KR20110088098A - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Abstract

PURPOSE: An organic light-emitting compound is provided to ensure excellent luminous efficiency and lifetime property of materials, and to prepare an organic light emitting diode with excellent driving durability. CONSTITUTION: An organic light-emitting compound has the structure represented by chemical formula 1. An organic electroluminescence device comprises a first electrode, a second electrode, and one or more organic material layers interposed between first and second electrodes. The organic material layer comprises one or more organic light-emitting compounds and one or more host compounds represented by chemical formula 2: (Ar_11)_c-L_11-(Ar_12)_d or chemical formula 3: (Ar_13)_e-L_12-(Ar_14)_f.

Description

Novel organic electroluminescent compounds and organic electroluminescent device using the same

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

[Formula 1]

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

An organic EL device is a device that emits light when an electron is injected into an organic film formed between an electron injection electrode (cathode) and a hole injection electrode (anode) and then disappears after pairing electrons and holes. The device can be formed on a flexible transparent substrate such as plastic, and can be driven at a lower voltage (less than 10V) compared to a plasma display panel or an inorganic EL display, and also consumes power. It is relatively small and has the advantage of excellent color. In addition, the organic EL device can display three colors of green, blue, and red, and thus, has become a subject of much interest as a next-generation rich color display device.

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

The organic EL device is usually composed of anode / HIL / HTL / EML / ETL / EIL / cathode. The organic electroluminescent device of blue, green, and red can be realized depending on how the emission layer (EML) is formed.

The light emitting material can be classified into a host material and a dopant material in terms of its function. In general, a device structure having excellent EL characteristics is known to make a light emitting layer by doping a host with a dopant. Recently, the development of high efficiency and long life organic EL devices has emerged as an urgent task, and considering the level of EL characteristics required in medium and large OLED panels, it is urgent to develop materials that are much superior to existing light emitting materials.

On the other hand, in the case of the conventional blue material, many materials have been developed and commercialized since Idemitsu-high acid diphenylvinyl-biphenyl (DPVBi, compound a), and the Idemitsu-high acid blue material system and Kodak's dinaphthyl Although anthracene (dinaphthylanthracen; DNA, compound b), tetra (t-butyl) perylene (compound c) system, etc. are known, many research and developments are still required.

The system of Idemitsu-high acid disryl compound, which is known to be the most efficient so far, has a power efficiency of 6 lm / W and a device life of more than 30,000 hours, but the color purity decreases with driving time. When applied to a full-color display, its lifetime is only thousands of hours. Blue light emission is advantageous in terms of luminous efficiency even if the light emission wavelength is shifted toward the longer wavelength, but it is not easy to apply to high-quality display because it does not satisfy pure blue color, and there is a problem in color purity, efficiency and thermal stability, so that research and development It is an urgent part.

As described above, the conventional materials are composed of a single layer without forming a host-dopant thin film layer, and it is determined that commercialization is difficult in terms of color purity and efficiency, and reliable data on long life is insufficient.

Accordingly, an object of the present invention is to firstly provide an organic light emitting compound having excellent luminous efficiency and device life, and having an appropriate color coordinate, in order to solve the above problems, and secondly, to solve the above organic light emitting compound. radiation

The present invention relates to an organic light emitting compound represented by the following formula (1) and an organic electroluminescent device comprising the same, the organic light emitting compound according to the present invention has good luminous efficiency and excellent life characteristics of the material OLED excellent in driving life of the device There is an advantage to manufacture the device.

[Formula 1]

[In Formula 1,

Ar ₁ and Ar ₂ are each independently substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (C3-C30) heteroarylene;

R ₁ to R ₈ 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) hetero Aryl, substituted or unsubstituted (C3-C30) cycloalkyl, cyano, nitro, -NR ₁₁ R ₁₂ , -BR ₁₃ R ₂₁₄ , -PR ₁₅ R ₁₆ , -P (= O) R ₁₇ R ₁₈ , R ₁₉ R ₂₀ R ₂₁ Si-, R ₂₂ Y-, substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted A cycloaliphatic ring that is linked to a (C2-C30) alkynyl, substituted or unsubstituted (C3-C30) alkylene, or a substituted or unsubstituted (C3-C30) alkenylene, with or without adjacent substituents and fused rings A ring and a monocyclic or polycyclic aromatic ring may be formed, and the carbon atoms of the monocyclic or polycyclic aromatic ring formed may be substituted with nitrogen;

