KR20150012488A - 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 including the same. The organic electroluminescent compound of the present invention has a high glass transition temperature, thereby leading to a thermal stability, and is used for manufacturing an electroluminescent device with outstanding current efficiency.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic electroluminescent compound and an organic electroluminescent device including the same. BACKGROUND ART < RTI ID = 0.0 >

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 included in the hole transport layer or the like is recognized as a means for improving device characteristics such as hole transport efficiency, luminous 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.

WO02 / 34627A1 discloses that a diarylamine, a heteroarylamine, or a heteroaryl group containing a nitrogen atom is bonded to a benzene ring of a spirobifluorene as a substituent directly or via a linker such as an aryl group, Discloses a compound which is only one compound as an organic electroluminescent device compound.

However, this document does not specifically disclose a compound having two substituents bonded to the same benzene ring of the spirobifluorene or the same linker, and an organic electroluminescent device using the compound as a hole transport layer.

International publication publication WO 2012/034627 A1 (disclosure on March 22, 2012)

An object of the present invention is to provide an organic electroluminescent compound having excellent current efficiency and high glass transition temperature (Tg) and excellent thermal stability.

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.

The organic electroluminescent compound according to the present invention represented by the following formula (1) has a high glass transition temperature (Tg) and excellent thermal stability because it has a spirobifluorene mother nucleus.

In Formula 1,

Ar ₁ to Ar ₄ are each independently a substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, or substituted or unsubstituted (5-30 membered) (3-30 membered) monovalent or polycyclic alicyclic or aromatic ring, 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 ;

Ar ₅ to Ar ₈ each independently represent hydrogen, deuterium, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, or substituted or unsubstituted (5-30 membered) Aryl or a substituted or unsubstituted (3-30 membered) 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 nitrogen, oxygen and sulfur ≪ / RTI >

m and n are each independently an integer of 0 to 2, and when m or n is 2, each of -N (Ar ₁ ) (Ar ₂ ) and each -N (Ar ₃ ) (Ar ₄ ) You can;

m + n is 2;

When m is 1 or 2, L ₁ is a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5-30 membered heteroarylene) L ₁ is selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 2 -C 30) alkenyl, substituted or unsubstituted (C 2 -C 30) alkynyl, (C6-C30) aryl, or substituted or unsubstituted (5-30 membered) heteroaryl;

When n is 1 or 2, L ₂ is a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (5-30 membered heteroarylene) L ₂ is selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 2 -C 30) alkenyl, substituted or unsubstituted (C 2 -C 30) alkynyl, (C6-C30) aryl, or substituted or unsubstituted (5-30 membered) heteroaryl;

o is 1 or 2, and when Ar 2 is 2, each Ar ₅ may be the same or different;

each of p, q and r is independently an integer of 1 to 4, and when p, q or r is an integer of 2 or more, each Ar ₆ , each Ar ₇ , and each Ar ₈ may be the same or different;

,

및

인 경우(여기서, X는 -O-, -S-, -C(R₁)(R₂)- 또는 -N(R₃)-이며; R₁ 내지 R₃는 각각 독립적으로 수소, 중수소, 할로겐, 시아노, 카르복실, 니트로, 히드록시, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 (C3-C30)시클로알케닐, 치환 또는 비치환된 (3-7원)헤테로시클로알킬, 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (5-30원)헤테로아릴이거나; R₁과 R₂는 서로 연결되어 (3-30원) 단일환 또는 다환의 지환족 또는 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 또는 방향족 환의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있다)는 제외하고;only,

,

And

If (wherein, X is _{-O-, -S-, -C (R 1} ) (R 2) - or -N (R ₃₎ -, and; R ₁ to R ₃ are each independently hydrogen, deuterium, halogen (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl , substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5-30 membered) heteroaryl or; R ₁ and R ₂ is (3-30 membered) monovalent or polycyclic alicyclic or aromatic ring, and the carbon atom of the alicyclic or aromatic ring formed may be replaced with one or more heteroatoms selected from nitrogen, oxygen and sulfur );

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

In one embodiment of the present invention, the compound represented by the formula (1) is preferably represented by the following formula (2) or (3).

