KR20200086233A - 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, wherein the compound is represented by chemical formula 1. The compound can improve life characteristics of the organic light emitting device.

Description

A novel compound and an organic light emitting device using the same{NOVEL COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

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

In general, the organic light emitting phenomenon refers to a phenomenon that converts electrical energy 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, and fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies have been conducted.

The 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. In order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often formed of a multi-layered structure composed of different materials, for example, may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected at the anode, and electrons are injected at the cathode, and an exciton is formed when the injected holes meet the electrons. When it falls to the ground again, it will shine.

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

Korean Patent Publication No. 10-2000-0051826

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

The present invention provides a compound represented by Formula 1:

[Formula 1]

In Chemical Formula 1,

Any one of Q is a substituent represented by the following Chemical Formula 2, any one of the other is a substituent represented by the following Chemical Formula 3, and the other is CH,

However, the substituent represented by the following formula (2) and the substituent represented by the following formula (3) are connected to an ortho position,

n is an integer from 0 to 4,

R ₁ is hydrogen; heavy hydrogen; halogen; Cyano; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _2-60 alkynyl; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _6-60 aryl; Or C _5-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,

[Formula 2]

In Chemical Formula 2,

X are each independently N or CH, provided that at least one of them is N,

Ar ₁ and Ar ₂ are each independently substituted or unsubstituted C _6-60 aryl; Or C _5-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,

[Formula 3]

In Chemical Formula 3,

Y is O or S.

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

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

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.
Figure 2 is a substrate (1), anode (2), hole injection layer (5), hole transport layer (6), hole blocking layer (7), light emitting layer (3), electron transport layer (8), electron injection layer (9) And an example of an organic light-emitting device comprising the cathode 4.

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

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

, 또는

는 다른 치환기에 연결되는 결합을 의미한다. In this specification,

, or

Means a linkage to another substituent.

The term "substituted or unsubstituted" in this specification is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amino group; Phosphine oxide group; Alkoxy groups; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Aryl sulfoxyl group; Silyl group; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; An alkenyl group; Alkyl aryl groups; Alkylamine groups; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups containing one or more of N, O and S atoms, or substituted or unsubstituted with two or more substituents among the exemplified substituents above . For example, "a substituent having two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.

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

In the present specification, the oxygen of the ester group may be substituted with a straight chain, 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 this specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.

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

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

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

In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, steelbenyl 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 cycloalkyl group has 3 to 20 carbon atoms. 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 is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., as a monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

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

It can be back. However, it is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si and S as heterogeneous elements, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrol group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, Acridil group, pyridazine group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, Isooxazolyl groups, oxadiazolyl groups, thiadiazolyl groups, benzothiazolyl groups, phenothiazinyl groups and dibenzofuranyl groups, and the like, but are not limited thereto.

In the present specification, an aryl group in an aralkyl group, an alkenyl group, an alkylaryl group, and an 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, alkylaryl group, and alkylamine group is the same as the above-described alkyl group. In the present specification, heteroarylamine among heteroarylamines may be applied to the description of the aforementioned heterocyclic group. In the present specification, the alkenyl group among the alkenyl groups is the same as the exemplified alkenyl group. In the present specification, the description of the aryl group described above may be applied, except that the arylene is a divalent group. In the present specification, the description of the heterocyclic group described above may be applied, except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and a description of the aryl group or cycloalkyl group described above may be applied, except that two substituents are formed by bonding. In the present specification, the heterocycle is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied, except that two substituents are formed by bonding.

Preferably, the formula 1 may be any one selected from compounds represented by the following formulas 1-1 to 1-6:

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

In Chemical Formulas 1-1 to 1-6,

Descriptions of X, Y, Ar ₁ , Ar ₂ , R ₁ and n are as defined above.

Preferably, n can be 0 or 1.

Preferably, R ₁ is hydrogen; heavy hydrogen; methyl; Or phenyl.

Preferably, X can all be N.

Preferably, Ar ₁ and Ar ₂ may be any one selected from the group consisting of each independently.

In the above formula,

m is an integer from 0 to 5,

k is an integer from 0 to 4,

R ₂ is hydrogen; heavy hydrogen; halogen; Cyano; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _2-60 alkynyl; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _6-60 aryl; Or C _5-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S.

Preferably, R ₂ is hydrogen; heavy hydrogen; methyl; Or phenyl.

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

Meanwhile, the compound represented by Chemical Formula 1-1 may be prepared, for example, by the same method as in Scheme 1 below, and the compound represented by Chemical Formula 1-2 may be prepared by the same method as in Scheme 2, for example. The compound represented by Chemical Formula 1-3 may be prepared by, for example, a production method as shown in Reaction Scheme 3 below, and the compound represented by Chemical Formula 1-4 may be prepared by a production method as shown in Reaction Scheme 4 as an example. A compound represented by Formula 1-5 may be prepared by a manufacturing method such as Reaction Scheme 5 below, and a compound represented by Formula 1-6 may be prepared by a manufacturing method such as Reaction Scheme 6 below as an example. have.

[Scheme 1]

[Scheme 2]

[Scheme 3]

[Scheme 4]

[Scheme 5]

[Scheme 6]

In Reaction Schemes 1 to 6, definitions other than Z are as defined above, and Z is halogen and more preferably bromo or chloro. The reaction is a Suzuki coupling reaction, and is preferably performed in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be modified as known in the art. The manufacturing method may be more specific in the manufacturing examples to be described later.

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

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

In addition, the organic material layer may include a hole injection layer, a hole transport layer, or a layer that simultaneously performs hole injection and transport, and the hole injection layer, a hole transport layer, or a layer that simultaneously performs hole injection and transport is represented by Formula 1 It may contain a compound to be displayed.

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

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

Further, the electron transport layer, the electron injection layer, or the layer that simultaneously performs electron transport and electron injection may include a compound represented by Chemical Formula 1.

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

Further, the organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. Further, the organic light emitting device according to the present invention may be an organic light emitting device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, the structure of 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 3, and a cathode 4. In such a structure, the compound represented by Chemical Formula 1 may be included in the light emitting layer.

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

Specifically, the organic material layer may include a light emitting layer, and the light emitting layer may include two or more host materials.

At this time, the two or more host materials may include a compound represented by Chemical Formula 1.

The organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1. Further, 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, a positive electrode is formed by depositing a metal or conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. Then, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed thereon, and a material that can be used as a cathode is deposited thereon. In addition to this method, an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

In addition, the compound represented by Chemical 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 means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.

In addition to such a method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and a cathode 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.

The positive electrode material is preferably a material having a large work function so that hole injection into the organic material layer is smooth. Specific examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide 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 an organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There is 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 an electrode, and has the ability to transport holes as a hole injection material, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is produced in the light emitting layer. A compound which prevents migration of the excitons to the electron injection layer or the electron injection material, and has excellent thin film formation ability is preferable. 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 substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances. Organic materials, anthraquinones, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes from the hole injection layer to the light emitting layer. It is a material that transports holes from the anode or the hole injection layer as a hole transport material and transfers them to the light emitting layer. This is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.

