KR20130118059A - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Abstract

PURPOSE: An organic electroluminescent compound prevents the crystallization of a device by having high electron transfer efficiency and improving the current performance of a device by uniformly forming a layer. CONSTITUTION: An organic electroluminescent compound is represented by chemical formula 1. In chemical formula 1, L1 is a single bond, a substituted or unsubstituted 3-30 membered heteroarylene, a substituted or unsubstituted C6-30 arylene, or a substituted or unsubstituted C6-30 arylamine; Y1 and Y2 is -O-, -S-, -CR4R5-, -NR6-, or -SiR7R8-; each of R1-R3 is hydrogen, deuterium, halogen, a substituted or unsubstituted (C1-30)alkyl, a substituted or unsubstituted (C6-30)aryl, a substituted or unsubstituted 3-30 membered heteroaryl, -NR9R10, SR11, -OR12, or - SiR13R14R15, or form a monocyclic or polycyclic (C5-30) alicyclic or aromatic ring together with a neighboring substituent.

Description

Novel organic electroluminescent compounds and organic electroluminescent device using the same

The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device (hereinafter referred to as 'OLED') containing the same.

Among the display elements, an electroluminescence device (EL device) is a self-luminous display element and has advantages of wide viewing angle, excellent contrast and fast response speed. In 1987, Eastman Kodak Company developed an organic EL device using an aromatic diamine and an aluminum complex having low molecular weight as a light emitting layer forming material [Appl. Phys. Lett. 51, 913, 1987].

The most important factor determining the luminous efficiency in an OLED is a light emitting material. Fluorescent materials are widely used as the light emitting materials to date, but the development of phosphorescent materials is one of the best ways to improve the luminous efficiency theoretically up to four times. To date, the iridium (III) complex is widely known as a phosphorescent material, and for each RGB, (acac) Ir (btp) ₂ (bis (2- (2'-benzothienyl) -pyridinato-N, C- 3 ') Iridium (acetylacetonate)), Ir (ppy) ₃ (tris (2-phenylpyridine) iridium) and Firpic (bis (4,6-difluorophenylpyridinato-N, C2) picolinato Materials such as iridium) are known. In particular, many phosphorescent materials have recently been studied in Japan and Europe.

As the host material of the phosphor, CBP (4,4'-N, N'-dicarbazole-biphenyl) is the most widely known, and BCP (Batocuproine) and BAlq (Aluminum (III)) High-efficiency OLEDs with a hole blocking layer, such as bis (2-methyl-8-quinolinato) (4-phenylphenolate)), are known.In Japan, Pioneer and others use BAlq derivatives as hosts to provide high-performance OLEDs. It was developed.

However, existing materials are advantageous from the viewpoint of luminescence properties, but they have a disadvantage in that the materials are changed when the glass transition temperature is low and the thermal stability is not very good and the high temperature deposition process is performed under vacuum. In the OLED, power efficiency = [(π / voltage) x current efficiency], so power efficiency is inversely proportional to voltage. Therefore, to lower the power consumption of the OLED, power efficiency must be increased. In the case of conventional materials such as BAlq or CBP used as a host of a phosphorescent material, the OLED using an actual phosphorescent material has a higher current efficiency (cd / A) than an OLED using a fluorescent material, (Lm / w) because the driving voltage is higher than that of the conventional device. In addition, when used for an OLED device, the lifetime was never satisfactory.

Meanwhile, as the hole injection and transport material, copper phthalocyanine (CuPc), 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB), N, N'-diphenyl- N, N'-bis (3-methylphenyl)-(1,1'-biphenyl) -4,4'-diamine (TPD), 4,4 ', 4 "-tris (3-methylphenylphenylamino) tri Phenylamine (MTDATA), etc. A device incorporating such a material into the hole injection and transport layer has a problem of deterioration in efficiency and life, because when the organic EL device is driven at a high current, the anode and the hole injection layer This is because thermal stress is generated between them, and the lifespan of the device is drastically reduced due to such thermal stress.In addition, since organic materials used in the hole injection layer have very high hole mobility, The hole-electron charge balance is broken, resulting in lower quantum efficiency (cd / A).

