KR20120044517A - Novel compounds for organic electronic material and organic electroluminescent device using the same - Google Patents

Abstract

PURPOSE: An organic electronic material compound is provided to have good luminous efficiency, to reduce driving voltage of device, and to manufacture an organic electroluminescence diode device with improved power efficiency. CONSTITUTION: An organic electronic material compound is in chemical formula 1. In chemical formula 1, A ring is 5-membered heteroaromatic ring containing one selected from -O-, -S- and -N(L1-Ar1)-, Y is -O-, -S- or -N(L2-Ar2)-, R1-R3 is respectively hydrogen, deuterium, (C1-30) alkyl, halo (C1-30) alkyl, halogen, cyano, (C3-30) cycloalkyl, 5-7 membered heterocycloalkyl, (C2-30) alkenyl, (C2-30) alkynyl, (C6-30) aryl, (C1-30) alkoxy, (C6-30) aryloxy, (C3-30) heteroaryl, (C6-30) ar (C1-30) alkyl, (C6-30) arylthio, mono or the di (C1-30) alkyl amino, and mono or di (C6-30) arylamino, tri (C1-30) alkylsilyl, di (C1-30) alkyl (C6-30) arylsilyl, tri (C6-30) arylsilyl, nitro, or the hydroxy.

Description

Novel compounds for organic electronic material and organic electroluminescent device using the same

The present invention relates to a novel compound for organic electronic materials and an organic electroluminescent device comprising the same.

Among the display elements, an electroluminescence device (EL device) is a self-luminous display element that has a wide viewing angle, excellent contrast, and high response speed.Eastman Kodak Co., Ltd. in 1987 An organic EL device using a low molecular aromatic diamine and an aluminum complex as a light emitting layer formation material was first developed [Appl. Phys. Lett. 51, 913, 1987].

The organic EL element injects charge into an organic film formed between the electron injection electrode (cathode) and the hole injection electrode (anode) to generate excitons by pairing electrons and holes. Light is emitted by using light emission (phosphorescence or fluorescence) when the excitons are inactive. The organic EL device emits polarized light with a voltage of about 10V and a high luminance of about 100 to 10,000 cd / m 2, and emits light in a spectrum from blue to red by simply selecting a fluorescent material. The device can be formed on a flexible transparent substrate such as plastic, and can be driven at a lower voltage (less than 10V) compared to a plasma display panel or an inorganic EL display, and has a relatively low power consumption. It has a small and excellent color.

In organic EL devices, the most important factor that determines the performance of light emission efficiency, lifetime, etc. is a light emitting material. Some characteristics required for such a light emitting material include high quantum fluorescence yield in solid state, and mobility of electrons and holes. It should be high, not easily decomposed during vacuum deposition, and form a stable thin film.

Organic light emitting materials can be classified into high molecular materials and low molecular materials. Low molecular materials include pure organic light emitting materials that do not contain metal complexes and metals in terms of molecular structure. As such light emitting materials, light emitting materials such as chelate complexes such as tris (8-quinolinolato) aluminum complexes, coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives and oxadiazole derivatives are known. Has been reported to obtain visible region luminescence from blue to red.

In order to realize a full color OLED display, three kinds of RGB light emitting materials are used, and development of high efficiency long life RGB light emitting materials is an important task to improve the characteristics of the entire organic EL. The light emitting material can be classified into a host material and a dopant material in terms of its function. In general, a device structure having excellent EL characteristics is known to make a light emitting layer by doping a host with a dopant. Recently, the development of high efficiency and long life organic EL devices has emerged as an urgent task, and considering the level of EL characteristics required in medium and large OLED panels, it is urgent to develop materials that are much superior to existing light emitting materials. In this respect, the development of host materials is one of the most important factors to be solved. In this case, the desirable properties of the host material serving as a solvent and energy transporter in the solid state should be high in purity and have an appropriate molecular weight to enable vacuum deposition. In addition, high glass transition temperature and pyrolysis temperature should ensure thermal stability, high electrochemical stability is required for long life, easy to form amorphous thin film, good adhesion with other adjacent materials, Should not.

When an organic EL device is manufactured using a doping technique, energy transfer from the host molecule to the dopant in the excited state is less than 100%, and not only the dopant but also the host material emits light. In particular, in the case of a red light emitting device, since the host material emits light in a wavelength range where visibility is greater than that of the dopant, color purity is deteriorated by light emission of the host material. In addition, the light emission life and the sustainability need to be improved in practical application.

