KR101584753B1 - 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. As a result, it can be used as a host, a hole transporting material, and an organic light emitting device which can be used as an electron transporting material, which can improve the luminous efficiency of a phosphorescent light emitting material because of its excellent electrical stability, electron and hole transporting ability, A compound and an organic electroluminescent device 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,

Ar ¹ 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 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 C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, Or a substituted or unsubstituted C1 to C30 heteroaryl group,

이고,X ¹ represents an oxygen atom, a sulfur atom, or

ego,

Ar ² 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 ² to R ⁵ may be the same or different from one another and each of R ² to R ⁵ 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, or at least any one of R ² to R ⁵ is a substituted or unsubstituted C1 to C30 heterocycloalkyl group, A substituted or unsubstituted fused C3 to C30 cycloalkyl group, 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.

In one embodiment of the present invention, preferably,

,

,

,

,

,

,

,

,

,

,

,

,

, 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 C1 내지 C30 헤테로시클로알킬기이고,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,

R ⁶ to R ⁴³ may be the same or different from each other and each of R ⁶ to R ⁴³ 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,

, 또는

이고,X ² To X ⁸ may be the same or different from each other, and X ² To X < ⁸ > each independently represent an oxygen atom, a sulfur atom,

, or

ego,

Ar ³ 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,

이고, Y ¹ to Y ²⁴ may be the same or different from each other, Y ¹ to Y ²⁴ each independently represent a nitrogen atom or

ego,

, 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 C1 내지 C30 헤테로시클로알킬기이고,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,

이고,Y ²⁵ to Y ²⁷ may be the same or different from each other, and Y ²⁵ to Y ²⁷ are each independently a nitrogen atom or

ego,

R ⁴⁴ to R ⁴⁹ may be the same or different from each other, and R ⁴⁴ to R ⁴⁹ each independently represent a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, Substituted C1 to C30 heterocycloalkyl groups, substituted or unsubstituted C6 to C30 aryl groups, or substituted or unsubstituted C1 to C30 heteroaryl groups.

According to another embodiment of the present invention, preferably,

,

,

,

,

,

, 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 C1 내지 C30 헤테로시클로알킬기이고,R ⁶ to R ⁴³ may be the same or different from each other, and R ⁶ to R ⁴³ 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,

, 또는

이고,X ⁹ To X ¹² may be the same or different from each other, and X ⁹ To X ¹² each independently represent an oxygen atom, a sulfur atom,

, or

ego,

Ar ⁴ 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,

이고, Y ²⁸ to Y ³⁰ may be the same or different from each other, and each of Y ²⁸ to Y ³⁰ is independently a nitrogen atom or

ego,

R ⁵⁰ to R ⁷¹ may be the same or different from each other, and each of R ⁵⁰ to R ⁷¹ 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,

, 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 C1 내지 C30 헤테로시클로알킬기이고,Ar ³ 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,

X ¹³ is an oxygen atom or a sulfur atom,

이고,Y ³¹ represents a nitrogen atom or

ego,

R ⁷² to R ⁷⁴ may be the same or different from each other, and each of R ⁷² to R ⁷⁴ independently represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, Substituted C1 to C30 heterocycloalkyl groups, substituted or unsubstituted C6 to C30 aryl groups, or substituted or unsubstituted C1 to C30 heteroaryl groups.

According to another embodiment of the present invention, preferably,

, 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 C1 내지 C30 헤테로시클로알킬기이고,Ar ⁴ 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,

X ¹⁴ is an oxygen atom or a sulfur atom,

이고,Y ³² represents a nitrogen atom or

ego,

R ⁷⁵ to R ⁷⁷ may be the same or different from each other, and each of R ⁷⁵ to R ⁷⁷ independently represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, Substituted C1 to C30 heterocycloalkyl groups, substituted or unsubstituted C6 to C30 aryl groups, or substituted or unsubstituted 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 acridinyl 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 80 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 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

Pyrido [3,4-b] indole (10.9 g, 0.054 mol / sigma aldrich) and NaH (3.2 g, 0.04 mol) were added to 4-chlorodibenzo [b, d] thiophene (10.0 g, 0.045 mol / 0.135 mol / sigma Aldrich), and the mixture was reacted at room temperature for 24 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: EA) to obtain 12.2 g (yield 70%) of Intermediate 1-1.

