KR20140013351A - Novel compound for organic electroluminescent device and organic electroluminescent device comprising the same - Google Patents

Abstract

A compound for an organic electroluminescent device and an organic electroluminescent device comprising the same are disclosed. According to an embodiment of the present invention, the compound represented by structural formula 1 has outstanding electrical stability and electron- and hole-transporting ability. The compound for the organic electroluminescent device capable of improving a light-emitting efficiency of phosphorescent light-emitting materials by having a high-level of triplet state energy and the organic electroluminescent device comprising the same are provided.

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 a polymer chain to produce a multifunctional material. However, it is difficult to purify a compound or to form an element, and a low-molecular substance can synthesize a substance having various properties. However, There is a limit to the synthesis.

On the other hand, the organic electroluminescent devices 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 Thereby facilitating the formation of excitons and improving the luminous efficiency.

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

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

Organic metal compounds using a transition metal (iridium) have been developed as phosphorescent light emitting materials because organic phosphors are difficult to emit phosphorescence due to the nature of organic materials, and organic materials are used as host materials to assist them. The material that assists the phosphorescent material (host) should have a wide bandgap and a high triplet state energy. Although phosphorescent materials having excellent current efficiency and luminous efficiency are in the spotlight, there is no need to develop a host material having high electron transporting ability, hole transporting ability, thermal and electrical stability and especially high triplet state energy.

United States Published Patent Application US 2002-0045061

The present invention relates to a compound capable of being used in 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 electroluminescent device can be provided.

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

According to an aspect of the present invention, a compound for an organic light emitting device represented by Structural Formula 1 is provided.

[Structural formula 1]

In the above formula 1,

,

,

,

, 치환 또는 비치환된 C1 내지 C30의 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로 아릴기이거나, 또는 R¹ 및 R²는 중 어느 하나는 그 어느 하나가 결합된 탄소원자의 이웃한 탄소원자와 추가로 결합하여 치환 또는 비치환된 융합된 C6 내지 C30 아릴기 또는 치환 또는 비치환된 융합된 C1 내지 C30 헤테로 아릴기를 형성할 수 있고,R ¹ and R ² may be the same or different from each other, and R ¹ and R ² 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 C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or R ¹ and R < ² > is a fused C6 to C30 aryl group or a substituted or unsubstituted fused C1 to C30 hetero ring which is further substituted with a neighboring carbon atom of a carbon atom to which both are bonded, An aryl group,

Ar ¹ and Ar ² may be the same or different from each other, Ar ¹ and Ar ² are each independently a hydrogen atom, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,

R ⁷ to R ¹¹ may be the same or different from each other, and R ⁷ to R ¹¹ each independently represent 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 R ⁷ to R ¹¹ Either of which may be further fused with a neighboring carbon atom of the carbon atom to which it is attached to form a substituted or unsubstituted fused C6 to C30 aryl group or a substituted or unsubstituted fused C2 to C30 heteroaryl group However,

Y ¹ is an oxygen atom or a sulfur atom,

m is 0 or 1,

R ³ to R ⁶ may be the same or different from each other and each of R ³ to R ⁶ independently represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, Or a substituted or unsubstituted C1 to C30 heteroaryl group, or any one of R ³ to R ⁶ may be further substituted with a neighboring carbon atom of a carbon atom to which any of R ³ to R ⁶ is bonded to form a substituted or unsubstituted C 6 to C 30 aryl group, Or an unsubstituted fused C6 to C30 aryl group or a substituted or unsubstituted fused C1 to C30 heteroaryl group.

,

,

,

, 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로 아릴기이거나, 또는 R¹ 및 R²는 중 어느 하나는 그 어느 하나가 결합된 탄소원자의 이웃한 탄소원자와 추가로 결합하여 치환 또는 비치환된 융합된 C6 내지 C30 아릴기 또는 치환 또는 비치환된 융합된 C1 내지 C30 헤테로 아릴기를 형성할 수 있고,In the present invention, preferably, R ¹ and R ² may be the same or different from each other, and R ¹ and R ² are each independently

,

,

,

, A substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or any one of R ¹ and R ² is a carbon atom adjacent thereto, Which may be further joined to form a substituted or unsubstituted fused C6 to C30 aryl group or a substituted or unsubstituted fused C1 to C30 heteroaryl group,

Ar ¹ and Ar ² may be the same or different from each other, Ar ¹ and Ar ² are each independently a hydrogen atom, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,

R ⁷ to R ¹¹ may be the same or different from each other, and R ⁷ to R ¹¹ each independently represent 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 R ⁷ to R ¹¹ Either of which may be further fused with a neighboring carbon atom of the carbon atom to which it is attached to form a substituted or unsubstituted fused C6 to C30 aryl group or a substituted or unsubstituted fused C2 to C30 heteroaryl group However,

Y ¹ is an oxygen atom or a sulfur atom,

m may be 0 or 1.

In the present invention, the substituted or unsubstituted C6 to C30 aryl group is preferably 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 thienyl group, a substituted or unsubstituted anthracenyl 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, And may be an unsubstituted perylenyl group.

In the present invention, the substituted or unsubstituted C1 to C30 heteroaryl group is preferably a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, Substituted or unsubstituted thiophenyl groups, substituted or unsubstituted pyrrolyl groups, substituted or unsubstituted benzothiophenyl groups, substituted or unsubstituted indolyl groups, substituted or unsubstituted imidazo [1,2-a] pyridinyl groups, substituted A substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted benzothiazolyl group, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted tetrazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, A substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted thiazolyl group, 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 quinolinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted quinoxaline group, A substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted acridinyl group, or a substituted or unsubstituted phenanthrolinyl group.