On the other hand, CBP is the most widely known host material for phosphorescent emitters, and high-efficiency OLEDs using a hole blocking layer such as BCP and BAlq are known, and high-performance OLEDs using BAlq derivatives as a host are known in Pioneer, Japan. Is known.

However, existing materials have advantages in terms of luminescence properties, but the glass transition temperature is low and the thermal stability is not very good, and thus has a disadvantage such that the material changes when undergoing a high temperature deposition process under vacuum. Since power efficiency = (π / voltage) × current efficiency in OLEDs, power efficiency is inversely proportional to voltage. However, low power consumption of OLEDs requires high power efficiency. Actually, OLEDs using phosphorescent materials have significantly higher current efficiency (cd / A) than OLEDs using fluorescent materials.However, when a conventional material such as BAlq or CBP is used as a host of phosphorescent materials, OLEDs using fluorescent materials Compared with the higher driving voltage, there was no significant advantage in terms of power efficiency (lm / w). In addition, in terms of lifespan in OLED devices, they are never satisfactory, and development of a more stable and more excellent host material is required.

Accordingly, an object of the present invention is to firstly provide a compound for organic electronic material having a good skeleton having an excellent luminous efficiency and device life, and having an appropriate color coordinate, in order to solve the above problems. It is to provide a high efficiency and long life organic electroluminescent element employing a compound for a material as a light emitting material.

The present invention relates to a compound for an organic electronic material represented by the following formula (1) and an organic electroluminescent device comprising the same, the compound for an organic electronic material according to the present invention has better luminous efficiency and excellent life characteristics of the material than the conventional material The driving life of the device is very excellent and there is an advantage of manufacturing an OLED device with improved power consumption by inducing an increase in power efficiency.

[Formula 1]

[In Formula 1,

로부터 선택된 어느 하나를 포함하는 5원의 헤테로방향족 고리이고;Ring A is -O-, -S- and

A 5 membered heteroaromatic ring comprising any one selected from;

이며;Y is -O-, -S- or

Is;

L ₁ and L ₂ are independently of each other a chemical bond, (C6-C30) arylene or (C3-C30) heteroarylene;

Ar ₁ And Ar ₂ independently of one another is a 5-7 membered heterocyclo comprising at least one selected from (C1-C30) alkyl, halo (C1-C30) alkyl, (C3-C30) cycloalkyl, N, O and S Alkyl, (C6-C30) aryl, (C1-C30) alkoxy, (C6-C30) aryloxy, (C3-C30) heteroaryl, (C6-C30) arylthio, mono or di (C1-C30) alkylamino , Mono or di (C6-C30) arylamino, (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, tri (C1-C30) alkylsilyl, di (C1 -C30) alkyl (C6-C30) arylsilyl or tri (C6-C30) arylsilyl;

R ₁ to R ₃ are independently of each other hydrogen, deuterium, (C1-C30) alkyl, halo (C1-C30) alkyl, halogen, cyano, (C3-C30) cycloalkyl, 5- to 7-membered heterocycloalkyl , (C2-C30) alkenyl, (C2-C30) alkynyl, (C6-C30) aryl, (C1-C30) alkoxy, (C6-C30) aryloxy, (C3-C30) heteroaryl, (C6- C30) Ar (C1-C30) alkyl, (C6-C30) arylthio, mono or di (C1-C30) alkylamino, mono or di (C6-C30) arylamino, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, nitro or hydroxy;

L ₁ And arylene, heteroarylene of L ₂ ; Ar ₁ And Ar ₂ of the alkyl, haloalkyl, cycloalkyl, heterocycloalkyl, aryl, alkoxy, aryloxy, heteroaryl, arylthio, alkylamino, arylamino, aralkyl, alkylaryl, trialkylsilyl, dialkylamino arylsilyl and Triarylsilyl; And alkyl, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, aryl and heteroaryl of R ₁ to R ₃ are independently of each other deuterium, (C 1 -C 30) alkyl, halo (C 1 -C 30) alkyl, halogen, cyan Furnace, (C3-C30) cycloalkyl, 5- to 7-membered heterocycloalkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C6-C30) aryl, (C1-C30) alkoxy, (C6-C30) aryloxy, (C3-C30) heteroaryl, (C6-C30) ar (C1-C30) alkyl, (C6-C30) arylthio, mono or di (C1-C30) alkylamino, mono or Group consisting of di (C6-C30) arylamino, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, nitro and hydroxy May be further substituted with one or more selected from;

