WO2016089080A1 - Organic luminescent compound and organic electroluminescent device comprising same - Google Patents

Abstract

The present invention relates to a novel tertiary substituted benzene-based compound having excellent hole injection, transfer ability and luminescent ability, and an organic electroluminescent device comprising the same. The compound according to the present invention can improve the light-emitting efficiency, driving voltage, and life of the organic electroluminescent device by using the compound in an organic material layer, preferably a luminescent layer, of the organic electroluminescent device.

Description

Organic light emitting compound and organic electroluminescent device comprising the same

The present invention relates to a novel organic light emitting compound and an organic electroluminescent device comprising the same, and more particularly, by including a novel tertiary substituted benzene-based compound having excellent hole injection, transporting ability, and luminescent ability in one or more organic material layers, The present invention relates to an organic EL device having improved characteristics such as efficiency, driving voltage, and lifetime.

The study of organic electroluminescent (EL) devices (hereinafter referred to simply as 'organic EL devices') that led to blue electroluminescence using anthracene monocrystals in 1965 from the observation of Bernanose organic thin film emission from the 1950s In 1987, Tang presented an organic electroluminescent device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer. Since then, in order to make high-efficiency, high-life organic electroluminescent device, it has been developed in the form of introducing each characteristic organic material layer in the device, leading to the development of specialized materials used therein.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine. In this case, the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.

The light emitting layer forming material of the organic EL device may be classified into blue, green, and red light emitting materials according to light emission colors. In addition, yellow and orange light emitting materials are also used to achieve a better natural color. In addition, a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.

The dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. At this time, since the phosphorescent material can theoretically improve the luminous efficiency up to 4 times as compared with the fluorescent material, research on phosphorescent host materials as well as phosphorescent dopants has been conducted.

Hole injection layer, hole transport layer to date. As the hole blocking layer and the electron transporting layer, NPB, BCP, Alq ₃ and the like represented by the following formulas are widely known, and anthracene derivatives have been reported as fluorescent dopant / host materials in the light emitting material. Particularly, phosphorescent materials having great advantages in terms of efficiency improvement among light emitting materials include metal complex compounds including Ir such as Firpic, Ir (ppy) ₃ , and (acac) Ir (btp) ₂ as blue, green, and red dopant materials. It is used. To date, 4,4-dicarbazolybiphenyl (CBP) has shown excellent properties as a phosphorescent host material.

However, the existing materials have advantages in terms of light emission characteristics, but the thermal stability is low due to the low glass transition temperature, and thus the materials are not satisfactory in terms of lifespan of the organic EL device.

In order to solve the above problems, an object of the present invention is to provide a novel organic compound having a high glass transition temperature, excellent thermal stability, and improving the bonding force between holes and electrons.

In addition, an object of the present invention is to provide an organic electroluminescent device including the organic compound exhibiting a low driving voltage and high luminous efficiency.

In order to achieve the above object, the present invention provides a compound represented by the following formula (1):

[Formula 1]

In Chemical Formula 1,

Ar ₁ is a C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl group, C Aryl group of ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C ₁ to C ₄₀ , aryloxy group of C ₆ to C ₆₀ , alkylsilyl group of C ₃ to C ₄₀ , C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₆₀ aryl boron group, C ₆ to C ₆₀ arylphosphine group, C ₆ to C ₆₀ mono or diaryl phosph It is selected from the group consisting of a pinyl group and an arylamine group of C ₆ ~ C ₆₀ ,

Y ₁ is O or S;

Z ₁ is selected from the group consisting of a single bond, C (R ₁₁ ) (R ₁₂ ), N (R ₁₃ ), O and S;

L ₁ and L ₂ are each independently a single bond, C ₆ ~ C ₄₀ aryl group and a nuclear atoms of 5 to 4O hetero arylene group is selected from the group consisting of;

R ₁ to R ₉ and R ₁₁ to R ₁₃ are each independently hydrogen, deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, nuclear atoms 5 to 40 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, A C ₆ to C ₄₀ arylphosphine group, a C ₆ to C ₄₀ mono or diarylphosphinyl group and a C ₆ to C ₄₀ arylsilyl group, or a condensed aromatic ring or condensation in combination with an adjacent group Can form a heteroaromatic ring;

m is an integer from 0 to 4;

R ₁₀ is deuterium, halogen, cyano group, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group, C ₂ -C ₄₀ alkynyl group, C ₆ -C ₄₀ aryl group, nuclear atom 5 to 40 heteroaryl groups, C ₆ to C ₄₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₄₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₄₀ arylboron groups, C ₆ to C ₄₀ arylphosphine groups, C ₆ to C ₄₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ selected from the group consisting arylsilyl of C ₄₀ or, by combining groups of adjacent, may form a fused aromatic ring, or a condensed heteroaromatic ring, a plurality of the R ₁₀ is In individuals they are the same or different from one another;

Any one of R ₁ to R ₉ forms a bond with L ₂ ;

The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkyl boron group, aryl of the above R ₁ to R ₁₃ Boron group, arylphosphine group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, 5 to 40 heteroaryl group of nuclear atoms, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ Arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₄₀ the arylboronic group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₄₀ aryl silyl groups at least one member selected from the group consisting of If the ring is substituted or unsubstituted, substituted by a plurality of substituent group, they may be the same or different from each other.

In addition, the present invention is an organic electroluminescent device comprising (i) an anode, (ii i) cathode and (ii i) one or more organic material layers interposed between the anode and the cathode, at least one of the one or more organic material layers It provides an organic electroluminescent device comprising a compound represented by the formula (1).

"Alkyl" in the present invention is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl And the like, but are not limited thereto.

"Alkenyl" in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon of 2 to 40 carbon atoms having one or more carbon-carbon double bonds. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.

"Alkynyl" in the present invention means a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.

"Aryl" in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. In addition, a form in which two or more rings are attached to each other (pendant) or condensed may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

"Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are pendant or condensed with each other may be included, and may also include a form in which the two or more rings are condensed with an aryl group. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R 'means alkyl having 1 to 40 carbon atoms, and is linear, branched or cyclic. It may include a structure. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.

"Arylamine" in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.

By "cycloalkyl" in the present invention is meant monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

"Heterocycloalkyl" in the present invention means a monovalent substituent derived from 3 to 40 non-aromatic hydrocarbons of nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons is N, O, Substituted with a hetero atom such as S or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

In the present invention, "alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 40 carbon atoms.

"Condensed ring" in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combination thereof.

The compound represented by Formula 1 according to the present invention can be used as a material of the organic material layer of the organic electroluminescent device because of its excellent thermal stability and phosphorescence properties. In particular, when the compound represented by Chemical Formula 1 according to the present invention is used as a phosphorescent host material, an organic electroluminescent device having excellent light emission performance, low driving voltage, high efficiency, and long life compared to a conventional host material can be manufactured. Full color display panels with significantly improved performance and lifetime can also be manufactured.

The present invention provides a compound represented by Formula 1:

[Formula 1]

In Chemical Formula 1,

Ar ₁ is a C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl group, C Aryl group of ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C ₁ to C ₄₀ , aryloxy group of C ₆ to C ₆₀ , alkylsilyl group of C ₃ to C ₄₀ , C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₆₀ aryl boron group, C ₆ to C ₆₀ arylphosphine group, C ₆ to C ₆₀ mono or diaryl phosph It is selected from the group consisting of a pinyl group and an arylamine group of C ₆ ~ C ₆₀ ,

Y ₁ is O or S;

Z ₁ is selected from the group consisting of a single bond, C (R ₁₁ ) (R ₁₂ ), N (R ₁₃ ), O and S;

L ₁ and L ₂ are each independently selected from the group consisting of a single bond, an arylene group having ₆ to ₄₀ carbon atoms and a heteroarylene group having 5 to 40 nuclear atoms;

R ₁ to R ₉ and R ₁₁ to R ₁₃ are each independently hydrogen, deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, nuclear atoms 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, A C ₆ to C ₄₀ arylphosphine group, a C ₆ to C ₄₀ mono or diarylphosphinyl group and a C ₆ to C ₄₀ arylsilyl group, or a condensed aromatic ring or condensation in combination with an adjacent group Can form a heteroaromatic ring;

m is an integer from 0 to 4;

R ₁₀ is deuterium, halogen, cyano group, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group, C ₂ -C ₄₀ alkynyl group, C ₆ -C ₄₀ aryl group, nuclear atom 5 to 40 heteroaryl groups, C ₆ to C ₄₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₄₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₄₀ arylboron groups, C ₆ to C ₄₀ arylphosphine groups, C ₆ to C ₄₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ selected from the group consisting arylsilyl of C ₄₀ or, by combining groups of adjacent, may form a fused aromatic ring, or a condensed heteroaromatic ring, a plurality of the R ₁₀ is In individuals they are the same or different from one another;

Any one of R ₁ to R ₉ forms a bond with L ₂ ;

The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkyl boron group, aryl of the above R ₁ to R ₁₃ Boron group, arylphosphine group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, 5 to 40 heteroaryl group of nuclear atoms, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ Arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₄₀ the arylboronic group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₄₀ aryl silyl groups at least one member selected from the group consisting of If the ring is substituted or unsubstituted, substituted by a plurality of substituent group, they may be the same or different from each other.

Hereinafter, the present invention will be described in detail.

1. New Organic Compounds

The present invention provides a novel tertiary substituted benzene compound having a higher molecular weight than the conventional organic electroluminescent device material [for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as CBP)] and having excellent driving voltage characteristics and efficiency. to provide.

The novel tertiary substituted benzene compound of the present invention can be represented by the following general formula (1):

[Formula 1]

In Chemical Formula 1,

Ar ₁ is a C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl group, C Aryl group of ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C ₁ to C ₄₀ , aryloxy group of C ₆ to C ₆₀ , alkylsilyl group of C ₃ to C ₄₀ , C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₆₀ aryl boron group, C ₆ to C ₆₀ arylphosphine group, C ₆ to C ₆₀ mono or diaryl phosph A pinyl group and a C ₆ -C ₆₀ arylamine group;

Y ₁ is O or S;

Z ₁ is selected from the group consisting of a single bond, C (R ₁₁ ) (R ₁₂ ), N (R ₁₃ ), O and S;

L ₁ and L ₂ are each independently selected from the group consisting of a single bond, an arylene group having ₆ to ₄₀ carbon atoms and a heteroarylene group having 5 to 40 nuclear atoms;

R ₁ to R ₉ and R ₁₁ to R ₁₃ are each independently hydrogen, deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, nuclear atoms 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, A C ₆ to C ₄₀ arylphosphine group, a C ₆ to C ₄₀ mono or diarylphosphinyl group and a C ₆ to C ₄₀ arylsilyl group, or a condensed aromatic ring or condensation in combination with an adjacent group Can form a heteroaromatic ring;

m is an integer from 0 to 4;

R ₁₀ is deuterium, halogen, cyano group, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group, C ₂ -C ₄₀ alkynyl group, C ₆ -C ₄₀ aryl group, nuclear atom 5 to 40 heteroaryl groups, C ₆ to C ₄₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₄₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₄₀ arylboron groups, C ₆ to C ₄₀ arylphosphine groups, C ₆ to C ₄₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ selected from the group consisting arylsilyl of C ₄₀ or, by combining groups of adjacent, may form a fused aromatic ring, or a condensed heteroaromatic ring, a plurality of the R ₁₀ is In individuals they are the same or different from one another;

Any one of R ₁ to R ₉ forms a bond with L ₂ ;

The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkyl boron group, aryl of the above R ₁ to R ₁₃ Boron group, arylphosphine group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, 5 to 40 heteroaryl group of nuclear atoms, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ Arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₄₀ the arylboronic group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₄₀ aryl silyl groups at least one member selected from the group consisting of If the ring is substituted or unsubstituted, substituted by a plurality of substituent group, they may be the same or different from each other.

