WO2019132545A1 - Organic light-emitting device - Google Patents

Abstract

The present invention provides an organic light-emitting device.

Description

 2019/132545 1 »(: 1 ^ 1 {2018/016773

Title of the Invention

 Organic light emitting device

 TECHNICAL FIELD

 Cross-reference with related application (s)

 This application claims the benefit of priority based on Korean Patent Application No. 10-2017-0181543, dated December 27, 2017, and Korean Patent Application No. 10-2018-0169819, dated December 26, 2018, The entire contents of which are incorporated herein by reference. The present invention relates to an organic light emitting device.

 BACKGROUND ART [0002]

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. Organic light emitting devices which utilize organic light emitting phenomenon have a wide viewing angle, excellent contrast _, fast response time, excellent characteristics of luminance, driving voltage and response speed, and much research has been conducted. The organic light emitting device generally has a structure including an anode and a cathode, and an organic 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 may have a multilayer structure composed of different materials. For example, the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. If voltage is applied between the two electrodes in the structure of the organic light emitting element in the anode when the hole is, the cathode being so electrons are injected to the organic layer, the injected holes and electrons are met exciton _{(6 X (: 11: 011} ) the And the light is emitted when the exciton falls back to the ground state. There is a continuing need for the development of new materials for the organic materials used in such organic light emitting devices.

[Prior Art Document] 2019/132545 1 »(: 1 ^ 1 {2018/016773

[Patent Literature]

 (Patent Document 0001) Korean Patent Publication No. 10-2000-0051826

 DISCLOSURE OF THE INVENTION

 [Problem to be solved]

 The present invention relates to an organic light emitting device.

 MEANS FOR SOLVING THE PROBLEMS

 The present invention provides the following organic light emitting device:

 anode; A negative electrode opposed to the positive electrode; And at least one organic material layer provided between the anode and the cathode,

 Wherein the organic layer includes a light emitting layer,

 Wherein the light emitting layer comprises a compound represented by the following formula (1) and a compound represented by the following formula (2)

 Organic Light Emitting Device:

 [Chemical Formula 1]

 In Formula 1,

Silver and silver alloy; Or substituted or unsubstituted 0 _6-60 arylenes, 2 is a single bond; Substituted or unsubstituted 0 _{6-60 arylenes} ,

Substituted or unsubstituted 0 _3-60 cycloalkyl; Substituted or unsubstituted 0 _1-60 alkyl, substituted or unsubstituted 0 _6-60 aryl; Or a substituted or unsubstituted one 0 _2-60 heteroaryl group containing one or more heteroatoms 0, selected from the group consisting of and,

2 and 3 are each independently hydrogen, cyano, substituted or unsubstituted 01 ₆₀ alkyl, substituted or unsubstituted 0 _6-60 aryl; Or a substituted or unsubstituted one 0 _2-60 heteroaryl group containing one or more heteroatoms 0, selected from the group consisting of and, 2019/132545 1 »(: 1 ^ 1 {2018/016773

 In Formula 2,

¾ _1, 1¾ _{2, 3 ¾,} and ¾ ₄ Heavy I - and _21-1, is hydrogen or off,

And _{¾ 1, ¾ 2, 1¾ 3} , Heavy mityo ₃₄ _ I feel _22-2, and the other is hydrogen,

- or _{22- 2, 3} is 1½ 1½ -1 ₂厂₁ and the - or _{22- 2, 4} ¾ _2-21 / ₁ and ¾ ₄ is - except紅₂ Ann crying, - ₂

2 is a divalent bond or a substituted or unsubstituted 0 _6-60 arylene,

¾ is 0, or,

 Show Galactic Formula 3,

 (3)

 In Formula 3,

 Are each independently or a group, and at least one of the groups is

3 and ₄ are each independently a substituted or unsubstituted 0 _6-60 aryl; Or a substituted or unsubstituted 0, and either 0 _2-60 heteroaryl group containing one or more hetero atoms selected from the configuration in doeneungun, 2019/132545 1 is selected from the group consisting of:

 In the above,

 Lt; / RTI > are each independently or predominant, at least one of the groups is N,

 9 is 0, or £,

5 _{, 6} and ₇ are each independently a substituted or unsubstituted 0 _6-60 aryl; Or 0 _2-60 heteroaryl group containing one or more hetero atoms selected from substituted or unsubstituted 0, and configured to doeneungun ring.

 【Effects of the Invention】

 The organic light emitting device described above can improve the efficiency, the lower the driving voltage and / or the lifetime characteristics of the organic light emitting device by controlling the compound included in the light emitting layer.

 BRIEF DESCRIPTION OF THE DRAWINGS

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

 2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is.

 Fig. 3 is a cross-sectional view of a light emitting device according to a first embodiment of the present invention, which includes a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, an electron blocking layer 9, a light emitting layer 7, an electron transporting layer 8, And a cathode (4).

 4 shows an example in which the substrate 1, the anode 2, the hole injecting layer 5, the hole transporting layer 6, the light emitting layer 7, the hole blocking layer 11, the electron transporting layer 8, And a cathode (4).

 DETAILED DESCRIPTION OF THE INVENTION

Hereinafter, the present invention will be described in detail in order to facilitate understanding of the present invention. 2019/132545 1 »(: 1/10 公 018/016773

In the present specification,

Means a bond connected to another substituent. The term " substituted or unsubstituted ", as used herein, refers to a substituent selected from the group consisting of deuterium, halogen group, nitrile group, nitro group, hydroxyl group, carbonyl group, ester group, imide group, amino group, phosphine oxide group, An aryloxy group, an aryloxy group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamine group, An arylamine group, an arylphosphine group, or a heterocyclic group containing at least one of 0 and < RTI ID = 0.0 > atoms, < / RTI > or substituted or unsubstituted with one or more substituents selected from the group consisting of A substituent having two or more substituents connected thereto may be a biphenyl group, that is, a biphenyl group may be an aryl group, In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but it is preferably 1 to 40. Specifically, the compound may have the following structure, It is not.

In the present specification, 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 in the ester group. Specifically, it may be a compound of the following structural formula, but is not limited thereto. 2019/132545 1 »(: 1 ^ 1 {2018/016773

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

In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group

A silyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group. In the present specification, the boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a 1-butyldimethylboron group, a triphenylboron group, a phenylboron group and the like. In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine. In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. Work 2019/132545 1 »(: 1 ^ 1 {2018/016773

According to the embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group roneun methyl, ethyl, propyl, _11-propyl, isopropyl, butyl, _11-butyl, isobutyl, _1-butyl-6 _,

1-methyl-butyl, 1-ethyl-butyl, pentyl, _11-pentyl, isopentyl, neopentyl, La卜pendoel, haeksil, ₁₁ haeksil, 1-methylpentyl, 2-methylpentyl,

2-ethylbutyl, heptyl, II-heptyl, 1 -methylnucleyl, cyclopentylmethyl, cyclohectylmethyl, octyl, ₁₁ -octyl, myo-octyl, 1-methyl-2-pentyl, 3-methylbutyl, Methylheptyl, 2-ethylhexyl, 2-propylpentyl, ₁₁ -nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, haeksil, 5-methyl haeksil but are _not limited to these. In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-