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

(2) Manufacturing example  1-2: Compound 1 synthesis

Dibenzo [b, d] thiophen-2-ylboronic acid (7.1 g, 0.031 mol / Chinese acid), Pd (PPh3) 4 (1.5 g, 0.0013 mol / P & H TECH) 200 ml of THF was added to potassium carbonate (7.2 g, 0.052 mol / sigma Aldrich), and the mixture was reacted at 85 ° C for 18 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 9.9 g (yield: 71%) of Compound 1.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.18 / D, 8.41 / D, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D, 8.56 / S, 8.23 / S, 8.31 / D , 7.89 / D, 8.51 / S) 2H (7.50 / M, 8.45 / D, 7.52 / M, 7.98 / D)

LC / MS: m / z = 534 [(M + 1) ^< ^{+ &}

Example  2: Synthesis of compound 2

Dibenzo [b, d] thiophen-1-ylboronic acid (7.1 g, 0.031 mol / Chinese acid), Pd (PPh3) 4 (1.5 g, 0.0013 mol), potassium carbonate 7.2 g, 0.052 mol) was added 200 ml of THF, and the mixture was reacted at 85 캜 for 18 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 10.1 g (yield: 73%) of Compound 2.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.18 / D, 7.94 / D, 8.41 / D, 7.33 / M, 7.25 / M, 8.55 / D, 8.56 / S, 8.23 / S, 8.33 / D , 7.59 / M, 8.00 / D) 2H (7.98 / D, 7.50 / M, 7.52 / M, 8.45 / D)

LC / MS: m / z = 534 [(M + 1) ^< ^{+ &}

Example  3: Synthesis of compound 4

3-ylboronic acid (8.9 g, 0.031 mol / Chinese acid), Pd (PPh3) 4 (1.5 g, 0.0013 mol) and potassium carbonate (10.0 g, 0.026 mol) 7.2 g, 0.052 mol) was added 200 ml of THF, and the mixture was reacted at 85 캜 for 18 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 10.9 g (yield: 71%) of Compound 4.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.45 / M, 7.72 / D, 8.38 / D, 8.28 / D, 8.23 / S, 8.56 / S, 8.41 / D, 8.18 / D, 8.45 / D , 7.52 / M) 2H (7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D)

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

Example  4: Synthesis of compound 9

4,6-diphenyl-1,3,5-triazin-2-ylboronic acid (8.6 g, 0.031 mol / Chinese acid) and Pd (PPh3) 4 (1.5 g, 0.0013 mol) were added to Intermediate 1-1 (10.0 g, 0.026 mol) mol) and potassium carbonate (7.2 g, 0.052 mol) were added 200 ml of THF and the mixture was reacted at 85 ° C for 18 hours with stirring. After completion of the reaction, the reaction mixture was cooled, subjected to column separation on H ₂ O: MC, and subjected to column purification (n-hexane: MC) to obtain 11.2 g (yield: 74%) of Compound 9.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.98 / D, 7.50 / M, 7.52 / M, 8.45 / D, 8.18 / D, 8.41 / D, 7.94 / D, 7.33 / M, 7.25 / M , 8.55 / D, 8.65 / S, 8.29 / S) 2H (7.41 / M) 4H (8.28 / D, 7.51 /

LC / MS: m / z = 583 [(M + 1) ^< ^{+ &}

Example  5: Compound 10 Synthesis

4-ylboronic acid (8.5 g, 0.031 mol / Chinese acid), Pd (PPh3) 4 (1.5 g, 0.0013 mol) and potassium carbonate (7.2 g, , 0.052 mol) was added 200 ml of THF, and the mixture was reacted at 85 ° C for 18 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 10.9 g (yield: 72%) of Compound 10.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.98 / D, 7.50 / M, 7.52 / M, 8.45 / D, 8.18 / D, 8.41 / D, 7.94 / D, 7.33 / M, 7.25 / M , 8.55 / D, 8.65 / S, 8.29 / S) 2H (7.47 / M, 8.56 /

