KR20100118700A - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel organic light emitting compound and an organic electroluminescent device comprising the same, in detail, the organic light emitting compound according to the invention is characterized in that represented by the formula (1) or (2).

  [Formula 1] [Formula 2]

In Formulas 1 and 2, A ₁ to A ₄ , B ₁ to B ₈ , L ₁ , L _2, and R ₁ to R ₃ are each as defined in the detailed description of the invention.

The organic light emitting compound according to the present invention has the advantage of being able to manufacture an OLED device having a good luminous efficiency and excellent life characteristics of the material and excellent driving life of the device.

Description

Novel organic electroluminescent compounds and organic electroluminescent device using the same

The present invention relates to a novel organic light emitting compound and an organic electroluminescent device comprising the same, in detail, the organic light emitting compound according to the invention is characterized in that represented by the formula (1) or (2).

  [Formula 1] [Formula 2]

Among the display elements, an electroluminescence device (EL device) is a self-luminous display element, which has a wide viewing angle, excellent contrast, and fast response speed.In 1987, Eastman Kodak Co., Ltd. He first developed an organic EL device using a low molecular aromatic diamine and an aluminum complex as a light emitting layer forming material [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 10 V 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.

The most important factor that determines the performance of light emission efficiency, lifespan, etc. in the organic EL device is a light emitting material. Some characteristics required for such a light emitting material include a high fluorescence quantum yield in the solid state, and mobility of electrons and holes. It should be high, not easily decomposed during vacuum deposition, and should form and stabilize a uniform 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 an organic light emitting compound having excellent luminous efficiency and device life, and having an appropriate color coordinate, in order to solve the above problems, and secondly, to solve the above organic light emitting compound. It is to provide a high efficiency and long life organic electroluminescent element employed as a light emitting material.

The present invention relates to an organic light emitting compound represented by the following Chemical Formula 1 or 2 and an organic electroluminescent device comprising the same, the organic light emitting compound according to the present invention has better luminous efficiency and excellent life characteristics of the device than the conventional host material There is an advantage that can manufacture an OLED device having a very excellent driving life.

 [Formula 1] [Formula 2]

[In Formula 1 and 2,

A ₁ to A ₅ and B ₁ to B ₈ are independently of each other N or CR ₂₁ , and when adjacent A ₁ to A ₅ or B ₁ to B ₈ are CR ₂₁ , each R ₂₁ includes or includes a fused ring; Unsubstituted (C3-C30) alkylene or (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, wherein the carbon atoms of the alkylene are from NR ₃₁ , O or S May be substituted with one or more heteroatoms selected, and the carbon atoms of the alkenylene may be substituted with N;

L ₁ and L ₂ are independently a chemical bond, a substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (C3-C30) heteroarylene each other, at the same time chemically bonding L ₁ and L ₂ is Not;

또는

이고;R ₁ to R ₃ , R ₂₁ and R ₃₁ are each independently Substituted or unsubstituted fused with one or more hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) cycloalkyl Substituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted aromatic ring 5 1-7 membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted aromatic ring (C3-C30) cycloalkyl, substituted or unsubstituted adamantyl , Substituted or unsubstituted (C7-C30) bicycloalkyl, cyano, NR ₁₁ R ₁₂ , BR ₁₃ R ₁₄ , PR ₁₅ R ₁₆ , P (= 0) R ₁₇ R ₁₈ [R ₁₁ to R ₁₈ are mutually Independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl.], Substituted or unsubstituted Tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted (C6 -C30) ar (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkyloxy, substituted or unsubstituted (C1-C30) alkylthio, substituted or unsubstituted (C6-C30) aryloxy, Substituted or unsubstituted (C6-C30) arylthio, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl,

or

ego;

W is-(CR ₅₁ R ₅₂ ) _m -,-(R ₅₁ ) C = C (R ₅₂ )-, -N (R ₅₃ )-, -S-, -O-, -Si (R ₅₄ ) (R ₅₅ )-, -P (R ₅₆ )-, -P (= 0) (R ₅₇ )-, -C (= 0)-, or -B (R ₅₈ )-,

R ₄₁ to R ₄₃ and R ₅₁ to R ₅₈ are the same as defined for R ₁ to R ₃ and R ₂₁ , wherein R ₅₁ to R ₅₈ each include or may not include adjacent substituents and fused rings (C3- C30) alkylene or (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;

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

m is an integer of 0, 1 or 2.]

