KR101554859B1 - Novel Compounds for Organic Electronic Material and Organic Electronic Device Using the Same - Google Patents

Abstract

상기 화학식 1에서, X, Y, L₁, L₂ 및 R₁ 내지 R₄는 각각 발명의 상세한 설명에서 정의한 바와 같다.
본 발명에 따른 유기 전자재료용 화합물은 정공전달층 또는 전자전달층, 정공주입층에 포함되거나 호스트 또는 도판트로 사용될 수 있으며, 발광효율이 좋고 재료의 수명특성이 뛰어나 소자의 구동수명이 매우 양호한 OLED 소자를 제조할 수 있는 장점이 있다.BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel compound for an organic electronic material and an organic electronic device including the same. More particularly, the compound for an organic electronic material according to the present invention is represented by the following formula (1).
[Chemical Formula 1]

In Formula 1, X, Y, L ₁ , L ₂ and R ₁ to R ₄ are each as defined in the description of the invention.
The compound for an organic electronic material according to the present invention can be contained in a hole transporting layer, an electron transporting layer, a hole injecting layer, or can be used as a host or a dopant. The OLED has excellent luminescent efficiency and excellent lifetime characteristics, There is an advantage that a device can be manufactured.

Description

TECHNICAL FIELD [0001] The present invention relates to a novel compound for organic electronic materials and an organic electronic device comprising the compound.

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel compound for an organic electronic material and an organic electronic device including the compound. More particularly, the compound for organic electronic material according to the present invention comprises a hole transport layer or an electron transport layer, Or may be used as a host or a dopant.

Among the display elements, an electroluminescence device (EL device) is a self-luminous display device having a wide viewing angle, excellent contrast, and fast response speed. In 1987, Eastman Kodak Company An organic EL device using an aromatic diamine and an aluminum complex having a low molecular weight as a material for forming a light emitting layer has been developed for the first time [Appl. Phys. Lett. 51, 913, 1987].

An organic EL device is a device that injects electric charge into an organic film formed between an electron injection electrode (cathode) and a hole injection electrode (anode) to form an electron and a hole. It is possible to form a device on a flexible transparent substrate such as a plastic substrate and to operate at a lower voltage (10 V or less) than a plasma display panel or an inorganic EL display, It is relatively small and has an advantage of excellent color. The most important factors for determining the performance such as luminous efficiency and lifetime in an organic EL device are the luminescent material. Some characteristics required for such a luminescent material are that the fluorescent quantum yield in a solid state must be large, and the mobility of electrons and holes And should not be easily decomposed during vacuum deposition, and a uniform thin film should be formed and stabilized.

Organic light emitting materials can be roughly divided into polymer materials and low molecular materials. In the molecular structure, there are pure organic light emitting materials which do not contain metal complex compounds and metals. As such light emitting materials, there are known light emitting materials such as chelate complexing agents such as tris (8-quinolinolato) aluminum complexing agent, coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives and oxadiazole derivatives. It is reported that visible light emission from blue to red can be obtained. In order to realize a full-color OLED display, three kinds of light emitting materials for RGB are used. Development of a high-efficiency, long-life RGB light emitting material is an important task to improve the characteristics of the entire organic EL. The luminescent material can be divided into a host material and a dopant material in terms of function. Generally, it is known that an EL material has the best EL structure to form a light emitting layer by doping a host with a dopant. In recent years, development of high-efficiency, long-life organic EL devices has become an urgent task. In particular, considering the level of EL characteristics required for medium to large-sized OLED panels, it is urgent to develop materials that are superior to conventional light emitting materials.

On the other hand, in the case of the blue material, many materials have been developed and commercialized since the DPVBi (compound d) of Idemitsu-Gosan, and the blue material system of Idemitsu-Gosan, the dinaphthylanthracene (compound e) (t-butyl) perlyene, compound f) system are known, but many research and development are still required. The distill compound system of Idemitsu-Gosan, which is known to be the most efficient to date, has a power efficiency of 6 lm / W and a device life of more than 30,000 hours. Sky-Blue is not suitable for. In general, blue light emission is advantageous in terms of light emission efficiency even if the emission wavelength shifts a little toward the long wavelength side, but it can not satisfy the purple light color and it is not easy to apply to a high quality display. Therefore, research and development on color purity, efficiency and thermal stability It is an urgent part.

As the hole injecting and transporting material, copper phthalocyanine (CuPc), 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (4,4'- NPB), N, N'-diphenyl-N, N'-bis (3-methylphenyl) - (1,1'-biphenyl) -4,4'-di TPD), MTDATA (4, 4 ', 4 "-tris (3-methylphenyl) (3-methylphenylphenylamino) triphenylamine), etc. When a device including such a material in a hole injecting and transporting layer has a problem that efficiency and lifetime are lowered, when the organic EL device is driven at a high current, Since the thermal stress is generated between the injection layers and the life of the device is rapidly lowered due to the thermal stress. Further, since the organic material used for the hole injection layer has a very high mobility of holes, The electron-hole charge-balance This causes the quantum efficiency (cd / A) is lowered.

In order to enhance the durability of an organic EL device, it is reported that a compound having a good thin film stability and a compound having a high amorphous property have high film stability. At this time, the glass transition point (Tg) is used as an index of amorphousness. The glass transition temperature of conventional MTDATA is 76 ° C, which is not necessarily high. These materials have not obtained satisfactory characteristics in terms of durability of the organic EL device and also in luminous efficiency due to the characteristics of hole injection and transportation.

Typical examples of conventional electron transfer materials include aluminum complexes such as tris (8-hydroxyquinoline) aluminum (III) (Alq), which was used before Kodak's multilayer thin film OLED in 1987, and bis (Bebq) such as 10-hydroxybenzo- [ h ] quinolinato beryllium (Bebq) [T. Sato et al. J. Mater . Chem . 10 (2000) 1151). However, in the case of these materials, since the OLED has been commercialized since 2002, the limit has begun to emerge. Since then, a number of high-performance electron-transporting materials have been studied and commercialized.

On the other hand, as non-metal complex series, the electron transfer materials of good characteristics that have been published so far include spiro- PBD [N. Johansson et al. Adv . Mater . 10 (1998) 1136], PyPySPyPy [M. Uchida et al. Chem . Mater . 13 (2001) 2680; and Kodak's TPBI [Y.-T. Tao et al. Appl . Phys . Lett . 77 (2000) 1575). However, there is still room for improvement in terms of electroluminescence characteristics and life span.

Particularly noteworthy in the conventional electron transferring material is that the driving voltage is merely slightly improved or the driving life of the device is remarkably lowered compared to the contents to be announced. Side effects. In order to achieve the target such as power consumption and brightness increase which are obstacles to the enlargement of OLED panel up to now, it is a reality that the above-mentioned side effects are a big obstacle.

CBP is the most widely known host material for a phosphorescent light emitting material. Highly efficient OLEDs using a hole blocking layer such as BCP and BAlq are known. In Pioneer, Japan, a high performance OLED using a BAlq derivative as a host Is known.

However, existing materials have advantages in terms of luminescent properties, but they have disadvantages such as low glass transition temperature and very poor thermal stability, which can cause material changes when subjected to a high temperature deposition process under vacuum. Since the power efficiency in OLED = (π / voltage) × current efficiency, the power efficiency is inversely proportional to the voltage, and the power efficiency of the OLED should be high if the power consumption is low. OLEDs using real phosphorescent materials have significantly higher current efficiency (cd / A) than OLEDs using fluorescent materials. However, when conventional materials such as BAlq and CBP are used as hosts for phosphorescent materials, OLEDs using fluorescent materials (Lm / w) because the driving voltage is higher than that of the conventional device. In addition, since the lifetime of the OLED device is never satisfactory, development of a more stable and more excellent host material is required.

