KR20110088118A - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Abstract

PURPOSE: An organic electroluminescent compound is provided to ensure excellent luminous efficiency, lifetime property, and driving durability, and to obtain an organic light emitting diode with improved power consumption by inducing the increase of power efficiency. CONSTITUTION: An organic electroluminescent compound is represented by chemical formula 1. An organic electro luminescence device comprises the organic luminescent compound. The organic electroluminescence device includes a first electrode, a second electrode, and one or more organic material layers interposed between the first and second electrodes. The organic material layer includes one or more organic luminescent compounds and one or more dopants.

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, and more particularly to a novel organic light emitting compound used as a light emitting material and an organic electroluminescent device employing the same as a host.

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 the solid state, and mobility of electrons and holes. It should be high, not easily decomposed during vacuum deposition, and a stable thin film should be formed.

The organic electroluminescent device is usually composed of a multilayer structure such as an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode. The three colors of blue, green, and red vary depending on how the EML is formed. This device is suitable for the next generation flat panel display because it can be easily implemented.

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 light emitting diodes has emerged as an urgent task. In particular, considering the EL characteristic level required for medium and large OLED panels, it is urgent to develop materials that are much superior to existing light emitting materials.

Disclosure of Invention An object of the present invention is to provide an organic light emitting compound having an excellent luminescence efficiency and device lifetime, and having an appropriate color coordinate, in order to solve the above problems, and to emit the organic light emitting compound as another object. It is to provide an organic electroluminescent device having high efficiency and long life, which is employed as a material.

The present invention relates to an organic light emitting compound represented by the following Chemical Formula 1 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 material than the conventional host material to drive the device In addition to having a very long lifespan, there is an advantage of manufacturing an OLED device having improved power consumption by inducing an increase in power efficiency.

[Formula 1]

[In Formula 1,

또는

이고;A ring

or

ego;

X is -C (R ₁₂ ) (R ₁₃ )-, -N (R ₁₄ )-, -S-, -O- or -Si (R ₁₅ ) (R ₁₆ )-;

Ar ₁ and Ar ₂ are each independently substituted or unsubstituted (C6-C30) arylene or substituted or unsubstituted (C3-C30) heteroarylene; Ar ₃ to Ar ₅ are each independently substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl;

,

,

이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리, 단일환 또는 다환의 헤테로방향족고리를 형성할 수 있고; 상기 B고리 및 C고리는 서로 독립적으로 치환 또는 비치환된(C5-C30)사이클로알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C6-C30)헤테로아릴이며; 상기 R₂₁ 내지 R₃₂는 서로 독립적으로 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 치환 또는 비치환된(C3-C30)헤테로아릴이고; 상기 Y는 S 또는 O이며; W는 -(CR₅₁R₅₂)_m-, -(R₅₁)C=C(R₅₂)-, -N(R₅₃)-, -S-, -O-, -Si(R₅₄)(R₅₅)-, -P(R₅₆)-, -P(=O)(R₅₇)-, -C(=O)- 또는 -B(R₅₈)-이고, R₄₁ 내지 R₄₃ 및 R₅₁ 내지 R₅₈은 상기 R₁ 내지 R₁₆에서의 정의와 동일하며; 상기 헤테로시클로알킬, 헤테로아릴 및 헤테로방향족고리는 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함하고; m은 0 내지 2의 정수이며; a, b는 0 내지 4의 정수이고; a, b가 2 이상일 경우에는 서로 동일하거나 상이할 수 있다.]
R ₁ to R ₁₆ are independently of each other hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) cyclo Substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted, with one or more alkyl fused To 7-membered heterocycloalkyl fused with one or more aromatic rings, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted aromatic rings with one or more fused (C3-C30) cycloalkyl , Cyano, nitro, NR ₂₁ R ₂₂ , BR ₂₃ R ₂₄ , PR ₂₅ R ₂₆ , P (= O) R ₂₇ R ₂₈ , R ₂₉ R ₃₀ R ₃₁ Si-, R ₃₂ Y-, substituted or unsubstituted Substituted (C6-C30) ar (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl,

