KR101948208B1

KR101948208B1 - Organic compound for optoelectronic device and organic optoelectronic device and display device

Info

Publication number: KR101948208B1
Application number: KR1020150110203A
Authority: KR
Inventors: 한수진; 고채혁; 김영권; 유은선; 이한일; 정호국
Original assignee: 삼성에스디아이 주식회사
Priority date: 2015-08-04
Filing date: 2015-08-04
Publication date: 2019-02-14
Also published as: KR20170016734A

Abstract

A compound for an organic optoelectronic device represented by the general formula (I), an organic optoelectronic device using the same, and a display device including the organic optoelectronic device.
Details of the above formula (I) are as defined in the specification.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic electroluminescent device,

A compound for an organic optoelectronic device, an organic optoelectronic device and a display device.

An organic optoelectronic device is an element capable of converting electrical energy to optical energy.

Organic optoelectronic devices can be roughly classified into two types according to the operating principle. One is an optoelectronic device in which an exciton formed by light energy is separated into an electron and a hole, the electron and hole are transferred to different electrodes to generate electric energy, and the other is a voltage / Emitting device that generates light energy from energy.

Examples of organic optoelectronic devices include organic optoelectronic devices, organic light emitting devices, organic solar cells, and organic photo conductor drums.

In recent years, organic light emitting diodes (OLEDs) have attracted considerable attention due to the demand for flat panel display devices. The organic light emitting diode is a device for converting electrical energy into light by applying an electric current to the organic light emitting material, and usually has an organic layer inserted between an anode and a cathode. The organic layer may include a light emitting layer and an optional auxiliary layer. The auxiliary layer may include, for example, a hole injecting layer, a hole transporting layer, an electron blocking layer, an electron transporting layer, And a hole blocking layer.

The performance of the organic light emitting device is greatly influenced by the characteristics of the organic layer, and the organic layer is highly affected by the organic material contained in the organic layer.

In particular, in order for the organic light emitting device to be applied to a large-sized flat panel display device, it is necessary to develop an organic material capable of increasing the mobility of holes and electrons and increasing the electrochemical stability.

High efficiency, long life, and the like.

An organic optoelectronic device including the compound, and a display device including the organic optoelectronic device.

According to one embodiment, there is provided a compound for an organic optoelectronic device represented by the following general formula (I).

(I)

In the above formula (I)

X ¹ and X ² are each independently N, O, or S,

Wherein ^{one of} X < ¹ ^> and X < ² > is N,

R ¹ and R ² are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted C6 to C30 arylamine group, or a combination thereof ,

R ³ and R ⁴ are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, Substituted or unsubstituted C2 to C30 heteroaryl groups, substituted or unsubstituted C6 to C30 arylamine groups, substituted or unsubstituted C1 to C30 alkoxy groups, substituted or unsubstituted C3 to C40 silyl groups, substituted or unsubstituted C3 to C40 A substituted or unsubstituted C1 to C30 alkylthiol group, a substituted or unsubstituted C6 to C30 arylthiol group, a halogen group, a halogen-containing group, a cyano group, a hydroxyl group, or a combination thereof,

L ¹ and L ² are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,

The term "substituted" as used herein means that at least one hydrogen is substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a hydroxy group, a C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, To C30 aryl group, a C2 to C30 heterocyclic group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, or a cyano group.

According to another embodiment, there is provided an organic optoelectronic device including an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, wherein the organic layer comprises the compound for the organic optoelectronic device .

According to another embodiment, there is provided a display device including the organic optoelectronic device.

High-efficiency long-lived organic optoelectronic devices can be realized.

1 and 2 are sectional views showing an organic light emitting device according to an embodiment, respectively.

Hereinafter, embodiments of the present invention will be described in detail. However, it should be understood that the present invention is not limited thereto, and the present invention is only defined by the scope of the following claims.

The term "substituted" as used herein means that at least one hydrogen is replaced by a substituent selected from the group consisting of deuterium, a halogen group, a hydroxy group, a C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group , A C6 to C30 aryl group, a C2 to C30 heterocyclic group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, or a cyano group.

The substituted or unsubstituted C 1 to C 40 silyl group, the C 1 to C 30 alkyl group, the C 1 to C 10 alkylsilyl group, the C 3 to C 30 cycloalkyl group, the C 3 to C 30 heterocycloalkyl group, the C 6 to C 30 aryl group , A C6 to C30 heterocyclic group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group or a cyano group may be fused to form a ring. For example, the substituted C6 to C30 aryl group may be fused with another adjacent substituted C6 to C30 aryl group to form a substituted or unsubstituted fluorene ring.

Means one to three heteroatoms selected from the group consisting of N, O, S, P and Si in one functional group, and the remainder being carbon unless otherwise defined .

As used herein, the term "alkyl group" means an aliphatic hydrocarbon group, unless otherwise defined. The alkyl group may be a " saturated alkyl group " which does not contain any double or triple bonds.

The alkyl group may be an alkyl group of C1 to C30. More specifically, the alkyl group may be a C1 to C20 alkyl group or a C1 to C10 alkyl group. For example, C1 to C4 alkyl groups mean that from 1 to 4 carbon atoms are included in the alkyl chain and include methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec- Indicating that they are selected from the group.

Specific examples of the alkyl group include a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, hexyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, And the like.

As used herein, the term " aryl group " is intended to encompass groups having one or more hydrocarbon aromatic moieties, in which all the elements of the hydrocarbon aromatic moiety have a p-orbital, Such as a biphenyl group, a terphenyl group, a quaterphenyl group, and the like, which include two or more hydrocarbon aromatic moieties including a phenyl group, a naphthyl group, and the like, in which two or more hydrocarbon aromatic moieties are connected through a sigma bond, May also include non-aromatic fused rings fused directly or indirectly. For example, a fluorenyl group and the like.

The aryl groups include monocyclic, polycyclic or fused ring polycyclic (i. E., Rings that divide adjacent pairs of carbon atoms) functional groups. For example, the aryl group means a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a klycenyl group, and the like.

As used herein, the term " heterocyclic group " is a superordinate concept including a heteroaryl group, and includes N, O, and S substituents in the ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof, Means at least one heteroatom selected from the group consisting of S, P and Si. When the heterocyclic group is a fused ring, the heterocyclic group or the ring may include one or more heteroatoms.

As used herein, the term " heteroaryl group " means that at least one heteroatom selected from the group consisting of N, O, S, P and Si is contained in the aryl group instead of carbon (C). Two or more heteroaryl groups may be directly connected through a sigma bond, or when the C2 to C60 heteroaryl group includes two or more rings, two or more rings may be fused with each other. When the heteroaryl group is a fused ring, it may contain 1 to 3 heteroatoms in each ring.

