KR20120032054A - Novel organic luminescent compounds and organic electroluminescent device using the same - Google Patents

Abstract

PURPOSE: An organic electroluminescent compound is provided to have excellent luminous efficiency and lifetime comparison with existing dopant material, and to have moderate color coordination. CONSTITUTION: An organic electroluminescent compound is in chemical formula 1. In chemical formula 1, L1 is an organic ligand, R1-R5 is respectively deuterium, halogen, substituted or non-substituted C3-30 cycloalkyl, substituted or non-substituted 5-7 membered heterocycloalkyl, cyano, nitro, BR21R22, PR23R24, P(=O)R25R26, R27R28R29Si-, substituted or non-substituted C6-30 ar C1-30 alkyl. R21-R26 is respectively substituted or non-substituted C1-30 alky, substituted or non-substituted C6-30 aryl, or substituted or non-substituted C3-30 heteroaryl. R27-R29 is respectively substituted or non-substituted C1-30 alkyl, substituted or non-substituted C6-30 aryl, or substituted or non-substituted C3-30 heteroaryl.

Description

Novel organic luminescent 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 using the same as a dopant.

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 up to four times in theory.

To date, the iridium (III) complexes are widely known as phosphorescent materials, and materials such as (acac) Ir (btp) ₂ , Ir (ppy) ₃ and Firpic are known for each RGB. In particular, many phosphorescent materials have recently been studied in Japan and Europe.

Among the conventional red phosphorescent materials, some have been reported as materials showing good EL properties, but the materials that have reached the level of commercialization are known to be very small. The best material is an iridium complex of 1-phenyl isoquinoline, which is known to have excellent EL characteristics, showing a deep red color purity and high luminous efficiency. (Ref. A. Tsuboyama, et. Al. , J. Am. Chem. Soc. 2003 , 125 (42), 12971-12979)

Moreover, in the case of the red material, there is no big problem in lifespan, and if it is excellent in color purity or luminous efficiency, it tends to be commercialized easily. Therefore, the iridium complex can be said to be a material having a high possibility of commercialization due to its excellent color purity and luminous efficiency.

However, the iridium complex is still judged to be a material applicable to a small display or the like, and in fact, the EL characteristic level required for medium and large OLED panels has a problem that should be superior to known materials.

Accordingly, the present inventors have endeavored to solve the above-mentioned conventional problems, and as a result, have invented a new light emitting compound for realizing an organic electroluminescent device having excellent luminous efficiency and a markedly improved lifetime.

Accordingly, an object of the present invention is to provide an organic light emitting compound having an excellent skeleton having an excellent luminous efficiency and device life and suitable color coordinates to solve the above problems.

Another object of the present invention is to provide a high efficiency and long life organic electroluminescent device employing the organic light emitting compound as a light emitting material.

The present invention relates to an organic light emitting compound represented by formula (I):

[Formula I]

In Formula I,

L ₁ is an organic ligand;

R ₁ to R ₅ are each independently deuterium, halogen, substituted or unsubstituted (C ₃ -C ₃₀ ) cycloalkyl, substituted or unsubstituted 5 to 7 membered heterocycloalkyl, cyano, nitro, BR ₂₁ R ₂₂ , PR ₂₃ R ₂₄ , P (═O) R ₂₅ R ₂₆ [R ₂₁ to R ₂₆ are independently of each other substituted or unsubstituted (C ₁ -C ₃₀ ) alkyl, substituted or unsubstituted (C ₆ -C ₃₀ ) aryl or substituted or unsubstituted (C ₃ -C ₃₀ ) heteroaryl.], R ₂₇ R ₂₈ R ₂₉ Si- [R ₂₇ to R ₂₉ are each independently substituted or unsubstituted (C ₁ -C ₃₀ ) alkyl, substituted or unsubstituted (C ₆ -C ₃₀ ) aryl or substituted or unsubstituted (C ₃ -C ₃₀ ) heteroaryl], substituted or unsubstituted (C ₆ -C ₃₀ ) Ar (C ₁ -C ₃₀ ) alkyl;

R is hydrogen, substituted or unsubstituted (C ₁ -C ₃₀ ) alkyl, substituted or unsubstituted (C ₁ -C ₃₀ ) alkoxy, substituted or unsubstituted (C ₆ -C ₃₀ ) aryl or substituted or unsubstituted (C ₃ -C ₃₀ ) heteroaryl;

R ₆ to R ₉ are hydrogen, deuterium, halogen, substituted or unsubstituted (C ₁ -C ₃₀ ) alkyl, substituted or unsubstituted (C ₆ -C ₃₀ ) aryl, substituted or unsubstituted (C ₅ -C ₃₀₎ heteroaryl, substituted or unsubstituted (C ₃ -C ₃₀₎ cycloalkyl-alkyl, substituted or a 5-to 7-membered heterocycloalkyl, cyano, nitro _{unsubstituted, BR 21 R 22, PR 23} R 24 , P (= 0) R ₂₅ R _26, NR ₃₀ R ₃₁ [R ₂₁ to R ₂₆ , R ₃₀ to R ₃₁ are each independently substituted or unsubstituted (C ₁ -C ₃₀ ) alkyl, substituted or unsubstituted (C ₆ -C ₃₀ ) aryl or substituted or unsubstituted (C ₃ -C ₃₀ ) heteroaryl.], R ₂₇ R ₂₈ R ₂₉ Si- [R ₂₇ to R ₂₉ are each independently substituted or unsubstituted. (C ₁ -C ₃₀ ) alkyl, substituted or unsubstituted (C ₆ -C ₃₀ ) aryl or substituted or unsubstituted (C ₃ -C ₃₀ ) heteroaryl], R ₃₂ Y- [Y is S or O, R ₃₂ is substituted or unsubstituted (C ₁ -C ₃₀ ) alkyl, substituted or unsubstituted (C ₆ -C ₃₀ ) aryl, or Substituted or unsubstituted (C ₃ -C ₃₀ ) heteroaryl], substituted or unsubstituted (C ₂ -C ₃₀ ) alkenyl, substituted or unsubstituted (C ₂ -C ₃₀ ) alkynyl, substituted or Unsubstituted (C ₆ -C ₃₀ ) ar (C ₁ -C ₃₀ ) alkyl or adjacent substituents may combine to form a fused ring;

n and m are each independently an integer from 1 to 3;

