WO2013183851A1

WO2013183851A1 - Novel organic electroluminescent element compound and organic electroluminescent element comprising same

Info

Publication number: WO2013183851A1
Application number: PCT/KR2013/002321
Authority: WO
Inventors: 현서용; 윤용호; 송정한
Original assignee: (주)피엔에이치테크
Priority date: 2012-06-04
Filing date: 2013-03-21
Publication date: 2013-12-12

Abstract

Disclosed are: an organic electroluminescent element compound represented by structural formula 1 or 2 below; and an organic electroluminescent element comprising same. In this way, it is possible to provide an organic electroluminescent element compound which can be used as a host, hole-transport material and electron-transport material that has outstanding electrical stability and electron- and hole-transporting ability, a high level of triplet state energy and is able to improve the light-emitting efficiency of phosphorescent light-emitting materials, and an organic electroluminescent element.

Description

New compound for organic electroluminescent device and organic electroluminescent device comprising same

The present invention relates to a compound for an organic light emitting device and an organic light emitting device comprising the same, and more particularly, a compound for an organic light emitting device that can improve the luminous efficiency of the organic light emitting device and an organic light emitting device comprising the same. It relates to an element.

As the movement to the information society accelerates, the proportion of flat panel displays is gradually increasing. Among them, liquid crystal display (LCD) is the most widely used, but it is a method of making a screen by applying voltage to the liquid crystal and passing the light from the backlight through a color filter to obtain three primary colors, and organic light emitting diodes (OLED) As a self-luminous device, it has excellent viewing angle, contrast ratio, etc., is light and thin, and can be used for flexible substrates, so that it is possible to be transparent and flexible display, attracting attention as a next generation display device.

Organic EL is a phenomenon in which electrons and holes injected through an anode and an anode into an organic thin film are recombined to form excitons, and light of a specific wavelength is generated from the formed excitons from a single crystal of anthracene by Pope et al. In 1963. It has been discovered for the first time and has been actively studied since it was reported by CW Tang et al. (CW Tang, SA Vanslyke, Applied physics Letters. 51, 913p, 1987).

Organic materials used in organic electroluminescent devices are largely divided into high molecular and low molecular forms, and low molecules may be divided into pure organic materials and metal complexes forming metals and chelates.

High molecular materials can produce multifunctional materials by combining various functional units with polymer chains, but there are difficulties in refining composites and forming devices, and low molecular materials can synthesize materials of different characteristics, There is a limit to the material synthesis.

The organic light emitting diode can be formed in a stacked structure. The advantage of the laminated structure is that the material can be selected and used according to each function. In general, the device structure forms a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer between an anode and a cathode, thereby emitting a light emitting layer. The exciton can be easily formed and the luminous efficiency can be increased.

Luminescent materials can be broadly divided into host materials and luminescent materials (dopant) materials, and luminescent materials are classified into fluorescence and phosphorescence according to the emission mechanism.

The excited state of the former in the compound is 1: 3 with singlet to triplet ratios and three times more triplet states. Therefore, the internal quantum efficiency of fluorescence falling from the singlet state to the ground state is only 25%, while the internal quantum efficiency of phosphorescence falling from the triplet state to the ground state is 75%. In addition, the theoretical limit of the internal quantum efficiency reaches 100% in the case of a quarterly transition from singlet to triplet. Phosphorescent light emitting material is a light emitting material that improved the luminous efficiency by using this point.

Due to the nature of organic materials, phosphorescence emission is difficult, and as a phosphorescent light emitting material, an organic metal compound using a transition metal (iridium) has been developed, and an organic material is used as a host material to assist this. Substances (hosts) that assist in phosphorescent materials should have a wide bandgap and a high energy in the middle phase. Phosphors with excellent current and luminous efficiencies are in the spotlight, but development is urgent as there is no host material with high electron transport capacity, hole transport capacity, thermal and electrical safety, and especially high triplet energy.

The present invention has excellent electrical stability and electron and hole transport ability, and the triplet state energy is high, the compound for an organic light emitting device that can be used in the light emitting layer as a host that can improve the luminous efficiency of the phosphorescent material and an organic electric field comprising the same A light emitting device can be provided.

In addition, the present invention can provide an electron transport material or an organic light emitting device compound that can be used in the hole transport material and an organic electroluminescent device comprising the same.

However, the problem to be solved by the present application is not limited to the above-mentioned problem, and other problems not mentioned will 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 light emitting device represented by the following Structural Formula 1 or 2 may be provided.

In the above formula 1 or 2,

R ⁴ to R ⁶ may be the same as or different from each other, R ⁴ to R ⁶ are each independently a hydrogen atom,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

, Substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C1 to C30 heteroaryl group, substituted or unsubstituted C3 to C30 cycloalkyl group, or substituted or unsubstituted Or a C 1 to C 30 heterocycloalkyl group, or at least any one of R ⁴ to R ⁶ is a fused C 3 to C 30 cycloalkyl group further bonded with a neighboring carbon atom of the carbon atom to which one is bonded, A substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused C1 to C30 hetero aryl group,

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

ego,

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

, or

ego,

R ⁸ to R ⁷⁰ may be the same as or different from each other, R ⁸ to R ⁷⁰ are each independently a hydrogen atom,

,

,

,

, Substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C1 to C30 heterocycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted Or a C1 to C30 heteroaryl group, or at least one of R ⁸ to R ⁷⁰ is a fused C3 to C30 cycloalkyl group which is further substituted with an adjacent carbon atom of the carbon atom to which one is bonded, or substituted or unsubstituted, 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 hetero aryl group,

Ar ³ to Ar ⁷ may be the same as or different from each other, Ar ³ to Ar ⁷ are each independently

,

,

,

, Substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C1 to C30 heterocycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C1 to C30 heteroaryl group,

Ar ¹ and Ar ² may be the same as or different from each other, and Ar ¹ and Ar ² are each independently

,

,

,

, Substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C1 to C30 heterocycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted Or a C1 to C30 heteroaryl group, or Ar ¹ and Ar ² are bonded to each other and form a substituted or unsubstituted C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, together with a nitrogen atom therebetween. Can do it,

X ³⁸ to X ⁴⁰ may be the same or different from each other, X ³⁸ to X ⁴⁰ are each independently a nitrogen atom, or

ego,

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

, or

ego,

R ⁷¹ to R ¹¹⁶ may be the same as or different from each other, R ⁷¹ to R ¹¹⁶ may be independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to A C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,

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

R ¹ to R ³ , and R ⁷ may be the same or different from each other, R ¹ to R ³ , and R ⁷ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to A C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or R ¹ to R ³ , and R At least one of ⁷ is a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, further bonded to a neighboring carbon atom of the carbon atom to which one is bonded, Substituted or unsubstituted fused C6 to C30 aryl groups, or substituted or unsubstituted fused C1 to C30 heteroaryl groups.

Examples of the substituted or unsubstituted C6 to C30 aryl group include 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, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted spirofluorenyl group, substituted or unsubstituted pyrenyl group, or substituted or unsubstituted phenyl It may be a rillenyl group.

Examples of the substituted or unsubstituted C2 to C30 heteroaryl group include 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 phenothiazinyl group, substituted or unsubstituted phenazinyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted dibenzo Thiophenyl 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 Flag, Cyclic or unsubstituted thiatriazolyl group, substituted or unsubstituted benzotriazolyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted pyridazinyl group, substituted or unsubstituted purinyl group, substituted or Unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted phthalazinyl group, substituted or unsubstituted naphpyridinyl group, substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted Quinazolinyl group, substituted or unsubstituted acridinyl group, or substituted or unsubstituted phenanthrolinyl group, preferably 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 already Polyzo [1,2-a] pyridinyl groups, substituted or unsubstituted benzimidazolyl groups, substituted or unsubstituted indazolyl groups, substituted or unsubstituted phenothiazinyl groups, substituted or unsubstituted phenazinyl groups , A substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted dibenzothiophenyl group.

The organic light emitting device compound may be a compound for an organic light emitting device, characterized in that any one selected from compounds 1 to 92 represented by the following structural formula.

According to another aspect of the invention, an organic electroluminescent device comprising the compound for an organic electroluminescent device may be provided.

According to another aspect of the present invention, in the organic light emitting device comprising a single electrode or a plurality of organic material layer between the first electrode, the second electrode and the first electrode and the second electrode, 1 selected from the single or plurality of organic material layer At least one organic material layer may include the compound for an organic light emitting device.

