KR101527181B1 - Novel compound for organic electroluminescent device and organic electroluminescent device comprising the same - Google Patents

Abstract

An organic electroluminescent device compound represented by the following structural formula 1 or 2 and an organic electroluminescent device comprising the same are disclosed. As a result, it is possible to provide a compound for an organic light emitting device that can be used as a host, a hole transporting material, and an electron transporting material, which is excellent in electrical stability, electron and hole transporting ability and high in triplet state energy, And an organic electroluminescent device.

Description

TECHNICAL FIELD [0001] The present invention relates to a compound for a novel organic electroluminescent device and an organic electroluminescent device including the same. BACKGROUND OF THE INVENTION [0002]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a compound for an organic electroluminescent device and an organic electroluminescent device including the same, and more particularly to a compound for an organic electroluminescent device capable of improving the luminous efficiency of the organic electroluminescent device, Device.

As the move to the information society accelerates, the proportion of flat panel displays is gradually increasing. LCD (liquid crystal display) is the most widely used method, but it is a method to make a screen by applying voltage to liquid crystal and passing light from backlight through color filter to obtain three primary colors. Organic light emitting diodes (OLED) As a self-luminous element, it has excellent viewing angle and contrast ratio, is lightweight and thin, can be used for a substrate having a bending property, and is capable of transparent and flexible display, and has attracted attention as a next generation display element.

Organic EL is a phenomenon in which excitons are formed by recombination of electrons and holes injected through a cathode and an anode into an organic thin film, and light of a specific wavelength is generated from the excitons formed. In 1963, Pope et al. Reported that an anthracene single crystal (CW Tang, SA Vanslyke, Applied Physics Letters, Vol. 51, No. 913p, 1987) by Eastman Kodak Co., Ltd. (CW Tang) et al.

Organic materials used in organic electroluminescent devices are classified into polymer and small molecule, and small molecules can be divided into pure organic material and metal complex which forms metal and chelate.

Polymers can combine diverse functional units into polymer chains to produce multifunctional materials. However, it is difficult to purify compounds or to form devices, while low-molecular materials can synthesize materials of various properties. There is a limit to the synthesis of the substances.

The organic electroluminescent device can be formed in a laminated structure. In general, the device structure is formed by forming a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer between an anode and a cathode to form a light emitting layer It is possible to facilitate the formation of excitons and increase the luminous efficiency.

The luminescent material can be roughly divided into a host material and a luminescent material (dopant) material, and the luminescent material is distinguished by fluorescence and phosphorescence depending on the luminescence mechanism.

The excited state of the electrons in the compound is 1: 3 ratio of singlet to triplet, and triplet state is generated about 3 times more. Thus, the internal quantum efficiency of phosphorescence falling from the triplet state to the base state is 75% while the internal quantum efficiency of the fluorescence falling from the singlet state to the ground state is only 25%. In addition, the theoretical limit of internal quantum efficiency reaches 100% when the interplanar transition from singlet state to triplet state occurs. A light emitting material that improves the light emitting efficiency by using this point is a phosphorescent material.

Due to the nature of organic materials, it is difficult to emit phosphorescence. As a phosphorescent material, transition metal (iridium) is utilized as an organometallic compound, and an organic material is used as a host material to assist it. The material that assists the phosphorescent material (host) should have a wide bandgap and a high half-energy state energy. Although the phosphorescent material having excellent current efficiency and luminous efficiency is in the spotlight, development is urgent because there is no electron transporting ability, hole transporting ability, thermal and electrical safety, and particularly, host material having high energy of triplet state.

The present invention relates to a compound capable of being used for a light emitting layer as a host which is excellent in electrical stability, electron and hole transporting ability, and has high triplet state energy and can improve the luminous efficiency of a phosphorescent light emitting material, A light emitting element can be provided.

In addition, the present invention can provide an organic electroluminescent compound that can be used for an electron transporting material and a hole transporting material of an organic electroluminescent device, and an organic electroluminescent device including the same.

However, the problems to be solved by the present invention are not limited to the above-mentioned problems, and other problems not mentioned can be clearly understood by those skilled in the art from the following description.

According to an aspect of the present invention, there is provided a compound for an organic electroluminescence device represented by the following structural formula 1 or 2:

In the above structural formula 1 or 2,

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, 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 치환 또는 비치환된 C1 내지 C30 헤테로아릴기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로시클로알킬기이거나, 또는 R⁴ 내지 R⁶중 적어도 어느 하나는 그 어느 하나가 결합된 탄소원자의 이웃한 탄소원자와 추가로 결합하여 치환 또는 비치환된 융합된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 융합된 C1 내지 C30 헤테로시클로알킬기, 치환 또는 비치환된 융합된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 융합된 C1 내지 C30 헤테로 아릴기를 형성할 수 있고,R ⁴ to R ⁶ may be the same or different from each other, and R ⁴ to R ⁶ are each independently a hydrogen atom,

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, A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, Or a fused C3 to C30 cycloalkyl group which is further substituted or unsubstituted by at least any one of R ⁴ to R ⁶ bonded to the adjacent carbon atom of the carbon atom to which at least any one of R ⁴ to R ⁶ is bonded, A substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group,

이고,X ¹ to X ³⁷ may be the same or different from each other, X ¹ to X ³⁷ each independently represents a nitrogen atom, or

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이고,Y ¹ to Y ¹³ may be the same or different from each other, and Y ¹ To Y ¹³ each independently represent an oxygen atom, a sulfur atom,

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, 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 C1 내지 C30 헤테로시클로알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로아릴기이고, 또는 R⁸ 내지 R⁷⁰중 적어도 어느 하나는 그 어느 하나가 결합된 탄소원자의 이웃한 탄소원자와 추가로 결합하여 치환 또는 비치환된 융합된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 융합된 C1 내지 C30 헤테로시클로알킬기, 치환 또는 비치환된 융합된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 융합된 C1 내지 C30 헤테로 아릴기를 형성할 수 있고,R ⁸ to R ⁷⁰ may be the same or different from each other, and R ⁸ to R ⁷⁰ each independently represent a hydrogen atom,

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, A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, Or a fused C3 to C30 cycloalkyl group which is further substituted or unsubstituted by at least any one of R ⁸ to R ⁷⁰ bonded to a neighboring carbon atom of a carbon atom to which any one of R ⁸ to R ⁷⁰ is bonded, A substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group,

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, 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 C1 내지 C30 헤테로시클로알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로아릴기이고,Ar ³ to Ar ⁷ may be the same or different from each other, Ar ³ to Ar ⁷ each independently represent

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, A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, RTI ID = 0.0 > Cl-C30 < / RTI > heteroaryl group,

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, 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 C1 내지 C30 헤테로시클로알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 치환 또는 비치환된 C1 내지 C30 헤테로아릴기이거나, 또는 Ar¹ 및 Ar²는 서로 결합되고 그들 사이의 질소원자와 함께 치환 또는 비치환된 C1 내지 C30 헤테로시클로알킬기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로아릴기를 형성할 수 있고,Ar ¹ and Ar ² may be the same or different from each other, Ar ¹ and Ar ² are each independently

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, A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, C1 to C30 heteroaryl group, or is Ar ¹ and Ar ² are combined and together with the nitrogen atom between them, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, or form a substituted or unsubstituted C1-C30 heteroaryl each other You can,

이고,X ³⁸ to X ⁴⁰ may be the same or different from each other, and each of X ³⁸ to X ⁴⁰ is independently a nitrogen atom or

ego,

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이고,Y ¹⁴ to Y ¹⁷ may be the same or different from each other, Y ¹⁴ to Y ¹⁷ represents an oxygen atom, a sulfur atom, each independently,

, or

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R ⁷¹ To R < ¹¹⁶ > may be the same or different from each other, and R < ⁷¹ > To R < ¹¹⁶ > independently represent a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group , Or a substituted or unsubstituted C1 to C30 heteroaryl group,

Ar ⁸ represents a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, An unsubstituted C1 to C30 heteroaryl group,

R ¹ to R ³ and R ⁷ may be the same or different from each other, and R ¹ to R ³ and R ⁷ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 aryl group, C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or R ¹ to R ³ and R ⁷ At least one of them is a fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C3 to C30 heterocycloalkyl group, Or an unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group.

