KR20230080359A - 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 containing the same. The present invention provides a compound represented by chemical formula 1. The compound represented by the chemical formula 1 can be used as a material for an organic material layer of the organic light emitting device, and 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 including the same.

In general, the organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, and a fast response time, and has 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, a cathode, and an organic material layer between the anode and the cathode. In order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often composed of a multi-layered structure composed of different materials, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. In the structure of this organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and when the injected holes and electrons meet, excitons are formed. When it falls back to the ground state, it glows.

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

Meanwhile, in recent years, an organic light emitting device using a solution process, particularly an inkjet process, instead of a conventional deposition process has been developed to reduce process costs. In the early days, an attempt was made to develop an organic light emitting device by coating all organic light emitting device layers with a solution process, but the current technology has limitations, so only HIL, HTL, and EML in the form of a regular structure are carried out as a solution process, and the subsequent process is the existing deposition process A hybrid process that utilizes is being studied.

Accordingly, the present invention provides a novel organic light emitting device material that can be used in an organic light emitting device and can be used in a solution process at the same time.

Korean Patent Publication No. 10-2000-0051826

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

The present invention provides a compound represented by Formula 1 below:

[Formula 1]

In Formula 1,

One of X ₁ to X ₄ is CR, and the others are each independently N, CH, or CD;

Here, R is a substituent represented by Formula 2 below,

X ₅ to X ₁₀ are each independently N, CH, or CD;

However, one of X ₁ to X ₁₀ is N,

[Formula 2]

In Formula 2,

L ₁ is a direct bond; Substituted or unsubstituted C _6-60 arylene; Or a C _2-60 heteroarylene containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,

L ₂ is a direct bond; Substituted or unsubstituted C _6-60 arylene; Or a substituted or unsubstituted C _2-60 heteroarylene containing at least one heteroatom selected from the group consisting of N, O and S, and

L ₃ is a direct bond; Substituted or unsubstituted C _6-60 arylene; Or a C _2-60 heteroarylene containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,

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

Ar ₂ is a substituted or unsubstituted C _6-60 aryl; Or a C _2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S.

In addition, the present invention is a first electrode; a second electrode provided to face the first electrode; and an organic material layer provided between the first electrode and the second electrode, wherein the organic material layer includes the compound represented by Chemical Formula 1. Specifically, the organic material layer including the compound may be a light emitting layer.

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

1 shows an example of an organic light emitting device composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
2 is an example of an organic light emitting device composed of a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (7), an electron injection and transport layer (8) and a cathode (4). is shown.

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

(Definition of Terms)

또는

는 다른 치환기에 연결되는 결합을 의미하고, "D"는 중수소를 의미한다.In this specification,

or

means a bond connected to another substituent, and "D" means deuterium.

In this specification, the term "substituted or unsubstituted" means deuterium; halogen group; cyano group; nitro group; hydroxy group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy group; Alkyl thioxy group; Arylthioxy group; an alkyl sulfoxy group; aryl sulfoxy groups; silyl group; boron group; an alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; Aralkenyl group; Alkyl aryl group; Alkylamine group; Aralkylamine group; heteroarylamine group; Arylamine group; Arylphosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heteroaryl containing at least one of N, O, and S atoms, or substituted or unsubstituted with two or more substituents linked to each other among the substituents exemplified above. . 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 or 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 is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the ester group may be substituted with an aryl group having 6 to 25 carbon atoms or a straight-chain, branched-chain or cyclic chain alkyl group having 1 to 25 carbon atoms in the ester group. 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 is preferably 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 is specifically 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. but not limited to

In the present specification, the boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, but is not limited thereto.

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

In the present specification, the alkyl group may be straight-chain or branched-chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 10. 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, etc., but is 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 one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. 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, etc., but is 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 number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. 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 are 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 one embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc. as a monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., 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. However, it is not limited thereto.

In the present specification, heteroaryl is a heteroaryl containing at least one of O, N, Si, and S as a heterogeneous element, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms. Examples of the heteroaryl include xanthene, thioxanthen, thiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, triazole, pyridyl, bipyridyl, Pyrimidyl group, triazine group, acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl 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 ( phenanthroline), an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto.

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

(compound)

The present invention provides a compound represented by Formula 1 above.

One of X ₁ to X ₄ is CR, and the others are each independently N, CH, or CD, wherein R is a substituent represented by Formula 2 below, and X ₅ to X ₁₀ are each independently N, CH, or CD, provided that one of X ₁ to X ₁₀ is N.

Specifically, one of X ₁ to X ₄ is CR, the other is N, the others are each independently CH or CD, and X ₅ to X ₁₀ are each independently CH or CD; or one of X ₁ to X ₄ is CR, the others are each independently CH or CD, one of X ₅ to X ₁₀ is N, and the others are each independently CH or CD.

L ₁ is a direct bond; Substituted or unsubstituted C _6-60 arylene; Or a C _2-60 heteroarylene containing at least one heteroatom selected from the group consisting of substituted or unsubstituted N, O and S. Preferably, L ₁ is a direct bond; or phenylene. When L ₁ is phenylene, it may be unsubstituted or substituted with one or more deuterium atoms.

L ₂ is a direct bond; Substituted or unsubstituted C _6-60 arylene; Or a C _2-60 heteroarylene containing at least one heteroatom selected from the group consisting of substituted or unsubstituted N, O and S. Preferably, L ₂ is a direct bond; phenylene; naphthylene; biphenylylene; 9,9-dimethyl-fluorenylene; or 9,9-diphenyl-fluorenylene. L ₂ is phenylene; naphthylene; biphenylylene; 9,9-dimethyl-fluorenylene; or 9,9-diphenyl-fluorenylene, they may be unsubstituted or substituted with one or more deuterium atoms.

L ₃ is a direct bond; Substituted or unsubstituted C _6-60 arylene; Or a C _2-60 heteroarylene containing at least one heteroatom selected from the group consisting of substituted or unsubstituted N, O and S. Preferably, L ₃ is a direct bond; phenylene; naphthylene; biphenylylene; 9,9-dimethyl-fluorenylene; or 9,9-diphenyl-fluorenylene. L ₃ is phenylene; naphthylene; biphenylylene; 9,9-dimethyl-fluorenylene; or 9,9-diphenyl-fluorenylene, they may be unsubstituted or substituted with one or more deuterium atoms.