,

,

Or an alicyclic ring and a monocyclic or polycyclic aromatic ring, monocyclic or polycyclic heteroaromatic linked with (C3-C30) alkylene or (C3-C30) alkenylene with or without adjacent substituents and fused rings May form a ring; Ring B and ring C are independently substituted or unsubstituted (C5-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C6-C30) heteroaryl; R ₂₁ to R ₃₂ are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl; Y is S or O; 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 )-, and R ₄₁ to R ₄₃ and R ₅₁ to R ₅₈ is the same as defined above for R ₁ to R ₁₆ ; The heterocycloalkyl, heteroaryl and heteroaromatic ring comprises one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P; m is an integer from 0 to 2; a, b are integers from 0 to 4; When a and b are 2 or more, they may be the same as or different from each other.]

는 하기 구조로 예시될 수 있으나 이에 한정하지는 않는다.Also specifically above

May be illustrated by the following structure, but is not limited thereto.

[R ₁ to R ₁₀ and R ₁₂ to R ₁₆ are independently of each other hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, NR ₂₁ R ₂₂ , BR ₂₃ R ₂₄ , PR ₂₅ R ₂₆ , P (= O) R ₂₇ R ₂₈ , R ₂₉ R ₃₀ R ₃₁ Si- or R ₃₂ Y- or adjacent Linked with (C3-C30) alkylene or (C3-C30) alkenylene with or without fused ring substituents to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, monocyclic or polycyclic heteroaromatic ring Can do it; R ₂₁ to R ₃₂ are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl; Y is S or O; Wherein said heteroaryl and heteroaromatic rings comprise one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P.]

Substituents comprising the 'alkyl', 'alkoxy' and other 'alkyl' moieties described herein include both straight or crushed forms, and 'cycloalkyl' is substituted or unsubstituted as well as a single ring system Or several ring-based hydrocarbons such as substituted or unsubstituted (C7-C30) bicycloalkyl. In addition, * indicated in the chemical structure of the present invention means a part bonded in the structure.

'Aryl' described in the present invention is an organic radical derived from an aromatic hydrocarbon by one hydrogen removal, and includes a single or fused ring system containing 4 to 7 members, preferably 5 or 6 members, and at least one aryl It also includes structures bonded through this chemical bond. Specific examples of the aryl include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl and the like. Including but not limited to. 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. 'Heteroaryl' described in the present invention includes 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. It means an aryl group which is a 5-6 membered monocyclic heteroaryl or polycyclic heteroaryl condensed with one or more benzene rings, and may be partially saturated. In addition, heteroaryl in the present invention also includes a structure in which one or more heteroaryl is bonded through a chemical 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 of the heteroaryl include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxdiazolyl, triazinyl, tetrazinyl, Monocyclic heteroaryl such as phenazinyl, phenothiazineyl, phenooxazineyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, Dibenzofuranyl, dibenzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzooxazolyl, isoindolinyl, indolyl, indazolyl, benzothia Polycyclic heteroaryls such as diazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, carborinyl, phenanthridinyl, benzodioxolyl and their corresponding N-oxides (E.g., pyridyl N-oxide, quinolyl N-oxa D), quaternary salts thereof, and the like, but are not limited thereto.

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.

In addition, in the description of "substituted or unsubstituted" in the description of "substituted" means a case that is further substituted with an unsubstituted substituent, the Ar ₁ To Ar ₅ , R ₁ To R ₁₆ , R ₂₁ to R ₃₂ , R ₄₁ to R ₄₃ , and R ₅₁ to R ₅₈ are each independently substituted with deuterium, halogen, halogen substituted or unsubstituted (C1-C30) alkyl, (C6 -C30) aryl, (C6-C30) aryl substituted or unsubstituted (C3-C30) heteroaryl, (C3-C30) heteroaryl, 5- to 7-membered heterocycloalkyl, aromatic ring at least one fused 5- to 7-membered heterocycloalkyl, (C3-C30) cycloalkyl, (C3-C30) cycloalkyl fused with one or more aromatic rings, NR ₆₁ R ₆₂ , BR ₆₃ R ₆₄ , PR ₆₅ R ₆₆ , P ( = O) R ₆₇ R ₆₈ , R ₆₉ R ₇₀ R ₇₁ Si-, R ₇₂ Z-, R ₇₃ C (= O)-, R ₇₄ C (= O) O-, (C2-C30) alkenyl, ( C2-C30) alkynyl, cyano, carbazolyl, (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, carboxyl, nitro or hydroxy May be further substituted with one or more selected from or substituents adjacent to each other may be connected to form a ring; R ₆₁ above To R ₇₂ independently of one another are (C1-C30) alkyl, (C6-C30) aryl or (C3-C30) heteroaryl; Z is S or O; R ₇₃ above And R ₇₄ independently of one another includes (C 1 -C 30) alkyl, (C 1 -C 30) alkoxy, (C 6 -C 30) aryl or (C 6 -C 30) aryloxy.

