KR20150039673A - An Organic Electroluminescent Compound and an Organic Electroluminescent Device Comprising the Same - Google Patents

Abstract

The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device comprising the same. The organic electroluminescent compound of the present invention has a high glass transition temperature and is excellent in thermal stability. When the organic electroluminescent compound of the present invention is used, an organic electroluminescent device having excellent current / power efficiency and lifetime can be manufactured.

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 inversely proportional to the voltage because of the relationship of power efficiency = [(? Voltage) > current efficiency]. In the organic electroluminescent device using the phosphorescent host material, The current efficiency (cd / A) is higher than that of the device, but the driving voltage is also very high, so there is no great advantage in 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.

Japanese Patent Publication JP 3065125B discloses a compound in which diarylamine is substituted at the carbon position 2 of fluorene, as a compound for an organic electroluminescence device. However, the above document does not specifically disclose an organic electroluminescent device using a compound in which a diarylamine or a heteroarylamine and a fluorene, dibenzothiophene or dibenzofuran are substituted at the 9-carbon position of the fluorene .

Japanese Patent Publication JP 3065125B (issued on July 12, 2000)

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,

Ar ₁ and Ar ₂ are each independently substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl; (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 >

X is -O-, -S- or _{-C (R 5) (R 6} ) - is;

R ₁ to R ₄ are each independently hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxy, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 2 -C 30) , Substituted or unsubstituted (C2-C30) alkynyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, -NR ₇ R _{8, -SiR 9 R 10 R 11, -SR} 12, -OR 13, -COR 14 or _{-B (oR 15) (oR 16} ) , or; (C3-C30) monosubstituted or polycyclic substituted or unsubstituted alicyclic or aromatic ring, and the carbon atom of the alicyclic or aromatic ring formed is selected from nitrogen, oxygen and sulfur Lt; / RTI > may be replaced by one or more heteroatoms;

R ₅ to R ₁₆ are each independently substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl; May be connected to adjacent substituents to form a (C3-C30) mono or poly substituted or unsubstituted alicyclic or aromatic ring;

n is an integer from 0 to 2;

when n is 1 or 2, L < ₁ > is a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3-30 membered) heteroarylene;

When n is 0, L ₁ is substituted or unsubstituted (C ₁ -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl;

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

c is an integer of 1 to 3, and when c is an integer of 2 or more, 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 present invention has been made to provide a hole transporting material for use in an organic electroluminescent device capable of solving the problems of the prior art. An ideal hole-transporting material requires a glass transition temperature of at least a certain level, hole injection, hole conduction, proper triplet energy and LUMO energy. When the glass transition temperature is low, crystallization may occur due to the thermal stress applied after the thin film formation process or the thin film formation process, which is a direct cause of degradation of the device life. The arylamine derivative exhibits excellent hole transporting ability and low driving voltage, but many arylamine derivatives are required to increase the molecular weight by introducing a large amount of substituent to achieve an appropriate level of glass transition temperature. However, in this case, the pi-conjugation is prolonged and the triplet energy or the LUMO energy is lowered, resulting in deterioration of the device performance. The reason is that if the triplet energy is high, the exciton formed at the host is prevented from passing to the hole transport layer, and if the LUMO energy is high, the electron coming from the host to the host is prevented from passing to the hole transport layer It contributes.

Another problem that arises when the molecular weight of the hole transporting material is increased by introducing a large number of substituent groups is the deterioration of the ease of deposition. When the molecular weight is increased, the deposition temperature also increases, and the probability of decomposition or damage of the molecule to various forms becomes very high. Therefore, it is important to maintain a proper glass transition temperature by appropriately introducing a substituent, while maintaining a low deposition temperature as compared with a large molecular weight. Accordingly, the present invention provides a solution to introduce an arylamine and a selected heteroaryl or fluorene at the 9-position of the fluorene.

When the selected heteroaryl or fluorene is introduced at the 9-position of fluorene, the deposition temperature can be lowered compared with the case where the substituent is introduced at the 2-position while improving the glass transition temperature. This is because the relative linearity of the molecules decreases. The closer the molecule is to the linear, the stronger the intermolecular force and the higher the deposition temperature.

On the other hand, the reason why the arylamine is introduced into the 9-position rather than the 2-position is to obtain a relatively high triplet energy through short conjugation. In order to obtain a high triplet energy, it is most advantageous not to introduce a substituent. However, even when triplet energy is lowered, introduction of arylamine results in excellent hole injection / transportability, excellent power efficiency and longevity. In addition, heteroaryl or fluorene may be introduced at position 9 instead of position 2 to reduce the relative linearity of the molecule, thereby obtaining an appropriate level of glass transition temperature without significantly increasing the deposition temperature compared with the molecular weight.