More specifically, the substituted or unsubstituted C6 to C30 aryl group and / or the substituted or unsubstituted C2 to C30 heterocyclic group may be substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthra A substituted or unsubstituted phenanthryl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted naphthacenyl group, A substituted or unsubstituted aryl group, a substituted m-terphenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furanyl group , A substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted pyrazolyl group, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group , A substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzothiophenyl group, A substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinolinyl group, Substituted or unsubstituted quinoxalinyl groups, substituted or unsubstituted naphthyridinyl groups, substituted or unsubstituted benzoxazinyl groups, substituted or unsubstituted benzthiazinyl groups, substituted or unsubstituted quinoxalinyl groups, substituted or unsubstituted quinoxalinyl groups, A substituted or unsubstituted phenanthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted phenothiazyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group , A substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted benzothiophene pyrimidinyl group, a substituted or unsubstituted benzothiophene pyridyl group, a substituted or unsubstituted benzofuranpyri A substituted or unsubstituted pyrazolyl group, a substituted pyrazolyl group, a substituted pyrazolyl group, a substituted pyrazolyl group, a substituted pyrazolyl group, a substituted pyrazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted benzopyranyl group, A substituted or unsubstituted thiazoloquinolinyl group, a substituted or unsubstituted oxazolinoquinolinyl group, or a combination thereof, but is not limited thereto.

In the present specification, a single bond means a bond directly connected to a carbon atom or a hetero atom other than carbon. Specifically, L means a single bond, meaning that the substituent connected to L is directly connected to the center core do. That is, in the present specification, a single bond does not mean methylene or the like via carbon.

In the present specification, the hole property refers to a property of forming holes by donating electrons when an electric field is applied, and has a conduction property along the HOMO level so that the injection of holes formed in the anode into the light emitting layer, Quot; refers to the property of facilitating the movement of the hole formed in the light emitting layer to the anode and the movement of the hole in the light emitting layer.

In addition, the electron characteristic refers to a characteristic that electrons can be received when an electric field is applied. The electron characteristic has a conduction characteristic along the LUMO level to inject electrons formed in the cathode into the light emitting layer, move electrons formed in the light emitting layer to the cathode, It is a characteristic that facilitates movement.

The compounds for organic optoelectronic devices according to one embodiment will be described below.

The compound for organic optoelectronic devices according to one embodiment is represented by the following formula (I).

(I)

In the above formula (I)

X ¹ and X ² are each independently N, O, or S,

Wherein ^{one of} X < ¹ ^> and X < ² > is N,

The dotted line represented by X ¹ -CX ² means that a double bond can be located on X ¹ -C or X ² -C.

The compound for organic optoelectronic devices represented by Formula (I) is a compound in which a thiazole group or an oxazole group is fused to quinoline.

The compound for the organic optoelectronic device has an effect of facilitating charge injection and movement, and has a driving voltage lowered. In addition, due to the steric hindrance of the molecule itself, the intermolecular interaction is small and crystallization is inhibited, Can be improved.

Further, a C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted C6 to C30 arylamine group, or a combination thereof may be selected from substituted or unsubstituted C6 to C30 aryl groups at the R ¹ and R ² positions It is possible to realize a long-life device stable to oxidation reaction and the like.

The compound for an organic optoelectronic device can be represented by, for example, the following Formula I-1 or I-2 according to the position of N.

[Formula (I-1)] [Formula (I-2)

In the above formulas (I-1) and (I-2), R ¹ to R ⁴ , L ¹ and L ² are as defined above, and X ¹ and X ² are each independently O or S.

At least one of R ¹ and R ² is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted naphthacenyl group A substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted quaterphenyl group, A substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrazinyl group, A substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted thiazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted pyrazinyl group, A substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted arylthio group, A substituted or unsubstituted thiazoloquinolinyl group, or a combination thereof.

Here, "substituted" is as described above.

According to an embodiment of the present invention, at least one of R ¹ and R ² is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p- A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, Or a substituted or unsubstituted thiazoloquinolinyl group,

According to another embodiment of the present invention, at least one of R ¹ and R ² is a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuranyl group, A substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted fluorenyl group.

Specifically, at least one of R ¹ and R ² may be selected from a substituted or unsubstituted group listed in Group I below.

[Group I]

In the group I,

Z is N or CR ^a ,

W is ^{N, O, S, CR b} R c,

R ^a to R ⁿ are each independently selected from the group consisting of hydrogen, deuterium, C1 to C30 alkyl groups, C3 to C30 cycloalkyl groups, C1 to C30 alkoxy groups, C3 to C40 silyl groups, C3 to C40 silyloxy groups, C1 to C30 alkylthiol groups , A halogen group, a halogen-containing group, a cyano group, a hydroxyl group, an amino group, a nitro group,

* Is a linking point connected to L ¹ or L ² of the above formula (I)

n and m each independently represent an integer of 0 to 2;

More specifically, according to one embodiment of the present invention among the substituted or unsubstituted groups listed in Group I, at least one of R ¹ and R ² is a substituted or unsubstituted group listed in Group I-A below Can be selected.

[Group I-A]

In Group I-A

* Is a connecting point connecting with L ¹ or L ² in the above formula (I).

When at least one of R < ¹ > and R < ² > is selected from the substituents listed in the group I-A, the compound for an organic optoelectronic device has a stronger electron acceptor or electron transporting ability It can have a driving characteristic at a low voltage.

In addition, two or more meta-bonded substituted or unsubstituted phenylene groups centering on (L ¹ , L ² ) can increase the stability of the core by appropriately controlling the flow of charge moving toward the core. In particular, the stability of the organic compound can be improved by reducing the oxidation. Thus, the lifetime of the organic compound can be improved.

As a most specific example, at least one of R ¹ and R ² is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted triazinyl group, Substituted or unsubstituted thiazoloquinolinyl group, but is not limited thereto.

According to another embodiment of the present invention, at least one of R ¹ and R ² is selected from substituted or unsubstituted groups listed in Group I-B below .

[Group I-B]

In said Group I-B,

* Is a connecting point connecting with L ¹ or L ² in the above formula (I).

When at least one of R < ¹ > and R < ² > is selected from the substituents listed in the group I-B, the group having a hole characteristic easily susceptible to holes is included together with the substituted or unsubstituted core to form a bipolar structure So that the flow of holes and electrons can be properly balanced, thereby improving the efficiency of the organic optoelectronic device using the organic compound.

In the above-described bipolar structure compound, localization of a core portion which is susceptible to electrons and a portion which is susceptible to electrons around the linking groups (L ¹ and L ² ) and / or phenylene groups is appropriately localized and the flow of the conjugated system is controlled And can exhibit excellent bipolar characteristics. Accordingly, the lifetime of the organic optoelectronic device to which the organic compound is applied can be improved.

As a most specific example, at least one of R ¹ and R ² may be a substituted or unsubstituted carbazole group, or a substituted or unsubstituted dibenzofuranyl group, but is not limited thereto.

L ¹ and L ² each independently represent a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted quaterphenylene group , A substituted or unsubstituted pyridylene group, a substituted or unsubstituted pyrimidylene group, and a substituted or unsubstituted triazinylene group.

Here, "substituted" is as described above.

The compound for organic optoelectronic devices may be, for example, compounds listed in Groups A and B below, but is not limited thereto.

[Group A]

[Group B]

Hereinafter, the organic optoelectronic device to which the compound for an organic optoelectronic device described above is applied will be described.

The organic optoelectronic device is not particularly limited as long as it is an element capable of converting electric energy and optical energy. Examples of the organic optoelectronic device include organic light emitting devices, organic solar cells, and organic photoconductor drums.

The organic optoelectronic device may include an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, and the organic layer may include the compound for the organic optoelectronic device described above.

Here, an organic light emitting device, which is an example of an organic optoelectronic device, will be described with reference to the drawings.

1 and 2 are cross-sectional views illustrating an organic light emitting device according to an embodiment.

