KR101638074B1 - Novel compound for organic electroluminescent device and organic electroluminescent device comprising the same - Google Patents

Abstract

Organic electroluminescent device compounds and organic electroluminescent devices comprising the same are disclosed. As a result, it is possible to provide a compound for an organic electroluminescent device which can be used as a host and a hole transporting material which is excellent in electrical stability and hole transporting ability and has high triplet state energy and can improve the luminous efficiency of a phosphorescent light emitting material, Can be 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 diverse functional units into polymer chains to produce multifunctional materials. However, it is difficult to purify compounds or to form devices, while low-molecular materials can synthesize materials of various properties. There is a limit to the synthesis of the substances.

The organic electroluminescent device can be formed in a laminated structure. In general, the device structure is formed by forming a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer between an anode and a cathode to form a light emitting layer The exciton formation can be facilitated and the emission efficiency can be enhanced.

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

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

Due to the nature of organic materials, it is difficult to emit phosphorescence. As a phosphorescent material, transition metal (iridium) is utilized as an organometallic compound, and an organic material is used as a host material to assist it. The material that assists the phosphorescent material (host) should have a wide bandgap and a high triplet state energy. A phosphorescent material having excellent current efficiency and luminous efficiency is received in the spotlight, but the electron transporting ability, the hole transporting ability, the host material which is thermally and electrically stable, and the organic electroluminescent device It is necessary to develop a compound for use.

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

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

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

According to an aspect of the present invention, a compound for an organic electroluminescence device represented by the following structural formula 1 may be provided.

[Structural formula 1]

In the above formula 1,

Q is a fused phenyl group, or a fused cyclohexyl group,

L represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthalenylene group, a substituted or unsubstituted carbazolylene group, or a substituted or unsubstituted fluorenylene group,

이고, A is a valence bond, or

ego,

Ar ² represents a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, An unsubstituted C1 to C30 heteroaryl group,

B is selected from the group consisting of hydrogen, deuterium, cyano, halogen, hydroxy, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C6 to C30 aryloxy, substituted or unsubstituted C1 to C30 alkylamino, A substituted or unsubstituted C6 to C30 arylamino group, a substituted or unsubstituted C7 to C30 arylalkylamino group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C1 to C30 alkyl group, A substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,

Ar ¹ represents a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, An unsubstituted C1 to C30 heteroaryl group,

R ¹ and R ² may be the same or different from each other and each of R ¹ and R ² is independently hydrogen, deuterium, 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 ³ is selected from the group consisting of hydrogen, deuterium, 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 is a substituted or unsubstituted C1 to C30 heteroaryl group, or R ³ is R ³ are combined with the adjacent carbon atoms and more characters combined carbon substituted or unsubstituted phenyl group, or a substituted or unsubstituted fused ring Can form a fused cyclohexyl group,

The term "substituted" means that at least one hydrogen of the substituent or the compound is substituted with a substituent selected from the group consisting of deuterium, a halogen group, a hydroxyl group, an amino group, a cyano group, a C2 to C30 dialkylamino group, a C12 to C30 diarylamino group, a C7 to C30 alkylarylamino group, , A C1 to C30 alkyl group, a silyl group, a C3 to C30 trialkylsilyl group, a C18 to C30 triarylsilyl group, a C8 to C30 dialkylarylsilyl group, a C13 to C30 diarylalkylsilyl group, a trihalosilyl group, a C3 A C7 to C30 heteroaryl group, a C7 to C30 arylheteroaryl group, a C7 to C30 arylheteroaryl group, a C2 to C30 heteroaryl group, a C6 to C30 heteroaryl group, a C1 to C30 heteroaryl group, C30 heteroarylheteroaryl group, a C1 to C20 alkoxy group, or a C1 to C10 trihaloalkyl group.

According to an embodiment of the present invention, preferably,

이고, B is

ego,

Q 'is a fused phenyl group, or a fused cyclohexyl group,

Ar ³ represents a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, An unsubstituted C1 to C30 heteroaryl group,

R ⁴ and R ⁵ may be the same or different from each other, and R ⁴ and R ⁵ are each independently selected from the group consisting of hydrogen, deuterium, 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 ⁶ is selected from the group consisting of hydrogen, deuterium, 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 is a substituted or unsubstituted C1 to C30 heteroaryl group, or R ⁶ is R ⁶ is in combination with the adjacent carbon atoms and more characters combined carbon substituted or unsubstituted phenyl group, or a substituted or unsubstituted fused ring To form a fused cyclohexyl group.

Specific examples of the alkyl group as the substituent include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isoamyl group, a hexyl group, a heptyl group, A halogen atom, a hydroxyl group, a nitro group, a cyano group, a trifluoromethyl group, a silyl group (in this case, an "alkylsilyl group"), a hydroxyl group ), Amino group (-NH2, -NH (R), -N (R ') (R "), R' and R" are independently an alkyl group having 1 to 20 carbon atoms, An alkyl group having 1 to 20 carbon atoms, a halogenated alkyl group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 1 to 20 carbon atoms, A heteroalkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, An arylalkyl group having 6 to 60 carbon atoms, a heteroaryl group having 4 to 40 carbon atoms, or a heteroarylalkyl group having 4 to 40 carbon atoms.

Specific examples of the cycloalkyl group as a substituent may include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and an adamantyl group

Specific examples of the alkoxy group as the substituent may be methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, isoamyloxy or hexyloxy.

Specific examples of the halogen group which is a substituent used in the compound of the present invention include fluorine (F), chlorine (Cl), bromine (Br) and the like.

Examples of the C6 to C30 aryl group include a phenyl group, a biphenyl group, a terphenyl group, a naphthalenyl group, an anthracenyl group, a phenanthrenyl group, a fluorenyl group, a spirobifluorenyl group, a chrysene group, a tetracene group, a pentacene group, A naphthyl group, a pyrenyl group, or a perylenyl group.

Examples of the C2 to C30 heteroaryl group include pyridinyl, pyrimidinyl, triazinyl, thiophenyl, pyrrolyl, benzothiophenyl, indolyl, imidazo [1,2- A benzothiazolyl group, a benzothiazolyl group, a benzimidazolyl group, an indazolyl group, a phenothiazinyl group, a phenazinyl group, a carbazolyl group, a dibenzothiophenyl group, an imidazolyl group, a triazolyl group, A thiazolyl group, a thiazolyl group, a benzothiazolyl group, a pyrazinyl group, a pyridazinyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, A pyridinyl group, a pyrimidinyl group, a triazinyl group, a thiophenyl group, a pyrrolyl group, a benzothiophenyl group, an indolyl group, an imidazo [1,2-a] A pyridinyl group, a benzimidazolyl group, an indazolyl group, a phenothiazinyl group, A carbamoyl group, a dibenzothiophenyl group, or a dibenzothiophenyl group.

The organic electroluminescence device compound may be any one selected from compounds 1 to 841 represented by the following formulas.

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

According to another aspect of the present invention, there is provided a light emitting device comprising a first electrode, a second electrode, and a light emitting layer and a hole transporting layer between the first electrode and the second electrode, wherein at least one of the light emitting layer and the hole transporting layer comprises: The organic electroluminescent device according to the present invention can be provided as an organic electroluminescent device.

The organic electroluminescent device may further include at least one selected from the group consisting of an electron injecting layer, an electron transporting layer, a hole blocking layer, an electron blocking layer, and a hole injecting layer between the first electrode and the second electrode.

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

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

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

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

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

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

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

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

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

As used herein, unless otherwise defined, "substituent" means that at least one hydrogen in the substituent or the compound for organic electroluminescence device is at least one selected from the group consisting of deuterium, a halogen group, a hydroxyl group, an amino group, a C1 to C30 amine group, a nitro group, , A C1 to C30 alkyl group, a C1 to C30 alkylsilyl group, a C6 to C30 arylsilyl group, a C7 to C30 alkylarylsilyl group, a C7 to C30 arylalkylsilyl group, a C3 to C30 cycloalkyl group, a C1 to C30 heterocycloalkyl group, To C30 aryl group, a C1 to C30 heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, or a cyano group.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

"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, at least one ring of the fused rings may contain from 1 to 4 heteroatoms.

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, .

Will be described with reference to Figs. 1 and 2. Fig. According to an embodiment of the present invention, the organic electroluminescent device 1 including the compound for an organic electroluminescent device can be provided.

According to another embodiment of the present invention, a light emitting layer 134 and a hole transporting layer 136 are provided between a first electrode 110, a second electrode 150, and the first and second electrodes, An organic electroluminescent device 1 may be provided, wherein at least one of the hole transporting layers includes the compound for an organic electroluminescent device.

The organic electroluminescent device 1 further includes an electron injecting layer 131, an electron transporting layer 132, a hole blocking layer 133, an electron blocking layer 135, and a hole injecting layer 132 between the first electrode and the second electrode. (137) may be further included.

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

At least one of the electron injecting layer 131, the electron transporting layer 132, the hole blocking layer 133, the light emitting layer 134, the electron blocking layer 135, the hole transporting layer 136 and the hole injecting layer 137, (130).

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

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

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

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

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

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

N, N'-di (1-naphthyl) -N, N, N'-dicarbazolyl-3, 5-benzene (mCP) as a hole transporting material, poly (3,4-ethylenedioxythiophene): polystyrenesulfonate (NPD), N, N'-diphenyl-N, N'-di (3-methylphenyl) -4,4'- diaminobiphenyl (TPD) N, N'N'-tetra-p-tolyl-4, 4'-diaminobiphenyl, 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, phthalocyanines such as nonmetal phthalocyanine and copper phthalocyanine Starburst amine derivatives, enamine stilbene derivatives, derivatives of aromatic tertiary amines and styryl amine compounds, and polysilanes.

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- (5-phenyl-2-oxazolyl) benzene, 1,4-bis (4-methylstyryl) benzene, 2-benzoxazolyl) thiophene, 1,4-diphenyl-1,3-butadiene, 1,6-diphenyl-1, Liquid scintillation scintillators such as 1,3,5-hexatriene, 1,1,4,4-tetraphenyl-1,3-butadiene, metal complexes of oxine derivatives, coumarin dyes, dicyanomethylenepyran dyes, dicyanomethylene Cyopyran pigment, polymethine pigment, oxobenzene Xanthine 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 manufactured using a material used in each layer. The thickness of each of these layers is not particularly limited and may be appropriately selected depending on the characteristics of the material, but may be determined usually within a range of 2 nm to 5,000 nm.

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

[Example]

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

Example  1: Synthesis of compound 1

(One) Manufacturing example  1-1: Intermediate 1-A Synthesis

Pd (OAc) 2 (0.04 g, 0.002 mol) and 2-Dicyclohexylphosphino-2 (2 g) were added to a solution of 2-bromonaphthalene (2.1 g, 0.010 mol), benzophenonehydrazone (2.4 g, 0.012 mol) '.4', 6'-triisopropylbiphenyl 0.1 g (0.002 mol) were dissolved in 30 ml of TOL, and the mixture was stirred at 90 ° C for 3 hours. Distilled water was added to the reaction mixture cooled to room temperature, and the mixture was extracted twice with 100 mL of diethyl ether and once with 100 mL of dichloromethane. The extracted organic material was cooled, layered on H ₂ O: MC, and subjected to column purification (n-hexane: MC) to obtain 3.0 g (yield: 92%) of intermediate 1-A.