In order to obtain high-efficiency phosphorescence emission, energy transfer from the host to the dopant is important. The host must have triplet energy greater than the dopant to prevent the energy transferred to the dopant from being reversed to the host and have high luminous efficiency.

Accordingly, the compound of the present invention may have a triplet energy higher than that of the linearly bonded compound, in which each moiety is bonded in three directions with respect to benzene, as shown in Chemical Formula 1, and thus the dopant The exciton transition to the furnace is easy, and in view of confining the excitons generated in the light emitting layer, the light emission efficiency can be increased when used in the light emitting layer.

In addition, in the compound of Formula 1 of the present invention, the substituent connected to the benzene moiety by L ₁ has an electron donating group (EDG) characteristic of electron donating, and the substituent connected to L ₂ by the benzene moiety is electron As it has high absorbing electron withdrawing group (EWG) characteristics, the electron withdrawing group (EWG) with high electron absorption in one compound and the electron donating group with large electron donor EDG), so that the entire molecule is bipolar (bipolar) properties. For this reason, the compound of Formula 1 of the present invention may not only have a wide band gap, but also increase the binding force between holes and electrons. Accordingly, the phosphorescent property of the organic EL device may be improved, and the carrier injection ability, the transport ability, or the luminous efficiency may be improved.

In addition, the compound represented by the formula (1) of the present invention is significantly increased in molecular weight of the compound due to the bonding of the aromatic ring (aromatic ring) or heteroaromatic ring (heteroaromatic ring), the glass transition temperature is improved according to the conventional CBP (4 , 4-dicarbazolybiphenyl) shows a higher thermal stability, and due to the asymmetric structure is also effective in suppressing the crystallization of the organic layer.

Therefore, when the compound represented by Formula 1 of the present invention is used as a material for a hole injection layer, a hole transport layer, or a light emitting layer of an organic electroluminescent device, the efficiency of the organic electroluminescent device and the conventional organic material layer (for example, CBP) and It can improve the service life. In addition, the lifespan of the organic EL device may maximize the performance of the full color OLED panel.

According to a preferred embodiment of the present invention, Ar ₁ may be a 6-membered nitrogen-containing heterocyclic moiety, and the substituent linked to L ₁ may be dibenzofuran (dibenzo [b, d] furan) or dibenzothiophene (dibenzo). [b, d] thiophene) and the substituents linked by L ₂ are from the group consisting of carbazole, phenoxazine, phenothiazine, phenazine and acridine By any one selected, the said effect can be heightened further.

In addition, according to a preferred embodiment of the present invention, L ₁ and L ₂ are each independently a single bond, a phenylene group, a biphenylene group, naphthylene group, anthracenylene group, indenylene group, pyrantrenylene group, car Basolylene group, thiophenylene group, indolylene group, furinylene group, quinolinyl group, pyrroylene group, imidazolylene group, oxazolylene group, thiazolylene group, triazolylene group, pyridinylene group and pyrimidinylene group It may be selected from the group consisting of, more preferably, L ₁ and L ₂ may be each independently selected from the group consisting of a single bond, a phenylene group and a biphenylene group.

According to one preferred embodiment of the invention, Ar ₁ may be a substituent represented by the formula (2):

[Formula 2]

In Chemical Formula 2,

* Means a moiety bonded to Formula 1 above:

L ₃ is selected from the group consisting of a single bond, an arylene group having ₆ to ₄₀ carbon atoms and a heteroarylene group having 5 to 40 nuclear atoms;

X ₁ to X ₅ are each independently N or C (R ₁₄ );

R ₁₄ is hydrogen, deuterium, halogen, cyano group, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group, C ₂ -C ₄₀ alkynyl group, C ₆ -C ₄₀ aryl group, nuclear atom number 5 to 40 heteroaryl groups, C ₆ to C ₄₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₄₀ arylamine groups, C ₃ to C ₄₀ cycloalkyl groups, nuclear atoms 3 to 40 heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₄₀ arylboron groups, C ₆ to C ₄₀ arylphosphine groups, C ₆ ~ C ₄₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₄₀ selected from the group consisting of aryl silyl, or as in the combination group and adjacent, may form a fused aromatic ring, or fused heteroaromatic ring, wherein R ₁₄ Are plural, they are the same or different from each other;

The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group of R ₁₄ , cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkyl boron group, aryl boron group, an aryl phosphine group, a mono- or diaryl phosphine blood group and an aryl silyl group, each independently, a deuterium, a halogen, a cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl Neyl group, C ₆ ~ C ₄₀ aryl group, 5 to 40 heteroaryl groups, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, an aryl boronic of C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, a alkyl boronic of _{C 1 ~ C 40, C 6} ~ C 40 group, C ₆ ~ C ₄₀ of the aryl phosphine group, C ₆ ~ C ₄₀ mono or diaryl phosphine blood group and one or more substituents selected from the group consisting of aryl silyl C ₆ ~ C ₄₀ of When substituted or unsubstituted and substituted with a plurality of substituents, they may be the same or different from each other.

According to one preferred embodiment of the present invention, examples of the substituent represented by Formula 2 include a substituent represented by the following Formula A-1 to A-15, but is not limited thereto:

In Chemical Formulas A-1 to A-15,

n is an integer from 0 to 4;

R ₂₁ is deuterium (D), halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₄₀ aryl group, 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ aryloxy group , C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₄₀ Aryl boron group , C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ mono or diaryl phosphinyl group and C ₆ ~ C ₄₀ arylsilyl group, or combine with adjacent groups to form a condensed ring When R ₂₁ is plural, they are the same as or different from each other;

The alkyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphine group, mono or diarylphosphinyl group and aryl of R ₂₁ . The silyl groups are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, nuclear atom A number of 5 to 40 heteroaryl groups, C ₆ to C ₄₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₄₀ arylamine groups, C ₃ to C ₄₀ cycloalkyl groups, nuclear atoms C ₃ to C ₄₀ heterocycloalkyl group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₄₀ aryl boron group, C ₆ to C ₄₀ arylphosphine group, C substituted with ₆ ~ C ₄₀ mono or diaryl phosphine blood group and one or more substituents selected from the group consisting of a C ₆ ~ C ₄₀ aryl silyl or of being unsubstituted, light is substituted with plural substituents They are the same or different from each other;

*, L ₃ and R ₁₄ are as defined in the formula (2).

According to one preferred embodiment of the present invention, L ₃ is a single bond, a phenylene group, a biphenylene group, a naphthylene group, anthracenylene group, an indenylene group, a pyrantrenylene group, a carbazolylene group, a thiophenylene group, It may be selected from the group consisting of indolylene group, furinylene group, quinolinyl group, pyrroylene group, imidazolylene group, oxazolylene group, thiazolylene group, triazolylene group, pyridinylene group and pyrimidinylene group, More preferably, L ₃ may be a single bond or a phenylene group or a biphenylene group.

According to one preferred embodiment of the present invention, the compound represented by Formula 1 may be any one of the compounds represented by the following Formulas 3 to 7, but is not limited thereto. However, in view of the luminescence properties of the organic electroluminescent device, a compound of formula 3 or formula 6 is preferred:

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

In Chemical Formulas 3 to 7,

Ar ₁ , Y ₁ , Z ₁ , L ₁ , L ₂ , R ₁ to R ₁₀ and m are as defined in Formula 1 above.

Compounds of the present invention may specifically be represented by compounds of the structures illustrated below, but are not limited to:

2. Organic Electric field  Light emitting element

On the other hand, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by the formula (1) according to the present invention.

More specifically, the organic electroluminescent device according to the present invention includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers. May include a compound represented by Chemical Formula 1. In this case, the compound may be used alone, or two or more may be used in combination.

The at least one organic material layer may be at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. Herein, the organic material layer including the compound represented by Chemical Formula 1 is preferably a light emitting layer.

The light emitting layer of the organic electroluminescent device of the present invention may include a host material, and in this case, the host material may include a compound represented by Formula 1 above. When the compound represented by Chemical Formula 1 is included as a light emitting layer material of the organic electroluminescent device, preferably a blue, green, or red phosphorescent host material, the binding force between the holes and the electrons in the light emitting layer increases, so that the efficiency of the organic electroluminescent device (Luminescence efficiency and power efficiency), lifetime, brightness and driving voltage can be improved. Specifically, the compound represented by Chemical Formula 1 is preferably included in the organic electroluminescent device as a green and / or red phosphorescent host, fluorescent host, or dopant material.

The structure of the organic EL device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked. An electron injection layer may be further stacked on the electron transport layer.

In addition, the structure of the organic EL device according to the present invention may be a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.

The organic electroluminescent device of the present invention is another organic material layer using materials and methods known in the art, except that at least one layer (eg, the light emitting layer) of the organic material layer is formed to include the compound represented by Formula 1 above. And it can be manufactured by forming an electrode.

The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

As the substrate included in the organic EL device of the present invention, a silicon wafer, quartz, glass plate, metal plate, plastic film, sheet, or the like may be used.

In addition, the anode material may be a metal such as vanadium, chromium, copper, zinc, gold or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black and the like can be used, but is not limited thereto.

In addition, the negative electrode material may be magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or a metal such as lead or an alloy thereof, and a multilayer such as LiF / Al or LiO ₂ / Al. Structural materials and the like may be used, but are not limited thereto.

In addition, the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, and conventional materials known in the art may be used. Hereinafter, the present invention will be described in detail with reference to Examples. However, the following examples are merely to illustrate the invention, the present invention is not limited by the following examples.