In the above Formulas 2 and 3,

Ar ₁ to Ar ₄ are each independently substituted or unsubstituted (C6-C30) aryl;

m and n are each 1;

L ₁ , L ₂ , Ar ₅ to Ar ₈ , and o to r are as defined in formula (1).

In a further embodiment of the present invention, the compound represented by the formula (1) is preferably represented by the following formula (4)

In Formula 4,

Ar ₁ and Ar ₂ are each independently substituted or unsubstituted (C 6 -C 30) aryl;

L ₁ 'is substituted or unsubstituted (C 6 -C 30) arylene;

Two -N (Ar ₁ ) (Ar ₂ ) are bonded to each other at a meta position to L ₁ ';

Ar ₅ to Ar ₈ , and o to r are as defined in formula (1).

In the organic electroluminescent compound in which two diarylamines are meta-connected in the same aryl group as in the above formulas (2) to (4), the band gap is reduced by conjugation. Therefore, when used in the hole transporting layer, it can have a relatively high triplet energy and can prevent the excitons of the phosphorescent light emitting layer from being transferred to the hole transporting layer.

The organic electroluminescent compound according to the present invention is advantageous in manufacturing an organic electroluminescent device having excellent current efficiency and high glass transition temperature (Tg) and excellent thermal stability.

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, "(C2-C30) alkynyl" means straight 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 in the general formula 1 Ar ₁ to Ar _8, R ₁ to R _3, L ₁ and substituted at the L ₂ alkyl, substituted alkenyl, substituted alkynyl, substituted cycloalkyl, substituted cycloalkenyl, substituted heterocycloalkyl, substituted aryl (C1-C30) alkoxy, (C6-C30) aryl, (C6-C30) aryl (C6) (C3-C30) cycloalkyl, (3-7 membered) heterocycloalkyl, tri (C1-C30) alkylsilyl, tri (C6-30) (C2-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1- (C6-C30) arylamino, di (C6-C30) arylamino, di (C6-C30) arylamino substituted with (C6-C30) aryl (C1-C30) arylcarbonyl, di (C1-C30) alkylboronyl, (C1-C60) alkyl, (C6-C30) aryl, carboxyl, nitro and hydroxy, each of which is independently selected from the group consisting of , And di (C1-C6) alkyl (C6-C15) aryl.

Wherein Ar ₁ to Ar ₄ each independently represents a substituted or unsubstituted (C 1 -C 30) alkyl, a substituted or unsubstituted (C 6 -C 30) aryl, or a substituted or unsubstituted (5-30 membered) Heteroaryl, or may be connected to adjacent substituents (3-30 members) to form a monocyclic or polycyclic alicyclic or aromatic ring; The carbon atom of the alicyclic or aromatic ring formed may be replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur; Preferably a substituted or unsubstituted (C6-C20) aryl; More preferably (C6-C20) aryl which is unsubstituted or substituted by (C1-C6) alkyl, (C6-C15) aryl or di (C1-C6) alkyl (C6-C15) aryl.

Ar ₅ to Ar ₈ each independently represent hydrogen, deuterium, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, or substituted or unsubstituted (5-30 membered) Aryl, or a substituted or unsubstituted (3-30 membered) monocyclic or polycyclic alicyclic or aromatic ring linked to an adjacent substituent; The carbon atom of the alicyclic or aromatic ring formed may be replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur; Or a hydrogen atom or a substituted or unsubstituted (3-20 membered) monovalent or polycyclic aromatic ring linked to an adjacent substituent, and the carbon atom of the formed aromatic ring may be substituted with one or more Lt; / RTI > may be replaced by a heteroatom; More preferably hydrogen, or a (1-3-15 membered) monocyclic or polycyclic aromatic ring which is connected to the adjacent substituent to be substituted or unsubstituted (C1-C6) alkyl or (C6-C15) aryl, The carbon atom of the aromatic ring may be replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur.