및

는 서로 독립적으로 하기 구조로 예시될 수 있다.In addition, specifically

And

May be exemplified by the following structures independently of each other.

[R ₄₃ and R ₅₁ to R ₅₈ are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl R ₅₁ to R ₅₈ may be each linked to (C3-C30) alkylene or (C3-C30) alkenylene, which may or may not include adjacent substituents and fused rings, to form an alicyclic ring and a monocyclic or polycyclic aromatic ring. Can form.]

Substituents comprising the "alkyl", "alkoxy" and other "alkyl" moieties described herein include both straight and pulverized forms.

"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, the heteroaryl in the present invention also includes a form in which one or more heteroaryls are linked 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. .

Also described herein are “(C1-C30) alkyl, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C6-C30) ar (C1-C30) Alkyl, such as) alkyl, (C1-C30) alkyloxy, (C1-C30) alkylthio ”, etc., may be limited to 1 to 20 carbon atoms, and may be limited to 1 to 10 carbon atoms. “(C6-C30) aryl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, (C6-C30) ar (C1-C30) alkyl, (C6-C30) Aryl, such as aryloxy, (C6-C30) arylthio ", may be limited to 6 to 20 carbon atoms, and may be limited to 6 to 12 carbon atoms. Heteroaryl of "(C3-C30) heteroaryl" may be limited to 4 to 20 carbon atoms, it may be limited to 4 to 12 carbon atoms. The cycloalkyl of "(C3-C30) cycloalkyl" may be limited to 3 to 20 carbon atoms, and may be limited to 3 to 7 carbon atoms. Alkenyl or alkynyl of "(C2-C30) alkenyl or alkynyl" may be limited to 2 to 20 carbon atoms, and may be limited to 2 to 10 carbon atoms.

In addition, the description of "substituted or unsubstituted" described in the present invention, the substituents of L ₁ , L ₂ , R ₁ to R ₃ , R ₁₁ to R ₁₈ , R ₂₁ and R ₃₁ are each independently deuterium, halogen, Halogen-substituted or unsubstituted (C1-C30) alkyl, (C6-C30) aryl, (C6-C30) aryl-substituted or unsubstituted (C3-C30) heteroaryl, 5- to 7-membered heterocycloalkyl , 5- to 7-membered heterocycloalkyl fused with one or more aromatic rings, (C3-C30) cycloalkyl, (C6-C30) cycloalkyl with one or more aromatic rings, tri (C1-C30) alkylsilyl, Di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, adamantyl, (C7-C30) bicycloalkyl, (C2-C30) alkenyl, (C2-C30) Alkynyl, cyano, carbazolyl, NR ₆₁ R ₆₂ , BR ₆₃ R ₆₄ , PR ₆₅ R ₆₆ , P (= O) R ₆₇ R ₆₈ [R ₆₁ to R ₆₈ are independently substituted or unsubstituted (C1 -C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or non- Substituted (C3-C30) heteroaryl], (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, (C1-C30) alkyloxy, (C1- C30) alkylthio, (C6-C30) aryloxy, (C6-C30) arylthio, (C1-C30) alkoxycarbonyl, (C1-C30) alkylcarbonyl, (C6-C30) arylcarbonyl, (C6 -C30) aryloxycarbonyl, (C1-C30) alkoxycarbonyloxy, (C1-C30) alkylcarbonyloxy, (C6-C30) arylcarbonyloxy, (C6-C30) aryloxycarbonyloxy, carbon It means further substituted with one or more selected from the group consisting of a compound, nitro or hydroxy, or a substituent adjacent to each other is connected to form a ring.

는 하기 구조에서 선택되며, 이에 한정되지는 않는다.remind

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

또는

이고, W 및 R₄₃은 화학식 1 및 2에서의 정의와 동일하다.][R ₂₁ and R ₃₁ independently of one another are halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) cycloalkyl Fused substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, NR ₁₁ R ₁₂ [R ₁₁ and R ₁₂ are independently substituted or unsubstituted (C1-C30) C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl], substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted Di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyloxy, substituted or unsubstituted (C6 -C30) aryloxy, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl,

or

And W and R ₄₃ are the same as defined in Formulas 1 and 2.]