As the light-emitting material, a material capable of emitting light in the visible region by receiving and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, is preferably a material having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly(p-phenylenevinylene) (PPV)-based polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.

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

Examples of the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periplanene, etc. having an arylamino group, and substituted or unsubstituted as a styrylamine compound. A compound in which at least one arylvinyl group is substituted with the arylamine, a substituent selected from 1 or 2 or more from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, metal complexes include, but are not limited to, iridium complexes, platinum complexes, and the like.

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

The electron injection layer is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from a cathode, an excellent electron injection effect on a light emitting layer or a light emitting material, and injects holes generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato) zinc, bis(8-hydroxyquinolinato) copper, bis(8-hydroxyquinolinato) manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato) zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.

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

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

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

Preparation Example 1: Preparation of compound sub 1

(1) Preparation of compound A-1

2-bromo-3-chloro-1,4-difluorobenzene (100 g, 442.7 mmol) and (2-hydroxyphenyl)boronic acid (61.1 g, 442.7 mmol) in tetrahydrofuran (2000) in a nitrogen atmosphere. ml) and stirred and refluxed. Thereafter, potassium carbonate (183.5 g, 1328 mmol) was dissolved in water (184 ml), stirred thoroughly, and then tetrakistriphenyl-phosphino palladium (15.3 g, 13.3 mmol) was added. After the reaction for 3 hours, after cooling to room temperature, the organic layer and the water layer were separated, and then the organic layer was distilled. This was again dissolved in chloroform (2125 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered to distill the filtrate under reduced pressure. The concentrated compound was white solid compound A-1 (74.4 g, yield 70%, MS: [M+H] ⁺ = 241) by recrystallization of chloroform and ethyl acetate.

(2) Preparation of compound A-2

In a nitrogen atmosphere, A1 (50 g, 208.3 mmol) and bis(pinacolato)diboron (55.6 g, 208.3 mmol) were added to dimethylformamide (250 ml), potassium carbonate was added thereto, followed by stirring and heating to 140°C. Did. After 4 hours, after cooling to room temperature, water was added. The solid formed was then filtered. This was again dissolved in chloroform (458 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a yellow solid compound A-2 (24.3 g, yield 53%, MS: [M+H] ⁺ = 221).

(3) Preparation of compound A-3

In a nitrogen atmosphere, A-2 (20 g, 90.9 mmol) and bis(pinacolato)diboron (46.2 g, 181.8 mmol) were added to dioxane (400 ml), stirred and refluxed. Then, potassium acetate (26.2 g, 272.7 mmol) was added and stirred sufficiently, followed by palladium dibenzylidene acetone palladium (1.6 g, 2.7 mmol) and tricyclohexylphosphine (1.5 g, 5.5 mmol). After the reaction was cooled to room temperature for 6 hours, the organic layer was filtered to remove salt, and then the filtered organic layer was distilled. This was again dissolved in chloroform (284 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was white solid compound A-3 (23.3 g, yield 82%, MS: [M+H] ⁺ = 313.1) by recrystallization of chloroform and ethanol.

(4) Preparation of compound sub 1

In a nitrogen atmosphere, A-3 (20 g, 64.1 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (17.1 g, 64.1 mmol) were added to tetrahydrofuran (400 ml). Stirring and reflux. Subsequently, potassium carbonate (26.6 g, 192.2 mmol) was dissolved in water (27 ml), stirred thoroughly, and then tetrakistriphenyl-phosphino palladium (2.2 g, 1.9 mmol) was added. After the reaction was cooled to room temperature for 1 hour, the organic layer and the water layer were separated, and then the organic layer was distilled. This was again dissolved in chloroform (535 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was white solid compound sub 1 (18.4 g, yield 69%, MS: [M+H] ⁺ = 418.1) by recrystallization of chloroform and ethyl acetate.

Preparation Example 2: Preparation of compound sub 2

(1) Preparation of compound B-1

1-bromo-4-chloro-2,5-difluorobenzene (100 g, 442.7 mmol) and (2-hydroxyphenyl)boronic acid (61.1 g, 442.7 mmol) in tetrahydrofuran (2000) in a nitrogen atmosphere. ml) and stirred and refluxed. Thereafter, potassium carbonate (183.5 g, 1328 mmol) was dissolved in water (184 ml), stirred thoroughly, and then tetrakistriphenyl-phosphino palladium (15.3 g, 13.3 mmol) was added. After the reaction for 3 hours, after cooling to room temperature, the organic layer and the water layer were separated, and then the organic layer was distilled. This was again dissolved in chloroform (2125 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered to distill the filtrate under reduced pressure. The concentrated compound was white solid compound B-1 (56.3 g, yield 53%, MS: [M+H] ⁺ = 241) by recrystallization of chloroform and ethyl acetate.

(2) Preparation of compound B-2

In nitrogen atmosphere, B-1 (50 g, 208.3 mmol) and bis(pinacolato)diboron (55.6 g, 208.3 mmol) were added to dimethylformamide (250 ml), potassium carbonate was added thereto, followed by stirring and 140°C. Heated to. After the reaction for 6 hours, the mixture was cooled to room temperature, and then water was added. The solid formed was then filtered. This was again dissolved in chloroform (458 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound B-2 (30.2 g, yield 66%, MS: [M+H] ⁺ = 221).

(3) Preparation of compound B-3

In a nitrogen atmosphere, B-2 (20 g, 71.9 mmol) and bis(pinacolato)diboron (36.6 g, 143.9 mmol) were added to dioxane (400 ml), stirred and refluxed. Then, potassium acetate (20.7 g, 215.8 mmol) was added and stirred sufficiently, followed by palladium dibenzylidene acetone palladium (1.2 g, 2.2 mmol) and tricyclohexylphosphine (1.2 g, 4.3 mmol). After the reaction for 7 hours, after cooling to room temperature, the organic layer was filtered to remove salt, and then the filtered organic layer was distilled. This was again dissolved in chloroform (225 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was white solid compound B-3 (11.7 g, yield 52%, MS: [M+H] ⁺ = 313.1) by recrystallization of chloroform and ethanol.

(4) Preparation of compound sub 2

In a nitrogen atmosphere, B-3 (20 g, 43.5 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (11.6 g, 43.5 mmol) were added to tetrahydrofuran (400 ml). Stirring and reflux. Subsequently, potassium carbonate (18 g, 130.4 mmol) was dissolved in water (18 ml), stirred thoroughly, and then tetrakistriphenyl-phosphino palladium (1.5 g, 1.3 mmol) was added. After the reaction was cooled to room temperature for 1 hour, the organic layer and the water layer were separated, and then the organic layer was distilled. This was again dissolved in chloroform (363 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was white solid compound sub 2 (9.8 g, yield 54%, MS: [M+H] ⁺ = 418.1) by recrystallization of chloroform and ethyl acetate.