Examples of the substituted or unsubstituted C6 to C30 aryl group include a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthalenyl group, a substituted or unsubstituted naphthalenyl group, A substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted pyrenyl group, or a substituted or unsubstituted furanyl group, Lt; / RTI >

Examples of the substituted or unsubstituted C2 to C30 heteroaryl group include a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted thiazinyl group, a substituted or unsubstituted thiophenyl group , A substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted imidazo [1,2-a] pyridinyl group, a substituted or unsubstituted A substituted or unsubstituted indazolyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzoyl group, Substituted or unsubstituted imidazolyl groups, substituted or unsubstituted thiazolyl groups, substituted or unsubstituted tetrazolyl groups, substituted or unsubstituted oxadiazolyl groups, substituted or unsubstituted oxatriazolyl groups, However, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thiazolyl group, A substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted naphthyridinyl group, Or a substituted or unsubstituted phenanthrolinyl group, preferably a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted aryidinyl group, a substituted or unsubstituted pyrazolinyl group, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted indolyl group, A substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted phenothiazyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted benzothiazolyl group, , A substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted dibenzothiophenyl group.

The organic electroluminescent device compound may be any one selected from compounds 1 to 92 represented by the following structural formulas.

According to another aspect of the present invention, there is provided an organic electroluminescent device comprising the compound for an organic electroluminescent device.

According to another aspect of the present invention, there is provided an organic electroluminescent device comprising a first electrode, a second electrode, and a single or a plurality of organic layers between a first electrode and a second electrode, The organic or more organic compound layer may include the compound for an organic electroluminescence device.

The singular or plural organic layers may include a light emitting layer.

The plurality of organic layers may include a light emitting layer, and the plurality of organic layers may further include at least one selected from an electron injecting layer, an electron transporting layer, a hole blocking layer, an electron blocking layer, a hole transporting layer, and a hole injecting layer.

The light emitting layer may include a host and a dopant.

The present invention relates to a host, a hole injecting material, a hole transporting material, an electron transporting material, an electron injecting material, and a hole injecting material which are excellent in electrical stability and electron and hole transporting ability and have high triplet state energy, A compound for an organic light emitting device which can be used as a sealing material having an excellent refractive index in a top emission method and an organic electroluminescent device including the same can be provided.

1 is a cross-sectional view illustrating an organic electroluminescent device according to an embodiment of the present invention.
2 is a cross-sectional view illustrating an organic electroluminescent device according to another embodiment of the present invention.

The invention is capable of various modifications and may have various embodiments, and particular embodiments are exemplified and will be described in detail in the detailed description. It is to be understood, however, that the invention is not to be limited to the specific embodiments, but includes all modifications, equivalents, and alternatives falling within the spirit and scope of the invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, the present invention will be described in detail with reference to the accompanying drawings.

Furthermore, terms including an ordinal number such as the first, second, etc. to be used below can be used to describe various elements, but the constituent elements are not limited by the terms. The terms are used only for the purpose of distinguishing one component from another. For example, without departing from the scope of the present invention, the first component may be referred to as a second component, and similarly, the second component may also be referred to as a first component.

Also, when an element is referred to as being "formed" or "laminated" on another element, it may be directly attached or laminated to the front surface or one surface of the other element, It will be appreciated that other components may be present in the < / RTI >

The singular expressions include plural expressions unless the context clearly dictates otherwise. In the present application, the terms "comprises" or "having" and the like are used to specify that there is a feature, a number, a step, an operation, an element, a component or a combination thereof described in the specification, But do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.

As used herein, "atomic bond" means a single bond, a double bond or a triple bond, unless otherwise defined.

As used herein, unless otherwise defined, "substituent" means that at least one hydrogen in the substituent or compound is substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a hydroxy group, an amino group, a C1 to C30 amine group, a nitro group, a C1 to C30 silyl group, An alkyl group, a C1 to C30 alkylsilyl group, a C3 to C30 cycloalkyl group, a C1 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C1 to C30 heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, It means that it has been replaced by anger.

A C1 to C30 alkyl group, a C1 to C30 alkylsilyl group, a C3 to C30 cycloalkyl group, a C6 to C30 aryl group, a C1 to C20 aryl group, a C1 to C30 aryl group, a C1 to C30 aryl group, An alkoxy group, a C1 to C10 trifluoroalkyl group or a cyano group may be fused to form a ring.

As used herein, unless otherwise defined, it is meant that one functional group contains 1 to 4 heteroatoms selected from the group consisting of N, O, S, and P, and the remainder is carbon.

In the present specification, the term "combination thereof" means that two or more substituents are bonded to each other via a linking group or two or more substituents are condensed and bonded.

As used herein, "hydrogen" means monohydrogen, double hydrogen, or tritium, unless otherwise defined.

As used herein, unless otherwise defined, the term "alkyl group" means an aliphatic hydrocarbon group.

The alkyl group may be a "saturated alkyl group" which does not contain any double or triple bonds.

The alkyl group may be an "unsaturated alkyl group" comprising at least one double bond or triple bond.

"Alkynylene group" means a functional group in which at least two carbon atoms are composed of at least one carbon-carbon double bond, and "alkynylene group" means that at least two carbon atoms have at least one carbon- Quot; means a functional group formed by bonding. The alkyl group, whether saturated or unsaturated, can be branched, straight chain or cyclic.

The alkyl group may be a C1 to C30 alkyl group. More specifically, the alkyl group may be a C1 to C20 alkyl group, a C1 to C10 alkyl group or a C1 to C6 alkyl group.

For example, the C1 to C4 alkyl groups may have 1 to 4 carbon atoms in the alkyl chain, i.e., the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of methyl, ethyl, propyl, iso-propyl, n-butyl, Indicating that they are selected from the group.

Specific examples of the alkyl group include a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, hexyl group, ethenyl group, Butyl group, cyclopentyl group, cyclohexyl group, and the like.

The "amine group" includes an arylamine group, an alkylamine group, an arylalkylamine group, or an alkylarylamine group.

"Cycloalkyl group" includes monocyclic or fused-ring polycyclic (i. E., Rings that divide adjacent pairs of carbon atoms) functional groups.

"Heterocycloalkyl group" means that the cycloalkyl group contains 1 to 4 hetero atoms selected from the group consisting of N, O, S and P in the cycloalkyl group, and the remainder is carbon. When the heterocycloalkyl group is a fused ring, it may contain 1 to 4 heteroatoms in each ring.

"An aromatic group" means a functional group in which all elements of a functional group in the form of a ring have a p-orbital, and these p-orbital forms a conjugation. Specific examples thereof include an aryl group and a heteroaryl group.

An "aryl group" includes a monocyclic or fused ring polycyclic (i. E., A ring that divides adjacent pairs of carbon atoms) functional groups.

"Heteroaryl group" means that the aryl group contains 1 to 4 hetero atoms selected from the group consisting of N, O, S and P, and the remainder is carbon. When the heteroaryl group is a fused ring, it may contain 1 to 4 heteroatoms in each ring.

In the aryl group and the heteroaryl group, the number of atoms in the ring is the sum of carbon number and non-carbon atom number.

When used in combination, such as "alkylaryl" or "arylalkyl group ", the terms alkyl and aryl of each of the above have the meanings and contents indicated above.

The term "arylalkyl group " means an aryl substituted alkyl radical, such as benzyl, and is included in the alkyl group.

The term "alkylaryl group " means an alkyl substituted aryl radical and is included in the aryl group.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENT Hereinafter, embodiments of the present invention will be described with reference to the accompanying drawings. Referring to the accompanying drawings, the same or corresponding components are denoted by the same reference numerals, .

Referring to FIGS. 1 and 2, an organic electroluminescent device 1 including the compound for an organic electroluminescent device according to the present invention can be provided according to an embodiment of the present invention.

According to another embodiment of the present invention, the organic electroluminescent device includes a first electrode 110; A second electrode (150); And one or more organic layers 130 between the first and second electrodes and at least one organic layer selected from the single or plurality of organic layers 130 include the compound for an organic light emitting device according to the present invention can do.

Here, the single or plural organic layers 130 may include a light emitting layer 134.

The plurality of organic layers 130 may include a light emitting layer 134 and the plurality of organic layers may include an electron injection layer 131, an electron transport layer 132, a hole blocking layer 133, an electron blocking layer 135, Transporting layer 136 and hole-injecting layer 137 may be further included.

The light emitting layer 134 may include a host and a dopant.

The organic electroluminescent device is preferably supported by a transparent substrate. The material of the transparent substrate is not particularly limited as long as it has good mechanical strength, thermal stability and transparency. Specific examples thereof include glass, transparent plastic film, and the like.

