KR20150073233A - An Organic Electroluminescent Compound and an Organic Electroluminescent Device Comprising the Same - Google Patents

Abstract

The present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device comprising the same. The organic electroluminescent device having excellent current/power efficiency and lifespan can be manufactured by using the organic electroluminescent compounds. The organic electroluminescent compounds are represented by chemical formula 1.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescent compound and an organic electroluminescent compound containing the same,

The present invention relates to an organic electroluminescent compound and an organic electroluminescent device including the same.

Among display devices, an electroluminescent device (EL device) is a self-luminous display device having a wide viewing angle, an excellent contrast, and a high response speed. In 1987, Eastman Kodak Company developed an organic EL device using an aromatic diamine and an aluminum complex having low molecular weight as a light emitting layer forming material [Appl. Phys. Lett. 51, 913, 1987].

The most important factor determining the luminous efficiency in an organic electroluminescent device is a light emitting material. Fluorescent materials have been widely used as luminescent materials to date, but the development of phosphorescent materials has been widely studied in that phosphorescent materials can improve luminous efficiency up to 4 times the theoretical efficiency of phosphorescent materials in terms of the mechanism of electroluminescence . Until now, an iridium (III) complex series has been widely known as a phosphorescent material. Each RGB has bis (2- (2'-benzothienyl) -pyridinate-N, C-3 ') iridium (acetylacetonate ) [(acac) Ir (btp ) 2], tris (2-phenylpyridine) iridium [Ir (ppy) _3] and bis (4,6-difluorophenyl pyridinyl Nei Sat -N, C2) avoid collision Ney And materials such as tolidium (Firpic) are known.

In the prior art, 4,4'-N, N'-dicarbazole-biphenyl (CBP) is the most widely known phosphorescent host material. In recent years, Pioneer et al. Of Japan have been using bathocuproine (BCP) and aluminum (III) bis (2-methyl-8-quinolinate) (4-phenyl phenolate) Balq) as a host material and developed a high-performance organic electroluminescent device.

However, existing materials have advantages in terms of luminescence properties, but they have the following disadvantages: (1) They have a low glass transition temperature and a low thermal stability, which deteriorate during a high-temperature deposition process under vacuum, and the lifetime of the device deteriorates. (2) In the organic electroluminescent device, the power efficiency is in the relation of [(? / Voltage) x current efficiency], so that the power efficiency is inversely proportional to the voltage. In the organic electroluminescent device using the phosphorescent host material, The current efficiency (cd / A) is higher than that of the light emitting device, but the driving voltage is also very high, so there is no great advantage in terms of power efficiency (lm / w). (3) In addition, when used in an organic electroluminescent device, it is unsatisfactory in terms of operating life, and luminous efficiency is still required to be improved.

On the other hand, the organic electroluminescent device has a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer in order to improve its efficiency and stability. At this time, the selection of a compound contained in the hole transport layer or the like is recognized as a means for improving device characteristics such as hole transport efficiency, luminescence efficiency, and lifetime of the light emitting layer.

(NPB), N, N (1-naphthyl) -NPhenylamino] biphenyl (NPB) as a hole injection and transport material in organic electroluminescent devices, (TPD), 4,4 ', 4 "-tris (3-methylphenyl) -4,4'-diamine Phenylamino) triphenylamine (MTDATA). However, when such a material is used, there is a problem that the quantum efficiency and lifetime of the organic electroluminescent device are lowered. This is because when the organic electroluminescent device is driven at a high current , Thermal stress is generated between the anode and the hole injection layer, and the lifetime of the device is rapidly lowered due to the thermal stress. The organic material used for the hole injection layer has a very high mobility Therefore, the hole-electron charge balance of holes and electrons is broken and the quantum efficiency (cd / A) is low It becomes.

Therefore, development of a hole transport layer for improving the durability of an organic electroluminescent device is still required.

United States Patent Application Publication No. US2013 / 0126792 A1 discloses a compound in which an indole-benzothiophene is fused as a compound for an organic electroluminescence device. However, the above document discloses that the structure in which indole and benzothiophene are fused is directly or by a linker, and a compound in which a benzene ring is fused with a pyrazine, pyridazine, pyrimidine or triazine ring, But does not specifically disclose the above.

