KR101438080B1 - 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 and an organic electroluminescent device comprising the same are disclosed. Thus, a compound for an organic electroluminescent device and an organic electroluminescent device which can be used as a host and an electron transporting material, which are excellent in electrical stability, electron and hole transporting ability, and have high triplet state energy, A light emitting element can be provided.
[Structural formula 1]

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 various functional units into polymer chains to produce multifunctional materials. However, it is difficult to purify compounds or to form devices, and low-molecular materials can synthesize materials of various properties, but they exhibit multifunctional properties There is a limit to the synthesis of materials.

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 The exciton formation can be facilitated and the emission efficiency can be enhanced.

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 triplet state energy. A phosphorescent material having excellent current efficiency and luminous efficiency is received in the spotlight, but the electron transporting ability, the hole transporting ability, the host material which is thermally and electrically stable, and the organic electroluminescent device It is necessary to develop a compound for use.

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, a compound for an organic electroluminescence device represented by the following structural formula 1 may be provided.

[Structural formula 1]

In the above formula 1,

Ring a, ring b and ring c may be the same or different, and at least one of ring a, ring b and ring c is a substituted or unsubstituted 5-membered or 6-membered heteroaromatic ring containing a nitrogen atom,

또는

이고,Y ¹ represents an oxygen atom, a sulfur atom,

or

ego,

R ⁴ and R ⁵ may be the same or different from each other, and R ⁴ and R ⁵ are each independently a hydrogen atom or a substituted or unsubstituted C1 to C30 alkyl group,

,

, 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 ¹ is

,

, 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,

,

, 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,R ¹ is 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, RTI ID = 0.0 > Cl-C30 < / RTI > heteroaryl group,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

, 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 ² And Ar < ³ > may be the same or different from each other, Ar < ² > And Ar < ³ > 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, RTI ID = 0.0 > Cl-C30 < / RTI > heteroaryl group,

,

, 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 ⁴ to Ar ¹⁰ may be the same or different from each other, Ar ⁴ to Ar ¹⁰ 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, RTI ID = 0.0 > Cl-C30 < / RTI > heteroaryl group,

, 또는

이고,Y ² To Y ¹⁰ may be the same or different from each other, and Y ² To Y < ¹⁰ > each independently represent an oxygen atom, a sulfur atom,

, or

ego,

이고, X ⁴ to X ²³ may be the same or different from each other, and each of X ⁴ to X ²³ independently represents a nitrogen atom or

ego,

이고, X¹ 내지 X³은 동시에 모두

은 아니고, X ¹ to X ³ may be the same or different from each other, and X ¹ to X ³ are each independently a nitrogen atom or

, X ¹ to X ³ are both simultaneously

However,

R ¹² to R ⁴⁶ may be the same or different from each other, and each of R ¹² to R ⁴⁶ independently represents 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 C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,

R ² , R ³ and R ⁶ to R ¹¹ may be the same or different from each other, and R ² , R ³ and R ⁶ to R ¹¹ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl 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 ² , R ³ and at least any one of R ⁶ to R ¹¹ is a fused C3 to C30 cycloalkyl group further bonded to a neighboring carbon atom of a carbon atom to which either of them is bonded to form a 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.

The organic electroluminescent device compound may be represented by the following structural formula (2).

[Structural formula 2]

In the above formula 2,

또는

이고,Y ¹ represents an oxygen atom, a sulfur atom,

or

ego,

R ⁴ and R ⁵ may be the same or different from each other, and R ⁴ and R ⁵ are each independently a hydrogen atom or a substituted or unsubstituted C1 to C30 alkyl group,

,

, 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 ¹ is

,

, 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,

,

, 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,R ¹ is 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, RTI ID = 0.0 > Cl-C30 < / RTI > heteroaryl group,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

, 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 ² And Ar < ³ > may be the same or different from each other, Ar < ² > And Ar < ³ > 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, RTI ID = 0.0 > Cl-C30 < / RTI > heteroaryl group,

,

, 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 ⁴ to Ar ¹⁰ may be the same or different from each other, Ar ⁴ to Ar ¹⁰ 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, RTI ID = 0.0 > Cl-C30 < / RTI > heteroaryl group,

, 또는

이고,Y ² To Y ¹⁰ may be the same or different from each other, and Y ² To Y < ¹⁰ > each independently represent an oxygen atom, a sulfur atom,

, or

ego,

이고, X ⁴ to X ²³ may be the same or different from each other, and each of X ⁴ to X ²³ independently represents a nitrogen atom or

ego,

이고, X¹ 내지 X³은 동시에 모두

은 아니고, X ¹ to X ³ may be the same or different from each other, and X ¹ to X ³ are each independently a nitrogen atom or

, X ¹ to X ³ are both simultaneously

However,

R ¹² to R ⁴⁶ may be the same or different from each other, and each of R ¹² to R ⁴⁶ independently represents 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 C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,

R ² , R ³ and R ⁶ to R ¹¹ may be the same or different from each other, and R ² , R ³ and R ⁶ to R ¹¹ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl 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 ² , R ³ and at least any one of R ⁶ to R ¹¹ is a fused C3 to C30 cycloalkyl group further bonded to a neighboring carbon atom of a carbon atom to which either of them is bonded to form a 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.