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.

Also, 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. Wherein Ar ₁ and Ar _2, R ₁ to R ₄ and substituted (C1-C30) in ₁ L of the above formula (1) alkyl, alkenyl substituted (C2-C30), substituted (C2-C30) alkynyl, substituted (C1- (C3-C30) cycloalkyl, substituted (C3-C30) cycloalkenyl, substituted (3-7 membered) heterocycloalkyl, substituted (C1-C30) alkyl, halo (C1-C30) alkyl, halogen, (C3-C30) alkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, Substituted or unsubstituted (3- to 30-membered) heterocycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio, (C6-C30) alkylsilyl, tri (C6-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) aryl substituted with (C1-C30) arylsilyl, (C1-C30) aryl (C6-C30) arylsilyl, amino, mono- or di- (C1-C30) alkylamino, mono- or di- (C1-C30) alkylcarbonyl, (C1-C30) alkoxycarbonyl, (C6-C30) arylcarbonyl, di (C6-C30) arylboronyl, di (C1-C30) alkyl (C6-C30) arylcarbonyl, (C6-C30) And each independently is preferably at least one selected from the group consisting of (C1-C6) alkyl and (C6-C15) aryl.

Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 membered) Heteroaryl; (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, more preferably each independently (C1-C6) alkyl, (C6-C20) aryl unsubstituted or substituted by alkyl or (C6-C12) aryl; Or (5-20 membered) heteroaryl which is unsubstituted or substituted by (C6-C12) aryl.

Each of R ₁ to R ₄ is independently hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxy, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 2 -C 30) Substituted or unsubstituted (C3-C30) alkynyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3- cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, -NR ₇ R _{8 , -SiR 9 R 10 R 11,} -SR 12, -OR 13, -COR 14 or _{-B (oR 15) (oR 16} ) , or; (C3-C30) monosubstituted or polycyclic substituted or unsubstituted alicyclic or aromatic ring, and the carbon atom of the alicyclic or aromatic ring formed is selected from nitrogen, oxygen and sulfur Which may be substituted by one or more heteroatoms, preferably each independently hydrogen or -NR < ₇ > R < _{8 &} gt ;; Is connected to an adjacent substituent via (C6-C20) or a monocyclic or polycyclic substituted or can form an aliphatic or aromatic ring, more preferably it is each independently hydrogen or -NR ₇ R _8, or; May be connected to adjacent substituents to form an unsubstituted aromatic ring of a single (C6-C20) ring.

Each of R ₅ to R ₁₆ is independently a substituted or unsubstituted (C 1 -C 30) alkyl, a substituted or unsubstituted (C 6 -C 30) aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl; (C3-C30) mono- or polycyclic substituted or unsubstituted alicyclic or aromatic ring which may be connected to adjacent substituents and is preferably independently substituted or unsubstituted (C1-C6) alkyl, or Substituted or unsubstituted (C6-C20) aryl; (C3-C30) monosubstituted or polycyclic substituted or unsubstituted alicyclic or aromatic ring, more preferably each independently represents an unsubstituted (C1-C6) alkyl or a Or (C6-C20) aryl; (C3-C30) monosubstituted or polycyclic substituted or unsubstituted alicyclic or aromatic ring linked to adjacent substituents.

When n is 1 or 2, L ₁ is a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered heteroarylene), preferably a single (C6-C20) arylene, more preferably unsubstituted (C6-C20) arylene.

When n is 0, L ₁ is substituted or unsubstituted (C ₁ -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl , Preferably substituted or unsubstituted (C6-C20) aryl, more preferably unsubstituted (C6-C20) aryl.

According to one aspect of the present invention, in the above formula (1), Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted (C6-C20) aryl or a substituted or unsubstituted (5-20 membered) heteroaryl; X is -O-, -S- or _{-C (R 5) (R 6} ) - is; R ₁ to R ₄ are each independently hydrogen or -NR ₇ R ₈ or may be connected to adjacent substituents to form a (C6-C20) monocyclic or polycyclic substituted or unsubstituted alicyclic or aromatic ring; R ₅ to R ₈ are each independently a substituted or unsubstituted (C 1 -C 6) alkyl, or a substituted or unsubstituted (C 6 -C 20) aryl, or (C 3 -C 30) monocyclic or polycyclic A substituted or unsubstituted alicyclic or aromatic ring; when n is 1 or 2, L ₁ is a single bond or a substituted or unsubstituted (C6-C20) arylene, and; When n is 0, L < ₁ > is substituted or unsubstituted (C6-C20) aryl.