Meanwhile, although US Patent Publication No. US2011 / 0279020 A1 mentions a compound for an OLED in which carbazole and carbazole are bonded by a carbon-carbon single bond, there is still a need for a new compound for OLED having improved luminous efficiency and device life. do.

United States Patent Application Publication No. US2011 / 0279020 A1 (Nov. 17, 2011)

 Appl. Phys. Lett. 51, 913, 1987

Accordingly, an object of the present invention is firstly to provide an organic electroluminescent compound having better luminous efficiency and device life than conventional materials, and secondly, to provide a high efficiency and long life organic electroluminescent device using the organic electroluminescent compound. It is.

As a result of earnest research to solve the above technical problem, the present inventors have found that the compounds of the following Chemical Formula 1 achieve the above-mentioned objects, and completed the present invention.

[Formula 1]

In Formula 1,

L ₁ is a single bond, substituted or unsubstituted 3-30 membered heteroarylene, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (C6-C30) arylamine, preferably 5-7 membered heteroarylene or diphenylamine containing a single bond, phenyl, nitrogen;

Y ₁ And Y ₂ are independently of each other —O—, —S—, —CR ₄ R ₅ —, —NR ₆ —, or —SiR ₇ R ₈ —, preferably —O—, —S—, —C (CH ₃ ) ₂ --N (C ₆ H ₅ )-, -Si (CH ₃ ) _2- , fluorene or -N- (4,6-diphenyl-1,3,5-triazine)-, Y ₁ and Y ₂ are different from each other;

R ₁ to R ₃ are independently of each other hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted 3-30 membered heteroaryl , -NR ₉ R ₁₀ , -SR ₁₁ , -OR ₁₂ Or -SiR ₁₃ R ₁₄ R ₁₅ Or, together with adjacent substituents, form a monocyclic or polycyclic (C5-C30) alicyclic or aromatic ring, wherein the carbon atoms of the monocyclic or polycyclic alicyclic or aromatic rings formed are selected from nitrogen, oxygen and sulfur May be replaced with one or more heteroatoms, preferably R ₁ to R ₃ are hydrogen, —C (CH ₃ ) ₃ , —Si (CH ₃ ) ₃ or phenyl;

R ₄ to R ₁₅ are substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted 3-30 membered heteroaryl, or monocyclic with adjacent substituents Polycyclic (C5-C30) alicyclic or aromatic rings may be formed, preferably (C1-C6) alkyl, phenyl or 3-6 membered heteroaryl;

Ar ₁ is substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted 3-30 membered heteroaryl, substituted or unsubstituted (C3-C30) Cycloalkyl, substituted or unsubstituted 5-7 membered heterocycloalkyl, or (C6-C30) cycloalkyl wherein one or more aromatic rings are fused, preferably phenyl or (C3-C6) cycloalkyl,

The heteroarylene, heteroaryl and heterocycloalkyl include one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P.

Substituted 3-30 membered heteroarylene of L ₁ , substituted (C6-C30) arylene, substituted (C6-C30) arylamine, and substituted (C1-C30) alkyl of R ₁ to R ₁₅ , substituted (C6 -C30) aryl, substituted 3-30 membered heteroaryl substituents independently of each other deuterium, halogen, (C1-C30) alkyl, halo (C1-C30) alkyl, (C6-C30) aryl, 3-30 membered heteroaryl 3-30 membered heteroaryl substituted with (C6-C30) aryl, (C6-C30) aryl substituted with 3-30 membered heteroaryl, (C3-C30) cycloalkyl, 5-7 membered heterocycloalkyl, Tri (C1-C30) alkylsilyl, tri (C6-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1-C30) alkyldi (C6-C30) arylsilyl, (C2 -C30) alkenyl, (C2-C30) alkynyl, cyanocarbazolyl, di (C1-C30) alkylamino, di (C6-C30) arylamino, (C1-C30) alkyl (C6-C30) arylamino , Di (C6-C30) arylboronyl, di (C1-C30) alkylboronyl, (C1-C30) alkyl (C6-C30) arylboronyl, (C6-C30) ar (C1-C30) Alkyl, (C1-C30) alkyl (C6-C30) aryl, carboxy, nitro and hydrate It may be selected from the group consisting of a hydroxyl group.