LC / MS: m / z = 581 [(M + 1) ^< ^{+ &}

Example  6: Compound 18 Synthesis

(One) Manufacturing example  6-1: Synthesis of Intermediate 18-1

Phthalazine-1,4-diyldiboronic acid (6.8 g, 0.031 mol / Chinese acid), Pd (PPh3) 4 (1.5 g, 0.0013 mol) and potassium carbonate (7.2 g, 0.052 mol) were added to Intermediate 1-1 (10.0 g, 0.026 mol) mol) was added 200 ml of THF, and the mixture was reacted at 85 DEG C for 18 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC, and subjected to column purification (n-hexane: MC) to obtain 9.5 g (yield 70%) of Intermediate 18-1.

LC / MS: m / z = 524 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  6-2: Compound 18 Synthesis

150ml of THF was added to bromobenzene (3.6g, 0.023mol / Chinese acid), Pd (PPh3) 4 (1.1g, 0.0001mol) and potassium carbonate (5.3g, 0.038mol) The reaction was carried out with stirring at 85 ° C for 18 hours. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and column-purified (n-hexane: MC) to obtain 8.0 g (yield 76%) of Compound 18.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.41 / M, 8.29 / S, 8.55 / D, 7.25 / M, 7.33 / M, 7.94 / D, 8.65 / S, 8.41 / D, 8.18 / D , 7.94 / D, 7.52 / M, 7.50 / M, 7.98 / D)

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

Example  7: Compound 19 Synthesis

To the intermediate 18-1 (10.0 g, 0.019 mol) was added 1-bromodibenzo [b, d] thiophene (6.1 g, 0.023 mol / Chinese acid), Pd (PPh3) 4 (1.1 g, 0.0001 mol) 0.038 mol), 150 ml of THF was added, and the mixture was reacted at 85 캜 for 18 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 12.6 g (yield: 73%) of Compound 19.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.18 / D, 8.41 / D, 8.65 / S, 7.33 / M, 7.25 / M, 8.29 / S, 7.82 / S, 7.56 / D) 2H (7.94 / D, 7.85 / M, 7.93 / M, 7.50 / M, 7.98 / D, 7.52 / M,

LC / MS: m / z = 662 [(M + 1) ^< ^{+ &}

Example  8: Compound 20 Synthesis

4-bromodibenzo [b, d] thiophene (6.1 g, 0.023 mol / Chinese acid), Pd (PPh3) 4 (1.1 g, 0.0001 mol), potassium carbonate (5.3 g, 0.038 mol), 150 ml of THF was added, and the mixture was reacted at 85 캜 for 18 hours with stirring. After completion of the reaction, the reaction mixture was cooled, and subjected to column separation on H ₂ O: MC, followed by column purification (n-hexane: MC) to obtain 8.9 g (yield: 71%) of Compound 20.

D, 7.94 / D, 8.41 / D, 8.65 / S, 7.33 / M, 7.25 / M, 8.55 / D, 8.29 / S, 7.80 / D (200 MHz, CDCl ₃ ) 7.85 / M, 7.93 / D, 7.50 / M, 7.98 / D, 7.52 / M, 8.45 / D)

LC / MS: m / z = 662 [(M + 1) ^< ^{+ &}

Example  9: Compound 21 Synthesis

(One) Manufacturing example  9-1: Synthesis of Intermediate 21-1

150 ml of THF was added to 4-chlorodibenzo [b, d] thiophene (10.0 g, 0.045 mol / Chinese acid), acetyl hypofluorite (4.2 g, 0.054 mol / Chinese acid) and dibromomethane (15.6 g, 0.09 mol / The mixture was reacted with stirring for a period of time. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 9.2 g (yield: 71%) of Intermediate 21-1.

