KR20220136247A - Novel compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a novel compound and an organic light emitting device using the same. The present invention provides a compound represented by chemical formula 1. The compound represented by chemical formula 1 can be used as a material for an organic layer of the organic light emitting device, and thus can improve efficiency, lower driving voltage, and/or improve lifespan characteristics of the organic light emitting device.

Description

Novel compound and organic light emitting device using the same

The present invention relates to a novel compound and an organic light emitting device comprising the same.

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, and excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.

An organic light emitting device generally has a structure including an anode and a cathode and an organic material layer between the anode and the cathode. The organic layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light-emitting device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons It lights up when it falls back to the ground state.

The development of new materials for organic materials used in organic light emitting devices as described above is continuously required.

Korean Patent Publication No. 10-2000-0051826

The present invention relates to a novel compound and an organic light emitting device comprising the same.

The present invention provides a compound represented by the following formula (1):

[Formula 1]

In Formula 1,

A ₁ is represented by the following formula 1-a,

[Formula 1-a]

In Formula 1-a,

The dotted line is the part that is fused with the adjacent ring,

X is O or S;

Ar ₁ is substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S,

A ₂ is the following formula 1-b; Or a substituent represented by the following formula 1-c,

[Formula 1-b]

[Formula 1-c]

In Formulas 1-b and 1-c,

L ₁ to L ₄ are each independently, a single bond; substituted or unsubstituted C _6-60 arylene; Or substituted or unsubstituted C _2-60 heteroarylene containing any one or more heteroatoms selected from the group consisting of N, O and S,

Ar ₂ to Ar ₅ are each independently, substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S,

D is deuterium,

n is an integer from 0 to 5;

In addition, the present invention is a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Formula 1 above. do.

The compound represented by Chemical Formula 1 described above may be used as a material for the organic layer of the organic light emitting device, and may improve efficiency, low driving voltage and/or lifespan characteristics in the organic light emitting device. In particular, the compound represented by Chemical Formula 1 described above may be used as a material for hole injection, hole transport, hole injection and transport, electron blocking, light emission, electron transport, or electron injection material.

1 shows an example of an organic light emitting device including a substrate 1 , an anode 2 , an organic material layer 3 , and a cathode 4 .
2 is a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (8), a hole blocking layer (9), an electron transport layer (10) , an example of an organic light emitting device comprising an electron injection layer 11 and a cathode 4 is shown.
3 is a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (8), a hole blocking layer (9), an electron injection and transport layer ( 12) and an example of an organic light-emitting device including a cathode 4 are shown.

Hereinafter, it will be described in more detail to help the understanding of the present invention.

The present invention provides a compound represented by the above formula (1).

및

는 다른 치환기에 연결되는 결합을 의미한다. In this specification,

and

means a bond connected to another substituent.

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkyl thiooxy group; arylthioxy group; an alkyl sulfoxy group; arylsulfoxy group; silyl group; boron group; an alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; heteroarylamine group; arylamine group; an aryl phosphine group; or N, O, and S atom means that it is substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group containing one or more, or substituted or unsubstituted, in which two or more substituents of the above-exemplified substituents are connected . For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but it is preferably from 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, in the ester group, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but it is preferably from 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. However, the present invention is not limited thereto.

In the present specification, the boron group specifically includes a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like, but is not limited thereto.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the carbon number of the alkenyl group is 2 to 10. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 30. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a monocyclic aryl group, such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,

etc. can be However, the present invention is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group including at least one of O, N, Si and S as a heterogeneous element, and the number of carbon atoms is not particularly limited, but it is preferably from 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, an acridyl group , pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, isoxazolyl group, thiadia and a jolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but is not limited thereto.

In the present specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group is the same as the example of the aryl group described above. In the present specification, the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the above-described alkyl group. In the present specification, the description of the heterocyclic group described above for heteroaryl among heteroarylamines may be applied. In the present specification, the alkenyl group among the aralkenyl groups is the same as the examples of the above-described alkenyl groups. In the present specification, the description of the above-described aryl group may be applied except that arylene is a divalent group. In the present specification, the description of the above-described heterocyclic group may be applied, except that heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the above-described aryl group or cycloalkyl group may be applied, except that it is formed by combining two substituents. In the present specification, the heterocyclic group is not a monovalent group, and the description of the above-described heterocyclic group may be applied, except that it is formed by combining two substituents.

The compound represented by Formula 1 includes a core in which benzoxazole or a benzothiazole ring is fused to a benzothiophene ring, and includes a triazine or amine substituent bonded thereto. As the above structure is satisfied, the compound represented by Chemical Formula 1 exhibits a low voltage when applied to an organic light emitting device, and has excellent efficiency and lifespan characteristics.

Formula 1 may be specifically represented by any one of the following Formulas 1-1 to 1-4:

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4,

X, L ₁ to L ₄ , Ar ₁ to Ar ₅ , D, and n are as defined in Formula 1.

Preferably, L ₁ and L ₂ are each independently a single bond; or substituted or unsubstituted C _6-20 arylene. More preferably, L ₁ and L ₂ are each independently a single bond; phenylene; biphenyldiyl; or naphthalenediyl.

Preferably, L ₃ and L ₄ are each independently a single bond; or substituted or unsubstituted C _6-20 arylene. More preferably, L ₃ and L ₄ are each independently a single bond; phenylene; biphenyldiyl; or naphthalenediyl.

Preferably, Ar ₁ is substituted or unsubstituted C _6-20 aryl; or C _2-20 heteroaryl including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S.

More preferably, Ar ₁ is phenyl; biphenylyl; naphthyl; dibenzofuranyl; or dibenzothiophenyl.

Preferably, Ar ₂ to Ar ₅ are each independently, substituted or unsubstituted C _6-20 aryl; Or a substituted or unsubstituted C _2-20 heteroaryl containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S.

Preferably, Ar ₂ and Ar ₃ are each independently phenyl; biphenylyl; naphthyl; phenylnaphthyl (ie, naphthyl substituted with one phenyl); naphthylphenyl (ie, phenyl substituted with one naphthyl); phenanthrenylphenyl (ie, phenyl substituted with one phenanthrenyl); dibenzofuranyl; dibenzothiophenyl; or phenanthrenyl.

Preferably, Ar ₄ and Ar ₅ are each independently phenyl; biphenylyl; terphenylyl; naphthyl; naphthylphenyl; phenylnaphthyl; phenanthrenyl; 9-phenylcarbazolyl; dibenzofuranyl; or dibenzothiophenyl.

Meanwhile, in the compound represented by Formula 1, one or more hydrogens may be substituted with deuterium. That is, in Formula 1, n may be an integer of 1 or more, and/or, one or more substituents of L ₁ to L ₄ and Ar ₁ to Ar ₅ in Formula 1 may be substituted with deuterium.

Representative examples of the compound represented by Formula 1 are as follows:

In addition, the present invention provides a method for preparing the compound represented by the formula (1).

For example, Chemical Formula 1 may be prepared by a preparation method as shown in Scheme 1 below.

[Scheme 1]

In the above, the rest except for X' is the same as defined in Formula 1, X' is halogen, preferably X' is chloro or bromo.

Reaction Scheme 1 is a Suzuki coupling reaction, which is preferably performed in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be changed as known in the art.

Alternatively, in Formula 1, when A ₂ is Formula 1-c and L ₂ is a single bond, the compound of Formula 1 may be prepared by the preparation method shown in Scheme 2 below.

[Scheme 2]

In the above, the rest except for X' is the same as defined in Formula 1, X' is halogen, preferably X' is chloro or bromo.

Scheme 2 is an amine substitution reaction, preferably performed in the presence of a palladium catalyst and a base, and the reactor for the amine substitution reaction can be changed as known in the art.

The manufacturing method may be more specific in Preparation Examples to be described later.

In addition, the present invention provides an organic light emitting device including the compound represented by the formula (1). In one example, the present invention provides a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Formula 1 above. do.

The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

In addition, the organic layer may include an emission layer, and the emission layer includes the compound represented by Formula 1 above. In particular, the compound according to the present invention can be used as a host for the light emitting layer.

Also, the organic layer may include a hole injection layer, a hole transport layer, or an electron blocking layer, and the hole injection layer, the hole transport layer, or the electron blocking layer includes a compound represented by Formula 1 above.

In addition, the organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. Also, the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 to 3 .

1 shows an example of an organic light emitting device including a substrate 1 , an anode 2 , an organic material layer 3 , and a cathode 4 . In such a structure, the compound represented by Formula 1 may be included in the organic material layer.

2 is a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (8), a hole blocking layer (9), an electron transport layer (10) , an example of an organic light emitting device including an electron injection layer 11 and a cathode 4 is shown. In such a structure, the compound represented by Formula 1 may be included in one or more of the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer, and the electron injection layer.

3 is a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (8), a hole blocking layer (9), an electron injection and transport layer ( 12) and an example of an organic light-emitting device including a cathode 4 are shown. In such a structure, the compound represented by Formula 1 may be included in at least one of the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole suppression layer, and the electron injection and transport layer, for example, the light emitting layer or the electron It may be included in the blocking layer.

The organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Formula 1 above. Also, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode. and, after forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, it can be prepared by depositing a material that can be used as a cathode thereon. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition, the compound represented by Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.

