KR20210142556A - Novel compound and organic light emitting device comprising the same - Google Patents

Abstract

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

Description

Novel compound and organic light emitting device comprising the same

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

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

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

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

Korean Patent Publication No. 10-2013-073537

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

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

[Formula 1]

In Formula 1,

Y is S or O;

A is a naphthalene ring,

L ₁ and L ₂ are each independently a direct bond or a substituted or unsubstituted C _6-60 arylene;

Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ are each independently substituted or unsubstituted C _6-60 aryl or substituted or unsubstituted containing any one or more heteroatoms selected from the group consisting of N, O and S cyclic C _2-60 heteroaryl;

R ₁ is each independently hydrogen, deuterium, substituted or unsubstituted C _1-60 alkyl or substituted or unsubstituted C _6-60 aryl;

m is an integer from 0 to 6.

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 organic material layer includes the compound of the present invention.

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

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

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

(Definition of Terms)

및

는 다른 치환기에 연결되는 결합을 의미한다. In this specification,

and

means a bond connected to another substituent.

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkyl thiooxy group; arylthioxy group; an alkyl sulfoxy group; arylsulfoxy group; silyl group; boron group; an alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; heteroarylamine group; arylamine group; an arylphosphine group; or N, O, and S atom means that it is substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group containing one or more atoms, or substituted or unsubstituted with two or more substituents connected among the above-exemplified substituents . 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 in the carbonyl group is not particularly limited, but 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, in the ester group, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

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

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

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

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

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl, and the like, 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 an exemplary embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the carbon number of the alkenyl group is 2 to 10. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.

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

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

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

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

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

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

(compound)

The present invention provides a compound represented by the above formula (1). The compound represented by Formula 1 has a core structure of naphthobenzofuran (naphthobenzothiophene), and is a compound in which two amine groups are directly bonded to the benzene ring of the core structure or are substituted by an arylene linker. , can facilitate energy transfer from the host to the red dopant when applied to the light emitting layer. In particular, the stability of electrons and holes is high compared to compounds having different substitution positions of amine groups or compounds in which the amine group is substituted by a heteroarylene linker or compounds including a hetero group in addition to the naphthalene ring, and thus, organic light emitting When applied as a host compound for the light emitting layer of a device, excellent efficiency, low driving voltage, high brightness and long life can be realized. The structure of Chemical Formula 1 is as follows.

Preferably, the compound represented by Formula 1 is a compound represented by the following Formulas 1-1 to 1-3:

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3,

Y, L ₁ , L ₂ , Ar ₁ , Ar ₂ , Ar ₃ , Ar ₄ , R ₁ and m are as defined above.

Preferably, the compound represented by Formula 1 is a compound represented by the following Formulas 2-1 to 2-6:

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

In Formulas 2-1 to 2-6,

Y, L ₁ , L ₂ , Ar ₁ , Ar ₂ , Ar ₃ , Ar ₄ , R ₁ and m are as defined above.

Preferably, L ₁ and L ₂ are each independently a direct bond, phenylene, biphenylrylene or naphthylene, more preferably, a direct bond or phenylene.

Preferably, Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ are each independently, biphenylyl, terphenylyl, naphthyl, naphthylphenyl, phenylnaphthyl, phenanthrenyl, triphenylenyl, dimethylfluore nyl, diphenylfluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazol-9-yl, or 9-phenyl-9H-carbazolyl.

More preferably, Ar ₁ and Ar ₂ are each independently biphenylyl, terphenylyl, naphthyl, naphthylphenyl, phenylnaphthyl, triphenylenyl, dimethylfluorenyl, dibenzofuranyl or dibenzo thiophenyl.

Preferably, _{each R 1} is independently hydrogen, deuterium, C _1-10 alkyl or phenyl, more preferably _{each R 1} is independently hydrogen, deuterium.

Preferably, m is an integer from 0 to 2, more preferably 0 or 1.

Preferably, the compound represented by Formula 1 may be any one selected from the group consisting of:

.

.

The compound represented by Formula 1 may be prepared through the following Reaction Scheme 1:

[Scheme 1]

In the above scheme 1, the definition of the other substituents except for X ₁ and X ₂ are as defined above, X ₁ and X ₂ is a halogen, each independently, preferably bromo, or chloro.

Specifically, the compound represented by Formula 1 is prepared by combining starting materials SM1, SM2 and SM2' through an amine substitution reaction. These amine substitution reactions are preferably performed in the presence of a palladium catalyst and a base, respectively. In addition, the reactive group for the amine substitution reaction may be appropriately changed, and the method for preparing the compound represented by Formula 1 may be more specific in Preparation Examples to be described later.

(organic light emitting element)

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

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

In addition, the organic layer may include 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 The compounds shown are included.

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

In addition, the organic layer may include an emission layer, and the emission layer includes the compound represented by Formula 1 above. In this case, the compound represented by Formula 1 may be used as a host compound of the emission layer, preferably a red host compound. In this case, as the host compound, a compound other than the compound represented by Formula 1 may be used as the cohost compound.

In addition, the organic layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound represented by Formula 1 above.

In addition, the organic layer may include a hole blocking layer, the hole blocking layer includes the compound represented by the formula (1).

In addition, in the organic light emitting diode according to the present invention, an anode, one or more organic material layers and a cathode are sequentially stacked on a substrate, wherein the first electrode is an anode and the second electrode is a cathode. may be small. In addition, in the organic light emitting device according to the present invention, the first electrode is a cathode and the second electrode is an anode, and the cathode, one or more organic material layers and the anode are sequentially stacked on a substrate of an inverted type organic structure. It may be a light emitting device. For example, the structure of the organic light emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2 .

FIG. 1 shows an example of an organic light emitting device including a substrate 1 , an anode 2 , a light emitting layer 4 , and a cathode 6 . In such a structure, the compound represented by Formula 1 may be included in the emission layer 4 .

2 is a substrate (1), an anode (2), a hole injection layer (7), a hole transport layer (3), an electron blocking layer (8), a light emitting layer (4), a hole blocking layer (9), an electron injection and transport layer ( 5) and an example of an organic light emitting device comprising a cathode 6 are shown. In such a structure, the compound represented by Formula 1 may be included in the emission layer 4 .

