where the carbon position number of the anthracene is

Can be expressed as:

In addition, the compound of Formula 1 may be introduced into a phenyl group or naphthyl group at position 2 of the anthracene-based basic skeleton, the emission wavelength is adjusted to improve the color purity as a green / blue light emitting material. In particular, the compound of Formula 1 may be applied as a host material of the green light emitting device.

In addition, the compound of Formula 1 has a wide bandgap due to the anthracene basic skeleton, and thus has excellent characteristics as a host material, thereby exhibiting luminous efficiency, durability of a device, and improvement of lifespan.

In the compound of Formula 1 according to the present invention, Ar ₁ may be a substituent represented by any one of the following Formulas B-1 to B-12, but is not limited thereto. However, Ar ₁ is

Except in the same case.

Examples of the compound represented by Formula 1 of the present invention include a compound represented by the following Formula 2 to Formula 4, but is not limited thereto.

[Formula 2]

[Formula 3]

[Formula 4]

In Chemical Formulas 2 to 4,

Ar ₁ is as defined in formula (1).

According to the present invention, the anthracene-based compound represented by Chemical Formula 1 may be more specifically represented by the compounds represented by the following Chemical Formulas Mat-1 to Mat-34, but is not limited thereto.

The compound of formula 1 of the present invention can be synthesized in various ways with reference to the following synthesis examples. Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.

The organic electroluminescent device according to the present invention comprises (i) an anode, (ii) a cathode, and (iii) one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers. Includes a compound represented by the above formula (1).

The organic layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, and among these, the hole injection layer, the hole transport layer, or the light emitting layer may include a compound represented by Chemical Formula 1, and preferably, a light emitting layer. It may include a compound represented by the formula (1).

Here, the compound represented by Chemical Formula 1 may be included as a fluorescent host material, and may be preferably included as a fluorescent host material of green or blue color.

In this case, the organic EL device may improve luminous efficiency, brightness, power efficiency, thermal stability, and device life.

The light emitting layer of the organic EL device according to the present invention may include a dopant. Examples of such dopants include coumarin derivatives (eg, C 545T), quinacridone derivatives, compounds of Formula 5, and the like. Among them, the compound of Formula 5 is substituted with at least one aryl amine group in the aromatic ring, and the luminous efficiency and lifespan may be improved compared to other conventional dopants.

When the compound of Formula 5 and the compound of Formula 1 are used together, the color purity of the device is higher and the luminous efficiency is further improved, compared with the case of using the compound of Formula 1 with other dopants known in the art. The lifetime of the device can be increased.

[Formula 5]

In Chemical Formula 5,

Ar ₂ is selected from the group consisting of a substituted or unsubstituted C ₁₀ ~ C ₆₀ aromatic ring and a substituted or unsubstituted heteroaromatic ring having 10 to 60 nuclear atoms, preferably naphthalene, anthracene, phenanthrene, pi Lene, chrysene, fluoranthene, benzofluoranthene and the like, more preferably anthracene, pyrene, chrysene;

Ar ₃ and Ar ₄ are each independently selected from the group consisting of C ₆ ~ C ₆₀ aryl group and heteroaryl group having 5 to 60 nuclear atoms, preferably phenyl, naphthyl, dibenzofuran or dibenzothiophene Is;

The aryl group and heteroaryl group of Ar ₃ to Ar ₄ are each independently deuterium, halogen group, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₆ to C ₆₀ aryl group, nuclear atom 5 to 60 heteroaryl group, C ₁ to C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ the arylboronic group, C _{6 ~} C ₆₀ aryl phosphine group of, C ₆ ~ C aryl phosphine oxide ₆₀ group and a C _{6 ~} substituted with one or more substituents selected from the group consisting of an aryl amine of the C ₆₀ or unsubstituted be ring Wherein when the substituents are plural, they are the same or different from each other;

n is an integer of 1 to 4, preferably 2 may be.