When m is 1 or 2, 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 or Unsubstituted (C6-C20) arylene, more preferably a single bond or unsubstituted (C6-C15) arylene; when m is 0, L ₁ is selected from hydrogen, heavy hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl , Substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5-30 membered) heteroaryl; Preferably hydrogen.

When n is 1 or 2, L ₂ is a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5-30 membered heteroarylene), preferably a single bond or Unsubstituted (C6-C20) arylene, more preferably a single bond or unsubstituted (C6-C15) arylene; When n is 0, L ₂ is hydrogen, deuterium, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 2 -C 30) alkenyl, substituted or unsubstituted (C 2 -C 30) , Substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5-30 membered) heteroaryl; Preferably hydrogen.

According to one embodiment of the present invention, Ar ₁ to Ar ₄ in the general formula (1) are each independently substituted or unsubstituted (C 6 -C 20) aryl; Ar ₅ to Ar ₈ are each independently hydrogen or a (3-20 membered) monovalent or polycyclic aromatic ring connected with an adjacent substituent to form a substituted or unsubstituted aromatic ring, and the carbon atom of the formed aromatic ring may be substituted with nitrogen, Lt; / RTI > may be replaced by one or more heteroatoms selected from sulfur; When m is 1 or 2, L ₁ is a single bond or unsubstituted (C6-C20) arylene, and when m is 0, L ₁ is hydrogen; When n is 1 or 2, L ₂ is a single bond or unsubstituted (C 6 -C 20) arylene, and when n is 0, L ₂ is hydrogen.

According to another embodiment of the present invention, Ar ₁ to Ar ₄ are each independently selected from the group consisting of (C 1 -C 6) alkyl, (C 6 -C 15) aryl or di (C 1 -C 6) (C6-C20) aryl optionally substituted with aryl; Ar ₅ to Ar ₈ are each independently hydrogen or a ( ₁ to ₅ membered) monocyclic or polycyclic aromatic ring which is connected to an adjacent substituent to be substituted or unsubstituted with (C1-C6) alkyl or (C6-C15) And the carbon atom of the aromatic ring formed may be replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur; When m is 1 or 2, L ₁ is a single bond or unsubstituted (C6-C15) arylene, and when m is 0, L ₁ is hydrogen; When n is 1 or 2, L ₂ is a single bond or unsubstituted (C 6 -C 15) arylene, and when n is 0, L ₂ is hydrogen.

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, Ar ₁ to Ar ₈ , L ₁ , L ₂ , m, n and o to r are the same as defined in Chemical Formula 1, and Hal is halogen.

The Buchwald-Hartwig reaction of Scheme 1 reacts the arylamine and the aryl halide under basic conditions such as sodium t-butoxide to form a carbon-nitrogen bond. The reaction is carried out in an aromatic organic solvent such as toluene or xylene, and the combination of palladium acetate and s-force (e.g., S-force (2-dicyclophosphino-2 ', 6'-dimethoxyphenyl) And proceeds under reflux using the same palladium complex system as a catalyst.

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)

_{H- (Cz-L 4) h} -M

[Chemical Formula 12]

H- (Cz) _i -L ₄ -M

[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, a and b are each independently an integer of 0 to 4, and when h, i, j, k, a or b 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 each independently represent hydrogen, deuterium, halogen, or (C 1 -C 30) alkyl unsubstituted or substituted with halogen; c and d are each independently an integer of 1 to 3, and when c or d 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.

In addition, 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 is disposed on at least one surface of the pair of electrodes thus fabricated 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 light emitting 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-2

Preparation of Compound 1-1

To the reaction vessel were added 2,2,4-dichlorophenylboronic acid (20 g, 104 mmol), 1-bromo-2-iodobenzene (44 g, 157 mmol), tetrakis (triphenylphosphine) palladium g, 3.14 mmol), sodium carbonate (27 g, 262 mmol), toluene (520 mL) and ethanol (130 mL) were added, and the mixture was stirred at 120 ° C for 6 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. The product was purified by column chromatography to give compound 1-1 (15 g, 50%).