1 - phenylvinyl - 1 - yl, 2 - phenylvinyl - 1 - phenylphenyl, 1 - phenylpentenyl, 3 - pentenyl, 3 - methyl - 1 - butenyl, 1,3 - butadienyl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-

(Naphthyl-1-yl) vinyl-1-il, 2,2-bis (diphenyl-1-yl) vinyl-1-il, such as steel bay group, a styryl group LES ^0), but is not limited to these. In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, mention may be made of 4-methylcyclohexyl, 3-methylcyclohexyl, 3-methylcyclohexyl, 3-methylcyclopentyl, 2019/132545 1 »(: 1 ^ 1 {2018/016773

Haeksil methylcyclohexyl, 2, 3-dimethyl-bicyclo haeksil, 3,4, 5-trimethyl-bicyclo haeksil, 4 Ah ₆₁寸_ butyl cycloalkyl include but haeksil, cycloheptyl, cyclooctyl, and the like. In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group. In the present specification, a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,

And so on. However, the present invention is not limited thereto. In the present specification, the heterocyclic group is a hetero atom such as 0, I and < RTI ID = 0.0 >

The number of carbon atoms is not particularly limited, but is preferably 2 to 6 占 폚. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrolyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, , A pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyranyl group, a pyrazinopyranyl group, an isoquinoline group, , A carbazole group, a benzoxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, 2019/132545 1 »(: 1 ^ 1 {2018/016773

A dibenzothiophene group, a benzofuranyl group,

An isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but is not limited thereto. In the present specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group and the arylamine group is the same as the aforementioned aryl group. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the alkyl group described above. In the present specification, the heteroaryl among the heteroarylamines can be applied to the description of the above-mentioned heterocyclic groups. In the present specification, the alkenyl group in the aralkenyl group is the same as the above-mentioned alkenyl group. In the present specification, the description of the aryl group described above can be applied, except that the arylthene is divalent. In the present specification, the description of the above-mentioned heterocyclic group can be applied except that the heteroarylene is a divalent group _. In this specification, the description of the aryl group or the cycloalkyl group described above can be applied, except that the hydrocarbon ring is not a monocyclic and the two substituents are bonded to each other. In the present specification, the description of the above-mentioned heterocyclic group can be applied, except that the heterocyclic ring is not a monovalent group and two substituents are bonded to each other. According to the present invention, A negative electrode opposed to the positive electrode; And at least one organic compound layer disposed between the anode and the cathode, wherein the organic compound layer includes a light emitting layer, and the light emitting layer includes a compound represented by Formula 1 and a compound represented by Formula 2 , And an organic light emitting element. The organic light emitting device according to the present invention can improve the efficiency, the driving voltage and / or the lifetime of the organic light emitting device by controlling the compound included in the light emitting layer. Hereinafter, the present invention will be described in detail. Anode and cathode

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted to the organic material layer. 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, rhodium oxide, indium tin oxide ((1), indium zinc oxide (1-0)

A combination of the same metal and oxide; Poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene; | Table 0) 1 '), conductive polymers such as polypyrrole and polyaniline, but are not limited thereto. The negative electrode material is preferably a material having a small work function to facilitate electron injection into the 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; Layer structure materials such as LiF / Al or Li 占 l l, but the present invention is not limited thereto. In addition, a hole injection layer may be further included on the anode. The hole injecting layer is formed of a hole injecting material. The hole injecting material has a hole injecting effect on the anode, an excellent hole injecting effect on the light emitting layer or the light emitting material due to its ability to transport holes, A compound which prevents migration to the electron injection layer or the electron injecting material and is excellent in the thin film forming ability is preferable. It is preferable that the work function of the highest occupied molecular orbital (H0M0) of the hole injecting material is between the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include organic materials such as metal porphyrin, oligothiophene, arylamine-based organic materials, quinacridone-based organic materials, quinacridone-based organic materials, perylene perylene series organic matter, 2019/132545 1 »(: 1 ^ 1 {2018/016773

Anthraquinone, polyaniline and a polythiophene-based conductive polymer, but are not limited thereto. Hole transport layer

 The hole transport layer used in the present invention is a layer for transporting holes from a hole injection layer formed on an anode or an anode to a light emitting layer and transporting holes from the anode or the hole injection layer to the light emitting layer Materials with high mobility to holes are suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto. The light-

The light emitting material contained in the light emitting layer is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. The light emitting layer may include a host material and a dopant material. In particular, the host material includes the compound represented by Formula 1 and the compound represented by Formula 2 in the present invention. In the above formula (1), preferably, silver is a single bond or phenylene. Preferably, _{2 is a} single bond or phenylene. Preferably,

Phenyl, tert-butyl substituted phenyl, 2019/132545 1 »(: 1 ^ 1 {2018/016773

A substituted or unsubstituted dibenzothiophene such as phenyl substituted with cyano, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylenyl, dimethylfluorenyl, pyridinyl, dibenzofuranyl, dibenzothiophenyl, Phenyl, or 9-phenylcarbazolyl. Preferably, ₂ ¾ and ¾ ₃ are each independently hydrogen, cyano, tert-phenyl-carbazolyl-butyl, phenyl, cyano substituted phenyl, pyridinyl, or 9. Preferably, ¾ ₄ is phenyl, or biphenylyl. Representative examples of the compound represented by the formula (1) are as follows:

2019/132545 1 »(: 1 ^ 1 {2018/016773

In addition, the compound represented by the formula (1) can be prepared by the following reaction scheme 1.

5 [Reaction Scheme 1] 2019/132545 1 »(: 1 ^ 1 {2018/016773

In the above Reaction Scheme 1, the remainder excluding X " is as defined above, and X " is halogen, more preferably bromo, or chloro. The reaction is preferably carried out in the presence of a palladium catalyst and a base as a Suzuki coupling reaction, and the reactor for the Suzuki coupling reaction can be modified as known in the art. The above production method can be further specified in the production example to be described later. In the formula (2), preferably, the formula (2)

Preferably, nu ₂₁ is a single bond or phenylene. Preferably, _{2 is a} single bond or phenylene. Preferably, ₃ and ₄ are each independently phenyl, biphenyl, biphenyl substituted with cyano, or dibenzofuranyl. 2019/132545 1 »(: 1 ^ 1 {2018/016773

Preferably, ₅ and ₆ are each independently selected from the group consisting of phenyl, phenyl substituted with carbazolyl, biphenyl, biphenylyl substituted with cyano, dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, or 9 - < / RTI > phenylcarbazolyl. Preferably, ₇ is phenyl, phenyl substituted with fluoro, phenyl substituted with trifluoromethyl, phenyl substituted with cyano, or biphenyl. Representative examples of the compound represented by the formula (2) are as follows:

32

41

54

2019/132545 1 »(: 1 ^ 1 {2018/016773

In addition, some of the compounds represented by the above formula (2) can be prepared in the same manner as in the following reaction scheme 2, and can be applied to the remaining compounds.

