KR102546268B1 - 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.

Description

Novel compound and organic light emitting device using the same {NOVEL COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING 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. The organic material layer is often composed of a multi-layer 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, an electron suppression layer, a light emitting layer, a hole blocking layer, an electron transport layer, It may consist of an injection layer or the like. 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.

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,

Each Y is independently a single bond, O or S, provided that at least one of Y is O or S;

R ₁ are each independently hydrogen; heavy hydrogen; halogen; cyano; Substituted or unsubstituted C _1-60 Alkyl; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _2-60 alkynyl; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _6-60 aryl; A C _2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,

n1 and n2 are integers from 0 to 4;

n3 is an integer from 0 to 3;

R ₂ is represented by the following formula (2),

[Formula 2]

In Formula 2,

L is a single bond; or a substituted or unsubstituted C _6-60 arylene;

X is N or CH, provided that at least two of X are N;

Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C _6-60 aryl; It is a C _2-60 heteroaryl containing at least one heteroatom 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 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. to provide.

The compound represented by Chemical Formula 1 may be used as a material for an organic layer of an organic light emitting diode, and may improve efficiency, low driving voltage, and/or lifespan characteristics of an organic light emitting diode. In particular, the compound represented by Formula 1 described above may be used as a material for hole injection, hole transport, hole injection and transport, 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 shows a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (6), a light emitting layer (3), a hole blocking layer (8), an electron injection and transport layer ( 9) and an example of an organic light emitting element composed of a cathode 4 is shown.

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

또는

는 다른 치환기에 연결되는 결합을 의미한다. In this specification,

or

means a bond connected to another substituent.

In this specification, the term "substituted or unsubstituted" means deuterium; halogen group; nitrile 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 group; 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 a heterocyclic group 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, 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 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, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, 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. However, it is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing at least one of O, N, Si, and S as heterogeneous elements, and the number of carbon atoms is not particularly limited, but preferably has 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, and an acridyl group. , pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinoline group, indole group , carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group (phenanthroline), isoxazolyl group, thiadia A zolyl 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, and an aryl group among arylamine 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 heterocyclic group described above may be applied to the heteroaryl of the heteroarylamine. 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 the heterocyclic group 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 heterocyclic group may be applied, except that it is formed by combining two substituents.

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

In the compound represented by Formula 1, a heterocyclic ring containing two or more N is bonded to a specific position of a mother nucleus structure in which a fluoranthene ring and a bicyclic heterocyclic ring containing O or S are condensed, thereby using the same. The characteristics of the organic light emitting device may be improved. In particular, the compound represented by Chemical Formula 1 uses a polycyclic aromatic core in which a plurality of aromatic rings are connected, thereby increasing molecular rigidity, increasing stability for electrons and holes, and exhibiting better light emitting characteristics. As a result, quantum efficiency and lifetime can be improved.

In Formula 1, the compound represented by Formula 1 may be represented by any one of the following Formulas 1-1 to 1-8, depending on the specific position at which the heterocycle containing two or more N atoms is bonded:

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

[Formula 1-8]

In Formulas 1-1 to 1-8,

Z is O or S;

R ₁ , n1, n2, n3, L, X, Ar ₁ and Ar ₂ are as defined in Formula 1 above.

Specifically, in Formula 1, one of Y is O or S, and the others are single bonds.

Specifically, in Formula 1 and Formulas 1-1 to 1-8, R ₁ is each hydrogen, deuterium, halogen, or cyano, or substituted or unsubstituted C _1-20 alkyl, or C _1-12 alkyl , or C _1-6 alkyl, or substituted or unsubstituted C _1-20 alkoxy, or C _1-12 alkoxy, or C _1-6 alkoxy, or substituted or unsubstituted C _2-20 alkenyl, or C _2-12 alkenyl, or C _2-6 alkenyl, or substituted or unsubstituted C _2-20 alkynyl, or C _2-12 alkynyl, or C _2-6 alkynyl, or substituted or unsubstituted cyclic C _3-30 cycloalkyl, or C _3-25 cycloalkyl, or C _3-20 cycloalkyl, or substituted or unsubstituted C _6-30 aryl, or C _6-28 aryl, or C _6-25 aryl, or C _6-20 aryl or substituted or unsubstituted C _3-30 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S, or C _5-28 heteroaryl; or C _5-25 heteroaryl, or C _6-20 heteroaryl, or C _12-18 heteroaryl.

For example, each of R ₁ may be hydrogen or deuterium. Also, all of R ₁ may be hydrogen.

Specifically, in Chemical Formula 1 and Chemical Formulas 1-1 to 1-8, n1, n2, and n3 may each be an integer of 0 to 2, or 0 or 1.

Specifically, in Formula 1 and Formulas 1-1 to 1-8, L is a single bond; Alternatively, it may be substituted or unsubstituted C _6-30 arylene, C _6-28 arylene, C _6-25 arylene, or C _6-20 arylene. Preferably, L is a single bond; or phenylene, biphenylylene, terphenylylene, quaterphenylylene, or naphthylene.

For example, L is a single bond; Or it may be displayed as any one selected from the group consisting of.

.

.

Specifically, in Formula 1 and Formulas 1-1 to 1-8, two of X's may be N and the rest may be CH, or all of X's may be N.

Specifically, in Formula 1 and Formulas 1-1 to 1-8, Ar ₁ and Ar ₂ are each substituted or unsubstituted C _6-30 aryl, C _6-28 aryl, or C _6-25 aryl, or C _6-20 aryl; Or a substituted or unsubstituted C _3-30 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S, or C _5-28 heteroaryl, or C _5-25 heteroaryl, or C _6-20 heteroaryl, or C _12-18 heteroaryl.

More specifically, Ar ₁ and Ar ₂ are each phenyl, naphthyl-substituted phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, or phenyl substituted carbazolyl.