LC / MS: m / z = 322 [(M + 1) ^< ^{+ &}

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

40 mL of EtOH and 40 mL of TOL were added to a mixture of Intermediate 1-A (3.2 g, 0.010 mol) and p-toluenesulfonic acid monohydrate (3.8 g, 0.020 mol), followed by stirring at 110 ° C for 24 hours. Distilled water was added to the reaction mixture cooled to room temperature, and extracted twice with 100 mL of diethyl ether and twice with 100 mL of dichloromethane. The extracted organic material was cooled, layered on H ₂ O: MC, and subjected to column purification (n-hexane: MC) to obtain 1.2 g (yield 70%) of Intermediate 1-B.

LC / MS: m / z = 167 [(M + 1) ^< ^{+ &}

(3) Manufacturing example  1-3: Intermediate 1 -1 synthesis

100 ml of THF was added to N-bromosuccinimide (3.2 g, 0.018 mol) in Intermediate 1-B (3.0 g, 0.018 mol) and the mixture was reacted at 0 ° C for 4 hours with stirring. After completion of the reaction H ₂ 0: to give the intermediate 1-1 by: (MC n-Hexane) 2.1g ( yield 48%) after column purification separation layer with ethyl acetate.

LC / MS: m / z = 246 [(M + 1) ^< ^{+ &}

(4) Manufacturing example  1-4: Intermediate 1-2 Synthesis

80 ml of toluene was added to bromobenzene (2.4 g, 0.015 mol), Pd (dba) 2 (0.7 g, 0.0008 mol) and sodium tert-butoxide (2.9 g, 0.030 mol) Followed by stirring at 95 ° C for 4 hours. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 3.9 g (yield 80%) of Intermediate 1-2.

LC / MS: m / z = 322 [(M + 1) ^< ^{+ &}

(5) Manufacturing example  1-5: Intermediate 1 -3 synthesis

To the intermediate 1-2 (3.5 g, 0.011 mol) was added bis (pinacolato) dibron (3.3 g, 0.013 mol) PdCl 2 (dppf) (0.4 g, 0.0006 mol) and potassium acetate (3.0 g, 0.022 mol) -dioxane (100 ml) were added and reacted at 95 ° C for 24 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 2.9 g (71% yield) of Intermediate 1-3.

LC / MS: m / z = 369 [(M + 1) ^< ^{+ &}

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

2-bromo-9,9-dimethyl-9H-fluorene (4.6 g, 0.017 mol) was added to 4-bromoaniline (3.0 g, 0.017 mol) 4> (yield: 77%).

LC / MS: m / z = 364 [(M + 1) ^< ^{+ &}

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

3.1 g (yield: 74%) of Intermediate 1-5 was synthesized in the same manner as in Preparation Example 1-4, except that 4-bromobiphenyl (1.9 g, 0.008 mol) was added to Intermediate 1-4 (3.0 g, 0.008 mol) ≪ / RTI >

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

(8) Manufacturing example  1-8: Synthesis of compound 1

100 ml of THF was added to intermediate 1-3 (3.0 g, 0.008 mol), intermediate 1-6 (3.5 g, 0.007 mol), Pd (pph3) 4 (0.4 g, 0.0004 mol) and potassium carbonate (2.0 g, 0.014 mol) The mixture was stirred at 65 占 폚 for 18 hours to react. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 3.4 g (yield 72%) of Compound 1.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.51 / d, 8.16 / d, 7.87 / d 7.62 / d, 7.55 / d, 7.45 / m, 7.41 / m, 7.38 / m, 7.36 / s, 7.58 / d, 6.71 / d, 7.69 / d, 7.58 / m, 7.58 / d)

LC / MS: m / z = 679 [(M + 1) ^< ^{+ &}

Example  2: Synthesis of compound 3

(One) Manufacturing example  2-1: Intermediate 3-1 Synthesis

2-methyl-1H-benzo [g] indole (3.0 g, 0.017 mol) synthesized in the same manner as in Production Example 1-3 to give 1.9 g (yield 43%) of Intermediate 3-1.

LC / MS: m / z = 260 [(M + 1) ^< ^{+ &}

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

Bromobenzene (2.2 g, 0.014 mol) was added to Intermediate 3-1 (3.6 g, 0.014 mol), and 3.6 g (yield 76%) of Intermediate 3-2 was obtained in the same manner as in Preparation Example 1-4 .

LC / MS: m / z = 336 [(M + 1) ^< ^{+ &}

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

Intermediate 3-2 (3.4g, 0.010mol) was added with bis (pinacolato) dibron (3.0g, 0.012mol) and synthesized in the same manner as in Example 1-5 to give 2.8g (yield: 74% %).

LC / MS: m / z = 383 [(M + 1) ^< ^{+ &}

(4) Manufacturing example  2-4: Intermediate 3-4 Synthesis

3-bromo-9-phenyl-9H-carbazole (2.6 g, 0.008 mol) was added to Intermediate 1-4 (3.0 g, 0.008 mol) (Yield: 76%).

LC / MS: m / z = 605 [(M + 1) ^< ^{+ &}

(5) Manufacturing example  2-5: Synthesis of Compound 3

Intermediate 3-4 (4.2 g, 0.007 mol) was added to Intermediate 3-3 (3.0 g, 0.008 mol), and 3.9 g (yield 71%) of Compound 3 was synthesized in the same manner as in Production Example 1-8 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.51 / d, 8.16 / d, 8.13 / d, 8.12 / d, 7.87 / d, 7.69 / d, 7.63 / s, 7.63 / d, 7.62 / d 7.58 / d, 7.55 / d, 7.50 / m, 7.45 / m, 6.75 / s, 6.58 / d, 5.93 / d) 2H (7.67 / / m, 7.50 / d)

LC / MS: m / z = 782 [(M + 1) ^< ^{+ &}

Example  3: Synthesis of Compound 7

(One) Manufacturing example  3-1: Synthesis of Intermediate 7-1

4-bromo-9,9-dimethyl-9H-thioxanthene (2.4 g, 0.008 mol) was added to Intermediate 1-4 (3.0 g, 0.008 mol) -1> 3.5 g (yield: 74%).

LC / MS: m / z = 588 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  3-2: Synthesis of Compound 7

Intermediate 7-1 (4.1 g, 0.007 mol) was added to Intermediate 1-3 (3.0 g, 0.008 mol), and 3.7 g (yield 71%) of Compound 7 was synthesized in the same manner as in Production Example 1-8 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.51 / d, 8.16 / d, 7.87 / d, 7.69 / d, 7.62 / d, 7.55 / d, 7.45 / m, 7.38 / m, 7.36 / s D, 7.67 / m, 7.58 / m, 6.75 / s, 6.58 / d, 6.46 / , 7.54 / d, 7.50 / d, 6.69 / d) 4H (1.72 / s)

LC / MS: m / z = 751 [(M + 1) ^< ^{+ &}

Example  4: Compound 17 Synthesis

(One) Manufacturing example  4-1: Synthesis of Intermediate 17-1

Intermediate 17-1> 3.2 (4-bromodibenzo [b, d] thiophene (2.1 g, 0.008 mol) was added to Intermediate 1-4 (3.0 g, 0.008 mol) g (yield: 74%).

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

(2) Manufacturing example  4-2: Compound 17 Synthesis

Intermediate 17-1 (3.8 g, 0.007 mol) was added to Intermediate 1-3 (3.0 g, 0.008 mol), and 3.9 g (yield 75%) of Compound 17 was synthesized in the same manner as in Production Example 1-8 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.51 / d, 8.45 / d, 8.16 / d, 7.98 / d, 7.87 / d, 7.81 / d, 7.62 / d, 7.55 / d, 7.52 / m 7.50 / m, 7.50 / m, 7.36 / s, 7.27 / m, 6.86 / d, 6.75 / , 7.38 / m, 6.69 / d, 1.72 / s)

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

Example  5: Compound 22 Synthesis

(One) Manufacturing example  5-1: Synthesis of Intermediate 22-1

1,4-dibromobenzene (2.5 g, 0.011 mol) was added to 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (3.0 g, 0.011 mol) To obtain 3.7 g (yield 70%) of Intermediate 22-1.

LC / MS: m / z = 440 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  5-2: Intermediate 22-2 Synthesis

(Pinacolato) dibron (2.0 g, 0.008 mol) was added to Intermediate 22-1 (3.0 g, 0.007 mol), and 2.4 g (yield: 70%) of Intermediate 22-2 %).

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

(3) Manufacturing example  5-3: Intermediate 22-3 Synthesis

Intermediate 22-3 was synthesized in the same manner as in Preparation Example 1-8, except that 1,3-dibromo-5-chlorobenzene (2.2 g, 0.008 mol) was added to Intermediate 22-2 (5.0 g, 0.010 mol) g (yield: 73%).

LC / MS: m / z = 831 [(M + 1) ^< ^{+ &}

(4) Manufacturing example  5-4: Compound 22 Synthesis

Intermediate 22-3 (5.8 g, 0.007 mol) was added to Intermediate 1-3 (3.0 g, 0.008 mol), and 4.9 g (Yield: 68%) of Compound 22 was synthesized in the same manner as in Production Example 1-8 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.51 / d, 8.16 / d, 7.45 / m, 7.36 / s) 2H (8.05 / d, 7.87 / d, 7.67 / m, 7.62 / d, 7.58 7.58 / d, 7.50 / d, 6.81 / m, 6.75 / d, 6.58 / d) 3H (7.54 / d, 7.28 / m, 7.20 / , 1.72 / s)

LC / MS: m / z = 1039 [(M + 1) ^< ^{+ &}

Example  6: Compound 33 Synthesis

(One) Manufacturing example  6-1: Synthesis of Intermediate 33-1

(Biphenyl-4-yl) -9,9-dimethyl-9H-fluoren-2-amine (3.6g, 0.010mol) was added to 3,3'-dibromobiphenyl (3.0g, 0.010mol) 4, < Intermediate 33-1 > (yield: 77%) was obtained.

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

(2) Manufacturing example  6-2: Compound 33 Synthesis

Synthesis was conducted in the same manner as in Preparation Example 1-8, except that Intermediate 33-1 (4.1 g, 0.007 mol) was added to Intermediate 1-3 (3.0 g, 0.008 mol), and 3.8 g (71% .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.51 / d, 8.16 / d, 7.87 / d, 7.70 / d, 7.62 / d, 7.57 / m, 7.55 / d, 7.44 / m, 7.38 / m 7.56 / s, 6.59 / d, 6.58 / d) 2H (8.05 / d, 7.67 / m, 7.58 / m, 7.54 / d, 7.52 / d , 7.51 / m, 7.50 / d, 7.48 / d, 6.69 / d, 1.72 / s)

LC / MS: m / z = 755 [(M + 1) ^&lt; ^{+ &}

Example  7: Compound 35 Synthesis

(One) Manufacturing example  7-1: Synthesis of Intermediate 35-1

Bis (9,9-dimethyl-9H-fluoren-2-yl) amine (4.0 g, 0.010 mol) was added to 3,3'-dibromobiphenyl (3.0 g, 0.010 mol) To obtain 5.0 g (yield 79%) of < Intermediate 35-1 >.