Preparation Example 3: Preparation of compound sub 3

(1) Preparation of compound C-1

1-bromo-4-chloro-2,3-difluorobenzene (100 g, 442.7 mmol) and (2-hydroxyphenyl)boronic acid (159.6 g, 442.7 mmol) in tetrahydrofuran (2000) in a nitrogen atmosphere. ml) and stirred and refluxed. Thereafter, potassium carbonate (183.5 g, 1328 mmol) was dissolved in water (184 ml), stirred thoroughly, and then tetrakistriphenyl-phosphino palladium (15.3 g, 13.3 mmol) was added. After the reaction was cooled to room temperature for 2 hours, the organic layer and the water layer were separated, and then the organic layer was distilled. This was again dissolved in chloroform (2125 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered to distill the filtrate under reduced pressure. The concentrated compound was white solid compound C-1 (60.6 g, yield 57%, MS: [M+H] ⁺ = 241) by recrystallization of chloroform and ethyl acetate.

(2) Preparation of compound C-2

In a nitrogen atmosphere, C-1 (50 g, 208.3 mmol) and bis(pinacolato)diboron (55.6 g, 208.3 mmol) were added to dimethylformamide (250 ml), potassium carbonate was added thereto, followed by stirring and 140°C. Heated to. After 5 hours, the mixture was cooled to room temperature, and then water was added. The solid formed was then filtered. This was again dissolved in chloroform (458 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound C-2 (26.6 g, yield 58%, MS: [M+H] ⁺ = 221).

(3) Preparation of compound C-3

In a nitrogen atmosphere, C-2 (20 g, 50 mmol) and bis(pinacolato)diboron (25.4 g, 100 mmol) were added to dioxane (400 ml), stirred and refluxed. Then, potassium acetate (14.4 g, 150 mmol) was added and stirred sufficiently, followed by palladium dibenzylidene acetone palladium (0.9 g, 1.5 mmol) and tricyclohexylphosphine (0.8 g, 3 mmol). After the reaction for 7 hours, after cooling to room temperature, the organic layer was filtered to remove salt, and then the filtered organic layer was distilled. This was again dissolved in chloroform (156 ml), washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was white solid compound C-3 (11.7 g, yield 75%, MS: [M+H] ⁺ = 313.1) by recrystallization of chloroform and ethanol.

(4) Preparation of compound sub 3

In a nitrogen atmosphere, C-3 (20 g, 43.5 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (11.6 g, 43.5 mmol) were added to tetrahydrofuran (400 ml). Stirring and reflux. Subsequently, potassium carbonate (18 g, 130.4 mmol) was dissolved in water (18 ml), stirred thoroughly, and then tetrakistriphenyl-phosphino palladium (1.5 g, 1.3 mmol) was added. After the reaction was cooled to room temperature for 2 hours, the organic layer and the water layer were separated, and then the organic layer was distilled. This was again dissolved in chloroform (363 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was white solid compound sub 3 (10.5 g, yield 58%, MS: [M+H] ⁺ = 418.1) by recrystallization of chloroform and ethyl acetate.

Preparation Example 4: Preparation of compound sub 4

(1) Preparation of compound D-1

1-bromo-3-chloro-2,4-difluorobenzene (100 g, 442.7 mmol) and (2-hydroxyphenyl)boronic acid (151.9 g, 442.7 mmol) in tetrahydrofuran (2000) in a nitrogen atmosphere. ml) and stirred and refluxed. Thereafter, potassium carbonate (183.5 g, 1328 mmol) was dissolved in water (184 ml), stirred thoroughly, and then tetrakistriphenyl-phosphino palladium (15.3 g, 13.3 mmol) was added. After the reaction for 3 hours, after cooling to room temperature, the organic layer and the water layer were separated, and then the organic layer was distilled. This was again dissolved in chloroform (2125 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered to distill the filtrate under reduced pressure. The concentrated compound was white solid compound D-1 (80.8 g, yield 76%, MS: [M+H] ⁺ = 241) by recrystallization of chloroform and ethyl acetate.

(2) Preparation of compound D-2

D-1 (50 g, 208.3 mmol) and bis(pinacolato)diboron (55.6 g, 208.3 mmol) were added to dimethylformamide (250 ml) in a nitrogen atmosphere, followed by stirring with potassium carbonate and 140°C. Heated to. After the reaction for 7 hours, the mixture was cooled to room temperature, and then water was added. The solid formed was then filtered. This was again dissolved in chloroform (458 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound D-2 (28.4 g, yield 62%, MS: [M+H] ⁺ = 221).

(3) Preparation of compound D-3

D-2 (20 g, 40 mmol) and bis(pinacolato)diboron (20.3 g, 80 mmol) were added to dioxane (400 ml) in a nitrogen atmosphere, stirred and refluxed. Then, potassium acetate (11.5 g, 120 mmol) was added and stirred sufficiently, followed by palladium dibenzylidene acetone palladium (0.7 g, 1.2 mmol) and tricyclohexylphosphine (0.7 g, 2.4 mmol). After the reaction was cooled to room temperature for 4 hours, the organic layer was filtered to remove salt, and then the filtered organic layer was distilled. This was again dissolved in chloroform (125 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was white solid compound D-3 (8.6 g, yield 69%, MS: [M+H] ⁺ = 313.1) by recrystallization of chloroform and ethanol.

(4) Preparation of compound sub 4

In a nitrogen atmosphere, D-3 (20 g, 43.5 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (11.6 g, 43.5 mmol) were added to tetrahydrofuran (400 ml). Stirring and reflux. Subsequently, potassium carbonate (18 g, 130.4 mmol) was dissolved in water (18 ml), stirred thoroughly, and then tetrakistriphenyl-phosphino palladium (1.5 g, 1.3 mmol) was added. After the reaction was cooled to room temperature for 1 hour, the organic layer and the water layer were separated, and then the organic layer was distilled. This was again dissolved in chloroform (363 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was prepared by recrystallization of chloroform and ethyl acetate to prepare a white solid compound sub 4 (9.6 g, yield 53%, MS: [M+H] ⁺ = 418.1).

Preparation Example 5: Preparation of compound sub 5

(1) Preparation of compound E-1

1-bromo-5-chloro-2,4-difluorobenzene (100 g, 442.7 mmol) and (2-hydroxyphenyl)boronic acid (151.9 g, 442.7 mmol) in tetrahydrofuran (2000) in a nitrogen atmosphere. ml) and stirred and refluxed. Thereafter, potassium carbonate (183.5 g, 1328 mmol) was dissolved in water (184 ml), stirred thoroughly, and then tetrakistriphenyl-phosphino palladium (15.3 g, 13.3 mmol) was added. After the reaction for 3 hours, after cooling to room temperature, the organic layer and the water layer were separated, and then the organic layer was distilled. This was again dissolved in chloroform (2125 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered to distill the filtrate under reduced pressure. The concentrated compound was prepared by recrystallization of chloroform and ethyl acetate to prepare a yellow solid compound E-1 (85 g, yield 80%, MS: [M+H] ⁺ = 241).