According to another embodiment of the present invention, in Formula 1, Ar ₁ and Ar ₂ are each independently (C6-C20) aryl substituted or unsubstituted with (C1-C6) alkyl or (C6-C12) aryl; Or (5-20 membered) heteroaryl, which is unsubstituted or substituted by (C6-C12) aryl; X is -O-, -S- or _{-C (R 5) (R 6} ) - is; R ₁ to R ₄ are each independently hydrogen or -NR ₇ R ₈ or may be connected to adjacent substituents to form an unsubstituted aromatic ring of a (C6-C20) single ring; R ₅ to R ₈ are each independently an unsubstituted (C 1 -C 6) alkyl or unsubstituted (C 6 -C 20) aryl or may be connected to adjacent substituents to form a (C3-C30) monocyclic or polycyclic substituted or unsubstituted ring Lt; RTI ID = 0.0 > alicyclic < / RTI > or aromatic ring; when n is 1 or 2, L ₁ is an unsubstituted (C6-C20) arylene, and; When n is 0, L < _{1 >} is unsubstituted (C6-C20) aryl.

The molecular weight of the organic electroluminescent material of the present invention is preferably 1,000 or less, more preferably 950 or less, still more preferably 925 or less, in view of the fact that the molecular weight is too large to facilitate thermal decomposition during sublimation deposition , And even more preferably 900 or less.

For good thermal stability, the glass transition temperature is preferably 90 占 폚 or higher, and more preferably 110 占 폚 or higher.

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, R ₁ to R ₄ , X, Ar ₁ , Ar ₂ , L ₁ , n and a to d 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 (13) desirable.

(11)

[Chemical Formula 12]

[Chemical Formula 13]

In the above Formulas 11 to 13,

Cz has the following structure,

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.

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).

[Formula 101] < 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-6

Preparation of Compound 1-1

Dibenzofuran (30 g, 178 mmol) and 500 mL of tetrahydrofuran were added to the reaction vessel, and the temperature was lowered to -78 ° C under a nitrogen atmosphere. To this was added 71 mL (2.5 M, 178 mmol) of n-butyl lithium slowly dropwise. The mixture was stirred at -78 ° C for 30 minutes, stirred at room temperature for 3 hours, and then cooled to -78 ° C again. Then, fluorene (32 g, 178 mmol) dissolved in 500 mL of tetrahydrofuran was slowly added dropwise. When the addition was over, the reaction temperature was gradually raised to room temperature and stirred for 16 hours. The ammonium chloride aqueous solution was added to the reaction solution to terminate the reaction and extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by a rotary evaporator. Thereafter, it was purified by column chromatography to obtain Compound 1-1 (43 g, 70%).

Preparation of Compound 1-2

Nitrogen conditions were prepared by adding Compound 1-1 (10 g, 28.7 mmol), 4-bromodiphenylamine (7.4 g, 30.1 mmol) and methylene chloride (MC) (570 mL) into a reaction vessel. Boron trifluoride diethyl ether (3.8 mL, 30.1 mmol) dissolved in 120 mL of methylene chloride was slowly added dropwise thereto. After stirring at room temperature for 2 hours, ethanol and distilled water were added to terminate the reaction and extracted with methylene chloride. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by a rotary evaporator. Thereafter, the residue was purified by column chromatography to obtain Compound 1-2 (15 g, 95%).

Preparation of compounds 1-3

To the reaction vessel was added compound 1-2 (15 g, 26.9 mmol), phenylboronic acid (3.6 g, 29.6 mmol), tetrakis (triphenylphosphine) palladium (1.5 g, 1.34 mmol) and potassium carbonate (8.9 g, mmol), 160 mL of toluene, 40 mL of ethanol and 40 mL of distilled water were added, followed by stirring at 120 DEG C for 1 hour. After the reaction was completed, the organic layer was washed with distilled water and extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by a rotary evaporator. Thereafter, it was purified by column chromatography to obtain Compound 1-3 (12.3 g, 80%).

compound C-6 Manufacturing

To the reaction vessel was added compound 1-3 (8 g, 13.8 mmol), 4-bromobiphenyl (3.4 g, 14.5 mmol), palladium acetate (0.12 g, 0.55 mmol), S- 1.38 mmol), sodium tert-butoxide (3.3 g, 34.7 mmol) and toluene (70 mL) were added and the mixture was stirred under reflux for 1 hour. When the reaction was completed, the organic layer was washed with distilled water and extracted with methylene chloride (MC). The extracted organic layer was dried with magnesium sulfate and the solvent was removed by a rotary evaporator. Thereafter, the residue was purified by column chromatography to obtain Compound C-6 (8.2 g, 81%).

