WO2015053524A1 - Organic compound and organic electroluminescent device including same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent device including same. The compound according to the present invention is used in an organic layer of an organic electroluminescent device and preferably in a light emitting layer in order to be capable of having improved light emitting efficiency, driving voltage, and service life in an organic electroluminescent device.

Description

Organic compound and organic electroluminescent device comprising the same

The present invention relates to a novel organic compound and an organic electroluminescent device comprising the same.

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 material may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to realize better natural colors according to light emission colors. In addition, in order to increase luminous efficiency through an increase in color purity and energy transfer, a host / dopant system may be used as a light emitting material.

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 phosphorescent dopants can theoretically improve luminous efficiency up to 4 times compared to fluorescent dopants, studies on phosphorescent dopants as well as phosphorescent hosts are being conducted.

At present, anthracene derivatives are known as fluorescent dopant / host materials used in the light emitting layer. In addition, as a phosphorescent dopant material used in the light emitting layer, metal complex compounds containing Ir such as Firpic, Ir (ppy) ₃ , and (acac) Ir (btp) ₂ are known, and as a phosphorescent host material, 4,4-dicarbazolybiphenyl (CBP) is known.

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.

Another object of the present invention is to provide an organic electroluminescent device having an improved driving voltage, luminous efficiency, and the like, including the organic compound.

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,

L ₁ and L ₂ are each independently selected from the group consisting of a single bond, a substituted or unsubstituted C ₆ to C ₁₈ arylene group, and a substituted or unsubstituted heteroarylene group having 5 to 18 nuclear atoms,

X ₁ to X ₃ are each independently N or C (R ₁₁ ), wherein at least one is N,

R ₁ to R ₄ 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 the aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ of the aryloxy group, C ₁ ~ C ₄₀ of the alkyloxy group, C ₆ ~ C ₄₀ aryl amine group, a C ₃ ~ C ₄₀ cycloalkyl, nuclear atoms silyl of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ aryl boronic of C _40, a C ₆ ~ C ₄₀ An arylphosphine group, a C ₆ -C ₄₀ arylphosphine oxide group and a C ₆ -C ₄₀ arylsilyl group, or combine with an adjacent group to form a condensed ring,

R ₁₁ and Ar ₁ 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 the aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ of the aryloxy group, C ₁ ~ C ₄₀ of the alkyloxy group, C ₆ ~ C ₄₀ aryl amine group, a C ₃ ~ C ₄₀ cycloalkyl, nuclear atoms silyl of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ aryl boronic of C _40, a C ₆ ~ C ₄₀ An aryl phosphine group, a C ₆ ~ C ₄₀ aryl phosphine oxide group and a C ₆ ~ C ₄₀ arylsilyl group,

The arylene group and heteroarylene group of L ₁ and L ₂ , the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group of R ₁ to R ₄ , R ₁₁ and Ar ₁ , Arylamine group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group, arylsilyl group are each independently deuterium, halogen, cyano group, C ₁ a ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ of the 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 group, C ₁ to C ₄₀ alkylsilyl group, a C ₁ ~ C ₄₀ group, the alkyl boron C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide of the group and a C ₆ ~ C ₄₀ arylsilyl group Substituted or unsubstituted with one or more selected from the group consisting of, wherein, when substituted with a plurality of substituents, they are the same or different from each other,

m and n are each independently an integer of 0-4.

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 provides an organic electroluminescent device comprising the compound of Formula 1. .

Herein, the organic material layer including the compound of Formula 1 may be a phosphorescent layer.

Alkyl in the present invention is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like. There is no limitation.

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

Alkynyl in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having one or more carbon-carbon triple bonds. Examples thereof include ethynyl, 2- Propanyl (2-propynyl) and the like, but are not limited thereto.

Aryl in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 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 pendant or condensed with each other 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 simply attached or condensed with each other may be included, and is also construed to include a form 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.

Aryloxy in the present invention is a monovalent substituent represented by RO-, wherein R means aryl having 6 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

Alkyloxy in the present invention is a monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl, and includes a linear, branched or cyclic structure. Interpret it. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

Aryl amine in the present invention means an amine substituted with aryl having 6 to 40 carbon atoms.

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

Alkylsilyl in the present invention is silyl substituted with alkyl having 1 to 40 carbon atoms, arylsilyl means silyl substituted with aryl having 6 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.

Hereinafter, the present invention will be described in detail.

1. New Organic Compounds

The novel compound according to the present invention forms a basic skeleton by combining dibenzofuran (dibenzo [b, d] furan), a 6-membered heterocycle, an indole moiety, and a structure in which various substituents are bonded to the basic skeleton. It is characterized in that represented by the formula (1).