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

The compounds of formula I also include compounds having the structure of formula II or III:

≪ RTI ID = 0.0 &

[Formula III]

In Formula II or Formula III, R ₁ to R ₅ , R, R ₆ to R ₉ , L ₁ , n are the same as defined in Formula I above.

L ₁ described above is selected from compounds having the following structure, but not limited thereto:

In the above formula,

R ₂₀₁ to R ₂₀₃ are each independently hydrogen, deuterium, (C ₁ -C ₃₀ ) alkyl with or without halogen, (C ₁ -C ₃₀ ) alkyl with or without (C ₁ -C ₃₀ ) Aryl or halogen;

R ₂₀₄ to R ₂₁₉ are each independently hydrogen, deuterium, substituted or unsubstituted (C ₁ -C ₃₀ ) alkyl, substituted or unsubstituted (C ₁ -C ₃₀ ) alkoxy, substituted or unsubstituted (C _3- C ₃₀ ) cycloalkyl, substituted or unsubstituted (C ₂ -C ₃₀ ) alkenyl, substituted or unsubstituted (C ₆ -C ₃₀ ) aryl, substituted or unsubstituted mono or substituted or unsubstituted di (C _1- C ₃₀ ) alkylamino, substituted or unsubstituted mono or di (C ₆ -C ₃₀ ) arylamino, SF ₅ , substituted or unsubstituted tri (C ₁ -C ₃₀ ) alkylsilyl, substituted or unsubstituted Di (C ₁ -C ₃₀ ) alkyl (C ₆ -C ₃₀ ) arylsilyl, substituted or unsubstituted tri (C ₆ -C ₃₀ ) arylsilyl, cyano or halogen;

R ₂₂₀ through R ₂₂₃ independently represent hydrogen, deuterium, halogen-substituted or unsubstituted (C ₁ -C ₃₀₎ alkyl or (C ₁ -C ₃₀₎ alkyl is optionally substituted (C ₆ -C ₃₀₎ with each other Aryl;

R ₂₂₄ and R ₂₂₅ are independently of each other hydrogen, deuterium, substituted or unsubstituted (C ₁ -C ₃₀ ) alkyl, substituted or unsubstituted (C ₆ -C ₃₀ ) aryl or halogen, or R ₂₂₄ and R ₂₂₅ are does not contain a fused ring with or (C ₃ -C ₁₂₎ alkylene or (C ₃ -C ₁₂₎ alkenylene with an alicyclic ring, or a monocyclic or polycyclic form a ring;

R ₂₂₆ is substituted or unsubstituted (C ₁ -C ₃₀ ) alkyl, substituted or unsubstituted (C ₆ -C ₃₀ ) aryl, substituted or unsubstituted (C ₅ -C ₃₀ )) heteroaryl or halogen;

R ₂₂₇ to R ₂₂₉ are independently of each other hydrogen, deuterium, substituted or unsubstituted (C ₁ -C ₃₀ ) alkyl, substituted or unsubstituted (C ₆ -C ₃₀ ) aryl or halogen;

,

또는

이며, 여기에서 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 융합 고리를 형성할 수 있다.
Q is

,

or

Wherein R ₂₃₁ to R ₂₄₂ are independently of each other hydrogen, deuterium, (C ₁ -C ₃₀ ) alkyl, optionally substituted with (C ₁ -C ₃₀ ) alkyl, (C ₁ -C ₃₀ ) alkoxy, halogen, substituted or unsubstituted ( C ₆ -C ₃₀ ) aryl, cyano, substituted or unsubstituted (C ₅ -C ₃₀ ) cycloalkyl, or may be linked to adjacent substituents with alkylene or alkenylene to form a spiro ring or fused ring, or R ₂₀₇ or R ₂₀₈ can be linked to alkylene or alkenylene to form a saturated or unsaturated fused ring.

Substituents including the "alkyl", "alkoxy" and other "alkyl" moieties described herein include all linear or pulverized forms, and "cycloalkyl" is not only a monocyclic system but also substituted or unsubstituted adamantyl Or several ring-based hydrocarbons such as substituted or unsubstituted (C7-C30) bicycloalkyl. "Aryl" described in the present invention is an organic radical derived from an aromatic hydrocarbon by one hydrogen removal, and a single or fused ring containing 4 to 7, preferably 5 or 6 ring atoms in each ring as appropriate. It includes a system, including a form in which a plurality of aryl is connected by a single bond. Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, peryleneyl, chrysenyl, naphthasenyl, fluoranthenyl, and the like. It is not limited to this. Said naphthyl includes 1-naphthyl and 2-naphthyl, anthryl includes 1-anthryl, 2-anthryl and 9-anthryl, and fluorenyl is 1-fluorenyl, 2- Fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl. The "heteroaryl" described in the present invention contains 1 to 4 heteroatoms selected from B, N, O, S, P (= O), Si, and P as aromatic ring skeleton atoms, and the remaining aromatic ring skeleton atoms are carbon. Meaning an aryl group which is 5 to 6 membered monocyclic heteroaryl, and polycyclic heteroaryl condensed with one or more benzene rings, which may be partially saturated. In addition, 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. .

