KR20170076292A - Organic light-emitting compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device using the same. More specifically, the present invention relates to a novel compound having excellent electron transporting ability and a method for producing the same. To an organic electroluminescent device having improved characteristics.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic electroluminescent compound, and an organic electroluminescent device using the same. BACKGROUND ART [0002]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same. More particularly, the present invention relates to a compound having excellent electron transporting ability and an organic electroluminescent device having improved characteristics such as luminous efficiency, Emitting device.

Generally, an organic light emitting phenomenon refers to a phenomenon in which light appears when electric energy is applied to an organic material. That is, when a voltage is applied between the two electrodes when the organic layer is positioned between the anode and the cathode, holes are injected into the organic layer and holes are injected into the organic layer. When the injected holes and electrons meet, an exciton is formed. When the exciton falls back to the ground state, light is emitted.

As a method for efficiently forming an organic electroluminescent device, research has been conducted to manufacture an organic material layer in a device in a multilayer structure instead of a single layer. In 1987, an organic electroluminescent device having a multilayer structure divided into a hole layer and a functional layer of a light emitting layer by Tang has been proposed. Most organic electroluminescent devices currently used include a hole injecting hole Layer, a hole transporting layer for transporting holes, a light emitting layer for recombining holes and electrons to emit light, an electron transporting layer for transporting electrons, an electron injection layer for receiving electrons from the cathode, and a cathode. The reason why the organic electroluminescent devices are formed in a multilayer structure is that the moving speeds of holes and electrons are different from each other. Therefore, when an appropriate hole injecting layer, a transporting layer, an electron transporting layer and an electron injecting layer are formed, holes and electrons can be effectively transferred, The balance between the holes and the electrons can be balanced to increase the luminous efficiency.

The first reports on the materials of electron transport include oxadiazole derivatives (PBD). It has been reported that the triazole derivative (TAZ) and the phenanthroline derivative (BCP) exhibit electron transportability. Organic metal complexes with excellent electron stability and electron transport rate are good candidates for the electron transport layer. Alq _3, which has excellent stability and electron affinity, is the most excellent candidate , It is still used most basically. European Patent Publication No. 0700917 by Motorola has already reported on a blue light emitting layer or a cyan light emitting layer of an organic light emitting device to which such metal complex compounds are applied.

In addition, organic single molecule materials having an imidazole group, an oxazole group, and a thiazole group have been reported to be applicable to conventional electron injecting and transporting layers. TPBI disclosed in US Patent No. 5,645,948 issued to Kodak in 1996 is known as a representative electron transport layer material having an imidazole group and its structure is composed of three N-phenyl Benzimidazole group and functions not only to have the ability to transport electrons but also to block holes passing through the light emitting layer, but has a low thermal stability to be applied to actual devices.

Therefore, in order to overcome the problems of the prior art and further improve the characteristics of the organic electroluminescent device, there is a continuing need to develop a more stable and efficient material that can be used as an electron injecting and transporting material in the organic electroluminescent device do.

United States Patent No. 5645948

In order to solve the above problems, it is an object of the present invention to provide a novel organic compound which can be applied to an organic electroluminescent device and has excellent electron transporting ability.

It is another object of the present invention to provide an organic electroluminescent device including the novel organic compound and exhibiting a low driving voltage and a high luminous efficiency and having an improved lifetime.

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

In Formula 1,

L ₁ to L ₃ are the same or different and are each independently a single bond or a group selected from the group consisting of C ₆ to C ₆₀ arylene groups and heteroarylene groups having 5 to 60 nuclear atoms,

X ₁ to X ₃ are the same or different and each independently N or C (R ₅ ), provided that at least two of X ₁ to X ₃ are N, and when R ₅ is plural, they are the same Or different,

R ₁ to R ₅ are the same or different, each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the An alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyl aryloxy group, C ₆ ~ aryloxy C _60, C group ₃ ~ C ₄₀ alkylsilyl, C ₆ ~ C aryl silyl group of _60, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ aryl of C ₆₀ boron group, by combining C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ selected from the group consisting of an aryl amine or of, or adjacent group to form a condensed ring You can,

Ar ₁ is C ₆ ~ C ₆₀ aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ of the aryloxy group, C group ₆ ~ C ₆₀ aryl silyl, C ₆ ~ aryl of C ₆₀ boron group, by combining C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ selected from the group consisting of an aryl amine or of, or adjacent group to form a condensed ring You can,

Ar ₂ is a heteroaryl group having 6 to 60 nuclear atoms and containing at least 2 N,

The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyl group of R ₁ to R ₅ , Ar ₁ and Ar ₂ of L ₁ to L ₃ , An aryloxy group, an aryl phosphine group, an aryl phosphine oxide group, and an arylamine group are each independently selected from the group consisting of hydrogen, deuterium, a halogen, a cyano group, a nitro group , C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atoms, heterocycloalkyl group of 3 to 40 of the, C ₆ ~ for C ₆₀ aryl group, the nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyl silyl group, C ₆ ~ group C ₆₀ aryl silyl group, C ₁ ~ alkyl boron C ₄₀ of, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C of ₆ to ₆ An arylamine group having 1 to 4 carbon atoms, and an arylamine group having 1 to ₀ carbon atoms. When the substituents are plural, they may be the same or different from each other.

In addition, the present invention provides a light emitting device comprising at least one organic compound layer interposed between the anode and the cathode, (i) a cathode, (ii) a cathode, and (iii) And an organic electroluminescent device comprising the compound represented by the formula

The one or more organic layers may include a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer, and an electron injecting layer. In this case, It may be a transport layer.

The compound represented by the formula (1) according to the present invention is excellent in thermal stability and phosphorescence properties and can be used as a material of an organic material layer of an organic electroluminescent device.

In particular, when the compound represented by Formula 1 according to the present invention is used as an electron transporting layer material of an organic electroluminescent device, an organic electroluminescent device having excellent light emitting performance, low driving voltage, high efficiency, A full-color display panel can be manufactured which has a significantly improved performance and life span.

Hereinafter, the present invention will be described in detail.

1. Organic compounds

The novel organic compound according to the present invention is a compound having three substituents around 'phenyl', 'an indene derivative containing two or more nitrogen (N)', 'an aromatic ring or a heteroaromatic ring (Ar ₁ )', N) -containing heteroaromatic ring (Ar ₂ ) 'are directly connected to each other or connected to each other through a linker to form a basic skeleton. More specifically, the compound represented by Formula 1 may be prepared by introducing two 'heteroaromatic rings (N-containing indene derivative, Ar ₂ )' and one aromatic ring (Ar ₁ ) (N-containing indene derivative, Ar ₁ , Ar ₂ ) 'are introduced into the basic skeleton.

The compound represented by the formula (1) is a material for an organic electroluminescence device, which has a higher glass transition temperature than that of a conventionally known six-membered heteroaromatic ring structure and thus has excellent thermal stability. In addition, And so on. Therefore, when the compound of Formula 1 is applied to an organic compound layer of an organic electroluminescent device, the driving voltage, efficiency, lifetime, etc. of the device can be improved.

More specifically, the compound of the formula (1) according to the present invention includes the 'two N-containing indene derivatives', which makes it possible to obtain a stronger electron donating group (EWG) (Triazolepyridine) ', the triazolopyridine is not a known EWG but has a high EWG power and a high glass transition temperature .