Dibenzofuran (dibenzo [b, d] furan) has a large triplet energy and is electrochemically stable. A six-membered nitrogen-containing heterocyclic ring (eg, pyridine, pyrimidine, triazine), which is an electron withdrawing group (EWG), to the dibenzofuran (dibenzo [b, d] furan), and an electron donor group ( Compound represented by the formula (1) of the present invention combined with an indole moiety (EDG), an electron donating group (EDG) is an electron withdrawing group (EWG) and electron donor having a large electron donor Since the entire molecule has an electron donating group (EDG) and exhibits bipolar characteristics, the bonding force between the holes and the electrons is high, so that the molecules can be used not only as a host in the phosphorescent layer but also in the hole transport layer and the hole injection layer.

In addition, the compound represented by the general formula (1) of the present invention is significantly increased in molecular weight of the compound due to the aromatic ring (aromatic ring) or heteroaromatic ring (heteroaromatic ring) substituents, the glass transition temperature is improved as the conventional CBP (4, 4-dicarbazolybiphenyl) shows higher thermal stability. The compound represented by the formula (1) of the present invention is also effective in suppressing crystallization of the organic material 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.

In the compound represented by Formula 1 of the present invention, L ₁ and L ₂ are a divalent group linker, a single bond, a substituted or unsubstituted C ₆ ~ C ₄₀ arylene group, or substituted or It is an unsubstituted heteroarylene group having 5 to 40 nuclear atoms.

Although the C ₆ to C ₄₀ arylene group and the heteroarylene group having 5 to 40 nuclear atoms are not particularly limited, a phenylene group, a biphenylene group, a naphthylene group, an anthracenylene group, an indenylene group, and a pyrantrenylene group , Carbazolylene group, thiophenylene group, indolylene group, furinylene group, quinolinyl group, pyrroylene group, imidazolylene group, oxazolylene group, thiazolylene group, triazolylene group, pyridinylene group, pyrimididi And a nylene group.

Specifically, it is preferable that L ₁ and L ₂ are each independently a single bond, a phenylene group, or a biphenylene group.

In the compound represented by the formula (1) of the present invention, X ₁ to X ₃ are each independently N or C (R ₁₁ ), at least one includes N, it is preferable that all of X ₁ to X ₃ are N Do. In addition, when two or more of X ₁ to X ₃ are C (R ₁₁ ), a plurality of R ₁₁ are the same or different from each other, and R ₁₁ is preferably hydrogen.

In the compound represented by Formula 1 of the present invention, R ₁ and R ₂ may be bonded to each other to form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, and a condensed heteroaromatic ring. Specifically, R ₁ and R ₂ are preferably bonded to each other to form benzene, naphthalene, indole, fluorene, carbazole.

In the compound represented by Formula 1 of the present invention, R ₃ and R ₄ are each independently hydrogen, a C ₆ ~ C ₄₀ aryl group, or a heteroaryl group having 5 to 40 nuclear atoms.

In particular, R ₃ is more preferably selected from the group consisting of hydrogen, phenyl group, naphthyl group, fluorene group, carbazole group, dibenzothiophene group, dibenzofuran group, dibenzoselenophene group and dibenzosilol group.

In the compound represented by Formula 1 of the present invention, Ar ₁ is preferably a hydrogen, a C ₆ ~ C ₄₀ aryl group, or a heteroaryl group having 5 to 40 nuclear atoms.

The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group of R ₁ to R ₄ , R ₁₁ and Ar ₁ , Alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl silyl group 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, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C ₆ ~ C _40, alkyloxy group of C ₁ ~ C ₄₀ of, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C group ₁ ~ C ₄₀ alkyl silyl, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ aryl group of boron, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ 1 or more substituents selected from the group consisting of C ₄₀ aryl silyl Substituted or unsubstituted, and when substituted with a plurality of substituents they are the same or different from each other.

The compound represented by the formula (1) of the present invention is preferably selected from the group consisting of the compound represented by the following formula (2 to 10).

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

In Formulas 2 to 10, X ₁ to X ₃ , L ₁ , L ₂ , R ₁ to R ₄ , Ar ₁ , m and n are the same as defined in Formula 1,

Y ₁ is selected from the group consisting of N (R ₁₂ ), O, S, Se, C (R ₁₃ ) (R ₁₄ ) and Si (R ₁₅ ) (R ₁₆ ),

R ₅ , R ₆ and R ₁₂ to R ₁₆ 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 atom 5 ~ 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, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group and C ₆ ~ C _{40 It} is selected from the group consisting of arylsilyl group,

The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group of R _5, R ₆ , R ₁₂ to R ₁₆ , Alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl silyl 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, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ to C ₄₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkylboron group, C group _{of 6} to arylboronic of C _40, C ₆ to C ₄₀ aryl phosphine group, C ₆ to C ₄₀ aryl substituted with phosphine oxide groups and C ₆ to 1 or more selected from the group consisting of C ₄₀ arylsilyl of Is unsubstituted, l is an integer from 0 to 4.