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 60 represented by the following 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 the first electrode and the second electrode, The organic electroluminescent device may further include at least one organic compound layer including the organic electroluminescent compound.

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 compound for an organic electroluminescent device which can be used for a light emitting layer as a host which is excellent in electrical stability and electron and hole transporting ability and has high triplet state energy and can improve the luminous efficiency of a phosphorescent light emitting material, An organic electroluminescent device can be provided.

In addition, the present invention can provide an organic electroluminescent compound which 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.

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  1-1: Intermediate 1-1 Synthesis

Ni (dppp) Cl2 (3.61g, 0.0066mol, Sigma Aldrich) and 300ml of THF were added to 4,4-dichloro-3,3-bipyridine (30g, 0.1332mol, China) and dissolved. After dissolution, vinylmagnesium bromide , 0.2665 mol, Sigma Aldrich) was slowly added thereto, followed by stirring at room temperature for 12 hours. After the completion of the reaction, n-hexane and distilled water were added to the reaction solution as much as the solvent volume, and the organic layer was separated and concentrated. 5 ~ 10 ml of MC was added to the concentrated Crude compound, and after dissolution, excessive MeOH was added to recrystallize the product. The formed powder was vacuum dried to obtain 18.04 g (yield 65%) of 4,4'-divinyl-3,3'-bipyridine as intermediate 1-1.

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

Ruthenium carbene complexes (35.65 g, 0.0433 g, China) and 720 ml of toluene were placed in Intermediate 1-1 (18.04 g, 0.0866 mol) and reacted at 20 ° C for 1 hour. After completion of the reaction, water was added to the reaction mixture 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 12.17 g of 2,9-phenanthroline (yield 78%) as intermediate 1-2.

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

365 ml of KBr (20.10 g, 0.1689 mol, sigma aldrich), Selectfluor (47.88 g, 0.1351 mol, sigma Aldrich) and CH ₃ CN / MeOH (25: 1) were added to Intermediate 1-2 (12.17 g, 0.0675 mol) And reacted for 30 minutes. After completion of the reaction, distilled water was added to the reaction solution as much as the reaction solution, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 14.53 g (yield: 83%) of 5-bromo-2,9-phenanthroline .

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

Pyridine-4-thiol (6.23 g, 0.0560 mol, Sigma Aldrich), Pd (OAc) 2 (0.377 g, 0.0016 mol, P & H Tech), DiPPF (28.25 g, 0.1346 mol, China), sodium tert-butoxide (6.46 g, 0.0673 mol, TCI) and 581 ml of Dioxane were added and reacted at 100 ° C. After completion of the reaction, the reaction mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with n-hexane to obtain 12.98 g (yield: 80%) of 5- (pyridin-4-ylthio) -2,9-phenanthroline, ).

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

Intermediate 1-5 Pd (OAc) 2 (0.3022g , 0.0013mol) in _{(12.98g, 0.0448mol), K 2} CO 3 (0.620 g, 0.0044 mol, sigma aldrich) and 3890 ml of AcOH are reacted at 110 ° C. After completion of the reaction, the reaction mixture was cooled to room temperature, distilled water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 10.18 g (yield 79%) of Intermediate 1-5.

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

407.4 ml of N- Iodosuccinimide (3.98 g, 0.0177 mol, China) and Solvent Chloroform / Acetone (3: 1) were added to Intermediate 1-5 (10.18 g, 0.0354 mol) 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 3.66 g (yield: 25%) of intermediate 1-6.

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

400 ml of N- Iodosuccinimide (6.10 g, 0.0271 mol) and Solvent Chloroform / Acetone (3: 1) were added to 2-dibenzothiophene (10 g, 0.0542 mol, China) and reacted at 25 ° 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) to obtain 4.20 g (yield: 25%) of 4-iododibenzothiophene as intermediate 1-7.

(8) Manufacturing example  1-8: Intermediate 1-8 Synthesis

1,3-diiodobenzene (4.47g, 0.0135mol, China), Catalyst Copper (II) (0.086g, 0.0013mol) and base Potassium fluoride (0.788g, 0.0135mol) were added to intermediate 1-7 (4.20g, 0.0135mol) And 168 ml of DMSO were added and reacted 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 3.93 g (yield 75%) of 4- (4-iodophenyl) dibenzothiophene as Intermediate 1-8 .

(9) Manufacturing example  1-9: Compound 1 Synthesis

Intermediate 1-8 (3.42g, 0.0088mol), Copper (II) (0.056g, 0.0086mol, sigma Aldrich), KF (0.518g, 0.0088mol, sigma aldrich) were added to Intermediate 1-6 (3.66g, 0.0088mol) And 73 ml of DMSO were added and reacted at 130 占 폚. After completion of the reaction, the reaction mixture was cooled to room temperature, distilled water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 3.62 g (yield 75%) of Compound 1.