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

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

The emission layer may include a host and a dopant.

The present invention is excellent in electrical stability and electron and hole transport ability, high triplet energy, host, hole injection material, hole transport material, electron transport material, electron injection material and the like which can improve the luminous efficiency of phosphorescent material A compound for an organic light emitting device that can be used as a sealing material having excellent refractive index in a top emission method, and an organic light emitting device including the same can be provided.

1 is a cross-sectional view showing a cross section of an organic light emitting display device according to an embodiment of the present invention.

2 is a cross-sectional view showing a cross section of an organic light emitting display device according to another embodiment of the present invention.

As the invention allows for various changes and numerous embodiments, particular embodiments will be illustrated and described in detail in the detailed description. However, this is not intended to limit the present invention to specific embodiments, it should be understood to include all transformations, equivalents, and substitutes included in the spirit and scope of the present invention. In the following description of the present invention, if it is determined that the detailed description of the related known technology may obscure the gist of the present invention, the detailed description thereof will be omitted.

In addition, terms including ordinal numbers such as first and second to be used below may be used to describe various components, but the components 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 the second component, and similarly, the second component may also be referred to as the first component.

In addition, when a component is referred to as being "formed" or "laminated" on another component, it may be directly attached to, or laminated to, the front or one side on the surface of the other component, It will be understood that other components may exist in the.

Singular expressions include plural expressions unless the context clearly indicates otherwise. In this application, the terms "comprise" or "have" 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 disclosure does not exclude the possibility of the presence or the addition of numbers, steps, operations, components, components, or combinations thereof.

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

As used herein, unless otherwise defined, “substituted” means that at least one hydrogen in a substituent or compound is 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, a C1 to C30 Alkyl group, C1 to C30 alkylsilyl group, C3 to C30 cycloalkyl group, C1 to C30 heterocycloalkyl group, C6 to C30 aryl group, C1 to C30 heteroaryl group, C1 to C20 alkoxy group, C1 to C10 trifluoroalkyl group or cyan It means what is substituted by a nog.

In addition, the substituted halogen group, hydroxy group, amino group, C1 to C30 amine group, C3 to C30 silyl group, C1 to C30 alkyl group, C1 to C30 alkylsilyl group, C3 to C30 cycloalkyl group, C6 to C30 aryl group, C1 to C20 Two adjacent substituents among the alkoxy group, C1 to C10 trifluoroalkyl group or cyano group may be fused to form a ring.

As used herein, "hetero" means one to four heteroatoms selected from the group consisting of N, O, S, and P in one functional group, and the remainder is carbon unless otherwise defined.

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

In the present specification, "hydrogen" means monotium, dihydrogen, or tritium unless otherwise defined.

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

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

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

"Alkenylene group" means a functional group consisting of at least two carbon atoms of at least one carbon-carbon double bond, and "alkynylene group" means at least two carbon atoms of at least one carbon-carbon triplet. It means a functional group consisting of a bond. The alkyl group, whether saturated or unsaturated, may 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, a C1 to C4 alkyl group has 1 to 4 carbon atoms in the alkyl chain, i.e., the alkyl chain is methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and t-butyl Selected from the group consisting of:

For example, the alkyl group is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, hexyl, ethenyl, propenyl, butenyl, cyclopropyl, cyclo A butyl group, a cyclopentyl group, a cyclohexyl group, etc. are meant.

"Amine group" includes an arylamine group, an alkylamine group, an arylalkylamine group, or an alkylarylamine group.

A "cycloalkyl group" includes monocyclic or fused polycyclic (ie, rings that divide adjacent pairs of carbon atoms) functional groups.

"Heterocycloalkyl group" means containing 1 to 4 heteroatoms selected from the group consisting of N, O, S and P in the cycloalkyl group, and the rest are carbon. When the heterocycloalkyl group is a fused ring, each ring may include 1 to 4 heteroatoms.

"Aromatic group" means a functional group in which all elements of the functional group in the ring form have p-orbitals, and these p-orbitals form conjugation. Specific examples include an aryl group and a heteroaryl group.

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

"Heteroaryl group" means containing 1 to 4 heteroatoms selected from the group consisting of N, O, S and P in the aryl group, the rest being carbon. When the heteroaryl group is a fused ring, each ring may include 1 to 4 heteroatoms.

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

When used in combination with an "alkylaryl group" or an "arylalkyl group", the terms of each of the above alkyl and aryl have the meanings and content 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 an aryl group.

Hereinafter, embodiments of the present invention will be described with reference to the accompanying drawings, and in the following description with reference to the accompanying drawings, the same or corresponding components will be given the same reference numerals and redundant description thereof will be omitted. .

1 and 2, according to an embodiment of the present invention, an organic light emitting display device 1 including the compound for an organic light emitting display device according to the present invention may be provided.

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

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

In addition, the organic layer 130 includes a light emitting layer 134, and the organic layer includes an electron injection layer 131, an electron transport layer 132, a hole blocking layer 133, an electron blocking layer 135, a hole At least one selected from the transport layer 136 and the hole injection layer 137 may be further included.

The emission 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. For example, glass, a transparent plastic film, etc. can be used.

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

As the negative electrode 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 can be used. Specifically, Na, Na-K alloy, calcium, magnesium, lithium, lithium alloy, indium, aluminum, magnesium alloy, aluminum alloy is 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 hundred Ω / mm or less. The thickness of the electrode is 10 nm to 1 m, more preferably 10 to 400 nm. Such an electrode may be manufactured by forming the above electrode material into a thin film through vapor deposition or sputtering such as chemical vapor deposition (CVD), physical vapor deposition (PVD), or the like.

In addition, when the compound for an organic electroluminescent device of the present invention is used to suit the purpose of the present invention, a known hole transport material, a hole injection material, a light emitting layer material, a host material of the light emitting layer, an electron transport material, and an electron injection material, respectively, It may be used alone or in combination with the compound for an organic electroluminescent device of the present invention.

N, N-dicarbazolyl-3,5-benzene (mCP), poly (3,4-ethylenedioxythiophene): polystyrenesulfonate (PEDOT: PSS), N, N'-di (1-naphthyl) -N, N '-diphenylbenzidine (NPD), N, N'-diphenyl-N, N'-di (3-methylphenyl) -4,4'-diaminobiphenyl (TPD), N, N'-diphenyl-N, N'-Dinaphthyl-4,4'-diaminobiphenyl, N, N, N'N'-tetra-p-tolyl-4,4'-diaminobiphenyl, N, N, N'N ' Porphyrin compound derivatives such as tetraphenyl-4,4'-diaminobiphenyl, copper (II) 1,10,15,20-tetraphenyl-21H, 23H-porphyrin, aromatic tertiary in the main chain or side chain Polymer with amine, 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane, N, N, N-tri (p-tolyl) amine, 4, 4 ', 4'-tris [N- Triarylamine derivatives such as (3-methylphenyl) -N-phenylamino] triphenylamine, carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, phthalocyanine derivatives such as metal-free phthalocyanine, copper phthalocyanine, stabus And triamine derivatives, enamine steelbene derivatives, derivatives of aromatic tertiary amines and styryl amine compounds, and polysilanes.

As the electron transporting substance, diphenylphosphine oxide-4- (triphenylsilyl) phenyl (TSPO1), Alq ₃ , 2,5-diaryl silol derivative (PyPySPyPy), perfluorinated compound (PF-6P), Octasubstituted cyclooctatetraene compound (COTs) Can be mentioned.

In the organic electroluminescent device of the present invention, the electron injection layer, the electron transport layer, the hole transport layer and the hole injection layer may be formed of a single layer containing one or more kinds of the above-mentioned compounds, or may be stacked with different kinds of compounds. It may consist of a plurality of layers to contain.