Examples of the compound represented by Formula 1 of the present invention include the following compounds (C-1 to C-129), but the compound represented by Formula 1 of the present invention is not limited to the following compounds.

The compound represented by Chemical Formula 1 of the present invention can be synthesized in various ways with reference to the following synthesis examples.

2. Organic electroluminescent device

The present invention includes an anode, a cathode and at least one organic layer interposed between the anode and the cathode, and at least one of the at least one organic layer includes the compound represented by Formula 1 It provides an organic electroluminescent device. 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, or the like may be used.

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.

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 can be used.

The hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer are 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 the following Examples. However, the following examples are merely to illustrate the invention, the present invention is not limited by the following examples.

Preparation Example 1 Synthesis of IC-1

Dissolve magnesium (14.5 g, 598 mmol) and iodine (3.0 g, 12 mmol) in 50 ml of anhydrous tetrahydrofuran solvent, then add 4-bromodibenzo [b, d] furan (147.7 g, 598 mmol) in 130 ml of anhydrous tetrahydrofuran. The dissolved solution is added dropwise for 30 minutes. The mixture is stirred at 80 ° C. for 2 hours and then cooled at room temperature. Then, a solution of 1,3,5-trichlorotriazine (110.3 g, 598 mmol) dissolved in 390 ml of anhydrous tetrahydrofuran is added dropwise while stirring for 3 hours.

After the reaction was completed, the mixture was distilled under reduced pressure to remove the organic solvent, the residue was purified by column chromatography, and the crystals obtained by recrystallization with methanol were filtered to obtain IC-1 (40.89 g, yield 65%).

¹ H-NMR: δ 7.32 (m, 3 H), 7.66 (d, 1 H), 7.85 (m, 3 H)

Preparation Example 2 Synthesis of IC-2

The same procedure as in Preparation Example 1 was performed except that 2-bromodibenzo [b, d] furan (147.7 g, 598 mmol) was used instead of 4-bromodibenzo [b, d] furan used in Preparation Example 1. -2 was obtained.

¹ H-NMR: δ 7.35 (m, 2H), 7.70 (m, 3H), 7.85 (m, 2H)

Preparation Example 3 Synthesis of IC-3

9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole (2.59 g, 7.03 mmol), 3-bromo-9H- under nitrogen stream carbazole (2.07 g, 8.43 mmol), NaOH (0.84 g, 21.08 mmol) and THF / H ₂ O (40 ml / 20 ml) were mixed and then Pd (PPh ₃ ) ₄ (0.48 g, 5 mol) at 40 ° C. %) Was added and stirred at 80 ° C. for 12 hours.

After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain IC-3 (2.15 g, yield 75%).

¹ H-NMR: δ 7.29 (m, 3H), 7.55 (m, 11H), 7.88 (m, 3H), 8.12 (d, 1H), 8.53 (d, 1H), 10.33 (s, 1H)

Preparation Example 4 Synthesis of IC-4

IC-3 (18.85 g, 46.17 mmol), 1-bromo-3-iodobenzene (19.59 g, 69.26 mmol), Cu powder (0.29 g, 4.62 mmol), K ₂ CO ₃ ( 6.38 g, 46.17 mmol) and nitrobenzene (200 ml) were mixed and stirred at 190 ° C. for 12 hours.

After completion of the reaction, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . After removing the solvent in the organic layer was removed from water and purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to give the IC-4 (20.81 g, yield 80%).

¹ H-NMR: δ 7.30 (m, 5H), 7.60 (m, 12H), 7.91 (m, 4H), 8.51 (m, 2H)

Preparation Example 5 Synthesis of IC-5

7-chloro-3-phenyl-3,10-dihydropyrrolo [3,2-a] carbazole (2.23 g, 7.03 mmol) under a nitrogen stream. 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole (3.11 g, 8.43 mmol), X-phos (0.33 g, 0.70 mmol ), Cs ₂ CO ₃ (4.58 g, 14.06 mmol) and Toluene / Ethanol / H ₂ O (80 ml / 20 ml / 20 ml) were mixed, followed by Pd (OAc) ₂ (0.08 g, 5 mol%). Put and stirred at 110 ℃ for 6 hours.

After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. The solvent was removed from the organic layer and purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain IC-5 (2.21 g, yield 60%).