In particular, at least one of Ar ₁ and Ar ₂ may be phenyl, naphthyl-substituted phenyl, biphenyl, naphthyl, or phenyl-substituted naphthyl, preferably phenyl, biphenyl, or naphthyl.

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

.

Meanwhile, the compound represented by Chemical Formula 1 can be prepared by a manufacturing method shown in Reaction Scheme 1 below. The preparation method may be more specific in a synthesis example to be described later.

[Scheme 1]

In Reaction Scheme 1, Y, R ₁ , R ₂ , n1, and n2 are as defined in Formula 1, Q ₁ is BO ₂ C ₂ (CH ₃ ) ₄ , or B(OH) ₂ , and Q ₂ is a halogen group, preferably Cl, Br or I, more preferably Cl.

Specifically, Scheme 1 above is a reaction of introducing a heteroaryl substituent containing at least two or more N at a specific position in a parent structure in which a fluoranthene ring and a bicyclic hetero ring containing O or S are condensed. .

For example, in Scheme 1, Q ₁ is a pinacolborane group, BO ₂ C ₂ (CH ₃ ) ₄ , or a boronic acid group, B(OH) ₂ , and a fluoranthene ring and O Or, a polycyclic compound in which a bicyclic heterocyclic ring including S is condensed, a heterocyclic compound including Q ₂ which is a halogen group, and at least two or more Ns are mixed with a palladium catalyst (Pd catalyst) in the presence of a base. It is done by reacting with Through this reaction, inacolborone group BO ₂ C ₂ (CH ₃ ) ₄ , or B(OH ) is to introduce a heteroaryl group containing at least two or more N at the Q ₁ position of ₂ . Preferably, in Reaction Scheme 1, Q ₁ is BO ₂ C ₂ (CH ₃ ) ₄ , and Q ₂ may be chlorine. Specific reaction conditions of this Reaction Scheme 1 can be performed with reference to known reactions known in the art. The preparation method may be more specific in a synthesis example to be described later.

In addition, as the base component, potassium carbonate (K ₂ CO ₃ ), sodium bicarbonate (NaHCO ₃ ), cesium carbonate (Cs ₂ CO ₃ ), sodium acetate (NaOAc) , potassium acetate (KOAc), sodium tert-butoxide (NaOtBu), sodium ethoxide (NaOEt), or triethylamine (Et ₃ N), N,N- Diisopropylethylamine (N,N-diisopropylethylamine, EtN(iPr) ₂ ) and the like can be used. Preferably, the basic component is potassium carbonate (K ₂ CO ₃ ), cesium carbonate (Cs ₂ CO ₃ ), potassium acetate (KOAc), sodium tert-butoxide (sodium tert- butoxide, NaOtBu), or N,N-diisopropylethylamine (N,N-diisopropylethylamine, EtN(iPr) ₂ ).

In addition, as the palladium catalyst, bis(tri-(tert-butyl)phosphine)palladium (0) (bis(tri-(tert-butyl)phosphine)palladium(0), Pd(P-tBu ₃ ) ₂ ), tetrakis(triphenylphosphine)palladium (0) (tetrakis(triphenylphosphine)palladium (0), tris(dibenzylideneacetone)-dipalladium (0) (tris(dibenzylideneacetone)-dipalladium (0), Pd ₂ (dba) ₃ ), bis(dibenzylideneacetone)palladium (0) (bis(dibenzylideneacetone)palladium (0), Pd(dba) ₂ ), Pd(PPh ₃ ) ₄ ) or palladium(II) acetate , Pd(OAc) ₂ ) and the like can be used. Preferably, the palladium catalyst is bis(tri-(tert-butyl)phosphine)palladium (0) (bis(tri-(tert-butyl)phosphine)palladium(0), Pd(P-tBu ₃ ) ₂ ) , tetrakis(triphenylphosphine)palladium (0), Pd(PPh ₃ ) ₄ ), or bis(dibenzylideneacetone)palladium (0) (bis(dibenzylideneacetone)palladium ( 0), Pd(dba) ₂ ). In particular, bis(tri-(tert-butyl)phosphine)palladium (0) (bis(tri-(tert-butyl)phosphine)palladium(0), Pd(P-tBu ₃ ) ₂ ) in Scheme 1 is catalyzed can be used as

Equivalent weight (eq.) in this specification means a molar equivalent.

Meanwhile, 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. do.

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, an electron blocking 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. Contains the indicated compounds.

In addition, the organic material layer may include an electron blocking layer, and the electron blocking layer includes the compound represented by Chemical Formula 1.

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

In addition, the light emitting layer further includes a dopant compound.

In addition, the light emitting layer includes the compound of Formula 1 and a dopant.

For example, the light emitting layer includes the compound of Formula 1 and a dopant, and includes the compound of Formula 1 and the dopant in a content ratio of 100:1 to 1:1.

In addition, the light emitting layer includes the compound of Formula 1 and the dopant, and includes the compound of Formula 1 and the dopant in a content ratio of 100:1 to 2:1.

In addition, the light emitting layer includes the compound of Formula 1 and the dopant, and includes the compound of Formula 1 and the dopant in a content ratio of 100:1 to 5:1.

For example, the dopant is a metal complex.

Specifically, the dopant is an iridium-based metal complex.

In addition, the organic material layer includes a light emitting layer, the light emitting layer includes a dopant, and the dopant material is selected from the following structural formulas.

.

.

The structures specified above are not limited to dopant compounds.

In addition, the organic layer may include a hole blocking layer, and the hole blocking layer includes the compound represented by Chemical Formula 1.

In addition, the organic material layer may include an electron transport layer, an electron injection layer, or a layer that simultaneously injects and transports electrons, and the electron transport layer, electron injection layer, or layer that simultaneously injects and transports electrons is represented by Formula 1 above. Contains the indicated compounds.