LC / MS: m / z = 289 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  9-2: Intermediate 21-2 Synthesis

3-chloro-9H-pyrido [3,4-b] indole (8.5g, 0.042mol), Pd (PPh3) 4 (2.0g, 0.0018mol), potassium (9.7 g, 0.07 mol) in THF (200 ml), and the mixture was reacted at 85 ° C for 18 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and column-purified (n-hexane: MC) to obtain 11.9 g (yield: 73%) of Intermediate 21-2.

LC / MS: m / z = 465 [(M + 1) ^< ^{+ &}

(3) Manufacturing example  9-3: Intermediate 21-3 Synthesis

2-ylboronic acid (7.2 g, 0.026 mol) and Pd (PPh3) 4 (1.3 g, 0.0011 mol) were added to Intermediate 21-2 (10.0 g, 0.022 mol) , potassium carbonate (6.1 g, 0.044 mol), and the mixture was reacted at 85 ° C for 18 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 10.1 g (yield: 74%) of Intermediate 21-3.

LC / MS: m / z = 618 [(M + 1) ^< ^{+ &}

(4) Manufacturing example  9-4: Compound 21 Synthesis

Dibenzo [b, d] thiophen-1-ylboronic acid (4.4 g, 0.019 mol), Pd (PPh3) 4 (0.1 g, 0.0008 mol) and potassium carbonate (4.4 g, 0.016 mol) , 0.032 mol) was added 200 ml of THF, and the mixture was reacted at 85 ° C for 18 hours with stirring. After completion of the reaction, the reaction mixture was cooled, and subjected to column separation on H ₂ O: MC, followed by column purification (n-hexane: MC) to obtain 8.8 g (yield: 72%) of Compound 21.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.29 / S, 8.56 / S, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D, 8.23 / S, 8.33 / D, 7.59 / M (8.8 / D, 7.51 / M), 8.00 / D) 2H (7.41 / M, 7.98 / D, 7.50 / M, 7.52 /

LC / MS: m / z = 765 [(M + 1) ^< ^{+ &}

Example  10: Compound 25 Synthesis

3-ylboronic acid (5.5 g, 0.019 mol), Pd (PPh3) 4 (0.1 g, 0.0008 mol) and potassium carbonate (4.4 g, 0.016 mol) were added to Intermediate 21-3 , 0.032 mol) was added 200 ml of THF, and the mixture was reacted at 85 ° C for 18 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 9.6 g (yield: 73%) of Compound 25.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.29 / S, 8.56 / S, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D, 8.23 / S, 8.33 / D, 7.59 / M (8.8 / D, 7.51 / M), 8.00 / D) 2H (7.41 / M, 7.98 / D, 7.50 / M, 7.52 /

LC / MS: m / z = 824 [(M + 1) ^< ^{+ &}

Example  11: Compound 30 Synthesis

Dibenzo [b, d] thiophen-2-ylboronic acid (4.3 g, 0.019 mol), Pd (PPh3) 4 (0.1 g, 0.0008 mol), potassium carbonate (4.4 g, 0.016 mol) , 0.032 mol) was added 200 ml of THF, and the mixture was reacted at 85 ° C for 18 hours with stirring. After completion of the reaction, the reaction mixture was cooled, and subjected to column separation on H ₂ O: MC, followed by column purification (n-hexane: MC) to obtain 9.1 g (yield: 74%) of Compound 30.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.29 / S, 8.56 / S, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D, 8.23 / S, 8.33 / D, 7.59 / M (8.8 / D, 7.51 / M), 8.00 / D) 2H (7.41 / M, 7.98 / D, 7.50 / M, 7.52 /

LC / MS: m / z = 765 [(M + 1) ^< ^{+ &}

Example  12: Compound 31 Synthesis

Dibenzo [b, d] thiophen-2-ylboronic acid (4.3 g, 0.019 mol), Pd (PPh3) 4 (0.1 g, 0.0008 mol), potassium carbonate (4.4 g, 0.016 mol) , 0.032 mol) was added 200 ml of THF, and the mixture was reacted at 85 ° C for 18 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC, and subjected to column purification (n-hexane: MC) to obtain 9.3 g (yield 75%) of Compound 30.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.29 / S, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D, 8.23 / S, 8.33 / D, 7.59 / M, 8.00 / D ) H (7.47 / M, 7.98 / D, 7.50 / M, 7.52 / M, 8.45 / D)