In addition, the '(C 1 -C 30) alkyl' groups described herein mean straight or branched alkyl, preferably (C 1 -C 20), more preferably (C 1 -C 6), for example methyl, Ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl.

A '(C2-C30) alkenyl' group described herein means a straight or branched chain alkenyl, preferably (C2-C20), more preferably (C2-C10), for example vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl and the like.

A '(C2-C30) alkynyl' group described herein means a straight or branched chain alkynyl, preferably (C2-C20), more preferably (C2-C10), for example ethynyl , 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl and the like.

'(C6-C30) aryl' group means a monocyclic or fused ring radical derived from an aromatic hydrocarbon, preferably (C6-C20), for example phenyl, biphenyl, terphenyl, naphthyl, flu Orenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetrasenyl, fluoranthenyl and the like.

'3-30 membered heteroaryl' group is an aryl group containing one or more heteroatoms selected from the group consisting of B, N, O, S, P (= O), Si and P as ring skeleton atoms and the remaining ring skeleton atoms being carbon Means. 5-30 member is preferable and 5-20 member is more preferable. The number of heteroatoms is preferably 1 to 4, and may be monocyclic or a fused ring system condensed with one or more benzene rings, and may be partially saturated. For example, furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxdiazolyl, triazinyl, tetrazinyl, triazolyl Monocyclic heteroaryl such as tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, benzoimida Zolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindoleyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinolinyl, quinazolinyl, quinol Fused ring heteroaryl such as salinyl, carbazolyl, phenoxazyl, phenantridinyl, and benzodioxolyl.

The "(C3-C30) cycloalkyl" group is cycloalkyl, preferably (C3-C20), more preferably (C3-C7), and examples thereof include cyclopropyl, cyclobutyl, cyclopentyl and the like.

'5-7 membered heterocycloalkyl' herein includes one or more heteroatoms selected from O, S and N, for example oxirane, aziridine, oxetane, azetidine, tetrahydrofuran, pyrroli Dine, thiolane, tetrahydropyran and the like.

'Halogen' herein includes F, Cl, Br and I atoms.

As an organic electroluminescent compound which concerns on this invention, the following compound is mentioned typically.

The organic electroluminescent compound according to the present invention may be prepared by a synthesis method known to those skilled in the art, and the following Scheme 1 is illustrated.

[Reaction Scheme 1]

In Scheme 1, L_One, Y_One, Y₂, R_One, R₂, R₃ And Ar_OneIs the same as defined in formula (1).

In addition, the present invention provides an organic electroluminescent device, the organic electroluminescent device according to the present invention comprises a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer includes at least one organic electroluminescent compound of Chemical Formula 1. The organic electroluminescent compound of Chemical Formula 1 of the present invention may be included in one or more of the light emitting layer and the hole transport layer. The organic material layer may include a light emitting layer, and in the light emitting layer, the compound of the formula may be used as a host material, and another host material may be added to the compound of Formula 1. In addition, the organic material layer includes a hole transport layer, it may include a compound of the formula as a hole transport material.

When the organic electroluminescent compound of Formula 1 is used as a host material in the light emitting layer, it further includes at least one phosphorescent dopant material. The phosphorescent dopant material applied to the organic electroluminescent device of the present invention is not particularly limited, but is preferably an ortho metal of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt). Use complexes. Among them, phosphorescent dopants selected from the following Chemical Formulas 2 and 3 are preferred in terms of luminous efficiency and color purity.

