KR20120021215A - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Abstract

PURPOSE: An organic electroluminescent compound is provided to have excellent red-light luminous efficiency and life time properties. CONSTITUTION: An organic electroluminescent compound is in chemical formula 1. In chemical formula 1, L is single bond, substituted or non-substituted (C1-30) alkylene, substituted or non-substituted (C6-30) arylene, substituted or non-substituted heteroarylene, substituted or non-substituted 5-7 membered heterocycloalkylene of substituted or non-substituted (C3-30) cycloalkylene, or substituted or non-substituted (C6-C30) arylene - (C1-C30) alkylene. An organic electroluminescent device comprises a first electrode, a second electrode, and one or more layers of organic material inserted between the first electrode and the second electrode. The organic material layer comprises one or more of the organic electroluminescent compounds, and one or more of photo-dopant.

Description

Novel organic electroluminescent 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 comprising 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 first developed [Appl. Phys. Lett. 51, 913, 1987].

The organic EL element injects charge into an 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

Accordingly, an object of the present invention is to firstly provide a compound for organic electronic material having a good skeleton having an excellent luminous efficiency and device life, and having an appropriate color coordinate in order to solve the above problems, and secondly, the organic electron. It is to provide a high efficiency and long life organic electroluminescent element employing a compound for a material as a light emitting material.

The present invention relates to a compound for an organic electronic material represented by the following formula (1) and an organic electroluminescent device comprising the same, the compound for an organic electronic material according to the present invention has better luminous efficiency and excellent life characteristics of the material than the conventional material The driving life of the device is very excellent and there is an advantage of manufacturing an OLED device with improved power consumption by inducing an increase in power efficiency.

[Formula 1]

[In Formula 1,

X ₁ To X ₃ is independently of each other Or N;

L is a single bond, substituted or unsubstituted (C1-C30) alkylene, substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (C2-C30) heteroarylene, substituted or unsubstituted 5- to 7-membered heterocycloalkylene, substituted or unsubstituted (C3-C30) cycloalkylene, or substituted or unsubstituted (C6-C30) arylene- (C1-C30) alkylene;

Ar ₁ To Ar ₅ independently from each other hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C2-C30) heteroaryl, Substituted or unsubstituted 5- to 7-membered heterocycloalkyl, (C3-C30) cycloalkyl fused with one or more substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted aromatic ring fused with one or more A substituted or unsubstituted (C2-C30) heteroaryl, a substituted or unsubstituted aromatic ring, a 5- to 7-membered heterocycloalkyl, fused with one or more fused or without or containing a fused ring with adjacent substituents (C3- C30) alkylene or (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;

Y is a single bond, -C (R ₁ ) (R ₂ )-, -N (R ₃ )-, -O- or -S-;

R ₁ R ₃ is independently of each other hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) cycloalkyl One or more fused substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C2-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted aromatic 5- to 7-membered heterocycloalkyl, at least one ring fused, substituted or unsubstituted (C3-C30) cycloalkyl, at least one fused (C3-C30) cycloalkyl, at least one fused ring Furnace, carbazolyl, nitro, -NR ₂₁ R ₂₂ , -BR ₂₃ R ₂₄ , -PR ₂₅ R ₂₆ , -P (= O) R ₂₇ R _28, R ₂₉ R ₃₀ R ₃₁ Si-, substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, R ₃₂ Z-, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, or fused with an adjacent substituent Contain or catch rings Unsubstituted or unsubstituted (C3-C30) alkylene or substituted or unsubstituted (C3-C30) alkenylene, linked to an alicyclic ring and a monocyclic or polycyclic aromatic ring, a monocyclic or polycyclic heteroaromatic ring Can form;

R ₂₁ to R ₂₈ are independently of each other substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) a, yl or substituted or unsubstituted (C2-C30) heteroaryl;

R ₂₉ to R ₃₁ are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (C2-C30) heteroaryl;