In addition, the "(C ₁ -C ₃₀ ) alkyl group" described in the present invention includes (C ₁ -C ₂₀ ) alkyl or (C ₁ -C ₁₀ ) alkyl, and the "(C ₆ -C ₃₀ ) aryl group "Includes (C ₆ -C ₂₀ ) aryl or (C ₆ -C ₁₂ ) aryl. "(C ₃ -C ₃₀ ) heteroaryl group" includes (C ₃ -C ₂₀ ) heteroaryl or (C ₃ -C ₁₂ ) heteroaryl and "(C ₃ -C ₃₀ ) cycloalkyl group" means (C ₃ -C ₂₀ ) cycloalkyl or (C ₃ -C ₇ ) cycloalkyl. "(C ₂ -C ₃₀ ) alkenyl or alkynyl" groups include (C ₂ -C ₂₀ ) alkenyl or alkynyl, (C ₂ -C ₁₀ ) alkenyl or alkynyl.

In addition, in the description of "substituted or unsubstituted" described in the present invention, 'substituted' refers to a case where it is further substituted with an unsubstituted substituent, and the substituents further substituted are each independently substituted or unsubstituted deuterium, halogen or halogen. a (C ₁ -C ₃₀₎ alkyl, (C ₆ -C ₃₀₎ aryl, (C ₆ -C ₃₀₎ aryl substituted or unsubstituted (C ₃ -C ₃₀₎ heteroaryl, 5-to 7 hetero won Cycloalkyl, 5- to 7-membered heterocycloalkyl fused at least one aromatic ring, (C ₃ -C ₃₀ ) cycloalkyl, (C ₆ -C ₃₀ ) cycloalkyl fused at least one aromatic ring, R ₉₁ R ₉₂ R ₉₃ Si-, (C ₂ -C ₃₀ ) alkenyl, (C ₂ -C ₃₀ ) alkynyl, cyano, carbazolyl, NR ₉₄ R ₉₅ , BR ₉₆ R ₉₇ , PR ₉₈ R ₉₉ , P (= O) R ₁₀₀ R ₁₀₁ , (C ₆ -C ₃₀ ) ar (C ₁ -C ₃₀ ) alkyl, (C ₁ -C ₃₀ ) alkyl (C ₆ -C ₃₀ ) aryl, R ₁₀₂ S-, R ₁₀₃ O- , R ₁₀₄ C (= 0)-, R ₁₀₅ C (= 0) O-, carboxyl, nitro or hydroxy One or more, and R ₉₁ to R ₁₀₃ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C ₁ -C ₃₀ ) alkyl, substituted or unsubstituted (C ₆ -C ₃₀ ) aryl, substituted or unsubstituted Substituted (C ₃ -C ₃₀ ) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl or substituted or unsubstituted (C ₃ -C ₃₀ ) with or without fused ring with adjacent substituents It may be linked with alkylene or substituted or unsubstituted (C ₃ -C ₃₀ ) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, and the alicyclic ring and monocyclic or polycyclic aromatic ring formed above The carbon atom of may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur; R ₁₀₄ and R ₁₀₅ mean (C ₁ -C ₃₀ ) alkyl, (C ₁ -C ₃₀ ) alkoxy, (C ₆ -C ₃₀ ) aryl or (C ₆ -C ₃₀ ) aryloxy.

The organic light emitting compound according to the present invention is exemplified by a compound having the following structure, but is not limited to these compounds:

The compound of Formula 1 may be prepared as shown in Scheme 1 below, and the following preparation method does not limit the method of preparing the organic light emitting compound of Formula I, and modifications of the following preparation method are obvious to those skilled in the art. something to do.

Scheme 1

In Scheme 1

L ₁ , R, R ₁ to R ₅ , R ₆ to R ₉ , n and m are the same as defined in the above formula (I).

The present invention also relates to an organic electroluminescent device comprising the compound of formula (I).

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 includes at least a layer including the organic light emitting compound of Formula (I).

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 (I) 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 Formula I, a group consisting of Group 1, 2, 4, 5 cycle transition metals, lanthanide series metals and organic metals of d-transition elements 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 (I) 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 red, green, or blue 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 device using the organic light emitting compound according to the present invention as a dopant material of the light emitting layer, in particular, has an advantage of producing an OLED device having excellent light emission efficiency and excellent life characteristics of the device, and having 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.

[Production Example 1]

compound One Manufacture

compound 1-1 Manufacture

5 g (21 mmol) of 2,5-dibromopyridine, 2.6 g (21 mmol) of phenyl boronic acid, and 1.3 g (1.1 mmol) of Pd (PPh ₃ ) _{4 in the} presence of nitrogen, toluene It was dissolved in 50 mL, 25 mL of ethanol, 25 mL of 2 M sodium carbonate, and stirred under reflux at 120 ° C. After 2 hours, the reaction was washed with distilled water, extracted with ethyl acetate, the organic layer was dried over MgSO ₄ and the solvent was removed using a rotary evaporator and purified by column chromatography to give the title compound 1-1 2.6 g (11 mmol).

compound 1-2 Manufacture

Compound 1-1 2.6 g (11 mmol), d ⁵ -phenylboronic acid 1.8 g (13 mmol), Pd (PPh ₃ ) ₄ 0.7 g (0.6 mmol) in the presence of nitrogen, 40 mL of toluene, 20 mL of ethanol It was dissolved in 20 mL of 2 M sodium carbonate and stirred under reflux at 120 ° C. After 2 hours, the reaction was washed with distilled water, extracted with ethyl acetate, the organic layer was dried over MgSO ₄ and the solvent was removed using a rotary evaporator and purified by column chromatography to give 2.2 g (9.3 mmol) of the title compound 1-2 .