1, an organic optoelectronic device 100 according to an embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 located between the anode 120 and the cathode 110 .

The anode 120 may be made of a conductor having a high work function to facilitate, for example, hole injection, and may be made of, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 120 is made of a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of ZnO and Al or a metal and an oxide such as SnO ₂ and Sb; Conductive polymers such as poly (3-methylthiophene), poly (3,4- (ethylene-1,2-dioxy) thiophene), polypyrrole and polyaniline, It is not.

The cathode 110 may be made of a conductor having a low work function, for example, to facilitate electron injection, and may be made of, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 is made of a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium or the like or an alloy thereof; Layer structure materials such as LiF / Al, LiO ₂ / Al, LiF / Ca, LiF / Al and BaF ₂ / Ca.

The organic layer 105 includes the above-described compound for an organic optoelectronic device or the above-described light emitting layer 130 including a composition for an organic optoelectronic device.

The light emitting layer 130 may include, for example, the compound for organic optoelectronic devices described above alone, or may include at least two of the compounds for organic optoelectronic devices described above, or may include the composition for the organic optoelectronic device described above .

Referring to FIG. 2, the organic light emitting diode 200 further includes a hole-assist layer 140 in addition to the light-emitting layer 130. The hole auxiliary layer 140 can further enhance hole injection and / or hole mobility between the anode 120 and the light emitting layer 130 and block electrons. The hole-assist layer 140 may be, for example, a hole transport layer, a hole injection layer, and / or an electron blocking layer, and may include at least one layer. The compound for the organic optoelectronic device described above may be included in the light emitting layer 230.

1 or 2, the organic layer 105 may further include an electron transport layer, an electron injection layer, a hole injection layer, and the like.

The organic light emitting devices 100 and 200 may be formed by forming an anode or a cathode on a substrate and then forming an organic layer by a dry film forming method such as evaporation, sputtering, plasma plating, or ion plating, A negative electrode or a positive electrode.

The organic light emitting device described above can be applied to an organic light emitting display.

Hereinafter, specific embodiments of the present invention will be described. However, the embodiments described below are only intended to illustrate or explain the present invention, and thus the present invention should not be limited thereto.

The starting materials and reactants used in the synthesis examples and examples were purchased from Sigma-Aldrich or TCI unless otherwise noted.

Synthetic example 1: Synthesis of intermediate I-1

[Reaction Scheme 1]

After dissolving 3-bromo-1,1'-biphenyl (20 g, 85.8 mmol) in dimethylformamide (DMF) in a nitrogen atmosphere, bis (pinacolato) diboron (26 g, 103 mmol) -bis (diphenylphosphine) ferrocene) dichloropalladium (II) (0.7 g, 0.85 mmol) and potassium acetate (21 g, 214.5 mmol) were heated and refluxed at 150 ° C for 5 hours. After completion of the reaction, water was added to the reaction solution, the mixture was filtered, and then dried in a vacuum oven. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-1 (20 g, 85%).

HRMS (70 eV, EI +): m / z calcd for C18H21BO2: 280.1635, found: 280.

Elemental Analysis: C, 77%; H, 7%

Synthetic example 2: Synthesis of intermediate I-2

[Reaction Scheme 2]

The intermediate I-1 (20 g, 71 mmol) was dissolved in 1 L of THF in a nitrogen atmosphere and then 1-bromo-3-iodobenzene (22 g, 78 mmol) and tetrakis (triphenylphosphine) palladium mmol) were added and stirred. Saturated water-saturated potassium carbonate (25 g, 177 mmol) was added and heated at 80 ° C for 12 hours to reflux. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-2 (20 g, 91%).

HRMS (70 eV, EI +): m / z calcd for C18H13Br: 308.0201, found: 308 Elemental Analysis: C, 70%; H, 4%

Synthetic example 3: Synthesis of Intermediate I-3

[Reaction Scheme 3]

Bis (pinacolato) diboron (20 g, 77 mmol) and (1,1'-bis (diphenylphosphine) ferrocene) were dissolved in 1 L of dimethylformamide (DMF) ) dichloropalladium (II) (0.5 g, 0.64 mmol) and potassium acetate (16 g, 161 mmol) were added and the mixture was refluxed by heating at 150 ° C for 5 hours. After completion of the reaction, water was added to the reaction solution, the mixture was filtered, and then dried in a vacuum oven. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-3 (21 g, 90%).

HRMS (70 eV, EI +): m / z calcd for C24H25BO2: 356.1948, found: 356.

Elemental Analysis: C, 91%; H, 7%

Synthetic example 4: Synthesis of intermediate I-4

[Reaction Scheme 4]

(21 g, 78 mmol) and tetrakis (triphenylphosphine) palladium (0.8 g, 0.35 mmol) were dissolved in THF (1 L) in a nitrogen atmosphere and the compound ethyl 2-bromothiazole- 0.71 mmol) were added thereto and stirred. Saturated water-saturated potassium carbonate (25 g, 177 mmol) was added and heated at 80 ° C for 12 hours to reflux. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-4 (19 g, 70%).

HRMS (70 eV, EI +): m / z calcd for C24H19NO2S: 385.1136, found: 385 Elemental Analysis: C, 75%; H, 5%

Synthetic example 5: Synthesis of intermediate I-5

[Reaction Scheme 5]

Intermediate I-4 (20 g, 71 mmol) was dissolved in 1 L of CHCl ₃ in a nitrogen atmosphere, and then n-bromosuccinimide (12.6 g, 71 mmol) was slowly added thereto at 0 ° C and stirred for 30 minutes. The mixture was heated at room temperature for 12 hours to reflux. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-5 (26 g, 80%).

HRMS (70 eV, EI +): m / z calcd for C24Hi8BrNO2S: 463.0242, found: 463 Elemental Analysis: C, 62%; H, 4%

Synthetic example 6: Synthesis of Intermediate I-6

[Reaction Scheme 6]

The intermediate I-5 (26 g, 71 mmol) was dissolved in 1 L of DME (dimethyl glycol) in a nitrogen atmosphere, and then 2-aminophenyl boronic acid (9 g, 71 mmol) and tetrakis (triphenylphosphine) palladium 0.8 g, 0.71 mmol) were added and stirred. Saturated water-saturated potassium carbonate (10 g, 177 mmol) was added and the mixture was refluxed by heating at 80 ° C for 12 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-6 (19 g, 70%).

HRMS (70 eV, EI +): m / z calcd for C28H18N2OS: 430.1140, found: 430 Elemental Analysis: C, 78%; H, 4%

Synthetic example 7: Synthesis of Intermediate I-7

[Reaction Scheme 7]

Intermediate I-6 (19 g, 44 mmol) was added POCl ₃ (33 g, 220 mmol) in a nitrogen atmosphere and heated at reflux for 12 hours at room temperature. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The thus-obtained residue was separated and purified by flash column chromatography to obtain Intermediate I-7 (15 g, 75%).

HRMS (70 eV, EI +): m / z calcd for C28H17ClN2S: 448.0801, found: 448 Elemental Analysis: C, 75%; H, 4%

Synthetic example 8: Synthesis of Intermediate I-8

[Reaction Scheme 8]

(22 g, 78 mmol) and tetrakis (triphenylphosphine) palladium (0.8 g) were dissolved in 1 L of THF in a nitrogen atmosphere, and the ethyl 2-bromothiazole-5-carboxylate g, 0.71 mmol) were added and stirred. Saturated water-saturated potassium carbonate (25 g, 177 mmol) was added and heated at 80 ° C for 12 hours to reflux. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-8 (15 g, 70%).