[ Preparation  1] Synthesis of CDT-1

<Step 1> 3- (3- Bromo -5- ( Dibenzo [b, d] thiophene -4-yl) phenyl) -9-phenyl-9H- Carbazole  synthesis

23.9 g (50.0 mmol) of 3- (3,5-dibromophenyl) -9-phenyl-9H-carbazole, 11.4 g (50.0 mmol) of dibenzo [b, d] thiophene-4 under nitrogen stream Ilboonic acid, 6.0 g (150.0 mmol) of NaOH, 2.89 g (5 mol%) of Pd (PPh ₃ ) ₄ was added 250 ml / 120 ml of THF / H ₂ O and stirred at 90 ° C. for 12 hours. . After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, using column chromatography, the target compound 3- (3-bromo-5- (dibenzo [b, d] thiophen-4-yl) phenyl) -9-phenyl-9H -Carbazole (21.0 g, 36.1 mmol, yield 72%) was obtained.

Mass: [(M + H) ⁺ ]: 582, 580

Elemental Analysis: C, 74.48; H, 3. 82; Br, 13.76; N, 2.41; S, 5.52

Step 2 Synthesis of CDT-1

17.4 g (30.0 mmol) and 3,4,3- (3-bromo-5- (dibenzo [b, d] thiophen-4-yl) phenyl) -9-phenyl-9H-carbazole under a nitrogen stream 4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-ratio (1,3,2-dioxaborolane) 9.11 g (36.0 mmol), Pd (dppf) Cl ₂ Add 1.0 g (5 mol%), KOAc 8.79 g (90.0 mmol), 400 ml of 1,4-dioxane, stir at 110 ° C. for 12 hours, terminate the reaction, extract with methylene chloride and remove water with MgSO ₄ . It was. The reaction product from which the solvent was removed obtained the target compound CDT-1 (16.6 g, 26.4 mmol, yield 88%) using column chromatography.

Mass: [(M + H) ⁺ ]: 628

¹ H-NMR: δ 1.23 (s, 12H), 7.16 (t, 1H), 7.35 (t, 1H), 7.52 (m, 5H), 7.61 (m, 2H), 7.70 (m, 4H), 7.93 ( m, 5H), 8.32 (d, 1H), 8.52 (m, 3H)

[ Preparation  2] Synthesis of CDT-2

<Step 1> 3- (3- Bromo -5- ( Dibenzo [ b, d ] -Thiophen-2-yl) phenyl) -9-phenyl-9H- Carbazole  synthesis

<Step 1 of Preparation Example 1, except that dibenzo [b, d] thiophen-2-ylboronic acid (11.4 g, 50.0 mmol) was used instead of dibenzo [bd] thiophen-4-ylboronic acid. 3- (3-bromo-5- (dibenzo [b, d] -thiophen-2-yl) phenyl) -9-phenyl-9H-carbazole (18.9 g, 32.5 mmol) , Yield 65%) was obtained.

Mass: [(M + H) ⁺ ]: 582, 580

Elemental Analysis: C, 74.48; H, 3. 82; Br, 13.76; N, 2.41; S, 5.52

Step 2 Synthesis of CDT-2

3- (3-bromo-5- (di instead of 3- (3-bromo-5- (dibenzo [b, d] -thiophen-4-yl) phenyl) -9-phenyl-9H-carbazole Same procedure as in <Step 2> of Preparation Example 1, except using benzo [b, d] -thiophen-2-yl) phenyl) -9-phenyl-9H-carbazole (17.4 g, 30.0 mmol) Was carried out to give CDT-2 (14.0 g, 22.3 mmol, yield 74%).

Mass: [(M + H) ⁺ ]: 628

¹ H-NMR: δ 1.23 (s, 12H), 7.17 (t, 1H), 7.36 (t, 1H), 7.52 (m, 5H), 7.63 (m, 2H), 7.71 (m, 3H), 7.94 ( m, 6H), 8.12 (m, 2H), 8.50 (m, 2H)

[ Preparation  3] Synthesis of CDT-3

<Step 1> 3- (3- Bromo -5- ( Dibenzo [b, d] furan -4-yl) phenyl) -9-phenyl-9H- Carbazole  synthesis

<Step of Preparation Example 1, except that dibenzo [b, d] furan-4-ylboronic acid (10.6 g, 50.0 mmol) was used instead of dibenzo [b, d] thiophen-4-ylboronic acid. 1> was subjected to the same process as 3- (3-bromo-5- (dibenzo [b, d] furan-4-yl) phenyl) -9-phenyl-9H-carbazole (22.1 g, 39.2 mmol, Yield 78%).

Mass: [(M + H) ⁺ ]: 564, 566

Elemental Analysis: C, 76.60; H, 3.93; Br, 14.16; N, 2.48; O, 2.83

<Step 2> Synthesis of CDT-3

3- (3-bromo-5- (dibenzo) instead of 3- (3-bromo-5- (dibenzo [b, d] thiophen-4-yl) phenyl) -9-phenyl-9H-carbazole Except for using [b, d] furan-4-yl) phenyl) -9-phenyl-9H-carbazole (17.0 g, 30.0 mmol), the same procedure as in <Step 2> of Preparation Example 1 was performed. CDT-3 (14.1 g, 23.1 mmol, yield 77%) was obtained.

Mass: [(M + H) ⁺ ]: 612

¹ H-NMR: δ 1.23 (s, 12H), 7.16 (t, 1H), 7.35 (m, 3H), 7.52 (m, 5H), 7.62 (m, 2H), 7.77 (m, 3H), 7.94 ( m, 4H), 8.02 (m, 3H), 8.51 (d, 1H)

[ Preparation  4] Synthesis of CDT-4

<Step 1> 3- (3- Bromo -5- ( Dibenzo [b, d] furan -2-yl) phenyl) -9-phenyl-9H- Carbazole  synthesis

<Step of Preparation Example 1, except that dibenzo [b, d] furan-2-ylboronic acid (10.6 g, 50.0 mmol) was used instead of dibenzo [b, d] thiophen-4-ylboronic acid. 1> by the same process as 3- (3-bromo-5- (dibenzo [b, d] furan-2-yl) phenyl) -9-phenyl-9H-carbazole (18.5 g, 32.8 mmol, Yield 66%).

Mass: [(M + H) ⁺ ]: 564, 566

Elemental Analysis: C, 76.60; H, 3.93; Br, 14.16; N, 2.48; O, 2.83

Step 2 Synthesis of CDT-4

3- (3-bromo-5- (dibenzo) instead of 3- (3-bromo-5- (dibenzo [b, d] thiophen-4-yl) phenyl) -9-phenyl-9H-carbazole Except for using [b, d] furan-2-yl) phenyl) -9-phenyl-9H-carbazole (17.0 g, 30.0 mmol), the same procedure as in <Step 2> of Preparation Example 1 was performed. CDT-4 (13.4 g, 21.9 mmol, yield 73%) was obtained.

Mass: [(M + H) ⁺ ]: 612

¹ H-NMR: δ 1.24 (s, 12H), 7.16 (t, 1H), 7.35 (m, 3H), 7.51 (m, 4H), 7.63 (m, 2H), 7.77 (m, 4H), 7.84 ( m, 3H), 8.00 (m, 4H), 8.55 (d, 1H)

[ Preparation  5] Synthesis of CDT-5

<Step 1> 9 -(3,5- Dibromophenyl ) -9H- Carbazole  synthesis

9H-carbazole (16.7 g, 100.0 mmol), 1,3,5-tribromobenzene (47.1 g, 150.0 mmol), Pd ₂ (dba) ₃ (4.60 g, 5 mol%), under nitrogen stream (t -Bu) ₃ P (4.00 g, 20.0 mmol) and sodium tert-butoxide (28.8 g, 300.0 mmol) were added to 300 ml toluene and stirred at 110 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound 9- (3,5-dibromophenyl) -9H-carbazole (29.0 g, 72.1 mmol, 72% yield).

Mass: [(M + H) ⁺ ]: 402

Elemental Analysis: C, 53.90; H, 2.76; Br, 39.84; N, 3.49

<Step 2> 9- (3- Bromo -5- ( Dibenzo [b, d] thiophene -4-yl) phenyl-9H- Carbazole  synthesis

The use of 9- (3,5-dibromophenyl) -9H-carbazole (20.1 g, 50.0 mmol) instead of 3- (3,5-dibromophenyl) -9-phenyl-9H-carbazole Except for the same procedure as in <Step 1> of Preparation Example 1, 9- (3-bromo-5- (dibenzo [b, d] thiophen-4-yl) phenyl-9H-carbazole (16.2 g, 32.1 mmol, 64% yield).

Mass: [(M + H) ⁺ ]: 504, 506

Elemental Analysis: C, 71.43; H, 3. 60; Br, 15.84; N, 2.78; S, 6.36

Step 3 Synthesis of CDT-5

3- (3-bromo-5- (dibenzo [b, d] thiophen-4-yl) phenyl) -9-phenyl-9H-carbazole instead of 9- (3-bromo-5- (dibenzo CDT-5 was prepared by the same procedure as in <Step 2> of Preparation Example 1, except that [b, d] thiophen-4-yl) phenyl) -9H-carbazole (15.2 g, 30.0 mmol) was used. (11.7 g, 21.3 mmol, 71% yield).

Mass: [(M + H) ⁺ ]: 552

¹ H-NMR: δ 1.23 (s, 12H), 7.19 (m, 2H), 7.35 (t, 1H), 7.52 (m, 5H), 7.63 (s, 1H), 7.70 (d, 1H), 7.94 ( m, 2H), 8.20 (m, 3H), 8.52 (m, 3H)

[ Preparation  6] Synthesis of CDT-6

<Step 1> 9- (3- Bromo -5- ( Dibenzo [b, d] thiophene -2-yl) phenyl) -9H- Carbazole  synthesis

The use of 9- (3,5-dibromophenyl) -9H-carbazole (20.1 g, 50.0 mmol) instead of 3- (3,5-dibromophenyl) -9-phenyl-9H-carbazole Except for the same procedure as in <Step 1> of Preparation Example 2, 9- (3-bromo-5- (dibenzo [b, d] thiophen-2-yl) phenyl) -9H-carbazole ( 15.4 g, 30.5 mmol, 61% yield).

Mass: [(M + H) ⁺ ]: 504, 506

Elemental Analysis: C, 71.43; H, 3. 60; Br, 15.84; N, 2.78; S, 6.36

<Step 2> Synthesis of CDT-6

[Revision 20.01.2016 under Rule 91]

3- (3-bromo-5- (dibenzo [b, d] -thiophen-4-yl) phenyl) -9-phenyl-9H-carbazole instead of 9- (3-bromo-5- (di The same procedure as in <Step 2> of Preparation Example 1 was carried out except that benzo [b, d] thiophen-2-yl) phenyl-9H-carbazole (15.2 g, 30.0 mmol) was used. (13.7 g, 24.8 mmol, 83% yield).