The reaction is carried out in the Suzuki coupling reaction in the presence of a palladium catalyst and in the presence of a base, in the presence of a base, The compound represented by the general formula (1) and the compound represented by the general formula (1) in the light-emitting layer may be the same as those in the general formula 2 is preferably from 99: 1 to 1:99, or from 95: 5 to 5:95. 2019/132545 1 »(: 1 ^ 1 {2018/016773

On the other hand, examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected 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. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto. Electron transport layer

The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Do. Specific examples include: a 1-complex of 8-hydroxyquinoline; Complexes including show _13; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or silver oxide. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer. Electron injection layer

The organic light emitting device according to the present invention may include an electron injection layer between the electron transport layer and the cathode, if necessary. The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has the ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. To prevent migration to the layer, 2019/132545 1 »(: 1 ^ 1 {2018/016773

Further, a compound having excellent thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A nitrogen-containing 5-membered ring derivative, and the like, 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- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10 -hydroxybenzo [ Bis (2-methyl-8-quinolinato), bis (2-methyl-8-quinolinato) ( _0- cresolato ), Gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) . Organic light emitting device

The structure of the organic light emitting device according to the present invention is illustrated in FIG. Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4. Fig. In this structure, the compound represented by Formula 1 and the compound represented by Formula 2 may be included in the light emitting layer. 2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is. In this structure, the compound represented by Formula 1 and the compound represented by Formula 2 may be included in the light emitting layer. 3 is a cross-sectional view of a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, 2019/132545 1 »(: 1 ^ 1 {2018/016773

Emitting layer composed of an electron blocking layer 9, a light-emitting layer 7, an electron transporting layer 8, an electron injection layer 10, and a cathode 4 are shown. In such a structure, the compound represented by Formula 1 and the compound represented by Formula 2 may be included in the light emitting layer. 4 shows an example in which the substrate 1, the anode 2, the hole injecting layer 5, the hole transporting layer 6, the light emitting layer 7, the hole blocking layer 11, the electron transporting layer 8, And a cathode (4). In such a structure, the compound represented by Formula 1 and the compound represented by Formula 2 may be included in the light emitting layer. The organic electroluminescent device according to the present invention is characterized in that the above-

₁₁₎ method, a metal or a metal oxide having conductivity or an alloy thereof is deposited on a substrate to form a positive electrode, and the above-mentioned layers are formed thereon, and then a material usable as a negative electrode is deposited thereon Can be manufactured. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate. Further, the light emitting layer can be formed by a solution coating method as well as a vacuum deposition method for the host and the dopant. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto. In addition to such a method, an organic light emitting device can be manufactured by sequentially depositing an organic material layer and a cathode material on a substrate from a cathode material. However, the manufacturing method is not limited thereto. Meanwhile, the organic light emitting diode according to the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used. The production of the organic light-emitting device according to the present invention will be described in detail below. However, the following specific details are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.

[Production Example 1]

 Production Example 1-1: Preparation of Intermediate 4 Compound

 A-3

 1) Preparation of Compound A-1

 Bromo-3-fluoro-2-iodobenzene (75 g, 249.3 mmol), (5-chloro-

2-methoxyphenyl) boronic acid (51.1 g, 249.3 mmol) was dissolved in tetrahydrofuran (550 mL). To this was added a 2M solution of sodium carbonate (Na ₂ CO ₃₎ (350 mL) and tetrakis (triphenylphosphine) palladium (0) (2.88 g, 2.49 _ol) and refluxed for 11 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the water layer was separated and removed. The mixture was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was recrystallized from chloroform and ethanol to obtain 63.2 g of Compound A- + H] < ⁺ > = 314).

2) Preparation of compound 2

compound

200.3 _{° 0} 1) was dissolved in dichloromethane (750 ₁ )

0 < / RTI > Boron tribromide (20.0 g, 210.3 _ ₀ 1) was slowly added dropwise and stirred for 12 hours. After the reaction was completed, The filtrate was dried over magnesium sulfate and filtered. The filtrate was distilled under reduced pressure and purified by column chromatography to obtain Compound Show-2 (57.9, yield: 96%; 3: [1/1] + ratio ⁺ = 300).

3) Preparation of Compound 3

Compound A-2 (57.9 g, 192.0 mmol) and calcium carbonate (79.6 g, 576.0 mol) were dissolved in N-methyl-2-pyrrolidone (350 mL) and the mixture was heated with stirring for 2 hours. The temperature was lowered to room temperature and reprecipitated in water. (42.1 g, yield: 1%, MS: [M + H] < ⁺ >] was obtained as a colorless oil from Compound A-3 after completely dissolving in dichloromethane, washing with water and drying with anhydrous magnesium sulfate. = 280).

4) Preparation of Compound A-4

Compound A-3 (42.1 g, 149.5_ol) was dissolved in tetrahydrofuran (330 mL), the temperature was lowered to -78 ° C and 2.5 M tert- butyllithium (t_BuLi) (60.4 mL, 151.0 mmol) . After stirring at the same temperature for 1 hour, triisopropylborate (51.8 mL, 224.3 mmol) was added, and the mixture was stirred at room temperature for 3 hours while gradually warming to room temperature. To the reaction mixture was added a 2 N aqueous hydrochloric acid solution (300 mL) and the mixture was stirred at room temperature for 1.5 hours. The resulting precipitate was filtered, washed with water and ethyl ether, and vacuum dried to obtain Compound A-4 (34.3 g, yield 93%; MS: [M + H] ⁺ = 247).

B-3 6-4 B-5 1) Preparation of compound B-1

After dissolving 1-bromo-3-chloro-2-methoxybenzene (100.0 g, 451.5 mmol) in tetrahydrofuran (1000 mL), the temperature was lowered to -78 ° C and 2.5 M tertiary butyl nitrate t-BuLi) (182.4 mL, 456.0 mmol) was slowly added dropwise. After stirring at the same temperature for 1 hour, triisopropylborate (B (iPr) _{3) (156.3} mL, 677.3 mmol) was added and stirred for 3 hours while gradually warming to room temperature. To the reaction mixture was added a 2 N aqueous hydrochloric acid solution (150 mL) and the mixture was stirred at room temperature for 1.5 hours. The resulting precipitate was filtered, washed with water and ethyl ether, and vacuum dried. After drying, the product was recrystallized from chloroform and ethyl acetate and dried to give 84.2 g of compound B-K, yield 90%; MS: [M + H] < ⁺ > = 230).

2) Preparation of compound B-2

Except that Compound B-K84.2 g (451.7 mmol) was used instead of (5-chloro-2-methoxyphenyl) boronic acid as a starting material. -2 (74.6 g, yield 52%; MS: [M + H] < ⁺ > = 314).

3) Production of compound B-3

Compound A-1 in place of the compound ^{B _ 2 (74.6 g, 236.4} mmol) to the process to produce the compound A-2 in the same manner as compound B-3 (60.3 g, 85% yield, except that; MS: [M + H] < ⁺ > = 300). 4) Preparation of compound B-4

(48.1 g, yield 85%; MS: [M + H] +) was prepared in the same manner as Compound A-3 except that Compound B-3 (60.3 g, 199.9 mmol) H] < ⁺ > = 280).