Accordingly, an object of the present invention is to provide a compound for an organic electronic material having an excellent skeleton having a good color coordinate and good luminescent efficiency and device lifetime over conventional host or dopant materials in order to solve the above problems, A hole transporting layer, an electron transporting layer, or a light emitting layer, which is a novel organic electroluminescent material.

The present invention relates to a compound for an organic electronic material represented by the following general formula (1), and an organic electronic device comprising the same, wherein the compound for organic electronic material according to the present invention is contained in a hole injection layer, a hole transport layer or an electron transport layer Can be used as a host or a dopant, has an advantage of being able to manufacture an OLED device having a good luminous efficiency and excellent lifetime characteristics of a material and a very good driving life of the device.

[Chemical Formula 1]

[In the above formula (1)

X and Y are each independently _{-C (R 51) (R 52} ) -, -N (R 53) -, -S-, -O-, -Si (R 54) (R 55) -, -P ( R ₅₆ ) -, -P (= O) (R ₅₇ ) -, -C (= O) - or -B (R ₅₈ ) -;

또는

이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며;R ₁ To R ₄ and R ₅₁ to R ₅₈ are each independently (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) cycloalkyl, (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted aromatic rings, (C3-C30) cycloalkyl, substituted or unsubstituted arylcarbonyl, substituted or unsubstituted arylcarbonyl, substituted or unsubstituted arylcarbonyl, substituted or unsubstituted arylcarbonyl, a substituted or unsubstituted (C7-C30) bicycloalkyl, cyano, are each _{NR 21 R 22, BR 23 R} 24, PR 25 R 26, P (= O) R 27 R 28 [R 21 to R ₂₈ Substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted (C6-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted Substituted or unsubstituted (C 1 -C 30) alkyloxy, substituted or unsubstituted (C 1 -C 30) alkylthio, substituted or unsubstituted (C 6 -C 30) aryloxy, Substituted or unsubstituted (C 6 -C 30) arylthio, substituted or unsubstituted (C 1 -C 30) alkoxycarbonyl, substituted or unsubstituted (C 1 -C 30) alkylcarbonyl, substituted or unsubstituted Substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, substituted or unsubstituted (C6-C30) aryloxycarbonyl, substituted or unsubstituted Substituted or unsubstituted (C 1 -C 30) alkoxycarbonyloxy, substituted or unsubstituted (C 1 -C 30) alkylcarbonyloxy, substituted or unsubstituted (C 6 -C 30) arylcarbonyloxy, ) Aryloxycarbonyloxy, carboxyl, nitro, hydroxy,

or

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

R ₁₁ to R ₁₃ are the same as defined in R ₁ to R ₄ , and W is - (CR ₅₁ R ₅₂ ) _m -, -N (R ₅₉ ) -, -S-, -O-, _{R 54) (R 55) -} , -P (R 56) -, -P (= O) (R 57) -, -C (= O) -, -B (R 58) - or - (R ₅₁₎ C = C (R < ₅₂ >)-;

R ₅₉ is the same as defined above for R ₁ to R ₄ ;

또는

이고;L ₁ and L ₂ are independently a chemical bond, a substituted or unsubstituted (C 6 -C 30) arylene, a substituted or unsubstituted (C 3 -C 30) heteroarylene, a substituted or unsubstituted 5- to 7-membered A substituted or unsubstituted aromatic ring, a substituted or unsubstituted heterocycloalkylene, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic ring, (C3-C30) cycloalkylene, substituted or unsubstituted adamantylene, substituted or unsubstituted (C7-C30) bicycloalkylene, substituted or unsubstituted (C2-C30) alkenylene Substituted or unsubstituted (C 1 -C 30) alkylene, substituted or unsubstituted (C 1 -C 30) alkylene thio, substituted or unsubstituted (C 1 -C 30) alkyleneoxy, substituted or unsubstituted (C6-C30) aryleneoxy, substituted or unsubstituted (C6-C30) arylthio, -O-, -S-,

or

ego;

A, B, D and E are, independently of one another, a chemical bond, a substituted or unsubstituted (C6-C30) arylene or a substituted or unsubstituted (C3-C30) heteroarylene;

Wherein said heterocycloalkyl and heteroaryl comprise at least one heteroatom selected from B, N, O, S, P (= O), Si and P;

and m is an integer of 1 or 2.]

Substituents comprising " alkyl ", " alkoxy " and other " alkyl " moieties described in the present invention include both straight chain and branched forms.

&Quot; Aryl " in the present invention means an organic radical derived from an aromatic hydrocarbon by one hydrogen elimination and is a single or fused ring containing 4 to 7, preferably 5 or 6 ring atoms, And includes a form in which a plurality of aryls are connected by a single bond. Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, crycenyl, naphthacenyl, fluoranthenyl, But is not limited thereto. The naphthyl includes 1-naphthyl and 2-naphthyl, anthryl includes 1-anthryl, 2-anthryl and 9-anthryl, and fluorenyl includes 1-fluorenyl, 2- Fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl. "Heteroaryl" in the present invention includes 1 to 4 heteroatoms selected from B, N, O, S, P (= O), Si and P as aromatic ring skeletal atoms and the remaining aromatic ring skeletal atoms are carbon Means a 5 to 6 membered monocyclic heteroaryl and a polycyclic heteroaryl condensed with at least one benzene ring and may be partially saturated. The heteroaryl in the present invention also includes a form in which at least one heteroaryl is linked by a single bond. The heteroaryl groups include divalent aryl groups in which the heteroatoms in the ring are oxidized or trisubstituted to form, for example, an N-oxide or a quaternary salt. Specific examples include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetra Monocyclic heteroaryl such as pyrrolyl, pyrrolyl, pyrrolyl, pyrrolyl, pyrrolyl, pyrrolyl, pyrrolyl, pyrazinyl, pyrrolyl, pyrrolyl, pyrazinyl, pyrimidinyl, pyridazinyl, Benzyloxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenanthridinyl (Such as pyridyl N-oxide, quinolyl N-oxide), quaternary salts thereof, and the like, and the like, but are not limited thereto .

(C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C6- (C1-C30) alkyloxycarbonyl, (C1-C30) alkyloxycarbonyl, (C1-C30) alkylthio, C1-C30) alkylcarbonyloxy "and the like may be limited to a carbon number of 1 to 20, and may be limited to a carbon number of 1 to 10. (C6-C30) aryl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) aryloxycarbonyloxy, (C6-C30) arylthio, (C6-C30) arylcarbonyl, Quot; and the like can be limited to 6 to 20 carbon atoms, and may be limited to 6 to 12 carbon atoms. The heteroaryl of " (C3-C30) heteroaryl " may be limited to from 4 to 20 carbon atoms and may be limited to from 4 to 12 carbon atoms. The heteroaryl of the "(C3-C30) cycloalkyl" may be limited to 3 to 20 carbon atoms and may be limited to 3 to 7 carbon atoms. The "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.