U.S. Patent Application Publication No. US2013 / 0126792 A1 (issued on February 23, 2013)

It is an object of the present invention to provide an organic electroluminescent compound excellent in current / power efficiency and lifetime.

As a result of intensive studies to solve the above technical problems, the present inventors have found that an organic electroluminescent compound represented by the following general formula (1) achieves the above-mentioned object and completed the present invention.

[Chemical Formula 1]

In Formula 1,

X ₁ to X ₃ each represent -CR- or -N-, at least two of X ₁ to X ₃ represent -N-;

L ₁ is a single bond, substituted or unsubstituted (C 6 -C 30) arylene, or substituted or unsubstituted (5-30 membered) heteroarylene;

R and R ₁ to R ₃ are each independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) Substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) _{, -N (R 11) (R} 12), -Si (R 13) (R 14) (R 15), -S (R 16), -O (R 17), cyano, nitro, or hydroxy, or ; (C3-C30) monocyclic or polycyclic alicyclic or aromatic ring linked to an adjacent substituent, and the carbon atom of the alicyclic or aromatic ring formed may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur ≪ / RTI >

R ₁₁ To R ₁₇ are each independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, substituted or unsubstituted (5-30 membered) , Substituted or unsubstituted (3-7 membered) heterocycloalkyl, or substituted or unsubstituted (C3-C30) cycloalkyl; (C3-C30) monocyclic or polycyclic alicyclic or aromatic ring linked to an adjacent substituent, and the carbon atom of the alicyclic or aromatic ring formed may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur ≪ / RTI >

a to c are each independently an integer of 1 to 4; When a, b, or c is an integer of 2 or more, each R ₁ , each R ₂ , and each R ₃ may be the same or different;

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

The organic electroluminescent compound according to the present invention is advantageous in manufacturing an organic electroluminescent device having excellent current / power efficiency and lifetime.

The present invention will now be described in more detail, but this should not be construed as limiting the scope of the present invention.

The present invention relates to an organic electroluminescent compound represented by Formula 1, an organic electroluminescent material including the organic electroluminescent compound, and an organic electroluminescent device including the same.

The organic electroluminescent compound represented by Formula 1 will be described in more detail as follows.

The term "(C 1 -C 30) alkyl" as used in the present invention means straight-chain or branched alkyl having 1 to 30 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms . Specific examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl. As used herein, "(C2-C30) alkenyl" means straight or branched chain alkenyl having 2 to 30 carbon atoms, preferably 2 to 20 carbon atoms, more preferably 2 to 10 carbon atoms. Specific examples of the alkenyl include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl and the like. As used herein, the term "(C2-C30) alkynyl" means straight chain or branched chain alkynyl having 2 to 30 carbon atoms, preferably 2 to 20 carbon atoms, more preferably 2 to 10 carbon atoms. Examples of the alkynyl include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl and 1-methylpent-2-onyl. The term "(C3-C30) cycloalkyl" as used herein means a monocyclic or polycyclic hydrocarbon having 3 to 30 carbon atoms, preferably 3 to 20 carbon atoms, more preferably 3 to 7 carbon atoms. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like. The term " (3-7 member) heterocycloalkyl "as used herein refers to a heterocycloalkyl group having 3 to 7 ring skeletal atoms and at least one heteroatom selected from the group consisting of B, N, O, S, P (= O) Preferably one or more heteroatoms selected from O, S and N, and includes, for example, tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran and the like. The term "(C6-C30) aryl (phenylene)" as used herein refers to a single ring or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 carbon atoms, wherein the number of carbon atoms in the ring is 6 to 20, 15 < / RTI > Examples of the aryl include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenan Naphthacenyl, fluoranthenyl, and the like can be given as examples of the aryl group, the arylthio group, the arylthio group, the arylthio group, and the arylthio group. As used herein, the term "(5-30) heteroaryl (phenylene)" refers to a heteroaryl group having 5 to 30 ring skeletal atoms and one or more heteroatoms selected from the group consisting of B, N, O, S, P Quot; means an aryl group containing an atom. The number of heteroatoms is preferably 1 to 4, and may be a monocyclic ring system or a fused ring system condensed with at least one benzene ring, and may be partially saturated. In addition, the heteroaryl (phenylene) also includes a heteroaryl group in which at least one heteroaryl or aryl group is linked to a heteroaryl group by a single bond. Examples of such heteroaryls include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl , Monocyclic heteroaryl such as triazolyl, tetrazolyl, furanzyl, pyridyl, pyrazinyl, pyrimidinyl and pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, di Benzoimidazolyl, benzothiazolyl, benzothiazolyl, benzoisothiazolyl, benzooxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, Fused heterocyclic heteroaryl such as norbornyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxaphyl, phenanthridinyl, benzodioxolyl and the like. As used herein, "halogen" includes F, Cl, Br, and I atoms.

