TW201520307A - Organic electroluminescent compound and organic electroluminescent device comprising the same - Google Patents

Abstract

The present disclosure relates to a novel organic electroluminescent compound and an organic electroluminescent device comprising the same. The organic electroluminescent compound of the present disclosure has high glass transition temperature, and thus shows good thermal stability. By using the organic electroluminescent compound of the present disclosure, an organic electroluminescent device showing excellent current efficiency can be provided.

Description

Organic electroluminescent compound and organic electric field illuminating device containing the same

Disclosed herein are organic electroluminescent compounds and organic electric field illuminating devices containing the same.

An electric field illuminating (EL) device is a self-illuminating device that has the advantage of providing a wider viewing angle, a larger contrast ratio, and faster response time. The organic EL device was first developed by Eastman Kodak Company by using a small aromatic diamine 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 been widely used as luminescent materials up to now. However, from the viewpoint of the electric field illuminating mechanism, phosphorescent materials have been extensively studied because the phosphorescent material theoretically enhances the luminous efficiency by four (4) times compared with the fluorescent material. The ruthenium (III) complex is widely known as a phosphorescent luminescent material, including bis(2-(2'-benzothienyl)-pyridine-N,C-3') oxime (acetoxime) ((acac) Ir (btp) ₂ ), ginseng (2-phenylpyridinium) ruthenium (Ir(ppy) ₃ ), ruthenium (4,6-difluorophenylpyridine-N, C2), Firpic, respectively, as red , green, and blue luminescent materials.

Currently, 4,4'-N,N'-dicarbazole-biphenyl (CBP) is the most widely known host material for phosphorescent materials. Recently, Pioneer (Japan) and others used bathocopper (BCP) and bismuth (2-methyl-8-hydroxyquinoline) (4-phenylphenol) aluminum (III) (BAlq) as the main material (which A high-performance organic EL device has been developed as a hole blocking material.

Although these materials provide good luminescent properties, they have the following disadvantages: (1) Due to their low glass transition temperature and poor thermal stability, they may degrade in a vacuum during high temperature deposition, resulting in poor service life. (2) The power efficiency of the organic EL device is obtained by [(π/voltage) × current efficiency], and the power efficiency is inversely proportional to the voltage. Although an organic EL device including a phosphorescent host material provides higher current efficiency (candle light (cd) / ampere (A)) than a device containing a fluorescent material, a relatively high driving voltage is required. Thus, it is not useful in terms of power efficiency (lumens (lm) / watt (W)). (3) Again, the operating life of the organic EL device is short, so it is still necessary to improve the luminous efficiency.

In order to improve efficiency and stability, the organic EL device can be fabricated to have a multilayer structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like. In this structure, the compound for the hole transport layer is important for the characteristics of the lifting device, such as the efficiency of transmitting the hole to the light-emitting layer, the luminous efficiency, and the service life.

In this respect, copper phthalocyanine (CuPc), 4,4'-贰[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-diphenyl -N,N'-贰(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine (TPD), 4,4',4"-para (3-A Phenylphenylamino)triphenylamine (MTDATA) is used as organic EL The cavity of the device is injected and transported. However, organic EL devices using such materials have problems in terms of quantum efficiency and service life. The reason is that when the organic EL device is driven at a high current, thermal stress occurs between the anode and the hole injection layer. Thermal stress significantly reduces the life of the device. Again, the organic material used in the hole injection layer has extremely high hole mobility, which may break the hole-electron charge balance and may reduce the quantum yield (cd/A). There is a need to develop a hole transport layer to enhance the durability of the organic EL device.

WO 2012/034627 discloses compounds for organic EL devices in which only one substituent selected from the group consisting of a diarylamine, a heteroarylamine, and a nitrogen-containing heteroaryl group is directly or through a linking group such as an aryl group. And the bond to the benzene ring of the snail. Therefore, this reference does not specifically disclose a compound in which two substituents are bonded to a linking group or bonded to a benzene ring of a snail, and an organic electric field illuminating device using the compound for a hole transport layer.

The object disclosed herein is to provide an organic electroluminescent compound which exhibits excellent current efficiency and thermal stability due to high glass transition temperature.

The inventors have found that the aforementioned object can be achieved by an organic electroluminescent compound represented by the following formula (1).

The organic electroluminescent compound represented by the formula (1) disclosed herein includes a spiro structure as a mother core, which provides high glass transition temperature and excellent thermal stability.

Wherein Ar ₁ to Ar ₄ each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted one ( 5 to 30 members) a heteroaryl group, or may be linked to one or more adjacent substituents to form a (3 to 30 membered) monocyclic or polycyclic cycloaliphatic or aromatic ring, the carbon atom of which may be At least one hetero atom selected from the group consisting of nitrogen, oxygen, and sulfur; Ar ₅ to Ar ₈ each independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted a (C6-C30) aryl group, or a substituted or unsubstituted (5 to 30 membered) heteroaryl group, or may be linked to one or more adjacent substituents to form a (3 to 30 membered) monocyclic ring or a polycyclic cycloaliphatic or aromatic ring, the carbon atom of which may be substituted with at least one hetero atom selected from the group consisting of nitrogen, oxygen, and sulfur; m and n each independently represent an integer from 0 to 2; When n is 2, each -N(Ar ₁ )(Ar ₂ ) or each -N(Ar ₃ )(Ar ₄ ) may be the same or different; m+n is 2; when m is 1 or 2, L ₁ represents a single bond, a substituted or non-substituted (C6-C30) arylene group, or a substituted or non-take The (5-30) extending heteroaryl; and when m is 0, L ₁ represents hydrogen, deuterium, substituted or non-substituted (C1-C30) alkyl, substituted or non-substituted (the C2- C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5 to 30 member) An aryl group; when n is 1 or 2, L ₂ represents a single bond, a substituted or unsubstituted (C6-C30) extended aryl group, or a substituted or unsubstituted (5 to 30 member) exo... When n is 0, L ₂ represents hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted Substituted (C2-C30) alkynyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5 to 30 membered) heteroaryl; o represents 1 or 2; When o is 2, each Ar ₅ may be the same or different; p, q, and r each independently represent an integer of 1 to 4; when p, q, or r is an integer of 2 or more, each Ar ₆ Each of Ar ₇ or each of Ar ₈ may be the same or different; and the heterocycloalkyl and (extended) heteroaryl groups each independently contain a group selected from the group consisting of B, N, O, S, P(=O), Si, And at least one hetero atom in P, the restriction is to exclude , ,and (wherein X represents -O-, -S-, -C(R ₁ )(R ₂ )-, or -N(R ₃ )-; R ₁ to R ₃ each independently represent hydrogen, deuterium, halogen, cyano , carboxy, nitro, hydroxy, substituted or unsubstituted (C1-C30) alkyl, 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 substituted or unsubstituted (5 to 30) a heteroaryl group; or R ₁ and R ₂ may be linked to each other to form a (3 to 30 membered) monocyclic or polycyclic cycloaliphatic or aromatic ring, the carbon atom of which may be selected from nitrogen, oxygen, And replacement of at least one hetero atom in the sulfur).