¹ H NMR: δ 6.52 (d, 1H), 7.30 (m, 2H), 7.54 (m, 15H), 7.94 (m, 5H), 8.55 (d, 1H), 10.33 (s, 1H)

Preparation Example 6 Synthesis of IC-6

Except for using IC-5 (24.17 g, 46.17 mmol) instead of IC-3 IC-6 was obtained by the same procedure as in Preparation Example 4.

¹ H NMR: δ 6.52 (d, 1H), 7.30 (m, 3H), 7.58 (m, 14H), 7.69 (d, 1H), 7.77 (m, 2H), 7.98 (m, 5H), 8.18 (d , 1H), 8.57 (d, 1H)

Preparation Example 7 Synthesis of IC-7

2- (dibenzo [b, d] thiophen-4-yl)-instead of 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.18 g, 7.03 mmol), and 8-bromo-11H-benzo [a] carbazole (2.50 g instead of 3-bromo-9H-carbazole , 8.43 mmol) was used in the same manner as in Preparation Example 3, except that IC-7 was obtained.

¹ H-NMR: δ 7.57 (m, 7H), 7.77 (s, 1H), 7.87 (d, 1H), 7.98 (d, 1H), 8.16 (m, 3H), 8.45 (m, 3H), 10.24 ( s, 1 H)

Preparation Example 8 Synthesis of IC-8

IC-7 (18.44 g, 46.17 mmol) is used instead of IC-3, and 1-bromo-4-iodobenzene (19.59 g, 69.26 mmol) is used instead of 1-bromo-3-iodobenzene (19.59 g, 69.26 mmol). Except for the same procedure as in Preparation Example 4 to obtain an IC-8.

¹ H NMR: δ 7.55 (m, 10H), 7.76 (s, 1H), 7.99 (m, 2H), 8.16 (m, 4H), 8.45 (m, 3H)

Preparation Example 9 Synthesis of IC-9

2- (dibenzo [b, d] furan-4-yl)-instead of 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.06 g, 7.03 mmol) was used and 10-bromo-7H-benzo [c] carbazole (2.50 g instead of 3-bromo-9H-carbazole , 8.43 mmol) was subjected to the same procedure as in Preparation Example 3, except that IC-9 was obtained.

¹ H-NMR: δ 7.36 (m, 3H), 7.66 (m, 6H), 7.81 (m, 5H), 8.16 (d, 1H), 8.54 (d, 1H), 10.12 (s, 1H)

Preparation Example 10 Synthesis of IC-10

2- (9,9-dimethyl-9H-fluoren-3-yl instead of 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole ) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.25 g, 7.03 mmol), and 2-bromo-11,11-dimethyl-5, instead of 3-bromo-9H-carbazole, IC-10 was obtained by the same procedure as in Preparation Example 3 except for using 11-dihydroindeno [1,2-b] carbazole (3.05 g, 8.43 mmol).

¹ H-NMR: δ 1.73 (s, 12H), 7.26 (m, 2H), 7.40 (m, 2H), 7.58 (m, 5H), 7.69 (d, 1H), 7.77 (s, 1H), 7.87 ( m, 2H), 8.09 (m, 3H), 10.19 (s, 1H)

Synthesis Example 1 Synthesis of C-1

Step 1 Synthesis of 2-chloro-4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine

Dissolve magnesium (14.5 g, 598 mmol) and iodine (3.0 g, 12 mmol) in 50 ml of anhydrous tetrahydrofuran solvent, and add a dropwise solution of bromobenzene (93.89 g, 598 mmol) in 130 ml of anhydrous tetrahydrofuran for 30 minutes. do. The mixture is stirred at 80 ° C. for 2 hours and then cooled at room temperature. Thereafter, a solution of IC-1 (189.05 g, 598 mmol) dissolved in 390 ml of anhydrous tetrahydrofuran is added dropwise with stirring for 3 hours.

After completion of the reaction, the reaction mixture was distilled under reduced pressure to remove the organic solvent, purified by column chromatography, and recrystallized with methanol. The obtained crystals were filtered to give 2-chloro-4- (dibenzo [b, d] furan-4-yl). -6-phenyl-1,3,5-triazine (162.58 g, yield 86%) was obtained.

GC-Mass (Theoretical value: 357.79 g / mol, Measured value: 357 g / mol)

<Step 2> Synthesis of C-1

IC-3 (8.45 g, 20.7 mmol), 2-chloro-4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine (8.87 g, 24.8) under nitrogen stream mmol), NaH (746 mg, 31.1 mmol) and DMF (300 ml) were mixed and stirred at room temperature for 3 hours. After the reaction was completed, water was added, the solid compound was filtered and purified by column chromatography to obtain the title compound C-1 (8.91 g, yield 59%).