As the cathode material of the organic electroluminescent device of the present invention, a metal, an alloy, an electroconductive compound or a mixture thereof having a work function of 4 eV or more can be used. Specifically, transparent conductive materials such as Au or CuI, ITO (indium tin oxide), SnO ₂ and ZnO, which are metals, can be mentioned. The thickness of the positive electrode film is preferably 10 to 200 nm.

As the anode material of the organic electroluminescent device of the present invention, a metal, an alloy, an electrically conductive compound or a mixture thereof having a work function of less than 4 eV may be used. Specifically, Na, Na-K alloy, calcium, magnesium, lithium, lithium alloy, indium, aluminum, magnesium alloy and aluminum alloy can be mentioned. In addition, aluminum / AlO ₂ , aluminum / lithium, magnesium / silver or magnesium / indium may be used. The thickness of the negative electrode film is preferably 10 to 200 nm.

In order to increase the luminous efficiency of the organic EL device, at least one electrode preferably has a light transmittance of 10% or more. The sheet resistance of the electrode is preferably several hundreds? / Mm or less. The thickness of the electrode is 10 nm to 1 탆, more preferably 10 to 400 nm. Such an electrode can be manufactured by forming the electrode material into a thin film by a vapor deposition method such as chemical vapor deposition (CVD) or physical vapor deposition (PVD) or a sputtering method.

When the compound for an organic electroluminescence device of the present invention is used for the purpose of the present invention, the known hole transporting material, hole injecting material, light emitting layer material, host material of the light emitting layer, electron transporting material, Or may be used in combination with the organic electroluminescent device compound of the present invention selectively.

N-dicarbazolyl-3,5-benzene (mCP), poly (3,4-ethylenedioxythiophene): polystyrenesulfonate (PEDOT: PSS), N, N'- (NPD), N, N'-diphenyl-N, N'-di (3-methylphenyl) -4,4'- diaminobiphenyl (TPD) N, N'N'-tetra-p-tolyl-4,4'-diaminobiphenyl, N, N'N'N'N'- Porphyrin compound derivatives such as tetraphenyl-4,4'-diaminobiphenyl, copper (II) 1,10,15,20-tetraphenyl-21H, 23H-porphyrin and the like, aromatic tertiary (4-di-p-tolylaminophenyl) cyclohexane, N, N, N-tri (3-methylphenyl) -N-phenylamino] triphenylamine, carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, phthalocyanine derivatives such as nonmetal phthalocyanine and copper phthalocyanine, An aminostilbene derivative, a derivative of an aromatic tertiary amine and a styrylamine compound, and polysilane.

The diphenylphosphine oxide-4- (triphenylsilyl) phenyl (TSPO1), Alq 3, 2,5- diaryl silole derivatives (PyPySPyPy), perfluoro rineyi suited compound (PF-6P), Octasubstituted cyclooctatetraene compound (COTs) as an electron transport material .

In the organic electroluminescent device of the present invention, the electron injecting layer, the electron transporting layer, the hole transporting layer, and the hole injecting layer may be formed of a single layer containing at least one kind of the above-mentioned compounds, And the like.

Examples of the light emitting material include a phosphorescent fluorescent material, a fluorescent whitening agent, a laser dye, an organic scintillator, and a reagent for fluorescence analysis. Specifically, a carbazole compound, a phosphine oxide compound, a carbazole-based phosphine oxide compound, bis (3,5-difluoro-4-cyanophenyl) pyridine, iridium picolinate (FCNIrpic), tris (8-hydroxyquinoline) aluminum Alq ₃ ), polyaromatic compounds such as anthracene, phenanthrene, pyrene, chrysene, perylene, coronene, rubrene and quinacridone, oligophenylene compounds such as quaterphenyl, 1,4- Bis (4-methylstyryl) benzene, 1,4-bis (4-methyl- Bis (5-t-butyl-2-benzoxazolyl) thiophene, 1,4-diphenyl-1,3-butadiene, 1,6- Liquid scintillation scintillators such as 3,5-hexatriene and 1,1,4,4-tetraphenyl-1,3-butadiene, metal complexes of oxine derivatives, coumarin dyes, dicyanomethylenepyran dyes, dicyanomethylene Cyopyran pigment, polymethine pigment, oxobenzanthracene There may be mentioned a colorant, a xanthene colorant, a carbostyryl colorant, a perylene colorant, an oxazine compound, a stilbene derivative, a spiro compound, and an oxadiazole compound.

Each layer constituting the organic EL device of the present invention can be formed into a thin film through a known method such as vacuum deposition, spin coating or casting, or can be manufactured using a material used in each layer. The thickness of each of these layers is not particularly limited and may be appropriately selected according to the characteristics of the material, but may be determined usually in the range of 2 nm to 5,000 nm.

The compound for an organic electroluminescence device according to the present invention can be formed by a vacuum deposition method, so that it is advantageous that a thin film forming process is simple and a homogeneous thin film having almost no pinhole can be easily obtained.

[Example]

Hereinafter, the compound for an organic electroluminescent device according to the present invention and the method for manufacturing the organic electroluminescent device including the same will be described in more detail with reference to the following examples. However, this is for the purpose of illustration only and is not intended to limit the scope of the invention.

Example  1: Synthesis of compound 1

(One) Manufacturing example  1: Synthesis of intermediate 1-1

(1.14 g, 0.006 mol, sigma aldrich), sodium hydride (2.2 g, 0.09 mol) were added to a mixture of 1,2-diiodobenzene (19.8 g, 0.06 mol, sigma aldrich), triisopropyl borate , Sigma aldrich), and the mixture was reacted at 25 ° C for 12 hours with stirring. After completion of the reaction, distilled water was added thereto, and the mixture was extracted and purified by column (n-hexane: methylene chloride) to obtain 15.3 g (yield 77%) of Intermediate 1-1.

LC / MS: m / z = 331 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  1-2: Intermediate 1-2 Synthesis

Pd (OAc) 2 (0.34 g, 0.0015 mol, sigma aldrich), P (tBu) 2 (0.13 g, 0.046 mol), 1-iodo-2- 2Me (0.48 g, 0.003 mol, Sigma aldrich), 600 ml of t-butyl alcohol was added to KOtBu (10.1 g, 0.09 mol, Sigma aldrich) and reacted at 25 ° C with stirring. After completion of the reaction, distilled water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 8.5 g (yield: 57%) of intermediate 1-2.

LC / MS: m / z = 325 [(M + 1) ^< ^{+ &}

(3) Manufacturing example  1-3: Synthesis of intermediate 1-3

Dichlorobenzene (340 ml) was added to the reaction mixture, and the mixture was refluxed at 180 ° C. After completion of the reaction, the reaction mixture was cooled, distilled water was added thereto, n-Hexane: methylene chloride) to obtain 6.8 g (yield 89%) of intermediate 1-3.

LC / MS: m / z = 293 [(M + 1) ^< ^{+ &}

(4) Manufacturing example  1-4: Intermediate 1-4 Synthesis

Pd (dba) 3 (1.1 g, 0.0012 mol, sigma aldrich), P (t-Bu) 3 (0.28 g, 0.023 mol), bromobenzene (3.6 g, 0.023 mol, sigma aldrich) , 0.0014 mol, sigma aldrich) and NatOBu (2.7 g, 0.028 mol, Sigma aldrich) were charged with 280 ml of toluene and reacted at 80 ° C with stirring. After completion of the reaction, the reaction mixture was cooled, distilled water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain Intermediate 1-4 (6.4 g, yield 75%).

LC / MS: m / z = 368 [(M + 1) ^< ^{+ &}

(5) Manufacturing example  1-5: Intermediate 1-5 Synthesis

800ml of Dibenzothiophene (20g, 0.109mol, Sigma aldrich), N-Iodosuccinimide (12.1g, 0.054mol, Sigma aldrich) and Solvent Chloroform / Acetone (3: 1) were added and reacted at 25 ° C. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane) to obtain 9 g (yield: 27%) of Intermediate 1-5.

LC / MS: m / z = 310 [(M + 1) ^< ^{+ &}

(6) Manufacturing example  1-6: Intermediate 1-6 Synthesis

0.029 mol, sigma aldrich), Catalyst Copper (II) (0.52 g, 0.0029 mol, sigma aldrich), Potassium fluoride (1.7 g, 0.029 mol) mol, Sigma aldrich), and the reaction was carried out at 130 ° C. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 7.1 g (yield 63%) of Intermediate 1-6.