The term " substituted or unsubstituted ", as used herein, refers to a group of the above-mentioned R ₁ to R ₄ , R ₁₁ to R ₁₃ , R ₂₁ to R ₂₈ , R ₅₁ to R ₅₉ , L ₁ , L ₂ , , The substituents of D and E are each independently selected from the group consisting of deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, (C6-C30) aryl, C30) heteroaryl, 5- to 7-membered heterocycloalkyl containing one or more heteroatoms selected from B, N, O, S, P (= O), Si and P, 5- to 7-membered (C6-C30) cycloalkyl, (C3-C30) cycloalkyl, (C6-C30) cycloalkyl having one or more aromatic rings fused thereto, tri (C1- (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, carbazolyl, NR < ₃₁ > R _{32, BR 33 R 34, PR} 35 R 36, P (= O) R 37 R 38 [R 31 to R ₃₈ are independently of each other (C1-C30) alkyl, (C6-C30) aryl or (C3-C30) heteroaryl, (C1-C30) alkoxy, (C1-C30) alkylthio, (C6-C30) aryloxy, (C6-C30) aryloxycarbonyl, (C1-C30) alkoxycarbonyloxy, (C1-C30) alkylcarbonyloxy, (C6-C30) arylcarbonyloxy , (C6-C30) aryloxycarbonyloxy, carboxyl, nitro, and hydroxy, or adjacent substituents are connected to form a ring.

는 하기 구조에서 선택되어지나, 이에 한정되는 것은 아니다.remind

Are selected from the following structures, but are not limited thereto.

[R ₁ , R ₂ and R ₅₁ To R ₅₈ is independently selected from substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, and substituted or unsubstituted (C 3 -C 30) heteroaryl.

,

및

로부터 선택되어지나, 이에 한정되는 것은 아니며, 상기 화학식 1에서와 같이 더 치환될 수 있다.Wherein L ₁ and L ₂ are each independently a chemical bond or a group selected from the group consisting of phenylene, naphthylene, anthracenylene, biphenylene, fluorenylene, triphenylenylene, fluoranthenylene, Examples of the heteroarylene include heteroarylene such as phenanthrene, phenanthrylene, pyrenylene, perylene, and the like, arylene, pyridinylene, pyrazinylene, furanylene, thienylene, selenophenylene, quinolinylene, quinoxalinylene, phenanthrolinylene ,

,

And

However, the present invention is not limited thereto, and it can be further substituted as shown in Formula 1.

R ₃ and R ₄ are independently of each other an aryl such as phenyl, naphthyl, anthryl, biphenyl, fluorenyl, phenanthryl, pyrenyl or perylenyl, pyridinyl, pyrazinyl, , Heteroaryl such as selenophenyl, quinolinyl, quinoxalinyl, phenanthrolinyl, carbazolyl, benzopyraridinyl and the like, aryl in which cycloalkyl such as tetrahydronaphthyl is fused, benzopiperidino, dibenzo Heterocycloalkyl fused with at least one aromatic ring such as morpholino, dibenzoazepino, NR ₂₁ R ₂₂ , BR ₂₃ R ₂₄ , PR ₂₅ R ₂₆ Or P (= O) R < ₂₇ > R < _{28 &} gt ;, but not limited thereto.

및

는 구체적으로 하기 구조로 예시될 수 있다.In addition,

And

Can be specifically exemplified by the following structures.

Wherein R ₅₁ to R ₅₈ are each independently a substituted or unsubstituted (C 1 -C 30) alkyl, a substituted or unsubstituted (C 6 -C 30) aryl, or a substituted or unsubstituted (C 3 -C 30) heteroaryl, (C3-C30) alkylene or (C3-C30) alkenylene with or without a fused ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring.

The compounds for organic electronic materials according to the present invention can be exemplified more specifically as the following compounds, but the following compounds are not intended to limit the present invention.

The compound for an organic electronic material according to the present invention can be prepared as shown in the following reaction formula (1).

[Reaction Scheme 1]

Wherein R ₁ , R ₂ , R ₃ , R ₄ , L ₁ , L ₂ , X and Y are the same as defined in the above formula (1).

The present invention provides an organic electronic device, wherein the organic electronic device according to the present invention comprises: a first electrode; A second electrode; And at least one organic compound layer interposed between the first electrode and the second electrode, wherein the organic compound layer comprises at least one compound for organic electronic materials of Formula 1. The compound for an organic electronic material may be used as a material for a hole injection layer, a hole transporting layer, or an electron transporting layer, or as a dopant or a host material for a light emitting layer.

In addition, the organic layer may include a light emitting layer, and the light emitting layer may include at least one dopant or a host in addition to one or more compounds for the organic electronic material of Formula 1. In the organic electronic device of the present invention, The host or host is not particularly limited.

The dopant or host to be applied to the organic electronic device of the present invention is preferably selected from compounds represented by the following formulas (2) to (6).

(2)

[In the formula (2), R ₁₀₁ to R ₁₀₄ are each independently Substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted B, 5 to 7 membered heterocycloalkyl containing one or more heteroatoms selected from N, O, S, P (O), Si and P, 5- to 7-membered heteroaryl having one or more fused substituted or unsubstituted aromatic rings (C7-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, cycloalkyl substituted by one or more fused aromatic rings, substituted or unsubstituted adamantyl, substituted or unsubstituted bicycloalkyl, cyano, NR ₁₁ R _12, in _{BR 13 R 14, PR 15 R} 16, P (= O) R 17 R 18 [R 11 to R ₁₈ independently represent a substituted or unsubstituted (C1-C30 each other (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted tri Substituted or unsubstituted (C6-C30) aryl (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted Substituted or unsubstituted (C1-C30) alkylthio, substituted or unsubstituted (C6-C30) aryloxy, substituted or unsubstituted (C6- Substituted or unsubstituted (C 1 -C 30) alkoxycarbonyl, substituted or unsubstituted (C 1 -C 30) alkylcarbonyl, substituted or unsubstituted (C 6 -C 30) arylcarbonyl, C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, substituted or unsubstituted (C6-C30) aryloxycarbonyl, substituted or unsubstituted (CrC30) alkoxycarbonyloxy, substituted or unsubstituted Substituted or unsubstituted (C1-C30) alkylcarbonyloxy, substituted or unsubstituted (C6-C30) arylcarbonyloxy, substituted or unsubstituted (C6-C30) aryloxycarbonyloxy, carboxyl, nitro, Lt; / RTI > is hydrogen, or includes, or includes, a fused ring with adjacent carbons (C3-C30) alkylene or (C3-C30) alkenylene to form a fused ring.

(3)

Wherein Ar ₁ and Ar ₂ are independently selected from the group consisting of substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, substituted or unsubstituted (C 4 -C 30) Substituted or unsubstituted (C1-C30) alkylamino, substituted or unsubstituted B, N, O, S, P (O) A 5- to 7-membered heterocycloalkyl containing one or more selected hetero-cycloalkyl, a 5- to 7-membered heterocycloalkyl having one or more fused or unsubstituted aromatic rings, a substituted or unsubstituted (C3-C30) cycloalkyl a, fused substituted or unsubstituted aromatic ring by one or more (C6-C30) cycloalkyl, wherein, Ar ₁ and Ar ₂ are with or without a fused ring (C3-C30) alkylene or (C3-C30) An alicyclic ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;

when e is 1, Ar ₃ is substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C4-C30) heteroaryl or a substituent selected from the following structures;

When e is 2, Ar ₃ is a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (C4-C30) heteroarylene or a substituent selected from the following structures;

Ar ₄ and Ar ₅ are independently of each other a substituted or unsubstituted (C6-C30) arylene or a substituted or unsubstituted (C4-C30) heteroarylene;

R ₁₁₁ to R ₁₁₃ are independently of each other hydrogen, deuterium, substituted or unsubstituted (C 1 -C 30) alkyl or substituted or unsubstituted (C 6 -C 30) aryl;

f is an integer of 1 to 4, and g is an integer of 0 or 1.]

[Chemical Formula 4]

M ^One L ¹⁰¹ L ¹⁰² L ¹⁰³

Wherein M ¹ is 7 Group 8 Group 9 Group, Group 10, Group 11, Group 13, Group 14, is selected from the group consisting of metals of Group 15 and Group 16 ligands L ^101, L ¹⁰² and L ¹⁰³ are each Independently selected from the following structures.