Accordingly, when the compound of Chemical Formula 1 is used in an organic electroluminescence device, excellent thermal stability and carrier transport ability (in particular, electron transportation ability and light emission ability) can be expected, and driving voltage, efficiency, And can exhibit excellent efficiency gains due to the triplet-triplet fusion (TTF) effect as the latest ETL material due to the high triplet energy.

In addition, since the compound of Formula 1 has two EWG (dual EWG concepts) including 'two or more N-containing indene derivatives' and 'two or more N-containing hetero aromatic rings (Ar ₂ )', And exhibits high efficiency and fast mobility in an organic electroluminescent device using such a compound.

The compound of Formula 1 may further include an aromatic ring or a heteroaromatic ring (Ar ₁ ) 'together with at least two N-containing indene derivatives, at least two N-containing heteroaromatic rings (Ar ₂ ) , The electron transporting ability is further improved, and the efficiency and mobility of the organic electroluminescent device using such compounds can be further improved.

The compound of Formula 1 has a broad band gap (sky blue to red) by controlling the HOMO and LUMO energy levels according to the type of substituent by introducing various substituents (R ₁ to R ₇ ) into the basic skeleton And high electron transportability can be shown in an organic electroluminescent device using such a compound.

In addition, the compound of the formula (1) can increase the molecular weight of the compound through various substituents (R ₁ to R ₇ ), particularly an aryl group and / or a heteroaryl group introduced into the basic skeleton, And can have higher thermal stability than conventional electron transporting layer materials (for example, Alq ₃ ). Accordingly, the organic electroluminescent device including the compound of Formula 1 can greatly improve performance and lifetime characteristics. As a result, the organic light emitting device having improved performance and lifetime characteristics can maximize the performance of the full color organic light emitting panel.

The novel compound according to the present invention is a compound represented by the above formula (1).

In the compound represented by the formula (1), L ₁ to L ₃ are the same or different from each other and are each independently a single bond or a divalent linking group having a C ₆ to C ₆₀ arylene group and a heteroatom having 5 to 60 nuclear atoms Arylene group.

Preferably, each of L ₁ to L ₃ is independently a single bond or may be selected from the group consisting of a phenylene group, a naphthalenerene group and a biphenylene group. At this time, the bonding positions of the phenylene group, the naphthaleneylene group and the biphenylene group are not limited, and ortho-, meta-, and para- are all possible.

X ₁ to X ₃ are the same or different from each other and each independently N or C (R ₅ ), with at least two of X ₁ to X ₃ being N and the others being C (R ₅ ). When a plurality of R < ₅ > s are present, they may be the same or different from each other.

Preferably, X ₁ to X ₃ may all be N.

(*는 화학식 1에 결합되는 부위를 의미함)는 하기 화학식 A-1 내지 A-4로 표시되는 구조 중 어느 하나로 표시될 수 있다. 상기 화학식 1의 화합물을 적용한 유기 전계 발광 소자의 효율을 고려할 때, 하기 A-4(트리아졸로피리딘)인 것이 바람직하다.More specifically, the compound represented by formula (1) including X ₁ to X ₃

(* Denotes a moiety bonded to the formula (1)) may be represented by any one of the structures represented by the following formulas (A-1) to (A-4). Considering the efficiency of the organic electroluminescent device to which the compound of Formula 1 is applied, it is preferably the following A-4 (triazolopyridine).

In the structures represented by the above formulas (A-1) to (A-4), R ₁ to R ₅ are each as defined in the above formula (1).

R ₁ to R ₅ are the same or different, each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the An alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyl aryloxy group, C ₆ ~ aryloxy C _60, C group ₃ ~ C ₄₀ alkylsilyl, C ₆ ~ C aryl silyl group of _60, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ aryl of C ₆₀ boron group, by combining C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ selected from the group consisting of an aryl amine or of, or adjacent group to form a condensed ring can do.

Preferably, R ₁ to R ₅ are the same as or different from each other and each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₆ to C ₆₀ aryl, atoms of 5 to 60 heteroaryl group, and a C ₆ ~, or selected from the group consisting of C ₆₀ aryl amine of the group bonded to adjacent or may form a condensed ring.

Ar ₁ is C ₆ ~ C ₆₀ aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ of the aryloxy group, C group ₆ ~ C ₆₀ aryl silyl, C ₆ ~ aryl of C ₆₀ boron group, by combining C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ selected from the group consisting of an aryl amine or of, or adjacent group to form a condensed ring can do.

Preferably, the Ar ₁ may be selected from the group consisting of a C ₆ to C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms.

More preferably, Ar ₁ may be represented by any one of the structures represented by the following formulas (B-1) to (B-25).

In the formulas (B-1) to (B-25), * denotes a moiety bonded to the formula (1).

Ar ₂ can be selected from the group consisting of commonly known electron withdrawing groups (EWG), and is a heteroaryl group having 6 to 60 nuclear atoms and containing at least 2 N atoms.

Preferably, Ar ₂ may be a substituent represented by the following formula (2) or (3).

In the above formula (2) or (3), * denotes a moiety bonded to the formula (1).

Y ₁ to Y ₆ are the same or different and are each independently N or C (R ₆ ), with at least three of Y ₁ to Y ₆ being N and the others being C (R ₆ ). At this time, when a plurality of R < ₆ > are present, they are the same as or different from each other.

Z ₁ to Z ₅ are the same or different from each other and each independently N or C (R ₇ ), with at least two of Z ₁ to Z ₅ being N and the remainder being C (R ₇ ). Here, when a plurality of R < ₇ > s are present, they are the same or different.

R ₆ and R ₇ are the same or different, each independently represent hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the An alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyl aryloxy group, C ₆ ~ aryloxy C _60, C group ₃ ~ C ₄₀ alkylsilyl, C ₆ ~ C aryl silyl group of _60, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ aryl of C ₆₀ boron group, by combining C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ selected from the group consisting of an aryl amine or of, or adjacent group to form a condensed ring can do.

Alkyl group of the R ₆ and R _7, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, ~ C ₄₀ of the alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms, 3 to 40 hetero cycloalkyl group, C ₆ ~ heteroaryl group of C ₆₀ aryl group, the nuclear atoms of 5 to 60, C ₁ ~ alkyloxy of C _40, C ₆ ~ C ₆₀ of the aryloxy group, an alkyl boronic of C ₁ ~ C ₄₀ alkyl silyl group, the group C ₆ ~ C ₆₀ aryl silyl, C ₁ ~ C ₄₀ group, C ₆ ~ arylboronic group of C _60, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ value with at least one member selected from the group consisting of C ₆₀ arylamine And when the substituent is plural, they may be the same or different.

More preferably, Ar ₂ may be represented by any one of the structures represented by the following formulas (C-1) to (C-15).

In the above formulas C-1 to C-15, * denotes a moiety bonded to the above formula (1).

R ₆ and R ₇ are the same as defined in the above formula (2) or (3), respectively.

In this case, the aryl group of the above L ₁ to L ₃ and a heteroarylene group, R ₁ to R _5, the alkyl group of Ar _1, Ar _2, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, heteroaryl group , An alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron group, an arylboron group, an arylphosphine group, an arylphosphine oxide group and an arylamine group are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, A nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C An aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C of the group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ aryl phosphine oxide of the C ₆₀ group And An arylamine group having ₆ to ₆₀ carbon atoms, and an arylamine group having ₆ to ₆₀ carbon atoms. When the substituent is plural, they may be the same as or different from each other.

The compound represented by the formula (1) may be further represented by any one of the following formulas (4) to (8).