Ring A and Ring B are each independently a 5- to 7-membered heterocyclic amino group, wherein the heterocyclic amino group may be fused with one or more aromatic rings, and is also selected from NR ₂₃ , O, S or SiR ₂₄ R ₂₅ May further comprise one or more hetero atoms;

R ₁₁ to R ₂₅ are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl, or an adjacent substituent. Linking with substituted or unsubstituted (C3-C30) alkylene or substituted or unsubstituted (C3-C30) alkenylene with or without fused ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring Can;

Y is S or O;

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

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

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

In addition, the description of "substituted or unsubstituted" described in the present invention, Ar ₁ , Ar ₂ , R _{1 To} R ₆ And R _{11 To} R ₂₅ are each independently deuterium, halogen, halogen substituted or unsubstituted ( C1-C30) alkyl, (C6-C30) aryl, (C6-C30) aryl substituted or unsubstituted (C3-C30) heteroaryl, 5- to 7-membered heterocycloalkyl, aromatic ring at least one fused 5- to 7-membered heterocycloalkyl, (C3-C30) cycloalkyl, (C6-C30) cycloalkyl fused with one or more aromatic rings, R ^a R ^b R ^c Si-, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, carbazolyl, -NR ^d R ^e , -BR ^f R ^g , -PR ^h R ⁱ , -P (= O) R ^j R ^k , (C6-C30) ar ( C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, R ^l T-, R ^m C (= 0)-, R ^m C (= 0) O-, carboxyl, nitro or hydro Further substituted with one or more selected from the group consisting of hydroxy, or substituents adjacent to each other connected to form a ring Mihanda. In addition, R ^a to R ^l are independently of each other (C1-C30) alkyl, (C6-C30) aryl or (C3-C30) heteroaryl; T is S or O; R ^m means (C1-C30) alkyl, (C1-C30) alkoxy, (C6-C30) aryl or (C6-C30) aryloxy.

The ring A and ring B are independently selected from the following structures.

[Z is a chemical bond or-(CR ₄₁ R ₄₂ ) _m -,-(R ₄₁ ) C = C (R ₄₂ )-, -N (R ₄₃ )-, -S-, -O-, -Si ( R ₄₄ ) (R ₄₅ )-, -P (R ₄₆ )-, -P (= 0) (R ₄₇ )-, -C (= 0)-, or -B (R ₄₈ )-; R ₃₁ to R ₄₈ 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) hetero Aryl, substituted or unsubstituted (C3-C30) cycloalkyl, cyano, nitro, -NR ₁₁ R ₁₂ , -BR ₁₃ R ₂₁₄ , -PR ₁₅ R ₁₆ , -P (= O) R ₁₇ R ₁₈ , R ₁₉ R ₂₀ R ₂₁ Si-, R ₂₂ Y-, substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted A cycloaliphatic ring that is linked to a (C2-C30) alkynyl, substituted or unsubstituted (C3-C30) alkylene, or a substituted or unsubstituted (C3-C30) alkenylene, with or without adjacent substituents and fused rings A ring and a monocyclic or polycyclic aromatic ring may be formed, and the carbon atoms of the monocyclic or polycyclic aromatic ring formed may be substituted with nitrogen; m is an integer from 1 to 4.]

More specifically, the ring A and ring B are independently selected from the following structures, but are not limited thereto.

는 하기 구조에서 선택되나, 이에 한정되지는 않는다.remind

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

[R ₁ , R ₂ , R ₃ and R ₆ are independently of each other deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl or substituted or unsubstituted (C6-C30) aryl.]

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

[Ar ₁ , Ar ₂ , R ₁ to R ₈ , Ring A and Ring B in Scheme 1 are the same as defined in Formula 1 above.]

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 light emitting compound is used as the dopant material of the light emitting layer.

The organic material layer may include a light emitting layer, and the light emitting layer may further include one or more hosts in addition to the one or more organic light emitting compounds of Formula 1, and the host applied to the organic light emitting device of the present invention is not particularly limited. Do not.

The host applied to the organic electroluminescent device of the present invention is preferably selected from the compound of formula (2) or (3).