compound 1-3 Manufacture

2.2 g (9.3 mmol) of compound 1-2 , 1.1 g (4.2 mmol) of iridium chloride (IrCl ₃ ), 45 mL of 2-ethoxyethanol, and 15 mL of distilled water were added thereto, and the mixture was stirred under reflux for 24 hours. Upon completion of the reaction, it was cooled to room temperature and the precipitate was filtered off. The obtained solid was washed with water and methanol and recrystallized with nucleic acid to obtain 1.9 g (1.4 mmol) of the title compound 1-3 .

compound 20 Manufacture

1.9 g (1.4 mmol) of Compound 1-3 , 0.82 g (8.4 mmol) of sodium carbonate, and 2.3 ml (4.2 mmol) of 2,4-pentanedione were dissolved in 30 mL of 2-ethoxyethanol and stirred under reflux for 5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the solid precipitate thus formed was filtered, separated by silica gel column chromatography, and recrystallized to obtain 0.67 g (0.9 mmol) of the title compound 20 as yellow crystals.

Preparation of Compound 1

1.4 g (1.8 mmol) of Compound 20 , 0.85 g (3.6 mmol) of Compound 1-2 , and 20 mL of glycerol were refluxed at 220 ° C. for 12 hours to cool to room temperature. The mixture was washed with water and methanol, dissolved in methylene chloride, separated by silica gel column chromatography to obtain 0.8 g (0.9 mmol) of crystalline compound 1 of the iridium complex represented by the formula of yellow crystals.

¹ H NMR (CDCl ₃ , 200 MHz) δ = 7.47 (3H, m), 7.53-7.54 (6H, m), 7.69 (3H, m), 8.03 (3H, m), 8.3 (3H, m), 8.78 (3H, m); MS / FAB found 899, calculated 898.16

[Production Example 2]

compound 8 Manufacture

compound 2-1 Manufacture

5 g (21 mmol) of 2,5-dibromopyridine, 3,4-difluorophenylboronic acid (3,4-difluorophenylboronic acid) 3.3 g (21 mmol), Pd ( 1.3 g (1.1 mmol) of PPh ₃ ) ₄ were dissolved in 50 mL of toluene, 25 mL of ethanol, and 25 mL of 2 M sodium carbonate in the presence of nitrogen, followed by stirring at reflux at 120 ° C. After 2 hours, the reaction was washed with distilled water, extracted with ethyl acetate, the organic layer was dried over MgSO ₄ and the solvent was removed using a rotary evaporator and purified by column chromatography to give the title compound 2-1 2.6 g (9.6 mmol).

compound 2-2 Manufacture

2.6 g (11 mmol) of the prepared compound 2-1 , 1.6 g (11.3 mmol) of 4-fluorophenylboronic acid, and 0.7 g (0.52 mmol) of Pd (PPh ₃ ) _{4 in the} presence of nitrogen, 40 mL of toluene It was dissolved in 20 mL of ethanol and 20 mL of 2 M sodium carbonate and stirred at reflux at 120 ° C. After 2 hours, the reaction was washed with distilled water, extracted with ethyl acetate, the organic layer was dried over MgSO ₄ and the solvent was removed using a rotary evaporator, purified by column chromatography to give the title compound 2-2 2.3 g (8.6 mmol).

compound 2-3 Manufacture

2.3 g (8.6 mmol) of compound 2-2 , 1.1 g (3.9 mmol) of iridium chloride (IrCl ₃ ), 45 mL of 2-ethoxyethanol, and 15 mL of distilled water were added thereto, and the mixture was stirred under reflux for 24 hours. Upon completion of the reaction, it was cooled to room temperature and the precipitate was filtered off. The obtained solid was washed with water and methanol and recrystallized with nucleic acid to give 2.7 g (1.7 mmol) of the title compound 2-3 .

compound 2-4 Manufacture

Compound 2-3 1.9 g (1.7 mmol), sodium carbonate 0.82 g (8.5 mmol), and 2.3 ml (4.3 mmol) of 2,4-pentanedione were dissolved in 30 mL of 2-ethoxyethanol and stirred under reflux for 5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the solid precipitate produced was filtered, separated by silica gel column chromatography, and recrystallized to obtain 0.8 g (0.93 mmol) of the title compound 2-4 as yellow crystals.

compound 8 Manufacture

Compound 2-4 1.4 g (1.8 mmol), compound 2-2 0.85 g (3.6 mmol), 12 sigan the reflux 20 mL of glycerol at 220 ℃ stirred to cool to room temperature. The mixture was washed with water and methanol, dissolved in methylene chloride, separated by silica gel column chromatography to obtain 0.8 g (0.9 mmol) of the title compound 8 as yellow crystals.

¹ H NMR (CDCl ₃ , 200 MHz) δ = 7.22 (3H, m), 7.3 (6H, m), 7.39 (6H, m), 7.69 (3H, m), 8.01-8.03 (6H, m), 8.78 (3H, m); MS / FAB found 1045, calculated 1044.98

[Manufacture example 3]

compound 15 Manufacture

compound 3-1 Manufacture

5 g (21 mmol) of 2,5-dibromo-4-methylpyridine, 2.6 g (21 mmol) of phenylboronic acid, and 1.3 g (1.1 mmol) of Pd (PPh ₃ ) _{4 in the} presence of nitrogen, toluene 50 mL, 25 mL of ethanol, and 25 mL of 2 M sodium carbonate were stirred at reflux at 120 ° C. After 2 hours, the reaction was washed with distilled water, extracted with ethyl acetate, the organic layer was dried over MgSO ₄ and the solvent was removed using a rotary evaporator and purified by column chromatography to give the title compound 3-1 4 g (17 mmol).