(2) Preparation of compound E-2

In a nitrogen atmosphere, E-1 (50 g, 208.3 mmol) and bis(pinacolato)diboron (55.6 g, 208.3 mmol) were added to dimethylformamide (250 ml), potassium carbonate was added thereto, followed by stirring and 140°C. Heated to. After the reaction for 7 hours, the mixture was cooled to room temperature, and then water was added. The solid formed was then filtered. This was again dissolved in chloroform (458 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound E-2 (29.8 g, yield 65%, MS: [M+H] ⁺ = 221).

(3) Preparation of compound E-3

In a nitrogen atmosphere, E-2 (20 g, 33.3 mmol) and bis(pinacolato)diboron (16.9 g, 66.7 mmol) were added to dioxane (400 ml), stirred and refluxed. Then, potassium acetate (9.6 g, 100 mmol) was added and stirred sufficiently, followed by palladium dibenzylidene acetone palladium (0.6 g, 1 mmol) and tricyclohexylphosphine (0.6 g, 2 mmol). After the reaction was cooled to room temperature for 6 hours, the organic layer was filtered to remove salt, and then the filtered organic layer was distilled. This was again dissolved in chloroform (104 ml), washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was white solid compound E-3 (8 g, yield 77%, MS: [M+H] ⁺ = 313.1) by recrystallization of chloroform and ethanol.

(4) Preparation of compound sub 5

In a nitrogen atmosphere, E-3 (20 g, 43.5 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (11.6 g, 43.5 mmol) were added to tetrahydrofuran (400 ml). Stirring and reflux. Subsequently, potassium carbonate (18 g, 130.4 mmol) was dissolved in water (18 ml), stirred thoroughly, and then tetrakistriphenyl-phosphino palladium (1.5 g, 1.3 mmol) was added. After the reaction was cooled to room temperature for 1 hour, the organic layer and the water layer were separated, and then the organic layer was distilled. This was again dissolved in chloroform (363 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was prepared by recrystallization of chloroform and ethyl acetate to prepare a yellow solid compound sub 5 (10.9 g, yield 60%, MS: [M+H] ⁺ = 418.1).

Preparation Example 6: Preparation of compound sub 6

(1) Preparation of compound F-1

2-bromo-4-chloro-1,3-difluorobenzene (100 g, 442.7 mmol) and (2-hydroxyphenyl)boronic acid (151.9 g, 442.7 mmol) in tetrahydrofuran (2000) in a nitrogen atmosphere. ml) and stirred and refluxed. Thereafter, potassium carbonate (183.5 g, 1328 mmol) was dissolved in water (184 ml), stirred thoroughly, and then tetrakistriphenyl-phosphino palladium (15.3 g, 13.3 mmol) was added. After the reaction was cooled to room temperature for 2 hours, the organic layer and the water layer were separated, and then the organic layer was distilled. This was again dissolved in chloroform (2125 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered to distill the filtrate under reduced pressure. The concentrated compound was prepared by recrystallization of chloroform and ethyl acetate to prepare a yellow solid compound F-1 (62.7 g, yield 59%, MS: [M+H] ⁺ = 241).

(2) Preparation of compound F-2

In a nitrogen atmosphere, F-1 (50 g, 208.3 mmol) and bis(pinacolato)diboron (55.6 g, 208.3 mmol) were added to dimethylformamide (250 ml), potassium carbonate was added thereto, followed by stirring and 140°C. Heated to. After 4 hours, after cooling to room temperature, water was added. The solid formed was then filtered. This was again dissolved in chloroform (458 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound F-2 (27.5 g, yield 60%, MS: [M+H] ⁺ = 221).

(3) Preparation of compound F-3

In a nitrogen atmosphere, F-2 (20 g, 33.3 mmol) and bis(pinacolato)diboron (16.9 g, 66.7 mmol) were added to dioxane (400 ml), stirred and refluxed. Then, potassium acetate (9.6 g, 100 mmol) was added and stirred sufficiently, followed by palladium dibenzylidene acetone palladium (0.6 g, 1 mmol) and tricyclohexylphosphine (0.6 g, 2 mmol). After the reaction for 3 hours, after cooling to room temperature, the organic layer was filtered to remove salt, and then the filtered organic layer was distilled. This was again dissolved in chloroform (104 ml), washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was white solid compound F-3 (7.8 g, yield 75%, MS: [M+H] ⁺ = 313.1) by recrystallization of chloroform and ethanol.

(4) Preparation of compound sub 6

In a nitrogen atmosphere, F-3 (20 g, 43.5 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (11.6 g, 43.5 mmol) were added to tetrahydrofuran (400 ml). Stirring and reflux. Subsequently, potassium carbonate (18 g, 130.4 mmol) was dissolved in water (18 ml), stirred thoroughly, and then tetrakistriphenyl-phosphino palladium (1.5 g, 1.3 mmol) was added. After the reaction for 3 hours, after cooling to room temperature, the organic layer and the water layer were separated, and then the organic layer was distilled. This was again dissolved in chloroform (363 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was prepared by recrystallization of chloroform and ethyl acetate to prepare a yellow solid compound sub 6 (12.9 g, yield 71%, MS: [M+H] ⁺ = 418.1).

Preparation Example 7: Preparation of compound G-2

(1) Preparation of compound G-1

In a nitrogen atmosphere, A-2 (50 g, 227.3 mmol) and int G (79.3 g, 227.3 mmol) were added to dimethylformamide (1000 ml), stirred and refluxed. Then, sodium tertiary-butoxide (144.7 g, 681.8 mmol) was added and stirred sufficiently, followed by bis(tritary-butylphosphine)palladium (3.5 g, 6.8 mmol). After the reaction for 3 hours, after cooling to room temperature, the organic layer was filtered to remove salt, and then the filtered organic layer was distilled. This was again dissolved in chloroform (1248 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound G-1 (97.3 g, yield 78%, MS: [M+H] ⁺ = 550.1).

(2) Preparation of compound G-2

In a nitrogen atmosphere, G-1 (20 g, 36.4 mmol) and bis(pinacolato)diboron (18.5 g, 72.8 mmol) were added to dioxane (400 ml), stirred and refluxed. Then, potassium acetate (10.5 g, 109.3 mmol) was added and stirred sufficiently, followed by palladium dibenzylidene acetone palladium (0.6 g, 1.1 mmol) and tricyclohexylphosphine (0.6 g, 2.2 mmol). After the reaction was cooled to room temperature for 4 hours, the organic layer was filtered to remove salt, and then the filtered organic layer was distilled. This was again dissolved in chloroform (234 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the filtrate was distilled under reduced pressure. The concentrated compound was white solid compound G-2 (17.8 g, yield 76%, MS: [M+H] ⁺ =642.2) by recrystallization of chloroform and ethanol.

