KR102040226B1 - Organic light emitting device - Google Patents

Abstract

The present invention provides an organic light emitting device.

Description

Organic light emitting element {ORGANIC LIGHT EMITTING DEVICE}

The present invention relates to an organic light emitting device.

In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent brightness, driving voltage and response speed characteristics, many studies have 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 layer is often formed of a multi-layered structure composed of different materials. For example, the organic layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. When it falls back to the ground, it glows.

There is a continuous demand for the development of new materials for organic materials used in such organic light emitting devices.

Korean Patent Publication No. 10-2000-0051826

The present invention relates to an organic light emitting device.

The present invention is a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes a first host represented by Chemical Formula 1 and An organic light emitting device including a second host represented by Formula 2 is provided.

[Formula 1]

In Chemical Formula 1,

Ar ₁ is substituted or unsubstituted C _6-60 aryl,

[Formula 2]

In Chemical Formula 2,

X is O or S,

R ₁ to R ₄ are each independently hydrogen, substituted or unsubstituted C _6-60 aryl, substituted or unsubstituted C _2-60 heteroaryl including one or more of O, N, Si and S, or Formula 3,

R ₅ is a substituted or unsubstituted C _6-60 aryl group, C _2-60 heteroaryl including one or more of substituted or unsubstituted O, N, Si and S, or

At least one of R ₁ to R ₅ is the formula (3),

[Formula 3]

In Chemical Formula 3,

Z ₁ to Z ₅ are each independently N or CR ₆ ,

R ₆ is hydrogen, substituted or unsubstituted C _6-60 aryl, or C _2-60 heteroaryl including one or more of substituted or unsubstituted O, N, Si, and S.

The first host represented by Chemical Formula 1 and the second host represented by Chemical Formula 2 may be used as a light emitting material of the organic light emitting device to improve low driving voltage and / or lifetime characteristics and efficiency of the organic light emitting device. .

FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG.
2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4. It is.

Hereinafter, the present invention will be described in more detail to help understand the present invention.

The present invention provides an organic light emitting device using a first host represented by Chemical Formula 1 and a second host represented by Chemical Formula 2 as a host of the light emitting layer.

는 다른 화합물에 연결되는 결합을 의미한다. In this specification,

Means a bond that is linked to another compound.

In this specification the term "substituted or unsubstituted" may be substituted or means a unsubstituted by R _a, R _a is heavy hydrogen, a halogen, a cyano group, a nitro group, an amino group, an alkyl group having 1 to 40 carbon atoms, 1 to 40 haloalkyl groups, substituted or unsubstituted O, N, Si and S containing at least one heteroalkyl group containing 1 to 40 carbon atoms, substituted or unsubstituted O, N, Si and S at least one It may be a heterohaloalkyl group having 1 to 40 carbon atoms, or an alkenyl group having 2 to 40 carbon atoms.

Halogen herein may be fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group having 1 to 40 carbon atoms may be a straight chain, branched chain or cyclic alkyl group. Specifically, the alkyl group having 1 to 40 carbon atoms is a straight chain alkyl group having 1 to 40 carbon atoms; Linear alkyl groups having 1 to 20 carbon atoms; Straight chain alkyl groups having 1 to 10 carbon atoms; Branched or cyclic alkyl groups having 3 to 40 carbon atoms; Branched or cyclic alkyl groups having 3 to 20 carbon atoms; Or a branched or cyclic alkyl group having 3 to 10 carbon atoms. More specifically, the alkyl group having 1 to 40 carbon atoms is methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, t-butyl, n-pentyl, iso-pentyl, neo-pentyl group or cyclohexyl group. However, the present invention is not limited thereto.

In the present specification, the heteroalkyl group having 1 to 40 carbon atoms may be one or more carbons of the alkyl group are each independently substituted with O, N, Si or S. For example, as an example of a linear alkyl group, the heteroalkyl group in which carbon number 1 of the n-butyl group is substituted with O is n-propoxy group, the heteroalkyl group substituted with N is n-propylamino group, and the heteroalkyl group substituted with Si is n And a heteroalkyl group substituted with S is an n-propylthio group. As an example of the branched alkyl group, the heteroalkyl group in which carbon number 1 of the neo-pentyl group is substituted with O is a t-butoxy group, the heteroalkyl group substituted with N is a t-butylamino group, and the heteroalkyl group substituted with Si is t A -butylsilyl group, and the heteroalkyl group substituted with S is a t-butylthio group. In addition, as an example of a cyclic alkyl group, the heteroalkyl group in which the carbon number 2 of the cyclohexyl group is substituted with O is a 2-tetrahydropyranyl group, the heteroalkyl group substituted with N is a 2-piperidinyl group, The heteroalkyl group substituted with Si is a 1-sila-cyclohexyl group, and the heteroalkyl group substituted with S is a 2-tetrahydrothiopyranyl group. Specifically, the heteroalkyl group having 1 to 40 carbon atoms has a straight, branched or cyclic hydroxyalkyl group having 1 to 40 carbon atoms; Linear, branched or cyclic alkoxy groups having 1 to 40 carbon atoms; Linear, branched or cyclic alkoxyalkyl groups having 2 to 40 carbon atoms; Linear, branched or cyclic aminoalkyl groups having 1 to 40 carbon atoms; Linear, branched or cyclic alkylamino groups having 1 to 40 carbon atoms; Linear, branched or cyclic alkylaminoalkyl groups having 1 to 40 carbon atoms; Linear, branched or cyclic silylalkyl (oxy) groups having 1 to 40 carbon atoms; Linear, branched or cyclic alkyl (oxy) silyl groups having 1 to 40 carbon atoms; Linear, branched or cyclic alkyl (oxy) silylalkyl (oxy) groups having 1 to 40 carbon atoms; Linear, branched or cyclic mercaptoalkyl groups having 1 to 40 carbon atoms; Linear, branched or cyclic alkylthio groups having 1 to 40 carbon atoms; Or a straight, branched or cyclic alkylthioalkyl group having 2 to 40 carbon atoms. More specifically, the heteroalkyl group having 1 to 40 carbon atoms has a hydroxymethyl group, methoxy group, ethoxy group, n-propoxy group, iso-propoxy group, t-butoxy group, cyclohexoxy group, methoxymethyl group, iso-prop Foxymethyl group, cyclohexoxymethyl group, 2-tetrahydropyranyl group, aminomethyl group, methylamino group, n-propylamino group, t-butylamino group, methylaminopropyl group, 2-piperidinyl group, n- Propylsilyl group, trimethylsilyl group, dimethylmethoxysilyl group, t-butylsilyl group, 1-sila-cyclohexyl group, n-propylthio group, t-butylthio group or 2-tetra Hydrotepyyranyl (2-tetrahydrothiopyranyl) group, etc. are mentioned. However, the present invention is not limited thereto.