Wherein R ₁₃₁ to R ₁₃₃ independently represent hydrogen, (C 1 -C 30) alkyl in which halogen is substituted or unsubstituted, (C 6 -C 30) aryl in which (C 1 -C 30) alkyl is unsubstituted or substituted, or Halogen;

R ₁₃₄ to R ₁₄₉ independently represent hydrogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 1 -C 30) alkoxy, substituted or unsubstituted (C 3 -C 30) Substituted or unsubstituted (C6-C30) arylamino, substituted or unsubstituted (C6-C30) arylamino, substituted or unsubstituted _5, a substituted or unsubstituted tree (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted tree (C6-C30) arylsilyl, Cyano or halogen;

R ₁₅₀ to R ₁₅₃ are each independently hydrogen, (C 1 -C 30) alkyl in which the halogen is substituted or unsubstituted, or (C 6 -C 30) aryl in which the (C 1 -C 30) alkyl is unsubstituted or substituted;

R ₁₅₄ and R ₁₅₅ independently of one another are hydrogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl or halogen, or R ₁₅₄ and R ₁₅₅ comprise or consist of a fused ring (C3-C12) alkylene or (C3-C12) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;

R ₁₅₆ 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 ₁₅₇ to R ₁₅₉ are independently of each other hydrogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl or halogen;

,

또는

이며, R₁₆₁ 내지 R₁₇₂는 서로 독립적으로 수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬, (C1-C30)알콕시, 할로겐, 치환 또는 비치환된(C6-C30)아릴, 시아노, 치환 또는 비치환된(C5-C30)시클로알킬이거나, R₁₃₇ 또는 R₁₃₈과 알킬렌 또는 알케닐렌으로 연결되어 포화 또는 불포화의 융합고리를 형성할 수 있다.]Q is

,

or

And, R ₁₆₁ to R ₁₇₂ are independently H, halogen-substituted or unsubstituted (C1-C30) alkyl, (C1-C30) alkoxy, halogen, substituted or unsubstituted (C6-C30) aryl, cyano each other , or substituted or unsubstituted cycloalkyl, unsubstituted (C5-C30), connected to R ₁₃₇ or R ₁₃₈ and alkylene or alkenylene to form a fused ring, saturated or unsaturated.]

[Chemical Formula 5]

(Ar ₁₁ ) _h -L ₁₁ - (Ar ₁₂ ) _i

[Chemical Formula 6]

_{(Ar 13) j -L 12 -} (Ar 14) k

[In the formulas (5) and (6)

L ₁₁ is substituted or unsubstituted (C6-C30) arylene or substituted or unsubstituted (C4-C30) heteroarylene;

L ₁₂ is substituted or unsubstituted anthracenylene;

Ar ₁₁ to Ar ₁₄ independently represent hydrogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 1 -C 30) alkoxy, halogen, substituted or unsubstituted (C 4 -C 30) Substituted or unsubstituted (C5-C30) cycloalkyl or substituted or unsubstituted (C6-C30) aryl; And

h, i, j and k are each independently an integer of 0 to 4.]

In the organic electronic device of the present invention, the organic electronic device may include a compound for an organic electronic material represented by the general formula (1), and at the same time, at least one compound selected from the group consisting of an arylamine compound or a styrylarylamine compound. The arylamine-based compound or styrylarylamine-based compound is exemplified in Application Nos. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but is not limited thereto.

In addition, in the organic electronic device of the present invention, in addition to the organic luminescent compound of Formula 1, an organic compound of Group 1, 2, 4, 5 period transition metal, lanthanide metal and d- The organic layer may further include at least one metal or complex compound to be selected, and the organic layer may include a light emitting layer and a charge generating layer.

Further, a white organic electroluminescent device can be formed by simultaneously including at least one organic light emitting layer emitting red, green or blue light in addition to the organic light emitting compound in the organic material layer. The compounds emitting blue, green or red light are exemplified in Application Nos. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.

In the organic electronic device of the present invention, at least one inner surface of the pair of electrodes is provided with one or more layers selected from a chalcogenide layer, a metal halide layer and a metal oxide layer (hereinafter referred to as "surface layer " . 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 and SiAlON. Examples of the halogenated metal include LiF, MgF ₂ , CaF ₂ , Rare-earth metals and the like. Preferable examples of the metal oxides include Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO and the like.

In the organic electronic device of the present invention, it is also preferable to dispose a mixed region of the electron transfer compound and the reducing dopant or a mixed region of the hole transfer compound and the oxidative dopant on at least one surface of the pair of electrodes thus fabricated Do. In this way, since the electron transfer compound is reduced to the anion, it becomes easy to inject and transfer electrons from the mixed region to the light emitting medium. Further, since the hole transport compound is oxidized and becomes a cation, it becomes easy to inject and transport holes from the mixed region into the light emitting medium. Preferred oxidizing 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.

Also, a white organic electronic device having two or more light emitting layers can be manufactured using a reducing dopant layer as a charge generating layer.

The organic electroluminescent material according to the present invention has an advantage of being able to produce an OLED device having a good luminous efficiency and excellent lifetime characteristics of a material and a very good driving life of the device.

Hereinafter, for the purpose of a detailed understanding of the present invention, the compound for organic electronic materials according to the present invention, the method for producing the same and the luminescent characteristics of the device according to the present invention will be described with reference to the representative compound of the present invention, , And are not intended to limit the scope of the present invention.

[Preparation Example 1] Preparation of Compound 19

compound A Manufacturing

30.0 g (282.6 mmol) of 1,3-dimethylbenzene and 2.3 g (14.1 mmol) of FeCl ₃ were dissolved in CCl ₄ and 32.0 mL (621.7 mmol) of Br ₂ was slowly added at 0 ° C. The mixture was stirred at room temperature for 2 hours, neutralized with KOH aqueous solution, extracted with MC, dried with MgSO ₄ , and distilled under reduced pressure. This was separated into a column to obtain 32.5 g (123.12 mmol, 43.7%) of Compound A.

compound B Manufacturing

Compound A 32.5 g (123.12 mmol), phenylboronic acid 37.5 g (307.8 mmol), Pd (PPh 3) 4 5.7 g (4.9 mmol), toluene 300 mL, ethanol, _{l 150 mL, K 2 CO 3} 51.1 g (369.4 mmol , 2M aqueous solution) were added, and the mixture was stirred under reflux. After 12 hours, the reaction mixture was cooled to room temperature, extracted with EA, washed with distilled water and dried over MgSO ₄ . This was distilled off under reduced pressure and subjected to column separation to obtain 28.1 g (108.8 mmol, 88.4%) of Compound B.

compound C Manufacturing

28.1 g (108.8 mmol) of Compound B was dissolved in 500 mL of pyridine, and then 90.0 g of KMnO ₄ was dissolved in 60 mL of distilled water. After refluxing for 5 hours, 500 mL of distilled water was added thereto, and the mixture was refluxed and stirred for 12 hours. The reaction mixture was cooled to room temperature and the resulting solid was filtered, and the filtrate was collected, and hydrochloric acid was added until acidic. At this time, the resulting solid was filtered off under reduced pressure and dried to obtain Compound ( C ) (30.7 g, 96.4 mmol, 88.7%).

compound D Manufacturing

30.7 g (96.4 mmol) of Compound C was slowly added to 600 mL of sulfuric acid. This was stirred at room temperature for 2 hours and the ice water was slowly added to the reaction solution. At this time, a purple precipitate was formed, which was filtered under reduced pressure, and washed with distilled water, K ₂ CO ₃ aqueous solution and distilled water in that order to obtain 22.4 g (79.31 mmol, 82.3%) of compound D.