_{H-NMR (200MHz, CDCl 3} ): δ ppm 1H (7.57 / M, 7.58 / M, 7.70 / S, 7.98 / D, 8.20 / M, 8.41 / M, 8.98 / S, 9.24 / S) 2H (7.48 / M, 8.91 / S) 3H (7.50 / M, 8.45 / M)

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

Example  2: Synthesis of compound 2

(3.51 g, 0.0088 mol, China), Copper (II) (0.056 g, 0.0086 mol) was added to Intermediate 1-6 (3.66 g, 0.0088 mol) mol), KF (0.518 g, 0.0088 mol) and DMSO (73 ml) were added and reacted at 130 ° C. After completion of the reaction, the reaction mixture was cooled to room temperature, distilled water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 3.62 g (yield 75%) of Compound 2.

_{H-NMR (200MHz, CDCl 3} ): δ ppm 1H (7.45 / M, 7.59 / M, 8.56 / M, 8.98 / S, 9.24 / S) 2H (7.22 / M, 7.25 / M, 7.58 / M, 7.85 / D, 8.45 / D, 8.91 / S) 4 (7.50 / M)

LC / MS: m / z = 556 [(M + 1) ^< ^{+ &}

Example  3: Synthesis of compound 3

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

 Diiodobenzene (5.31 g, 0.0161 mol, China), Catalyst Copper (II) (0.102 g, 0.0016 mol) and base Potassium fluoride (5 g, 0.0161 mol, China) were added to 3-iododibenzo [b, d] thiophene 0.936 g, 0.0161 mol) and DMSO (200 ml) were added and 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 4.67 g (yield 75%) of Intermediate 3-1.

(2) Manufacturing example  3-2: Synthesis of Compound 3

Intermediate 3-1 (3.42g, 0.0088mol), Copper (II) (0.056g, 0.0086mol, sigma Aldrich), KF (0.518g, 0.0088mol, sigma aldrich) was added to Intermediate 1-6 (3.66g, 0.0088mol) And 73 ml of DMSO were added and reacted at 130 占 폚. After completion of the reaction, the reaction mixture was cooled to room temperature, distilled water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 3.62 g (yield 75%) of Compound 3.

_{H-NMR (200MHz, CDCl 3} ): δ ppm 1H (7.98 / D, 8.05 / M, 8.08 / M, 8.11 / M, 8.98 / S, 9.24 / S) 2H (8.91 / S) 3H (8.45 / D) 4H (7.25 / S, 7.50 / M)

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

Example  4: Synthesis of compound 5

(One) Manufacturing example  4-1: Intermediate 5-1 Synthesis

 1,4iodiodobenzene (4.65g, 0.0141mol, China), Catalyst Copper (II) (0.089g, 0.0014mol) and base Potassium fluoride (0.820g, 0.0141mol) were added to 2-iodotriphenylene (5g, 0.0141mol, And DMSO (200 ml), and the mixture was reacted at 130 占 폚. After the reaction mixture was cooled, water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 4.55 g (yield 75%) of Intermediate 5-1.

(2) Manufacturing example  4-2: Compound 5 Synthesis

Intermediate 5-1 (3.81 g, 0.0088 mol), Copper (II) (0.056 g, 0.0086 mol, sigma Aldrich), KF (0.518 g, 0.0088 mol, sigma aldrich) were added to Intermediate 1-6 (3.66 g, 0.0088 mol) And 73 ml of DMSO were added and reacted at 130 占 폚. After completion of the reaction, the reaction mixture was cooled to room temperature, distilled water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 3.65 g of Compound 5 (yield: 70%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm 1H (8.04 / D, 8.18 / D, 8.98 / S, 9.15 / S, 9.24 / S) 2H (7.50 / D, 7.82 / M, 7.88 / M, 8.12 / D, 8.45 / D, 8.91 / S, 8.93 / M) 4H (7.25 / S)

LC / MS: m / z = 590 [(M + 1) ^< ^{+ &}

Example  5: Synthesis of Compound 7

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

 1,4-diiodobenzene (4.63 g, 0.0140 mol), Catalyst Copper (II) (0.089 g, 0.0014 mol) and base Potassium fluoride (5 g, 0.0140 mol) were added to 6-iodobenzo [f] [1,10] phenanthroline (0.815 g, 0.0140 mol) and DMSO (200 ml) were added and reacted at 130 占 폚. After the reaction mixture was cooled, water was added thereto and the mixture was extracted and purified by column (n-hexane: methylene chloride) to obtain 4.55 g (yield 75%) of Intermediate 7-1.