In the present specification, an alkenyl group having 2 to 40 carbon atoms may be a straight chain, branched chain or cyclic alkenyl group. Specifically, the alkenyl group having 2 to 40 carbon atoms has a straight chain alkenyl group having 2 to 40 carbon atoms; Linear alkenyl groups having 2 to 20 carbon atoms; Linear alkenyl groups having 2 to 10 carbon atoms; Branched alkenyl groups having 3 to 40 carbon atoms; Branched alkenyl groups having 3 to 20 carbon atoms; Branched alkenyl groups having 3 to 10 carbon atoms; Cyclic alkenyl groups having 5 to 40 carbon atoms; Cyclic alkenyl groups having 5 to 20 carbon atoms; Or a cyclic alkenyl group having 5 to 10 carbon atoms. More specifically, the alkenyl group having 2 to 40 carbon atoms may be an ethenyl group, propenyl group, butenyl group, pentenyl group or cyclohexenyl group. However, the present invention is not limited thereto.

In the present specification, the aryl group having 6 to 60 carbon atoms may be a monocyclic aryl group or a polycyclic aryl group. Specifically, the aryl group having 6 to 60 carbon atoms is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms. More specifically, the aryl group having 6 to 60 carbon atoms may be a phenyl group, a biphenyl group or a terphenyl group as a monocyclic aryl group, and as a polycyclic aryl group, a naphthyl group, anthracenyl group, phenanthryl group, triphenylenyl group, pyre Or a phenyl group, a perrylenyl group, a chrysenyl group, or a fluorenyl group. However, the present invention is not limited thereto.

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.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 heteroaryl group having 2 to 60 carbon atoms may be one or more carbons of the aryl group are each independently substituted with O, N, Si or S. For example, the heteroaryl group in which the carbon number 9 of the fluorenyl group is substituted with O is a dibenzofuranyl group, the heteroaryl group substituted with N is a carbazolyl group, and the heteroaryl group substituted with Si is a 9-sila-fluoroenyl group The heteroaryl group substituted with S is a dibenzothiophenyl group. Specifically, a heteroaryl group having 2 to 60 carbon atoms is a heteroaryl group having 2 to 30 carbon atoms; Or a heteroaryl group having 2 to 20 carbon atoms. More specifically, a heteroaryl group having 2 to 60 carbon atoms has a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, Triazine group, triazole group, acridil group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazinopyra Genyl group, isoquinoline group, indole group, carbazole group, 9-phenylcarbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group , Phenanthroline, thiazolyl, isooxazolyl, oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, and dibenzofuranyl, but are not limited thereto. no.

Ar ₁ in Formula 1 may be C _6-20 aryl. Specifically, Ar ₁ in Formula 1 may be a phenyl group or a biphenyl group.

In Formula 1, 1a, 2a, 3a or 4a of carbazole is connected to 1b, 2b, 3b or 4b of central dibenzofuran. Specifically, in Formula 1, 2a may be connected to 1b, 2b, 3b, or 4b, or 3a may be connected to 1b, 2b, 3b, or 4b.

In addition, 1c, 2c, 3c or 4c of the central dibenzofuran in Formula 1 is connected to 1d, 2d, 3d or 4d of the terminal dibenzofuran. Specifically, in Formula 1, 1c may be linked with 1d or 3d, or 3c may be linked with 1d or 3d.

The first host represented by Formula 1 may be selected from the group consisting of the following compounds.

Meanwhile, the compound represented by Chemical Formula 1 may be prepared by the same method as in Scheme 1 below.

Scheme 1

In Scheme 1, Ar ₁ is as defined above, X 'is halogen and preferably bromo, or chloro.

Scheme 1 is a Suzuki coupling reaction, preferably carried out in the presence of a palladium catalyst and a base, the reactor for the Suzuki coupling reaction can be changed as known in the art. The manufacturing method may be more specific in the production examples to be described later.

In Formula 2, at least one of R ₁ to R ₅ is Formula 3.

Specifically, when R ₅ is the formula 3 R _{1 To} R _{4 It} may be as follows.

R ₁ to R ₄ are each independently hydrogen, substituted or unsubstituted C _6-60 aryl, or C _2-60 heteroaryl including one or more of substituted or unsubstituted O, N, Si, and S have.

Specifically, at least one of R ₁ to R ₄ is substituted or unsubstituted C _6-60 aryl, or C _2-60 heteroaryl including one or more of substituted or unsubstituted O, N, Si, and S , The remainder may be hydrogen.