The content of the dopant is not particularly limited, but may be 1 to 10 parts by weight based on 100 parts by weight of the compound represented by Formula 1.

The structure of the organic electroluminescent device according to the present invention is not particularly limited, but non-limiting examples thereof may include a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode sequentially stacked. In this case, the emission layer may include a compound represented by Chemical Formula 1. 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 at an interface between the electrode and the organic material layer.

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.

In the present invention, "alkyl" is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples of such alkyl include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.

"Alkenyl" in the present invention is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples of such alkenyl include vinyl, allyl, isopropenyl, 2-butenyl, and the like.

"Alkynyl" in the present invention is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond. Examples of such alkynyl include ethynyl, 2-propynyl, and the like.

"Aryl" in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms combined with a single ring or two or more rings. In addition, a form in which two or more rings are pendant or condensed with each other may also be included. Examples of such aryls include phenyl, naphthyl, phenanthryl, anthryl and the like.

"Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are simply attached or condensed with each other may be included, and is also construed to include a form condensed with an aryl group. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like.

In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.

In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl and has a linear, branched or cyclic structure. Interpret as included. Examples of such alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

"Arylamine" in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.

"Cycloalkyl" in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine and the like.

"Heterocycloalkyl" in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons is N, O, Substituted with a hetero atom such as S or Se. Examples of such heterocycloalkyl include morpholine, piperazine and the like.

In the present invention, "alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 40 carbon atoms.

"Condensed ring" in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combination thereof.

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.

Synthesis Example 1 Preparation of Compound Mat-1

<Step 1>

Phthadialdehyde (50 g, 0.37 mol) and tetrahydrofuran (1 L) were added to a round bottom flask (3 L) and stirred, followed by dropwise addition of 4-biphenyl magnesium bromide (1 L, 1.5 M in THF, 1.5 mol) at room temperature. After stirring for 1 hour at room temperature, the reaction was terminated with an aqueous solution of ammonium chloride. After the reaction was completed, the mixture was extracted with ethyl acetate, dried over magnesium sulfate, and the organic solvent was concentrated to obtain the target compound.

<Step 2>

Methylene chloride (1 L) was added to the compound (210 g, 0.48 mol) obtained in <Step 1>, followed by stirring. Triethylamine (309 mL, 2.22 mol), acetic hydride (140 mL, 1.48 mol) and dimethylaminopyridine (9 g, 0.074 mol) were added thereto, followed by stirring for one hour. Then, the reaction was terminated using an aqueous sodium hydrogen carbonate solution, and the methylene chloride layer was extracted. This was dried over sodium sulfate, the organic solvent was filtered and concentrated, and then recrystallized with methylene chloride and hexane to obtain a white solid diacetate compound (155 g, yield 80%).

To methylene chloride (4L), diacetate (150 g, 0.28 mol) and trifluoromethanesulfonic acid (4 mL, 0.056 mol) obtained above were added, followed by stirring at room temperature for 10 minutes, which was filtered through silica gel. The filtrate was concentrated and then recrystallized from methanol / methylene chloride solution to give a yellow solid (114g, 82% yield).

¹ H NMR (CDCl 3): 7.25-7.60 (m, 12H), 7.69-7.80 (m, 6H), 7.95 (s, 1H), 8.00 (d, 1H), 8.07 (d, 1H), 8.46 (s, 1H); HRMS for C 32 H 22 [M] +: calcd 406, found 406.

<Step 3>

To dimethylformamide (1L), a yellow solid (110 g, 0.27 mol) and N-bromosuccinimide (48 g, 0.27 mol) obtained in <Step 2> were added thereto, and stirred at 60 ° C. for 5 hours. , Cooled to room temperature. Thereafter, the reaction solution was filtered through silica gel, concentrated, and dried under vacuum to obtain a compound.