According to one aspect disclosed herein, the compound of the formula (1) can be preferably represented by the following formula (2) or (3).

Wherein, Ar ₁ to Ar ₄ each independently represent a substituted or unsubstituted (C6-C30) aryl group; m and n represent 1; and L ₁ , L ₃ , Ar ₅ to Ar ₈ , and o to r system As defined in equation (1).

According to another aspect disclosed herein, the compound of the formula (1) can be preferably represented by the following formula (4).

Wherein, Ar ₁ and Ar ₂ each independently represent a substituted or unsubstituted (C6-C30) aryl group; L ₁ ' represents a substituted or unsubstituted (C6-C30) extended aryl group; N(Ar ₁ )(Ar ₂ ) is meta-bonded to L ₁ '; and Ar ₅ to Ar ₈ and o to r are as defined in formula (1).

As shown in the formulas (2) to (4), an organic electroluminescent compound in which two diarylamines are meta-linked to the same aryl group has a small band gap due to conjugation. Therefore, when it is used in a hole transport layer, the layer has a relatively high triplet energy level, thereby blocking the transfer of excitons from the phosphorescent layer to the hole transport layer.

The organic electroluminescent compound disclosed herein can provide an organic electric field illuminating device exhibiting excellent current efficiency and thermal stability because of its high glass transition temperature (Tg).

In the following, the disclosure will be described in detail. However, the following detailed description is intended to explain the present invention and is not intended to limit the scope of the present invention. herein.

Disclosed herein are organic electroluminescent compounds of the above formula (1), organic electroluminescent materials comprising the same, and organic electroluminescent devices comprising the same.

The details of the organic electroluminescent compound of the formula (1) are as follows.

Here, "(C1-C30)alkyl" means a linear or branched alkyl group having 1 to 30, preferably 1 to 10, and more preferably 1 to 6 carbon atoms, including methyl, ethyl and n-propyl groups. , isopropyl, n-butyl, isobutyl, tert-butyl, and the like. "(C2-C30)alkenyl" means a linear or branched alkenyl group containing 2 to 30, preferably 2 to 20, and more preferably 2 to 10 carbon atoms, including vinyl, 1-propenyl, 2 a propylene group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 2-methylbut-2-enyl group, or the like. "(C2-C30)alkynyl" means a linear or branched alkynyl group having 2 to 30, preferably 2 to 20, and more preferably 2 to 10 carbon atoms, including ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, and the like. "(C3-C30)cycloalkyl" means a monocyclic or polycyclic hydrocarbon having from 3 to 30, preferably from 3 to 20, and more preferably from 3 to 7 carbon atoms, including cyclopropyl, cyclobutyl , cyclopentyl, cyclohexyl and the like. "(3 to 7 membered) heterocycloalkyl" is intended to include at least one selected from the group consisting of B, N, O, S, P(=O), Si, and P (preferably O, S, and N). A cycloalkyl group having a hetero atom and having 3 to 7 ring main chain atoms, including tetrahydrofuran, pyrrolidine, tetrahydrothiophene, tetrahydropyran, and the like. Further, "(C6-C30) (extended) aryl" means a monocyclic ring derived from an aromatic hydrocarbon and having 6 to 30, preferably 6 to 20, and more preferably 6 to 15 ring main chain carbon atoms. Or a fused ring, including phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, anthracenyl, phenylfluorenyl, benzindenyl, diphenyl Further, anthracenyl, phenanthryl, phenylphenanthrenyl, anthracenyl, fluorenyl, a tert-triphenyl, anthracenyl, condensed tetraphenyl, anthracenyl, anthracenyl, naphtylnaphthyl, a propadienyl fluorenyl, and the like. "(5 to 30 members) (extended) heteroaryl" means at least one selected from the group consisting of B, N, O, S, P(=O), Si, and P, preferably 1 to 4 An aryl group having 5 to 30 ring-chain atoms of a hetero atom; may be a monocyclic ring or a fused ring fused to at least one benzene ring; may be partially saturated; may be at least one impurity through a single bond An aryl or aryl group is bonded to a heteroaryl group; includes a monocyclic ring type heteroaryl group such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, iso Thiazolyl, different Azolyl, Azolyl, Diazolyl, three Base, four Base, triazolyl, tetrazolyl, furazolyl, pyridyl, pyridyl Base, pyrimidinyl, oxime And fused cycloheteroaryl such as benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, Benzoisothiazolyl, benzoid Azolyl, benzo Azolyl, isodecyl, fluorenyl, oxazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, porphyrinyl, quinazolinyl, quin Orolinyl, carbazolyl, brown Peptidyl, benzodiyl 呃基等. Further, "halogen" includes F, Cl, Br, and I.