Wherein L ₁ to L ₃ , R ₁ to R ₄ , and Ar ₁ are as defined in Formula 1, and R ₆ and R ₇ are as defined in Formula 2 or 3, respectively.

As described above, the compound represented by the formula (1) according to the present invention can be further exemplified by any one of the compounds 1 to 192 exemplified below.

In the present invention, "alkyl" means a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples of such alkyl include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl.

In the present invention, "alkenyl" means a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples of such alkenyl include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.

In the present invention, "alkynyl" means a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples of such alkynyls 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. Also, a form in which two or more rings are pendant or condensed with each other may 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 60 nuclear atoms. Wherein at least one of the carbons, preferably one to three carbons, is replaced by 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 further, a condensed form with an aryl group may be included. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and the like. ring; And 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-, and R represents aryl having 6 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" means a monovalent substituent group represented by R'O-, wherein R 'represents alkyl having 1 to 40 carbon atoms, and may be a linear, branched or cyclic structure . ≪ / RTI > Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy and pentoxy.

"Arylamine" in the present invention means an amine substituted with aryl having 6 to 60 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 cycloalkyls 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 of the carbons, preferably one to three carbons, Or < RTI ID = 0.0 > Se. ≪ / RTI > 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 3 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 6 to 60 carbon atoms.

In the present invention, "alkylboron" means boron substituted with alkyl having 1 to 40 carbon atoms, and "arylboron" means boron substituted with aryl having 6 to 60 carbon atoms.

In the present invention, "arylphosphine" means a phosphine substituted with aryl having 6 to 60 carbon atoms.

In the present invention, the term "condensed rings" means condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, condensed heteroaromatic rings, or a combination thereof.

The compound represented by formula (1) of the present invention can be synthesized in various ways with reference to the synthesis process of the following examples.

2. Organic Field  Light emitting element

The present invention provides an organic electroluminescent device comprising a compound represented by the above formula (1).

More specifically, the organic electroluminescent device according to the present invention includes one or more organic layers interposed between the anode and the cathode, (i) an anode, (ii) a cathode, and (iii) , And at least one of the one or more organic layers includes a compound represented by the general formula (1). At this time, the compound of formula (1) may be used alone or in combination of two or more.

The at least one organic material layer may include at least one of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer, and an electron injecting layer. have. Specifically, the organic material layer containing the compound of Formula 1 is preferably an electron transporting layer.

The light emitting layer of the organic electroluminescent device of the present invention may include a host material (preferably, a phosphorescent host material), which may include a compound of the above formula (1) as a host material. The light emitting layer of the organic electroluminescent device of the present invention may contain a compound other than the compound of Formula 1 as a host.

The structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer, . At least one of the hole injecting layer, the hole transporting layer, the light-emitting auxiliary layer, the light emitting layer, the electron transporting layer, and the electron injecting layer may include the compound represented by Formula 1, ≪ / RTI > Here, the structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic layer.

Meanwhile, the organic electroluminescent device of the present invention can be manufactured by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by the above formula have.

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.

The substrate used in the fabrication of the organic electroluminescent device of the present invention is not particularly limited, but silicon wafer, quartz, glass plate, metal plate, plastic film and sheet can be used.

Examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of a metal and an oxide such as ZnO: Al or SnO2: Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.

Examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; And multi-layer structure materials such as LiF / Al or LiO2 / Al, but are not limited thereto.

Hereinafter, the present invention will be described in detail with reference to the following examples. However, the following examples are illustrative of the present invention, and the present invention is not limited by the following examples.

[Nitrogen containing Heteroaromatic ring  synthesis]

<Scheme 1>

<Scheme 2>

In Scheme 1 and 2, a plurality of Xs are the same or different from each other, and each independently is hydrogen or bromine (Br), the plurality of Rs are the same as or different from each other, and each independently hydrogen or C ₆ -C ₆₀ aryl .

[ Preparation Example  1] 2,2 ' - (5- chloro -1,3- henylene ) bis (4,4,5,5- tetramethyl -1,3,2-dioxaborolane)

2-chloro-4,6-diphenyl-1,3,5-triazine (200 g, 1102.2 mmol) and 4,4,4 ', 4', 5,5,5,5'-octamethyl- dioxane was added to 1000 ml of 1,4-dioxane, and the mixture was stirred at room temperature for 3 hours to obtain the title compound (307.8 g, 1212.4 mmol) and Pd (dppf) Cl ₂ (45.0 g, 5.4 mmol) And heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the target compound, 2,2 '- (5-chloro-1,3-phenylene) bis (4,4,5,5-tetramethyl- -dioxaborolane (220.8 g, yield 55%).

¹ H-NMR:? 1.24 (s, 24H), 7.32 (s, 1 H), 7.45 (s,

[LCMS]: 364

[ Preparation Example  2] 2,2 '-( 5- (4,4,5,5- tetramethyl -1,3,2- dioxaborolan -2- yl ) -1,3-phenylene) di- [1,2,4] triazolo [1,5-a] pyridine

&Lt; Step 1 > 2,2 '- (5- chloro -1,3- henylene ) di - [1,2,4] triazolo [1,5-a] Synthesis of pyridine

(5,4-dichloro-1,3-phenylene) bis (4, 4-dihydroxyphenyl) 5,5-tetramethyl-1,3,2-dioxaborolane) a (20.0 g, 54.8 mmol) and _{Pd (PPh 3) 4 (1.8} g, 1.4 mmol), K 2 CO 3 (7.6 g, 54.8 mmol) Toluene 200ml , 40 ml of EtOH and 40 ml of H ₂ O, and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the target compound, 2,2 '- (5-chloro-1,3-phenylene) di- [1,2,4] triazolo [ pyridine (9.4 g, yield 78%).

^{1 H-NMR: δ 7.36-7.38 (} m, 4H), 7.58 (s, 1H), 7.97 (s, 2H), 8.59 (d, 2H), 8.98 (t, 2H)

[LCMS]: 346

&Lt; Step 2 > 2,2 '- (5- (4,4,5,5- tetramethyl -1,3,2- dioxaborolan -2- yl ) -1,3-phenylene) di- [1,2,4] triazolo [1,5-a] pyridine

(5-chloro-1,3-phenylene) di- [1,2,4] triazolo [1,5-a] pyridine (9.0 g, 25.9 mmol) synthesized in the above Step 1 Dioxaborolane (6.6 g, 25.9 mmol) and Pd (dppf) Cl (4), 4,4,4 ', 5,5,5', 5'-octamethyl-2,2'- ₂ (1.0 g, 1.3 mmol), KOAc (5.1 g, 51.8 mmol) and Xphos (1.2 g, 2.6 mmol) were placed in 100 ml of 1,4-dioxane and heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the desired compound, 2,2 '- (5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- , 3-phenylene) di- [1,2,4] triazolo [1,5-a] pyridine (5.7 g, yield 51%).

^{1 H-NMR: δ 1.24 (} s, 12H), 7.36-7.38 (m, 4H), 7.62 (s, 2H), 7.88 (s, 1H), 8.59 (d, 2H), 8.98 (t, 2H)

[LCMS]: 438

[ Preparation Example  3] 2,2 '-( 5- (4,4,5,5- tetramethyl -1,3,2- dioxaborolan -2- yl ) -1,3-phenylene) di- [1,2,4] triazolo [1,5-a] pyridine

Except that 2-bromo-6-phenyl- [1,2,4] triazolo [1,5-a] pyridine was used instead of 2-bromo- [1,2,4] triazolo [ Was prepared in the same manner as in [Preparation Example 2] to obtain the objective compound 2,2 '- (5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -phenylene) di- [1,2,4] triazolo [1,5-a] pyridine (6.6 g, yield 41%).