Mass: [(M + H) ⁺ ]: 552

¹ H-NMR: δ 1.24 (s, 12H), 7.19 (m, 2H), 7.35 (t, 1H), 7.51 (m, 5H), 7.63 (s, 1H), 7.93 (m, 3H), 8.12 ( m, 3H), 8.21 (s, 1H), 8.51 (m, 2H)

[ Preparation  7] Synthesis of CDT-7

<Step 1> 9- (3- Bromo -5- ( Dibenzo [b.d] furan -4-yl) phenyl) -9H- Carbazole  synthesis

[Revision 20.01.2016 under Rule 91]

The use of 9- (3,5-dibromophenyl) -9H-carbazole (20.1 g, 50.0 mmol) instead of 3- (3,5-dibromophenyl) -9-phenyl-9H-carbazole Except for the same procedure as in <Step 1> of Preparation Example 3, 9- (3-bromo-5- (dibenzo [b, d] furan-4-yl) phenyl) -9H-carbazole (15.1 g, 30.9 mmol, yield 62%).

Mass: [(M + H) ⁺ ]: 488, 490

Elemental Analysis: C, 73.78; H, 3.72; Br, 16.36; N, 2.87; O, 3.28

Step 2 Synthesis of CDT-7

3- (3-bromo-5- (dibenzo [b, d] thiophen-4-yl) phenyl) -9-phenyl-9H-carbazole instead of 9- (3-bromo-5- (dibenzo CDT-7 (11.7) was carried out in the same manner as in <Step 2> of Preparation Example 1, except that [b, d] furan-4-yl) phenyl-9H-carbazole (14.7 g, 30.0 mmol) was used. g, 21.9 mmol, yield 73%).

Mass: [(M + H) ⁺ ]: 536

¹ H-NMR: δ 1.24 (s, 12H), 7.20 (m, 3H), 7.36 (t, 1H), 7.54 (m, 4H), 7.64 (s, 1H), 7.85 (m, 3H), 8.02 ( m, 4H), 8.19 (s, 1H), 8.55 (d, 1H)

[ Preparation  8] Synthesis of CDT-8

<Step 1> 9- (3- Bromo -5- ( Dibenzo [b, d] furan -2-yl) phenyl) -9-phenyl-9H- Carbazole  synthesis

The use of 9- (3,5-dibromophenyl) -9H-carbazole (20.1 g, 50.0 mmol) instead of 3- (3,5-dibromophenyl) -9-phenyl-9H-carbazole Except for the same procedure as in <Step 1> of Preparation Example 4, except that 9- (3-bromo-5- (dibenzo [b, d] furan-2-yl) phenyl) -9-phenyl-9H- Carbazole (15.3 g, 31.2 mmol, yield 62%) was obtained.

Mass: [(M + H) ⁺ ]: 488, 490

Elemental Analysis: C, 73.78; H, 3.72; Br, 16.36; N, 2.87; O, 3.28

Step 2 Synthesis of CDT-8

3- (3-bromo-5- (dibenzo [b, d] thiophen-4-yl) phenyl) -9-phenyl-9H-carbazole instead of 9- (3-bromo-5- (dibenzo Except for using [b, d] furan-2-yl) phenyl) -9-phenyl-9H-carbazole (14.7 g, 30.0 mmol), the same procedure as in <Step 2> of Preparation Example 1 was performed. CDT-8 (12.1 g, 22.7 mmol, 76% yield) was obtained.

Mass: [(M + H) ⁺ ]: 536

¹ H-NMR: δ 1.24 (s, 12H), 7.19 (m, 2H), 7.36 (m, 2H), 7.54 (m, 4H), 7.65 (s, 1H), 7.85 (m, 2H), 8.00 ( m, 3H), 8.19 (s, 1H), 8.55 (m, 2H)

[ Preparation  9] Synthesis of CDT-9

<Step 1> 9- (3 ', 5'- Dichloro -[1,1'-biphenyl] -3-yl) -9H- Carbazole  synthesis

<Step of Preparation Example 5, except that 3'-bromo-3,5-dichloro-1,1'-biphenyl (45.3 g, 150.0 mmol) was used instead of 1,3,5-tribromobenzene. 1- (3 ', 5'-dichloro- [1,1'-biphenyl] -3-yl) -9H-carbazole (28.4 g, 73.2 mmol, 73% yield) Got it.

Mass: [(M + H) ⁺ ]: 388

Elemental Analysis: C, 74.24; H, 3.89; Cl, 18.26; N, 3.61

<Step 2> 9- (3'- Chloro - 5 '(dibenzo [b, d] thiophene Synthesis of 4-yl)-[1,1'-biphenyl] -3-yl) -9H-carbazole

19.4 g (50.0 mmol) of 9- (3 ', 5'-dichloro- [1,1'-biphenyl] -3-yl) -9H-carbazole, 11.4 g (50.0 mmol) of dibenzox under nitrogen stream [b, d] thiophen-4-ylboronic acid, 20.7 g (150.0 mmol) of K ₂ CO ₃ , 2.89 g (5 mol%) of Pd (PPh ₃ ) _{4 ,} 2.4 g (5.00 mmol) of X- Phosphorus 250 ml / 120 ml THF / H ₂ O was added and stirred at 90 ℃ for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, using column chromatography, the target compound 9- (3'-chloro-5 '-(dibenzo [b, d] thiophen-4-yl)-[1,1'- Biphenyl] -3-yl) -9H-carbazole (16.1 g, 30.1 mmol, yield 60%) was obtained.

Mass: [(M + H) ⁺ ]: 535

Elemental Analysis: C, 80.66; H, 4.14; Cl, 6.61; N, 2.61; S, 5.98

Step 3 Synthesis of CDT-9

16.0 g of 9- (3'-chloro-5 '(dibenzo [b, d] thiophen-4-yl)-[1,1'-biphenyl] -3-yl) -9H-carbazole under a nitrogen stream (30.0 mmol) and 9.11 g (36.0 mmol) of 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-(1,3,2-dioxaborolane ), Pd (dppf) Cl ₂ 1.0 g (5 mol%), KOAc 8.79 g (90.0 mmol), X-Phos 1.43 g (3.00 mmol), 400 ml of 1,4-Dioxane and stirred at 110 ℃ for 12 hours The reaction was terminated and extracted with methylene chloride to remove moisture with MgSO _{4. The} solvent was removed using column chromatography to obtain the title compound CDT-9 (14.7 g, 23.4 mmol, yield 78%). .

Mass: [(M + H) ⁺ ]: 628

¹ H-NMR: δ 1.25 (s, 12H), 7.19 (m, 2H), 7.35 (t, 1H), 7.55 (m, 5H), 7.64 (m, 2H), 7.72 (m, 3H), 7.95 ( m, 3H), 8.22 (m, 2H), 8.29 (d, 1H), 8.55 (m, 3H)

[ Preparation  10] ADT Synthesis of -1

<Step 1> 2- (3,5- Dibromophenyl ) -9,9-dimethyl-10-phenyl-9,10- Of dihydroacridine  synthesis

32.9 g (100.0 mmol) of (9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-yl) boronic acid, 47.3 g (150.0 mmol) of 1,3,5 under nitrogen stream Tribromobenzene, 12.0 g (300.0 mmol) of NaOH, 5.78 g (5 mol%) of Pd (PPh ₃ ) ₄ was added 500 ml / 180 ml of THF / H ₂ O and stirred at 90 ° C. for 12 hours. It was. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, using column chromatography, the target compound 2- (3,5-dibromophenyl) -9,9-dimethyl-10-phenyl-9,10-dihydroacridine ( 32.3 g, 62.1 mmol, 62% yield).

Mass: [(M + H) ⁺ ]: 520

Elemental Analysis: C, 62.45; H, 4.08; Br, 30.77; N, 2.70

<Step 2> 2- (3- Bromo -5- ( Dibenzo [b, d] thiophene Synthesis of -4-yl) phenyl-9,9-dimethyl-10-phenyl-9,10-dihydroacridine

2- (3,5-dibromophenyl) -9,9-dimethyl-10-phenyl-9,10-di instead of 3- (3,5-dibromophenyl) -9-phenyl-9H-carbazole A 2- (3-bromo-5- (dibenzo [b, d]] was carried out in the same manner as in <Step 1> of Preparation Example 1, except that hydroacridine (26.0 g, 50.0 mmol) was used. Thiophen-4-yl) phenyl-9,9-dimethyl-10-phenyl-9,10-dihydroacridine (19.8 g, 31.8 mmol, 63% yield) was obtained.

Mass: [(M + H) ⁺ ]: 622, 624

Elemental Analysis: C, 75.23; H, 4.53; Br, 12.83; N, 2.25; S, 5.15

<Step 3> ADT Synthesis of -1

3- (3-bromo-5- (dibenzo [b, d] thiophen-4-yl) phenyl) -9-phenyl-9H-carbazole instead of 2- (3-bromo-5- (dibenzo Preparation Example, except using [b, d] thiophen-4-yl) phenyl) -9,9-dimethyl-10-phenyl-9,10-dihydroacridine (18.7 g, 30.0 mmol) The same procedure as in <Step 2> of 1 was carried out to obtain ADT-1 (16.6 g, 24.7 mmol, 82% yield).

Mass: [(M + H) ⁺ ]: 670

¹ H-NMR: δ 1.24 (s, 12H), 1.69 (s, 6H), 7.01 (m, 4H), 7.14 (m, 3H), 7.24 (m, 2H), 7.35 (d, 1H), 7.45 ( m, 3H), 7.72 (m, 4H), 8.01 (m, 2H), 8.32 (d, 1H), 8.46 (m, 2H)

[ Preparation  11] ADT Synthesis of -2

<Step 1> 2- (3- Bromo -5- ( Dibenzo [b, d] thiophene Synthesis of 2-yl) phenyl-9,9-dimethyl-10-phenyl-9,10-dihydroacridine

Preparation <10 of Preparation 10, except that dibenzo [b, d] thiophen-2-ylboronic acid (11.4 g, 50.0 mmol) was used instead of dibenzo [b, d] thiophen-4-ylboronic acid. Follow the same procedure as in step 2> to give 2- (3-bromo-5- (dibenzo [b, d] thiophen-2-yl) phenyl-9,9-dimethyl-10-phenyl-9,10- Dihydroacridine (19.4 g, 31.1 mmol, yield 62%) was obtained.