UV: 360 nm (in toluene), PL: 396 nm (in toluene), MP: 270 캜, MW: 727.89, Tg: 140 캜

[ Example  2] Preparation of compound C-8

Preparation of Compound 2-2

Compound 2-1 (30 g, 86.1 mmol), 4-bromotriphenylamine (84 g, 259 mmol) and 600 mL of methylene chloride (MC) were placed in a reaction vessel to make nitrogen. Then 3 mL of Eaton's reagent was slowly added dropwise to the mixture. After stirring at room temperature for 2 hours, ethanol and distilled water were added to terminate the reaction and extracted with methylene chloride. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by a rotary evaporator. Thereafter, the residue was purified by column chromatography to obtain Compound 2-2 (42 g, 74%).

compound C-8 Manufacturing

To the reaction vessel was added compound 2-2 (10 g, 26.9 mmol), 2-naphthylboronic acid (3.2 g, 18.4 mmol), tetrakis (triphenylphosphine) palladium (0.7 g, 1.08 mmol) g, 38.3 mmol), 60 mL of toluene, 20 mL of ethanol and 20 mL of distilled water were added, and the mixture was stirred at 120 ° C for 3 hours. After the reaction was completed, the organic layer was washed with distilled water and extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by a rotary evaporator. Thereafter, the resultant product was purified by column chromatography to obtain Compound C-8 (7.7 g, 72%).

UV: 324 nm (in toluene), PL: 407 nm (in toluene), MP: 145 캜, MW: 701.27, Tg: 134 캜

[ Example  3] Preparation of compound C-38

Preparation of Compound 3-1

To the reaction vessel was added 2-bromodibenzothiophene (27 g, 103 mmol) and 340 mL of tetrahydrofuran, and the temperature was lowered to -78 ° C under a nitrogen atmosphere. 33 mL (2.5 M, 82 mmol) of n-butyllithium was slowly added dropwise thereto. After stirring for 2 h at -78 [deg.] C, 9H-fluoren-9-one (19 g, 103 mmol) dissolved in 340 mL of tetrahydrofuran was slowly added dropwise. After dropwise addition, the reaction temperature was gradually raised to room temperature and stirred for 30 minutes. The ammonium chloride aqueous solution was added to the reaction solution to terminate the reaction and extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by a rotary evaporator. Thereafter, the residue was purified by column chromatography to obtain Compound 3-1 (23 g, 61%).

Preparation of Compound 3-2

Compound 3-1 (23 g, 63 mmol) and 4-bromotriphenylamine (41 g, 126 mmol) were dissolved in 315 mL of dichloromethane, and 1.4 mL (0.9 M, 1.3 mmol) of Eaton's reagent I dropped it slowly. After stirring at room temperature for 30 minutes, the reaction was terminated with sodium bicarbonate and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and then the solvent was removed using a rotary evaporator. Thereafter, the residue was purified by column chromatography to obtain Compound 3-2 (27 g, 65%).

compound C-38 Manufacturing

(10 g, 14.91 mmol), 2-naphthylboronic acid (3.1 g, 17.89 mmol), tetrakis (triphenylphosphine) palladium (0.5 g, 0.45 mmol) and sodium carbonate , 37.28 mmol), 76 mL of toluene, 19 mL of ethanol and 19 mL of distilled water were added, followed by stirring at 120 ° C for 6 hours. When the reaction was completed, it was washed with distilled water and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and then the solvent was removed using a rotary evaporator. Thereafter, the residue was purified by column chromatography to obtain a compound C-38 (1.2 g, 11%).