[Formula 2]

(Ar ₁₁ ) _c -L _11- (Ar ₁₂ ) _d

(3)

(Ar ₁₃ ) _e -L _12- (Ar ₁₄ ) _f

[In Formula 2 to 3,

L ₁₁ is substituted or unsubstituted (C6-C60) arylene or substituted or unsubstituted (C4-C60) heteroarylene;

L ₁₂ is substituted or unsubstituted anthracenylene;

,

또는

이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 치환 또는 비치환된(C3-C30)알킬렌 또는 치환 또는 비치환된(C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며; Ar ₁₁ to Ar ₁₄ 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, substituted or unsubstituted (C3-C30) cycloalkyl, cyano, nitro, -NR ₁₀₁ R ₁₀₂ , -BR ₁₀₃ R ₁₀₄ ,- PR ₁₀₅ R ₁₀₆ , -P (= 0) R ₁₀₇ R ₁₀₈ , R ₁₀₉ R ₁₁₀ R ₁₁₁ Si-, R ₁₁₂ X-, substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, substituted or Unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl,

,

or

Or an alicyclic ring and a monocyclic or polycyclic ring linked with a substituted or unsubstituted (C3-C30) alkylene or a substituted or unsubstituted (C3-C30) alkenylene, with or without adjacent substituents and fused rings. Can form an aromatic ring;

Ring C and ring D are each independently a substituted or unsubstituted (C5-C30) alicyclic ring, a substituted or unsubstituted (C6-C30) aromatic ring, or a substituted or unsubstituted (C6-C30) heteroaromatic ring ;

R ₁₀₁ to R ₁₁₂ are independently of each other substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl;

X is S or O;

W is a chemical bond,-(CR ₁₃₁ R ₁₃₂ ) _n -,-(R ₁₃₁ ) C = C (R ₁₃₂ )-, -N (R ₁₃₃ )-, -S-, -O-, -Si (R ₁₃₄ ) (R ₁₃₅ )-, -P (R ₁₃₆ )-, -P (= 0) (R ₁₃₇ )-, -C (= 0)-or -B (R ₁₃₈ )-;

R ₁₂₁ to R ₁₂₃ and R ₁₃₁ to R ₁₃₈ are the same as defined for Ar ₁₁ to Ar ₁₄ ;

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

n is an integer from 1 to 3;

c, d, e and f are each independently an integer from 0 to 4.]

The host compound of Formula 2 or 3 may be exemplified as a compound having the following structure, but is not limited thereto.

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

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

In addition, an organic electroluminescent device that emits white light may be formed by simultaneously including one or more organic light emitting layers including blue, red, or green light emitting compounds in addition to the organic light emitting compound. The compound emitting blue, green, or red light is 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, at least one inner surface of a pair of electrodes is selected from a chalcogenide layer, a halogenated metal layer, and a metal oxide layer (hereinafter, these are referred to as "surface layers"). It is preferable to arrange | position the above. 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, the reducing dopant layer The white organic electroluminescent device having two or more light emitting layers may be manufactured using the charge generating layer.

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

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

Preparation Example 1 Preparation of Compound 3

compound 1-1 Manufacture

7.0 g (32.11 mmol) of 9,9'-diethyl-9H-fluorene and 9.4 g (32.11 mmol) of paraformaldehyde were dissolved in 50 mL of 30% HBr and stirred at 60 ° C for 24 hours. Upon completion of the reaction, the mixture was extracted with chloroform and water, and water was removed with MgSO ₄ , and distilled under reduced pressure, followed by column separation (MC / Hexane) to obtain compound 1-1 13 g (31.8 mmol, 99%).

compound 1-2 Manufacture

5.0 g (12.24 mmol) of Compound 1-1 were dissolved in 8.1 mL (48.96 mmol) of triethylphosphite, and the mixture was stirred under reflux at 185 ° C for 6 hours. Upon completion of the reaction, the remaining triethyl phosphite was removed by a vacuum distillation apparatus, washed with distilled water, and extracted with ethyl acetate. The organic layer was dried with MgSO ₄ , distilled under reduced pressure, and separated by column (EA) to obtain 4.9 g (9.37 mmol, 76%) of Compound 1-2 .

compound 1-3 Manufacture

1,2,3,4-tetrahydroquinoline 10 g (75.0 mmol), 5.6 g (37.5 mmol) 4-formylphenylboronic acid, 0.02 g (1.9 mmol) Pd (OAc) ₂ , P (t-Bu) ₃ 1.5 mL (3.7 mmol) (50% in toluene) and 36.7 g (112.5 mmol) of Cs ₂ CO ₃ were dissolved in 75 mL of toluene and stirred at 110 ° C. for 5 hours. After completion of the reaction, the mixture was cooled to room temperature, extracted with ethyl acetate / water (1: 1), water was removed with MgSO ₄ , and distillation under reduced pressure was carried out to obtain a compound 1-3 (4.9 g, 20.6 mmol, 55%).

compound 3 Manufacture

Compound 1-2 5 g (9.56 mmol) and Compound 1-3 4.5 g (19.13 mmol) was dissolved in tetrahydrofuran 50 mL, and then lowered to 0 ℃ potassium tert- butoxide (1.0M in THF) was slowly added to 19mL It was. The temperature was gradually raised and stirred at room temperature for 1 hour, followed by addition of excess distillation. At this time, a precipitate was formed, which was filtered. The obtained solid was washed several times with ethanol to obtain 3.5 g (5.1 mmol, 53%) of compound 3 .

