KR20120042634A - Novel organic luminescent compounds and organic electroluminescent device using the same - Google Patents

Abstract

PURPOSE: An organic electroluminescence compound is provided to have excellent red light emitting efficiency especially in case of using as host material in an organic electroluminescence device, thereby offering an OLED having very excellent driving life time, and improved power consumption. CONSTITUTION: An organic electroluminescence compound is in chemical formula 1. In chemical formula 1, a functional group in chemical formula 1-a is (C3-6) alkylene, L and L1 is respectively (C6-30) arylene or (C2-30) heteroarylene, L2 is a single bond or (C2-30) heteroarylene, R1, Ar1-Ar3 is respectively hydrogen, deuterium, (C1-30)alkyl, halo(C1-30)alkyl, halogen, cyano, (C3-30)cycloalkyl, 5-7 membered heterocycloalkyl, (C2-30)alkenyl, (C2-30)alkynyl, (C6-30)aryl, (C1-30)alkoxy, (C6-30)aryloxy, (C2-30)heteroaryl, (C1-30)alkyl-substituted (C2-30)heteroaryl, (C6-30)aryl-substituted (C2-30)heteroaryl, (C6-30)ar(C1-30)alkyl, arylthio, mono or di (C1-30)alkylamino, mono or di (C6-30)arylamino, tri(C1-30)alkylsilyl, di(C1-30)alkyl(C6-30)arylsilyl, tri(C6-30)arylsilyl, nitro, or hydroxy.

Description

Novel organic luminescent compounds and organic electroluminescent device using the same

The present invention relates to a novel compound for organic electronic materials and an organic electroluminescent device employing the same.

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 developed for the first time [Reference: Appl. Phys. Lett. 51, 913, 1987].

The organic EL element injects electric charge into the organic film formed between the electron injection electrode (cathode) and the hole injection electrode (anode) to generate excitons by pairing electrons and holes. Light is emitted by using light emission (phosphorescence or fluorescence) when the excitons are inactive. The organic EL device emits polarized light with a voltage of about 10V and a high luminance of about 100 to 10,000 cd / m 2, and emits light in a spectrum from blue to red by simply selecting a fluorescent material. The device can be formed on a flexible transparent substrate such as plastic, and can be driven at a lower voltage (less than 10V) compared to a plasma display panel or an inorganic EL display, and has a relatively low power consumption. It has a small and excellent color.

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

Organic light emitting materials can be classified into high molecular materials and low molecular materials. Low molecular materials include pure organic light emitting materials that do not contain metal complexes and metals in terms of molecular structure. As such light emitting materials, light emitting materials such as chelate complexes such as tris (8-quinolinolato) aluminum complexes, coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives and oxadiazole derivatives are known. Has been reported to obtain visible region luminescence from blue to red.

In order to realize a full color OLED display, three kinds of RGB light emitting materials are used, and development of high efficiency long life RGB light emitting materials is an important task to improve the characteristics of the entire organic EL. The light emitting material can be classified into a host material and a dopant material in terms of its function. In general, a device structure having excellent EL characteristics is known to make a light emitting layer by doping a host with a dopant. Recently, the development of high efficiency and long life organic EL devices has emerged as an urgent task, and considering the level of EL characteristics required in medium and large OLED panels, it is urgent to develop materials that are much superior to existing light emitting materials. In this respect, the development of host materials is one of the most important factors to be solved. In this case, the desirable properties of the host material serving as a solvent and energy transporter in the solid state should be high in purity and have an appropriate molecular weight to enable vacuum deposition. In addition, high glass transition temperature and pyrolysis temperature should ensure thermal stability, high electrochemical stability is required for long life, easy to form amorphous thin film, good adhesion with other adjacent materials, Should not.

When an organic EL device is manufactured using a doping technique, energy transfer from the host molecule to the dopant in the excited state is less than 100%, and not only the dopant but also the host material emits light. In particular, in the case of a red light emitting device, since the host material emits light in a wavelength range where visibility is greater than that of the dopant, color purity is deteriorated by light emission of the host material. In addition, the light emission life and the sustainability need to be improved in practical application.