Z is S or O;

R ₃₂ is substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C2-C30) heteroaryl;

M and n are each independently an integer of 1 to 4, when m is an integer of 2 or more, each Ar ₁ may be the same or different from each other, and when n is an integer of 2 or more, each Ar ₂ may be the same or different from each other Can;

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

Substituents including the "alkyl", "alkoxy" and other "alkyl" moieties described herein include all linear or pulverized forms, and "cycloalkyl" is not only a monocyclic system but also substituted or unsubstituted adamantyl Or several ring-based hydrocarbons such as substituted or unsubstituted (C7-C30) bicycloalkyl. "Aryl" described in the present invention is an organic radical derived from an aromatic hydrocarbon by one hydrogen removal, and 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. The naphthyl includes 1-naphthyl and 2-naphthyl, anthryl includes 1-anthryl, 2-anthryl and 9-anthryl, and biphenyl is 2-biphenyl, 3-biphenyl , 4-biphenyl, terphenyl is p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m- Terphenyl-3-yl, m-terphenyl-2-yl, where fluorenyl is 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-flu Orenyl, phenanthryl includes 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, and pyrenyl is 1-pyrenyl, 2-pyrenyl, 4 -Pyrenyl, naphthacenyl includes all 1-naphthacenyl, 2-naphthacenyl, 9-naphthacenyl. The "heteroaryl" described in the present invention contains 1 to 4 heteroatoms selected from B, N, O, S, P (= O), Si, and P as aromatic ring skeleton atoms, and the remaining aromatic ring skeleton atoms are carbon. Meaning an aryl group which is 5 to 6 membered monocyclic heteroaryl, and polycyclic heteroaryl condensed with one or more benzene rings, which may be partially saturated. In addition, the heteroaryl in the present invention also includes a form in which one or more heteroaryls are linked by a single bond. Such heteroaryl groups include divalent aryl groups in which heteroatoms in the ring are oxidized or quaternized to form, for example, N-oxides or quaternary salts. Specific examples include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, 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, Cinolinyl, Quinazolinyl, Quinoxalinyl, Carbazolyl, Acridinyl, Phenantri Polycyclic heteroaryls such as dinyl, phenanthrolinyl, phenoxazinyl, phenazinyl, phenothiazinyl, benzodioxolyl, dibenzofuranyl, dibenzothiophenyl and their corresponding N-oxides (e.g., pyri) Dill N-oxide, quinolyl N-oxide), these Including the quaternary salts, but is not limited to this. The pyrrolyl comprises 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyridyl includes 2-pyridyl, 3-pyridyl, 4-pyridyl, and indolyl is 1-indolyl , 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, isoindoleyl includes 1-isoindoleyl, 2-isoindoleyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolinyl, 7-isoindolinyl, furyl includes 2-furyl, 3-furyl, benzofuranyl is 2 -Benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, isobenzofuranyl is 1-isobenzofuranyl, 3 Isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, and quinolyl is 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, wherein isoquinolyl includes 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, quinoxalinyl includes 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl Carbazolyl includes 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, and phenantridinyl is 1-phenanthridinyl, 2-phenanthridinyl, 3 Phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, and acridinyl is 1- Acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, phenanthrolinyl is 1,7-phenanthrolin-2-yl, 1,7 -Phenanthrolin-3-yl, 1,7-phenanthrolin-4-yl, 1,7-phenanthroline-5-yl,, 7-phenanthroline-6-yl, 1,7-phenanthrol Lin-8-yl, 1,7-phenanthroline-9-yl, 1,7-phenanthroline-10-yl, 1,8-phenanthroline-2-yl, 1,8-phenanthroline- 3-day, 1,8-phenanthroline-4-yl, 1,8-phenanthrole -5-day, 1,8-phenanthroline-6-day, 1,8-phenanthroline-7-day, 1,8-phenanthroline-9-day, 1,8-phenanthroline-10 -Day, 1,9-phenanthrolin-2-yl, 1,9-phenanthrolin-3-yl, 1,9-phenanthrolin-4-yl, 1,9-phenanthroline-5-yl , 1,9-phenanthroline-6-day, 1,9-phenanthroline-7-day, 1,9-phenanthroline-8-day, 1,9-phenanthroline-10-day, 1 , 10-phenanthrolin-2-yl, 1,10-phenanthrolin-3-yl, 1,10-phenanthrolin-4-yl, 1,10-phenanthroline-5-yl, 2,9 -Phenanthrolin-1-yl, 2,9-phenanthrolin-3-yl, 2,9-phenanthrolin-4-yl, 2,9-phenanthroline-5-yl, 2,9-phenan Troolin-6-yl, 2,9-phenanthroline-7-yl, 2,9-phenanthroline-8-yl, 2,9-phenanthroline-10-yl, 2,8-phenanthroline -1-yl, 2,8-phenanthroline-3-yl, 2,8-phenanthroline-4-yl, 2,8-phenanthroline-5-yl, 2,8-phenanthroline-6 -Day, 2,8-phenanthroline-7-day, 2,8-phenanthroline-9-day, 2,8-phenanthroline-10-day, 2,7-phenanthroline-1-yl , 2,7-phenanthrolin-3-yl, 2,7-phenanthrolin-4-yl, 2,7-phenanthroline-5-yl, 2,7-phenan Rolin-6-yl, 2,7-phenanthroline-8-yl, 2,7-phenanthroline-9-yl, 2,7-phenanthroline-10-yl, and phenazinyl is 1- Phenazinyl, 2-phenazinyl, phenothiazinyl includes 1-phenothiazinyl, 2-phenothiazinyl, 3-phenothiazinyl, 4-phenothiazinyl, 10-phenothiazinyl, phenoxa Genyls include 1-phenoxazinyl, 2-phenoxazinyl, 3-phenoxazinyl, 4-phenoxazinyl, 10-phenoxazinyl, and oxazolyl is 2-oxazolyl, 4-oxazolyl, 5- Oxazolyl, oxadiazoles include 2-oxadiazolyl, 5-oxadiazolyl, furazanyl includes 3-furazanyl, dibenzofuranyl is 1-dibenzofuranyl, 2-di Benzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, dibenzothiophenyl being 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dio Includes all benzothiophenyls.