LC / MS: m / z = 632 [(M + 1) ^&lt; ^{+ &}

(2) Manufacturing example  7-2: Compound 35 Synthesis

Intermediate 35-1 (4.4 g, 0.007 mol) was added to Intermediate 1-3 (3.0 g, 0.008 mol), and 4.1 g (yield 74%) of Compound 35 was synthesized in the same manner as in Production Example 1-8 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.16 / d, 7.70 / s, 7.57 / m, 7.45 / m, 7.44 / m, 7.36 / s, 6.89 / s, 6.88 / d, 6.59 / d 7.58 / d, 7.50 / d, 7.48 / d, 7.38 / m, 7.28 / m, 6.75 / ) &Lt; / RTI &gt; 4H (1.72 / s)

LC / MS: m / z = 796 [(M + 1) ^&lt; ^{+ &}

Example  8: Compound 38 Synthesis

(One) Manufacturing example  8-1: Synthesis of Intermediate 38-1

4.4 g (yield: 74%) of Intermediate 38-1 was synthesized by the same method as in Preparation Example 1-4, except that 4-bromobiphenyl (3.5 g, 0.015 mol) was added to Intermediate 1-1 (3.6 g, 0.015 mol) &Lt; / RTI >

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

(2) Manufacturing example  8-2: Intermediate 38-2 Synthesis

Intermediate 38-2 (3.2g, Yield: 72%) was synthesized in the same manner as in Preparation Example 1-5, except that bis (pinacolato) dibron (3.0g, 0.012mol) %).

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

(3) Manufacturing example  8-3: Compound 38 Synthesis

Intermediate 33-1 (3.3 g, 0.006 mol) was added to Intermediate 38-2 (3.0 g, 0.007 mol), and 3.5 g (yield 71%) of Compound 38 was synthesized in the same manner as in Production Example 1-8 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.51 / d, 8.16 / d, 7.87 / d, 7.70 / s, 7.62 / d, 7.57 / m, 7.55 / d, 7.44 / m, 7.38 / m D, 7.79 / d, 7.68 / d, 7.67 / m, 7.54 / d), 7.38 / d, 7.28 / m, 6.89 / s, 6.88 / d, 6.75 / , 7.48 / d, 7.41 / m, 6.69 / d, 1.72 / s) 4H (7.52 / d, 7.51 /

LC / MS: m / z = 832 [(M + 1) ^&lt; ^{+ &}

Example  9: Compound 46 Synthesis

(One) Manufacturing example  9-1: Synthesis of Intermediate 46-1

4-ylamine (2.9 g, 0.009 mol) was added to 2,7-dibromo-9,9-dimethyl-9H-fluorene (3.0 g, 0.009 mol) (Yield: 74%) of Intermediate 46-1.

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

(2) Manufacturing example  9-2: Compound 46 Synthesis

Synthesis was conducted in the same manner as in Preparation Example 1-8, except that Intermediate 46-1 (4.1 g, 0.007 mol) was added to Intermediate 1-3 (3.0 g, 0.008 mol) to obtain 3.8 g (yield 71%) of Compound 46 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.16 / d, 7.93 / d, 7.77 / s, 7.63 / d, 7.62 / d, 7.45 / m, 7.36 / s, 6.75 / s, 6.58 / d 7.54 / d, 7.51 / m, 6.69 / d) 2H (8.05 / d, 7.67 / m, 7.58 / m, 7.50 / d, 7.41 /

LC / MS: m / z = 755 [(M + 1) ^&lt; ^{+ &}

Example  10: Compound 49 Synthesis

(One) Manufacturing example  10-1: Synthesis of Intermediate 49-1

N- (biphenyl-4-yl) -9,9-dimethyl-9H-fluoren-2-amine (3.6 g, 0.010 mol) was added to 2,6-dibromonaphthalene (3.0 g, 0.010 mol) (Yield: 76%) of Intermediate 49-1.

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

(2) Manufacturing example  10-2: Compound 49 Synthesis

3.6 g (71%) of Compound 49 was synthesized in the same manner as in Preparation Example 1-8, except that Intermediate 49-1 (1.9 g, 0.007 mol) was added to Intermediate 1-3 (3.0 g, 0.008 mol) .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.51 / d, 8.16 / d, 7.87 / d, 7.84 / d, 7.74 / s, 7.69 / d, 7.64 / d, 7.62 / d, 7.55 / d 7.58 / m, 7.48 / m, 7.48 / m, 7.36 / s, 7.28 / , 7.52 / d, 7.51 / m, 7.50 / d, 6.69 / d, 1.72 / s)

LC / MS: m / z = 729 [(M + 1) ^&lt; ^{+ &}

Example  11: Compound 66 Synthesis

(One) Manufacturing example  11-1: Intermediate 66-1 Synthesis

(3.1 g, 0.009 mol) was added to 3,6-diphenyl-9H-carbazole (3.0 g, 0.009 mol) in the same manner as in Preparation Example 1-4 to give Intermediate 66- 1 &gt; (yield: 78%).

LC / MS: m / z = 565 [(M + 1) ^&lt; ^{+ &}

(2) Manufacturing example  11-2: Intermediate 66-2 Synthesis

4-bromobiphenyl (2.4 g, 0.015 mol) was added to 3-bromo-1H-indole (3.0 g, 0.015 mol) and the reaction was conducted in the same manner as in Preparation Example 1-4 to give 3.3 g 80%).

LC / MS: m / z = 272 [(M + 1) ^&lt; ^{+ &}

(3) Manufacturing example  11-3: Synthesis of Intermediate 66-2-1

(Pinacolato) dibron (3.3 g, 0.013 mol) was added to Intermediate 66-2 (3.0 g, 0.011 mol), and 2.5 g of Intermediate 66-2-1 Yield: 74%).

LC / MS: m / z = 304 [(M + 1) ^&lt; ^{+ &}

(4) Manufacturing example  11-4: Intermediate 66-3 Synthesis

(2.4 g, 0.010 mol) was added to Intermediate 66-2-1 (3.0 g, 0.010 mol) and 2.6 g (Intermediate 66-3) of Intermediate 66-3 was synthesized in the same manner as in Production Example 1-8 Yield: 74%). (M / z = 348)

LC / MS: m / z = 348 [(M + 1) ^&lt; ^{+ &}

(5) Manufacturing example  11-5: Intermediate 66-4 Synthesis

Intermediate 66-3 (3.1 g, 0.009 mol) was added to Intermediate 66-1 (5.0 g, 0.009 mol), and 5.2 g (yield 70%) of Intermediate 66-4 was synthesized in the same manner as in Production Example 1-4, ).

LC / MS: m / z = 832 [(M + 1) ^&lt; ^{+ &}

(6) Manufacturing example  11-6: Compound 66 Synthesis

Intermediate 66-4 (5.8 g, 0.007 mol) was added to Intermediate 1-3 (3.0 g, 0.008 mol), and 5.9 g (yield 74%) of Compound 66 was synthesized in the same manner as in Production Example 1-8 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.18 / d, 8.17 / d, 8.16 / d, 8.00 / d, 7.87 / d, 7.71 / d, 7.69 / d) 2H (8.05 / d, 7.77 7.58 / m, 7.41 / m, 7.37 / d, 7.36 / s, 6.63 / d) 4H (7.58 / m, 7.54 / / d, 6.69 / d)

LC / MS: m / z = 996 [(M + 1) ^&lt; ^{+ &}

Example  12: Compound 73 Synthesis

(One) Manufacturing example  12-1: Synthesis of Intermediate 73-1

9H-carbazol-3-ylboronic acid (2.9 g, 0.010 mol) was added to a solution of bis (4-bromophenyl) amine (3.0 g, 0.008 mol) To obtain 2.9 g (yield: 75%) of Intermediate 73-1.

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

(2) Manufacturing example  12-2: Intermediate 73-2 Synthesis

Intermediate 1-2 (2.8 g, 0.010 mol) was added to Intermediate 73-1 (5.0 g, 0.010 mol), and 5.6 g of Intermediate 73-2 (yield: 77% ).

LC / MS: m / z = 730 [(M + 1) ^&lt; ^{+ &}

(3) Manufacturing example  12-3: Compound 73 Synthesis

Intermediate 1-3 (3.0 g, 0.008 mol) was added to Intermediate 73-2 (5.1 g, 0.007 mol), and 4.4 g (yield 71%) of Compound 73 was synthesized in the same manner as in Production Example 1-8 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 7.94 / d, 7.87 / d, 7.77 / s, 7.69 / d, 7.33 / m, 7.25 / m) 2H (8.51 / d, 8.16 d, 7.36 / s) 3H (7.45 / m) 4H (8.05 / d, 7.67 /

LC / MS: m / z = 894 [(M + 1) ^&lt; ^{+ &}

Example  13: Compound 76 Synthesis

(One) Manufacturing example  13-1: Synthesis of Intermediate 76-1

9H-fluoren-2-ylboronic acid (2.8 g, 0.010 mol) was added to tris (4-bromophenyl) amine (5.0 g, 0.010 mol) 4.3 g (yield: 72%) of Intermediate 76-1 was obtained.

LC / MS: m / z = 595 [(M + 1) ^&lt; ^{+ &}

(2) Manufacturing example  13-2: Intermediate 76-2 Synthesis

(2.7g, 0.010mol) of triphenylen-2-ylboronic acid was added to Intermediate 76-1 (5.0g, 0.008mol), and 4.5g of Intermediate 76-2 76%).

LC / MS: m / z = 742 [(M + 1) ^&lt; ^{+ &}

(3) Manufacturing example  13-3: Compound 76 Synthesis

The compound 76-2 (5.2 g, 0.007 mol) was added to Intermediate 1-3 (3.0 g, 0.008 mol) and the compound was synthesized in the same manner as in Production Example 1-8 to give 4.4 g (yield 70%) of Compound 76 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (9.15 / s, 8.51 / d, 8.18 / d, 8.16 / d, 8.04 / d, 7.93 / d, 7.87 / d, 7.77 / s, 7.63 / d 7.85 / m, 7.38 / m, 7.28 / m) 2H (8.93 d, 8.12 d, 8.05 d, 7.88 m, 7.82 m, 7.67 m, 7.58 m , 7.50 / d, 1.72 / s) 6H (7.54 / d, 6.69 / d)

LC / MS: m / z = 906 [(M + 1) ^&lt; ^{+ &}

Example  14: Compound 93 Synthesis

(One) Manufacturing example  14-1: Intermediate 93-A Synthesis

9-bromophenanthrene (2.6 g, 0.010 mol) was synthesized in the same manner as in Production Example 1-1 to give 3.3 g (yield: 88%) of Intermediate 93-A.

LC / MS: m / z = 372 [(M + 1) ^&lt; ^{+ &}

(2) Manufacturing example  14-2: Synthesis of intermediate 93-B

Intermediate 93-A (3.7 g, 0.010 mol) was synthesized in the same manner as in Production Example 1-2 to give 1.5 g (yield 67%) of Intermediate 93-B.

LC / MS: m / z = 217 [(M + 1) ^&lt; ^{+ &}

(3) Manufacturing example  14-3: Synthesis of intermediate 93-1

Intermediate 93-B (2.2 g, 0.010 mol) was synthesized in the same manner as in Preparation Example 1-3 to give 1.2 g (yield 41%) of Intermediate 93-1.

LC / MS: m / z = 296 [(M + 1) ^&lt; ^{+ &}

(4) Manufacturing example  14-4: Intermediate 93-2 Synthesis

Bromobenzene (1.9 g, 0.012 mol) was added to Intermediate 93-1 (3.6 g, 0.012 mol), and 2.9 g (yield: 74%) of Intermediate 93-2 was obtained in the same manner as in Production Example 1-4 .

LC / MS: m / z = 322 [(M + 1) ^&lt; ^{+ &}

(5) Manufacturing example  14-5: Intermediate 93-3 Synthesis

(Pinacolato) dibron (3.0 g, 0.012 mol) was added to Intermediate 93-2 (3.2 g, 0.010 mol), and 2.9 g (yield: 70%) of Intermediate 93-3 %).