[Formula 2] [Formula 3]

In the above Formulas 2 and 3,

L is selected from the following structures;

R is hydrogen, substituted or unsubstituted (C1-C30) alkyl;

R ₁ to R ₁₈ are independently of each other hydrogen, deuterium, halogen, (C 1 -C 30) alkyl substituted or unsubstituted, cyano, substituted or unsubstituted (C 1 -C 30) alkoxy;

R ₂₀₁ to R ₂₁₁ are each independently hydrogen, deuterium, halogen, or a substituted or unsubstituted (C1-C30) alkyl group;

a and b are each independently an integer of 1 to 3, and when a or b are each an integer of 2 or more, each R may be the same or different from each other;

n is an integer of 0 to 3;

Specifically, it is preferable to use the following compounds as the dopant compound of Formula 2 or 3 above.

The present invention also provides a composition for an organic electroluminescent device, the composition comprising a first host material and a second host material, wherein the first host material uses the organic electroluminescent compound of the present invention. In this case, the weight ratio of the first host material and the second host material is preferably in the range of 1:99 to 99: 1.

The second host material may be any known phosphorescent host, but is preferably selected from phosphorescent hosts represented by the following general formulas (4) and (5) in view of luminous efficiency.

[Formula 4]

[Chemical Formula 5]

In the above formulas (4) and (5)

L is a single bond, a substituted or unsubstituted (C6-C30) arylene;

X ₁ , X ₂ and X ₃ are independently of each other C or N, and X ₁ , X ₂ and X ₃ At least one of is N;

R ₁ to R ₄ independently of one another are hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted 3-30 membered heteroaryl Is;

Y is NR ₅ , O or S, wherein R ₅ is substituted or unsubstituted (C6-C30) aryl;

m is 0 or 1 and n is 1.

Specifically, preferred examples of the second host material are as follows.

The organic electroluminescent device of the present invention may include one or more compounds selected from the group consisting of an arylamine-based compound and a styrylarylamine-based compound in addition to the compound of Formula 1 in the organic material layer.

In addition, in the organic electroluminescent device of the present invention, in addition to the compound of Formula 1, an organic compound selected from the group consisting of Group 1, Group 2, Group 4, Group 5 transition metal, Lanthanide series metal and d- And the organic layer may further include a light emitting layer and a charge generating layer.

In addition, the organic material layer may include at least one organic light emitting layer including a blue, red, or green light emitting compound in addition to the organic electroluminescent compound to form an organic electroluminescent device emitting white light.

In the organic electroluminescent device of the present invention, one layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer (hereinafter referred to as "surface layer ") is formed on the inner surface of at least one of the pair of electrodes, Or more. Concretely, it is preferable to dispose a halogenated metal layer or a metal oxide layer on the surface of the anode on the side of the light emitting medium layer and on the surface of the cathode on the side of the light emitting medium layer, with a chalcogenide (including oxide) layer of a metal of silicon and aluminum Do. Thus, stabilization of the drive can be obtained. Preferred examples of the chalcogenide include SiO _x (1? _X ? 2), AlO _x (1? _X ? 1.5), SiON or SiAlON, and preferred examples of the halogenated metal include LiF, MgF ₂ , CaF ₂ , Rare-earth metals, etc. Preferred examples of the metal oxides include Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO, and the like.

In addition, in the organic electroluminescent device of the present invention, a mixed region of the electron transfer compound and the reducing dopant or a mixed region of the hole transport compound and the oxidative dopant is disposed on at least one surface of the pair of electrodes thus fabricated desirable. In this way, since the electron transfer compound is reduced to an anion, it becomes easy to inject and transfer electrons from the mixed region to the light emitting medium. Further, since the hole transport compound is oxidized and becomes a cation, it becomes easy to inject and transport holes from the mixed region into the light emitting medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds, and preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, a white organic electroluminescent device having two or more light emitting layers may be manufactured using a reducing dopant layer as a charge generating layer.

The organic electroluminescent compound according to the present invention has an advantage of being able to manufacture an OLED device having excellent luminous efficiency and excellent life characteristics of the material, and having an excellent driving life of the device. In addition, the organic electroluminescent compound according to the present invention is used as a phosphorescent host material, a hole transporting material and a mixed host material, and has high electron transfer efficiency to prevent crystallization during device fabrication and to improve layer formation to improve current characteristics of the device. By improving the driving voltage of the device is reduced and at the same time has the advantage of manufacturing an OLED device with improved power efficiency.