는 하기 구조에서 선택되며, 이에 한정되지는 않는다.remind

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

[R ₈₁ To R ₁₀₉ are independently of each other hydrogen, (C6-C30) aryl, (C3-C30) heteroaryl or tri (C6-C30) arylsilyl.]

는 하기 구조에서 선택되며, 이에 한정되지는 않는다.More preferably

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

Also above R ₁ To R ₁₆ are independently of each other hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n -Octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, fluorine, cyano, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy , t-butoxy, n-pentoxy, i-pentoxy, n-hexyloxy, n-heptoxy, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl Trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, Chrysenyl, naphthacenyl, peryleneyl, pyridyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimidazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, triazinyl, Phenyltriazinyl, phenothiazineyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyrazolyl, indolyl, N-phenylpyridoindolyl, N-phenylpyrazinoindolyl, carba Zolyl, N-phenylcarbazolyl, N-phenylbenzocarbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzooxazolyl, trimethylsilyl, triethylsilyl, tripropylsilyl, tri (t-butyl) silyl, t- Butyldimethylsilyl, dimethylphenylsilyl, triphenylsilyl or benzyl, but is not limited thereto.

More preferably R ₁ To R ₁₆ is selected from the following structures, but is not limited thereto.

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

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. The organic material layer may include a light emitting layer, and the light emitting layer may include one or more dopants using at least one organic light emitting compound of Formula 1 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 a compound represented by the following formula (2).

 [Formula 2]

M ¹ L ¹⁰¹ L ¹⁰² L ¹⁰³

[In the formula (2)

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

R ₂₀₁ to R ₂₀₃ are independently of each other hydrogen, (C1-C30) alkyl with or without halogen, (C6-C30) aryl or halogen with or without (C1-C30) alkyl; 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, deuterium, (C1-C30) alkyl with or without halogen, or (C6-C30) aryl with or without (C1-C30) alkyl; R ₂₂₄ and R ₂₂₅ are independently of each other hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen, or R ₂₂₄ and R ₂₂₅ contain fused rings Linked with (C3-C12) alkylene or (C3-C12) alkenylene with or without formation 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, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen;

,

또는

이며, R₂₃₁ 내지 R₂₄₂는 서로 독립적으로 수소, 중수소, 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 of the other hydrogen, deuterium, (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 with R ₂₀₇ or R ₂₀₈ and alkylene or alkenylene To form a saturated or unsaturated fused ring.]

The dopant compound of Formula 2 may be exemplified as a compound having the following structure, but is not limited thereto.

The organic electroluminescent device of the present invention may include one or more compounds selected from the group consisting of an organic light emitting compound of Formula 1 and an arylamine compound or a styrylarylamine compound, and the arylamine compound Or styrylarylamine-based compounds include, but are not limited to, those exemplified in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606, or 10-2008-0118428.

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 exemplified in Korean Patent 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 halogenated metal layer, and a metal oxide layer on at least one inner surface of a pair of electrodes (hereinafter, these are referred to as 'surface layers'). It is preferable to arrange | position the above. 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 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 13

Preparation of Compound 1-1

50 g (0.23 mol) of 2- (phenylamino) benzoic acid was dissolved in 1 L of MeOH, and stirred in an ice bath for 10 minutes. 60 mL (0.58 mol) of SOCl ₂ was slowly added at 0 ° C., followed by stirring under reflux at 90 ° C. for 12 hours. When the reaction was terminated, washed with distilled water and extracted with ethyl acetate. The organic layer was dried over MgSO ₄ , and the solvent was removed using a rotary evaporator. The mixture was purified by column chromatography with ethyl acetate as a developing solvent, to obtain compound 1-1 47 g (92%).