LC / MS: m / z = 386 [(M + 1) ^< ^{+ &}

(7) Manufacturing example  1-7: Synthesis of compound 1

280 ml of DMSO was added to Intermediate 1-6 (7.1 g, 0.018 mol), Intermediate 1-4 (6.4 g, 0.018 mol), Catalyst Copper (II) (0.33 g, 0.0018 mol) and Potassium fluoride (1.1 g, And reacted at 130 ° C. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 4.6 g (yield: 51%) of Compound 1.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.50 / M, 7.45 / M, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D, 7.59 / D, 7.43 / M, 7.79 / D D, 7,98 / D, 7.52 / M, 8.45 / D, 8.41 / D, 8.20 / D) 2H (7.50 / D)

LC / MS: m / z = 502 [(M + 1) ^< ^{+ &}

Example  2: Synthesis of compound 2

(One) Manufacturing example  2-1: Synthesis of Intermediate 2-1

800 ml of N-Iodosuccinimide (12.1 g, 0.054 mol) and Solvent Chloroform / Acetone (3: 1) were added and stirred at 25 ° C. Lt; / RTI > After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane) to obtain 9.3 g (yield: 27%) of intermediate 2-1.

LC / MS: m / z = 320 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  2-2: Intermediate 2-2 Synthesis

370 ml of DMSO was added to Intermediate 2-1 (9.3 g, 0.029 mol), 1,4-diiodobenzene (9.6 g, 0.029 mol), Catalyst Copper (II) (0.52 g, 0.0029 mol) And the reaction was carried out at 130 ° C. After the reaction mixture was cooled, water was added in an amount corresponding to the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 7.1 g (yield 62%) of Intermediate 2-2.

LC / MS: m / z = 396 [(M + 1) ^< ^{+ &}

(3) Manufacturing example  2-3 Synthesis of compound 2

280 ml of DMSO was added to Intermediate 2-2 (7.1 g, 0.018 mol), Intermediate 1-4 (6.4 g, 0.018 mol), Catalyst Copper (II) (0.33 g, 0.0018 mol) and Potassium fluoride (1.1 g, And reacted at 130 ° C. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 4.6 g of Compound 2 (yield: 50%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.50 / M, 7.29 / M, 8.12 / D, 7.63 / D, 7.90 / D, 7.39 / M, 8.10 / D, 7.59 / D, 8.56 / D ) 2H (7.45 / M, 7.22 / M, 7.25 / D, 7.85 / D)

LC / MS: m / z = 512 [(M + 1) ^< ^{+ &}

Example  3: Compound 5 Synthesis

(One) Manufacturing example  3-1: Intermediate 5-1 Synthesis

800 ml of triphenylene (24.9 g, 0.109 mol, Sigma aldrich), N-Iodosuccinimide (12.1 g, 0.054 mol) and Solvent Chloroform / Acetone (3: 1) were added and reacted at 25 ° C. After cooling the reaction mixture, water was added by the amount of the reaction solvent and the mixture was extracted and subjected to column purification (n-hexane) to obtain 10.3 g (yield: 24%) of intermediate 5-1.

LC / MS: m / z = 354 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  3-2: Intermediate 5-2 Synthesis

370 ml of DMSO was added to Intermediate 5-1 (10.3 g, 0.029 mol), 1,4-diiodobenzene (9.6 g, 0.029 mol), Catalyst Copper (II) (0.52 g, 0.0029 mol) and Potassium fluoride (1.7 g, 0.029 mol) And the reaction was carried out at 130 ° C. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 7.7 g (m / z = 430)

LC / MS: m / z = 430 [(M + 1) ^< ^{+ &}

(3) Manufacturing example  3-3: Compound 5 Synthesis

280 ml of DMSO was added to Intermediate 5-2 (7.7 g, 0.018 mol), Intermediate 1-4 (6.4 g, 0.018 mol), Catalyst Copper (II) (0.33 g, 0.0018 mol) and Potassium fluoride (1.1 g, And reacted at 130 ° C. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 4.6 g (yield: 47%) of Compound 5.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.50 / M, 7.45 / M, 7.63 / D, 7.29 / M, 7.90 / D, 7.39 / M, 8.34 / D, 8.99 / D) 2H (8.10 D, 8.93 / D, 7.88 / M, 7.82 / M, 7.50 / D, 7.58 /

LC / MS: m / z = 546 [(M + 1) ^< ^{+ &}

Example  4: Synthesis of Compound 6

(One) Manufacturing example  4-1: Synthesis of Intermediate 6-1

800 ml of N-phenyldibenzo [b, d] thiophene-4-amine (30g, 0.109mol, Sigma aldrich) and N-Iodosuccinimide (12.1g, 0.054mol) and Solvent Chloroform / Acetone And reacted with stirring. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane) to obtain 11.6 g (yield: 24%) of intermediate 6-1.

LC / MS: m / z = 401 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  4-2: Intermediate 6-2 Synthesis

DMSO (370 ml) was added to Intermediate 6-1 (11.6 g, 0.029 mol), 1,4-diiodobenzene (9.6 g, 0.029 mol), Catalyst Copper (II) (0.52 g, 0.0029 mol) and Potassium fluoride And the reaction was carried out at 130 ° C. After the reaction mixture was cooled, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 8.6 g (62% yield) of Intermediate 6-2.

LC / MS: m / z = 477 [(M + 1) ^< ^{+ &}

(3) Manufacturing example  4-3: Synthesis of Compound 6

280 ml of DMSO was added to Intermediate 6-2 (8.6 g, 0.018 ol), Intermediate 1-4 (6.4 g, 0.018 mol), Catalyst Copper (II) (0.33 g, 0.0018 mol), Potassium fluoride (1.1 g, And reacted at 130 ° C. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 4.6 g (yield: 43%) of Compound 6.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.45 / M, 7.63 / D, 7.29 / M, 8.12 / D, 7.90 / D, 7.39 / M, 8.10 / D, 6.81 / M, 6.86 / D 7.50 / D, 7.58 / M, 7.54 / D, 6.69 / D, 7.20 / M, 6.63 / D )

LC / MS: m / z = 593 [(M + 1) ^< ^{+ &}

Example  5: Synthesis of Compound 7

(One) Manufacturing example  5-1: Intermediate 7-1 Synthesis

800 ml of benzo [f] [1,9] phenanthroline (25.1 g, 0.109 mol, Sigma aldrich) and N-Iodosuccinimide (12.1 g, 0.054 mol) and Solvent Chloroform / Acetone Lt; / RTI > The reaction mixture was cooled, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane) to obtain 10.3 g (yield: 27%) of Intermediate 7-1.

LC / MS: m / z = 356 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  5-2: Intermediate 7-2 Synthesis

370 ml of DMSO was added to Intermediate 7-1 (11.6 g, 0.029 mol), 1,4-diiodobenzene (9.6 g, 0.029 mol), Catalyst Copper (II) (0.52 g, 0.0029 mol) And the reaction was carried out at 130 ° C. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 8.6 g (yield: 69%) of Intermediate 7-2.

LC / MS: m / z = 432 [(M + 1) ^< ^{+ &}

(3) Manufacturing example  5-3: Synthesis of Compound 7

DMSO (300 ml) was added to Intermediate 7-2 (8.6 g, 0.020 mol), Intermediate 1-4 (6.8 g, 0.020 mol), Catalyst Copper (II) (0.38 g, 0.0020 mol) and Potassium fluoride And reacted at 130 ° C. The reaction mixture was cooled, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 4.6 g (yield: 42%) of Compound 7.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.50 / M, 7.45 / M, 7.63 / D, 7.29 / M, 8.12 / D, 7.90 / D, 7.39 / M, 8.10 / D, 7.58 / M D, 8.38 / D, 8.34 / S, 7.73 / D, 8.06 / D, 7.50 / D, 8.45 / D, 8.91 / S) 2H (7.50 / D, 7.58 /

LC / MS: m / z = 548 [(M + 1) ^< ^{+ &}

Example  6: Synthesis of compound 12

(One) Manufacturing example  6-1: Synthesis of Intermediate 12-1

(32.1 g, 0.109 mol, Sigma aldrich), N-Iodosuccinimide (12.1 g, 0.054 mol) and Solvent Chloroform / Acetone (3: 1), and the mixture was reacted at 25 ° C with stirring. After cooling the reaction mixture, water was added by the amount of the reaction solvent and the mixture was extracted and subjected to column purification (n-hexane) to obtain 10.3 g (yield: 22%) of Intermediate 12-1.