HRMS (70 eV, EI +): m / z calcd for C18H15NO2S: 309.0823, found: 309 Elemental Analysis: C, 70%; H, 5%

Synthetic example 9: Synthesis of intermediate I-9

[Reaction Scheme 9]

Intermediate I-8 (15 g, 48 mmol) was dissolved in 1 L of CHCl ₃ in a nitrogen atmosphere, and then n-bromosuccinimide (8.5 g, 48 mmol) was slowly added thereto at 0 ° C and stirred for 30 minutes. The mixture was heated at room temperature for 12 hours to reflux. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-9 (15 g, 80%).

HRMS (70 eV, EI +): m / z calcd for C18H14BrNO2S: 386.9929, found: 386 Elemental Analysis: C, 56%; H, 4%

Synthetic example 10: Synthesis of intermediate I-10

[Reaction Scheme 10]

The intermediate I-9 (15 g, 38 mmol) was dissolved in 1 L of DME (dimethyl glycol) in a nitrogen atmosphere, and then 2-aminophenyl boronic acid (5 g, 38 mmol) and tetrakis (triphenylphosphine) palladium 0.4 g, 0.38 mmol) were added and stirred. Saturated water-saturated potassium carbonate (13 g, 95 mmol) was added and heated at 80 ° C for 12 hours to reflux. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-10 (9 g, 70%).

HRMS (70 eV, EI +): m / z calcd for C22H14N2OS: 354.0827, found: 354 Elemental Analysis: C, 75%; H, 4%

Synthetic example 11: Synthesis of Intermediate I-11

[Reaction Scheme 11]

Intermediate I-6 (9 g, 27 mmol) was added to POCl ₃ (20 g, 133 mmol) in a nitrogen atmosphere and heated at room temperature for 12 hours to reflux. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-11 (8 g, 80%).

HRMS (70 eV, EI +): m / z calcd for C22H13ClN2S: 372.0488, found: 372 Elemental Analysis: C, 71%; H, 4%

Synthetic example 12: Synthesis of intermediate I-12

[Reaction Scheme 12]

The compound ethyl 2-bromothiazole-5-carboxylate (20 g, 71 mmol) was dissolved in 1 L of THF in a nitrogen atmosphere and then phenylboronic acid (9.5 g, 78 mmol) and tetrakis (triphenylphosphine) palladium mmol) were added and stirred. Saturated water-saturated potassium carbonate (25 g, 177 mmol) was added and heated at 80 ° C for 12 hours to reflux. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-12 (14 g, 85%).

HRMS (70 eV, EI +): m / z calcd for C12H11NO2S: 233.0510, found: 233 Elemental Analysis: C, 62%; H, 5%

Synthetic example 13: Synthesis of intermediate I-13

[Reaction Scheme 13]

Intermediate I-12 (14 g, 60 mmol) was dissolved in 1 L of CHCl ₃ in a nitrogen atmosphere, and then n-bromosuccinimide (10 g, 60 mmol) was slowly added thereto at 0 ° C and stirred for 30 minutes. The mixture was heated at room temperature for 12 hours to reflux. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-13 (16 g, 80%).

HRMS (70 eV, EI +): m / z calcd for C12H10BrNO2S: 310.9616, found: 310 Elemental Analysis: C, 46%; H, 3%

Synthetic example 14: Synthesis of Intermediate I-14

[Reaction Scheme 14]

Intermediate 1-13 (16 g, 51 mmol) was dissolved in DME (dimethyl glycol) (1 L) in a nitrogen atmosphere and then 2-aminophenyl boronic acid (7 g, 51 mmol) and tetrakis (triphenylphosphine) palladium 0.6 g, 0.51 mmol) were added and stirred. Saturated water-saturated potassium carbonate (17 g, 127 mmol) was added and the mixture was refluxed by heating at 80 ° C for 12 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-14 (10 g, 75%).

HRMS (70 eV, EI +): m / z calcd for C16H10N2OS: 278.0514, found: 278 Elemental Analysis: C, 69%; H, 4%

Synthetic example 15: Synthesis of intermediate I-15

[Reaction Scheme 15]

POCl ₃ (29 g, 191 mmol) was added to the intermediate I-14 (10 g, 38 mmol) in a nitrogen atmosphere and the mixture was heated at room temperature for 12 hours to reflux. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-15 (9 g, 80%).

HRMS (70 eV, EI +): m / z calcd for C16H9ClN2S: 296.0175, found: 296 Elemental Analysis: C, 65%; H, 3%

Synthetic example 16: Synthesis of Intermediate I-16

[Reaction Scheme 16]

Bis (pinacolato) diboron (9 g, 36 mmol) and (1,1'-bis (diphenylphosphine)) were dissolved in 1 L of dimethylformamide (DMF) ferrocene dichloropalladium (II) (0.3 g, 0.3 mmol) and potassium acetate (10 g, 75 mmol) were added and the mixture was refluxed by heating at 150 ° C for 5 hours. After completion of the reaction, water was added to the reaction solution, the mixture was filtered, and then dried in a vacuum oven. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-16 (11 g, 95%).

HRMS (70 eV, EI +): m / z calcd for C22H21BN2O2S: 388.1417, found: 388.

Elemental Analysis: C, 68%; H, 5%

Synthetic example 17: Synthesis of Intermediate I-17

[Reaction Scheme 17]

The intermediate I-16 (9 g, 23 mmol) was dissolved in 1 L of THF in a nitrogen atmosphere and then 1-bromo-3-chlorobenzene (4.3 g, 23 mmol) and tetrakis (triphenylphosphine) palladium mmol) were added and stirred. Saturated water-saturated potassium carbonate (8 g, 57.5 mmol) was added and the mixture was refluxed by heating at 80 ° C for 12 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-17 (7 g, 85%).

HRMS (70 eV, EI +): m / z calcd for C22H13ClN2S: 372.0488, found: 372 Elemental

Analysis: C, 71%; H, 4%

Synthetic example 18: Synthesis of Intermediate I-18

[Reaction Scheme 18]

Bis (pinacolato) diboron (5 g, 19 mmol) and (1,1'-bis (diphenylphosphine) borate) were dissolved in 1 L of dimethylformamide (DMF) ferrocene dichloropalladium (II) (0.2 g, 0.2 mmol) and potassium acetate (5 g, 48 mmol) were added and the mixture was refluxed by heating at 150 ° C for 5 hours. After completion of the reaction, water was added to the reaction solution, the mixture was filtered, and then dried in a vacuum oven. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-18 (11 g, 95%).

HRMS (70 eV, EI +): m / z calcd for C28H25BN2O2S: 464.1730, found: 464.

Elemental Analysis: C, 72%; H, 5%

Synthetic example 19: Synthesis of intermediate I-19

[Reaction Scheme 19]

The compound 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (50 g, 128 mmol) was dissolved in 1 L of THF in a nitrogen atmosphere, and then 3-chlorophenyl boronic acid (24 g, 155 mmol) and tetrakis (triphenylphosphine) palladium (1.5 g, 1.3 mmol) were added and stirred. Saturated water-saturated potassuim carbonate (44 g, 320 mmol) was added and heated at 80 ° C for 12 hours to reflux. After the completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-19 (51 g, 95%).