Preparation of Compound 1-2

90 g (0.3 mol) of Compound 1-1 was added to 1.5 L of THF, and 462 mL (1.38 mol) of MeMgBr (3.0M) was added slowly, followed by stirring at room temperature for 12 hours. After the reaction was completed, the mixture was neutralized with distilled water and extracted with ethyl acetate. The organic layer was dried over MgSO ₄ , and the solvent was removed using a rotary evaporator. Purification by column chromatography using ethyl acetate as a developing solvent gave 80 g (90%) of compound 1-2.

Preparation of Compound 1-3

80 g (0.35 mol) of Compound 1-2 was added to 1.7 L of H ₃ PO _4, followed by stirring at room temperature for 12 hours. When the reaction was terminated, the mixture was neutralized with distilled water and filtered while washing the resulting solid with water. The solid was extracted by dissolving with dichloromethane and neutralized with NaOH. The organic layer was dried over MgSO ₄ , the solvent was removed with a rotary evaporator, and recrystallized with hexane to obtain 64 g (87%) of compound 1-3.

Preparation of Compound 1-4

Compound 1-3 64 g (0.30 mol), Bromobenzene 52.8 g (0.33 mol), Pd (OAc) ₂ 1.37 g (6.11 mmol), P (t-Bu) ₃ 50% 7.3 mL (15.28 mmol) ) And 58 g (0.61 mol) of NaOt-Bu were dissolved in 1.2 L of toluene and stirred at 120 ° C. for 12 hours. After the reaction was completed, the mixture was neutralized with distilled water and extracted with ethyl acetate. The organic layer was dried over MgSO ₄ , and the solvent was removed using a rotary evaporator. The mixture was purified by column chromatography with ethyl acetate as a developing solvent, to obtain 71 g (81%) of Compound 1-4.

Preparation of Compound 1-5

20 g (0.07 mol) of Compound 1-4 were dissolved in 800 mL of DMF and stirred at 0 ° C. for 10 minutes. A solution of 12.5 g (0.07 mol) of NBS dissolved in 350 mL of DMF was slowly added thereto, followed by stirring at 0 ° C. for 6 hours. After the reaction was completed, the mixture was neutralized with distilled water and extracted with ethyl acetate. The organic layer was dried over MgSO ₄ , and the solvent was removed using a rotary evaporator. The mixture was purified by column chromatography with ethyl acetate as a developing solvent, to obtain 21 g (84%) of Compound 1-5.

Preparation of Compound 1-6

Compound 1-5 20 g (0.054 mol), 2-chloroaniline 8.4 g (0.065 mol), Pd (OAc) ₂ 370 mg (1.64 mmol), P (t-Bu) ₃ 50% 3.6 mL (5.49 mmol) and 35.7 g (0.109 mol) of Cs ₂ CO ₃ were dissolved in 300 mL of toluene and stirred at 120 ° C. for 4 hours. After the reaction was completed, the mixture was neutralized with distilled water and extracted with ethyl acetate. The organic layer was dried over MgSO ₄ , and the solvent was removed using a rotary evaporator. Purification by column chromatography using ethyl acetate as a developing solvent gave 13.6 g (60%) of compound 1-6.

Preparation of Compound 1-7

12.6 g (0.03 mol) of Compound 1-6, 1.37 mg (6.13 mmol) of Pd (OAc) ₂ , 3 g (12.26 mmol) of Di-tert-butyl (methyl) phosponium tetrafluoroborate and 50 g (0.15 mol) of Cs ₂ CO ₃ Was dissolved in 240 mL of DMA and stirred at 190 ° C. for 4 h. After the reaction was completed, the mixture was neutralized with distilled water and extracted with ethyl acetate. The organic layer was dried over MgSO ₄ , and the solvent was removed using a rotary evaporator. Purification by column chromatography using ethyl acetate as a developing solvent gave 7 g (70%) of compound 1-7.