5) Preparation of compound B-5

Compound B-4 (48.1 g, 170.9 mmol) was used instead of Compound A-3 2019/132545 1 »(: 1 ^ 1 {2018/016773

The compound 8-5 (40.1 < RTI ID = 0.0 >

 +

 1) Preparation of compound

A (2-methoxyphenyl 4-chloro) boronic acid _{(51.1 §, 249.3 _ 0 1} ) of the compound 1 and is, in Production Example 1, except for using (5-chloro-2-methoxyphenyl) boronic acid instead of The compound 0-1 (60.1

Yield: 76%; 1 state] ⁺ = 314).

2) Preparation of Compound 02

Compound 0-2 (54.0 yield: 94%; 1: [lambda] < ₂ >) was obtained in the same manner as in the preparation of compound { Large] ⁺ = 300).

3) Preparation of compound 03

0.0 > 02 < / RTI > (54. ¾, 179.1 _ How to manufacture the compound 3 rule except that the _0: 1) and by the same method compound 0-3 (42.2 Deng, yield: 83%; 13: ¾ +} 1] + = 280 were prepared).

4) Preparation of compound 04

Compound 34-4 (34.1) was obtained in the same manner as in the preparation of Compound Show-4 except that Compound 03 (for 42.2, 170.9 _01) was used instead of Compound Show- 2019/132545 1 »(: 1 ^ 1 {2018/016773

₁ yield: 92%; 1: [non ⁺ = 247].

 13-3

 [)-4

 1) Preparation of compound [

1 was prepared in the same manner as in Production Example 1 except that 1-bromo-2-fluoro-3-iodobenzene was used in place of 1-bromo-3-fluoro-2- , The compound 0-1 (58

Yield 74%;

¾3: [¾1] ⁺ = 315).

2) Preparation of compound 1) -2

Compound 0-1 (58

183.8 _ ₀ except for using 1) and compound 71-2 in the same manner as the method for producing the compound 0-2 (49.5 Yield 89%; ¾犯: the ^{[¾1 + 1 {] + =} 300) was prepared.

3) Preparation of compound 1) -3

(40.6 yield 88%; 1: [ū1] ⁺ = 280) was obtained in the same manner as in the preparation of the compound 3, except that the compound [2] (49.5 parts, .

4) Compound 1) Preparation of 4 ^'instead of Compound 3 Compound 1) 3 (40.6 I, 144.2 _ and method for producing the compound rule 4, except that the _0: 1) in the same manner as the compound [1-4 (31.9 (Yield: 90% for 2018/016773; ¾: large) ⁺ = 247).

One

Was the same as the method for producing Compound 1 of Production Example 1 except that 4-bromo-2-fluoro-1-iodobenzene was used in place of 1-bromo-3-fluoro-2- (Yield: 79%; 3: [? 1 + non ⁺ = 315] for 62.3.

2) Preparation of compound 2 £ ^_

Compounds show -1 in place of the compound _{£ -1 (62.3 § 197.4 _ 0} 1) for the £ -2 and compounds in the same method as that for preparing Compound (2) except that (51.7, yield 87%; 1 \ ¾: [ ¾1 + ¾ ⁺ = 300).

3) Preparation of compound table _3

Compound 2 instead of Compound _{£ -2 (51.7 171.5 _ 0 1} ) and the compound I -3 in the same way that the rule Preparation £ -3 (41.8, 87% yield, except for using sugar; ¾13: [1 \ 1+ } 1] ⁺ = 280).

4) Preparation of compound 4

Compound 3 instead of a compound _{3 (41.8 §, 148.5 ■ 0} 1) for a yield of 85%, and compound 4 in a manner the same method to manufacture the compound rule £ -4 (31.2 per except that: 1 [1_] ⁺ = 247 ) Was prepared

 3 4

 1) Preparation of Compound-1

Bromo-2-fluoro-3-iodobenzene and (4-chloro-2-fluorophenyl) boronic acid in place of 1-bromo-3-fluoro- - 2-methoxy-phenyl) and _is, in the same method as that for preparing the compound ₁ of Preparation example 1 compound 1 (60.8 _§ except that the boronic _acid, yield 77%;

[13]: [1] = ⁺ 315).

2) Preparation of compound F-2

2-C (52.0 g, yield 90%); MS: [M + H] < + > was prepared in the same manner as Compound A- H] < ⁺ > = 300).

3) Preparation of Compound F-3

Compound F-3U 2.0 g (yield 86%); MS: [M + H] < + > was obtained in the same manner as in the preparation of Compound A-3, except that Compound F-2 (52.0 g, 172.4 mmol) H] < ⁺ > = 280).

4) Preparation of Compound F-4

(29.8 g, yield 81%; MS: [M + H]) was obtained in the same manner as Compound A-4, except that Compound F-3 (42.0 g, 148.5 mmol) ⁺ = 247). 2019/132545 1 »(: 1 ^ 1 {2018/016773

Preparation Example 1-7: Preparation of Intermediate (5 Compound

 1) Preparation of compound (1)

 Bromo-3-chlorobenzene and (2-chloro-2-methoxyphenyl) boronic acid in place of 1-bromo-3-fluoro-

(Methylthio) phenyl) boronic acid was used in place of the compound (1) in the same manner as in the preparation of the compound 1 of Preparation Example 1,

Yield: 79%; 3: [= within 1] ⁺ = 235).

2) Preparation of compound () -2

Put acetate (420此) in a nitrogen atmosphere to Compound 0-3 (148.5 49.0 ₀ _ 1) In the bromine (13.9此_1, 271 _ ₀ 1), and 651: and the mixture was stirred for 3 hours. After cooling, water was added to the mixture and the precipitated solid was filtered and washed three times with water. The filtered filtrate was recrystallized from acetonitrile and toluene to give compound 0-2 (50.3 g, yield 77%; 1: [1]] ⁺ = 314).

3) Preparation of compound (3)

In compound 0-3 (160 _01 per 50.3) was added acetic acid (530此) was added 35% hydrogen peroxide (16.4 _§) was stirred at room temperature for 5 hours. To the reaction mixture was added an aqueous solution of culprits, stirred for 20 minutes, and ethyl acetate was added thereto to remove the aqueous layer. Dried over anhydrous magnesium sulfate, concentrated under reduced pressure, recrystallized using a mixed solution of tetrahydrofuran and ethyl acetate, and dried to obtain the compound 0-3 (43.2 yield: 87%, 1: [1 1 +} 1] ⁺ = 308) 2019/132545 1 »(: 1 ^ 1 {2018/016773

.

4) Preparation of compound (? -4)

Compound 0-3 (43.2

160 _ ₀ 1) was added to sulfuric acid (220 g) and stirred at room temperature for 5 hours. After the reaction mixture was stirred for 30 minutes, chloroform was added and the mixture was washed three times with water, and ethyl acetate was added thereto to remove the aqueous layer, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, mixed with tetrahydrofuran and ethyl acetate , And dried to give Compound 04 (30.6

Yield 74%,! : ¾ + ¾ ⁺ = 296).