compound 3-2 Manufacture

Compound 3-1 4 g (17 mmol), 4-fluorophenylboronic acid 2.8 g (20 mmol), and Pd (PPh ₃ ) ₄ 1 g (0.9 mmol) in the presence of nitrogen, 80 mL of toluene, ethanol 40 mL, dissolved in 40 mL of 2 M sodium carbonate, and stirred under reflux at 120 ℃. After 2 hours, the reaction was washed with distilled water, extracted with ethyl acetate, the organic layer was dried over MgSO ₄ and the solvent was removed using a rotary evaporator and purified by column chromatography to give the title compound 3-2 4 g (15 mmol).

compound 3-3 Manufacture

4 g (15 mmol) of Compound 3-2 , 2 g (6.8 mmol) of iridium chloride (IrCl ₃ ), 90 mL of 2-ethoxyethanol, and 30 mL of distilled water were added and stirred under reflux for 24 hours. Upon completion of the reaction, it was cooled to room temperature and the precipitate was filtered off. The obtained solid was washed with water and methanol and recrystallized with nucleic acid to give 3 g (2 mmol) of the title compound 3-3 .

compound 3-4 Manufacture

3 g (2 mmol) of compound 3-3, 1.3 g (12 mmol) of sodium carbonate, and 3.7 ml (6 mmol) of 2,4-pentanedione were dissolved in 30 mL of 2-ethoxyethanol and stirred under reflux for 5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the solid precipitate thus formed was filtered, separated by silica gel column chromatography, and recrystallized to obtain 1.5 g (1.8 mmol) of the title compound 3-4 as yellow crystals.

Preparation of Compound 15

1.5 g (1.8 mmol) of compound 3-4, 1 g (3.6 mmol) of compound 3-2 and 20 mL of glycerol were refluxed at 220 ° C. for 12 hours to cool to room temperature. The mixture was washed with water and methanol, dissolved with methylene chloride, separated by silica gel column chromatography to obtain 1 g (1 mmol) of crystalline compound 15 of the iridium complex represented by the formula of yellow crystals.

¹ H NMR (CDCl ₃ , 200 MHz) δ = 2.61 (9H, s), 7.3 (6H, m), 7.39 (6H, m), 7.47 (3H, m), 7.53-7.54 (6H, m), 8.02 (3H, s), 8.3 (3H, m), 8.79 (3H, s); MS / FAB found 980, calculated 979.12

[Production Example 4]

compound 23 Manufacture

compound 4-1 Manufacture

5 g (21 mmol) of 2-bromopyridine, 2.6 g (21 mmol) of phenylboronic acid, and 1.3 g (1.1 mmol) of Pd (PPh ₃ ) ₄ were added in the presence of nitrogen, 50 mL of toluene, 25 mL of ethanol, 2 It was dissolved in 25 mL of M sodium carbonate and stirred at reflux at 120 ° C. After 2 hours, the reaction was washed with distilled water, extracted with ethyl acetate, the organic layer was dried over MgSO ₄ and the solvent was removed using a rotary evaporator and purified by column chromatography to obtain the title compound 4-1 4 g (17 mmol).

compound 23 Manufacture

14 g (13 mmol) of Compound 3-3, 9.8 g (39 mmol) of Compound 4-1 , 10 g (39 mmol) of AgCF ₃ SO ₃ , and 50 mL of 2-methoxy-ethylether were refluxed under reflux for 12 hours, followed by room temperature. To cool. The mixture was washed with water and methanol, dissolved in methanol and separated by silica gel column chromatography to obtain 3.5 g (4.5 mmol) of crystalline compound 23 of the iridium complex represented by the formula of red crystals.

¹ H NMR (CDCl ₃ , 200 MHz) δ = 2.61 (6H, s), 7 (1H, m), 7.3 (4H, m), 7.39 (4H, m), 7.47-7.54 (10H, m), 7.97 (1H, m), 8.02 (2H, s), 8.3 (3H, m), 8.56 (1H, m), 8.79 (2H, s); MS / FAB found 872, calculated 871.01

[Production Example 5]

compound 33 Manufacture

compound 5-1 Manufacture

5 g (21 mmol) of 2-bromopyridine, 2.6 g (21 mmol) of o-tolylboronic acid, 1.3 g (1.1 mmol) of Pd (PPh ₃ ) _{4 in the} presence of nitrogen, toluene 50 Dissolve in 25 mL of ethanol, 25 mL of ethanol and 25 mL of 2 M sodium carbonate, and stir to reflux at 120 ° C. After 2 hours, the reaction was washed with distilled water, extracted with ethyl acetate, the organic layer was dried over MgSO ₄ , and the solvent was removed by rotary evaporator. Then purified by column chromatography to give the title compound 5-1 4 g (17 mmol).

compound 5-2 Manufacture

4 g (15 mmol) of compound 5-1 , 2 g (6.8 mmol) of iridium chloride (IrCl ₃ ), 90 mL of 2-ethoxyethanol, and 30 mL of distilled water were added and stirred under reflux for 24 hours. Upon completion of the reaction, it was cooled to room temperature and the precipitate was filtered off. The obtained solid was washed with water and methanol and recrystallized with nucleic acid to give 3 g (2 mmol) of the title compound 5-2 .

compound 33 Manufacture

14 g (13 mmol) of Compound 5-2, 9.8 g (39 mmol) of Compound 3-2 , 10 g (39 mmol) of AgCF ₃ SO ₃ , and 50 mL of 2-methoxy-ethylether were refluxed under reflux for 12 hours, followed by room temperature. To cool. The mixture was washed with water and methanol, dissolved in methanol, separated by silica gel column chromatography to obtain 3.5 g (4.5 mmol) of the crystalline compound 33 of the iridium complex represented by the formula of red crystals.