In the present invention, the substituted or unsubstituted C1 to C30 heteroaryl group is preferably a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, Substituted or unsubstituted thiophenyl groups, substituted or unsubstituted pyrrolyl groups, substituted or unsubstituted benzothiophenyl groups, substituted or unsubstituted indolyl groups, substituted or unsubstituted imidazo [1,2-a] pyridinyl groups, substituted Or a substituted or unsubstituted benzothiazyl group, a substituted or unsubstituted benzothiazyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted benzothiazolyl group, Or an unsubstituted dibenzothiophenyl group.

According to another aspect of the present invention, R ¹ to R ⁶ in the structural formula 1 may be the same or different from each other, and R ¹ to R ⁶ are each independently a hydrogen atom or any one selected from the group consisting of the following U1 to U56: And m is 0 or 1.

According to another aspect of the present invention, there is provided a compound for an organic electroluminescence device, which is selected from the group consisting of compounds represented by the following formulas.

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

According to another aspect of the present invention, there is provided an organic electroluminescent device comprising a first electrode, a second electrode, and a single or a plurality of organic layers between a first electrode and a second electrode, An organic electroluminescent device characterized in that at least two kinds of organic material layers include the compound for an organic electroluminescent device according to the present invention can be provided.

In the present invention, the singular or plural organic layers may include a light emitting layer.

In the present invention, 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 the group consisting of an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transporting layer, have.

In the present invention, the light emitting layer may include a host and a dopant.

The present invention relates to a compound capable of being used in 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 electroluminescent device can be provided.

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

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 >

Singular expressions include plural expressions unless the context clearly indicates otherwise. In this application, the terms "comprise" or "having" are intended to indicate that there is a feature, number, step, operation, component, part, or combination thereof described in the specification, and one or more other features. It is to be understood that the present invention does not exclude the possibility of the presence or the addition of numbers, steps, operations, components, components, or a combination thereof.

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, 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, .

Hereinafter, the organic electroluminescent device of the present invention will be described.

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), SnO2 and ZnO which are metals can be cited. 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) Production Example 1 -1: Synthesis of intermediate 1-1

93.5 g (1.05 eq., 0.561 mol / Sigma Aldrich) of carbazole and 56.5 g (1.1 eq., 0.588 mol / acros) of NaOtBu were added to 100 g (1 eq., 0.535 mol / Sigma Aldrich) of 4-bromobenzene- _{Pd 2 (dba) 3 9.79g (} 0.02 eq, 0.0107mol / Pienza HI Tech), P (t-Bu) 3 4.33g (0.04 eq, 0.0214mol / Sigma Aldrich) and the reaction to insert the Toluene 1000ml stirred at 100 ℃ do. After completion of the reaction, distilled water was added thereto, and the mixture was extracted and purified by column (n-hexane: methylene chloride) to obtain 146.2 g of Intermediate 1-1 (4- (9H-carbazol-9-yl) benzene-1,2-diamine). (yiled 60%)

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

(1.05 equivalent, 0.461 mol / Sigma Aldrich) was added to 120 g (1 equivalent, 0.439 mol) of Intermediate 1-1 synthesized in Preparation Example 1-1 and stirred at 0 ° C for 1 hour. Then, 82 g (1.05 eq., 0.461 mol / acros) is added thereto, and the mixture is stirred at room temperature overnight. After completion of the reaction, the reaction mixture was neutralized by adding 10% NaOH and extracted with water to remove n-hexane (methylene chloride) to obtain intermediate 1-2 (9- (2- (4-bromophenyl) -1H-benzo [d] imidazol -5-yl) -9H-carbazole) (yield 50%).

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

(1.1 eq, 0.401 mol) of NaOtBu, 6.69 g (0.02 eq., 0.007 mol) of the catalyst Pd2 (dba) 3, 60.2 g (1.05 eq, 0.137 mol) of intermediate 1-2, 26 g 2.95 g (0.04 eq., 0.0146 mol) of P (t-Bu) 3 and 700 ml of Toluene are added and reacted at 100 ° C under reflux. After completion of the reaction, the reaction mixture was cooled, distilled water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 56.4 g of intermediate 1-3. (yiled 80%)

(4) Manufacturing example  1-4: Synthesis of Compound 1

94.1 g (1.1 eq., 0.320 mol) of 2-bromotriphenylene, 9.3 g (0.5 eq., 0.145 mol) of the catalyst Copper (II) and 24.81 g (1 eq) of base Potassium fluoride were added to 150 g 0.291 mol) were added to 2000 ml of DMSO, and the mixture was reacted at 130 ° C with stirring. After completion of the reaction, the reaction mixture was cooled, distilled water was added thereto, and the mixture was extracted and purified by column (n-hexane: methylene chloride)

_{HNMR (200MHz, CDCl 3):} δppm, 1H (7.50 / M, 7.70 / S, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D, 7.29 / M, 7.63 / D, 7.15 / D, 7.59 / D, 7.55 / D, 7.58 / M, 7.82 / M, 7.88 / M, 8.93 / D) 3H (8.12 / D)