5) Preparation of Compound 5

Compound 0-4 (42.0

148.5 _ ₀ 1) was used in place of Compound 5 (20.4

 +

Compound 11-5 (42) was obtained in the same manner as in the method for producing compound (1-5) of Production Example 1-7, except that 1-bromo-2-chlorobenzene was used in place of 1-bromo-3- _§] : [ū1 + non ⁺ = 235). Preparation Example 1-9: Preparation of Intermediate 1-5 Compound

 5 was prepared in the same manner as in the production of the compound (1-5) of Production Example 1-7, except that 1-bromo-4-chlorobenzene was used in place of 1-bromo-3-chlorobenzene.

 A-6

 1) Preparation of Compound A-5

Compound A-4 (20.0 g, 61 mmol) and 2-chloro-4,6-diphenyltriazine (16.3 g, 61-ol) were dissolved in tetrahydrofuran (200 mL) in a 500 mL round- (100 mL) was added 1.5 M potassium carbonate aqueous solution, tetrakis- (triphenylphosphine) palladium (0.93 g, 1.8 mmol) was added thereto, and the mixture was heated with stirring for 7 hours. The temperature was lowered to room temperature, and the aqueous layer was separated, removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure 2019/132545 1 »(: 1/10 公 018/016773

The compound A-5 (20.5 g, yield 78%, MS: [M + H] ⁺ = 434) was prepared by recrystallization using a mixed solution of tetrahydrofuran and ethyl acetate. 2) Preparation of Compound A-6

 (20.5 g, 47 mmol), bis (pinacolato) diboron (13.2 g, 52 mmol) and potassium acetate (16.2 g, 165 mmol) were mixed in a nitrogen atmosphere and dioxane And heated with stirring. Bis (dibenzylidineacetone) palladium (0.81 g, 1 mmol) and tricyclohexylphosphine (0.8 g, 2 mmol) were added under reflux and heated and stirred for 13 hours. After completion of the reaction, the temperature was lowered to room temperature and then filtered. Water was poured into the filtrate, extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, the residue was recrystallized from ethyl acetate to obtain Compound A-6 (20.7 g, 83%). Preparation Example 2-2: Preparation of intermediate compound 8 Compound

 1) Preparation of compound show-7

Instead of 2-chloro-4,6-diphenyltriazine

2019/132545 1 »(: 1 ^ 1 {2018/016773

Chloro-6-phenyl-1,3,5-triazine was used in place of the compound 7 (14.2

Yield: 68%, ¾: [¾ state 1] ⁺ = 510). ^' 2) Preparation of compound show-8

Compounds show -5 in place of the compound except for using the compound shows _7 and 8 in the same method as that for preparing the compound shows -6 (13.9 _§, yield 82%, 13: [¾ + Non ⁺ = 602!) Preparing a Respectively. [Production Example 3]

 1) Preparation of Compound 6

Compound 6 - 6 (14.2 g) was obtained in the same manner as in the preparation of compound-5 except that Compound 5 was used instead of Compound 5

Yield: 82%,: [!! +}] ⁺ = 434).

2) Preparation of Compound 7

The compound to compound and methods for preparing the compounds I _6 except that the show -5 place of compound 8_6 in the same manner as 8-7 (15.0 _§ 82% yield, 2019/132545 1 »(: 1/10 公 018/016773

¾ 13: [¾! + Ratio ⁺ = 526].

 1) Preparation of Compound 8

Compound 5 and 2-chloro-4- (dibenzothiophen-4-yl) -6-phenyl-1,3,5-triazine were used instead of compound 4 and 2-chloro-4,6- The compound 6-8 (14.5 dinges, yield 66%, < RTI ID = 0.0 > : [占 1 1] ⁺ = 541).

2) Preparation of Compound 9

Instead of compound 5, compound

The compound 6-9 (for 10.6, yield 63%, 隆 13: [隆 1 province] ⁺ = 632) was prepared in the same manner as the compound 6 was prepared.

[Production Example 4]

Production Example 4-1: Preparation of Intermediate 06 Compound 2019/132545 1 »(: 1/10 公 018/016773

 1) Preparation of compound 05

Except compound ¾ with compound 04 instead of compound 04, compound show 5

2) Production of compound (: -6

Compound (5) was used instead of Compound-5

3: ¾ + ratio ⁺ = 526). Production Example 4-2: Preparation of Intermediate 0-8 Compound

2019/132545 1 »(: 1/10 公 018/016773

1) Preparation of compound ^O_7

(4-chloro-6-phenyl-1,3,5-triazine-2-yl) -acetic acid was used instead of compound 04 and 2- chloro-4,6- 5 was prepared in the same manner as in the method for producing compound-5 except that the sol was used,

The yield was 56%, 1: [1 + 1] ⁺ = 523).

2) Preparation of compound 08

Compound I 0-8 (10.8 _§, yield 77% of the compound by the same method as that for preparing a compound shows -6 except for using Compound 07 instead of _5,

.

[Production Example 5]

Production Example 5-1: Preparation of Intermediate 0-6 Compound

2019/132545 1 »(: 1/10 公 018/016773

 1) Preparation of compound 1) -5

Compound 5 was prepared in the same manner as Compound 1 except that Compound 1) -4 and 2-chloro-4,6-diphenylpyrimidine were used instead of Compound 4 and 2-chloro-4,6-diphenyltriazine respectively.

13: Be ⁺ = 433).

2) Preparation of compound [

Compounds show ^_ 5 instead of compound 1) and the compound according to the same method as for the preparation of compounds show _6 except that the -5 1) -6 (9.8 _§, yield 85%, ¾13: [! 1 ] + = 525 ). Production Example 5-2: Preparation of Intermediate 0-8 Compound

2019/132545 1 »(: 1/10 公 018/016773

 1) Preparation of compound 1) -7

Compound 1) -4 and 2-chloro-4- (dibenzothiophen-4-yl) -6-phenyl-1,3,5- The compound 0-7 (14.0 _,, yield 64%, 1: [in 1] ⁺ = 541) was prepared in the same manner as the compound 5 except that triazine was used.

2) Preparation of compound [

The compound 0-8 (12.4 < RTI ID = 0.0 >

Yield: 75%, 꺿 꺿 꺿 꺿 꺿 꺿 꺿 꺿 꺿 꺿 꺿 꺿 꺿 꺿 꺿 1 1] ⁺ = 632.

[Production Example 6]

Production Example 6-1: Preparation of intermediate compound 6

2019/132545 1 »(: 1/10 公 018/016773

(13 _§, yield: 74%, ¾13: [¾1 + non ⁺ = 434]) was prepared in the same manner as in the method for producing Compound show 5 except that Compound 4 was used in place of Compound 4 Respectively.

2) Preparation of compound £ -6

(11.5 _§, yield: 73%, ¾: [¾1] ⁺ = 526) was obtained in the same manner as in the method for producing compound 6 except that compound £ _5 was used instead of compound 5 .