On the other hand, CBP is the most widely known host material for phosphorescent emitters, and high-efficiency OLEDs using a hole blocking layer such as BCP and BAlq are known, and high-performance OLEDs using BAlq derivatives as a host are known in Pioneer, Japan. Is known.

However, existing materials have advantages in terms of luminescence properties, but the glass transition temperature is low and the thermal stability is not very good, and thus has a disadvantage such that the material changes when undergoing a high temperature deposition process under vacuum. Since power efficiency = (π / voltage) × current efficiency in OLEDs, power efficiency is inversely proportional to voltage. However, low power consumption of OLEDs requires high power efficiency. Actually, OLEDs using phosphorescent materials have significantly higher current efficiency (cd / A) than OLEDs using fluorescent materials.However, when a conventional material such as BAlq or CBP is used as a host of phosphorescent materials, OLEDs using fluorescent materials Compared with the higher driving voltage, there was no significant advantage in terms of power efficiency (lm / w). In addition, in terms of lifespan in OLED devices, they are never satisfactory, and development of a more stable and more excellent host material is required.

 Appl. Phys. Lett. 51, 913, 1987

Therefore, the present invention has been made to solve the problems of the prior art, the object of the present invention is used as a host material of the organic light emitting material in the OLED device is superior red light emission efficiency and excellent life characteristics compared to the conventional host material It is to provide a compound for an organic electronic material and an organic field device.

The present invention relates to a compound for an organic electronic material represented by Chemical Formula 1, and an organic electronic device including the same, wherein the compound for an organic electronic material according to the present invention is included in a hole injection layer, a hole transport layer, or an electron transport layer. It can be used as a host or a dopant, and has an advantage of manufacturing an OLED device having good luminous efficiency and excellent material life characteristics, and thus having a very good driving life.

The present invention relates to a compound for an organic electronic material represented by the following general formula (I).

[Formula I]

[In Formula I,

는 (C3-C6)알킬렌이고;

Is (C3-C6) alkylene;

L and L ₁ are independently of each other (C6-C30) arylene or (C2-C30) heteroarylene;

L ₂ is a single bond or (C2-C30) heteroarylene;

R ₁ , Ar ₁ to Ar ₃ are each independently hydrogen, deuterium, (C1-C30) alkyl, halo (C1-C30) alkyl, halogen, cyano, (C3-C30) cycloalkyl, 5- to 7-membered Heterocycloalkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C6-C30) aryl, (C1-C30) alkoxy, (C6-C30) aryloxy, (C2-C30) heteroaryl, (C2-C30) heteroaryl substituted with (C1-C30) alkyl, (C2-C30) heteroaryl substituted with (C6-C30) aryl, (C6-C30) ar (C1-C30) alkyl, (C6- C30) arylthio, mono or di (C1-C30) alkylamino, mono or di (C6-C30) arylamino, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl , Tri (C6-C30) arylsilyl, nitro or hydroxy;

The arylene and heteroarylene of L and L _1, the heteroarylene of L ₂ , and the alkyl, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, aryl and heteroaryl of R ₁ , Ar ₁ to Ar ₃ are Independently from each other deuterium, (C1-C30) alkyl, halo (C1-C30) alkyl, halogen, cyano, (C3-C30) cycloalkyl, 5- to 7-membered heterocycloalkyl, (C2-C30) alkenyl (C2) substituted with (C2-C30) alkynyl, (C6-C30) aryl, (C1-C30) alkoxy, (C6-C30) aryloxy, (C2-C30) heteroaryl, (C1-C30) alkyl -C30) heteroaryl, (C6-C30) aryl substituted (C2-C30) heteroaryl, (C6-C30) ar (C1-C30) alkyl, (C6-C30) arylthio, mono or di (C1- C30) alkylamino, mono or di (C6-C30) arylamino, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, nit And one or more selected from the group consisting of hydroxy and hydroxy;

R ₁ may be linked to each other with a carbon atom of the benzene ring to which it is bonded to form a ring;

L and L ₁ may combine with each other to form a fused ring;

Ar ₁ to Ar ₃ may be bonded to each other to form a fused ring.]