Further, the '(C1-C30) alkyl' group described in the present invention is preferably (C1-C20) alkyl, more preferably (C1-C10) alkyl, and the '(C6-C30) aryl' group is preferred. Preferably (C6-C20) aryl. The '(C2-C30) heteroaryl' group is preferably (C2-C20) heteroaryl. The '(C3-C30) cycloalkyl' group is preferably (C3-C20) cycloalkyl, more preferably (C3-C7) cycloalkyl. The '(C2-C30) alkenyl or alkynyl' group is preferably (C2-C20) alkenyl or alkynyl, more preferably (C2-C10) alkenyl or alkynyl.

In addition, in the description of "substituted or unsubstituted" described in the present invention, "substituted" means a case where is further substituted with an unsubstituted substituent, the L, Ar ₁ to Ar ₅ , Substituents further substituted with R ₁ to R ₃ , R ₂₁ to R ₂₈ , R ₂₉ to R ₃₁ and R ₃₂ independently of one another are deuterium, halogen, (C1-C30) alkyl substituted or unsubstituted, (C6- C30) aryl, (C6-C30) aryl substituted or unsubstituted (C2-C30) heteroaryl, 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused at least one aromatic ring , (C3-C30) cycloalkyl, (C3-C30) cycloalkyl fused with one or more aromatic rings, R ^a R ^b R ^c Si-, (C2-C30) alkenyl, (C2-C30) alkynyl, cya Furnace, carbazolyl, -NR ^d R ^e , -BR ^f R ^g , -PR ^h R ⁱ , -P (= 0) R ^j R ^k , (C6-C30) ar (C1-C30) alkyl, (C1- C 30) alkyl (C 6 -C 30) aryl, R ¹ S—, R ¹ O—, R ^m C (═O) —, R ^m C (═O) O—, carboxyl, nitro or hydroxy At least one selected, and R ^a to R ^l are independently of each other (C1-C30) alkyl, (C6-C30) aryl or (C2-C30) heteroaryl; R ^m means (C1-C30) alkyl, (C1-C30) alkoxy, (C6-C30) aryl or (C6-C30) aryloxy.