 Compound 4 and 2-chloro-4,6-diphenyltriazine were used instead of Compound 4 and 2-chloro-4,5-

Using 2-chloro-4- (dibenzofuran-4-yl) -6-phenyl-1,3,5-triazine 2019/132545 1 »(: 1/10 公 018/016773

(13.3 mol%, yield: 63%, 1: [1 1 +} 1] ⁺ = 524) was prepared in the same manner as the compound 5 was prepared.

2) Preparation of compound Table-8

Compound 10 was obtained in the same manner as in the method for producing Compound-6 except that Compound No. 5-7 was used instead of Compound No. 5-8

Yield: 64%, 꺿 꺿 13 13: [베 ber] ⁺ = 616).

[Production Example 7]

 Production Example 7-1: Preparation of intermediate 6 compound

 1) Preparation of compound 15

Compound 4 was obtained in the same manner as Compound 4 except that Compound 4 was used instead of Compound 4 and 2-chloro-4,6-diphenyltriazine was used instead of Compound 4 and 2- (4-chloro-6-phenyl-1,3,5- 5 was prepared in the same manner as the compound-5 except that the sol was used, the compound

Yield: 54%, 1: [1 1 + non ⁺ = 599).

2) Preparation of Compound-6

Compound 1 ^ 6 (10.1 yield 66%, ¾6: [¾1 + 11] ⁺ = 691) was prepared in the same manner as in the preparation of Compound 6 except that compound 5 was used instead of compound 5 . 2019/132545 1 »(: 1/10 公 018/016773

Production Example 7-2: Preparation of Intermediate 1? -8 Compound

 1) Preparation of Compound 7

Except that Compound 4 and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine were used instead of Compound 4 and 2-chloro-4,6- The compound 7 (14 _,, yield 68%, 1: [] tert-butyl {) ⁺ = 510) was prepared in the same manner as the compound 5.

2) Preparation of compound-8-The compound 8 (12.7 g, yield) was obtained in the same manner as in the preparation of the compound 6 except that 1 -7 of the compound was used instead of 5

Yield: 77%, 3: [1 \ 1 state] ⁺ = 602). [Production Example 8]

Preparation Example 8-1: Preparation of intermediate 7 compound 2019/132545 1 »(: 1/10 公 018/016773

 1) Preparation of compound (6) -6

(13 _§, yield: 56%, ¾: [¾! +} 1] ⁺⁾ was obtained in the same manner as the compound-5 except that the compound = 450).

2) Preparation of compound (-7

The compound 0-7 (10.9 balls, 70% yield, 3: [ū1] ⁺ = 542) was prepared in the same manner as the compound-6 except that Compound-6 was used instead of Compound- Respectively.

 1) Preparation of compound [1-6

Except that Compound 11-5 was used instead of Compound Show-4. 2019/132545 1 »(: 1/10 公 018/016773

(13.9 ding yield 58%, 짹 13: [짹 1 +} {] ⁺ = 450) was prepared in the same manner as the above compound.

2) Preparation of compound 11-7

Instead of compound-5

Compound 11-7 (12.1 < RTI ID = 0.0 >

Yield: 72%, ¾: [ū1] ⁺ = 542). Preparation Example 8-3: Preparation of Intermediate 1-7 Compound

 1) Preparation of compound 1-6

Compound 1 was prepared in the same manner as Compound 1 and Compound 1 was used in place of Compound 4 and 2-chloro-4,6-diphenyltriazine. (20.3 mass%, yield: 67%, 1: ¾ + 11] ⁺ = 526) was prepared in the same manner as Compound 5 except that 3, 5-triazine was used.

2) Preparation of compound 1-7

The compound 1-7 (13.9 < RTI ID = 0.0 >

Yield: 58%, 3: [1 & lt ^; + ^& gt ^; + ratio = 618).

[Production Example 9] Production Example 9-1: Preparation of Intermediate] -1 Compound

 (15 g, 57.8 mmol) and phenylboronic acid (7.9 g, 64.7 mmol) were dissolved in tetrahydrofuran (250 mL), followed by the addition of 1.5 M aqueous potassium carbonate solution (120 mL) was added and tetrakis-

(Triphenylphosphine) palladium (1.4 g, 1.28 mmol) was added thereto, followed by heating and stirring for 7 hours. The mixture was cooled to room temperature and the water layer was separated and removed. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, recrystallized from chloroform and ethanol, and dried to obtain 14.1 g of the compound J-K, yield 83% + H] < ⁺ > = 297). Production Example 9-2: Preparation of Intermediate 3-2 Compound

ᅩ 2

The compound 2 was prepared in the same manner as in the preparation of the compound _1-1 except that [1,1'-biphenyl] -4-ylboronic acid was used in place of the phenylboronic acid. Production Example 9-3: Preparation of Intermediate-3 Compound

The compound I-3 was prepared in the same manner as in the preparation of the compound 1-1. Production Example 9-4: Preparation of Intermediate 1 to 4 Compound

Except that dichlorobenzofura [3,2-1] pyrimidine was used as a starting material. Production Example 9-5: Preparation of intermediate: -5 compound

(21.4 g, 0.06 mol) was dissolved in dioxane (200 rnL), K ₃ PO ₄ (21.4 g, 0.1 mol) was added (0.26 g, 0.5-ol), and the mixture was heated with stirring for 13 hours. The temperature was lowered to room temperature, and the aqueous layer was separated and removed, followed by drying with anhydrous magnesium sulfate Concentration under reduced pressure and ethyl acetate It was prepared -5 (14.1 _§ yield 81%, [¾ +} { !] + = 373): after recrystallization using dried compound. Production Example 9-6: Preparation of Intermediate-6 Compound

 -6 was prepared in the same manner as in the preparation of the compound 5, except that (3-chlorophenyl) boronic acid was used in place of (4-chlorophenyl) boronic acid.

[Example]

 Example 1: Preparation of Compound 1

Compound A-6 (10 g, 19ol) and compound J-K (5.46 g, 19 mmol) were placed in tetrahydrofuran (120 mL) under nitrogen atmosphere and stirred and refluxed. Potassium carbonate (7.89 g, 57 mmol) was dissolved in water (50 mL), and the mixture was sufficiently stirred. Bis (tri-1-butylphosphine) palladium (0) (0.1 g, 0.2 mmol) was added thereto. After 9 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried with magnesium sulfate. Thereafter, the organic layer was distilled off under reduced pressure, and recrystallized using a mixed solution of tetrahydrofuran and ethyl acetate. The resulting solid was filtered and dried to give Compound 1 (7.8 g, yield 62%, MS: [M + H] ⁺ = 660). 2019/132545 1 »(: 1 ^ 1 {2018/016773

Examples 2 to 43: Preparation of compounds 2 to 43

 The starting materials were prepared in the same manner as in Example 1, except that the starting materials were changed according to the following Tables 1 and 2 to prepare the compounds 2 to 43. The structure, shape, yield, and ¾ are summarized in the following table.