^{1 H-NMR: δ 1.24 (} s, 12H), 7.40-7.41 (m, 2H), 7.51-7.52 (m, 8H), 7.62 (s, 2H), 7.88 (s, 1H), 8.42 (d, 2H ), 8.49 (d, 2H), 8.81 (s, 2H)

[LCMS]: 590

[ Preparation Example  4] 2,2 ' - (5- (4,4,5,5- tetramethyl -1,3,2- dioxaborolan -2- yl ) -1,3-phenylene) bis (8-phenyl- [1,2,4] triazolo [1,5-a]

Except that 2-bromo-8- phenyl- [1,2,4] triazolo [1,5-a] pyridine was used instead of 2-bromo- [1,2,4] triazolo [ Was prepared in the same manner as in [Preparation Example 2] to obtain the objective compound 2,2 '- (5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -phenylene) bis (8-phenyl- [1,2,4] triazolo [1,5-a] pyridine (6.5 g, yield 40%).

^{1 H-NMR: δ 1.24 (} s, 12H), 7.40-7.41 (m, 4H), 7.51-7.52 (m, 8H), 7.62 (s, 2H), 7.88 (s, 1H), 8.42 (d, 2H ), 8.55 (d, 2H)

[LCMS]: 590

[ Preparation Example  5] 2,2 ' - (5- (4,4,5,5- tetramethyl -1,3,2- dioxaborolan -2- yl ) -1,3-phenylene) bis (6,8-diphenyl- [1,2,4] triazolo [1,5-a]

The use of 2-bromo-6,8-diphenyl- [1,2,4] triazolo [1,5-a] pyridine instead of 2-bromo- [1,2,4] triazolo [ (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1 (4,4,5,5-tetramethyl- , 3-phenylene) bis (6,8-diphenyl- [1,2,4] triazolo [1,5-a] pyridine) (8.7 g, yield 43%).

^{1 H-NMR: δ 1.24 (} s, 12H), 7.40-7.41 (m, 4H), 7.51-7.53 (m, 16H), 7.62 (s, 2H), 7.88 (s, 1H), 8.19 (s, 2H ), 8.77 (s, 2 H)

[LCMS]: 742

[ Preparation Example  6] 2- (3 '- ([1,2,4] triazolo [1,5-a] pyridin-2-yl) -5' - (4,4,5,5-tetramethyl- -dioxaborolan-2-yl) - [1,1'-biphenyl] -4-yl) -3-phenyl-3H-imidazo [4,5-b] pyridine

&Lt; Step 1 > 2- (3- chloro -5- (4,4,5,5- tetramethyl -1,3,2- dioxaborolan -2-yl) phenyl) - [1,2,4] triazolo [1,5-a] pyridine

(5,4-dichloro-1,3-phenylene) bis (4, 4-dihydroxyphenyl) 5,5-tetramethyl-1,3,2-dioxaborolane) a (10.0 g, 27.4 mmol) and _{Pd (PPh 3) 4 (1.8} g, 1.4 mmol), K 2 CO 3 (7.6 g, 54.8 mmol) Toluene 200ml , 40 ml of EtOH and 40 ml of H ₂ O, and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After the solvent of the filtered organic layer was removed, the desired compound, 2- (3-chloro-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- ) - [1,2,4] triazolo [1,5-a] pyridine (6.5 g, yield 67%).

^{1 H-NMR: δ 1.24 (} s, 12H), 7.36-7.41 (m, 3H), 7.54 (s, 1H), 8.01 (s, 1H), 8.59 (d, 1H), 8.98 (t, 1H)

 [LCMS]: 355

<Step 2> Synthesis of 2- (3 '- ( [1,2,4] triazolo [1,5-a] pyridine -2- yl ) -5'- chloro - [1,1'-biphenyl] -4-yl) -3-phenyl-3H-imidazo [4,5- b] pyridine

3- (4-bromophenyl) -3-phenyl-3H-imidazo [4,5-b] pyridine (5.9 g, 16.8 mmol) , 4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) - [1,2,4] triazolo [1,5-a] pyridine (6.0 g, 16.8 mmol) PPh ₃ ) ₄ (1.0 g, 0.8 mmol) and K ₂ CO ₃ (4.6 g, 33.6 mmol) were placed in 200 ml of toluene, 40 ml of EtOH and 40 ml of H ₂ O and refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the target compound, 2- (3 '- ([1,2,4] triazolo [1,5- a] pyridin- - [1,1'-biphenyl] -4-yl) -3-phenyl-3H-imidazo [4,5- b] pyridine (6.6 g, yield 79%).

^{1 H-NMR: δ 7.22-7.25 (} m, 3H), 7.37-7.38 (m, 2H), 7.45-7.46 (m, 1H), 7.49-7.51 (m, 2H), 7.58-7.60 (m, 3H) , 7.84-7.86 (m, 3H), 7.98 (s, 2H), 8.43 (d,

 [LCMS]: 498

Step 3: Synthesis of 2- (3 '- ([1,2,4] triazolo [1,5-a] pyridin-2-yl) -5' - (4,4,5,5-tetramethyl- , 2-dioxaborolan-2-yl) - [1,1'-biphenyl] -4-yl) -3-phenyl-3H-imidazo [4,5-b] pyridine

(3'- ([1,2,4] triazolo [1,5-a] pyridin-2-yl) -5'-chloro- [1,1'- biphenyl] Imidazo [4,5-b] pyridine (6.0 g, 12.0 mmol) and 4,4,4 ', 4', 5,5,5 ' Dioxaborolane (3.4 g, 13.2 mmol) and Pd (dppf) Cl ₂ (0.5 g, 0.6 mmol), KOAc (2.3 g, 24.0 mmol), Xphos (0.5 g, 1.2 mmol) were added to 100 ml of 1,4-dioxane and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the desired compound, 2- (3 '- ([1,2,4] triazolo [1,5-a] pyridin- 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) - [1,1'-biphenyl] -4-yl) -3-phenyl-3H-imidazo [4,5- b ] pyridine (3.6 g, yield 51%).

^{1 H-NMR: δ 1.24 (} s, 12H), 7.22-7.25 (m, 3H), 7.38 (d, 1H), 7.43-7.46 (m, 2H), 7.50-7.52 (m, 2H), 7.57-7.58 (m, 2H), 7.62 (s, 2H), 7.84-7.88 (m, 4H), 8.48 (s,

 [LCMS]: 590

[ Preparation Example  7] 6-phenyl-2- (4 '- (3-phenyl-3H-imidazo [4,5- b] pyridin-2-yl) -5- (4,4,5,5-tetramethyl- , 2-dioxaborolan-2-yl) - [1,1'-biphenyl] -3-yl) - [1,2,4] triazolo [1,5-

Except that 2-bromo-6-phenyl- [1,2,4] triazolo [1,5-a] pyridine was used instead of 2-bromo- [1,2,4] triazolo [ 3-phenyl-3H-imidazo [4,5-b] pyridin-2-yl) -5- ( 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) - [1,1'-biphenyl] -3-yl) - [1,2,4] triazolo [ a] pyridine (5.4 g, yield 30%).