In addition, the organic material layer may include a light emitting layer and a hole transport layer, and the light emitting layer or hole 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. In this structure, the compound represented by Chemical Formula 1 may be included in the light emitting layer.

2 shows a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (6), a light emitting layer (3), a hole blocking layer (8), an electron injection and transport layer ( 9) and an example of an organic light emitting element composed of a cathode 4 is shown. In this structure, the compound represented by Formula 1 may be included in at least one layer of the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, and the electron injection and transport layer. Specifically, the compound represented by Chemical Formula 1 may be included in the light emitting layer or the hole transport layer, and may be included as a host material of the light emitting layer, for example.

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 a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by 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 and forming an organic material layer including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer thereon, and then depositing a material that can be used as a cathode thereon. can do. 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. In particular, the compound represented by Chemical Formula 1 has excellent solubility in the solvent used in the solution application method, and thus the solution application method is easy to apply. 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.

Accordingly, the present invention provides a coating composition comprising the compound represented by Formula 1 and a solvent.

The solvent is not particularly limited as long as it can dissolve or disperse the compound according to the present invention, and examples thereof include chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o -Chlorinated solvents such as dichlorobenzene; ether solvents such as tetrahydrofuran and dioxane; aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, and mesitylene; aliphatic hydrocarbon-based solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; Ketone solvents, such as acetone, methyl ethyl ketone, and cyclohexanone; Ester solvents, such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; Ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol, etc. alcohol and its derivatives; alcohol solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; and amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; benzoate solvents such as butyl benzoate and methyl-2-methoxy benzoate; tetralin; and solvents such as 3-phenoxy-toluene. In addition, the above-mentioned solvent may be used alone or in combination of two or more solvents.

In addition, the viscosity of the coating composition is preferably 1 cP to 10 cP, and coating is easy within the above range. In addition, the concentration of the compound according to the present invention in the coating composition is preferably 0.1 wt / v% to 20 wt / v%.

In addition, the present invention provides a method for forming a functional layer using the coating composition described above. Specifically, coating the coating composition according to the present invention described above by a solution process; and heat-treating the coated coating composition.

In the heat treatment step, the heat treatment temperature is preferably 150 ℃ to 230 ℃. In addition, the heat treatment time is 1 minute to 3 hours, more preferably 10 minutes to 1 hour. In addition, the heat treatment is preferably performed in an inert gas atmosphere such as argon or nitrogen.

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 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 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 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 materials, anthraquinone, polyaniline, and polythiophene-based conductive polymers, 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. As a hole transport material, a material capable of receiving holes from the anode or the hole injection layer and transferring them to the light emitting layer is a material having high hole mobility. this is suitable Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, 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 light emitting layer may include a host material and a dopant material. The host material includes a condensed aromatic ring derivative or a compound containing a hetero ring. 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. Preferably, the compound according to the present invention is used as the host material.

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. Preferably, an iridium-based metal complex is used as the dopant material.

The light emitting layer may be a red light emitting layer, and when the compound according to the present invention is used as a host material, stability for electrons and holes is increased, and energy transfer from the host to the red dopant is well performed, driving voltage of the organic light emitting device, Luminous efficiency and lifetime characteristics can be improved.

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.

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.

Preparation Example 1. Preparation of Intermediate Compound AA

In a nitrogen atmosphere, compound subA (20 g, 91.6 mmol) and N-bromosuccinimide (NBS, 17.1 g, 96.2 mmol) were added to 400 mL of chloroform (CHCl ₃ ) and stirred at room temperature. After reacting for 6 hours, the organic layer was separated after washing twice with water, stirred with anhydrous magnesium sulfate, and 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 subA-1. (Yield 75%, MS: [M+H] ⁺ = 297).

In a nitrogen atmosphere, compound subA-1 (10 g, 33.7 mmol) and compound sub1 (6.5 g, 37 mmol) were added to 200 mL of tetrahydrofuran (THF), followed by stirring and reflux. After that, potassium carbonate (K ₂ CO ₃ , 14 g, 101 mmol) was dissolved in 42 mL of water, added, stirred sufficiently, and bis(tri-tert-butylphosphine)palladium(0) [Pd(P-tBu ₃ ) ₂ ] (0.2 g, 0.3 mmol) was added. After reacting for 10 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 7.8 g of compound AA_P1. (Yield 67%, MS: [M+H] ⁺ = 347).

In a nitrogen atmosphere, compound AA_P1 (10 g, 28.8 mmol) and potassium carbonate (12 g, 86.5 mmol) were added to 200 mL of N,N-Dimethylacetamide (DMAc) and stirred and refluxed. After reacting for 9 hours, the mixture was cooled to room temperature and the organic solvent was distilled under reduced pressure. 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 7 g of compound AA_P2. (Yield 74%, MS: [M+H] ⁺ = 327).

Compound AA_P2 (15 g, 45.9 mmol) and bis(pinacolato)diboron (12.8 g, 50.5 mmol) were stirred while refluxing in 300 mL of 1,4-dioxane in a nitrogen atmosphere. Afterwards, potassium acetate (KOAc, 6.8 g, 68.9 mmol) was added, and after sufficiently stirred, bis(dibenzylideneacetone)palladium (0) [Pd(dba) ₂ ] (0.8 g, 1.4 mmol) and tricyclohexylphosphine (PCy ₃ , 0.8 g , 2.8 mmol) was added. After reacting for 10 hours, cooling to room temperature and separating the organic layer using chloroform and water, 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 12.9 g of Compound AA. (Yield 67%, MS: [M+H] ⁺ = 419).

Preparation Example 2. Preparation of Intermediate Compound AB

12.7 g of Compound AB was prepared in the same manner as in Preparation Example 1, except that Compound sub2 was used instead of Compound sub1 as a starting material in Preparation Example 1. (Yield 66%, MS: [M+H] ⁺ = 419).