UV: 382 nm (in toluene), PL: 405 nm (in toluene), MP: 230 ° C, MW: 717.92, Tg: 140 ° C

[ Example  4] Preparation of Compound C-9

Preparation of Compound 4-1

Dibenzothiophene (30 g, 163 mmol) and 400 mL of tetrahydrofuran were added to the reaction vessel, and the temperature was lowered to -78 ° C under a nitrogen atmosphere. 65 mL (2.5 M, 163 mmol) of n-butyllithium was slowly added dropwise thereto. After stirring for 2 h at -78 [deg.] C, 9H-fluoren-9-one (29 g, 163 mmol) dissolved in 400 mL of tetrahydrofuran was slowly added dropwise. After dropwise addition, the reaction temperature was gradually raised to room temperature and stirred for 30 minutes. The ammonium chloride aqueous solution was added to the reaction solution to terminate the reaction and extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by a rotary evaporator. Thereafter, the residue was purified by column chromatography to obtain Compound 4-1 (20 g, 34%).

Preparation of Compound 4-2

Compound 4-1 (7 g, 19 mmol) and 4-bromotriphenylamine (16 g, 48 mmol) were dissolved in 96 mL of dichloromethane, and then 0.5 mL (0.9 M, 0.4 mmol) of Eaton's reagent I dropped it slowly. After stirring at room temperature for 30 minutes, the reaction was terminated with sodium bicarbonate and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and then the solvent was removed using a rotary evaporator. Thereafter, the residue was purified by column chromatography to obtain Compound 4-2 (8 g, 62%).

compound C-9 Manufacturing

To the reaction vessel was added compound 4-2 (8 g, 11.93 mmol), 2-naphthylboronic acid (2.5 g, 14.31 mmol), tetrakis (triphenylphosphine) palladium (0.4 g, 0.36 mmol) , 29.83 mmol), 60 mL of toluene, 15 mL of ethanol and 15 mL of distilled water were added thereto, followed by stirring at 120 ° C for 6 hours. When the reaction was completed, it was washed with distilled water and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and then the solvent was removed using a rotary evaporator. Thereafter, the residue was purified by column chromatography to obtain the compound C-9 (4.3 g, 50%).

UV: 390 nm (in toluene), PL: 407 nm (in toluene), MP: 215 캜, MW: 717.92, Tg: 151 캜

[ Example  5] Preparation of Compound C-78

compound C-78 Manufacturing

To the reaction vessel were added compound 1-3 (5.6 g, 9.72 mmol), 2-bromo-9,9-dimethylfluorene (2.9 g, 10.7 mmol), palladium acetate (0.08 g, 0.38 mmol) g, 0.97 mmol), sodium tert-butoxide (2.3 g, 24.3 mmol) and toluene (50 mL) were added and the mixture was stirred under reflux for 1 hour. When the reaction was completed, the organic layer was washed with distilled water and extracted with methylene chloride (MC). The extracted organic layer was dried with magnesium sulfate, and then the solvent was removed using a rotary evaporator. Thereafter, the residue was purified by column chromatography to obtain Compound C-78 (6.2 g, 83%).

UV: 322 nm (in toluene), PL: 398 nm (in toluene), MP: 242 캜, MW: 767.95, Tg: 151 캜

[ Example  6] Preparation of Compound C-12

Preparation of Compound 5-2

The reaction vessel was charged with compound 1-1 (10 g, 28.7 mmol), diphenylamine (14 g, 86.1 mmol) and methylene chloride (MC) (570 mL) under nitrogen. Boron trifluoride diethyl ether (3.8 mL, 30.1 mmol) dissolved in 120 mL of methylene chloride was slowly added dropwise thereto. After stirring at room temperature for 2 hours, ethanol and distilled water were added to complete the reaction, and the mixture was extracted with methylene chloride. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by a rotary evaporator. Thereafter, the residue was purified by column chromatography to obtain Compound 5-2 (11 g, 78%).

compound C-12 Manufacturing

(11 g, 22.1 mmol), 2-bromo-9,9-dimethylfluorene (6.6 g, 24.4 mmol), palladium acetate (0.19 g, 0.88 mmol), S- g, 2.21 mmol), sodium tert-butoxide (5.3 g, 55.4 mmol), and toluene (110 mL) were added and the mixture was stirred under reflux for 1 hour. When the reaction was completed, the organic layer was washed with distilled water and extracted with methylene chloride (MC). The extracted organic layer was dried with magnesium sulfate and the solvent was removed by a rotary evaporator. Thereafter, the residue was purified by column chromatography to obtain the compound C-12 (12 g, 79%).