More specifically, at least one of R ₁ to R ₃ is substituted or unsubstituted C _6-60 aryl, or C _2-60 heteroaryl including at least one of substituted or unsubstituted O, N, Si and S , The remainder is hydrogen, and R ₄ may be hydrogen.

Meanwhile, when any one of R ₁ to R ₄ is formula 3, the remaining R and R ₅ may be as follows.

Any one of R ₁ to R ₄ is formula (3), and the other is hydrogen, substituted or unsubstituted C _6-60 aryl, or C comprising one or more of substituted or unsubstituted O, N, Si, and S _2-60 heteroaryl, R ₅ may be substituted or unsubstituted C _6-60 aryl, or C _2-60 heteroaryl including one or more of substituted or unsubstituted O, N, Si, and S .

Specifically, any one of R ₁ to R ₄ is formula (3), the remaining is hydrogen, R ₅ is substituted or unsubstituted C _6-60 aryl, or substituted or unsubstituted O, N, Si and S C _2-60 heteroaryl, including one or more.

More specifically, any one of R ₁ to R ₃ is formula 3, the remaining is hydrogen, R ₄ is hydrogen, R ₅ is substituted or unsubstituted C _6-60 aryl, or substituted or unsubstituted O _Or C _2-60 heteroaryl including at least one of N, Si, and S.

In Chemical Formula 2, R ₁ to R ₄ are each independently hydrogen; Or monovalent moieties derived from arene or heteroarene selected from the group consisting of biphenyl, terphenyl, phenanthrene, triphenylene, 9-phenylcarbazole and dibenzofuran; Or Formula 3,

R ₅ is a monovalent moiety derived from arene or heteroarene selected from the group consisting of biphenyl, terphenyl, phenanthrene, triphenylene, 9-phenylcarbazole and dibenzofuran; Or Formula 3 above,

At least one of R ₁ to R ₅ may be represented by Chemical Formula 3.

In Formula 3, at least two or more of Z ₁ , Z ₃ and Z ₅ may be N.

Specifically, in Formula 3, at least two or more of Z ₁ , Z ₃ and Z ₅ are N, the remainder is CH, Z ₂ and Z ₄ is CR ₆ , wherein R ₆ is a phenyl group, a biphenyl group or a terphenyl group Can be.

The second host represented by Formula 2 may be selected from the group consisting of the following compounds.

On the other hand, when R ₅ of the compound represented by the formula (2) is represented by the formula (3), it can be prepared by the same method as in Scheme 2, it can be applied to the remaining compounds.

Scheme 2

In Reaction Scheme 2, except for X ″ is as defined above, X ″ is halogen and preferably bromo, or chloro.

Scheme 2 is a Suzuki coupling reaction, preferably carried out in the presence of a palladium catalyst and a base, the reactor for the Suzuki coupling reaction can be changed as known in the art. The manufacturing method may be more specific in the production examples to be described later.

The organic light emitting device of the present invention comprises a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode.

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

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

FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG. In such a structure, the emission layer includes a first host represented by Formula 1 and a second host represented by Formula 2.

2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4. It is. Even in such a structure, the emission layer includes a first host represented by Formula 1 and a second host represented by Formula 2.

The organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that the emission layer includes a first host represented by Chemical Formula 1 and a second host represented by Chemical Formula 2 Can be. In addition, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode. In addition, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer may be formed thereon, and then, a material that may be used as a cathode may be deposited thereon. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.

In addition, the first host represented by Chemical Formula 1 and the second host represented by Chemical Formula 2 may be formed of an organic material layer by a solution coating method as well as a vacuum deposition method in manufacturing an organic light emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.

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

As the anode material, a material having a large work function is generally preferred to facilitate hole injection into 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, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO: Al or SNO ₂ : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.

It is preferable that the cathode material is 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; Multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like, but are not limited thereto.

The hole injection layer is a layer for injecting holes from an electrode. The hole injection material has a capability of transporting holes with a hole injection material, and has a hole injection effect at an anode, an excellent hole injection effect with respect to a light emitting layer, or a light emitting material. The compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer for receiving holes from the hole injection layer and transporting holes to the light emitting layer. A hole transporting material is a material capable of transporting holes from an anode or a hole injection layer and transferring them to the light emitting layer. This is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.

The light emitting layer may include a host material and a dopant material.

The host material may include a first host represented by Formula 1 and a second host represented by Formula 2. Since the first and second hosts have been described in detail above, detailed descriptions thereof will be omitted.

Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and a styrylamine compound may be substituted or unsubstituted. At least one arylvinyl group is substituted with the substituted arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like, but is not limited thereto. In addition, the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.

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

The electron injection layer is a layer for injecting electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, excellent electron injection effect to the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer The compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the derivatives thereof, metal Complex compounds and nitrogen-containing five-membered ring derivatives;

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

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

Preparation of the compound represented by Chemical Formula 1, the compound represented by Chemical Formula 2, and an organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are only for illustrating the present invention, and the scope of the present invention is not limited thereto.

[ Production Example  One]

Production Example  1-1: Preparation of Compound 1-1

1) Preparation of Compound 1-1-A

Dibenzo [b, d] furan (20.0 g, 118.9 mmol) was dissolved in acetic acid (300 mL) in a two-necked flask by heating under argon atmosphere. Bromine (13 mL, 261.6 mmol) was slowly added dropwise thereto, followed by stirring for 20 hours while cooling to room temperature. After the reaction was completed, the resulting solid was filtered, washed with acetic acid and water, and recrystallized with methanol to obtain compound 1-1-A (16.3 g, yield 42%, MS: [M + H] ⁺ = 326).