Preparation Example 3. Preparation of Intermediate Compound AC

13.2 g of Compound AC was prepared in the same manner as in Preparation Example 1, except that Compound sub3 was used instead of Compound sub1 as a starting material in Preparation Example 1. (Yield 69%, MS: [M+H] ⁺ = 419).

Preparation Example 4. Preparation of intermediate compound AD

13.6 g of Compound AD was prepared in the same manner as in Preparation Example 1, except that Compound sub4 was used instead of Compound sub1 as a starting material in Preparation Example 1. (Yield 71%, MS: [M+H] ⁺ = 419).

Preparation Example 5. Preparation of Intermediate Compound BA

In a nitrogen atmosphere, compound subB (10 g, 35.6 mmol) and compound sub5 (7.9 g, 39.1 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (14.7 g, 106.7 mmol) was dissolved in 44 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 11 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 10.1 g of compound BA_P1. (Yield 79%, MS: [M+H] ⁺ = 359).

In a nitrogen atmosphere, compound BA_P1 (10 g, 27.9 mmol) and hydrogen peroxide (H ₂ O ₂ , 1 g, 30.7 mmol) were added to 200 mL of acetic acid (AcOH), stirred and refluxed. After 3 hours, the reaction mixture was poured into water to remove 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 7.6 g of compound BA_P2. (Yield 73%, MS: [M+H] ⁺ = 375).

In a nitrogen atmosphere, compound BA_P2 (10 g, 26.7 mmol) was added to 200 mL of H ₂ SO ₄ and stirred. When the reaction was completed after 2 hours, the reactant was poured into water, and crystals were removed and filtered. The filtered solid was again 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 6.1 g of compound BA_P3. (Yield 67%, MS: [M+H] ⁺ = 343).

Compound BA_P3 (15 g, 43.8 mmol) and bis(pinacolato)diboron (12.2 g, 48.1 mmol) were stirred while refluxing in 300 mL of 1,4-dioxane in a nitrogen atmosphere. Then, potassium acetate (6.4 g, 65.6 mmol) was added, and after sufficient stirring, bis(dibenzylideneacetone)palladium(0) (0.8 g, 1.3 mmol) and tricyclohexylphosphine (0.7 g, 2.6 mmol) were added. After reacting for 10 hours, cooling to room temperature and separating the organic layer using chloroform and water, 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 15.2 g of compound BA. (Yield 80%, MS: [M+H] ⁺ = 435).

Preparation Example 6. Preparation of Intermediate Compound BB

12.9 g of compound BB was prepared in the same manner as in Preparation Example 5, except that compound sub6 was used instead of compound sub5 as a starting material in Preparation Example 5. (Yield 68%, MS: [M+H] ⁺ = 435).

Preparation Example 7. Preparation of Intermediate Compound BC

13.9 g of Compound BC was prepared in the same manner as in Preparation Example 5, except that Compound sub7 was used instead of Compound sub5 as a starting material in Preparation Example 5. (Yield 73%, MS: [M+H] ⁺ = 435).

Preparation Example 8. Preparation of Intermediate Compound BD

14.2 g of compound BD was prepared in the same manner as in Preparation Example 5, except that compound sub8 was used instead of compound sub5 as a starting material in Preparation Example 5. (Yield 75%, MS: [M+H] ⁺ = 435).

Preparation Example 9. Preparation of Intermediate Compound C

13.8 g of compound CA was prepared in the same manner as in Preparation Example 1, except that compound subC was used instead of compound subA as a starting material in Preparation Example 1. (Yield 72%, MS: [M+H] ⁺ = 419).

Preparation Example 10. Preparation of Intermediate Compound CB

13.6 g of compound CB was prepared in the same manner as in Preparation Example 1, except that compound subC was used instead of compound subA and sub2 was used instead of sub1 as the starting material in Preparation Example 1. (Yield 71%, MS: [M+H] ⁺ = 419).

Preparation Example 11. Preparation of Intermediate Compound CC

13.6 g of compound CC was prepared in the same manner as in Preparation Example 1, except that compound subC was used instead of compound subA and sub3 was used instead of sub1 as the starting material in Preparation Example 1. (Yield 71%, MS: [M+H] ⁺ = 419).

Preparation Example 12. Preparation of intermediate compound CD

13.6 g of compound CD was prepared in the same manner as in Preparation Example 1, except that compound subC was used instead of compound subA and sub4 was used instead of sub1 as the starting material in Preparation Example 1. (Yield 71%, MS: [M+H] ⁺ = 419).

Preparation Example 13. Preparation of Intermediate Compound DA

12.9 g of compound DA was prepared in the same manner as in Preparation Example 5, except that compound subD was used instead of compound subB as a starting material in Preparation Example 5. (Yield 68%, MS: [M+H] ⁺ = 435).

Preparation Example 14. Preparation of Intermediate Compound DB

14.1 g of compound DB was prepared in the same manner as in Preparation Example 5, except that compound subD was used instead of compound subB and compound sub6 was used instead of sub5 as a starting material in Preparation Example 5. (Yield 74%, MS: [M+H] ⁺ = 435).

Preparation Example 15. Preparation of Intermediate Compound DC

14.4 g of compound DC was prepared in the same manner as in Preparation Example 5, except that compound subD was used instead of compound subB and compound sub7 was used instead of sub5 as a starting material in Preparation Example 5. (Yield 76%, MS: [M+H] ⁺ = 435).

Preparation Example 16. Preparation of Intermediate Compound DD

13.3 g of compound DD was prepared in the same manner as in Preparation Example 5, except that compound subD was used instead of compound subB and compound sub8 was used instead of sub5 as a starting material in Preparation Example 5. (Yield 70%, MS: [M+H] ⁺ = 435).

Synthesis Example 1. Synthesis of Compound 1

In a nitrogen atmosphere, compound AA (10 g, 23.9 mmol) and compound Trz1 (8.4 g, 24.4 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 12 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 11.2 g of Compound 1. (Yield 78%, MS: [M+H] ⁺ = 600).