[M-H] < + >: 660.79

Example  2: Synthesis of Compound 2

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

중간체 1-1 50g(1당량, 0.183mol)에 3-Bromobenzaldehyde 37.2g(1.1당량, 0.201mol/시그마알드리치)을 MC 800ml를 넣고 0℃에서 1시간 교반 후 NBS 84g(1.1당량, 0.201mol)을 투입한 후 상온에서 overnight교반하여 반응한다. 반응 종료 후 10%NaOH를 넣어 중화한 뒤 추출하여 수분 제거하여 칼럼 정제(n-Hexane : methylene chloride)하여 중간체 2-1을 36g수득하였다.(yield 45%)

(1.1 eq., 0.201 mol / Sigma Aldrich) was added to 50 g (1 eq., 0.183 mol) of Intermediate 1-1, and the mixture was stirred at 0 ° C for 1 hour. Then, 84 g (1.1 eq., 0.201 mol) of NBS After the addition, the mixture is reacted at room temperature overnight. After completion of the reaction, the reaction mixture was neutralized by adding 10% NaOH and extracted with water to remove 36 g of intermediate 2-1 (yield 45%) by column purification (n-hexane: methylene chloride)

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

(1.1 eq, 0.2 mol) of NaOtBu, 3.4 g (0.02 eq., 0.0035 mol) of the catalyst Pd2 (dba) 3, 30 g (1. eq, 0.068 mol) of Intermediate 2-1, 13 g 1.5 g (0.04 eq., 0.0078 mol) of P (t-Bu) 3 and 400 ml of Toluene are added and reacted at 100 ° C under reflux. After completion of the reaction, the reaction mixture was cooled, distilled water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 28 g of intermediate 2-2. (yiled 80%)

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

30 g (1 eq., 0.114 mol / Sigma Aldrich) of 4-bromodibenzothiopen was dissolved in 400 ml of purified THF and then cooled down to -78 ° C under nitrogen reflux. 8.8 g (1.2 eq, 0.137 mol) of n-BuLi was added dropwise thereto, Followed by stirring. After that, trimethyl borate (8.31 g, 0.08 mol / Sigma Aldrich) was added slowly at a low temperature, and then the temperature was raised, and the mixture was reacted at room temperature for 24 hours with stirring. Hydrochloric acid (10 M) was added (confirmed by litmus paper) and the reaction was terminated after neutralization. The mixture was extracted with dichloromethane and then recrystallized with hexane to obtain 11.7 g (yield: 45%) of intermediate 2-3

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

(1.2eq, 0.047mol) of Intermediate 2-3, 0.9g (2mol%, 0.00078mol) of Pd (pph) 4 as a catalyst, 10.8g (2eq, 0.078) in toluene (250 ml) and water (80 ml), and the mixture was stirred under reflux for 12 hours under a nitrogen atmosphere. After completion of the reaction, the reaction mixture was extracted with dichloromethane and purified by silica column (EA: hexane) to obtain 19.7 g (yield: 82%) of Compound 2.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.63 / D, 7.29 / M, 8.12 / D, 8.55 / D, 7.25 / M, 7.33 / M, 7.94 / D, 7.15 / D, 7.59 / D 7.50 / D, 7.50 / D, 7.50 / D, 7.44 / D, 8.24 / D, 7.57 / M, 7.48 / D, 7.98 / D, 7.52 / M, 8.45 / D, M), 3H (7.58 / M)

[M-H] < + >: 616.76

Example  3: Synthesis of Compound 3

1-phenylbenzoimidazole (4.9 g, 0.025 mol / Sigma Aldrich) was added to 200 ml of purified THF, and the mixture was stirred at room temperature for 2 hours with sodium hydride (0.70 g, 0.03 mol) added dropwise at 0 ° C. After the temperature was raised to room temperature, After completion of the reaction, the reaction mixture was extracted with water and dichloromethane, and purified by silica column (EA: hexane) to obtain 9.4 g of Compound 3. The resulting residue was purified by silica gel column chromatography (Yield: 60%).

(7.50 / M, 8.56 / D, 7.15 / D, 7.63 / D, 7.29 / M, 8.12 / D, 8.55 / D, 7.25 / M, 7.33 / M, 7.59 / D, 7.70 / S), 2H (7.45 / M, 7.59 / D, 7.22 /

[M-H] < + >: 626.73

Example  4: Synthesis of Compound 4

(2 mol%, 0.00078 mol) of Pd (pph) 4 as a catalyst, Na2CO3 10.0 g (0.07 mol) of dibenzothiopen-3yl-boronic acid (0.07 mol / g (2 eq, 0.078) In 400 ml of toluene and 80 ml of water, the mixture was stirred under reflux for 12 hours under a nitrogen atmosphere. After completion of the reaction, the reaction mixture was extracted with dichloromethane and purified by silica column (EA: hexane) to obtain 19 g (yield: 79%) of Compound 4

D, 7.29 / M, 8.12 / D, 8.55 / D, 7.25 / M, 7.33 / M, 7.94 / D, 7.15 / D, 7.59 / D, 7.50 / D, 7.58 / D, 7.50 / D, 7.50 / M, 8.08 / , 7.25 / D)

[M-H] < + >: 616.76

Example  5: Synthesis of Compound 5

(1.1 eq., 0.0228 mol / acros) of NaOtBu and 0.17 g (0.025 mmol) of catalyst Pd ₂ (dba) _{3 were added to the} intermediate 1-3 (10 g, 0.019 mol) (T-Bu) ₃ (0.077 g, 0.00038 mol / Sigma Aldrich) were added to 500 ml of toluene, and the mixture was stirred at 100 ° C for 6 hours. After completion of the reaction, distilled water was added thereto, and the mixture was extracted with MC. Column purification (n-hexane: methylene chloride) was conducted to obtain 11.9 g of Compound 5. (yiled 89%)