UV: 344 nm (in toluene), PL: 387 nm (in toluene), MP: 225 캜, MW: 691.86, Tg: 137 캜

[ Example  7] Preparation of Compound C-79

compound C-79 Manufacturing

To the reaction vessel, compound 2-2 (6.7 g, 10.2 mmol), 4-biphenylboronic acid (2.4 g, 12.2 mmol), tetrakis (triphenylphosphine) palladium (0.47 g, 0.41 mmol) g, 25.5 mmol), toluene (45 mL), ethanol (15 mL) and distilled water (15 mL) were added, followed by stirring at 120 ° C for 3 hours. After the reaction was completed, the organic layer was washed with distilled water and extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by a rotary evaporator. Thereafter, the residue was purified by column chromatography to obtain the compound C-79 (5.0 g, 67%).

UV: 344 nm (in toluene), PL: 397 nm (in toluene), MP: 255 캜, MW: 727.29, Tg: 141 캜

[ Example  8] Preparation of Compound C-81

Preparation of Compound 6-1

The reaction vessel was charged with 2-bromo-9,9'-dimethylfluorene (40 g, 146 mmol) and 500 mL of tetrahydrofuran, under nitrogen atmosphere, and then cooled to -78 ° C. 60 mL (2.5 M, 146 mmol) of n-butyllithium was slowly added dropwise thereto. After stirring for 90 minutes at -78 [deg.] C, fluorene (26 g, 146 mmol) dissolved in 500 mL of tetrahydrofuran was slowly added dropwise. When the dropwise addition was over, the reaction temperature was gradually raised to room temperature and stirred for 16 hours. The ammonium chloride aqueous solution was added to the reaction solution to terminate the reaction and extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by a rotary evaporator. Thereafter, the residue was purified by column chromatography to obtain Compound 6-1 (41 g, 72%).

compound C-81 Manufacturing

(10 g, 26.7 mmol), compound 6-2 (CAS number: 122215-84-3) (10.6 g, 26.7 mmol) and methylene chloride (MC) (134 mL) made. Then 0.6 mL of Eaton's reagent was slowly added dropwise. After stirring at room temperature for 2 hours, ethanol and distilled water were added to terminate the reaction and extracted with methylene chloride. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by a rotary evaporator. Thereafter, the residue was purified by column chromatography to obtain a compound C-81 (17 g, 85%).

UV: 378 nm (in toluene), PL: 395 nm (in toluene), MP: 178 캜, MW: 753.34, Tg: 143 캜

[Device Manufacturing Example 1] Production of OLED Device Using Organic Electroluminescent Compound According to the Present Invention

An OLED device was prepared using the light emitting material of the present invention. First, a transparent electrode ITO thin film (10? /?) Obtained from a glass for OLED (manufactured by Geomatec) was subjected to ultrasonic cleaning using acetone and isopropanol sequentially, and then stored in isopropanol for storage. 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, a compound C-6 was added to another cell in a vacuum deposition apparatus, and a current was applied to the cell to evaporate it, thereby depositing 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. In one of the cells in a vacuum deposition apparatus, 9- (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) -9'- , 3'-bicarbazole and D-1 as a dopant in another cell, and then evaporating the two materials at different rates to dope the dopant and dopant to the entire host at 15 wt% A light emitting layer with a thickness of 30 nm was deposited on the hole transport layer. Then, on one side of the luminescent layer as an electron transporting layer was added a solution of 2- (4- (9,10-di (naphthalen-2-yl) anthracen- And lithium quinolate was added to another cell. Then, the two materials were evaporated at the same rate and doped with 50 wt% each, thereby depositing a 30 nm electron transport 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 1.9 mA / cm < ² > flowed and green luminescence of 900 cd / m < ² > was confirmed.

Further, it took more than 250 hours for the luminescence to fall to 80% at a luminance of 15000 nits.

[Device preparation example 2] Manufacture of OLED device using organic electroluminescence compound according to the present invention

Compound C-9 was deposited as a hole transporting layer to a thickness of 20 nm and, as a luminescent layer, 7- (4 - ([1,1'-biphenyl] -4-yl) quinazolin- ) -7H-benzo [c] carbazole, and the other cell was charged with Compound D-87 as a dopant. Then, the two materials were evaporated at different rates to obtain a dopant and a dopant in an amount of 3 wt% OLED devices were fabricated in the same manner as in Device Manufacturing Example 1 except that a light emitting layer with a thickness of 30 nm was deposited on the hole transport layer.

As a result, a current of 6.7 mA / cm < ² > flowed and red luminescence of 1000 cd / m < ² > was confirmed.

Also, it took more than 200 hours for the emission to fall to 80% at a luminance of 5000 nits.