Hereinafter, the organic electroluminescent compound according to the present invention, the method for producing the same, and the luminescent characteristics of the device will be described with reference to the representative compound of the present invention for a detailed understanding of the present invention. However, the following examples are merely for illustrating or explaining the present invention in detail, and the present invention is not limited thereto.

Preparation Example 1 Preparation of Compound C-17

Preparation of compounds 1-4

In a 250 ml round bottom flask (RBF) 12.5 g (34 mmol) of compound 1-3 (2-bromo-7,7-dimethyl-indeno [2,1-b] carbazole), 3.2 g (17 mmol) of CuI ), 21 g (102 mmol) of K ₃ PO ₄ , 3.4 ml (51 mmol) of ethylenediamine, and 100 ml of toluene were added and stirred at 120 ° C. for 18 hours. The reaction mixture was worked up with ethyl acetate (EA) / H ₂ O, water was removed with MgSO ₄ , and then distilled under reduced pressure. The crude product was silica filtered with methylene chloride (MC) to give 10 g (67%) of white solid compound 1-4.

Preparation of Compound C-17

7.5 g (17 mmol) of compound 1-4 (2-bromo-7,7-dimethyl-5-phenyl-indeno [2,1-b] carbazole) in 250 ml RBF, compound 3 (5H-benzoti Feneno [3,2-c] carbazole) 4.3 g (15.5 mmol), CuI 1.5 g (7.9 mmol), 2 ml (31 mmol) ethylenediamine, 10 g (47 mmol) K ₃ PO ₄ and 90 ml toluene Was added and stirred at 120 ° C for 22 hours. The reaction mixture was worked up with EA / H ₂ O, water was removed with MgSO ₄ , and then distilled under reduced pressure. The crude product was column chromatographed with MC: hexane (Hx) and then recrystallized in toluene to give 5.7 g (58%) of a white solid compound C-17.

MS / ESI measurement 614.73; Calculated 614.70

Preparation Example 2 Preparation of Compound C-27

6.8 g (15.5 mmol) of compound 1-4 (2-bromo-7,7-dimethyl-5-phenyl-indeno [2,1-b] carbazole) in 250 ml RBF, compound 2 (5H-benzofu 4.7 g (18.6 mmol) of Rho [3,2-c] carbazole), 174 mg (0.7 mmol) of Pd (OAc) ₂ , 9.8 g (46.5 mmol) of K ₃ PO ₄ and 80 ml of toluene were added thereto, and the mixture was heated to 120 ° C. Stir for 5 hours. The reaction mixture was worked up with EA / H ₂ O, water was removed with MgSO ₄ , and then distilled under reduced pressure. The crude product was column chromatographed with MC: Hx and then recrystallized in toluene to give 27.5 g (54%) of a white solid.

MS / ESI measurement 630.80; Calculated 630.21

Example 1 Fabrication of an OLED Device Using an Organic Electroluminescent Compound According to the Present Invention