D, 7.25 / D, 8.12 / D, 7.29 / M, 7.63 / D, 7.15 / D, 7.59 / D, 7.45 / M, 6.81 / M, 6.86 / D, 7.27 / M, 7.81 / D, 7.98 / D, 7.52 / , 6.69 / D, 6.63 / D, 7.20 / M, 7.58 / M)

[M-H] < + >: 707.32

Example  6: Synthesis of Compound 6

Intermediate 1-3 (5g, 0.009mol) N- phenyl-1H-dipyrrolthiopen (2.38g, 0.01mol / China) and NaOtBu (1.2g, 0.0114mol), catalyst _{Pd 2 (dba) 3 (0.09g} , 0.00009mol in ) And P (t-Bu) ₃ (0.039 g, 0.00019 mol) were added to 200 ml of toluene, and the mixture was reacted for 12 hours at 100 ° C. After completion of the reaction, distilled water was added thereto and extracted with MC to obtain n-hexane To give 6.6 g of compound (yiled 75%).

(7.70 / S, 7.50 / M, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D, 8.12 / D, 7.29 / M, 7.63 / D, (7.50 / D, 7.59 / D), 2H (7.45 / M, 7.79 / D, 6.19 / D, 7.26 / D, 7.68 / D)

[M-H] < + >: 670.81

Example  7: Synthesis of Compound 7

(Biphenyl-4yl) -9,9-dimetylfluoren-2-amie (7.6 g, 0.021 mol / in China) and 2.25 g (1.1 eq., 0.0228 mol) of NaOtBu were added to Intermediate 1-3 (10 g, 0.019 mol) 300 ml of Toluene was added to 0.17 g (0.02 equivalent, 0.00019 mol) of Pd ₂ (dba) ₃ and 0.077 g (0.00038 mol) of P (t-Bu) ₃ and the mixture was stirred at 100 ° C. for 6 hours. After completion of the reaction, distilled water was added thereto, and the mixture was extracted with MC. Column purification (n-hexane: methylene chloride) was conducted to obtain 13.4 g of Compound 5. (yiled 89%)

M, 7.48 / M, 6.58 / D, 7.62 / D, 7.25 / M, 7.94 / D, 7.87 / D, 7.38 / M, 7.28 / M, 7.55 / D, 6.75 / S, 7.45 / M, 7.59 / D, 7.15 / D, 7.63 / D, 7.29 / M, 8.12 / D, 8.55 / D, 7.33 / M, 7.70 / , 7.90 / D, 7.51 / M, 7.52 / D, 7.54 / D, 7.58 / M, 1.72 / S)

[M-H] < + >: 793.98

Example  8: Synthesis of Compound 8

Bis (dibenzothiopen-4yl) amin (3.81 g, 0.01 mol / in China), NaOtBu (1.2 g, 0.0114 mol) and catalyst Pd ₂ (dba) ₃ (0.09 g, 0.00009 mol ) And P (t-Bu) ₃ (0.039 g, 0.00019 mol) were added to 200 ml of toluene, and the mixture was reacted for 8 hours at 100 ° C. After completion of the reaction, distilled water was added thereto and extracted with MC to obtain n-hexane To give 5 g of the compound (yiled 68%).

(7.98 / D, 7.98 / M, 7.59 / D, 7.15 / D, 7.63 / D, 7.29 / M, 8.12 / D, 8.55 / D, 7.25 / M, M, 7.94 / D, 7.70 / S, 7.45 / M), 2H (7.90 / D, 7.50 / M, 6.69 / D, 6.86 / D, 7.58 / , 8.45 / D), 3H (7.50 / D)

[M-H] < + >: 814.02

Example  9: Synthesis of Compound 9

(1) Production example 9-1: Synthesis of intermediate 9-1 Synthesis of

Intermediate 1-3 (20 g, 0.038 mol) was dissolved in 200 ml of purified THF, cooled to -78 ° C under nitrogen reflux, n-BuLi (2.7 g, 0.042 mol) was added dropwise and the mixture was stirred for 2 hours. After that, trimethyl borate (4.3 g, 0.042 mol / Sigma Aldrich) was slowly added at a low temperature, and the temperature was raised. The mixture was reacted at room temperature for 24 hours with stirring. Hydrochloric acid (10 M) was added (confirmed by litmus paper) and the reaction was terminated after neutralization. The mixture was extracted with dichloromethane and then recrystallized with hexane to obtain 7.65 g (yield: 43%) of intermediate 9-1

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

To a solution of Intermediate 9-1 (10 g, 0.021 mol) was added 2-bromo-N-phenyldibenzoindole (7.8 g, 0.021 mol / China), NaOtBu (2.64 g, 0.0252 mol), Catalyst Pd ₂ (dba) ₃ (0.172 g, 0.00019 mol ) And P (t-Bu) ₃ (0.08 g, 0.00042) in 200 ml of toluene, and the mixture is stirred at 100 ° C. for 4 hours. After completion of the reaction, distilled water was added, extracted with MC, and subjected to column purification (n-hexane: methylene chloride) to obtain 10.98 g of a compound. (yiled 72%)