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

Substituents including the "alkyl", "alkoxy" and other "alkyl" moieties described herein include all linear or pulverized forms, and "cycloalkyl" is not only a monocyclic system but also substituted or unsubstituted adamantyl Or several ring-based hydrocarbons such as substituted or unsubstituted (C7-C30) bicycloalkyl. "Aryl" described in the present invention is an organic radical derived from an aromatic hydrocarbon by one hydrogen removal, and a single or fused ring containing 4 to 7, preferably 5 or 6 ring atoms in each ring as appropriate. It includes a system, including a form in which a plurality of aryl is connected by a single bond. Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, peryleneyl, chrysenyl, naphthasenyl, fluoranthenyl, and the like. It is not limited to this. Said naphthyl includes 1-naphthyl and 2-naphthyl, anthryl includes 1-anthryl, 2-anthryl and 9-anthryl, and fluorenyl is 1-fluorenyl, 2- Fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl. The "heteroaryl" described in the present invention contains 1 to 4 heteroatoms selected from B, N, O, S, P (= O), Si, and P as aromatic ring skeleton atoms, and the remaining aromatic ring skeleton atoms are carbon. Meaning an aryl group which is 5 to 6 membered monocyclic heteroaryl, and polycyclic heteroaryl condensed with one or more benzene rings, which may be partially saturated. In addition, heteroaryl in the present invention also includes a form in which one or more heteroaryl is connected by a single bond. Such heteroaryl groups include divalent aryl groups in which heteroatoms in the ring are oxidized or quaternized to form, for example, N-oxides or quaternary salts. Specific examples include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetra Monocyclic heteroaryl such as zolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl, benzoisothia Zolyl, Benzoisoxazolyl, Benzoxazolyl, Isoindoleyl, Indolyl, Indazolyl, Benzothiadiazolyl, Quinolyl, Isoquinolyl, Cinolinyl, Quinazolinyl, Quinoxalinyl, Carbazolyl, Phenantridinyl , Polycyclic heteroaryls such as benzodioxolyl and the like, and their corresponding N-oxides (eg, pyridyl N-oxides, quinolyl N-oxides), quaternary salts thereof, and the like. .

In addition, the '(C1-C30) alkyl' groups described herein include (C1-C20) alkyl or (C1-C10) alkyl, and the '(C6-C30) aryl' group is a (C6-C20) aryl or (C6-C12) aryl. '(C3-C30) heteroaryl' group includes (C3-C20) heteroaryl or (C3-C12) heteroaryl, and the '(C3-C30) cycloalkyl' group is (C3-C20) cycloalkyl or (C3- C7) cycloalkyl. '(C2-C30) alkenyl or alkynyl' groups include (C2-C20) alkenyl or alkynyl, (C2-C10) alkenyl or alkynyl.

The compound for an organic electronic material according to the present invention may be selected from the following Chemical Formulas 2 to 9, but is not limited thereto.

  [Formula 2] [Formula 3] [Formula 4]

      [Formula 5] [Formula 6]

      [Formula 7] [Formula 8] [Formula 9]

[In Formula 2 to Formula 9,

L ₁ And L ₂ is independently of each other a chemical bond, (C6-C30) arylene or (C3-C30) heteroarylene;

Ar ₁ And Ar ₂ are independently of each other (C6-C30) aryl, (C3-C30) heteroaryl, mono or di (C1-C30) alkylamino, mono or di (C6-C30) arylamino, (C1-C30) alkyl (C6-C30) aryl, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl or tri (C6-C30) arylsilyl;

R ₁ to R ₃ are independently of each other hydrogen, deuterium, (C1-C30) alkyl, (C6-C30) aryl or (C3-C30) heteroaryl;

L ₁ And arylene, heteroarylene of L ₂ ; Ar ₁ And aryl, heteroaryl, alkylamino, arylamino, alkylaryl, trialkylsilyl, dialkylarylsilyl and triarylsilyl of Ar ₂ ; And alkyl, aryl and heteroaryl of R ₁ to R ₃ are independently of each other (C1-C30) alkyl, (C3-C30) cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-C30) aryl, ( C3-C30) heteroaryl, (C6-C30) ar (C1-C30) alkyl, mono or di (C1-C30) alkylamino, mono or di (C6-C30) arylamino, tri (C1-C30) alkylsilyl , Di (C1-C30) alkyl (C6-C30) arylsilyl and tri (C6-C30) arylsilyl may be further substituted with one or more selected from the group consisting of.]