LC / MS: m / z = 423 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  6-2: Intermediate 12-2 Synthesis

400ml DMSO was added to Intermediate 12-1 (10.3g, 0.024mol), 1,4-diiodobenzene (7.9g, 0.024mol), Catalyst Copper (II) (0.43g, 0.0024mol) and Potassium fluoride (1.4g, 0.024mol) And the reaction was carried out at 130 ° C. After the reaction mixture was cooled, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 8.6 g (yield: 72%) of Intermediate 12-2.

LC / MS: m / z = 499 [(M + 1) ^< ^{+ &}

(3) Manufacturing example  6-3: Compound 12 Synthesis

300 ml of DMSO was added to Intermediate 12-2 (8.6 g, 0.017 mol), Intermediate 1-4 (6.8 g, 0.017 mol), Catalyst Copper (II) (0.33 g, 0.0017 mol) and Potassium fluoride And reacted at 130 ° C. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 4.6 g (yield: 44%) of Compound 12.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.50 / M, 7.45 / M, 7.63 / D, 7.29 / M, 8.12 / D, 7.90 / D, 7.39 / M, 8.10 / D, 6.77 / M D, 7.59 / D, 7.44 / D, 7.07 / S, 4.07 / S, 4.32 / S, 7.48 / D, 8.51 / D, 7.67 / D, 6.94 / , 7.58 / M, 6.60 / D, 7.23 / M)

LC / MS: m / z = 615 [(M + 1) ^< ^{+ &}

Example  7: Compound 14 Synthesis

(One) Manufacturing example  7-1: Synthesis of Intermediate 14-1

800 ml of pyrido [2,3-f] [1,7] phenanthroline (25.2g, 0.109mol, Sigma aldrich) and N-Iodosuccinimide (12.1g, 0.054mol) and Solvent Chloroform / Acetone RTI ID = 0.0 > C < / RTI > After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane) to obtain 10.3 g (yield: 26%) of intermediate 14-1.

LC / MS: m / z = 357 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  7-2: Intermediate 14-2 Synthesis

400ml DMSO was added to Intermediate 14-1 (10.3g, 0.029mol), 1,4-diiodobenzene (9.4g, 0.029mol), Catalyst Copper (II) (0.33g, 0.0029mol) and Potassium fluoride (1.7g, 0.029mol) And the reaction was carried out at 130 ° C. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 8.6 g (yield: 68%) of intermediate 14-2.

LC / MS: m / z = 499 [(M + 1) ^< ^{+ &}

(3) Manufacturing example  7-3: Compound 14 Synthesis

300 ml of DMSO was added to Intermediate 14-2 (8.6 g, 0.020 mol), Intermediate 1-4 (8.0 g, 0.020 mol), Catalyst Copper (II) (0.38 g, 0.0020 mol) and Potassium fluoride (1.2 g, And reacted at 130 ° C. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 4.6 g (yield: 42%) of Compound 14.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.50 / M, 7.45 / M, 7.63 / D, 7.29 / M, 8.12 / D, 7.90 / D, 7.39 / M, 8.10 / D, 8.57 / S , 8.22 / S) 2H (8.38 / D, 8.83 / D, 7.50 / D)

LC / MS: m / z = 549 [(M + 1) ^< ^{+ &}

Example  8: Compound 15 Synthesis

(One) Manufacturing example  8-1: Synthesis of Intermediate 15-1

800 ml of diphenylamine (18.4 g, 0.109 mol, Sigma aldrich), N-Iodosuccinimide (12.1 g, 0.054 mol) and Solvent Chloroform / Acetone (3: 1) were added and reacted at 25 ° C. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane) to obtain 10.3 g (yield: 32%) of intermediate 15-1.

LC / MS: m / z = 295 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  8-2: Intermediate 15-2 Synthesis

400ml DMSO was added to Intermediate 15-1 (10.3g, 0.035mol), 1,4-diiodobenzene (11.3g, 0.035mol), Catalyst Copper (II) (0.40g, 0.0029mol) and Potassium fluoride (2.05g, 0.029mol) And the reaction was carried out at 130 ° C. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 8.6 g (yield 66%) of intermediate 15-2.

LC / MS: m / z = 371 [(M + 1) ^< ^{+ &}

(3) Manufacturing example  8-3: Compound 15 Synthesis

340 ml of DMSO was added to Intermediate 15-2 (8.6 g, 0.023 mol), Intermediate 1-4 (9.2 g, 0.023 mol), Catalyst Copper (II) (0.44 g, 0.0020 mol) and Potassium fluoride (1.4 g, 0.020 mol) And reacted at 130 ° C. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 4.6 g (yield: 41%) of Compound 15.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.50 / M, 7.45 / M, 7.63 / D, 7.29 / M, 8.12 / D, 7.90 / D, 7.39 / M, 8.10 / D) 2H (6.81 M, 6.69 / D, 7.54 / D, 7.50 / D, 7.58 /

LC / MS: m / z = 487 [(M + 1) ^< ^{+ &}

Example  9: Compound 18 Synthesis

(One) Manufacturing example  9-1: Synthesis of Intermediate 18-1

4-bromophenylboronic acid (7.5 g, 0.037 mol, Sigma Aldrich), Pd (PPh) 4 (1.0 g, 0.0009 mol, Sigma Aldrich) (10 g, 0.031 mol, Sigma Aldrich) ) And NaOH (3.7 g, 0.093 mol, sigma aldrich), and the mixture was stirred under reflux for 3 hours under nitrogen. The reaction mixture was cooled, extracted with dichloromethane, and purified by silica column (MC: HEX) to obtain 9.1 g (yield: 74%) of intermediate 18-1.

LC / MS: m / z = 398 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  9-2: Compound 18 Synthesis

(5.9 g, 0.028 mol, sigma aldrich), Catalyst Copper (II) (0.29 g, 0.0023 mol) was added to a solution of Intermediate 18-1 (9.1 g, 0.023 mol), 9H- ), 400 ml of DMSO was added to potassium fluoride (1.65 g, 0.023 mol), and the reaction was carried out at 130 ° C. The reaction mixture was cooled, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 8.6 g (yield: 77%) of Compound 18.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.45 / M, 7.25 / M, 8.55 / D, 7.33 / M, 7.94 / D, 7.59 / D, 7.43 / M) 2H (8.78 / S, 9.26 / S, 7.68 / D, 7.50 / D, 7.58 / D) 3H (7.79 / D)

LC / MS: m / z = 489 [(M + 1) ^< ^{+ &}

Example  10: Compound 21 Synthesis

2-ylboronic acid (7.8 g, 0.028 mol, sigma aldrich), Catalyst Copper (II) (0.29 g, 0.023 mol) 0.0023 mol), Potassium fluoride (1.65 g, 0.023 mol) was added with 400 ml of DMSO and reacted at 130 ° C. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 8.6 g (yield: 68%) of Compound 21.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.25 / M, 7.45 / M, 7.33 / M, 8.55 / D, 7.94 / D, 7.59 / D, 7.43 / M, 7.79 / D) 2H (7.41 7.58 / D, 7.58 / D) 4H (8.28 / D, 7.51 / M)

LC / MS: m / z = 551 [(M + 1) ^< ^{+ &}

Example  11: Compound 22 Synthesis

4-ylboronic acid (7.4 g, 0.028 mol, sigma aldrich), Catalyst Copper (II) (0.29 g, 0.023 mol), 43.5-diphenyl- g, 0.0023mol) and Potassium fluoride (1.65g, 0.023mol) were added to 400ml of DMSO and reacted at 130 ° C. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 8.6 g (69%) of Compound 22.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.45 / M, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D, 7.43 / M) 2H (7.41 / M, 7.68 / D, 7.50 / D, 7.58 / M) 3H (7.79 / D) 4H (7.51 / M, 8.28 / D)

LC / MS: m / z = 539 [(M + 1) ^< ^{+ &}

Example  12: Compound 23 Synthesis

Intermediate 18-1 (9.1 g, 0.023 mol), 3,5-bis (1-phenyl- 1H-benzo [d] imidazol-2-yl) phenylboronic acid (14.2 g, 0.028 mo, sigma aldrich) II) (0.29g, 0.0023mol) and Potassium fluoride (1.65g, 0.023mol), and the reaction was carried out at 130 ° C. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 8.6 g (yield: 48%) of Compound 23.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / D, 7.33 / M, 7.94 / D, 7.25 / M, 7.43 / M, 7.79 / D) 2H (8.56 / D, 7.58 / D) 3H (7.59 / D, 7.45 / M, 7.66 / S) 4H (7.58 / M, 7.25 / D, 7.22 /