Herein, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is replaced by another atom or a group, that is, a substituent. In the formula (1) disclosed herein, the substituted alkyl group, the substituted alkenyl group, the substituted alkynyl group, and the substituted alkyl group in Ar ₁ to Ar ₈ , R ₁ to R ₃ , L ₁ , and L ₂ Substituted cycloalkyl, substituted cycloalkenyl, substituted heterocycloalkyl, substituted (extended) aryl, and substituted (extended) heteroaryl are each independently selected from the group consisting of At least one of the group consisting of: hydrazine, halogen, unsubstituted or halogen-substituted (C1-C30) alkyl, (C1-C30) alkoxy, (C6-C30) aryl, unsubstituted Or (C6-C30) aryl substituted (3 to 30 membered) heteroaryl, (C3-C30)cycloalkyl, (3 to 7 membered) heterocycloalkyl, tri(C1-C30)alkylfluorene Base, tris(C6-C30)arylfluorenyl, di(C1-C30)alkyl(C6-C30)arylfluorenyl, (C1-C30)alkylbis(C6-C30)aryldecyl, C2-C30) alkenyl, (C2-C30)alkynyl, cyano, bis(C1-C30)alkylamino, unsubstituted or substituted by (C1-C30)alkyl (C6-C30) aryl Amino group, (C1-C30)alkyl (C6-C30) arylamino group, di(C6-C30) aryl boron group, di(C1-C30)alkylboryl group, (C1-C30)alkyl group (C6-C30) aryl boron group, (C6-C30) aryl (C1-C30) alkyl group, di(C1-C30) a (C6-C30) aryl group, a carboxyl group, a nitro group, and a hydroxyl group; and preferably selected from the group consisting of (C1-C6)alkyl, (C6-C15)aryl, and di(C1-C6)alkyl (C6) -C15) at least one of the group consisting of aryl groups.

Ar ₁ to Ar ₄ each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted group (5 to 30 members) a heteroaryl group, or may be linked to one or more adjacent substituents to form a (3 to 30 membered) monocyclic or polycyclic cycloaliphatic or aromatic ring, the carbon atom of which may be selected from Displacement of at least one of nitrogen, oxygen, and sulfur; preferably, substituted or unsubstituted (C6-C20) aryl; and more preferably, unsubstituted or via (C1-C6) An alkyl group, a (C6-C15) aryl group, or a (C6-C15) aryl group substituted with a (C6-C20) aryl group. Specifically, each of Ar ₁ to Ar ₄ may independently be a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenylnaphthyl group, a naphthylphenyl group, a fluorenyl group, a phenyl fluorenyl group, a benzofluorenyl group. , phenanthryl, tert-triphenyl, or propadienyl fluorenyl. Preferably, in the formula (2) or (3), at least one of Ar ₁ to Ar ₂ may be the same as Ar ₃ or Ar ₄ , wherein Ar ₃ and Ar ₄ may be the same or different.

Ar ₅ to Ar ₈ each independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted a (5 to 30 membered) heteroaryl group, or may be linked to one or more adjacent substituents to form a (3 to 30 membered) monocyclic or polycyclic cycloaliphatic or aromatic ring, the carbon atom of the ring Substituting at least one heteroatom selected from nitrogen, oxygen, and sulfur; preferably hydrogen, or may be linked to one or more adjacent substituents to form substituted or unsubstituted (3 to 20 members) a monocyclic or polycyclic aromatic ring, the carbon atom of which may be substituted with at least one hetero atom selected from the group consisting of nitrogen, oxygen, and sulfur; and more preferably hydrogen, or may be linked to one or more phases a (1 to 15 membered) monocyclic or polycyclic aromatic ring formed by an ortho substituent, the carbon atom of the ring being interrupted by at least one hetero atom selected from the group consisting of nitrogen, oxygen, and sulfur, and may be Substituted or substituted with (C1-C6)alkyl or (C6-C15)aryl. More specifically, Ar ₅ may be hydrogen; and one of Ar ₆ to Ar ₈ may be linked to one or more adjacent substituents to form a substituted or unsubstituted benzene ring, substituted or unsubstituted a benzofuran ring, a substituted or unsubstituted benzothiophene ring, or a substituted or unsubstituted anthracene ring.

When m is 1 or 2, L ₁ represents a single bond, a substituted or unsubstituted (C6-C30) extended aryl group, or a substituted or unsubstituted (5 to 30 membered) heteroaryl group; Preferably, it represents a single bond, or an unsubstituted (C6-C20) extended aryl group; more preferably represents a single bond, or an unsubstituted (C6-C15) extended aryl group; and specifically represents a phenyl group, a stretch Biphenyl, or naphthyl. When m is 0, L ₁ represents hydrogen, deuterium, 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 to 30 membered) heteroaryl; and specifically hydrogen.

When n is 1 or 2, L ₂ represents a single bond, a substituted or unsubstituted (C6-C30) extended aryl group, or a substituted or unsubstituted (5 to 30 membered) heteroaryl group; Preferably, it represents a single bond, or an unsubstituted (C6-C20) extended aryl group; more preferably represents a single bond, or an unsubstituted (C6-C15) extended aryl group; and specifically represents a phenyl group, a stretch Biphenyl, or naphthyl. When n is 0, L ₂ represents hydrogen, deuterium, 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 to 30 membered) heteroaryl; and specifically hydrogen.

According to a specific embodiment disclosed herein, in the formula (1), Ar ₁ to Ar ₄ each independently represent a substituted or unsubstituted (C6-C20) aryl group; and Ar ₅ to Ar ₈ each independently represent hydrogen. Or may be linked to one or more adjacent substituents to form a substituted or unsubstituted (3 to 20 membered) monocyclic or polycyclic aromatic ring, the carbon atom of which may be selected from nitrogen, oxygen And at least one hetero atom in the sulfur is substituted; when m is 1 or 2, L ₁ represents a single bond or an unsubstituted (C6-C20) extended aryl group; when m is 0, L ₁ represents hydrogen; When n is 1 or 2, L ₂ represents a single bond or an unsubstituted (C6-C20) extended aryl group; when n is 0, L ₂ represents hydrogen.

According to a specific embodiment disclosed herein, in the formula (1), Ar ₁ to Ar ₄ each independently represent unsubstituted or via (C1-C6)alkyl, (C6-C15)aryl, or di( C1-C6)alkyl (C6-C15) aryl substituted (C6-C20) aryl; Ar ₅ to Ar ₈ each independently represent hydrogen or may be linked to one or more adjacent substituents to form a monocyclic or polycyclic aromatic ring substituted with (C1-C6)alkyl or (C6-C15) aryl (3 to 15 member), the carbon atom of the ring may be selected from nitrogen, oxygen, and At least one hetero atom in sulfur is displaced; when m is 1 or 2, L ₁ represents a single bond or an unsubstituted (C6-C15) extended aryl group; when m is 0, L ₁ represents hydrogen; when n is When 1 or 2, L ₂ represents a single bond or an unsubstituted (C6-C15) extended aryl group; when n is 0, L ₂ represents hydrogen.