¹ H NMR (CDCl ₃ , 200 MHz) δ = 2.59 (6H, s), 2.61 (3H, s), 7 (2H, m), 7.3-7.39 (10H, m), 7.47-7.54 (5H, m) , 7.97 (2H, m), 8.02 (1H, s), 8.3 (1H, m), 8.56 (2H, m), 8.79 (1H, s); MS / FAB found 791, calculated 790.95

Production Example 6

compound 39 Manufacture

compound 6-1 Manufacture

5 g (21 mmol) of 2,5-dibromo-4-methylpyridine, 2.6 g (21 mmol) of naphthalen-1-ylboronic acid, and 1.3 g (1.1 mmol) of Pd (PPh ₃ ) _{4 in the} presence of nitrogen 50 mL of toluene, 25 mL of ethanol, and 25 mL of 2 M sodium carbonate were stirred at reflux at 120 ° C. After 2 hours, the reaction was washed with distilled water, extracted with ethyl acetate, the organic layer was dried over MgSO ₄ and the solvent was removed using a rotary evaporator and purified by column chromatography to give the title compound 6-1 2.6 g (11 mmol).

compound 6-2 Manufacture

Compound 6-1 2.6 g (11 mmol), d ⁵ -phenylboronic acid 1.8 g (13 mmol), Pd (PPh ₃ ) ₄ 0.7 g (0.6 mmol) in the presence of nitrogen, 40 mL of toluene, 20 mL of ethanol It was dissolved in 20 mL of 2 M sodium carbonate and stirred under reflux at 120 ° C. After 2 hours, the reaction was washed with distilled water, extracted with ethyl acetate, the organic layer was dried over MgSO ₄ and the solvent was removed using a rotary evaporator and purified by column chromatography to give the title compound 6-2 2.2 g (9.3 mmol).

compound 6-3 Manufacture

2.2 g (9.3 mmol) of compound 6-2 , 1.1 g (4.2 mmol) of iridium chloride (IrCl ₃ ), 45 mL of 2-ethoxyethanol, and 15 mL of distilled water were added thereto, and the mixture was stirred under reflux for 24 hours. Upon completion of the reaction, it was cooled to room temperature and the precipitate was filtered off. The obtained solid was washed with water and methanol and recrystallized with nucleic acid to obtain 1.9 g (1.4 mmol) of the title compound 6-3 .

compound 6-4 Manufacture

1.9 g (1.4 mmol) of Compound 6-3 , 0.82 g (8.4 mmol) of sodium carbonate, and 2.3 ml (4.2 mmol) of 2,4-pentanedione were dissolved in 30 mL of 2-ethoxyethanol and stirred under reflux for 5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the resulting solid precipitate was filtered, separated by silica gel column chromatography, and recrystallized to obtain 0.67 g (0.9 mmol) of the title compound 6-4 as yellow crystals.

Preparation of Compound 39

Compound 6-4 1.4 g (1.8 mmol), compound 6-2 0.85 g (3.6 mmol), 12 sigan the reflux 20 mL of glycerol at 220 ℃ stirred to cool to room temperature. The mixture was washed with water and methanol, dissolved with methylene chloride, separated by silica gel column chromatography to obtain 0.8 g (0.9 mmol) of crystalline compound 1 of the yellow iridium complex.

¹ H NMR (CDCl ₃ , 200 MHz) δ = 2.61 (9H, s), 7.55 (6H, m), 7.69 (3H, m), 8.02 (3H, s), 8.08-8.1 (6H, m), 8.55 (3H, m), 8.79 (3H, s); MS / FAB found 1091, calculated 1090.42

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, an ITO substrate is placed in the substrate folder of the vacuum deposition apparatus, and 2-TNATA [4,4 ', 4 "-tris (N, N- (2-naphthyl))-phenylamino is placed in the cell in the vacuum deposition apparatus. ) Triphenylamine], evacuated until the vacuum in the chamber reached 10 ^-6 torr, and applied a current to the cell to evaporate 2-TNATA to deposit a 60 nm thick hole injection layer on the ITO substrate. Subsequently, NPB [N, N'-bis (α-naphthyl) -N, N'-diphenyl-4,4'-diamine] was added to another cell in the vacuum deposition equipment, and a current was applied to the cell. NBP was evaporated to deposit a 20 nm thick hole transport layer on the hole injection layer, and then a light emitting layer was deposited thereon as follows: as a host in one cell in the vacuum deposition equipment. CBP [4,4'-N, N'-dicarbazole-biphenyl] was added, and another cell was added with compound 11 of the present invention, respectively, and then the two materials were evaporated at different rates to 4-20. A light emitting layer having a thickness of 30 nm was deposited on the hole transport layer by doping by weight by weight, followed by bis (2-methyl-8-quinolinate) ( p -phenylphenolraito) aluminum (III) as a hole blocking layer on the light emitting layer. (BAlq) was deposited to a thickness of 10 nm, and then Alq [tris (8-hydroxyquinoline) -aluminum (III)] was deposited to a thickness of 20 nm as an electron transport layer, followed by Alq [tris (8) to an electron transport layer. -Hydroxyquinazolin) -aluminum (III)] was deposited to a thickness of 20 nm, and then Liq [lithium quinolate] was deposited to a thickness of 1 to 2 nm with an electron injection layer. An Al cathode was deposited to a thickness of 150 nm to fabricate 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 3.6 mA / cm ² flowed at a voltage of 6.8 V, and green light emission of 1080 cd / m ² was confirmed.

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

An OLED device was manufactured in the same manner as in Example 1, except that Compound 13 of the present invention was used as the dopant material.

As a result, a current of 3.5 mA / cm ² flowed at a voltage of 6.7 V, and green light emission of 1075 cd / m ² was confirmed.

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

An OLED device was manufactured in the same manner as in Example 1, except that Compound 20 of the present invention was used as a dopant material.