2) Preparation of Compound 1-1-B

Dissolve compound 1-1-A (16.0 g, 49.1 mmol), (9-phenyl-9H-carbazol-3-yl) boronic acid (15.5 g, 54.0 mmol) in THF (240 mL) in a three neck flask and ₂ CO ₃ (27.1 g, 196.3 mmol) was dissolved in water (120 mL). Pd (PPh ₃ ) ₄ (2.3 g, 2.0 mmol) was added thereto, followed by stirring for 8 hours under reflux condition of argon atmosphere. After the reaction was completed, after cooling to room temperature, the reaction solution was transferred to a separatory funnel, and extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to give compound 1-1-B (18.7 g, yield 78%, MS: [M + H] ⁺ = 488).

3) Preparation of Compound 1-1

In a three-necked flask, compound 1-1-B (18.0 g, 36.9 mmol), 2- (dibenzo [b, d] furan-2-yl) -4,4,5,5-tetramethyl-1,3, 2-dioxaborolane (11.9 g, 40.5 mmol) was dissolved in THF (270 mL) and K ₂ CO ₃ (20.4 g, 147.4 mmol) was dissolved in water (135 mL). Pd (PPh ₃ ) ₄ (1.7 g, 1.5 mmol) was added thereto, followed by stirring for 10 hours under reflux condition of argon atmosphere. After the reaction was completed, after cooling to room temperature, the reaction solution was transferred to a separatory funnel, and extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and then the sample was purified by silica gel column chromatography to give compound 1-1 through sublimation purification (6.8 g, yield 32%, MS: [M + H] ⁺ = 576).

Production Example  1-2: Preparation of Compound 1-2

Using (9-([1,1'-biphenyl] -4-yl) -9H-carbazol-3-yl) boronic acid instead of (9-phenyl-9H-carbazol-3-yl) boronic acid Except that Compound 1-2 was prepared in the same manner as in the preparation of Compound 1-1 (6.5 g, MS: [M + H] ⁺ = 652).

Production Example  1-3: Preparation of Compound 1-3

Dibenzo [b, d] furan-4- instead of 2- (dibenzo [b, d] furan-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolan Except for using ilboronic acid, Compound 1-3 was prepared in the same manner as in the preparation of Compound 1-1 (5.8 g, MS: [M + H] ⁺ = 576).

Production Example  1-4: Preparation of Compound 1-4

Use (9-([1,1'-biphenyl] -3-yl) -9H-carbazol-3-yl) boronic acid instead of (9-phenyl-9H-carbazol-3-yl) boronic acid , Instead of 2- (dibenzo [b, d] furan-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane dibenzo [b, d] furan-4 Compound 1-4 was prepared by the same method as the method for preparing compound 1-1, except that ilboronic acid was used (6.7 g, MS: [M + H] ⁺ = 652).

Production Example  1-5: Preparation of Compound 1-5

1) Preparation of Compound 1-5-A

(2-hydroxyphenyl) boronic acid (20.0 g, 145.0 mmol) and 2-bromo-1-chloro-3-fluorobenzene (33.4 g, 159.5 mmol) were dissolved in THF (300 mL) in a three-necked flask. K ₂ CO ₃ (80.2 g, 580.0 mmol) was dissolved in water (150 mL). Pd (PPh ₃ ) ₄ (6.7 g, 5.8 mmol) was added thereto, and the mixture was stirred for 8 hours under reflux conditions under argon. After the reaction was completed, after cooling to room temperature, the reaction solution was transferred to a separatory funnel, and extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to give compound 1-5-A (23.6 g, yield 73%, MS: [M + H] ⁺ = 223).

2) Preparation of Compound 1-5-B

Compound 1-5-A (23.0 g, 103.3 mmol), NBS (19.3 g, 108.5 mmol) and DMF (450 mL) were added to a two-necked flask and stirred for 8 hours at room temperature under argon atmosphere. After the reaction was completed, the reaction solution was transferred to a separatory funnel, and the organic layer was extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to give compound 1-5-B (26.5 g, yield 85%, MS: [M + H] ⁺ = 302).

3) Preparation of Compound 1-5-C

Compound 1-5-B (25.0 g, 82.9 mmol), K ₂ CO ₃ (22.9 g, 165.8 mmol) and DMF (325 mL) were added to a three neck flask and stirred overnight under reflux conditions. After the reaction was completed, the reaction mixture was cooled to room temperature, and water (200 mL) was added dropwise thereto. The reaction solution was then transferred to a separatory funnel, and the organic layer was extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to give compound 1-5-C (15.6 g, yield 67%, MS: [M + H] ⁺ = 282).

4) Preparation of Compound 1-5-D

Dissolve compound 1-5-C (15.0 g, 53.3 mmol) and (9-phenyl-9H-carbazol-3-yl) boronic acid (16.8 g, 58.6 mmol) in THF (225 mL) in a three neck flask and ₂ CO ₃ (29.5 g, 213.1 mmol) was dissolved in water (113 mL). Pd (PPh ₃ ) ₄ (2.5 g, 2.1 mmol) was added thereto, followed by stirring for 8 hours under reflux condition of argon atmosphere. After the reaction was completed, after cooling to room temperature, the reaction solution was transferred to a separatory funnel, and extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to give compound 1-5-D (18.5 g, yield 78%, MS: [M + H] ⁺ = 445).

5) Preparation of Compound 1-5

In a three-necked flask, compound 1-5-D (18.0 g, 40.5 mmol), 2- (dibenzo [b, d] furan-2-yl) -4,4,5,5-tetramethyl-1,3, 2-dioxaborolane (13.1 g, 44.5 mmol) was dissolved in 1,4-dioxane (270 mL) and K ₂ CO ₃ (22.4 g, 161.8 mmol) was dissolved in water (135 mL). Pd (PPh ₃ ) ₄ (1.9 g, 1.6 mmol) was added thereto, followed by stirring for 8 hours under reflux conditions under argon. After the reaction was completed, after cooling to room temperature, the reaction solution was transferred to a separatory funnel, and extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and then the sample was purified by silica gel column chromatography to give compound 1-5 via sublimation purification (7.2 g, yield 31%, MS: [M + H] ⁺ = 576).