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

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

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

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

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

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

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

The hole injection layer is a layer for injecting holes from the electrode, and as a hole injection material, it has the ability to transport holes, so it has a hole injection effect at the anode, an excellent hole injection effect on the light emitting layer or the light emitting material, and is produced in the light emitting layer A compound which prevents the movement of excitons to the electron injection layer or the electron injection material and is excellent in the ability to form a thin film is preferred. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, and conductive polymers of polyaniline and polythiophene series, 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. material is suitable. As the hole transport material, the compound represented by Formula 1 may be used, or an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion may be used, but the present invention is not limited thereto. .

The electron blocking layer (or electron blocking layer, electron blocking layer) is formed on the hole transport layer, preferably provided in contact with the light emitting layer, to control hole mobility and prevent excessive movement of electrons between holes and electrons It refers to a layer that serves to improve the efficiency of the organic light emitting device by increasing the bonding probability. The electron blocking layer includes an electron blocking material, and as an example of the electron blocking material, a compound represented by Formula 1 may be used, and an arylamine-based organic material may be additionally used, but is not limited thereto.

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. The compound represented by Formula 1 may be used. In addition, specific examples of the light-emitting material that can be used together include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

The light emitting layer may include a host material and a dopant material as described above. The host material may further include a condensed aromatic ring derivative or a heterocyclic compound containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

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

Preferably, the light emitting layer may include the following iridium complex compound as a dopant material, but is not limited thereto:

.

.

The hole blocking layer (or hole blocking layer, hole blocking layer) is formed on the light emitting layer, preferably provided in contact with the light emitting layer, to control the electron mobility and prevent excessive movement of holes hole-electron coupling probability It refers to a layer that serves to improve the efficiency of the organic light emitting device by increasing it. The hole blocking layer includes a hole blocking material. Specific examples include azine derivatives including triazine; triazole derivatives; oxadiazole derivatives; phenanthroline derivatives; A compound into which an electron withdrawing group is introduced, such as a phosphine oxide derivative, may be used, but the present invention is not limited thereto.

The electron injection and transport layer is a layer that simultaneously serves as an electron transport layer and an electron injection layer for injecting electrons from the electrode and transporting the received electrons to the emission layer, and is formed on the emission layer or the hole blocking layer. As the electron injection and transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high electron mobility is suitable. Specific examples of the electron injection and transport material include Al complex of 8-hydroxyquinoline; complexes containing Alq _{3 ;} organic radical compounds; hydroxyflavone-metal complexes; and triazine derivatives, but is not limited thereto. or fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metal complex compounds , or may be used together with a nitrogen-containing 5-membered ring derivative, etc., but is not limited thereto.

The electron injection and transport layer may also be formed as a separate layer such as an electron injection layer and an electron transport layer. In this case, the electron transport layer is formed on the emission layer or the hole blocking layer, and the electron injection and transport material described above may be used as the electron transport material included in the electron transport layer. In addition, the electron injection layer is formed on the electron transport layer, and the electron injection material included in the electron injection layer is LiF, NaCl, CsF, Li ₂ O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, Thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, anthrone, etc. derivatives thereof, metal complex compounds and nitrogen-containing 5-membered ring derivatives may be used.

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

The organic light emitting device according to the present invention may be a top emission type, a back emission type, or a double side emission type depending on the material used.

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

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

[Preparation Example - Synthesis of Intermediate Compound]

Preparation Example 1: Preparation of compound A-a

In a nitrogen atmosphere, (1-hydroxynaphthalen-2-yl)boronic acid (10g, 53.2mmol) and 2-bromo-1-chloro-4-fluoro-3-iodobenzene (35.7g, 106.4mmol) were added to 200ml of THF, stirred and refluxed. After that, potassium carbonate (22.1g, 159.6mmol) was dissolved in 66ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.5mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.3 g of Formula A-a_P-1. (Yield 77%, MS: [M+H] ⁺ = 351)

Formula A-a_P-1 (10 g, 28.4 mmol) and potassium carbonate (11.8 g, 85.3 mmol) were added to 200 ml of DMAc in a nitrogen atmosphere, stirred and refluxed. After the reaction for 9 hours, it was cooled to room temperature, and the organic solvent was distilled under reduced pressure. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 6.8 g of Compound Aa. (Yield 72%, MS: [M+H] ⁺ = 331)

Preparation Example 2: Preparation of compound A-b

Compound A-b was prepared in the same manner as in Preparation Example 1, except that 1-bromo-5-chloro-3-fluoro-2-iodobenzene was used instead of 2-bromo-1-chloro-4-fluoro-3-iodobenzene.

Preparation Example 3: Preparation of compound A-c

Compound A-c was prepared in the same manner as in Preparation Example 1, except that 1-bromo-4-chloro-3-fluoro-2-iodobenzene was used instead of 2-bromo-1-chloro-4-fluoro-3-iodobenzene.

Preparation Example 4: Preparation of compound A-d

Compound A-d was prepared in the same manner as in Preparation Example 1, except that 1-bromo-2-chloro-4-fluoro-5-iodobenzene was used instead of 2-bromo-1-chloro-4-fluoro-3-iodobenzene.

Preparation Example 5: Preparation of compound A-e

Compound A-e was prepared in the same manner as in Preparation Example 1, except that 5-bromo-1-chloro-2-fluoro-3-iodobenzene was used instead of 2-bromo-1-chloro-4-fluoro-3-iodobenzene.

Preparation Example 6: Preparation of compound A-f

Compound A-f was prepared in the same manner as in Preparation Example 1, except that 1-bromo-2-chloro-3-fluoro-4-iodobenzene was used instead of 2-bromo-1-chloro-4-fluoro-3-iodobenzene.

Preparation Example 7: Preparation of compound A-g

Compound A-g was prepared in the same manner as in Preparation Example 1, except that (3-hydroxynaphthalen-2-yl)boronic acid was used instead of (1-hydroxynaphthalen-2-yl)boronic acid.

Preparation 8: Preparation of compound A-h

Use (3-hydroxynaphthalen-2-yl)boronic acid instead of (1-hydroxynaphthalen-2-yl)boronic acid and 1-bromo-5-chloro instead of 2-bromo-1-chloro-4-fluoro-3-iodobenzene Compound Ah was prepared in the same manner as in Preparation Example 1 except that -3-fluoro-2-iodobenzene was used.