LC / MS: m / z = 765 [(M + 1) ^< ^{+ &}

Example  13: Compound 35 Synthesis

3-ylboronic acid (5.5 g, 0.019 mol), Pd (PPh3) 4 (0.1 g, 0.0008 mol) and potassium carbonate (4.4 g, 0.016 mol) were added to Intermediate 21-3 , 0.032 mol) was added 200 ml of THF, and the mixture was reacted at 85 ° C for 18 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 9.4 g (yield: 71%) of Compound 25.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.23 / S, 8.28 / S, 8.38 / D, 7.72 / D, 7.45 / M, 7.98 / D, 7.52 / M, 8.45 / D, 8.29 / S D, 7.54 / M) 2H (7.47 / M, 7.58 / M, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D)

LC / MS: m / z = 824 [(M + 1) ^< ^{+ &}

Example  14: Compound 36 Synthesis

Pyridin-2-ylboronic acid (5.5g, 0.019mol), Pd (PPh3) 4 (0.1g, 0.0008mol) was added to Intermediate 21-3 (10.0g, 0.016mol) 200 ml of THF was added to potassium carbonate (4.4 g, 0.032 mol), and the mixture was reacted at 85 ° C for 18 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC, and subjected to column purification (n-hexane: MC) to obtain 9.5 g (yield: 72%) of Compound 36.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.29 / S, 8.45 / D, 7.52 / M, 7.50 / M, 7.98 / D, 8.59 / S, 9.19 / S, 9.30 / D, 7.57 / M , 7.64 / D, 7.63 / D, 7.50 / M, 7.29 / M, 8.12 / D) 2H (7.47 / M, 8.56 / S, 7.94 / D, 7.33 / / D, 7.54 / M)

LC / MS: m / z = 823 [(M + 1) ^< ^{+ &}

Example  15: Compound 37 Synthesis

250 ml of THF was added to terphenylboronicacid (14.2 g, 0.052 mol), Pd (PPh3) 4 (1.3 g, 0.0011 mol) and potassium carbonate (6.1 g, 0.044 mol) For 18 hours with stirring. After completion of the reaction, the reaction mixture was cooled, and subjected to column separation on H ₂ O: MC, followed by column purification (n-hexane: MC) to obtain 13.2 g (yield: 74%) of Compound 37.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.98 / D, 7.50 / M, 7.52 / M, 8.45 / D, 8.65 / S, 8.55 / D, 7.25 / M, 7.33 / M, 7.94 / D ) 2H (8.29 / S) 4H (7.47 / M, 8.56 /

LC / MS: m / z = 810 [(M + 1) ^< ^{+ &}

Example  16: Compound 40 Synthesis

200 ml of THF was added to bromobenzene (8.2 g, 0.052 mol), Pd (PPh3) 4 (1.3 g, 0.0011 mol) and potassium carbonate (6.1 g, 0.044 mol) For 18 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 7.8 g (yield 70%) of Compound 40.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.98 / D, 7.50 / M, 7.52 / M, 8.45 / D, 8.23 / S, 8.56 / S, 8.55 / D, 7.25 / M, 7.33 / M , 7.94 / D) 2H (7.47 / M) 4H (8.30 / D, 7.54 / M)

LC / MS: m / z = 504 [(M + 1) ^< ^{+ &}

Example  17: Compound 27 Synthesis

4-diphenyl-1,3,5-triazin-2-ylboronic acid (14.4 g, 0.052 mol) and Pd (PPh3) 4 (1.3 g, 0.0011 mol) were added to Intermediate 21-2 (10.0 g, 0.022 mol) , potassium carbonate (6.1 g, 0.044 mol), and the mixture was reacted at 85 ° C for 18 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC, and subjected to column purification (n-hexane: MC) to obtain 12.8 g (yield: 71%) of Compound 27.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / D, 7.25 / M, 7.33 / M, 7.94 / D, 8.65 / S, 8.45 / D, 7.52 / M, 7.50 / M, 7.98 / D ) 2H98.29 / S) 4H97.41 / M) 8H (8.28 / D, 7.51 / M)