Production Example  1-6: Preparation of Compound 1-6

Dibenzo [b, d] furan-4- instead of 2- (dibenzo [b, d] furan-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolan Except for using ilboronic acid, Compound 1-6 was prepared by the same method as the method for preparing Compound 1-5 (6.5 g, MS: [M + H] ⁺ = 576).

[ Production Example  2]

Production Example  2-1: Preparation of Compound 2-1

1) Preparation of Compound 2-1-A

Compound 1-5-C (20.0 g, 71.0 mmol), bis (pinacolato) diboron (21.6 g, 85.2 mmol), Pd (dba) ₂ (0.8 g, 1.4 mmol), tricyclohexyl in a three neck flask Phosphine (0.8 g, 2.8 mmol), KOAc (13.9 g, 142.1 mmol), 1,4-dioxane (300 mL) were added, and the mixture was stirred for 12 hours under reflux conditions under argon atmosphere. After the reaction was completed, after cooling to room temperature, the reaction solution was transferred to a separatory funnel, water (200 mL) was added, and extracted with ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to give compound 2-1-A (19.4 g, yield 83%, MS: [M + H] ⁺ = 329).

2) Preparation of Compound 2-1-B

In a three neck flask, compound 2-1-A (18.0 g, 54.8 mmol), 9-bromophenanthren (15.5 g, 60.3 mmol) was dissolved in THF (270 mL), and K ₂ CO ₃ (30.3 g, 219.1 mmol) Was dissolved in water (135 mL). Pd (PPh ₃ ) ₄ (2.5 g, 2.2 mmol) was added thereto, followed by stirring for 8 hours under reflux condition of argon atmosphere. After the reaction was completed, after cooling to room temperature, the reaction solution was transferred to a separatory funnel, and extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to give compound 2-1-B (15.6 g, yield 75%, MS: [M + H] ⁺ = 379).

3) Preparation of Compound 2-1-C

Compound 2-1-B (15.0 g, 39.6 mmol), bis (pinacolato) diboron (12.1 g, 47.5 mmol), Pd (dba) ₂ (0.5 g, 0.8 mmol), tricyclohexyl in a three neck flask Phosphine (0.4 g, 1.6 mmol), KOAc (7.8 g, 79.2 mmol), 1,4-dioxane (225 mL) were added thereto, and the mixture was stirred for 12 hours under reflux conditions under argon atmosphere. After the reaction was completed, after cooling to room temperature, the reaction solution was transferred to a separatory funnel, water (200 mL) was added, and extracted with ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to give compound 2-1-C (15.1 g, yield 81%, MS: [M + H] ⁺ = 470).

4) Preparation of Compound 2-1

Compound 2-1-C (15.0 g, 31.9 mmol), 2-([1,1'-biphenyl] -3-yl) -4-chloro-6-phenyl-1,3,5- in a three neck flask Triazine (12.1 g, 35.1 mmol) was dissolved in 1,4-dioxane (225 mL) and K ₂ CO ₃ (17.6 g, 127.6 mmol) was dissolved in water (113 mL). Pd (PPh ₃ ) ₄ (1.5 g, 1.3 mmol) was added thereto, followed by stirring for 8 hours under reflux conditions under argon atmosphere. After the reaction was completed, after cooling to room temperature, the reaction solution was transferred to a separatory funnel, and extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and then the sample was purified by silica gel column chromatography to give compound 2-1 through sublimation purification (6.0 g, yield 29%, MS: [M + H] ⁺ = 652).

Production Example  2-2: Preparation of Compound 2-2

3-bromo-9-phenyl-9H-carbazole is used instead of 9-bromophenanthrene and 2-([1,1'-biphenyl] -3-yl) -4-chloro-6-phenyl- Compound 2-2 in the same manner as in the preparation of Compound 2-1, except that 2-chloro-4,6-diphenyl-1,3,5-triazine was used instead of 1,3,5-triazine Was prepared (6.3 g, MS: [M + H] ⁺ = 641).

Production Example  2-3: Preparation of Compound 2-3

2-bromotriphenylene is used in place of 9-bromophenanthrene and 2-([1,1'-biphenyl] -3-yl) -4-chloro-6-phenyl-1,3,5- Compound 2-3 was prepared in the same manner as in the preparation of Compound 2-1, except that 2-chloro-4,6-diphenyl-1,3,5-triazine was used instead of triazine (5.8 g , MS: [M + H] ⁺ = 626).

Production Example  2-4: Preparation of Compound 2-4

Compound 2-4 was prepared by the same method as the method for preparing compound 2-1, except that 2-bromodibenzo [b, d] furan was used instead of 9-bromophenanthrene (6.1 g, MS: [M + H] ⁺ = 642).

Production Example  2-5: Preparation of Compound 2-5

1) Preparation of Compound 2-5-A

Compound 1-5-A (30.0 g, 134.7 mmol), NBS (50.4 g, 283.0 mmol) and DMF (600 mL) were added to a two-necked flask, and the mixture was stirred at room temperature for 8 hours under argon atmosphere. After the reaction was completed, the reaction solution was transferred to a separatory funnel, and the organic layer was extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to give compound 2-5-A (39.5 g, yield 77%, MS: [M + H] ⁺ = 380).