Preparation Example 8: Preparation of compound int A

In a nitrogen atmosphere, 2-bromo-9H-carbazole (50 g, 222.2 mmol) and dibenzo[b,d]furan-4-ylboronic acid (47.1 g, 222.2 mmol) were added to tetrahydrofuran (1000 ml). Stirring and reflux. Subsequently, potassium carbonate (92.1 g, 666.7 mmol) was dissolved in water (92 ml), stirred thoroughly, and then tetrakistriphenyl-phosphino palladium (7.7 g, 6.7 mmol) was added. After the reaction for 3 hours, after cooling to room temperature, the organic layer and the water layer were separated and the organic layer was distilled. This was again dissolved in chloroform (1481 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the filtrate was distilled under reduced pressure. The concentrated compound was prepared by recrystallization of chloroform and ethyl acetate to prepare a white solid compound int A (54.8 g, yield 74%, MS: [M+H] ⁺ = 334.1).

Preparation Example 9: Preparation of compound int B

In a nitrogen atmosphere, 2-bromo-9H-carbazole (50 g, 222.2 mmol) and dibenzo[b,d]furan-3-ylboronic acid (47.1 g, 222.2 mmol) were added to tetrahydrofuran (1000 ml). Stirring and reflux. Subsequently, potassium carbonate (92.1 g, 666.7 mmol) was dissolved in water (92 ml), stirred thoroughly, and then tetrakistriphenyl-phosphino palladium (7.7 g, 6.7 mmol) was added. After the reaction for 3 hours, after cooling to room temperature, the organic layer and the water layer were separated, and then the organic layer was distilled. This was again dissolved in chloroform (1481 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the filtrate was distilled under reduced pressure. The concentrated compound was prepared by recrystallization of chloroform and ethyl acetate to prepare a white solid compound int B (43.7 g, yield 59%, MS: [M+H] ⁺ = 334.1).

Preparation Example 10: Preparation of compound int C

In a nitrogen atmosphere, 2-bromo-9H-carbazole (50 g, 222.2 mmol) and dibenzo[b,d]furan-2-ylboronic acid (47.1 g, 222.2 mmol) were added to tetrahydrofuran (1000 ml). Stirring and reflux. Subsequently, potassium carbonate (92.1 g, 666.7 mmol) was dissolved in water (92 ml), stirred thoroughly, and then tetrakistriphenyl-phosphino palladium (7.7 g, 6.7 mmol) was added. After the reaction for 3 hours, after cooling to room temperature, the organic layer and the water layer were separated, and then the organic layer was distilled. This was again dissolved in chloroform (1481 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the filtrate was distilled under reduced pressure. The concentrated compound was prepared by recrystallization of chloroform and ethyl acetate to prepare a white solid compound int C (41.5 g, yield 56%, MS: [M+H] ⁺ = 334.1).

Preparation Example 11: Preparation of compound int D

In a nitrogen atmosphere, 2-bromo-9H-carbazole (50 g, 222.2 mmol) and dibenzo[b,d]furan-1-ylboronic acid (47.1 g, 222.2 mmol) were added to tetrahydrofuran (1000 ml). Stirring and reflux. Subsequently, potassium carbonate (92.1 g, 666.7 mmol) was dissolved in water (92 ml), stirred thoroughly, and then tetrakistriphenyl-phosphino palladium (7.7 g, 6.7 mmol) was added. After the reaction for 3 hours, after cooling to room temperature, the organic layer and the water layer were separated, and then the organic layer was distilled. This was again dissolved in chloroform (1481 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the filtrate was distilled under reduced pressure. The concentrated compound was prepared by recrystallization of chloroform and ethyl acetate to prepare a white solid compound int D (45.2 g, yield 61%, MS: [M+H] ⁺ = 334.1).

Preparation Example 12: Preparation of compound int E

2-bromo-9H-carbazole (50 g, 222.2 mmol) and dibenzo[b,d]thiophen-4-ylboronic acid (50.7 g, 222.2 mmol) in tetrahydrofuran (1000 ml) in a nitrogen atmosphere. The mixture was stirred and refluxed. Subsequently, potassium carbonate (92.1 g, 666.7 mmol) was dissolved in water (92 ml), stirred thoroughly, and then tetrakistriphenyl-phosphino palladium (7.7 g, 6.7 mmol) was added. After the reaction for 3 hours, after cooling to room temperature, the organic layer and the water layer were separated, and then the organic layer was distilled. This was again dissolved in chloroform (1552 ml), washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was prepared by recrystallization of chloroform and ethyl acetate to prepare a white solid compound int E (52 g, yield 67%, MS: [M+H] ⁺ = 350.1).

Preparation 13: Preparation of compound int F

In a nitrogen atmosphere, 1-bromo-9H-carbazole (50 g, 222.2 mmol) and dibenzo[b,d]thiophen-4-ylboronic acid (50.7 g, 222.2 mmol) were added to tetrahydrofuran (1000 ml). The mixture was stirred and refluxed. Subsequently, potassium carbonate (92.1 g, 666.7 mmol) was dissolved in water (92 ml), stirred thoroughly, and then tetrakistriphenyl-phosphino palladium (7.7 g, 6.7 mmol) was added. After the reaction was cooled to room temperature for 1 hour, the organic layer and the water layer were separated, and then the organic layer was distilled. This was again dissolved in chloroform (1552 ml), washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was prepared by recrystallization of chloroform and ethyl acetate to prepare a white solid compound int F (50.4 g, yield 65%, MS: [M+H] ⁺ = 350.1).

Preparation 14: Preparation of compound int G

3-bromo-9H-carbazole (50 g, 222.2 mmol) and dibenzo[b,d]thiophen-4-ylboronic acid (50.7 g, 222.2 mmol) in tetrahydrofuran (1000 ml) in a nitrogen atmosphere. The mixture was stirred and refluxed. Subsequently, potassium carbonate (92.1 g, 666.7 mmol) was dissolved in water (92 ml), stirred thoroughly, and then tetrakistriphenyl-phosphino palladium (7.7 g, 6.7 mmol) was added. After the reaction was cooled to room temperature for 2 hours, the organic layer and the water layer were separated, and then the organic layer was distilled. This was again dissolved in chloroform (1552 ml), washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was prepared by recrystallization of chloroform and ethyl acetate to prepare a white solid compound int G (39.6 g, yield 51%, MS: [M+H] ⁺ = 350.1).