M, 7.25 / M, 7.95 / D, 7.70 / S, 7.94 / D, 7.33 / M, 7.25 / M, D), 3H (8.12 / D), 4H (7.50 / D, 7.63 / D, 7.29 / M), 2H (7.82 / M, 7.88 / M, 8.93 / D, 8.30 / D, 7.45 / / D, 7.58 / M)

[M-H] < + >: 725.86

Example  10: Synthesis of Compound 10

2-bromo-N-phenylpyrolopenanthrolin (7.86 g, 0.021 mol / in China), NaOtBu (2.64 g, 0.0252 mol) and catalyst Pd ₂ (dba) ₃ (0.172 g, 0.00019 mol ) And P (t-Bu) ₃ (0.08 g, 0.00042) in 200 ml of toluene, and the mixture is stirred at 100 ° C. for 4 hours. After completion of the reaction, distilled water was added, and the mixture was extracted with MC, and column purification (n-hexane: methylene chloride) was conducted to obtain 10.55 g of a compound. (yiled 69%)

(7.50 / M, 7.59 / D, 7.15 / D, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D, 8.12 / D, 7.29 / M, D), 4H (7.50 / D), 6H (7.58 / M)), 2H (8.38 / D, 8.83 / D, 7.45 /

[M-H] < + >: 727.84

Example  11: Synthesis of Compound 11

To a solution of Intermediate 9-1 (10 g, 0.021 mol) was added brombenzene (D: Deuterium) (4.08 g, 0.0252 mol / Sigma Aldrich), NaOtBu (2.64 g, 0.0252 mol), Catalyst Pd ₂ (dba) ₃ (0.172 g, 0.00019 mol ) And P (t-Bu) ₃ (0.08 g, 0.00042) in 200 ml of toluene, and the mixture is stirred at 100 ° C. for 8 hours. After the completion of the reaction, distilled water was added, extracted with MC, and subjected to column purification (n-hexane: methylene chloride) to obtain 9.1 g of a compound. (yiled 84%)

D, 7.15 / D, 7.94 / D, 7.33 / M, 8.55 / D, 8.12 / D, 7.59 / M, 7.63 / D, 7.70 / S) 2H (7.25 / D, 7.85 / D, 7.50 / D, 7.58 /

[M-H] < + >: 515.65

Example  12: Synthesis of Compound 12

To a solution of Intermediate 9-1 (10 g, 0.021 mol) was added bromopyridophenanthrolin (7.8 g, 0.0252 mol), NaOtBu (2.64 g, 0.0252 mol), catalyst Pd ₂ (dba) ₃ (0.172 g, 0.00019 mol) ₃ (0.08 g, 0.00042) mol was added to 200 ml of toluene, and the mixture was stirred at 100 ° C for 8 hours. After completion of the reaction, distilled water was added thereto, and the mixture was extracted with MC. Column purification (n-hexane: methylene chloride) was conducted to obtain 12.4 g of a compound. (yiled 89%)

(7.50 / M, 7.25 / M, 7.29 / M, 7.63 / D, 7.15 / D, 7.59 / D, 7.70 / S, 8.57 / S, 8.22 / S, D, 8.38 / D, 7.50 / D, 7.85 / D, 7.25 / D), 4H (7.58 / M)

[M-H] < + >: 663.75

Example  13: Synthesis of Compound 25

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

800 ml of MC was added to benzaldehyde (21.3.2 g, 0.201 mol / Sigma Aldrich) in N-phenylcarbazole-1,2diamin (50g, 0.183mol / TCI) and stirred at 0 ° C for 1 hour. NBS 84g (1.1eq, 0.201mol) After the addition, the mixture is reacted at room temperature overnight. After completion of the reaction, the reaction mixture was neutralized by adding 10% NaOH and then extracted with water to remove 26.3 g (yield: 40%) of Intermediate 13-1 by column purification (n-Hexane: methylene chloride)

(One) Manufacturing example  13-2: Compound 26 Synthesis

Intermediate 13-1 (10g, 0.028mol) in 2 (4-bromopheny) N- phenylbenzoimidazole (7.6g, 0.021mol / Sigma-Aldrich) and NaOtBu (4.41g, 0.042mol), catalyst Pd ₂ (dba) ₃ (0.254g , 0.00028 mol) and P (t-Bu) ₃ (0.113 g, 0.00056 mol) were added to 300 ml of toluene and stirred at 100 ° C for 6 hours. After completion of the reaction, distilled water was added thereto, and the mixture was extracted with MC. Column purification (n-hexane: methylene chloride) was conducted to obtain 12.3 g of Compound 26. (yiled 70%)

(8.56 / D, 7.59 / D, 8.22 / D, 7.85 / D, 8.55 / D, 7.25 / M, 7.33 / M, 7.94 / D, 7.41 / M) M, 7.50 / D), 4H (7.58 / M, 7.50 / D)

[M-H] < + >: 626.73

Example  14: Synthesis of Compound 27

To a solution of Intermediate 13-1 (10 g, 0.028 mol) 3 (4-bromopheny) dibenzothiopen (7.12 g, 0.021 mol / Sigma Aldrich), NaOtBu (4.41 g, 0.042 mol), Catalyst Pd ₂ (dba) ₃ (0.254 g, 0.00028 (t-Bu) ₃ (0.113 g, 0.00056 mol) were added to 300 ml of toluene, and the mixture was stirred at 100 ° C for 6 hours. After completion of the reaction, distilled water was added, and the mixture was extracted with MC, and column purification (n-hexane: methylene chloride) was conducted to obtain 13 g of Compound 27. (yiled 81%)