LC / MS: m / z = 419 [(M + 1) ^&lt; ^{+ &}

(6) Manufacturing example  14-6: Compound 93 Synthesis

Intermediate 1-4 (3.0 g, 0.008 mol) was added to Intermediate 93-3 (4.2 g, 0.008 mol), and 4.1 g (yield 71%) of Compound 93 was synthesized in the same manner as in Production Example 1-8 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.87 / d, 7.62 / d, 7.55 / d, 7.38 / m, 7.36 / s, 7.28 / m, 6.75 / s, 6.58 / d) 2H (8.93 d, 7.52 / d, 7.51 / m, 6.69 / d)

LC / MS: m / z = 729 [(M + 1) ^&lt; ^{+ &}

Example  15: Compound 114 Synthesis

(One) Manufacturing example  15-1: Synthesis of intermediate 114-1

Biphenyl-4-amine (1.7 g, 0.010 mol) was added to 1-bromo-3-iodobenzene (3.0 g, 0.010 mol) (Yield: 74%).

LC / MS: m / z = 324 [(M + 1) ^&lt; ^{+ &}

(2) Manufacturing example  15-2: Intermediate 114-2 Synthesis

3-bromo-9,9-dimethyl-dipyridine (2.5 g, 0.009 mol) was added to Intermediate 114-1 (3.0 g, 0.009 mol) (Yield: 70%).

LC / MS: m / z = 518 [(M + 1) ^&lt; ^{+ &}

(3) Manufacturing example  15-3: Compound 114 Synthesis

Intermediate 114-2 (3.1 g, 0.006 mol) was added to Intermediate 93-3 (3.0 g, 0.007 mol), and 3.4 g (yield 77%) of Compound 114 was synthesized in the same manner as in Production Example 1-8 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.51 / d, 7.48 / d, 7.45 / m, 7.44 / m, 7.41 / m, 7.36 / s, 7.17 / d, 6.89 / s, 6.88 / d M, 7.58 / d, 7.51 / m, 7.50 / d, 7.81 / , 6.69 / d, 1.72 / s)

LC / MS: m / z = 731 [(M + 1) ^&lt; ^{+ &}

Example  16: Compound 171 Synthesis

(One) Manufacturing example  16-1: Synthesis of intermediate 171-1

Intermediate 1-3 (3.0 g, 0.008 mol) was added thereto, and 1.7 g (yield: 48%) of Intermediate 171-1 was obtained in the same manner as in Production Example 1-3.

LC / MS: m / z = 448 [(M + 1) ^&lt; ^{+ &}

(2) Manufacturing example  16-2: Intermediate 171-2 Synthesis

2.3 g (yield: 74%) of Intermediate 171-2 was obtained by adding bromobenzene (0.9 g, 0.006 mol) to Intermediate 171-1 (3.0 g, 0.007 mol) in the same manner as in Preparation Example 1-8 .

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

(3) Manufacturing example  16-3: Intermediate 171-3 Synthesis

Bis (9,9-dimethyl-9H-fluoren-2-yl) amine (5.1 g, 0.013 mol) was added to 1,4-dibromobenzene (3.0 g, 0.013 mol) To obtain 5.3 g (yield: 74%) of Intermediate 171-3.

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

(4) Manufacturing example  16-4: Synthesis of Compound 171

Intermediate 171-2 (4.8 g, 0.011 mol) was added to Intermediate 171-3 (5.0 g, 0.009 mol) and synthesized in the same manner as in Production Example 1-8 to give 5.3 g (yield 74%) of Compound 171 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.51 / d, 8.16 / d) 2H (8.05 / d, 7.87 / d, 7.79 / d, 7.67 / m, 7.62 / d, 7.58 / m, 7.55 d, 7.54 / d, 7.51 / m, 7.50 / d, 7.41 / m, 7.38 / m, 7.28 / m, 6.75 / s, 6.69 / d, 6.58 /

LC / MS: m / z = 796 [M + 1) ^&lt; ^{+ &}

Example  17: Compound 172 Synthesis

Intermediate 1-4 (3.1 g, 0.006 mol) was added to Intermediate 171-2 (3.0 g, 0.007 mol), and 3.4 g (yield: 74%) of Compound 172 was synthesized in the same manner as in Production Example 1-8 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (8.16 / d, 7.87 / d, 7.62 / d, 7.38 / m, 7.28 / m, 6.75 / s, 1.72 / s) 4H (8.05 / d, 7.79 7.51 / m, 7.50 / d, 7.41 / m, 6.69 / d)

LC / MS: m / z = 755 [(M + 1) ^&lt; ^{+ &}

Example  18: Compound 174 Synthesis

(One) Manufacturing example  18-1: Synthesis of intermediate 174-1

Dibiphenyl-4-ylamine (4.1 g, 0.013 mol) was added to 1,4-dibromobenzene (3.0 g, 0.013 mol), and the compound was synthesized in the same manner as in Preparation Example 1-4 to give 4.8 g 77%).

LC / MS: m / z = 476 [(M + 1) ^&lt; ^{+ &}

(2) Manufacturing example  18-2: Compound 174 Synthesis

Intermediate 174-1 (2.9 g, 0.006 mol) was added to Intermediate 171-2 (3.0 g, 0.007 mol) and synthesized in the same manner as in Production Example 1-8 to give 3.0 g (yield 70%) of Compound 174 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.51 / d, 8.16 / d, 7.45 / m) 2H (8.05 / d, 7.79 / d, 7.67 / m, 7.58 / m, 7.50 / d) 3H (7.41 / m) 4H (7.52 / d) 6H (7.54 / d, 7.51 / m, 6.69 / d)

LC / MS: m / z 715 [(M + 1) ^&lt; ^{+ &}

Example  19: Compound 220 Synthesis

(One) Manufacturing example  19-1: Synthesis of intermediate 220-1

3.1 g (yield: 74%) of Intermediate 220-1 was synthesized in the same manner as in Preparation Example 1-4, except that 3-bromopyridine (2.4 g, 0.015 mol) was added to Intermediate 1-1 (3.6 g, 0.015 mol) &Lt; / RTI >

LC / MS: m / z = 323 [(M + 1) ^&lt; ^{+ &}

(2) Manufacturing example  19-2: Synthesis of intermediate 220-2

Intermediate 220-2 (2.8 g, yield: 74%) was synthesized by the same method as in Preparation Example 1-5, except that bis (pinacolato) dibron (3.0 g, 0.012 mol) %).

LC / MS: m / z = 370 [(M + 1) ^&lt; ^{+ &}

(3) Manufacturing example  19-3: Compound 220 Synthesis

Intermediate 1-4 (3.5 g, 0.007 mol) was added to Intermediate 220-2 (3.0 g, 0.008 mol), and 3.5 g (yield 74%) of Compound 220 was synthesized in the same manner as in Production Example 1-8 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.60 / s, 8.51 / d, 8.45 / d, 8.16 / d, 7.87 / d, 7.80 / d, 7.62 / d, 7.55 / d, 7.41 / m 7.58 / d, 7.67 / m, 7.52 / d, 7.51 / m, 1.72 / s) 4H (7.54 / d, 6.69 / d)

LC / MS: m / z = 680 [(M + 1) ^&lt; ^{+ &}

Example  20: Synthesis of compound 258

(One) Manufacturing example  20-1: Intermediate 258-A Synthesis

(2.5 g, 0.010 mol) of 6-bromo-1,2,3,4-tetrahydronaphthalene synthesized in the same manner as in Production Example 1-1 to give 2.8 g (yield: 85%) of Intermediate 258-A .

LC / MS: m / z = 326 [(M + 1) ^&lt; ^{+ &}

(2) Manufacturing example  20-2: Intermediate 258-B Synthesis

Intermediate 258-A (3.3 g, 0.010 mol) was added thereto, and 1.2 g (yield 72%) of Intermediate 258-B was obtained in the same manner as in Production Example 1-2.

LC / MS: m / z = 171 [(M + 1) ^&lt; ^{+ &}

(3) Manufacturing example  20-3: Synthesis of intermediate 258-1

Intermediate 258-B (3.4 g, 0.020 mol) was added thereto, and 1.8 g (yield: 37%) of Intermediate 258-1 was obtained in the same manner as in Production Example 1-5.

LC / MS: m / z = 250 [(M + 1) ^&lt; ^{+ &}

(4) Manufacturing example  20-4: Synthesis of intermediate 258-2

Intermediate 258-1 (3.8 g, 0.015 mol) and bromobenzene (2.4 g, 0.015 mol) were added to the reaction mixture to obtain 3.5 g (yield 72%) of Intermediate 258-2 .

LC / MS: m / z = 326 [(M + 1) ^&lt; ^{+ &}

(5) Manufacturing example  20-5: Synthesis of intermediate 258-2-1

Intermediate 258-2 (2.8 g, 0.011 mol) and bis (pinacolato) dibron (3.3 g, 0.013 mol) Yield: 74%).

LC / MS: m / z = 373 [(M + 1) ^&lt; ^{+ &}

(6) Manufacturing example  20-6: Intermediate 258-3 Synthesis

Intermediate 258-2-1 (3.0 g, 0.008 mol) and 1,4-dibromobenzene (1.6 g, 0.007 mol) were added and the reaction mixture was reacted with 2.4 g of Intermediate 258-3 Yield: 74%).

LC / MS: m / z = 403 [(M + 1) ^&lt; ^{+ &}

(7) Manufacturing example  20-7: Intermediate 258-4 Synthesis

Intermediate 258-3 (5.0 g, 0.007 mol) and 9,9-dimethyl-9H-fluoren-2-amine (1.6 g, 0.007 mol) -4> 2.7 g (yield 72%).

LC / MS: m / z = 530 [(M + 1) ^&lt; ^{+ &}

(8) Manufacturing example  20-8: Synthesis of compound 258

The compound 258-4 (5.0 g, 0.010 mol) and 4-bromodibenzo [b, d] thiophene (2.6 g, 0.010 mol) Yield: 77%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.87 / d, 7.82 / d, 7.62 / d, 7.55 / d, 7.45 / m, 7.41 / m, 7.38 / m, 7.36 / s, 7.28 / m M, 7.52 / d, 7.51 / m, 7.50 / d, 2.74 / d, 1.72 / s, 1.72 /

LC / MS: m / z = 904 [(M + 1) ^&lt; ^{+ &}

Example  21: Compound 320 Synthesis

(One) Manufacturing example  21-1: Synthesis of Intermediate 320-1

Synthesis was conducted in the same manner as in Preparation Example 1-4, except that Intermediate 258-3 (5.0 g, 0.007 mol) and biphenyl-4-amine (1.2 g, 0.007 mol) %).

LC / MS: m / z = 490 [(M + 1) ^&lt; ^{+ &}

(2) Manufacturing example  21-2: Intermediate 320-2 Synthesis

(2.7g, 0.011mol) was added to the reaction mixture, and 2.7g (Intermediate 320-2) of Intermediate 320-2 was synthesized in the same manner as in Production Example 1-8 Yield: 73%).