Substituents comprising the "alkyl", "alkoxy" and other "alkyl" moieties described herein include both straight or pulverized forms, and "cycloalkyl" is substituted or unsubstituted as well as a single ring system Or several ring-based hydrocarbons such as substituted or unsubstituted (C7-C30) bicycloalkyl. "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. It means an aryl group which is a 5-6 membered monocyclic heteroaryl, and polycyclic heteroaryl condensed with one or more benzene rings, and 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, fura Monocyclic heteroaryl such as residue, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoy Soxazolyl, Benzoxazolyl, Isoindoleyl, Indolyl, Indazolyl, Benzothiadiazolyl, Quinolyl, Isoquinolyl, Cynolinyl, Quinazolinyl, Quinoxalinyl, Carbazolyl, Phenantridinyl, Benzodioxol Polycyclic heteroaryls such as solyl and their corresponding N-oxides (eg, pyridyl N-oxides, quinolyl N-oxides), quaternary salts thereof, and the like.

In addition, the "(C1-C30) alkyl group" described in the present invention includes (C1-C20) alkyl or (C1-C10) alkyl, and "(C6-C30) aryl group" is (C6-C20) aryl Or (C6-C12) aryl. "(C2-C30) heteroaryl group" includes (C2-C20) heteroaryl or (C2-C12) heteroaryl, and "(C3-C30) cycloalkyl group" means (C3-C20) cycloalkyl or (C3 -C7) cycloalkyl. "(C2-C30) alkenyl or alkynyl" groups include (C2-C20) alkenyl or alkynyl, (C2-C10) alkenyl or alkynyl.

는 하기 구조로부터 선택된다.Specifically, the

Is selected from the following structure.

[Ar ₁ and Ar ₃ are the same as defined in Formula 1;

X ₁ to X ₅ are independently of each other CR ₁₀ or N;

R ₂ to R ₄ and R ₁₀ are each independently of deuterium, (C 1 -C 30) alkyl, halo (C 1 -C 30) alkyl, halogen, cyano, (C 3 -C 30) cycloalkyl, 5- to 7-membered heterocyclo Alkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C6-C30) aryl, (C1-C30) alkoxy, (C6-C30) aryloxy, (C2-C30) heteroaryl, (C1 (C2-C30) heteroaryl substituted with alkyl, (C2-C30) heteroaryl substituted with (C6-C30) aryl, (C6-C30) ar (C1-C30) alkyl, (C6-C30) Arylthio, mono or di (C1-C30) alkylamino, mono or di (C6-C30) arylamino, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, nitro or hydroxy.]

The compound for an organic electronic material according to the present invention is exemplified as a compound having the following structure, but is not limited to these compounds:

Compound 2 of the compounds described above may be prepared as illustrated in Scheme 1 below, and the following preparation method does not limit the preparation of the compound of formula (I), and the modification of the following preparation method is the specification of the present invention. It will be apparent to those skilled in the art.

Scheme 1

In addition, the present invention provides an organic electroluminescent device, the organic electroluminescent device according to the present invention comprises a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer includes at least one compound for an organic electronic material of Chemical Formula 1. The organic material layer includes a light emitting layer, and the compound for the organic electronic material of Chemical Formula 1 is used as a host material in the light emitting layer.

When the compound for the organic electronic material of Formula 1 is used as a host in the light emitting layer is characterized in that it comprises at least one phosphorescent dopant. The phosphorescent dopant applied to the organic electroluminescent device of the present invention is not particularly limited, but the phosphorescent dopant applied to the organic electroluminescent device of the present invention is preferably selected from compounds represented by the following Chemical Formula 2.

[Formula 2]

M ^One L ¹⁰¹ L ¹⁰² L ¹⁰³

[In the formula (2)

Wherein M ¹ is selected from the group consisting of Ir, Pt, Pd and Os,

The ligands L ¹⁰¹ , L ¹⁰² and L ¹⁰³ are independently selected from the following structures.