Ar ₁ is a substituted or unsubstituted C _6-60 aryl; Or a C _2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S. Ar ₁ is phenyl; biphenylyl; terphenylyl; naphthyl; 9,9-dimethyl-fluorenyl; 9,9-diphenyl-fluorenyl; dibenzofuranyl; dibenzothiophenyl; 9-phenyl-carbazolyl; 9-naphthyl-carbazolyl; or 9,9'-spirobi[9H-fluorene]yl. Ar ₁ may be unsubstituted or substituted with one or more deuterium atoms.

Ar ₂ is a substituted or unsubstituted C _6-60 aryl; Or a C _2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S. Ar ₂ is phenyl; biphenylyl; terphenylyl; naphthyl; 9,9-dimethyl-fluorenyl; 9,9-diphenyl-fluorenyl; dibenzofuranyl; dibenzothiophenyl; 9-phenyl-carbazolyl; 9-naphthyl-carbazolyl; or 9,9'-spirobi[9H-fluorene]yl. Ar ₂ may be unsubstituted or substituted with one or more deuterium.

In addition, the compound may be a compound represented by any one of Chemical Formulas 1-1 to 1-4.

[Formula 1-1]

In Formula 1-1,

One of X ₂ to X ₁₀ is N, and the others are each independently CH or CD;

L ₁ to L ₃ , Ar ₁ and Ar ₂ are as defined in Formula 1,

[Formula 1-2]

In Formula 1-2,

One of X ₁ and X ₃ to X ₁₀ is N, and the others are each independently CH or CD;

L ₁ to L ₃ , Ar ₁ and Ar ₂ are as defined in Formula 1,

[Formula 1-3]

In Formula 1-3 above.

One of X ₁ , X ₂ and X ₄ to X ₁₀ is N, and the others are each independently CH or CD;

L ₁ to L ₃ , Ar ₁ and Ar ₂ are as defined in Formula 1,

[Formula 1-4]

In Chemical Formulas 1-4,

One of X ₁ to X ₃ and X ₅ to X ₁₀ is N, and the others are each independently CH or CD,

L ₁ to L ₃ , Ar ₁ and Ar ₂ are as defined in Formula 1.

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

In addition, the compound may contain no deuterium or one or more deuterium atoms.

On the other hand, the present invention provides a method for producing a compound represented by Formula 1, such as the following Reaction Schemes 1 and 2, for example:

[Scheme 1]

[Scheme 2]

In Reaction Schemes 1 and 2, X ₁ to X ₁₀ , L ₁ to L ₃ , and Ar ₁ and Ar ₂ are defined as in Chemical Formulas 1 and 2, respectively. In Schemes 1 and 2, Z is halogen, preferably chloro.

Reaction Scheme 1 is a reaction for preparing the core structure of Chemical Formula 1 through a Suzuki coupling reaction. In addition, Scheme 2 is also a Suzuki coupling reaction, and it is preferable to carry out in the presence of a palladium catalyst, and the reactor for the Suzuki coupling reaction can be changed as known in the art. The preparation method may be more specific in Preparation Examples and Synthesis Examples to be described later.

(organic light emitting element)

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

The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, or 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, a hole blocking layer, an electron transport layer, an electron injection layer, and the like as organic layers. However, the structure of the organic light emitting device is not limited thereto and may include fewer organic layers.

In addition, the organic material layer may include a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes, and the hole injection layer, the hole transport layer, or a layer that simultaneously injects and transports holes is represented by Formula 1 above. may contain the indicated compounds.

Also, the organic material layer may include a light emitting layer, and the light emitting layer may include the compound represented by Chemical Formula 1.

In addition, the organic material layer may include a hole blocking layer, an electron transport layer, an electron injection layer, or a layer that simultaneously transports and injects electrons, and the hole blocking layer, the electron transport layer, the electron injection layer, or the electron transport and electron injection layer. The layer to be simultaneously injected may include the compound represented by Chemical Formula 1 above.

Also, the organic material layer may include a light emitting layer and an electron injection and transport layer, and the electron injection and transport layer may include the compound represented by Chemical Formula 1.

Also, 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. In addition, the organic light emitting device according to the present invention may be an organic light emitting device of an inverted type 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 and 2 .

1 shows an example of an organic light emitting device composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.

2 is an example of an organic light emitting device composed of a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (7), an electron injection and transport layer (8) and a cathode (4). is shown. In this structure, the compound represented by Chemical Formula 1 may be included in the light emitting 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 of the organic layers includes the compound represented by Chemical Formula 1. 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 an anode, an organic material layer, and a cathode on a substrate. At this time, using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, depositing a metal or a metal oxide having conductivity or an alloy thereof on the substrate to form an anode 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, and depositing a material that can be used as a cathode thereon, it can be prepared. 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 Chemical 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 means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

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

In one example, the first electrode is an anode and 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 high work function is generally preferred so that holes can be smoothly injected into the organic material layer. Specific examples of the cathode material include metals such as vanadium, chromium, copper, zinc, and 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 compounds such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; and the like, but are not limited thereto.

The cathode material is preferably a material having a small work function so as to easily inject electrons 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; There are multi-layered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode, and the hole injection material has the ability to transport holes and has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and generated in the light emitting layer A compound that prevents migration of excitons to the electron injecting layer or electron injecting material and has excellent thin film formation ability is preferred. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrins, oligothiophenes, arylamine-based organic materials, hexanitrilehexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene-based organic materials. of organic matter, anthraquinone, and polyaniline and polythiophene-based conductive compounds, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light emitting layer, and has high hole mobility. material is suitable. Specific examples include, but are not limited to, arylamine-based organic materials, conductive compounds, and block copolymers having both conjugated and non-conjugated parts.

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-hydroxybenzoquinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; Polyfluorene, rubrene, etc., but are not limited thereto.

The electron blocking layer is a layer placed between the hole transport layer and the light emitting layer to prevent electrons injected from the cathode from passing to the hole transport layer without recombination in the light emitting layer, and is also called an electron blocking layer. A material having a smaller electron affinity than the electron transport layer is preferable for the electron blocking layer. Preferably, the compound represented by Chemical Formula 1 may be included as a material of the electron blocking layer.