Further, in the phrase "substituted or unsubstituted" described in the present invention, "substituted" means that a hydrogen atom is replaced with another atom or another functional group (ie, a substituent) in a certain functional group. The ₁ L, R, R ₁ to R ₃ and a R-substituted (C1-C30) alkyl, substituted (C3-C30) from ₁₁ to R ₁₇ of said formula (1) cycloalkyl, substituted (3-7 membered) heterocycloalkyl, Substituents for substituted (C6-C30) aryl (R), substituted (5-30 membered heteroaryl), substituted (C6- (C1-C30) alkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C6-C30) alkylthio, (C3-C30) cycloalkyl, (C3-C30) cycloalkenyl, (3-7 membered) heterocycloalkyl, (C6-C30) aryl substituted with (5-30) heteroaryl, (C6-C30) arylsilyl, C6-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1- Amino, mono- or di- (C6-C30) (C6-C30) aryloxycarbonyl, (C6-C30) arylcarbonyl, di (C6-C30) arylamino, (C1- (C1-C30) alkylcarbonyl, (C1-C30) alkylcarbonyl, di (C1-C30) alkylboronyl, Alkyl (C6-C30) aryl, and is independently at least one member selected from the group consisting of (C1-C6) alkyl and (C6-C15) aryl.

In the general formula (1), X ₁ to X ₃ each represent -CR- or -N-, and at least two of X ₁ to X ₃ represent -N-.

Wherein L ₁ is a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5-30 membered heteroarylene), preferably a single bond, a substituted or unsubstituted (C6-C15) arylene, or substituted or unsubstituted (5-15 membered heteroarylene), more preferably a single bond, (C6-C15) arylene substituted or unsubstituted with (C1- Or unsubstituted (5-15 membered) heteroarylene.

Wherein R and R ₁ to R ₃ are each independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) Substituted or unsubstituted (C6-C30) aryl (C1-C30) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, _{alkyl, -N (R 11) (R} 12), -Si (R 13) (R 14) (R 15), -S (R 16), -O (R 17), cyano, nitro, or hydroxy ; (C3-C30) monocyclic or polycyclic alicyclic or aromatic ring linked to an adjacent substituent, and the carbon atom of the alicyclic or aromatic ring formed may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur (C6-C20) aryl, or substituted or unsubstituted (5-20 membered) heteroaryl, each optionally substituted with one or more substituents selected from the group consisting of hydrogen, substituted or unsubstituted (C1-C6) alkyl, substituted or unsubstituted ; (C3-C15) monocyclic or polycyclic alicyclic or aromatic ring linked to adjacent substituents, more preferably each independently hydrogen; Unsubstituted (CrC6) alkyl; (C6-C20) aryl unsubstituted or substituted by (C1-C6) alkyl or (C6-C15) aryl; Or (5-20 membered) heteroaryl, which is unsubstituted or substituted by (C6-C15) aryl; May be connected to adjacent substituents to form a (C3-C15) monocyclic aromatic ring.

R ₁₁ to R ₁₇ each independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-30 W) Heteroaryl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, or substituted or unsubstituted (C3-C30) cycloalkyl; (C3-C30) monocyclic or polycyclic alicyclic or aromatic ring linked to an adjacent substituent, and the carbon atom of the alicyclic or aromatic ring formed may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur .

a to c are each independently an integer of 1 to 4, preferably each independently an integer of 1 to 3; When a, b, or c is an integer of 2 or more, each R ₁ , each R ₂ , and each R ₃ may be the same or different.