Preparation Example 15: Preparation of compound int H

4-bromo-9H-carbazole (50 g, 222.2 mmol) and dibenzo[b,d]thiophen-4-ylboronic acid (50.7 g, 222.2 mmol) in tetrahydrofuran (1000 ml) in a nitrogen atmosphere. The mixture was stirred and refluxed. Subsequently, potassium carbonate (92.1 g, 666.7 mmol) was dissolved in water (92 ml), stirred thoroughly, and then tetrakistriphenyl-phosphino palladium (7.7 g, 6.7 mmol) was added. After the reaction was cooled to room temperature for 1 hour, the organic layer and the water layer were separated, and then the organic layer was distilled. This was again dissolved in chloroform (1552 ml), washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was prepared by recrystallization of chloroform and ethyl acetate to prepare a white solid compound int H (42.7 g, yield 55%, MS: [M+H] ⁺ = 350.1).

Example 1: Synthesis of Compound 1

In nitrogen atmosphere, sub 1 (10 g, 24 mmol) and int A (8 g, 24 mmol) were added to dimethylformamide (200 ml), stirred and refluxed. Subsequently, sodium tertiary-butoxide (15.3 g, 71.9 mmol) was added, stirred sufficiently, and after 4 hours of reaction, cooled to room temperature, and the organic layer was filtered to remove salts, and then the filtered organic layer was distilled. This was again dissolved in chloroform (175 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare yellow solid compound 1 (11.6 g, yield 66%, MS: [M+H] ⁺ = 731.2).

Example 2: Synthesis of Compound 2

In a nitrogen atmosphere, sub 1 (10 g, 24 mmol) and int B (8 g, 24 mmol) were added to dimethylformamide (200 ml), stirred and refluxed. Subsequently, sodium tertiary-butoxide (15.3 g, 71.9 mmol) was added, stirred sufficiently, and after 4 hours of reaction, cooled to room temperature, and the organic layer was filtered to remove salts, and then the filtered organic layer was distilled. This was again dissolved in chloroform (175 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound 2 (13.1 g, yield 75%, MS: [M+H] ⁺ = 731.2).

Example 3: Synthesis of Compound 3

In nitrogen atmosphere, sub 1 (10 g, 24 mmol) and int C (8 g, 24 mmol) were added to dimethylformamide (200 ml), stirred and refluxed. Subsequently, sodium tertiary-butoxide (15.3 g, 71.9 mmol) was added, stirred sufficiently, cooled for 5 hours, cooled to room temperature, and the organic layer was filtered to remove salts, and then the filtered organic layer was distilled. This was again dissolved in chloroform (175 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound 3 (13.8 g, yield 79%, MS: [M+H] ⁺ = 731.2).

Example 4: Synthesis of Compound 4

In a nitrogen atmosphere, sub 1 (10 g, 24 mmol) and int D (8 g, 24 mmol) were added to dimethylformamide (200 ml), stirred and refluxed. Subsequently, sodium tertiary-butoxide (15.3 g, 71.9 mmol) was added, stirred sufficiently, cooled for 3 hours after reaction, and the organic layer was filtered to remove salt, and then the filtered organic layer was distilled. This was again dissolved in chloroform (175 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound 4 (13.5 g, yield 77%, MS: [M+H] ⁺ = 731.2).

Example 5: Synthesis of Compound 5

In nitrogen atmosphere, sub 1 (10 g, 24 mmol) and int E (8.4 g, 24 mmol) were added to dimethylformamide (200 ml), stirred and refluxed. Subsequently, sodium tertiary-butoxide (15.3 g, 71.9 mmol) was added, stirred sufficiently, cooled for 3 hours after reaction, and the organic layer was filtered to remove salt, and then the filtered organic layer was distilled. This was again dissolved in chloroform (179 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a yellow solid compound 5 (10.9 g, yield 61%, MS: [M+H] ⁺ = 747.2).

Example 6: Synthesis of Compound 6

In nitrogen atmosphere, sub 1 (10 g, 24 mmol) and int F (8.4 g, 24 mmol) were added to dimethylformamide (200 ml), stirred and refluxed. Subsequently, sodium tertiary-butoxide (15.3 g, 71.9 mmol) was added, stirred sufficiently, cooled for 5 hours, cooled to room temperature, and the organic layer was filtered to remove salts, and then the filtered organic layer was distilled. This was again dissolved in chloroform (179 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound 6 (10.9 g, yield 61%, MS: [M+H] ⁺ = 747.2).

Example 7: Synthesis of Compound 7

In a nitrogen atmosphere, sub 1 (10 g, 24 mmol) and int G (8.4 g, 24 mmol) were added to dimethylformamide (200 ml), stirred and refluxed. Subsequently, sodium tertiary-butoxide (15.3 g, 71.9 mmol) was added, stirred sufficiently, cooled to room temperature after 7 hours of reaction, the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was again dissolved in chloroform (179 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound 7 (9.3 g, yield 52%, MS: [M+H] ⁺ = 747.2).

Example 8: Synthesis of Compound 8

In a nitrogen atmosphere, sub 1 (10 g, 24 mmol) and int H (8.4 g, 24 mmol) were added to dimethylformamide (200 ml), stirred and refluxed. Subsequently, sodium tertiary-butoxide (15.3 g, 71.9 mmol) was added, stirred sufficiently, and after 4 hours of reaction, cooled to room temperature, and the organic layer was filtered to remove salts, and then the filtered organic layer was distilled. This was again dissolved in chloroform (179 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound 8 (12.7 g, yield 71%, MS: [M+H] ⁺ = 747.2).

Example 9: Synthesis of Compound 9

In a nitrogen atmosphere, sub 2 (10 g, 24 mmol) and int G (8.4 g, 24 mmol) were added to dimethylformamide (200 ml), stirred and refluxed. Subsequently, sodium tertiary-butoxide (15.3 g, 71.9 mmol) was added, stirred sufficiently, and after 4 hours of reaction, cooled to room temperature, and the organic layer was filtered to remove salts, and then the filtered organic layer was distilled. This was again dissolved in chloroform (179 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a yellow solid compound 9 (12.3 g, yield 69%, MS: [M+H] ⁺ = 747.2).

Example 10: Synthesis of Compound 10

In nitrogen atmosphere, sub 3 (10 g, 24 mmol) and int G (8.4 g, 24 mmol) were added to dimethylformamide (200 ml), stirred and refluxed. Subsequently, sodium tertiary-butoxide (15.3 g, 71.9 mmol) was added, stirred sufficiently, cooled for 5 hours, cooled to room temperature, and the organic layer was filtered to remove salts, and then the filtered organic layer was distilled. This was again dissolved in chloroform (179 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound 10 (10.2 g, yield 57%, MS: [M+H] ⁺ = 747.2).

Example 11: Synthesis of Compound 11

In a nitrogen atmosphere, sub 4 (10 g, 24 mmol) and int G (8.4 g, 24 mmol) were added to dimethylformamide (200 ml), stirred and refluxed. Subsequently, sodium tertiary-butoxide (15.3 g, 71.9 mmol) was added, stirred sufficiently, cooled for 3 hours after reaction, and the organic layer was filtered to remove salt, and then the filtered organic layer was distilled. This was again dissolved in chloroform (179 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound 11 (13.1 g, yield 73%, MS: [M+H] ⁺ = 747.2).