^{1 H-NMR: δ 1.24 (} s, 12H), 7.22-7.25 (m, 3H), 7.41-7.45 (m, 2H), 7.50-7.52 (m, 6H), 7.57-7.58 (m, 2H), 7.62 (s, 2H), 7.84-7.88 (m, 4H), 8.42-8.43 (m, 2H), 8.49

 [LCMS]: 666

[ Preparation Example  8] 2- (3- (4 - ([1,1'-biphenyl] -4-yl) -6-phenyl-1,3,5-triazin-2-yl) -5- , 5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -8-phenyl- [1,2,4] triazolo [1,5-

2-bromo-8- phenyl- [1,2,4] triazolo [1,5-a] pyridine, 2- (4-methoxyphenyl) 4-yl) -4-chloro-6-phenyl-1,3,5-thiophene instead of 2 - ([1,1'-biphenyl] 4-yl) -6-phenyl-1 (3H) -triazine was obtained by carrying out the same processes as in [Preparation Example 6] , 3,5-triazin-2-yl) -5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -8- ] triazolo [1,5-a] pyridine (5.9 g, yield 31%).

¹ H-NMR:? 1.24 (s, 12H), 7.25 (d, 2H), 7.41-7.43 (m, 4H), 7.50-7.52 ), 7.88 (s, IH), 8.28 (d, 2H), 8.42

 [LCMS]: 704

[ Preparation Example  9] 2- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5- (4,4,5,5-tetramethyl- , 2-dioxaborolan-2-yl) phenyl) -8-phenyl- [1,2,4] triazolo [1,5-

2-bromo-8- phenyl- [1,2,4] triazolo [1,5-a] pyridine, 2- (4-methoxyphenyl) except that 4 - ([1,1'-biphenyl] -4-yl) -6-chloro-2-phenylpyrimidine was used in place of 3-phenyl-3H-imidazo [4,5- 4-yl) -2-phenylpyrimidin-4-yl) -5- (4-methylpiperazin-1- , 4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -8-phenyl- [1,2,4] triazolo [1,5- a] pyridine (5.4 g, %).

^{1 H-NMR: δ 1.24 (} s, 12H), 7.41-7.43 (m, 4H), 7.50-7.52 (m, 10H), 7.62 (s, 2H), 7.85 (d, 2H), 7.88 (s, 1H ), 8.23 (s, IH), 8.28 (d, 2H), 8.30 (d, 2H), 8.42

 [LCMS]: 703

[ Preparation Example  10] 2- (3- (4,6- 피덴 -1,3,5- triazin -2- yl ) -5- (4,4,5,5- tetramethyl -1,3,2-dioxaborolan-2-yl) phenyl) -8-phenyl- [1,2,4] triazolo [1,5- a] pyridine

2-bromo-8- phenyl- [1,2,4] triazolo [1,5-a] pyridine, 2- (4-methoxyphenyl) -bromophenyl) -3-phenyl-3H-imidazo [4,5-b] pyridine was used instead of 2-chloro-4,6-diphenyl-1,3,5- (4,6-diphenyl-1,3,5-triazin-2-yl) -5- (4,4,5,5-tetramethyl-1,3,2 -dioxaborolan-2-yl) phenyl) -8-phenyl- [1,2,4] triazolo [1,5- a] pyridine (5.3 g, yield 31%).

^{1 H-NMR: δ 1.24 (} s, 12H), 7.41-7.43 (m, 4H), 7.50-7.52 (m, 8H), 7.62 (s, 2H), 7.88 (s, 1H), 8.27-8.29 (m , 4H), 8.42 (d, IH), 8.55 (d, IH)

 [LCMS]: 628

[ Synthetic example  1] Synthesis of Compound 19

A solution of 2,2 '- (5- (4,4,5,5-tetramethyl-9H-fluorene) (3.6 g, 10.5 mmol) 1,3,2-dioxaborolan-2-yl) -1,3-phenylene) di- [1,2,4] triazolo [1,5-a] pyridine (5 g, 12.5 mmol) and Pd (PPh _{3) 4} (0.6 g, 0.5 mmol) and K ₂ CO ₃ (2.7 g, 21.0 mmol) were placed in 200 ml of toluene, 40 ml of EtOH and 40 ml of H ₂ O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the target compound, 2,2 '- (4' - (9,9-dimethyl-9H-fluoren-2-yl) - [1,1'- biphenyl] -3,5-diyl) di- [1,2,4] triazolo [1,5-a] pyridine (4.2 g, yield 70%).

[LCMS]: 580

[ Synthetic example  2] Synthesis of Compound 21

2- (4-bromophenyl) triphenylene (4.0 g, 10.5 mmol) and 2,2 '- (5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- -yl) -1,3-phenylene) di- [ 1,2,4] triazolo [1,5-a] pyridine (5 g, 12.5 mmol) and _{Pd (PPh 3) 4 (0.6} g, 0.5 mmol), K ₂ CO ₃ (2.7 g, 21.0 mmol) was added to 200 ml of toluene, 40 ml of EtOH and 40 ml of H ₂ O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the target compound, 2,2 '- (3' - (triphenylen-2-yl) - [1,1'- biphenyl] -3,5-diyl) di - [1,2,4] triazolo [1,5-a] pyridine (4.1 g, yield 63%).

[LCMS]: 614

 [ Synthetic example  3] Synthesis of Compound 38

2-bromo-9,9'-spirobi [fluorene] (4.1 g, 10.5 mmol), 2,2 '- (5- (4,4,5,5-tetramethyl- 2-dioxaborolan-2-yl) -1,3-phenylene) bis (6-phenyl- [1,2,4] triazolo [1,5-a] pyridine) (7.4 g, 12.5 mmol) and Pd (PPh ₃ ) ₄ (0.6 g, 0.5 mmol) and K ₂ CO ₃ (2.7 g, 21.0 mmol) were placed in 200 ml of toluene, 40 ml of EtOH and 40 ml of H ₂ O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the target compound, 2,2 '- (5- (9,9'-spirobi [fluoren] -2-yl) -1,3-phenylene) bis -phenyl- [1,2,4] triazolo [1,5-a] pyridine (6.3 g, yield 71%).

[LCMS]: 854

[ Synthetic example  4] Synthesis of Compound 44

(4.9 g, 10.5 mmol) of 2- (3-bromophenyl) -9,9-diphenyl-9H-fluorene and 2,2 '- (5- (4,4,5,5-tetramethyl- 1,3,4-phenylene) bis (6-phenyl- [1,2,4] triazolo [1,5-a] pyridine) (7.4 g, 12.5 mmol) and _{Pd (PPh 3) 4 (0.6} g, 0.5 mmol), K 2 CO 3 (2.7 g, 21.0 mmol) is put into a 200ml Toluene, EtOH 40ml, 40ml H ₂ O was heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the target compound, 2,2 '- (3' - (9,9-diphenyl-9H-fluoren-2-yl) - [1,1'- biphenyl] -3,5-diyl) bis (6-phenyl- [1,2,4] triazolo [1,5-a] pyridine) (5.0 g, yield 62%).

[LCMS]: 778

[ Synthetic example  5] Synthesis of Compound 46

(3.4 g, 10.5 mmol) of 3-bromo-9-phenyl-9H-carbazole and 2,2 '- (5- (4,4,5,5-tetramethyl- dioxaborolan-2-yl) -1,3- phenylene) bis (6-phenyl- [1,2,4] triazolo [1,5-a] pyridine) (7.4 g, 12.5 mmol) and Pd (PPh _{3) 4} (0.6 g, 0.5 mmol) and K ₂ CO ₃ (2.7 g, 21.0 mmol) were placed in 200 ml of toluene, 40 ml of EtOH and 40 ml of H ₂ O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the desired compound 3- (3,5-bis (6-phenyl- [1,2,4] triazolo [1,5-a] pyridin- ) phenyl) -9-phenyl-9H-carbazole (5.2 g, yield 70%).

