TW201434815A - Organic electroluminescent compounds and organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. By using the organic electroluminescent compound according to the present invention, an organic electroluminescent device having excellent current efficiency and luminous efficiency can be produced.

Description

Organic electric field luminescent compound and organic electric field illuminating device comprising the same

The present invention relates to an organic electroluminescent compound and an organic electric field illuminating device comprising the same.

The electric field illuminating device (EL device) is a self-illuminating device which has the advantages of providing a wider viewing angle, higher contrast, and faster reaction time. Eastman Kodak first developed an organic EL device using an aromatic diamine small molecule and an aluminum complex as a material for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].

The most important factor determining the luminous efficiency in an organic EL device is a luminescent material. Fluorescent materials have hitherto been widely used as luminescent materials. However, in view of the electric field illuminating mechanism, since phosphorescent materials are theoretically four (4) times more luminous efficiency than fluorescent materials, the development of phosphorescent materials has been extensively studied. The ruthenium (III) complex has been widely known as a phosphorescent material comprising bis(2-(2'-benzothienyl)-pyridine-N,C3') fluorene (ethyl fluorenyl) as red, green and blue materials, respectively. Acetone) ((acac)Ir(btp) ₂ ), ginseng (2-phenylpyridine) ruthenium (Ir(ppy) ₃ ) and bis(4,6-difluorophenylpyridine-N,C 2 )methylpyridinium ( Firpic).

Currently, 4,4'-N,N'-dicarbazole-biphenyl (CBP) is the most widely known phosphorescent host material. Recently, Pioneer et al. developed the use of bathocuproine (BCP) and aluminum (III) bis(2-methyl-8-hydroxyquinoline) (4-phenylphenol) (BAlq) as the main body. High-performance organic EL devices for materials, which are known as hole barrier materials.

Although these materials provide good luminescent properties, they have the following disadvantages: (1) They may degrade in a vacuum high temperature deposition process due to their low glass transition temperature and poor thermal stability. (2) The power efficiency of the organic EL device is given by [(π / voltage) × current efficiency], and therefore, the power efficiency is inversely proportional to the voltage. Compared to organic EL devices including phosphor materials, including phosphorescent host materials provide higher current efficiency (candle (cd) / ampere (A)), a significantly higher drive voltage is necessary. Therefore, there is no advantage in terms of power efficiency (lumens (lm) / watt (W)). (3) Further, the operational life of the organic EL device is short and the luminous efficiency still needs to be improved.

At the same time, copper phthalocyanine (CuPc), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-diphenyl-N , N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine (TPD), 4,4',4"-gin (3-methylbenzene) Phenylamino)triphenylamine (MTDATA) and the like have been used as a hole injection and transport material.

However, EL devices using such materials have problems in quantum efficiency and operational life. The reason is that when the organic EL device is driven at a high current, thermal stress is generated between the anode and the electric injection layer. Thermal Stress Significantly reduce the operational life of the device. Further, since the organic material used for the hole injection layer has a very high hole mobility, the hole-electron charge balance may be destroyed and the quantum yield (Cd/A) may be lowered.

Korean Patent No. 10-1153910 and Japanese Patent Application Laid-Open No. 2008-133225 disclose a compound in which a diarylamine is bonded to a benzene ring carbon atom of a fluorene skeleton via a linker such as an aryl group. A hole transport material for an organic EL device.

However, the above documents do not disclose a compound in which a diarylamine is bonded to a benzene ring nitrogen atom of a fluorene skeleton via a linker such as an aryl group.

An object of the present invention is to provide an organic electroluminescent compound having excellent current efficiency and luminous efficiency.

The inventors of the present invention have found that the above object can be attained by an organic electroluminescent compound represented by the following formula (1):

Wherein L ₁ represents a substituted or unsubstituted (C6-C30) extended aryl group or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; and L ₂ and L ₃ each independently represent a single a bond, a substituted or unsubstituted (C6-C30) extended aryl group or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; Ar ₁ and Ar ₂ each independently represent substituted or Unsubstituted (C6-C30) aryl or substituted or unsubstituted (3- to 30-membered) heteroaryl; R ₁ to R ₅ each independently represent hydrogen, deuterium, halogen, cyano, carboxy , nitro, hydroxy, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl , substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, Substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) an aryl _{group, -NR 11 R 12, -SiR 13} R 14 R 15, -SR 16, -OR 17, -COR 18 , or _{-B (oR 19) (oR 20} ); or linked to phase a substituent (group) to form a monocyclic or polycyclic substituted or unsubstituted (3- to 30-membered) alicyclic ring or an aromatic ring, wherein the carbon atom (group) may be selected from nitrogen, At least one hetero atom of oxygen and sulfur is substituted; R ₂ and R _{3 may} be bonded to each other to form a double bond; the restriction is that R _{5 is} not -NR ₁₁ R ₁₂ ; and R ₁₁ to R ₂₀ each independently represent hydrogen, deuterium, Halogen, cyano, carboxyl, nitro, hydroxy, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted ( C2-C30) alkynyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30 a cycloalkenyl group, a substituted or unsubstituted (3- to 7-membered) heterocycloalkyl group, a substituted or unsubstituted (C6-C30) aryl group or a substituted or unsubstituted (3- To a 30-membered heteroaryl; or to an adjacent substituent (group) to form a monocyclic or polycyclic (3- to 30-membered) alicyclic or aromatic ring, such as a carbon atom ( Group) may be selected from at least one heteroatom substitution of nitrogen, oxygen and sulfur; a represents an integer from 1 to 4; When a is an integer of 2 or more, each of R ₅ may be the same or different; the (hetero)heteroaryl group contains at least one selected from the group consisting of B, N, O, S, P(=O), Si, and P. a hetero atom; and the heterocycloalkyl group contains at least one hetero atom selected from the group consisting of O, S and N.