The organic light emitting compounds 1 to compound 29 were prepared using the method of Preparation Example 1, and the ¹ H NMR and the MS / FAB of the organic light emitting compounds prepared in Table 1 are shown.

compound ¹ H NMR (CDCl ₃ , 200 MHz) MS / FAB found calculated One δ = 0.9 (6H, m), 1.91 (4H, m), 3.05 (4H, m), 4.14 (4H, m), 6.55-6.6 (6H, m), 6.72 (2H, m), 6.95 (4H, m), 7.05 to 7.07 (4H, m), 7.54 (2H, m), 7.71 (2H, m), 7.8 (4H, m), 7.87 (2H, m) 660.89 660.35 2 δ = 0.9 (6H, m), 1.91 (4H, m), 6.52 (2H, m), 6.87 (2H, m), 6.95 (4H, m), 7.33 (2H, m), 7.5-7.82 (12H, m), 7.71 (2H, m), 7.87 to 7.94 (6H, m) 656.86 656.32 3 δ = 0.9 (6H, m), 1.91-1.96 (8H, m), 2.76 (4H, m), 3.06 (4H, m), 6.55-6.6 (6H, m), 6.72 (2H, m), 6.95 ( 4H, m), 7.05 to 7.07 (4H, m), 7.54 (2H, m), 7.71 (2H, m), 7.8 (4H, m), 7.87 (2H, m) 688.94 688.38 4 δ = 0.9 (6H, m), 1.25 (12H, m), 1.77 (4H, m), 1.91 (4H, m), 2.79 (2H, m), 2.94 (2H, m), 6.52 (2H, m) , 6.6 (4H, m), 6.69 (2H, m), 6.95 (4H, m), 7.05-7.08 (4H, m), 7.54 (2H, m), 7.71 (2H, m), 7.8 (4H, m ), 7.87 (2H, m) 745.05 744.44 5 δ = 0.9 (6H, m), 1.91-1.96 (8H, m), 2.76 (4H, m), 3.06 (4H, m), 6.55-6.6 (4H, m), 6.72 (2H, m), 6.95 ( 4H, m), 7.04-7.07 (5H, m), 7.53-7.56 (6H, m), 7.64 (2H, m), 7.71 (2H, m), 7.78-7.8 (3H, m), 7.87 (2H, m), 8.07 (1H, m), 8.49 (1H, m) 815.09 814.43 6 δ = 0.9 (6H, m), 1.91 (4H, m), 3.81 (4H, s), 6.51 (4H, m), 6.63 (4H, m), 6.69 (4H, m), 6.95-7.01 (12H, m), 7.54 (2H, m), 7.71-7.77 (6H, m), 7.87 (2H, m) 785.03 784.38 7 δ = 0.9 (6H, m), 1.72 (12H, s), 1.91 (4H, m), 6.55 (4H, m), 6.63 (4H, m), 6.73 (4H, m), 6.95 (4H, m) , 7.02 ~ 7.05 (8H, m), 7.54 (2H, m), 7.71 ~ 7.77 (6H, m), 7.87 (2H, m) 841.13 840.44 8 δ = 0.9 (6H, m), 1.91 (4H, m), 6.63 (4H, m), 6.95-6.97 (8H, m), 7.16-7.21 (12H, m), 7.54 (2H, m), 7.71- 7.77 (6 H, m), 7.87 (2 H, m) 821.10 820.29 9 δ = 0.9 (6H, m), 1.91 (4H, m), 6.59-6.63 (8H, m), 6.77 (4H, m), 6.89-6.95 (12H, m), 7.54 (2H, m), 7.71- 7.77 (6 H, m), 7.87 (2 H, m) 788.97 788.34 10 δ = 0.66 (12H, s), 0.9 (6H, m), 