The light emitting layer may include a host material and a dopant material. As the host material, the compound represented by Chemical Formula 1 may be used. In addition, as a host material that can be further used, a condensed aromatic ring derivative or a compound containing a heterocyclic ring can be used. 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, etc., but are not limited thereto.

Dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, periplanthene, etc. having an arylamino group, and styrylamine compounds include substituted or unsubstituted arylamine is substituted with at least one arylvinyl group, wherein 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, etc., but is not limited thereto. In addition, metal complexes include, but are not limited to, iridium complexes and platinum complexes.

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

The electron injection layer is a layer for injecting electrons from an electrode, has the ability to transport electrons, has an excellent electron injection effect from a cathode, an excellent electron injection effect for a light emitting layer or a light emitting material, and injects holes of excitons generated in the light emitting layer. A compound that prevents migration to a layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preonylidene methane, anthrone, etc. and their derivatives, 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)( There are o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtolato)gallium. Not limited to this.

On the other hand, in the present invention, the "electron injection and transport layer" is a layer that performs both the roles of the electron injection layer and the electron transport layer, and materials that play the role of each layer may be used alone or in combination, but are limited thereto. It doesn't work. Preferably, the compound represented by Formula 1 may be included as a material for 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 light emitting efficiency.

In addition, the compound according to the present invention may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

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

Synthesis Example A-1-1: Preparation of Intermediate Compound A-1-1

3-Bromo-2-chloropyridine (15g, 77.9 mmol) and (1-(methylthio)naphthalen-2-yl)boronic acid (17.8g, 81.8 mmol) were added to 300 ml of THF, stirred and refluxed. Thereafter, potassium carbonate (32.3g, 233.8 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.4g, 0.8 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, and the organic layer and the water layer were separated, and the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.8 g of compound A-1-1_P1. (Yield 62%, MS:[M+H] ⁺ =286)

Compound A-1-1_P1 (15g, 52.5 mmol) and hydrogen peroxide (2.7g, 78.7 mmol) were added to 300 ml of acetic acid, stirred and refluxed. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the reaction mixture was poured into 600 ml of water, and crystals were dropped and filtered. The filtered solid was dissolved in chloroform, washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 8.1 g of compound A-1-1_P2. (Yield 51%, MS: [M+H]+=302)

Compound A-1-1_P2 (15g, 49.7 mmol) was added to 300 ml of sulfuric acid, stirred and refluxed. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the reaction mixture was poured into 600 ml of water, and crystals were dropped and filtered. The filtered solid was dissolved in chloroform, washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 6.2 g of intermediate compound A-1-1. (Yield 49%, MS:[M+H] ⁺ =254)

Synthesis Example A-1-6: Preparation of Intermediate Compound A-1-6

1-Bromo-2-chlorobenzene (15g, 78.3 mmol) and (5-(methylthio)isoquinolin-6-yl)boronic acid (18g, 82.3 mmol) were added to 300 ml of THF, stirred and refluxed. Thereafter, potassium carbonate (32.5g, 235 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.4g, 0.8 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, and the organic layer and the water layer were separated, and the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.4 g of compound A-1-6_P1. (Yield 69%, MS:[M+H] ⁺ =286)

Compound A-1-6_P1 (15g, 52.5 mmol) and hydrogen peroxide (2.7g, 78.7 mmol) were added to 300 ml of acetic acid, stirred and refluxed. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the reaction mixture was poured into 600 ml of water, and crystals were dropped and filtered. The filtered solid was dissolved in chloroform, washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, 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 compound A-1-6_P2. (Yield 52%, MS:[M+H] ⁺ =302)

Compound A-1-6_P2 (15g, 49.7mmol) was added to 300ml of sulfuric acid and stirred and refluxed. After reacting for 5 hours, the reaction mixture was cooled to room temperature, and the reaction mixture was poured into 600 ml of water to drop crystals and filtered. The filtered solid was dissolved in chloroform, washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 5.9 g of intermediate compound A-1-6. (Yield 47%, MS: [M+H]+=254)

Synthesis Example A-2-2: Preparation of Intermediate Compound A-2-2

4-Bromo-2-chloropyridine (15g, 77.9 mmol) and (1-(methylthio)naphthalen-2-yl)boronic acid (17.8g, 81.8 mmol) were added to 300 ml of THF, stirred and refluxed. Thereafter, potassium carbonate (32.3g, 233.8 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.4g, 0.8 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, and the organic layer was distilled after separating the organic layer and the water layer. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.8 g of compound A-2-2_P1. (Yield 62%, MS:[M+H] ⁺ =286)

Compound A-2-2_P1 (15g, 52.5 mmol) and hydrogen peroxide (2.7g, 78.7 mmol) were added to 300 ml of acetic acid, stirred and refluxed. After reacting for 4 hours, the reaction mixture was cooled to room temperature, and the reaction mixture was poured into 600 ml of water, and crystals were dropped and filtered. The filtered solid was dissolved in chloroform, washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, 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 compound A-2-2_P2. (Yield 55%, MS:[M+H] ⁺ =302)

Compound A-2-2_P2 (15g, 49.7 mmol) was added to 300 ml of sulfuric acid and stirred and refluxed. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the reaction mixture was poured into 600 ml of water, and crystals were dropped and filtered. The filtered solid was dissolved in chloroform, washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 6.8 g of intermediate compound A-2-2. (Yield 54%, MS:[M+H] ⁺ =254)

Synthesis Example A-2-4: Preparation of Intermediate Compound A-2-4

1-Bromo-3-chlorobenzene (15g, 78.3 mmol) and (8-(methylthio)quinolin-7-yl)boronic acid (18g, 82.3 mmol) were added to 300 ml of THF, stirred and refluxed. Thereafter, potassium carbonate (32.5g, 235 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.4g, 0.8 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, and the organic layer and the water layer were separated, and the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.8 g of compound A-2-4_P1. (Yield 62%, MS:[M+H] ⁺ =286)