By using the organic electroluminescent compound according to the present invention, an organic electric field light-emitting device having excellent current efficiency and luminous efficiency can be produced.

Hereinafter, the present invention will be described in detail. However, the following disclosure is intended to be illustrative of the invention, and is not intended to limit the scope of the invention in any way.

The present invention relates to an organic electroluminescent compound of the formula (1), an organic electroluminescent material comprising the same, and an organic electric field emitting device comprising the same.

The electroluminescent compound of the above formula 1 will be described in detail.

Herein, "alkyl" includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, etc.; "alkenyl" includes vinyl, 1-propenyl, 2 - propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.; "alkynyl" includes ethynyl, 1-propynyl, 2- Propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 2-methylpent-2-ynyl, etc.; "cycloalkyl" includes cyclopropyl, cyclobutyl, cyclopentane Or a cyclohexyl group; "(3- to 7-membered) heterocycloalkyl" is selected from the group consisting of B, N, O, S, P(=O), Si and P (preferably O, S and N) a cycloalkyl group having 3 to 7 ring skeleton atoms of at least one hetero atom and including tetrahydrofuran, pyrrolidine, thietane, tetrahydropyran, etc.; "(extended) aryl group" is derived from an aromatic hydrocarbon Monocyclic or fused ring, and includes phenyl, biphenyl, terphenyl; naphthyl; binaphthyl, phenylnaphthyl, naphthylphenyl, anthracenyl, phenylfluorenyl, benzene And fluorenyl, dibenzofluorenyl, phenanthryl, phenylphenanthrenyl, anthryl, fluorenyl, triphenylenyl, fluorenyl, fused tetraphenyl, fluorene , chrysenyl, naphthylnaphthyl, fluoranthenyl, etc.; "(3- to 30-member) (extended) heteroaryl" is selected from the group consisting of B, N, O, S An aryl group having 3 to 30 ring skeleton atoms of at least one hetero atom of P(=O), Si and P (preferably O, S and N); a fused ring condensed with at least one benzene ring; And may be partially saturated; at least one heteroaryl or aryl group may be bonded to the heteroaryl group by a single bond (group); and includes a monocyclic heteroaryl group including a furyl group, a thienyl group, a pyrrolyl group, Imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, iso Azolyl, Azolyl, Diazolyl, three Base, four , triazolyl, tetrazolyl, furazolyl, pyridyl, bipyridyl, pyridyl Base, pyrimidinyl, oxime And the fused ring heteroaryl includes benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzo Isothiazolyl, benzoid Azolyl, benzo Azolyl, isodecyl, fluorenyl, oxazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, porphyrinyl, quinazoline, quin Orolinyl, carbazolyl, brown Peptidyl, benzodiyl Benzodioxolyl and the like. Further, "halogen" includes F, Cl, Br, and I.

According to a specific example of the present invention, the compound represented by Formula 1 is a compound represented by the following Formula 2.

Wherein L ₁ to L ₃ , Ar ₁ , Ar ₂ , R ₁ , R ₄ , R ₅ and a are as defined in the formula 1.

Herein, "substituted" in "substituted or unsubstituted" means that a hydrogen atom in a functional group is substituted with another atom or a group, that is, a substituent. L ₁ to _{L 3, Ar 1, Ar 2} , R 1 to R ₅ and R ₁₁ to R ₂₀ via the substituted (C1-C30) alkyl, substituted (C2-C30) alkenyl, substituted ( C2-C30) alkynyl, substituted (C1-C30) alkoxy, substituted (C3-C30) cycloalkyl, substituted (C3-C30) cycloalkenyl, substituted (3- to 7-membered) heterocycloalkyl, substituted (C6-C30) (extended) aryl, and substituted (3- to 30-membered) (extended) heteroaryl substituents, each independently selected from At least one of the following groups: anthracene, halogen, cyano, carboxyl, nitro, hydroxy, (C1-C30)alkyl, halo(C1-C30)alkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C1-C30)alkoxy, (C1-C20)alkylthio, (C3-C30)cycloalkyl, (C3-C30)cycloalkenyl, (3- to 7) - Member) Heterocycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio, unsubstituted or substituted by (C6-C30) aryl (3- to 30-member) Heteroaryl, unsubstituted or substituted (3- to 30-membered) heteroaryl (C6-C30) aryl, tri(C1-C30)alkyl fluorenyl, tris(C6-C30) aryl fluorene , bis(C1-C30)alkyl (C6-C30) aryl fluorenyl, (C1-C30)alkyl bis(C6-C30)aryl fluorenyl, amine, mono or di(C1-C30) Alkylamino, mono or di(C6-C30)arylamino, (C1-C30)alkyl(C6-C30)arylamino, (C1-C30)alkylcarbonyl, (C1-C30)alkane Oxycarbonyl, (C6-C30) arylcarbonyl, bis(C6-C30) aryl boron, bis(C1-C30)alkylboron, (C1-C30)alkyl(C6-C30) aryl boron a (C6-C30)aryl(C1-C30)alkyl group and a (C1-C30)alkyl(C6-C30)aryl group, and preferably each independently selected from (C1-C30)alkyl, At least one of 3- to 30-membered heteroaryl, (C6-C30) aryl, and di(C6-C30)arylamine groups.

In the above formula 1, L ₁ represents a substituted or unsubstituted (C6-C30) extended aryl group or a substituted or unsubstituted (3- to 30-membered) heteroaryl group, preferably represented by substitution. Or unsubstituted (C6-C20) extended aryl or substituted or unsubstituted (5- to 20-membered) heteroaryl, and more preferably unsubstituted or via (C1-C6) alkane A substituted (C6-C15) extended aryl group or an unsubstituted (5- to 7-membered) heteroaryl group.