The compound for an organic electronic material of the present invention includes a compound represented by the following Chemical Formulas 2 to 8.

[Formula 2]

(3)

[Formula 4]

[Chemical Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Ar ₁ above To Ar ₅ , Y, L, m and n are the same as defined in Formula 1 above.]

More specifically, L is (C6-C30) arylene or (C2-C30) heteroarylene; Ar ₁ To Ar ₅ are independently of each other hydrogen, deuterium, halogen, (C1-C30) alkyl, (C6-C30) aryl or (C2-C30) heteroaryl or (C3-C30) with or without fused ring with adjacent substituents Can be linked to alkylene or (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring; Y is —C (R ₁ ) (R ₂ ) —, —N (R ₃ ) —, —O— or —S—; R ₁ To R ₃ are each independently halogen, (C 1 -C 30) alkyl, (C 6 -C 30) aryl, (C 2 -C 30) heteroaryl, (C 3 -C 30) cycloalkyl or (C 6 -C 30) ar (C 1 -C 30) Alkyl; Arylene or heteroarylene of L, Ar ₁ To Ar ₅ of the alkyl, aryl or heteroaryl, R ₁ Alkyl, aryl, heteroaryl, cycloalkyl or aralkyl of R ₃ to (C 1 -C 30) alkyl, (C 6 -C 30) aryl, (C 6 -C 30) aryl, substituted or unsubstituted by deuterium, halogen, halogen, respectively. Substituted or unsubstituted (C2-C30) heteroaryl, 5- to 7-membered heterocycloalkyl, (C3-C30) cycloalkyl, (C6-C30) ar (C1-C30) alkyl and (C1-C30) alkyl It may be further substituted with one or more selected from the group consisting of (C6-C30) aryl.

The compound for an organic electronic material according to the present invention may be more specifically exemplified as the following compound, but the following compound is not intended to limit the present invention.

The compound for an organic electronic material according to the present invention may be prepared, for example, as shown in Scheme 1 below, but is not limited thereto.

Scheme 1

[Ar ₁ in Scheme _1] To Ar ₅ , X ₁ To X ₃ , Y, L, m and n are the same as defined in Formula 1 above.]

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 organic light emitting compound of Formula 1. In addition, the organic material layer may include one or more phosphorescent dopants in addition to the compound for an organic electronic material of Chemical Formula 1.

In the organic electroluminescent device of the present invention, it may include at least one compound selected from the group consisting of an arylamine compound or a styrylarylamine compound, including a compound for the organic electronic material of Formula 1, at the same time, arylamine Specific examples of the compound or styrylarylamine compound are exemplified in identification numbers <212> to <224> of Patent Application No. 10-2008-0060393, but are not limited thereto.

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 metal, lanthanum series metal and organic metal of d-transition element It may further include one or more metals or complex compounds selected from the group consisting of, the organic material layer may include a light emitting layer and a charge generating layer.

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

In addition, an organic light emitting device that emits white light may be formed by simultaneously including one or more organic light emitting layers including blue, red, or green light emitting compounds in addition to the organic electroluminescent compound. The compound emitting blue, green, or red light is exemplified in Application Nos. 10-2008-0123276, 10-2008-0107606, or 10-2008-0118428, but is not limited thereto.

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

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

The organic electroluminescent device using the compound for an organic electronic material according to the present invention has an advantage in that the OLED device can be manufactured with excellent luminous efficiency and excellent material life characteristics and excellent driving life of the device.