compound E Manufacturing

133.5 g (2380.5 mmol) of KOH was added to 300 mL of diethylene glycol, and the mixture was stirred. Then, Compound D (22.4 g, 79.35 mmol) and hydrazine monohydrate (78.9 mL, 1626.6 mmol) Respectively. When the reaction was complete, it was slowly cooled to room temperature and slowly added to a solution of hydrochloric acid in ice. The solid thus formed was dried under reduced pressure and recrystallized from acetic acid to obtain 17.2 g (67.62 mmol, 85.2%) of Compound E.

compound F Manufacturing

17.2 g (67.6 mmol) of compound E are dissolved in 1.5 L of THF and cooled to -78 < 0 > C. Add 73.0 mL (182.6 mmol, 2.5 M in hexane) of N-BuLi slowly. After one hour, add 15.1 mL (202.9 mmol) of bromoethane. After stirring for one hour, slowly add 86.6 mL (216.4 mmol, 2.5 M in hexane) of n-BuLi at -78 ° C again. After stirring for one hour, add 15.1 mL (202.9 mmol) of bromoethane. After 5 hours, add distilled water and extract with MC. Dried with MgSO ₄ and evaporated under reduced pressure. Hexane to obtain 14.8 g (40.4 mmol, 59.7%) of Compound ( F ).

compound G Manufacturing

14.8 g (40.4 mmol) of Compound F was dissolved in CHCl ₃ , 0.3 g (2.0 mmol) of FeCl ₃ was added at 0 ° C, and 4.5 mL (88.8 mmol) of Br ₂ was added thereto. After stirring at room temperature for 12 hours, it is neutralized with aqueous KOH solution. And extracted with MC, it dried with MgSO _4. The mixture was distilled under reduced pressure and recrystallized with hexane to obtain 15.7 g (29.9 mmol, 74.9%) of Compound G.

compound 19 Manufacturing

Compound G 15.7 g (29.9 mmol), phenyl boronic acid 9.1 g (74.9 mmol), Pd (PPh 3) 4 0.8 g (1.2 mmol), toluene 200 mL, ethanol _{100 mL, K 2 CO 3 12.4} g (89.8 mmol, 2M aqueous solution) were mixed and refluxed and stirred. After 12 hours, the reaction mixture was cooled to room temperature, methanol was added thereto, and the resulting solid was filtered under reduced pressure. Wash with distilled water and methanol. Recrystallization from EA and THF gave 8.5 g (16.4 mmol, 54.7%) of compound 19 .

[Preparation Example 2] Preparation of Compound 33

compound H Manufacturing

37.0 g (153.8 mmol) of K ₂ O ( ₃ -dibromo-4,6-diiodobenzene, 30.0 g, 61.6 mmol) _{PO 47 H 2 O 31.2 g (} 92.3 mmol), Pd (PPh 3) mix _{4 1.4 g (1.2 mmol),} DMF and stirred at 100 ℃ 20 hours. Cool to room temperature, extract with EA and wash with distilled water. Dried with MgSO ₄ and evaporated under reduced pressure. The column was separated to obtain 7.3 g (13.4 mmol, 21.7%) of Compound ( H ).

compound  I Manufacturing

7.3 g (13.4 mmol) of compound H are dissolved in 2 L of diethyl ether, and slowly add 26.7 mL (66.9 mmol, 2.5 M in hexane) of n-BuLi at 0 ° C. After stirring for 4 hours, add 4.8 mL (40.1 mmol) of dichlorodimethylsilane. Stir 12 hours at room temperature and add distilled water. The mixture is extracted with diethyl ether, dried over MgSO ₄ and distilled under reduced pressure. Color separation afforded 1.4 g (4.1 mmol, 30.6%) of compound I.

compound J Manufacturing

1.4 g (4.1 mmol) of Compound ( I ), 0.8 g (4.5 mmol) of NBS and 50 mL of THF were added and the mixture was stirred at 0 ° C for 8 hours. When the reaction is complete, extract with distilled water and EA. The organic layer was dried over MgSO ₄ and then the solvent was removed using a rotary evaporator. Then, 1.2 g (2.8 mmol) of Compound J was separated by column chromatography using hexane and EA as eluent.

compound 33 Manufacturing

Compound J 1.2 g (2.8 mmol), 4-di-phenylamine 0.7 g (4.2 mmol), Pd (OAc) 2 0.06 g (0.1 mmol), P (t-Bu) 3 (in toluene 50%) 0.09 mL ( 0.2 mmol) and Cs ₂ CO ₃ 0.4 g (8.4 mmol) were dissolved in 50 mL of toluene, and the mixture was refluxed and stirred at 110 ° C for 5 hours. After completion of the reaction, the reaction mixture was cooled at room temperature, extracted with EA and distilled water, and dried under reduced pressure. This was subjected to column separation to obtain 0.9 g (1.7 mmol) of Compound 33 .

[Preparation Example 3] Preparation of Compound 40

compound K Manufacturing

3-Bromophenylhydrazine hydrochloride is dissolved in distilled water and 2M NaOH aqueous solution is added. The resulting solid was filtered under reduced pressure to obtain 3-bromophenylhydrazine. 30.0 g (267.5 mmol) of cyclohexane-1,3-dione are placed in 1000 mL of ethanol. Slowly add 3-bromophenylhydrazine in the absence of light. After 20 minutes, put in ice water. The resulting solid is filtered under reduced pressure and washed with cold ethanol. And dried under reduced pressure to obtain 46.2 g (102.6 mmol, 38.4%) of Compound ( K ).

compound  L Manufacturing

Slowly add 46.2 g (102.6 mmol) of the compound K to 140 mL of a mixed solution of acetic acid and sulfuric acid (1: 4) at 0 ° C. After stirring for 5 minutes, quickly raise to 50 ° C and slowly raise to 110 ° C. After 20 minutes, the mixture was cooled to room temperature and stirred for 12 hours. Ethanol is added and after one hour, the resulting solid is filtered under reduced pressure to neutralize. And dried under reduced pressure to obtain 21.7 g (52.4 mmol, 51.1%) of the compound L

compound M Manufacturing

Compound L 21.7 g (52.4 mmol), iodo-benzene, 23.4 mL (209.6 mmol), 18- crown -6 2.8 g (10.5 mmol), Cu (Copper) 2.0 g (31.4 mmol ), K 2 CO 3 32.6 g (235.8 mmol) and 300 mL of 1,2-dichlorobenzene were mixed and stirred at 180 ° C for 12 hours. The reaction mixture is cooled to room temperature and the reaction solvent is distilled off under reduced pressure. Extract with EA and wash with distilled water. Dried with MgSO ₄ and evaporated under reduced pressure. Column separation afforded 24.3 g (42.9 mmol, 81.9%) of compound M.

compound 40 Manufacturing

Compound M 24.3 g (42.9 mmol), diphenylamine, 18.2 g (107.3 mmol), Pd (OAc) 2 0.36 g (1.7 mmol), P (t-Bu) 3 (50% in toluene) 1.5 mL (3.4 mmol) And 6.6 g (128.7 mmol) of Cs ₂ CO ₃ were dissolved in 500 mL of toluene, and the mixture was refluxed and stirred at 110 ° C for 5 hours. After completion of the reaction, the reaction mixture is cooled at room temperature, 1000 mL of methanol is added, and the resulting solid is filtered under reduced pressure. Wash the solid again with distilled water, methanol and hexane. The solid was mixed with 100 mL of EA and refluxed for 2 hours. After filtration under reduced pressure, the solid is separated from the column. The resulting solid was dissolved in THF, methanol was added, and the resulting solid was filtered under reduced pressure to obtain 15.3 g (20.6 mmol) of Compound 40 .