As a result, a current of 3.3 mA / cm ² flowed at a voltage of 6.8 V, and green light emission of 1085 cd / m ² was confirmed.

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

Compound 36 of the present invention as a dopant material An OLED device was manufactured in the same manner as in Example 1 except for using the same.

As a result, a current of 3.5 mA / cm ² flowed at a voltage of 6.7 V, and green light emission of 1070 cd / m ² was confirmed.

Comparative Example 1 Luminescence Characteristics of OLED Devices Using Conventional Luminescent Materials

An OLED device was manufactured in the same manner as in Example 1, except that Ir (ppy) ₃ [tris (2-phenylpyridine) iridium] was used instead of the compound of the present invention as a dopant material in one cell in a vacuum deposition equipment.

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 dopant material has a low LUMO value, which is well matched with the host, and thus has excellent characteristics such as efficiency and lifespan. By inducing the power consumption could be improved.

Claims (11)

An organic light emitting compound represented by formula (I)
(I)

In Formula I,
L ₁ is an organic ligand;
R ₁ to R ₅ are each independently deuterium, halogen, substituted or unsubstituted (C ₃ -C ₃₀ ) cycloalkyl, substituted or unsubstituted 5 to 7 membered heterocycloalkyl, cyano, nitro, BR ₂₁ R ₂₂ , PR ₂₃ R ₂₄ , P (═O) R ₂₅ R ₂₆ [R ₂₁ to R ₂₆ are independently of each other substituted or unsubstituted (C ₁ -C ₃₀ ) alkyl, substituted or unsubstituted (C ₆ -C ₃₀ ) aryl or substituted or unsubstituted (C ₃ -C ₃₀ ) heteroaryl.], R ₂₇ R ₂₈ R ₂₉ Si- [R ₂₇ to R ₂₉ are each independently substituted or unsubstituted (C ₁ -C ₃₀ ) alkyl, substituted or unsubstituted (C ₆ -C ₃₀ ) aryl or substituted or unsubstituted (C ₃ -C ₃₀ ) heteroaryl], substituted or unsubstituted (C ₆ -C ₃₀ ) Ar (C ₁ -C ₃₀ ) alkyl;
R is hydrogen, substituted or unsubstituted (C ₁ -C ₃₀ ) alkyl, substituted or unsubstituted (C ₁ -C ₃₀ ) alkoxy, substituted or unsubstituted (C ₆ -C ₃₀ ) aryl or substituted or unsubstituted (C ₃ -C ₃₀ ) heteroaryl;
R ₆ to R ₉ are hydrogen, deuterium, halogen, substituted or unsubstituted (C ₁ -C ₃₀ ) alkyl, substituted or unsubstituted (C ₆ -C ₃₀ ) aryl, substituted or unsubstituted (C ₅ -C ₃₀₎ heteroaryl, substituted or unsubstituted (C ₃ -C ₃₀₎ cycloalkyl-alkyl, substituted or a 5-to 7-membered heterocycloalkyl, cyano, nitro _{unsubstituted, BR 21 R 22, PR 23} R 24 , P (= 0) R ₂₅ R _26, NR ₃₀ R ₃₁ [R ₂₁ to R ₂₆ , R ₃₀ to R ₃₁ are each independently substituted or unsubstituted (C ₁ -C ₃₀ ) alkyl, substituted or unsubstituted (C ₆ -C ₃₀ ) aryl or substituted or unsubstituted (C ₃ -C ₃₀ ) heteroaryl.], R ₂₇ R ₂₈ R ₂₉ Si- [R ₂₇ to R ₂₉ are each independently substituted or unsubstituted. (C ₁ -C ₃₀ ) alkyl, substituted or unsubstituted (C ₆ -C ₃₀ ) aryl or substituted or unsubstituted (C ₃ -C ₃₀ ) heteroaryl], R ₃₂ Y- [Y is S or O, R ₃₂ is substituted or unsubstituted (C ₁ -C ₃₀ ) alkyl, substituted or unsubstituted (C ₆ -C ₃₀ ) aryl, or Substituted or unsubstituted (C ₃ -C ₃₀ ) heteroaryl], substituted or unsubstituted (C ₂ -C ₃₀ ) alkenyl, substituted or unsubstituted (C ₂ -C ₃₀ ) alkynyl, substituted or Unsubstituted (C ₆ -C ₃₀ ) ar (C ₁ -C ₃₀ ) alkyl or adjacent substituents may combine to form a fused ring;
n and m are each independently an integer from 1 to 3;
The heterocycloalkyl and heteroaryl include one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P. The method of claim 1,
remind Substituents further substituted with substituents are each independently substituted with deuterium, halogen, halogen-substituted (C ₁ -C ₃₀ ) alkyl, (C ₆ -C ₃₀ ) aryl, (C ₆ -C ₃₀ ) aryl or Unsubstituted (C ₃ -C ₃₀ ) heteroaryl, 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic rings, (C ₃ -C ₃₀ ) cycloalkyl, One or more aromatic rings fused with (C ₆ -C ₃₀ ) cycloalkyl, R ₉₁ R ₉₂ R ₉₃ Si-, (C ₂ -C ₃₀ ) alkenyl, (C ₂ -C ₃₀ ) alkynyl, cyano, carba Zolyl, NR ₉₄ R ₉₅ , BR ₉₆ R ₉₇ , PR ₉₈ R ₉₉ , P (= O) R ₁₀₀ R ₁₀₁ , (C ₆ -C ₃₀ ) ar (C ₁ -C ₃₀ ) alkyl, (C ₁ -C ₃₀ ) Alkyl (C ₆ -C ₃₀ ) aryl, consisting of R ₁₀₂ S-, R ₁₀₃ O-, R ₁₀₄ C (= 0)-, R ₁₀₅ C (= 0) O-, carboxyl, nitro or hydroxy represents at least one selected from the group, R ₉₁ to R ₁₀₃ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C ₁ -C ₃₀₎ alkyl, substituted Is unsubstituted (C ₆ -C ₃₀₎ aryl, substituted or unsubstituted (C ₃ -C ₃₀₎ heteroaryl, a substituted or unsubstituted fused ring including a heterocycloalkyl or adjacent substituents of the 5-to 7-membered ring Linked with substituted or unsubstituted (C ₃ -C ₃₀ ) alkylene or substituted or unsubstituted (C ₃ -C ₃₀ ) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, with or without inclusions. The carbon atoms of the alicyclic ring and the monocyclic or polycyclic aromatic ring formed may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur; R ₁₀₄ and R ₁₀₅ are (C ₁ -C ₃₀ ) alkyl, (C ₁ -C ₃₀ ) alkoxy, (C ₆ -C ₃₀ ) aryl or (C ₆ -C ₃₀ ) aryloxy, characterized in that . The organic light emitting compound according to claim 1, wherein the compound of formula I is a compound of formula II or III:
[Formula II]