HRMS (70 eV, EI +): m / z calcd for C27H18ClN3: 419.1189, found: 419.

Elemental Analysis: C, 77%; H, 4%

Synthetic example 20: Synthesis of intermediate I-20

[Reaction Scheme 20]

Bis (pinacolato) diboron (72.5 g, 285 mmol) and (1,1'-bis (diphenylphosphine)) were dissolved in 1 L of dimethylformamide (DMF) ferrocene dichloropalladium (II) (2 g, 2.38 mmol) and potassium acetate (58 g, 595 mmol) were added and heated at 150 ° C for 48 hours to reflux. After completion of the reaction, water was added to the reaction solution, the mixture was filtered, and then dried in a vacuum oven. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-20 (107 g, 88%).

HRMS (70 eV, EI +): m / z calcd for C33H30BN3O2: 511.2431, found: 511

Elemental Analysis: C, 77%; H, 6%

Synthetic example 21: Synthesis of Intermediate I-21

[Reaction Scheme 21]

The compound 3-bromo-9-phenyl-9H-carbazole (115 g, 366 mmol) was dissolved in 1 L of THF in a nitrogen atmosphere, followed by addition of 3-chlorophenyl boronic acid (57 g, 366 mmol) triphenylphosphine) palladium (4.2 g, 3.66 mmol) were added and stirred. Saturated water-saturated potassuim carbonate (126 g, 915 mmol) was added and heated at 80 ° C for 12 hours to reflux. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-21 (118 g, 92%).

HRMS (70 eV, EI +): m / z calcd for C24H16ClN: 353.0971, found: 278.

Elemental Analysis: C, 81%; H, 5%

Synthetic example 22: Synthesis of Intermediate I-22

[Reaction Scheme 22]

Bis (pinacolato) diboron (100 g, 393 mmol) and (1, 1'-bis (diphenylphosphine)) were dissolved in 1 L of dimethylformamide (DMF) ferrocene) dichloropalladium (II) (2.68 g, 3.28 mmol) and potassium acetate (80 g, 820 mmol) were added and the mixture was refluxed by heating at 150 ° C for 48 hours. After completion of the reaction, water was added to the reaction solution, the mixture was filtered, and then dried in a vacuum oven. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-22 (131 g, 90%).

HRMS (70 eV, EI +): m / z calcd for C30H28BNO2: 445.2213, found: 445

Elemental Analysis: C, 81%; H, 6%

Synthetic example 23: Synthesis of Intermediate I-23

[Reaction Scheme 23]

Intermediate I-22 (110 g, 269 mmol) was dissolved in 1 L of THF in a nitrogen atmosphere and then 1-bromo-3-chlorobenzene (62 g, 322 mmol) and tetrakis (triphenylphosphine) palladium mmol) were added and stirred. Saturated water-saturated potassium carbonate (93 g, 672 mmol) was added and heated at 80 ° C for 12 hours to reflux. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-23 (99 g, 89%).

HRMS (70 eV, EI +): m / z calcd for C30 H20 ClN: 429.1284, found: 429.

Elemental Analysis: C, 84%; H, 5%

Synthetic example 24: Synthesis of Intermediate I-24

[Reaction Scheme 24]

Bis (pinacolato) diboron (67 g, 265 mmol) and (1,1'-bis (diphenylphosphine)) were dissolved in 1 L of dimethylformamide (DMF) ferrocene) dichloropalladium (II) (1.8 g, 2.21 mmol) and potassium acetate (54 g, 552 mmol) were added and the mixture was refluxed by heating at 150 ° C for 48 hours. After completion of the reaction, water was added to the reaction solution, the mixture was filtered, and then dried in a vacuum oven. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-24 (98 g, 90%).

HRMS (70 eV, EI +): m / z calcd for C36H32BNO2: 521.2526, found: 521

Elemental Analysis: C, 83%; H, 6%

Synthetic example 25: Synthesis of intermediate I-25

[Reaction Scheme 25]

(3-chlorophenyl) boronic acid (57 g, 366 mmol) and tetrakis (triphenylphosphine) were dissolved in 1 L of THF in a nitrogen atmosphere and the compound 4-bromodibenzo [b, palladium (4.2 g, 3.66 mmol) were added thereto and stirred. Saturated water-saturated potassuim carbonate (126 g, 915 mmol) was added and heated at 80 ° C for 12 hours to reflux. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-25 (93 g, 92%).

HRMS (70 eV, EI +): m / z calcd for C18 H11 ClO: 278.0498, found: 278.

Elemental Analysis: C, 78%; H, 4%

Synthetic example 26: Synthesis of Intermediate I-26

[Reaction Scheme 26]

Bis (pinacolato) diboron (100 g, 393 mmol) and (1, 1'-bis (diphenylphosphine)) were dissolved in 1 L of dimethylformamide (DMF) ferrocene) dichloropalladium (II) (2.68 g, 3.28 mmol) and potassium acetate (80 g, 820 mmol) were added and the mixture was refluxed by heating at 150 ° C for 48 hours. After completion of the reaction, water was added to the reaction solution, the mixture was filtered, and then dried in a vacuum oven. The thus-obtained residue was purified by flash column chromatography to obtain Intermediate I-26 (112 g, 90%).

HRMS (70 eV, EI +): m / z calcd for C24H23BO3: 370.1740, found: 370

Elemental Analysis: C, 78%; H, 6%

Synthetic example 27: Synthesis of Intermediate I-27

[Reaction Scheme 27]

The intermediate I-26 (100 g, 277 mmol) was dissolved in 1 L of THF in a nitrogen atmosphere and then 1-bromo-3-chlorobenzene (53 g, 377 mmol) and tetrakis (triphenylphosphine) palladium mmol) were added and stirred. Saturated water-saturated potassium carbonate (96 g, 692 mmol) was added and heated at 80 ° C for 12 hours to reflux. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The thus-obtained residue was purified by flash column chromatography to obtain Intermediate I-27 (96 g, 92%).

HRMS (70 eV, EI +): m / z calcd for C24H15ClO: 354.0811, found: 354.

Elemental Analysis: C, 81%; H, 4%

Synthetic example 28: Synthesis of intermediate I-28

[Reaction Scheme 28]

Bis (pinacolato) diboron (96 g, 378 mmol) and (1, 1'-bis (diphenylphosphine)) were dissolved in 1 L of dimethylformamide (DMF) ferrocene dichloropalladium (II) (2.57 g, 3.15 mmol) and potassium acetate (77 g, 787 mmol) were added and heated at 150 ° C. for 48 hours to reflux. After completion of the reaction, water was added to the reaction solution, the mixture was filtered, and then dried in a vacuum oven. The thus-obtained residue was purified by flash column chromatography to obtain Intermediate I-28 (128 g, 91%).

HRMS (70 eV, EI +): m / z calcd for C30H27BO3: 446.2053, found: 446

Elemental Analysis: C, 81%; H, 6%

Synthetic example 29: Synthesis of Intermediate I-29

[Reaction Scheme 29]

The intermediate compound I-24 (39 g, 78 mmol) and tetrakis (triphenylphosphine) palladium (0.8 g, 71 mmol) were dissolved in 1 L of THF in the presence of nitrogen in the presence of ethyl 2-bromothiazole- g, 0.71 mmol) were added and stirred. Saturated water-saturated potassium carbonate (25 g, 177 mmol) was added and heated at 80 ° C for 12 hours to reflux. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-29 (14 g, 85%).