(2) Manufacturing example  5-2: Synthesis of Compound 7

73ml of Intermediate 7-1 (3.83g, 0.0088mol), Copper (II) (0.056g, 0.0088mol), KF (0.514g, 0.0088mol) and DMSO were added to Intermediate 1-6 (3.66g, 0.0088mol) And reacted at 130 캜. After completion of the reaction, the reaction mixture was cooled to room temperature, distilled water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 3.67 g (yield 70%) of Compound 7.

_{H-NMR (200MHz, CDCl 3} ): δ ppm 1H (7.73 / D, 8.06 / D, 8.34 / M, 8.98 / S, 9.24 / S) 2H (7.50 / D, 7.58 / M, 8.38 / M, 8.45 / D, 8.83 / D, 8.91 / S) 4H (7.25 / S)

LC / MS: m / z = 592 [(M + 1) ^< ^{+ &}

Example  6; Compound 13 Synthesis

(One) Manufacturing example  6-1: Synthesis of Intermediate 13-1

1,4-diiodobenzene (7.89g, 0.0239mol, China), Catalyst Copper (II) (0.151g, 0.0023mol) and base Potassium fluoride (1.38g, 0.0239mol) were added to iodobenzene-d5 (5g, 0.0239mol, Sigma aldrich) ) And DMSO (200 ml), and the mixture was reacted at 130 占 폚. After the reaction mixture was cooled, water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 5.11 g (yield 75%) of Intermediate 13-1.

(2) Manufacturing example  6-1: Compound 13 Synthesis

Intermediate 13-1 (2.52 g, 0.0088 mol), Copper (II) (0.056 g, 0.0088 mol, sigma Aldrich), KF (0.514 g, 0.0088 mol, sigma aldrich) were added to Intermediate 1-6 (3.66 g, 0.0088 mol) And 73 ml of DMSO were added and reacted at 130 占 폚. After completion of the reaction, the reaction mixture was cooled to room temperature, distilled water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 3.93 g (yield: 70%) of Compound 13.

_{H-NMR (200MHz, CDCl 3} ): δ ppm 1H (9.24 / S) 2H (7.50 / D, 8.45 / D, 8.91 / S, 8.98 / S) 4H (7.25 / S)

LC / MS: m / z = 445 (M + 1) ^< ^{+ &}

Example  7: Compound 14 Synthesis

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

 1,4-diiodobenzene (4.61 g, 0.014 mol) and a catalyst Copper (II) (0.0889 g, 0.0014 mol) were added to a solution of 2-iodopyrido [2,3-f] [1,7] phenanthroline (5 g, 0.014 mol, , Base Potassium fluoride (0.813g, 0.014mol) and DMSO (200ml) were added and reacted at 130 ° C. After the reaction mixture was cooled, water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 4.54 g (yield 75%) of Intermediate 14-1.

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

73ml of Intermediate 14-1 (3.83g, 0.0088mol), Copper (II) (0.056g, 0.0088mol), KF (0.514g, 0.0088mol) and DMSO were added to Intermediate 1-6 (3.66g, 0.0088mol) And reacted at 130 캜. After completion of the reaction, the reaction mixture was cooled to room temperature, distilled water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 3.93 g (yield 75%) of Compound 14.

_{H-NMR (200MHz, CDCl 3} ): δ ppm 1H (7.35 / D, 8.10 / D, 8.91 / S, 8.98 / S, 9.24 / S) 2H (7.28 / D, 7.50 / D, 7.58 / M, 8.38 / D, 8.45 / D, 8.81 / M, 8.83 / M)

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

Example  8: Compound 15 Synthesis

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

3-iodopyridine (18.71g, 0.0913mol, Sigma aldrich), sodium tert-butoxide (13.16g, 0.1369mol, sigma aldrich) and Pd2 (dba) 3 (1.67g, 0.0366mol, Sigma aldrich) were added to 4-iodoaniline , 0.0018mol, P & H Tech), t-buthyl phosphine (0.739g, 0.0036mol, Sigma aldrich) and refluxed under nitrogen for 4 hours. The reaction mixture was cooled, water was added by the amount of the reaction solvent, the toluene layer was extracted, and MgSO _{4 was} used. The water was removed, and the filtrate was concentrated to obtain 9.37 g (yield: 55%) of intermediate 15-1.

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

73 ml of Intermediate 15-1 (3.30 g, 0.0088 mol), Copper (II) (0.056 g, 0.0088 mol), KF (0.514 g, 0.0088 mol) and DMSO were added to Intermediate 1-6 (3.66 g, 0.0088 mol) And reacted at 130 캜. After completion of the reaction, the reaction mixture was cooled to room temperature, distilled water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 3.54 g (yield 75%) of Compound 15.