또는

는 하기 구조에서 선선택되며, 이에 한정되지는 않는다.remind

or

Is selected from the following structure, but is not limited thereto.

또는

이고, W 및 R₄₃은 화학식 1 및 2에서의 정의와 동일하다.][R ₁ to R ₃ are independently of each other substituted or unsubstituted (C1-C30) alkyl or substituted or unsubstituted (C6-C30) aryl; R ₂₁ is hydrogen, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) cycloalkyl substituted with one or more fused or Unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, NR ₁₁ R ₁₂ [R ₁₁ to R ₁₈ are independently substituted or unsubstituted (C1-C30) alkyl, substituted Or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl.], Substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1- C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted (C6-C30) aryloxy,,

or

And W and R ₄₃ are the same as defined in Formulas 1 and 2.]

The organic light emitting compound according to the present invention may be more specifically exemplified as the following compound, but the following compound does not limit the present invention.

The organic light emitting compound according to the present invention can be prepared as shown in Scheme 1 below.

Scheme 1

[A ₁ to A ₄ , B ₁ to B ₈ , L ₁ , L ₂ and R ₁ to R ₃ in Scheme 1 are the same as defined in Formulas 1 and 2, and X is a halogen.]

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 light emitting compound of Formula 1 or 2 above. The organic material layer may include a light emitting layer, and the light emitting layer may include one or more dopants having at least one organic light emitting compound of Formula 1 or 2 as a host. The dopant applied to the organic electroluminescent device of the present invention is not particularly limited, but the dopant applied to the organic electroluminescent device of the present invention is preferably selected from the compound represented by the following formula (3).

[Formula 3]

M ¹ L ¹⁰¹ L ¹⁰² L ¹⁰³

Wherein M ¹ is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16, and the ligands L ¹⁰¹ , L ¹⁰² and L ¹⁰³ Are independently selected from the following structures.

[R ₂₀₁ to R ₂₀₃ are each independently hydrogen, (C1-C30) alkyl unsubstituted or substituted, (C6-C30) aryl or unsubstituted (C6-C30) aryl or halogen;

R ₂₀₄ to R ₂₁₉ are each independently hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or Unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted mono or substituted or unsubstituted di- (C1-C30) alkylamino, substituted or unsubstituted Mono or di- (C6-C30) arylamino, SF ₅ , substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted Or unsubstituted tri (C6-C30) arylsilyl, cyano or halogen;

R ₂₂₀ to R ₂₂₃ are each independently hydrogen, a substituted or unsubstituted (C1-C30) alkyl, or a (C1-C30) aryl optionally substituted (C6-C30) aryl;

R ₂₂₄ and R ₂₂₅ are independently of each other hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen, or R ₂₂₄ and R ₂₂₅ contain or contain fused rings Unsubstituted (C3-C12) alkylene or (C3-C12) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;

R ₂₂₆ is substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C5-C30) heteroaryl or halogen;

R ₂₂₇ to R ₂₂₉ are each independently hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen;

,

또는

이며, R₂₃₁ 내지 R₂₄₂는 서로 독립적으로 수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬, (C1-C30)알콕시, 할로겐, 치환 또는 비치환된(C6-C30)아릴, 시아노, 치환 또는 비치환된(C5-C30)시클로알킬이거나, 인접한 치환체와 알킬렌 또는 알케닐렌으로 연결되어 스피로 고리 또는 융합고리를 형성할 수 있거나, R₂₀₇ 또는 R₂₀₈과 알킬렌 또는 알케닐렌으로 연결되어 포화 또는 불포화의 융합고리를 형성할 수 있다.]Q is

,

or

R ₂₃₁ to R ₂₄₂ are each independently hydrogen, halogen substituted or unsubstituted (C1-C30) alkyl, (C1-C30) alkoxy, halogen, substituted or unsubstituted (C6-C30) aryl, cyano , Substituted or unsubstituted (C5-C30) cycloalkyl, or may be linked to adjacent substituents with alkylene or alkenylene to form a spiro ring or fused ring, or to R ₂₀₇ or R ₂₀₈ with alkylene or alkenylene To form saturated or unsaturated fused rings.]

The dopant compound of Formula 3 may be exemplified as a compound having the following structure, but is not limited thereto.