Preparation Example 9: Preparation of compound A-i

Use (3-hydroxynaphthalen-2-yl)boronic acid instead of (1-hydroxynaphthalen-2-yl)boronic acid and 1-bromo-4-chloro instead of 2-bromo-1-chloro-4-fluoro-3-iodobenzene Compound Ai was prepared in the same manner as in Preparation Example 1 except that -3-fluoro-2-iodobenzene was used.

Preparation 10: Preparation of compound A-j

Use (3-hydroxynaphthalen-2-yl)boronic acid instead of (1-hydroxynaphthalen-2-yl)boronic acid and 1-bromo-2-chloro instead of 2-bromo-1-chloro-4-fluoro-3-iodobenzene Compound Aj was prepared in the same manner as in Preparation Example 1, except that -4-fluoro-5-iodobenzene was used.

Preparation Example 11: Preparation of compound A-k

Use (3-hydroxynaphthalen-2-yl)boronic acid instead of (1-hydroxynaphthalen-2-yl)boronic acid and 5-bromo-1-chloro instead of 2-bromo-1-chloro-4-fluoro-3-iodobenzene Compound Aj was prepared in the same manner as in Preparation Example 1 except that -2-fluoro-3-iodobenzene was used.

Preparation 12: Preparation of compound A-1

Use (3-hydroxynaphthalen-2-yl)boronic acid instead of (1-hydroxynaphthalen-2-yl)boronic acid and 1-bromo-2-chloro instead of 2-bromo-1-chloro-4-fluoro-3-iodobenzene Compound Al was prepared in the same manner as in Preparation Example 1 except that -3-fluoro-4-iodobenzene was used.

Preparation 13: Preparation of compound A-m

Compound A-m was prepared in the same manner as in Preparation Example 1, except that (2-hydroxynaphthalen-1-yl)boronic acid was used instead of (1-hydroxynaphthalen-2-yl)boronic acid.

Preparation 14: Preparation of compound A-n

Use (2-hydroxynaphthalen-1-yl)boronic acid instead of (1-hydroxynaphthalen-2-yl)boronic acid and 1-bromo-5-chloro instead of 2-bromo-1-chloro-4-fluoro-3-iodobenzene Compound An was prepared in the same manner as in Preparation Example 1 except that -3-fluoro-2-iodobenzene was used.

Preparation 15: Preparation of compound A-o

Use (2-hydroxynaphthalen-1-yl)boronic acid instead of (1-hydroxynaphthalen-2-yl)boronic acid and 1-bromo-4-chloro instead of 2-bromo-1-chloro-4-fluoro-3-iodobenzene Compound Ao was prepared in the same manner as in Preparation Example 1 except that -3-fluoro-2-iodobenzene was used.

Preparation 16: Preparation of compound A-p

Use (2-hydroxynaphthalen-1-yl)boronic acid instead of (1-hydroxynaphthalen-2-yl)boronic acid and 1-bromo-2-chloro instead of 2-bromo-1-chloro-4-fluoro-3-iodobenzene Compound Ap was prepared in the same manner as in Preparation Example 1 except that -4-fluoro-5-iodobenzene was used.

Preparation 17: Preparation of compound A-q

Use (2-hydroxynaphthalen-1-yl)boronic acid instead of (1-hydroxynaphthalen-2-yl)boronic acid and 5-bromo-1-chloro instead of 2-bromo-1-chloro-4-fluoro-3-iodobenzene Compound Aq was prepared in the same manner as in Preparation Example 1 except that -2-fluoro-3-iodobenzene was used.

Preparation 18: Preparation of compound A-r

Use (2-hydroxynaphthalen-1-yl)boronic acid instead of (1-hydroxynaphthalen-2-yl)boronic acid and 1-bromo-2-chloro instead of 2-bromo-1-chloro-4-fluoro-3-iodobenzene Compound Ar was prepared in the same manner as in Preparation Example 1 except that -3-fluoro-4-iodobenzene was used.

Preparation 19: Preparation of compound B-a

In a nitrogen atmosphere, (1-(methylthio)naphthalen-2-yl)boronic acid (10g, 45.9mmol) and 2-bromo-1-chloro-3-iodobenzene (16g, 50.4mmol) were added to 200ml of THF, stirred and refluxed. . After that, potassium carbonate (19g, 137.6mmol) was dissolved in 57ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.5mmol) was added. After the reaction for 12 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.1 g of Formula B-a_P-2. (Yield 73%, MS: [M+H] ⁺ = 363)

Formula B-a_P-2 (10g, 27.5mmol) and Hydrogen Peroxide (1g, 30.2mmol) were added to 200ml of acetic acid in a nitrogen atmosphere, stirred and refluxed. After 3 hours, the reaction product was poured into water to drop crystals and filtered. The filtered solid was dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 7.4 g of Formula B-a_P-1. (Yield 71%, MS: [M+H] ⁺ = 379)

Formula B-a_P-1 (10g, 26.3mmol) was put in 200ml of _{H 2} SO _{4 and stirred in a nitrogen atmosphere.} When the reaction was completed after 2 hours, the reaction product was poured into water to drop crystals and filtered. The filtered solid was dissolved again in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 7.1 g of compound Ba. (Yield 78%, MS: [M+H] ⁺ = 347)

Preparation 20: Preparation of compound B-b

Compound B-b was prepared in the same manner as in Preparation Example 19, except that 2-bromo-4-chloro-1-iodobenzene was used instead of 2-bromo-1-chloro-3-iodobenzene.

Preparation 21: Preparation of compound B-c

Compound B-c was prepared in the same manner as in Preparation Example 19, except that 1-bromo-4-chloro-2-iodobenzene was used instead of 2-bromo-1-chloro-3-iodobenzene.

Preparation 22: Preparation of compound B-d

Compound B-d was prepared in the same manner as in Preparation Example 19, except that 2-bromo-1-chloro-4-iodobenzene was used instead of 2-bromo-1-chloro-3-iodobenzene.

Preparation 23: Preparation of compound B-e

Compound B-e was prepared in the same manner as in Preparation Example 19, except that 1-bromo-3-chloro-5-iodobenzene was used instead of 2-bromo-1-chloro-3-iodobenzene.