LC / MS: m / z = 333 [(M + 1) ^&lt; ^{+ &}

(3) Manufacturing example  21-3: Compound 320 Synthesis

5.5 g (yield 75%) of Compound 320 was synthesized by the same method as in Preparation Example 1-4, with the intermediate 320-1 (5.0 g, 0.010 mol) and the intermediate 320-2 (3.3 g, 0.010 mol) .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.45 / d, 7.98 / d, 7.87 / d, 7.82 / d, 7.81 / d, 7.62 / d, 7.55 / d, 7.52 / m, 7.50 / m M, 7.54 / d, 7.50 / d), 7.48 / m, 7.38 / m, 7.36 / s, 7.28 / m, 7.27 / m, 6.98 / d, 6.86 / , 6.69 / d, 2.74 / d, 1.72 / s, 1.72 / m)

LC / MS: m / z = 738 [(M + 1) ^&lt; ^{+ &}

Example  22: Compound 243 Synthesis

The compound 253-4 (5.0 g, 0.010 mol) and 4-bromobiphenyl (2.3 g, 0.010 mol) were added to the reaction mixture to obtain 5.6 g (yield: 77%) of <compound 243> .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.93 / s, 7.82 / d, 7.45 / m, 7.41 / m, 7.36 / s, 6.98 / d) 2H (8.93 / d, 8.12 / d, 7.88 7.52 / d, 7.51 / m, 7.50 / d, 2.74 / d, 1.72 / m) 6H (7.54 / d, 6.69 / d)

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

Example  23: Compound 334 Synthesis

(One) Manufacturing example  23-1: Synthesis of intermediate 334-1

Compound 243 (5.0 g, 0.007 mol) was added thereto, and 1.7 g (yield: 31%) of Intermediate 334-1 was obtained in the same manner as in Production Example 1-3.

LC / MS: m / z = 761 [(M + 1) ^&lt; ^{+ &}

(2) Manufacturing example  23-2: Compound 334 Synthesis

4.7 g (Yield: 71%) of Compound 334 was synthesized by the same method as in Production Example 1-8, except that Intermediate 334-1 (5.0 g, 0.007 mol) and phenylboronic acid (1.0 g, 0.008 mol) .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.87 / d, 7.82 / d, 7.62 / d, 7.55 / d, 7.45 / m, 7.38 / m, 7.28 / m, 7.00 / d, 6.75 / s , 7.58 / d) 2H (7.79 / d, 7.58 / m, 7.52 / d, 7.50 / d, 7.41 / m, 2.74 / d, 1.72 / / d)

LC / MS: m / z = 942 [(M + 1) ^&lt; ^{+ &}

Example  24: Compound 373 Synthesis

(One) Manufacturing example  24-1: Synthesis of intermediate 373-1

2-chloro-4,6-diphenyl-1,3,5-triazine (4.0 g, 0.015 mol) was added to Intermediate 1-1 (3.6 g, 0.015 mol) 3.1 g (yield: 74%) of Intermediate 373-1 was obtained.

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

(2) Manufacturing example  24-2: Synthesis of intermediate 373-1-1

(Pinacolato) dibron (4.0 g, 0.016 mol) was added to Intermediate 373-1 (5.6 g, 0.013 mol), and 4.9 g of Intermediate 373-1-1 Yield: 72%).

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

(3) Manufacturing example  24-3: Intermediate 373-2 Synthesis

Triphenylen-2-ylboronic acid (4.8g, 0.018mol) was added to 1,3-dibromobenzene (3.5g, 0.015mol) and the reaction was conducted in the same manner as in Preparation 1-8 to give 4.0g Yield: 70%).

LC / MS: m / z = 383 [(M + 1) ^&lt; ^{+ &}

(4) Manufacturing example  24-4: Compound 373 Synthesis

(2.2g, 0.006mol) was added to intermediate 373-1-1 (3.7g, 0.007mol), and 2.7g (yield 65%) of compound 373 was synthesized in the same manner as in Production Example 1-8, ).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (9.15 / s, 8.51 / d, 8.18 / d, 8.16 / d, 8.04 / d, 7.70 / s, 7.57 / m, 7.36 / s) 2H (8.93 d, 8.08 / d, 7.88 / m, 7.82 / 7.67 / m, 7.48 / d, 7.41 /

LC / MS: m / z = 701 [(M + 1) ^&lt; ^{+ &}

Example  25: Compound 377 Synthesis

(One) Manufacturing example  25-1: Synthesis of intermediate 377-1

(1.9 g, 0.008 mol) was added to Intermediate 373-1-1 (5.2 g, 0.010 mol) and 3.2 g (Intermediate 377-1) was synthesized in the same manner as in Production Example 1-8 Yield: 72%).

LC / MS: m / z = 553 [(M + 1) ^&lt; ^{+ &}

(2) Manufacturing example  25-2: Intermediate 377-2 Synthesis

(2.8 g, 0.011 mol) of bis (pinacolato) dibron was added to Intermediate 377-1-1 (5.0 g, 0.009 mol), and 3.9 g of Intermediate 377-2 Yield: 72%).

LC / MS: m / z = 600 [(M + 1) ^&lt; ^{+ &}

(3) Manufacturing example  25-3: Compound 377 Synthesis

2-bromo-9,9-dimethyl-10-phenyl-9,10-dihydroacridine (2.9 g, 0.008 mol) was added to Intermediate 377-2 (6.0 g, 0.010 mol) To obtain 4.5 g (yield 74%) of < Compound 377 >.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.51 / d, 8.16 / d, 7.70 / d, 7.61 / s, 7.57 / m, 7.36 / s, 7.05 / d, 7.02 / m, 6.81 / m D, 7.47 / m, 7.20 / m, 6.63 / d, 1.72 / s) d, 7.51 / m)

LC / MS: m / z = 758 [(M + 1) ^&lt; ^{+ &}

Example  26: Compound 392 Synthesis

(One) Manufacturing example  26-1: Synthesis of intermediate 392-1

1,3-dibromobenzene (1.9 g, 0.008 mol) was added to Intermediate 373-1-1 (5.0 g, 0.010 mol), and 3.3 g (Intermediate 392-1) Yield: 74%).

LC / MS: m / z = 553 [(M + 1) ^&lt; ^{+ &}

(2) Manufacturing example  26-2: Synthesis of intermediate 392-2

Intermediate 392-1 (5.0 g, 0.009 mol) was synthesized in the same manner as in Production Example 1-4 except that 1,10-dihydropyrrolo [2,3-a] carbazole (1.9 g, 0.009 mol) -2> (yield: 67%).

LC / MS: m / z = 678 [(M + 1) ^&lt; ^{+ &}

(3) Manufacturing example  26-3: Compound 392 Synthesis

Bromobenzene (1.2 g, 0.007 mol) was added to Intermediate 392-2 (5.0 g, 0.007 mol) and was synthesized in the same manner as in Production Example 1-4 to obtain 3.9 g (yield: 74%) of Compound 392.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 8.51 / d, 8.43 / d, 8.16 / d, 8.09 / s, 7.94 / d, 7.88 / d, 7.60 / d, 7.52 / d D, 7.46 / d, 7.45 / m, 7.36 / s, 7.33 / m, 7.25 / m, 6.52 / d) 2H98.05 / d, 7.67 / m, 7.58 / m, 7.50 / ) 4H (8.28 / d, 7.51 / m)

LC / MS: m / z = 755 [(M + 1) ^&lt; ^{+ &}

Example  27: Compound 394 Synthesis

4.0 g (yield 60%) of <compound 394> was obtained by synthesizing dihydroindeno-dibenzothiophene (2.5 g, 0.009 mol) in Intermediate 392-1 (5.0 g, 0.009 mol) .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 8.51 / d, 8.45 / d, 8.16 / d, 8.09 / s, 8.05 / m, 7.98 / d, 7.94 / d, 7.60 / d D, 8.07 / d, 7.79 / d, 7.67 / m, 7.52 / m, 7.36 / ) 5H (7.51 / m)

LC / MS: m / z = 745 [(M + 1) ^&lt; ^{+ &}

Example  28: Compound 396 Synthesis

(One) Manufacturing example  28-1: Synthesis of intermediate 396-1

Synthesis was conducted in the same manner as in Production Example 1-4 except that 11,12-dihydroindolo [2,3-a] carbazole (2.3 g, 0.009 mol) was added to Intermediate 392-1 (5.0 g, 0.009 mol) -1> (yield: 65%).

LC / MS: m / z = 727 [(M + 1) ^&lt; ^{+ &}

(2) Manufacturing example  28-2: Compound 396 Synthesis

Bromobenzene (1.1 g, 0.007 mol) was added to Intermediate 396-1 (5.0 g, 0.007 mol) and was synthesized in the same manner as in Production Example 1-4 to obtain 4.0 g (yield: 71%) of Compound 396.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.51 / d, 8.16 / d, 8.12 / d, 8.09 / s, 7.57 / d, 7.52 / m, 7.51 / m, 7.46 / d, 7.45 / m M, 7.36 / s) 2H (8.55 / d, 8.05 / d, 7.94 / d, 7.67 / m, 7.58 / m, 7.50 / d, 7.41 / / m)

LC / MS: m / z = 803 [(M + 1) ^&lt; ^{+ &}

Example  29: Compound 399 Synthesis

(One) Manufacturing example  29-1: Synthesis of intermediate 399-1

Bis (pinacolato) dibron (2.5 g, 0.010 mol) was added to 9- (biphenyl-4-yl) -3-bromo-9H-carbazole (3.0 g, 0.008 mol) To obtain 2.6 g (yield: 74%) of Intermediate 399-1.

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

(2) Manufacturing example  29-2: Synthesis of intermediate 399-2

Synthesis was conducted in the same manner as in Preparation Example 1-8, except that 3, 3'-dibromobiphenyl (2.9 g, 0.009 mol) was added to Intermediate 399-1 (5.0 g, 0.011 mol) 71%).

LC / MS: m / z = 550 [(M + 1) ^&lt; ^{+ &}

(3) Manufacturing example  29-3: Compound 399 Synthesis

Intermediate 377-1 (5.0 g, 0.010 mol) was added to Intermediate 399-2 (4.4 g, 0.008 mol), and 4.9 g (Yield: 70%) of Compound 399 was synthesized in the same manner as in Production Example 1-8 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.51 / d, 8.18 / d, 8.16 / d, 8.12 / d, 8.00 / d, 7.77 / s, 7.63 / d, 7.57 / m, 7.50 / m , 7.36 / s, 7.29 / m) 2H (8.05 / d, 7.79 / d, 7.70 / s, 7.68 / d, 7.67 / ) 6H (7.51 / m)

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

Example  30: Compound 435 Synthesis

(One) Manufacturing example  30-1: Synthesis of Intermediate 435-1

(4.2 g, 0.015 mol) was added to Intermediate 1-1 (3.6 g, 0.015 mol) and 4.5 g (Intermediate 435-1) was synthesized in the same manner as in Preparation Example 1-4 Yield: 74%).

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

(2) Manufacturing example  30-2: Intermediate 435-2 Synthesis

Intermediate 435-2 was synthesized in the same manner as in Preparation Example 1-8, except that 1,8-naphthyridin-2-ylboronic acid (1.4 g, 0.008 mol) was added to Intermediate 435-1 (3.6 g, 0.009 mol) 2.4 g (yield: 68%) was obtained.