1.91 (4H, m), 6.63 (4H, m), 6.73 (8H, m), 6.95 (4H, m), 7.21 (4H, m) , 7.3 (4H, m), 7.54 (2H, m), 7.71-7.77 (6H, m), 7.87 (2H, m) 873.28 872.40 11 δ = 0.9 (6H, m), 1.91 (4H, m), 6.38 (8H, m), 6.56 (8H, m), 6.63 (8H, m), 6.81 (2H, m), 6.95 (4H, m) , 7.2 (4H, m), 7.54 (2H, m), 7.71-7.77 (6H, m), 7.87 (2H, m) 939.19 938.43 12 δ = 0.9 (6H, m), 1.91 (4H, m), 2.88 (8H, m), 6.58-6.63 (8H, m), 6.76 (4H, m), 6.95 (4H, m), 7.02-7.04 ( 8H, m), 7.54 (2H, m), 7.71-7.77 (6H, m), 7.87 (2H, m) 813.08 812.41 13 δ = 0.9 (6H, m), 1.91 (4H, m), 6.63 (4H, m), 6.69 (4H, m), 6.87 (4H, m), 6.95 (4H, m), 7.16 (4H, m) , 7.47 (4H, m), 7.54 (6H, m), 7.71-7.77 (6H, m), 7.85-7.87 (6H, m) 909.16 908.41 14 δ = 0.9 (6H, m), 1.91 (4H, m), 6.63 (8H, m), 6.81 (4H, m), 6.95-7.05 (12H, m), 7.25 (4H, m), 7.54 (2H, m), 7.71 to 7.77 (6H, m), 7.87 (2H, m) 809.05 808.38 15 δ = 0.9 (6H, m), 1.25 (6H, m), 1.81 (2H, m), 1.91 (6H, m), 2.79-2.8 (6H, m), 6.55-6.6 (6H, m), 6.72 ( 2H, m), 6.95 (4H, m), 7.05-7.07 (4H, m), 7.54 (2H, m), 7.71 (2H, m), 7.8 (4H, m), 7.87 (2H, m) 716.99 716.41 16 δ = 0.9 (6H, m), 1.33 (6H, m), 1.91 (4H, m), 3.48 (2H, m), 5.92 (2H, m), 6.55-6.6 (6H, m), 6.72 (2H, m), 6.82 (2H, m), 6.95 (4H, m), 7.11-7.16 (4H, m), 7.54 (2H, m), 7.71 (2H, m), 7.8 (4H, m), 7.87 (2H , m) 712.96 712.38 17 δ = 0.9 (6H, m), 1.91 (4H, m), 3.73 (4H, m), 5.92 (2H, m), 6.55-6.6 (6H, m), 6.72 (2H, m), 6.82 (2H, m), 6.95 (4H, m), 7.11-7.16 (4H, m), 7.54 (2H, m), 7.71 (2H, m), 7.8 (4H, m), 7.87 (2H, m) 684.91 684.35 18 δ = 0.9 (6H, m), 1.91 (4H, m), 2.34 (6H, s), 3.05 (4H, m), 4.14 (4H, m), 6.43 (2H, m), 6.6 (4H, m) , 6.83 (2H, m), 6.94-6.95 (6H, m), 7.54 (2H, m), 7.71 (2H, m), 7.8 (4H, m), 7.87 (2H, m) 688.94 688.38 19 δ = 0.9 (6H, m), 1.25 (6H, m), 1.81 (6H, m), 1.91 (4H, m), 2.12 (6H, s), 2.34 (6H, s), 2.79-2.8 (4H, m), 6.6 (4H, m), 6.7-6.75 (4H, m), 6.95 (4H, m), 7.54 (2H, m), 7.71 (2H, m), 7.8 (4H, m), 7.87 (2H , m) 773.10 772.48 20 δ = 0.9 (6H, m), 1.91 (4H, m), 6.52 (2H, m), 6.95 (4H, m), 7.41 (2H, m), 7.5-7.82 (20H, m), 