In one example, the first electrode is an anode, the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

As the anode material, a material having a large work function is generally preferred so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multi-layered material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode, and as a hole injection material, it has the ability to transport holes, so it has a hole injection effect at the anode, an excellent hole injection effect on the light emitting layer or the light emitting material, and is produced in the light emitting layer A compound which prevents the movement of excitons to the electron injection layer or the electron injection material and is excellent in the ability to form a thin film is preferred. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, polyaniline and polythiophene-based conductive polymers, and the like, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light emitting layer. A material capable of transporting holes from the anode or hole injection layer to the light emitting layer as a hole transport material. A material with high hole mobility. This is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.

The electron blocking layer serves to improve the efficiency of the organic light emitting device by suppressing electrons injected from the cathode from being transferred to the anode without recombination in the light emitting layer. For the electron blocking layer, a material having a lower electron affinity than the electron transport layer is preferable. Preferably, the material represented by Formula 1 of the present invention may be used as the electron blocking layer material.

The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

The emission layer may include a host material and a dopant material. The host material includes a condensed aromatic ring derivative or a heterocyclic compound containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto. In particular, in the present invention, the compound represented by Chemical Formula 1 may be used as a host material for the light emitting layer, and in this case, low voltage, high efficiency and/or high lifespan characteristics of the organic light emitting device may be obtained.

Specifically, in Formula 1, when A ₂ is a triazine substituent represented by Formula 1-b, it is suitable for use as an N-type host material, and when A ₂ is an amine substituent represented by Formula 1-c, P -type May be suitable for use as host material. Accordingly, in Formula 1, at least one of the compounds in which A ₂ is a triazine substituent represented by Formula 1-b and at least one of the compounds in which A ₂ is an amine substituent represented by Formula 1-c are simultaneously included in the light emitting layer can do.

Examples of the dopant material include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamino group. As the styrylamine compound, a substituted or unsubstituted It is a compound in which at least one arylvinyl group is substituted in the arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but is not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. do. Specific examples include Al complex of 8-hydroxyquinoline; complexes comprising Alq ₃ ; organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function and followed by a layer of aluminum or silver. Specifically cesium, barium, calcium, ytterbium and samarium, followed in each case by an aluminum layer or a silver layer.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer. A compound which prevents movement to a layer and is excellent in the ability to form a thin film is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metals complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. However, the present invention is not limited thereto.

According to one embodiment of the present invention, the electron transport material and the electron injection material may be simultaneously deposited to form a single layer of the electron injection and transport layer.

The organic light emitting device according to the present invention may be a bottom emission device, a top emission device, or a double-sided light emitting device, and in particular, may be a bottom emission device requiring relatively high luminous efficiency.

In addition, the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

The compound represented by Formula 1 and the preparation of an organic light emitting device including the same will be described in detail in Examples below. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.

[Example]

<Preparation Example: Preparation of the core of the compound of Formula 1>

(Synthesis scheme of Preparation Examples 1-4)

Preparation Example 1: Synthesis of Formula AA

In a nitrogen atmosphere, 2-amino-6-bromophenol (15g, 79.8mmol) and (3-chloro-2-(methylthio)phenyl)boronic acid (17g, 83.8mmol) were added to 300ml of THF, stirred and refluxed. After that, potassium carbonate (33.1g, 239.3mmol) was dissolved in 99ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.4g, 0.8mmol) was added. After the reaction for 11 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16.1 g of formula AA_P1. (Yield 76%, MS: [M+H]+= 266)

Chemical formula AA_P1 (15g, 56.6mmol) and hydrogen peroxide (3.8g, 113.2mmol) were added to 300ml of acetic acid in a nitrogen atmosphere, and the mixture was stirred and refluxed. After 10 hours of reaction, the mixture was cooled to room temperature and the organic layer was distilled off. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.8 g of formula AA_P2. (Yield 74%, MS: [M+H]+= 282)

Formula AA_P2 (15g, 53.2mmol) and Trifluoromethanesulfonic acid (12g, 79.9mmol) were added to 300ml of Pyiridine in a nitrogen atmosphere and stirred at room temperature. After 11 hours of reaction, it was poured into 600 ml of water to solidify and filtered. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 8.2 g of formula AA_P3. (Yield 62%, MS: [M+H]+= 250)

Chemical formula AA_P3 (15g, 60.2mmol), carbon disulfide (5.5g, 72mmol), and potassium hydroxide (4.1g, 77mmol) were added to 150ml of EtOH in a nitrogen atmosphere, and stirred and refluxed. After 12 hours of reaction, the mixture was cooled to room temperature and the organic solvent was distilled under reduced pressure. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 9.9 g of formula AA_P4. (Yield 64%, MS: [M+H] + = 258)

Chemical formula AA_P4 (15g, 58.4mmol) and Phosphorus pentachloride (12.2g, 70mmol) were added to 150ml of toluene in a nitrogen atmosphere, and stirred and refluxed. After 12 hours of reaction, the mixture was cooled to room temperature and the organic solvent was distilled under reduced pressure. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 10.1 g of Formula AA. (Yield 67%, MS: [M+H] + = 260)

Preparation Example 2: Synthesis of Formula AB

Chemical formula AB was prepared in the same manner as in Preparation Example 1 except that (4-chloro-2-(methylthio)phenyl)boronic acid was used instead of (3-chloro-2-(methylthio)phenyl)boronic acid.

Preparation Example 3: Synthesis of Formula AC

Chemical formula AC was prepared in the same manner as in Preparation Example 1, except that (5-chloro-2-(methylthio)phenyl)boronic acid was used instead of (3-chloro-2-(methylthio)phenyl)boronic acid.

Preparation Example 4: Synthesis of Formula AD

Chemical formula AD was prepared in the same manner as in Preparation Example 1, except that (2-chloro-6-(methylthio)phenyl)boronic acid was used instead of (3-chloro-2-(methylthio)phenyl)boronic acid.

(Synthesis scheme of Preparation Examples 5 to 6)

Preparation Example 5: Synthesis of Formula AE

Use 2-amino-6-bromo-4-chlorophenol instead of 2-amino-6-bromophenol, and use (2-(methylthio)phenyl)boronic acid instead of (3-chloro-2-(methylthio)phenyl)boronic acid. Chemical formula AE was prepared in the same manner as in Preparation Example 1, except that.

Preparation Example 6: Synthesis of Formula AF

Use 2-amino-6-bromo-3-chlorophenol instead of 2-amino-6-bromophenol, and use (2-(methylthio)phenyl)boronic acid instead of (3-chloro-2-(methylthio)phenyl)boronic acid. Chemical formula AE was prepared in the same manner as in Preparation Example 1, except that.

(Synthesis scheme of Preparation Examples 7 to 10)

Preparation Example 7: Synthesis of Formula BA

Chemical formula BA was prepared in the same manner as in Preparation Example 1, except that 2-amino-3-bromophenol was used instead of 2-amino-6-bromophenol.

Preparation 8: Synthesis of Formula BB

Use 2-amino-3-bromophenol instead of 2-amino-6-bromophenol, and use (4-chloro-2-(methylthio)phenyl)boronic acid instead of (3-chloro-2-(methylthio)phenyl)boronic acid. Chemical formula BB was prepared in the same manner as in Preparation Example 1, except that.

Preparation Example 9: Synthesis of Formula BC

Use 2-amino-3-bromophenol instead of 2-amino-6-bromophenol, and use (5-chloro-2-(methylthio)phenyl)boronic acid instead of (3-chloro-2-(methylthio)phenyl)boronic acid. Chemical formula BC was prepared in the same manner as in Preparation Example 1, except that.

Preparation 10: Synthesis of Formula BD

Use 2-amino-3-bromophenol instead of 2-amino-6-bromophenol, and use (2-chloro-6-(methylthio)phenyl)boronic acid instead of (3-chloro-2-(methylthio)phenyl)boronic acid. Chemical formula BD was prepared in the same manner as in Preparation Example 1 except that.

(Synthesis scheme of Preparation Examples 11-12)

Preparation Example 11: Synthesis of Chemical Formula BE

Use 2-amino-3-bromo-5-chlorophenol instead of 2-amino-6-bromophenol, and use (2-(methylthio)phenyl)boronic acid instead of (3-chloro-2-(methylthio)phenyl)boronic acid. Chemical formula BE was prepared in the same manner as in Preparation Example 1 except that.

Preparation Example 12: Synthesis of Formula BF

Use 2-amino-3-bromo-6-chlorophenol instead of 2-amino-6-bromophenol, and use (2-(methylthio)phenyl)boronic acid instead of (3-chloro-2-(methylthio)phenyl)boronic acid. Chemical formula BF was prepared in the same manner as in Preparation Example 1, except that.