Preparation 24: Preparation of compound B-f

Compound B-f was prepared in the same manner as in Preparation Example 19, except that 1-bromo-2-chloro-4-iodobenzene was used instead of 2-bromo-1-chloro-3-iodobenzene.

Preparation 25: Preparation of compound B-g

Compound B-g was prepared in the same manner as in Preparation Example 19, except that (3-(methylthio)naphthalen-2-yl)boronic acid was used instead of (1-(methylthio)naphthalen-2-yl)boronic acid.

Preparation 26: Preparation of compound B-h

Use (3-(methylthio)naphthalen-2-yl)boronic acid instead of (1-(methylthio)naphthalen-2-yl)boronic acid and 2-bromo-4 instead of 2-bromo-1-chloro-3-iodobenzene Compound Bh was prepared in the same manner as in Preparation Example 19 except that -chloro-1-iodobenzene was used.

Preparation 27: Preparation of compound B-i

Use (3-(methylthio)naphthalen-2-yl)boronic acid instead of (1-(methylthio)naphthalen-2-yl)boronic acid and 1-bromo-4 instead of 2-bromo-1-chloro-3-iodobenzene Compound Bi was prepared in the same manner as in Preparation Example 19, except that -chloro-2-iodobenzene was used.

Preparation 28: Preparation of compound B-j

Use (3-(methylthio)naphthalen-2-yl)boronic acid instead of (1-(methylthio)naphthalen-2-yl)boronic acid and 2-bromo-1 instead of 2-bromo-1-chloro-3-iodobenzene Compound Bj was prepared in the same manner as in Preparation Example 19, except that -chloro-4-iodobenzene was used.

Preparation 29: Preparation of compound B-k

Use (3-(methylthio)naphthalen-2-yl)boronic acid instead of (1-(methylthio)naphthalen-2-yl)boronic acid and 1-bromo-3 instead of 2-bromo-1-chloro-3-iodobenzene Compound Bk was prepared in the same manner as in Preparation Example 19, except that -chloro-5-iodobenzene was used.

Preparation 30: Preparation of compound B-1

Use (3-(methylthio)naphthalen-2-yl)boronic acid instead of (1-(methylthio)naphthalen-2-yl)boronic acid and 1-bromo-2 instead of 2-bromo-1-chloro-3-iodobenzene Compound Bl was prepared in the same manner as in Preparation Example 19, except that -chloro-4-iodobenzene was used.

Preparation 31: Preparation of compound B-m

Compound B-m was prepared in the same manner as in Preparation Example 19, except that (2-(methylthio)naphthalen-1-yl)boronic acid was used instead of (1-(methylthio)naphthalen-2-yl)boronic acid.

Preparation 32: Preparation of compound B-n

Use (2-(methylthio)naphthalen-1-yl)boronic acid instead of (1-(methylthio)naphthalen-2-yl)boronic acid and 2-bromo-4 instead of 2-bromo-1-chloro-3-iodobenzene Compound Bn was prepared in the same manner as in Preparation Example 19, except that -chloro-1-iodobenzene was used.

Preparation 33: Preparation of compound B-o

Use (2-(methylthio)naphthalen-1-yl)boronic acid instead of (1-(methylthio)naphthalen-2-yl)boronic acid and 1-bromo-4 instead of 2-bromo-1-chloro-3-iodobenzene Compound Bo was prepared in the same manner as in Preparation Example 19, except that -chloro-2-iodobenzene was used.

Preparation 34: Preparation of compound B-p

Use (2-(methylthio)naphthalen-1-yl)boronic acid instead of (1-(methylthio)naphthalen-2-yl)boronic acid and 2-bromo-1 instead of 2-bromo-1-chloro-3-iodobenzene Compound Bp was prepared in the same manner as in Preparation Example 19, except that -chloro-4-iodobenzene was used.

Preparation 35: Preparation of compound B-q

Use (2-(methylthio)naphthalen-1-yl)boronic acid instead of (1-(methylthio)naphthalen-2-yl)boronic acid and 1-bromo-3 instead of 2-bromo-1-chloro-3-iodobenzene Compound Bq was prepared in the same manner as in Preparation Example 19 except that -chloro-5-iodobenzene was used.

Preparation 36: Preparation of compound B-r

Use (2-(methylthio)naphthalen-1-yl)boronic acid instead of (1-(methylthio)naphthalen-2-yl)boronic acid and 1-bromo-2 instead of 2-bromo-1-chloro-3-iodobenzene Compound Br was prepared in the same manner as in Preparation Example 19, except that -chloro-4-iodobenzene was used.

[Synthesis Example - Synthesis of Example Compounds]

Synthesis Example 1: Synthesis of Compound 1

Formula Aa (10 g, 30.2 mmol), sub1 (15.2 g, 61.8 mmol), and sodium tert-butoxide (7.2 g, 75.4 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.4 g of Compound 1. (Yield 68%, MS: [M+H] ⁺ = 705)

Synthesis Example 2: Synthesis of compound 2

Formula Aa (10 g, 30.2 mmol), sub2 (8.2 g, 30.5 mmol), and sodium tert-butoxide (3.5 g, 36.2 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.4 g of Formula Aa-1. (Yield 60%, MS: [M+H] ⁺ = 520)

Formula Aa-1 (10 g, 19.2 mmol), sub3 (5.4 g, 19.6 mmol), and sodium tert-butoxide (2.4 g, 25 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.6 g of Compound 2. (Yield 52%, MS: [M+H] ⁺ = 759)

Synthesis Example 3: Synthesis of compound 3

Formula Ab (10 g, 30.2 mmol), sub4 (5.2 g, 30.5 mmol), and sodium tert-butoxide (3.5 g, 36.2 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.1 g of Formula Ab-1. (Yield 56%, MS: [M+H] ⁺ = 420)

Formula Ab-1 (10 g, 23.8 mmol), sub5 (6.3 g, 24.3 mmol), and sodium tert-butoxide (3 g, 31 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.8 g of compound 3. (Yield 51%, MS: [M+H] ⁺ = 643)