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

According to one aspect of the present invention, in the above formula (1), X ₁ to X ₃ each represent -CR- or -N-, at least two of X ₁ to X ₃ represent -N-; L ₁ is a single bond, substituted or unsubstituted (C6-C15) arylene, or substituted or unsubstituted (5-15 membered) heteroarylene; R and R ₁ to R ₃ are each independently hydrogen, substituted or unsubstituted (C 1 -C 6) alkyl, substituted or unsubstituted (C 6 -C 20) aryl, or substituted or unsubstituted Aryl; May be connected to adjacent substituents to form a (C3-C15) monocyclic or polycyclic alicyclic or aromatic ring; a to c are each independently an integer of 1 to 3; When a, b, or c is an integer of 2 or more, each R ₁ , each R ₂ , and each R ₃ may be the same or different.

According to another embodiment of the present invention, in Formula 1, X ₁ to X ₃ each represent -CR- or -N-, at least two of X ₁ to X ₃ represent -N-; L ₁ is a single bond, (C 6 -C 15) arylene substituted or unsubstituted with (C ₁ -C 6) alkyl, or unsubstituted (5-15 member) heteroarylene; R and R ₁ to R ₃ are each independently hydrogen; Unsubstituted (CrC6) alkyl; (C6-C20) aryl unsubstituted or substituted by (C1-C6) alkyl or (C6-C15) aryl; Or (5-20 membered) heteroaryl, which is unsubstituted or substituted by (C6-C15) aryl; May be connected to adjacent substituents to form a (C3-C15) monocyclic aromatic ring; a to c are each independently an integer of 1 to 3; When a, b, or c is an integer of 2 or more, each R ₁ , each R ₂ , and each R ₃ may be the same or different.

The organic electroluminescent compound of Formula 1 may be more specifically exemplified by the following compounds, but is not limited thereto.

The organic electroluminescent compound according to the present invention can be prepared by a synthesis method known to a person skilled in the art and can be prepared, for example, as shown in the following reaction formula.

[Reaction Scheme 1]

In the above Reaction Scheme 1, X ₁ to X ₃ , L ₁ , R ₁ to R ₃ , and a to c are the same as defined in Formula 1, and Hal is halogen.

The present invention also provides an organic electroluminescent material comprising an organic electroluminescent compound of Formula 1 and an organic electroluminescent device comprising the same.

The material may be made of the organic electroluminescent compound of the present invention alone, and may further include common materials included in the organic electroluminescent material.

An organic electroluminescent device according to the present invention includes a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, and the organic material layer may include at least one organic electroluminescent compound represented by Formula 1.

One of the first electrode and the second electrode may be an anode and the other may be a cathode. The organic material layer may further include one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer.

The organic electroluminescent compound of the present invention may be included in at least one of the light emitting layer and the hole transporting layer. When used in the hole transporting layer, the organic electroluminescent compound of the present invention can be included as a hole transporting material. When used in the light emitting layer, the organic electroluminescent compound of the present invention can be included as a host material.

The organic electroluminescent device comprising the organic electroluminescent compound of the present invention may further include at least one other compound other than the organic electroluminescent compound of the present invention as a host material, and may further include at least one dopant.

When the organic electroluminescent compound of the present invention is contained as the host material (first host material) of the light emitting layer, other compounds may be included as the second host material. Here, the weight ratio of the first host material to the second host material ranges from 1:99 to 99: 1.

The host material of the compound other than the organic electroluminescent compound of the present invention may be any phosphorescent host known in the art, but is preferably selected from the group consisting of compounds represented by the following general formulas (11) to (15) desirable.