(Synthesis scheme of Preparation Examples 13-16)

Preparation 13: Synthesis of Chemical Formula CA

In a nitrogen atmosphere, 3-bromo-2-fluoroaniline (15g, 78.9mmol) and (3-chloro-2-(methylthio)phenyl)boronic acid (24g, 118.4mmol) were added to 300ml of THF, followed by stirring and reflux. After that, potassium carbonate (32.7g, 236.8mmol) was dissolved in 98ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.4g, 0.8mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 10.8 g of formula CA_P1. (Yield 51%, MS: [M+H] + = 268)

Chemical formula CA_P1 (15g, 56.2mmol) and hydrogen peroxide (2.9g, 84.3mmol) were added to 300ml of acetic acid in a nitrogen atmosphere, stirred and refluxed. After 10 hours of reaction, the mixture was cooled to room temperature and the organic layer was distilled off. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 8.6 g of formula CA_P2. (Yield 54%, MS: [M+H]+= 284)

Chemical formula CA_P2 (15g, 53mmol) and Trifluoromethanesulfonic acid (11.9g, 79.5mmol) were added to 300ml of Pyiridine in a nitrogen atmosphere and stirred at room temperature. After 11 hours of reaction, it was poured into 600 ml of water to solidify and filtered. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 6.9 g of formula CA_P3. (Yield 52%, MS: [M+H]+= 252)

Chemical formula CA_P3 (15g, 59.7mmol) and Potassium O -ethyl dithiocarbonate (21.0g, 131mmol) were added to 150ml of DMF in a nitrogen atmosphere, and stirred and refluxed. After reaction for 9 hours, the mixture was cooled to room temperature and the organic solvent was distilled under reduced pressure. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.7 g of formula CA_P4. (yield 80%, MS: [M+H]+= 308)

In a nitrogen atmosphere, formula CA_P4 (15g, 48.7mmol) was placed in 150ml of CHCl3 and cooled to 0°C with an ice bath. Then, Thionyl chloride (12.8g, 107.5mmol) was slowly added dropwise, followed by stirring. After the reaction for 4 hours, it was cooled to room temperature, and the organic solvent was distilled under reduced pressure. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was subjected to silica gel column chromatography to prepare 10.3 g of formula CA_P5. (Yield 68%, MS: [M+H] + = 310)

Preparation 14: Synthesis of Chemical Formula CB

Chemical formula CB was prepared in the same manner as in Preparation Example 13, except that (4-chloro-2-(methylthio)phenyl)boronic acid was used instead of (3-chloro-2-(methylthio)phenyl)boronic acid.

Preparation 15: Synthesis of Chemical Formula CC

Chemical formula CC was prepared in the same manner as in Preparation Example 13, except that (5-chloro-2-(methylthio)phenyl)boronic acid was used instead of (3-chloro-2-(methylthio)phenyl)boronic acid.

Preparation 16: Synthesis of Chemical Formula CD

Chemical formula CD was prepared in the same manner as in Preparation Example 13, except that (2-chloro-6-(methylthio)phenyl)boronic acid was used instead of (3-chloro-2-(methylthio)phenyl)boronic acid.

(Synthesis scheme of Preparation Examples 17 to 18)

Preparation 17: Synthesis of Chemical Formula CE

Use 3-bromo-5-chloro-2-fluoroaniline instead of 3-bromo-2-fluoroaniline, and use (2-(methylthio)phenyl)boronic acid instead of (3-chloro-2-(methylthio)phenyl)boronic acid. Chemical formula CE was prepared in the same manner as in Preparation Example 13, except that.

Preparation 18: Synthesis of Formula CF

Use 3-bromo-6-chloro-2-fluoroaniline instead of 3-bromo-2-fluoroaniline, and use (2-(methylthio)phenyl)boronic acid instead of (3-chloro-2-(methylthio)phenyl)boronic acid. Chemical formula CF was prepared in the same manner as in Preparation Example 13, except that.

(Synthesis scheme of Preparation Examples 19-22)

Preparation 19: Synthesis of Formula DA

Chemical formula DA was prepared in the same manner as in Preparation Example 13, except that 2-bromo-6-fluoroaniline was used instead of 3-bromo-2-fluoroaniline.

Preparation Example 20: Synthesis of Chemical Formula DB

Use 2-bromo-6-fluoroaniline instead of 3-bromo-2-fluoroaniline, and use (4-chloro-2-(methylthio)phenyl)boronic acid instead of (3-chloro-2-(methylthio)phenyl)boronic acid. Chemical formula DB was prepared in the same manner as in Preparation Example 13, except that.

Preparation 21: Synthesis of Formula DC

Use 2-bromo-6-fluoroaniline instead of 3-bromo-2-fluoroaniline, and use (5-chloro-2-(methylthio)phenyl)boronic acid instead of (3-chloro-2-(methylthio)phenyl)boronic acid. Chemical formula DC was prepared in the same manner as in Preparation Example 13, except that.

Preparation 22: Synthesis of Formula DD

Use 2-bromo-6-fluoroaniline instead of 3-bromo-2-fluoroaniline, and use (2-chloro-6-(methylthio)phenyl)boronic acid instead of (3-chloro-2-(methylthio)phenyl)boronic acid. Chemical formula DD was prepared in the same manner as in Preparation Example 13, except that

(Synthesis scheme of Preparation Examples 23-24)

Preparation 23: Synthesis of Formula DE

Use 2-bromo-4-chloro-6-fluoroaniline instead of 3-bromo-2-fluoroaniline, and use (2-(methylthio)phenyl)boronic acid instead of (3-chloro-2-(methylthio)phenyl)boronic acid. Chemical formula DE was prepared in the same manner as in Preparation Example 13, except that.

Preparation 24: Synthesis of Formula DF

Use 6-bromo-3-chloro-2-fluoroaniline instead of 4-bromo-2-fluoroaniline, and use (2-(methylthio)phenyl)boronic acid instead of (3-chloro-2-(methylthio)phenyl)boronic acid. Chemical formula DF was prepared in the same manner as in Preparation Example 13, except that.

<Synthesis Example: Preparation of the compound of Formula 1>

Synthesis Example 1-1

Formula AA (15g, 51mmol) and [1,1'-biphenyl]-4-ylboronic acid (10.6g, 53.5mmol) were added to 300ml of THF in a nitrogen atmosphere, and stirred and refluxed. After that, potassium carbonate (21.1g, 153mmol) was dissolved in 63ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.8 g of subAA-1. (Yield 61%, MS: [M+H]+= 412)

In a nitrogen atmosphere, subAA-1 (15g, 36.4mmol) and bis(pinacolato)diboron (10.2g, 40.1mmol) were refluxed in 300ml of 1,4-dioxane and stirred. After that, potassium acetate (5.4g, 54.6mmol) was added, and after sufficient stirring, bis(dibenzylideneacetone)palladium(0) (0.6g, 1.1mmol) and tricyclohexylphosphine (0.6g, 2.2mmol) were added. After reacting for 7 hours, cooling to room temperature, and separating the organic layer using chloroform and water, the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.5 g of subAA-2. (Yield 63%, MS: [M+H]+= 504)

In a nitrogen atmosphere, subAA-2 (15g, 29.8mmol) and Trz1 (9.9g, 31.3mmol) were added to 300ml of THF, stirred and refluxed. After that, potassium carbonate (12.4g, 89.4mmol) was dissolved in 37ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After the reaction for 12 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.7 g of compound 1-1. (Yield 70%, MS: [M+H]+= 659)

Synthesis Example 1-2

Chemical formula AB (15g, 51mmol) and phenylboronic acid (6.5g, 53.5mmol) were added to 300ml of THF in a nitrogen atmosphere, and stirred and refluxed. After that, potassium carbonate (21.1g, 153mmol) was dissolved in 63ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 9.6 g of subAB-1. (Yield 56%, MS: [M+H]+= 336)

In a nitrogen atmosphere, subAB-1 (15g, 44.7mmol) and bis(pinacolato)diboron (12.5g, 49.1mmol) were refluxed in 300ml of 1,4-dioxane and stirred. After that, potassium acetate (6.6g, 67mmol) was added, and after sufficient stirring, bis(dibenzylideneacetone)palladium(0) (0.8g, 1.3mmol) and tricyclohexylphosphine (0.8g, 2.7mmol) were added. After reacting for 6 hours, cooling to room temperature, and separating the organic layer using chloroform and water, the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.6 g of subAB-2. (Yield 66%, MS: [M+H]+= 428)

In a nitrogen atmosphere, subAB-2 (15g, 35.1mmol) and Trz2 (9.9g, 36.9mmol) were added to 300ml of THF, followed by stirring and reflux. After that, potassium carbonate (14.6g, 105.3mmol) was dissolved in 44ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12 g of compound 1-2. (Yield 64%, MS: [M+H]+= 533)

Synthesis Example 1-3

Chemical formula AE (15g, 51mmol) and phenylboronic acid (6.5g, 53.5mmol) were added to 300ml of THF in a nitrogen atmosphere, and stirred and refluxed. After that, potassium carbonate (21.1g, 153mmol) was dissolved in 63ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After the reaction for 11 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 9.4 g of subAE-1. (Yield 55%, MS: [M+H]+= 336)

In a nitrogen atmosphere, subAE-1 (15g, 44.7mmol) and Trz3 (22.5g, 46.9mmol) were added to 300ml of THF, followed by stirring and reflux. After that, potassium carbonate (18.5 g, 134 mmol) was dissolved in 56 ml of water, and after sufficient stirring, bis (tri-tert-butylphosphine) palladium (0) (0.2 g, 0.4 mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 20 g of compound 1-3. (Yield 61%, MS: [M+H]+= 735)

Synthesis Example 1-4

In a nitrogen atmosphere, subAE-1 (15g, 44.7mmol) and Trz4 (20.8g, 46.9mmol) were added to 300ml of THF, followed by stirring and reflux. After that, potassium carbonate (18.5 g, 134 mmol) was dissolved in 56 ml of water, and after sufficient stirring, bis (tri-tert-butylphosphine) palladium (0) (0.2 g, 0.4 mmol) was added. After the reaction for 12 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16.8 g of compound 1-4. (Yield 54%, MS: [M+H]+= 699)

Synthesis Example 1-5

Formula AF (15g, 51mmol) and naphthalen-2-ylboronic acid (9.2g, 53.5mmol) were added to 300ml of THF in a nitrogen atmosphere, stirred and refluxed. After that, potassium carbonate (21.1g, 153mmol) was dissolved in 63ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After the reaction for 11 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.5 g of subAF-1. (yield 69%, MS: [M+H] + = 386)