Compound A-2-4_P1 (15g, 52.5 mmol) and hydrogen peroxide (2.7g, 78.7 mmol) were added to 300 ml of acetic acid, stirred and refluxed. After reacting for 5 hours, the reaction mixture was cooled to room temperature, and the reaction mixture was poured into 600 ml of water, and crystals were dropped and filtered. The filtered solid was dissolved in chloroform, washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, 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 compound A-2-4_P2. (Yield 59%, MS:[M+H] ⁺ =302)

Compound A-2-4_P2 (15g, 49.7 mmol) was added to 300 ml of sulfuric acid and stirred and refluxed. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the reaction mixture was poured into 600 ml of water, and crystals were dropped and filtered. The filtered solid was dissolved in chloroform, washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 7.2 g of intermediate compound A-2-4. (Yield 57%, MS:[M+H] ⁺ =254)

Synthesis Example A-2-7: Preparation of Intermediate Compound A-2-7

1-Bromo-3-chlorobenzene (15g, 78.3 mmol) and (5-(methylthio)quinolin-6-yl)boronic acid (18g, 82.3 mmol) were added to 300 ml of THF, stirred and refluxed. Thereafter, potassium carbonate (32.5g, 235 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.4g, 0.8 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the organic layer was distilled after separating the organic layer and the water layer. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, 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 A-2-7_P1. (Yield 64%, MS:[M+H] ⁺ =286)

Compound A-2-7_P1 (15g, 52.5 mmol) and hydrogen peroxide (2.7g, 78.7 mmol) were added to 300 ml of acetic acid, stirred and refluxed. After reacting for 5 hours, the reaction mixture was cooled to room temperature, and the reaction mixture was poured into 600 ml of water, and crystals were dropped and filtered. The filtered solid was dissolved in chloroform, washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, 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 compound A-2-7_P2. (Yield 58%, MS:[M+H] ⁺ =302)

Compound A-2-7_P2 (15g, 49.7 mmol) was added to 300 ml of sulfuric acid, stirred and refluxed. After reacting for 4 hours, the reaction mixture was cooled to room temperature, and the reaction mixture was poured into 600 ml of water, and crystals were dropped and filtered. The filtered solid was dissolved in chloroform, washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 5.4 g of intermediate compound A-2-7. (Yield 43%, MS:[M+H] ⁺ =254)

Synthesis Example A-3-5: Preparation of Intermediate Compound A-3-5

1-Bromo-4-chlorobenzene (15g, 78.3 mmol) and (8-(methylthio)isoquinolin-7-yl)boronic acid (18g, 82.3 mmol) were added to 300 ml of THF, stirred and refluxed. Thereafter, potassium carbonate (32.5g, 235 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.4g, 0.8 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, and the organic layer and the water layer were separated, and the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.4 g of compound A-3-5_P1. (Yield 69%, MS:[M+H] ⁺ =286)

Compound A-3-5_P1 (15g, 52.5 mmol) and hydrogen peroxide (2.7g, 78.7 mmol) were added to 300 ml of acetic acid, stirred and refluxed. After reacting for 4 hours, the reaction mixture was cooled to room temperature, and the reaction mixture was poured into 600 ml of water, and crystals were dropped and filtered. The filtered solid was dissolved in chloroform, washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 9 g of compound A-3-5_P2. (Yield 57%, MS:[M+H] ⁺ =302)

Compound A-3-5_P2 (15g, 49.7 mmol) was added to 300 ml of sulfuric acid and stirred and refluxed. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the reaction mixture was poured into 600 ml of water, and crystals were dropped and filtered. The filtered solid was dissolved in chloroform, washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 5.9 g of intermediate compound A-3-5. (Yield 47%, MS:[M+H] ⁺ =254)

Synthesis Example A-3-9: Preparation of Intermediate Compound A-3-9

1-Bromo-4-chlorobenzene (15g, 78.3 mmol) and (4-(methylthio)isoquinolin-3-yl)boronic acid (18g, 82.3 mmol) were added to 300 ml of THF, stirred and refluxed. Thereafter, potassium carbonate (32.5g, 235 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.4g, 0.8 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.4 g of compound A-3-9_P1. (Yield 60%, MS:[M+H] ⁺ =286)

Compound A-3-9_P1 (15g, 52.5 mmol) and hydrogen peroxide (2.7g, 78.7 mmol) were added to 300 ml of acetic acid, stirred and refluxed. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the reaction mixture was poured into 600 ml of water, and crystals were dropped and filtered. The filtered solid was dissolved in chloroform, washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 8.1 g of compound A-3-9_P2. (Yield 51%, MS:[M+H] ⁺ =302)

Compound A-3-9_P2 (15g, 49.7 mmol) was added to 300 ml of sulfuric acid and stirred and refluxed. After reacting for 5 hours, the reaction mixture was cooled to room temperature, and the reaction mixture was poured into 600 ml of water, and crystals were dropped and filtered. The filtered solid was dissolved in chloroform, washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 5 g of intermediate compound A-3-9. (Yield 40%, MS:[M+H] ⁺ =254)

Synthesis Example A-4-3: Preparation of Intermediate Compound A-4-3

4-Bromo-2-chloropyridine (15g, 77.9 mmol) and (1-(methylthio)naphthalen-2-yl)boronic acid (17.8g, 81.8 mmol) were added to 300 ml of THF, stirred and refluxed. Thereafter, potassium carbonate (32.3g, 233.8 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.4g, 0.8 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the organic layer was distilled after separating the organic layer and the water layer. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.6 g of compound A-4-3_P1. (Yield 70%, MS:[M+H] ⁺ =286)

Compound A-4-3_P1 (15g, 52.5 mmol) and hydrogen peroxide (2.7g, 78.7 mmol) were added to 300 ml of acetic acid, stirred and refluxed. After reacting for 4 hours, the reaction mixture was cooled to room temperature, and the reaction mixture was poured into 600 ml of water, and crystals were removed and filtered. The filtered solid was dissolved in chloroform, washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 9 g of compound A-4-3_P2. (Yield 57%, MS:[M+H] ⁺ =302)

Compound A-4-3_P2 (15g, 49.7 mmol) was added to 300 ml of sulfuric acid, stirred and refluxed. After reacting for 5 hours, the reaction mixture was cooled to room temperature, and the reaction mixture was poured into 600 ml of water, and crystals were dropped and filtered. The filtered solid was dissolved in chloroform, washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 5.7 g of intermediate compound A-4-3. (Yield 45%, MS:[M+H] ⁺ =254)