More specifically, the organic electroluminescent compound of the formula (1) includes the following, but is not limited thereto:

The organic electroluminescent compounds disclosed herein can be prepared by synthetic methods known to those skilled in the art. For example, it can be prepared according to the following Reaction Scheme 1.

[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 as defined in the above formula 1, and Hal represents a halogen.

According to the Buchwald-Hartwig reaction in Reaction Scheme 1, the arylamine and the aryl halide are reacted with each other under basic conditions (for example, sodium tributoxide) to form a carbon-nitrogen bond. . The reaction is carried out in an aromatic organic solvent such as toluene or xylene; and is usually carried out under reflux using a palladium complex such as palladium acetate and S-Phos (2-bicyclohexylphosphine-2',6'-dimethyl The combination of oxybiphenyl) is carried out as a catalyst.

Further, disclosed herein is an organic electroluminescent material that provides an organic electroluminescent compound of formula (1), and an organic electric field illuminating device comprising the same.

The material can comprise an organic electroluminescent compound disclosed herein. Otherwise, in addition to the compounds disclosed herein, the material may further comprise conventional compounds that have been used in organic electroluminescent devices.

The organic electric field light-emitting device may include a first electrode, a second electrode, and at least one organic layer disposed between the first and second electrodes. The organic layer may comprise at least one compound of formula (1).

One of the first electrode and the second electrode may be an anode, and the other may be a cathode. The organic layer may include 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 barrier layer, and an electron blocking layer. .

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

The organic electroluminescent device comprising the organic electroluminescent compound disclosed herein may further comprise at least one compound other than the organic electroluminescent compound disclosed herein as a host material. Further, the organic electric field light-emitting device may further comprise at least one dopant.

When the organic electroluminescent compound disclosed herein is included as a host material (first host material) of the light-emitting layer, another compound may be included as the second host material. The weight ratio between the first body material and the second body material is in the range of 1:99 to 99:1.

The second host material can be obtained from any of the known phosphorescent host materials. More specifically, in view of luminous efficiency, a compound selected from the group consisting of compounds of the formulae (11) to (13) is preferred as the second host material.

H-(Cz-L ₄ ) _h -M (11)

H-(Cz) _i -L ₄ -M (12)

Among them, 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 Substituted (C6-C30) aryl; L ₄ represents a single bond, substituted or unsubstituted (C6-C30) extended aryl, or substituted or unsubstituted (5 to 30 members) 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 each independently represent -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 not Substituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5 to 30 membered) heteroaryl; R ₃₂ and R ₃₃ may Identical or different; h and i each independently represent an integer from 1 to 3; j, k, a, and b each independently represent an integer from 0 to 4; and when h, i, j, When k, a, or b is an integer of 2 or more, each (Cz-L ₄ ), each (Cz), each R ₂₁ , each R ₂₂ , each R ₂₃ , or each R ₂₄ may be the same or different.

More specifically, the second subject material includes the following:

The dopant used in the organic electroluminescent compound disclosed herein is preferably at least one phosphorescent dopant. The phosphorescent dopant used in the organic electroluminescent compound disclosed herein is not particularly limited, but may be preferably selected from the group consisting of iridium (Ir), osmium (Os), copper (Cu), and palladium (Pt). a compound, more preferably selected from the group consisting of ortho-metallization complexes of iridium (Ir), osmium (Os), copper (Cu), and palladium (Pt), and even more preferably ortho-metalization Combined Compound.

The phosphorescent dopant may preferably be selected from the group consisting of compounds represented by the following formulas (101) to (103).

Wherein L is selected from the following structures:

R ₁₀₀ represents hydrogen, or substituted or unsubstituted (C1-C30)alkyl; R ₁₀₁ to R ₁₀₉ and R ₁₁₁ to R ₁₂₃ each independently represent hydrogen, deuterium, halogen, unsubstituted or substituted by halogen. (C1-C30) alkyl, cyano, substituted or unsubstituted (C1-C30) alkoxy, or substituted or unsubstituted (C3-C30) cycloalkyl; R ₁₂₀ to R ₁₂₃ Linked to one or more adjacent substituents to form a (3 to 30 membered) monocyclic or polycyclic cycloaliphatic or aromatic ring, such as a quinoline; R ₁₂₄ to R ₁₂₇ each independently represent hydrogen, deuterium, halogen , substituted or unsubstituted (C1-C30)alkyl, or substituted or unsubstituted (C6-C30) aryl; when R ₁₂₄ to R ₁₂₇ are aryl, they may be linked to one or more a (1 to 30 membered) monocyclic or polycyclic cycloaliphatic or aromatic ring, such as anthracene; and R ₂₀₁ to R ₂₁₁ each independently represent hydrogen, deuterium, halogen, unsubstituted or via a halogen-substituted (C1-C30)alkyl group; c and d each independently represent an integer of 1 to 3; when c or d is an integer of 2 or more, R ₁₀₀ each may be the same or different; and e represents An integer from 1 to 3.

More specifically, phosphorescent dopant materials include the following:

A mixture or composition for the preparation of an organic electric field illuminating device is provided in accordance with the additional aspects disclosed herein. The mixture or composition comprises a compound disclosed herein as a host material or a hole transport material. The mixture or composition may be a mixture or composition for the preparation of an emissive layer or a hole transport layer of an organic electroluminescent device.

The organic electric field light-emitting device disclosed herein may include a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode. The organic layer can comprise a light-emitting layer that can comprise a mixture or composition for use in the organic electric field illumination devices disclosed herein.

In addition to the compound of the formula (1), the organic electroluminescent device disclosed herein may further comprise at least one compound selected from the group consisting of an arylamine-based compound and a styrylarylamine-based compound. .

In the organic electric field light-emitting device disclosed herein, in addition to the compound of the formula (1), the organic layer may further comprise at least one metal selected from the group consisting of: Group 1, metal of the periodic table, Group 2 a metal, a fourth periodic transition metal, a fifth periodic transition metal, an organometallic of a lanthanide and a d-transition element; or at least one miscible compound comprising the metal. The organic layer may further include a light emitting layer and a charge generating layer.

Moreover, in addition to the compounds disclosed herein, the organic electric field illuminating device disclosed herein further comprises at least one layer of the following The light layer emits white light, and the light-emitting layer contains a blue (light) electric field luminescent compound, a red electric field luminescent compound, or a green electric field luminescent compound. The device may comprise an orange or yellow luminescent layer if desired.