7.71-7.77 ( 4H, m), 7.87 (2H, m), 8 (2H, m), 8.18 (2H, m) 809.05 808.38 21 δ = 3.05 (4H, m), 4.14 (4H, m), 6.55-6.6 (6H, m), 6.72 (2H, m), 6.95 (4H, m), 7.05-7.07 (4H, m), 7.16- 7.19 (4H, m), 7.35 (2H, m), 7.54 (2H, m), 7.71-7.8 (8H, m), 7.87 (2H, m) 754.96 754.33 22 δ = 0.9 (6H, m), 1.91-1.96 (8H, m), 2.76 (4H, m), 3.06 (4H, m), 6.55-6.6 (4H, m), 6.66-6.72 (4H, m), 6.95 (4H, m), 7.05-7.07 (4H, m), 7.54-7.57 (6H, m), 7.64 (2H, m), 7.71 (2H, m), 7.8 (2H, m), 7.87 (2H, m) 765.04 764.41 23 δ = 1.96 (4H, m), 2.76 (4H, m), 3.06 (4H, m), 6.55-6.6 (6H, m), 6.72 (2H, m), 6.95 (4H, m), 7.05-7.11 ( 8H, m), 7.26 (2H, m), 7.33 (4H, m), 7.54 (2H, m), 7.71 (2H, m), 7.8 (4H, m), 7.87 (2H, m) 785.03 784.38 24 δ = 0.9 (6H, m), 1.91-1.96 (8H, m), 2.76 (4H, m), 3.06 (4H, m), 6.55 (2H, m), 6.72 (2H, m), 6.96 (2H, m), 7.05 to 7.07 (4H, m), 7.2 (2H, m), 7.42 to 7.45 (4H, m), 7.56 to 7.59 (4H, m), 7.69 (2H, m), 7.82 (2H, m) 690.92 690.37 25 δ = 0.9 (6H, m), 1.91-1.96 (8H, m), 2.76 (4H, m), 3.06 (4H, m), 6.55-6.6 (6H, m), 6.72 (2H, m), 6.95 ( 4H, m), 7.05-7.07 (4H, m), 7.51-7.6 (3H, m), 7.77-7.8 (5H, m), 7.94 (1H, m), 8.09 (1H, m), 8.22 (1H, s), 8.52 (1 H, m) 739.00 738.40 26 δ = 0.9 (6H, m), 1.91-1.96 (8H, m), 2.76 (4H, m), 3.06 (4H, m), 6.55-6.6 (6H, m), 6.72 (2H, m), 6.95 ( 4H, m), 7.05-7.07 (4H, m), 7.51-7.54 (4H, m), 7.8 (4H, m), 7.94 (2H, m), 8.22 (2H, s), 8.52 (2H, m) 789.06 788.41 27 δ = 0.9 (6H, m), 1.91-1.96 (8H, m), 2.48 (6H, s), 2.76 (4H, m), 3.06 (4H, m), 6.55-6.6 (6H, m), 6.72 ( 2H, m), 6.78 (2H, m), 7.05-7.07 (4H, m), 7.22 (2H, m), 7.59 (2H, s), 7.64 (2H, s), 7.8 (4H, m) 716.99 716.41 28 δ = 0.9 (6H, m), 1.91-1.96 (8H, m), 2.76 (4H, m), 3.06 (4H, m), 6.55-6.6 (6H, m), 6.72 (2H, m), 6.95 ( 4H, m), 7.05-7.07 (4H, m), 7.51 (1H, s), 7.54-7.6 (2H, m), 7.77-7.8 (5H, m), 8.09 (1H, m), 8.39 (1H, m), 8.82 (1 H, m) 739.99 739.39 29 δ = 0.9 (6H, m), 1.91-1.96 (8H, m), 2.76 (4H, m), 3.06 (4H, m), 6.6 (4H, m), 6.95 (4H, m), 7.54 (2H, m), 7.71 (2H, m), 7.8 (4H, m), 7.87 (2H, m) 696.99 696.43