HRMS (70 eV, EI +): m / z calcd for C36 H26 N2 O2 S: 550.1715, found: 550 Elemental

Analysis: C, 79%; H, 5%

Synthetic example 30: Synthesis of Intermediate I-30

[Reaction Scheme 30]

The intermediate I-29 (33 g, 60 mmol) was dissolved in 1 L of CHCl ₃ in a nitrogen atmosphere, and then n-bromosuccinimide (10 g, 60 mmol) was slowly added thereto at 0 ° C. and stirred for 30 minutes. The mixture was heated at room temperature for 12 hours to reflux. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-30 (31 g, 82%).

HRMS (70 eV, EI +): m / z calcd for C36H25BrN2O2S: 628.0820, found: 628

Elemental Analysis: C, 69%; H, 4%

Synthetic example 31: Synthesis of Intermediate I-31

[Reaction Scheme 31]

Intermediate 1-30 (27 g, 51 mmol) was dissolved in 1 L of DME (dimethyl glycol) in a nitrogen atmosphere, and then 2-aminophenyl boronic acid (7 g, 51 mmol) and tetrakis (triphenylphosphine) palladium 0.6 g, 0.51 mmol) were added and stirred. Saturated water-saturated potassium carbonate (17 g, 127 mmol) was added and the mixture was refluxed by heating at 80 ° C for 12 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-31 (22 g, 73%).

HRMS (70 eV, EI +): m / z Calcd for C40H25N3OS: 595.1718, found: 595 Elemental

Analysis: C, 81%; H, 4%

Synthetic example 32: Synthesis of Intermediate I-32

[Reaction Scheme 32]

Intermediate I-31 (22 g, 38 mmol) was added to POCl ₃ (29 g, 191 mmol) in a nitrogen atmosphere and heated at room temperature for 12 hours to reflux. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-32 (18 g, 80%).

HRMS (70 eV, EI +): m / z calcd for C40H24ClN3S: 613.1379, found: 613 Elemental

Analysis: C, 78%; H, 4%

Synthetic example 33: Synthesis of Intermediate I-33

[Reaction Scheme 33]

1-bromo-3-iodobenzene (34 g, 119.7 mmol) and tris (diphenylideneacetone) dipalladium (0) (1 g, 119.7 mmol) were dissolved in 0.18 L of toluene in a nitrogen atmosphere, 1.2 mmol), tris-tert butylphosphine (1 g, 4.7 mmol) and sodium tert-butoxide (14 g, 143 mmol) were successively added and refluxed by heating at 100 ° C for 18 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was purified by flash column chromatography to obtain intermediate I-33 (30 g, 79%).

HRMS (70 eV, EI +): m / z calcd for C18H12BrN: 321.0153, found: 321.

Elemental Analysis: C, 67%; H, 4%

Synthetic example 34: Synthesis of Intermediate I-34

[Reaction Scheme 34]

Bis (pinacolato) diboron (24 g, 93 mmol) and (1,1'-bis (diphenylphosphine) borane) were dissolved in 1 L of dimethylformamide (DMF) ferrocene) dichloropalladium (II) (759 g, 0.93 mmol) and potassium acetate (23 g, 232 mmol) were added and the mixture was refluxed by heating at 150 ° C for 48 hours. After completion of the reaction, water was added to the reaction solution, the mixture was filtered, and then dried in a vacuum oven. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-34 (30 g, 90%).

HRMS (70 eV, EI +): m / z calcd for C24H24BNO2: 369.1900, found: 369

Elemental Analysis: C, 78%; H, 7%

Synthetic example 35: Synthesis of Intermediate I-35

[Reaction Scheme 35]

Intermediate I-34 (30 g, 81 mmol) was dissolved in 1 L of THF in a nitrogen atmosphere and 1-bromo-3-chlorobenzene (19 g, 98 mmol) and tetrakis (triphenylphosphine) palladium mmol) were added and stirred. Saturated water-saturated potassuim carbonate (28 g, 202 mmol) was added and heated at 80 ° C for 12 hours to reflux. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-35 (26 g, 90%).

HRMS (70 eV, EI +): m / z calcd for C24H16ClN: 353.0971, found: 353.

Elemental Analysis: C, 81%; H, 5%

Synthetic example 36: Synthesis of Intermediate I-36

[Reaction Scheme 36]

Bis (pinacolato) diboron (23 g, 88 mmol) and (1,1'-bis (diphenylphosphine) boron) were dissolved in 1 L of dimethylformamide (DMF) ferrocene dichloropalladium (II) (0.63 g, 0.74 mmol) and potassium acetate (18 g, 185 mmol) were added and heated at 150 ° C for 48 hours. After completion of the reaction, water was added to the reaction solution, the mixture was filtered, and then dried in a vacuum oven. The thus-obtained residue was purified by flash column chromatography to obtain Intermediate I-36 (30 g, 92%).

HRMS (70 eV, EI +): m / z calcd for C30H28BNO2: 445.2213, found: 445

Elemental Analysis: C, 81%; H, 6%

Synthetic example 37: Synthesis of Intermediate I-37

[Reaction Scheme 37]

The intermediate compound I-36 (34 g, 78 mmol) and tetrakis (triphenylphosphine) palladium (0.8 g, 71 mmol) were dissolved in 1 L of THF in a nitrogen atmosphere, and the ethyl 2-bromothiazole- g, 0.71 mmol) were added and stirred. Saturated water-saturated potassium carbonate (25 g, 177 mmol) was added and heated at 80 ° C for 12 hours to reflux. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-37 (30 g, 90%).

HRMS (70 eV, EI +): m / z calcd for C30 H22 N2 O2 S: 474.1402, found: 474

Elemental Analysis: C, 76%; H, 5%

Synthetic example 38: Synthesis of intermediate I-38

[Reaction Scheme 38]

The intermediate I-37 (28 g, 60 mmol) was dissolved in 1 L of CHCl ₃ in a nitrogen atmosphere, and then n-bromosuccinimide (10 g, 60 mmol) was slowly added thereto at 0 ° C and stirred for 30 minutes. The mixture was heated at room temperature for 12 hours to reflux. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-38 (30 g, 82%).

HRMS (70 eV, EI +): m / z calcd for C30H21BrN2O2S: 552.0507, found: 552

Elemental Analysis: C, 65%; H, 4%

Synthetic example 39: Synthesis of Intermediate I-39

[Reaction Scheme 39]

Intermediate 1-38 (28 g, 51 mmol) was dissolved in 1 L of DME (dimethyl glycol) in a nitrogen atmosphere and then 2-aminophenyl boronic acid (7 g, 51 mmol) and tetrakis (triphenylphosphine) palladium 0.6 g, 0.51 mmol) were added and stirred. Saturated water-saturated potassium carbonate (17 g, 127 mmol) was added and the mixture was refluxed by heating at 80 ° C for 12 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-39 (20 g, 73%).

HRMS (70 eV, EI +): m / z calcd for C34H21N3OS: 519.1405, found: 519 Elemental

Analysis: C, 79%; H, 4%

Synthetic example 40: Synthesis of intermediate I-40

[Reaction Scheme 40]

To reflux into the intermediate I-39 (20 g, 38 mmol) of _{POCl 3 (29 g, 191 mmol} ) in a nitrogen atmosphere is heated at room temperature for 12 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Intermediate I-40 (16 g, 80%).