M, 7.44 / D, 7.33 / M, 7.25 / M, 8.55 / D, 7.85 / D, 8.22 / D, 7.41 / M, (7.50 / D, 7.58 / M, 7.51 / M, 7.79 / D, 7.68 / D, 8.28 / D) 8.08 / S, 8.05 / D, 8.11 / D, 8.45 / D, 7.52 /

[M-H] < + >: 616.76

Example  15: Synthesis of Compound 28

Intermediate 13-1 (10 g, 0.028 mol), NaOtBu (4.41 g, 0.042 mol), and catalyst Pd ₂ (0.04 mol) were added to N, N (4-bromophenyl) (phenyl) (4- (dibenzothiopen) (dba) ₃ (0.254 g, 0.00028 mol) and P (t-Bu) ₃ (0.113 g, 0.00056 mol) were added to 300 ml of toluene and the mixture was reacted for 6 hours at 100 ° C. After completion of the reaction, (N-hexane: methylene chloride) to obtain 12.05 g of Compound 28 (yiled 81%).

(7.50 / M, 7.27 / M, 6.86 / D, 6.81 / M, 7.98 / D, 7.52 / M, 8.45 / D, 7.81 / D, 7.41 / M, M, 7.37 / D, 7.51 / M, 8.28 / D, 7.58 / M, 7.32 / D, 7.85 / D, 8.55 / D, 7.25 / , 7.50 / D), 4H (6.63 / D)

[M-H] < + >: 707.87

Example  16: Synthesis of compound 29

Intermediate 13-1 (10 g, 0.028 mol), NaOtBu (4.41 g, 0.042 mol), and catalyst Pd ₂ (dba) ₃ (0.254 g, 0.042 mol) were added to 2- (4-bromophenyl) tripenylene (9.58 g, 0.025 mol / Sigma Aldrich) 0.00028 mol) and P (t-Bu) ₃ (0.113 g, 0.00056 mol) were added to 300 ml of toluene, followed by stirring at 100 ° C for 6 hours. After completion of the reaction, distilled water was added thereto, and the mixture was extracted with MC, and column purification (n-hexane: methylene chloride) was carried out to obtain 11.59 g of Compound 29. (yiled 70%)

M, 7.45 / M, 87.85 / D, 8.55 / D, 7.25 / M, 7.33 / M, 8.08 / D, 8.04 / D, 7.94 / M) 2H (8.12 / D, 8.93 / D, 8.28 / D, 7.82 / M, 7.88 / M, 7.51 / M, 7.50 / D, 7.68 / D, 7.58 /

[M-H] < + >: 660.79

Example  17: Synthesis of compound 30

Intermediate 13-1 (10g, 0.028mol), NaOtBu (4.41g, 0.042mol), catalyst Pd ₂ (dba (0.028mol)) were added to N- (4-bromophenyl) N-phenyl-dipyrolothiopen (9.83g, 0.025mol / ) ₃ (0.254 g, 0.00028 mol) and P (t-Bu) ₃ (0.113 g, 0.00056 mol) were added to 300 ml of toluene and stirred at 100 ° C for 6 hours. After completion of the reaction, distilled water was added thereto, and the mixture was extracted with MC. Column purification (n-hexane: methylene chloride) was conducted to obtain 15.45 g of Compound 30. (yiled 92%)

(7.26 / D, 6.19 (1H, d, J = 7.6 Hz). 1H NMR (200MHz, CDCl3)? Ppm, 1H (7.41 / M, 8.22 / D, 7.85 / D, 8.55 / D, 7.25 / D, 7.45 / M, 8.28 / D, 7.51 / M) 4H (7.50 / D, 7.62 / D, 7.58 /

[M-H] < + >: 670.81

Example  18: Synthesis of Compound 31

Intermediate 13-1 (10 g, 0.028 mol) and NaOtBu (4.41 g, 0.042 mol) were added to N- (4-bromophenyl) N- (biphenyl-4yl) 9,9methylfluoren-2amine (10.8 g, 0.021 mol / ), catalytic _{Pd 2 (dba) 3 (0.254g} , 0.00028mol), P (t-Bu) 3 (0.113g, 0.00056mol) into a 300ml Toluene the reaction mixture was stirred at 100 ℃ 8 hours. After the completion of the reaction, distilled water was added thereto, and the mixture was extracted with MC. Column purification (n-hexane: methylene chloride) was conducted to obtain 14.5 g of Compound 31. (yiled 87%)

7.85 / D, 7.38 / M, 7.28 / M, 7.55 / D, 6.75 / S, 8.22 / D, 7.85 / D, D, 7.54 / D, 6.69 / D, 6.63 / D, 7.58 / M, 7.37 / D, 8.28 / D , 7.41 / M, 7.50 / D, 1.72 / S), 4H (7.51 / M)

[M-H] < + >: 793.98

Example  19: Synthesis of Compound 32

N-(4-bromophenyl)N-bis(dibenzothiopen-4yl)amin (11.3g, 0.021mol/시안(중국))에 중간체 13-1(10g, 0.028mol)과 NaOtBu (4.41g, 0.042mol), 촉매 Pd₂(dba)₃ (0.254g, 0.00028mol), P(t-Bu)₃ (0.113g, 0.00056mol)을 Toluene 300ml를 넣고 100℃에서 교반하여 12시간 반응한다. 반응 종료 후 증류수를 넣고 MC로 추출하여 칼럼 정제(n-Hexane: methylene chloride)하여 화합물 32을 11.46g을 수득하였다. (yiled 67%)