Examples of the light emitting material include photoluminescent fluorescent materials, fluorescent brighteners, laser dyes, organic scintillators, and reagents for fluorescence analysis. Specifically, carbazole compounds, phosphine oxide compounds, carbazole phosphine oxide compounds, 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 quiterphenyl, 1,4-bis (2-methyl Styryl) benzene, 1,4-bis (4-methylstyryl) benzene, 1,4-bis (4-methyl-5-phenyl-2-oxazolyl) benzene, 1,4-bis (5-phenyl- 2-oxazolyl) benzene, 2,5-bis (5-t-butyl-2-benzoxazolyl) thiophene, 1,4-diphenyl-1,3-butadiene, 1,6-diphenyl-1, Scintillators for liquid scintillation such as 3,5-hexatriene, 1,1,4,4-tetraphenyl-1,3-butadiene, metal complexes of auxin derivatives, coumarin pigments, dicyano methylene pyran pigments and dicyano methylene Thiopyran pigment, polymethine pigment, oxobenzanthracene Dyes, xanthene dyes, carbostyryl dyes, perylene dyes, oxazine compounds, stilbene derivatives, spiro compounds, oxadiazole compounds and the like.

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 produced using a material used in each layer. There is no particular limitation on the film thickness of each layer, and it can be appropriately selected depending on the properties of the material, but can usually be determined in the range of 2 nm to 5,000 nm.

Since the compound for an organic light emitting device according to the present invention can be formed by a vacuum deposition method, there is an advantage that the thin film forming process is simple and can be easily obtained as a homogeneous thin film with little pin hole.

EXAMPLE

Hereinafter, the compound for an organic light emitting diode and the method for manufacturing the organic light emitting diode including the same according to the present invention will be described in more detail with reference to Examples. However, this is for illustrative purposes and the scope of the present invention is not limited thereby.

Example 1 Compound 1 Synthesis

(1) Preparation Example 1 Synthesis of Intermediate 1-1

1,2-diiodobenzene (19.8g, 0.06mol, sigma aldrich), triisopropyl borate (16.9g, 0.09mol, sigma aldrich), catalyst CuI (1.14 g, 0.006 mol, sigma aldrich), Sodium hydride (2.2 g, 0.09mol , Sigma aldrich) was added to 800ml THF and stirred for 12 hours at 25 ℃. After completion of the reaction, distilled water was added, followed by extraction. The column was purified (n-Hexane: methylene chloride) to obtain 15.3 g (yield 77%) of intermediate 1-1.

LC / MS: m / z = 331 [(M + l) ⁺ ]

(2) Preparation Example 1-2: Intermediate 1-2 Synthesis

Intermediate 1-1 (15.3 g, 0.046 mol), 1-iodo-2-nitrobenzene (7.5 g, 0.03 mol, sigma aldrich), Pd (OAc) 2 (0.34 g, 0.0015 mol, sigma aldrich), P (tBu) 600 ml of t-Butyl alcohol was added to 2Me (0.48 g, 0.003 mol, sigma aldrich) and KOtBu (10.1 g, 0.09 mol, sigma aldrich), followed by stirring at 25 ° C. After completion of the reaction, distilled water was added, followed by extraction. The column was purified (n-Hexane: methylene chloride) to obtain 8.5 g of an intermediate 1-2 (yield 57%).

LC / MS: m / z = 325 [(M + l) ⁺ ]

(3) Preparation Example 1-3: Intermediate 1-3 Synthesis

Intermediate 1-2 (8.5 g, 0.026 mol) and triphenylphosphine (20.5 g, 0.078 mol, sigma aldrich) were added with 340 ml of o-dichlorobenzene and refluxed at 180 ° C. After completion of the reaction, the mixture was cooled, and distilled water was extracted and extracted. n-Hexane: methylene chloride) afforded 6.8 g of intermediate 1-3 (yield 89%).

LC / MS: m / z = 293 [(M + l) ⁺ ]

(4) Preparation Example 1-4: Intermediate 1-4 Synthesis

Intermediate 1-3 (6.8 g, 0.023 mol), bromobenzene (3.6 g, 0.023 mol, sigma aldrich), Pd2 (dba) 3 (1.1 g, 0.0012 mol, sigma aldrich), P (t-Bu) 3 (0.28 g , 0.0014mol, sigma aldrich) and NatOBu (2.7g, 0.028mol, sigma aldrich) were added 280ml of Toluene and stirred at 80 ° C. After the completion of the reaction, the mixture was cooled, distilled water was extracted, and the column was purified (n-Hexane: methylene chloride) to obtain 6.4 g (yield 75%) of the intermediate 1-4.

LC / MS: m / z = 368 [(M + 1) ⁺ ]

(5) Preparation Example 1-5: Intermediate 1-5 Synthesis

Dibenzothiophene (20g, 0.109mol, sigma aldrich), N-Iodosuccinimide (12.1g, 0.054mol, sigma aldrich) and Solvent Chloroform / Acetone (3: 1) were added and stirred at 25 ° C. After cooling the reaction mixture, water was added in the amount of the reaction solvent, followed by extraction and column purification (n-Hexane) to obtain 9g (yield 27%) of the intermediate 1-5.

LC / MS: m / z = 310 [(M + l) ⁺ ]

(6) Preparation Example 1-6: Intermediate 1-6 Synthesis

Intermediate 1-5 (9g, 0.029mol), 1,4-diiodobenzene (9.6g, 0.029mol, sigma aldrich), catalyst Copper (II) (0.52g, 0.0029mol, sigma aldrich), Potassium fluoride (1.7g, 0.029 mol, sigma aldrich) DMSO 360ml was added and reacted at 130 ℃. After the reaction mixture was cooled, water was added as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to obtain 7.1 g (yield 63%) of intermediate 1-6.

LC / MS: m / z = 386 [(M + l) ⁺ ]

(7) Preparation Example 1-7: Compound 1 Synthesis

280 ml of DMSO in Intermediate 1-6 (7.1 g, 0.018 mol), Intermediate 1-4 (6.4 g, 0.018 mol), Catalytic Copper (II) (0.33 g, 0.0018 mol), Potassium fluoride (1.1 g, 0.018 mol) Put and reacted at 130 ℃. After the reaction mixture was cooled, water was added as much as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to obtain 4.6 g (yield 51%) of compound 1.

H-NMR (200 MHz, CDCl ₃ ): δ ppm, 1H (7.50 / M, 7.45 / M, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D, 7.59 / D, 7.43 / M, 7.79 / D , 7.98 / D, 7.52 / M, 8.45 / D, 8.41 / D, 8.20 / D) 2H (7.50 / D) 3H (7.58 / M) 4H (7.25 / D)

LC / MS: m / z = 502 [(M + 1) ⁺ ]

Example 2: Compound 2 Synthesis

(1) Preparation Example 2-1: Intermediate 2-1 Synthesis

Add 800 ml of 1-phenyl-1H-benzo [d] imidazole (21.2g, 0.109mol, sigma aldrich), N-Iodosuccinimide (12.1g, 0.054mol) and Solvent Chloroform / Acetone (3: 1) and stir at 25 ℃ The reaction was carried out. After the reaction mixture was cooled, water was added in the amount of the reaction solvent, followed by extraction and column purification (n-Hexane) to obtain 9.3 g (yield 27%) of intermediate 2-1.

LC / MS: m / z = 320 [(M + 1) ⁺ ]

(2) Preparation Example 2-2: Intermediate 2-2 Synthesis

Intermediate 2-1 (9.3 g, 0.029 mol), 1,4-diiodobenzene (9.6 g, 0.029 mol), catalyst Copper (II) (0.52 g, 0.0029 mol), DMSO 370 ml in Potassium fluoride (1.7 g, 0.029 mol) Was added and reacted at 130 ° C. After cooling the reaction mixture, water was added as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to give 7.1 g (yield 62%) of the intermediate 2-2.

LC / MS: m / z = 396 [(M + 1) ⁺ ]

(3) Preparation Example 2-3: Compound 2 Synthesis

280 ml of DMSO in Intermediate 2-2 (7.1 g, 0.018 mol), Intermediate 1-4 (6.4 g, 0.018 mol), Catalytic Copper (II) (0.33 g, 0.0018 mol), Potassium fluoride (1.1 g, 0.018 mol) Put and reacted at 130 ℃. After the reaction mixture was cooled, water was added as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to obtain 4.6 g (yield 50%) of compound 2.

