KR20120044529A - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Abstract

PURPOSE: An organic electroluminescent compound is provided to have excellent luminous efficiency and life time property, and to improve powder efficiency, thereby manufacturing an organic electroluminescence device of which power consumption is improved. CONSTITUTION: An organic electroluminescent compound is in chemical formula 1, In chemical formula 1, R1-R4 is respectively hydrogen, deuterium, halogen, substituted or unsubstituted (C1-30) alkyl, or substituted or unsubstituted C6-30 aryl, L1 and L2 is respectively a chemical bond, substituted or unsubstituted (C6-30)arylene, substituted or unsubstituted (C3-30)heteroarylene. An organic electroluminescence device comprises a first electrode, a second electrode, and an organic material layer of one or more layers inserted between the first electrode and the second electrode. The organic material layer comprises one or more of the organic electroluminescent compounds, and one or more phosphorescent dopant.

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.

The most important factor determining the luminous efficiency in OLEDs is the luminous material. Fluorescent materials are widely used as the light emitting materials to date, but the development of phosphorescent materials is one of the best ways to improve the luminous efficiency theoretically up to 4 times. To date, iridium (III) complexes are widely known as phosphorescent materials, and for each RGB, materials such as (acac) Ir (btp) ₂ , Ir (ppy) _3, and Firpic are known. In particular, many phosphorescent materials have recently been studied in Japan and Europe.

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. It is.

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 provide an organic light emitting compound having an excellent luminescence efficiency and device life, and having an excellent color coordinate, in order to solve the above problems, and having a novel organic light emitting compound as a light emitting material. It is to provide a high efficiency and long life organic electroluminescent element to be employed.

The present invention relates to an organic light emitting compound represented by 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 There is an advantage that an OLED having a very long life can be manufactured.

[Formula 1]

[In Formula 1,

R ₁ To R ₄ are independently of each other hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl or substituted or unsubstituted (C6-C30) aryl;

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

,

이거나 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며;Ar ₁ And Ar ₂ independently of each other 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) cycloalkyl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C3-C30) heteroaryl , Substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, substituted or unsubstituted (C6-C30) arylthio,

,

Or (C3-C30) alkenylene, with or without adjacent substituents and fused rings, to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;

Y ₁ and Y ₂ are each independently a chemical bond, -O-, -S-, -C (R ₁₃ R ₁₄ )-, -Si (R ₁₅ R ₁₆ )-, -N (R ₁₇ )-, P ( R ₁₈ )-, -P (= O) (R ₁₉ )-, -C (= O)-, B (R ₂₀ )-or-(R ₂₁ ) C = C (R ₂₂ ), provided that Y ₁ and Except when Y ₂ is a chemical bond at the same time;

A ₁ to A ₈ are independently of each other N or CR ₂₃ , and when adjacent A ₁ to A ₈ are CR ₂₃ , each R ₂₃ may or may not include a fused ring (C3-C30) alkylene or ( C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;

R ₁₁ to R ₁₂ are hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl or adjacent May be linked to a (C3-C30) alkylene or (C3-C30) alkenylene with or without a substituent and a fused ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;

R ₁₃ to R ₂₂ , R ₂₃ And R ₃₁ independently of one another are hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl ;

,

은 서로 동일하거나 상이할 수 있으며;m and n are each independently integers of 0 to 3, except that m and n are 0 at the same time, and when m and n are integers of 2 or more,

,

May be the same or different from each other;

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

Substituents comprising the 'alkyl' and other 'alkyl' moieties described herein include both straight and pulverized forms, and 'cycloalkyl' is substituted or unsubstituted adamantyl or substituted or unsubstituted as well as a single ring system It also includes several ring-based hydrocarbons such as cyclic (C7-C30) bicycloalkyl. "Aryl" described in the present invention is an organic radical derived from an aromatic hydrocarbon by one hydrogen removal, and a single or fused ring containing 4 to 7, preferably 5 or 6 ring atoms in each ring as appropriate. It includes a system, including a form in which a plurality of aryl is connected by a single bond. Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, peryleneyl, chrysenyl, naphthacenyl, 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. "Heteroaryl" described in the present invention contains 1 to 4 heteroatoms selected from B, N, O, S, P, P (= O), Si and Se as aromatic ring skeleton atoms, and the remaining aromatic ring skeletons. Means an aryl group whose atoms are carbon, 5-6 membered monocyclic heteroaryl, and polycyclic heteroaryl condensed with one or more benzene rings, which may be partially saturated. 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, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl Monocyclic heteroaryl such as furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuryl, benzothienyl, isobenzofuryl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoy Soxazolyl, Benzoxazolyl, Isoindoleyl, Indolyl, Indazolyl, Benzothiadiazolyl, Quinolyl, Isoquinolyl, Cinolinyl, Quinazolinyl, Quinolizinyl, Quinoxalinyl, Carbazolyl, Phenantri Polycyclic heteroaryls such as diyl, benzodioxyl, naphthyridinyl, dibenzofuryl, dibenzothiophenyl and their corresponding N-oxides (e.g. pyridyl N-oxides, quinolyl N-oxides) , Quaternary salts thereof, and the like, No.