HRMS (70 eV, EI +): m / z calcd for C34H20ClN3S: 537.1066, found: 537 Elemental Analysis: C, 76%; H, 4%

Synthetic example 41: Synthesis of compound a-1

[Reaction Scheme 41]

The intermediate I-3 (12 g, 33 mmol) and tetrakis (triphenylphosphine) palladium (0.38 g, 0.33 mmol) were dissolved in 1 L of THF in a nitrogen atmosphere, And the mixture was stirred. Saturated water-saturated potassium carbonate (11 g, 82.5 mmol) was added and the mixture was refluxed by heating at 80 ° C for 12 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain the above compound a-1 (18 g, 87%).

HRMS (70 eV, EI +): m / z calcd for C46H30N2S: 642.2130, found: 642.

Elemental Analysis: C, 86%; H, 5%

Synthetic example 42: Synthesis of compound d-3

[Reaction Scheme 42]

Intermediate I-20 (12 g, 33 mmol) and tetrakis (triphenylphosphine) palladium (0.57 g, 0.99 mmol) were dissolved in 1 L of THF in a nitrogen atmosphere, And stirred. Water saturated potassium solution (27 g, 82 mmol) were successively added thereto, followed by heating at 100 占 폚 for 18 hours to reflux. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain compound d-3 (19 g, 88%).

HRMS (70 eV, EI +): m / z calcd for C43H27N5S: 645.1987, found: 645.

Elemental Analysis: C, 80%; H, 4%

Synthetic example 43: Synthesis of compound d-52

[Reaction Scheme 43]

Intermediate I-18 (12 g, 26.8 mmol) and (tetrakis (triphenylphosphine) palladium (0.95 g, 0.80 mmol) were dissolved in 1 L of THF in a nitrogen atmosphere, Was added and stirred. Water-saturated potassium salt carbonate (22 g, 67 mmol) were successively added thereto, followed by heating at 100 占 폚 for 18 hours to reflux. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain a compound d-52 (15 g, 85%).

HRMS (70 eV, EI +): m / z Calcd for C44H26N4S2: 674.1599, found: 674.

Elemental Analysis: C, 78%; H, 4%

Synthetic example 44: Synthesis of compound d-53

[Reaction Scheme 44]

Intermediate I-18 (12 g, 26.8 mmol) and Bis (dibenzylideneacetone) palladium (0) were dissolved in 1 L of dioxane in a nitrogen atmosphere,

0.46 g, 0.80 mmol) tris-tert butylphosphine (0.81 g, 4 mmol) and Cesium Carbonate (Cs₂CO₃)(22 g, 67 mmol) were successively added thereto, followed by heating at 100 占 폚 for 18 hours to reflux. After completion of the reaction, water was added to the reaction solution, extracted with dichloromethane (DCM), dried over anhydrous MgSO 4₄After removing moisture, the solution was filtered and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain a compound d-53 (16 g, 88%).

HRMS (70 eV, EI +): m / z Calcd for C44H26N4S2: 674.1599, found: 674.

Elemental Analysis: C, 78%; H, 4%

Synthetic example 45 Synthesis of compound c-51

[Reaction Scheme 45]

Intermediate I-24 (17 g, 33 mmol) and tetrakis (triphenylphosphine) palladium (90.57 g, 0.99 mmol) were added to the reaction mixture in a nitrogen atmosphere and the intermediate I-15 Lt; / RTI > Potassium hydroxide (27 g, 82 mmol), saturated with water, was added sequentially and heated at 100 ° C for 18 hours to reflux. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain a compound c-51 (18 g, 84%).

HRMS (70 eV, EI +): m / z calcd for C46H29N3S: 655.2082, found: 655.

Elemental Analysis: C, 84%; H, 4%

Synthetic example 46: Synthesis of compound c-54

[Reaction Scheme 46]

Intermediate I-28 (14 g, 33 mmol) and tetrakis (triphenylphosphine) palladium (0.57 g, 0.99 mmol) were added to the reaction mixture in a nitrogen atmosphere and the intermediate I-11 Lt; / RTI > Potassium hydroxide (27 g, 82 mmol), saturated with water, was added sequentially and heated at 100 ° C for 18 hours to reflux. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain a compound c-54 (17 g, 80%).

HRMS (70 eV, EI +): m / z calcd for C46H28N2OS: 656.1922, found: 656.

Elemental Analysis: C, 84%; H, 4%

Synthetic example 47: Synthesis of Compound c-2

[Reaction Scheme 47]

I-36 (15 g, 33 mmol) and tetrakis (triphenylphosphine) palladium (0.57 g, 0.99 mmol) were added to 1 L of THF in a nitrogen atmosphere, followed by stirring . Potassium hydroxide (27 g, 82 mmol), saturated with water, was added sequentially and heated at 100 ° C for 18 hours to reflux. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Compound c-2 (21 g, 80%).

HRMS (70 eV, EI +): m / z calcd for C58H36N4S: 820.2661, found: 820.

Elemental Analysis: C, 85%; H, 4%

Fabrication of organic light emitting device

Example One

An organic light emitting device was fabricated using acetylacetonatobis (2-phenylquinolinato) iridium (Ir (pq) ₂ acac) as a dopant by using the compound a-1 obtained in Synthesis Example 41 as a host.

As the anode, ITO was used to a thickness of 1500 Å, and aluminum (Al) was used as a cathode to a thickness of 1000 Å. Specifically, an explanation will be given of a method of manufacturing an organic light emitting device. An ITO glass substrate having a sheet resistance of 15 Ω / cm 2 is cut into a size of 50 mm × 50 mm × 0.7 mm, and is cut in acetone, isopropyl alcohol and pure water After ultrasonic cleaning for 15 minutes, UV ozone cleaning was used for 30 minutes.

The degree of vacuum in the upper substrate 650 × 10 ^-7 Pa, the deposition rate of 0.1 to 0.3 nm / s in terms 4,4'-bis [N- [4- { N, N-bis (3-methylphenyl) amino} -phenyl ] -N-phenylamino] biphenyl [DNTPD] was vacuum-deposited to form a hole injection layer having a thickness of 600 Å. Subsequently, HT-1 was vacuum vapor deposited under the same vacuum deposition conditions to form a 300 Å thick hole transport layer. Next, a light emitting layer having a thickness of 300 angstroms was formed using the compound 1 obtained in Synthesis Example 21 under the same vacuum deposition condition, wherein acetylacetonatobis (2-phenylquinolinato) iridium (Ir (pq) ₂ acac) Respectively. At this time, the deposition rate of the phosphorescent dopant was adjusted so that the phosphorescent dopant content was 7% by weight when the total amount of the light emitting layer was 100% by weight.

Bis (2-methyl-8-quinolinolate) -4- (phenylphenolato) aluminum (BAlq) was deposited on the light emitting layer using the same vacuum deposition conditions to form a hole blocking layer having a thickness of 50 Å. Then, Tris (8-hydroxyquinolinato) aluminum (Alq ₃ ) was deposited under the same vacuum deposition conditions to form an electron transport layer having a thickness of 250 ANGSTROM. LiF and Al were sequentially deposited on the electron transport layer as cathodes to fabricate an organic photoelectric device.