및

는 하기 구조로부터 선택될 수 있으며, 이에 한정되지는 않는다.Specifically, the substituent

And

May be selected from the following structures, but is not limited thereto.

The compound for an organic electronic material according to the present invention may be more specifically exemplified as the following compound, but the following compound is not intended to limit the present invention.

The compound for an organic electronic material according to the present invention may be prepared, for example, as shown in Scheme 1 below, but is not limited thereto.

Scheme 1

[Ar ₁ , L ₁ , R ₁ to R ₃ and Y in Scheme 1 are the same as defined in Formula 1 above.]

In another aspect, 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 compound for an organic electronic material of Formula 1 and at least one phosphorescent dopant. It features.

In the organic electroluminescent device of the present invention, it may include at least one compound selected from the group consisting of an arylamine compound or a styrylarylamine compound, including a compound for the organic electronic material of Formula 1, at the same time, arylamine Specific examples of the compound or styrylarylamine compound are exemplified in identification numbers <212> to <224> of Patent Application No. 10-2008-0060393, but are not limited thereto.

In addition, in the organic electroluminescent device of the present invention, in the organic material layer, in addition to the compound for the organic electronic material of Formula 1, Group 1, Group 2, 4 cycle, 5 cycle transition metals, lanthanum series metals and organic metal of d-transition element It may further include one or more metals or complex compounds selected from the group consisting of, the organic material layer may include a light emitting layer and a charge generating layer.

An organic electroluminescent device comprising a compound for an organic electronic material of Formula 1 of the present invention is a subpixel, and includes Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, An organic EL device having an independent light emitting pixel structure in which at least one subpixel including at least one metal compound selected from the group consisting of Au and Ag is simultaneously patterned in parallel may be implemented.

In addition, an organic light emitting device that emits white light may be formed on the organic material layer by simultaneously including one or more organic light emitting layers including blue, red, or green light emitting compounds in addition to the organic electronic material compound. The compound emitting blue, green, or red light is exemplified in Application Nos. 10-2008-0123276, 10-2008-0107606, or 10-2008-0118428, but is not limited thereto.

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 &quot;) 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. Examples of the chalcogenide include SiO _x (1 ≦ _X ≦ ₂ ), AlO _X (1 ≦ _X ≦ 1.5), SiON, SiAlON, and the like, and examples of the metal halide include LiF, MgF ₂ , CaF ₂ , and fluoride. Rare earth metals and the like are preferable. Examples of the metal oxides include Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO and the like.

Further, in the organic electroluminescent device of the present invention, disposing a mixed region of an electron transfer compound and a reducing dopant or a mixed region of a hole transfer compound and an oxidative dopant on at least one surface of the pair of electrodes thus produced desirable. In this way, the electron transfer compound is reduced to an anion, thereby facilitating injection and transfer of electrons from the mixed region into the light emitting medium. In addition, since the hole transport compound is oxidized to become a cation, it is easy to inject and transfer holes from the mixed region to the light emitting medium. Preferred oxidative dopants include various Lewis acids and acceptor compounds. 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 generation layer.

The compound for an organic electronic material according to the present invention has an advantage of being able to manufacture an OLED device having good luminous efficiency and lowering driving voltage of the device and at the same time improving power efficiency.

Hereinafter, for the detailed understanding of the present invention, a compound for an organic electronic material according to the present invention, a method for preparing the same, and a light emitting property of the device will be described with reference to a representative compound of the present invention, but only for the purpose of illustrating the embodiments thereof. It does not limit the scope of the present invention.