Mass: [(M + H) ⁺ ]: 622, 624

Elemental Analysis: C, 75.23; H, 4.53; Br, 12.83; N, 2.25; S, 5.15

<Step 2> ADT Synthesis of -2

2- (3-bromo-5- (dibenzo [b, d] thiophen-4-yl) phenyl-9,9-dimethyl-10-phenyl-9,10-dihydroacridine instead of 2- ( 3-bromo-5- (dibenzo [b, d] thiophen-2-yl) phenyl-9,9-dimethyl-10-phenyl-9,10-dihydroacridine (18.7 g, 30.0 mmol) Except for using the same process as in <Step 3> of Preparation Example 10 to obtain ADT-2 (15.4 g, 23.0 mmol, yield 77%).

Mass: [(M + H) ⁺ ]: 670

¹ H-NMR: δ 1.25 (s, 12H), 1.68 (s, 6H), 7.02 (m, 4H), 7.14 (m, 3H), 7.25 (m, 2H), 7.36 (d, 1H), 7.51 ( m, 3H), 7.77 (m, 4H), 8.01 (m, 2H), 8.12 (m, 2H), 8.46 (d, 1H)

[ Preparation  12] ADT Synthesis of -3

<Step 1> 2- (3- Bromo -5- ( Dibenzo [b, d] furan Synthesis of -4-yl) phenyl) -9,9-dimethyl-10-phenyl-9,10-dihydroacridine

<Step of Preparation Example 10, except that dibenzo [b, d] purin-4-ylboronic acid (10.6 g, 50.0 mmol) was used instead of dibenzo [b, d] thiophen-4-ylboronic acid. 2> to the same process as 2- (3-bromo-5- (dibenzo [b, d] furan-4-yl) phenyl) -9,9-dimethyl-10-phenyl-9,10-di Hydroacridine (18.8 g, 30.9 mmol, yield 62%) was obtained.

Mass: [(M + H) ⁺ ]: 606, 608

Elemental Analysis: C, 77.23; H, 4.65; Br, 13.17; N, 2.31; O, 2.64

<Step 2> ADT Synthesis of -3

2- (3-bromo-5- (dibenzo [b, d] thiophen-4-yl) phenyl-9,9-dimethyl-10-phenyl-9,10-dihydroacridine instead of 2- ( 3-bromo-5- (dibenzo [b, d] furan-4-yl) phenyl) -9,9-dimethyl-10-phenyl-9,10-dihydroacridine (18.2 g, 30.0 mmol) Except for using the same process as in <Step 3> of Preparation Example 10 to obtain the ADT-3 (15.2 g, 23.2 mmol, yield 77%).

Mass: [(M + H) ⁺ ]: 654

¹ H-NMR: δ 1.25 (s, 12H), 1.69 (s, 6H), 7.08 (m, 4H), 7.14 (m, 4H), 7.25 (m, 2H), 7.36 (d, 1H), 7.52 ( m, 4H), 7.77 (m, 3H), 8.01 (s, 1H), 8.12 (m, 2H), 8.45 (d, 1H)

[ Preparation  13] ADT Synthesis of -4

<Step 1> 2- (3- Bromo -5- ( Dibenzo [b, d] furan 2-yl) phenyl) -9,9-dimethyl-10-phenyl-9,10-dihydroacridine

<Step of Preparation Example 10, except that dibenzo [b, d] furan-2-ylboronic acid (10.6 g, 50.0 mmol) was used instead of dibenzo [b, d] thiophen-4-ylboronic acid. 2> by following the same procedure as for 2- (3-bromo-5- (dibenzo [b, d] furan-2-yl) phenyl) -9,9-dimethyl-10-phenyl-9,10-di Hydroacridine (20.0 g, 32.9 mmol, 66% yield) was obtained.

Mass: [(M + H) ⁺ ]: 606, 608

Elemental Analysis: C, 77.23; H, 4.65; Br, 13.17; N, 2.31; O, 2.64

<Step 2> ADT Synthesis of -4

2- (3-bromo-5- (dibenzo [b, d] thiophen-4-yl) phenyl-9,9-dimethyl-10-phenyl-9,10-dihydroacridine instead of 2- ( 3-bromo-5- (dibenzo [b, d] furan-2-yl) phenyl) -9,9-dimethyl-10-phenyl-9,10-dihydroacridine (18.2 g, 30.0 mmol) Except for using the same process as in <Step 3> of Preparation Example 10 to obtain ADT-3 (13.0 g, 19.8 mmol, 66% yield).

Mass: [(M + H) ⁺ ]: 654

¹ H-NMR: δ 1.25 (s, 12H), 1.68 (s, 6H), 7.10 (m, 4H), 7.19 (m, 4H), 7.25 (m, 2H), 7.37 (d, 1H), 7.52 ( m, 5H), 7.75 (m, 2H), 8.00 (s, 1H), 8.12 (m, 2H), 8.45 (d, 1H)

[ Preparation  14] ADT Synthesis of -5

<Step 1> 10- (3,5- Dibromophenyl ) -9,9-dimethyl-9,10- Of dihydroacridine  synthesis

Except for using 9,9-dimethyl-9,10-dihydroacridine (20.9 g, 100.0 mmol) instead of 9H- carbazole, the same procedure as in <Step 1> of Preparation Example 5 was performed. (3,5-Dibromophenyl) -9,9-dimethyl-9,10-dihydroacridine (23.5 g, 58.4 mmol, yield 58%) was obtained.

Mass: [(M + H) ⁺ ]: 402

Elemental Analysis: C, 53.90; H, 2.76; Br, 39.84; N, 3.49

<Step 2> 10- (3- Bromo -5- ( Dibenzo [b, d] thiophene Synthesis of -4-yl) phenyl) -9,9-dimethyl-9,10-dihydroacridine

10- (3,5-dibromophenyl) -9,9- instead of 2- (3,5-dibromophenyl) -9,9-dimethyl-10-phenyl-9,10-dihydroacridine Except for using dimethyl-9,10-dihydroacridine (20.1 g, 50.0 mmol) was carried out the same procedure as in <Step 2> of Preparation Example 10 to 10- (3-bromo-5- ( Dibenzo [b, d] thiophen-4-yl) phenyl) -9,9-dimethyl-9,10-dihydroacridine (16.4 g, 30.0 mmol, yield 60%) was obtained.

Mass: [(M + H) ⁺ ]: 546, 548

Elemental Analysis: C, 72.52; H, 4. 43; Br, 14.62; N, 2.56; S, 5.87

<Step 3> ADT Synthesis of -5

10- instead of 2- (3-bromo-5- (dibenzo [b, d] thiophen-4-yl) phenyl) -9,9-dimethyl-10-phenyl-9,10-dihydroacridine Using (3-bromo-5- (dibenzo [b, d] thiophen-4-yl) phenyl) -9,9-dimethyl-9,10-dihydroacridine (16.4 g, 30.0 mmol) Except for the same procedure as in <Step 3> of Preparation Example 10 to obtain ADT-5 (14.0 g, 23.6 mmol, yield 79%).

Mass: [(M + H) ⁺ ]: 594

¹ H-NMR: δ 1.25 (s, 12H), 1.69 (s, 6H), 6.95 (t, 2H), 7.15 (m, 6H), 7.22 (m, 2H), 7.33 (s, 1H), 7.47 ( t, 1H), 7.56 (t, 1H), 7.72 (t, 1H), 8.00 (d, 1H), 8.32 (d, 1H), 8.48 (m, 2H)

[ Preparation  15] ADT Synthesis of -6

<Step 1> 10- (3- Bromo -5- ( Dibenzo [b, d] thiophene Synthesis of 2-yl) phenyl) -9,9-dimethyl-9,10-dihydroacridine

Preparation of Example 14 except that dibenzo [b, d] thiophen-2-ylboronic acid (11.4 g, 50.0 mmol) was used instead of dibenzo [b, d] thiophen-4-ylboronic acid. 10- (3-bromo-5- (dibenzo [b, d] thiophen-2-yl) phenyl) -9,9-dimethyl-9,10-dihydroa by following the same procedure as in step 2> Credin (18.4 g, 33.6 mmol, yield 67%) was obtained.

Mass: [(M + H) ⁺ ]: 546, 548

Elemental Analysis: C, 72.52; H, 4. 43; Br, 14.62; N, 2.56; S, 5.87

<Step 2> ADT Synthesis of -6

10- instead of 2- (3-bromo-5- (dibenzo [b, d] thiophen-4-yl) phenyl) -9,9-dimethyl-10-phenyl-9,10-dihydroacridine (3-bromo-5- (dibenzo [b, d] thiophen-2-yl) phenyl) -9,9-dimethyl-9,10-dihydroacridine (16.4 g, 30.0 mmol)) Except for using the same procedure as in <Step 3> of Preparation Example 10 to obtain ADT-6 (12.2 g, 20.5 mmol, yield 68%).

Mass: [(M + H) ⁺ ]: 594

¹ H-NMR: δ 1.25 (s, 12H), 1.69 (s, 6H), 6.96 (t, 2H), 7.18 (m, 6H), 7.22 (m, 2H), 7.33 (s, 1H), 7.48 ( t, 1H), 7.56 (t, 1H), 7.73 (t, 1H), 8.00 (d, 1H), 8.12 (m, 2H), 8.48 (d, 1H)

[ Preparation  16] ADT Synthesis of -7

<Step 1> 10- (3- Bromo -5- ( Dibenzo [b, d] furan -4-yl) phenyl) -9,9-dimethyl-9,10- Of dihydroacridine  synthesis

<Step of Preparation 14, except dibenzo [b, d] furan-4-ylboronic acid (10.6 g, 50.0 mmol) was used instead of dibenzo [b, d] thiophen-4-ylboronic acid. 2>-(3-bromo-5- (dibenzo [b, d] furan-4-yl) phenyl) -9,9-dimethyl-9,10-dihydroacridine (16.1 g, 30.4 mmol, yield 61%).

Mass: [(M + H) ⁺ ]: 530, 532

Elemental Analysis: C, 74.72; H, 4.56; Br, 15.06; N, 2.64; O, 3.02

<Step 2> ADT Synthesis of -7

10- instead of 2- (3-bromo-5- (dibenzo [b, d] thiophen-4-yl) phenyl) -9,9-dimethyl-10-phenyl-9,10-dihydroacridine (3-bromo-5- (dibenzo [b, d] furan-4-yl) phenyl) -9,9-dimethyl-9,10-dihydroacridine (15.9 g, 30.0 mmol) using Except for the same procedure as in <Step 3> of Preparation Example 10 to obtain ADT-7 (12.2 g, 21.1 mmol, 70% yield).