LC / MS: m / z = 780 [(M + 1) ^< ^{+ &}

Example  13: Compound 25 Synthesis

0.025 mol, Sigma aldrich), Catalyst Copper (II) (0.29 g, 0.0023 mol), Potassium fluoride (1.65 g, 0.023 mol), Intermediate 18-1 (9.1 g, 0.023 mol), dipyridin-3-ylboramidic acid ), 400 ml of DMSO was added and reacted at 130 캜. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 8.6 g (yield: 77%) of Compound 25.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.45 / M, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D, 7.59 / D, 7.43 / M, 7.79 / D) 2H (7.58 7.54 / D, 6.69 / D, 8.04 / S, 8.09 / D, 7.36 / M, 7.27 / D)

LC / MS: m / z = 489 [(M + 1) ^< ^{+ &}

Example  14: Compound 29 Synthesis

Imidazo [1,2-a] pyridin-7-ylboronic acid (4.5 g, 0.028 mol, sigma aldrich), Catalyst Copper (II) (0.29 g, 0.0023 mol) DMSO (400 ml) was added to potassium fluoride (1.65 g, 0.023 mol) and the reaction was allowed to proceed at 130 ° C. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 8.6 g (yield 86%) of Compound 29.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.25 / M, 7.45 / M, 7.94 / D, 7.33 / M, 8.55 / D, 7.59 / D, 7.43 / M, 7.79 / D, 7.73 / S , 6.87 / D, 8.54 / D) 2H (7.48 / D, 7.50 / D, 7.58 /

LC / MS: m / z = 435 [(M + 1) ^< ^{+ &}

Example  15: Compound 30 Synthesis

(5.9 g, 0.028 mol, sigma aldrich), Catalyst Copper (II) (0.29 g, 0.0023 mol), Potassium fluoride (1.65 g, 0.023 mol), Intermediate 18-1 (9.1 g, 0.023 mol), 9H- 0.03 mol), 400 ml of DMSO was added, and the reaction was allowed to proceed at 130 占 폚. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 8.6 g (yield: 63%) of Compound 30.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.50 / M, 7.63 / D, 7.29 / M, 8.12 / D, 7.45 / M, 7.59 / D, 7.43 / M) 2H (7.50 / D, 7.68 / D, 7.58 / M, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D)

LC / MS: m / z = 485 [(M + 1) ^< ^{+ &}

Example  16: Compound 31 Synthesis

9-yl) -9H-carbazol-9-ylboronic acid (18.9, 0.028 mol, sigma aldrich), 9.1 g DMSO (400 ml) was added to Copper (II) (0.29 g, 0.0023 mol) and Potassium fluoride (1.65 g, 0.023 mol) After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 15.9 g (yield: 69%) of Compound 31.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.28 / D, 7.45 / M, 7.59 / D, 7.43 / M, 7.55 / S, 7.31 / D, 8.00 / D, 8.31 / D, 6.80 / D , 7.20 / D) 2H (7.50 / D, 7.55 / D, 7.68 / M, 7.58 / M, 8.55 / D, 8.55 / , 7.38 / M) 5H (7.33 / M)

LC / MS: m / z = 966 [(M + 1) ^< ^{+ &}

Example  17: Compound 34 Synthesis

2-ylboronic acid (7.8 g, 0.028 mol, sigma aldrich), Catalyst Copper (II) (0.29 g, 0.023 mol) 0.0023 mol), and potassium fluoride (1.65 g, 0.023 mol) were added to 400 ml of DMSO and reacted at 130 ° C. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 8.6 g (yield: 68%) of Compound 34.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.25 / M, 7.45 / M, 7.94 / D, 7.33 / M, 8.55 / D, 7.59 / D, 7.43 / M, 7.79 / D) 2H (7.25 / D, 7.85 / D, 7.41 / M, 7.58 / M, 7.50 / D)

LC / MS: m / z = 551 [(M + 1) ^< ^{+ &}

Example  18: Compound 35 Synthesis

(7.9 g, 0.028 mol, Sigma aldrich), Catalyst Copper (II) (0.29 g, 0.0023 mol), Potassium fluoride (1.65 g, 0.023 mol), Intermediate 18-1 (9.1 g, 0.023 mol), 2,6-diphenylpyridin- g, 0.023 mol), 400 ml of DMSO was added, and the reaction was allowed to proceed at 130 占 폚. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 10.1 g (yield 80%) of Compound 35.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.45 / M, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D, 7.59 / D, 7.43 / M, 7.79 / D) 2H (8.20 7.50 / D, 7.58 / M) 4H (8.30 / M, 7.54 / M, 7.25 / D)

LC / MS: m / z = 549 [(M + 1) ^< ^{+ &}

Example  19: Compound 39 Synthesis

D] imidazol-1-ylboronic acid (11.3 g, 0.028 mol, Sigma aldrich) was added to a solution of intermediate 18-1 (9.1 g, 0.023 mol) , 400 ml of DMSO was added to Catalyst Copper (II) (0.29 g, 0.0023 mol) and Potassium fluoride (1.65 g, 0.023 mol), and the reaction was carried out at 130 ° C. After cooling the reaction mixture, 400 ml of water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 9.1 g (yield: 62%) of Compound 39.

D, 7.25 / M, 7.33 / M (1 H-NMR (200 MHz, CDCl ₃ ):? Ppm, 1H (7.45 / M, 7.90 / D, 7.39 / 7.50 / D, 7.79 / D, 7.70 / D, 7.70 / S, 7.41 / M) 2H (7.50 / M, 7.50 / D, 7.79 / D, 7.68 / D, 8.28 / D, 7.51 / M, 7.58 / , 7.63 / D)

LC / MS: m / z = 677.81 [(M + 1) ^< ^{+ &}

Example  20: Compound 44 Synthesis

(7.6 g, 0.028 mol, sigma aldrich), Catalyst Copper (II) (0.29 g, 0.0023 mol), Potassium fluoride (1.65 g, 0.023 mol), triphenylen-2-ylboronic acid ), 400 ml of DMSO was added, and the reaction was allowed to proceed at 130 占 폚. The reaction mixture was cooled, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 8.8 g (yield 70%) of Compound 44.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.45 / M, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D, 7.59 / D, 7.43 / M, 7.79 / D, 9.15 / S , 8.04 / D, 8.18 / D) 2H (8.12 / D, 7.82 / M, 7.88 / M, 8.93 / D, 7.58 / M, 7.50 / D)

LC / MS: m / z = 546 [(M + 1) ^< ^{+ &}

Example  21: Compound 46 Synthesis

(9.1 g, 0.023 mol), 9,9-diphenyl-9H-fluoren-2-ylboronic acid (10.1 g, 0.028 mol, sigma aldrich), Catalyst Copper (II) (0.29 g, 0.0023 mol) DMSO (400 ml) was added to potassium fluoride (1.65 g, 0.023 mol) and the reaction was carried out at 130 ° C. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 9.0 g of Compound 46 (yield: 62%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.50 / M, 7.45 / M, 7.29 / M, 8.12 / D, 7.90 / D, 7.39 / M, 8.10 / D, 7.77 / S, 7.93 / D D, 7.58 / M, 7.63 / D, 7.26 / M) 4H (7.11 / D, 7.33 / M, 7.25 / D)

LC / MS: m / z = 636 [(M + 1) ^< ^{+ &}

Example  22: Compound 56 Synthesis

4- (9H-carbazol-9-yl) phenyl (biphenyl-4-yl) boramidic acid (12.7g, 0.028mol, sigma aldrich), Catalyst Copper (II) 0.29g, 0.0023mol) and Potassium fluoride (1.65g, 0.023mol), and the mixture was reacted at 130 占 폚. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 10.4 g (yield: 62%) of Compound 56.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.41 / M, 7.63 / D, 7.50 / M, 7.29 / M, 8.12 / D, 7.45 / M, 7.59 / D, 7.43 / M, 7.79 / D 7.55 / D, 7.54 / D, 7.37 / D, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D, 7.51 / M, 7.52 / ) 4H (6.69 / D)

LC / MS: m / z = 728 [(M + 1) ^< ^{+ &}

Example  23: Compound 60 Synthesis

2-yl) boramidic acid (16.9 g, 0.028 mol, sigma aldrich), Catalyst Copper (II) (9.1 g, 0.023 mol), 9,9- (0.29g, 0.0023mol) and Potassium fluoride (1.65g, 0.023mol), and the mixture was reacted at 130 占 폚. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and purified by column (n-hexane: methylene chloride) to obtain 14.2 g (yield 70%) of Compound 60.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.45 / M, 7.94 / D, 7.25 / M, 8.55 / D, 7.59 / D, 7.43 / M, 7.79 / D, 7.02 / D, 8.13 / S D, 7.62 / D, 6.75 / D, 7.55 / D, 7.28 / M, 7.38 / , 7.54 / D, 6.69 / D, 7.26 / M, 7.87 / D) 4H (7.11 / D)