Preparation of Compound 1-8

13.2 g (56.12 mmol) of Compound 1-7, 1.7 g (28.06 mmol) of Cu, 7.7 g (56.12 mol) of K ₂ CO ₃ , and 395 mg (1.49 mmol) of 18-crown-6 were converted to 1,2-dichlorobenzene ( 1,2-dichlorobenzene) was dissolved in 200 mL and stirred under reflux at 180 ° C. for 24 hours. After the reaction was completed, the cellite was filtered through MC, MC was removed by a rotary evaporator, and distillation was performed to remove 1,2-dichlorobenzene. The mixture from which the solvent was removed was dissolved in MC, neutralized with water, and extracted with MC. The organic layer was dried over MgSO ₄ , the solvent was removed using a rotary evaporator, and purified by column chromatography with ethyl acetate as a developing solvent to obtain compound 1-8 8 g (80%).

Preparation of Compound 1-9

8 g (15.10 mmol) of Compound 1-8 were dissolved in 250 mL of THF, cooled to −78 ° C., and 9 mL (22.66 mmol) of n-BuLi (2,5M) was added slowly. After stirring at low temperature for 1 hour, 2.5 mL (22.66 mmol) of B (OMe) ₃ was added at -78 ° C and stirred for 1 hour. After the reaction for 24 hours, 1M HCl was added at 0 ° C, washed with distilled water after 10 minutes and extracted with ethyl acetate. The organic layer was dried over MgSO ₄ , the solvent was removed with a rotary evaporator, and purified by column chromatography to obtain 5 g (67%) of Compound 1-9.

Preparation of Compound 1-10

2,4,6-trichloropyrimidine 20 g (0.109 mol), phenylboronic acid 29.2 g (0.239 mol), Pd (PPh ₃ ) ₄ 6.3 g (0.005 mol), 163 mL Na ₂ CO ₃ (2M) and 163 mL EtOH were added to 320 mL of toluene and then heated at 120 ° C. After stirring for 3 hours, the reaction was terminated, washed with distilled water and extracted with ethyl acetate. The organic layer was dried over MgSO ₄ , the solvent was removed with a rotary evaporator, and purified by column chromatography to obtain 25 g (86%) of Compound 1-10.

Preparation of Compound 13

2.7 g (10.11 mmol) of compound 1-10, 5 g (10.11 mmol) of compound 1-9, 584 mg (0.50 mmol) of Pd (PPh ₃ ) ₄ , 15 mL of K ₂ CO ₃ (2M) and 15 mL of EtOH were dissolved in toluene. Dissolved in 30 mL and heated at 120 ° C. After stirring for 3 hours, the reaction was terminated, washed with distilled water and extracted with ethyl acetate. The organic layer was dried over MgSO ₄ , the solvent was removed with a rotary evaporator, and purified by column chromatography to obtain 5 g (72%) of compound 13.

Preparation Example 2 Preparation of Compound 48

Preparation of Compound 2-1

22 g (61 mmol) of compound 1-5, 20 g (136 mmol) of methyl 2-amino benzoate, 0.41 g (1.8 mmol) of palladium acetate, tri-tert-butyl phosphine 1.69 g (6.1 mmol) and 39.4 g (120 mmol) of cesium carbonate were dissolved in 350 mL of toluene, followed by stirring under reflux at 100 ° C. for 12 hours. At the end of the reaction, extraction was performed with H ₂ O / EA. The organic layer was dried over MgSO ₄ , the solvent was removed using a rotary evaporator, and the residue was separated by a column to obtain compound 2-2 16 g (61%).

Preparation of Compound 2-2

16 g (37 mmol) of Compound 2-1 was dissolved in 180 mL of THF, and 49.1 mL of 3M methylmagnesium bromide was added thereto, and the mixture was stirred at 60 ° C. for 4 hours. Extraction was performed with EA / H ₂ O, the organic layer was dried over MgSO ₄ , the solvent was removed with a rotary evaporator, and silica filtration to obtain Compound 2-2 14 g (87%).