[LCMS]: 705

 [ Synthetic example  6] Synthesis of Compound 62

2-bromo-9,9'-spirobi [fluorene] (4.1 g, 10.5 mmol) and 2,2 '- (5- (4,4,5,5-tetramethyl- 2-dioxaborolan-2-yl) -1,3-phenylene) bis (8-phenyl- [1,2,4] triazolo [1,5-a] pyridine) (7.4 g, 12.5 mmol) and Pd (PPh ₃ ) ₄ (0.6 g, 0.5 mmol) and K ₂ CO ₃ (2.7 g, 21.0 mmol) were placed in 200 ml of toluene, 40 ml of EtOH and 40 ml of H ₂ O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the target compound, 2,2 '- (5- (9,9'-spirobi [fluoren] -2-yl) -1,3- phenylene) bis -phenyl- [1,2,4] triazolo [1,5-a] pyridine (6.3 g, yield 71%).

[LCMS]: 854

[ Synthetic example  7] Synthesis of Compound 68

(4.9 g, 10.5 mmol) of 2- (3-bromophenyl) -9,9-diphenyl-9H-fluorene, 2,2 '- (5- (4,4,5,5-tetramethyl- 1,3,4-phenylene) bis (8-phenyl- [1,2,4] triazolo [1,5-a] pyridine) (7.4 g, 12.5 mmol) and _{Pd (PPh 3) 4 (0.6} g, 0.5 mmol), K 2 CO 3 (2.7 g, 21.0 mmol) is put into a 200ml Toluene, EtOH 40ml, 40ml H ₂ O was heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the target compound, 2,2 '- (3' - (9,9-diphenyl-9H-fluoren-2-yl) - [1,1'- biphenyl] -3,5-diyl) bis (8-phenyl- [1,2,4] triazolo [1,5-a] pyridine) (5.0 g, yield 62%).

[LCMS]: 778

[ Synthetic example  8] Synthesis of Compound 70

(3.4 g, 10.5 mmol) of 3-bromo-9-phenyl-9H-carbazole and 2,2 '- (5- (4,4,5,5-tetramethyl- dioxaborolan-2-yl) -1,3- phenylene) bis (8-phenyl- [1,2,4] triazolo [1,5-a] pyridine) (7.4 g, 12.5 mmol) and Pd (PPh _{3) 4} (0.6 g, 0.5 mmol) and K ₂ CO ₃ (2.7 g, 21.0 mmol) were placed in 200 ml of toluene, 40 ml of EtOH and 40 ml of H ₂ O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the desired compound 3- (3,5-bis (8-phenyl- [1,2,4] triazolo [1,5-a] pyridin- ) phenyl) -9-phenyl-9H-carbazole (5.2 g, yield 70%).

[LCMS]: 705

[ Synthetic example  9] Compound 91 Synthesis

A mixture of 2,2 '- (5- (4,4,5,5-tetramethyl-9H-fluorene) 1,3,2-dioxaborolan-2-yl) -1,3-phenylene) bis (6,8-diphenyl- [1,2,4] triazolo [1,5-a] pyridine) (9.3 g, 12.5 mmol ) And Pd (PPh ₃ ) ₄ (0.6 g, 0.5 mmol) and K ₂ CO ₃ (2.7 g, 21.0 mmol) were placed in 200 ml of toluene, 40 ml of EtOH and 40 ml of H ₂ O and refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the target compound, 2,2 '- (4' - (9,9-dimethyl-9H-fluoren-2-yl) - [1,1'- biphenyl] -3,5-diyl bis (6,8-diphenyl- [1,2,4] triazolo [1,5-a] pyridine) (6.5 g, yield 70%).

[LCMS]: 885

[ Synthetic example  10] Synthesis of compound 93

2- (4-bromophenyl) triphenylene (4.0 g, 10.5 mmol), 2,2 '- (5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- -yl) -1,3-phenylene) bis ( 6,8-diphenyl- [1,2,4] triazolo [1,5-a] pyridine) (9.3 g, 12.5 mmol) and Pd (PPh _{3) 4} ( 0.6 g, 0.5 mmol) and K ₂ CO ₃ (2.7 g, 21.0 mmol) were placed in 200 ml of toluene, 40 ml of EtOH and 40 ml of H ₂ O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the target compound, 2,2 '- (3' - (triphenylen-2-yl) - [1,1'- biphenyl] -3,5-diyl) bis (6,8-diphenyl- [1,2,4] triazolo [1,5-a] pyridine) (5.7 g, yield 59%).

[LCMS]: 919

[ Synthetic example  11] Synthesis of Compound 105

9- bromophenanthrene (2.7 g, 10.5 mmol), 2- (3 '- ([1,2,4] triazolo [1,5- a] pyridin- 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) - [1,1'-biphenyl] -4-yl) -3-phenyl-3H-imidazo [4,5- b ] pyridine (7.4 g, 12.5 mmol), Pd (PPh ₃ ) ₄ (0.6 g, 0.5 mmol) and K ₂ CO ₃ (2.7 g, 21.0 mmol) were placed in 200 ml of toluene, 40 ml of EtOH and 40 ml of H ₂ O Was heated to reflux. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the desired compound, 2- (3 '- ([1,2,4] triazolo [1,5-a] pyridin- 4-yl) -3-phenyl-3H-imidazo [4,5-b] pyridine (4.2 g, yield 63%).

[LCMS]: 640

[ Synthetic example  12] Synthesis of Compound 113

(3.4 g, 10.5 mmol), 9- bromo-7,7-dimethyl-7H-benzo [c] yl] -5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) - [1,1'-biphenyl] -4-yl) -3-phenyl-3H-imidazo [ 4,5-b] pyridine (7.4 g, 12.5 mmol) and _{Pd (PPh 3) 4 (0.6} g, 0.5 mmol), K 2 CO 3 (2.7 g, 21.0 mmol) to 200 ml of toluene, 40 ml of EtOH and 40 ml of H ₂ O, and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the desired compound, 2- (3 '- ([1,2,4] triazolo [1,5-a] pyridin- 7H-benzo [c] fluoren-9-yl) - [1,1'-biphenyl] -4-yl) -3-phenyl-3H-imidazo [4,5- b] pyridine (4.4 g, yield: 62%).

[LCMS]: 706

[ Synthetic example  13] Synthesis of Compound 129

3-phenyl-3H-imidazo [4,5-b] pyridin-2-yl) -5- (4-fluorophenyl) - (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) - [1,1'-biphenyl] -3-yl) - [1,2,4] triazolo [ 5-a] the pyridine (8.3 g, 12.5 mmol) and _{Pd (PPh 3) 4 (0.6} g, 0.5 mmol), K 2 CO 3 (2.7 g, 21.0 mmol) in _{Toluene 200ml, EtOH 40ml, H 2} O 40ml And heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the desired compound 2- (5- (phenanthren-9-yl) -4'- (3-phenyl-3H-imidazo [4,5- b] pyridin- 2-yl) - [1,1'-biphenyl] -3-yl) -6-phenyl- [1,2,4] triazolo [1,5- a] pyridine (4.4 g, yield 59%).