L ₂ and L ₃ each independently represent a single bond, a substituted or unsubstituted (C6-C30) extended aryl group or a substituted or unsubstituted (3- to 30-membered) heteroaryl group, preferably. Each independently represents a single bond, a substituted or unsubstituted (C6-C20) extended aryl group or a substituted or unsubstituted (5- to 20-membered) heteroaryl group, and more preferably independently The group represents a (C6-C18) extended aryl group which is unsubstituted or substituted with a (C1-C6)alkyl group, or an unsubstituted (5- to 7-membered) heteroaryl group.

Ar ₁ and Ar ₂ each independently represent a substituted or unsubstituted (C6-C30) aryl group or a substituted or unsubstituted (3- to 30-membered) heteroaryl group, preferably each independently represented Substituted or unsubstituted (C6-C25) aryl or substituted or unsubstituted (5- to 20-membered) heteroaryl, and more preferably each independently represents unsubstituted or via (C1- C6) alkyl, (C6-C18) aryl, (5- to 15-membered) heteroaryl or di(C6-C10) arylamino substituted (C6-C18) aryl; or unsubstituted or (5- to 7-membered) heteroaryl substituted by (C6-C10) aryl or (5- to 7-membered) heteroaryl.

R ₁ to R ₅ each independently represent hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxy, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2- C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) naphthenic (C3-C30)cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) Aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, -NR ₁₁ R ₁₂ , -SiR ₁₃ R ₁₄ R ₁₅ , -SR ₁₆ , -OR ₁₇ , -COR ₁₈ or -B (OR ₁₉ )(OR ₂₀ ); or a substituted or unsubstituted (3- to 30-membered) alicyclic or aromatic ring bonded to an adjacent substituent (group) to form a monocyclic or polycyclic ring. And the carbon atom (group) thereof may be selected from at least one hetero atom of nitrogen, oxygen and sulfur, preferably each independently represents hydrogen, substituted or unsubstituted (C1-C10) alkyl, substituted Or unsubstituted (C6-C20) aryl or substituted or unsubstituted (5- to 20-membered) heteroaryl; or linked to the phase An ortho substituent (group) to form a monocyclic substituted or unsubstituted (5- to 20-membered) alicyclic ring, and more preferably each independently represents hydrogen, unsubstituted (C1-C6) An alkyl group, an unsubstituted or (C1-C6)alkyl substituted (C6-C18) aryl group, or an unsubstituted (5- to 15-membered) heteroaryl group; or linked to an adjacent substituent ( Group) to form a cyclopentyl or cyclohexyl group which is unsubstituted or substituted with a (C1-C6)alkyl group or a (C6-C10) aryl group.

R ₂ and R ₃ may be bonded to each other to form a double bond; and the limitation is that R _{5 is} not -NR ₁₁ R ₁₂ .

R ₁₁ to R ₂₀ each independently represent hydrogen, deuterium, halogen, cyano, carboxy, nitro, hydroxy, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2- C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) naphthenic (C3-C30)cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) An aryl group or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; or linked to an adjacent substituent (group) to form a monocyclic or polycyclic (3- to 30-membered) alicyclic ring A family ring or an aromatic ring, such as a carbon atom, may be substituted with at least one hetero atom selected from the group consisting of nitrogen, oxygen, and sulfur.

According to a specific embodiment of the present invention, in the above formula 1, L ₁ represents a substituted or unsubstituted (C6-C20) extended aryl group or a substituted or unsubstituted (5- to 20-membered) hydrazine group. And L ₂ and L ₃ each independently represent a single bond, a substituted or unsubstituted (C6-C20) extended aryl group or a substituted or unsubstituted (5- to 20-membered) heteroaryl group; Ar ₁ and Ar ₂ each independently represent a substituted or unsubstituted (C6-C25) aryl group or a substituted or unsubstituted (5- to 20-membered) heteroaryl group; and each of R ₁ to R ₅ Independently represents hydrogen, substituted or unsubstituted (C1-C10) alkyl, substituted or unsubstituted (C6-C20) aryl or substituted or unsubstituted (5- to 20-member) a heteroaryl group; or a substituted (unsubstituted or unsubstituted) (5- to 20-membered) alicyclic ring bonded to an adjacent substituent (group); and R ₂ and R ₃ may be bonded to each other; To form a double bond.

According to another embodiment of the present invention, in the above formula 1, L ₁ represents a (C6-C15) extended aryl group which is unsubstituted or substituted by a (C1-C6) alkyl group, or an unsubstituted (5- to 7) - member) heteroaryl; L ₂ and L ₃ each independently represent a single bond, unsubstituted or substituted by (C1-C6)alkyl (C6-C18) extended aryl, or unsubstituted (5 - to 7-member) heteroaryl; Ar ₁ and Ar ₂ each independently represent unsubstituted or via (C1-C6)alkyl, (C6-C18) aryl, (5- to 15-member) Aryl or di(C6-C10)arylamino substituted (C6-C18) aryl; or unsubstituted or substituted by ((C6-C10) aryl or (5- to 7-membered) heteroaryl (5- to 7-membered) heteroaryl; and R ₁ to R ₅ each independently represent hydrogen, unsubstituted (C1-C6)alkyl, unsubstituted or substituted by (C1-C6)alkyl (C6-C18) aryl, or unsubstituted (5- to 15-membered) heteroaryl; or linked to adjacent substituents (group) to form unsubstituted or (C1-C6) alkyl Or (C6-C10) aryl-substituted cyclopentyl or cyclohexyl; and R ₂ and R ₃ may be bonded to each other to form a double bond.

Specific compounds of the invention include, but are not limited to, the following:

The organic electroluminescent compound of the present invention can be synthesized by a method known to those skilled in the art. For example, they can be prepared according to the following Reaction Schemes 1 and 2.

Wherein L ₁ to L ₃ , Ar ₁ , Ar ₂ , R ₁ to R ₅ and a are as defined in the above formula 1, and Hal represents a halogen.