In the organic electroluminescent device of the present invention, it may include one or more compounds selected from the group consisting of an organic light emitting compound of Formula 1 or 2, and at the same time arylamine-based compound or styrylarylamine-based compound. The arylamine-based compound or styrylarylamine-based compound is exemplified in Patent Application Nos. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but is not limited thereto.

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

In addition, an organic electroluminescent device that emits white light may be formed by simultaneously including one or more organic light emitting layers including blue, red, or green light emitting compounds in addition to the organic light emitting compound. The compound emitting blue, green or red light is illustrated 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, at least one inner surface of a pair of electrodes is selected from a chalcogenide layer, a halogenated metal layer, and a metal oxide layer (hereinafter, these are referred to as "surface layers"). It is preferable to arrange | position the above. Specifically, it is preferable to dispose a chalcogenide (containing oxide) layer of a metal of silicon and aluminum on the anode surface of the light emitting medium layer side and a metal halide or metal oxide layer on the cathode surface of the light emitting medium layer side. Do. As a result, drive stabilization 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, the reducing dopant layer The white organic electroluminescent device having two or more light emitting layers may be manufactured using the charge generating layer.

The organic light emitting compound according to the present invention has the advantage of being able to manufacture an OLED device having a good luminous efficiency and excellent life characteristics of the material and excellent driving life of the device.

Hereinafter, the organic light emitting compound according to the present invention, a method for preparing the same and a light emitting property of the device are described for the detailed understanding of the present invention, but the present invention is only intended to illustrate the embodiments of the present invention. It does not limit the scope of the invention.

Preparation Example 1 Preparation of Compound 10

compound 1-1 Manufacture

20 g (84.77 mmol) of 1,3-dibromobenzene was dissolved in 500 mL of THF, and then cooled to -78 ° C. 33.9 mL (84.77 mmol) of n-BuLi 2.5M was slowly added thereto, followed by stirring at −78 ° C. for 1 hour. 29.9 g of chlorotriphenylsilane ((C ₆ H ₅ ) ₃ SiCl) was dissolved in 100 mL of THF and added to the reaction mixture. After slowly raising to room temperature, the mixture was stirred for 12 hours. Extracted with EA, washed with distilled water and NaCl aqueous solution, dried over anhydrous MgSO ₄ and distilled under reduced pressure. Recrystallization with MC: MeOH = 1: 10 gave 18 g (95%) of compound 1-1 .

compound 1-2 Manufacture

20 g (90.06 mmol) of Compound 1-1 were dissolved in 600 mL of THF, and then cooled to -78 ° C. 43.2 mL (108.08 mmol) of n-BuLi 2.5M was slowly added thereto, followed by stirring at -78 ° C for one hour. 16.06 mL (144.11 mmol) of trimethylborate was added. After slowly raising to room temperature, the mixture was stirred for 12 hours. Extracted with EA, washed with distilled water and NaCl aqueous solution, dried over anhydrous MgSO ₄ and distilled under reduced pressure. MC: Hexane = 1: 10 in re-crystallization to obtain the compound 1-2 12 g (35%).

compound 1-3 Manufacture

3.3 g (83.90 mmol) of NaH (60% in mineral oil) were diluted in 10 mL of DMF. 11.2 g (67.12 mmol) of carbazole were dissolved in 60 mL of DMF and added to the reaction solution. Stirred at room temperature for 1 hour. 10 g (67.12 mmol) of 2,4-dichloropyrimidine was dissolved in 60 mL of DMF, and then added to the reaction solution. After stirring at room temperature for 4 hours, 40 mL of distilled water was added thereto. Extracted with MC, washed with distilled water and NaCl aqueous solution, dried over anhydrous MgSO ₄ and distilled under reduced pressure, purified by column chromatography to give compound 1-3 4.0 g (21%).

compound 10 Manufacture

Compound 1-3 3.8 g (13.58 mmol), compound 1-2 6.2 g (16.30 mmol), Pd (PPh 3) 4 784 mg (0.67 mmol), 2M Na 2 CO 3 aqueous solution of 70 mL, 50 mL EtOH and toluene 200 Add mL and stirred at reflux for 12 hours at 120 ℃. After cooling to room temperature, extracted with EA, washed with distilled water and aqueous NaCl solution and recrystallized with EA to obtain compound 10 5.5 g (69%).