H-NMR (200 MHz, CDCl ₃ ): δ ppm, 1H (7.50 / M, 7.29 / M, 8.12 / D, 7.63 / D, 7.90 / D, 7.39 / M, 8.10 / D, 7.59 / D, 8.56 / D ) 2H (7.45 / M, 7.22 / M, 7.25 / D, 7.85 / D) 4H (7.50 / D, 7.58 / M)

LC / MS: m / z = 512 [(M + 1) ⁺ ]

Example 3: Compound 5 Synthesis

(1) Preparation Example 3-1: Intermediate 5-1 Synthesis

800 ml of triphenylene (24.9 g, 0.109 mol, sigma aldrich), N-Iodosuccinimide (12.1 g, 0.054 mol), and Solvent Chloroform / Acetone (3: 1) were added and stirred at 25 ° C. After the reaction mixture was cooled, water was added as much as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane) to obtain 10.3 g (yield 24%) of intermediate 5-1.

LC / MS: m / z = 354 [(M + l) ⁺ ]

(2) Preparation Example 3-2: Intermediate 5-2 Synthesis

Intermediate 5-1 (10.3 g, 0.029 mol), 1,4-diiodobenzene (9.6 g, 0.029 mol), catalytic Copper (II) (0.52 g, 0.0029 mol), DMSO 370 ml in Potassium fluoride (1.7 g, 0.029 mol) Was added and reacted at 130 ° C. After cooling the reaction mixture, water was added as much as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to obtain 7.7 g (yield 62%) of intermediate 5-2. (M / z = 430)

LC / MS: m / z = 430 [(M + l) ⁺ ]

(3) Preparation Example 3-3: Compound 5 Synthesis

280 ml of DMSO in Intermediate 5-2 (7.7 g, 0.018 mol), Intermediate 1-4 (6.4 g, 0.018 mol), Catalytic Copper (II) (0.33 g, 0.0018 mol) and Potassium fluoride (1.1 g, 0.018 mol) Put and reacted at 130 ℃. After the reaction mixture was cooled, water was added as much as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to give 4.6 g (yield 47%) of compound 5.

H-NMR (200 MHz, CDCl ₃ ): δ ppm, 1H (7.50 / M, 7.45 / M, 7.63 / D, 7.29 / M, 7.90 / D, 7.39 / M, 8.34 / D, 8.99 / D) 2H (8.10 / D, 8.93 / D, 7.88 / M, 7.82 / M, 7.50 / D, 7.58 / M) 3H (8.12 / D) 4H (7.25 / D)

LC / MS: m / z = 546 [(M + l) ⁺ ]

Example 4: Compound 6 Synthesis

(1) Preparation Example 4-1: Intermediate 6-1 Synthesis

Add 800 ml of N-phenyldibenzo [b, d] thiophene-4-amine (30g, 0.109mol, sigma aldrich), N-Iodosuccinimide (12.1g, 0.054mol) and Solvent Chloroform / Acetone (3: 1) at 25 ℃ The reaction was stirred. After cooling the reaction mixture, water was added as much as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane) to obtain 11.6 g (yield 24%) of intermediate 6-1.

LC / MS: m / z = 401 [(M + l) ⁺ ]

(2) Preparation Example 4-2: Intermediate 6-2 Synthesis

Intermediate 6-1 (11.6 g, 0.029 mol), 1,4-diiodobenzene (9.6 g, 0.029 mol), catalyst Copper (II) (0.52 g, 0.0029 mol), DMSO 370 ml in Potassium fluoride (1.7 g, 0.02 mol) Was added and reacted at 130 ° C. After cooling the reaction mixture, water was added as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to give 8.6g (yield 62%) of intermediate 6-2.

LC / MS: m / z = 477 [(M + l) ⁺ ]

(3) Preparation Example 4-3: Compound 6 Synthesis

280 ml of DMSO in Intermediate 6-2 (8.6 g, 0.018 mol), Intermediate 1-4 (6.4 g, 0.018 mol), Catalytic Copper (II) (0.33 g, 0.0018 mol), Potassium fluoride (1.1 g, 0.018 mol) Put and reacted at 130 ℃. After the reaction mixture was cooled, water was added as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to obtain 4.6 g (yield 43%) of compound 6.

H-NMR (200 MHz, CDCl ₃ ): δ ppm, 1H (7.45 / M, 7.63 / D, 7.29 / M, 8.12 / D, 7.90 / D, 7.39 / M, 8.10 / D, 6.81 / M, 6.86 / D , 7.27 / M, 7.81 / D, 8.45 / D, 7.52 / M, 7.98 / D) 2H (7.50 / M, 7.50 / D, 7.58 / M, 7.54 / D, 6.69 / D, 7.20 / M, 6.63 / D )

LC / MS: m / z = 593 [(M + l) ⁺ ]

Example 5: Compound 7 Synthesis

(1) Preparation Example 5-1: Intermediate 7-1 Synthesis

800 ml of benzo [f] [1,9] phenanthroline (25.1g, 0.109mol, sigma aldrich), N-Iodosuccinimide (12.1g, 0.054mol) and Solvent Chloroform / Acetone (3: 1) were added and stirred at 25 ° C. Reacted. After the reaction mixture was cooled, water was added as much as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane) to obtain 10.3 g of an intermediate 7-1 (yield 27%).

LC / MS: m / z = 356 [(M + l) ⁺ ]

(2) Preparation Example 5-2: Intermediate 7-2 Synthesis

Intermediate 7-1 (11.6 g, 0.029 mol), 1,4-diiodobenzene (9.6 g, 0.029 mol), catalyst Copper (II) (0.52 g, 0.0029 mol), DMSO 370 ml in Potassium fluoride (1.7 g, 0.029 mol) Was added and reacted at 130 ° C. After cooling the reaction mixture, water was added as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to give 8.6g (yield 69%) of the intermediate 7-2.

LC / MS: m / z = 432 [(M + 1) ⁺ ]

(3) Preparation Example 5-3: Compound 7 Synthesis

300 ml of DMSO in Intermediate 7-2 (8.6 g, 0.020 mol), Intermediate 1-4 (6.8 g, 0.020 mol), Catalytic Copper (II) (0.38 g, 0.0020 mol) and Potassium fluoride (1.2 g, 0.020 mol) Put and reacted at 130 ℃. After cooling the reaction mixture, water was added as much as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to give 4.6g (yield 42%) of compound 7.

H-NMR (200 MHz, CDCl ₃ ): δ ppm, 1H (7.50 / M, 7.45 / M, 7.63 / D, 7.29 / M, 8.12 / D, 7.90 / D, 7.39 / M, 8.10 / D, 7.58 / M , 8.83 / D, 8.38 / D, 8.34 / S, 7.73 / D, 8.06 / D, 7.50 / D, 8.45 / D, 8.91 / S) 2H (7.50 / D, 7.58 / M) 4H (7.25 / D)

LC / MS: m / z = 548 [(M + 1) ⁺ ]

Example 6: Compound 12 Synthesis

(1) Preparation Example 6-1: Intermediate 12-1 Synthesis

5-phenyl-5,7a-dihydro-4bH-pyrrolo [3,2-f] [1,10] phenanthroline (32.4 g, 0.109 mol, sigma aldrich), N-Iodosuccinimide (12.1 g, 0.054 mol) with Solvent Chloroform 800 ml of / Acetone (3: 1) was added thereto, followed by stirring at 25 ° C. After the reaction mixture was cooled, water was added as much as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane) to obtain 10.3 g of intermediate 12-1 (yield 22%).

LC / MS: m / z = 423 [(M + 1) ⁺ ]

(2) Preparation Example 6-2: Intermediate 12-2 Synthesis

Intermediate 12-1 (10.3g, 0.024mol), 1,4-diiodobenzene (7.9g, 0.024mol), Catalytic Copper (II) (0.43g, 0.0024mol), Potassium fluoride (1.4g, 0.024mol) DMSO 400ml Was added and reacted at 130 ° C. After the reaction mixture was cooled, water was added as much as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to obtain 8.6 g (yield 72%) of intermediate 12-2.

LC / MS: m / z = 499 [(M + 1) ⁺ ]

(3) Preparation Example 6-3: Compound 12 Synthesis

Intermediate 12-2 (8.6 g, 0.017 mol), Intermediate 1-4 (6.8 g, 0.017 mol), Catalytic Copper (II) (0.33 g, 0.0017 mol), Potassium fluoride (1.1 g, 0.017 mol) Put and reacted at 130 ℃. After the reaction mixture was cooled, water was added as much as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to give 4.6 g (yield 44%) of compound 12.