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 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenylamine ( 2-TNATA), 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, N , N' -bis (α-naphthyl) -N , N' -diphenyl-4,4'-diamine (NPB) was added to another cell in the vacuum deposition apparatus, and the current was applied to the cell to give NPB. A 20 nm-thick hole transport layer was deposited on the hole injection layer by evaporation, and then a light emitting layer was deposited on the hole injection layer as described below. Naphthylanthracene (DNA) was added and in another cell each compound 7 according to the invention as a dopant was added and the two materials at different rates. A 30 nm thick light emitting layer was deposited on the hole transport layer by evaporation and doping at 2 to 5% by weight, followed by 20 nm of tris (8-hydroxyquinoline) aluminum (III) (Alq) as an electron transporting layer on the light emitting layer. After depositing to a thickness, the lithium quinolate (Liq) was deposited to a thickness of 1 to 2 nm with an electron injection layer, and then 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 7.4 mA / cm ² flowed at a voltage of 7.0 V, and blue light emission of 980 cd / m ² was confirmed.

[Example 2]

An OLED device was manufactured in the same manner as in Example 1, except that Compound 15 was added as a dopant material in a light emitting layer and dinaphthylanthracene (DNA) was used as a light emitting host.

As a result, a current of 9.8 mA / cm ² flowed at a voltage of 7.2 V, and blue light emission of 1260 cd / m ² was confirmed.

Example 3

An OLED device was manufactured in the same manner as in Example 1, except that Compound 21 was added as a dopant material in a light emitting layer and dinaphthylanthracene (DNA) was used as a light emitting host.

As a result, a current of 8.8 mA / cm ² flowed at a voltage of 7.1 V, and blue light emission of 1200 cd / m ² was confirmed.

Example 4

An OLED device was manufactured in the same manner as in Example 1, except that Compound 29 was added as a dopant material in a light emitting layer and dinaphthylanthracene (DNA) was used as a light emitting host.

As a result, a current of 9.6 mA / cm ² flowed at a voltage of 7.2 V, and blue light emission of 1250 cd / m ² was confirmed.

Comparative Example 1

An OLED device was manufactured in the same manner as in Example 1, except that Compound A, instead of the compound of the present invention, was used as a dopant material in one cell of the vacuum deposition apparatus and dinaphthylanthracene (DNA) was used as the dopant. It was.

As a result, a current of 11.0 mA / cm ² flowed at a voltage of 7.5 V, and blue light emission of 1300 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 was confirmed that the luminous efficiency was improved while maintaining the color purity of equal or more.

Claims (11)

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

[In Formula 1, Ar ₁ and Ar ₂ are independently substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (C3-C30) heteroarylene; R ₁ to R ₈ 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) hetero Aryl, substituted or unsubstituted (C3-C30) cycloalkyl, cyano, nitro, -NR ₁₁ R ₁₂ , -BR ₁₃ R ₂₁₄ , -PR ₁₅ R ₁₆ , -P (= O) R ₁₇ R ₁₈ , _{R 19 R 20 R 21 Si-,} R 22 Y-, substituted or unsubstituted (C6-C30) aralkyl (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl ring, substituted or unsubstituted A cycloaliphatic ring that is linked to a (C2-C30) alkynyl, substituted or unsubstituted (C3-C30) alkylene, or a substituted or unsubstituted (C3-C30) alkenylene, with or without adjacent substituents and fused rings A ring and a monocyclic or polycyclic aromatic ring may be formed, and the carbon atoms of the monocyclic or polycyclic aromatic ring formed may be substituted with nitrogen; Ring A and Ring B are each independently a 5- to 7-membered heterocyclic amino group, wherein the heterocyclic amino group may be fused with one or more aromatic rings, and also selected from NR ₂₃ , O, S or SiR ₂₄ R ₂₅ May further comprise one or more hetero atoms; R ₁₁ to R ₂₅ are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl, or an adjacent substituent. Linking with substituted or unsubstituted (C3-C30) alkylene or substituted or unsubstituted (C3-C30) alkenylene with or without fused ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring Can;
Y is S or O; Wherein said heteroaryl comprises 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 , Ar ₂ , R ₁ to R _6, and R ₁₁ to R ₂₅ are each independently deuterium, halogen, (C1-C30) alkyl unsubstituted or substituted with halogen, (C6-C30) Aryl, (C6-C30) aryl substituted or unsubstituted (C3-C30) heteroaryl, 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic rings, ( C3-C30) cycloalkyl, (C6-C30) cycloalkyl fused with one or more aromatic rings, R ^a R ^b R ^c Si-, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, Carbazolyl, -NR ^d R ^e , -BR ^f R ^g , -PR ^h R ⁱ , -P (= 0) R ^j R ^k , (C6-C30) ar (C1-C30) alkyl, (C1-C30) At least one selected from the group consisting of alkyl (C6-C30) aryl, R ¹ T-, R ^m C (= 0)-, R ^m C (= 0) O-, carboxyl, nitro or hydroxy, R ^a to R ^l are independently of each other (C1-C30) alkyl, (C6-C30) aryl or (C3-C30) heteroaryl; T is S or O; R ^m is (C1-C30) alkyl, (C1-C30) alkoxy, (C6-C30) aryl or (C6-C30) aryloxy. The method of claim 1,
The ring A and ring B are independently selected from the following structures, the organic light emitting compound, characterized in that.