[Device preparation example 3] Manufacture of OLED device using organic electroluminescence compound according to the present invention

An OLED device was produced in the same manner as in the Device Production Example 1 except that the compound C-8 was used as the hole transporting layer, and the following compound H-1 was used as a host and the following compound FD-1 was used as a dopant.

As a result, a current of 16.3 mA / cm < ² > flowed and blue light emission of 800 cd / m < ² >

Also, the time taken for the luminescence to drop to 50% at a brightness of 2000 nits was more than 170 hours.

[Device preparation example 4] Manufacture of OLED device using organic electroluminescence compound according to the present invention

An OLED device was fabricated in the same manner as in Device Manufacturing Example 2 except that Compound C-78 was deposited as a hole transporting layer to a thickness of 20 nm.

As a result, a current of 11.7 mA / cm < ² > flowed and a red emission of 1700 cd / m < ² > was confirmed.

Also, it took more than 210 hours for the emission to fall to 80% at a luminance of 5000 nits.

[Device preparation example 5] Manufacture of OLED device using organic electroluminescence compound according to the present invention

An OLED device was prepared in the same manner as in the Device Production Example 1 except that Compound C-79 was deposited as a hole transporting layer to a thickness of 20 nm.

As a result, a current of 4.2 mA / cm < ² > flowed and green luminescence of 3000 cd / m < ² > was confirmed.

In addition, it took more than 240 hours for the luminescence to fall to 80% at a luminance of 15000 nits.

[Device production example 6] Production of OLED device using organic electroluminescent compound according to the present invention

An OLED device was manufactured in the same manner as in the Device Production Example 1 except that the compound C-12 was deposited to a thickness of 20 nm as a hole transporting layer.

As a result, a current of 3.2 mA / cm < ² > flowed and green luminescence of 1500 cd / m < ² > was confirmed.

Also, it took more than 270 hours for the emission to fall to 80% at a luminance of 15000 nits.

[Device production example 7] Production of OLED device using organic electroluminescent compound according to the present invention

An OLED device was manufactured in the same manner as in the Device Production Example 3 except that the compound C-81 was deposited to a thickness of 20 nm as the hole transport layer.

As a result, a current of 22.6 mA / cm < ² > flowed and blue luminescence of 1200 cd / m < ² > was confirmed.

Also, it took more than 130 hours for light emission to fall to 50% at a brightness of 2000 nits.

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

Except that N, N'-di (4-biphenyl) -N, N'-di (4-biphenyl) -4,4'- diaminobiphenyl was deposited to a thickness of 20 nm as a hole transporting layer. An OLED device was prepared in the same manner as in Example 1.

As a result, a current of 32.6 mA / cm < ² > flowed and a green luminescence of 12000 cd / m < ² > was confirmed.

Also, it took more than 230 hours for light emission to drop to 80% at a luminance of 15000 nits.

[ Comparative Example  2] Conventional organic Field  Using a luminescent compound OLED  Device Manufacturing

Except that N, N'-di (4-biphenyl) -N, N'-di (4-biphenyl) -4,4'- diaminobiphenyl was deposited to a thickness of 20 nm as a hole transporting layer. An OLED device was prepared in the same manner as in Example 3.

As a result, a current of 138.1 mA / cm < ² > flowed and blue light emission of 5000 cd / m < ² >

Also, it took more than 130 hours for light emission to drop to 50% at a brightness of 2000 nits.

[ Comparative Example  3] Conventional organic Field  Using a luminescent compound OLED  Device Manufacturing

Except that N, N'-di (4-biphenyl) -N, N'-di (4-biphenyl) -4,4'- diaminobiphenyl was deposited to a thickness of 20 nm as a hole transporting layer. An OLED device was prepared in the same manner as in Example 2.

As a result, a current of 131.6 mA / cm < ² > flowed and red luminescence of 10000 cd / m < ² > was confirmed.

Also, it took more than 180 hours for the emission to fall to 80% at a luminance of 5000 nits.

[ Comparative Example  4] Conventional organic Field  Using a luminescent compound OLED  Device Manufacturing

Except that 9,9-dimethyl-N, N-diphenyl-9H-fluorene-2-amine (Tg = 43 ° C) was deposited as a hole transporting layer to a thickness of 20 nm. .

As a result, a current of 20.8 mA / cm < ² > flowed and green light emission of 9000 cd / m < ² >

Also, it took more than 25 hours for the emission to fall to 80% at a luminance of 15000 nits.