In a nitrogen atmosphere, subAF-1 (15g, 38.9mmol) and Trz5 (16.5g, 40.8mmol) were placed in 300ml of THF, stirred and refluxed. After that, potassium carbonate (16.1g, 116.6mmol) was dissolved in 48ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After the reaction for 11 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18.2 g of compound 1-5. (Yield 66%, MS: [M+H]+=709)

Synthesis Example 1-6

Formula BA (15g, 51mmol) and phenylboronic acid (6.5g, 53.5mmol) were added to 300ml of THF in a nitrogen atmosphere, and stirred and refluxed. After that, potassium carbonate (21.1g, 153mmol) was dissolved in 63ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.8 g of subBA-1. (yield 69%, MS: [M+H]+= 336)

In a nitrogen atmosphere, subBA-1 (15g, 44.7mmol) and bis(pinacolato)diboron (12.5g, 49.1mmol) were refluxed in 300ml of 1,4-dioxane and stirred. After that, potassium acetate (6.6g, 67mmol) was added, and after sufficient stirring, bis(dibenzylideneacetone)palladium(0) (0.8g, 1.3mmol) and tricyclohexylphosphine (0.8g, 2.7mmol) were added. After reacting for 8 hours, cooling to room temperature, and separating the organic layer using chloroform and water, the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.9 g of subBA-2. (Yield 78%, MS: [M+H]+= 428)

In a nitrogen atmosphere, subBA-2 (15g, 35.1mmol) and Trz6 (14.5g, 36.9mmol) were added to 300ml of THF, stirred and refluxed. After that, potassium carbonate (14.6g, 105.3mmol) was dissolved in 44ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After the reaction for 12 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.6 g of compound 1-6. (yield 59%, MS: [M+H]+= 659)

Synthesis Example 1-7

Chemical formula BB (15g, 51mmol) and phenylboronic acid (6.5g, 53.5mmol) were added to 300ml of THF in a nitrogen atmosphere, and stirred and refluxed. After that, potassium carbonate (21.1g, 153mmol) was dissolved in 63ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 10.3 g of subBB-1. (Yield 60%, MS: [M+H]+= 336)

In a nitrogen atmosphere, subBB-1 (15g, 44.7mmol) and Trz7 (18.9g, 46.9mmol) were added to 300ml of THF, stirred and refluxed. After that, potassium carbonate (18.5 g, 134 mmol) was dissolved in 56 ml of water, and after sufficient stirring, bis (tri-tert-butylphosphine) palladium (0) (0.2 g, 0.4 mmol) was added. After the reaction for 12 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17.9 g of compound 1-7. (Yield 61%, MS: [M+H]+= 659)

Synthesis Example 1-8

Chemical formula BE (15g, 51mmol) and dibenzo[b,d]thiophen-1-ylboronic acid (12.2g, 53.5mmol) were added to 300ml of THF in a nitrogen atmosphere, and stirred and refluxed. After that, potassium carbonate (21.1g, 153mmol) was dissolved in 63ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.7 g of subBE-1. (Yield 52%, MS: [M+H]+= 442)

In a nitrogen atmosphere, subBE-1 (15g, 33.9mmol) and Trz8 (14.4g, 35.6mmol) were added to 300ml of THF, followed by stirring and reflux. After that, potassium carbonate (14.1g, 101.8mmol) was dissolved in 42ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After the reaction for 12 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.8 g of compound 1-8. (Yield 57%, MS: [M+H] + = 765)

Synthesis Example 1-9

Chemical formula BF (15g, 51mmol) and phenylboronic acid (6.5g, 53.5mmol) were added to 300ml of THF in a nitrogen atmosphere, and stirred and refluxed. After that, potassium carbonate (21.1g, 153mmol) was dissolved in 63ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.3 g of subBF-1. (Yield 66%, MS: [M+H]+= 336)

In a nitrogen atmosphere, subBF-1 (15g, 44.7mmol) and Trz9 (22.5g, 46.9mmol) were placed in 300ml of THF, stirred and refluxed. After that, potassium carbonate (18.5 g, 134 mmol) was dissolved in 56 ml of water, and after sufficient stirring, bis (tri-tert-butylphosphine) palladium (0) (0.2 g, 0.4 mmol) was added. After the reaction for 12 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16.7 g of compound 1-9. (Yield 51%, MS: [M+H]+= 735)

Synthesis Example 1-10

Chemical formula CA (15g, 48.4mmol) and phenylboronic acid (6.2g, 50.8mmol) were added to 300ml of THF in a nitrogen atmosphere, and stirred and refluxed. After that, potassium carbonate (20g, 145.1mmol) was dissolved in 60ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After the reaction for 11 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 9.3 g of subCA-1. (Yield 55%, MS: [M+H]+= 352)

In a nitrogen atmosphere, subCA-1 (15g, 42.6mmol) and Trz10 (19.2g, 44.8mmol) were added to 300ml of THF, stirred and refluxed. After that, potassium carbonate (17.7g, 127.9mmol) was dissolved in 53ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 20.6 g of Compound 1-10. (yield 69%, MS: [M+H]+= 701)

Synthesis Example 1-11

Chemical formula CB (15g, 48.4mmol) and phenylboronic acid (6.2g, 50.8mmol) were placed in 300ml of THF in a nitrogen atmosphere, stirred and refluxed. After that, potassium carbonate (20g, 145.1mmol) was dissolved in 60ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 9.2 g of subCB-1. (Yield 54%, MS: [M+H]+= 352)

In a nitrogen atmosphere, subCB-1 (15g, 42.6mmol) and bis(pinacolato)diboron (11.9g, 46.9mmol) were refluxed in 300ml of 1,4-dioxane and stirred. After that, potassium acetate (6.3g, 63.9mmol) was added, and after sufficient stirring, bis(dibenzylideneacetone)palladium(0) (0.7g, 1.3mmol) and tricyclohexylphosphine (0.7g, 2.6mmol) were added. After reacting for 5 hours, cooling to room temperature, and separating the organic layer using chloroform and water, the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.2 g of subCB-2. (Yield 75%, MS: [M+H]+= 444)

In a nitrogen atmosphere, subCB-2 (15g, 33.8mmol) and Trz11 (14g, 35.5mmol) were added to 300ml of THF, followed by stirring and reflux. After that, potassium carbonate (14g, 101.5mmol) was dissolved in 42ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.2 g of compound 1-11. (Yield 58%, MS: [M+H]+= 675)

Synthesis Example 1-12

In a nitrogen atmosphere, subCB-1 (15g, 42.6mmol) and Trz12 (18g, 44.8mmol) were added to 300ml of THF, followed by stirring and reflux. After that, potassium carbonate (17.7g, 127.9mmol) was dissolved in 53ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After the reaction for 12 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.8 g of compound 1-12. (Yield 55%, MS: [M+H] + = 675)

Synthesis Example 1-13

Chemical formula CE (15g, 48.4mmol) and dibenzo[b,d]furan-1-ylboronic acid (10.8g, 50.8mmol) were added to 300ml of THF in a nitrogen atmosphere, and stirred and refluxed. After that, potassium carbonate (20g, 145.1mmol) was dissolved in 60ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.4 g of subCE-1. (Yield 58%, MS: [M+H]+= 442)

In a nitrogen atmosphere, subCE-1 (15g, 33.9mmol) and Trz13 (12.6g, 35.6mmol) were added to 300ml of THF, followed by stirring and reflux. After that, potassium carbonate (14.1g, 101.8mmol) was dissolved in 42ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After the reaction for 12 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.5 g of compound 1-13. (Yield 64%, MS: [M+H]+= 715)

Synthesis Example 1-14

Chemical formula CF (15g, 48.4mmol) and naphthalen-2-ylboronic acid (10.8g, 50.8mmol) were added to 300ml of THF in a nitrogen atmosphere, stirred and refluxed. After that, potassium carbonate (20g, 145.1mmol) was dissolved in 60ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After the reaction for 12 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13 g of subCF-1. (Yield 67%, MS: [M+H] + = 402)

In a nitrogen atmosphere, subCF-1 (15g, 37.3mmol) and Trz5 (15.8g, 39.2mmol) were added to 300ml of THF, stirred and refluxed. Thereafter, potassium carbonate (15.5 g, 112 mmol) was dissolved in 46 ml of water, and after sufficient stirring, bis (tri-tert-butylphosphine) palladium (0) (0.2 g, 0.4 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18.4 g of compound 1-14. (Yield 68%, MS: [M+H]+= 725)

Synthesis Example 1-15

Chemical formula DA (15g, 48.4mmol) and phenylboronic acid (6.2g, 50.8mmol) were added to 300ml of THF in a nitrogen atmosphere, and stirred and refluxed. After that, potassium carbonate (20g, 145.1mmol) was dissolved in 60ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.7 g of subDA-1. (yield 69%, MS: [M+H]+= 352)

In a nitrogen atmosphere, subDA-1 (15g, 42.6mmol) and bis(pinacolato)diboron (11.9g, 46.9mmol) were refluxed in 300ml of 1,4-dioxane and stirred. After that, potassium acetate (6.3g, 63.9mmol) was added, and after sufficient stirring, bis(dibenzylideneacetone)palladium(0) (0.7g, 1.3mmol) and tricyclohexylphosphine (0.7g, 2.6mmol) were added. After reacting for 9 hours, cooling to room temperature, and separating the organic layer using chloroform and water, the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.7 g of subDA-2. (Yield 78%, MS: [M+H]+= 444)