Synthesis Example A-4-3: Preparation of Intermediate Compound A-4-8

1-Bromo-3-chlorobenzene (15g, 78.3 mmol) and (5-(methylthio)quinolin-6-yl)boronic acid (18g, 82.3 mmol) were added to 300 ml of THF, stirred and refluxed. Thereafter, potassium carbonate (32.5g, 235 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.4g, 0.8 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, and the organic layer was distilled after separating the organic layer and the water layer. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.8 g of compound A-4-8_P1. (Yield 62%, MS:[M+H] ⁺ =286)

Compound A-4-8_P1 (15g, 52.5 mmol) and hydrogen peroxide (2.7g, 78.7 mmol) were added to 300 ml of acetic acid, stirred and refluxed. After reacting for 5 hours, the reaction mixture was cooled to room temperature, and the reaction mixture was poured into 600 ml of water to drop crystals and filtered. The filtered solid was dissolved in chloroform, washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, 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 compound A-4-8_P2. (Yield 52%, MS:[M+H] ⁺ =302)

Compound A-4-8_2 (15 g, 49.7 mmol) was added to 300 ml of sulfuric acid and stirred and refluxed. After reacting for 5 hours, the reaction mixture was cooled to room temperature, and the reaction mixture was poured into 600 ml of water, and crystals were dropped and filtered. The filtered solid was dissolved in chloroform, washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 7 g of intermediate compound A-4-8. (Yield 56%, MS:[M+H] ⁺ =254)

Synthesis Example 1

Intermediate compound A-1-1 (15 g, 55.6 mmol), amine1 (19.6 g, 58.4 mmol), and potassium phosphate (35.4 g, 166.8 mmol) were added to 300 ml of xylene in a nitrogen atmosphere, followed by stirring and reflux. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and 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 19.3 g of Compound 1. (Yield 61%, MS:[M+H] ⁺ =569)

Synthesis Example 2

In a nitrogen atmosphere, intermediate compound A-1-1 (15 g, 55.6 mmol), amine2 (20.4 g, 58.4 mmol), and potassium phosphate (35.4 g, 166.8 mmol) were added to 300 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and 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 23.6 g of Compound 2. (Yield 73%, MS:[M+H] ⁺ =583)

Synthesis Example 3

First, the same method as in Synthesis Example A-1-1 was performed except that 3-bromo-4-chloropyridine was used instead of 3-bromo-2-chloropyridine as a starting material in Synthesis Example A-1-1. Intermediate compound A-1-3 was prepared using

Next, in a nitrogen atmosphere, intermediate compound A-1-3 (15 g, 55.6 mmol), amine3 (20.4 g, 58.4 mmol), and potassium phosphate (35.4 g, 166.8 mmol) were added to 300 ml of xylene, stirred and refluxed. . Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and 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 23.3 g of Compound 3. (Yield 72%, MS:[M+H] ⁺ =583)

Synthesis Example 4

Intermediate compound A-1-6 (15 g, 55.6 mmol), amine4 (19.6 g, 58.4 mmol), and potassium phosphate (35.4 g, 166.8 mmol) were added to 300 ml of xylene in a nitrogen atmosphere, followed by stirring and reflux. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and 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 20.2 g of Compound 4. (Yield 64%, MS:[M+H] ⁺ =569)

Synthesis Example 5

First, except for using (5-(methylthio)quinolin-6-yl)boronic acid instead of (5-(methylthio)isoquinolin-6-yl)boronic acid as a starting material in Synthesis Example A-1-6 prepared intermediate compound A-1-7 using the same method as Synthesis Example A-1-6.

Next, intermediate compound A-1-7 (15g, 55.6 mmol) and amine5 (29.5g, 58.4 mmol) were added to 300 ml of THF, stirred and refluxed. Thereafter, potassium carbonate (23.1g, 166.8 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, and the organic layer and the water layer were separated, and the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 24.7 g of Compound 5. (Yield 64%, MS:[M+H] ⁺ =694)

Synthesis Example 6

First, except for using (5-(methylthio)isoquinolin-3-yl)boronic acid instead of (5-(methylthio)isoquinolin-6-yl)boronic acid as a starting material in Synthesis Example A-1-6 Then, an intermediate compound A-1-9 was prepared by the same method as in Synthesis Example A-1-6.

Next, intermediate compound A-1-9 (15g, 55.6 mmol) and amine6 (26.5g, 58.4 mmol) were added to 300ml of THF, stirred and refluxed. Thereafter, potassium carbonate (23.1g, 166.8 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, and the organic layer and the water layer were separated, and the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 22.2 g of Compound 6. (Yield 62%, MS:[M+H] ⁺ =644)

Synthesis Example 7

Intermediate compound A-2-2 (15g, 55.6 mmol) and amine7 (25.8g, 58.4 mmol) were added to 300ml of THF, stirred and refluxed. Thereafter, potassium carbonate (23.1g, 166.8 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 26.6 g of Compound 7. (Yield 76%, MS:[M+H] ⁺ =631)

Synthesis Example 8

First, the same method as in Synthesis Example A-2-2 was carried out, except that 3-bromo-5-chloropyridine was used instead of 4-bromo-2-chloropyridine as a starting material in Synthesis Example A-2-2. Intermediate compound A-2-3 was prepared using

Next, in a nitrogen atmosphere, intermediate compound A-2-3 (15 g, 55.6 mmol), amine8 (20.5 g, 58.4 mmol), and potassium phosphate (35.4 g, 166.8 mmol) were added to 300 ml of xylene, stirred and refluxed. . Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and 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 23.4 g of Compound 8. (Yield 72%, MS:[M+H] ⁺ =585)

Synthesis Example 9

Intermediate compound A-2-4 (15g, 55.6 mmol) and amine9 (27.5g, 58.4 mmol) were added to 300 ml of THF, stirred and refluxed. Thereafter, potassium carbonate (23.1g, 166.8 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 29.4 g of Compound 9. (Yield 80%, MS:[M+H] ⁺ =661)

Synthesis Example 10

First, except for using (4-(methylthio)quinolin-3-yl)boronic acid instead of (5-(methylthio)quinolin-6-yl)boronic acid as a starting material in Synthesis Example A-2-7 , Intermediate compound A-2-8 was prepared using the same method as Synthesis Example A-2-7.