Preparation of Compound 2-3

14 g (32.2 mmol) of Compound 2-2 was dissolved in 300 mL of phosphoric acid, and then stirred at room temperature for 12 hours. Extraction was performed with EA / H ₂ O, the organic layer was dried with MgSO ₄ , the solvent was removed with a rotary evaporator, and filtered through silica to obtain compound 2-3 (10 g, 75%).

Preparation of Compound 2-4

Compound 2-3 10 g (24 mmol), 4-bromoiodobenzene 20.37 g (72 mmol), copper powder 3.05 g (48 mmol), 18-crown-6 1.52 g (5.8 mmol) and 9.95 g (72 mmol) of potassium carbonate was dissolved in 200 mL of 1,2-dichlorobenzene and stirred under reflux at 180 ° C. for 12 hours. 1,2-dichlorobenzene (1,2-dichlorobenzene) was distilled off and extracted with EA / H ₂ O. The organic layer was dried over MgSO ₄ , the solvent was removed with a rotary evaporator, and the mixture was separated by a column to obtain 6.5 g (47%) of Compound 2-4.

Preparation of Compound 2-5

6.5 g (11 mmol) of Compound 2-4 were dissolved in 100 mL of THF, and 5.91 mL of 2.5M n-Butyl lithium was added at -78 ° C, stirred for 1 hour, and then 4.45 mL (19 mmol) of tri-isopropyl borate was added thereto. Stir for 12 hours. EA / H ₂ O extraction, the organic layer was dried over MgSO ₄ and the solvent was removed by a rotary evaporator, and recrystallized with dichloromethane / methanol to give compound 2-5 3 g (41%).

Preparation of Compound 2-6

15 g (100 mmol) of 2,4-dichloropyrimidine, 12.28 g (100 mL) of phenyl boronic acid, 5.82 g (5 mmol) of tetrakis (triphenylphosphine) palladium, sodium 25.61 g (240 mmol) of carbonate and 200 mL of ethanol were dissolved in 500 mL of toluene and stirred at reflux at 70 ° C. for 3 hours. The mixture was extracted with EA / H ₂ O, the organic layer was dried over MgSO ₄ , the solvent was removed with a rotary evaporator, and separated by a column to obtain 16 g (83%) of Compound 2-6.

Preparation of Compound 48

0.75 g (3.9 mmol) of Compound 2-6, 2.53 g (4.7 mmol) of Compound 2-5, 0.23 g (0.2 mmol) of Tetrakis (triphenylphosphine) palladium, 1.31 g (9.4 mmol) of potassium carbonate and 50 mL of ethanol 150 mL It was dissolved in and stirred under reflux at 120 ° C. for 5 hours. Extraction was performed with EA / H ₂ O, the organic layer was dried over MgSO ₄ , the solvent was removed with a rotary evaporator, and separated by a column to obtain compound 48 0.76 g (30%).

The organic light emitting compounds 1 to compound 60 were manufactured by using the methods of Preparation Example 1 and Preparation Example 2, and the ¹ H NMR and the 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? It was used after. Next, the ITO substrate is installed in the substrate folder of the vacuum deposition apparatus, and 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenylamine (2-TNATA) is installed in the cell in the vacuum deposition apparatus. 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. N, N '-bis (α- naphthyl) - N, N' to another cell of the vapor deposition devices placed -diphenyl-4,4'-diamine (NPB) , and evaporation of the NPB by applying 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 the hole transport layer was then deposited on the light emitting layer as follows: Compound 20 according to the invention as a host in one cell in a vacuum deposition apparatus; In another cell, add Ir (ppy) ₃ [tris (2-phenylpyridine) iridium] as a dopant, respectively, and add the two substances at different rates. A light emitting layer of 30 nm thickness was deposited on the hole transport layer by flashing and doping to 4 to 10% by weight, followed by 20 nm thickness of tris (8-hydroxyquinoline) -aluminum (III) (Alq) as an electron transporting layer on the light emitting layer. After depositing, the lithium quinolate (Liq) was deposited with an electron injection layer to a thickness of 1 to 2 nm, and an Al cathode was deposited to a thickness of 150 nm using another vacuum deposition equipment to manufacture 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 3.5 mA / cm ² flowed at a voltage of 6.6 V, and green light emission of 1270 cd / m ² was confirmed.