The present invention provides an organic electroluminescent material comprising an organic electroluminescent compound of Formula 1, and an organic electric field illuminating device comprising the same.

The above materials may be composed of the organic electroluminescent compound of the present invention, or may further include conventional materials generally used in organic electroluminescent materials.

The organic electric field illuminating device comprises a first electrode; a second electrode; and at least one organic layer is bounded between the first electrode and the second electrode. The organic layer may comprise at least one organic electroluminescent compound according to the invention.

One of the first electrode and the second electrode is an anode and the other is a cathode. The organic layer includes a light emitting layer, and may further include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer. .

The hole transport layer may be composed of two or more layers of hole transport layers, and when there are two or more layers of hole transport layers, the efficiency and lifetime of the organic electric field light-emitting device may be improved.

The organic electroluminescent compound according to the present invention may be included in at least one of the light-emitting layer and the hole transport layer. When used in a hole transport layer, the organic electric field luminescent compound represented by Formula 1 can be included as a hole transport material. When used in a light-emitting layer, the organic electroluminescent compound of Formula 1 can be contained as a host material.

Organic electroluminescent compound containing according to the invention The organic electric field light-emitting device may comprise at least one compound different from the organic electroluminescent compound according to the present invention as a host material, and may further comprise at least one dopant.

When the organic electroluminescent compound according to the present invention is contained as a host material (first host material), another compound may be contained as the second host material. Herein, the ratio of the first host material to the second host material is in the range of 1:99 to 99:1.

Another host material different from the organic electroluminescent compound according to the present invention may be from any of the known phosphorescent bodies. Specifically, from the viewpoint of luminous efficiency, a phosphorescent host selected from the group consisting of compounds of the following formulas 3 to 5 is preferred.

H-(Cz-L ₄ ) _h -M----------(3)

H-(Cz) _i -L ₄ -M----------(4)

Where Cz represents the following structure:

R ₂₁ to R ₂₄ each independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted Substituted (3- to 30-membered) heteroaryl or R ₂₅ R ₂₆ R ₂₇ Si-; R ₂₅ to R ₂₇ each independently represent substituted or unsubstituted (C1-C30)alkyl or substituted or Unsubstituted (C6-C30) aryl; L ₄ represents a single bond, substituted or unsubstituted (C6-C30) extended aryl or substituted or unsubstituted (5- to 30-membered) a heteroaryl group; M represents a substituted or unsubstituted (C6-C30) aryl group or a substituted or unsubstituted (5- to 30-membered) heteroaryl group; Y ₁ and Y ₂ are each independently represented - O-, -S-, -N(R ₃₁ )- or -C(R ₃₂ )(R ₃₃ )-, the restriction condition is that Y ₁ and Y _{2 are} not present at the same time; R ₃₁ to R ₃₃ each independently represent substituted Or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (5- to 30-membered) heteroaryl, R ₃₂ and R ₃₃ may be the same or different; H and i each independently represents an integer of 1 to 3; j, k, l and m are each independently an integer of 0 to 4; and when h, i, j, k, l m is an integer of 2 or more, each of the (Cz-L _4), each (HCz), each of R _21, each R _22, each R ₂₃ or R ₂₄ each may be the same or different.

Specifically, preferred embodiments of the host material are as follows;

The dopant is preferably at least one phosphorescent dopant. The phosphorescent dopant material applied to the electric field light-emitting device according to the present invention is not limited, but is preferably selected from the group consisting of metal-formed complex compounds of ruthenium, osmium, copper and platinum, more preferably selected from the group consisting of ruthenium, osmium, and copper. The ortho-metallization complex compound of platinum and, more preferably, the ortho-metallated ruthenium complex compound.

The phosphorescent dopant may preferably be selected from the compounds represented by the following formulas 6 to 8.

Wherein L is selected from the following structures:

R ₁₀₀ represents hydrogen, substituted or unsubstituted (C1-C30) alkyl or substituted or unsubstituted (C3-C30) cycloalkyl; R ₁₀₁ to R ₁₀₉ , and R ₁₁₁ to R ₁₂₃ are each independently Hydrogen; hydrazine; halogen; unsubstituted or substituted (C1-C30) alkyl substituted by halogen (group); substituted or unsubstituted (C3-C30)cycloalkyl; cyano; or substituted or Unsubstituted (C1-C30) alkoxy; adjacent substituents of R ₁₂₀ to R ₁₂₃ may be bonded to each other to form a fused ring, such as quinoline; R ₁₂₄ to R ₁₂₇ each independently represent hydrogen, deuterium, halogen, a substituted or unsubstituted (C1-C30) alkyl group or a substituted or unsubstituted (C6-C30) aryl group; when R ₁₂₄ to R ₁₂₇ are an aryl group, adjacent substituents may be bonded to each other To form a fused ring, such as hydrazine; R ₂₀₁ to R ₂₁₁ each independently represent hydrogen, deuterium, halogen, unsubstituted or halogen (group) substituted (C1-C30) alkyl or substituted or unsubstituted ( C3-C30)cycloalkyl; o and p each independently represent an integer from 1 to 3; when o or p is an integer of 2 or more, each R ₁₀₀ may be the same or different; and n is an integer from 1 to 3. .

Specifically, the phosphorescent dopant material comprises the following:

In another embodiment of the present invention, a composition for an organic electric field light-emitting device is provided. The composition comprises a compound according to the invention as a host material or a hole transport layer.

Further, an organic electric field light-emitting device according to the present invention includes a first electrode; a second electrode; and at least one organic layer interposed between the first electrode and the second electrode. The organic layer comprises a light-emitting layer, and the light-emitting layer may comprise a composition for use in an organic electric field light-emitting device according to the present invention.

The organic electric field light-emitting device according to the present invention may further comprise, in addition to the organic electroluminescent compound represented by Formula 1, a compound selected from the group consisting of an arylamine-based compound and a styrylarylamine-based compound. At least one compound of the group.