GC-Mass (Theoretical value: 729.82 g / mol, Measured value: 729 g / mol)

Synthesis Example 2 Synthesis of C-2

<Step 1> Synthesis of 2-([1,1'-biphenyl] -3-yl) -4-chloro-6- (dibenzo [b, d] furan-2-yl) -1,3,5-triazine

<Step of Synthesis Example 1 except that 3-bromo-1,1'-biphenyl (139.39 g, 598 mmol) was used instead of bromobenzene and IC-2 (189.05 g, 598 mmol) was used instead of IC-1. 1 (2) [(1,1'-biphenyl] -3-yl) -4-chloro-6- (dibenzo [b, d] furan-2-yl) -1,3,5 -triazine (176.43 g, yield 68%) was obtained.

GC-Mass (Theoretical value: 433.89 g / mol, Measured value: 433 g / mol)

<Step 2> Synthesis of C-2

IC-4 (336.96 g, 598 mmol) was used instead of bromobenzene, and 2-([1,1'-biphenyl] -3-yl) -4-chloro-6- (dibenzo [b, d] was used instead of IC-1. Except for using furan-2-yl) -1,3,5-triazine (259.46 g, 598 mmol), the same procedure as in <Step 1> of Synthesis Example 1 was performed, thereby obtaining C-2 (369.21) as a target compound. g, yield 70%) was obtained.

GC-Mass (Theoretical value: 882.02 g / mol, Measured value: 882 g / mol)

Synthesis Example 3 Synthesis of C-3

Step 1 Synthesis of 2-chloro-4,6-bis (dibenzo [b, d] furan-4-yl) -1,3,5-triazine

Except for using 4-bromodibenzo [b, d] furan (147.75 g, 598 mmol) instead of bromobenzene, the same procedure as in <Step 1> of Synthesis Example 1 was carried out to provide 2-chloro-4,6-bis (dibenzo [b, d] furan-4-yl) -1,3,5-triazine (203.54 g, yield 76%) was obtained.

GC-Mass (Theoretical value: 447.87 g / mol, Measured value: 447 g / mol)

<Step 2> Synthesis of C-3

IC-4 (336.96 g, 598 mmol) is used instead of bromobenzene, and 2-chloro-4,6-bis (dibenzo [b, d] furan-4-yl) -1,3,5-triazine is used instead of IC-1. Except for using (267.82 g, 598 mmol) was carried out in the same manner as in <Step 1> of Synthesis Example 1 to obtain the target compound C-3 (289.33 g, yield 54%).

GC-Mass (Theoretical value: 896.00 g / mol, Measured value: 896 g / mol)

Synthesis Example 4 Synthesis of C-4

Synthesis of 2-chloro-4- (dibenzo [b, d] furan-4-yl) -6- (naphthalen-1-yl) -1,3,5-triazine

Except for using 1-bromonaphthalene (123.82 g, 598 mmol) instead of bromobenzene to the same procedure as in <Step 1> of Synthesis Example 1 2-chloro-4- (dibenzo [b, d] furan-4- yl) -6- (naphthalen-1-yl) -1,3,5-triazine (187.79 g, yield 77%) was obtained.

GC-Mass (Theoretical value: 407.85 g / mol, Measured value: 407 g / mol)

Step 2 Synthesis of C-4

Use IC-5 (10.83 g, 20.7 mmol) instead of IC-3, and instead of 2-chloro-4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine Except using 2-chloro-4- (dibenzo [b, d] furan-4-yl) -6- (naphthalen-1-yl) -1,3,5-triazine (10.11 g, 24.8 mmol) Was obtained in the same manner as in <Step 2> of Synthesis Example 1 to obtain the title compound C-4 (11.85 g, yield 64%).

GC-Mass (Theoretical value: 895.02 g / mol, Measured value: 895 g / mol)

Synthesis Example 5 Synthesis of C-5

Step 1 Synthesis of 2-chloro-4- (dibenzo [b, d] furan-4-yl) -6- (pyridin-2-yl) -1,3,5-triazine

Except for using 2-bromopyridine (94.48g, 598 mmol) instead of bromobenzene to the same procedure as in <Step 1> of Synthesis Example 1 2-chloro-4- (dibenzo [b, d] furan-4- yl) -6- (pyridin-2-yl) -1,3,5-triazine (128.73 g, yield 60%) was obtained.

GC-Mass (Theoretical value: 358.78 g / mol, Measured value: 358 g / mol)

Step 2 Synthesis of C-5

IC-6 (405.81 g, 598 mmol) was used instead of bromobenzene, and 2-chloro-4- (dibenzo [b, d] furan-4-yl) -6- (pyridin-2-yl)-was used instead of IC-1. Except for using 1,3,5-triazine (214.55 g, 598 mmol) to carry out the same process as in <Step 1> of Synthesis Example 1 to give the target compound C-5 (181.95 g, 33% yield) Got it.