Z is a chemical bond or-(CR ₄₁ R ₄₂ ) _m -,-(R ₄₁ ) C = C (R ₄₂ )-, -N (R ₄₃ )-, -S-, -O-, -Si (R ₄₄ ) (R ₄₅ )-, -P (R ₄₆ )-, -P (= 0) (R ₄₇ )-, -C (= 0)-, or -B (R ₄₈ )-; R ₃₁ to R ₄₈ 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) hetero Aryl, substituted or unsubstituted (C3-C30) cycloalkyl, cyano, nitro, -NR ₁₁ R ₁₂ , -BR ₁₃ R ₂₁₄ , -PR ₁₅ R ₁₆ , -P (= O) R ₁₇ R ₁₈ , R ₁₉ R ₂₀ R ₂₁ Si-, R ₂₂ Y-, substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted A cycloaliphatic ring that is linked to a (C2-C30) alkynyl, substituted or unsubstituted (C3-C30) alkylene, or a substituted or unsubstituted (C3-C30) alkenylene, with or without adjacent substituents and fused rings A ring and a monocyclic or polycyclic aromatic ring may be formed, and the carbon atoms of the monocyclic or polycyclic aromatic ring formed may be substituted with nitrogen; m is an integer from 1 to 4.] The method of claim 3, wherein
The ring A and ring B are independently selected from the following structures, the organic light emitting compound, characterized in that.

The method of claim 1,
remind

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

[R ₁ , R ₂ , R ₃ and R ₆ are independently of each other deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl or substituted or unsubstituted (C6-C30) aryl.] The method of claim 3, wherein
An organic light emitting compound, which is selected from the following compounds.

An organic light emitting device comprising the organic light emitting compound according to any one of claims 1 to 6. The method of claim 7, wherein
The organic light emitting diode 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 one organic light emitting compound and at least one host compound represented by Formula 2 or Formula 3 below. Organic light emitting device.
(2)
(Ar ₁₁ ) _c -L _11- (Ar ₁₂ ) _d
(3)
(Ar ₁₃ ) _e -L _12- (Ar ₁₄ ) _f
[In Formula 2 to 3,
L ₁₁ is substituted or unsubstituted (C6-C60) arylene or substituted or unsubstituted (C4-C60) heteroarylene;
L ₁₂ is substituted or unsubstituted anthracenylene;
Ar ₁₁ to Ar ₁₄ 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, substituted or unsubstituted (C3-C30) cycloalkyl, cyano, nitro, -NR ₁₀₁ R ₁₀₂ , -BR ₁₀₃ R ₁₀₄ ,- PR ₁₀₅ R ₁₀₆ , -P (= 0) R ₁₀₇ R ₁₀₈ , R ₁₀₉ R ₁₁₀ R ₁₁₁ Si-, R ₁₁₂ X-, substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, substituted or Unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl,

,

or

Or an alicyclic ring and a monocyclic or polycyclic ring linked with a substituted or unsubstituted (C3-C30) alkylene or a substituted or unsubstituted (C3-C30) alkenylene, with or without adjacent substituents and fused rings. Can form an aromatic ring;
Ring C and ring D are each independently a substituted or unsubstituted (C5-C30) alicyclic ring, a substituted or unsubstituted (C6-C30) aromatic ring, or a substituted or unsubstituted (C6-C30) heteroaromatic ring ;
R ₁₀₁ to R ₁₁₂ are independently of each other substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl;
X is S or O;
W is a chemical bond,-(CR ₁₃₁ R ₁₃₂ ) _n -,-(R ₁₃₁ ) C = C (R ₁₃₂ )-, -N (R ₁₃₃ )-, -S-, -O-, -Si (R ₁₃₄ ) (R ₁₃₅ )-, -P (R ₁₃₆ )-, -P (= 0) (R ₁₃₇ )-, -C (= 0)-or -B (R ₁₃₈ )-;
R ₁₂₁ to R ₁₂₃ and R ₁₃₁ to R ₁₃₈ are the same as defined for Ar ₁₁ to Ar ₁₄ ;
The heterocycloalkyl and heteroaryl include one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P;
n is an integer from 1 to 3;
c, d, e and f are each independently an integer from 0 to 4.] The method of claim 8,
At least one compound selected from at least one amine compound selected from the group consisting of an arylamine compound or a styrylarylamine compound or a group 1, group 2, 4 cycle, 5 cycle transition metal, lanthanum series metal in the organic layer An organic light emitting device further comprising at least one metal or complex compound selected from the group consisting of organometallics of transition elements. The method of claim 8,
The organic material layer is an organic light emitting device comprising a light emitting layer and a charge generating layer. The method of claim 8,
The organic light emitting device of claim 1, further comprising at least one organic light emitting layer emitting blue, red or green light to the organic material layer.