Intermediate 13-1 (10g, 0.028mol), NaOtBu (4.41g, 0.042mol), and catalyst 13-1 (10g, 0.028mol) were added to N- (4-bromophenyl) N-bis (dibenzothiopen- 300 ml of Toluene were added to Pd ₂ (dba) ₃ (0.254 g, 0.00028 mol) and P (t-Bu) ₃ (0.113 g, 0.00056 mol) and stirred at 100 ° C. for 12 hours. After completion of the reaction, distilled water was added thereto, and the mixture was extracted with MC, followed by column purification (n-hexane: methylene chloride) to obtain 11.46 g of Compound 32. (yiled 67%)

(7.51 / D, 7.51 / M, 7.98 / M, 7.98 / D, 7.41 / M, 8.22 / D, 7.85 / D, 7.45 / M, 7.94 / D, M, 7.25 / M, 8.55 / D), 2H (7.50 / D, 7.50 / M, 7.58 / M, 6.86 / D, 7.81 / D, 8.45 / D, 7.52 / , 7.37 / D, 8.28 / D)

[M-H] < + >: 814.02

The abbreviations used in the test examples 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

Test Example 1

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. Ir (ppy) ₃ was doped so that the deposition rate ratio became 9%, thereby forming a light emitting layer having a thickness of 30 nm on the hole transport layer. Balq was deposited thereon to a thickness of 10 nm to form a hole blocking layer for preventing holes from moving to the electron transporting layer through the light emitting layer, and Alq ₃ was deposited thereon to form an electron transporting layer of 40 nm, and lithium fluoride Thereby forming an electron injection layer having a thickness of 1 nm. Aluminum was deposited on the electron injecting layer to form a 120 nm cathode, thereby fabricating an organic electroluminescent device.

Compound 1, NPB, Alq ₃ , and Balq were deposited at a rate of 0.1 nm / sec. The deposition rate of each material was 0.01 nm / second for lithium fluoride and 0.5 nm / second for aluminum.

Test Example  2

An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound 2 was used instead of Compound 1.

Test Example  3

An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound 3 was used instead of Compound 1.

Test Example  4

An organic electroluminescent device was fabricated in the same manner as in Example 1 except that Compound 4 was used instead of Compound 1.

Test Example  5

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 5 was used instead of Compound 1.

Test Example  6

An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound 6 was used instead of Compound 1.

Test Example  7

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 7 was used instead of Compound 1.

Test Example  8

An organic electroluminescent device was produced in the same manner as in Example 1, except that Compound 8 was used instead of Compound 1.

Test Example  9

An organic electroluminescent device was fabricated in the same manner as in Example 1, except that Compound 9 was used instead of Compound 1.

Test Example  10

An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound 10 was used instead of Compound 1.

Test Example  11

An organic electroluminescent device was fabricated in the same manner as in Example 1, except that Compound 11 was used instead of Compound 1.

Test Example  12

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 12 was used instead of Compound 1.

Test Example  13

An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound 26 was used instead of Compound 1.

Test Example  14

An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound 27 was used instead of Compound 1.

Test Example  15

An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound 28 was used instead of Compound 1.

Test Example  16

An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound 29 was used instead of Compound 1.

Test Example  17

An organic electroluminescent device was fabricated in the same manner as in Example 1, except that Compound 30 was used instead of Compound 1.

Test Example  18

An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound 31 was used instead of Compound 1.

Test Example  19

An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound 32 was used instead of Compound 1.

Comparative test example  One

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

Table 1 below shows the results of comparing the characteristics of the organic electroluminescent device manufactured according to the test examples and the comparative test examples.

Host substance The driving voltage (V)
(at 1000cd / m2) Luminous efficiency
(cd / A) Color coordinates CIE
(x, y) Test Example 1 Compound 1 4.5 45 0.30, 0.60 Test Example 2 Compound 2 4.2 35 0.34, 0.65 Test Example 3 Compound 3 5 41 0.33, 0.64 Test Example 4 Compound 4 5.5 40 0.33, 0.63 Test Example 5 Compound 5 5.1 40 0.33, 0.64 Test Example 6 Compound 6 4.7 47 0.31, 0.61 Test Example 7 Compound 7 5.1 32 0.32, 0.59 Test Example 8 Compound 8 4.7 30 0.29, 0.60 Test Example 9 Compound 9 4 28 0.31, 0.59 Test Example 10 Compound 10 5.3 40 0.29, 0.58 Test Example 11 Compound 11 5 44 0.30, 0.64 Test Example 12 Compound 12 5.0 46 0.33, 0.64 Test Example 13 Compound 26 4.5 48 0.33, 0.63 Test Example 14 Compound 27 4.7 50 0.30, 0.59 Test Example 15 Compound 28 4.1 35 0.29, 0.63 Test Example 16 Compound 29 4.3 37 0.30, 0.63 Test Example 17 Compound 30 4.4 35 0.33, 0.63 Test Example 18 Compound 31 5.5 38 0.32, 0.60 Test Example 19 Compound 32 5.7 48 0.33, 0.65 Comparative Test Example 1 CBP 6.5 19 0.33, 0.63

How to measure driving voltage

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

Referring to Table 1, 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, the driving voltage is considerably lowered and the luminescent efficiency is considerably lower than that of a conventional host material (CBP) It shows excellent.