LC / MS: m / z = 450 [(M + 1) ^&lt; ^{+ &}

(3) Manufacturing example  30-3: Compound 435 Synthesis

Intermediate 373-2 (3.1 g, 0.009 mol) was added to Intermediate 435-2 (3.2 g, 0.007 mol), and 3.3 g (yield 71%) of Compound 435 was synthesized in the same manner as in Production Example 1-6 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (9.15 / s, 8.70 / d, 8.60 / s, 8.51 / d, 8.39 / d, 8.30 / d, 8.18 / d, 8.16 / d, 8.11 / d D, 8.04 / d, 7.70 / s, 7.61 / d, 7.57 / m, 7.54 / m, 7.52 / d, 7.41 / , 7.82 / m, 7.67 / m, 7.48 / d)

LC / MS: m / z = 674 [(M + 1) ^&lt; ^{+ &}

Example  31: Compound 467 Synthesis

(One) Manufacturing example  31-1: Synthesis of intermediate 467-1

4, 6-diphenyl-1,3,5-triazin-2-ylboronic acid (4.9 g, 0.018 mol) was added to 1,4-dibromobenzene (3.6 g, 0.015 mol) To obtain 5.8 g (yield 74%) of Intermediate 467-1.

LC / MS: m / z = 388 [(M + 1) ^&lt; ^{+ &}

(2) Manufacturing example  31-2: Compound 467 Synthesis

Intermediate 467-1 (2.7 g, 0.007 mol) was added to Intermediate 1-3 (3.0 g, 0.008 mol), and 2.9 g (yield 75%) of Compound 467 was synthesized in the same manner as in Production Example 1-8 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.51 / d, 8.16 / d, 7.45 / m) 2H (8.05 / d, 7.85 / d, 7.67 / m, 7.58 / m, 7.50 / d, 7.41 / m, 7.25 / d) 4H (8.28 / d, 7.51 / m)

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

Example  32: Compound 469 Synthesis

(One) Manufacturing example  32-1: Synthesis of intermediate 469-1

4,6-diphenylpyrimidin-2-ylboronic acid (4.9 g, 0.018 mol) was added to 1,4-dibromobenzene (3.6 g, 0.015 mol) (Yield: 72%).

LC / MS: m / z = 387 [(M + 1) ^&lt; ^{+ &}

(2) Manufacturing example  32-2: Compound 469 Synthesis

Intermediate 469-1 (2.7 g, 0.007 mol) was added to Intermediate 1-3 (3.0 g, 0.008 mol), and 2.8 g (yield 72%) of Compound 469 was synthesized in the same manner as in Production Example 1-8 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.51 / d, 8.23 / s, 8.16 / d, 7.45 / m, 7.36 / s) 2H (8.05 / d, 7.85 / d, 7.67 / m, 7.58 7.50 / d, 7.41 / m, 7.25 / d) 4H (7.79 / d, 7.51 / m)

LC / MS: m / z = 550 [(M + 1) ^&lt; ^{+ &}

Example  33: Compound 474 Synthesis

(One) Manufacturing example  33-1: Synthesis of intermediate 474-1

Synthesis was conducted in the same manner as in Production Example 1-8, except that 1,3-dibromobenzene (1.6 g, 0.007 mol) was added to 9-phenyl-9H-carbazol-3-ylboronic acid (2.6 g, 0.009 mol) -1> 2.1 g (yield: 74%).

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

(2) Manufacturing example  33-2: Synthesis of compound 474

3.0 g (Yield: 76%) of Compound 474 was synthesized by the same method as in Preparation Example 1-8, except that Intermediate 474-1 (2.8 g, 0.007 mol) was added to Intermediate 1-3 (3.0 g, 0.008 mol) .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H98.55 / d, 8.51 / d, 8.16 / d, 7.94 / d, 7.87 / d, 7.77 / s, 7.70 / s, 7.69 / d, 7.57 / m (7.58 / m, 7.50 / d), 7.36 / s, 7.33 /

LC / MS: m / z = 560 [(M + 1) ^&lt; ^{+ &}

Example  34: Compound 481 Synthesis

(One) Manufacturing example  34-1: Synthesis of intermediate 481-1

1-bromo-3-iodobenzene (4.2 g, 0.015 mol) was added to Intermediate 1-1 (3.6 g, 0.015 mol) and the reaction was conducted in the same manner as in Preparation Example 1-4 to give 5.0 g (Intermediate 481-1) Yield: 74%).

LC / MS: m / z = 448 [(M + 1) ^&lt; ^{+ &}

(2) Manufacturing example  34-2: Intermediate 481-2 Synthesis

Triphenylen-2-ylboronic acid (2.7 g, 0.010 mol) was added to Intermediate 481-1 (3.6 g, 0.008 mol), and 3.2 g of Intermediate 481-2 74%).

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

(3) Manufacturing example  34-3: Intermediate 481-3 Synthesis

4-ylboronic acid (5.0 g, 0.018 mol) was added to 1,4-dibromobenzene (3.6 g, 0.015 mol) in the same manner as in Preparation Example 1-8 to obtain Intermediate 481-3 (Yield: 70%).

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

(4) Manufacturing example  34-4: Intermediate 481-4 Synthesis

(2.5g, 0.010mol) of bis (pinacolato) dibron was added to Intermediate 481-3 (3.9g, 0.008mol), and 2.4g (yield 69 %). (M / z = 433)

LC / MS: m / z = 433 [(M + 1) ^&lt; ^{+ &}

(5) Manufacturing example  34-5: Synthesis of compound 481

3.4 g (yield 74%) of <compound 481> was obtained by synthesizing 4-bromobiphenyl (2.9 g, 0.006 mol) in Intermediate 481-4 (3.0 g, 0.007 mol) by the same method as in Preparation Example 1-8 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (9.15 / s, 8.51 / d, 8.18 / d, 8.16 / d, 8.09 / s, 8.04 / d, 7.52 / d, 7.51 / m, 7.46 / d D, 7.54 / m, 7.25 / d), 7.36 / s) 2H (8.93 d, 8.20 s, 8.12 d, 8.05 d, 7.88 m, 7.82 m, 7.67 m)

LC / MS: m / z = 775 [(M + 1) ^&lt; ^{+ &}

Example  35: Compound 508 Synthesis

(One) Manufacturing example  35-1: Synthesis of intermediate 508-1

Intermediate 469-1 (3.5 g, 0.009 mol) was added to 3,6-dibromo-9H-carbazole (3.0 g, 0.009 mol) g (yield: 74%).

LC / MS: m / z = 631 [(M + 1) ^&lt; ^{+ &}

(2) Manufacturing example  35-2: Synthesis of compound 508

Intermediate 1-3 (7.0 g, 0.019 mol) was added to Intermediate 508-1 (5.0 g, 0.008 mol), and 5.4 g (Yield: 70%) of Compound 508 was synthesized in the same manner as in Production Example 1-8 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.23 / s, 8.18 / d, 8.00 / d, 7.87 / d, 7.69 / d) 2H (8.51 / d, 8.16 / d, 7.77 / s, 7.68 d, 7.45 / m, 7.41 / m, 7.36 / s) 4H (8.05 / d, 7.67 / m, 7.58 / m, 7.51 / m, 7.50 / d)

LC / MS: m / z = 957 [(M + 1) ^&lt; ^{+ &}

Example  36: Compound 505 Synthesis

(One) Manufacturing example  36-1: Synthesis of intermediate 505-1

Intermediate 467-1 (3.5 g, 0.009 mol) was added to 3,6-dibromo-9H-carbazole (3.0 g, 0.009 mol) g (yield: 76%).

LC / MS: m / z = 632 [(M + 1) ^&lt; ^{+ &}

(2) Manufacturing example  36-2: Compound 505 Synthesis

Intermediate 1-3 (7.0 g, 0.019 mol) was added to Intermediate 508-1 (5.0 g, 0.008 mol), and 5.7 g (yield 75%) of Compound 505 was synthesized in the same manner as in Production Example 1-8 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.18 / d, 8.00 / d, 7.87 / d, 7.69 / d) 2H (8.51 / d, 8.16 / d, 7.79 / d, 7.77 / s, 7.68 7.55 / m, 7.41 / m, 7.36 / s) 4H (8.28 / d, 8.05 / d, 7.67 / m, 7.58 /

LC / MS: m / z = 957 [(M + 1) ^&lt; ^{+ &}

Example  37: Compound 506 Synthesis

(One) Manufacturing example  37-1: Synthesis of intermediate 506-1

Intermediate 481-1 (3.5 g, 0.009 mol) was added to 3,6-dibromo-9H-carbazole (3.0 g, 0.009 mol) g (yield 70%).

LC / MS: m / z = 630 [(M + 1) ^&lt; ^{+ &}

(2) Manufacturing example  37-2: Compound 506 Synthesis

Intermediate 1-3 (7.0 g, 0.019 mol) was added to Intermediate 506-1 (5.0 g, 0.008 mol) and synthesized according to the same method as that of Preparation Example 1-8 to give 5.3 g (Yield: 70%) of Compound 506 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.18 / d, 8.00 / d, 7.87 / d, 7.69 / d) 2H (8.51 / d, 8.20 / s, 8.16 / d, 7.79 / d, 7.77 d, 8.05 / d, 7.67 / m, 7.58 / m, 7.54 / m, 7.50 / d)

LC / MS: m / z = 956 [(M + 1) ^&lt; ^{+ &}

Example  38: Compound 509 Synthesis

(One) Manufacturing example  38-1: Synthesis of intermediate 509-1

2-bromo-4,6-diphenyl-1,3,5-triazine (2.8 g, 0.009 mol) was added to 3,6-dibromo-9H-carbazole (3.0 g, 0.009 mol) (Intermediate 509-1) (4.0 g, yield 80%).

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

(2) Manufacturing example  38-2: Compound 509 Synthesis

Intermediate 1-3 (8.0 g, 0.021 mol) was added to Intermediate 509-1 (5.0 g, 0.009 mol), and 6.2 g (yield 78%) of Compound 509 was synthesized in the same manner as in Production Example 1-8 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.18 / d, 8.00 / d, 7.87 / d, 7.69 / d) 2H (8.51 / d, 8.16 / d, 7.79 / d, 7.77 / s, 7.68 d, 8.05 / d, 7.67 / m, 7.58 / m, 7.54 / m, 7.50 / d)

LC / MS: m / z = 882 [(M + 1) ^&lt; ^{+ &}

Example  39: Compound 519 Synthesis

(One) Manufacturing example  39-1: Synthesis of intermediate 519-1

Dibromobenzene (1.2 g, 0.005 mol) was added to 3,6-dibromo-9H-carbazole (3.0 g, 0.009 mol), and <Intermediate 519-1> (Yield: 81%).

LC / MS: m / z = 724 [(M + 1) ^&lt; ^{+ &}

(2) Manufacturing example  39-2: Synthesis of intermediate 519-2

5.5 g (yield: 74%) of Intermediate 519-2 (5.0 g, 0.007 mol) was used in place of Intermediate 1-3 (3.0 g, 0.008 mol) ).

LC / MS: m / z = 1048 [(M + 1) ^&lt; ^{+ &}

(3) Manufacturing example  39-3: Compound 519 Synthesis

Phenyl-1H-benzo [d] imidazole (1.9 g, 0.010 mol) was added to Intermediate 519-2 (5.0 g, 0.005 mol) g (yield: 74%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.18 / d, 8.00 / d, 7.87 / d, 7.69 / d) 2H (8.56 / d, 8.51 / d, 8.16 / d, 7.77 / s, 7.59 7.50 / d, 7.50 / d, 7.52 / m), and the like.

LC / MS: m / z = 1276 [(M + 1) ^&lt; ^{+ &}

Example  40: Compound 542 Synthesis

(One) Manufacturing example  40-1: Synthesis of intermediate 542-1

Synthesis was conducted in the same manner as in Preparation Example 1-8, except that 1,3-dibromo-5-chlorobenzene (0.8 g, 0.003 mol) was added to Intermediate 1-3 (3.0 g, 0.008 mol) g (yield: 69%).