_{H-NMR (200MHz, CDCl 3} ): δ ppm 2H (6.69 / D, 7.27 / D, 7.36 / M, 7.50 / M, 7.54 / M, 8.04 / S, 8.09 / D, 8.45 / D, 8.91 / S, 8.98 / S, 9.24 / S)

LC / MS: m / z = 533 [(M + 1) ^< ^{+ &}

Example  9: Compound 19 Synthesis

(One) Manufacturing example  9-1: Synthesis of intermediate 19-1

400 ml of N- Iodosuccinimide (6.04 g, 0.0268 mol) and Solvent Chloroform / Acetone (3: 1) were added to the reagent 19-1-1 (10 g, 0.0536 mol, China) 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 4.19 g (yield: 25%) of intermediate 19-1.

(2) Manufacturing example  9-2: Intermediate 19-2 Synthesis

To a solution of Intermediate 19-1 (4.19 g, 0.0134 mol) was added 1,3-diiodobenzene (4.42 g, 0.0134 mol, China), Catalyst Copper (II) (0.085 g, 0.0013 mol) and base Potassium fluoride (0.779 g, 0.0134 mol) And 167 ml of DMSO, and the mixture was reacted at 130 ° C. After cooling the reaction mixture, water was added by the amount of the reaction solvent, and after extraction, column purification (n-Hexane: methylene chloride) was conducted to obtain 3.90 g (yield 75%) of intermediate 19-2.

(3) Manufacturing example  9-3: Compound 19 Synthesis

(3.44 g, 0.0088 mol), Copper (II) (0.056 g, 0.0088 mol), KF (0.514 g, 0.0088 mol) and DMSO were added to Intermediate 1-6 (3.66 g, 0.0088 mol) And reacted at 130 캜. After completion of the reaction, the reaction mixture was cooled to room temperature, distilled water was added thereto, and after extraction, column purification (n-Hexane: methylene chloride) was conducted to obtain 3.64 g (yield 75%) of Compound 19.

_{H-NMR (200MHz, CDCl 3} ): δ ppm 1H (7.38 / D, 7.70 / S, 8.43 / S, 8.45 / D, 9.51 / S) 2H (7.48 / M, 7.50 / M, 7.57 / M, 8.91 / S, 8.98 / S, 9.24 / S)

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

Example  10: Compound 51 Synthesis

(One) Manufacturing example  10-1: Synthesis of Intermediate 51-1

To a solution of the intermediate 1-3 (14.53 g, 0.0560 mol), pyridin-4-amine (5.27 g, 0.0560 mol), Pd2 (dba) 3 (2.56 g, 0.0028 mol), P (t- mol), sodium tert-butoxide (6.46 g, 0.0673 mol) and 580 ml of toluene were added and reacted at 80 ° C. After completion of the reaction, the reaction mixture was cooled to room temperature, distilled water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 13.59 g (yield: 89%) of Intermediate 51-1.

(2) Manufacturing example  10-2: Intermediate 51-2 Synthesis

Pd (OAc) 2 (0.336 g, 0.0014 mol), K2CO3 (0.689 g, 0.0049 mol) and 407 ml of AcOH were added to Intermediate 51-1 (13.59 g, 0.0499 mol) and reacted at 110 占 폚. After completion of the reaction, the reaction mixture was cooled to room temperature and distilled water was added thereto, followed by extraction and column purification (n-Hexane: methylene chloride) to obtain 10.65 g (yield: 79%) of Intermediate 51-2.

(3) Manufacturing example  10-3: Compound 51 Synthesis

To a solution of intermediate 51-2 (10.65 g, 0.0394 mol) was added 2- (4-chloro-phenyl) -4,6-diphenyl- (1,3,5) tiriazine (13.55 g, 0.0394 mol), Pd2 (T-Bu) 3 (0.957 g, 0.0047 mol), sodium tert-butoxide (4.54 g, 0.0473 mol) and 426 ml of toluene were added and reacted at 80 ° C. After completion of the reaction, the reaction mixture was cooled to room temperature, distilled water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 15.94 g (yield 70%) of Compound 51.

_{H-NMR (200MHz, CDCl 3} ): δ ppm 1H (9.34 / S) 2H (7.41 / M, 7.50 / M, 7.68 / D, 7.79 / D, 8.91 / S) 3H (8.45 / M) 4H (8.28 / M) < / RTI > 5H (7.51 / M)

LC / MS: m / z = 578 [(M + 1) ^< ^{+ &}

Example  11: Compound 52 Synthesis

To a solution of Intermediate 52-1 (16.69 g, 0.0394 mol, China), Pd2 (dba) 3 (1.80 g, 0.0019 mol) and P (t-Bu) 3 (0.957 g, 0.0394 mol) 0.0047mol), sodium tert-butoxide (4.54g, 0.0473mol) and 426ml of toluene are added and reacted at 80 ° C. After completion of the reaction, the reaction mixture was cooled to room temperature, distilled water was added thereto, and the mixture was extracted and purified by column (n-hexane: methylene chloride) to obtain 15.61 g (yield 70%) of Compound 52.