Preparation of compounds 1-3

To the reaction vessel was added Compound 1-1 (15 g, 50 mmol) and tetrahydrofuran (170 mL), and the mixture was cooled to -78 ° C under a nitrogen atmosphere. 21 mL (2.5 M, 52 mmol) of n-butyllithium was slowly added dropwise thereto. After stirring for 2 hours at -78 [deg.] C, 100 mg of fluorene (9.4 g, 52 mmol) dissolved in tetrahydrofuran was slowly added dropwise. When the addition was over, the reaction temperature was gradually raised to room temperature and further 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 organic layer was dried over magnesium sulfate, and then the solvent was removed using a rotary evaporator. 500 mL of acetic acid and 0.2 mL of HCl were added to the resultant compound 1-2, and the mixture was stirred overnight at 120 ° C. The solvent was removed using a rotary evaporator and then purified by column chromatography to obtain Compound 1-3 (13 g, 70%).

compound C-2 Manufacturing

To the reaction vessel were added compound 1-3 (7 g, 18.1 mmol), N-phenylbiphenyl-4-amine (10.7 g, 43.6 mmol), tris (dibenzylindeneacetone) dipalladium (1.9 g, 2.18 mmol) S-Phos (2 g, 4.36 mmol), sodium tert-butoxide (6.9 g, 72 mmol) and 90 mL of o-xylene were added and refluxed for 2 hours. The reaction mixture was cooled to room temperature and the solid was then filtered and washed with methylene chloride (MC). The filtrate was distilled under reduced pressure and purified by column chromatography to obtain the compound C-2 (12 g, 84%).

[ Example 2 ] Preparation of Compound C-29

Preparation of Compound 2-1

To the reaction vessel was added 2-bromoiodobenzene (29.7 g, 105 mmol), 2,4-dichlorophenyl-4-boronic acid (20 g, 105 mmol), tetrakis (triphenylphosphine) palladium mmol), sodium carbonate (28 g, 263 mmol), toluene (600 mL) and ethanol (150 mL) were added. 150 mL of distilled water was added and the mixture was stirred at 120 ° C for 6 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. The product was purified by column chromatography to obtain Compound 2-1 (19.5 g, 61%).

Preparation of Compound 2-2

To the reaction vessel were added 1-indanone (45 g, 340 mmol), phthalaldehyde (50 g, 374 mmol), sodium ethoxide (25 mL, 20 wt%, 70 mmol) and 1 L of ethanol, Lt; / RTI > for 5 hours. After the reaction was completed, the solution was cooled to room temperature, and the precipitated solid was washed with a small amount of methanol to obtain Compound 2-2 (50 g, 64%).

Preparation of compound 2-4

Compound 2-1 (18.5 g, 61.3 mmol) and 200 mL of tetrahydrofuran were placed in a reaction vessel, and the temperature was lowered to -78 ° C in a nitrogen atmosphere. 25 mL (2.5 M, 61.3 mmol) of n-butyllithium was slowly added dropwise thereto. After stirring for 2 hours at -78 캜, Compound 2-2 dissolved in 200 mL of tetrahydrofuran was slowly added dropwise. When the addition was over, the reaction temperature was gradually raised to room temperature and further 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 organic layer was dried over magnesium sulfate, and then the solvent was removed by a rotary evaporator to obtain Compound 2-3. 600 mL of acetic acid and 0.3 mL of HCl were added to the resulting compound 2-3, and the mixture was stirred overnight at 120 ° C. The solvent was removed using a rotary evaporator and then purified by column chromatography to obtain Compound 2-4 (14.3 g, 54%).

compound C-29 Manufacturing

(12 g, 27.6 mmol), diphenylamine (10.3 g, 60.7 mmol), palladium (II) acetate (0.93 g, 4.14 mmol), 2-dicyclohexylphosphino- Dimethoxybiphenyl (2.3 g, 5.5 mmol), sodium tert-butoxide (6.6 g, 70 mmol) and o-xylene (150 mL) were added and refluxed for 8 hours. The reaction mixture was cooled to room temperature and the solid was then filtered and washed with methylene chloride (MC). The filtrate was distilled under reduced pressure and purified by column chromatography to obtain the compound C-29 (10 g, 53%).