In a nitrogen atmosphere, subDA-2 (15g, 33.8mmol) and Trz14 (14g, 35.5mmol) were added to 300ml of THF, followed by stirring and reflux. After that, potassium carbonate (14g, 101.5mmol) was dissolved in 42ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After the reaction for 11 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.7 g of compound 1-15. (yield 69%, MS: [M+H]+= 675)

Synthesis Example 1-16

Chemical formula DB (15g, 48.4mmol) and naphthalen-2-ylboronic acid (10.8g, 50.8mmol) were added to 300ml of THF in a nitrogen atmosphere, stirred and refluxed. After that, potassium carbonate (20g, 145.1mmol) was dissolved in 60ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 9.9 g of subDB-1. (Yield 51%, MS: [M+H] + = 402)

In a nitrogen atmosphere, subDB-1 (15g, 37.3mmol) and bis(pinacolato)diboron (10.4g, 41.1mmol) were refluxed in 300ml of 1,4-dioxane and stirred. After that, potassium acetate (5.5g, 56mmol) was added, and after sufficient stirring, bis(dibenzylideneacetone)palladium(0) (0.6g, 1.1mmol) and tricyclohexylphosphine (0.6g, 2.2mmol) were added. After reacting for 7 hours, cooling to room temperature, and separating the organic layer using chloroform and water, the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.3 g of subDB-2. (Yield 67%, MS: [M+H]+= 494)

In a nitrogen atmosphere, subDB-2 (15g, 30.4mmol) and Trz2 (8.5g, 31.9mmol) were added to 300ml of THF, followed by stirring and reflux. After that, potassium carbonate (12.6g, 91.2mmol) was dissolved in 38ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.6 g of compound 1-16. (Yield 64%, MS: [M+H]+= 599)

Synthesis Example 1-17

Chemical formula DF (15g, 48.4mmol) and phenylboronic acid (6.2g, 50.8mmol) were added to 300ml of THF in a nitrogen atmosphere, and stirred and refluxed. After that, potassium carbonate (20g, 145.1mmol) was dissolved in 60ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 9 g of subDF-1. (Yield 53%, MS: [M+H]+= 352)

In a nitrogen atmosphere, subDF-1 (15g, 42.6mmol) and Trz15 (18g, 44.8mmol) were added to 300ml of THF, followed by stirring and reflux. After that, potassium carbonate (17.7g, 127.9mmol) was dissolved in 53ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After the reaction for 12 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 19.5 g of compound 1-17. (Yield 68%, MS: [M+H]+=675)

Synthesis Example 2-1

Formula AA (15g, 51mmol) and naphthalen-2-ylboronic acid (9.2g, 53.5mmol) were added to 300ml of THF in a nitrogen atmosphere, stirred and refluxed. After that, potassium carbonate (21.1g, 153mmol) was dissolved in 63ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.2 g of subAA-3. (Yield 57%, MS: [M+H] + = 386)

In a nitrogen atmosphere, subAA-3 (10 g, 25.9 mmol), amine1 (8.7 g, 25.9 mmol), and sodium tert-butoxide (8.3 g, 38.9 mmol) were added to 200 ml of Xylene, followed by stirring and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.6 g of compound 2-1. (Yield 54%, MS: [M+H] + = 685)

Synthesis Example 2-2

In a nitrogen atmosphere, subAB-1 (10 g, 29.8 mmol), amine2 (8.8 g, 29.8 mmol), and sodium tert-butoxide (9.5 g, 44.7 mmol) were added to 200 ml of Xylene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 2 hours, the reaction was terminated, cooled to room temperature, and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.6 g of compound 2-2. (Yield 54%, MS: [M+H]+= 595)

Synthesis Example 2-3

Chemical formula AC (15g, 51mmol) and phenylboronic acid (6.5g, 53.5mmol) were added to 300ml of THF in a nitrogen atmosphere, and stirred and refluxed. After that, potassium carbonate (21.1g, 153mmol) was dissolved in 63ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After the reaction for 11 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 9.4 g of subAC-1. (Yield 55%, MS: [M+H]+= 336)

In a nitrogen atmosphere, subAC-1 (10 g, 29.8 mmol), amine3 (12.2 g, 29.8 mmol), and sodium tert-butoxide (9.5 g, 44.7 mmol) were added to 200 ml of Xylene, followed by stirring and reflux. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.2 g of compound 2-3. (Yield 53%, MS: [M+H] + = 710)

Synthesis Example 2-4

In a nitrogen atmosphere, subAC-1 (15g, 44.7mmol) and amine4 (22.8g, 46.9mmol) were added to 300ml of THF, stirred and refluxed. After that, potassium carbonate (18.5 g, 134 mmol) was dissolved in 56 ml of water, and after sufficient stirring, bis (tri-tert-butylphosphine) palladium (0) (0.2 g, 0.4 mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16.5 g of compound 2-4. (Yield 50%, MS: [M+H]+= 741)

Synthesis Example 2-5

Chemical formula AE (15g, 51mmol) and [1,1'-biphenyl]-4-ylboronic acid (10.6g, 53.5mmol) were added to 300ml of THF in a nitrogen atmosphere, and stirred and refluxed. After that, potassium carbonate (21.1g, 153mmol) was dissolved in 63ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.1 g of subAE-2. (Yield 53%, MS: [M+H]+= 412)

In a nitrogen atmosphere, subAE-2 (10 g, 24.3 mmol), amine5 (7.2 g, 24.3 mmol), and sodium tert-butoxide (7.7 g, 36.4 mmol) were added to 200 ml of Xylene, followed by stirring and reflux. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.9 g of compound 2-5. (Yield 55%, MS: [M+H] + = 671)

Synthesis Example 2-6

Formula AF (15g, 51mmol) and phenylboronic acid (6.5g, 53.5mmol) were added to 300ml of THF in a nitrogen atmosphere, and stirred and refluxed. After that, potassium carbonate (21.1g, 153mmol) was dissolved in 63ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After the reaction for 11 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.3 g of subAF-2. (Yield 66%, MS: [M+H]+= 336)

In a nitrogen atmosphere, subAF-2 (15g, 44.7mmol) and amine6 (20.7g, 46.9mmol) were added to 300ml of THF, stirred and refluxed. After that, potassium carbonate (18.5 g, 134 mmol) was dissolved in 56 ml of water, and after sufficient stirring, bis (tri-tert-butylphosphine) palladium (0) (0.2 g, 0.4 mmol) was added. After the reaction for 12 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16.8 g of compound 2-6. (Yield 54%, MS: [M+H]+= 697)

Synthesis Example 2-7

In a nitrogen atmosphere, subBA-1 (15g, 44.7mmol) and amine7 (18.5g, 46.9mmol) were added to 300ml of THF, stirred and refluxed. After that, potassium carbonate (18.5 g, 134 mmol) was dissolved in 56 ml of water, and after sufficient stirring, bis (tri-tert-butylphosphine) palladium (0) (0.2 g, 0.4 mmol) was added. After the reaction for 11 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17.1 g of compound 2-7. (yield 59%, MS: [M+H]+= 651)

Synthesis Example 2-8

In a nitrogen atmosphere, subBB-1 (15g, 44.7mmol) and amine8 (23g, 46.9mmol) were added to 300ml of THF, followed by stirring and reflux. After that, potassium carbonate (18.5 g, 134 mmol) was dissolved in 56 ml of water, and after sufficient stirring, bis (tri-tert-butylphosphine) palladium (0) (0.2 g, 0.4 mmol) was added. After the reaction for 11 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 22 g of compound 2-8. (Yield 66%, MS: [M+H]+=747)

Synthesis Example 2-9

In a nitrogen atmosphere, subBB-1 (10 g, 29.8 mmol), amine9 (12.6 g, 29.8 mmol), and sodium tert-butoxide (9.5 g, 44.7 mmol) were added to 200 ml of Xylene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 2 hours, the reaction was terminated, cooled to room temperature, and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.4 g of compound 2-9. (Yield 53%, MS: [M+H]+= 724)

Synthesis Example 2-10

Chemical formula BC (15g, 51mmol) and naphthalen-2-ylboronic acid (9.2g, 53.5mmol) were added to 300ml of THF in a nitrogen atmosphere, stirred and refluxed. After that, potassium carbonate (21.1g, 153mmol) was dissolved in 63ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.7 g of subBC-1. (Yield 70%, MS: [M+H] + = 386)

In a nitrogen atmosphere, subBC-1 (10 g, 25.9 mmol), amine10 (8.3 g, 25.9 mmol), and sodium tert-butoxide (8.3 g, 38.9 mmol) were added to 200 ml of Xylene, followed by stirring and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9 g of compound 2-10. (Yield 52%, MS: [M+H] + = 671)

Synthesis Example 2-11

Chemical formula BC (15g, 51mmol) and phenylboronic acid (6.5g, 53.5mmol) were added to 300ml of THF in a nitrogen atmosphere, and stirred and refluxed. After that, potassium carbonate (21.1g, 153mmol) was dissolved in 63ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After the reaction for 11 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 10.3 g of subBC-2. (Yield 60%, MS: [M+H]+= 336)

In a nitrogen atmosphere, subBC-2 (15g, 44.7mmol) and amine11 (17.8g, 46.9mmol) were added to 300ml of THF, stirred and refluxed. After that, potassium carbonate (18.5 g, 134 mmol) was dissolved in 56 ml of water, and after sufficient stirring, bis (tri-tert-butylphosphine) palladium (0) (0.2 g, 0.4 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.4 g of compound 2-11. (Yield 51%, MS: [M+H]+= 635)