Preparation Example 2 Preparation of Compound 16

compound 2-1 Manufacture

25 g (157.6 mmol) of 2-chloro-3-nitropyridine, 24.9 g (204.9 mmol) of phenylboronic acid, 5.4 g (4.73 mmol) of Pd (PPh ₃ ) ₄ , 54.48 g (394.2 mmol) of K ₂ CO ₃ , distilled water 150 mL, toluene 300 mL and ethanol 100 mL were added and stirred under reflux. After 12 hours, the mixture was cooled to room temperature and distilled water was added thereto. Extracted with MC, dried over anhydrous MgSO ₄ and distilled under reduced pressure. Purification by column chromatography gave 30 g (149.85 mmol, 95.45%) of compound 2-1 .

compound 2-2 Manufacture

30 g (149.85 mmol) of compound 2-1 were mixed with 150 mL of triethylphosphite and stirred at 180 ° C. for 4 hours. After cooling to room temperature, the mixture was distilled under reduced pressure and purified by column chromatography to obtain 2.1 g (12.48 mmol, 8.37%) of the compound 2-2 .

compound 2-3 Manufacture

Synthesis Example 1 was prepared in the same manner as compound 1-3 to obtain 2.6 g (7.99 mmol, 60.1%) of compound 2-3 .

compound 16 Manufacture

Compound 16 3.1 g (5.33 mmol, 67%) was obtained by the same method as compound 10 in Preparation Example 1.

Preparation Example 3 Preparation of Compound 19

compound 3-1 Manufacture

30 g (148.5 mmol) of bromo-2-nitrobenzene, 30.6 g (178.2 mmol) of 1-naphthyleneboronic acid, 5.14 g (4.45 mmol) of Pd (PPh ₃ ) ₄ , aqueous 2M K ₂ CO ₃ solution (297.01 mmol) 500 mL of toluene and 200 mL of ethanol were added thereto, and the mixture was stirred under reflux. After 4 hours, the mixture was cooled to room temperature and distilled water was added. Extracted with EA, dried over anhydrous MgSO ₄ and distilled under reduced pressure. Purification by column chromatography gave 31 g (123.3 mmol, 84.03%) of compound 3-1 .

compound 3-2 Manufacture

31 g (124.3 mmol) of Compound 3-1 and 300 mL of triethylphosphite were added thereto, and the mixture was stirred under reflux. After 10 hours, the mixture was cooled to room temperature, and the organic solvent was distilled off under reduced pressure. Distilled water was added and extracted with EA, dried over anhydrous MgSO ₄ and distilled under reduced pressure. Purification by column chromatography gave 18 g (82.84 mmol, 66.81%) of compound 3-2 .

compound 3-3 Manufacture

19 g (51.04 mmol, 61.6%) of Compound 3-3 was obtained by the same method as Compound 1-3 in Preparation Example 1.

compound 19 Manufacture

Synthesized in Production Example 1 in the same manner as compound 10 to give compound 19 16.3 g (25.9 mmol, 50.1 %).

Preparation Example 4 Preparation of Compound 61

compound 4-1 Manufacture

19 g (42.54 mmol) of compound 19 were dissolved in 200 mL of DMF and 8.33 g (46.80 mmol) of NBS were added. After stirring for 10 hours at room temperature, the organic solvent was distilled under reduced pressure. Distilled water was added and extracted with EA. It was dried over anhydrous MgSO ₄ and distilled under reduced pressure. Purification by column chromatography gave 20 g (38.06 mmol, 89.47%) of compound 4-1 .

compound 4-2 Manufacture

Compound 4-2 (8.31 mmol, 42.86%) was obtained by synthesizing according to the same method as Compound 1-2 in Preparation Example 1.

compound 4-3 Manufacture

In Preparation Example 3, the compound 4-1 was synthesized in the same manner as the compound 4-3, 7 g (12.33 mmol, 75.62%).

compound 4-4 Manufacture

In Preparation Example 3, the compound 4-4 (7.46 mmol, 58.33%) was obtained by the same method as the compound 3-2 .

compound 61 Manufacture

Compound 4-4 4 g (7.46 mmol), 1.25 mL (11.20 mmol) iodobenzene, 0.71 g (11.20 mmol) copper, 0.15 g (0.59 mmol) 18-crown-6, 3.1 g (11.20 mmol) K ₂ CO ₃ ) And 100 mL of 1,2-dichlorobenzene were stirred and refluxed at 180 ° C. for 15 hours. After cooling to room temperature, distillation under reduced pressure, extraction with EA and washing with distilled water. The residue obtained by drying over anhydrous MgSO ₄ and distillation under reduced pressure was purified by column chromatography to give 3.6 (61.88 mmol, 78.88%) of Compound 61 .