Synthesis Example 2. Synthesis of Compound 2

In a nitrogen atmosphere, compound AA (10 g, 23.9 mmol) and compound Trz2 (9.1 g, 24.4 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 11 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 9.8 g of Compound 2. (Yield 65%, MS: [M+H] ⁺ = 630).

Synthesis Example 3. Synthesis of Compound 3

In a nitrogen atmosphere, compound AA (10 g, 23.9 mmol) and compound Trz3 (9.6 g, 24.4 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 10 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 11.6 g of Compound 3. (Yield 75%, MS: [M+H] ⁺ = 650).

Synthesis Example 4. Synthesis of Compound 4

In a nitrogen atmosphere, compound AA (10 g, 23.9 mmol) and compound Trz4 (12.1 g, 24.4 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 10 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 14 g of Compound 4. (Yield 78%, MS: [M+H] ⁺ = 752).

Synthesis Example 5. Synthesis of Compound 5

In a nitrogen atmosphere, compound AB (10 g, 23.9 mmol) and compound Trz5 (7.7 g, 24.4 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 12 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 10.3 g of Compound 5. (Yield 75%, MS: [M+H] ⁺ = 574).

Synthesis Example 6. Synthesis of Compound 6

In a nitrogen atmosphere, compound AB (10 g, 23.9 mmol) and compound Trz6 (10.2 g, 24.4 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 11 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 11.9 g of Compound 6. (Yield 74%, MS: [M+H] ⁺ = 676).

Synthesis Example 7. Synthesis of Compound 7

In a nitrogen atmosphere, compound AB (10 g, 23.9 mmol) and compound Trz7 (10.6 g, 24.4 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 9 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 11.2 g of Compound 7. (Yield 68%, MS: [M+H] ⁺ = 690).

Synthesis Example 8. Synthesis of Compound 8

In a nitrogen atmosphere, compound AC (10 g, 23.9 mmol) and compound Trz8 (9.6 g, 24.4 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 8 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 11.3 g of Compound 8. (Yield 73%, MS: [M+H] ⁺ = 650).

Synthesis Example 9. Synthesis of Compound 9

In a nitrogen atmosphere, compound AC (10 g, 23.9 mmol) and compound Trz9 (8.4 g, 24.4 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 8 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 again 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 11 g of Compound 9. (Yield 77%, MS: [M+H] ⁺ = 600).

Synthesis Example 10. Synthesis of Compound 10

In a nitrogen atmosphere, compound AC (10 g, 23.9 mmol) and compound Trz10 (11 g, 24.4 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 9 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 12.3 g of Compound 10. (Yield 73%, MS: [M+H] ⁺ = 706).

Synthesis Example 11. Synthesis of Compound 11

In a nitrogen atmosphere, compound AC (10 g, 23.9 mmol) and compound Trz11 (8.7 g, 24.4 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 11 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 11.1 g of compound 11. (Yield 76%, MS: [M+H] ⁺ = 613).

Synthesis Example 12. Synthesis of Compound 12

In a nitrogen atmosphere, compound AD (10 g, 23.9 mmol) and compound Trz12 (9.6 g, 24.4 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 12 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 again 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 9.8 g of Compound 12. (Yield 63%, MS: [M+H] ⁺ = 650).

Synthesis Example 13. Synthesis of Compound 13

In a nitrogen atmosphere, compound AD (10 g, 23.9 mmol) and compound Trz13 (9.1 g, 24.4 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 11 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 10.2 g of Compound 13. (Yield 68%, MS: [M+H] ⁺ = 630).

Synthesis Example 14. Synthesis of Compound 14

In a nitrogen atmosphere, compound BA (10 g, 23 mmol) and compound Trz14 (8.4 g, 23.5 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 9 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 10.3 g of Compound 14. (Yield 71%, MS: [M+H] ⁺ = 630).

Synthesis Example 15. Synthesis of Compound 15

In a nitrogen atmosphere, compound BA (10 g, 23 mmol) and compound Trz15 (9.2 g, 23.5 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 11 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 9.2 g of Compound 15. (Yield 60%, MS: [M+H] ⁺ = 666).

Synthesis Example 16. Synthesis of Compound 16

In a nitrogen atmosphere, compound BA (10 g, 23 mmol) and compound Trz16 (8.6 g, 23.5 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 12 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 9.9 g of Compound 16. (Yield 67%, MS: [M+H] ⁺ = 640).

Synthesis Example 17. Synthesis of Compound 17

In a nitrogen atmosphere, compound BA (10 g, 23 mmol) and compound Trz17 (6.3 g, 23.5 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 12 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 again 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 9.8 g of Compound 17. (Yield 79%, MS: [M+H] ⁺ = 540).

Synthesis Example 18. Synthesis of Compound 18

In a nitrogen atmosphere, compound BB (10 g, 23 mmol) and compound Trz18 (9.9 g, 23.5 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 9 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 11.5 g of compound 18. (Yield 72%, MS: [M+H] ⁺ = 692).

Synthesis Example 19. Synthesis of Compound 19

In a nitrogen atmosphere, compound BB (10 g, 23 mmol) and compound Trz19 (9.2 g, 23.5 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 8 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 11 g of Compound 19. (Yield 72%, MS: [M+H] ⁺ = 666).

Synthesis Example 20. Synthesis of Compound 20

In a nitrogen atmosphere, compound BB (10 g, 23 mmol) and compound Trz20 (9.2 g, 23.5 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 10 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 10.3 g of Compound 20. (Yield 67%, MS: [M+H] ⁺ = 666).

Synthesis Example 21. Synthesis of Compound 21

In a nitrogen atmosphere, compound BC (10 g, 23 mmol) and compound Trz3 (9.2 g, 23.5 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 8 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 9.5 g of Compound 21. (Yield 62%, MS: [M+H] ⁺ = 666).