(11)

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

In the above Formulas 11 to 15,

Cz has the following structure,

X is -O- or -S-;

R ₂₁ to R ₂₄ each independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, substituted or unsubstituted Heteroaryl or R ₂₅ R ₂₆ R ₂₇ Si-, R ₂₅ to R ₂₇ are each independently substituted or unsubstituted (C 1 -C 30) alkyl, or substituted or unsubstituted (C 6 -C 30) aryl; L ₄ is a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (5-30 membered) heteroarylene; M is a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5-30 membered) heteroaryl; Y ₁ and Y ₂ are -O-, -S-, -N (R ₃₁ ) -, -C (R ₃₂ ) (R ₃₃ ) -, and Y ₁ and Y ₂ are not simultaneously present; R ₃₁ to R ₃₃ each independently represent a substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-30 W) heteroaryl ring, R ₃₂ And R ₃₃ may be the same or different; each of h and i is independently an integer of 1 to 3, j, k, p and q are each independently an integer of 0 to 4, and when h, i, j, k, p or q is an integer of 2 or more, (Cz-L ₄ ), each (Cz), each R ₂₁ , each R ₂₂ , each R _23, or each R ₂₄ may be the same or different.

Specifically, preferred examples of the host material are as follows.

[Wherein TPS is triphenylsilyl]

The dopant included in the organic electroluminescent device of the present invention is preferably at least one phosphorescent dopant. The phosphorescent dopant material to be applied to the organic electroluminescent device of the present invention is not particularly limited, but a complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt) And more preferably an ortho-metallated complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and still more preferably an orthometallated iridium complex compound.

The phosphorescent dopant is preferably selected from the group consisting of compounds represented by the following Chemical Formulas (101) to (103).

(101)

≪ EMI ID =

≪ EMI ID =

In Formulas 101 to 103, L is selected from the following structures;

R ₁₀₀ is hydrogen or substituted or unsubstituted (C 1 -C 30) alkyl; R ₁₀₁ to R ₁₀₉ and R ₁₁₁ to R ₁₂₃ are each independently selected from the group consisting of hydrogen, deuterium, halogen, (C 1 -C 30) alkyl, cyano, substituted or unsubstituted (C 1 -C 30) alkoxy, Or substituted or unsubstituted (C3-C30) cycloalkyl; R ₁₂₀ to R ₁₂₃ may be connected to adjacent substituents to form a (3-30 membered) monocyclic or polycyclic alicyclic or aromatic ring (e.g., quinoline); R ₁₂₄ to R ₁₂₇ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, or substituted or unsubstituted (C 6 -C 30) aryl; When R ₁₂₄ to R ₁₂₇ are aryl groups, they may be connected to adjacent groups to form (3-30 membered) monocyclic or polycyclic alicyclic or aromatic rings (for example, fluorene); R ₂₀₁ to R ₂₁₁ are each independently hydrogen, deuterium, halogen, or (C1-C30) alkyl in which the halogen is substituted or unsubstituted; r and s are each independently an integer of 1 to 3, and when r or s is an integer of 2 or more, each R ₁₀₀ may be the same or different from each other; and e is an integer of 1 to 3.

Specific examples of the phosphorescent dopant material are as follows.

The present invention provides a composition for preparing an organic electroluminescent device in a further aspect. The composition includes a compound of the present invention as a host material or a hole transporting layer material.

Further, the organic electroluminescent device of the present invention includes a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer includes a light emitting layer, and the light emitting layer may include the composition for an organic electroluminescent device of the present invention.

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

Further, in the organic electroluminescent device of the present invention, in addition to the organic electroluminescent compound of Formula 1, an organic electroluminescent compound of the group 1, 2, 4, 5 period transition metal, lanthanide series and d- The organic compound layer may further include at least one metal or complex compound selected from the group consisting of a light emitting layer and a charge generating layer.

In addition, the organic electroluminescent device of the present invention may emit white light by further including at least one light emitting layer containing a blue, red or green light emitting compound known in the art, in addition to the compound of the present invention. Further, if necessary, it may further include a yellow or orange light emitting layer.

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 ") 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. Preferable examples of the chalcogenide include SiO _X (1? _X ? 2), AlO _x (1? _X ? 1.5), SiON or SiAlON. Preferred examples of the halogenated metal include LiF, MgF ₂ , CaF ₂ , Rare-earth metals, etc. Preferred examples of the metal oxides include Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO and the like.