GC-Mass (Theoretical value: 922.04 g / mol, Measured value: 922 g / mol)

Synthesis Example 6 Synthesis of C-6

<Step 1> Synthesis of 4- (4-chloro-6- (dibenzo [b, d] furan-4-yl) -1,3,5-triazin-2-yl) -N, N-diphenylaniline

Except for using 4-bromo-N, N-diphenylaniline (193.87g, 598 mmol) instead of bromobenzene was carried out the same procedure as in <Step 1> of Synthesis Example 1 4- (4-chloro-6- (dibenzo [b, d] furan-4-yl) -1,3,5-triazin-2-yl) -N, N-diphenylaniline (244.88 g, yield 78%) was obtained.

GC-Mass (Theoretical value: 525.00 g / mol, Measured value: 525 g / mol)

<Step 2> Synthesis of C-6

Use IC-7 (8.27 g, 20.7 mmol) instead of IC-3, and instead of 2-chloro-4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine 4- (4-chloro-6- (dibenzo [b, d] furan-4-yl) -1,3,5-triazin-2-yl) -N, N-diphenylaniline (13.02 g, 24.8 mmol) was used Except that, the same procedure as in <Step 2> of Synthesis Example 1 was performed to obtain C-6 (9.19 g, yield 50%) as a target compound.

GC-Mass (Theoretical value: 888.04 g / mol, Measured value: 888 g / mol)

Synthesis Example 7 Synthesis of C-7

Step 1 Synthesis of 9- (4- (4-chloro-6- (dibenzo [b, d] furan-2-yl) -1,3,5-triazin-2-yl) phenyl) -9H-carbazole

Synthesis Example 1 except that 9- (4-bromophenyl) -9H-carbazole (192.67g, 598 mmol) was used instead of bromobenzene and IC-2 (189.05g, 598 mmol) was used instead of IC-1. Follow the same procedure as in step 1> to obtain 9- (4- (4-chloro-6- (dibenzo [b, d] furan-2-yl) -1,3,5-triazin-2-yl) phenyl)- 9H-carbazole (134.47 g, yield 43%) was obtained.

GC-Mass (Theoretical value: 522.98 g / mol, Measured value: 522 g / mol)

Step 2 Synthesis of C-7

IC-8 (331.59 g, 598 mmol) was used instead of bromobenzene, and 9- (4- (4-chloro-6- (dibenzo [b, d] furan-2-yl) -1,3, Except for using 5-triazin-2-yl) phenyl) -9H-carbazole (312.74 g, 598 mmol), and was subjected to the same process as in <Step 1> of Synthesis Example 1 C-7 (253.15 g, yield 44%).

GC-Mass (Theoretical value: 962.12 g / mol, Measured value: 962 g / mol)

Synthesis Example 8 Synthesis of C-8

<Step 1> of 2-chloro-4- (dibenzo [b, d] furan-2-yl) -6- (9,9-dimethyl-9H-fluoren-3-yl) -1,3,5-triazine synthesis

Synthesis Example 1 except that 3-bromo-9,9-dimethyl-9H-fluorene (163.35g, 598 mmol) was used instead of bromobenzene and IC-2 (189.05g, 598 mmol) was used instead of IC-1. Perform the same process as in <Step 1> of the compound 2-chloro-4- (dibenzo [b, d] furan-2-yl) -6- (9,9-dimethyl-9H-fluoren-3-yl)- 1,3,5-triazine (161.55 g, yield 57%) was obtained.

GC-Mass (Theoretical value: 473.95 g / mol, Measured value: 473 g / mol)

Step 2 Synthesis of C-8

Use IC-9 (7.94 g, 20.7 mmol) instead of IC-3, and instead of 2-chloro-4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine 2-chloro-4- (dibenzo [b, d] furan-2-yl) -6- (9,9-dimethyl-9H-fluoren-3-yl) -1,3,5-triazine (11.75 g, 24.8 Except for using mmol), the same process as in <Step 2> of Synthesis Example 1 was performed, to obtain C-8 (13.42 g, yield 79%) of the title compound.

GC-Mass (Theoretical value: 820.93 g / mol, Measured value: 820 g / mol)

Synthesis Example 9 Synthesis of C-9

<Step 1> Synthesis of 2-chloro-4- (dibenzo [b, d] furan-2-yl) -6- (6-phenylpyridin-3-yl) -1,3,5-triazine

5-Bromo-2-phenylpyridine (139.98g, 598 mmol) was used instead of bromobenzene, and IC-2 (189.05g, 598 mmol) was used instead of IC-1. The same procedure was followed for 2-chloro-4- (dibenzo [b, d] furan-2-yl) -6- (6-phenylpyridin-3-yl) -1,3,5-triazine (161.23 g, yield 62 %) Was obtained.