2) Preparation of Compound 2-5-B

Compound 2-5-A (38.0 g, 99.9 mmol), K ₂ CO ₃ (27.6 g, 199.8 mmol) and DMF (494 mL) were added to a three neck flask and stirred overnight under reflux conditions. After the reaction was completed, the mixture was cooled to room temperature, and water (300 mL) was added dropwise to the reaction solution. The reaction solution was then transferred to a separatory funnel, and the organic layer was extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to give compound 2-5-B (22.0 g, yield 61%, MS: [M + H] ⁺ = 360).

3) Preparation of Compound 2-5-C

In a three neck flask, compound 2-5-B (20.0 g, 55.5 mmol) and biphenyl-4-ylboronic acid (23.1 g, 116.5 mmol) were dissolved in THF (300 mL) and K ₂ CO ₃ (30.7 g, 222.0 mmol). ) Was dissolved in water (150 mL). Pd (PPh ₃ ) ₄ (2.6 g, 2.2 mmol) was added thereto, followed by stirring for 8 hours under argon atmosphere reflux conditions. After the reaction was completed, after cooling to room temperature, the reaction solution was transferred to a separatory funnel, and extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to give compound 2-5-C (21.1 g, yield 75%, MS: [M + H] ⁺ = 507).

4) Preparation of Compound 2-5-D

Compound 2-5-C (20.0 g, 39.4 mmol), bis (pinacolato) diboron (12.0 g, 47.3 mmol), Pd (dba) ₂ (0.5 g, 0.8 mmol), tricyclohexyl in a three neck flask Phosphine (0.4 g, 1.6 mmol), KOAc (7.7 g, 78.9 mmol), 1,4-dioxane (300 mL) were added, and the mixture was stirred for 12 hours under reflux conditions under argon atmosphere. After the reaction was completed, after cooling to room temperature, the reaction solution was transferred to a separatory funnel, water (200 mL) was added and extracted with ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to give compound 2-5-D (19.1 g, yield 81%, MS: [M + H] ⁺ = 599).

5) Preparation of Compound 2-5

Compound 2-5-D (18.0 g, 30.1 mmol), 2-([1,1'-biphenyl] -3-yl) -4-chloro-6-phenyl-1,3,5- in a three neck flask Triazine (11.4 g, 33.1 mmol) was dissolved in 1,4-dioxane (270 mL) and K ₂ CO ₃ (16.6 g, 120.3 mmol) was dissolved in water (135 mL). Pd (PPh ₃ ) ₄ (1.4 g, 1.2 mmol) was added thereto, followed by stirring for 8 hours under reflux condition of argon atmosphere. After the reaction was completed, after cooling to room temperature, the reaction solution was transferred to a separatory funnel, and extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and then the sample was purified by silica gel column chromatography to give compound 2-5 via sublimation purification (8.0 g, yield 34%, MS [M + H) ] ⁺ = 780).

Production Example  2-6: Preparation of Compound 2-6

1) Preparation of Compound 2-6-A

In a three-necked flask, 6-bromo-1-chlorodibenzo [b, d] furan (15.0 g, 53.3 mmol), (9-phenyl-9H-carbazol-3-yl) boronic acid (16.8 g, 58.6 mmol ) Was dissolved in THF (225 mL) and K ₂ CO ₃ (29.5 g, 213.1 mmol) was dissolved in water (113 mL). Pd (PPh ₃ ) ₄ (2.5 g, 2.1 mmol) was added thereto, followed by stirring for 8 hours under reflux condition of argon atmosphere. After the reaction was completed, after cooling to room temperature, the reaction solution was transferred to a separatory funnel, and extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to give compound 2-6-A (16.8 g, yield 71%, MS: [M + H] ⁺ = 444).

2) Preparation of Compound 2-6-B

Compound 2-6-A (15.0 g, 33.8 mmol), bis (pinacolato) diboron (10.3 g, 40.5 mmol), Pd (dba) 2 (0.4 g, 0.7 mmol), tricyclohexyl in a three neck flask Phosphine (0.4 g, 1.4 mmol), KOAc (6.6 g, 67.6 mmol), 1,4-dioxane (225 mL) were added, and the mixture was stirred for 12 hours under reflux conditions under argon atmosphere. After the reaction was completed, after cooling to room temperature, the reaction solution was transferred to a separatory funnel, water (300 mL) was added, and extracted with ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to give compound 2-6-B (14.3 g, yield 79%, MS: [M + H] ⁺ = 535).

3) Preparation of Compound 2-6

In a three-necked flask, compound 2-6-B (14.0 g, 26.1 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (7.7 g, 28.8 mmol) were added with 1,4-di It was dissolved in oxane (210 mL) and K ₂ CO ₃ (14.5 g, 104.6 mmol) was dissolved in water (105 mL). Pd (PPh ₃ ) ₄ (1.2 g, 1.0 mmol) was added thereto, followed by stirring for 8 hours under reflux condition of argon atmosphere. After the reaction was completed, the reaction mixture was cooled to room temperature, the reaction solution was transferred to a separatory funnel, extracted with water and ethyl acetate. The extract was dried with MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography. , Compound 2-6 via sublimation purification (5.2 g, yield 31%, MS: [M + H] ⁺ = 641).

Production Example  2-7: Preparation of Compound 2-7

1) Preparation of Compound 2-7-A

6-bromo-1-chlorodibenzo [b, d] furan (15.0 g, 53.3 mmol), 2,4-diphenyl-6- (4,4,5,5-tetramethyl-1) in a three-necked flask Dissolve 3,2-dioxaborolan-2-yl) -1,3,5-triazine (21.1 g, 58.6 mmol) in THF (225 mL) and add K ₂ CO ₃ (29.5 g, 213.1 mmol). It was dissolved in water (113 mL). Pd (PPh ₃ ) ₄ (2.5 g, 2.1 mmol) was added thereto, followed by stirring for 8 hours under reflux condition of argon atmosphere. After the reaction was completed, after cooling to room temperature, the reaction solution was transferred to a separatory funnel, and extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to give Compound 2-7-A (15.7 g, yield 68%, MS: [M + H] ⁺ = 434).