[ Example  3] Preparation of Compound C-49

Preparation of Compound 3-1

The reaction vessel was charged with 1-bromo-3-iodobenzene (20 g, 164 mol), phenylboronic acid (70 g, 246 mol), tetrakis (triphenylphosphine) palladium (5.7 g, 0.49 mol) (43 g, 410 mol), toluene (820 mL) and ethanol (200 mL) were added, and 200 mL of distilled water was added thereto, followed by stirring at 120 DEG C for 6 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 Compound 3-1 (60 g, 150%).

Preparation of Compound 3-2

The reaction vessel was charged with Compound 3-1 (60 g, 257 mol), aniline (70 mL, 46 mol), palladium (II) acetate (2.3 g, 103 mol), S- 800 mL of phenol was added thereto, followed by stirring at 120 DEG C for 6 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 Compound 3-2 (26 g, 65%).

Preparation of Compound C-49

Compound 3 (6 g, 155 mmol), compound 3-2 (9 g, 373 mmol), tris (dibenzylindeneacetone) dipalladium (1.7 g, 1.87 mmol), S- g, 3.73 mmol), sodium tert-butoxide (6.0 g, 62 mmol), and o-xylene (100 mL) were added and refluxed for 8 hours. The reaction mixture was cooled to room temperature and the solid was then filtered and washed with methylene chloride (MC). The filtrate was distilled under reduced pressure and purified by column chromatography to obtain the compound C-49 (6.4 g, 51%).

[ Example  4] Preparation of Compound C-8

Preparation of Compound 4-1

To the reaction vessel were added 2-bromo-9,9-dimethyl-9H-fluorene (25 g, 91 mol), aniline (10 mL, 109 mmol), palladium (II) acetate (1.03 g, 4.58 mmol) Butylphosphine (1.85 g, 9.15 mol) and 500 mL of xylene were added thereto, followed by stirring at 120 ° C for 6 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 Compound 4-1 (20 g, 76%).

Preparation of Compound C-8

To the reaction vessel were added compound 1-3 (7 g, 18.2 mmol), compound 4-1 (12.4 g, 436 mmol), tris (dibenzylindeneacetone) dipalladium (2.0 g, 2.18 mmol) g, 4.36 mmol), sodium tert-butoxide (7.0 g, 73 mmol) and o-xylene (120 mL) were added and refluxed for 8 hours. The reaction mixture was cooled to room temperature and the solid was then filtered and washed with methylene chloride (MC). The filtrate was distilled under reduced pressure and purified by column chromatography to obtain the compound C-8 (4 g, 25%).

[ Example  5] Preparation of Compound C-40

compound C-40 Manufacturing

(5.2 g, 13.5 mmol), 4- (diphenylamino) phenylboronic acid (9.3 g, 32.4 mmol) and tris (dibenzylindeneacetone) dipalladium (1.2 g, 1.35 mmol) , S-Phos (1.1 g, 2.67 mmol), potassium tert-butoxide (5.3 g, 53.9 mmol) and 70 mL of 1,4-dioxane were placed and refluxed for 9 hours. After 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-40 (8.0 g, 77%).

Compounds C-1 to C-48 were synthesized in the same manner as the compounds prepared in Examples 1 to 5 above. Specific physical property data of the representative compounds are shown in Table 1 below.