Mass: [(M + H) ⁺ ]: 578

¹ H-NMR: δ 1.25 (s, 12H), 1.69 (s, 6H), 6.96 (t, 2H), 7.18 (m, 6H), 7.25 (m, 2H), 7.33 (m, 3H), 7.50 ( m, 2H), 8.01 (m, 2H), 8.08 (d, 1H)

[ Preparation  17] ADT Synthesis of -8

<Step 1> 10- (3- Bromo -5- ( Dibenzo [b, d] furan -2-yl) phenyl) -9,9-dimethyl-9,10- Of dihydroacridine  synthesis

<Step of Preparation 14, except dibenzo [b, d] furan-2-ylboronic acid (10.6 g, 50.0 mmol) was used instead of dibenzo [b, d] thiophen-4-ylboronic acid. 2> by the same process as 10- (3-bromo-5- (dibenzo [b, d] furan-2-yl) phenyl-9,9-dimethyl-9,10-dihydroacridine ( 16.4 g, 30.9 mmol, yield 62%).

Mass: [(M + H) ⁺ ]: 530, 532

Elemental Analysis: C, 74.72; H, 4.56; Br, 15.06; N, 2.64; O, 3.02

<Step 2> ADT Synthesis of -8

2- (3-bromo-5- (dibenzo [b, d] thiophen-4-yl) phenyl) -9,9-dimethyl-10-phenyl-9,10-dihydroacridine instead of 1 0 -(3-bromo-5- (dibenzo [b, d] furan-2-yl) phenyl) -9,9-dimethyl-9,10-dihydroacridine (15.9 g, 30.0 mmol) was used Aside from the same procedure as in <Step 3> of Preparation Example 10 to obtain ADT-8 (14.3 g, 24.7 mmol, yield 82%).

Mass: [(M + H) ⁺ ]: 578

¹ H-NMR: δ 1.25 (s, 12H), 1.69 (s, 6H), 6.96 (t, 2H), 7.17 (m, 6H), 7.23 (m, 2H), 7.33 (m, 3H), 7.54 ( d, 1H), 8.01 (m, 3H), 8.08 (d, 1H)

[ Preparation  18] ADT Synthesis of -9

<Step 1> 10- (3 ', 5'- Dichloro -[One, 1'biphenyl ] -3-yl) -9,9-dimethyl-9,10- Of dihydroacridine  synthesis

Except for using 9,9-dimethyl-9,10-dihydroacridine (10.6 g, 100.0 mmol) instead of 9H- carbazole, the same procedure as in <Step 1> of Preparation Example 9 was performed. (3 ', 5'-dichloro- [1,1'-biphenyl] -3-yl) -9,9-dimethyl-9,10-dihydroacridine (32.9 g, 76.4 mmol, yield 76%) Got.

Mass: [(M + H) ⁺ ]: 430

Elemental Analysis: C, 75.35; H, 4.92; Cl, 16.47; N, 3.25

<Step 2> 10- (3'- Chloro -5 '-( Dibenzo [b, d] thiophene Synthesis of 4-yl)-[1,1'-biphenyl] -3-yl) -9,9-dimethyl-9,10-dihydroacridine

10- (3 ', 5'-dichloro- [1,1'-biphenyl instead of 9- (3', 5'-dichloro- [1,1'-biphenyl] -3-yl) -9H-carbazole ] -3-yl) -9,9-dimethyl-9,10-dihydroacridine (21.5 g, 50.0 mmol) was subjected to the same procedure as in <Step 2> of Preparation Example 9 10- (3'-chloro-5 '-(dibenzo [b, d] thiophen-4-yl)-[1,1'-biphenyl] -3-yl) -9,9-dimethyl-9, 10-dihydroacridine (18.0 g, 31.2 mmol, yield 62%) was obtained.

Mass: [(M + H) ⁺ ]: 578

Elemental Analysis: C, 81.02; H, 4.88; Cl, 6.13; N, 2.42; S, 5.55

<Step 3> ADT Synthesis of -9

9- (3'-chloro-5 '-(dibenzo [b, d] thiophen-4-yl)-[1,1'-biphenyl] -3-yl) -9H-carbazole instead of 10- ( 3'-chloro-5 '-(dibenzo [b, d] thiophen-4-yl)-[1,1'-biphenyl] -3-yl) -9,9-dimethyl-9,10-di Except for using hydroacridine (17.3 g, 30.0 mmol) was carried out the same procedure as in <Step 3> of Preparation Example 9 to obtain ADT-9 (14.1 g, 21.0 mmol, yield 70%).

Mass: [(M + H) ⁺ ]: 670

¹ H-NMR: δ 1.25 (s, 12H), 1.69 (s, 6H), 6.95 (t, 2H), 7.17 (m, 8H), 7.27 (s, 1H), 7.43 (t, 1H), 7.54 ( m, 2H), 7.72 (m, 3H), 8.01 (m, 2H), 8.32 (d, 1H), 8.42 (m, 2H)

[ Preparation  19] Synthesis of PDT-1

<Step 1> 3- (3,5- Dibromophenyl ) -10-phenyl-10H- Phenothiazine  synthesis

10-phenyl-3- (4,4,5,5, -tetramethyl-1,3 instead of (9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-yl) boronic acid Except for using 2-2-dioxaborolan-2-yl) -10H-phenoazine (40.1 g, 100.0 mmol), the same procedure as in <Step 1> of Preparation Example 10 was performed. 3,5-Dibromophenyl) -10-phenyl-10H-phenoazine (29.9 g, 58.8 mmol, yield 59%) was obtained.

Mass: [(M + H) ⁺ ]: 509

Elemental Analysis: C, 56.60; H, 2.97; Br, 31.38; N, 2.75; S, 6.30

<Step 2> 3- (3- Bromo -5- ( Dibenzo [b, d] thiophene -4-yl) phenyl) -10-phenyl-10H- Phenothiazine  synthesis

3- (3,5-dibromophenyl) -10-phenyl- instead of 2- (3,5-dibromophenyl) -9,9-dimethyl-10-phenyl-9,10-dihydroacridine Except for using 10H-phenoazine (25.5 g, 50.0 mmol) was carried out the same procedure as in <Step 2> of Preparation Example 10 to 3- (3-bromo-5- (dibenzo [b, d ] Thiophen-4-yl) phenyl) -10-phenyl-10H-phenoazine (18.5 g, 30.2 mmol, yield 60%) was obtained.

Mass: [(M + H) ⁺ ]: 612, 614

Elemental Analysis: C, 70.58; H, 3.62; Br, 13.04; N, 2.29; S, 10.47

Step 3 Synthesis of PDT-1

3- (3-bromo-5- (dibenzo [b, d] thiophen-4-yl) phenyl) -9,9-dimethyl-10-phenyl-9,10-dihydroacridine instead of 3- Preparation, except using (3-bromo-5- (dibenzo [b, d] thiophen-4-yl) phenyl) -10-phenyl-10H-phenoazine (18.4 g, 30.0 mmol) PDT-1 (16.9 g, 25.6 mmol, yield 85%) was obtained by the same process as <Step 3> of Example 10.

Mass: [(M + H) ⁺ ]: 660

¹ H-NMR: δ 1.22 (s, 12H), 7.05 (m, 4H), 7.25 (m, 6H), 7.33 (m, 2H), 7.49 (t, 1H), 7.56 (t, 1H), 7.72 ( m, 3H), 8.01 (m, 2H), 8.32 (d, 1H), 8.47 (m, 2H)

[ Preparation  20] Synthesis of PDT-2

<Step 1> 3- (3- Bromo -5- ( Dibenzo [b, d] furan -2-yl) phenyl) -10-phenyl-10H- Phenothiazine  synthesis

<Step of Preparation Example 19 except that dibenzo [b, d] furan-2-ylboronic acid (10.6 g, 50.0 mmol) was used instead of dibenzo [b, d] thiophen-4-ylboronic acid. 2> to the same procedure as in 3- (3-bromo-5- (dibenzo [b, d] furan-2-yl) phenyl) -10-phenyl-10H-phenoazine (20.0 g, 33.5 mmol , Yield 67%) was obtained.

Mass: [(M + H) ⁺ ]: 596, 598

Elemental Analysis: C, 72.48; H, 3.72; Br, 13.39; N, 2.35; 0, 2.68; S, 5.37

Step 2 Synthesis of PDT-2

3- (3-bromo-5- (dibenzo [b, d] thiophen-4-yl) phenyl) -10-phenyl-10H-phenoazine instead of 3- (3-bromo-5- (di The same procedure as in <Step 3> of Preparation Example 19 was performed except that benzo [b, d] furan-2-yl) phenyl) -10-phenyl-10H-phenoazine (17.9 g, 30.0 mmol) was used. PDT-2 (12.1 g, 18.9 mmol, yield 63%) was obtained.

Mass: [(M + H) ⁺ ]: 644

¹ H-NMR: δ 1.22 (s, 12H), 7.03 (m, 4H), 7.27 (m, 5H), 7.35 (m, 3H), 7.39 (t, 1H), 7.54 (d, 1H), 7.72 ( m, 3H), 8.01 (m, 3H), 8.32 (m, 2H)

[ Preparation  21] Synthesis of PDT-3

<Step 1> 3- (3,5- Dibromophenyl ) -10-phenyl-10H- Phenox Photo  synthesis

10-phenyl-3- (4,4,5,5, -tetramethyl-1,3,2-dioxaborolan-2-yl) -10-phenyl-3- (4 instead of 10H-phenoazine Preparation Example 19, except that, 4,5,5, -tetramethyl-1,3,2-dioxaborolan-2-yl) -10H-phenoxazine (38.5 g, 100.0 mmol) was used. 3- (3,5-dibromophenyl) -10-phenyl-10H-phenoxazine (31.2 g, 63.2 mmol, 63% yield) was obtained in the same manner as in <Step 1>.

Mass: [(M + H) ⁺ ]: 494

Elemental Analysis: C, 58.45; H, 3.07; Br, 32.40; N, 2.84; O, 3.24

<Step 2> 3- (3- Bromo -5- ( Dibenzo [b, d] thiophene -4-yl) phenyl) -10-phenyl-10H- Phenox Photo  synthesis

3- (3,5-dibromophenyl) -10-phenyl-10H-phenoxazine (24.7 g, 50.0 mmol instead of 3- (3,5-dibromophenyl) -10-phenyl-10H-phenoazine ) Was subjected to the same procedure as in <Step 2> of Preparation Example 19, except that 3- (3-bromo-5- (dibenzo [b, d] thiophen-4-yl) phenyl)- 10-phenyl-10H-phenoxazine (18.9 g, 31.7 mmol, yield 64%) was obtained.

Mass: [(M + H) ⁺ ]: 596, 598

Elemental Analysis: C, 72.48; H, 3.72; Br, 13.39; N, 2.35; 0, 2.68; S, 5.37

Step 3 Synthesis of PDT-3

3- (3-bromo-5- (dibenzo [b, d] thiophen-4-yl) phenyl) -10-phenyl-10H-phenoazine instead of 3- (3-bromo-5- (di The same procedure as in <Step 3> of Preparation Example 19 was carried out except that benzo [b, d] thiophen-4-yl) phenyl) -10-phenyl-10H-phenoxazine (17.9 g, 30.0 mmol) was used. PDT-3 (15.6 g, 24.2 mmol, yield 81%) was obtained.