In the organic electric field light-emitting device disclosed herein, preferably, at least one layer (hereinafter referred to as "surface layer") is selected from the group consisting of a chalcogenide layer, a metal halide layer and a metal oxide layer. Or on the inner surface of the two electrodes. More specifically, the chalcogenide or aluminum chalcogenide (including oxide) layer is preferably placed on the anode surface of the electroluminescent medium layer, and the metal halide layer or metal oxide layer is preferably placed in the electric field. On the cathode surface of the luminescent medium layer. Such a surface layer provides operational stability of the organic electric field illuminating device. Preferably, the chalcogenide comprises SiO _X (1 X 2), AlO _X (1 X 1.5), SiON, SiAlON, etc.; metal halides include LiF, MgF ₂ , CaF ₂ , rare earth metal fluorides, and the like; and metal oxides include Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO, and the like.

In the organic electric field light-emitting device disclosed herein, a mixed region of the electron transporting compound and the reducing dopant, or a mixed region of the hole transporting compound and the oxidizing dopant may be placed on at least one surface of the pair of electrodes. In this case, the electron transporting compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to the electric field illuminating medium. Further, the hole transporting compound is oxidized to a cation, and thus it becomes easier to inject and transport holes 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, a rare earth metal, and mixtures thereof. Reduced dopant layer As the charge generating layer, an organic electric field light-emitting device having two or more light-emitting layers and emitting white light can be employed.

In order to form the layers of the organic electric field light-emitting device disclosed herein, a dry film formation method such as a vacuum evaporation method, a sputtering method, a plasma plating method, and an ion plating method may be used, or a wet film formation method such as a spin coating method may be used. Dip coating method, and flow coating method.

When a wet film formation method is used, the film can be dissolved or dispersed by dissolving or dispersing a material forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, An alkane or the like is formed therefrom. The solvent may be any solvent in which the materials forming the layers are soluble or dispersible, and in which the film forming ability of the solvent is not problematic.

Hereinafter, the compounds disclosed herein, the preparation method of the compound, and the luminescent properties of the device will be explained in detail with reference to the following examples.

Example 1: Preparation of Compound C-2

Preparation of Compound 1-1

2,2,4-dichlorophenylboronic acid (20 g (g), 104 mmol (mmol)), 1-bromo-2-iodobenzene (44 g, 157 mmol), hydrazine (triphenyl) Palladium (0) (3.6 g, 3.14 mmol), sodium carbonate (27 g, 262 mmol), toluene 520 ml (mL) and 130 ml of ethanol were introduced into the reaction vessel and 130 ml of distilled water was added thereto. Thereafter, the mixture was stirred at 120 ° C for 6 hours. reaction Thereafter, the mixture was washed with distilled water and extracted with ethyl acetate. The extracted organic layer was dehydrated with magnesium sulfate. After removing the solvent by a rotary evaporator, the product was purified by column chromatography to afford Compound 1-1 (15 g, 50%).

Preparation of Compound 1-3

After introducing compound 1-1 (15 g, 50 mmol) and 170 ml of tetrahydrofuran into the reaction vessel, the mixture was cooled to -78 ° C under a nitrogen atmosphere, and then n-butyllithium 21 ml (2.5 M, 52 m Moer) slowly added to it. The mixture was stirred at -78 °C for 2 hours, and then anthrone (9.4 g, 52 mmol) was dissolved in 100 ml of tetrahydrofuran and added dropwise thereto. After the dropwise addition, the mixture was slowly warmed to room temperature and then stirred for an additional 30 minutes. After the aqueous ammonium chloride solution was added to the reaction mixture to complete the reaction, the mixture was extracted with ethyl acetate. The organic layer was dehydrated with magnesium sulfate, and the solvent was removed by a rotary evaporator to obtain Compound 1-2. After 500 ml of acetic acid and 0.2 ml of hydrochloric acid were added to the obtained compound 1-2, the mixture was stirred at 120 ° C overnight. After removing the solvent by a rotary evaporator, the products were purified by column chromatography to afford compound 1-3 (13 g, 70%).

Preparation of Compound C-2

Compound 1-3 (7 g, 18.1 mmol), N-phenylbiphenyl-4-amine (10.7 g, 43.6 mmol), bis(dibenzylideneacetone) dipalladium (1.9 g, 2.18) Millol), S-Phos (2 g, 4.36 mmol), sodium butoxide (6.9 g, 72 mmol), and 90 ml of o-xylene were introduced into a reaction vessel, and the mixture was refluxed for 2 hours. The reaction mixture was cooled to room temperature and then filtered. The resulting solid was washed with dichloromethane (MC). The filtrate was distilled under reduced pressure and purified by column chromatography to afford Compound C-2 (12 g, 84%).

Example 2: Preparation of Compound C-29

Preparation of Compound 2-1

In 2-bromoiodobenzene (29.7 g, 105 mmol), 2,4-dichlorophenyl-4-boronic acid (20 g, 105 mmol), hydrazine (triphenylphosphine) palladium (0) (3.6 g, 3.2 mmol), sodium carbonate (28 g, 263 mmol), 600 ml of toluene and 150 ml of ethanol were introduced into the reaction vessel and 150 ml of distilled water was added thereto, and the mixture was stirred at 120 ° C for 6 hours. . After the reaction, the mixture was washed with distilled water and extracted with ethyl acetate. The extracted organic layer was dehydrated with magnesium sulfate. After removing the solvent by a rotary evaporator, the product was purified by column chromatography to afford Compound 2-1 (19.5 g, 61%).

Preparation of Compound 2-2

In 1-indolinone (45 g, 340 mmol), o-phthalaldehyde (50 g, 374 mmol), sodium ethoxide (25 ml, 20 wt%, 70 mmol), and ethanol 1 After the liter (L) was introduced into the reaction vessel, the mixture was stirred at 120 ° C for 5 hours. After the reaction, the solution was cooled to room temperature, and the precipitated solid was washed with a small amount of methanol to afford compound 2-2 (50 g, 64%).