The structure of the organic photoelectric device was ITO / DNTPD (60 nm) / HT-1 (30 nm) / EML (compound a-1 (93 wt%) + Ir (pq) ₂ acac (7 wt% / Balq (5 nm) / Alq ₃ (25 nm) / LiF (1 nm) / Al (100 nm).

Example 2 to 7

An organic luminescent device was prepared in the same manner as in Example 1 except that the compounds of Synthesis Examples 42 to 47 were used instead of the compound of Synthesis Example 41 (a-1).

Comparative Example One

An organic light emitting device was prepared in the same manner as in Example 1 except that 4,4'-di (9H-carbazol-9-yl) biphenyl (CBP) was used in place of the compound a-1 in Synthesis Example 41.

The structures of DNTPD, BAlq, HT-1, CBP, and Ir (pq) ₂ acac used in the production of the organic light emitting device are as follows.

evaluation

The current density change, the luminance change, and the light emitting efficiency of the organic light emitting device according to Examples 1 to 7 and Comparative Example 1 were measured according to the voltage.

The specific measurement method is as follows, and the results are shown in Table 1.

(1) Measurement of change in current density with voltage change

For the organic light emitting device manufactured, the current flowing through the unit device was measured using a current-voltmeter (Keithley 2400) while raising the voltage from 0 V to 10 V, and the measured current value was divided by the area to obtain the result.

(2) Measurement of luminance change according to voltage change

For the organic light-emitting device manufactured, luminance was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0 V to 10 V, and the result was obtained.

(3) Measurement of luminous efficiency

The current efficiency (cd / A) at the same current density (10 mA / cm ² ) was calculated using the luminance, current density and voltage measured from the above (1) and (2).

(4) Life measurement

The initial luminance (cd / m ² ) was emitted at 3000 cd / m ² , and the decrease in luminance over time was measured to determine the time to reduce to 90% of the initial luminance.

No. compound The driving voltage (V) color
(EL color) Luminous efficiency
(cd / A) 90% lifetime (h)
At 3000 cd / m ² Example 1 Compound a-1 7.0 Red 49.4 77 Example 2 Compound d-3 6.8 Red 48.5 93 Example 3 Compound d-52 5.2 Red 48.2 83 Example 4 Compound d-53 5.3 Red 49.0 80 Example 5 Compound c-51 6.9 Red 47.2 75 Example 6 Compound c-54 7.0 Red 47.3 62 Example 7 Compound c-2 7.2 Red 45.5 100 Comparative Example 1 CBP 7.4 Red 37.2 50

Referring to Table 1, it can be seen that the organic electroluminescent device according to Examples 1 to 7 has significantly improved driving voltage, luminous efficiency and lifetime characteristics as compared with the organic electroluminescent device according to Comparative Example 1.

It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present invention as defined by the following claims. As will be understood by those skilled in the art. It is therefore to be understood that the above-described embodiments are illustrative in all aspects and not restrictive.

100, 200: Organic light emitting device
105: organic layer
110: cathode
120: anode
130: light emitting layer
140: hole assist layer

Claims

A compound for an organic optoelectronic device represented by the following formula (I):
(I)

In the above formula (I)
X ¹ and X ² are each independently N or S,
Wherein ^{one of} X < ¹ ^> and X < ² > is N,
R ¹ and R ² are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
R ³ and R ⁴ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a halogen group, a cyano group, a hydroxy group,
L ¹ and L ² are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group,
The term "substituted" as used herein means that at least one hydrogen is substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a hydroxy group, a C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, To C30 aryl group, a C2 to C30 heterocyclic group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group, or a cyano group.

The method according to claim 1,
A compound for an organic optoelectronic device represented by the following formula (I-1) or (I-2):
[Formula (I-1)] [Formula (I-2)

In the above Formulas I-1 and I-2,
X ¹ and X ² are each independently S,
R ¹ and R ² are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
R ³ and R ⁴ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a halogen group, a cyano group, a hydroxy group,
L ¹ and L ² are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group,
&Quot; Substitution " is the same as defined in the above item 1.

The method according to claim 1,
At least one of R ¹ and R ² is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted naphthacenyl group A substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted quaterphenyl group, Substituted or unsubstituted pyrazinyl groups, substituted or unsubstituted pyrazinyl groups, substituted or unsubstituted pyrazinyl groups, substituted or unsubstituted pyrazinyl groups, substituted or unsubstituted pyrazinyl groups, substituted or unsubstituted pyrazinyl groups, substituted or unsubstituted pyrazinyl groups, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted benzothiophenyl group, A substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted oxazoloquinolinyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted oxazolinoquinolinyl group, A thiazoloquinolinyl group, or a combination thereof,
The term "substituted" as used herein means that at least one hydrogen is substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a hydroxy group, a C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, To C30 aryl group, a C2 to C30 heterocyclic group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group, or a cyano group.

The method according to claim 1,
Wherein at least one of R < ¹ > and R < ² > is selected from a substituted or unsubstituted group listed in the following Group I:
[Group I]

In the group I,
Z is N or CR ^a ,
W is ^{N, O, S, CR b} R c,
R ^a to R ⁿ each independently represent hydrogen, deuterium, a C1 to C30 alkyl group, a phenyl group, a halogen group, a cyano group, a hydroxyl group, an amino group, a nitro group,
* Is a linking point connected to L ¹ or L ² of the above formula (I)
n and m are each independently an integer of 0 to 2,
&Quot; Substitution " is the same as defined in the above item 1.

5. The method of claim 4,
Wherein the substituted or unsubstituted groups listed in Group I are selected from the groups listed in the following Group I-A:
[Group I-A]

In the group I-A,
* Is a connecting point connecting with L ¹ or L ² in the above formula (I).

5. The method of claim 4,
Wherein the substituted or unsubstituted groups listed in Group I are selected from the groups listed in the following Group I-B:
[Group I-B]

In said Group I-B,
* Is a connecting point connecting with L ¹ or L ² in the above formula (I).

The method according to claim 1,
L ¹ and L ² each independently represent a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, or a substituted or unsubstituted quaterphenylene group ,
The term "substituted" as used herein means that at least one hydrogen is substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a hydroxy group, a C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, Wherein the aryl group is substituted with a C30 to C30 aryl group, a C2 to C30 heterocyclic group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group, or a cyano group.

The method according to claim 1,
A compound for an organic optoelectronic device, which is any one of the compounds listed in Group A below:
[Group A]

.

The method according to claim 1,
A compound for an organic optoelectronic device, which is any one of the compounds listed in Group B below:
[Group B]

.

Positive and negative facing each other, and
And at least one organic layer positioned between the anode and the cathode,
Wherein the organic layer comprises the compound for an organic optoelectronic device according to any one of claims 1 to 9.

11. The method of claim 10,
Wherein the organic layer includes a light emitting layer,
Wherein the light emitting layer comprises the compound for an organic optoelectronic device.

12. The method of claim 11,
Wherein the compound for an organic optoelectronic device is included as a host of the light emitting layer.

11. The method of claim 10,
Wherein the organic layer includes at least one auxiliary layer selected from a hole injecting layer, a hole transporting layer, a hole transporting auxiliary layer, an electron transporting auxiliary layer, an electron transporting layer and an electron injecting layer,
Wherein the auxiliary layer comprises the compound for an organic optoelectronic device.

A display device comprising the organic opto-electronic device according to claim 10.