 [Table 1]

2019/132545 1 »(: 1/10 公 018/016773

2019/132545 1 »(: 1/10 公 018/016773

2019/132545 1 »(: 1/10 公 018/016773

 [Table 2]

2019/132545 1 »(: 1/10 公 018/016773

2019/132545 1 »(: 1/10 公 018/016773

2019/132545 1 »(: 1/10 公 018/016773

 2-1

To a solution of dibenzo [b, d] furan-2-ylboronic acid (5.7 g, 27 mmol) and dibenzo [b, d] biphenyl-4-yl) , 27 mmol) was dispersed in tetrahydrofuran (80 mL), and a 2M aqueous potassium carbonate solution (aq. K ₂ CO _{3) (40} mL, 81 mmol) was added and tetrakis triphenylphosphinopaladdom [Pd PPh _{3) 4] (0.3} g, 1 mol%) was added thereto, and the mixture was refluxed for 6 hours. The temperature was lowered to room temperature, the water layer was removed, and the filtrate was concentrated under reduced pressure. Ethyl acetate was added thereto, and the mixture was stirred under reflux for 1 hour. After cooling to room temperature, the solid was filtered. The resulting solid was dissolved in reflux, and ethyl acetate was added thereto to recrystallize the compound 2-1 (11.5 g, yield 73%, MS: [M + H] ⁺ = 486). Example 45: Preparation of compound 2-2

A solution of 9 - ([l, r-biphenyl] -3-yl) -3-bromo-9H-carbazole (16 g, (19.7 g, yield: 77%) was obtained in the same manner as in the production of the compound 2-1, using the compound (2-b) 2019/132545 1 »(: 1/10/01/0/016773 3: [State of 1] ⁺ = ^: 637). Example 46: Preparation of compound 2-3

Compound 20 (20.6, yield: 80%, 13: [= in] ⁺ = 637) was prepared in the same manner as the compound 2-1. Example 47: Preparation of compound 2-4

9 - ([1, 1 '- biphenyl] - 4 - yl) - 3-Bromo-carbazol-911- (per 16 40 ₀ _ 1) and 9 - ([1,1'_-biphenyl] - 4-yl) -hex-carbazole-

40 _ _0: 1) to obtain compound 2-4 (22.5 Ding, 88% yield in the same manner as in preparation of compounds 2-1 using, ¾: was prepared [for ¾1] ⁺ = 637). Example 48: Preparation of compound 2-5 2019/132545 1 »(: 1 ^ 1 {2018/016773

9 - ([1,1'_-biphenyl] - 4 - yl) - 3-bromo-For-carbazole (16 I, 50 _ ₀₁₎ and 9 - ([1,1'_-biphenyl] - 4 Yl) -ac-carbazol-3-yl) boronic acid (18.03

50 _ ₀₁₎ the production method and 2-11, the same method as compound 2-4 (yield: 19.7 71% of compound was obtained was prepared a [^ chopping] ⁺ = 561).

[Experimental Example]

 Experimental Example 1

^ _0, 1111 ₍₁₆₎ into a thin film-coated glass substrate to a thickness of 1,300 were dissolved in distilled water人detergent and washed with ultrasonic waves. At this time, the detergent was used as a Fischer Inc. (nyora _0. 0) was used as a product is in millimeters of distilled water pore Inc. (出11 ₀ 0 ₀₎ 2 filtered distilled water to a filter drive () of the product. After washing for 30 minutes, the plate was washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator. On the prepared 110 transparent electrodes, the following compound was thermally vacuum-deposited to a thickness of 50 to form a hole injection layer. Then, a hole transport layer was formed by thermally vacuum depositing the following compound (1) in a thickness of 250 angstroms, and an electron blocking layer was formed thereon by vacuum evaporation of the following compound: Compound 1 (host), compound 2-5 (host), and compound-1 (phosphorescent dopant) shown below were co-deposited at a weight ratio of 44:44:12 2019/132545 1 »(: 1/10 公 018/016773

A light-emitting layer having a thickness of 400 was formed. The following compound (1) was vacuum deposited on the light emitting layer to a thickness of 250 angstroms. Further, the following ET-2 compound was co-deposited with a dye having a thickness of 100% to a thickness of 2% to form an electron transport layer and an electron injection layer. Aluminum was deposited on the electron injecting layer to a thickness of 1,000 to form a cathode.

In the above process, the deposition rate of the organic material is 0.4 0.7

The deposition rate of aluminum was maintained for 2 persons and the degree of vacuum during deposition was maintained at 1><10 ^_7 5X 1 ( ⁸ pcs). Experimental Examples 2 to 14

 An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the host compound used in forming the light emitting layer was used as shown in Table 3 below. Comparative Experimental Examples 1 to 13

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the host compound used in forming the light emitting layer was used as shown in Table 3 below. In the following Table 3, the compounds 01, 02 and 03 are respectively as follows. 2019/132545 1 »(: 1 ^ 1 {2018/016773

The voltage, efficiency, color coordinates, and lifetime were measured by applying current to the organic light emitting device manufactured in Experimental Examples 1 to 14 and Comparative Experimental Examples 1 to 13, and the results are shown in Table 3 below. 195 denotes the time required for the luminance to be reduced to 95% from the initial luminance.

 [Table 3]

2019/132545 1 »(: 1 ^ 1 {2018/016773

As shown in Table 3, the organic luminescent device manufactured using the compound of the present invention as a host of the luminescent layer exhibits excellent performance in terms of driving voltage and lifetime in comparison with the organic luminescent device of the comparative example . In addition, when the compound represented by the formula (1) and the compound represented by the formula (2) were used together, it was confirmed that the compound exhibited the high efficiency and long life characteristics as compared with the case without the compound. Experimental Example 15

 On the transparent electrode prepared as in Experimental Example 1, the following compound

A hole injection layer was formed by thermal vacuum deposition at a thickness of 500 angstroms. The following compound-1 was thermally vacuum-deposited on the hole injection layer to a thickness of 800 pixels, and the following compound-3 was sequentially vacuum-deposited to a thickness of 500 to form a hole transport layer. Compound (host), Compound 2-3 (host) and Compound (00) (phosphorescent dopant) prepared above were co-deposited on the hole transport layer at a weight ratio of 47: 47: 6 to form a 350 nm thick light emitting layer. The seedlings 3 on the light emitting compound to the vacuum vapor deposition to form a hole blocking layer, and to increase on the hole blocking -4 compounds and needle ninae _{八™ 0 11 ^ 01 ^ 6} ) with a thickness of 1 to 50: 1 in a weight ratio of Vacuum evaporation was performed to form an electron transport layer having a thickness of 250 mm. Lithium fluoride (Ni) was sequentially deposited on the electron transport film to a thickness of 10, and aluminum was deposited thereon to a thickness of 1,000 to form a cathode.