Synthesis Example 2-12

Chemical formula BC (15g, 51mmol) and dibenzo[b,d]furan-1-ylboronic acid (11.4g, 53.5mmol) were added to 300ml of THF in a nitrogen atmosphere, and stirred and refluxed. After that, potassium carbonate (21.1g, 153mmol) was dissolved in 63ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.3 g of subBC-3. (Yield 66%, MS: [M+H]+= 426)

In a nitrogen atmosphere, subBC-3 (15g, 35.2mmol) and amine12 (16.3g, 37mmol) were added to 300ml of THF, followed by stirring and reflux. After that, potassium carbonate (14.6g, 105.7mmol) was dissolved in 44ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After the reaction for 11 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 19.1 g of compound 2-12. (yield 69%, MS: [M+H]+=787)

Synthesis Example 2-13

Chemical formula BE (15g, 51mmol) and phenylboronic acid (6.5g, 53.5mmol) were added to 300ml of THF in a nitrogen atmosphere, and stirred and refluxed. After that, potassium carbonate (21.1g, 153mmol) was dissolved in 63ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 8.5 g of subBE-2. (Yield 50%, MS: [M+H]+= 336)

In a nitrogen atmosphere, subBE-2 (10 g, 29.8 mmol), amine13 (10.3 g, 29.8 mmol), and sodium tert-butoxide (9.5 g, 44.7 mmol) were added to 200 ml of Xylene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.5 g of compound 2-13. (Yield 60%, MS: [M+H]+= 645)

Synthesis Example 2-14

In a nitrogen atmosphere, subBE-2 (15g, 44.7mmol) and amine14 (21.4g, 46.9mmol) were added to 300ml of THF, stirred and refluxed. After that, potassium carbonate (18.5 g, 134 mmol) was dissolved in 56 ml of water, and after sufficient stirring, bis (tri-tert-butylphosphine) palladium (0) (0.2 g, 0.4 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 20.3 g of compound 2-14. (Yield 64%, MS: [M+H]+=711)

Synthesis Example 2-15

In a nitrogen atmosphere, subBF-1 (15g, 44.7mmol) and amine15 (22.1g, 46.9mmol) were added to 300ml of THF, stirred and refluxed. After that, potassium carbonate (18.5 g, 134 mmol) was dissolved in 56 ml of water, and after sufficient stirring, bis (tri-tert-butylphosphine) palladium (0) (0.2 g, 0.4 mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17.8 g of compound 2-15. (Yield 55%, MS: [M+H]+= 727)

Synthesis Example 2-16

Chemical formula CA (15g, 48.4mmol) and dibenzo[b,d]thiophen-3-ylboronic acid (11.6g, 50.8mmol) were added to 300ml of THF in a nitrogen atmosphere, and stirred and refluxed. After that, potassium carbonate (20g, 145.1mmol) was dissolved in 60ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.3 g of subCA-2. (Yield 51%, MS: [M+H]+=458)

In a nitrogen atmosphere, subCA-2 (15g, 32.8mmol) and amine16 (14.3g, 34.4mmol) were added to 300ml of THF, stirred and refluxed. After that, potassium carbonate (13.6g, 98.3mmol) was dissolved in 41ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.3 g of compound 2-16. (Yield 55%, MS: [M+H]+=793)

Synthesis Example 2-17

In a nitrogen atmosphere, subCB-1 (10 g, 28.4 mmol), amine17 (12 g, 28.4 mmol), and sodium tert-butoxide (9 g, 42.6 mmol) were added to 200 ml of Xylene, followed by stirring and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.2 g of Compound 2-17. (Yield 63%, MS: [M+H]+=737)

Synthesis Example 2-18

In a nitrogen atmosphere, subCB-1 (15g, 42.6mmol) and amine18 (21.1g, 44.8mmol) were added to 300ml of THF, followed by stirring and reflux. After that, potassium carbonate (17.7g, 127.9mmol) was dissolved in 53ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After the reaction for 12 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18 g of compound 2-18. (Yield 57%, MS: [M+H]+= 743)

Synthesis Example 2-19

Chemical formula CC (15g, 48.4mmol) and phenylboronic acid (6.2g, 50.8mmol) were added to 300ml of THF in a nitrogen atmosphere, and stirred and refluxed. After that, potassium carbonate (20g, 145.1mmol) was dissolved in 60ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 8.7 g of subCC-1. (Yield 51%, MS: [M+H]+= 352)

In a nitrogen atmosphere, subCC-1 (10 g, 28.4 mmol), amine19 (11.7 g, 28.4 mmol), and sodium tert-butoxide (9 g, 42.6 mmol) were added to Xylene 200 ml, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.4 g of Compound 2-19. (Yield 65%, MS: [M+H]+= 727)

Synthesis Example 2-20

In a nitrogen atmosphere, subCC-1 (10 g, 28.4 mmol), amine20 (10.6 g, 28.4 mmol), and sodium tert-butoxide (9 g, 42.6 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.3 g of Compound 2-20. (Yield 63%, MS: [M+H]+= 687)

Synthesis Example 2-21

In a nitrogen atmosphere, subCC-1 (15g, 42.6mmol) and amine21 (22g, 44.8mmol) were added to 300ml of THF, followed by stirring and reflux. After that, potassium carbonate (17.7g, 127.9mmol) was dissolved in 53ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After the reaction for 11 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 21.1 g of compound 2-21. (Yield 65%, MS: [M+H]+= 763)

Synthesis Example 2-22

Chemical formula CD (15g, 48.4mmol) and phenylboronic acid (6.2g, 50.8mmol) were added to 300ml of THF in a nitrogen atmosphere, and stirred and refluxed. After that, potassium carbonate (20g, 145.1mmol) was dissolved in 60ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 8.7 g of subCD-1. (Yield 51%, MS: [M+H]+= 352)

In a nitrogen atmosphere, subCD-1 (15g, 42.6mmol) and amine22 (19.8g, 44.8mmol) were added to 300ml of THF, stirred and refluxed. Thereafter, potassium carbonate (17.7 g, 127.9 mmol) was dissolved in 53 ml of water, and after sufficient stirring, bis (tri-tert-butylphosphine) palladium (0) (0.2 g, 0.4 mmol) was added. After the reaction for 11 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17.3 g of compound 2-22. (Yield 57%, MS: [M+H] + = 713)

Synthesis Example 2-23

Chemical formula CE (15g, 48.4mmol) and phenylboronic acid (6.2g, 50.8mmol) were added to 300ml of THF in a nitrogen atmosphere, and stirred and refluxed. After that, potassium carbonate (20g, 145.1mmol) was dissolved in 60ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.2 g of subCE-2. (Yield 66%, MS: [M+H]+= 352)

In a nitrogen atmosphere, subCE-2 (10 g, 28.4 mmol), amine23 (9.8 g, 28.4 mmol), and sodium tert-butoxide (9 g, 42.6 mmol) were added to 200 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.1 g of compound 2-23. (yield 59%, MS: [M+H] + = 661)

Synthesis Example 2-24

Chemical formula CF (15g, 48.4mmol) and phenylboronic acid (6.2g, 50.8mmol) were added to 300ml of THF in a nitrogen atmosphere, and stirred and refluxed. After that, potassium carbonate (20g, 145.1mmol) was dissolved in 60ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After the reaction for 11 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 9.8 g of subCF-2. (Yield 58%, MS: [M+H]+= 352)

In a nitrogen atmosphere, subCF-2 (10 g, 28.4 mmol), amine24 (10 g, 28.4 mmol), and sodium tert-butoxide (9 g, 42.6 mmol) were added to 200 ml of Xylene, followed by stirring and reflux. After this, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.2 g of compound 2-24. (Yield 54%, MS: [M+H]+= 667)

Synthesis Example 2-25

In a nitrogen atmosphere, subDB-1 (15g, 37.3mmol) and amine25 (17.3g, 39.2mmol) were added to 300ml of THF, stirred and refluxed. After that, potassium carbonate (15.5 g, 112 mmol) was dissolved in 46 ml of water, and after sufficient stirring, bis (tri-tert-butylphosphine) palladium (0) (0.2 g, 0.4 mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.8 g of compound 2-25. (Yield 52%, MS: [M+H] + = 763)

Synthesis Example 2-26

Chemical formula DC (15g, 48.4mmol) and phenylboronic acid (6.2g, 50.8mmol) were added to 300ml of THF in a nitrogen atmosphere, and stirred and refluxed. After that, potassium carbonate (20g, 145.1mmol) was dissolved in 60ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After the reaction for 12 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.2 g of subDB-2. (Yield 66%, MS: [M+H]+= 352)

In a nitrogen atmosphere, subDB-2 (10 g, 29.8 mmol), amine26 (12.3 g, 29.8 mmol), and sodium tert-butoxide (9.5 g, 44.7 mmol) were added to 200 ml of Xylene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 2 hours, the reaction was terminated, cooled to room temperature, and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.4 g of compound 2-26. (Yield 54%, MS: [M+H] + = 711)

Synthesis Example 2-27

Chemical formula DC (15g, 48.4mmol) and naphthalen-2-ylboronic acid (8.7g, 50.8mmol) were added to 300ml of THF in a nitrogen atmosphere, stirred and refluxed. After that, potassium carbonate (20g, 145.1mmol) was dissolved in 60ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.1 g of subDC-1. (Yield 57%, MS: [M+H] + = 402)