H-NMR (200 MHz, CDCl ₃ ): δ ppm, 1H (7.50 / M, 7.45 / M, 7.63 / D, 7.29 / M, 8.12 / D, 7.90 / D, 7.39 / M, 8.10 / D, 6.77 / M , 5.07 / S, 4.07 / S, 4.32 / S, 7.48 / D, 8.51 / D, 7.67 / D, 6.94 / M, 8.53 / D, 6.81 / M) 2H (7.50 / D, 7.59 / D, 7.44 / D , 7.58 / M, 6.60 / D, 7.23 / M)

LC / MS: m / z = 615 [(M + 1) ⁺ ]

Example 7: Compound 14 Synthesis

(1) Preparation Example 7-1: Intermediate 14-1 Synthesis

Add 800 ml of pyrido [2,3-f] [1,7] phenanthroline (25.2g, 0.109mol, sigma aldrich), N-Iodosuccinimide (12.1g, 0.054mol) and Solvent Chloroform / Acetone (3: 1) The reaction was stirred at 占 폚. After cooling the reaction mixture, water was added as much as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane) to obtain 10.3 g of intermediate 14-1 (yield 26%).

LC / MS: m / z = 357 [(M + l) ⁺ ]

(2) Preparation Example 7-2: Intermediate 14-2 Synthesis

400 ml of DMSO in Intermediate 14-1 (10.3 g, 0.029 mol), 1,4-diiodobenzene (9.4 g, 0.029 mol), Catalytic Copper (II) (0.33 g, 0.0029 mol), Potassium fluoride (1.7 g, 0.029 mol) Was added and reacted at 130 ° C. After the reaction mixture was cooled, water was added as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to give 8.6 g (yield 68%) of intermediate 14-2.

LC / MS: m / z = 499 [(M + 1) ⁺ ]

(3) Preparation Example 7-3: Compound 14 Synthesis

300 ml of DMSO in Intermediate 14-2 (8.6 g, 0.020 mol), Intermediate 1-4 (8.0 g, 0.020 mol), Catalytic Copper (II) (0.38 g, 0.0020 mol) and Potassium fluoride (1.2 g, 0.020 mol) Put and reacted at 130 ℃. After the reaction mixture was cooled, water was added as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to obtain 4.6 g (yield 42%) of compound 14.

H-NMR (200 MHz, CDCl ₃ ): δ ppm, 1H (7.50 / M, 7.45 / M, 7.63 / D, 7.29 / M, 8.12 / D, 7.90 / D, 7.39 / M, 8.10 / D, 8.57 / S , 8.22 / S) 2H (8.38 / D, 8.83 / D, 7.50 / D) 4H (7.25 / D, 7.58 / M)

LC / MS: m / z = 549 [(M + l) ⁺ ]

Example 8: Compound 15 Synthesis

(1) Preparation Example 8-1: Intermediate 15-1 Synthesis

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

LC / MS: m / z = 295 [(M + 1) ⁺ ]

(2) Preparation Example 8-2: Intermediate 15-2 Synthesis

Intermediate 15-1 (10.3g, 0.035mol), 1,4-diiodobenzene (11.3g, 0.035mol), Catalytic Copper (II) (0.40g, 0.0029mol), Potassium fluoride (2.05g, 0.029mol) DMSO 400ml Was added and reacted at 130 ° C. After the reaction mixture was cooled, water was added as much as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to obtain 8.6 g (yield 66%) of intermediate 15-2.

LC / MS: m / z = 371 [(M + 1) ⁺ ]

(3) Preparation Example 8-3: Compound 15 Synthesis

340 ml of DMSO in Intermediate 15-2 (8.6 g, 0.023 mol), Intermediate 1-4 (9.2 g, 0.023 mol), Catalytic Copper (II) (0.44 g, 0.0020 mol) and Potassium fluoride (1.4 g, 0.020 mol) Put and reacted at 130 ℃. After the reaction mixture was cooled, water was added as much as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to give 4.6 g (yield 41%) of compound 15.

H-NMR (200 MHz, CDCl ₃ ): δ ppm, 1H (7.50 / M, 7.45 / M, 7.63 / D, 7.29 / M, 8.12 / D, 7.90 / D, 7.39 / M, 8.10 / D) 2H (6.81 / M, 6.69 / D, 7.54 / D, 7.50 / D, 7.58 / M) 4H (7.20 / M, 6.63 / D)

LC / MS: m / z = 487 [(M + l) ⁺ ]

Example 9: Compound 18 Synthesis

(1) Preparation Example 9-1: Intermediate 18-1 Synthesis

4-bromo-9-phenyl-9H-carbazole (10g, 0.031mol, sigma aldrich), 4-bromophenylboronic acid (7.5g, 0.037mol, sigma aldrich), Pd (pph) 4 (1.0g, 0.0009 mol, sigma Aldrich ), NaOH (3.7g, 0.093mol, sigma aldrich) was added to THF 360ml and reacted by stirring under reflux for 3 hours under nitrogen. After cooling the reaction mixture, dichloromethane extraction and silica column purification (MC: HEX) to obtain 9.1g (74% yield) of intermediate 18-1.

LC / MS: m / z = 398 [(M + 1) ⁺ ]

(2) Preparation Example 9-2: Compound 18 Synthesis

Intermediate 18-1 (9.1 g, 0.023 mol), 9H-pyrido [3,4-b] indol-9-ylboronic acid (5.9 g, 0.028 mol, sigma aldrich), catalyst Copper (II) (0.29 g, 0.0023 mol ), 400 ml of DMSO was added to Potassium fluoride (1.65 g, 0.023 mol) and reacted at 130 ° C. After the reaction mixture was cooled, water was added as much as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to give 8.6 g (yield 77%) of compound 18.

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

LC / MS: m / z = 489 [(M + 1) ⁺ ]

Example 10: Compound 21 Synthesis

Intermediate 18-1 (9.1 g, 0.023 mol), 4,6-diphenyl-1,3,5-triazin-2-ylboronic acid (7.8 g, 0.028 mol, sigma aldrich), catalyst Copper (II) (0.29 g, 0.0023 mol), 400 ml of DMSO was added to Potassium fluoride (1.65 g, 0.023 mol) and reacted at 130 ° C. After the reaction mixture was cooled, water was added as much as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to give 8.6 g (yield 68%) of compound 21.

H-NMR (200 MHz, CDCl ₃ ): δ ppm, 1H (7.25 / M, 7.45 / M, 7.33 / M, 8.55 / D, 7.94 / D, 7.59 / D, 7.43 / M, 7.79 / D) 2H (7.41 / M, 7.85 / D, 7.25 / D, 7.50 / D, 7.58 / D) 4H (8.28 / D, 7.51 / M)

LC / MS: m / z = 551 [(M + 1) ⁺ ]

Example 11: Compound 22 Synthesis

Intermediate 18-1 (9.1 g, 0.023 mol), 3,5-diphenyl-4H-1,2,4-triazol-4-ylboronic acid (7.4 g, 0.028 mol, sigma aldrich), catalyst Copper (II) (0.29 g, 0.0023 mol) and 400 ml of DMSO were added to Potassium fluoride (1.65 g, 0.023 mol) and reacted at 130 ° C. After cooling the reaction mixture, water was added as much as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to give 8.6 g (69%) of compound 22.

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

LC / MS: m / z = 539 [(M + 1) ⁺ ]

Example 12: Compound 23 Synthesis

Intermediate 18-1 (9.1g, 0.023mol), 3,5-bis (1-phenyl-1H-benzo [d] imidazol-2-yl) phenylboronic acid (14.2g, 0.028 mol, sigma aldrich), catalyst Copper ( II) (0.29g, 0.0023mol) and Potassium fluoride (1.65g, 0.023mol) were added 400ml of DMSO and reacted at 130 ° C. After the reaction mixture was cooled, water was added as much as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to give 8.6g (yield 48%) of compound 23.

H-NMR (200 MHz, CDCl ₃ ): δ ppm, 1H (8.55 / D, 7.33 / M, 7.94 / D, 7.25 / M, 7.43 / M, 7.79 / D) 2H (8.56 / D, 7.58 / D) 3H (7.59 / D, 7.45 / M, 7.66 / S) 4H (7.58 / M, 7.25 / D, 7.22 / M) 6H (7.50 / D)

LC / MS: m / z = 780 [(M + l) ⁺ ]

Example 13: Compound 25 Synthesis

Intermediate 18-1 (9.1g, 0.023mol), dipyridin-3-ylboramidic acid (6.0g, 0.028mol, sigma aldrich), catalyst Copper (II) (0.29g, 0.0023mol), Potassium fluoride (1.65g, 0.023mol 400ml of DMSO was added and reacted at 130 ° C. After cooling the reaction mixture, water was added as much as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to give 8.6g (yield 77%) of compound 25.