2019/132545 1 »(: 1 ^ 1 {2018/016773

In the above process, the deposition rate of the organic material was maintained in the range of 0.4 to 0.7, the lithium fluoride in the cathode was 0.3 to 8%, and the deposition rate in the aluminum was maintained to be 2 to 8, () - ⁷ 5X 10 ^{· ®} is maintained a ^. Experimental Examples 16 to 33

 An organic light emitting device was prepared in the same manner as in Experimental Example 15, except that the host compound used in forming the light emitting layer was used as shown in Table 4 below. When a mixture of two kinds of compounds is used as a host, parentheses mean the weight ratio between the host compounds. Comparative Experimental Examples 14 to 30

An organic light emitting device was prepared in the same manner as in Experimental Example 15, except that the host compound used in forming the light emitting layer was used as shown in Table 4 below. When a mixture of two kinds of compounds is used as a host, parentheses mean the weight ratio between the host compounds. In Table 4, compounds 01, 02 and 03 are the same compounds as those used in Table 3, respectively. The organic compounds prepared in Experimental Examples 15 to 33 and Comparative Experimental Examples 14 to 30 2019/132545 1 »(: 1 ^ 1 {2018/016773

The current, voltage, efficiency and lifetime of the light emitting device were measured, and the results are shown in Table 4 below. 195 represents the time required for the luminance to be reduced to 95% from the initial luminance.

 [Table 4]

As shown in Table 4 above, the combination of the compounds of the present invention 2019/132545 1 »(: 1 ^ 1 {2018/016773

In comparison with the comparative example, it was confirmed that the emissive layer exhibits excellent characteristics in terms of driving voltage and lifetime similarly to the experiment described above.

 DESCRIPTION OF REFERENCE NUMERALS

 Electron blocking layer 10: electron injection layer

 11: hole blocking layer

Claims

2019/132545 1 (: 1 ^ {2018/016773 [Patent Claims]

 [Claim 1]

 anode; A negative electrode opposed to the positive electrode; And at least one organic material layer provided between the anode and the cathode,

 Wherein the organic layer includes a light emitting layer,

 Wherein the light emitting layer comprises a compound represented by the following formula (1) and a compound represented by the following formula (2)

 Organic Light Emitting Device:

 [Chemical Formula 1]

 In Formula 1,

[Clay marbling; Or substituted or unsubstituted _3-60 arylene,

2 union coupling; Substituted or unsubstituted 0 _{6-60 arylenes} ,

0 _1-60 alkyl, substituted or unsubstituted 0 _6-60 aryl; Or a substituted or unsubstituted ratio 0, and 0 _2-60 heteroaryl comprising 0 or 2 heteroatoms selected from the group consisting of &lt; RTI ID = 0.0 &gt;

Cyano, substituted or unsubstituted- ₆₀ alkyl, substituted or unsubstituted 0 _6-60 aryl; Or a substituted or unsubstituted one 0 _2-60 heteroaryl group containing one or more heteroatoms 0, selected from the group consisting of and,

₄ is a substituted or unsubstituted 0 _6-60 aryl, 2019/132545 1 »(: 1 ^ 1 {2018/016773

(2)

 In Formula 2,

¾ and _{1, 2 ¾,} ¾ _3, and ₄ ¾ Medium I -1 _{^ 21-1,} and the other is hydrogen,

And _2, and the other is hydrogen, with the proviso that, a ₁ ¾ - - 1¾ _1, ¾ _{2, 3} ¾, and ¾ ₄ Heavy _I-22厂slow or 1½ and the -1 _22, a ¾ _2-厂 I and this ¾ -1 _{2 22} ^_ ₂ or, ₃ ¾ -1 _{^ 21- 1} and 1½ or a ₂ ^_ _2, I ₂₄ -1 _{^ 21- 1} and ¾ _{4 2-22} Ann crying, except,

Or substituted or unsubstituted 0 _{6-60 arylenes} ,

2 is a divalent bond or a substituted or unsubstituted 0 _6-60 arylene,

¾ is 0, or,

(3)

(3)

 In Formula 3,

 Lt; / RTI &gt; are each, independently,

3 and ₄ are each independently a substituted or unsubstituted 0 _6-60 aryl; Or a substituted or unsubstituted 0, and either 0 _2-60 heteroaryl group containing one or more hetero atoms selected from the configuration in doeneungun,

 2 is selected from the group consisting of:

2019/132545 1 »(: 1 ^ 1 {2018/016773

In the above,

 Are each independently or a group, at least one of them is a group,

 Is 0, or 3,

5 _{, 6} and ₇ are each independently a substituted or unsubstituted 0 _6-60 aryl; Or a substituted or unsubstituted ratio 0, and 0 _2-60 heteroaryl comprising at least one heteroatom selected from the group consisting of:

[Claim 2]

 The method according to claim 1,

 Lt; RTI ID = 0.0 &gt; phenylene, &lt; / RTI &

 Organic light emitting device.

[Claim 3]

 The method according to claim 1,

 2 &lt; / RTI &gt; is a single bond,

 Organic light emitting device.

[4]

 The method according to claim 1,

And _n is an integer of ₁ to 3. [0042] In formula ( ₁₎ , R &lt; ₁ &gt; is a cyclohexyl group, phenyl, tert- Benzofuranyl, dibenzothiophenyl, dibenzothiophenyl substituted with phenyl, or 9-phenylcarbazolyl,

 Organic light emitting device.

[Claim 5]

 The method according to claim 1,

2 and 3 are each independently selected from the group consisting of hydrogen, cyano, tert-butyl, phenyl, phenyl substituted with cyano, pyridinyl, or 9- 0 2019/132545 1 »(1 ^ 1 {2018/016773

Organic light emitting device.

[Claim 6]

 The method according to claim 1,

 Organic light emitting device.

[7]

In the ^low, 11,

 The compound represented by the formula (1) is any one selected from the group consisting of

Organic Light Emitting Device:

110 2019/132545 1 »(1 ^ {2018/016773

[8]

 The method according to claim 1,

Wherein the formula (2) is represented by any one of the following formulas: 2019/132545 1 »(: 1/10 公 018/016773

Organic light emitting device

[Claim 9]

 The method according to claim 1,

1 &_lt; / RTI &gt; _{21 is an} acyl group,

 Organic light emitting device.

Claim 10

 The method according to claim 1,

2 &lt; ₂ &gt; is a single bond,

 Organic light emitting device.

Claim 111

 The method according to claim 1,

3 and ₄ are each independently phenyl, biphenyl, biphenylyl substituted with cyano, or dibenzofuranyl,

 Organic light emitting device.

Claim 12

 The method according to claim 1,

5 and ₆ are each independently selected from the group consisting of phenyl, phenyl substituted with carbazolyl, biphenyl, biphenyl substituted with cyano, dimethylfluorenyl, dibenzofuranyl, 2019/132545 1 »(: 1 ^ 1 {2018/016773

Dibenzothiophenyl, or 9-phenylcarbazolyl,

 Organic light emitting device.

Claim 13

 The method according to claim 1,

 7 is phenyl, phenyl substituted with fluoro, phenyl substituted with trifluoromethyl, phenyl substituted with cyano, or biphenyl,

 Organic light emitting device. 14.

 The method according to claim 1,

 Wherein the compound represented by Formula 2 is any one selected from the group consisting of

Organic Light Emitting Device:

120

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