Hereinafter, for the detailed understanding of the present invention, a compound for an organic electronic material according to the present invention, a method for preparing the same, and a light emitting property of the device will be described with reference to a representative compound of the present invention, but only for the purpose of illustrating the embodiments thereof. It does not limit the scope of the present invention.

Preparation Example 1 Preparation of Compound 6

compound  A-1 Manufacture

15 g (63.58 mmol) of 1,3-dibromobenzene was dissolved in 300 mL of THF, and 26.7 mL (2.5 M in hexane, 66.76 mmol) of n-buLi were slowly added at -78 ° C. After one hour, 20.6 mL of chlorotriphenylsilane was dissolved in 70 mL of THF, and then added to the reaction solution. After stirring at room temperature for 12 hours, the white solid produced was filtered off and the filtrate was extracted with EA and washed with distilled water. The obtained organic layer was dried over magnesium sulfate, distilled under reduced pressure, and recrystallized with EA and methanol to obtain 17.5 g (42.12 mmol, 66.25%) of Compound A-1 .

compound A-2 Manufacture

20 g (48.14 mmol) of Compound A-1 was dissolved in 500 mL of THF, and 23.1 mL (2.5 M in Hexane, 57.5 mmol) of n-buLi was slowly added at -78 ° C. After one hour, 8.5 mL (77.03 mmol) of trimethylborate was added to the reaction solution. After stirring for 12 hours at room temperature, extracted with EA and washed with distilled water. The resulting organic layer was dried over magnesium sulfate, distilled under reduced pressure, and recrystallized with EA and Hexane to obtain Compound A-2 14g (36.81 mmol, 76.46%).

compound A-3 Manufacture

2.1 g (13.86 mmol) of 2,4-dichloropyrimidine, 5.8 g (15.25 mmol) of Compound A-2 , 0.814 g (0.70 mmol) of Pd (PPh ₃ ) ₄ , 80 mL of toluene, 40 mL of 2M Na ₂ CO ₃ and ethanol 20 mL was added and stirred at reflux. After 12 hours, the mixture was cooled to room temperature, extracted with EA, and washed with distilled water. The obtained organic layer was dried over magnesium sulfate, distilled under reduced pressure, and column separated to obtain 5.9 g (13.13 mmol, 94.80%) of compound A-3 .

compound  6 Manufacture

Compound A-3 5.9 g (13.13 mmol), 9,9-dimethyl-9,10-dihydroacridine 3.0 g (14.45 mmol), Pd ₂ (dba) ₃ 0.6 g (0.65 mmol), Dave-phos 0.517 g (1.31 mmol), NaOt-bu 3.7 g (39.41 mmol), and toluene 130 mL were mixed and stirred under reflux. After 12 hours, the mixture was cooled to room temperature, extracted with EA, and washed with distilled water. The obtained organic layer was dried over magnesium sulfate, distilled under reduced pressure, and then column separated to obtain compound 6 2.9 g (4.66 mmol, 35.51%).

MS / FAB found 621, calculated 621.26

Preparation Example 2 Preparation of Compound 4

Synthesis proceeded in a procedure similar to Preparation Example 1. 2,4-dichlorotriazine was substituted for 2,4-dichloropyrimidine in the preparation step of Compound A-3 of Preparation Example 1, and 9,9-dimethyl-9,10-di was used in the preparation step of Compound 6 Compound 4 was obtained in the same manner except that 9,9-diphenyl-9,10-dihydroacridine was used instead of hydroacridine.

MS / FAB found 746.9, calculated 746.29

Preparation Example 3 Preparation of Compound 40

Synthesis proceeded in a procedure similar to Preparation Example 1. 2,4-dichlorotriazine was substituted for 2,4-dichloropyrimidine in the preparation step of Compound A-3 of Preparation Example 1, and 9,9-dimethyl-9,10-di was used in the preparation step of Compound 6 Compound 40 was obtained in the same manner except using phenothiazine instead of hydroacridine.