Preparation of compound 2-4

After introducing Compound 2-1 (18.5 g, 61.3 mmol) and 200 ml of tetrahydrofuran into the reaction vessel, the mixture was cooled to -78 under a nitrogen atmosphere. °C, and then n-butyl lithium 25 ml (2.5 M, 61.3 mmol) was slowly added dropwise thereto. The mixture was stirred at -78 ° C for 2 hours, and a compound 2-2 dissolved in 200 ml of tetrahydrofuran was added dropwise thereto. After the dropwise addition, the mixture was slowly warmed to room temperature and then stirred for an additional 30 minutes. After the aqueous ammonium chloride solution was added to the reaction mixture to complete the reaction, the mixture was extracted with ethyl acetate. The organic layer was dehydrated with magnesium sulfate, and then the solvent was removed by a rotary evaporator to obtain Compound 2-3. After 600 ml of acetic acid and 0.3 ml of hydrochloric acid were added to the obtained compound 2-3, the mixture was stirred at 120 ° C overnight. After removing the solvent by a rotary evaporator, the product was purified by column chromatography to afford compound 2-4 (14.3 g, 54%).

Preparation of Compound C-29

Compound 2-4 (12 g, 27.6 mmol), diphenylamine (10.3 g, 60.7 mmol), palladium(II) acetate (0.93 g, 4.14 mmol), 2-dicyclohexylphosphine- 2',6'-dimethoxybiphenyl (2.3 g, 5.5 mmol), sodium butoxide (6.6 g, 70 mmol), and 150 ml of o-xylene were introduced into the reaction vessel, and the mixture was refluxed. 8 hours. The reaction mixture was cooled to room temperature and then filtered. The resulting solid was washed with dichloromethane (MC). The filtrate was distilled under reduced pressure and purified by column chromatography to afford Compound C-29 (10 g, 53%).

Example 3: Preparation of Compound C-49

Preparation of Compound 3-1

In 1-Bromo-3-iodobenzene (20 g, 164 mol), phenylboronic acid (70 g, 246 mol), hydrazine (triphenylphosphine) palladium (0) (5.7 g, 0.49 mol), After sodium carbonate (43 g, 410 mol), 820 ml of toluene and 200 ml of ethanol were introduced into the reaction vessel and 200 ml of distilled water was added thereto, the mixture was stirred at 120 ° C for 6 hours. After the reaction, the mixture was washed with distilled water and extracted with ethyl acetate. The extracted organic layer was dehydrated with magnesium sulfate. After removing the solvent by a rotary evaporator, the product was purified by column chromatography to afford compound 3-1 (60 g, 150%).

Preparation of Compound 3-2

Compound 3-1 (60 g, 257 mol), aniline (70 ml, 46 mol), palladium (II) acetate (2.3 g, 103 m), S-Phos (11 g, 26 m), 800 ml of xylene was introduced into the reaction vessel, and the mixture was stirred at 120 ° C for 6 hours. After the reaction, the mixture was washed with distilled water and extracted with ethyl acetate. The extracted organic layer was dehydrated with magnesium sulfate. After removing the solvent by a rotary evaporator, the product was purified by column chromatography to afford compound 3-2 (26 g, 65%).

Preparation of Compound C-49

Compound 1-3 (6 g, 155 mmol), compound 3-2 (9 g, 373 mmol), bis(dibenzylideneacetone) dipalladium (1.7 g, 1.87 mmol), S -Phos (1.5 g, 3.73 mmol), sodium butoxide (6.0 g, 62 mmol), and 100 ml of o-xylene were introduced into a reaction vessel, and the mixture was refluxed for 8 hours. The reaction mixture was cooled to room temperature and then filtered. The resulting solid was washed with dichloromethane (MC). The filtrate is distilled under reduced pressure, and pure by column chromatography. Compound C-49 (6.4 g, 51%) was obtained.

Example 4: Preparation of Compound C-8

Preparation of Compound 4-1

2-Bromo-9,9-dimethyl-9H-indole (25 g, 91 mol), aniline (10 ml, 109 mmol), palladium (II) acetate (1.03 g, 4.58 mmol) Tributylphosphine (1.85 g, 9.15 mol) and 500 ml of xylene were introduced into the reaction vessel, and the mixture was stirred at 120 ° C for 6 hours. After the reaction, the mixture was washed with distilled water and extracted with ethyl acetate. The extracted organic layer was dehydrated with magnesium sulfate. After removing the solvent by a rotary evaporator, the product was purified by column chromatography to afford compound 4-1 (20 g, 76%).

Preparation of Compound C-8

Compound 1-3 (7 g, 18.2 mmol), compound 4-1 (12.4 g, 436 mmol), bis(dibenzylideneacetone) dipalladium (2.0 g, 2.18 mmol), S -Phos (1.79 g, 4.36 mmol), sodium butoxide (7.0 g, 73 mmol), and 120 ml of o-xylene were introduced into a reaction vessel, and the mixture was refluxed for 8 hours. The reaction mixture was cooled to room temperature and filtered. The resulting solid was washed with dichloromethane (MC). The filtrate was distilled under reduced pressure and purified by column chromatography to afford compound C-8 (4 g, 25%).

Example 5: Preparation of Compound C-40

Preparation of Compound C-40

Compound 1-3 (5.2 g, 13.5 mmol), 4-(diphenylamino)phenylboronic acid (9.3 g, 32.4 mmol), bis(dibenzylideneacetone) dipalladium (1.2 g) , 1.35 millimoles), S-Phos (1.1 grams, 2.67 millimoles), potassium butoxide (5.3 grams, 53.9 millimoles), and 1,4-two 70 ml of alkane was introduced into the reaction vessel, and the mixture was refluxed for 9 hours. After the reaction, the mixture was washed with distilled water and extracted with dichloromethane (MC). The extracted organic layer was dehydrated with magnesium sulfate. The solvent was removed by a rotary evaporator. These products were purified by column chromatography to afford compound C-40 (8.0 g, 77%).

Compounds C-1 to C-48 were prepared in a manner similar to the foregoing Examples 1 to 5. The physical properties of representative compounds in the prepared compounds are shown in Table 1 below.