R ₂₀₁ to R ₂₀₃ are independently of each other hydrogen, deuterium, (C1-C30) alkyl with or without halogen, (C6-C30) aryl or halogen with or without (C1-C30) alkyl;

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

R ₂₂₀ to R ₂₂₃ are each independently hydrogen, deuterium, (C1-C30) alkyl with or without halogen, or (C6-C30) aryl with or without (C1-C30) alkyl;

R ₂₂₄ and R ₂₂₅ are independently of each other hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen, or R ₂₂₄ and R ₂₂₅ contain fused rings Linked with (C3-C12) alkylene or (C3-C12) alkenylene with or without formation to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;

R ₂₂₆ is substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C2-C30) heteroaryl or halogen;

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

,

또는

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

,

or

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

Specifically, it is preferable to use the following compounds as the dopant compound of Chemical Formula 2.

The organic electroluminescent device of the present invention includes a compound for an organic electronic material of Formula 1, and at the same time may include one or more compounds selected from the group consisting of arylamine-based compounds or styrylarylamine-based compounds.

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

In addition, the organic material layer may include one or more organic light emitting layers including blue, red, or green light emitting compounds in addition to the compound for organic electronic materials to form an organic light emitting device that emits white light.

In the organic electroluminescent device of the present invention, one layer selected from a chalcogenide layer, a halogenated metal layer and a metal oxide layer on at least one inner surface of a pair of electrodes (hereinafter, these are referred to as "surface layers"). It is preferable to arrange | position the above. Concretely, it is preferable to dispose a halogenated metal layer or a metal oxide layer on the surface of the anode on the side of the light emitting medium layer and on the surface of the cathode on the side of the light emitting medium layer, with a chalcogenide (including oxide) layer of a metal of silicon and aluminum Do. This can stabilize driving. Preferred examples of the chalcogenide include SiO _X (1 ≦ _X ≦ ₂ ), AlO _X (1 ≦ _X ≦ 1.5), SiON or SiAlON, and preferred examples of the halogenated metal include LiF, MgF ₂ , CaF ₂ , and fluoride. Rare earth metals and the like, and preferred 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 to the light emitting medium. In addition, since the hole transport compound is oxidized to become a cation, it is easy to inject and transfer holes from the mixed region to the light emitting medium. Preferred oxidative dopants include various Lewis acids and acceptor compounds. Preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, a white organic electroluminescent device having two or more light emitting layers may be manufactured using a reducing dopant layer as a charge generating layer.

The compound for an organic electronic material according to the present invention is used as a host material of the organic light emitting material in the OLED device has a good red light emission efficiency and excellent life characteristics of the material compared to the existing host material can produce an OLED having a very good driving life of the device There is an advantage.

Hereinafter, for the purpose of understanding the present invention, the compounds for organic electronic materials according to the present invention will be described with reference to the compounds of the present invention, methods for their preparation, and luminescence properties of devices, which are only intended to illustrate the embodiments thereof. It does not limit the scope of the present invention.

Preparation Example 1 Preparation of Compound 2

compound  1-1 Manufacture

20 g (84.77 mmol) of 1,3-dibromobenzene was added to 1 L one neck RBF, and the mixture was made in a nitrogen atmosphere in a vacuum state, and 500 mL of THF was added and stirred at -78 ° C for 10 minutes. 33.9 mL (84.77 mmol) of N-BuLi (2.5M) was added slowly, followed by stirring at −78 ° C. for 1 hour. 29.9 g (107.72 mmol) of chlorotriphenylsilane was dissolved in 100 mL of THF, and then slowly added thereto. Then, the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the mixture was washed with distilled water, extracted with EA and dried over MgSO ₄ . After removing the solvent by a rotary evaporator to recrystallized with MC and MeOH to give 62 g (63%) of compound 1-1 .