Next, intermediate compound A-2-8 (15g, 55.6 mmol) and amine10 (23.1g, 58.4 mmol) were added to 300 ml of THF, stirred and refluxed. Thereafter, potassium carbonate (23.1g, 166.8 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the organic layer was distilled after separating the organic layer and the water layer. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 26 g of Compound 10. (Yield 80%, MS:[M+H] ⁺ =585)

Synthesis Example 11

First, except that (4-(methylthio)isoquinolin-3-yl)boronic acid was used instead of (5-(methylthio)quinolin-6-yl)boronic acid as a starting material in Synthesis Example A-2-7. prepared intermediate compound A-2-9 using the same method as Synthesis Example A-2-7.

Next, in a nitrogen atmosphere, intermediate compound A-2-9 (15 g, 55.6 mmol), amine3 (20.4 g, 58.4 mmol), and potassium phosphate (35.4 g, 166.8 mmol) were added to 300 ml of xylene, stirred and refluxed. . Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and 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 20.1 g of Compound 11. (Yield 62%, MS:[M+H] ⁺ =583)

Synthesis Example 12

First, the same method as in Synthesis Example A-2-2 was carried out except that 2-bromo-5-chloropyridine was used instead of 4-bromo-2-chloropyridine as a starting material in Synthesis Example A-2-2. Intermediate compound A-3-1 was prepared using

Next, intermediate compound A-3-1 (15g, 55.6 mmol) and amine11 (26.6g, 58.4 mmol) were added to 300 ml of THF, stirred and refluxed. Thereafter, potassium carbonate (23.1 g, 166.8 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, and the organic layer was distilled after separating the organic layer and the water layer. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 25.4 g of Compound 12. (Yield 71%, MS:[M+H] ⁺ =645)

Synthesis Example 13

First, the same method as in Synthesis Example A-2-2 was carried out except that 5-bromo-2-chloropyridine was used instead of 4-bromo-2-chloropyridine as a starting material in Synthesis Example A-2-2. Intermediate compound A-3-2 was prepared using

Next, intermediate compound A-3-2 (15g, 55.6 mmol) and amine12 (26.6g, 58.4 mmol) were added to 300ml of THF, stirred and refluxed. Thereafter, potassium carbonate (23.1g, 166.8 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, and the organic layer and the water layer were separated, and the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 21.5 g of Compound 13. (Yield 60%, MS:[M+H] ⁺ =645)

Synthesis Example 14

First, the same method as in Synthesis Example A-2-2 was carried out, except that 5-bromo-2-chloropyridine was used instead of 4-bromo-2-chloropyridine as a starting material in Synthesis Example A-2-2. Intermediate compound A-3-2 was prepared using

Next, in a nitrogen atmosphere, compound A-3-2 (15 g, 55.6 mmol), amine13 (21.7 g, 58.4 mmol), and potassium phosphate (35.4 g, 166.8 mmol) were added to 300 ml of xylene, stirred and refluxed. did. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and 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 21.2 g of Compound 14. (Yield 63%, MS:[M+H] ⁺ =605)

Synthesis Example 15

First, the same method as in Synthesis Example A-2-2 was carried out except that 2-bromo-6-chloropyridine was used instead of 4-bromo-2-chloropyridine as a starting material in Synthesis Example A-2-2. Intermediate compound A-3-3 was prepared using

Next, intermediate compound A-3-3 (15 g, 55.6 mmol), amine14 (19.6 g, 58.4 mmol), and potassium phosphate (35.4 g, 166.8 mmol) were added to 300 ml of xylene in a nitrogen atmosphere, followed by stirring and reflux. . Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and 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 21.5 g of Compound 15. (Yield 68%, MS:[M+H] ⁺ =569)

Synthesis Example 16

First, the same method as in Synthesis Example A-2-2 was performed, except that 2-bromo-6-chloropyridine was used instead of 4-bromo-2-chloropyridine as a starting material in Synthesis Example A-2-2. Intermediate compound A-3-3 was prepared using

Next, intermediate compound A-3-3 (15 g, 55.6 mmol), amine15 (14.3 g, 58.4 mmol), and potassium phosphate (35.4 g, 166.8 mmol) were added to 300 ml of xylene in a nitrogen atmosphere, followed by stirring and reflux. . Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and 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 19.4 g of Compound 16. (Yield 73%, MS:[M+H] ⁺ =479)

Synthesis Example 17

First, except that (8-(methylthio)quinolin-7-yl)boronic acid was used instead of (8-(methylthio)isoquinolin-7-yl)boronic acid as a starting material in Synthesis Example A-3-5. prepared intermediate compound A-3-4 using the same method as Synthesis Example A-3-5.

Next, intermediate compound A-3-4 (15 g, 55.6 mmol), amine16 (28.2 g, 58.4 mmol), and potassium phosphate (35.4 g, 166.8 mmol) were added to 300 ml of xylene in a nitrogen atmosphere, followed by stirring and reflux. . Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and 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 27.9 g of Compound 17. (Yield 70%, MS:[M+H] ⁺ =717)

Synthesis Example 18

First, except that (4-(methylthio)quinolin-3-yl)boronic acid was used instead of (4-(methylthio)isoquinolin-3-yl)boronic acid as a starting material in Synthesis Example A-3-9. prepared intermediate compound A-3-8 using the same method as Synthesis Example A-3-9.