[Device Example 1] OLED using the organic electroluminescent compound disclosed herein

OLEDs are made using the compounds disclosed herein as follows. A transparent electrode indium tin oxide (ITO) film (10 ohm/square unit (Ω/sq)) on a glass substrate of an organic light-emitting diode (OLED) (Geomatec) is sequentially subjected to acetone and isopropyl The alcohol is washed and then stored in isopropanol. The ITO substrate is then mounted on a substrate holder of a vacuum vapor deposition apparatus. N ¹ ,N ^{1 '} -([1,1'-biphenyl]-4,4'-diyl)indole (N ¹ -(naphthalen-1-yl)-N ⁴ ,N ⁴ -diphenylbenzene- The 1,4-diamine) was introduced into two chambers of a vacuum vapor deposition apparatus, and then the in-chamber pressure of the apparatus was controlled at 10 ^-6 Torr. Thereafter, a current was applied to the chamber to evaporate the introduction material, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate. Compound C-2 was then introduced into another chamber of the vacuum vapor deposition apparatus, and a current was applied to the chamber, whereby a hole transport layer having a thickness of 20 nm was formed on the hole injection layer. Thereafter, 9-(3-(4,6-diphenyl-1,3,5-three -2-yl)phenyl)-9'-phenyl-9H,9'H-3,3'-bicarbazole was introduced into a chamber of the vacuum vapor deposition apparatus as a host material, and compound D-1 It is introduced into another chamber as a dopant. The two materials were evaporated at different rates, so that a dopant was deposited at a doping amount of 15 wt% based on the total amount of the host and the dopant, and a light-emitting layer having a thickness of 30 nm was formed on the hole transport layer. Then introduce 2-(4-(9,10-bis(naphthalen-2-yl)indol-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole into a small chamber, and Lithium 8-hydroxyquinoline was introduced into another chamber. The two materials were evaporated at an equal rate such that an electron transport layer having a thickness of 30 nm was formed on the light-emitting layer by deposition at a doping amount of 50 wt%, respectively. Depositing lithium quinolate having a thickness of 2 nm on the electron transport layer as an electron injecting layer, and then depositing 150 on the electron injecting layer by another vacuum vapor deposition apparatus. Aluminum cathode with a thickness of nanometer. An OLED is thus fabricated. The entire material used to make the OLED was borrowed from a ^10-6 vacuum sublimation purifier. The manufactured OLED showed green light emission with a luminance of 1,100 candelas per square meter (cd/m ² ) and a current density of 2.4 milliamps per square centimeter (mA/cm ² ).

[Device Example 2] OLED using the organic electroluminescent compound disclosed herein

OLED was fabricated in the same manner as in Device Example 1, except that Compound C-29 was used to form a hole transport layer having a thickness of 20 nm; and in the case of 7-(4-([1,1'-biphenyl]- 4-yl)quinazolin-2-yl)-7H-benzo[c]carbazole as a host material and compound D-87 as dopants are respectively introduced into two chambers of a vacuum vapor deposition apparatus, When the two materials are evaporated at different rates, a dopant is deposited on the dopant transport layer at a dopant concentration of 3 wt% based on the total amount of the host and the dopant, and a light-emitting layer having a thickness of 30 nm is formed on the hole transport layer. The manufactured OLED showed red light with a brightness of 1,880 candelas per square meter and a current density of 13.2 milliamps per square centimeter.

[Device Example 3] OLED using the compound disclosed herein

The OLED was fabricated in the same manner as in Device Example 1, except that Compound C-8 was used to form a hole transport layer having a thickness of 20 nm. The manufactured OLED showed green light emission with a brightness of 1,400 candelas per square meter and a current density of 2.9 milliamps per square centimeter.

[Device Example 4] OLED using the compound disclosed herein

The OLED was fabricated in the same manner as in Device Example 1, except that Compound C-49 was used to form a hole transport layer having a thickness of 20 nm. The manufactured OLED showed a green light emission with a brightness of 2,100 candelas per square meter and a current density of 4.4 milliamps per square centimeter.

[Device Example 5] OLED using the compound disclosed herein

The OLED was fabricated in the same manner as in Device Example 2, except that Compound C-40 was used to form a hole transport layer having a thickness of 20 nm. The manufactured OLED showed red light with a brightness of 2,500 candelas per square meter and a current density of 18.0 milliamps per square centimeter.

[Comparative Device Example 1] OLED using a conventional compound

OLED was fabricated in the same manner as in Device Example 1, but using N,N'-bis(4-biphenyl)-N,N'-bis(4-biphenyl)-4,4'-diaminobiphenyl To form a hole transport layer having a thickness of 20 nm. The manufactured OLED showed a green light emission with a brightness of 8,000 candelas per square meter and a current density of 20.9 milliamps per square centimeter.

[Comparative Device Example 2] OLED using a conventional compound

OLED was fabricated in the same manner as in Device Example 2, but using N,N'-bis(4-biphenyl)-N,N'-bis(4-biphenyl)-4,4'-diaminobiphenyl To form a hole transport layer having a thickness of 20 nm. The manufactured OLED shows emission Red light has a brightness of 6,000 candelas per square meter and a current density of 80.0 milliamps per square centimeter.

[Comparative Device Example 3] OLED using a conventional compound

The OLED was fabricated in the same manner as in Device Example 1, except that Compound-1 was used to form a hole transport layer having a thickness of 20 nm. The manufactured OLED showed a green light emission with a brightness of 9,000 candelas per square meter and a current density of 21.5 milliamps per square centimeter.

[Comparative Device Example 4] OLED using a conventional compound

The OLED was fabricated in the same manner as in Device Example 2, except that Compound-1 was used to form a hole transport layer having a thickness of 20 nm. The manufactured OLED showed red light with a brightness of 7,000 candelas per square meter and a current density of 62.5 milliamps per square centimeter.

As evidenced by the examples and device examples, the organic electroluminescent compounds disclosed herein have high glass transition temperatures and provide higher current efficiencies than conventional compounds. By using the organic electroluminescent compound disclosed herein, the organic electric field illuminating device exhibits excellent luminous efficiency, particularly current efficiency.