In addition, the alkyl of the '(C1-C30) alkyl or (C6-C30) ar (C1-C30) alkyl' group described in the present invention includes (C1-C20) alkyl or (C1-C10) alkyl, Aryl of the '(C6-C30) aryl and (C6-C30) ar (C1-C30) alkyl' groups includes (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. '(C3-C30) alkylene or alkenylene' groups include (C3-C20) alkylene or alkenylene, (C3-C10) alkylene or alkenylene.

In addition, in the description of "substituted or unsubstituted" described in the present invention, "substituted" means a case where is further substituted with an unsubstituted substituent, the L ₁ , L ₂ , Ar ₁ , Ar ₂ , R ₁ To R ₄ , R ₁₁ , R ₁₂ , R ₁₃ To substituents further substituted for R ₂₃ and R ₃₁ independently of each other deuterium, halogen, halogen substituted or unsubstituted (C1-C30) alkyl, (C6-C30) aryl, (C6-C30) aryl is substituted or unsubstituted Cyclic (C3-C30) heteroaryl, 5- to 7-membered heterocycloalkyl, at least one 5- to 7-membered heterocycloalkyl fused to at least one aromatic ring, (C3-C30) cycloalkyl, at least one aromatic ring Fused (C6-C30) cycloalkyl, R ₄₁ R ₄₂ R ₄₃ Si-, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, carbazolyl, NR ₄₄ R ₄₅ , BR ₄₆ R ₄₇ , PR ₄₈ R ₄₉ , P (= 0) R ₅₀ R ₅₁ , (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, R ₅₂ S-, R ₅₃ O -At least one selected from the group consisting of carboxyl, nitro or hydroxy, R ₄₁ to R ₅₃ independently of one another are hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted Substituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) he Roaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl or substituted or unsubstituted (C3-C30) alkylene with or without a fused ring with adjacent substituents or substituted or unsubstituted (C3- C30) may be linked to alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, wherein the carbon atoms of the formed alicyclic ring and monocyclic or polycyclic aromatic ring are one selected from nitrogen, oxygen and sulfur It means that can be substituted with the above heteroatoms.

In addition, the organic light emitting compound of the present invention includes a compound represented by the following formula (2).

[Formula 2]

(3)

[Formula 4]

[In Formulas 2 to 4,

R ₁ To R ₄ , L ₁ , L ₂ , Ar ₁ And Ar ₂ is the same as defined in Formula 1 above.]

More specifically, Ar ₁ and Ar ₂ are selected from the following structures, but are not limited thereto.

[In the structure, R ₁₁ , R ₁₂ and R ₁₇ are the same as defined in the formula (1).]

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 may be prepared, for example, as shown in Scheme 1 below, but is not limited thereto.

Scheme 1

[Ar ₁ , L ₁ and R ₁ to R ₄ in Scheme 1 are the same as defined in Formula 1 above.]

In another aspect, the present invention provides an organic electroluminescent device, the organic electroluminescent device according to the present invention comprises a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer includes at least one organic light emitting compound of Formula 1 and at least one phosphorescent dopant. It is done.

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), and at the same time an arylamine compound or a styrylarylamine compound, an arylamine compound Or specific examples of the styrylarylamine-based compound are exemplified in the identification number <212> to <224> of Patent Application No. 10-2008-0060393, 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.

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

In addition, an organic light emitting 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 electroluminescent compound. The compound emitting blue, green, or red light is exemplified in Application Nos. 10-2008-0123276, 10-2008-0107606, or 10-2008-0118428, but is not limited thereto.

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

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

The organic light emitting compound according to the present invention is used as the host material of the organic light emitting material in the OLED device has the advantage of excellent OLED emission efficiency and excellent life characteristics of the material compared to the existing host material can be produced OLED with a very good driving life of the device have.