Further, in the organic electroluminescent device of the present invention, a mixed region of the electron transfer compound and the reducing dopant, or a mixed region of the hole transport compound and the oxidative dopant, may be disposed on at least one surface of the pair of electrodes thus manufactured desirable. In this way, since the electron transfer compound is reduced to an 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, and preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. Also, a white organic electroluminescent device having two or more light emitting layers can be manufactured using a reducing dopant layer as a charge generating layer.

The formation of each layer of the organic electroluminescent device of the present invention may be performed by a dry film formation method such as vacuum deposition, sputtering, plasma or ion plating, or a wet film formation method such as spin coating, dip coating or flow coating Can be applied.

In the case of the wet film formation method, a thin film is formed by dissolving or dispersing a material forming each layer in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc., And it may be any thing that does not have a problem in the tabernacle.

Hereinafter, the organic electroluminescent compound according to the present invention, the method for producing the same, and the luminescent characteristics of the device will be described with reference to the representative compound of the present invention for a detailed understanding of the present invention.

[ Example 1 ] Preparation of compound C-42

Preparation of Compound 1-2

(24 g, 171 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bis (1,3,2- _{dioxaborolane) (B 2 (PIN) 2} ) (57 g, 171 mmol), potassium acetate (KOAc) (42 g, 342 mmol), Pd (PPh 3) 4 (6 g, 8.5 mmol) and dioxane And the mixture was stirred under reflux. After completion of the reaction, the mixture was cooled to room temperature, extracted, and then subjected to column separation using methylene chloride (MC) / hexane to obtain Compound 1-2 (30 g, 100%).

Preparation of compounds 1-4

Compound 1-2 (30 g, 171 mmol) , compound 1-3 (52 g, 171 mmol) , sodium carbonate _{(Na 2 CO 3) (55} g, 513 mmol) and _{Pd (PPh 3) 4 (10} g, 8.5 mmol) were added to a mixed solvent of 500 mL of toluene, 200 mL of ethanol and 200 mL of purified water, and the mixture was stirred at 90 to 100 ° C for 3 hours. After completion of the reaction, the mixture was cooled to room temperature, extracted, and triturated with MC, followed by filtration to obtain Compound 1-4 (33 g, 82%).

Preparation of compounds 1-5

Compound (1-4) (35 g, 140 mmol) was dissolved in 300 mL of triethyl phosphite (P (OEt) ₃ ) and stirred at 160 DEG C for one day. The mixture was distilled under reduced pressure to remove P (OEt) ₃ and then extracted with MC and distilled water. MC and then filtered to give compound 1-5 (15 g, 48%).

Preparation of Compound 1-7

(15 g, 67.3 mmol), 1-bromo-4-iodobenzene (29 g, 100 mmol), CuI (6.5 g, 33 mmol), ethylenediamine (EDA) 5 mL, 67.3 mmol) and 300 mL of toluene were placed, and the mixture was refluxed with stirring for 13 hours. When the reaction was completed, the reaction mixture was cooled to room temperature, extracted, and subjected to column separation to obtain Compound 1-7 (16 g, 62%).

Preparation of compounds 1-8

(16 g, 42 mmol), B ₂ (PIN) ₂ (17 g, 63 mmol), KOAc (8.5 g, 84 mmol) and PdCl ₂ (PPh ₃ ) ₂ (6 g, 8.5 mmol ) And 30 mL of dioxane were placed, and the mixture was stirred under reflux. After completion of the reaction, the mixture was cooled to room temperature, extracted, and subjected to column separation to obtain Compound 1-8 (11 g, 63%).

compound C-42 Manufacturing

Compound 1-10 (4 g, 21.6 mmol) , compound 1-8 (7.5 g, 18 mmol) , Na 2 CO 3 (4 g, 36 mmol) and _{Pd (PPh 3) 4 (1} g, 0.9 mmol) to And the mixture was poured into a mixed solvent of 100 mL of toluene, 50 mL of ethanol, and 50 mL of purified water, followed by stirring at 90 to 100 ° C for 3 hours. After completion of the reaction, the reaction product was cooled to room temperature and extracted, and the product was triturated with MC, followed by filtration to obtain a compound C-42 (5 g, 55%).