H-NMR (200 MHz, CDCl ₃ ): δ ppm, 1H (7.45 / M, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D, 7.59 / D, 7.43 / M, 7.79 / D) 2H (7.58 / M, 7.50 / D, 7.54 / D, 6.69 / D, 8.04 / S, 8.09 / D, 7.36 / M, 7.27 / D)

LC / MS: m / z = 489 [(M + 1) ⁺ ]

Example 14 Synthesis of Compound 29

Intermediate 18-1 (9.1 g, 0.023 mol), imidazo [1,2-a] pyridin-7-ylboronic acid (4.5 g, 0.028 mol, sigma aldrich), catalyst Copper (II) (0.29 g, 0.0023 mol), 400 ml of DMSO was added to Potassium fluoride (1.65 g, 0.023 mol) and reacted at 130 ° C. After the reaction mixture was cooled, water was added as much as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to give 8.6g (yield 86%) of compound 29.

H-NMR (200 MHz, CDCl ₃ ): δ ppm, 1H (7.25 / M, 7.45 / M, 7.94 / D, 7.33 / M, 8.55 / D, 7.59 / D, 7.43 / M, 7.79 / D, 7.73 / S , 6.87 / D, 8.54 / D) 2H (7.48 / D, 7.50 / D, 7.58 / M) 4H (7.25 / D)

LC / MS: m / z = 435 [(M + 1) ⁺ ]

Example 15: Compound 30 Synthesis

Intermediate 18-1 (9.1 g, 0.023 mol), 9H-carbazol-9-ylboronic acid (5.9 g, 0.028 mol, sigma aldrich), catalytic Copper (II) (0.29 g, 0.0023 mol), Potassium fluoride (1.65 g, 0.023mol) was added 400ml of DMSO and reacted at 130 ° C. After cooling the reaction mixture, water was added as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to give 8.6g (yield 63%) of compound 30.

H-NMR (200 MHz, CDCl ₃ ): δ ppm, 1H (7.50 / M, 7.63 / D, 7.29 / M, 8.12 / D, 7.45 / M, 7.59 / D, 7.43 / M) 2H (7.50 / D, 7.68 / D, 7.58 / M, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D) 3H (7.79 / D)

LC / MS: m / z = 485 [(M + 1) ⁺ ]

Example 16: Synthesis of Compound 31

Intermediate 18-1 (9.1 g, 0.023 mol), 2,7-bis (9-phenyl-9H-fluoren-9-yl) -9H-carbazol-9-ylboronic acid (18.9, 0.028mol, sigma aldrich), catalyst 400 ml of DMSO was added to Copper (II) (0.29 g, 0.0023 mol) and Potassium fluoride (1.65 g, 0.023 mol) and reacted at 130 ° C. After cooling the reaction mixture, water was added as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to give 15.9g (yield 69%) of compound 31.

H-NMR (200 MHz, CDCl ₃ ): δ ppm, 1H (7.28 / D, 7.45 / M, 7.59 / D, 7.43 / M, 7.55 / S, 7.31 / D, 8.00 / D, 8.31 / D, 6.80 / D , 7.20 / D) 2H (7.50 / D, 7.55 / D, 7.68 / M, 7.58 / M, 8.55 / D, 8.55 / S) 3H (7.28 / M, 7.79 / D) 4H (7.11 / D, 7.87 / D , 7.38 / M) 5H (7.33 / M)

LC / MS: m / z = 966 [(M + l) ⁺ ]

Example 17: Compound 34 Synthesis

Intermediate 18-1 (9.1 g, 0.023 mol), 4,6-diphenyl-1,3,5-triazin-2-ylboronic acid (7.8 g, 0.028 mol, sigma aldrich), catalyst Copper (II) (0.29 g, 0.0023mol), 400 ml of DMSO was added to Potassium fluoride (1.65g, 0.023mol) and reacted at 130 ° C. After the reaction mixture was cooled, water was added as much as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to give 8.6g (yield 68%) of compound 34.

H-NMR (200 MHz, CDCl ₃ ): δ ppm, 1H (7.25 / M, 7.45 / M, 7.94 / D, 7.33 / M, 8.55 / D, 7.59 / D, 7.43 / M, 7.79 / D) 2H (7.25 / D, 7.85 / D, 7.41 / M, 7.58 / M, 7.50 / D) 4H (8.28 / D, 7.51 / M)

LC / MS: m / z = 551 [(M + 1) ⁺ ]

Example 18: Compound 35 Synthesis

Intermediate 18-1 (9.1 g, 0.023 mol), 2,6-diphenylpyridin-4-ylboronic acid (7.7 g, 0.028 mol, sigma aldrich), catalyst Copper (II) (0.29 g, 0.0023 mol), Potassium fluoride (1.65 g, 0.023mol) was added 400ml DMSO and reacted at 130 ℃. After the reaction mixture was cooled, water was added as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to give 10.1 g (yield 80%) of compound 35.

H-NMR (200 MHz, CDCl ₃ ): δ ppm, 1H (7.45 / M, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D, 7.59 / D, 7.43 / M, 7.79 / D) 2H (8.20 / S, 7.47 / M, 7.50 / D, 7.58 / M) 4H (8.30 / M, 7.54 / M, 7.25 / D)

LC / MS: m / z = 549 [(M + l) ⁺ ]

Example 19: Compound 39 Synthesis

Intermediate 18-1 (9.1g, 0.023mol), 5- (9H-carbazol-9-yl) -2-phenyl-1H-benzo [d] imidazol-1-ylboronic acid (11.3g, 0.028mol, sigma aldrich) 400 ml of DMSO was added to the catalyst Copper (II) (0.29 g, 0.0023 mol) and Potassium fluoride (1.65 g, 0.023 mol) and reacted at 130 ° C. After the reaction mixture was cooled, 400 ml of water was added, followed by extraction and column purification (n-Hexane: methylene chloride) to obtain 9.1 g (yield 62%) of compound 39.

H-NMR (200 MHz, CDCl ₃ ): δ ppm, 1H (7.45 / M, 7.90 / D, 7.39 / M, 8.10 / D, 7.59 / D, 7.15 / D, 8.55 / D, 7.25 / M, 7.33 / M , 7.94 / D, 7.70 / S, 7.41 / M) 2H (7.50 / M, 7.50 / D, 7.79 / D, 7.68 / D, 8.28 / D, 7.51 / M, 7.58 / M, 7.29 / M, 8.12 / D , 7.63 / D)

LC / MS: m / z = 677.81 [(M + l) ⁺ ]

Example 20 Synthesis of Compound 44

Intermediate 18-1 (9.1g, 0.023mol), triphenylen-2-ylboronic acid (7.6g, 0.028mol, sigma aldrich), catalyst Copper (II) (0.29g, 0.0023mol), Potassium fluoride (1.65g, 0.023mol 400ml of DMSO was added and reacted at 130 ° C. After the reaction mixture was cooled, water was added as much as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to obtain 8.8 g (yield 70%) of compound 44.

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

LC / MS: m / z = 546 [(M + l) ⁺ ]

Example 21: Compound 46 Synthesis

Intermediate 18-1 (9.1 g, 0.023 mol), 9,9-diphenyl-9H-fluoren-2-ylboronic acid (10.1 g, 0.028 mol, sigma aldrich), catalyst Copper (II) (0.29 g, 0.0023 mol), 400 ml of DMSO was added to Potassium fluoride (1.65 g, 0.023 mol) and reacted at 130 ° C. After the reaction mixture was cooled, water was added as much as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to obtain 9.0 g of Compound 46 (yield 62%).

H-NMR (200 MHz, CDCl ₃ ): δ ppm, 1H (7.50 / M, 7.45 / M, 7.29 / M, 8.12 / D, 7.90 / D, 7.39 / M, 8.10 / D, 7.77 / S, 7.93 / D , 7.87 / D, 7.38 / M, 7.28 / M, 7.55 / D) 2H (7.50 / D, 7.58 / M, 7.63 / D, 7.26 / M) 4H (7.11 / D, 7.33 / M, 7.25 / D)

LC / MS: m / z = 636 [(M + l) ⁺ ]

Example 22: Compound 56 Synthesis

Intermediate 18-1 (9.1g, 0.023mol), 4- (9H-carbazol-9-yl) phenyl (biphenyl-4-yl) boramidic acid (12.7g, 0.028mol, sigma aldrich), catalytic Copper (II) ( 0.29 g, 0.0023 mol), 400 mL of DMSO was added to Potassium fluoride (1.65 g, 0.023 mol) and reacted at 130 ° C. After the reaction mixture was cooled, water was added as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to give 10.4 g (yield 62%) of compound 56.