LC / MS: m / z = 878 [(M + 1) ^< ^{+ &}

Example  24: Compound 64 Synthesis

Intermediate 18-1 (9.1 g, 0.023 mol), 4- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl (triphenylen-2-yl) boramidic acid (16.6 g, 0.028 mol, 400ml of DMSO was added to the catalyst Copper (II) (0.29g, 0.0023mol) and potassium fluoride (1.65g, 0.023mol), and the reaction was carried out at 130 ° C. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 15.1 g (yield: 76%) of Compound 64.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.45 / M, 7.59 / D, 7.43 / M, 7.79 / D, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D, 7.02 / D D, 7.50 / D, 7.58 / M) 4H (7.51 / 7.87 / D, 8.13 / S) 2H (8.93 / D, 7.88 / M, 7.82 / / M, 8.28 / D, 6.69 / D)

LC / MS: m / z = 869 [(M + 1) ^< ^{+ &}

Example  25: Compound 72 Synthesis

4-yl (9,9-diphenyl-9H-fluoren-2-yl) boramidic acid (12.2 g, 0.028 mol, sigma aldrich), Catalyst Copper (II) (0.29g, 0.0023mol) and Potassium fluoride (1.65g, 0.023mol), and the mixture was reacted at 130 占 폚. The reaction mixture was cooled, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 15.4 g (yield 83%) of Compound 72.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.45 / M, 7.59 / D, 7.43 / M, 7.79 / D, 7.94 / D, 7.25 / M, 8.55 / D, 6.75 / D, 6.58 / D (7.50 / D, 7.58 / M, 7.51 / M, 7.52 / D, 7.26 / M) / D, 7.54 / D, 6.69 / D) 5H (7.33 / M)

LC / MS: m / z = 804 [(M + 1) ^< ^{+ &}

Example  26: Compound 77 Synthesis

4-yl) boramidic acid (12.7 g, 0.028 mol, sigma aldrich), Catalyst Copper (II) (11.2 g, 0.023 mol) 0.29g, 0.0023mol) and Potassium fluoride (1.65g, 0.023mol), and the reaction was carried out at 130 占 폚. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 8.6 g (yield: 51%) of Compound 77.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.50 / M, 7.45 / M, 7.59 / D, 7.43 / M, 7.79 / D, 7.41 / M, 6.63 / D, 7.20 / M, 6.86 / D 7.50 / D, 7.51 / M, 7.94 / D, 7.33 / M, 7.25 / M, ) ≪ / RTI > 4H (7.54 / D, 6.69 / D)

LC / MS: m / z = 728 [(M + 1) ^< ^{+ &}

Example  27: Compound 80 synthesis

2-yl) boramidic acid (11.6 g, 0.028 mol, sigma aldrich), Catalyst Copper (II) (0.29 g, 0.0023 mol), and Naphthalen- DMSO (400 ml) was added to potassium fluoride (1.65 g, 0.023 mol) and the reaction was carried out at 130 ° C. The reaction mixture was cooled, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 8.6 g (yield: 54%) of Compound 80.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.50 / M, 7.45 / M, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D, 7.59 / D, 7.43 / M, 7.79 / D , 7.02 / D, 7.87 / D, 8.13 / S, 7.49 / D, 7.84 / D, 7.88 / D, 7.36 / , 8.12 / D, 7.54 / D, 6.69 / D, 7.50 / D, 7.58 / M)

LC / MS: m / z = 687 [(M + 1) ^< ^{+ &}

Example  28: Compound 83 Synthesis

(9.1 g, 0.023 mol), dibenzo [b, d] thiophen-3-yl (naphthalen-2-yl) boramidic acid (10.0 g, 0.028 mol, sigma aldrich), Catalyst Copper g, 0.0023mol) and Potassium fluoride (1.65g, 0.023mol) were added to 400ml of DMSO and reacted at 130 ° C. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 8.6 g (yield: 58%) of Compound 83.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.45 / M, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D, 7.59 / D, 7.43 / M, 7.79 / D, 7.98 / D , 7.52 / M, 8.45 / D, 7.36 / M, 7.88 / D, 7.81 / D, 7.27 / D, 6.86 / D, 7.49 / D, 7.84 / D, 7.74 / , 7.50 / D, 6.69 / D, 7.58 / M, 7.54 / D)

LC / MS: m / z = 643 [(M + 1) ^< ^{+ &}

Example  29: Compound 89 Synthesis

(8.9g, 0.028mol, sigma aldrich), Catalyst Copper (II) (0.29g, 0.0023mol) were added to a solution of intermediate 18-1 (9.1g, 0.023mol), dibenzo [b, d] thiophen- ), 400 ml of DMSO was added to potassium fluoride (1.65 g, 0.023 mol), and the reaction was carried out at 130 캜. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and purified by column (n-hexane: methylene chloride) to obtain 9.0 g (yield: 66%) of Compound 89.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.50 / M, 7.45 / M, 7.33 / M, 7.94 / D, 7.59 / D, 7.43 / M, 7.79 / D, 7.98 / D, 7.98 / D M, 7.25 / M, 7.20 / M, 8.55 / D, 8.45 / D, 7.52 / M, 6.88 / D, 6.63 / D, 7.34 / , 6.69 / D)

LC / MS: m / z = 593 [(M + 1) ^< ^{+ &}

Example  30: Compound 90 Synthesis

(One) Manufacturing example  30-1: Synthesis of intermediate 90-1

(0.2 g, 0.0023 mol), Potassium fluoride (1.65 g, 0.023 mol), Intermediate 1-4 (8.5 g, 0.023 mol), 6-bromonaphthalen-2-ylboronic acid (8.0 g, 0.028 mol, sigma aldrich) 0.03 mol), 400 ml of DMSO was added, and the reaction was allowed to proceed at 130 占 폚. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 7.5 g (yield 73%) of Intermediate 90-1

(2) Manufacturing example  30-2: Compound 90 Synthesis

A mixture of Intermediate 90-1 (7.5 g, 0.016 mol), 9-phenyl-9H-carbazol-4-ylboronic acid (5.7 g, 0.020 mol, sigma aldrich), Catalyst Copper (II) (0.20 g, 0.0016 mol) (1.14 g, 0.023 mol) was added 300 ml of DMSO and the reaction was carried out at 130 ° C. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 6.5 g (yield 67%) of Compound 90.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (8.55 / D, 7.33 / M, 7.58 / S, 7.94 / D, 7.25 / D, 7.45 / M, 7.59 / D, 7.43 / M, 7.79 / D , 7.73 / D, 7.92 / D) 4H (7.50 / D, 7.58 / M)

LC / MS: m / z = 611 [(M + 1) ^< ^{+ &}

Abbreviations used in the embodiment of the present invention are as follows.

NPB: N, N'-bis (naphthalen-1-yl) -N,

Ir (ppy) ₃ : Iridium, tris (2-phenylpyidine)

Balq: Bis (2-methyl-8-quinolinolato-N1, O8) - (1,1'-Biphenyl-4-olato) aluminum

Alq ₃ : tris (8-quinolinolato) -aluminium (III)

CBP: (4,4-N, N-dicarbazole) biphenyl

Device Example  1: Compound 1 The light-  As a host material Organic electroluminescent device  Produce

NPB was deposited on a glass substrate coated with ITO to form a hole transporting layer having a thickness of 120 nm and then Compound 1 was doped with Ir (ppy) ₃ at a rate of 9%, that is, a deposition rate of Compound 1 was 0.1 nm / sec And Ir (ppy) _{3 were} deposited at a deposition rate of 0.009 nm / sec. Ir (ppy) ₃ was doped to a deposition rate ratio of 8% to form a light emitting layer having a thickness of 30 nm on the hole transport layer. Balq was deposited thereon to a thickness of 10 nm to form a hole blocking layer to prevent holes from moving to the electron transporting layer through the light emitting layer, and Alq ₃ was deposited thereon to form an electron transporting layer having a thickness of 40 nm. Lithium fluoride Thereby forming an electron injection layer having a thickness of 1 nm. Aluminum was deposited on the electron injecting layer to form a 120 nm cathode, thereby fabricating an organic electroluminescent device.

At this time, the deposition rate of each material was evaporated at a rate of 0.1 nm / sec for the compound 1, NPB, Alq ₃ , and Balq, 0.01 nm / sec for lithium fluoride, and 0.5 nm / sec for aluminum Respectively.