compound  1-2 Manufacture

22.5 g (0.10 mol) of Compound 1-1 was added to 3 L one neck RBF, and the mixture was put in a nitrogen atmosphere in a vacuum state, and 1.3 L of THF was added and stirred at -78 ° C for 10 minutes. 48.6 mL (0.12 mol) of N-BuLi (2.5M) was added slowly, followed by stirring at -78 ° C for 1 hour. 18 mL (0.16 mmol) of triethyl borate was added slowly. Then, the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the mixture was washed with distilled water, extracted with EA and dried over MgSO ₄ . The solvent was removed using a rotary evaporator, and the residue was purified by column chromatography to obtain 10 g of Compound 1-2 (45%).

compound  1-3 Manufacture

6.5 g (0.04 mol) of 2,4-dichloropyrimidine was added to 500 ml two neck RBF, Compound 1-2 20 g (0.05 mol), Pd (PPh ₃ ) ₄ 2.5 g (0.002 mol), K ₂ CO ₃ (2M) 65 mL and 65 mL of EtOH were added thereto, 150 mL of toluene was added, and then heated to 80 ° C. Then it was stirred for 3 hours. After completion of the reaction, the mixture was washed with distilled water, extracted with EA, dried over MgSO ₄ , dried over MgSO ₄ , solvent was removed by rotary evaporation, and purified by column chromatography to obtain compound 1-3 13g (68%).

compound  2 Manufacture

Add 1.5 g (0.008 mol) of 2,3,4,9-tetrahydro-1H-carbazole to 250 ml two neck RBF, compound 1-3 6 g (0.013 mol), Pd ₂ (dba) ₃ 400 mg (0.0004 mol), 344 mg (0.87 mmol) of Dave-phos and 2.5 g (26.27 mmol) of NaOt-Bu were added thereto, and 100 mL of toluene was added thereto, followed by heating to 120 ° C. Then it was stirred for 12 hours. After completion of the reaction, the mixture was washed with distilled water, extracted with EA, dried over MgSO ₄ , dried over MgSO ₄ , solvent was removed by rotary evaporation, and purified by column chromatography to obtain 4.4 g (81%) of the title compound 2 .

¹ H NMR (CDCl ₃ , 200 MHz) δ = 1.73 (4H, m), 2.64 (2H, m), 2.76 (2H, m), 6.93 (1H, m), 7.37-7.46 (16H, m), 7.55 ( 3H, m), 7.61 (1H, m), 7.76 (1H, m), 7.89 (1H, m), 7.96 (1H, m), 8.57 (1H, m); MS / FAB found 583.80, calculated 583.24

Preparation Example 2-39 Preparation of Compound 1 and Compound 3-39

In the same manner as in Preparation Example 1, Compound 1 and Compound 3-39 were prepared.

Preparation Example 40 Preparation of Compound 40

compound  2-1 Manufacture

25 g (0.14 mol) of 2,3,4,9-tetrahydro-1H-carbazole was added to 1 L two neck RBF, 105 g (0.43 mol) of 1,4-dibromobenzene, 14 g (0.21 mol) of Cu, K ₂ CO ₃ 60 g (0.43 mol), 18-crown-6 3 g (0.01 mol) was added thereto, and 500 mL of 1,2-dichlorobenzene was added thereto, followed by heating to 200 ° C. Then it was stirred for 12 hours. After the reaction was completed, 1,2-dichlorobenzene was removed, washed with distilled water, extracted with EA, the organic layer was dried over MgSO ₄ , the solvent was removed with a rotary evaporator, and purified by column to obtain compound 2-1 17g (36%). Got it.

compound  2-2 Manufacture

15 g (0.045 mol) of Compound 2-1 was added to 1 L one neck RBF, and the mixture was put in a nitrogen atmosphere in a vacuum state, and 250 mL of THF was added and stirred at -78 ° C for 10 minutes. 27.5 mL (0.0.068 mol) of N-BuLi (2.5M) was added slowly, followed by stirring at −78 ° C. for 1 hour. 7.8 mL (0.0.068 mmol) of triethylborate was added slowly. Stir at room temperature for 12 hours. After completion of the reaction, the mixture was washed with distilled water, extracted with EA and dried over MgSO ₄ . The solvent was removed using a rotary evaporator, and the residue was purified by a column to obtain compound 2-2 8 g (40%).