In a nitrogen atmosphere, subDC-1 (10 g, 24.9 mmol), amine10 (8 g, 24.9 mmol), and sodium tert-butoxide (7.9 g, 37.3 mmol) were added to 200 ml of Xylene, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.7 g of compound 2-27. (Yield 51%, MS: [M+H]+= 687)

Synthesis Example 2-28

Chemical formula (15g, 48.4mmol) and phenylboronic acid (6.2g, 50.8mmol) were added to 300ml of THF in a nitrogen atmosphere, and stirred and refluxed. After that, potassium carbonate (20g, 145.1mmol) was dissolved in 60ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After the reaction for 12 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 9 g of subDC-2. (Yield 53%, MS: [M+H]+= 352)

In a nitrogen atmosphere, subDC-2 (15g, 42.6mmol) and amine27 (21g, 44.8mmol) were added to 300ml of THF, stirred and refluxed. After that, potassium carbonate (17.7g, 127.9mmol) was dissolved in 53ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 22.1 g of compound 2-28. (Yield 70%, MS: [M+H] + = 741)

Synthesis Example 2-29

Chemical formula (15g, 48.4mmol) and dibenzo[b,d]furan-2-ylboronic acid (10.8g, 50.8mmol) were added to 300ml of THF in a nitrogen atmosphere, and stirred and refluxed. After that, potassium carbonate (20g, 145.1mmol) was dissolved in 60ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.9 g of subDE-1. (Yield 56%, MS: [M+H]+= 442)

In a nitrogen atmosphere, subDE-1 (15g, 33.9mmol) and amine28 (17.5g, 35.6mmol) were added to 300ml of THF, stirred and refluxed. After that, potassium carbonate (14.1g, 101.8mmol) was dissolved in 42ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17.1 g of compound 2-29. (yield 59%, MS: [M+H] + = 853)

Synthesis Example 2-30

Chemical formula (15g, 48.4mmol) and [1,1'-biphenyl]-4-ylboronic acid (10.1g, 50.8mmol) were added to 300ml of THF in a nitrogen atmosphere, stirred and refluxed. After that, potassium carbonate (20g, 145.1mmol) was dissolved in 60ml of water and thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 10.5 g of subDF-2. (Yield 51%, MS: [M+H]+= 428)

In a nitrogen atmosphere, subDF-2 (15g, 35.1mmol) and amine29 (18.1g, 36.8mmol) were added to 300ml of THF, followed by stirring and reflux. After that, potassium carbonate (14.5g, 105.2mmol) was dissolved in 44ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After the reaction for 12 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17.3 g of compound 2-30. (yield 59%, MS: [M+H]+= 839)

<Examples and Comparative Examples>

Comparative Example A

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1000 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it was transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

The following compound HI-1 was formed to a thickness of 1150 Å as a hole injection layer on the prepared ITO transparent electrode, but the following compound A-1 was p-doped at a concentration of 1.5 wt%. The following compound HT-1 was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 800 Å. Then, the following compound EB-1 was vacuum-deposited to a film thickness of 150 Å on the hole transport layer to form an electron blocking layer. Next, the following compounds RH-1 and Dp-7 were vacuum-deposited on the EB-1 deposited film in a weight ratio of 98:2 to form a red light emitting layer having a thickness of 400 Å. A hole blocking layer was formed by vacuum-depositing the following compound HB-1 to a thickness of 30 Å on the light emitting layer. Then, on the hole blocking layer, the following compound ET-1 and the following compound LiQ were vacuum-deposited in a weight ratio of 2:1 to form an electron injection and transport layer to a thickness of 300 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1000 Å on the electron injection and transport layer.

In the above process, the deposition rate of organic material was maintained at 0.4 ~ 0.7 Å/sec, the deposition rate of lithium fluoride of the negative electrode was 0.3 Å/sec, and the deposition rate of aluminum was 2 Å/sec, and the vacuum degree during deposition was 2×10 ^-7 ~ 5×10 ^-6 torr was maintained, and an organic light emitting device was manufactured.

Examples 1 to 17

An organic light emitting device was manufactured in the same manner as in Comparative Example A, except that the compound shown in Table 1 was used instead of the compound RH-1 as a host in the organic light emitting device of Comparative Example A.

Comparative Examples 1 to 7

An organic light emitting device was manufactured in the same manner as in Comparative Example A, except that the compound shown in Table 1 was used instead of the compound RH-1 as a host in the organic light emitting device of Comparative Example A. The structures of compounds B-8 to B-14 of Table 1 are as follows.

Examples 18-47

An organic light emitting device was manufactured in the same manner as in Comparative Example A, except that the compound shown in Table 2 below was used as the electron blocking layer material instead of the compound EB-1 in the organic light emitting device of Comparative Example A.

Comparative Examples 8 to 14

An organic light emitting device was manufactured in the same manner as in Comparative Example A, except that the compound shown in Table 2 below was used as the electron blocking layer material instead of the compound EB-1 in the organic light emitting device of Comparative Example A. The structures of compounds B-1 to B-7 of Table 2 are as follows.

Examples 48 to 119

In the organic light emitting device of Comparative Example A, the organic light emitting device was used in the same manner as in Comparative Example A, except that the compound of the first host and the second host described in Table 3 was used in a weight ratio of 1:1 instead of the compound RH-1 as a host. A light emitting device was manufactured.

<Experimental example>

When a current is applied to the organic light emitting devices prepared in Examples 1 to 161 and Comparative Example A and Comparative Examples 1 to 88, voltage, efficiency, and lifetime are measured (based on 15 mA/cm ² ), The results are shown in Tables 1 to 3 below. The lifetime T95 means the time it takes for the lifetime to decrease to 95% from the initial luminance of 7,000 nits.

division host Driving voltage (V) Efficiency (cd/A) Life T95 (hr) luminous color Comparative Example A Compound RH-1 3.91 16.54 113 Red Example 1 compound 1-1 3.72 18.09 162 Red Example 2 compound 1-2 3.71 18.15 161 Red Example 3 compound 1-3 3.68 17.91 160 Red Example 4 compound 1-4 3.78 17.64 157 Red Example 5 compound 1-5 3.70 18.28 166 Red Example 6 compound 1-6 3.71 18.34 165 Red Example 7 compound 1-7 3.72 17.94 155 Red Example 8 compound 1-8 3.68 18.24 162 Red Example 9 compound 1-9 3.77 18.20 169 Red Example 10 compound 1-10 3.71 18.21 171 Red Example 11 compound 1-11 3.83 18.59 201 Red Example 12 compound 1-12 3.84 18.92 199 Red Example 13 compound 1-13 3.53 19.77 219 Red Example 14 compound 1-14 3.53 19.98 210 Red Example 15 compound 1-15 3.59 19.62 226 Red Example 16 compound 1-16 3.55 20.48 217 Red Example 17 compound 1-17 3.61 19.70 212 Red Comparative Example 1 compound B-8 4.06 15.55 127 Red Comparative Example 2 compound B-9 4.11 15.53 122 Red Comparative Example 3 compound B-10 4.11 15.68 118 Red Comparative Example 4 compound B-11 4.19 15.31 111 Red Comparative Example 5 compound B-12 4.29 14.71 113 Red Comparative Example 6 compound B-13 4.28 15.01 94 Red Comparative Example 7 compound B-14 4.07 15.63 117 Red

division electron blocking layer Driving voltage (V) Efficiency (cd/A) Life T95 (hr) luminous color Example 18 compound 2-1 3.67 17.26 172 Red Example 19 compound 2-2 3.71 17.44 168 Red Example 20 compound 2-3 3.71 17.64 186 Red Example 21 compound 2-4 3.69 17.64 175 Red Example 22 compound 2-5 3.61 17.59 184 Red Example 23 compound 2-6 3.68 17.65 182 Red Example 24 compound 2-7 3.70 17.40 171 Red Example 25 compound 2-8 3.77 18.35 209 Red Example 26 compound 2-9 3.85 18.81 184 Red Example 27 compound 2-10 3.81 18.82 185 Red Example 28 compound 2-11 3.86 18.51 202 Red Example 29 compound 2-12 3.75 18.57 198 Red Example 30 compound 2-13 3.80 18.42 204 Red Example 31 compound 2-14 3.85 18.57 208 Red Example 32 compound 2-15 3.72 17.84 157 Red Example 33 compound 2-16 3.77 17.59 171 Red Example 34 compound 2-17 3.79 17.52 169 Red Example 35 compound 2-18 3.79 17.81 160 Red Example 36 compound 2-19 3.79 18.06 164 Red Example 37 compound 2-20 3.76 17.92 156 Red Example 38 compound 2-21 3.62 20.66 214 Red Example 39 compound 2-22 3.63 19.99 218 Red Example 40 compound 2-23 3.58 19.41 219 Red Example 41 compound 2-24 3.53 19.23 205 Red Example 42 compound 2-25 3.54 20.27 206 Red Example 43 compound 2-26 3.55 20.40 215 Red Example 44 compound 2-27 3.61 20.72 218 Red Example 45 compound 2-28 3.53 19.98 210 Red Example 46 compound 2-29 3.58 19.52 214 Red Example 47 compound 2-30 3.57 20.96 221 Red Comparative Example 8 Compound B-1 4.18 14.85 96 Red Comparative Example 9 compound B-2 4.24 14.92 112 Red Comparative Example 10 compound B-3 4.28 15.34 115 Red Comparative Example 11 Compound B-4 4.16 14.95 91 Red Comparative Example 12 compound B-5 4.22 15.31 107 Red Comparative Example 13 compound B-6 4.12 15.94 121 Red Comparative Example 14 compound B-7 4.05 15.60 124 Red