Melting point: 220 占 폚, UV: 324 nm, PL: 462.87 nm, chemical formula (measured value / calculated value): 503.15 / 503.62

 [ Example 2 ] Preparation of Compound C-1

Compound 1-11 (4 g, 21.6 mmol) , compound 1-8 (7.5 g, 18 mmol) , Na 2 CO 3 (4 g, 36 mmol) and _{Pd (PPh 3) 4 (1} g, 0.9 mmol) to And the mixture was poured into a mixed solvent of 100 mL of toluene, 50 mL of ethanol, and 50 mL of purified water, followed by stirring at 90 to 100 ° C for 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, extracted and extracted with MC, followed by filtration to obtain Compound C-1 (6 g, 66%).

Melting point: 239 캜, UV: 393 nm, PL: 448.93 nm, Chemical formula (measured value / calculated value): 503.15 / 503.62

[device Manufacturing example  1] The organic Field  Using a luminescent compound OLED  Device Manufacturing

OLED devices were prepared using the organic electroluminescent compound of the present invention. First, a transparent electrode ITO thin film (15 OMEGA / square) obtained from a glass for OLED (manufactured by Samsung Corning) was subjected to ultrasonic cleaning using trichlorethylene, acetone, ethanol and distilled water sequentially and then stored in isopropanol Respectively. Next, an ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus, and N ¹ , N ^{1 '} - ([1,1'-biphenyl] -4,4'-diyl) bis ¹ - (naphthalene- ¹ -yl) -N ⁴ , N ⁴ -diphenylbenzene-1,4-diamine) was added and the chamber was evacuated until the degree of vacuum reached 10 ^-6 torr. And evaporated to deposit a 60 nm thick hole injection layer on the ITO substrate. Subsequently, N, N'-di (4-biphenyl) -N, N'-di (4-biphenyl) -4,4'- diaminobiphenyl was added to another cell in the vacuum vapor- And evaporated to deposit a hole transport layer having a thickness of 20 nm on the hole injection layer. In one of the cells in the vacuum deposition apparatus, a compound C-42 And another cell was loaded with Compound D-87 as a dopant Then, the two materials were evaporated at different rates, and dopants were doped to the entire dopant and the host in an amount of 4 wt% to deposit a light emitting layer with a thickness of 30 nm on the hole transport layer. Then, on one side of the luminescent layer as an electron transporting layer, a layer of 2- (4- (9,10-di (naphthalen-2-yl) anthracen- And lithium quinolate were added to another cell. Then, the two materials were evaporated at the same rate and doped in an amount of 50 wt%, respectively, to deposit an electron transport layer of 30 nm on the light emitting layer. Then, lithium quinolate was deposited to a thickness of 2 nm as an electron injecting layer, and an Al cathode was deposited to a thickness of 150 nm using another vacuum vapor deposition apparatus to produce an OLED device. Each compound was purified by vacuum sublimation under 10 ^-6 torr.

As a result, a current of 6.4 mA / cm ² was emitted at a voltage of 3.6 V, a red emission of 970 cd / m ² was confirmed, and the emission time of 90% at a luminance of 5000 nit was 20 hours or more.

[device Manufacturing example  2] The organic Field  Using a luminescent compound OLED  Device Manufacturing

An OLED device was manufactured in the same manner as in the Device Production Example 1 except that Compound C-1 was used as a host material and Compound D- 88 was used as a dopant.

As a result, a current of 11.1 mA / cm ² was emitted at a voltage of 3.8 V, red emission of 1180 cd / m ² was confirmed, and the time required for the emission to drop to 90% at a luminance of 5000 nit was more than 40 hours.

[ Comparative Example  1] Conventional organic Field  Using a luminescent compound OLED  Device Manufacturing

An OLED device was manufactured in the same manner as in the Device Production Example 1 except that the following compound H-1 was used as a host material and D-88 was used as a dopant.

As a result, a current of 11.3 mA / cm ² was emitted at a voltage of 3.8 V, red luminescence of 1000 cd / m ² was confirmed, and the time required for the luminescence to drop to 90% at a luminance of 5000 nit was over 10 hours.

[Compound H-1 ]

It was confirmed that the organic electroluminescent compounds developed in the present invention are superior in current efficiency to conventional organic electroluminescent compounds. Further, the device using the organic electroluminescent compound according to the present invention has excellent luminescence characteristics, particularly current / power efficiency and lifetime.