2) Preparation of Compound 2-7

In a three-necked flask, compound 2-7-A (15.0 g, 34.6 mmol) and (9-phenyl-9H-carbazol-3-yl) boronic acid (10.9 g, 38.0 mmol) were added with 1,4-dioxane (225 mL) and K ₂ CO ₃ (19.1 g, 138.3 mmol) was dissolved in water (113 mL). Pd (PPh ₃ ) ₄ (1.6 g, 1.4 mmol) was added thereto, followed by stirring for 8 hours under reflux condition of argon atmosphere. After the reaction was completed, the reaction mixture was cooled to room temperature, the reaction solution was transferred to a separatory funnel, extracted with water and ethyl acetate. The extract was dried with MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography. , Compound 2-7 was obtained via sublimation purification (6.2 g, yield 28%, MS: [M + H] ⁺ = 641).

Production Example  2-8: Preparation of Compound 2-8

2- (9-chlorodibenzo [b, d] thiophen-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane instead of compound 2-1-A Except for the use, the compound 2-8 was produced by the same method as the compound 2-2 (4.8 g, MS: [M + H] ⁺ = 657).

[ EXAMPLE ]

EXAMPLE  One

A glass substrate coated with a thin film of ITO (Indium Tin Oxide) having a thickness of 1,400Å was placed in distilled water dissolved in a detergent and washed with ultrasonic waves. Fischer Co. Decon ™ CON705 product was used as a detergent, and distilled water was filtered using a 0.22 μm sterilizing filter from Millerpore Co. After ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After the distilled water was washed, ultrasonic washing with a solvent of isopropyl alcohol, acetone and methanol for 10 minutes, dried and then transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.

On the thus prepared ITO transparent electrode, a mixture of 95 wt% of the following HT-A compound and 5 wt% of the following P-DOPANT compound was thermally vacuum deposited to a thickness of 100 kPa, followed by depositing only the following HT-A compound to a thickness of 1150 kPa A transport layer was formed. On the hole transport layer, the following HT-B compound was thermally vacuum deposited to a thickness of 450 kPa to form an electron blocking layer. On the electronic blocking layer, a mixture of 56.4 wt% of Compound 1-1 prepared as the first host, 37.6 wt% of Compound 2-1 prepared as the second host, and 6 wt% of the following GD compound as the dopant was added Vacuum deposition to a thickness to form a light emitting layer. On the light emitting layer, the following ET-A compound was vacuum deposited to a thickness of 50 kPa to form a hole blocking layer. On the hole blocking layer, the following ET-B compound and the following Liq compound were mixed at a weight ratio of 2: 1 to form a electron transport layer by thermal vacuum layering at a thickness of 250 kPa, followed by mixing LiF and magnesium at a weight ratio of 1: 1. Vacuum deposition was carried out to a thickness of 30 kHz to form an electron injection layer. Magnesium and silver were mixed at a weight ratio of 1: 4 on the electron injection layer and deposited to a thickness of 160 kPa to form a cathode, thereby manufacturing an organic light emitting device.

EXAMPLE  2 to 12

An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used as a host.

Comparative example  1 to 7

An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used as a host. In Table 1 below, GH-1, GH-2-A, GH-2-B and GH-2-C are as follows.

Voltage, efficiency, and lifetime (T95) were measured by applying current to the organic light emitting diodes manufactured in Examples and Comparative Examples, and the results are shown in Table 1 below. At this time, the voltage and efficiency were measured by applying a current density of 10 mA / cm ² , the life (T95) means the time until the initial luminance is reduced to 95% at a current density of 20 mA / cm ² .

First host 2nd host Voltage (V)
(@ 10mA / cm ² ) Efficiency (cd / A)
(@ 10mA / cm ² ) Life (T95, hr)
(@ 20mA / cm ² ) Example 1 Compound 1-1 Compound 2-1 3.85 57.55 120 Example 2 Compound 1-1 Compound 2-2 3.90 54.15 130 Example 3 Compound 1-1 Compound 2-3 3.91 56.43 110 Example 4 Compound 1-1 Compound 2-4 3.87 55.25 140 Example 5 Compound 1-2 Compound 2-5 3.81 57.39 130 Example 6 Compound 1-2 Compound 2-6 3.82 53.73 120 Example 7 Compound 1-2 Compound 2-7 3.84 55.12 130 Example 8 Compound 1-2 Compound 2-8 3.93 56.47 120 Example 9 Compound 1-3 Compound 2-1 3.87 57.15 140 Example 10 Compound 1-4 Compound 2-3 3.92 55.57 120 Example 11 Compound 1-5 Compound 2-5 3.90 56.91 130 Example 12 Compound 1-6 Compound 2-7 3.88 58.82 120 Comparative Example 1 GH-1 GH-2-A 4.56 32.11 80 Comparative Example 2 GH-1 GH-2-B 4.67 38.19 70 Comparative Example 3 GH-1 GH-2-C 4.65 36.55 60 Comparative Example 4 Compound 1-1 GH-2-A 4.81 32.11 30 Comparative Example 5 Compound 1-1 GH-2-B 4.88 38.19 40 Comparative Example 6 Compound 1-1 GH-2-C 4.76 36.55 70 Comparative Example 7 GH-1 Compound 2-1 4.91 21.15 30

As shown in Table 1, Examples 1 to 12 using the compound of Formula 1 of the present invention as the first host of the light emitting layer of the organic light emitting device, and at the same time using the compound of Formula 2 of the present invention as a second host Showed excellent characteristics as compared with Comparative Examples 1-7.