The compound obtained above was dissolved in toluene (1 L) in a nitrogen atmosphere, and then 1-naphthalenyl boronic acid (51.6 g, 0.3 mol), tetrakistriphenylphosphine palladium (9.3 g, 8.1 mmol) and sodium carbonate were added thereto. (31.4 g, 0.3 mol) and water (300 mL) were added. The reaction mixture was stirred at reflux for 3 hours. The reaction solution was cooled to about 60 ° C., filtered through silica gel, and the toluene layer was extracted. The extract was concentrated to remove organic solvent and methanol was added to give a solid. The solid was filtered to give a yellowish brown, which was dissolved in methylene chloride, and methanol was added in small portions to obtain anthracene derivative Mat-1 (122 g, yield 85%) as a pale off-white solid.

Elemental Analysis for C 42 H 28: calcd C 94.70, H 5.30, found C 94.90, H 5.10;

HRMS for C42H28 [M] + calcd 532, found 532

Synthesis Example 2 Preparation of Compound Mat-2

Except for using 2-naphthalenyl boronic acid (51.6g, 0.3mol) instead of 1- naphthalenyl boronic acid was carried out the same process as <Step 3> of Synthesis Example 1 to obtain the target compound Mat-2 .

Elemental Analysis for C 42 H 28: calcd C 94.70, H 5.30, found C 94.90, H 5.10;

HRMS for C42H28 [M] + calcd 532, found 532

Synthesis Example 3 Preparation of Compound Mat-4

Except for using 9-phenanthrenyl boronic acid (66.6g, 0.3mol) instead of 1- naphthalenyl boronic acid was carried out the same procedure as in <Step 3> of Synthesis Example 1 to obtain the target compound Mat-4 .

Elemental Analysis for C 46 H 30: calcd C 94.81, H 5.19, found C 94.80, H 5.20;

HRMS for C46H30 [M] + calcd 582, found 582

Synthesis Example 4 Preparation of Compound Mat-9

Except for using 3- (naphthalen-2-yl) phenylboronic acid (74.4g, 0.3mol) instead of 1-naphthalenyl boronic acid, the same compound as in <Step 3> of Synthesis Example 1 -9 was obtained.

Elemental Analysis for C 48 H 32: calcd C 94.70, H 5.30, found C 94.74, H 5.25;

HRMS for C48H32 [M] + calcd 608, found 608

Synthesis Example 5 Preparation of Compound Mat-13

Synthesis Example 1 In <Step 1> of Synthesis Example 1 except that 3 (4- (naphthalen-1-yl) phenyl) magnesium bromide (1L, 1.5M in THF, 1.5mol) was used instead of 4-biphenyl magnesium bromide. The same procedure as in 2 was carried out to obtain Mat-13, the target compound.

Elemental Analysis for C 50 H 32: calcd C 94.90, H 5.10, found C 94.90, H 5.10;

HRMS for C50H32 [M] + calcd 632, found 632

Synthesis Example 6 Preparation of Compound Mat-19

In <Step 1> of Synthesis Example 1, 3 (4- (naphthalen-1-yl) phenyl) magnesium bromide (1L, 1.5M in THF, 1.5mol) was used instead of 4-biphenyl magnesium bromide. Except for using biphenyl-4-ylboronic acid (51.6g, 0.3mol) instead of 1- naphthalenyl boronic acid in the same process was carried out to obtain the target compound Mat-19.

Elemental Analysis for C 50 H 32: calcd C 94.90, H 5.10, found C 94.90, H 5.10;

HRMS for C50H32 [M] + calcd 632, found 632

Synthesis Example 7 Preparation of Compound Mat-24

The same procedure as in <Step 1> of Synthesis Example 2 was performed except that (4- (naphthalen-2-yl) phenyl) magnesium bromide (1L, 1.5M in THF, 1.5mol) was used instead of 4-biphenyl magnesium bromide. To obtain Mat-24, which is the target compound.