compound 40 Manufacture

Add 7.4 g (0.025 mol) of compound 2-2 to 500 ml two neck RBF, add compound 1-3 8.1 g (0.018 mol), Pd (PPh ₃ ) ₄ 1 g (0.90 mmol), K ₂ CO ₃ (2M) 90 mL (0.054) mmol), EtOH 90mL, toluene 180mL were added and then heated to 120 ° C. Then it was stirred for 12 hours. After the reaction, the mixture was washed with distilled water, extracted with EA, dried over MgSO ₄ , dried over MgSO ₄ , solvent was removed on a rotary evaporator, and purified by column to obtain compound 40 (5 g, 42%).

MS / FAB found 659.89, calculated 659.28

Example 1 Fabrication of an OLED Device Using a Compound for Organic Electronic Materials 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 equipment, and N ¹ , N ^{1 ′} -([1,1′-biphenyl] -4,4′-diyl having the following structure in the cell in the vacuum deposition equipment. ) Bis (N 1-(naphthalen- ¹ -yl) -N ⁴ , N ⁴ -diphenylbenzene-1,4-diamine) (N ¹ , N ^{1 ′} -([1,1′-biphenyl] -4 Add 4'-diyl) bis (N ^1- (naphthalen-1-yl) -N ⁴ , N ⁴ -diphenylbenzene-1,4-diamine) and evacuate until the vacuum in the chamber reaches 10 ^-6 torr. The cell was then evaporated by applying a current to the cell to deposit a 60 nm thick hole injection layer on the ITO substrate, followed by N, N'-di (4-biphenyl) -N, N'-di (4-biphenyl) -4,4'-diaminobiphenyl (N, N'-di (4-biphenyl) -N, N'-di (4-biphenyl) -4,4'- diaminobiphenyl) was added to the cell, followed by evaporation to deposit a 20 nm-thick hole transport layer on the hole injection layer, and the hole injection layer and the hole transport layer were formed thereon. This was deposited. As the host on one cell of the vacuum deposition apparatus into the compound 2 according to the invention, and after the other cell, insert the D-56 respectively, as a dopant, evaporated to two materials at different rates, doped with 15% by weight A light emitting layer having a thickness of 30 nm was deposited on the hole transport layer, and then 2- (4- (9,10-di (naphthalen-2-yl) anthracen-2-yl) in one cell as an electron transport layer on the light emitting layer. Phenyl) -1-phenyl-1H-benzo [d] imidazole (2- (4- (9,10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole) was added, and another cell was charged with lithium quinolate, and the two materials were evaporated at the same rate to be doped at 50% by weight to deposit an electron transport layer of 30 nm. Lithium quinolate (Liq) was deposited to a thickness of 2 nm, and the Al cathode was deposited to a thickness of 150 nm using another vacuum deposition equipment. It was constructed characters.

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 5.1 mA / cm ² flowed at a voltage of 5.8 V, and green light emission of 2670 cd / m ² was confirmed.

[Example 2]

An OLED device was manufactured in the same manner as in Example 1, except that Compound 40 was used as the host material in the emission layer.

As a result, a current of 13.8 mA / cm ² flowed at a voltage of 6.1 V, and green light emission of 7200 cd / m ² was confirmed.

Comparative Example 1

CBP (4,4'-bis (carbazol-9-yl) biphenyl) is used as a host material in the light emitting layer, and Ir (ppy) ₃ [tris (2-phenylpyridine) iridium] is used as a dopant. Except that bis (2-methyl-8-quinolinate) (p-phenylphenolrato) aluminum (III) (BAlq) was used as the hole blocking layer between the light emitting layer and the electron transporting layer. An OLED device was manufactured in the same manner as in Example 1.

As a result, a current of 20 mA / cm ² flowed at a voltage of 8.2 V, and green light emission of 1000 cd / m ² was confirmed.