Preparation Example 5 Preparation of Compound 62

compound 5-1 Manufacture

Compound 5-1 11 g (38.02 mmol, 89.22%) was obtained by the same method as compound 3-1 in Preparation Example 3, except that dibenzo [b, d] furan-4-ylboronic acid was used.

compound 5-2 Manufacture

In Preparation Example 3, the compound 5-2 was synthesized in the same manner as the compound 3-2 , to obtain 8 g (31.09 mmol, 81.78%).

compound  5-3 Manufacture

7.4 g (20.01 mmol, 65.66%) of Compound 5-3 was obtained by the same method as Compound 1-3 in Preparation Example 1

compound 62 Manufacture

Synthesis was carried out in the same manner as in Compound 10 in Preparation Example 1 to obtain 5.8 g (8.65 mmol, 43.28%) of compound 62 .

The organic light emitting compounds 1 to compound 70 were prepared using the methods of Preparation Examples 1 to 5, and ¹ H NMR and MS / FAB of the organic light emitting compounds prepared in Table 1 are shown.

TABLE 1

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 Ω / □) obtained from an OLED glass (manufactured by Samsung Corning Corporation) was subjected to ultrasonic cleaning using trichloroethylene, acetone, ethanol and distilled water sequentially, and then stored in isopropanol. It was used after.

Next, the ITO substrate is placed in the substrate folder of the vacuum deposition equipment, and the 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) tree having the following structure is installed in the cell in the vacuum deposition equipment. Phenylamine (2-TNATA) was added and evacuated until the vacuum in the chamber reached 10 ^-6 torr. Then, a current was applied to the cell to evaporate 2-TNATA to inject a 60 nm thick hole injection layer onto the ITO substrate. Subsequently, the following structures N , N' -bis (α-naphthyl) -N , N' -diphenyl-4,4'-diamine (NPB) were added to another cell in the vacuum deposition apparatus, and NPB was evaporated by applying a current to deposit a 20 nm thick hole transport layer on the hole injection layer.

After the hole injection layer and the hole transport layer were formed, the light emitting layer was deposited thereon as follows. Compound 12 according to the present invention is put into one cell in a vacuum deposition apparatus as a host, and compound Ir (ppy) ₃ having the following structure as a dopant is put into another cell, respectively, and then the two materials are evaporated at different rates to 4 to 10 A 30 nm thick light emitting layer was deposited on the hole transport layer by depositing by weight%.

Subsequently, bis (2-methyl-8-quinolinate) ( p -phenylphenolrato) aluminum (III) (BAlq) was deposited to a thickness of 5 nm on the light emitting layer as a hole blocking layer, and as the electron transport layer, Tris (8-hydroxyquinoline) aluminum (III) (Alq) was deposited to a thickness of 20 nm, and then a compound lithium quinolate (Liq) having the following structure was deposited to a thickness of 1 to 2 nm using an electron injection layer. An OLED was fabricated by depositing an Al cathode to a thickness of 150 nm using another vacuum deposition equipment.

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

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

Except for the hole blocking layer, an OLED was manufactured in the same manner as in Example 1.

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

Compound 12 and dopant according to the invention as host in the emissive layer An OLED was manufactured in the same manner as in Example 1, except that Compound 19 and (piq) ₂ Ir (acac) were used instead of Ir (ppy) ₃ .

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

Except for the hole blocking layer, an OLED was manufactured in the same manner as in Example 3.

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

An OLED device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound of the present invention as a host material in one cell in a vacuum deposition apparatus.

Comparative Example 2 Light Emitting Characteristics of OLED Devices Using Conventional Light-Emitting Materials

An OLED device was manufactured in the same manner as in Example 3, except that CBP was used instead of the compound of the present invention as a host material in one cell in the vacuum deposition equipment.