[Formula III]

In Formula II or Formula III, R ₁ to R ₅ , R, R ₆ to R ₉ , L ₁ , n are the same as defined in Formula I above. The organic light emitting compound of claim 1, wherein L ₁ is selected from compounds having the structure:

In the above formulas,
R ₂₀₁ to R ₂₀₃ are each independently hydrogen, deuterium, (C ₁ -C ₃₀ ) alkyl with or without halogen, (C ₁ -C ₃₀ ) alkyl with or without (C ₁ -C ₃₀ ) Aryl or halogen;
R ₂₀₄ to R ₂₁₉ are each independently hydrogen, deuterium, substituted or unsubstituted (C ₁ -C ₃₀ ) alkyl, substituted or unsubstituted (C ₁ -C ₃₀ ) alkoxy, substituted or unsubstituted (C _3- C ₃₀ ) cycloalkyl, substituted or unsubstituted (C ₂ -C ₃₀ ) alkenyl, substituted or unsubstituted (C ₆ -C ₃₀ ) aryl, substituted or unsubstituted mono or substituted or unsubstituted di (C _1- C ₃₀ ) alkylamino, substituted or unsubstituted mono or di (C ₆ -C ₃₀ ) arylamino, SF ₅ , substituted or unsubstituted tri (C ₁ -C ₃₀ ) alkylsilyl, substituted or unsubstituted Di (C ₁ -C ₃₀ ) alkyl (C ₆ -C ₃₀ ) arylsilyl, substituted or unsubstituted tri (C ₆ -C ₃₀ ) arylsilyl, cyano or halogen;
R ₂₂₀ through R ₂₂₃ independently represent hydrogen, deuterium, halogen-substituted or unsubstituted (C ₁ -C ₃₀₎ alkyl or (C ₁ -C ₃₀₎ alkyl is optionally substituted (C ₆ -C ₃₀₎ with each other Aryl;
R ₂₂₄ and R ₂₂₅ are independently of each other hydrogen, deuterium, substituted or unsubstituted (C ₁ -C ₃₀ ) alkyl, substituted or unsubstituted (C ₆ -C ₃₀ ) aryl or halogen, or R ₂₂₄ and R ₂₂₅ are does not contain a fused ring with or (C ₃ -C ₁₂₎ alkylene or (C ₃ -C ₁₂₎ alkenylene with an alicyclic ring, or a monocyclic or polycyclic form a ring;
R ₂₂₆ is substituted or unsubstituted (C ₁ -C ₃₀ ) alkyl, substituted or unsubstituted (C ₆ -C ₃₀ ) aryl, substituted or unsubstituted (C ₅ -C ₃₀ ) heteroaryl or halogen;
R ₂₂₇ to R ₂₂₉ are independently of each other hydrogen, deuterium, substituted or unsubstituted (C ₁ -C ₃₀ ) alkyl, substituted or unsubstituted (C ₆ -C ₃₀ ) aryl or halogen;
Q is

,

or

Wherein R ₂₃₁ to R ₂₄₂ are independently of each other hydrogen, deuterium, (C ₁ -C ₃₀ ) alkyl, optionally substituted with (C ₁ -C ₃₀ ) alkyl, (C ₁ -C ₃₀ ) alkoxy, halogen, substituted or unsubstituted ( C ₆ -C ₃₀ ) aryl, cyano, substituted or unsubstituted (C ₅ -C ₃₀ ) cycloalkyl, or may be linked to adjacent substituents with alkylene or alkenylene to form a spiro ring or fused ring, or R ₂₀₇ or R ₂₀₈ can be linked to alkylene or alkenylene to form a saturated or unsaturated fused ring. The organic light emitting compound according to claim 1, wherein the compound of formula I is selected from compounds having the structure

An organic electroluminescent device comprising the compound according to any one of claims 1 to 5. The organic electroluminescent device according to claim 6, wherein the compound is used as a dopant material of the light emitting layer. The organic electroluminescent device of claim 6,
A first electrode;
A second electrode; And
An organic electroluminescent device comprising at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer includes a layer containing at least the organic light emitting compound of Formula (I). The method of claim 8, wherein the organic layer further comprises at least one metal or complex compound selected from the group consisting of Group 1, Group 2, 4 cycle, 5 cycle transition metal, lanthanide-based metal and d-transition element organic metal The organic electroluminescent element which is characterized by the above-mentioned. The organic electroluminescent device according to claim 8, wherein the organic material layer comprises a light emitting layer and a charge generating layer. The organic electroluminescent device of claim 8, wherein the organic material layer emits white light by including at least one organic light emitting layer emitting red, green, or blue light.