H-NMR (200 MHz, CDCl ₃ ): δ ppm, 1H (7.41 / M, 7.63 / D, 7.50 / M, 7.29 / M, 8.12 / D, 7.45 / M, 7.59 / D, 7.43 / M, 7.79 / D ) 2H (7.58 / M, 7.50 / D, 7.54 / D, 6.63 / D, 7.37 / D, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D, 7.51 / M, 7.52 / D, 7.54 / M ) 4H (6.69 / D)

LC / MS: m / z = 728 [(M + 1) ⁺ ]

Example 23: Compound 60 Synthesis

Intermediate 18-1 (9.1g, 0.023mol), 9,9-diphenyl-9H-fluoren-2-yl (triphenylen-2-yl) boramidic acid (16.9g, 0.028mol, sigma aldrich), catalyst Copper (II) (0.29g, 0.0023mol) and Potassium fluoride (1.65g, 0.023mol) were added 400ml of DMSO and reacted at 130 ° C. After the reaction mixture was cooled, water was added as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to give 14.2 g (yield 70%) of compound 60.

H-NMR (200 MHz, CDCl ₃ ): δ ppm, 1H (7.45 / M, 7.94 / D, 7.25 / M, 8.55 / D, 7.59 / D, 7.43 / M, 7.79 / D, 7.02 / D, 8.13 / S , 6.58 / D, 7.62 / D, 6.75 / D, 7.55 / D, 7.28 / M, 7.38 / M) 2H (8.12 / D, 7.82 / M, 7.88 / M, 8.93 / D, 7.50 / D, 7.58 / M , 7.54 / D, 6.69 / D, 7.26 / M, 7.87 / D) 4H (7.11 / D) 5H (7.33 / M)

LC / MS: m / z = 878 [(M + l) ⁺ ]

Example 24: Compound 64 Synthesis

Intermediate 18-1 (9.1g, 0.023mol), 4- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl (triphenylen-2-yl) boramidic acid (16.6g, 0.028mol, sigma aldrich), catalyst Copper (II) (0.29 g, 0.0023 mol) and Potassium fluoride (1.65 g, 0.023 mol) were added 400 ml of DMSO and reacted at 130 ° C. After the reaction mixture was cooled, water was added as much as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to give 15.1 g (yield 76%) of compound 64.

H-NMR (200 MHz, CDCl ₃ ): δ ppm, 1H (7.45 / M, 7.59 / D, 7.43 / M, 7.79 / D, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D, 7.02 / D , 7.87 / D, 8.13 / S) 2H (8.93 / D, 7.88 / M, 7.82 / M, 8.12 / D, 7.41 / M, 7.90 / D, 7.54 / D, 7.50 / D, 7.58 / M) 4H (7.51 / M, 8.28 / D, 6.69 / D)

LC / MS: m / z = 869 [(M + l) ⁺ ]

Example 25: Compound 72 Synthesis

Intermediate 18-1 (9.1g, 0.023mol), biphenyl-4-yl (9,9-diphenyl-9H-fluoren-2-yl) boramidic acid (12.2g, 0.028mol, sigma aldrich), catalyst Copper (II) (0.29g, 0.0023mol) and Potassium fluoride (1.65g, 0.023mol) were added 400ml of DMSO and reacted at 130 ° C. After the reaction mixture was cooled, water was added as much as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to give 15.4 g (yield 83%) of compound 72.

H-NMR (200 MHz, CDCl ₃ ): δ ppm, 1H (7.45 / M, 7.59 / D, 7.43 / M, 7.79 / D, 7.94 / D, 7.25 / M, 8.55 / D, 6.75 / D, 6.58 / D , 7.62 / D, 7.87 / D, 7.38 / M, 7.28 / M, 7.55 / D, 7.41 / M) 2H (7.50 / D, 7.58 / M, 7.51 / M, 7.52 / D, 7.26 / M) 4H (7.11 / D, 7.54 / D, 6.69 / D) 5H (7.33 / M)

LC / MS: m / z = 804 [(M + l) ⁺ ]

Example 26 Synthesis of Compound 77

Intermediate 18-1 (9.1g, 0.023mol), 3- (9H-carbazol-9-yl) phenyl (biphenyl-4-yl) boramidic acid (12.7g, 0.028mol, sigma aldrich), catalyst Copper (II) ( 0.29 g, 0.0023 mol) and 400 ml of DMSO were added to Potassium fluoride (1.65 g, 0.023 mol) and reacted at 130 ° C. After the reaction mixture was cooled, water was added as much as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to give 8.6 g (yield 51%) of compound 77.

H-NMR (200 MHz, CDCl ₃ ): δ ppm, 1H (7.50 / M, 7.45 / M, 7.59 / D, 7.43 / M, 7.79 / D, 7.41 / M, 6.63 / D, 7.20 / M, 6.86 / D , 7.63 / D, 6.50 / S, 7.29 / M, 8.12 / D) 2H (7.50 / D, 7.51 / M, 7.52 / D, 7.58 / M, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D ) 4H (7.54 / D, 6.69 / D)

LC / MS: m / z = 728 [(M + 1) ⁺ ]

Example 27: Compound 80 Synthesis

Intermediate 18-1 (9.1g, 0.023mol), naphthalen-2-yl (triphenylen-2-yl) boramidic acid (11.6g, 0.028mol, sigma aldrich), catalytic Copper (II) (0.29g, 0.0023mol), 400 ml of DMSO was added to Potassium fluoride (1.65 g, 0.023 mol) and reacted at 130 ° C. After the reaction mixture was cooled, water was added as much as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to give 8.6 g (yield 54%) of compound 80.

H-NMR (200 MHz, CDCl ₃ ): δ ppm, 1H (7.50 / M, 7.45 / M, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D, 7.59 / D, 7.43 / M, 7.79 / D , 7.02 / D, 7.87 / D, 8.13 / S, 7.49 / D, 7.84 / D, 7.88 / D, 7.36 / M, 7.77 / D, 7.74 / S) 2H (8.93 / D, 7.88 / M, 7.82 / M , 8.12 / D, 7.54 / D, 6.69 / D, 7.50 / D, 7.58 / M)

LC / MS: m / z = 687 [(M + l) ⁺ ]

Example 28: Compound 83 Synthesis

Intermediate 18-1 (9.1 g, 0.023 mol), dibenzo [b, d] thiophen-3-yl (naphthalen-2-yl) boramidic acid (10.0 g, 0.028 mol, sigma aldrich), catalyst Copper (II) (0.29 g, 0.0023 mol) and 400 ml of DMSO were added to Potassium fluoride (1.65 g, 0.023 mol) and reacted at 130 ° C. After the reaction mixture was cooled, water was added as much as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to give 8.6 g (yield 58%) of compound 83.

H-NMR (200 MHz, CDCl ₃ ): δ ppm, 1H (7.45 / M, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D, 7.59 / D, 7.43 / M, 7.79 / D, 7.98 / D , 7.52 / M, 8.45 / D, 7.36 / M, 7.88 / D, 7.81 / D, 7.27 / D, 6.86 / D, 7.49 / D, 7.84 / D, 7.74 / S, 7.77 / D) 2H (7.50 / M , 7.50 / D, 6.69 / D, 7.58 / M, 7.54 / D)

LC / MS: m / z = 643 [(M + l) ⁺ ]

Example 29: Compound 89 Synthesis

Intermediate 18-1 (9.1g, 0.023mol), dibenzo [b, d] thiophen-2-yl (phenyl) boramidic acid (8.9g, 0.028mol, sigma aldrich), catalytic Copper (II) (0.29g, 0.0023mol ), 400 ml of DMSO was added to Potassium fluoride (1.65 g, 0.023 mol) and reacted at 130 ° C. After the reaction mixture was cooled, water was added as much as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to obtain 9.0 g of Compound 89 (yield 66%).