Next, intermediate compound A-3-8 (15 g, 55.6 mmol), amine17 (28.2 g, 58.4 mmol), and potassium phosphate (35.4 g, 166.8 mmol) were added to 300 ml of xylene in a nitrogen atmosphere, stirred and refluxed. . Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and 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 25.5 g of Compound 18. (Yield 64%, MS:[M+H] ⁺ =717)

Synthesis Example 19

First, the same method as in Synthesis Example A-4-3 was performed, except that 2-bromo-4-chloropyridine was used instead of 4-bromo-2-chloropyridine as a starting material in Synthesis Example A-4-3. Intermediate compound A-4-1 was prepared using

Next, intermediate compound A-4-1 (15 g, 55.6 mmol), amine14 (19.6 g, 58.4 mmol), and potassium phosphate (35.4 g, 166.8 mmol) were added to 300 ml of xylene in a nitrogen atmosphere, followed by stirring and reflux. . Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and 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 22.7 g of Compound 19. (Yield 72%, MS:[M+H] ⁺ =569)

Synthesis Example 20

First, the same method as in Synthesis Example A-4-3 was performed, except that 2-bromo-4-chloropyridine was used instead of 4-bromo-2-chloropyridine as a starting material in Synthesis Example A-4-3. Intermediate compound A-4-1 was prepared using

Next, intermediate compound A-4-1 (15 g, 55.6 mmol), amine18 (21.3 g, 58.4 mmol), and potassium phosphate (35.4 g, 166.8 mmol) were added to 300 ml of xylene in a nitrogen atmosphere, followed by stirring and reflux. . Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and 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 20.6 g of Compound 20. (Yield 62%, MS:[M+H] ⁺ =599)

Synthesis Example 21

First, the same method as in Synthesis Example A-4-3 was performed, except that 2-bromo-4-chloropyridine was used instead of 4-bromo-2-chloropyridine as a starting material in Synthesis Example A-4-3. Intermediate compound A-4-1 was prepared using

Next, intermediate compound A-4-1 (15 g, 55.6 mmol), amine19 (28.4 g, 58.4 mmol), and potassium phosphate (35.4 g, 166.8 mmol) were added to 300 ml of xylene in a nitrogen atmosphere, stirred and refluxed. . Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and 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 29.2 g of Compound 21. (Yield 73%, MS:[M+H] ⁺ =719)

Synthesis Example 22

First, the same method as in Synthesis Example A-4-3 was performed, except that 3-bromo-5-chloropyridine was used instead of 4-bromo-2-chloropyridine as a starting material in Synthesis Example A-4-3. Intermediate compound A-4-2 was prepared using

Next, intermediate compound A-4-2 (15 g, 55.6 mmol), amine20 (21.1 g, 58.4 mmol), and potassium phosphate (35.4 g, 166.8 mmol) were added to 300 ml of xylene in a nitrogen atmosphere, followed by stirring and reflux. . Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and 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 24.8 g of Compound 22. (Yield 75%, MS:[M+H] ⁺ =595)

Synthesis Example 23

First, the same method as in Synthesis Example A-4-3 was performed, except that 3-bromo-5-chloropyridine was used instead of 4-bromo-2-chloropyridine as a starting material in Synthesis Example A-4-3. Intermediate compound A-4-2 was prepared using

Next, intermediate compound A-4-2 (15 g, 55.6 mmol), amine21 (17.2 g, 58.4 mmol), and potassium phosphate (35.4 g, 166.8 mmol) were added to 300 ml of xylene in a nitrogen atmosphere, followed by stirring and reflux. . Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and 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 20 g of Compound 23. (Yield 68%, MS:[M+H] ⁺ =529)

Synthesis Example 24

First, the same method as in Synthesis Example A-4-3 was performed, except that 3-bromo-5-chloropyridine was used instead of 4-bromo-2-chloropyridine as a starting material in Synthesis Example A-4-3. Intermediate compound A-4-2 was prepared using

Next, intermediate compound A-4-2 (15 g, 55.6 mmol), amine22 (32.8 g, 58.4 mmol), and potassium phosphate (35.4 g, 166.8 mmol) were added to 300 ml of xylene in a nitrogen atmosphere, stirred and refluxed. . Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and 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 29.2 g of Compound 24. (Yield 66%, MS:[M+H] ⁺ =795)

Synthesis Example 25

Intermediate compound A-4-8 (15 g, 55.6 mmol), amine23 (18.8 g, 58.4 mmol), and potassium phosphate (35.4 g, 166.8 mmol) were added to 300 ml of xylene in a nitrogen atmosphere, followed by stirring and reflux. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and 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 18.8 g of Compound 25. (Yield 61%, MS:[M+H] ⁺ =555)

Comparative Example 1

A glass substrate coated with ITO (indium tin oxide) to a thickness of 1,000 Å was put in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a Fischer Co. product was used as the detergent, and distilled water filtered through a second filter of a Millipore Co. product was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was performed twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, dried, and transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transferred to a vacuum deposition machine.

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%. A hole transport layer having a thickness of 800 Å was formed by vacuum depositing the following HT-1 compound on the hole injection layer. Subsequently, an electron blocking layer was formed by vacuum depositing the following EB-1 compound to a film thickness of 150 Å on the hole transport layer. Subsequently, the following RH-1 compound and the following Dp-39 compound 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 on the light emitting layer by vacuum depositing the following HB-1 compound to a film thickness of 30 Å. Subsequently, the following ET-1 compound and the following LiQ compound were vacuum-deposited at a weight ratio of 2:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 300 Å. A negative electrode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1,000 Å on the electron injection and transport layer.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7Å / sec, the deposition rate of lithium fluoride on the cathode was 0.3Å / sec, and the deposition rate of aluminum was 2Å / sec, and the vacuum level during deposition was 2ⅹ10 ^-7 ~ Maintaining 5x10 ^-6 torr, an organic light emitting device was manufactured.

Comparative Examples 2 to 6

Device performance was measured in the same manner as in Comparative Example 1, except that the following compounds RH-2 to RH-6 were used instead of RH-1 as a host material for the red light emitting layer.

Examples 1 to 25

Device performance was measured in the same manner as in Comparative Example 1, except that Compounds 1 to 25 prepared by Synthesis Example were used instead of Comparative Example 1 as the host material for the red light emitting layer.