_{H-NMR (200MHz, CDCl 3} ): δ ppm 1H (8.43 / S, 9.34 / S) 2H (7.41 / M, 7.50 / M, 8.45 / D, 8.91 / S) 4H (7.62 / S, 7.28 / D) 5H (7.51 / M)

LC / MS: m / z = 566 [(M + 1) ^< ^{+ &}

Example  12: Compound 53 Synthesis

Intermediate 53-1 (26.20 g, 0.0394 mol), Pd2 (dba) 3 (1.80 g, 0.0019 mol) and P (t-Bu) 3 (0.957 g, 0.0047 mol ), sodium tert-butoxide (4.54g, 0.0473mol) and 426ml of toluene were added and reacted at 80 ° C. After completion of the reaction, the reaction mixture was cooled to room temperature, distilled water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 22.27 g (yield 70%) of Compound 53.

(7.51 / M, 9.34 / S) 2H (7.45 / M, 7.59 / M, 7.68 / M, 7.79 / D, 8.56 / D, 8.91 / M, 8.45 / M) 4H (7.22 / M, 7.58 / M) 6H (7.50 / M)

LC / MS: m / z = 807 [(M + 1) ^< ^{+ &}

Example  13: Compound 54 Synthesis

To a solution of Intermediate 54-1 (15.5 g, 0.0394 mol, China), Pd2 (dba) 3 (1.80 g, 0.0019 mol), P (t-Bu) 3 (0.957 g, 0.0047mol), sodium tert-butoxide (4.54g, 0.0473mol) and 426ml of toluene were added and reacted at 80 ° C. After completion of the reaction, the reaction mixture was cooled to room temperature, distilled water was added thereto, and the mixture was extracted and purified by column chromatography (n-hexane: methylene chloride) to obtain 14.78 g (yield 70%) of Compound 54.

_{H-NMR (200MHz, CDCl 3} ): δ ppm 1H (7.51 / M, 7.52 / M, 7.98 / M, 8.05 / M, 9.34 / S) 2H (7.68 / D, 7.79 / D, 8.45 / M, 8.91 / S) 3H (7.50 / M)

LC / MS: m / z = 536 [(M + 1) ^< ^{+ &}

Example  14: Compound 55 Synthesis

Intermediate 55-1 (14.71 g, 0.0394 mol, China), Pd2 (dba) 3 (1.80 g, 0.0019 mol) and P (t-Bu) 3 (0.957 g, 0.0394 mol) 0.0047mol), sodium tert-butoxide (4.54g, 0.0473mol) and 426ml of toluene were added and reacted at 80 ° C. After completion of the reaction, the reaction mixture was cooled to room temperature, distilled water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 14.23 g (yield 70%) of Compound 55.

_{H-NMR (200MHz, CDCl 3} ): δ ppm 1H (7.51 / M, 8.43 / M, 9.34 / S) 2H (6.63 / D, 7.27 / M, 7.36 / M, 7.37 / M, 7.50 / M, 8.04 / S, 8.09 / D, 8.45 / M, 8.91 / S)

LC / MS: m / z = 516 [(M + 1) ^< ^{+ &}

Example  15: Compound 56 Synthesis

(16.09 g, 0.0394 mol, China), Pd2 (dba) 3 (1.80 g, 0.0019 mol) and P (t-Bu) 3 (0.957 g, 0.0394 mol) were added to Intermediate 51-2 0.0047mol), sodium tert-butoxide (4.54g, 0.0473mol) and 426ml of toluene are added and reacted at 80 ° C. After completion of the reaction, the reaction mixture was cooled to room temperature, distilled water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 15.20 g (yield 70%) of Compound 56.

_{H-NMR (200MHz, CDCl 3} ): δ ppm 1H (7.28 / D, 7.67 / D, 8.1 / S, 9.34 / S) 2H (7.41 / M, 7.50 / M, 8.91 / S) 3H (8.43 / M) 4H (7.47 / M) 5H (7.51 / M)

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

Example  16: Compound 57 Synthesis

Intermediate 57-1 (22.33 g, 0.0394 mol, China), Pd2 (dba) 3 (1.80 g, 0.0019 mol) and P (t-Bu) 3 (0.957 g, 0.0047mol), sodium tert-butoxide (4.54g, 0.0473mol) and 426ml of toluene were added and reacted at 80 ° C. After completion of the reaction, the reaction mixture was cooled to room temperature, distilled water was added thereto, and the mixture was extracted and purified by column (n-hexane: methylene chloride) to obtain 19.56 g of Compound 57 (yield: 70%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm 1H (9.34 / S) 2H (7.50 / M, 7.68 / D, 8.91 / S) 3H (7.41 / M, 8.43 / M) 4H (7.47 / M, 7.79 / D) 7H (7.51 / M)

LC / MS: m / z = 709 (M + 1) ^< ^{+ &}

Example  17: Compound 59 Synthesis

Pd2 (dba) 3 (1.80 g, 0.0019 mol) and P (t-Bu) 3 (0.957 g, 0.0394 mol) were added to Intermediate 51-2 (10.65 g, 0.0394 mol) 0.0047mol), sodium tert-butoxide (4.54g, 0.0473mol) and 426ml of toluene were added and reacted at 80 ° C. After completion of the reaction, the reaction mixture was cooled to room temperature, distilled water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 12.76 g (yield 70%) of Compound 59.