[LCMS]: 716

[ Synthetic example  14] Synthesis of Compound 138

2-bromo-9,9-dimethyl-9H-fluorene (2.8 g, 10.5 mmol), 6-phenyl-2- (4 ' b] pyridin-2-yl) -5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl) - [1,1'-biphenyl] 1,2,4] triazolo [1,5-a] pyridine (8.3 g, 12.5 mmol) and _{Pd (PPh 3) 4 (0.6} g, 0.5 mmol), K 2 CO 3 (2.7 g, 21.0 mmol) of Toluene , 40 ml of EtOH and 40 ml of H ₂ O, and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the target compound, 2- (5- (9,9-dimethyl-9H-fluoren-3-yl) -4'- (3-phenyl-3H-imidazo [ 4,5-b] pyridin-2-yl) - [1,1'-biphenyl] -3-yl) -6-phenyl- [1,2,4] triazolo [ , Yield: 60%).

[LCMS]: 732

[ Synthetic example  15] Synthesis of Compound 145

bromobenzene (1.6 g, 10.5 mmol), 2- (3- (4 - ([1,1'-biphenyl] -4-yl) -6- 2-yl) -5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -8- phenyl- [1,2,4] triazolo [ a] pyridine (8.8 g, 12.5 mmol) and _{Pd (PPh 3) 4 (0.6} g, 0.5 mmol), K 2 CO 3 (2.7 g, 21.0 mmol) placed in _{Toluene 200ml, EtOH 40ml, H 2} O 40ml 12 Lt; / RTI &gt; for one hour. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the target compound, 2- (5- (4 - ([1,1'-biphenyl] -4-yl) -6- triazin-2-yl) - [1,1'-biphenyl] -3-yl) -8-phenyl- [1,2,4] triazolo [1,5- a] pyridine (4.0 g, yield 59% .

[LCMS]: 654

[ Synthetic example  16] Synthesis of compound 152

2-Bromonaphthalene (2.2 g, 10.5 mmol), 2- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin- - (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -8-phenyl- [1,2,4] triazolo [1,5-a] pyridine , 12.5 mmol) and _{Pd (PPh 3) 4 (0.6} g, 0.5 mmol), K 2 CO 3 (2.7 g, 21.0 mmol) placed in _{Toluene 200ml, EtOH 40ml, H 2} O 40ml was heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the desired compound, 2- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin- - (naphthalen-2-yl) phenyl) -8-phenyl- [1,2,4] triazolo [1,5- a] pyridine (4.7 g, yield 64%).

[LCMS]: 703

[ Synthetic example  17] Synthesis of Compound 163

2- (4-bromophenyl) -9,9-dimethyl-9H-fluorene (3.6 g, 10.5 mmol) -2-yl) -5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -8-phenyl- [1,2,4] triazolo [ -a] pyridine (7.8 g, 12.5 mmol) and _{Pd (PPh 3) 4 (0.6} g, 0.5 mmol), K 2 CO 3 (2.7 g, 21.0 mmol) is put into a 200ml Toluene, EtOH 40ml, 40ml H ₂ O The mixture was heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the target compound, 2- (4 '- (9,9-dimethyl-9H-fluoren-2-yl) Triazin-2-yl) - [1,1'-biphenyl] -3-yl) -8-phenyl- 58%).

[LCMS]: 770

[ Synthetic example  18] Synthesis of Compound 166

3-bromo-9-phenyl-9H-carbazole (3.4 g, 10.5 mmol) and 6-phenyl-2- (4 ' pyridin-2-yl) -5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) - [1,1'-biphenyl] a 2,4] triazolo [1,5-a] pyridine (7.8 g, 12.5 mmol) and _{Pd (PPh 3) 4 (0.6} g, 0.5 mmol), K 2 CO 3 (2.7 g, 21.0 mmol) Toluene 200ml, 40 ml of EtOH, 40 ml of H ₂ O, and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the desired compound 3- (4,6-diphenyl-1,3,5-triazin-2-yl) -5- (8- 1,2,4] triazolo [1,5-a] pyridin-2-yl) phenyl) -9-phenyl-9H-carbazole (4.8 g, yield 62%).

[LCMS]: 743

[ Example  1 to 18] blue organic Field  Manufacturing of light emitting device

Compounds 19, 21, 38, 44, 46, 62, 68, 70, 91, 93, 105, 113, 129, 138, 145, 152, 163, 166 synthesized in Synthesis Examples were purified by high purity sublimation purification , A blue organic electroluminescent device was prepared as follows.

First, glass substrate coated with ITO (Indium tin oxide) thin film of 1500 Å thickness was cleaned with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, and methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech), and the substrate was cleaned using UV for 5 minutes The substrate was transferred to a vacuum evaporator.

(80 nm) / NPB (15 nm) / ADN + 5% DS-405 (Doosan Electronics Co., Ltd.) (30 nm) / each compound 19, (30 nm) / LiF (1 nm) / Al (200 nm) in the order of 21, 38, 44, 46, 62, 68, 70, 91, 93, 105, 113, 129, 138, 145, 152, To fabricate an organic electroluminescent device.

[ Comparative Example  1] Blue organic Field  Manufacturing of light emitting device

A blue organic electroluminescent device was manufactured in the same manner as in Example 1 except that Alq ₃ was used instead of Compound 19 as the electron transport layer material.

[ Comparative Example  2] Blue organic Field  Manufacturing of light emitting device

A blue organic electroluminescent device was manufactured in the same manner as in Example 1 except that the compound 19 was not used as the electron transport layer material.

The structures of NPB, AND and Alq ₃ used in Examples 1 to 18 and Comparative Examples 1 and 2 are as follows.

[ Evaluation example  One]

The driving voltage, current efficiency and emission peak at current densities of 10 mA / cm &lt; 2 &gt; were measured for each of the blue organic electroluminescent devices prepared in Examples 1 to 16 and Comparative Examples 1 and 2, Respectively.

Sample Electron transport layer The driving voltage (V) Emission peak (nm) Current efficiency (cd / A) Example 1 19 3.9 458 7.0 Example 2 21 3.9 459 6.9 Example 3 38 4.0 458 7.3 Example 4 44 4.2 455 6.8 Example 5 46 3.9 456 6.8 Example 6 62 4.3 457 6.7 Example 7 68 4.5 456 6.9 Example 8 70 4.5 452 6.8 Example 9 91 4.0 456 6.6 Example 10 93 4.2 448 6.4 Example 11 105 4.1 460 7.3 Example 12 113 4.0 468 6.8 Example 13 129 4.4 465 6.9 Example 14 138 4.2 457 6.8 Example 15 145 3.8 456 7.3 Example 16 152 4.0 455 6.8 Example 17 163 4.1 459 6.5 Example 18 166 3.9 456 6.4 Comparative Example 1 Alq ₃ 4.7 458 5.6 Comparative Example 2 - 4.8 460 6.2

As shown in Table 1, the blue organic electroluminescent devices (Examples 1 to 18) using the compound of the present invention in the electron transport layer (Comparative Examples 1 and 2) used conventional Alq ₃ as the electron transport layer and the blue organic electroluminescent devices It was found that the driving voltage, the luminescent peak and the current efficiency were superior to the blue organic electroluminescent device without the electron transport layer (Comparative Example 2).