Synthesis Example 4: Synthesis of compound 4

Formula Ab (10 g, 30.2 mmol), sub6 (15.2 g, 61.8 mmol), and sodium tert-butoxide (7.2 g, 75.4 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11 g of compound 4. (Yield 52%, MS: [M+H] ⁺ = 705)

Synthesis Example 5: Synthesis of compound 5

Formula Ab (10 g, 30.2 mmol), sub7 (10.2 g, 30.5 mmol), and sodium tert-butoxide (3.5 g, 36.2 mmol) were added to 200 ml of Xylene under a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, the reaction was terminated, cooled to room temperature, and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.8 g of Formula Ab-2. (Yield 61%, MS: [M+H] ⁺ = 586)

Formula Ab-2 (10 g, 17.1 mmol), sub4 (2.9 g, 17.4 mmol), and sodium tert-butoxide (2.1 g, 22.2 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.4 g of compound 5. (Yield 60%, MS: [M+H] ⁺ = 719)

Synthesis Example 6: Synthesis of compound 6

Chemical formula Ac (10 g, 30.2 mmol), sub8 (15.2 g, 61.8 mmol), and sodium tert-butoxide (7.2 g, 75.4 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.7 g of compound 6. (yield 69%, MS: [M+H] ⁺ = 705)

Synthesis Example 7: Synthesis of compound 7

Chemical formula Ae (10 g, 30.2 mmol), sub9 (17 g, 61.8 mmol), and sodium tert-butoxide (7.2 g, 75.4 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.3 g of compound 7. (Yield 62%, MS: [M+H] ⁺ = 765)

Synthesis Example 8: Synthesis of compound 8

Formula Ae (10 g, 30.2 mmol), sub10 (13.6 g, 61.8 mmol), and sodium tert-butoxide (7.2 g, 75.4 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.4 g of compound 8. (Yield 63%, MS: [M+H] ⁺ = 653)

Synthesis Example 9: Synthesis of compound 9

Formula Ah (10 g, 30.2 mmol), sub6 (15.2 g, 61.8 mmol), and sodium tert-butoxide (7.2 g, 75.4 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11 g of compound 9. (Yield 52%, MS: [M+H] ⁺ = 705)

Synthesis Example 10: Synthesis of compound 10

Formula Ah (10 g, 30.2 mmol), sub11 (16g, 61.8 mmol), and sodium tert-butoxide (7.2 g, 75.4 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.4 g of compound 10. (Yield 65%, MS: [M+H] ⁺ = 733)

Synthesis Example 11: Synthesis of compound 11

Formula Ai (10 g, 30.2 mmol), sub5 (7.9 g, 30.5 mmol), and sodium tert-butoxide (3.5 g, 36.2 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.6 g of Formula Ai-1. (Yield 56%, MS: [M+H] ⁺ = 510)

Formula Ai-1 (10 g, 19.6 mmol), sub6 (4.9 g, 20 mmol), and sodium tert-butoxide (2.4 g, 25.5 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.2 g of compound 11. (Yield 65%, MS: [M+H] ⁺ = 719)

Synthesis Example 12: Synthesis of compound 12

Chemical formulas Ai (10 g, 30.2 mmol), sub6 (7.5 g, 30.5 mmol), and sodium tert-butoxide (3.5 g, 36.2 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.8 g of Formula Ai-2. (yield 59%, MS: [M+H] ⁺ = 496)

Formula Ai-2 (10 g, 20.2 mmol), sub1 (5 g, 20.6 mmol), and sodium tert-butoxide (2.5 g, 26.2 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.5 g of compound 12. (Yield 53%, MS: [M+H] ⁺ = 705)

Synthesis Example 13: Synthesis of compound 13

Formula Aj (10 g, 30.2 mmol), sub4 (5.2 g, 30.5 mmol), and sodium tert-butoxide (3.5 g, 36.2 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.2 g of Formula Aj-1. (Yield 65%, MS: [M+H] ⁺ = 420)

Formula Aj-1 (10 g, 23.8 mmol), sub9 (6.7 g, 24.3 mmol), and sodium tert-butoxide (3 g, 31 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.2 g of compound 13. (Yield 65%, MS: [M+H] ⁺ = 659)

Synthesis Example 14: Synthesis of compound 14

Chemical formula Ak (10 g, 30.2 mmol), sub6 (7.5 g, 30.5 mmol), and sodium tert-butoxide (3.5 g, 36.2 mmol) were added to Xylene 200 ml in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.7 g of formula Ak-1. (Yield 65%, MS: [M+H] ⁺ = 496)

Chemical formula Ak-1 (10 g, 20.2 mmol), sub12 (5.3 g, 20.6 mmol), and sodium tert-butoxide (2.5 g, 26.2 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.4 g of compound 14. (Yield 65%, MS: [M+H] ⁺ = 719)

Synthesis Example 15: Synthesis of compound 15

Chemical formula Ak (10 g, 30.2 mmol), sub8 (7.5 g, 30.5 mmol), and sodium tert-butoxide (3.5 g, 36.2 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.7 g of formula Ak-2. (Yield 58%, MS: [M+H] ⁺ = 496)

Chemical formula Ak-2 (10 g, 20.2 mmol), sub1 (5 g, 20.6 mmol), and sodium tert-butoxide (2.5 g, 26.2 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.7 g of compound 15. (Yield 54%, MS: [M+H] ⁺ = 705)

Synthesis Example 16: Synthesis of compound 16

Formula Ao (10 g, 30.2 mmol), sub13 (9.8 g, 30.5 mmol), and sodium tert-butoxide (3.5 g, 36.2 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.5 g of Formula Ao-1. (Yield 61%, MS: [M+H] ⁺ = 572)

Chemical formulas Ao-1 (10 g, 17.5 mmol), sub6 (4.4 g, 17.8 mmol), and sodium tert-butoxide (2.2 g, 22.7 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.6 g of compound 16. (Yield 63%, MS: [M+H] ⁺ = 781)

Synthesis Example 17: Synthesis of compound 17

Formula Ao (10 g, 30.2 mmol), sub14 (10.6 g, 30.5 mmol), and sodium tert-butoxide (3.5 g, 36.2 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.4 g of Formula Ao-2. (Yield 63%, MS: [M+H] ⁺ = 600)