LC / MS: m / z = 595 [(M + 1) ^&lt; ^{+ &}

(2) Manufacturing example  40-2: Synthesis of intermediate 542-1-1

(2.5g, 0.010mol) of bis (pinacolato) dibron was added to Intermediate 542-1 (5.0g, 0.008mol), and 3.6g of Intermediate 542-2 (yield: 66 %).

LC / MS: m / z = 686 [(M + 1) ^&lt; ^{+ &}

(3) Manufacturing example  40-3: Intermediate 542-2 Synthesis

Synthesis was carried out in the same manner as in Preparation Example 1-8 except that 2-bromo-4,6-dichloro-1,3,5-triazine (1.6 g, 0.07 mol) was added to Intermediate 542-1 (5.0 g, 0.008 mol) To obtain 3.7 g (yield 66%) of Intermediate 542-2.

LC / MS: m / z = 708 [(M + 1) ^&lt; ^{+ &}

(4) Manufacturing example  40-4: Compound 542 Synthesis

Compound 542 was synthesized according to the same method as that of Preparation Example 1-4, except that 2-phenyl-1H-benzo [d] imidazole (2.7 g, 0.014 mol) was added to Intermediate 542-2 (5.0 g, 0.007 mol) g (yield: 74%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (8.56 / d, 8.51 / d, 8.16 / d, 7.59 / d, 7.45 / m, 7.36 / s) 3H (7.66 / s) 4H (8.28 / d , 8.005 / d, 7.67 / m, 7.58 / m, 7.51 / m, 7.50 / d, 7.22 /

LC / MS: m / z = 1025 [(M + 1) ^&lt; ^{+ &}

Example  41: Compound 563 Synthesis

(One) Manufacturing example  41-1: Synthesis of intermediate 563-1

2-bromotriphenylene (2.8 g, 0.009 mol) was added to 3,6-dibromo-9H-carbazole (3.0 g, 0.009 mol), and 3.7 g of Intermediate 563-1 (Yield: 74%).

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

(2) Manufacturing example  41-2: Compound 563 Synthesis

Intermediate 1-3 (4.1 g, 0.011 mol) was added to Intermediate 563-1 (3.0 g, 0.009 mol), and 5.8 g (yield 74%) of Compound 563 was synthesized in the same manner as in Production Example 1-8 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (9.15 / s, 8.18 / d, 8.04 / d, 8.00 / d, 7.87 / d, 7.69 / d) 2H (8.93 / d, 8.51 / d, 8.16 / d, 8.12 / d, 7.88 / m, 7.82 / m, 7.77 / s, 7.45 / m, 7.36 / s)

LC / MS: m / z = 877 [(M + 1) ^&lt; ^{+ &}

Example  42: Compound 588 Synthesis

(One) Manufacturing example  42-1: Synthesis of intermediate 588-1

(2.2 g, 0.007 mol) was added to a solution of Intermediate 258-2-1 (5.0 g, 0.008 mol) and N- (biphenyl-4-yl) -9,9- 8, 3.4 g (yield 75%) of Intermediate 588-1 was obtained.

LC / MS: m / z = 647 [(M + 1) ^&lt; ^{+ &}

(2) Manufacturing example  42-2: Intermediate 588-2 Synthesis

Intermediate 588-1 (5.0g, 0.008mol) and bis (pinacolato) dibron (2.5g, 0.010mol) were added to the reaction mixture to obtain 4.2g of Intermediate 588-2 %).

LC / MS: m / z = 694 [(M + 1) ^&lt; ^{+ &}

(3) Manufacturing example  42-3: Intermediate 588-3 Synthesis

Intermediate 588-2 (5.6 g, 0.008 mol) and 1,4-dibromobenzene (1.6 g, 0.007 mol) were added to the reaction mixture to obtain 3.8 g of Intermediate 588-3 (yield 75 %).

LC / MS: m / z = 723 [(M + 1) ^&lt; ^{+ &}

(4) Manufacturing example  42-4: Compound 588 Synthesis

Compound 588 was synthesized by the same method as Preparation Example 1-4, except that Intermediate 588-3 (5.0 g, 0.007 mol) and 2-phenyl-1H-benzo [d] imidazole (1.4 g, 0.007 mol) g (yield: 77%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (8.28 / d, 7.82 / d, 7.79 / d, 7.68 / d, 7.51 / m, 7.45 / m, 7.36 / s, 7.22 / m, 6.98 / d ) 3H (8.56 / d, 7.66 / s, 7.51 / d, 7.41 / m) 4H97.58 / m, 7.50 / d, 2.74 / d, 1.72 /

LC / MS: m / z = 767 [(M + 1) ^&lt; ^{+ &}

Example  43: Compound 597 Synthesis

(One) Manufacturing example  43-1: Synthesis of intermediate 597-1

Synthesis was conducted in the same manner as in Preparation Example 1-8, except that 3-bromo-9H-carbazole (2.0 g, 0.008 mol) was added to Intermediate 1-3 (3.0 g, 0.008 mol) Yield: 74%). (M / z = 408)

LC / MS: m / z = 408 [(M + 1) ^&lt; ^{+ &}

(2) Manufacturing example  43-2: Synthesis of intermediate 597-2

(1.4 g, 0.007 mol) was added to Intermediate 591-1 (3.0 g, 0.007 mol), and 2.7 g (yield 72%) of Intermediate 597-2 %).

LC / MS: m / z = 528 [(M + 1) ^&lt; ^{+ &}

(3) Manufacturing example  43-3: Compound 597 Synthesis

Triphenylene boronic acid (2.5 g, 0.008 mol) was added to Intermediate 597-2 (5.0 g, 0.010 mol) and was synthesized in the same manner as in Preparation Example 1-8 to give 4.2 g (yield 74%) of Compound 597 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (9.15 / s, 8.55 / d, 8.51 / d, 8.18 / d, 8.16 / d, 8.04 / d, 7.94 / d, 7.87 / d, 7.77 / s , 7.69 / d, 7.45 / m, 7.36 / s, 7.33 / m, 7.25 / m)

LC / MS: m / z = 711 [(M + 1) ^&lt; ^{+ &}

Example  44: Compound 598 Synthesis

To a solution of intermediate 597-2 (5.0 g, 0.010 mol) was added 4,6-diphenyl-1,3,5-triazin-2-ylboronic acid (2.1 g, 0.008 mol) To obtain 4.0 g (yield 70%) of < Compound 598 >.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 8.51 / d, 8.16 / d, 7.94 / d, 7.87 / d, 7.77 / s, 7.69 / d, 7.45 / m, 7.36 / s M), 7H (8.08 / d, 7.71 / d, 7.68 / d, 7.67 / m, 7.58 / m, 7.50 / d, 7.41 /

LC / MS: m / z = 716 [(M + 1) ^&lt; ^{+ &}

Example  45: Compound 648 Synthesis

(One) Manufacturing example  45-1: Synthesis of intermediate 648-1

100 ml of 1, 2-dichlorobenzene was added to triphenylphosphine (4.5 g, 0.017 mol) in 2-bromo-2'-nitrobiphenyl (5.0 g, 0.017 mol) and the mixture was reacted at 180 ° C for 24 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 4.2 g (yield: 83%) of Intermediate 648-1.

LC / MS: m / z = 246 [(M + 1) ^&lt; ^{+ &}

(2) Manufacturing example  45-2: Intermediate 648-2 Synthesis

Intermediate 648-1 (1.7 g, 0.007 mol) was added to Intermediate 93-3 (4.2 g, 0.008 mol), and 2.3 g of Intermediate 648-2 (yield: 71% ).

LC / MS: m / z = 458 [(M + 1) ^&lt; ^{+ &}

(3) Manufacturing example  45-3: Compound 648 Synthesis

4-chloro-2,6-diphenylpyridine (2.9 g, 0.011 mol) was added to Intermediate 648-2 (5.0 g, 0.011 mol) and the compound 648 was synthesized in the same manner as in Preparation Example 1-4 to obtain 5.6 g Yield: 74%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 7.94 / d, 7.79 / d, 7.59 / d, 7.43 / m, 7.36 / s, 7.33 / m, 7.25 / m) 2H (8.93 7.58 / m, 7.50 / d, 7.47 / m, 7.10 / s) 4H (8.30 / d, 7.54 /

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

Example  46: Compound 644 Synthesis

(One) Manufacturing example  46-1: Synthesis of intermediate 644-1

2.1 g (yield: 74%) of Intermediate 644-1 (1.7 g, 0.007 mol) was added to Intermediate 1-3 (3.0 g, 0.008 mol) ).

LC / MS: m / z = 408 [(M + 1) ^&lt; ^{+ &}

(2) Manufacturing example  46-2: Synthesis of intermediate 644-2

(1.6 g, 0.008 mol) was added to Intermediate 644-2 (3.0 g, 0.008 mol), and 2.9 g (yield: 68%) of Intermediate 644-2 %).

LC / MS: m / z = 528 [(M + 1) ^&lt; ^{+ &}

(3) Manufacturing example  46-3: Compound 644 Synthesis

4.5 g (yield 70%) of <compound 644> was obtained by synthesizing triphenylene boronic acid (2.4 g, 0.007 mol) in Intermediate 644-2 (5.0 g, 0.009 mol) by the same method as in Preparation Example 1-8 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (9.15 / s, 8.51 / d, 8.18 / d, 8.16 / d, 8.04 / d, 7.94 / d, 7.79 / d, 7.59 / d, 7.45 / m D, 8.08 / d, 7.88 / m, 7.82 / m, 7.79 / d, 7.68 / d, 7.67 / m , 7.58 / m, 7.50 / d)

LC / MS: m / z = 711 [(M + 1) ^&lt; ^{+ &}

Example  47: Compound 625 Synthesis

Synthesis was conducted in the same manner as in Production Example 1-8, except that 1.6 g (0.006 mol) of 4,6-diphenyl-1,3,5-triazine-boronic acid was added to Intermediate 644-2 (3.0 g, 0.007 mol) 3.1 g (yield 72%) of Compound 625 was obtained.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 8.51 / d, 8.16 / d, 7.94 / d, 7.59 / d, 7.45 / m, 7.43 / m, 7.33 / m, 7.25 / m ), 2H (8.05 / d, 7.68 / d, 7.67 / m, 7.58 / m, 7.50 /

LC / MS: m / z = 716 [(M + 1) ^&lt; ^{+ &}

Example  48: Synthesis of compound 654

(One) Manufacturing example  48-1: Synthesis of intermediate 654-1

2-chloro-4,6-diphenyl-1,3,5-triazine (3.2 g, 0.012 mol) was added to Intermediate 93-1 (3.0 g, 0.012 mol) To obtain 4.7 g (yield: 74%) of Intermediate 654-1.

LC / MS: m / z = 527 [(M + 1) ^&lt; ^{+ &}

(2) Manufacturing example  48-2: Synthesis of intermediate 654-2

(3.0 g, 0.012 mol) of bis (pinacolato) dibron was added to Intermediate 654-1 (5.0 g, 0.010 mol), and 4.0 g of Intermediate 654-2 %).