The luminous efficiency of the organic light emitting compound according to the present invention prepared in Examples 1 to 4 and Comparative Examples 1 and 2 and a conventional light emitting compound are measured at 1,000 cd / m ² and are shown in Table 2 below. It was.

TABLE 2

As shown in Table 2, it was confirmed that the light emission characteristics of the organic light emitting compounds developed in the present invention shows superior properties compared to the conventional material. In addition, the device using the organic light emitting compound of the present invention as a host material was confirmed that the luminous efficiency is improved by not only excellent light emission characteristics but also by lowering the driving voltage.

Claims (10)

An organic light emitting compound represented by Formula 1 or 2 below.  [Formula 1] [Formula 2]

[In Formula 1 and 2, A ₁ to A ₅ and B ₁ to B ₈ are independently of each other N or CR ₂₁ , and when adjacent A ₁ to A ₅ or B ₁ to B ₈ are CR ₂₁ , each R ₂₁ includes or includes a fused ring; Unsubstituted (C3-C30) alkylene or (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, wherein the carbon atoms of the alkylene are from NR ₃₁ , O or S May be substituted with one or more heteroatoms selected, and the carbon atoms of the alkenylene may be substituted with N; L ₁ and L ₂ are independently a chemical bond, a substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (C3-C30) heteroarylene each other, at the same time chemically bonding L ₁ and L ₂ is Not; R ₁ to R ₃ , R ₂₁ and R ₃₁ are each independently Substituted or unsubstituted fused with one or more hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) cycloalkyl Substituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted aromatic ring 5 1-7 membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted aromatic ring (C3-C30) cycloalkyl, substituted or unsubstituted adamantyl , Substituted or unsubstituted (C7-C30) bicycloalkyl, cyano, NR ₁₁ R ₁₂ , BR ₁₃ R ₁₄ , PR ₁₅ R ₁₆ , P (= 0) R ₁₇ R ₁₈ [R ₁₁ to R ₁₈ are mutually Independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl.], Substituted or unsubstituted Tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted (C6 -C30) ar (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkyloxy, substituted or unsubstituted (C1-C30) alkylthio, substituted or unsubstituted (C6-C30) aryloxy, Substituted or unsubstituted (C6-C30) arylthio, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl,

or

ego; W is-(CR ₅₁ R ₅₂ ) _m -,-(R ₅₁ ) C = C (R ₅₂ )-, -N (R ₅₃ )-, -S-, -O-, -Si (R ₅₄ ) (R ₅₅ )-, -P (R ₅₆ )-, -P (= 0) (R ₅₇ )-, -C (= 0)-, or -B (R ₅₈ )-, R ₄₁ to R ₄₃ and R ₅₁ to R ₅₈ are the same as defined for R ₁ to R ₃ and R ₂₁ , wherein R ₅₁ to R ₅₈ each include or may not include adjacent substituents and fused rings (C3- C30) alkylene or (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring; The heterocycloalkyl and heteroaryl include one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P; m is an integer of 0, 1 or 2.] The method of claim 1, Substituents of L ₁ , L ₂ , R ₁ to R ₃ , R ₁₁ to R ₁₈ , R ₂₁ and R ₃₁ may be (C 1 -C 30) alkyl, (C 6 -C 30) unsubstituted or substituted with deuterium, halogen, or halogen. Aryl, (C6-C30) aryl substituted or unsubstituted (C3-C30) heteroaryl, 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic rings, ( C3-C30) cycloalkyl, (C6-C30) cycloalkyl fused with one or more aromatic rings, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6- C30) arylsilyl, adamantyl, (C7-C30) bicycloalkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, carbazolyl, NR ₆₁ R ₆₂ , BR ₆₃ R ₆₄ , PR ₆₅ R ₆₆ , P (= O) R ₆₇ R ₆₈ [R ₆₁ to R ₆₈ are independently of each other substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or Unsubstituted (C3-C30) heteroaryl], (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, (C1-C30) Kiloxy, (C1-C30) alkylthio, (C6-C30) aryloxy, (C6-C30) arylthio, (C1-C30) alkoxycarbonyl, (C1-C30) alkylcarbonyl, (C6-C30) Arylcarbonyl, (C6-C30) aryloxycarbonyl, (C1-C30) alkoxycarbonyloxy, (C1-C30) alkylcarbonyloxy, (C6-C30) arylcarbonyloxy, (C6-C30) aryl An organic light emitting compound characterized in that it is further substituted with one or more selected from the group consisting of oxycarbonyloxy, carboxyl, nitro or hydroxy, or substituents adjacent to each other are connected to form a ring. The method of claim 1, remind

Is an organic light emitting compound, characterized in that selected from the following structure.