Claims (9)

A compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
L ₁ to L ₃ are the same or different and are each independently a single bond or a group selected from the group consisting of C ₆ to C ₆₀ arylene groups and heteroarylene groups having 5 to 60 nuclear atoms,
X ₁ to X ₃ are the same or different and each independently N or C (R ₅ ), provided that at least two of X ₁ to X ₃ are N, and when R ₅ is plural, they are the same Or different,
R ₁ to R ₅ are the same or different, each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the An alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyl aryloxy group, C ₆ ~ aryloxy C _60, C group ₃ ~ C ₄₀ alkylsilyl, C ₆ ~ C aryl silyl group of _60, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ aryl of C ₆₀ boron group, by combining C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ selected from the group consisting of an aryl amine or of, or adjacent group to form a condensed ring You can,
Ar ₁ is C ₆ ~ C ₆₀ aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ of the aryloxy group, C group ₆ ~ C ₆₀ aryl silyl, C ₆ ~ aryl of C ₆₀ boron group, by combining C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ selected from the group consisting of an aryl amine or of, or adjacent group to form a condensed ring You can,
Ar ₂ is a heteroaryl group having 6 to 60 nuclear atoms and containing at least 2 N,
The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyl group of R ₁ to R ₅ , Ar ₁ and Ar ₂ of L ₁ to L ₃ , An aryloxy group, an aryl phosphine group, an aryl phosphine oxide group, and an arylamine group are each independently selected from the group consisting of hydrogen, deuterium, a halogen, a cyano group, a nitro group , C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atoms, heterocycloalkyl group of 3 to 40 of the, C ₆ ~ for C ₆₀ aryl group, the nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyl silyl group, C ₆ ~ group C ₆₀ aryl silyl group, C ₁ ~ alkyl boron C ₄₀ of, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C of ₆ to ₆ An arylamine group having 1 to 4 carbon atoms, and an arylamine group having 1 to ₀ carbon atoms. When the substituents are plural, they may be the same or different from each other. The method according to claim 1,
In the formula 1

(* Denotes a moiety bonded to the formula (1)) is represented by any one of structures represented by the following formulas (A-1) to (A-4).

In the structures represented by the above Formulas A-1 to A-4,
R ₁ to R ₅ are each as defined in claim 1. The method according to claim 1,
Wherein R ₁ to R ₅ are the same or different, each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to the A heteroaryl group having ₆ to ₆₀ carbon atoms, and an arylamine group having ₆ to ₆₀ carbon atoms, or may be bonded to an adjacent group to form a condensed ring,
The alkyl, aryl, heteroaryl and arylamine groups of R ₁ to R ₅ are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 of the heteroaryl A C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkyl boron group, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ at least one selected from the group consisting of an aryl amine of the C ₆₀ And when the substituent is plural, they may be the same or different. The method according to claim 1,
Wherein Ar ₁ is represented by any one of structures represented by the following formulas (B-1) to (B-25).

In the above formulas (B-1) to (B-25)
* Represents a moiety bonded to the formula (1). The method according to claim 1,
Wherein Ar ₂ is a substituent to a compound represented by the formula 2 or 3.
(2)

(3)

In the general formula (2) or (3)
* Represents a moiety bonded to Formula 1,
Y ₁ to Y ₆ are the same or different and are each independently N or C (R ₆ ), provided that at least three of Y ₁ to Y ₆ are N, and when R ₆ is plural, they are the same Or different,
Z ₁ to Z ₅ are the same or different and are each independently N or C (R ₇ ), provided that at least two of Z ₁ to Z ₅ are N, and when R ₇ is plural, they are the same Or different,
R ₆ and R ₇ are the same or different, each independently represent hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the An alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyl aryloxy group, C ₆ ~ aryloxy C _60, C group ₃ ~ C ₄₀ alkylsilyl, C ₆ ~ C aryl silyl group of _60, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ aryl of C ₆₀ boron group, by combining C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ selected from the group consisting of an aryl amine or of, or adjacent group to form a condensed ring You can,
Alkyl group of the R ₆ and R _7, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, ~ C ₄₀ of the alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms, 3 to 40 hetero cycloalkyl group, C ₆ ~ heteroaryl group of C ₆₀ aryl group, the nuclear atoms of 5 to 60, C ₁ ~ alkyloxy of C _40, C ₆ ~ C ₆₀ of the aryloxy group, an alkyl boronic of C ₁ ~ C ₄₀ alkyl silyl group, the group C ₆ ~ C ₆₀ aryl silyl, C ₁ ~ C ₄₀ group, C ₆ ~ arylboronic group of C _60, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ value with at least one member selected from the group consisting of C ₆₀ arylamine And when the substituent is plural, they may be the same or different. The method according to claim 1,
Wherein Ar ₂ is represented by any one of structures represented by the following formulas (C-1) to (C-15).

In the above formulas C-1 to C-15,
* Represents a moiety bonded to Formula 1,
R ₆ and R ₇ are the same or different, each independently represent hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the An alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyl aryloxy group, C ₆ ~ aryloxy C _60, C group ₃ ~ C ₄₀ alkylsilyl, C ₆ ~ C aryl silyl group of _60, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ aryl of C ₆₀ boron group, by combining C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ selected from the group consisting of an aryl amine or of, or adjacent group to form a condensed ring You can,
Alkyl group of the R ₆ and R _7, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, ~ C ₄₀ of the alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms, 3 to 40 hetero cycloalkyl group, C ₆ ~ heteroaryl group of C ₆₀ aryl group, the nuclear atoms of 5 to 60, C ₁ ~ alkyloxy of C _40, C ₆ ~ C ₆₀ of the aryloxy group, an alkyl boronic of C ₁ ~ C ₄₀ alkyl silyl group, the group C ₆ ~ C ₆₀ aryl silyl, C ₁ ~ C ₄₀ group, C ₆ ~ arylboronic group of C _60, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ value with at least one member selected from the group consisting of C ₆₀ arylamine And when the substituent is plural, they may be the same or different. The method according to claim 1,
Wherein the compound represented by the formula (1) is represented by any one of the following formulas (4) to (12).
[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

In the above formulas 4 to 8,
L ₁ to L ₃ , R ₁ to R ₄ and Ar ₁ are each as defined in claim 1,
R ₆ and R ₇ are the same or different, each independently represent hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the An alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyl aryloxy group, C ₆ ~ aryloxy C _60, C group ₃ ~ C ₄₀ alkylsilyl, C ₆ ~ C aryl silyl group of _60, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ aryl of C ₆₀ boron group, by combining C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ selected from the group consisting of an aryl amine or of, or adjacent group to form a condensed ring You can,
Alkyl group of the R ₆ and R _7, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, ~ C ₄₀ of the alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms, 3 to 40 hetero cycloalkyl group, C ₆ ~ heteroaryl group of C ₆₀ aryl group, the nuclear atoms of 5 to 60, C ₁ ~ alkyloxy of C _40, C ₆ ~ C ₆₀ of the aryloxy group, an alkyl boronic of C ₁ ~ C ₄₀ alkyl silyl group, the group C ₆ ~ C ₆₀ aryl silyl, C ₁ ~ C ₄₀ group, C ₆ ~ arylboronic group of C _60, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ value with at least one member selected from the group consisting of C ₆₀ arylamine And when the substituent is plural, they may be the same or different. 1. An organic electroluminescent device comprising: (i) an anode, (ii) a cathode, and (iii) one or more organic layers sandwiched between the anode and the cathode,
Wherein at least one of the one or more organic layers includes a compound according to any one of claims 1 to 7. 9. The method of claim 8,
Wherein at least one organic compound layer containing the compound is selected from the group consisting of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer, and an electron injecting layer.