Formula Ao-2 (10 g, 16.7 mmol), sub4 (2.9 g, 17 mmol), and sodium tert-butoxide (2.1 g, 21.7 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 6.3 g of compound 17. (Yield 52%, MS: [M+H] ⁺ = 733)

Synthesis Example 18: Synthesis of compound 18

Formula Aq (10 g, 30.2 mmol), sub15 (13.1 g, 33.2 mmol), and sodium tert-butoxide (19.2 g, 90.5 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure and cooled to room temperature. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.9 g of Formula Aq-1. (Yield 54%, MS: [M+H] ⁺ = 546)

Formula Aq-1 (10 g, 18.3 mmol), sub10 (4.1 g, 18.7 mmol), and sodium tert-butoxide (2.3 g, 23.8 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.3 g of compound 18. (Yield 70%, MS: [M+H] ⁺ = 729)

Synthesis Example 19: Synthesis of compound 19

Chemical formulas Aq (10 g, 30.2 mmol), sub4 (10.5 g, 61.8 mmol), and sodium tert-butoxide (7.2 g, 75.4 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.3 g of compound 19. (Yield 56%, MS: [M+H] ⁺ = 553)

Synthesis Example 20: Synthesis of compound 20

Chemical formulas Aq (10 g, 30.2 mmol), sub5 (7.9 g, 30.5 mmol), and sodium tert-butoxide (3.5 g, 36.2 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.8 g of Formula Aq-2. (Yield 64%, MS: [M+ ^H ]+=510)

Formula Aq-2 (10 g, 19.6 mmol), sub4 (3.4 g, 20 mmol), and sodium tert-butoxide (2.4 g, 25.5 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.9 g of compound 20. (Yield 63%, MS: [M+H] ⁺ = 643)

Synthesis Example 21: Synthesis of compound 21

Formula Ar (10 g, 30.2 mmol), sub4 (5.2 g, 30.5 mmol), and sodium tert-butoxide (3.5 g, 36.2 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 6.6 g of Formula Ar-1. (Yield 52%, MS: [M+H] ⁺ = 420)

Formula A-r-1 (10 g, 23.8 mmol), sub1 (6 g, 24.3 mmol), and sodium tert-butoxide (3 g, 31 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10 g of compound 21. (Yield 67%, MS: [M+H] + = 629)

Synthesis Example 22: Synthesis of compound 22

Formula Ar (10 g, 30.2 mmol), sub16 (17 g, 61.8 mmol), and sodium tert-butoxide (7.2 g, 75.4 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 15.9 g of compound 22. (yield 69%, MS: [M+H] ⁺ = 765)

Synthesis Example 23: Synthesis of compound 23

In a nitrogen atmosphere, formula Ba (10 g, 28.8 mmol), sub1 (7.1 g, 29.1 mmol), and sodium tert-butoxide (3.3 g, 34.5 mmol) were added to 200 ml of Xylene, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.1 g of Formula Ba-1. (yield 69%, MS: [M+H] ⁺ = 512)

Formula Ba-1 (10 g, 19.5 mmol), sub6 (4.9 g, 19.9 mmol), and sodium tert-butoxide (2.4 g, 25.4 mmol) were added to Xylene 200 ml in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.2 g of compound 23. (Yield 58%, MS: [M+H] ⁺ = 721)

Synthesis Example 24: Synthesis of compound 24

Formula Bc (10 g, 28.8 mmol), sub13 (9.3 g, 29.1 mmol), and sodium tert-butoxide (3.3 g, 34.5 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.1 g of Formula Bc-1. (Yield 66%, MS: [M+H] ⁺ = 588)

Formula Bc-1 (10 g, 17mmol), sub6 (4.3g, 17.3 mmol), and sodium tert-butoxide (2.1 g, 22.1 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.5 g of compound 24. (Yield 70%, MS: [M+H] ⁺ = 797)

Synthesis Example 25: Synthesis of compound 25

Formula Bd (10 g, 28.8 mmol), sub3 (8 g, 29.1 mmol), and sodium tert-butoxide (3.3 g, 34.5 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.7 g of Formula Bd-1. (yield 69%, MS: [M+H] ⁺ = 542)

Formula Bd-1 (10 g, 18.4 mmol), sub11 (4.9 g, 18.8 mmol), and sodium tert-butoxide (2.3 g, 24 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.6 g of compound 25. (Yield 68%, MS: [M+H] ⁺ = 765)

Synthesis Example 26: Synthesis of compound 26

Formula Be (10 g, 28.8 mmol), sub1 (14.5 g, 59 mmol), and sodium tert-butoxide (6.9 g, 71.9 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11 g of compound 26. (Yield 53%, MS: [M+H] ⁺ = 721)

Synthesis Example 27: Synthesis of compound 27

Formula Be (10 g, 28.8 mmol), sub17 (8.6 g, 29.1 mmol), and sodium tert-butoxide (3.3 g, 34.5 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.4 g of Formula Be-1. (Yield 52%, MS: [M+H] ⁺ = 562)

Formula Be-1 (10 g, 17.8 mmol), sub10 (4 g, 18.1 mmol), and sodium tert-butoxide (2.2 g, 23.1 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.7 g of compound 27. (Yield 58%, MS: [M+H] ⁺ = 745)

Synthesis Example 28: Synthesis of compound 28

Formula Bf (10 g, 28.8 mmol), sub1 (7.1 g, 29.1 mmol), and sodium tert-butoxide (3.3 g, 34.5 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.3 g of Formula Bf-1. (Yield 63%, MS: [M+H] ⁺ = 512)

Formula Bf-1 (10 g, 19.5 mmol), sub4 (3.4 g, 19.9 mmol), and sodium tert-butoxide (2.4 g, 25.4 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7 g of compound 28. (Yield 56%, MS: [M+H] ⁺ = 645)

Synthesis Example 29: Synthesis of compound 29

Formula Bg (10 g, 28.8 mmol), sub4 (4.9 g, 29.1 mmol), and sodium tert-butoxide (3.3 g, 34.5 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.3 g of Formula Bg-1. (Yield 67%, MS: [M+H] ⁺ = 433)

Formula Bg-1 (10 g, 23.1 mmol), sub8 (5.8 g, 23.6 mmol), and sodium tert-butoxide (2.9 g, 30 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.4 g of compound 29. (Yield 63%, MS: [M+H] ⁺ = 645)