_{H-NMR (200MHz, CDCl 3} ): δ ppm 1H (6.87 / D, 7.51 / M, 7.73 / S, 8.43 / M, 8.54 / D, 9.34 / S) 2H (7.48 / M, 7.50 / M, 7.68 / D, 7.79 / D, 8.45 / M, 8.91 / S)

LC / MS: m / z = 463 (M + 1) ^< ^{+ &}

Example  18: Compound 60 Synthesis

To a solution of Intermediate 51-2 (10.65 g, 0.0394 mol) was added intermediate 60-1 (14.56 g, 0.0394 mol, China), Pd2 (dba) 3 (1.80 g, 0.0019 mol), P (t- 0.0047mol), sodium tert-butoxide (4.54g, 0.0473mol) and 426ml of toluene were added and reacted at 80 ° C. After completion of the reaction, the reaction mixture was cooled to room temperature, distilled water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 14.12 g (yield 70%) of Compound 60.

_{H-NMR (200MHz, CDCl 3} ): δ ppm 1H (7.25 / M, 7.29 / M, 7.33 / M, 7.51 / M, 7.63 / D, 7.94 / D, 8.12 / D, 8.43 / M, 8.55 / D, 9.34 / S) 2H (8.45 / M, 8.91 / S) 3H (7.50 / M), 4H (7.62 /

LC / MS: m / z = 512 [(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

Depositing NPB on the glass substrate coated with ITO to form a hole transport layer was of 120nm, followed by Ir (ppy) the deposition rate of the compounds 1 to ₃ as the dopant 0.1nm / sec, Ir (ppy) ₃ deposition rate 0.009nm / sec, and Ir (ppy) ₃ was doped so that the deposition rate ratio was 9% to form a light emitting layer with 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 for preventing holes from moving to the electron transporting layer through the light emitting layer, and Alq3 was deposited thereon to form an electron transporting layer of 40 nm, and lithium fluoride was deposited thereon 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 set to 0.1 nm / sec for compound 1, NPB, Alq ₃ , Balq, 0.01 nm / sec for lithium fluoride, and 0.5 nm / sec for aluminum.

Device Example  2 to 15

An organic electroluminescent device of each of the device embodiments 2 to 15 was fabricated in the same manner as in the device example 1, except that the luminescent material described in the following Table 1 was used in place of the compound 1.

Device Example  16: Compound 3 was used as an electron transporting material Organic electroluminescent device  Produce

Except that (4,4-N, N-dicarbazole) biphenyl (CBP) was used instead of Compound 1 as the light emitting material and Compound 3 was used instead of Alq3 as the electron transporting material. Organic electroluminescent devices of 16 to 19 were fabricated.

Device Example  17 to 19

An organic electroluminescent device of each of the device examples 17 to 19 was fabricated in the same manner as in the device example 16, except that the electron transporting material described in Table 2 was used instead of the compound 3.

Device comparison example  One

An organic electroluminescent device of Comparative Example 1 was prepared in the same manner as in Example 1 except that (4,4-N, N-dicarbazole) biphenyl (CBP)

The results of comparing the characteristics of the organic electroluminescent devices manufactured according to the device embodiments 1 to 19 and the device comparison example 1 are shown in the following Tables 1 and 2.

Emitting material The driving voltage (V)
(at 1000 cd / m ² ) Luminous efficiency
(cd / A) color Device Embodiment 1 Compound 1 5.1 35 green Device Example 2 Compound 2 5.9 30 green Device Embodiment 3 Compound 3 6.0 25 green Device Example 4 Compound 5 5.4 22 green Element Embodiment 5 Compound 7 4.5 25 green Device Example 6 Compound 13 5.9 26 green Device Example 7 Compound 14 5.2 27 green Device Example 8 Compound 15 5.5 31 green Device Example 9 Compound 19 5.4 29 green Element Embodiment 10 Compound 21 5.5 32 green Element Embodiment 11 Compound 22 5.6 28 green Device Example 12 Compound 23 5.5 30 green Device Embodiment 13 Compound 24 6.0 24 green Device Embodiment 14 Compound 25 5.8 26 green Device Example 15 Compound 26 5.7 30 green Device Comparative Example 1 CBP 6.5 19 green

Electron transport material The driving voltage (V)
(at 1000 cd / m ² ) Luminous efficiency
(cd / A) color Device Embodiment 16 Compound 3 4.9 24 green Device Example 17  Compound 5 5.0 22 green Element Embodiment 18 Compound 4 5.0 21 green Element Embodiment 19 Compound 29 5.4 22 green Device Comparative Example 1 Alq ₃ 6.5 19 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) by the current deposition raises 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 The results are shown in Tables 1 and 2 above.