[Preparation Example 4] Preparation of Compound 46

compound N Manufacturing

Dissolve phenylhydrazine hydrochloride in distilled water and add 2 M aqueous NaOH solution. The resulting solid was filtered under reduced pressure to obtain phenylhydrazine. 30.0 g (267.5 mmol) of cyclohexane-1,3-dione are placed in 1000 mL of ethanol. Slowly add phenylhydrazine in the absence of light. After 20 minutes, put in ice water. The resulting solid is filtered under reduced pressure and washed with cold ethanol. And dried under reduced pressure to obtain 46.2 g of compound N (102.6 mmol, 38.4%).

compound O Manufacturing

Slowly add 46.2 g (102.6 mmol) of compound N to 140 mL of a mixed solution of acetic acid and sulfuric acid (1: 4) at 0 ° C. After stirring for 5 minutes, quickly raise to 50 ° C and slowly raise to 110 ° C. After 20 minutes, the mixture was cooled to room temperature and stirred for 12 hours. After adding ethanol, solid is formed after one hour, and the resulting solid is filtered under reduced pressure to make neutral. After drying under reduced pressure, 21.7 g (52.4 mmol, 51.1%) of compound O was obtained.

compound 46 Manufacturing

Compound O 10.0 g (39.0 mmol), iodo-benzene 5.2 mL (46.8 mmol), 18- crown -6 2.1 g (7.8 mmol), Cu (Copper) 1.5 g (23.4 mmol ), K 2 CO 3 24.3 g (175.5 mmol) of the above compound and 150 mL of 1,2-dichlorobenzene were mixed and stirred at 180 ° C for 5 hours. Then, 12.5 g (46.8 mmol) of 2-chloro-4,6-diphenyl- 2.1 g (7.8 mmol) of 18-crown-6, and 1.5 g (23.4 mmol) of copper. After stirring at 180 DEG C for 12 hours, the reaction mixture is cooled to room temperature and the reaction solvent is distilled off under reduced pressure. Extract with EA and wash with distilled water. Dried with MgSO ₄ and evaporated under reduced pressure. The mixture was subjected to column separation to obtain 3.8 g of compound 46 (6.7 mmol, 17.3%).

Organic luminescent compounds 1 to 69 were prepared using the methods of Preparation Examples 1 to 4, and ¹ H NMR and MS / FAB of the organic luminescent compounds prepared in Table 1 were shown.

[Table 1]

[Example 1] Production of OLED device using organic electronic material compound according to the present invention

An OLED device having a structure using the compound for electronic materials of the present invention was fabricated.

First, a transparent electrode ITO thin film (15 Ω / □) obtained from a glass for an OLED was subjected to ultrasonic cleaning using trichlorethylene, acetone, ethanol, and distilled water sequentially, and then stored in isopropanol and used.

Next, an ITO substrate was placed in a substrate folder of a vacuum deposition equipment, and 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) Phenylamine (2-TNATA) was added and the chamber was evacuated until the degree of vacuum reached 10 ^-6 torr. Then, 2-TNATA was evaporated by applying a current to the cell to form a 60 nm thick hole injection layer N , N' -bis (α-naphthyl) -N , N' -diphenyl-4,4'-diamine (NPB) was added to another cell in a vacuum deposition apparatus, Current was applied to evaporate NPB to deposit a hole transport layer having a thickness of 20 nm on the hole injection layer.

A hole injecting layer and a hole transporting layer were formed, and then a light emitting layer was deposited thereon as follows. The compound of the present invention (for example, Compound 1) was put into one cell in a vacuum deposition apparatus and DSA-Ph having the following structure was put in another cell. Then, the two cells were heated together and DSA-Ph A light emitting layer with a thickness of 30 nm was deposited on the hole transporting layer by depositing a speed ratio of 2 to 5 wt%.

Then, tris (8-hydroxyquinoline) -aluminum (III) (Alq) having the following structure was vapor-deposited as an electron transfer layer on the light emitting layer to a thickness of 20 nm and then compound lithium quinolate (Liq) Was deposited to a thickness of 1 to 2 nm, and then an Al cathode was deposited to a thickness of 150 nm using another vacuum deposition apparatus to fabricate an OLED.

Each material used in the OLED device was vacuum sublimated and purified at 10 ^-6 torr to be used as an OLED light emitting material.

[Example 2] Fabrication of OLED device using organic electronic material compound according to the present invention

After the hole injection layer and the hole transport layer were formed in the same manner as in Example 1, DNA (dinaphthylanthracene) was added as a host to one of the cells in the vacuum vapor deposition apparatus, and Compound 24 according to the present invention And then the two materials were evaporated at different rates and doped with 2 to 5 wt% based on the host to deposit a 30 nm thick emission layer on the hole transport layer.

Subsequently, an electron transport layer and an electron injection layer were deposited in the same manner as in Example 1, and then an Al cathode was deposited to a thickness of 150 nm using another vacuum vapor deposition apparatus to fabricate an OLED.

[Comparative Example 1] Luminescence characteristics of OLED device using conventional light emitting material

The hole injection layer and the hole transport layer were formed in the same manner as in Example 1, DNA (dinaphthylanthracene) as a light emitting host material was placed in one cell of the vacuum vapor deposition equipment, and DSA-Ph And then a light emitting layer with a thickness of 30 nm was deposited on the hole transport layer at a deposition rate of 100: 3.

Subsequently, an electron transport layer and an electron injection layer were deposited in the same manner as in Example 1, and then an Al cathode was deposited to a thickness of 150 nm using another vacuum vapor deposition apparatus to fabricate an OLED.

The luminescence efficiencies of the OLED device containing the compound for an electronic material according to the present invention and the conventional luminescent compound prepared in Example 1-2 and Comparative Example 1 were measured at 1,000 cd / m ² , respectively, and are shown in Table 2 below .

[Table 2]

As shown in Table 2, when the material of the present invention was applied to a blue light emitting device, it was confirmed that when the organic light emitting compounds of the present invention were used as a host, the light emitting efficiency was equal to or higher than that of Comparative Example 1, It was confirmed that the color purity was significantly improved to blue light emission compared with the orange light emission while maintaining the light emission efficiency equal to or higher than that of Comparative Example 1. [

[Example 3] Fabrication of OLED device using organic electronic material compound according to the present invention

A hole injecting layer was formed in the same manner as in Comparative Example 1 and then a compound 22 of the following structure was put in another cell in a vacuum vapor deposition apparatus and a current was applied to the cell to evaporate the hole injecting layer, Layer.

An OLED device was fabricated in the same manner as in Comparative Example 1 except for the above.

The luminous efficiencies of the OLED device containing the compound for electronic material according to the present invention and the OLED containing the conventional luminous compound prepared in Example 3 and Comparative Example 1 were measured at 1,000 cd / m ² , respectively, and are shown in Table 3 below.

[Table 3]

It was confirmed that the compounds developed in the present invention show superior properties in terms of performance compared to conventional materials.

[Example 4] Fabrication of OLED device using organic electronic material compound according to the present invention

In the same manner as in Comparative Example 1, an ITO substrate was placed in a substrate folder of a vacuum vapor deposition equipment, and a compound 40 having the following structure was placed in a cell in the equipment. After evacuation was performed until the degree of vacuum in the chamber reached 10 ^-6 torr, To give compound 40 Evaporated to deposit a 60 nm thick hole injection layer on the ITO substrate.

Next, N, N'-bis (α-naphthyl) -N, N'-diphenyl-4,4'-diamine (NPB) was added to another cell in the vacuum evaporation apparatus, A hole transporting layer having a thickness of 20 nm was deposited on the hole injecting layer.