Elemental Analysis for C 50 H 32: calcd C 94.90, H 5.10, found C 94.90, H 5.10;

HRMS for C50H32 [M] + calcd 632, found 632

Synthesis Example 8 Preparation of Compound Mat-25

The same procedure as in <Step 1> of Synthesis Example 2 was performed except that (4- (naphthalen-2-yl) phenyl) magnesium bromide (1L, 1.5M in THF, 1.5mol) was used instead of 4-biphenyl magnesium bromide. To obtain Mat-25 as the target compound.

Elemental Analysis for C 50 H 32: calcd C 94.90, H 5.10, found C 94.90, H 5.10;

HRMS for C50H32 [M] + calcd 632, found 632

Synthesis Example 9 Preparation of Compound Mat-31

In (Step 1) of Synthesis Example 1, (4- (naphthalen-2-yl) phenyl) magnesium bromide (1L, 1.5M in THF, 1.5mol) was used instead of 4-biphenyl magnesium bromide. Except for using biphenyl-4-ylboronic acid (51.6g, 0.3mol) instead of 1- naphthalenyl boronic acid was carried out the same process to obtain the target compound Mat-31.

Elemental Analysis for C 52 H 34: calcd C 94.80, H 5.20, found C 94.80, H 5.20;

HRMS for C52H34 [M] + calcd 658, found 658

Examples 1 to 9 Fabrication of Organic Electroluminescent Green Light-Emitting Element

Compounds synthesized in Synthesis Examples 1 to 9 were subjected to high purity sublimation purification by a conventionally known method, and then an organic electroluminescent green light emitting device was manufactured according to the following procedure.

First, the glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 kPa was washed with distilled water ultrasonic waves. After the washing of 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-HIL (Doosan Co., Ltd.) on the ITO (anode) prepared as described above is thermally vacuum deposited to a thickness of 800 kPa to form a hole injection layer, and α-NPB ( N , N- , which is a hole transport 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.

Compounds Mat-1, Mat-2, Mat-4, Mat-9, Mat-13, Mat-19, Mat-24, Mat-25, Mat, respectively prepared in Synthesis Examples 1 to 9 as green host materials thereon Each of -31 was used, and a light emitting layer was formed by vacuum evaporation to a thickness of 300 kPa with 5% doping of C-545T as a dopant. 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.

The structure of NPB and C-545T used is as follows.

[Examples 10 to 18] Fabrication of Organic Electroluminescent Green Light-Emitting Element

Except for using FGD-1 instead of C-545T as a dopant for forming the light emitting layer, the organic electroluminescent device of Examples 10 to 18 was prepared in the same manner as in Examples 1 to 9.

The structure of FGD-1 used is as follows.

Comparative Example 1 Fabrication of Organic Electroluminescent Green Light Emitting Device

An organic electroluminescent device of Comparative Example was manufactured by the same method as Example 1, except that DS-FGH (Doosan Corp.) was used instead of compound Mat-1 as a green host material when forming the emission layer.

Comparative Example 2 Fabrication of Organic Electroluminescent Green Light Emitting Device

An organic electroluminescent device of Comparative Example was manufactured by the same method as Example 10, except that DS-FGH (Doosan Corporation) was used instead of compound Mat-1 as a green host material when forming the emission layer.

Experimental Example 1 Performance Evaluation of Organic Electroluminescent Green Light Emitting Device

For each organic electroluminescent green light emitting device manufactured in Examples 1 to 18 and Comparative Examples 1 and 2, luminous efficiency, driving voltage, and lifetime (97%) were measured at a current density of 10 mA / cm 2, and the results are shown in the following table. 1 is shown.