Synthesis Example 22. Synthesis of Compound 22

In a nitrogen atmosphere, compound BC (10 g, 23 mmol) and compound Trz11 (8.4 g, 23.5 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 11 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 9.4 g of Compound 22. (Yield 65%, MS: [M+H] ⁺ = 629).

Synthesis Example 23. Synthesis of Compound 23

In a nitrogen atmosphere, compound BD (10 g, 23 mmol) and compound Trz12 (9.2 g, 23.5 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 8 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 11.6 g of Compound 23. (Yield 76%, MS: [M+H] ⁺ = 666).

Synthesis Example 24. Synthesis of Compound 24

In a nitrogen atmosphere, compound BD (10 g, 23 mmol) and compound Trz21 (9.2 g, 23.5 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 8 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 11.6 g of Compound 24. (Yield 76%, MS: [M+H] ⁺ = 666).

Synthesis Example 25. Synthesis of Compound 25

In a nitrogen atmosphere, compound BD (10 g, 23 mmol) and compound Trz22 (8.1 g, 23.5 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 11 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 9.6 g of Compound 25. (Yield 68%, MS: [M+H] ⁺ = 616).

Synthesis Example 26. Synthesis of Compound 26

In a nitrogen atmosphere, compound BD (10 g, 23 mmol) and compound Trz23 (10.4 g, 23.5 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 12 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 12.3 g of Compound 26. (Yield 75%, MS: [M+H] ⁺ = 716).

Synthesis Example 27. Synthesis of Compound 27

In a nitrogen atmosphere, compound CA (10 g, 23.9 mmol) and compound Trz24 (10.8 g, 24.4 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 11 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 13.2 g of Compound 27. (Yield 79%, MS: [M+H] ⁺ = 700).

Synthesis Example 28. Synthesis of Compound 28

In a nitrogen atmosphere, compound CA (10 g, 23.9 mmol) and compound Trz25 (9.1 g, 24.4 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 8 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 10.7 g of Compound 28. (Yield 71%, MS: [M+H] ⁺ = 630).

Synthesis Example 29. Synthesis of Compound 29

In a nitrogen atmosphere, compound CB (10 g, 23.9 mmol) and compound Trz8 (9.6 g, 24.4 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 12 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 11 g of compound 29. (Yield 71%, MS: [M+H] ⁺ = 650).

Synthesis Example 30. Synthesis of Compound 30

In a nitrogen atmosphere, compound CB (10 g, 23.9 mmol) and compound Trz11 (8.7 g, 24.4 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 10 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 9.7 g of compound 30. (Yield 66%, MS: [M+H] ⁺ = 613).

Synthesis Example 31. Synthesis of Compound 31

In a nitrogen atmosphere, compound CB (10 g, 23.9 mmol) and compound Trz26 (9.6 g, 24.4 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 12 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 11.3 g of compound 31. (Yield 73%, MS: [M+H] ⁺ = 650).

Synthesis Example 32. Synthesis of Compound 32

In a nitrogen atmosphere, compound CB (10 g, 23.9 mmol) and compound Trz27 (12.4 g, 24.4 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 11 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 13.5 g of Compound 32. (Yield 74%, MS: [M+H] ⁺ = 765).

Synthesis Example 33. Synthesis of Compound 33

In a nitrogen atmosphere, compound CC (10 g, 23.9 mmol) and compound Trz17 (6.5 g, 24.4 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 12 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 9.8 g of compound 33. (Yield 78%, MS: [M+H] ⁺ = 524).

Synthesis Example 34. Synthesis of Compound 34

In a nitrogen atmosphere, compound CC (10 g, 23.9 mmol) and compound Trz28 (8.7 g, 24.4 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 12 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 10 g of Compound 34. (Yield 68%, MS: [M+H] ⁺ = 614).

Synthesis Example 35. Synthesis of Compound 35

In a nitrogen atmosphere, compound CD (10 g, 23.9 mmol) and compound Trz14 (8.7 g, 24.4 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 8 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 10 g of compound 35. (Yield 68%, MS: [M+H] ⁺ = 614).

Synthesis Example 36. Synthesis of Compound 36

In a nitrogen atmosphere, compound CD (10 g, 23.9 mmol) and compound Trz29 (9 g, 24.4 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 11 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 11 g of compound 36. (Yield 74%, MS: [M+H] ⁺ = 624).

Synthesis Example 37. Synthesis of Compound 37

In a nitrogen atmosphere, compound CD (10 g, 23.9 mmol) and compound Trz30 (9.6 g, 24.4 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 9 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 11.5 g of Compound 37. (Yield 74%, MS: [M+H] ⁺ = 650).

Synthesis Example 38. Synthesis of Compound 38

In a nitrogen atmosphere, compound CD (10 g, 23.9 mmol) and compound Trz17 (6.5 g, 24.4 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 8 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 10 g of compound 38. (Yield 80%, MS: [M+H] ⁺ = 524).

Synthesis Example 39. Synthesis of Compound 39

In a nitrogen atmosphere, compound CD (10 g, 23.9 mmol) and compound Trz31 (8.4 g, 24.4 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 11 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 10 g of compound 39. (Yield 70%, MS: [M+H] ⁺ = 600).

Synthesis Example 40. Synthesis of Compound 40

In a nitrogen atmosphere, compound DA (10 g, 23 mmol) and compound Trz21 (9.2 g, 23.5 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 12 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 11.2 g of Compound 40. (Yield 73%, MS: [M+H] ⁺ = 666).

Synthesis Example 41. Synthesis of Compound 41

In a nitrogen atmosphere, compound DA (10 g, 23 mmol) and compound Trz30 (9.2 g, 23.5 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 12 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 obtain 9.2 g of Compound 41. (Yield 60%, MS: [M+H] ⁺ = 666).