GC-Mass (Theoretical value: 434.88 g / mol, Measured value: 434 g / mol)

Step 2 Synthesis of C-9

Use IC-10 (9.84 g, 20.7 mmol) instead of IC-3, and instead of 2-chloro-4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine The use of 2-chloro-4- (dibenzo [b, d] furan-2-yl) -6- (6-phenylpyridin-3-yl) -1,3,5-triazine (10.78 g, 24.8 mmol) Except for the same procedure as in <Step 2> of Synthesis Example 1 to obtain a target compound C-9 (9.95 g, 55% yield).

GC-Mass (Theoretical value: 874.04 g / mol, Measured value: 874 g / mol)

Examples 1 to 9 Fabrication of Green Organic Electroluminescent Devices

Compounds synthesized in Synthesis Examples 1 to 9 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 된 was ultrasonically washed with distilled water. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then the substrate is cleaned for 5 minutes by UV and vacuum evaporator The substrate was transferred to.

M-MTDATA (60 nm) / TCTA (80 nm) / each compound synthesized in Synthesis Examples 1 to 9 + 10% Ir (ppy) ₃ (30nm) / BCP (10 nm) on the thus prepared ITO transparent substrate (electrode) ) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) was laminated in order to manufacture a device.

Comparative Examples 1 and 2 Fabrication of Green Organic Electroluminescent Devices

A device was manufactured in the same manner as in Example 1, except that CBP and Ref-1 were used instead of the compound of Synthesis Example 1 as a light emitting host material when forming the emission layer.

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ , BCP, CBP and Ref-1 used in Examples 1 to 9 and Comparative Examples 1 and 2 are as follows.

[Evaluation Example 1]

For each of the green organic electroluminescent devices manufactured in Examples 1 to 9 and Comparative Examples 1 and 2, the driving voltage, current efficiency and emission peak at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 1 below. Indicated.

Table 1

Sample	Host	Drive voltage (V)	EL peak (nm)	Current efficiency (cd / A)
Example 1	C-1	6.60	519	42.0
Example 2	C-2	6.55	520	41.5
Example 3	C-3	6.45	518	41.2
Example 4	C-4	6.50	518	41.9
Example 5	C-5	6.50	518	41.7
Example 6	C-6	6.60	521	41.0
Example 7	C-7	6.40	522	40.7
Example 8	C-8	6.45	522	40.8
Example 9	C-9	6.50	521	41.5
Comparative Example 1	CBP	6.93	516	38.2
Comparative Example 2	Ref-1	6.75	517	40.2

As shown in Table 1, Examples 1 to 9 in which the compound of the present invention was applied to the light emitting layer of the green organic electroluminescent device were compared to Comparative Examples 1 and 2 in which the conventional CBP and Ref-1 were applied to the light emitting layer of the green organic electroluminescent device. It was confirmed that the efficiency and the driving voltage is excellent.

Examples 10 to 12 Red Organic Electroluminescent Device Manufacturing

After the high purity sublimation purification of the compound synthesized in Synthesis Examples 6 to 8 by a commonly known method, a red organic electroluminescent device was manufactured according to the following procedure.

First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 된 was ultrasonically washed with distilled water. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then washed the substrate for 5 minutes using UV and vacuum The substrate was transferred to the evaporator.

M-MTDATA (60 nm) / TCTA (80 nm) / each compound synthesized in Synthesis Examples 6 to 8 + 10% (piq) ₂ Ir (acac) (30nm) / BCP on the thus prepared ITO transparent substrate (electrode) The device was manufactured by stacking in the order of (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm).

Comparative Example 3 Manufacture of Red Organic Electroluminescent Device

A device was manufactured in the same manner as in Example 10, except that CBP was used instead of the compound of Synthesis Example 6 as a light emitting host material when forming the emission layer.

The structures of m-MTDATA, (piq) ₂ Ir (acac), BCP, NPB and CBP used in Examples 10 to 12 and Comparative Example 3 are as follows.

[Evaluation Example 2]

For each of the red organic electroluminescent devices prepared in Examples 10 to 12 and Comparative Example 3, the driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured, and the results are shown in Table 2 below.