Example 12: Synthesis of Compound 12

In nitrogen atmosphere, sub 5 (10 g, 24 mmol) and int G (8.4 g, 24 mmol) were added to dimethylformamide (200 ml), stirred and refluxed. Subsequently, sodium tertiary-butoxide (15.3 g, 71.9 mmol) was added, stirred sufficiently, cooled to room temperature after 7 hours of reaction, the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was again dissolved in chloroform (179 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a white solid compound 12 (11.6 g, yield 65%, MS: [M+H] ⁺ = 747.2).

Example 13: Synthesis of Compound 13

In a nitrogen atmosphere, sub 6 (10 g, 24 mmol) and int G (8.4 g, 24 mmol) were added to dimethylformamide (200 ml), stirred and refluxed. Subsequently, sodium tertiary-butoxide (15.3 g, 71.9 mmol) was added, stirred sufficiently, and after 4 hours of reaction, cooled to room temperature, and the organic layer was filtered to remove salts, and then the filtered organic layer was distilled. This was again dissolved in chloroform (179 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a yellow solid compound 13 (12.3 g, yield 69%, MS: [M+H] ⁺ = 747.2).

Example 14: Synthesis of Compound 14

G-2 (50 g, 78 mmol) and 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (26.8) in nitrogen atmosphere g, 78 mmol) was added to tetrahydrofuran (1000 ml), stirred and refluxed. Subsequently, potassium carbonate (32.3 g, 233.9 mmol) was dissolved in water (32 ml), stirred thoroughly, and then tetrakistriphenyl-phosphino palladium (2.7 g, 2.3 mmol) was added. After the reaction was cooled to room temperature for 1 hour, the organic layer and the water layer were separated, and then the organic layer was distilled. This was again dissolved in chloroform (1282 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the filtrate was distilled under reduced pressure. The concentrated compound was yellow solid compound 14 (50 g, yield 78%, MS: [M+H] ⁺ = 823.3) by recrystallization of chloroform and ethyl acetate.

Example 15: Synthesis of Compound 15

G-2 (50 g, 78 mmol) and 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (24.7 g, 78 mmol) in tetrahydrogen in a nitrogen atmosphere Put into furan (1000 ml) and stirred and refluxed. Subsequently, potassium carbonate (32.3 g, 233.9 mmol) was dissolved in water (32 ml), stirred thoroughly, and then tetrakistriphenyl-phosphino palladium (2.7 g, 2.3 mmol) was added. After the reaction was cooled to room temperature for 1 hour, the organic layer and the water layer were separated, and then the organic layer was distilled. This was again dissolved in chloroform (1242 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the filtrate was distilled under reduced pressure. A yellow solid compound 15 (34.8 g, yield 56%, MS: [M+H] ⁺ = 797.2) was prepared by recrystallization of the concentrated compound through chloroform and ethyl acetate.

Example 16: Synthesis of Compound 16

G-2 (50 g, 78 mmol) and 2-chloro-4-(4-(naphthalen-1-yl)phenyl)-6-phenyl-1,3,5-triazine (30.7 g, 78) in a nitrogen atmosphere mmol) was added to tetrahydrofuran (1000 ml), stirred and refluxed. Subsequently, potassium carbonate (32.3 g, 233.9 mmol) was dissolved in water (32 ml), stirred thoroughly, and then tetrakistriphenyl-phosphino palladium (2.7 g, 2.3 mmol) was added. After the reaction was cooled to room temperature for 2 hours, the organic layer and the water layer were separated, and then the organic layer was distilled. This was again dissolved in chloroform (1360 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the filtrate was distilled under reduced pressure. The concentrated compound was prepared by recrystallization of chloroform and ethyl acetate to prepare a yellow solid compound 16 (45.6 g, yield 67%, MS: [M+H] ⁺ = 873.3).

Example 17: Synthesis of Compound 17

G-2 (50 g, 78 mmol) and 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (27.8 g) in nitrogen atmosphere , 78 mmol) in tetrahydrofuran (1000 ml), stirred and refluxed. Subsequently, potassium carbonate (32.3 g, 233.9 mmol) was dissolved in water (32 ml), stirred thoroughly, and then tetrakistriphenyl-phosphino palladium (2.7 g, 2.3 mmol) was added. After the reaction was cooled to room temperature for 1 hour, the organic layer and the water layer were separated, and then the organic layer was distilled. This was again dissolved in chloroform (1304 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the filtrate was distilled under reduced pressure. The concentrated compound was yellow solid compound 17 (35.2 g, yield 54%, MS: [M+H] ⁺ = 837.2) by recrystallization of chloroform and ethyl acetate.

Example 18: Synthesis of Compound 18

G-2 (50 g, 78 mmol) and 2-chloro-4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine (29.1) in a nitrogen atmosphere g, 78 mmol) was added to tetrahydrofuran (1000 ml), stirred and refluxed. Subsequently, potassium carbonate (32.3 g, 233.9 mmol) was dissolved in water (32 ml), stirred thoroughly, and then tetrakistriphenyl-phosphino palladium (2.7 g, 2.3 mmol) was added. After the reaction for 3 hours, after cooling to room temperature, the organic layer and the water layer were separated and the organic layer was distilled. This was again dissolved in chloroform (1329 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was prepared by recrystallization of chloroform and ethyl acetate to give a yellow solid compound 18 (44.5 g, yield 67%, MS: [M+H] ⁺ = 853.2).

Example 19: Synthesis of Compound 19

G-2 (50 g, 78 mmol) and 9-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole (27.8 g, 78 mmol) in nitrogen atmosphere Was added to tetrahydrofuran (1000 ml), stirred and refluxed. Subsequently, potassium carbonate (32.3 g, 233.9 mmol) was dissolved in water (32 ml), stirred thoroughly, and then tetrakistriphenyl-phosphino palladium (2.7 g, 2.3 mmol) was added. After the reaction was cooled to room temperature for 1 hour, the organic layer and the water layer were separated, and then the organic layer was distilled. This was again dissolved in chloroform (1303 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. A yellow solid compound 19 (41 g, yield 63%, MS: [M+H] ⁺ = 836.2) was prepared by recrystallization of the concentrated compound through chloroform and ethyl acetate.

Example 20: Synthesis of Compound 20

G-2 (50 g, 78 mmol) and 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine (21.2 g, 78 mmol) in a nitrogen atmosphere in tetrahydrofuran ( 1000 ml) and stirred and refluxed. Subsequently, potassium carbonate (32.3 g, 233.9 mmol) was dissolved in water (32 ml), stirred thoroughly, and then tetrakistriphenyl-phosphino palladium (2.7 g, 2.3 mmol) was added. After the reaction was cooled to room temperature for 2 hours, the organic layer and the water layer were separated, and then the organic layer was distilled. This was again dissolved in chloroform (1172 ml), washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was prepared by recrystallization of chloroform and ethyl acetate to prepare a yellow solid compound 20 (42.8 g, yield 73%, MS: [M+H] ⁺ = 752.2).