Mass: [(M + H) ⁺ ]: 644

¹ H-NMR: δ 1.22 (s, 12H), 7.03 (m, 4H), 7.28 (m, 5H), 7.35 (m, 2H), 7.39 (t, 1H), 7.55 (d, 1H), 7.72 ( m, 3H), 8.01 (m, 2H), 8.32 (m, 2H), 8.48 (m, 2H)

[ Preparation  22] Synthesis of PDT-4

<Step 1> 3- (3- Bromo -5- ( Dibenzo [b, d] furan -2-yl) phenyl) -10-phenyl-10H- Phenox Photo  synthesis

3- (3,5-dibromophenyl) -10-phenyl-10H-phenoxazine (24.7 g, 50.0 mmol instead of 3- (3,5-dibromophenyl) -10-phenyl-10H-phenoazine Except for using), the same process as in <Step 1> of Preparation Example 20 was carried out to proceed with 3- (3-bromo-5- (dibenzo [b, d] furan-2-yl) phenyl) -10 -Phenyl-10H-phenoxazine (17.4 g, 30.0 mmol, yield 60%) was obtained.

Mass: [(M + H) ⁺ ]: 580, 582

Elemental Analysis: C, 74.49; H, 3. 82; Br, 13.77; N, 2.41; O, 5.51

Step 2 Synthesis of PDT-4

3- (3-bromo-5- (dibenzo) instead of 3- (3-bromo-5- (dibenzo [b, d] furan-2-yl) phenyl) -10-phenyl-10H-phenoazine Except for using [b, d] furan-2-yl) phenyl) -10-phenyl-10H-phenoxazine (17.4 g, 30.0 mmol), the same procedure as in <Step 2> of Preparation Example 20 was performed. PDT-4 (12.4 g, 19.7 mmol, yield 66%) was obtained.

Mass: [(M + H) ⁺ ]: 628

¹ H-NMR: δ 1.22 (s, 12H), 7.03 (m, 6H), 7.28 (m, 5H), 7.32 (m, 3H), 7.54 (d, 1H), 7.75 (m, 3H), 7.87 ( m, 2H), 8.01 (m, 2H)

[ Synthesis Example  1] Synthesis of C 11

6.27 g (10.0 mmol) of CDT-1, 2.67 g (10.0 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, 1.2 g (30.0 mmol) of NaOH, under nitrogen stream 0.58 g (5 mol%) of Pd (PPh ₃ ) ₄ was added with 150 ml / 70 ml of THF / H ₂ O and stirred at 90 ° C. for 6 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to obtain the target compound C 11 (5.95 g, yield 81%).

Mass: [(M + H) ⁺ ]: 733

[ Synthesis Example  2] Synthesis of C 12

Synthesis Example 1 except that 2-chloro-4,6-diphenylpyrimidine (2.66 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. The same procedure was followed to obtain the target compound C 12 (6.43 g, yield 88%).

Mass: [(M + H) ⁺ ]: 732

[ Synthesis Example  3] Synthesis of C 13

Synthesis Example 1 except that 4-chloro-2,6-diphenylpyrimidine (2.66 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. The same procedure was followed to obtain the target compound C 13 (5.86 g, yield 80%).

Mass: [(M + H) ⁺ ]: 732

[ Synthesis Example  4] Synthesis of C 14

Same as Synthesis Example 1, except that 4-chloro-2,6-diphenylpyridine (2.65 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. The process was carried out to obtain the title compound C 14 (4.97 g, yield 68%).

Mass: [(M + H) ⁺ ]: 731

[ Synthesis Example  5] Synthesis of C 15

Same as Synthesis Example 1 except that 2-chloro-4,6-diphenylpyridine (2.65 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. The process was carried out to obtain the title compound C 15 (5.69 g, yield 78%).

Mass: [(M + H) ⁺ ]: 731

[ Synthesis Example  6] Synthesis of C 21

2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (3.88 g, 10.00 Except for using mmol), the same procedure as in Synthesis Example 1 was carried out to obtain C 21 (6.80 g, yield 84%) as a target compound.

Mass: [(M + H) ⁺ ]: 809

[ Synthesis Example  7] Synthesis of C 22

2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.43 g, 10.00 mmol instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using), the same procedure as in Synthesis Example 1 was performed to obtain C 22 (7.03 g, yield 87%) as a target compound.

Mass: [(M + H) ⁺ ]: 809

[ Synthesis Example  8] Synthesis of C 23

2- (2-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.43 g, 10.00 mmol instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using), the same procedure as in Synthesis Example 1 was performed to obtain C 23 (5.41 g, yield 67%) as a target compound.

Mass: [(M + H) ⁺ ]: 809

[ Synthesis Example  9] Synthesis of C 41

Except for using CDT-2 (6.27 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 41 (5.94 g, 81% yield).

Mass: [(M + H) ⁺ ]: 733

[ Synthesis Example  10] Synthesis of C 52

Except for using CDT-2 (6.27 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 7 to obtain the target compound C 52 (5.82 g, 72% yield).

Mass: [(M + H) ⁺ ]: 809

[ Synthesis Example  11] Synthesis of C 71

Except for using CDT-3 (6.12 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 71 (6.38 g, 89% yield).

Mass: [(M + H) ⁺ ]: 717

[ Synthesis Example  12] Synthesis of C 82

Except for using CDT-3 (6.12 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 7 to obtain the target compound C 82 (6.19 g, yield 78%).

Mass: [(M + H) ⁺ ]: 793

[ Synthesis Example  13] Synthesis of C 101

Except for using CDT-4 (6.12 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 101 (6.09 g, yield 85%).

Mass: [(M + H) ⁺ ]: 717

[ Synthesis Example  14] Synthesis of C 112

Except for using CDT-4 (6.12 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 7 to obtain the target compound C 112 (5.71 g, 72% yield).

Mass: [(M + H) ⁺ ]: 793

[ Synthesis Example  15] Synthesis of C 121

Except for using CDT-5 (5.51 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 121 (4.86 g, yield 74%).

Mass: [(M + H) ⁺ ]: 657

[ Synthesis Example  16] Synthesis of C 131

Except for using CDT-5 (5.51 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 7 to obtain the target compound C 131 (5.87 g, yield 80%).

Mass: [(M + H) ⁺ ]: 734

[ Synthesis Example  17] Synthesis of C 136

Except for using CDT-6 (5.51 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 136 (4.60 g, yield 70%).

Mass: [(M + H) ⁺ ]: 657

[ Synthesis Example  18] Synthesis of C 146

Except for using CDT-6 (5.51 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 7 to obtain the target compound C 146 (6.02 g, 82% yield).

Mass: [(M + H) ⁺ ]: 734

[ Synthesis Example  19] Synthesis of C 151

Except for using CDT-7 (5.35 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 151 (4.49 g, yield 70%).

Mass: [(M + H) ⁺ ]: 641

[ Synthesis Example  20] Synthesis of C 161

Except for using CDT-7 (5.35 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 7 to obtain the target compound C 161 (6.02 g, 84% yield).

Mass: [(M + H) ⁺ ]: 717

[ Synthesis Example  21] Synthesis of C 166

Except for using CDT-8 (5.35 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 166 (4.94 g, yield 77%).

Mass: [(M + H) ⁺ ]: 641

[ Synthesis Example  22] Synthesis of C 176

Except for using CDT-8 (5.35 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 7 to obtain the target compound C 176 (5.81 g, 81% yield).

Mass: [(M + H) ⁺ ]: 717

[ Synthesis Example  23] Synthesis of C 126

Except for using CDT-9 (6.28 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 126 (5.28 g, 72% yield).

Mass: [(M + H) ⁺ ]: 733

[ Synthesis Example  24] Synthesis of C 181

Except for using ADT-1 (6.70 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 181 (5.88 g, yield 76%).

Mass: [(M + H) ⁺ ]: 775

[ Synthesis Example  25] Synthesis of C 196

Except for using ADT-2 (6.70 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 196 (5.50 g, 71% yield).

Mass: [(M + H) ⁺ ]: 775

[ Synthesis Example  26] Synthesis of C 211

Except for using ADT-3 (6.54 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 211 (5.24 g, 69% yield).

Mass: [(M + H) ⁺ ]: 759

[ Synthesis Example  27] Synthesis of C 226

Except for using ADT-4 (6.54 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 226 (5.54 g, 73% yield).

Mass: [(M + H) ⁺ ]: 759

[ Synthesis Example  28] Synthesis of C 241

Except for using ADT-5 (5.94 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 241 (5.03 g, 72% yield).

Mass: [(M + H) ⁺ ]: 699

[ Synthesis Example  29] Synthesis of C 256

Except for using ADT-6 (5.94 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 256 (5.03 g, 72% yield).

Mass: [(M + H) ⁺ ]: 699

[ Synthesis Example  30] Synthesis of C 271

Except for using ADT-7 (5.77 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 271 (5.74 g, 84% yield).

Mass: [(M + H) ⁺ ]: 683

[ Synthesis Example  31] Synthesis of C 286

Except for using ADT-8 (5.77 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 286 (6.01 g, yield 88%).

Mass: [(M + H) ⁺ ]: 683

[ Synthesis Example  32] Synthesis of C 246

Except for using ADT-9 (6.70 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 246 (6.20 g, yield 80%).

Mass: [(M + H) ⁺ ]: 775

[ Synthesis Example  33] Synthesis of C 301

Except for using PDT-1 (6.60 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 301 (5.36 g, yield 70%).

Mass: [(M + H) ⁺ ]: 765

[ Synthesis Example  34] Synthesis of C 346

Except for using PDT-2 (6.44 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 346 (5.46 g, 73% yield).

Mass: [(M + H) ⁺ ]: 748

[ Synthesis Example  35] Synthesis of C 421

Except for using PDT-3 (6.44 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 421 (5.45 g, 73% yield).

Mass: [(M + H) ⁺ ]: 748

[ Synthesis Example  36] Synthesis of C 466

Except for using PDT-4 (6.28 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 466 (5.79 g, yield 79%).

Mass: [(M + H) ⁺ ]: 733

[ Example  1 to 36] green organic Electric field  Fabrication of light emitting device

Compounds C 11 to C 466 synthesized in Synthesis Examples 1 to 36 were subjected to high purity sublimation purification by a conventionally known method, and then green organic EL devices were manufactured according to the following procedure.

First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 Å was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was transferred to.

M-MTDATA (60 nm) / TCTA (80 nm) / C 11 to C 466 each compound + 10% Ir (ppy) ₃ (30nm) / BCP (10 nm) / Alq ₃ ( 30 nm) / LiF (1 nm) / Al (200 nm) was laminated to fabricate an organic EL device.