[device Production Example 1 ] The organic Field  Using a luminescent compound OLED  Device fabrication

An OLED device was fabricated 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, Compound C-2 was placed in another cell in the vacuum vapor 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, a compound 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 each was doped with 50 wt%, thereby depositing a 30 nm electron transport layer. Next, 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 fabricate an OLED device. Each compound was purified by vacuum sublimation under 10 ^-6 torr.

As a result, a current of 2.4 mA / cm < ² > flowed and green luminescence of 1100 cd / m < ² > was confirmed.

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

Compound C-29 was deposited as a hole transporting layer to a thickness of 20 nm, and as a light emitting 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% To thereby form a light emitting layer having a thickness of 30 nm on the hole transporting layer, the OLED device was fabricated in the same manner as in Example 1.

As a result, a current of 13.2 mA / cm < ² > flowed and red emission of 1880 cd / m < ² > was confirmed.

[device Manufacturing example  3] The organic Field  Using a luminescent compound OLED  Device fabrication

An OLED device was fabricated in the same manner as in Device Manufacturing Example 1 except that Compound C-8 was deposited as a hole transporting layer to a thickness of 20 nm.

As a result, a current of 2.9 mA / cm < ² > flowed and a green emission of 1400 cd / m < ² > was confirmed.

[device Manufacturing example  4] The organic Field  Using a luminescent compound OLED  Device fabrication

An OLED device was fabricated in the same manner as in Device Manufacturing Example 1 except that Compound C-49 was deposited as a hole transporting layer to a thickness of 20 nm.

As a result, a current of 4.4 mA / cm < ² > flowed and a green emission of 2100 cd / m < ² > was confirmed.

[device Manufacturing example  5] The organic Field  Using a luminescent compound OLED  Device fabrication

An OLED device was fabricated in the same manner as in the Device Production Example 1 except that the compound C-40 was deposited to a thickness of 20 nm as a hole transporting layer.

As a result, a current of 18.0 mA / cm < ² > flowed and red emission of 2500 cd / m < ² > was confirmed.

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

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 fabricated in the same manner as in Example 1.

As a result, a current of 20.9 mA / cm < ² > flowed and a green luminescence of 8000 cd / m < ² > was confirmed.

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

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 fabricated in the same manner as in Example 2.

As a result, a current of 80.0 mA / cm < ² > flowed and red light emission of 6000 cd / m < ² >

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 is excellent in luminescence characteristics, particularly current efficiency.

Claims (8)

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

In Formula 1,
Ar ₁ to Ar ₄ are each independently a substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, or substituted or unsubstituted (5-30 membered) (3-30 membered) monovalent or polycyclic alicyclic or aromatic ring, 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 ;
Ar ₅ to Ar ₈ each independently represent hydrogen, deuterium, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, or substituted or unsubstituted (5-30 membered) Aryl or a substituted or unsubstituted (3-30 membered) 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 nitrogen, oxygen and sulfur ≪ / RTI >
m and n are each independently an integer of 0 to 2, and when m or n is 2, each of -N (Ar ₁ ) (Ar ₂ ) and each -N (Ar ₃ ) (Ar ₄ ) You can;
m + n is 2;
When m is 1 or 2, L ₁ is a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5-30 membered heteroarylene) L ₁ is selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 2 -C 30) alkenyl, substituted or unsubstituted (C 2 -C 30) alkynyl, (C6-C30) aryl, or substituted or unsubstituted (5-30 membered) heteroaryl;
When n is 1 or 2, L ₂ is a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (5-30 membered heteroarylene) L ₂ is selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 2 -C 30) alkenyl, substituted or unsubstituted (C 2 -C 30) alkynyl, (C6-C30) aryl, or substituted or unsubstituted (5-30 membered) heteroaryl;
o is 1 or 2, and when Ar 2 is 2, each Ar ₅ may be the same or different;
each of p, q and r is independently an integer of 1 to 4, and when p, q or r is an integer of 2 or more, each Ar ₆ , each Ar ₇ , and each Ar ₈ may be the same or different;
only,