Both the structure of formula (1) and the structure of formula (2) of the present invention are structures having substituents on both sides of dibenzofuran or dibenzothiophene. Structural similarity between the two structures allows the two materials to mix well without the possibility of agglomeration or phase separation of the two materials when they are deposited simultaneously.

In addition, the structure of Formula 1 has a substituent having p-type properties on both sides, the structure of Formula 2 has a substituent having n-type properties on one side and a substituent having a p-type property on the other side. Due to these structural differences, the structure of Formula 1 of the present invention is advantageous for hole transport, and the structure of Formula 2 of the present invention is advantageous for electron transport. Therefore, when two materials are used simultaneously as the host of the light emitting layer, it is easy to balance the charge balance between the holes and the electrons in the light emitting layer.

In conclusion, when the material having the structure of Formula 1 and the material having the structure of Formula 2 are simultaneously used as the light emitting layer host, an organic light emitting device having low voltage, high efficiency, and long life may be obtained.

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

Claims (15)

A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode.
The organic layer includes a light emitting layer,
The emission layer includes a first host represented by Formula 1 and a second host represented by Formula 2,
Organic light emitting device:
[Formula 1]

In Chemical Formula 1,
Ar ₁ is substituted or unsubstituted C _6-60 aryl,
1a, 2a, 3a or 4a is connected to 3b,
1d, 2d, 3d or 4d is linked to 3c or 4c,
[Formula 2]

In Chemical Formula 2,
X is O or S,
R ₁ to R ₄ are each independently hydrogen, substituted or unsubstituted C _6-60 aryl, substituted or unsubstituted C _2-60 heteroaryl including one or more of O, N, Si and S, or Formula 3,
R ₅ is a substituted or unsubstituted C _6-60 aryl group, C _2-60 heteroaryl including one or more of substituted or unsubstituted O, N, Si and S, or
At least one of R ₁ to R ₅ is the formula (3),
[Formula 3]

In Chemical Formula 3,
Z ₁ to Z ₅ are each independently N or CR ₆ ,
R ₆ is hydrogen, substituted or unsubstituted C _6-60 aryl, or C _2-60 heteroaryl including one or more of substituted or unsubstituted O, N, Si, and S.
The method of claim 1,
Ar ₁ in Formula 1 is a phenyl group or a biphenyl group,
Organic light emitting device.
delete The method of claim 1,
In Formula 1, 3c is connected to 1d or 3d,
Organic light emitting device.
The method of claim 1,
The first host represented by Formula 1 is selected from the group consisting of the following compounds,
Organic light emitting device:

The method of claim 1,
R ₅ is Formula 3,
R ₁ to R ₄ are each independently hydrogen, substituted or unsubstituted C _6-60 aryl, or C _2-60 heteroaryl including one or more of substituted or unsubstituted O, N, Si, and S,
Organic light emitting device.
The method of claim 1,
R ₅ is Formula 3,
At least one of R ₁ to R ₄ is substituted or unsubstituted C _6-60 aryl, or C _2-60 heteroaryl including one or more of substituted or unsubstituted O, N, Si, and S, with the remainder Hydrogen,
Organic light emitting device.
The method of claim 1,
R ₅ is Formula 3,
At least one of R ₁ to R ₃ is substituted or unsubstituted C _6-60 aryl, or C _2-60 heteroaryl including one or more of substituted or unsubstituted O, N, Si, and S; Hydrogen,
R ₄ is hydrogen,
Organic light emitting device.
The method of claim 1,
Any one of R ₁ to R ₄ is formula (3), and the other is hydrogen, substituted or unsubstituted C _6-60 aryl, or C comprising one or more of substituted or unsubstituted O, N, Si, and S _2-60 heteroaryl,
R ₅ is substituted or unsubstituted C _6-60 aryl, or C _2-60 heteroaryl including one or more of substituted or unsubstituted O, N, Si and S,
Organic light emitting device.
The method of claim 1,
Any one of R ₁ to R ₄ is Formula 3, and the others are hydrogen,
R ₅ is substituted or unsubstituted C _6-60 aryl, or C _2-60 heteroaryl including one or more of substituted or unsubstituted O, N, Si and S,
Organic light emitting device.
The method of claim 1,
Any one of R ₁ to R ₃ is formula (3), and the others are hydrogen,
R ₄ is hydrogen,
R ₅ is substituted or unsubstituted C _6-60 aryl, or C _2-60 heteroaryl including one or more of substituted or unsubstituted O, N, Si and S,
Organic light emitting device.
The method of claim 1,
R ₁ to R ₄ are each independently hydrogen; Or monovalent moieties derived from arene or heteroarene selected from the group consisting of biphenyl, terphenyl, phenanthrene, triphenylene, 9-phenylcarbazole and dibenzofuran; Or Formula 3,
R ₅ is a monovalent moiety derived from arene or heteroarene selected from the group consisting of biphenyl, terphenyl, phenanthrene, triphenylene, 9-phenylcarbazole and dibenzofuran; Or Formula 3 above,
At least one of R ₁ to R ₅ is the formula (3),
Organic light emitting device.
The method of claim 1,
In Formula 3, at least two or more of Z ₁ , Z _3, and Z ₅ are N,
Organic light emitting device.
The method of claim 1,
At least two of Z ₁ , Z ₃ and Z ₅ in Formula 3 is N, the remainder is CH, Z ₂ and Z ₄ is CR ₆ , wherein R ₆ is a phenyl group, biphenyl group or terphenyl group,
Organic light emitting device.
The method of claim 1,
The second host represented by Formula 2 is selected from the group consisting of the following compounds,
Organic light emitting device:

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