[Experimental Example]

Experimental Example 1

A glass substrate coated with a thin film of indium tin oxide (ITO) at a thickness of 1,300 Å was placed in distilled water in which detergent was dissolved, and then washed with ultrasonic waves. At this time, Fischer Co. was used as a detergent, and distilled water filtered secondarily by a filter of Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated for 2 minutes with distilled water twice. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying and transporting to a plasma cleaner. In addition, the substrate was washed for 5 minutes using oxygen plasma, and then transferred to a vacuum evaporator.

On the ITO transparent electrode prepared as above, the following HI-1 compound was thermally vacuum-deposited to a thickness of 50 Å to form a hole injection layer. The following HT-1 compound was thermally vacuum-deposited to a thickness of 250 Å on the hole injection layer to form a hole transport layer, and the following HT-2 compound was vacuum-deposited to a thickness of 50 위에 on the HT-1 deposition film to form an electron blocking layer. . As a light emitting layer on the HT-2 deposited film, a compound 1 prepared in Example 1, the following YGH-1 compound, and a phosphorescent dopant YGD-1 were co-deposited in a weight ratio of 44:44:12 to form a 400 mm thick light emitting layer. . An electron transport layer is formed by vacuum-depositing the following ET-1 compound to a thickness of 250 위에 on the light emitting layer, and the following ET-2 compound and Li are vacuum-deposited at a weight ratio of 98:2 to the electron transport layer to inject electrons having a thickness of 100 Å. A layer was formed. Aluminum was deposited on the electron injection layer to a thickness of 1000 Å to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å/sec, and the aluminum was maintained at the deposition rate of 2 Å/sec, and the vacuum degree during deposition was maintained at 1 × 10 ^-7 to 5 × 10 ^-8 torr. Did.

Experimental Examples 2 to 20 and Comparative Experimental Examples 1 to 2

An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except for using the compound described in Table 1 below instead of compound 1 of Preparation Example 1 in Experimental Example 1. The compounds of CE1 and CE2 in Table 1 are as follows.

In the Experimental Example and Comparative Experimental Example, the voltage and efficiency of the organic light emitting diode were measured at a current density of 10 mA/cm ² , and the life was measured at a current density of 50 mA/cm ² , and the results are shown in Table 1 below. . At this time, LT ₉₅ means the time to be 95% compared to the initial luminance.

Emitting layer Voltage (V,
@10 mA/cm ² ) Efficiency (Cd/A, @10 mA/cm ² ) Color coordinate
(x,y) Lifetime (hr, LT ₉₅ at 50 mA/cm ² ) Experimental Example 1 Compound 1 4.0 78 0.46, 0.54 200 Experimental Example 2 Compound 2 4.1 79 0.46, 0.54 210 Experimental Example 3 Compound 3 4.2 80 0.46, 0.54 195 Experimental Example 4 Compound 4 4.1 80 0.46, 0.54 215 Experimental Example 5 Compound 5 4.1 81 0.46, 0.53 275 Experimental Example 6 Compound 6 4.1 80 0.46, 0.54 210 Experimental Example 7 Compound 7 4.1 80 0.46, 0.54 280 Experimental Example 8 Compound 8 4.1 80 0.46, 0.54 244 Experimental Example 9 Compound 9 4.0 83 0.46, 0.54 220 Experimental Example 10 Compound 10 4.0 81 0.46, 0.54 215 Experimental Example 11 Compound 11 4.1 83 0.46, 0.54 230 Experimental Example 12 Compound 12 4.0 85 0.46, 0.54 244 Experimental Example 13 Compound 13 4.1 84 0.46, 0.54 199 Experimental Example 14 Compound 14 4.1 82 0.46, 0.54 185 Experimental Example 15 Compound 15 4.2 83 0.46, 0.53 266 Experimental Example 16 Compound 16 4.2 81 0.46, 0.54 275 Experimental Example 17 Compound 17 4.2 83 0.46, 0.54 246 Experimental Example 18 Compound 18 4.2 83 0.46, 0.54 251 Experimental Example 19 Compound 19 4.4 81 0.46, 0.54 305 Experimental Example 20 Compound 20 4.1 80 0.46, 0.54 320 Comparative Experimental Example 1 CE1 4.0 74 0.46, 0.54 110 Comparative Experimental Example 2 CE2 4.2 72 0.46, 0.55 90

As shown in Table 1, when the compound of the present invention is used as a light emitting layer material, it was confirmed that it exhibits excellent efficiency and lifetime compared to a comparative example. It seems that the electrical stability is increased as the triazine-based substituent and the carbazole-based substituent are connected to the ortho position in the dibenzofuran, and the dibenzofuranyl group or the dibenzothiophenyl group is substituted in the carbazole-based substituent.

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

Claims (11)

Compound represented by the formula (1):
[Formula 1]

In Chemical Formula 1,
Any one of Q is a substituent represented by the following Chemical Formula 2, any one of the other is a substituent represented by the following Chemical Formula 3, and the other is CH,
However, the substituent represented by the following formula (2) and the substituent represented by the following formula (3) are connected to the ortho (ortho) position,
n is an integer from 0 to 4,
R ₁ is hydrogen; heavy hydrogen; halogen; Cyano; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _2-60 alkynyl; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _6-60 aryl; Or C _5-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,
[Formula 2]

In Chemical Formula 2,
X are each independently N or CH, provided that at least one of them is N,
Ar ₁ and Ar ₂ are each independently substituted or unsubstituted C _6-60 aryl; Or C _5-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,
[Formula 3]

In Chemical Formula 3,
Y is O or S.
According to claim 1,
Chemical Formula 1 is a compound represented by the following Chemical Formulas 1-1 to 1-6:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

In Chemical Formulas 1-1 to 1-6,
Descriptions of X, Y, Ar ₁ , Ar ₂ , R ₁ and n are as defined in claim 1.
According to claim 1,
n is 0 or 1;
According to claim 1,
R ₁ is hydrogen; heavy hydrogen; methyl; Or phenyl.
According to claim 1,
A compound in which X is all N.
According to claim 1,
Ar ₁ and Ar ₂ are each independently any one selected from the group consisting of:

In the above formula,
m is an integer from 0 to 5,
k is an integer from 0 to 4,
R ₂ is hydrogen; heavy hydrogen; halogen; Cyano; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _2-60 alkynyl; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _6-60 aryl; Or C _5-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S.
The method of claim 6,
R ₂ is hydrogen; heavy hydrogen; methyl; Or phenyl.
According to claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of:

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 layer of the organic material layer includes the compound according to any one of claims 1 to 8. That is, an organic light emitting device.
The method of claim 9,
The organic material layer may include a light emitting layer, and the light emitting layer includes two or more host materials.
The method of claim 10,
The two or more host materials include a compound represented by Chemical Formula 1, an organic light emitting device.

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