In the organic electric field light-emitting device according to the present invention, the organic layer may further comprise a transition metal selected from the group 1 metal of the periodic table, the metal of the second group, the transition element of the fourth cycle, the transition element of the fifth cycle, the lanthanide system, and the d- At least one metal of the transition metal of the transition element, or at least one complex compound comprising the metal. The organic layer may further include a light emitting layer and a charge generating layer.

Furthermore, in addition to the organic electroluminescent compound according to the present invention, the organic layer may further comprise at least one luminescent layer comprising a blue electric field luminescent compound, a red electric field, which is well known to those of ordinary skill in the art. A luminescent compound or a green electric field luminescent compound forms an organic electric field illuminating device that emits white light.

According to the invention, it is preferred to provide at least one layer (hereinafter referred to as "surface layer") on the surface of one or both of the electrodes; a layer selected from the group consisting of a chalcogenide layer, a metal halide and a metal oxide layer . Specifically, it is preferable to provide a chalcogenide (including oxide) layer on the anode surface of the electric field luminescent medium layer, and preferably to provide a metal halide layer or a metal oxide layer on the cathode surface of the electric field luminescent medium layer. The surface layer is stable to the operation of the organic electric field illuminating device. Preferably, the chalcogenide SiO _X (1 X 2), AlO _X (1 X 1.5), SiON, SiAlON, etc.; the metal halide includes LiF, MgF ₂ , CaF ₂ , olefinic metal fluoride, etc.; and the metal oxide includes Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO, etc. .

In the organic electric field light-emitting device according to the present invention, it is preferable to provide an electron transporting compound and a reductive doping on at least one surface of the electrode pair. A mixed region of the dopant or a mixed region of the hole transporting compound and the oxidizing dopant. In this case, the electron transporting compound is reduced to an anion, and thus becomes easily injected and transported into the electric field illuminating medium by the mixed region. Further, the hole transporting compound is oxidized to a cation and thus becomes easily injected and transported from the mixed region to the electric field illuminating medium. Preferably, the oxidizing dopant comprises various Lewis acids and acceptor compounds; and the reducing dopant comprises an alkali metal, an alkali metal compound, an alkaline earth metal, an olefin metal, and mixtures thereof. The reducing dopant layer can be applied as a charge generating layer to prepare an electric field light-emitting device having two or more layers of an electroluminescent layer and emitting white light. In order to form the layers of the organic electric field light-emitting device according to the present invention, a dry film forming method such as vacuum evaporation, sputtering, plasma or ion plating, or a wet film forming method such as spin coating, dip coating, and flow coating may be used. law.

When a wet film formation method is used, the material forming the layers can be dissolved or diffused in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, Alkane, etc. The solvent may be any solvent in which a material forming each layer is soluble or diffusible, and there is no problem in film forming ability.

Hereinafter, an organic electroluminescent compound, a method for producing the compound, and a light-emitting property of the device will be described in detail with reference to the following examples.

Example 1: Preparation of Compound C-52

Preparation of compound 1-1

1H-indole (20g, 0.170mol), 4-bromo-4'-iodo-1,1'-biphenyl (61g, 0.187mol), copper iodide (CuI) (6.5g, 0.034mol), B After diamine (EDA) (23 mL, 0.341 mol) and potassium phosphate (K ₃ PO ₄ ) (72.5 g, 0.341 mol) were dissolved in 0.9 L of toluene, the mixture was stirred at 120 ° C for 3 hours, and then cooled to room temperature. The mixture was then extracted with ethyl acetate and the resulting organic layer was washed with distilled water. The organic solvent was removed under reduced pressure. The resulting solid was washed with methanol, filtered and dried. The product thus obtained was separated by column chromatography to give Compound 1-1 (39 g, 66%).

Preparation of Compound C-52

Compound 1-1 (10 g, 28 mmol), bis([1,1'-biphenyl]-4-yl)amine (10.2 g, 32 mmol), tris-(dibenzylideneacetone)-dipalladium (Pd _{2 )} (dba) ₃ ) (0.5 g, 0.57 mmol), tris(o-tolyl)phosphine (P(o-Tol) ₃ ) (0.7 g, 2.28 mmol) and sodium butoxide (NaOt-Bu) ( 4.1 g, 43.08 mmol) was dissolved in 150 mL of toluene, and the mixture was stirred at 120 ° C for 3 hours, and then cooled to room temperature. The mixture was then extracted with ethyl acetate and the resulting organic layer was washed with distilled water. The organic solvent was removed under reduced pressure. The resulting solid was washed with methanol, filtered and dried. The product thus obtained was separated by column chromatography to give Compound C-52 (2.7 g, 16%).

Physical property data: melting point 195 ° C, UV 386 nm (in toluene), PL 405 nm (in toluene), molecular weight 588.74

Example 2: Preparation of Compound C-101

Preparation of Compound 2-1

Compound 2-1 (31 g, obtained by the same synthesis procedure as used in Example 1 for the preparation of compound 1-1 except that 2,3,4,9-tetrahydrocarbazole (20 g, 170 mmol) was used instead of 1H-oxime. 66%).

Preparation of Compound C-101

Compound 2-1 (10 g, 25 mmol), bis([1,1'-biphenyl]-4-yl)amine (8 g, 25 mmol), palladium acetate (Pd(OAc) ₂ ) (0.11 g, 0.5 mmol) After P(t-Bu) ₃ (0.4 mL, 1 mmol) and NaOt-Bu (3.6 g, 38 mmol) were dissolved in O-xylene 150 mL, the mixture was stirred at 120 ° C for 3 hours and then cooled to room temperature. The mixture was then extracted with ethyl acetate and the resulting organic layer was washed with distilled water. The organic solvent was removed under reduced pressure. The resulting solid was washed with methanol, filtered and dried. The product thus obtained was separated by column chromatography to give Compound C-101 (6.5 g, 44%).