Claims (6)

An organic electroluminescent compound represented by the following formula (1).
[Chemical Formula 1]

In Formula 1,
X ₁ to X ₃ each represent -CR- or -N-, at least two of X ₁ to X ₃ represent -N-;
L ₁ is a single bond, substituted or unsubstituted (C 6 -C 30) arylene, or substituted or unsubstituted (5-30 membered) heteroarylene;
R and R ₁ to R ₃ are each independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) Substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) _{, -N (R 11) (R} 12), -Si (R 13) (R 14) (R 15), -S (R 16), -O (R 17), cyano, nitro, or hydroxy, or ; (C3-C30) monocyclic or polycyclic alicyclic or aromatic ring linked to an adjacent substituent, and the carbon atom of the alicyclic or aromatic ring formed may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur ≪ / RTI >
R ₁₁ To R ₁₇ are each independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, substituted or unsubstituted (5-30 membered) , Substituted or unsubstituted (3-7 membered) heterocycloalkyl, or substituted or unsubstituted (C3-C30) cycloalkyl; (C3-C30) monocyclic or polycyclic alicyclic or aromatic ring linked to an adjacent substituent, and the carbon atom of the alicyclic or aromatic ring formed may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur ≪ / RTI >
a to c are each independently an integer of 1 to 4, and when a, b, or c is an integer of 2 or more, each R ₁ , each R ₂ , and each R ₃ may be the same or different;
Wherein said heterocycloalkyl and heteroaryl each independently comprise at least one heteroatom selected from B, N, O, S, P (= O), Si and P; 2. The method of claim 1, wherein L _1, R, R ₁ to R ₃ and R substituted at the ₁₁ to R ₁₇ (C1-C30) alkyl, substituted (C3-C30) cycloalkyl, substituted (3-7 membered) heterocycloalkyl Substituents of alkyl, substituted (C6-C30) aryl (R), substituted (5-30) heteroaryl (C1-C30) alkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C6-C30) alkylthio, (C3-C30) cycloalkyl, (C3-C30) cycloalkenyl, (3-7 membered) heterocycloalkyl, (C6-C30) aryl optionally substituted with (C6-C30) aryl or (5-30 membered) heteroaryl substituted with (5-30 membered) (C6-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, ) Alkylamino, mono- or di- (C6-C30) (C6-C30) aryloxycarbonyl, (C6-C30) arylcarbonyl, di (C6-C30) arylamino, (C1- (C1-C30) alkylcarbonyl, (C1-C30) alkylcarbonyl, di (C1-C30) alkylboronyl, Alkyl (C6-C30) aryl, or an organic electroluminescent compound. The method according to claim 1,
L ₁ is a single bond, substituted or unsubstituted (C6-C15) arylene, or substituted or unsubstituted (5-15 membered) heteroarylene;
R and R ₁ to R ₃ are each independently hydrogen, substituted or unsubstituted (C 1 -C 6) alkyl, substituted or unsubstituted (C 6 -C 20) aryl, or substituted or unsubstituted Aryl; May be connected to adjacent substituents to form a (C3-C15) monocyclic or polycyclic alicyclic or aromatic ring;
and a to c are each independently an integer of 1 to 3. The method according to claim 1,
L ₁ is a single bond, (C 6 -C 15) arylene substituted or unsubstituted with (C ₁ -C 6) alkyl, or unsubstituted (5-15 member) heteroarylene;
R and R ₁ to R ₃ are each independently hydrogen; Unsubstituted (CrC6) alkyl; (C6-C20) aryl unsubstituted or substituted by (C1-C6) alkyl or (C6-C15) aryl; Or (5-20 membered) heteroaryl, which is unsubstituted or substituted by (C6-C15) aryl; May be connected to adjacent substituents to form a (C3-C15) monocyclic aromatic ring;
and a to c are each independently an integer of 1 to 3. The organic electroluminescent compound according to claim 1, wherein the compound represented by Formula 1 is selected from the following compounds.

An organic electroluminescent device comprising the organic electroluminescent compound of claim 1.