It was confirmed that the luminescent properties of the compounds for organic electronic materials developed in the present invention showed superior characteristics compared to the conventional materials. In addition, the device using the organic electronic material compound according to the present invention as a light emitting host material was not only excellent in the light emission characteristics, but also by lowering the driving voltage by 2V or more to induce an increase in power efficiency to improve the power consumption.

Claims (9)

A compound for an organic electronic material represented by formula (I):
(I)

[In Formula I,

Is (C3-C6) alkylene;
L and L ₁ are independently of each other (C6-C30) arylene or (C2-C30) heteroarylene;
L ₂ is a single bond or (C2-C30) heteroarylene;
R ₁ , Ar ₁ to Ar ₃ are each independently hydrogen, deuterium, (C1-C30) alkyl, halo (C1-C30) alkyl, halogen, cyano, (C3-C30) cycloalkyl, 5- to 7-membered Heterocycloalkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C6-C30) aryl, (C1-C30) alkoxy, (C6-C30) aryloxy, (C2-C30) heteroaryl, (C2-C30) heteroaryl substituted with (C1-C30) alkyl, (C2-C30) heteroaryl substituted with (C6-C30) aryl, (C6-C30) ar (C1-C30) alkyl, (C6- C30) arylthio, mono or di (C1-C30) alkylamino, mono or di (C6-C30) arylamino, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl , Tri (C6-C30) arylsilyl, nitro or hydroxy;
The arylene and heteroarylene of L and L _1, the heteroarylene of L ₂ , and the alkyl, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, aryl and heteroaryl of R ₁ , Ar ₁ to Ar ₃ are Independently from each other deuterium, (C1-C30) alkyl, halo (C1-C30) alkyl, halogen, cyano, (C3-C30) cycloalkyl, 5- to 7-membered heterocycloalkyl, (C2-C30) alkenyl (C2) substituted with (C2-C30) alkynyl, (C6-C30) aryl, (C1-C30) alkoxy, (C6-C30) aryloxy, (C2-C30) heteroaryl, (C1-C30) alkyl -C30) heteroaryl, (C6-C30) aryl substituted (C2-C30) heteroaryl, (C6-C30) ar (C1-C30) alkyl, (C6-C30) arylthio, mono or di (C1- C30) alkylamino, mono or di (C6-C30) arylamino, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, nit And may be further substituted with one or more selected from the group consisting of hydroxy and hydroxy;
R ₁ may be linked to each other with a carbon atom of the benzene ring to which it is bonded to form a ring;
L and L ₁ may combine with each other to form a fused ring;
Ar ₁ to Ar ₃ may be bonded to each other to form a fused ring.] The method of claim 1,
remind

The compound for an organic electronic material, characterized in that selected from the following structure:

[Wherein Ar ₁ and Ar ₃ are the same as defined in claim 1;
X ₁ to X ₅ are independently of each other CR ₁₀ or N;
R ₂ to R ₄ and R ₁₀ are each independently of deuterium, (C 1 -C 30) alkyl, halo (C 1 -C 30) alkyl, halogen, cyano, (C 3 -C 30) cycloalkyl, 5- to 7-membered heterocyclo Alkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C6-C30) aryl, (C1-C30) alkoxy, (C6-C30) aryloxy, (C2-C30) heteroaryl, (C1 (C2-C30) heteroaryl substituted with alkyl, (C2-C30) heteroaryl substituted with (C6-C30) aryl, (C6-C30) ar (C1-C30) alkyl, (C6-C30) Arylthio, mono or di (C1-C30) alkylamino, mono or di (C6-C30) arylamino, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, nitro or hydroxy.] The method of claim 2,
Compound for an organic electronic material, characterized in that selected from the following compounds:

An organic electroluminescent device comprising the compound for organic electronic material according to any one of claims 1 to 3. The method of claim 4, wherein
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. 6. The method of claim 5,
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. 6. The method of claim 5,
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. 6. The method of claim 5,
The organic material layer is an organic electroluminescent device comprising a light emitting layer and a charge generating layer. 6. The method of claim 5,
The organic light emitting device of claim 1, further comprising at least one organic light emitting layer for emitting blue, red or green light to the organic material layer.