LC / MS: m / z = 574 [(M + 1) ^&lt; ^{+ &}

(3) Manufacturing example  48-3: Synthesis of compound 654

Intermediate 373-2 (3.0 g, 0.008 mol) was added to Intermediate 654-2 (5.7 g, 0.010 mol), and 4.2 g (yield 70%) of Compound 654 was synthesized in the same manner as in Production Example 1-5 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (9.15 / s, 8.18 / d, 8.04 / d, 7.70 / s, 7.57 / m, 7.36 / s) 2H (7.48 / d, 7.41 / m) 4H (8.93 / d, 8.28 / d, 8.12 / d, 7.88 / m, 7.82 / m, 7.51 /

LC / MS: m / z = 751 [(M + 1) ^&lt; ^{+ &}

Example  49: Compound 773 Synthesis

(One) Manufacturing example  49-1: Synthesis of Intermediate 773-1

2-bromo-4,6-diphenyl-1,3,5-triazine (4.6 g, 0.015 mol) was added to Intermediate 258-1 (3.0 g, 0.015 mol) To obtain 4.9 g (yield 75%) of Intermediate 773-1.

LC / MS: m / z = 436 [(M + 1) ^&lt; ^{+ &}

(2) Manufacturing example  49-2: Synthesis of Intermediate 773-2

(1.8 g, 0.012 mol) was added to 11,12-dihydroindolo [2,3-a] carbazole (3.0 g, 0.012 mol) 3.2 g (yield 80%) was obtained.

LC / MS: m / z = 332 [(M + 1) ^&lt; ^{+ &}

(3) Manufacturing example  49-3: Synthesis of intermediate 773-3

(2.2 g, 0.011 mol) was added to Intermediate 773-2 (3.0 g, 0.009 mol), and 2.7 g (yield: 67%) of Intermediate 773-3 %).

LC / MS: m / z = 452 [(M + 1) ^&lt; ^{+ &}

(4) Manufacturing example  49-4: Intermediate 773-4 Synthesis

(2.3g, 0.009mol) of bis (pinacolato) dibron was added to Intermediate 773-1 (3.0g, 0.007mol), and 2.3g of Intermediate 773-4 was obtained in the same manner as in Preparation Example 1-5 %).

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

(5) Manufacturing example  49-5: Synthesis of compound 773

Intermediate 773-4 (4.3 g, 0.008 mol) was added to Intermediate 773-1 (3.0 g, 0.007 mol), and 3.6 g (yield 63%) of Compound 773 was synthesized in the same manner as in Production Example 1-6 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (9.15 / s, 8.18 / d, 8.04 / d, 7.70 / s, 7.57 / m, 7.36 / s) 2H (7.48 / d, 7.41 / m) 4H (8.93 / d, 8.28 / d, 8.12 / d, 7.88 / m, 7.82 / m, 7.51 /

LC / MS: m / z = 808 [(M + 1) ^&lt; ^{+ &}

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

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

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

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

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

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

Device Example  One: Compound 1 With hole transport material  So Organic electroluminescent device  Produce

Depositing a <compound 1> over a glass substrate coated with ITO to form a hole transport layer was of 120nm, followed by Ir (ppy) the deposition rate of CBP as a host and to a ₃ with a dopant 0.1nm / sec, Ir (ppy) ₃ The deposition rate was 0.009 nm / sec, and Ir (ppy) ₃ was doped so that the deposition rate ratio was 9% to form a light emitting layer with a thickness of 30 nm on the hole transport layer.

Balq was deposited thereon to a thickness of 10 nm to form a hole blocking layer for preventing holes from moving to the electron transporting layer through the light emitting layer, and 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.

At this time, the deposition rate of each material was set to 0.1 nm / sec for compound 1, CBP, Alq ₃ , Balq, 0.01 nm / sec for lithium fluoride, and 0.5 nm / sec for aluminum.

Device Example  2 to 23

The organic electroluminescent devices of the device embodiments 2 to 23 were fabricated in the same manner as in the device example 1, except that the compound described in the following Table 1 was used instead of the compound 1.

Device comparison example  One

The organic light emitting diode device for Comparative Example 1 was fabricated in the same manner except that NPB, which is generally used as a hole transport material, was used instead of the compound 1 produced by the invention in the device structure of the above embodiment.

Device Example  24: Compound 24 The light-  As a host material Organic electroluminescent device  Produce

NPB was deposited on a glass substrate coated with ITO to form a hole transporting layer having a thickness of 120 nm. Next, Ir (ppy) ₃ was used as a dopant, and the deposition rate was set to 0.1 nm / ) ₃ deposition rate of 0.009 nm / sec was deposited, and Ir (ppy) ₃ was doped so that the deposition rate ratio was 9% to form a light emitting layer with a thickness of 30 nm on the hole transport layer.

Balq was deposited thereon to a thickness of 10 nm to form a hole blocking layer for preventing holes from moving to the electron transporting layer through the light emitting layer, and 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.

At this time, the deposition rate of each material was set to 0.1 nm / sec for compound 24, NPB, Alq ₃ , Balq, 0.01 nm / sec for lithium fluoride, and 0.5 nm / sec for aluminum.

Device Example  25 to 49

The organic EL devices of the device examples 25 to 49 were fabricated in the same manner as in the device example 24, except that the compound described in the following Table 2 was used in place of the compound 24.

Device comparison example  2

The organic light emitting diode device for Comparative Example 2 was fabricated in the same manner except that CBP, which is generally used as a phosphorescent host material, was used instead of the compound 24 produced by the present invention in the device structure of the embodiment.

The structures of Ir (ppy) 3, CBP and NPB used in the above are as follows.

The results of comparison between the characteristics of the organic electroluminescent devices manufactured according to the device embodiments 1 to 49 and the device comparison examples 1 and 2 are shown in Tables 1 and 2 below.

division Hole transport material The driving voltage (V)
(at 1000 cd / m 2) Luminous efficiency
(cd / A) Color coordinates
(CIE (x, y)) Device Embodiment 1 Compound 1 5.0 53 (0.31, 0.63) Device Example 2 Compound 3 5.1 49 (0.31, 0.63) Device Embodiment 3 Compound 7 5.0 54 (0.32, 0.64) Device Example 4 Compound 17 4.4 61 (0.32, 0.64) Element Embodiment 5 Compound 22 4.5 49 (0.32, 0.64) Device Example 6 Compound 33 4.9 51 (0.32, 0.64) Device Example 7 Compound 35 4.9 51 (0.34, 0.62) Device Example 8 Compound 38 5.1 53 (0.35, 0.63) Device Example 9 Compound 48 4.9 60 (0.34, 0.62) Element Embodiment 10 Compound 49 4.5 55 (0.32, 0.64) Element Embodiment 11 Compound 66 5.1 53 (0.35, 0.64) Device Example 12 Compound 73 4.5 59 (0.32, 0.64) Device Embodiment 13 Compound 76 5.0 54 (0.35, 0.65) Device Embodiment 14 Compound 93 5.0 48 (0.34, 0.62) Device Example 15 Compound 114 5.0 51 (0.33, 0.63) Device Embodiment 16 Compound 171 4.9 48 (0.32, 0.62) Device Example 17 Compound 172 4.8 61 (0.33, 0.62) Element Embodiment 18 Compound 174 5.0 48 (0.35, 0.66) Element Embodiment 19 Compound 220 5.1 51 (0.32, 0.63) Device Embodiment 20 Compound 243 4.7 51 (0.31, 0.63) Device Example 21 Compound 258 4.4 53 (0.32, 0.62) Device Embodiment 22 Compound 320 4.8 52 (0.32, 0.63) Device Example 23 Compound 334 4.8 50 (0.33, 0.62) Device Comparative Example 1 N P B 6.8 37 (0.33, 0.62)

division Emitting material
The driving voltage (V)
(at 1000 cd / m 2) Luminous efficiency
(cd / A) Color coordinates
(CIE (x, y)) Device Embodiment 24 Compound 373 5.0 46 (0.31, 0.63) Device Example 25 Compound 377 5.1 46 (0.31, 0.63) Device Embodiment 26 Compound 392 5.0 47 (0.32, 0.64) Device Example 27 Compound 394 4.8 61 (0.32, 0.64) Device Example 28 Compound 396 4.5 54 (0.32, 0.64) Element Embodiment 29 Compound 399 4.9 45 (0.32, 0.64) Device Example 30 Compound 435 4.9 45 (0.34, 0.62) Element Embodiment 31 Compound 467 5.1 46 (0.35, 0.63) Device Example 32 Compound 469 4.8 60 (0.34, 0.62) Device Example 33 Compound 474 4.5 47 (0.32, 0.64) Device Example 34 Compound 481 5.1 52 (0.35, 0.64) Device Example 35 Compound 505 4.5 59 (0.32, 0.64) Device Example 36 Compound 506 5.0 51 (0.35, 0.65) Device Example 37 Compound 508 5.0 51 (0.34, 0.62) Device Example 38 Compound 509 5.0 47 (0.33, 0.63) Device Example 39 Compound 519 4.9 48 (0.32, 0.62) Device Example 40 Compound 542 4.8 61 (0.33, 0.62) Device Example 41 Compound 563 5.0 45 (0.35, 0.66) Device Example 42 Compound 588 5.1 47 (0.32, 0.63) Device Embodiment 43 Compound 597 4.8 58 (0.31, 0.63) Element Embodiment 44 Compound 598 5.1 46 (0.32, 0.62) Device Example 45 Compound 625 4.8 46 (0.32, 0.63) Device Embodiment 46 Compound 644 4.7 60 (0.33, 0.62) Device Embodiment 47 Compound 648 4.7 48 (0.31, 0.62) Device Example 48 Compound 654 4.8 52 (0.32, 0.63) Device Example 49 Compound 773 4.8 51 (0.32, 0.62) Device Comparative Example 2 C B P 6.8 37 (0.33, 0.62)

Measurement of driving voltage and luminous efficiency

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

According to Tables 1 and 2, when the compound for an organic electroluminescent device according to the present invention is used as a host material and a hole transport material of a light emitting layer of an organic electroluminescent device, conventional CBP (host material) and NPB (hole transport material) The driving voltage is lowered and the luminous efficiency is increased.

Claims (7)

A compound for an organic electroluminescence device represented by any of Structural Forms 1-1 to 1-6 shown below.
[Structural formula 1-1] [Structural formula 1-2]

[Structural Formula 1-3] [Structural Formula 1-4]

[Structural formulas 1-5] [Structural formulas 1-6]

In the structural formulas 1-1 to 1-6,
R &lt; _{1 &gt;} is hydrogen or a phenyl group,
Ar ₁ represents a phenyl group, a pyridine group, a biphenyl group, or

,

or

Lt;
L represents a phenyl group, a pyridine group, a biphenyl group, a naphthyl group,

,

or

Lt;
Ar ₂ and Ar ₃ may be the same or different from each other, Ar ₂ and Ar ₃ are each independently a biphenyl group,

,

,

,

,

,

,

,

,

,

,

, or

ego,
Ar ₄ represents a phenyl group or

ego,
Ar ₅ is

,

,

,

,

,

,

,

,

,

,

, or

ego,
Ar ₆ is

,

,

,

,

,

, or

to be. delete The method according to claim 1,
Wherein the compound for an organic electroluminescence device is any one selected from compounds represented by the following formulas.

An organic electroluminescent device comprising the compound for organic electroluminescent device according to claim 1. A light emitting layer and a hole transporting layer between the first electrode and the second electrode,
Wherein one of the light emitting layer and the hole transporting layer comprises the compound for an organic electroluminescence device according to claim 1. 6. The method of claim 5,
Wherein the organic electroluminescent device further comprises at least one selected from the group consisting of an electron injecting layer, an electron transporting layer, a hole blocking layer, an electron blocking layer, and a hole injecting layer between the first electrode and the second electrode. An electroluminescent device. 6. The method of claim 5,
Wherein the light emitting layer comprises a host and a dopant.

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