[Example 2]

An OLED device was manufactured in the same manner as in Example 1, except that Compound 30 was added as a host material in the light emitting layer and Ir (ppy) ₃ [tris (2-phenylpyridine) iridium] was used as the light emitting dopant.

As a result, a current of 3.7 mA / cm ² flowed at a voltage of 7.2 V, and green light emission of 1040 cd / m ² was confirmed.

Example 3

An OLED device was manufactured in the same manner as in Example 1, except that Compound 40 was added as a host material in the light emitting layer and Ir (ppy) ₃ [tris (2-phenylpyridine) iridium] was used as the light emitting dopant.

As a result, a current of 3.7 mA / cm ² flowed at a voltage of 6.7 V, and green light emission of 1170 cd / m ² was confirmed.

Example 4

An OLED device was manufactured in the same manner as in Example 1, except that Compound 48 was added as a host material in the light emitting layer and Ir (ppy) ₃ [tris (2-phenylpyridine) iridium] was used as the light emitting dopant.

As a result, a current of 4.1 mA / cm ² flowed at a voltage of 6.9 V, and green light emission of 1120 cd / m ² was confirmed.

Comparative Example 1

4,4'-bis (carbazol-9-yl) biphenyl (CBP) as a host material in one cell in a vacuum deposition apparatus, Ir (ppy) ₃ [tris (2-phenyl pyridine) iridium as dopant OLED was used in the same manner as in Example 1, except that bis (2-methyl-8-quinolinate) ( p -phenylphenolrato) aluminum (III) (BAlq) was used as the hole blocking layer. The device was produced.

As a result, a current of 3.8 mA / cm ² flowed at a voltage of 7.5 V, and green 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 was not only excellent in the light emission characteristics, but also by lowering the driving voltage to increase the power efficiency to improve the power consumption.

Claims (10)

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

[In the above formula (1)
A ring

or

ego;
X is -C (R ₁₂ ) (R ₁₃ )-, -N (R ₁₄ )-, -S-, -O- or -Si (R ₁₅ ) (R ₁₆ )-;
Ar ₁ and Ar ₂ are each independently substituted or unsubstituted (C6-C30) arylene or substituted or unsubstituted (C3-C30) heteroarylene; Ar ₃ to Ar ₅ are each independently substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl;
R ₁ to R ₁₆ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) cyclo Substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted, with one or more alkyl fused To 7-membered heterocycloalkyl fused with one or more aromatic rings, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted aromatic rings with one or more fused (C3-C30) cycloalkyl , Cyano, nitro, NR ₂₁ R ₂₂ , BR ₂₃ R ₂₄ , PR ₂₅ R ₂₆ , P (= O) R ₂₇ R ₂₈ , R ₂₉ R ₃₀ R ₃₁ Si-, R ₃₂ Y-, substituted or unsubstituted Substituted (C6-C30) ar (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl,

,

,

Or an alicyclic ring and a monocyclic or polycyclic aromatic ring, monocyclic or polycyclic heteroaromatic linked with (C3-C30) alkylene or (C3-C30) alkenylene with or without adjacent substituents and fused rings May form a ring; Ring B and ring C are independently substituted or unsubstituted (C5-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C6-C30) heteroaryl; R ₂₁ to R ₃₂ are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl; Y is S or O; 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 )-, and R ₄₁ to R ₄₃ and R ₅₁ to R ₅₈ is the same as defined above for R ₁ to R ₁₆ ; The heterocycloalkyl, heteroaryl and heteroaromatic ring comprises one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P; m is an integer from 0 to 2; a, b are integers from 0 to 4; When a and b are 2 or more, they may be the same as or different from each other.] The method of claim 1,
remind