Physical property data: melting point 304 ° C, UV 346 nm (in toluene), PL 396 nm (in toluene), molecular weight 642.83

Example 3: Preparation of Compound C-92

Preparation of compound 3-1

Tetrahydrofuran (THF) (700 mL) and 4-bromo-N,N-diphenylaniline (30 g, 0.093 mmol) were mixed in a flask, and after stirring the mixture in a nitrogen atmosphere, the mixture was slowly added at -78 ° C. n-BuLi (55 mL, 2.25 M). The mixture was then stirred at -78 °C for 1 hour, and trimethoxyborane (B(OMe) ₃ ) (21 mL, 0.19 mol) was slowly added to the mixture at -78 °C. The mixture was then heated to room temperature and allowed to react for 12 hours. After the reaction, the mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate (MgSO ₄₎ filtered and dried. The solvent was removed under reduced pressure, and the residue was crystallised to afford white solid compound 3-1 (17 g, 62%).

Preparation of Compound C-92

Compound 1-1 (7 g, 0.02 mol), compound 3-1 (7 g, 0.02 mol), hydrazine (triphenylphosphine) palladium (Pd(PPh ₃ ) ₄ ) (0.7 g, 0.6 mol), sodium carbonate ( After mixing 5.3 g, 0.05 mol), 100 mL of toluene, 25 mL of ethanol, and 25 mL of distilled water, the mixture was stirred at 120 ° C for 12 hours. After the reaction, the mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate, and filtered MgSO _4. The solvent was removed under reduced pressure, and the residue compound was purified by column chromatography to afford white solid compound C-92 (4.6 g, 45%).

Physical property data: melting point 205 ° C, UV 390 nm (in toluene), PL 411 nm (in toluene), molecular weight 512.64

Example 4: Preparation of Compound C-86

Preparation of Compound 4-1

4-Aminobiphenyl (19 g, 112 mmol), 2-(4-bromophenyl)naphthalene (26 g, 94 mmol), Pd(OAc) ₂ (0.5 g, 1.9 mmol), P(t-Bu)3 ( After 5 mL, 9.4 mmol), Cs ₂ CO ₃ (60 g, 190 mmol) and 500 mL of toluene were mixed in a flask, the mixture was reacted under reflux for 18 hours. Then, pure water was slowly added to the mixture to complete the reaction, and the reaction mixture was extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous MgSO _4, and the solvent removed. The residual material was then separated by column chromatography to give compound 4-1 (18 g, 52%).

Preparation of Compound C-86

Compound 4-1 (9 g, 24 mmol), Compound 1-1 (8.4 g, 24 mmol), Pd(OAc) ₂ (0.16 g, 0.72 mmol), P(t-Bu) ₃ (1 mL, 2.4 mmol), NaOt After -Bu (3.5 g, 36 mmol) and O-xylene 50 mL were mixed in a flask, the mixture was reacted under reflux for 1 hour. Purified water was then slowly added to the mixture to complete the reaction, and the reaction mixture was extracted with distilled water and ethyl acetate. After the organic layer was dried over anhydrous MgSO ₄ , solvent was evaporated. The residual material was then separated by column chromatography to give Compound Compound C-86 (9.1 g, 59%).

Physical property data: melting point 235 ° C, UV 346 nm (in toluene), PL 404nm (in toluene), molecular weight 638.80

Example 5: Preparation of Compound C-23

Preparation of compound 5-1

After mixing phenylhydrazine (60 g, 415 mmol), 2-methylcyclohexanone (47 g, 415 mmol) and acetic acid (AcOH) 270 mL in a flask, the mixture was stirred at 120 ° C for 5 hours. After the completion of the stirring, the mixture was slowly alkalized with a cooled 1 M aqueous sodium hydroxide solution. The reaction mixture was then extracted with dichloromethane (MC) and concentrated organic layer. The product was then chromatographed to give compound 5-1 (64 g, 84%).

Preparation of compound 5-2

After compound 5-1 (43 g, 230 mmol) and toluene 130 mL were mixed in a flask under a nitrogen atmosphere, the mixture was cooled to -20 °C. Then, 100 mL of 3 M methyllithium (Me-Li) was slowly added dropwise to the mixture, and the mixture was stirred at the same temperature for 3 hours. After the reaction, 150 mL of toluene and 150 mL of distilled water were slowly added to the mixture, and the organic layer was concentrated. The product was then isolated by column chromatography to afford compound 5-2 (36 g, 62%).

Preparation of compound 5-3

Compound 5-2 (36 g, 138 mmol), 4-bromo-4'-iodobiphenyl (74 g, 207 mmol), Pd(OAc) ₂ (1.2 g, 5.54 mmol), 2,2'-bisdiphenylphosphine After the base-1,1'-binaphthyl (BINAP) (3.45 g, 5.54 mmol) and NaOt-Bu (53 g, 554 mmol) were dissolved in toluene 700 mL, the mixture was reacted under reflux for 1 hour. After the reaction, the mixture was filtered, and the filtrate was concentrated. The concentrated mixture was then separated by column chromatography to give compound 5-3 (28 g, 50%).

Preparation of Compound C-23

Compound C-23 (5.4 g, 37%) was obtained by the same synthetic procedure used for the preparation of compound C-101 in Example 2 except that 5-3 (10 g, 23.1 mmol) was used instead of Compound 2-1.