 An OLED device was fabricated in the same manner as in Comparative Example 1 except for the above.

The luminous efficiencies of the OLED device containing the compound for an organic electronic material according to the present invention and the conventional luminous compound prepared in Example 4 and Comparative Example 1 were measured at 1,000 cd / m ² , respectively, and are shown in Table 4 below.

[Table 4]

It was confirmed that the compounds developed in the present invention show superior properties in terms of performance compared to conventional materials.

[Example 5] Fabrication of OLED device using organic electronic material compound according to the present invention

The hole injection layer and the hole transport layer were formed in the same manner as in Example 1, DNA (dinaphthylanthracene) as a light emitting host material was placed in one cell of the vacuum vapor deposition equipment, and DSA-Ph And then a light emitting layer with a thickness of 30 nm was deposited on the hole transport layer at a deposition rate of 100: 3.

Next, a compound (for example, Compound 42) according to the present invention is deposited as an electron transfer layer to a thickness of 20 nm, and lithium quinolate (Liq) having the following structure is deposited as an electron injecting layer to a thickness of 1 to 2 nm After that, an Al cathode was deposited to a thickness of 150 nm using another vacuum vapor deposition apparatus to fabricate an OLED.

The luminescence efficiencies of the compound for organic electronic material according to the present invention and the OLED device containing the conventional luminescent compound prepared in Example 5 and Comparative Example 1 were measured at 1,000 cd / m ² , respectively, and are shown in Table 5 below.

[Table 5]

It can be confirmed that the compounds developed in the present invention exhibit superior properties in terms of performance over conventional materials.

[Example 6] Fabrication of OLED device using organic electronic material compound according to the present invention

A hole injecting layer and a hole transporting layer were formed in the same manner as in Example 1, and then a phosphorescent host compound 47 according to the present invention was placed in one cell of the vacuum vapor deposition equipment. In another cell, a conventional green light emitting dopant, Ir ppy) ₃ , and the two materials were evaporated at different rates and doped to deposit a light emitting layer with a thickness of 30 nm on the hole transport layer. The doping concentration at this time is suitably 4 to 10% by weight based on the host.

Subsequently, an electron transport layer and an electron injection layer were deposited in the same manner as in Example 1, and an Al cathode was deposited to a thickness of 150 nm using another vacuum vapor deposition apparatus to fabricate an OLED.

[Comparative Example 2] Luminescence characteristics of OLED device using conventional light emitting material

4'-N, N'-dicarbazole-biphenyl (CBP), which is a light emitting host material, was added to one cell of a vacuum deposition apparatus after forming a hole injection layer and a hole transport layer in the same manner as in Example 1, Ir (ppy) _3, which is a conventional green light emitting dopant, was doped into the other cells, and then a light emitting layer with a thickness of 30 nm was deposited on the hole transport layer by evaporating the two materials at different rates. The doping concentration at this time is suitably 4 to 10% by weight based on the host.

Then, Bis (2-methyl-8-quinolinato) aluminum (III) (BAlq) was deposited as a hole blocking layer on the light emitting layer to a thickness of 5 nm. After the electron injection layer was deposited, an Al cathode was deposited to a thickness of 150 nm using another vacuum deposition apparatus to fabricate an OLED.

Table 6 shows the driving voltage and the green luminescence efficiency of the OLED device containing the organic luminescent compound according to the present invention and the conventional luminescent compound prepared in Example 6 and Comparative Example 2 at 10 mA / cm ² , respectively .

[Table 6]

In the device using the compound according to the present invention as a phosphorescent host, the position of the main peak of the EL did not change in comparison with CBP which is a conventional luminescent host material, but the x value of the color coordinate was greatly reduced because FWHM was decreased. In addition, the device was driven at a voltage lower than 0.6 V as compared with the device using CBP as a host. Therefore, when the compound according to the present invention is used as a green phosphorescent host, the power consumption can be remarkably lowered compared with the conventional materials, and the step of the device manufacturing process can be reduced by exhibiting the luminous efficiency without using the hole blocking layer Which is a good green phosphorescent host.

Claims (8)

A compound for an organic electronic material represented by the following formula (1).
[Chemical Formula 1]

[In the above formula (1)
X and Y are -N ( _R53 ) -;
Each R ₅₃ is independently selected from substituted or unsubstituted (C 6 -C 30) aryl, wherein (C 6 -C 30) aryl is not substituted with substituted or unsubstituted (C 3 -C 30) heteroaryl;
R ₁ and R ₂ are each independently (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) cycloalkyl, (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted aromatic rings, (C3-C30) cycloalkyl, substituted or unsubstituted arylcarbonyl, substituted or unsubstituted arylcarbonyl, substituted or unsubstituted arylcarbonyl, substituted or unsubstituted arylcarbonyl, a substituted or unsubstituted (C7-C30) bicycloalkyl, cyano, are each _{NR 21 R 22, BR 23 R} 24, PR 25 R 26, P (= O) R 27 R 28 [R 21 to R ₂₈ Substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted (C6-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted Substituted or unsubstituted (C 1 -C 30) alkyloxy, substituted or unsubstituted (C 1 -C 30) alkylthio, substituted or unsubstituted (C 6 -C 30) aryloxy, Substituted or unsubstituted (C 6 -C 30) arylthio, substituted or unsubstituted (C 1 -C 30) alkoxycarbonyl, substituted or unsubstituted (C 1 -C 30) alkylcarbonyl, substituted or unsubstituted Substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, substituted or unsubstituted (C6-C30) aryloxycarbonyl, substituted or unsubstituted Substituted or unsubstituted (C 1 -C 30) alkoxycarbonyloxy, substituted or unsubstituted (C 1 -C 30) alkylcarbonyloxy, substituted or unsubstituted (C 6 -C 30) arylcarbonyloxy, ) Aryloxycarbonyloxy, carboxyl, nitro, hydroxy,

or

Or (C3-C30) alkylene or (C3-C30) alkenylene with or without a fused ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
R ₃ and R ₄ are each independently NR ₂₁ R _{22, wherein} R ₂₁ and R ₂₂ are independently selected from the group consisting of (C 1 -C 30) alkyl, (C 1 -C 30) alkyl, substituted or unsubstituted (C3-C30) heteroaryl, < / RTI >
R ₁₁ to R ₁₃ are the same as defined in R ₁ to R ₄ , and W is - (CR ₅₁ R ₅₂ ) _m -, -N (R ₅₉ ) -, -S-, -O-, _{R 54) (R 55) -} , -P (R 56) -, -P (= O) (R 57) -, -C (= O) -, -B (R 58) - or - (R ₅₁₎ C = C (R < ₅₂ >)-;
R ₅₁ , R ₅₂ and R ₅₄ to R ₅₉ are the same as defined for R ₁ to R ₄ above;
L ₁ and L ₂ are chemical bonds;
Wherein said heterocycloalkyl and heteroaryl comprise at least one heteroatom selected from B, N, O, S, P (= O), Si and P;
and m is an integer of 1 or 2.] The method according to claim 1,
Wherein R ₁ and R _2, R ₁₁ to R _13, R ₂₁ to R ₂₈ and R ₅₁ to R ₅₉ substituents include deuterium, halogen, halogen (C6-C30) alkyl, (C1-C30) unsubstituted or substituted with a (C5-C30) aryl, (C6-C30) aryl or (C3-C30) heteroaryl substituted with at least one member selected from B, N, O, S, P (C3-C30) cycloalkyl, (C6-C30) cycloalkyl which is fused with one or more aromatic rings, tri (C1-C30) heterocycloalkyl which is fused with one or more aromatic rings, C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, adamantyl, (C7- C30) bicycloalkyl, (C2-C30) alkynyl, cyano, _{carbazolyl, NR 31 R 32, BR 33} R 34, PR 35 R 36, P (= O) R 37 R 38 [R 31 to R ₃₈ are independently selected from (C1 each other (C1-C30) alkyl, (C6-C30) aryl or (C3-C30) heteroaryl, C1-C (C6-C30) arylthio, (C1-C30) alkoxycarbonyl, (C1-C30) alkylcarbonyl, (C6- (C6-C30) arylcarbonyl, (C6-C30) aryloxycarbonyl, (C1-C30) alkoxycarbonyloxy, ) Aryloxycarbonyloxy, carboxyl, nitro, and hydroxy, or wherein adjacent substituents are connected to form a ring. 4. An organic electronic device comprising the compound for organic electronic material according to any one of claims 1 to 3. The method of claim 3,
The organic electronic device includes a first electrode; A second electrode; And at least one organic compound layer interposed between the first electrode and the second electrode, wherein the organic compound layer comprises at least one compound for the organic electronic material and at least one compound selected from the group consisting of a dopant represented by the following Chemical Formulas 2 to 4, 6 < / RTI >
(2)