Synthesis Example 30: Synthesis of compound 30

Formula Bh (10 g, 28.8 mmol), sub1 (7.1 g, 29.1 mmol), and sodium tert-butoxide (3.3 g, 34.5 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.1 g of Formula Bh-1. (Yield 55%, MS: [M+H] ⁺ = 512)

Formula Bh-1 (10 g, 23.1 mmol), sub8 (5.8 g, 23.6 mmol), and sodium tert-butoxide (2.9 g, 30 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.7 g of compound 30. (Yield 52%, MS: [M+H] ⁺ = 721)

Synthesis Example 31: Synthesis of compound 31

Formula Bi (10 g, 28.8 mmol), sub8 (14.5 g, 59 mmol), and sodium tert-butoxide (6.9 g, 71.9 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.4 g of compound 31. (Yield 60%, MS: [M+H] ⁺ = 721)

Synthesis Example 32: Synthesis of compound 32

Formula Bj (10 g, 28.8 mmol), sub4 (4.9 g, 29.1 mmol), and sodium tert-butoxide (3.3 g, 34.5 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 6.6 g of Formula Bj-1. (Yield 53%, MS: [M+H] ⁺ = 436)

Formula Bj-1 (10 g, 22.9 mmol), sub3 (6.4 g, 23.4 mmol), and sodium tert-butoxide (2.9 g, 29.8 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8 g of compound 32. (Yield 52%, MS: [M+H] ⁺ = 675)

Synthesis Example 33: Synthesis of compound 33

Formula Bl (10 g, 28.8 mmol), sub6 (7.1 g, 29.1 mmol), and sodium tert-butoxide (3.3 g, 34.5 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.2 g of Formula Bl-1. (Yield 56%, MS: [M+H] ⁺ = 512)

Formula Bl-1 (10 g, 19.5 mmol), sub13 (6.4 g, 19.9 mmol), and sodium tert-butoxide (2.4 g, 25.4 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.9 g of compound 33. (Yield 70%, MS: [M+H] ⁺ = 797)

Synthesis Example 34: Synthesis of compound 34

Formula Bm (10 g, 28.8 mmol), sub16 (8 g, 29.1 mmol), and sodium tert-butoxide (3.3 g, 34.5 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.4 g of Formula Bm-1. (Yield 67%, MS: [M+H] ⁺ = 542)

Formula Bm-1 (10 g, 18.4 mmol), sub3 (5.2 g, 18.8 mmol), and sodium tert-butoxide (2.3 g, 24 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.1 g of compound 34. (Yield 63%, MS: [M+H] ⁺ = 781)

Synthesis Example 35: Synthesis of compound 35

Formula Bn (10 g, 28.8 mmol), sub4 (10 g, 59 mmol), and sodium tert-butoxide (6.9 g, 71.9 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.3 g of compound 35. (Yield 57%, MS: [M+H] ⁺ = 569)

Synthesis Example 36: Synthesis of compound 36

Formula Bp (10 g, 28.8 mmol), sub1 (7.1 g, 29.1 mmol), and sodium tert-butoxide (3.3 g, 34.5 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.9 g of Formula Bp-1. (Yield 54%, MS: [M+H] ⁺ = 512)

Formula Bp-1 (10 g, 19.5 mmol), sub6 (4.9 g, 19.9 mmol), and sodium tert-butoxide (2.4 g, 25.4 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.4 g of compound 36. (Yield 60%, MS: [M+H] ⁺ = 721)

Synthesis Example 37: Synthesis of compound 37

Formula Bq (10 g, 28.8 mmol), sub5 (7.5 g, 29.1 mmol), and sodium tert-butoxide (3.3 g, 34.5 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.9 g of Formula Bq-1. (yield 59%, MS: [M+H] ⁺ = 526)

Formula Bq-1 (10 g, 19 mmol), sub18 (6.2 g, 19.4 mmol), and sodium tert-butoxide (2.4 g, 24.7 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.7 g of compound 37. (Yield 50%, MS: [M+H] ⁺ = 811)

Synthesis Example 38: Synthesis of compound 38

Formula Br (10 g, 28.8 mmol), sub4 (4.9 g, 29.1 mmol), and sodium tert-butoxide (3.3 g, 34.5 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.6 g of formula Br-1. (Yield 61%, MS: [M+H] ⁺ = 436)

Chemical formulas Br-1 (10 g, 22.9 mmol), sub9 (6.4 g, 23.4 mmol), and sodium tert-butoxide (2.9 g, 29.8 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9 g of compound 38. (Yield 58%, MS: [M+H] ⁺ = 675)

Synthesis Example 39: Synthesis of compound 39

Formula Br (10 g, 28.8 mmol), sub8 (7.1 g, 29.1 mmol), and sodium tert-butoxide (3.3 g, 34.5 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.3 g of formula Br-2. (Yield 63%, MS: [M+H] ⁺ = 512)

Formula Br-2 (10 g, 19.5 mmol), sub1 (4.9 g, 19.9 mmol), and sodium tert-butoxide (2.4 g, 25.4 mmol) were added to 200 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours, when the reaction was completed, the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8 g of compound 39. (Yield 57%, MS: [M+H] ⁺ = 721)

[Examples and Comparative Examples]

Example 1

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

The following HI-1 compound was formed as a hole injection layer on the prepared ITO transparent electrode to a thickness of 1150 Å, but the following A-1 compound was p-doped at a concentration of 1.5%. The following HT-1 compound was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 800 Å. Then, the following EB-1 compound was vacuum-deposited to a thickness of 150 Å on the hole transport layer to form an electron blocking layer. Then, on the EB-1 deposited film, the following RH-1 compound and compound 1 as a host and the following Dp-7 compound as a dopant were vacuum-deposited in a weight ratio of 49:49:2 to form a red light emitting layer with a thickness of 400 Å. A hole blocking layer was formed by vacuum-depositing the following HB-1 compound to a thickness of 30 Å on the light emitting layer. Then, on the hole blocking layer, the following ET-1 compound and the following LiQ compound were vacuum-deposited at a weight ratio of 2:1 to form an electron injection and transport layer to a thickness of 300 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1,000 Å on the electron injection and transport layer.