Device Example  2 to 26

The organic electroluminescent devices of the device embodiments 2 to 14 were fabricated in the same manner as in the device example 1 except that the compound 1 was used instead of the luminescent material described in the following Table 1. [

Device Example  27

Except that CBP ((4,4-N, N-dicarbazole) biphenyl) was used as a host material instead of Compound 1 and Compound 6 was used instead of NPB as a hole transporting material. .

Device Example  28 to 35

Organic electroluminescent devices of Device Examples 28 to 35 were fabricated in the same manner as in Example 27 except that the compound 6 was replaced with the hole transport material shown in Table 1 below.

Device comparison example  One

An organic electroluminescent device was prepared in the same manner as in Example 1 except that (4,4-N, N-dicarbazole) biphenyl (CBP) was used as a light emitting material instead of the compound 1.

Hereinafter, the characteristics of the organic electroluminescent devices manufactured according to the device embodiments 1 to 35 and the device comparative example 1 are shown in Table 1 below.

Emitting material
(Host) Hole transport material Driving voltage
(V at 1000 cd / m ² ) Luminous efficiency
(cd / A) color Device Embodiment 1 Compound 1 NPB 5.1 35 green Device Example 2 Compound 2 NPB 5.9 30 green Device Embodiment 3 Compound 5 NPB 6.0 25 green Device Example 4 Compound 6 NPB 5.4 22 green Element Embodiment 5 Compound 7 NPB 4.5 25 green Device Example 6 Compound 12 NPB 5.9 26 green Device Example 7 Compound 14 NPB 5.2 27 green Device Example 8 Compound 15 NPB 5.5 31 green Device Example 9 Compound 18 NPB 5.1 27 green Element Embodiment 10 Compound 21 NPB 5.4 29 green Element Embodiment 11 Compound 22 NPB 5.5 22 green Device Example 12 Compound 23 NPB 5.0 34 green Device Embodiment 13 Compound 29 NPB 4.9 30 green Device Embodiment 14 Compound 30 NPB 5.7 20 green Device Example 15 Compound 31 NPB 5.7 24 green Device Embodiment 16 Compound 34 NPB 5.9 25 green Device Example 17 Compound 35 NPB 5.6 26 green Element Embodiment 18 Compound 39 NPB 5.7 24 green Element Embodiment 19 Compound 44 NPB 5.8 28 green Device Embodiment 20 Compound 46 NPB 5.8 26 green Device Example 21 Compound 56 NPB 6.0 25 green Device Embodiment 22 Compound 60 NPB 6.1 20 green Device Example 23 Compound 64 NPB 5.2 22 green Device Embodiment 24 Compound 72 NPB 5.9 21 green Device Example 25 Compound 77 NPB 5.8 23 green Device Embodiment 26 Compound 80 NPB 5.4 26 green Device Example 27 CBP Compound 6 5.5 22 green Device Example 28 CBP Compound 15 6.0 21 green Element Embodiment 29 CBP Compound 25 5.4 22 green Device Example 30 CBP Compound 56 5.4 22 green Element Embodiment 31 CBP Compound 64 5.3 20 green Device Example 32 CBP Compound 77 5.8 22 green Device Example 33 CBP Compound 80 5.4 21 green Device Example 34 CBP Compound 83 5.2 21 green Device Example 35 CBP Compound 89 5.9 20 green Device Comparative Example 1 CBP NPB 7.5 17 green

Measurement of driving voltage and luminous efficiency

The organic light emitting element made from above (substrate size: 25 × 25mm ² / deposition area: ² × 2mm 2) an IVL measuring set (CS-2000 + fixture + IVL program) depositing sikimyeo a current rise by 1mA / m ² and then fixed to the the brightness of light emitted by the surface (cd / m ^2), a driving voltage (V), current density (a / m ^2), luminous efficiency (cd / a) drive voltage when measured brightness is 1000cd / m ² days and luminous efficiency Shown in Table 1 above.

According to Table 1, when the compound for an organic electroluminescence device according to the present invention is used as a host material of a light emitting layer of an organic electroluminescent device or as a hole transport material, conventional CBP may be used as a light emitting material, or NPB may be used as a hole transporting material The driving voltage is considerably lower than that in use, and the luminous efficiency is remarkably improved.

Claims (7)

An organic electroluminescent device compound represented by the following structural formula 1 or 2, wherein the structural formulas 1 and 2 are represented by the following structural formulas 1-1 and 2-1, respectively.

In the structural formulas 1-1 and 2-1,
R ⁴ is a hydrogen atom,
R ⁵ and R ⁶ may be the same or different from each other, and R ⁵ and R ⁶ are each independently

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

, A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, Or a fused C3 to C30 cycloalkyl group which is further substituted or unsubstituted by at least any one of R ⁵ and R ⁶ bonded to the adjacent carbon atom of the carbon atom to which either of R ⁵ and R ⁶ is bonded, A substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group,
X ¹ to X ¹⁸ , and X ²³ to X ³⁷ may be the same or different from each other, X ¹ to X ¹⁸ , and X ²³ to X ³⁷ each independently represent a nitrogen atom, or

ego,
Y ¹ to Y ¹³ may be the same or different from each other, Y ¹ to Y ¹³ each independently represent an oxygen atom, a sulfur atom,

, or

ego,
R ⁸ to R ²³ , and R ²⁶ to R ⁷⁰ may be the same or different from each other, and R ⁸ to R ²³ and R ²⁶ to R ⁷⁰ are each independently a hydrogen atom,

,

,

,

, A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, Or at least one of R ⁸ to R ²³ and R ²⁶ to R ⁷⁰ is further bonded to a neighboring carbon atom of a carbon atom to which either of R ⁸ to R ²³ and R ²⁶ to R ⁷⁰ is bonded to form a substituted or unsubstituted fused Substituted C3 to C30 cycloalkyl groups, substituted or unsubstituted fused C1 to C30 heterocycloalkyl groups, substituted or unsubstituted fused C6 to C30 aryl groups, or substituted or unsubstituted fused C1 to C30 heteroaryl groups Can,
Ar ³ to Ar ⁷ may be the same or different from each other, Ar ³ to Ar ⁷ each independently represent

,

,

,

, A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, RTI ID = 0.0 > Cl-C30 < / RTI > heteroaryl group,
Ar ¹ and Ar ² may be the same or different from each other, Ar ¹ and Ar ² are each independently

,

,

,

,

, A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, C1 to C30 heteroaryl group, or is Ar ¹ and Ar ² are combined and together with the nitrogen atom between them, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, or form a substituted or unsubstituted C1-C30 heteroaryl each other You can,
X ³⁸ to X ⁴⁰ may be the same or different from each other, and each of X ³⁸ to X ⁴⁰ is independently a nitrogen atom or

ego,
Y ¹⁴ to Y ¹⁷ may be the same or different from each other, Y ¹⁴ to Y ¹⁷ represents an oxygen atom, a sulfur atom, each independently,

, or

ego,
R ⁷¹ to R ¹¹⁶ may be the same or different from each other, and R ⁷¹ to R ¹¹⁶ independently represent a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
Ar ⁸ represents a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, An unsubstituted C1 to C30 heteroaryl group,
R ¹ to R ³ and R ⁷ may be the same or different from each other, and R ¹ to R ³ and R ⁷ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 aryl group, C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or R ¹ to R ³ and R ⁷ is a fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused substituted or unsubstituted fused C3 to C30 heterocycloalkyl group, A substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group. The method according to claim 1,
Wherein the organic electroluminescent device compound is any one selected from compounds represented by the following structural formulas.

An organic electroluminescent device comprising the compound for organic electroluminescent device according to any one of claims 1 and 2. A first electrode, a second electrode, and a single or a plurality of organic layers between the first electrode and the second electrode, the organic electroluminescent device comprising:
The organic electroluminescent device according to any one of claims 1 to 3, wherein the at least one organic layer selected from the single or plural organic layers comprises the compound for organic electroluminescent devices according to any one of claims 1 and 2. 5. The method of claim 4,
Wherein the single or plural organic layers include a light emitting layer. 5. The method of claim 4,
Wherein the plurality of organic layers include a light emitting layer and the plurality of organic layers further include at least one selected from an electron injecting layer, an electron transporting layer, a hole blocking layer, an electron blocking layer, a hole transporting layer and a hole injecting layer Organic electroluminescent device. 6. The method of claim 5,
Wherein the light emitting layer comprises a host and a dopant.

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