TABLE 2

Sample	Host	Drive voltage (V)	Current efficiency (cd / A)
Example 10	C-6	4.90	13.0
Example 11	C-7	4.95	12.5
Example 12	C-8	4.85	12.7
Comparative Example 3	CBP	5.25	8.2

As shown in Table 2, Examples 10 to 12 in which the compound of the present invention is applied to the light emitting layer of the red organic electroluminescent device have a higher efficiency and driving voltage compared to Comparative Example 3 in which the conventional CBP is applied to the light emitting layer of the red organic electroluminescent device. It was confirmed that it was excellent.

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.

Claims (9)

1. Compound represented by the following formula (1):

   [Formula 1]

   

   In Chemical Formula 1,

   L ₁ and L ₂ are each independently selected from the group consisting of a single bond, a substituted or unsubstituted C ₆ ~ C ₁₈ arylene group and a substituted or unsubstituted heteroarylene group having 5 to 18 nuclear atoms,

   X ₁ to X ₃ are each independently N or C (R ₁₁ ), wherein at least one is N,

   R ₁ to R ₄ 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 the aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ of the aryloxy group, C ₁ ~ C ₄₀ of the alkyloxy group, C ₆ ~ C ₄₀ aryl amine group, a C ₃ ~ C ₄₀ cycloalkyl, nuclear atoms silyl of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ aryl boronic of C _40, a C ₆ ~ C ₄₀ An arylphosphine group, a C ₆ -C ₄₀ arylphosphine oxide group and a C ₆ -C ₄₀ arylsilyl group, or combine with an adjacent group to form a condensed ring,

   R ₁₁ and Ar ₁ 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 the aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ of the aryloxy group, C ₁ ~ C ₄₀ of the alkyloxy group, C ₆ ~ C ₄₀ aryl amine group, a C ₃ ~ C ₄₀ cycloalkyl, nuclear atoms silyl of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ aryl boronic of C _40, a C ₆ ~ C ₄₀ An aryl phosphine group, a C ₆ ~ C ₄₀ aryl phosphine oxide group and a C ₆ ~ C ₄₀ arylsilyl group,

   The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group of R ₁ to R ₄ , R ₁₁ and Ar ₁ , Alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl silyl 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, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ to C ₄₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkylboron group, C value to ₆ ~ C ₄₀ aryl group of boron, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide groups and at least one member selected from the group consisting of C ₆ ~ C ₄₀ aryl group in the silyl Or it is unsubstituted,

   m and n are each independently an integer of 0-4.
2. The method of claim 1,

   Compound represented by Formula 1 is selected from the group consisting of compounds represented by the following formula 2 to 10:

   [Formula 2]

   

   [Formula 3]

   

   [Formula 4]

   

   [Formula 5]

   

   [Formula 6]

   

   [Formula 7]

   

   [Formula 8]

   

   [Formula 9]

   

   [Formula 10]

   

   In Chemical Formulas 2 to 10,

   X ₁ to X ₃ , L ₁ , L ₂ , R ₁ to R ₄ , Ar ₁ , n and m are the same as defined in claim 1,

   Y ₁ is selected from the group consisting of N (R ₁₂ ), O, S, Se, C (R ₁₃ ) (R ₁₄ ) and Si (R ₁₅ ) (R ₁₆ ),

   R _5, R ₆ , R ₁₂ to R ₁₆ 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 atom 5 ~ 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, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group and C ₆ ~ C _{40 It} is selected from the group consisting of arylsilyl group,

   The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group of R _5, R ₆ , R ₁₂ to R ₁₆ , Alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl silyl group 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, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ to C ₄₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkylboron group, C group _{of 6} to arylboronic of C _40, C ₆ to C ₄₀ aryl phosphine group, C ₆ to C ₄₀ aryl substituted with phosphine oxide groups and C ₆ to 1 or more selected from the group consisting of C ₄₀ arylsilyl of It is unsubstituted,

   l is an integer of 0-4.
3. The method of claim 2,

   Y ₁ is N (R ₁₂ ), and R ₁₂ is a phenyl group.
4. The method of claim 2,

   Y ₁ is C (R ₁₃ ) (R ₁₄ ), and R ₁₃ and R ₁₄ are methyl groups.
5. The method of claim 1,

   Wherein L ₁ and L ₂ are each independently a single bond, phenylene or biphenylene.
6. The method of claim 1,

   X ₁ to X ₃ is N characterized in that the N.
7. The method of claim 1,

   Ar ₁ is a C ₆ ~ C ₄₀ A aryl group or a nuclear atom, characterized in that a heteroaryl group of 5 to 40 atoms.
8. An anode, a cathode, and one or more organic material layers interposed between the anode and the cathode;

   At least one of the one or more organic material layers is an organic electroluminescent device comprising the compound according to any one of claims 1 to 7.
9. The method of claim 8,

   The organic material layer containing the compound is an organic electroluminescent device, characterized in that the phosphorescent layer.