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 44

compound 1-1 Manufacture

18.3 g (273 mmol) of pyrrole, 30 g (90.9 mmol) of 1,2-diiodobenzene, 17.3 g (90.9 mmol) of CuI, K ₃ PO in a round bottom flask (RBF) ₄ 77 g (364 mmol), ethylenediamine 10.8 g (182 mmol) and 450 mL of toluene were added thereto, and the mixture was stirred under reflux at 110 ° C. for 24 hours. After the reaction was terminated and filtered, the filtrate was extracted with EA. Washed with distilled water and dried over magnesium sulfate. Distillation under reduced pressure and column separation with MC / hexane afforded 13.6 g (72%) of compound 1-1 .

compound 1-2 Manufacture

Under shading conditions, 13 g (62.4 mmol) of 1,2-di (1-pyrrolyl) benzene (1,2-di (1-pyrrolyl) benzene) and 200 mL of DMF were added to a round bottom flask (RBF). A solution of 15.4 g (68.7 mmol) of NIS dissolved in 70 mL of DMF was slowly added dropwise over 30 minutes, followed by stirring at -10 ° C for 4 hours. The reaction mixture was diluted with EA and washed three times with water. Water was removed with MgSO ₄ , distilled under reduced pressure, and column separated with hexane to obtain 9.2 g (32%) of compound 1-2 .

compound 1-3 Manufacture

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

compound 1-4 Manufacture

20 g (80.2 mmol) of 1- (2-nitrophenyl) naphthalene (RBF) in a round bottom flask (RBF), 150 mL of P (OEt) ₃ , 1,2-dichlorobenzene (1, 2-dichlorobenzene) was added and stirred at 140 ° C. for 24 hours. The reaction mixture was distilled off to remove the solvent, and column separated with MC / hexane to give 11.3 g (65%) of Compound 1-4 .

compound 1-5 Manufacture

10 g (47 mmol) of benzo [c] carbazole, 44 g (141 mmol) of 4,4`-dibromobiphenyl (RBF) in a round bottom flask , CuI 4.5 g (23.5 mmol), K ₃ PO ₄ 29.9 g (141 mmol), 5.6 g (94 mmol) of ethylenediamine, and 350 mL of toluene were added thereto, and the mixture was stirred under reflux at 110 ° C. for 24 hours. After completion of the reaction, the filter (washed with MC and THF) and the filtrate was extracted with EA. Washed with distilled water and dried over magnesium sulfate. Distillation under reduced pressure and column separation with MC / hexane afforded 32 g (82%) of compound 1-5 .

compound 1-6 Manufacture

30 g (67 N- (4'-bromobiphenyl-4-yl) benzo [c] carbazole) N- (4'-bromobiphenyl-4-yl) benzo [c] carbazole (RBF) in a round bottom flask mmol), N _{2 was} substituted, and 350 mL of THF was added thereto. After the solution was cooled to -78 ° C, 32 mL of n-BuLi (2.5M in hexane, 80 mmol) was added thereto, followed by stirring for 1 hour. 23 mL (100 mmol) of triisopropylborate was added, followed by stirring for 1 hour. After the dry ice / acetone container was removed, the mixture was further stirred for 1 hour. The reaction mixture was terminated with NH ₄ Cl aqueous solution and extracted with EA. Washed with distilled water and dried over magnesium sulfate. Distillation under reduced pressure and column separation with MC / hexane afforded 18.6 g (67%) of compound 1-6 .

compound 44 Manufacture

3 g (6.5 mmol), 4 'of 1,2-di (2-iodo-1-pyrrolyl) benzene (R) in a round bottom flask (RBF) 8 g (4 '-(7H-benzo [c] carbazol-7-yl) biphenyl-4-ylboronic acid)-(7H-benzo [c] carbazol-7-yl) biphenyl-4-ylboronic acid 19.5 mmol), Pd ₂ (dba) ₃ CHCl ₃ 0.27 g (0.26 mmol), P (tBu) ₃ 0.2 g (0.98 mmol), Cs ₂ CO ₃ 8.5 g (26 mmol) and 35 mL of 1,4-dioxane (1,4-dioxane) were added thereto, and the resultant was stirred at 90 ° C for 6 hours. The reaction was terminated and extracted with EA. Washed with distilled water and dried over magnesium sulfate. Distillation under reduced pressure and column separation with MC / hexane afforded Compound 44 1.2 g (31%).

MS / FAB found 573.68, calculated 573.22

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 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, N , N' -bis (α-naphthyl) -N , N' -diphenyl-4,4'-diamine (NPB) was added to another cell in the vacuum deposition apparatus, and a current was applied to the cell. NPB was evaporated to deposit a 20 nm-thick hole transport layer on the hole injection layer, and then the light emitting layer was deposited on the hole injection layer as follows: One cell in the vacuum deposition apparatus. In a compound 18 according to the invention as a host, in another cell Ir (piq) ₃ [Tris (2-phenylpyridine) iridium (III)] as a dopant, respectively. After loading, the two materials were evaporated at different rates and doped at 4 to 10% by weight to deposit a 30 nm thick light emitting layer on the hole transport layer, followed by Alq [tris (8-hydroxyquinoline) — as an electron transport layer on the light emitting layer. aluminum (III)] is deposited to a thickness of 20 nm, and then lithium quinolate (Liq) is deposited to a thickness of 1 to 2 nm using an electron injection layer, and then another Al deposition is deposited to a thickness of 150 nm using another vacuum deposition apparatus. To produce an OLED device.