LC / MS: m / z = 812 [(M + 1) ^< ^{+ &}

Example  18: Compound 41  synthesis

(One) Manufacturing example  18-1: Synthesis of Intermediate 41-1

Phthalazine-1,4-diyldiboronic acid (6.8g, 0.031mol), Pd (PPh3) 4 (1.5g, 0.0013mol) and potassium carbonate (7.2g, 0.052mol) were added to Intermediate 1-1 (10.0g, 0.026mol) , 200 ml of THF was added, and the mixture was reacted at 85 DEG C for 18 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 9.7 g (71%) of Intermediate 41-1.

LC / MS: m / z = 524 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  18-2: Compound 41 Synthesis

2-bromodibenzo [b, d] thiophene (6.1 g, 0.023 mol), Pd (PPh3) 4 (0.1 g, 0.0010 mol) and potassium carbonate (5.3 g, 0.038 mol) were added to Intermediate 41-1 ), 200 ml of THF was added, and the mixture was reacted at 85 DEG C for 18 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 9.9 g (yield: 71%) of Compound 41.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.18 / D, 8.41 / D, 8.65 / S, 8.29 / S, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D, 7.80 / D (7.85 / M, 7.93 / D, 7.98 / D, 7.50 / M, 7.52 / M, 8.45 / D)

LC / MS: m / z = 663 [(M + 1) ^< ^{+ &}

Example  19: Compound 43 Synthesis

3-bromo-9-phenyl-9H-carbazole (7.4 g, 0.023 mol), Pd (PPh3) 4 (0.1 g, 0.0010 mol), potassium carbonate (5.3 g, 0.038 mol) was added 200 ml of THF, and the mixture was reacted at 85 캜 for 18 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and column-purified (n-hexane: MC) to obtain 10.0 g (yield: 73%) of Compound 43.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.98 / D, 7.52 / M, 8.45 / D, 8.29 / S, 7.69 / D, 8.18 / D, 8.41 / D, 8.65 / S, 7.87 / D (7.85 / M, 7.93 / D, 7.58 / M, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D)

LC / MS: m / z = 721 [(M + 1) ^< ^{+ &}

Example  20: Compound 45 Synthesis

Pd (PPh3) 4 (0.1 g, 0.0010 mol) and potassium carbonate (5.3 g, 0.023 mol) were added to Intermediate 41-1 (10.0 g, 0.019 mol) 0.038 mol) was added 200 ml of THF, and the mixture was reacted at 85 캜 for 18 hours with stirring. After completion of the reaction, the reaction mixture was cooled, subjected to column separation on H ₂ O: MC, and subjected to column purification (n-hexane: MC) to obtain 9.7 g (yield: 71%) of Compound 45.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.98 / D, 7.50 / M, 7.52 / M, 8.45 / D, 8.18 / D, 8.41 / D, 8.65 / S, 8.29 / S, 7.79 / D M, 7.49 / D, 8.09 / S, 7.63 / D, 7.50 / M, 7.29 / M, 8.12 / D) , 8.55 / D)

LC / MS: m / z = 721 [(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 20

Device Examples 2 to 20 An organic electroluminescent device was manufactured in the same manner as in Example 1 except that the compound described in Table 1 was used instead of Compound 1 as a light emitting material.

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)

Hereinafter, the characteristics of the organic electroluminescent device manufactured according to the device embodiments 1 to 20 and the device comparison example 1 are compared and the results are shown in Table 1 below.