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ , CBP and BCP are as follows.

Comparative Example 1 Fabrication of Green Organic Electroluminescent Device

A green organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound C 11 as a light emitting host material when forming the emission layer.

[Evaluation Example]

For each of the green organic EL devices produced in Examples 1 to 36 and Comparative Example 1, the driving voltage, current efficiency, and emission peak at current density (10) mA / cm 2 were measured, and the results are shown in Table 1 below. It was.

Sample Host Drive voltage (V) EL peak (nm) Current efficiency (cd / A) Example 1 C 11 6.83 517 41.1 Example 2 C 12 6.82 518 40.7 Example 3 C 13 6.49 518 38.9 Example 4 C 14 6.81 518 39.1 Example 5 C 15 6.82 518 40.7 Example 6 C 21 6.49 518 38.9 Example 7 C 22 6.81 518 39.1 Example 8 C 23 6.66 516 41.7 Example 9 C 41 6.68 518 41.7 Example 10 C 52 6.63 517 39.3 Example 11 C 71 6.61 518 38.5 Example 12 C 82 6.87 517 39.1 Example 13 C 101 6.66 517 41.1 Example 14 C 112 6.71 518 42.2 Example 15 C 121 6.82 517 42.2 Example 16 C 131 6.81 518 41.1 Example 17 C 136 6.83 518 41.7 Example 18 C 146 6.82 518 39.3 Example 19 C 151 6.82 518 39.1 Example 20 C 161 6.81 518 39.1 Example 21 C 166 6.81 518 40.7 Example 22 C 176 6.71 516 39.2 Example 23 C 126 6.68 517 39.8 Example 24 C 181 6.66 518 39.3 Example 25 C 196 6.66 518 39.7 Example 26 C 211 6.63 518 39.2 Example 27 C 226 6.62 518 39.1 Example 28 C 241 6.61 518 39.9 Example 29 C 256 6.49 518 42.2 Example 30 C 271 6.81 516 41.1 Example 31 C 286 6.81 518 41.1 Example 32 C 246 6.71 517 40.4 Example 33 C 301 6.68 518 41.7 Example 34 C 346 6.66 517 39.8 Example 35 C 421 6.73 517 40.7 Example 36 C 466 6.74 518 40.8 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1 above, when the compounds (C 11 to C 466) according to the present invention were used as the light emitting layer of the green organic EL device (Examples 1 to 36), the green organic EL device using the conventional CBP (compared to Compared with Example 1) it can be seen that the better performance in terms of efficiency and driving voltage.

The present invention relates to a novel organic light emitting compound and an organic electroluminescent device comprising the same, and more particularly, by including a novel tertiary substituted benzene-based compound having excellent hole injection, transporting ability, and luminescent ability in one or more organic material layers, The present invention relates to an organic EL device having improved characteristics such as efficiency, driving voltage, and lifetime.

Claims (12)

Compound represented by the following formula (1): [Formula 1]

In Chemical Formula 1, Ar ₁ is a C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl group, C Aryl group of ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C ₁ to C ₄₀ , aryloxy group of C ₆ to C ₆₀ , alkylsilyl group of C ₃ to C ₄₀ , C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₆₀ aryl boron group, C ₆ to C ₆₀ arylphosphine group, C ₆ to C ₆₀ mono or diaryl phosph A pinyl group and a C ₆ -C ₆₀ arylamine group; Y ₁ is O or S; Z ₁ is selected from the group consisting of a single bond, C (R ₁₁ ) (R ₁₂ ), N (R ₁₃ ), O and S; L ₁ and L ₂ are each independently selected from the group consisting of a single bond, an arylene group having ₆ to ₄₀ carbon atoms, and a heteroarylene group having 5 to 40 nuclear atoms; R ₁ to R ₉ and R ₁₁ to R ₁₃ are each independently hydrogen, deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, nuclear atoms 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, A C ₆ to C ₄₀ arylphosphine group, a C ₆ to C ₄₀ mono or diarylphosphinyl group and a C ₆ to C ₄₀ arylsilyl group, or a condensed aromatic ring with an adjacent group, or a condensed heteroaromatic Can form a ring; m is an integer from 0 to 4; R ₁₀ is deuterium, halogen, cyano group, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group, C ₂ -C ₄₀ alkynyl group, C ₆ -C ₄₀ aryl group, nuclear atom 5 to 40 heteroaryl groups, C ₆ to C ₄₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₄₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₄₀ arylboron groups, C ₆ to C ₄₀ arylphosphine groups, C ₆ to C ₄₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ selected from the group consisting arylsilyl of C ₄₀ or, by combining groups of adjacent, may form a fused aromatic ring, or a condensed heteroaromatic ring, a plurality of the R ₁₀ is In individuals they are the same or different from one another; Any one of R ₁ to R ₉ forms a bond with L ₂ ; The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkyl boron group, aryl of the above R ₁ to R ₁₃ Boron group, arylphosphine group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, 5 to 40 heteroaryl group of nuclear atoms, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ Arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₄₀ the arylboronic group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ mono or diaryl phosphine of blood group and a C ₆ ~ C at least one member selected from the ₄₀ group consisting of aryl silyl coming It may be substituted, and they may be the same or different from each other when a plurality of substituents to be substituted. The method of claim 1, L ₁ and L ₂ are each independently a single bond, a phenylene group, a biphenylene group, a naphthylene group, anthracenylene group, an indenylene group, pyrantrenylene group, carbazolylene group, thiophenylene group, indolylene group, A compound characterized in that it is selected from the group consisting of a furinylene group, a quinolinyl group, a pyrroylene group, an imidazolylene group, an oxazolylene group, a thiazolylene group, a triazolylene group, a pyridinylene group and a pyrimidinylene group. The method of claim 1, Ar ₁ is a six-membered nitrogen-containing heterocyclic moiety. The method of claim 3, Ar ₁ is a compound characterized in that the substituent represented by the formula (2): [Formula 2]

In Chemical Formula 2, * Means a moiety bonded to Formula 1 above: L ₃ is selected from the group consisting of a single bond, an arylene group having ₆ to ₄₀ carbon atoms and a heteroarylene group having 5 to 40 nuclear atoms; X ₁ to X ₅ are each independently N or C (R ₁₄ ); R ₁₄ is hydrogen, deuterium, halogen, cyano group, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group, C ₂ -C ₄₀ alkynyl group, C ₆ -C ₄₀ aryl group, nuclear atom number 5 to 40 heteroaryl groups, C ₆ to C ₄₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₄₀ arylamine groups, C ₃ to C ₄₀ cycloalkyl groups, nuclear atoms 3 to 40 heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₄₀ arylboron groups, C ₆ to C ₄₀ arylphosphine groups, C ₆ ~ C ₄₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₄₀ selected from the group consisting of aryl silyl, or as in the combination group and adjacent, may form a fused aromatic ring, or fused heteroaromatic ring, wherein R ₁₄ Are plural, they are the same or different from each other; The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group of R ₁₄ , cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkyl boron group, aryl boron group, an aryl phosphine group, a mono- or diaryl phosphine blood group and an aryl silyl group, each independently, a deuterium, a halogen, a cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl Neyl group, C ₆ ~ C ₄₀ aryl group, 5 to 40 heteroaryl groups, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, an aryl boronic of C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, a alkyl boronic of _{C 1 ~ C 40, C 6} ~ C 40 group, C ₆ ~ C ₄₀ of the aryl phosphine group, C ₆ ~ C ₄₀ mono or diaryl phosphine blood group and one or more substituents selected from the group consisting of aryl silyl C ₆ ~ C ₄₀ of When substituted or unsubstituted and substituted with a plurality of substituents, they may be the same or different from each other. The method of claim 4, wherein Ar ₁ is a compound, characterized in that the substituent represented by any one of the formulas A-1 to A-15:

In Chemical Formulas A-1 to A-15, n is an integer from 0 to 4; R ₂₁ is deuterium (D), halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₄₀ aryl group, 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ aryloxy group , C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₄₀ Aryl boron group , C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ mono or diaryl phosphinyl group C ₆ ~ C _{40 It} may be selected from the group consisting of arylsilyl group, or may be combined with adjacent groups to form a condensed ring When there are a plurality of R ₂₁ , they are the same as or different from each other; The alkyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphine group, mono or diarylphosphinyl group and aryl of R ₂₁ . The silyl groups are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, nuclear atom A number of 5 to 40 heteroaryl groups, C ₆ to C ₄₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₄₀ arylamine groups, C ₃ to C ₄₀ cycloalkyl groups, nuclear atoms C ₃ to C ₄₀ heterocycloalkyl group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₄₀ aryl boron group, C ₆ to C ₄₀ arylphosphine group, C substituted with ₆ ~ C ₄₀ mono or diaryl phosphine blood group and one or more substituents selected from the group consisting of a C ₆ ~ C ₄₀ aryl silyl or of being unsubstituted, light is substituted with plural substituents They are the same or different from each other; *, L ₃ and R ₁₄ are as defined in the formula (2). The method of claim 4, wherein L ₃ represents a single bond, a phenylene group, a biphenylene group, a naphthylene group, an anthracenylene group, an indenylene group, a pyrantrenylene group, a carbazolylene group, a thiophenylene group, an indolylene group, a furinylene group, and a quinolyne group A compound selected from the group consisting of a niylene group, a pyrroylene group, an imidazolylene group, an oxazolylene group, a thiazolylene group, a triazolylene group, a pyridinylene group and a pyrimidinylene group. The method of claim 1, The substituent connected to L ₁ is dibenzofuran (dibenzo [b, d] furan) or dibenzothiophene (dibenzo [b, d] thiophene) characterized in that the compound. The method of claim 1, The substituent connected to L ₂ is characterized in that any one selected from the group consisting of carbazole (cabazole), phenoxazine (phenoxazine), phenothiazine, phenazine (phenazine) and acridine (acridine) compound. The method of claim 1, The compound is a compound characterized in that the compound represented by any one of the following formulas 3 to: [Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

In Chemical Formulas 3 to 7, Ar ₁ , Y ₁ , Z ₁ , L ₁ , L ₂ , R ₁ to R ₁₀ and m are the same as defined in Chemical Formula 1. The method of claim 1, The compound is selected from the group consisting of the following compounds:

An anode, a cathode, and one or more organic material layers interposed between the anode and the cathode; At least one of the at least one organic material layer comprises an organic electroluminescent device comprising the compound of formula (1) according to any one of claims 1 to 10. The method of claim 11, The organic material layer including the compound of Formula 1 is selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron transport auxiliary layer, an electron injection layer, a life improvement layer, a light emitting layer and a light emitting auxiliary layer.