As in Comparative Examples 1 to 6 and Examples 1 to 25, the driving voltage, current efficiency and lifespan of the organic light emitting device prepared using each compound as a red host material were measured, and the results are shown in Table 1 below. was

Experimental example host substance driving voltage
(V) current efficiency
(cd/A) life span
(T95% @10mA, hr) Comparative Example 1 RH-1 5.70 14.01 50 Comparative Example 2 RH-2 5.65 13.93 66 Comparative Example 3 RH-3 5.81 13.02 61 Comparative Example 4 RH-4 5.80 13.05 57 Comparative Example 5 RH-5 5.88 12.96 65 Comparative Example 6 RH-6 5.79 12.72 60 Example 1 compound 1 4.10 23.46 180 Example 2 compound 2 4.23 24.01 179 Example 3 compound 3 4.15 24.31 165 Example 4 compound 4 4.31 23.91 171 Example 5 compound 5 4.19 23.00 178 Example 6 compound 6 4.18 23.12 189 Example 7 compound 7 4.26 24.63 185 Example 8 compound 8 4.21 25.01 181 Example 9 compound 9 4.33 25.31 175 Example 10 compound 10 4.51 23.99 179 Example 11 compound 11 4.19 25.13 187 Example 12 compound 12 4.20 25.92 199 Example 13 compound 13 4.34 25.30 171 Example 14 compound 14 4.33 26.10 183 Example 15 compound 15 4.65 25.99 188 Example 16 compound 16 4.17 24.06 179 Example 17 compound 17 4.16 23.49 190 Example 18 compound 18 4.23 23.93 191 Example 19 compound 19 4.51 24.12 190 Example 20 compound 20 4.15 25.03 193 Example 21 compound 21 4.61 23.99 185 Example 22 compound 22 4.13 25.03 179 Example 23 compound 23 4.15 24.28 175 Example 24 compound 24 4.34 24.96 177 Example 25 compound 25 4.41 25.03 188

Referring to Table 1, the organic light emitting device of Example using the compound represented by Formula 1 as a host material for the light emitting layer has a reduced driving voltage and improved efficiency and It can be seen that it represents the life characteristics.

1: substrate 2: anode
3: light emitting layer 4: cathode
5: hole injection layer 6: hole transport layer
7: light emitting layer 8: electron injection and transport layer

Claims (11)

A compound represented by Formula 1 below:
[Formula 1]

In Formula 1,
One of X ₁ to X ₄ is CR, and the others are each independently N, CH, or CD;
Here, R is a substituent represented by Formula 2 below,
X ₅ to X ₁₀ are each independently N, CH, or CD;
However, one of X ₁ to X ₁₀ is N,
[Formula 2]

In Formula 2,
L ₁ is a direct bond; Substituted or unsubstituted C _6-60 arylene; Or a C _2-60 heteroarylene containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,
L ₂ is a direct bond; Substituted or unsubstituted C _6-60 arylene; Or a C _2-60 heteroarylene containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,
L ₃ is a direct bond; Substituted or unsubstituted C _6-60 arylene; Or a C _2-60 heteroarylene containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,
Ar ₁ is a substituted or unsubstituted C _6-60 aryl; Or a C _2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,
Ar ₂ is a substituted or unsubstituted C _6-60 aryl; Or a C _2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S.
According to claim 1,
one of X ₁ to X ₄ is CR, the other is N, the others are each independently CH or CD, and X ₅ to X ₁₀ are each independently CH or CD; or
One of X ₁ to X ₄ is CR, the others are each independently CH or CD, one of X ₅ to X ₁₀ is N, and the others are each independently CH or CD,
compound.
According to claim 1,
L ₁ is a direct bond; or phenylene;
when L ₁ is phenylene, unsubstituted or substituted with one or more deuterium;
compound.
According to claim 1,
L ₂ is a direct bond; phenylene; naphthylene; biphenylylene; 9,9-dimethyl-fluorenylene; 9,9-diphenyl-fluorenylene; or carbazolylene;
L ₂ is phenylene; naphthylene; biphenylylene; 9,9-dimethyl-fluorenylene; 9,9-diphenyl-fluorenylene; or in the case of carbazolylene, which are unsubstituted or substituted with one or more deuterium,
compound.
According to claim 1,
L ₃ is a direct bond; phenylene; naphthylene; biphenylylene; 9,9-dimethyl-fluorenylene; or 9,9-diphenyl-fluorenylene;
L ₃ is phenylene; naphthylene; biphenylylene; 9,9-dimethyl-fluorenylene; or 9,9-diphenyl-fluorenylene, which are unsubstituted or substituted with one or more deuterium,
compound.
According to claim 1,
Ar ₁ is phenyl; biphenylyl; terphenylyl; naphthyl; 9,9-dimethyl-fluorenyl; 9,9-diphenyl-fluorenyl; dibenzofuranyl; dibenzothiophenyl; 9-phenyl-carbazolyl; 9-naphthyl-carbazolyl or 9,9'-spirobi[9H-fluorenyl]yl;
Ar ₁ is unsubstituted or substituted with one or more deuterium;
compound.
According to claim 1,
Ar ₂ is phenyl; biphenylyl; terphenylyl; naphthyl; 9,9-dimethyl-fluorenyl; 9,9-diphenyl-fluorenyl; dibenzofuranyl; dibenzothiophenyl; 9-phenyl-carbazolyl; or 9,9'-spirobi[9H-fluorene]yl;
Ar ₂ is unsubstituted or substituted with one or more deuterium;
compound.
According to claim 1,
The compound is represented by any one of Formulas 1-1 to 1-4,
compound:
[Formula 1-1]

In Formula 1-1,
One of X ₂ to X ₁₀ is N, and the others are each independently CH or CD;
L ₁ to L ₃ , Ar ₁ and Ar ₂ are as defined in claim 1,
[Formula 1-2]

In Formula 1-2,
One of X ₁ and X ₃ to X ₁₀ is N, and the others are each independently CH or CD;
L ₁ to L ₃ , Ar ₁ and Ar ₂ are as defined in claim 1,
[Formula 1-3]

In Formula 1-3 above.
One of X ₁ , X ₂ and X ₄ to X ₁₀ is N, and the others are each independently CH or CD;
L ₁ to L ₃ , Ar ₁ and Ar ₂ are as defined in claim 1,
[Formula 1-4]

In Chemical Formulas 1-4,
One of X ₁ to X ₃ and X ₅ to X ₁₀ is N, and the others are each independently CH or CD,
L ₁ to L ₃ , Ar ₁ and Ar ₂ are as defined in claim 1.
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 an organic material layer provided between the first electrode and the second electrode, wherein the organic material layer includes the compound according to any one of claims 1 to 9. .
According to claim 10,
The organic material layer containing the compound is a light emitting layer,
organic light emitting device.

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