Synthesis Example 42. Synthesis of Compound 42

In a nitrogen atmosphere, compound DA (10 g, 23 mmol) and compound Trz5 (7.5 g, 23.5 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 11 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 10.9 g of Compound 42. (Yield 80%, MS: [M+H] ⁺ = 590).

Synthesis Example 43. Synthesis of Compound 43

In a nitrogen atmosphere, compound DB (10 g, 23 mmol) and compound Trz32 (10.4 g, 23.5 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 9 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 12 g of Compound 43. (Yield 73%, MS: [M+H] ⁺ = 716).

Synthesis Example 44. Synthesis of Compound 44

In a nitrogen atmosphere, compound DB (10 g, 23 mmol) and compound Trz33 (9.9 g, 23.5 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 11 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 12.4 g of Compound 44. (Yield 78%, MS: [M+H] ⁺ = 692).

Synthesis Example 45. Synthesis of Compound 45

In a nitrogen atmosphere, compound DB (10 g, 23 mmol) and compound Trz34 (11 g, 23.5 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 9 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 11.6 g of Compound 45. (Yield 68%, MS: [M+H] ⁺ = 742).

Synthesis Example 46. Synthesis of Compound 46

In a nitrogen atmosphere, compound DB (10 g, 23 mmol) and compound Trz1 (8.1 g, 23.5 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 8 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 11 g of compound 46. (Yield 78%, MS: [M+H] ⁺ = 616).

Synthesis Example 47. Synthesis of Compound 47

In a nitrogen atmosphere, compound DC (10 g, 23 mmol) and compound Trz35 (10.2 g, 23.5 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 8 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 12 g of Compound 47. (Yield 74%, MS: [M+H] ⁺ = 705).

Synthesis Example 48. Synthesis of Compound 48

In a nitrogen atmosphere, compound DC (10 g, 23 mmol) and compound Trz36 (10.2 g, 23.5 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 8 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 12.3 g of Compound 48. (Yield 76%, MS: [M+H] ⁺ = 705).

Synthesis Example 49. Synthesis of Compound 49

In a nitrogen atmosphere, compound DC (10 g, 23 mmol) and compound Trz28 (8.4 g, 23.5 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 9 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 obtain 11.4 g of Compound 49. (Yield 79%, MS: [M+H] ⁺ = 630).

Synthesis Example 50. Synthesis of Compound 50

In a nitrogen atmosphere, compound DD (10 g, 23 mmol) and compound Trz22 (8.1 g, 23.5 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 10 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 10.9 g of compound 50. (Yield 77%, MS: [M+H] ⁺ = 616).

Synthesis Example 51. Synthesis of Compound 51

In a nitrogen atmosphere, compound DD (10 g, 23 mmol) and compound Trz14 (8.4 g, 23.5 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 9 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 10 g of compound 51. (Yield 69%, MS: [M+H] ⁺ = 630).

Synthesis Example 52. Synthesis of Compound 52

In a nitrogen atmosphere, compound DD (10 g, 23 mmol) and compound Trz29 (8.6 g, 23.5 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 11 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 10.6 g of Compound 52. (Yield 72%, MS: [M+H] ⁺ = 640).

Synthesis Example 53. Synthesis of Compound 53

In a nitrogen atmosphere, compound DD (10 g, 23 mmol) and compound Trz5 (7.5 g, 23.5 mmol) were added to 200 mL of THF, stirred and refluxed. Thereafter, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 12 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 9.6 g of compound 53. (Yield 71%, MS: [M+H] ⁺ = 590).

Example 1

A glass substrate coated with a thin film of indium tin oxide (ITO) to a thickness of 1,000 Angstrom (Å, angstrom) was placed 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 evaporator.

As a hole injection layer on the prepared ITO transparent electrode, the following compound HI-1 was thermally vacuum deposited to a thickness of 1150 Å to form a hole injection layer, and the following compound A-1 was p-doped at a concentration of 1.5%. 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. Subsequently, an electron blocking layer was formed by vacuum depositing the following compound EB-1 to a film thickness of 150 Å on the hole transport layer. Subsequently, the following compound 1 and the following compound 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 on the light emitting layer by vacuum depositing the following compound HB-1 to a film thickness of 30 Å. Subsequently, the following compound ET-1 and the following compound LiQ 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.

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

Examples 2 to 53

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compounds 2 to 53 in Table 1 were used instead of Compound 1 in the organic light emitting device of Example 1.

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Comparative Examples 1 to 13

An organic light emitting device was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of Compound 1 in the organic light emitting device of Example 1. The compounds of C-1 to C-13 used in Table 1 below are as follows.

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When current was applied to the organic light emitting devices prepared in Examples and Comparative Examples, voltage and efficiency were measured (15 mA/cm ² ), and the results are shown in Table 1 below. The lifetime T95 means the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.