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

[R ₁ to R ₁₀ And R ₁₂ to R ₁₆ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) Heteroaryl, NR ₂₁ R ₂₂ , BR ₂₃ R ₂₄ , PR ₂₅ R ₂₆ , P (= O) R ₂₇ R ₂₈ , R ₂₉ R ₃₀ R ₃₁ Si- or R ₃₂ Y- or include a fused ring with adjacent substituents May be linked with (C3-C30) alkylene or (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, a monocyclic or polycyclic heteroaromatic ring; R ₂₁ to R ₃₂ are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl; Y is S or O; Wherein said heteroaryl and heteroaromatic rings comprise one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P.] The method of claim 1,
Substituents further substituted with Ar ₁ to Ar ₅ , R ₁ to R ₁₆ , R ₂₁ to R ₃₂ , R ₄₁ to R ₄₃ , and R ₅₁ to R ₅₈ may be each independently substituted or unsubstituted with deuterium, halogen, or halogen. (C1-C30) alkyl, (C6-C30) aryl, (C6-C30) aryl substituted or unsubstituted (C3-C30) heteroaryl, (C3-C30) heteroaryl, 5- to 7-membered heterocyclo Alkyl, 5- to 7-membered heterocycloalkyl fused at least one aromatic ring, (C3-C30) cycloalkyl, (C3-C30) cycloalkyl fused at least one aromatic ring, NR ₆₁ R ₆₂ , BR ₆₃ R ₆₄ , PR ₆₅ R ₆₆ , P (= O) R ₆₇ R ₆₈ , R ₆₉ R ₇₀ R ₇₁ Si-, R ₇₂ Z-, R ₇₃ C (= O)-, R ₇₄ C (= O) O-, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, carbazolyl, (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, carboxyl Further substituted with one or more selected from the group consisting of nitro or hydroxy, or substituents adjacent to each other are connected to form a ring It can have; R ₆₁ to R ₇₂ independently of one another are (C1-C30) alkyl, (C6-C30) aryl or (C3-C30) heteroaryl; Z is S or O; R ₇₃ and R ₇₄ are independently from each other (C1-C30) alkyl, (C1-C30) alkoxy, (C6-C30) aryl or (C6-C30) aryloxy. The method of claim 1,
remind

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

[R ₈₁ To R ₁₀₉ are independently of each other hydrogen, (C6-C30) aryl, (C3-C30) heteroaryl or tri (C6-C30) arylsilyl.] The method of claim 1,
R ₁ to R ₁₆ are each independently hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n- Heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, fluorine, cyano, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i -Butoxy, t-butoxy, n-pentoxy, i-pentoxy, n-hexyloxy, n-heptoxy, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl , Cyclodecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, Pyrenyl, chrysenyl, naphthacenyl, peryleneyl, pyridyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimidazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, tri Genyl, diphenyltriazinyl, phenothiazineyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyrazolyl, indolyl, N-phenylpyridoindolyl, N-phenylpyrazinoin Doryl, carbazolyl, N-phenylcarbazolyl, N-phenylbenzocarbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzooxazolyl, trimethylsilyl, triethylsilyl, tripropylsilyl, tri (t-butyl) silyl and t-butyldimethylsilyl, dimethylphenylsilyl, triphenylsilyl or benzyl. An organic electroluminescent device comprising the organic light emitting compound according to any one of claims 1 to 5. The method of claim 6,
The organic electroluminescent device includes a first electrode; A second electrode; And one or more organic material layers interposed between the first electrode and the second electrode, wherein the organic material layer includes one or more organic light emitting compounds and one or more dopants represented by the following Chemical Formula 2. Light emitting element.
(2)
M ¹ L ¹⁰¹ L ¹⁰² L ¹⁰³
[In Formula 2,
M ¹ is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16, and ligands L ¹⁰¹ , L ¹⁰² and L ^103. Are independently selected from the following structures;

R ₂₀₁ to R ₂₀₃ are independently of each other hydrogen, (C1-C30) alkyl with or without halogen, (C6-C30) aryl or halogen with or without (C1-C30) alkyl; 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, deuterium, (C1-C30) alkyl with or without halogen, or (C6-C30) aryl with or without (C1-C30) alkyl; R ₂₂₄ and R ₂₂₅ are independently of each other hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen, or R ₂₂₄ and R ₂₂₅ contain fused rings Linked with (C3-C12) alkylene or (C3-C12) alkenylene with or without formation 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, deuterium, 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 of the other hydrogen, deuterium, (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 with R ₂₀₇ or R ₂₀₈ and alkylene or alkenylene To form a saturated or unsaturated fused ring.] 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
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.