division 1st host 2nd host Driving voltage (V) Efficiency (cd/A) Life T95 (hr) luminous color Example 48 compound 1-1 compound 2-1 3.45 22.22 247 Red Example 49 compound 1-1 compound 2-4 3.50 22.27 244 Red Example 50 compound 1-1 compound 2-10 3.43 22.02 237 Red Example 51 compound 1-1 compound 2-15 3.48 22.13 244 Red Example 52 compound 1-1 compound 2-22 3.42 22.65 238 Red Example 53 compound 1-1 compound 2-26 3.45 22.35 239 Red Example 54 compound 1-3 compound 2-2 3.50 22.07 245 Red Example 55 compound 1-3 compound 2-5 3.47 22.18 235 Red Example 56 compound 1-3 compound 2-11 3.45 22.06 249 Red Example 57 compound 1-3 compound 2-16 3.50 22.70 248 Red Example 58 compound 1-3 compound 2-23 3.62 22.16 212 Red Example 59 compound 1-3 compound 2-27 3.37 21.63 255 Red Example 60 compound 1-4 compound 2-3 3.32 21.99 256 Red Example 61 compound 1-4 compound 2-6 3.31 22.07 243 Red Example 62 compound 1-4 compound 2-12 3.33 21.86 251 Red Example 63 compound 1-4 compound 2-17 3.32 21.88 256 Red Example 64 compound 1-4 compound 2-24 3.37 22.16 248 Red Example 65 compound 1-4 compound 2-28 3.32 21.96 245 Red Example 66 compound 1-5 compound 2-1 3.31 22.20 256 Red Example 67 compound 1-5 compound 2-4 3.30 22.01 255 Red Example 68 compound 1-5 compound 2-13 3.34 21.65 250 Red Example 69 compound 1-5 compound 2-18 3.40 20.84 206 Red Example 70 compound 1-5 compound 2-25 3.45 23.20 275 Red Example 71 compound 1-5 compound 2-29 3.50 23.13 270 Red Example 72 compounds 1-8 compound 2-1 3.43 22.87 267 Red Example 73 compounds 1-8 compound 2-4 3.48 23.15 264 Red Example 74 compounds 1-8 compound 2-10 3.42 23.12 262 Red Example 75 compounds 1-8 compound 2-15 3.45 22.83 268 Red Example 76 compounds 1-8 compound 2-22 3.50 23.12 262 Red Example 77 compounds 1-8 compound 2-26 3.47 22.99 262 Red Example 78 compounds 1-9 compound 2-2 3.45 23.20 275 Red Example 79 compounds 1-9 compound 2-5 3.50 22.95 272 Red Example 80 compounds 1-9 compound 2-11 3.44 24.12 285 Red Example 81 compounds 1-9 compound 2-16 3.37 23.71 289 Red Example 82 compounds 1-9 compound 2-23 3.44 23.97 288 Red Example 83 compounds 1-9 compound 2-27 3.35 24.15 286 Red Example 84 compounds 1-10 compound 2-3 3.43 23.98 282 Red Example 85 compounds 1-10 compound 2-6 3.36 24.44 274 Red Example 86 compounds 1-10 compound 2-12 3.40 24.40 273 Red Example 87 compounds 1-10 compound 2-17 3.44 23.73 270 Red Example 88 compounds 1-10 compound 2-24 3.44 24.14 275 Red Example 89 compounds 1-10 compound 2-28 3.38 23.76 287 Red Example 90 compound 1-13 compound 2-1 3.38 23.76 287 Red Example 91 compound 1-13 compound 2-4 3.45 23.20 275 Red Example 92 compound 1-13 compound 2-13 3.50 23.13 270 Red Example 93 compound 1-13 compound 2-18 3.45 23.00 275 Red Example 94 compound 1-13 compound 2-25 3.47 23.21 274 Red Example 95 compound 1-13 compound 2-29 3.47 22.94 267 Red Example 96 compound 1-14 compound 2-1 3.54 22.81 260 Red Example 97 compound 1-14 compound 2-4 3.52 23.18 262 Red Example 98 compound 1-14 compound 2-10 3.46 23.25 266 Red Example 99 compound 1-14 compound 2-15 3.55 22.80 272 Red Example 100 compound 1-14 compound 2-22 3.51 23.30 263 Red Example 101 compound 1-14 compound 2-26 3.49 22.97 274 Red Example 102 compound 1-15 compound 2-2 3.45 22.23 236 Red Example 103 compound 1-15 compound 2-5 3.47 22.84 243 Red Example 104 compound 1-15 compound 2-11 3.47 22.07 247 Red Example 105 compound 1-15 compound 2-16 3.54 22.63 242 Red Example 106 compound 1-15 compound 2-23 3.52 22.62 238 Red Example 107 compound 1-15 compound 2-27 3.46 22.73 242 Red Example 108 compound 1-16 compound 2-3 3.55 22.83 250 Red Example 109 compound 1-16 compound 2-6 3.51 22.41 245 Red Example 110 compound 1-16 compound 2-12 3.40 24.49 273 Red Example 111 compound 1-16 compound 2-17 3.44 24.03 284 Red Example 112 compound 1-16 compound 2-24 3.42 24.47 270 Red Example 113 compound 1-16 compound 2-28 3.39 23.86 285 Red Example 114 compound 1-17 compound 2-1 3.36 23.80 275 Red Example 115 compound 1-17 compound 2-4 3.36 24.22 290 Red Example 116 compound 1-17 compound 2-10 3.39 24.47 272 Red Example 117 compound 1-17 compound 2-15 3.43 24.19 281 Red Example 118 compound 1-17 compound 2-22 3.37 24.34 289 Red Example 119 compound 1-17 compound 2-26 3.42 24.49 272 Red

When a current was applied to the organic light emitting diodes fabricated in Examples 1 to 119 and Comparative Examples 1 to 14, the results shown in Tables 1 to 3 were obtained.

When the compounds 1-1 to 1-17 of the present invention were used as a red host, it was confirmed that the driving voltage decreased compared to the compound of Comparative Example and the efficiency and lifespan were increased as shown in Table 1. In addition, even when the compounds 2-1 to 2-30 of the present invention were used as the electron blocking layer, as shown in Table 2, the driving voltage was decreased compared to the comparative example compound, and the efficiency and lifespan were increased.

In Table 3, a single material when used as a red host by selecting one of compounds 1-1 to 1-17 as a first host, and selecting one of compounds 2-1 to 2-30 as a second host and co-deposition It was confirmed that the driving voltage decreased and the efficiency and lifespan increased compared to when using a host of

From the results of Tables 1 to 3, when the compound of Formula 1 is used as a host or electron blocking layer material for a red light emitting layer in a device expressing red, the driving voltage, luminous efficiency and lifespan characteristics of the organic light emitting device can be improved. can confirm.

[Explanation of code]

1: substrate 2: Anode

3: organic layer 4: cathode

5: hole injection layer 6: hole transport layer

7: Electron blocking layer 8: light emitting layer

9: hole-inhibiting layer 10: electron transport layer

11: electron injection layer 12: electron injection and transport layer

Claims (10)

A compound represented by the following formula (1):
[Formula 1]

In Formula 1,
A ₁ is represented by the following formula 1-a,
[Formula 1-a]

In Formula 1-a,
The dotted line is the part that is fused with the adjacent ring,
X is O or S;
Ar ₁ is substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S,
A ₂ is the following formula 1-b; Or a substituent represented by the following formula 1-c,
[Formula 1-b]

[Formula 1-c]

In Formulas 1-b and 1-c,
L ₁ to L ₄ are each independently, a single bond; substituted or unsubstituted C _6-60 arylene; Or substituted or unsubstituted C _2-60 heteroarylene containing any one or more heteroatoms selected from the group consisting of N, O and S,
Ar ₂ to Ar ₅ are each independently, substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S,
D is deuterium,
n is an integer from 0 to 5;
According to claim 1,
Formula 1 is represented by any one of the following Formulas 1-1 to 1-4,
compound:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4,
X, L ₁ to L ₄ , Ar ₁ to Ar ₅ , D, and n are as defined in claim 1.
According to claim 1,
L ₁ and L ₂ are each independently a single bond; phenylene; biphenyldiyl; or naphthalenediyl,
compound.
According to claim 1,
Ar ₁ is phenyl; biphenylyl; naphthyl; dibenzofuranyl; or dibenzothiophenyl;
compound.
According to claim 1,
Ar ₂ and Ar ₃ are each independently, phenyl; biphenylyl; naphthyl; phenylnaphthyl; naphthylphenyl; dibenzofuranyl; dibenzothiophenyl; or phenanthrenyl;
compound.
According to claim 1,
L ₃ and L ₄ are each independently, a single bond; phenylene; biphenyldiyl; or naphthalenediyl,
compound.
According to claim 1,
Ar ₄ and Ar ₅ are each independently, phenyl; biphenylyl; terphenylyl; naphthyl; naphthylphenyl; phenylnaphthyl; phenanthrenyl; 9-phenylcarbazolyl; dibenzofuranyl; or dibenzothiophenyl;
compound.
According to claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of
compound:

a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers contains the compound according to any one of claims 1 to 8 which is an organic light emitting device.
10. The method of claim 9,
The organic material layer containing the compound is a light emitting layer and / or an electron blocking layer,
organic light emitting device.

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