Table 1

	Host	Dopant	Voltage (V)	Efficiency (cd / A)	Lifespan (hours)
Example 1	Mat-1	C-545T	5.2	31.3	155
Example 2	Mat-2	C-545T	5.1	32.5	150
Example 3	Mat-4	C-545T	5.2	30.1	130
Example 4	Mat-9	C-545T	5.4	31.0	135
Example 5	Mat-13	C-545T	5.3	30.7	130
Example 6	Mat-19	C-545T	5.3	30.4	125
Example 7	Mat-24	C-545T	5.45	31.0	140
Example 8	Mat-25	C-545T	5.5	31.2	130
Example 9	Mat-31	C-545T	5.3	30.4	135
Example 10	Mat-1	FGD-1	4.8	33.0	160
Example 11	Mat-2	FGD-1	4.9	34.5	170
Example 12	Mat-4	FGD-1	4.8	32.1	155
Example 13	Mat-9	FGD-1	4.8	32.3	150
Example 14	Mat-13	FGD-1	4.9	32.0	150
Example 15	Mat-19	FGD-1	4.85	32.5	140
Example 16	Mat-24	FGD-1	4.95	32.1	145
Example 17	Mat-25	FGD-1	5.0	31.9	150
Example 18	Mat-31	FGD-1	5.1	32.3	140
Comparative Example 1	DS-FGH	C-545T	6.8	23.0	100
Comparative Example 2	DS-FGH	FGD-1	6.5	26.0	100

As shown in the table, the organic electroluminescent device of Examples 1 to 18 using the compound according to the present invention as a green host showed improved performance in terms of driving voltage and efficiency, and in terms of lifetime, It was confirmed that the organic EL device significantly improved.

The organic electroluminescent device of the present invention exhibits excellent properties in terms of luminous efficiency, brightness, power efficiency, driving voltage and lifespan by including the compound represented by Chemical Formula 1 having excellent heat resistance, luminous ability, and the like. Maximizing performance and lifespan can be achieved in the light emitting panel.

Claims (6)

1. anode; cathode; And one or more organic material layers interposed between the anode and the cathode,

   At least one of the one or more organic material layer is an organic electroluminescent device comprising a compound represented by the following formula (1):

   [Formula 1]

   

   In Chemical Formula 1,

   A plurality of R ₁ are the same or different from each other,

   R ₁ is phenyl or naphthyl,

   Ar ₁ is a substituent represented by any one of the formulas A-1 to A-6,

   

   However, Ar ₁ is

   

   Except in the same case.
2. The method of claim 1,

   Ar ₁ is a substituent represented by any one of the following Formulas B-1 to B-12,

   However, Ar ₁ is

   

   An organic electroluminescent device characterized in that the same case as that except.

   
3. The method of claim 1,

   The compound represented by Formula 1 is an organic electroluminescent device, characterized in that the compound represented by any one of the following formulas (2) to (4).

   [Formula 2]

   

   [Formula 3]

   

   [Formula 4]

   

   Wherein Ar ₁ is as defined in claim ₁ .
4. The method of claim 1,

   The compound represented by Formula 1 is an organic electroluminescent device, characterized in that the compound selected from the group consisting of the following compounds Mat-1 to Mat-34.

   

   
5. The method of claim 1,

   An organic electroluminescent device, wherein the organic material layer including the compound represented by Formula 1 is a light emitting layer.
6. The method of claim 1,

   The organic material layer is an organic electroluminescent device comprising a compound represented by the formula (5) as a dopant:

   [Formula 5]

   

   In Chemical Formula 5,

   Ar ₂ is selected from the group consisting of a substituted or unsubstituted C ₁₀ ~ C ₆₀ aromatic ring and a substituted or unsubstituted heteroaromatic ring having 10 to 60 nuclear atoms,

   Ar ₃ and Ar ₄ are each independently selected from the group consisting of a C ₆ ~ C ₆₀ aryl group and a heteroaryl group of 5 to 60 nuclear atoms,

   The aryl group and heteroaryl group of Ar ₃ to Ar ₄ are each independently deuterium, halogen group, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₆ to C ₆₀ aryl group, nuclear atom 5 to 60 heteroaryl group, C ₁ to C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ the arylboronic group, C _{6 ~} C ₆₀ aryl phosphine group, substituted with one or more substituents, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C _{6 ~} selected from the group consisting of an aryl amine of the C ₆₀ in or unsubstituted be ring Where the substituents are plural, they are the same or different,

   n is an integer of 1-4.