An OLED device having a structure using the light emitting material of the present invention was fabricated. First, a transparent electrode ITO thin film (15? /?) Obtained from a glass for OLED (manufactured by Samsung Corning) was ultrasonically cleaned using trichlorethylene, acetone, ethanol and distilled water sequentially and stored in isopropanol Respectively. Next, the ITO substrate is mounted on the substrate holder of the vacuum deposition apparatus, and then N ¹ , N ^{1 ′} -([1,1′-biphenyl] -4,4′-diyl) bis ( N 1-(naphthalen- ¹ -yl) -N ⁴ , N ⁴ -diphenylbenzene-1,4-diamine) was added and evacuated until the vacuum in the chamber reached 10 ^-6 torr. Was applied and evaporated to deposit a 60 nm thick hole injection layer on the ITO substrate. Subsequently, Compound C-17 was placed in another cell in the vacuum deposition apparatus, and a 20 nm-thick hole transport layer was deposited on the hole injection layer by evaporation by applying a current to the cell. A hole injecting layer and a hole transporting layer were formed, and then a light emitting layer was deposited thereon as follows. 9- (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) -9'-phenyl-9H, 9'H-3 as a host in one cell in the vacuum deposition equipment Add 3'-bicarbazole, add D-1 as a dopant in each cell, and then evaporate the two materials at different rates to dope the sum of the two materials to 15% by weight on the hole transport layer. A 30 nm thick light emitting layer was deposited. Subsequently, one cell as the electron transporting layer on the light emitting layer, followed by 2- (4- (9,10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1 in one cell as the electron transporting layer on the light emitting layer -Phenyl-1H-benzo [d] imidazole was added, and another cell was charged with lithium quinolate, and the two materials were evaporated at the same rate to be doped so that the sum of the two materials was 50% by weight. A 30 nm electron transport layer was deposited. Then, lithium quinolate was deposited to a thickness of 2 nm as an electron injecting layer, and then an Al cathode was deposited to a thickness of 150 nm using another vacuum vapor deposition equipment to fabricate an OLED device. Each compound was used by vacuum sublimation purification under 10 ^-6 torr.

As a result, a current of 10.3 mA / cm ² flowed, and green light emission of 4600 cd / m ² was confirmed.

Example 2 Fabrication of OLED Device Using Organic Electroluminescent Compound According to the Present Invention

An OLED device was manufactured in the same manner as in Example 1, except that Compound C-27 was used as the hole transport layer.

As a result, a current of 15.2 mA / cm ² flowed, and green light emission of 7000 cd / m ² was confirmed.

Example 3 Fabrication of an OLED Device Using an Organic Electroluminescent Compound According to the Present Invention

N, N'-di (4-biphenyl) -N, N'-di (4-biphenyl) -4,4'-diaminobiphenyl was deposited to a thickness of 20 nm as a hole transport layer, and Compound C- as a light emitting layer. 17 and 9- (4,6-di ([1,1'-biphenyl] -4-yl) -1,3,5-triazin-2-yl) -9H-carbazole two substances in different cells In the same manner as in Example 1, except that a light emitting layer having a thickness of 30 nm was deposited on the hole transport layer by evaporating at the same rate and doping at 50% by weight, and using as a host and doping with D-75 at 15% by weight as a dopant. An OLED device was produced.

As a result, a current of 7.2 mA / cm ² flowed, and green light emission of 3000 cd / m ² was confirmed.

Example 4 Fabrication of OLED Device Using Organic Light Emitting Compound According to the Present Invention

Compound C-27 and 9- (4,6-di ([1,1'-biphenyl] -4-yl) -1,3,5-triazin-2-yl) -9H-carbazole as light emitting layer An OLED device was manufactured in the same manner as in Example 3, except that the material was evaporated at the same rate in each of the other cells to be doped at 50% by weight.

As a result, a current of 9.5 mA / cm ² flowed, and green light emission of 4000 cd / m ² was confirmed.

Comparative Example 1 Fabrication of OLED Device Using Conventional Light-Emitting Material

N, N'-di (4-biphenyl) -N, N'-di (4-biphenyl) -4,4'-diaminobiphenyl was deposited to a thickness of 20 nm as a hole transport layer and was transferred to the host as a light emitting material. 4,4'-N, N'-dicarbazole-biphenyl, compound Ir (ppy) 3 as a dopant, a light emitting layer having a thickness of 30 nm is deposited on the hole transport layer, and aluminum (III) is used as the hole blocking layer. An OLED device was manufactured in the same manner as in Example 1, except that 10) thick bis (2-methyl-8-quinolinato) 4-phenylphenolate was deposited.

As a result, a current of 6.4 mA / cm ² flowed, and green light emission of 2205 cd / m ² was confirmed.

It was confirmed that the luminescent properties of the compounds for organic electronic materials developed in the present invention exhibit excellent characteristics compared to the conventional materials. Moreover, the device using the compound for organic electronic materials which concerns on this invention is excellent in the light emission characteristic.