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

Examples 2 to 39

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.

Comparative Examples 1 to 8

An organic light emitting device was manufactured in the same manner as in Comparative Example 1, except that the compounds (C1 to C8) shown in Table 1 were used instead of Compound 1 in the organic light emitting device of Example 1.

[Experimental example]

When a current was applied to the organic light emitting diodes prepared in Examples 1 to 38 and Comparative Examples 1 to 8, 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 to 95% from the initial luminance (6000 nit).

division matter Driving voltage (V) Efficiency (cd/A) Life T95 (hr) luminous color Example 1 compound 1 3.85 18.79 220 Red Example 2 compound 2 3.78 19.00 217 Red Example 3 compound 3 3.76 18.93 222 Red Example 4 compound 4 3.80 18.19 214 Red Example 5 compound 5 3.87 19.06 226 Red Example 6 compound 6 3.83 19.25 218 Red Example 7 compound 7 3.86 18.65 227 Red Example 8 compound 8 3.76 19.00 214 Red Example 9 compound 9 3.68 20.43 224 Red Example 10 compound 10 3.68 20.40 223 Red Example 11 compound 11 3.73 19.35 226 Red Example 12 compound 12 3.69 20.14 233 Red Example 13 compound 13 3.76 19.23 221 Red Example 14 compound 14 3.70 19.57 231 Red Example 15 compound 15 3.76 19.76 226 Red Example 16 compound 16 3.56 22.93 186 Red Example 17 compound 17 3.65 20.63 194 Red Example 18 compound 18 3.60 19.55 180 Red Example 19 compound 19 3.60 22.37 183 Red Example 20 compound 20 3.60 21.44 199 Red Example 21 compound 21 3.65 22.57 183 Red Example 22 compound 22 3.60 22.76 195 Red Example 23 compound 23 3.55 20.94 286 Red Example 24 compound 24 3.58 22.20 310 Red Example 25 compound 25 3.64 22.91 294 Red Example 26 compound 26 3.64 19.82 306 Red Example 27 compound 27 3.55 22.30 310 Red Example 28 compound 28 3.60 21.72 301 Red Example 29 compound 29 3.80 19.09 215 Red Example 30 compound 30 3.89 18.62 222 Red Example 31 compound 31 3.75 19.45 212 Red Example 32 compound 32 3.78 19.09 221 Red Example 33 compound 33 3.87 18.41 214 Red Example 34 compound 34 3.57 17.76 190 Red Example 35 compound 35 3.63 17.97 182 Red Example 36 compound 36 3.61 17.07 194 Red Example 37 compound 37 3.57 18.31 194 Red Example 38 compound 38 3.65 17.91 180 Red Example 39 compound 39 3.60 18.32 189 Red Comparative Example 1 C-1 4.11 13.20 103 Red Comparative Example 2 C-2 3.91 16.35 148 Red Comparative Example 3 C-3 3.97 16.07 160 Red Comparative Example 4 C-4 4.05 13.80 117 Red Comparative Example 5 C-5 4.04 10.03 78 Red Comparative Example 6 C-6 4.02 12.62 124 Red Comparative Example 7 C-7 4.13 11.02 120 Red Comparative Example 8 C-8 4.28 10.43 109 Red

Referring to the results of Table 1, the organic light emitting device of Example used the compound represented by Formula 1 and RH-1 as the host compound of the light emitting layer, and was an organic light emitting device using Dp-7 as the dopant, and low driving It was confirmed that voltage, excellent luminous efficiency, and lifespan characteristics were remarkably improved.

In Comparative Examples 1 to 8, organic light emitting devices were manufactured using C-1 to C-8 instead of the compound represented by Formula 1 as the light emitting layer host compound, and compared to Examples, the driving voltage was significantly increased, and the efficiency and lifespan characteristics were significantly increased. It could be seen that there was a decrease.

Through this, it was found that when the compound represented by Formula 1 is applied as the host of the light emitting layer of the organic light emitting device, energy transfer to the red dopant is performed well. In addition, it was found that the lifetime characteristics can be greatly improved while maintaining high efficiency. This can be determined because the compound represented by Formula 1 has higher stability to electrons and holes than the compound used in Comparative Example.

1: Substrate 2: Anode
3: hole transport layer 4: light emitting layer
5: Electron injection and transport layer 6: Cathode
7: hole injection layer 8: electron suppression layer
9: hole blocking layer

Claims (10)

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

In Formula 1,
Y is S or O;
A is a naphthalene ring,
L ₁ and L ₂ are each independently a direct bond or a substituted or unsubstituted C _6-60 arylene;
Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ are each independently substituted or unsubstituted C _6-60 aryl or substituted or unsubstituted containing any one or more heteroatoms selected from the group consisting of N, O and S cyclic C _2-60 heteroaryl;
R ₁ is each independently hydrogen, deuterium, substituted or unsubstituted C _1-60 alkyl or substituted or unsubstituted C _6-60 aryl;
m is an integer from 0 to 6.
According to claim 1,
The compound represented by Formula 1 is represented by the following Formulas 1-1 to 1-3,
compound:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3,
Y, L ₁ , L ₂ , Ar ₁ , Ar ₂ , Ar ₃ , Ar ₄ , R ₁ and m are as defined in claim 1.
According to claim 1,
The compound represented by Formula 1 is represented by the following Formulas 2-1 to 2-6,
compound:
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

In Formulas 2-1 to 2-6,
Y, L ₁ , L ₂ , Ar ₁ , Ar ₂ , Ar ₃ , Ar ₄ , R ₁ and m are as defined in claim 1.
According to claim 1,
L ₁ and L ₂ are each independently a direct bond, phenylene, biphenylrylene or naphthylene,
compound.
According to claim 1,
Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ are each independently, biphenylyl, terphenylyl, naphthyl, naphthylphenyl, phenylnaphthyl, phenanthrenyl, triphenylenyl, dimethylfluorenyl, diphenyl which is fluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazol-9-yl, or 9-phenyl-9H-carbazolyl;
compound.
According to claim 1,
R ₁ is each independently hydrogen, deuterium, C _1-10 alkyl or phenyl;
compound.
According to claim 1,
m is an integer from 0 to 2.
According to claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of
compound:

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

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