Emitting material The driving voltage (V)
(at 1000 cd / m ² ) Luminous efficiency
(cd / A) Color coordinates
CIE (x, y) Device Embodiment 1 Compound 1 6.1 23 (0.33, 0.63) Device Example 2 Compound 2 6.0 22 (0.33, 0.63) Device Embodiment 3 Compound 4 6.2 22 (0.33, 0.63) Device Example 4 Compound 9 5.8 24 (0.33, 0.63) Element Embodiment 5 Compound 10 5.5 21 (0.33, 0.63) Device Example 6 Compound 18 5.8 26 (0.33, 0.64) Device Example 7 Compound 19 5.9 25 (0.33, 0.63) Device Example 8 Compound 20 5.7 25 (0.33, 0.63) Device Example 9 Compound 21 6.0 23 (0.33, 0.64) Element Embodiment 10 Compound 25 6.0 23 (0.33, 0.63) Element Embodiment 11 Compound 30 5.9 22 (0.32, 0.63) Device Example 12 Compound 31 5.8 23 (0.33, 0.63) Device Embodiment 13 Compound 35 6.1 24 (0.33, 0.63) Device Embodiment 14 Compound 36 6.1 22 (0.33, 0.63) Device Example 15 Compound 37 5.7 21 (0.32, 0.63) Device Embodiment 16 Compound 40 5.8 22 (0.33, 0.63) Device Example 17 Compound 27 5.8 23 (0.33, 0.63) Element Embodiment 18 Compound 41 5.9 22 (0.33, 0.63) Element Embodiment 19 Compound 43 5.7 25 (0.32, 0.63) Device Embodiment 20 Compound 45 6.0 22 (0.33, 0.64) Device Comparative Example 1 CBP 6.5 19 (0.33, 0.63)

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 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 electroluminescence device, the driving voltage is considerably lower than that of the conventional CBP as a light emitting material and the luminous efficiency is considerably improved Able to know.

Claims (10)

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

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

, R < ¹ > is a hydrogen atom or

Lt;
Wherein Ar ² is a phenyl group, and wherein Y ²⁵ to Y ²⁷ may be the same or different from each other, Y ²⁵ to Y ²⁷ each independently represent a nitrogen atom or

Lt;
Ar ¹ is

,

,

,

,

,

,

,

,

,

or

ego,
R ⁶ to R ⁴³ may be the same or different from each other and each of R ⁶ to R ⁴³ 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 C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
X ² to X ⁸ may be the same or different from each other, and X ² to X ⁸ each independently represent an oxygen atom, a sulfur atom,

, or

ego,
Ar ³ 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 ⁴⁴ to R ⁴⁹ may be the same or different from each other and each of R ⁴⁴ to R ⁴⁹ 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 C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group. delete The method according to claim 1,
R ⁶ to R ⁴³ may be the same or different from each other, and R ⁶ to R ⁴³ 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,
X ⁹ to X ¹² may be the same or different from each other, and each of X ⁹ to X ¹² independently represents an oxygen atom, a sulfur atom,

, or

ego,
Ar ⁴ 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,
Y ²⁸ to Y ³⁰ may be the same or different from each other, and each of Y ²⁸ to Y ³⁰ is independently a nitrogen atom or

ego,
R ⁵⁰ to R ⁷¹ may be the same or different from each other, and each of R ⁵⁰ to R ⁷¹ 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,
Ar ³ 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,
X ¹³ is an oxygen atom or a sulfur atom,
Y ³¹ represents a nitrogen atom or

ego,
R ⁷² to R ⁷⁴ may be the same or different from each other, and each of R ⁷² to R ⁷⁴ 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 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 of claim 3,
Ar ⁴ 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,
X ¹⁴ is an oxygen atom or a sulfur atom,
Y ³² represents a nitrogen atom or

ego,
R ⁷⁵ to R ⁷⁷ may be the same or different from each other, and each of R ⁷⁵ to R ⁷⁷ 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 C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group. delete An organic electroluminescent device comprising the compound for organic electroluminescent device according to claim 1. 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 claim 1, wherein the at least one organic layer selected from the single or plural organic layers comprises the compound for organic electroluminescent devices according to claim 1. 8. The method of claim 7,
Wherein the single or plural organic layers include a light emitting layer. 8. The method of claim 7,
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. 9. The method of claim 8,
Wherein the light emitting layer comprises a host and a dopant.

Images