Claims (6)

An organic electroluminescent compound represented by the following Formula 1:
[Chemical Formula 1]

In Formula 1,
L ₁ is a single bond, substituted or unsubstituted 3-30 membered heteroarylene, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (C6-C30) arylamine;
Y ₁ And Y ₂ are independently of each other —O—, —S—, —CR ₄ R ₅ —, —NR ₆ — or —SiR ₇ R ₈ —, wherein Y ₁ and Y ₂ are different from each other;
R ₁ to R ₃ are independently of each other hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted 3-30 membered heteroaryl , -NR ₉ R ₁₀ , -SR ₁₁ , -OR ₁₂ Or -SiR ₁₃ R ₁₄ R ₁₅ Or a monocyclic or polycyclic (C5-C30) alicyclic or aromatic ring with adjacent substituents, wherein the carbon atoms of the monocyclic or polycyclic alicyclic or aromatic rings formed are selected from nitrogen, oxygen and sulfur May be replaced by one or more heteroatoms;
R ₄ to R ₁₅ are substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted 3-30 membered heteroaryl, or monocyclic with adjacent substituents Polycyclic (C5-C30) alicyclic or aromatic rings may be formed;
Ar ₁ is substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted 3-30 membered heteroaryl, substituted or unsubstituted (C3-C30) Cycloalkyl, substituted or unsubstituted 5-7 membered heterocycloalkyl, or (C6-C30) cycloalkyl wherein one or more aromatic rings are fused;
The heteroarylene, heteroaryl and heterocycloalkyl include one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P. The method of claim 1,
Substituted 3-30 membered heteroarylene of L ₁ , substituted (C6-C30) arylene, substituted (C6-C30) arylamine, and substituted (C1-C30) alkyl of R ₁ to R ₁₅ , substituted (C6 -C30) aryl, substituted 3-30 membered heteroaryl substituents independently of each other deuterium, halogen, (C1-C30) alkyl, halo (C1-C30) alkyl, (C6-C30) aryl, 3-30 membered heteroaryl 3-30 membered heteroaryl substituted with (C6-C30) aryl, (C6-C30) aryl substituted with 3-30 membered heteroaryl, (C3-C30) cycloalkyl, 5-7 membered heterocycloalkyl, Tri (C1-C30) alkylsilyl, tri (C6-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1-C30) alkyldi (C6-C30) arylsilyl, (C2 -C30) alkenyl, (C2-C30) alkynyl, cyanocarbazolyl, di (C1-C30) alkylamino, di (C6-C30) arylamino, (C1-C30) alkyl (C6-C30) arylamino , Di (C6-C30) arylboronyl, di (C1-C30) alkylboronyl, (C1-C30) alkyl (C6-C30) arylboronyl, (C6-C30) ar (C1-C30) Alkyl, (C1-C30) alkyl (C6-C30) aryl, carboxy, nitro and hydrate An organic electroluminescent compound selected from the group consisting of hydroxyl groups. The method of claim 1,
remind

Is an organic electroluminescent compound selected from the following structures:

Y ₁ , R ₁ and Ar ₁ are the same as defined in claim ₁ . The method of claim 1,
An organic electroluminescent compound selected from the following compounds.

An organic electroluminescent device comprising the organic electroluminescent compound of claim 1. A composition for an organic electroluminescent device comprising a first host material and a second host material, wherein the first host material is the organic electroluminescent compound of claim 1, and the second host material is a compound of the following Chemical Formulas 4 and 5 An organic electroluminescent device composition, characterized in that the selected:
[Chemical Formula 4]

[Chemical Formula 5]

In the above formulas (4) and (5)
L is a single bond, a substituted or unsubstituted (C6-C30) arylene;
X ₁ , X ₂ and X ₃ are independently of each other C or N, and X ₁ , X ₂ and X ₃ At least one of is N;
R ₁ to R ₄ independently of one another are hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted 3-30 membered heteroaryl Is;
Y is NR ₅ , O or S, wherein R ₅ is substituted or unsubstituted (C6-C30) aryl;
m is 0 or 1 and n is 1.