MS / FAB found 612.8, calculated 612.18

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 apparatus, and 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenylamine ( 2-TNATA), evacuated until the vacuum in the chamber reached 10 ^-6 torr, and applied a current to the cell to evaporate 2-TNATA to deposit a 60 nm thick hole injection layer on the ITO substrate. Subsequently, N , N' -bis (α-naphthyl) -N , N' -diphenyl-4,4'-diamine (NPB) was added to another cell in the vacuum deposition apparatus, and NPB was applied by applying a current to the cell. A 20 nm-thick hole transport layer was deposited on the hole injection layer by evaporation, and after the hole injection layer and the hole transport layer were formed, the light emitting layer was deposited thereon as follows: As a host in one cell in the vacuum deposition apparatus. into the compound 4 according to the present invention, and then in the other cell as a dopant into the _{Ir (ppy) 3 [tris (} 2-phenylpyridine) iridium] , respectively, two water Was evaporated at different rates and doped at 4% by weight to deposit a 30 nm thick light emitting layer on the hole transport layer, followed by tris (8-hydroxyquinoline) aluminum (III) (Alq) as an electron transport layer on the light emitting layer. After deposition to a thickness of 20 nm, the lithium quinolate (Liq) was deposited to a thickness of 2 nm with an electron injection layer, and the Al cathode was deposited to a thickness of 150 nm using another vacuum deposition equipment to manufacture an OLED device.

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

As a result, a current of 4.0 mA / cm ² flowed at a voltage of 6.8 V, and green light emission of 1128 cd / m ² was confirmed.

[Example 2]

An OLED device was manufactured in the same manner as in Example 1, except that Compound 6 was used as the host material in the light emitting layer.

As a result, a current of 4.1 mA / cm ² flowed at a voltage of 6.3 V, and green light emission of 1168 cd / m ² was confirmed.

Example 3

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 4.3 mA / cm ² flowed at a voltage of 6.5 V, and green light emission of 1242 cd / m ² was confirmed.

Comparative Example 1

4,4'-bis (carbazol-9-yl) biphenyl (CBP) is used as the host material in the light emitting layer instead of the compound of the present invention, and bis (2-methyl-8-quinolinate) is used as the hole blocking layer. An OLED device was manufactured in the same manner as in Example 1, except that (p-phenylphenolrato) aluminum (III) (Balq) was used.

As a result, a current of 3.9 mA / cm ² flowed at a voltage of 7.5 V, and green light emission of 1000 cd / m ² was confirmed.

It was confirmed that the 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 excellent in the light emission characteristics, it was possible to improve the power consumption by inducing power efficiency increase by lowering the driving voltage 0.7 ~ 1.2V.

Claims (10)

The compound for organic electronic materials represented by following formula (1).
[Formula 1]