H-NMR (200 MHz, CDCl ₃ ): δ ppm, 1H (7.50 / M, 7.45 / M, 7.33 / M, 7.94 / D, 7.59 / D, 7.43 / M, 7.79 / D, 7.98 / D, 7.98 / D , 8.55 / D, 8.45 / D, 7.52 / M, 6.88 / D, 6.63 / D, 7.34 / D) 2H (7.50 / D, 6.63 / D, 7.54 / D, 7.58 / M, 7.25 / M, 7.20 / M , 6.69 / D)

LC / MS: m / z = 593 [(M + l) ⁺ ]

Example 30: Compound 90 Synthesis

(1) Preparation Example 30-1: Intermediate 90-1 Synthesis

Intermediate 1-4 (8.5 g, 0.023 mol), 6-bromonaphthalen-2-ylboronic acid (8.0 g, 0.028 mol, sigma aldrich), catalyst Copper (II) (0.29 g, 0.0023 mol), Potassium fluoride (1.65 g, 0.023mol) was added 400ml of DMSO and reacted at 130 ° C. After the reaction mixture was cooled, water was added as much as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to obtain 7.5 g (yield 73%) of the intermediate 90-1.

(2) Preparation Example 30-2: Compound 90 Synthesis

Intermediate 90-1 (7.5 g, 0.016 mol), 9-phenyl-9H-carbazol-4-ylboronic acid (5.7 g, 0.020 mol, sigma aldrich), catalyst Copper (II) (0.20 g, 0.0016 mol), Potassium fluoride (1.14g, 0.023mol) was added 300ml of DMSO and reacted at 130 ° C. After the reaction mixture was cooled, water was added as the amount of the reaction solvent, followed by extraction and column purification (n-Hexane: methylene chloride) to give 6.5 g (yield 67%) of the compound 90.

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

LC / MS: m / z = 611 [(M + 1) ⁺ ]

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

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

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 Fabrication of Organic Electroluminescent Device Using Compound 1 as Host Material of Light-Emitting Layer

NPB was deposited on a glass substrate coated with ITO to form a hole transport layer having a thickness of 120 nm. Then, Ir (ppy) ₃ was used as a dopant, and compound 1 was deposited at 9% rate, that is, the deposition rate of compound 1 was 0.1 nm / sec. , Ir (ppy) _{3 was} deposited at 0.009nm / sec to dope Ir (ppy) ₃ to a deposition rate of 8% to form a light emitting layer 30nm thick on the hole transport layer. Balq was deposited thereon to form a hole blocking layer that prevents holes from moving through the light emitting layer to the electron transport layer, and Alq ₃ was deposited thereon to form an electron transport layer having a thickness of 40 nm. By depositing, an electron injection layer having a thickness of 1 nm was formed. Aluminum was deposited on the electron injection layer to form a cathode of 120 nm, thereby manufacturing an organic light emitting display device.

At this time, the deposition rate of each material is an organic material, Compound 1, NPB, Alq ₃ , Balq was deposited at a rate of 0.1 nm / sec, lithium fluoride is deposited at a rate of 0.01 nm / sec, aluminum is 0.5 nm / sec It was.

Device Examples 2 to 26

An organic electroluminescent device of Device Examples 2 to 14 was manufactured by the same method as Device Example 1, except that Compound 1 was used as the light emitting material shown in Table 1 below.

Device Example 27

An organic light emitting display device was manufactured in the same manner as in Example 1, except that CBP ((4,4-N, N-dicarbazole) biphenyl) was used instead of Compound 1 and Compound 6 was used instead of NPB as the hole transport material. Was prepared.

Device Examples 28 to 35

An organic light emitting diode was manufactured according to the same method as Device Example 27, except that Compound 6 was used as the hole transport material shown in Table 1 below.

Device comparison example 1

An organic light emitting diode was manufactured according to the same method as Example 1 except for using (4,4-N, N-dicarbazole) biphenyl (CBP) as a light emitting material instead of Compound 1.

Hereinafter, the results of comparing the characteristics of the organic light emitting diodes manufactured according to Device Examples 1 to 35 and Device Comparative Example 1 are shown in Table 1 below.

Table 1

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

Driving voltage and luminous efficiency measurement

The organic light emitting element made from above (substrate size: 25x25mm ² / deposition area: 2x2mm ²⁾ an IVL measuring set (CS-2000 + fixture + IVL program) and then fixed to the raises the current by 1mA / m ² light emission luminance of the deposition surface (cd / m ² ), driving voltage (V), current density (A / m ² ), and luminous efficiency (cd / A), and the driving voltage and luminous efficiency are shown in Table 1 above when the luminance is 1000 cd / m ² . Indicated.

According to Table 1, when the compound for an organic light emitting device according to the present invention is used as a host material of the light emitting layer of the organic light emitting device or used as a hole transporting material, using conventional CBP as a light emitting material, or NPB as a hole transporting material It can be seen that the driving voltage is considerably lowered and the luminous efficiency is considerably improved than when used.

Claims

Compound for an organic light emitting device represented by the following Structural Formula 1 or 2.

In the above formula 1 or 2,

R 4 to R 6 may be the same as or different from each other, R 4 to R 6 are each independently a hydrogen atom,
,
,
,
,
,
,
,
,
,
,
,
,
,
,
,
,
,
,
,
,
,
,
, Substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C1 to C30 heteroaryl group, substituted or unsubstituted C3 to C30 cycloalkyl group, or substituted or unsubstituted Or a C 1 to C 30 heterocycloalkyl group, or at least any one of R 4 to R 6 is a fused C 3 to C 30 cycloalkyl group further bonded with a neighboring carbon atom of the carbon atom to which one is bonded, A substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused C1 to C30 hetero aryl group,

X 1 to X 37 may be the same as or different from each other, X 1 to X 37 are each independently a nitrogen atom, or
ego,

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

R 8 to R 70 may be the same as or different from each other, R 8 to R 70 are each independently a hydrogen atom,
,
,
,
, Substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C1 to C30 heterocycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted Or a C1 to C30 heteroaryl group, or at least one of R 8 to R 70 is a fused C3 to C30 cycloalkyl group which is further substituted with an adjacent carbon atom of the carbon atom to which one is bonded, or substituted or unsubstituted, 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 hetero aryl group,

Ar 3 to Ar 7 may be the same as or different from each other, Ar 3 to Ar 7 are each independently
,
,
,
, Substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C1 to C30 heterocycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C1 to C30 heteroaryl group,

Ar 1 and Ar 2 may be the same as or different from each other, and Ar 1 and Ar 2 are each independently
,
,
,
,
, Substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C1 to C30 heterocycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted Or a C1 to C30 heteroaryl group, or Ar 1 and Ar 2 are bonded to each other and form a substituted or unsubstituted C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, together with a nitrogen atom therebetween. Can do it,

X 38 to X 40 may be the same or different from each other, X 38 to X 40 are each independently a nitrogen atom, or
ego,

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

R 71 to R 116 may be the same as or different from each other, R 71 to R 116 may be independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to A C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,

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

R 1 to R 3 , and R 7 may be the same or different from each other, R 1 to R 3 , and R 7 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to A C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or R 1 to R 3 , and R At least one of 7 is a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, further bonded to a neighboring carbon atom of the carbon atom to which one is bonded, Substituted or unsubstituted fused C6 to C30 aryl groups, or substituted or unsubstituted fused C1 to C30 heteroaryl groups.
The method of claim 1,

The organic light emitting device compound is an organic light emitting device compound, characterized in that any one selected from compounds 1 to 92 represented by the following structural formula.
An organic electroluminescent device comprising a compound for an organic electroluminescent device according to any one of claims 1 and 2.
In an organic light emitting display device comprising a single electrode or a plurality of organic material layers between a first electrode, a second electrode, and a first electrode and a second electrode,

At least one organic material layer selected from the singular or plural organic material layers comprises an organic electroluminescent device compound according to any one of claims 1 and 2.
The method of claim 4, wherein

The organic light emitting device, characterized in that the singular or plural organic material layer comprises a light emitting layer.
The method of claim 4, wherein

The plurality of organic material layers may include a light emitting layer, and the plurality of organic material layers may further include at least one selected from an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transport layer, and a hole injection layer. Organic electroluminescent device.
The method of claim 5,

The light emitting layer is an organic light emitting device comprising a host and a dopant.