division matter Driving voltage (V) Efficiency (cd/A) Lifetime T95(hr) luminescent color Example 1 compound 1 3.91 17.6 138 Red Example 2 compound 2 3.98 17.0 114 Red Example 3 compound 3 3.93 17.3 121 Red Example 4 compound 4 3.97 17.1 108 Red Example 5 compound 5 3.95 17.3 111 Red Example 6 compound 6 3.94 17.5 124 Red Example 7 compound 7 3.91 18.1 132 Red Example 8 compound 8 4.06 17.3 110 Red Example 9 compound 9 4.03 17.1 116 Red Example 10 compound 10 4.07 17.0 103 Red Example 11 compound 11 4.08 17.6 108 Red Example 12 compound 12 3.93 18.4 147 Red Example 13 compound 13 3.99 17.9 115 Red Example 14 compound 14 4.03 18.1 124 Red Example 15 compound 15 4.01 18.0 128 Red Example 16 compound 16 4.02 17.8 125 Red Example 17 compound 17 4.05 17.5 120 Red Example 18 compound 18 4.08 17.8 106 Red Example 19 compound 19 4.11 17.3 112 Red Example 20 compound 20 4.13 17.6 103 Red Example 21 compound 21 4.12 17.2 104 Red Example 22 compound 22 4.16 17.9 108 Red Example 23 compound 23 4.03 18.3 135 Red Example 24 compound 24 3.97 18.8 142 Red Example 25 compound 25 4.01 17.9 117 Red Example 26 compound 26 4.04 17.3 104 Red Example 27 compound 27 3.85 18.6 145 Red Example 28 compound 28 3.89 18.0 121 Red Example 29 compound 29 3.94 18.8 124 Red Example 30 compound 30 3.91 19.3 129 Red Example 31 compound 31 3.96 18.2 117 Red Example 32 compound 32 3.98 18.0 108 Red Example 33 compound 33 4.01 17.8 103 Red Example 34 compound 34 4.03 17.5 109 Red Example 35 compound 35 3.73 19.7 154 Red Example 36 compound 36 3.79 19.2 142 Red Example 37 compound 37 3.83 18.8 137 Red Example 38 compound 38 3.77 19.4 140 Red Example 39 compound 39 3.70 19.8 162 Red Example 40 compound 40 3.81 18.9 153 Red Example 41 compound 41 3.89 18.1 124 Red Example 42 compound 42 3.83 18.5 131 Red Example 43 compound 43 3.91 18.4 117 Red Example 44 compound 44 3.90 18.6 122 Red Example 45 compound 45 3.95 17.9 108 Red Example 46 compound 46 3.93 18.0 115 Red Example 47 compound 47 4.01 18.1 124 Red Example 48 compound 48 4.07 17.2 121 Red Example 49 compound 49 4.04 17.5 120 Red Example 50 compound 50 3.78 18.8 132 Red Example 51 compound 51 3.69 19.5 153 Red Example 52 compound 52 3.72 19.1 144 Red Example 53 compound 53 3.71 19.0 141 Red Comparative Example 1 C-1 4.20 14.9 84 Red Comparative Example 2 C-2 4.25 13.6 72 Red Comparative Example 3 C-3 4.26 13.6 81 Red Comparative Example 4 C-4 4.28 14.6 73 Red Comparative Example 5 C-5 4.21 15.0 92 Red Comparative Example 6 C-6 4.62 6.2 19 Red Comparative Example 7 C-7 4.67 5.5 16 Red Comparative Example 8 C-8 4.41 8.7 41 Red Comparative Example 9 C-9 3.38 9.6 57 Red Comparative Example 10 C-10 4.71 4.5 8 Red Comparative Example 11 C-11 4.64 6.0 34 Red Comparative Example 12 C-12 4.23 15.6 94 Red Comparative Example 13 C-13 4.29 14.8 86 Red

When current was applied to the organic light emitting devices manufactured in Examples 1 to 53 and Comparative Examples 1 to 13, the results shown in Table 1 were obtained. As described above, the red organic light emitting device of Example 1 used a material widely used in the prior art, and had a structure using compound EB-1 as an electron blocking layer and compound 1 and compound Dp-7 as a red light emitting layer. In Comparative Examples 1 to 13, organic light emitting diodes were prepared using compounds C-1 to C-13 instead of compound 1.

As shown in Table 1, according to the present invention, the compound represented by Formula 1, that is, a fluoranthene ring and a bicyclic heterocyclic ring containing O or S is condensed at a specific position in the parent nucleus structure where N is 2 The organic light-emitting devices of Examples 1 to 22 using a compound having a specific polycyclic structure including at least two heteroaryl substituents in the light emitting layer are Comparative Examples 1 to 13 prepared using the compounds of C-1 to C-13. Compared to the organic light emitting device of , the driving voltage was significantly lowered, and the efficiency was greatly increased, indicating that energy transfer from the host to the red dopant was well achieved. In addition, it was found that the lifespan characteristics of the organic light emitting devices of Examples 1 to 53 can be greatly improved while maintaining high efficiency. This can eventually be determined because the compounds of Examples according to the present invention have higher stability to electrons and holes than the compounds of Comparative Examples. In conclusion, it can be confirmed that when the compound of the present invention is used as a host of the red light emitting layer, the driving voltage, luminous efficiency and lifetime characteristics of the organic light emitting device can be improved.

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

Claims (11)

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

In Formula 1,
One of Y is O or S, the other is a single bond,
R ₁ are each independently hydrogen; or deuterium;
n1 and n2 are integers from 0 to 4;
n3 is an integer from 0 to 3;
R ₂ is represented by the following formula (2),
[Formula 2]

In Formula 2,
L is a single bond; unsubstituted phenylene; Or unsubstituted naphthylene,
X is all N,
Ar ₁ and Ar ₂ are each independently selected from unsubstituted phenyl, naphthyl-substituted phenyl, unsubstituted naphthyl, phenyl-substituted naphthyl, unsubstituted biphenyl, unsubstituted terphenyl, unsubstituted phenanthryl, unsubstituted dibenzofuranyl, unsubstituted dibenzothiophenyl, unsubstituted carbazolyl, or phenyl substituted carbazolyl.
According to claim 1,
The compound represented by Formula 1 is one of those represented by any one of Formulas 1-1 to 1-8,
compound:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

[Formula 1-8]

In Formulas 1-1 to 1-8,
Z is O or S;
R ₁ , n1, n2, n3, L, X, Ar ₁ and Ar ₂ are as defined in claim 1.
delete delete According to claim 1,
L is a single bond; Or, which is represented by any one selected from the group consisting of
compound:

.
delete delete delete 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 one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers is one of claims 1, 2, 5, and 9. An organic light emitting device comprising the compound according to any one of claims.
According to claim 10,
The organic material layer containing the compound is a light emitting layer,
organic light emitting device.

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