[In the above formula (1)
X ₁ to X ₃ is independently of each other Or N;
L is a single bond, substituted or unsubstituted (C1-C30) alkylene, substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (C2-C30) heteroarylene, substituted or unsubstituted 5- to 7-membered heterocycloalkylene, substituted or unsubstituted (C3-C30) cycloalkylene, or substituted or unsubstituted (C6-C30) arylene- (C1-C30) alkylene;
Ar ₁ to Ar ₅ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C2-C30) hetero One or more substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted aromatic rings in which one or more aryl, substituted or unsubstituted 5 to 7 membered heterocycloalkyl, or (C3-C30) cycloalkyl is fused Or a fused substituted or unsubstituted (C2-C30) heteroaryl, a substituted or unsubstituted aromatic ring, a 5-7 membered heterocycloalkyl, fused with one or more fused rings, or without a fused ring with adjacent substituents ( C3-C30) alkylene or (C3-C30) alkenylene may be linked to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
Y is a single bond, -C (R ₁ ) (R ₂ )-, -N (R ₃ )-, -O- or -S-;
R ₁ to R ₃ are independently of each other hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) cyclo Substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C2-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted, with one or more alkyl fused To 7-membered heterocycloalkyl fused with one or more aromatic rings, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted aromatic rings with one or more fused (C3-C30) cycloalkyl , Cyano, carbazolyl, nitro, -NR ₂₁ R ₂₂ , -BR ₂₃ R ₂₄ , -PR ₂₅ R ₂₆ , -P (= O) R ₂₇ R _28, R ₂₉ R ₃₀ R ₃₁ Si-, substituted or Unsubstituted (C6-C30) ar (C1-C30) alkyl, R ₃₂ Z-, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, or adjacent substituents With fused rings Unsubstituted substituted or unsubstituted (C3-C30) alkylene or substituted or unsubstituted (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, monocyclic or polycyclic heteroaromatic May form a ring;
R ₂₁ to R ₂₈ are independently of each other substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) a, yl or substituted or unsubstituted (C2-C30) heteroaryl;
R ₂₉ to R ₃₁ are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (C2-C30) heteroaryl;
Z is S or O;
R ₃₂ is substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C2-C30) heteroaryl;
M and n are each independently an integer of 1 to 4;
Wherein said heterocycloalkyl, heteroaryl and heteroarylene comprise one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P.] The method of claim 1,
L, Ar ₁ To Ar ₅ , R ₁ Substituents further substituted with R ₃ , R ₂₁ to R ₂₈ , R ₂₉ to R ₃₁ and R ₃₂ independently of each other are deuterium, halogen, (C1-C30) alkyl unsubstituted or substituted with halogen, (C6-C30) Aryl, (C6-C30) aryl substituted or unsubstituted (C2-C30) heteroaryl, 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic rings, ( C3-C30) cycloalkyl, (C3-C30) cycloalkyl fused with one or more aromatic rings, R ^a R ^b R ^c Si-, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, Carbazolyl, -NR ^d R ^e , -BR ^f R ^g , -PR ^h R ⁱ , -P (= 0) R ^j R ^k , (C6-C30) ar (C1-C30) alkyl, (C1-C30) Selected from the group consisting of alkyl (C6-C30) aryl, R ^l S-, R ^l O-, R ^m C (= 0)-, R ^m C (= 0) O-, carboxyl, nitro or hydroxy At least one, and R ^a to R ^l are independently of each other (C1-C30) alkyl, (C6-C30) aryl or (C2-C30) heteroaryl; R ^m is (C1-C30) alkyl, (C1-C30) alkoxy, (C6-C30) aryl or (C6-C30) aryloxy, the compound for organic electronic materials. The method of claim 1,
The compound for organic electronic materials represented by following formula (2)-(8).
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Formula 6]

[Formula 7]

[Chemical Formula 8]

[Ar ₁ to Ar ₅ , Y, L, m and n are the same as defined in claim 1.] The method of claim 1,
A compound for organic electronic materials, characterized in that it is selected from the following compounds.

An organic electroluminescent device comprising the compound for organic electronic material according to any one of claims 1 to 4. 6. The method of claim 5,
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 compound for an organic electronic material and at least one phosphorescent dopant. The method of claim 6,
An organic electroluminescent device further comprising at least one amine compound selected from the group consisting of an arylamine compound or a styrylarylamine compound in the organic layer. The method of claim 6,
An organic electric field further comprising at least one metal or a complex compound selected from the group consisting of Group 1, Group 2, 4, 5 cycle transition metals, lanthanum series metals and organic metals of d-transition elements in the organic layer. Light emitting element. The method of claim 6,
The organic material layer is an organic electroluminescent device comprising a light emitting layer and a charge generating layer. The method of claim 6,
An organic electroluminescent device which emits white light by further comprising at least one organic light emitting layer emitting blue, red or green light in the organic material layer.