Claims (12)

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

In the above formula 1,
R ¹ and R ² may be the same or different from each other, and R ¹ and R ² 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 C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or R ¹ and R < ² > is a fused C6 to C30 aryl group or a substituted or unsubstituted fused C1 to C30 hetero ring which is further substituted with a neighboring carbon atom of a carbon atom to which both are bonded, An aryl group,
Ar ¹ and Ar ² may be the same or different from each other, Ar ¹ and Ar ² are each independently a hydrogen atom, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
R ⁷ to R ¹¹ may be the same or different from each other, and R ⁷ to R ¹¹ each independently represent 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 R ⁷ to R ¹¹ Either of which may be further fused with a neighboring carbon atom of the carbon atom to which it is attached to form a substituted or unsubstituted fused C6 to C30 aryl group or a substituted or unsubstituted fused C2 to C30 heteroaryl group However,
Y ¹ is an oxygen atom or a sulfur atom,
m is 0 or 1,
R ³ to R ⁶ may be the same or different from each other and each of R ³ to R ⁶ independently represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, Or a substituted or unsubstituted C1 to C30 heteroaryl group, or any one of R ³ to R ⁶ may be further substituted with a neighboring carbon atom of a carbon atom to which any of R ³ to R ⁶ is bonded to form a substituted or unsubstituted C 6 to C 30 aryl group, Or an unsubstituted fused C6 to C30 aryl group or a substituted or unsubstituted fused C1 to C30 heteroaryl group. The method of claim 1,
R ¹ and R ² may be the same as or different from each other, and R ¹ and R ² are each independently

,

,

,

, A substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or any one of R ¹ and R ² is a carbon atom adjacent thereto, Which may be further joined to form a substituted or unsubstituted fused C6 to C30 aryl group or a substituted or unsubstituted fused C1 to C30 heteroaryl group,
Ar ¹ and Ar ² may be the same or different from each other, Ar ¹ and Ar ² are each independently a hydrogen atom, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
R ⁷ to R ¹¹ may be the same or different from each other, and R ⁷ to R ¹¹ each independently represent 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 R ⁷ to R ¹¹ Either of which may be further fused with a neighboring carbon atom of the carbon atom to which it is attached to form a substituted or unsubstituted fused C6 to C30 aryl group or a substituted or unsubstituted fused C2 to C30 heteroaryl group However,
Y ¹ is an oxygen atom or a sulfur atom,
m is 0 or 1 compound for an organic light emitting device. 3. The method of claim 2,
The substituted or unsubstituted C6 to C30 aryl group is substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthalenyl group, substituted or unsubstituted anthracenyl Group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted pyrenyl group, or a substituted or unsubstituted perenyl group Compound for an organic light emitting device, characterized in that. 3. The method of claim 2,
The substituted or unsubstituted C1 to C30 heteroaryl group is substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted thiophenyl group, substituted or Unsubstituted pyrrolyl group, substituted or unsubstituted benzothiophenyl group, substituted or unsubstituted indolyl group, substituted or unsubstituted imidazo [1,2-a] pyridinyl group, substituted or unsubstituted benziimida Zolyl group, substituted or unsubstituted indazolyl group, substituted or unsubstituted phenothiazinyl group, substituted or unsubstituted phenazinyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted dibenzothiophenyl group , Substituted or unsubstituted imidazolyl group, substituted or unsubstituted triazolyl group, substituted or unsubstituted tetrazolyl group, substituted or unsubstituted oxadiazolyl group, substituted or unsubstituted oxatriazolyl group, substituted Is an unsubstituted thiatriazolyl group, a substituted or unsubstituted benzotriazolyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted purinyl group, a substituted or unsubstituted Substituted quinolinyl groups, substituted or unsubstituted isoquinolinyl groups, substituted or unsubstituted phthalazinyl groups, substituted or unsubstituted naphpyridinyl groups, substituted or unsubstituted quinoxalinyl groups, substituted or unsubstituted A compound for an organic light emitting device, characterized in that it is a quinazolinyl group, a substituted or unsubstituted acridinyl group, or a substituted or unsubstituted phenanthrolinyl group. 5. The method of claim 4,
The substituted or unsubstituted C1 to C30 heteroaryl group is substituted or unsubstituted
Pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted thiophenyl group, substituted or unsubstituted pyrrolyl group, substituted or unsubstituted benzothiophenyl group, substituted Or unsubstituted indolyl group, substituted or unsubstituted imidazo [1,2-a] pyridinyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted indazolyl group, substituted or unsubstituted A phenothiazinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted dibenzothiophenyl group. A compound for an organic electroluminescence device represented by Structural Formula (1) below.
[Structural formula 1]

In Structural Formula 1
R ¹ to R ⁶ may be the same as or different from each other and R ¹ to R ⁶ may each independently be a hydrogen atom or any one selected from the group consisting of U1 to U56,
m is 0 or 1;

Compound for an organic light emitting device, which is any one selected from compounds represented by the following formula.

An organic electroluminescent device comprising the compound for an organic electroluminescent device according to any one of claims 1 to 7. A first electrode, a second electrode, and a single or a plurality of organic layers between the first electrode and the second electrode, the organic electroluminescent device comprising:
Wherein at least one organic compound layer selected from the single or plural organic compound layers comprises the compound for organic electroluminescence device according to any one of claims 1 to 7. 10. The method of claim 9,
Wherein the single or plural organic layers include a light emitting layer. 10. The method of claim 9,
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. 11. The method of claim 10,
Wherein the light emitting layer comprises a host and a dopant.

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