[R ₂₁ and R ₃₁ independently of one another are halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) cycloalkyl Fused substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, NR ₁₁ R ₁₂ [R ₁₁ and R ₁₂ are independently substituted or unsubstituted (C1-C30) C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl], substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted Di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyloxy, substituted or unsubstituted (C6 -C30) aryloxy, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl,

or

And W and R ₄₃ are the same as defined in claim 1. The method of claim 1, remind

or

Is an organic light emitting compound, characterized in that selected from the following structure.

[R ₁ to R ₃ are independently of each other substituted or unsubstituted (C1-C30) alkyl or substituted or unsubstituted (C6-C30) aryl; R ₂₁ is hydrogen, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) cycloalkyl substituted with one or more fused or Unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, NR ₁₁ R ₁₂ [R ₁₁ to R ₁₈ are independently substituted or unsubstituted (C1-C30) alkyl, substituted Or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl.], Substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1- C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted (C6-C30) aryloxy,,

or

And W and R ₄₃ are the same as defined in claim 1. The method of claim 1, An organic light emitting compound, which is selected from the following compounds.

An organic light emitting device comprising the organic light emitting compound according to any one of claims 1 to 5. The method of claim 6, The organic light emitting diode includes a first electrode; A second electrode; And at least one organic layer interposed between the first electrode and the second electrode, wherein the organic material layer includes at least one organic light emitting compound and at least one dopant represented by Formula 3 below. Light emitting element.  [Formula 3] M ¹ L ¹⁰¹ L ¹⁰² L ¹⁰³ Wherein M ¹ is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16, and the ligands L ¹⁰¹ , L ¹⁰² and L ¹⁰³ Are independently selected from the following structures.

[R ₂₀₁ to R ₂₀₃ are each independently hydrogen, (C1-C30) alkyl unsubstituted or substituted, (C6-C30) aryl or unsubstituted (C6-C30) aryl or halogen; R ₂₀₄ to R ₂₁₉ are each independently hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or Unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted mono or substituted or unsubstituted di- (C1-C30) alkylamino, substituted or unsubstituted Mono or di- (C6-C30) arylamino, SF ₅ , substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted Or unsubstituted tri (C6-C30) arylsilyl, cyano or halogen; R ₂₂₀ to R ₂₂₃ are each independently hydrogen, a substituted or unsubstituted (C1-C30) alkyl, or a (C1-C30) aryl optionally substituted (C6-C30) aryl; R ₂₂₄ and R ₂₂₅ are independently of each other hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen, or R ₂₂₄ and R ₂₂₅ contain or contain fused rings Unsubstituted (C3-C12) alkylene or (C3-C12) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring; R ₂₂₆ is substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C5-C30) heteroaryl or halogen; R ₂₂₇ to R ₂₂₉ are each independently hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen; Q is

,

or

R ₂₃₁ to R ₂₄₂ are each independently hydrogen, halogen substituted or unsubstituted (C1-C30) alkyl, (C1-C30) alkoxy, halogen, substituted or unsubstituted (C6-C30) aryl, cyano , Substituted or unsubstituted (C5-C30) cycloalkyl, or may be linked to adjacent substituents with alkylene or alkenylene to form a spiro ring or fused ring, or to R ₂₀₇ or R ₂₀₈ with alkylene or alkenylene To form saturated or unsaturated fused rings.] The method of claim 7, wherein At least one amine compound selected from the group consisting of an arylamine compound or a styrylarylamine compound or an organic metal of Group 1, Group 2, 4 cycle, 5 cycle transition metal, lanthanide series metal and d-transition element in the organic layer The organic electroluminescent device further comprises at least one metal selected from the group consisting of. The method of claim 7, wherein The organic material layer is an organic electroluminescent device comprising a light emitting layer and a charge generating layer. The method of claim 7, wherein An organic electroluminescent device for emitting white light, further comprising at least one organic light emitting layer emitting blue, red, or green light in the organic material layer.