Preparation Example 1 Preparation of Compound 2

compound 1-1 Manufacture

20 g (120 mmol) of carbazole in a round bottom flask (RBF), 102 g (360 mmol) of 4-bromoiodobenzene, 11.4 g (60 mmol) of CuI, K ₃ PO ₄ 76 g (360 mmol), ethylenediamine 14.4 g (240 mmol) and 600 mL of toluene were added thereto, and the mixture was stirred under reflux at 110 ° C. The reaction was terminated after 24 hours, filtered and the filtrate was extracted with EA. Washed with distilled water and dried over magnesium sulfate. Distillation under reduced pressure and column separation with MC / hexane afforded 32 g (82%) of compound 1-1 .

compound 2 Manufacture

2 g (12.8 mmol) of 1,6-dihydropyrrolo [2,3-e] indole (12.8 mmol), N- (4- in 1,6-dihydropyrrolo [2,3-e] indole in a round bottom flask (RBF) 16.5 g (51.2 mmol) N- (4-bromophenyl) carbazole, 4.9 g (25.6 mmol) CuI, K ₃ PO ₄ 13.6 g (64 mmol), 3.1 g (51.2 mmol) of ethylenediamine, and 70 mL of toluene were added thereto, and the mixture was stirred under reflux at 110 ° C. After 36 hours the reaction was terminated, filtered and the filtrate was extracted with EA. Washed with distilled water and dried over magnesium sulfate. Distillation under reduced pressure and column separation with MC / hexane afforded 3.4 g (42%) of compound 2 .

MS / FAB found 638.76, calculated 638.25

Preparation Example 2 Preparation of Compound 45

compound 2-1 Manufacture

20 g (98.7 mmol) of 2-bromonitrobenzene, 20.4 g (118 mmol) of 1-naphthaleneboronic acid, 4.5 g (3.95 mmol) of Pd (PPh ₃ ) ₄ , 34 g (247 mmol) of K ₂ CO ₃ was added to a round bottom flask (RBF), 240 mL of toluene, 120 mL of ethanol, and 120 mL of H ₂ O were added thereto, and the mixture was stirred at 100 ° C. for 3 hours. The reaction was terminated and extracted with EA. Washed with distilled water and dried over magnesium sulfate. Distillation under reduced pressure and column separation with MC / hexane yielded 22 g (89%) of compound 2-1 .

compound 2-2 Manufacture

20 g (80.2 mmol) of 1- (2-nitrophenyl) naphthalene), 150 mL of P (OEt) _{3 and} 150 mL of 1,2-dichlorobenzene were added to a round bottom flask (RBF). Stir at 140 ° C. for 24 h. The reaction mixture was distilled off to remove the solvent, and column separated with MC / hexane to give 11.3 g (65%) of compound 2-2 .

compound 2-3 Manufacture

10 g (47 mmol) benzo [c] carbazole, 44 g (141 mmol) 4,4′-dibromobiphenyl (RBF) in a round bottom flask , 4.5 g (23.5 mmol) of CuI, 29.9 g (141 mmol) of K ₃ PO ₄ , 5.6 g (94 mmol) of ethylenediamine, and 350 mL of toluene were added thereto, and the mixture was stirred under reflux at 110 ° C. After 24 hours, the reaction was terminated, the filter was washed with MC and THF, and the filtrate was extracted with EA. Washed with distilled water and dried over magnesium sulfate. Distillation under reduced pressure and column separation with MC / hexane afforded 32 g (82%) of compound 2-3 .

compound 45 Manufacture

12.9 g of N- (4'-bromobiphenyl-4-yl) -benzo [c] carbazole (N- (4'-bromobiphenyl-4-yl) -benzo [c] carbazole) in a round bottom flask (28.8 mmol), 2 g (11.5 mmol) of 1H-thieno [2,3-g] indole, 1.1 g (5.75 mmol) of CuI, K ₃ PO ₄ 7.5 g (34.5 mmol), ethylenediamine 1.4 g (23 mmol), and 60 mL of toluene were added thereto, and the mixture was stirred under reflux at 110 ° C. After 24 hours, the reaction was terminated, the filter was washed with MC and THF, and the filtrate was extracted with EA. Washed with distilled water and dried over magnesium sulfate. Distillation under reduced pressure and column separation with MC / hexane gave 2.9 g (46%) of compound 45 .