,

And

If (wherein, X is _{-O-, -S-, -C (R 1} ) (R 2) - or -N (R ₃₎ -, and; R ₁ to R ₃ are each independently hydrogen, deuterium, halogen (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl , substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5-30 membered) heteroaryl or; R ₁ and R ₂ is (3-30 membered) monovalent or polycyclic alicyclic or aromatic ring, and the carbon atom of the alicyclic or aromatic ring formed may be replaced with one or more heteroatoms selected from nitrogen, oxygen and sulfur );
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 claim 1, wherein the compound represented by the formula (1) is represented by the following formula (2) or (3).
(2)

(3)

In the above Formulas 2 and 3,
Ar ₁ to Ar ₄ are each independently substituted or unsubstituted (C6-C30) aryl;
m and n are 1;
L ₁ , L ₂ , Ar ₅ to Ar ₈ , and o to r are as defined in formula (1). The organic electroluminescent compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 4 below.
[Chemical Formula 4]

In Formula 4,
Ar ₁ and Ar ₂ are each independently substituted or unsubstituted (C 6 -C 30) aryl;
L ₁ 'is substituted or unsubstituted (C 6 -C 30) arylene;
Two -N (Ar ₁ ) (Ar ₂ ) are bonded to each other at a meta position to L ₁ ';
Ar ₅ to Ar ₈ , and o to r are as defined in formula (1). 2. The compound according to claim 1, wherein in Ar ₁ to Ar ₈ , R ₁ to R ₃ , L ₁ and L ₂ are substituted alkyl, substituted alkenyl, substituted alkynyl, substituted cycloalkyl, substituted cycloalkenyl, substituted heterocycloalkyl, (C6-C30) aryl, (C1-C30) alkoxy, (C6-C30) aryl, (5-30 membered) heteroaryl, (C3-C30) cycloalkyl, (3-7 membered) heterocycloalkyl, tri (C1-C30) alkylsilyl, tri (C2-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1- (C6-C30) arylamino, (C1-C30) alkyl (C6-C30) alkyl optionally substituted by halogen, cyano, (C6-C30) arylcarbonyl, di (C1-C30) alkylcarbonyl, di (C1-C30) alkyl, di (C1-C30) alkyl (C6-C30) aryl, a carboxylic acid, an organic light emitting compound is at least one selected from the group consisting of nitro and hydroxyl. 2. The compound of claim 1, wherein Ar ₁ to Ar ₄ are each independently (C6-C20) aryl which is substituted or unsubstituted; Ar ₅ to Ar ₈ are each independently hydrogen or a (3-20 membered) monovalent or polycyclic aromatic ring connected with an adjacent substituent to form a substituted or unsubstituted aromatic ring, and the carbon atom of the formed aromatic ring may be substituted with nitrogen, Lt; / RTI > may be replaced by one or more heteroatoms selected from sulfur; When m is 1 or 2, L ₁ is a single bond or unsubstituted (C6-C20) arylene, and when m is 0, L ₁ is hydrogen; When n is 1 or 2, L ₂ is a single bond or unsubstituted (C 6 -C 20) arylene, and when n is 0, L ₂ is hydrogen. The compound of claim 1 wherein Ar ₁ to Ar ₄ are each independently selected from the group consisting of (C 1 -C 6) alkyl, (C 6 -C 15) aryl or di (C 1 -C 6) -C20) aryl; Ar ₅ to Ar ₈ are each independently hydrogen or a ( ₁ to ₅ membered) monocyclic or polycyclic aromatic ring which is connected to an adjacent substituent to be substituted or unsubstituted with (C1-C6) alkyl or (C6-C15) And the carbon atom of the aromatic ring formed may be replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur; When m is 1 or 2, L ₁ is a single bond or unsubstituted (C6-C15) arylene, and when m is 0, L ₁ is hydrogen; When n is 1 or 2, L ₂ is a single bond or unsubstituted (C 6 -C 15) arylene, and when n is 0, L ₂ is hydrogen. 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.