According to Tables 1 and 2, when the compound for an organic electroluminescent device according to the present invention is used as a host material of a light emitting layer of an organic electroluminescent device or as an electron transport material, conventional CBP is used as a light emitting material, or Alq ₃ is used as an electron It can be seen that the driving voltage is considerably lower than that in the case of using it as a transportation material and the luminous efficiency is considerably improved.

Claims (8)

A compound for an organic electroluminescence device represented by Structural Formula (1) below.
[Structural formula 1]

In the above formula 1,
Ring a, ring b and ring c may be the same or different from each other, and at least one of ring a, ring b and ring c is a substituted or unsubstituted 6-membered heteroaromatic ring containing a nitrogen atom,
Y ¹ represents an oxygen atom, a sulfur atom, or

ego,
Ar ¹ is

,

, A substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,
R ¹ is a hydrogen atom,

,

, A substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,
Ar ² and Ar ³ may be the same or different from each other, Ar ² and Ar ³ are each independently a hydrogen atom,

,

,

,

,

,

,

,

,

,

,

,

, A substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,
Ar ⁴ to Ar ⁶ , Ar ⁹ , and Ar ¹⁰ may be the same or different from each other, Ar ⁴ to Ar ⁶ , Ar ⁹ , and Ar ¹⁰ each independently represent a substituted or unsubstituted C1 to C30 alkyl 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,
Y ² and Y ⁵ may be the same or different from each other, Y ² and Y ⁵ are each independently an oxygen atom or a sulfur atom,
X ⁴ to X ⁷ , X ¹⁰ to X ¹⁸ , and X ²¹ to X ²³ may be the same or different from each other, and X ⁴ to X ⁷ , X ¹⁰ to X ¹⁸ , and X ²¹ to X ²³ each independently represent a nitrogen atom or

ego,
X ¹ to X ³ may be the same or different from each other, and X ¹ to X ³ are each independently a nitrogen atom or

, X ¹ to X ³ are both simultaneously

However,
R ¹² to R ¹⁴ , R ¹⁷ to R ²⁴ , R ²⁹ to R ³⁸ , R ⁴⁵ and R ⁴⁶ may be the same or different from each other and R ¹² to R ¹⁴ , R ¹⁷ to R ²⁴ , R ²⁹ to R ³⁸ , R ⁴⁵ and R ⁴⁶ 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 a substituted or unsubstituted C1 to C30 heteroaryl group,
R ² , R ³ and R ⁶ to R ¹¹ may be the same or different from each other, and R ² , R ³ and R ⁶ to R ¹¹ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl 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. The method according to claim 1,
Wherein the compound for an organic electroluminescence element is represented by the following structural formula (2).
[Structural formula 2]

In the above formula 2,
Y ¹ represents an oxygen atom, a sulfur atom, or

ego,
Ar ¹ is

,

, A substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,
R ¹ is a hydrogen atom,

,

, A substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,
Ar ² and Ar ³ may be the same or different from each other, Ar ² and Ar ³ are each independently a hydrogen atom,

,

,

,

,

,

,

,

,

,

,

,

, A substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,
Ar ⁴ to Ar ⁶ , Ar ⁹ , and Ar ¹⁰ may be the same or different from each other, Ar ⁴ to Ar ⁶ , Ar ⁹ , and Ar ¹⁰ each independently represent a substituted or unsubstituted C1 to C30 alkyl 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,
Y ² and Y ⁵ may be the same or different from each other, Y ² and Y ⁵ are each independently an oxygen atom or a sulfur atom,
X ⁴ to X ⁷ , X ¹⁰ to X ¹⁸ , and X ²¹ to X ²³ may be the same or different from each other, and X ⁴ to X ⁷ , X ¹⁰ to X ¹⁸ , and X ²¹ to X ²³ each independently represent a nitrogen atom or

ego,
X ¹ to X ³ are nitrogen atoms,
R ¹² to R ^14, R ¹⁷ to R ^24, R ²⁹ to R ^38, and R ⁴⁵ may be the same or different from each other, R ¹² to R ^14, R ¹⁷ to R ^24, R ²⁹ to R ^38, and R ⁴⁵ 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 a substituted or unsubstituted C1 to C30 heteroaryl group,
R ² , R ³ and R ⁶ to R ¹¹ may be the same or different from each other, and R ² , R ³ and R ⁶ to R ¹¹ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl 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. The method according to claim 1,
Wherein the compound for an organic electroluminescent device is any one selected from the group consisting of compounds represented by the following formulas.

An organic electroluminescent device comprising the compound for an organic electroluminescent device according to any one of claims 1 to 3. 1. An organic electroluminescent device comprising 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 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. 6. The method of claim 5,
Wherein the single or plural organic layers include a light emitting layer. 6. The method of claim 5,
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. The method according to claim 6,
Wherein the light emitting layer comprises a host and a dopant.

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