Claims (8)

An organic electroluminescent compound which is represented by the following formula (1): Wherein Ar ₁ to Ar ₄ each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted one ( 5 to 30 members) heteroaryl, or may be linked to one or more adjacent substituents to form a (3 to 30 membered) monocyclic or polycyclic cycloaliphatic or aromatic ring, one or more of which The carbon atom may be substituted with at least one hetero atom selected from the group consisting of nitrogen, oxygen, and sulfur; and Ar ₅ to Ar ₈ each independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted Or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5 to 30 membered) heteroaryl, or may be linked to one or more adjacent substituents (3 to 30 members) a monocyclic or polycyclic cycloaliphatic or aromatic ring, the carbon atom of which may be substituted with at least one hetero atom selected from the group consisting of nitrogen, oxygen, and sulfur; m and n each independently represent an integer from 0 to 2; When m or n is 2, each -N(Ar ₁ )(Ar ₂ ) or each -N(Ar ₃ )(Ar ₄ ) may be the same or different; m+n is 2; when m is 1 or 2, L ₁ represents a single bond, a substituted or non-substituted (C6-C30) arylene group, or by taking Or non-substituted (5-30) extending heteroaryl; and when m is 0, L ₁ represents hydrogen, deuterium, substituted or non-substituted (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 to 30 members)heteroaryl; when n is 1 or 2, L ₂ represents a single bond, substituted or unsubstituted (C6-C30) extended aryl, or substituted or unsubstituted (5 to 30 members) a heteroaryl group; when n is 0, L ₂ represents hydrogen, deuterium, 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 to 30 membered) heteroaryl; o represents 1 Or 2; when o is 2, each Ar ₅ may be the same or different; p, q, and r each independently represent an integer from 1 to 4; when p, q, or r is an integer of 2 or greater each of Ar _6, each of Ar _7, Ar _8, or each may be the same or different and heterocycloalkyl ;; and (stretch) heteroaryl is independently selected from a group B, N, O, S P (= O), Si, P, and the at least one hetero atom, with the proviso that excluded , ,and (wherein X represents -O-, -S-, -C(R ₁ )(R ₂ )-, or -N(R ₃ )-; R ₁ to R ₃ each independently represent hydrogen, deuterium, halogen, cyano , carboxy, nitro, hydroxy, substituted or unsubstituted (C1-C30) alkyl, 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 substituted or unsubstituted (5 to 30) a heteroaryl group; or R ₁ and R ₂ may be linked to each other to form a (3 to 30 membered) monocyclic or polycyclic cycloaliphatic or aromatic ring, the carbon atom of which may be selected from the group consisting of nitrogen, oxygen, and At least one hetero atom in the sulfur is replaced). The organic electroluminescent compound according to claim 1, wherein the compound of the formula (1) is represented by the following formula (2) or (3): Wherein, Ar ₁ to Ar ₄ each independently represent a substituted or unsubstituted (C6-C30) aryl group; m and n represent 1; and L ₁ , L ₃ , Ar ₅ to Ar ₈ , and o to r system For example, the definition of patent scope 1 is defined. The organic electroluminescent compound according to claim 1, wherein the compound of the formula (1) is represented by the following formula (4): Wherein, Ar ₁ and Ar ₂ each independently represent a substituted or unsubstituted (C6-C30) aryl group; and L ₁ ' represents a substituted or unsubstituted (C6-C30) extended aryl group; -N(Ar ₁ )(Ar ₂ ) is meta-bonded to L ₁ '; and Ar ₅ to Ar ₈ , and o to r are as defined in the first item of the patent application. The organic electroluminescent compound according to claim 1, wherein the substituted alkyl group, the substituted alkenyl group, and the substituted alkyl group in Ar ₁ to Ar ₈ , R ₁ to R ₃ , L ₁ , and L ₂ Substituted alkynyl, substituted cycloalkyl, substituted cycloalkenyl, substituted heterocycloalkyl, substituted (extended) aryl, and substituted (extended) heteroaryl Independently at least one selected from the group consisting of hydrazine, halogen, unsubstituted or halogen-substituted (C1-C30) alkyl, (C1-C30) alkoxy, (C6-C30) Aryl, unsubstituted or substituted by (C6-C30) aryl (5 to 30 membered) heteroaryl, (C3-C30)cycloalkyl, (3 to 7 membered) heterocycloalkyl, tri (C1) -C30)alkylmercapto, tris(C6-C30)aryldecyl, di(C1-C30)alkyl(C6-C30)arylindenyl, (C1-C30)alkyldi(C6-C30) Arylsulfonyl, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, bis(C1-C30)alkylamino, unsubstituted or substituted by (C1-C30)alkyl (C6-C30) arylamino group, (C1-C30)alkyl (C6-C30) arylamino group, di(C6-C30) arylboryl group, di(C1-C30)alkylboryl group, C1-C30)alkyl (C6-C30) aryl boron group, C6-C30) aryl (C1-C30) alkyl, di(C1-C30)alkyl (C6-C30) aryl, carboxyl, nitro, and hydroxy. The organic electroluminescent compound according to claim 1, wherein Ar ₁ to Ar ₄ each independently represent a substituted or unsubstituted (C6-C20) aryl group; and Ar ₅ to Ar ₈ each independently represent hydrogen. Or may be linked to one or more adjacent substituents to form a substituted or unsubstituted (3 to 20 membered) monocyclic or polycyclic aromatic ring, the carbon atom of which may be selected from nitrogen, oxygen And at least one hetero atom in the sulfur is substituted; when m is 1 or 2, L ₁ represents a single bond or an unsubstituted (C6-C20) extended aryl group; when m is 0, L ₁ represents hydrogen; When n is 1 or 2, L ₂ represents a single bond or an unsubstituted (C6-C20) extended aryl group; when n is 0, L ₂ represents hydrogen. The organic electroluminescent compound according to claim 1, wherein Ar ₁ to Ar ₄ each independently represent unsubstituted or (C1-C6)alkyl, (C6-C15)aryl, or di(C1) -C6) alkyl (C6-C15) aryl substituted (C6-C20) aryl; Ar ₅ to Ar ₈ each independently represent hydrogen or may be linked to one or more adjacent substituents to form an unsubstituted Or a (C1-C6) alkyl or (C6-C15) aryl substituted (3 to 15 membered) monocyclic or polycyclic aromatic ring, the carbon atom of the ring may be selected from the group consisting of nitrogen, oxygen, and sulfur At least one hetero atom is substituted; when m is 1 or 2, L ₁ represents a single bond or an unsubstituted (C6-C15) extended aryl group; when m is 0, L ₁ represents hydrogen; when n is 1 Or 2, L ₂ represents a single bond or an unsubstituted (C6-C15) extended aryl group; when n is 0, L ₂ represents hydrogen. The organic electroluminescent compound according to claim 1, wherein the compound of the formula (1) is selected from the group consisting of: An organic electric field light-emitting device comprising the organic electroluminescent compound according to claim 1 of the patent application.