It was confirmed that the organic electroluminescent compounds developed in the present invention have a high glass transition temperature and 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,
Ar ₁ and Ar ₂ are each independently substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl; (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 >
X is -O-, -S- or _{-C (R 5) (R 6} ) - is;
R ₁ to R ₄ are each independently hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxy, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 2 -C 30) , Substituted or unsubstituted (C2-C30) alkynyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, -NR ₇ R _{8, -SiR 9 R 10 R 11, -SR} 12, -OR 13, -COR 14 or _{-B (oR 15) (oR 16} ) , or; (C3-C30) monosubstituted or polycyclic substituted or unsubstituted alicyclic or aromatic ring, and the carbon atom of the alicyclic or aromatic ring formed is selected from nitrogen, oxygen and sulfur Lt; / RTI > may be replaced by one or more heteroatoms;
R ₅ to R ₁₆ are each independently substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl; May be connected to adjacent substituents to form a (C3-C30) mono or poly substituted or unsubstituted alicyclic or aromatic ring;
n is an integer of 0 or 2;
When n is 2, L < ₁ > is a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3-30 membered) heteroarylene;
When n is 0, L ₁ is substituted or unsubstituted (C ₁ -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl;
a, b, and d are each independently an integer of 1 to 4, and when a, b, or d is an integer of 2 or more, each R ₁ , each R ₂ , and each R ₄ may be the same or different;
c is an integer of 1 to 3, and when c is an integer of 2 or more, 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 Ar ₁ and Ar _2, R ₁ to R _16, and substituted in L ₁ (C1-C30) alkyl, alkenyl substituted (C2-C30), substituted (C2-C30) alkynyl, substituted ( (C3-C30) cycloalkyl, substituted (C3-C30) cycloalkenyl, substituted (3-7 membered) heterocycloalkyl, substituted (C1-C30) alkyl (C1-C30) alkyl, each of which is optionally substituted with one or more substituents independently selected from deuterium, halogen, cyano, carboxyl, nitro, (C3-C30) cycloalkyl, (C3-C30) alkoxy, (C1-C30) alkylthio, Substituted or unsubstituted (3-30 membered) heterocycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio or (C6- (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1-C30) aryl (C6-C30) arylsilyl, amino, mono- or di- (C1-C30) alkylamino, mono- or di- (C1-C30) alkylcarbonyl, (C1-C30) alkoxycarbonyl, (C6-C30) arylcarbonyl, di (C6-C30) arylboronyl, di (C1-C30) alkyl (C6-C30) aryl, (C6-C30) aryl Organic electroluminescent compound. 2. The compound of claim 1 wherein Ar < _{1 >} and Ar < ₂ > are each independently substituted or unsubstituted (C6-C20) aryl or substituted or unsubstituted (5-20 membered heteroaryl; X is -O-, -S- or _{-C (R 5) (R 6} ) - is; R ₁ to R ₄ are each independently hydrogen or -NR ₇ R ₈ or may be connected to adjacent substituents to form a (C6-C20) monocyclic or polycyclic substituted or unsubstituted alicyclic or aromatic ring; R ₅ to R ₈ are each independently a substituted or unsubstituted (C 1 -C 6) alkyl, or a substituted or unsubstituted (C 6 -C 20) aryl, or (C 3 -C 30) monocyclic or polycyclic A substituted or unsubstituted alicyclic or aromatic ring; when n is 2, L ₁ is a single bond or a substituted or unsubstituted (C6-C20) arylene, and; When n is 0, L ₁ is substituted or unsubstituted (C6-C20) aryl. The compound according to claim 1, wherein Ar ₁ and Ar ₂ are each independently (C6-C20) aryl unsubstituted or substituted by (C1-C6) alkyl or (C6-C12) aryl; Or (5-20 membered) heteroaryl, which is unsubstituted or substituted by (C6-C12) aryl; X is -O-, -S- or _{-C (R 5) (R 6} ) - is; R ₁ to R ₄ are each independently hydrogen or -NR ₇ R ₈ or may be connected to adjacent substituents to form an unsubstituted aromatic ring of a (C6-C20) single ring; R ₅ to R ₈ are each independently an unsubstituted (C 1 -C 6) alkyl or unsubstituted (C 6 -C 20) aryl or may be connected to adjacent substituents to form a (C3-C30) monocyclic or polycyclic substituted or unsubstituted ring Lt; RTI ID = 0.0 > alicyclic < / RTI > or aromatic ring; when n is 2, L ₁ is an unsubstituted (C6-C20) arylene, and; When n is 0, L ₁ is unsubstituted (C6-C20) aryl. 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.