Physical property data: melting point 232 ° C, UV 356 nm (in toluene), PL 404 nm (in toluene), molecular weight 672.90

Apparatus Example 1: Manufacture of an OLED device using an organic electroluminescent compound according to the present invention

An OLED device is fabricated using the luminescent material according to the invention. A transparent electrode indium tin oxide (ITO) film (15 Ω/sq) on a glass substrate (Samsung Corning, Republic of Korea) for organic light-emitting diode (OLED) device was ultrasonically washed with trichloroethylene, acetone, ethanol and distilled water. It is then stored in isopropanol. Then, the ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. N ¹ ,N ^{1 '} -([1,1'-biphenyl]-4,4'-diyl) bis(N ¹ -(naphthalen-1-yl)-N ⁴ ,N ⁴ -diphenylbenzene -1,4-Diamine) is introduced into the cell of the vacuum vapor deposition apparatus, and then the pressure of the chamber of the apparatus is adjusted to 10 ^-6 torr. Thereafter, a current was applied to the chamber to evaporate the introduced material, whereby a hole injection layer having a thickness of 60 nm was formed on the ITO substrate. Subsequently, the compound C-23 is introduced into another chamber of the vacuum vapor deposition apparatus, and is evaporated by applying a current to the chamber, whereby a hole transport layer having a thickness of 20 nm is formed on the hole injection layer. . After that, 9-(4,6-diphenyl-1,3,5-three -2-yl)-7,9'-diphenyl-9H,9'H-3,3'-bicarbazole was introduced into one of the chambers of the vacuum vapor deposition apparatus as a host and compound D-1 Introduced into another chamber as a dopant. The two materials were evaporated at different rates and deposited at a doping amount of 15% by weight based on the total amount of the host and the dopant to form a light-emitting layer having a thickness of 30 nm on the hole transport layer. Subsequently, the following compound E-1 was introduced into a small chamber, and lithium quinolate was introduced into another chamber. The two materials were evaporated at the same rate and deposited at a doping amount of 50% by weight, respectively, and an electron transport layer having a thickness of 30 nm was formed on the light-emitting layer. Subsequently, after depositing lithium hydroxyquinolate having a thickness of 2 nm as an electron injecting layer on the electron transporting layer, an aluminum (Al) cathode having a thickness of 150 nm was deposited on the electron injecting by another vacuum vapor deposition apparatus. On the floor. Thus, an OLED device is produced. All materials used to fabricate the OLED device were purified by vacuum sublimation at 10 ^-6 Torr prior to use.

The resulting OLED device showed green light having a luminance of 3660 candelas (cd) per square meter (m ² ) and a current density of 7.7 milliamperes (mA) per square centimeter (cm ² ).

Apparatus Example 2: Manufacture of an OLED device using an organic electroluminescent compound according to the present invention

In addition to forming a hole transport layer having a thickness of 20 nm by using the compound C-52 of the present invention, 9-phenyl-3-(4-(9-(4-phenylquinazolin-2-yl)-9H was introduced. -carbazol-3-yl)phenyl)-9H-carbazole to another chamber of a vacuum vapor deposition apparatus, introducing compound D-78 as a dopant, and evaporating the two materials at different rates, and An OLED device was fabricated in the same manner as in Device Example 1 except that a dopant amount of 3% by weight based on the total amount of the host and the dopant was deposited to form a light-emitting layer having a thickness of 30 nm on the hole transport layer. .

The prepared OLED device showed red light having a luminance of 1500 cd/m ² and a current density of 10.8 mA/cm ² .

Apparatus Example 3: Manufacture of an OLED device using an organic electroluminescent compound according to the present invention

An OLED device was fabricated in the same manner as in Device Example 1, except that Compound C-92 was used for the hole transport layer.

The prepared OLED showed green light having a luminance of 2800 cd/m ² and a current density of 5.8 mA/cm ² .

Apparatus Example 4: Manufacture of an OLED device using an organic electroluminescent compound according to the present invention

In addition to the use of compound C-86 in the hole transport layer, implemented by the device The OLED device was fabricated in the same manner as in Example 2.

The prepared OLED showed red light having a luminance of 2,600 cd/m ² and a current density of 19.7 mA/cm ² .

Comparative Example 1: Luminescence characteristics of OLEDs using conventional organic electroluminescent compounds

An OLED device was fabricated in the same manner as in Device Example 1, except that the compound R-1 shown below was evaporated as a 20 nm thick hole transport layer.

The prepared OLED showed green light having a luminance of 8730 cd/m ² and a current density of 21.4 mA/cm ² .

Comparative Example 2: Luminescence characteristics of OLEDs using conventional organic electroluminescent compounds

An OLED device was fabricated in the same manner as in Device Example 2, except that the compound R-2 shown below was evaporated as a 20 nm thick hole transport layer.

The prepared OLED showed red light having a luminance of 4,800 cd/m ² and a current density of 59.3 mA/cm ² .

By using the organic electroluminescent compound according to the present invention, an organic electric field light-emitting device having excellent current efficiency and luminous efficiency can be manufactured.

Claims (7)