MS / FAB found 540.68, calculated 540.17

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

An OLED device having a structure using the light emitting material of the present invention was produced. First, a transparent electrode ITO thin film (15? It was used after. Next, the ITO substrate is installed in the substrate folder of the vacuum deposition equipment, and 2-TNATA [4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenylamine] is installed in the cell in the vacuum deposition equipment. And evacuated until the vacuum in the chamber reached 10 ⁻⁶ torr, followed by applying a current to the cell to evaporate 2-TNATA to deposit a 60 nm thick hole injection layer on the ITO substrate. NPB to another cell of the vapor-deposit device - into a [N, N '-bis (α -naphthyl) N, N'-diphenyl-4,4'-diamine], to evaporate NPB to apply a current to the cell, the hole injection layer A 20 nm-thick hole transport layer was deposited on top of the hole injection layer, and then the light emitting layer was deposited thereon as follows: Compound according to the invention as a host in one cell in a vacuum deposition apparatus (Example : into a compound 8), and another cell as a dopant _{(piq) 2 Ir (acac)} [bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate] , respectively After evaporation, the two materials were evaporated at different rates and doped at 4 to 10% by weight to deposit a 30 nm thick light emitting layer on the hole transport layer, followed by Alq [tris (8-hydroxyquinoline) — as an electron transport layer on the light emitting layer. aluminum (III)] is deposited to a thickness of 20 nm, and then Liq (lithium quinolate) is deposited to a thickness of 1 to 2 nm using an electron injection layer, and then another Al deposition is deposited to a thickness of 150 nm using another vacuum deposition apparatus. To produce an OLED device.

Each compound was vacuum sublimated and purified under 10 ^-6 torr to be used as an OLED light emitting material.

As a result, a current of 14.9 mA / cm ² flowed at a voltage of 7.1 V, and red emission of 1030 cd / m ² was confirmed.

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

An OLED device was manufactured in the same manner as in Example 1, except that a compound (for example, Compound 33 ) according to the present invention was used as a host material in the emission layer.

As a result, a current of 15.8 mA / cm ² flowed at a voltage of 6.5 V, and red light emission of 1120 cd / m ² was confirmed.

Example 3 Fabrication of OLED Device Using Organic Light Emitting Compound According to the Present Invention

An OLED device was manufactured in the same manner as in Example 1, except that a compound (for example, Compound 35 ) according to the present invention was used as a host material in the emission layer.

As a result, a current of 14.8 mA / cm ² flowed at a voltage of 6.7 V, and red light emission of 1080 cd / m ² was confirmed.

[Comparative Example 1] Light emission characteristics of OLED device using conventional light emitting material

CBP [4,4'-bis (carbazol-9-yl) biphenyl] is used instead of the compound of the present invention as a host material in one cell in the vacuum deposition equipment, and bis (2-methyl-8-quinoli as hole blocking layer is used. An OLED device was manufactured in the same manner as in Example 1, except that Neato) ( p -phenylphenolrato) aluminum (III) (BAlq) was used.

As a result, a current of 15.2 mA / cm ² flowed at a voltage of 7.5 V, and red light emission of 1000 cd / m ² was confirmed.

It was confirmed that the luminescence properties of the organic light emitting compounds developed in the present invention showed superior properties compared to the conventional materials. In addition, the device using the organic light emitting compound according to the present invention as a light emitting host material without using a hole blocking layer in the device structure not only has excellent light emission characteristics but also lowers the driving voltage to induce an increase in power efficiency to improve power consumption. Could.

Claims (10)

Compound for an organic electronic material represented by the formula (1).
[Formula 1]

[In the above formula (1)
Ring A is -O-, -S- and

A 5 membered heteroaromatic ring comprising any one selected from;
Y is -O-, -S- or