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

As a result, a current of 17.4 mA / cm ² flowed at a voltage of 7.2 V, and red light emission of 1020 cd / m ² was confirmed.

It can be confirmed that the light emitting characteristics of the device using the organic light emitting compound developed in the present invention as a red light emitting host material. In addition, by increasing the triplet energy, the organic light emitting compounds of the present invention can be used as a light emitting material having high efficiency and long life.

Claims (10)

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

[In the above formula (1)
R ₁ To R ₄ are independently of each other hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl or substituted or unsubstituted (C6-C30) aryl;
L ₁ and L ₂ are each independently a chemical bond, a substituted or unsubstituted (C6-C30) arylene or a substituted or unsubstituted (C3-C30) heteroarylene;
Ar ₁ And Ar ₂ independently of each other 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) cycloalkyl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C3-C30) heteroaryl , Substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, substituted or unsubstituted (C6-C30) arylthio,

,

Or (C3-C30) alkenylene, with or without adjacent substituents and fused rings, to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
Y ₁ and Y ₂ are each independently a chemical bond, -O-, -S-, -C (R ₁₃ R ₁₄ )-, -Si (R ₁₅ R ₁₆ )-, -N (R ₁₇ )-, P ( R ₁₈ )-, -P (= O) (R ₁₉ )-, -C (= O)-, B (R ₂₀ )-or-(R ₂₁ ) C = C (R ₂₂ ), provided that Y ₁ and Except when Y ₂ is a chemical bond at the same time;
A ₁ to A ₈ are independently of each other N or CR ₂₃ , and when adjacent A ₁ to A ₈ are CR ₂₃ , each R ₂₃ may or may not include a fused ring (C3-C30) alkylene or ( C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
R ₁₁ to R ₁₂ are hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl or adjacent May be linked to a (C3-C30) alkylene or (C3-C30) alkenylene with or without a substituent and a fused ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
R ₁₃ to R ₂₂ , R ₂₃ and R ₃₁ are independently of each other hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) hetero Aryl;
m and n are each independently integers of 0 to 3, except that m and n are 0 at the same time, and when m and n are integers of 2 or more,

,

May be the same or different from each other;
Wherein said heterocycloalkyl and heteroaryl include one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P.] The method of claim 1,
L ₁ , L ₂ , Ar ₁ , Ar ₂ , R ₁ to R ₄ , R ₁₁ , R ₁₂ , Substituents further substituted with R ₁₃ to R ₂₃ and R ₃₁ are each independently substituted with deuterium, halogen, (C1-C30) alkyl, (C6-C30) aryl, or (C6-C30) aryl unsubstituted or substituted with halogen. 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, aromatic ring One or more fused (C6-C30) cycloalkyl, R ₄₁ R ₄₂ R ₄₃ Si-, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, carbazolyl, NR ₄₄ R ₄₅ , BR ₄₆ R ₄₇ , PR ₄₈ R ₄₉ , P (= O) R ₅₀ R ₅₁ , (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, R ₅₂ S-, R ₅₃ O-, carboxyl, nitro or hydroxy, and at least one selected from the group consisting of R ₄₁ to R ₅₃ independently of one another hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted Or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30 Heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl or substituted or unsubstituted (C3-C30) alkylene with or without fused ring with adjacent substituents or substituted or unsubstituted (C3) -C30) may be linked to alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, wherein the carbon atoms of the formed alicyclic ring and monocyclic or polycyclic aromatic ring are selected from nitrogen, oxygen and sulfur It may be substituted with one or more heteroatoms. The method of claim 1,
An organic light emitting compound represented by Chemical Formulas 2 to 4 below.
(2)

(3)

[Chemical Formula 4]

[In Formulas 2 to 4,
R ₁ To R ₄ , L ₁ , L ₂ , Ar ₁ And Ar ₂ is the same as defined in Formula 1 above.] The method of claim 1,
Ar ₁ and Ar ₂ is an organic light emitting compound, characterized in that selected from the following structure.

[In the structure, R ₁₁ , R ₁₂ and R ₁₇ are the same as defined in the formula (1).] The method of claim 1,
An organic light emitting compound, which is selected from the following compounds.

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 at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer comprises at least one organic light emitting compound and at least one phosphorescent dopant. The method of claim 7, wherein
An organic electroluminescent device further comprising at least one amine compound selected from the group consisting of an arylamine compound or a styrylarylamine compound in the organic layer. The method of claim 7, wherein
An organic electric field further comprising at least one metal or a complex compound selected from the group consisting of Group 1, Group 2, 4, 5 cycle transition metals, lanthanum series metals and organic metals of d-transition elements in the organic layer. Light emitting element. The method of claim 7, wherein
An organic electroluminescent device which emits white light by further comprising at least one organic light emitting layer emitting blue, red or green light in the organic material layer.