An organic electroluminescent compound of the following formula 1: Wherein L ₁ represents a substituted or unsubstituted (C6-C30) extended aryl group or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; and L ₂ and L ₃ each independently represent a single a bond, a substituted or unsubstituted (C6-C30) extended aryl group or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; Ar ₁ and Ar ₂ each independently represent substituted or Unsubstituted (C6-C30) aryl or substituted or unsubstituted (3- to 30-membered) heteroaryl; R ₁ to R ₅ each independently represent hydrogen, deuterium, halogen, cyano, carboxy , nitro, hydroxy, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl , substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, Substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) an aryl _{group, -NR 11 R 12, -SiR 13} R 14 R 15, -SR 16, -OR 17, -COR 18 , or _{-B (oR 19) (oR 20} ); or linked to phase a substituent (group) to form a monocyclic or polycyclic substituted or unsubstituted (3- to 30-membered) alicyclic ring or an aromatic ring, wherein the carbon atom (group) may be selected from nitrogen, At least one hetero atom of oxygen and sulfur is substituted; R ₂ and R ₃ may be bonded to each other to form a double bond; the restriction is that R _{5 is} not -NR ₁₁ R ₁₂ ; and R ₁₁ to R ₂₀ each independently represent hydrogen, deuterium, Halogen, cyano, carboxyl, nitro, hydroxy, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted ( C2-C30) alkynyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30 a cycloalkenyl group, a substituted or unsubstituted (3- to 7-membered) heterocycloalkyl group, a substituted or unsubstituted (C6-C30) aryl group or a substituted or unsubstituted (3- To a 30-membered heteroaryl; or to an adjacent substituent (group) to form a monocyclic or polycyclic (3- to 30-membered) alicyclic or aromatic ring, such as a carbon atom ( Group) may be selected from at least one heteroatom substitution of nitrogen, oxygen and sulfur; a represents an integer from 1 to 4; When a is an integer of 2 or more, each of R ₅ may be the same or different; the (hetero)heteroaryl group contains at least one selected from the group consisting of B, N, O, S, P(=O), Si, and P. a hetero atom; and the heterocycloalkyl group contains at least one hetero atom selected from the group consisting of O, S and N. An organic electroluminescent compound according to claim 1, which is a compound represented by the following formula 2: Wherein L ₁ to L ₃ , Ar ₁ , Ar ₂ , R ₁ , R ₄ , R ₅ and a are as defined in the first item of the patent application. The organic electroluminescent compound according to claim 1, wherein the substituted (C1-C30) alkane of L ₁ to L ₃ , Ar ₁ , Ar ₂ , R ₁ to R ₅ and R ₁₁ to R ₂₀ Substituted, substituted (C2-C30) alkenyl, substituted (C2-C30) alkynyl, substituted (C1-C30) alkoxy, substituted (C3-C30) cycloalkyl, substituted (C3-C30)cycloalkenyl, substituted (3- to 7-membered) heterocycloalkyl, substituted (C6-C30) (extended) aryl, and substituted (3- to 30-membered) a substituent of a heteroaryl group, each independently being at least one selected from the group consisting of hydrazine, halogen, cyano, carboxyl, nitro, hydroxy, (C1-C30)alkyl, Halogen (C1-C30)alkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C1-C30)alkoxy, (C1-C30)alkylthio, (C3-C30) ring Alkyl, (C3-C30)cycloalkenyl, (3- to 7-membered)heterocycloalkyl, (C6-C30)aryloxy, (C6-C30)arylthio, unsubstituted or via (C6-C30) aryl-substituted (3- to 30-membered) heteroaryl, unsubstituted or substituted (3- to 30-membered) heteroaryl (C6-C30) aryl, tri(C1 -C30) alkyl fluorenyl, tris(C6-C30) aryl fluorenyl, di(C1-C30)alkyl (C6-C30) aryl fluorenyl , (C1-C30)alkyl di(C6-C30)arylfluorenyl, amine, mono or di(C1-C30)alkylamino, mono or di(C6-C30)arylamino, (C1 -C30)alkyl (C6-C30) arylamino group, (C1-C30) alkylcarbonyl group, (C1-C30) alkoxycarbonyl group, (C6-C30) arylcarbonyl group, di(C6-C30) aryl group Boronyl, bis(C1-C30)alkylboron, (C1-C30)alkyl(C6-C30)arylboryl, (C6-C30)aryl(C1-C30)alkyl and (C1- C30) alkyl (C6-C30) aryl. The organic electroluminescent compound according to claim 1, wherein L ₁ represents a substituted or unsubstituted (C6-C20) extended aryl group or a substituted or unsubstituted (5- to 20-member) Heteroaryl; L ₂ and L ₃ each independently represent a single bond, substituted or unsubstituted (C6-C20) extended aryl or substituted or unsubstituted (5 to 20-membered) Aryl; Ar ₁ and Ar ₂ each independently represent a substituted or unsubstituted (C6-C25) aryl group or a substituted or unsubstituted (5- to 20-membered) heteroaryl group; and R ₁ to R ₅ each independently represents hydrogen, substituted or unsubstituted (C1-C10)alkyl, substituted or unsubstituted (C6-C20) aryl or substituted or unsubstituted (5 to 20) a member of the heteroaryl group; or a substituted (unsubstituted or unsubstituted) (5- to 20-membered) alicyclic ring bonded to an adjacent substituent (group); and R ₂ and R ₃ may be Bonded to each other to form a double bond. The organic electroluminescent compound according to claim 1, wherein L ₁ represents an unsubstituted or substituted (C6-C15) aryl group substituted by a (C1-C6) alkyl group, or unsubstituted (5- To 7-membered) heteroaryl; L ₂ and L ₃ each independently represent a single bond, unsubstituted or (C6-C18) extended aryl substituted by (C1-C6)alkyl, or unsubstituted (5- to 7-member) heteroaryl; Ar ₁ and Ar ₂ each independently represent unsubstituted or via (C1-C6)alkyl, (C6-C18) aryl, (5- to 15-member) a heteroaryl or di(C6-C10)arylamino substituted (C6-C18) aryl; or unsubstituted or via (C6-C10) aryl or (5- to 7-membered) heteroaryl Substituted (5- to 7-membered) heteroaryl; and R ₁ to R ₅ each independently represent hydrogen, unsubstituted (C1-C6)alkyl, unsubstituted or via (C1-C6)alkyl Substituted (C6-C18) aryl, or unsubstituted (5- to 15-membered) heteroaryl; or linked to adjacent substituents (group) to form unsubstituted or via (C1-C6) alkane Or a (C6-C10) aryl-substituted cyclopentyl or cyclohexyl group; and R ₂ and R ₃ may be bonded to each other to form a double bond. The organic electroluminescent compound according to claim 1, wherein the compound represented by the formula 1 is selected from the group consisting of: An organic electric field light-emitting device comprising the electric field light-emitting compound according to claim 1 of the patent application.