[In the formula (2), R ₁₀₁ to R ₁₀₄ are each independently Substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted B, 5 to 7 membered heterocycloalkyl containing one or more heteroatoms selected from N, O, S, P (O), Si and P, 5- to 7-membered heteroaryl having one or more fused substituted or unsubstituted aromatic rings (C7-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, cycloalkyl substituted by one or more fused aromatic rings, substituted or unsubstituted adamantyl, substituted or unsubstituted bicycloalkyl, cyano, NR ₁₁ R _12, in _{BR 13 R 14, PR 15 R} 16, P (= O) R 17 R 18 [R 11 to R ₁₈ independently represent a substituted or unsubstituted (C1-C30 each other (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted tri Substituted or unsubstituted (C6-C30) aryl (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted Substituted or unsubstituted (C1-C30) alkylthio, substituted or unsubstituted (C6-C30) aryloxy, substituted or unsubstituted (C6- Substituted or unsubstituted (C 1 -C 30) alkoxycarbonyl, substituted or unsubstituted (C 1 -C 30) alkylcarbonyl, substituted or unsubstituted (C 6 -C 30) arylcarbonyl, C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, substituted or unsubstituted (C6-C30) aryloxycarbonyl, substituted or unsubstituted (CrC30) alkoxycarbonyloxy, substituted or unsubstituted Substituted or unsubstituted (C1-C30) alkylcarbonyloxy, substituted or unsubstituted (C6-C30) arylcarbonyloxy, substituted or unsubstituted (C6-C30) aryloxycarbonyloxy, carboxyl, nitro, Lt; / RTI > is hydrogen, or includes, or includes, a fused ring with adjacent carbons (C3-C30) alkylene or (C3-C30) alkenylene to form a fused ring.
(3)

Wherein Ar ₁ and Ar ₂ are independently selected from the group consisting of substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, substituted or unsubstituted (C 4 -C 30) Substituted or unsubstituted (C1-C30) alkylamino, substituted or unsubstituted B, N, O, S, P (O) A 5- to 7-membered heterocycloalkyl containing one or more selected hetero-cycloalkyl, a 5- to 7-membered heterocycloalkyl having one or more fused or unsubstituted aromatic rings, a substituted or unsubstituted (C3-C30) cycloalkyl a, fused substituted or unsubstituted aromatic ring by one or more (C6-C30) cycloalkyl, wherein, Ar ₁ and Ar ₂ are with or without a fused ring (C3-C30) alkylene or (C3-C30) An alicyclic ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
when e is 1, Ar ₃ is substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C4-C30) heteroaryl or a substituent selected from the following structures;

When e is 2, Ar ₃ is a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (C4-C30) heteroarylene or a substituent selected from the following structures;

Ar ₄ and Ar ₅ are independently of each other a substituted or unsubstituted (C6-C30) arylene or a substituted or unsubstituted (C4-C30) heteroarylene;
R ₁₁₁ to R ₁₁₃ are independently of each other hydrogen, deuterium, substituted or unsubstituted (C 1 -C 30) alkyl or substituted or unsubstituted (C 6 -C 30) aryl;
f is an integer of 1 to 4, and g is an integer of 0 or 1.]
[Chemical Formula 4]
M ¹ L ¹⁰¹ L ¹⁰² L ¹⁰³
Wherein M ¹ is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16, and the ligands L ¹⁰¹ , L ¹⁰² and L ¹⁰³ Are independently selected from the following structures.

Wherein R ₁₃₁ to R ₁₃₃ independently represent hydrogen, (C 1 -C 30) alkyl in which halogen is substituted or unsubstituted, (C 6 -C 30) aryl in which (C 1 -C 30) alkyl is unsubstituted or substituted, or Halogen;
R ₁₃₄ to R ₁₄₉ independently represent hydrogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 1 -C 30) alkoxy, substituted or unsubstituted (C 3 -C 30) Substituted or unsubstituted (C6-C30) arylamino, substituted or unsubstituted (C6-C30) arylamino, substituted or unsubstituted _5, a substituted or unsubstituted tree (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted tree (C6-C30) arylsilyl, Cyano or halogen;
R ₁₅₀ to R ₁₅₃ are each independently hydrogen, (C 1 -C 30) alkyl in which the halogen is substituted or unsubstituted, or (C 6 -C 30) aryl in which the (C 1 -C 30) alkyl is unsubstituted or substituted;
R ₁₅₄ and R ₁₅₅ independently of one another are hydrogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl or halogen, or R ₁₅₄ and R ₁₅₅ comprise or consist of a fused ring (C3-C12) alkylene or (C3-C12) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
R ₁₅₆ 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 ₁₅₇ to R ₁₅₉ are independently of each other hydrogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl or halogen;
Q is

,

or

And, R ₁₆₁ to R ₁₇₂ are independently H, halogen-substituted or unsubstituted (C1-C30) alkyl, (C1-C30) alkoxy, halogen, substituted or unsubstituted (C6-C30) aryl, cyano each other , or substituted or unsubstituted cycloalkyl, unsubstituted (C5-C30), connected to R ₁₃₇ or R ₁₃₈ and alkylene or alkenylene to form a fused ring, saturated or unsaturated.]
[Chemical Formula 5]
(Ar ₁₁ ) _h -L ₁₁ - (Ar ₁₂ ) _i
[Chemical Formula 6]
_{(Ar 13) j -L 12 -} (Ar 14) k
[In the formulas (5) and (6)
L ₁₁ is substituted or unsubstituted (C6-C30) arylene or substituted or unsubstituted (C4-C30) heteroarylene;
L ₁₂ is substituted or unsubstituted anthracenylene;
Ar ₁₁ to Ar ₁₄ independently represent hydrogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 1 -C 30) alkoxy, halogen, substituted or unsubstituted (C 4 -C 30) Substituted or unsubstituted (C5-C30) cycloalkyl or substituted or unsubstituted (C6-C30) aryl; And
h, i, j and k are each independently an integer of 0 to 4.] 5. The method of claim 4,
Wherein the organic material layer comprises at least one compound selected from the group consisting of an arylamine-based compound and a styrylarylamine-based compound. 5. The method of claim 4,
Wherein the organic material layer further comprises at least one metal or complex compound selected from the group consisting of Group 1, Group 2, Group 4, Periodic transition metal, Lanthanide series metal and d-transition element organic metal. 5. The method of claim 4,
Wherein the organic layer comprises a light emitting layer and a charge generating layer. 5. The method of claim 4,
Wherein the organic material layer further comprises one or more organic luminescent layers emitting red, green or blue light to emit white light.