Is;
L ₁ And L ₂ is independently of each other a chemical bond, (C6-C30) arylene or (C3-C30) heteroarylene;
Ar ₁ And Ar ₂ independently of one another is a 5-7 membered heterocyclo comprising at least one selected from (C1-C30) alkyl, halo (C1-C30) alkyl, (C3-C30) cycloalkyl, N, O and S Alkyl, (C6-C30) aryl, (C1-C30) alkoxy, (C6-C30) aryloxy, (C3-C30) heteroaryl, (C6-C30) arylthio, mono or di (C1-C30) alkylamino , Mono or di (C6-C30) arylamino, (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, tri (C1-C30) alkylsilyl, di (C1 -C30) alkyl (C6-C30) arylsilyl or tri (C6-C30) arylsilyl;
R ₁ to R ₃ are independently of each other hydrogen, deuterium, (C1-C30) alkyl, halo (C1-C30) alkyl, halogen, cyano, (C3-C30) cycloalkyl, 5- to 7-membered heterocycloalkyl , (C2-C30) alkenyl, (C2-C30) alkynyl, (C6-C30) aryl, (C1-C30) alkoxy, (C6-C30) aryloxy, (C3-C30) heteroaryl, (C6- C30) Ar (C1-C30) alkyl, (C6-C30) arylthio, mono or di (C1-C30) alkylamino, mono or di (C6-C30) arylamino, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, nitro or hydroxy;
Arylene and heteroarylene of L ₁ and L ₂ ; Alkyl, haloalkyl, cycloalkyl, heterocycloalkyl, aryl, alkoxy, aryloxy, heteroaryl, arylthio, alkylamino, arylamino, aralkyl, alkylaryl, trialkylsilyl, dialkylaryl of Ar ₁ and Ar ₂ Silyl and triarylsilyl; And alkyl, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, aryl and heteroaryl of R ₁ to R ₃ are independently of each other deuterium, (C 1 -C 30) alkyl, halo (C 1 -C 30) alkyl, halogen, cyan Furnace, (C3-C30) cycloalkyl, 5- to 7-membered heterocycloalkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C6-C30) aryl, (C1-C30) alkoxy, (C6-C30) aryloxy, (C3-C30) heteroaryl, (C6-C30) ar (C1-C30) alkyl, (C6-C30) arylthio, mono or di (C1-C30) alkylamino, mono or Group consisting of di (C6-C30) arylamino, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, nitro and hydroxy May be further substituted with one or more selected from;
Wherein said heteroarylene, heterocycloalkyl and heteroaryl include one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P.] The method of claim 1,
A compound for an organic electronic material selected from the following formulas (2) to (9).
It may be, but is not limited to such.
[Formula 2] [Formula 3] [Formula 4]

[Formula 5] [Formula 6]

[Formula 7] [Formula 8] [Formula 9]

[In Formula 2 to Formula 9,
L ₁ And L ₂ is independently of each other a chemical bond, (C6-C30) arylene or (C3-C30) heteroarylene;
Ar ₁ and Ar ₂ are independently of each other (C6-C30) aryl, (C3-C30) heteroaryl, mono or di (C1-C30) alkylamino, mono or di (C6-C30) arylamino, (C1-C30 ) Alkyl (C6-C30) aryl, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl or tri (C6-C30) arylsilyl;
R ₁ to R ₃ are independently of each other hydrogen, deuterium, (C1-C30) alkyl, (C6-C30) aryl or (C3-C30) heteroaryl;
Arylene and heteroarylene of L ₁ and L ₂ ; Aryl, heteroaryl, alkylamino, arylamino, alkylaryl, trialkylsilyl, dialkylarylsilyl and triarylsilyl of Ar ₁ and Ar ₂ ; And alkyl, aryl and heteroaryl of R ₁ to R ₃ are independently of each other (C1-C30) alkyl, (C3-C30) cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-C30) aryl, ( C3-C30) heteroaryl, (C6-C30) ar (C1-C30) alkyl, mono or di (C1-C30) alkylamino, mono or di (C6-C30) arylamino, tri (C1-C30) alkylsilyl , Di (C1-C30) alkyl (C6-C30) arylsilyl and tri (C6-C30) arylsilyl may be further substituted with one or more selected from the group consisting of.] The method of claim 1,
The substituent

And

The compound for an organic electronic material, characterized in that it is selected from the following structure.

The method of claim 1,
Compound for organic electronic materials selected from the following compounds.

An organic electroluminescent device comprising the compound for organic electronic material according to any one of claims 1 to 4. 6. The method of claim 5,
The organic electroluminescent device includes 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 comprises at least one compound for an organic electronic material and at least one phosphorescent dopant. The method of claim 6,
An organic electroluminescent device further comprising at least one amine compound selected from the group consisting of an arylamine compound or a styrylarylamine compound in the organic layer. The method of claim 6,
An organic electric field further comprising at least one metal or a complex compound selected from the group consisting of Group 1, Group 2, 4, 5 cycle transition metals, lanthanum series metals and organic metals of d-transition elements in the organic layer. Light emitting element. The method of claim 6,
The organic material layer is an organic electroluminescent device comprising a light emitting layer and a charge generating layer. The method of claim 6,
The organic light emitting device of claim 1, further comprising at least one organic light emitting layer for emitting blue, red or green light to the organic material layer.