WO2013055132A2 - Compound for organic electrical device, organic electrical device using same, and electronic device thereof - Google Patents

Abstract

The present invention provides a novel compound capable of improving lighting efficiency, stability, and lifetime of a device, and an organic electrical device using the same, and an electronic device thereof.

Description

Compound for organic electric device, organic electric device using same and electronic device thereof

The present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device thereof.

In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic electric element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. The organic layer is often made of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic electrical device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.

Materials used as the organic material layer in the organic electric element may be classified into light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on their functions. The light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. Can be. In addition, the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.

In particular, various studies have been conducted on organic materials inserted into a hole transporting layer or a buffer layer for excellent life characteristics of the organic electric device, and for this, a thin film after deposition while giving high hole transporting characteristics from the anode to the organic layer There is a need for a hole injection layer material having high uniformity and low crystallinity in forming.

Delays penetration of metal oxide into the organic layer from the anode electrode (ITO), which is one of the causes of the shortening of the life of the organic electric device, and stable properties for Joule heating generated when driving the device, that is, high glass transition temperature. There is a need for development of a hole injection layer material having In addition, the low glass transition temperature of the hole transport layer material has been reported to have a significant effect on the device life, depending on the characteristics of the uniformity of the surface of the thin film when driving the device. In addition, the deposition method is the mainstream in the formation of the OLED device, a situation that requires a material that can withstand a long time, that is, a material having a strong heat resistance characteristics.

On the other hand, when only one material is used as the light emitting material, the maximum light emission wavelength is shifted to the long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the light emission attenuation effect. In order to increase the light emitting efficiency through the light emitting material, a host / dopant system may be used. The principle is that when a small amount of dopant having an energy band gap smaller than that of the host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant, thereby producing high efficiency light. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.

In order to fully exhibit the excellent characteristics of the above-described organic electroluminescent device, a material constituting the organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material. Although this should be preceded, the development of a stable and efficient organic material layer for an organic electric device has not been made sufficiently, and therefore, the development of new materials is still required.

An object of the present invention is to provide a compound capable of improving high luminous efficiency, low driving voltage, color purity, and lifetime of an element, an organic electric element using the same, and an electronic device thereof.

According to one aspect of the present invention, the present invention provides a compound represented by the following formula.

According to another aspect of the invention, the present invention provides an organic electric device comprising the formula (1) and an electronic device using the same.

By using the novel compound according to the present invention, it is possible to greatly improve the device's high luminous efficiency, low driving voltage, color purity, and lifetime.

1 is an exemplary view of an organic electroluminescent device according to an embodiment of the present invention.

Hereinafter, some embodiments of the present invention will be described in detail through exemplary drawings.

In adding reference numerals to the components of each drawing, it should be noted that the same reference numerals are assigned to the same components as much as possible even though they are shown in different drawings. In addition, in describing the present invention, when it is determined that the detailed description of the related well-known configuration or function may obscure the gist of the present invention, the detailed description thereof will be omitted.

In addition, in describing the component of this invention, terms, such as 1st, 2nd, A, B, (a), (b), can be used. These terms are only for distinguishing the components from other components, and the nature, order or order of the components are not limited by the terms. If a component is described as being "connected", "coupled" or "connected" to another component, that component may be directly connected to or connected to that other component, but there may be another configuration between each component. It is to be understood that the elements may be "connected", "coupled" or "connected".

As used herein, the term "halo" or "halogen" includes fluorine, chlorine, bromine, and iodine unless otherwise noted.

As used herein, the term "alkyl" or "alkyl group" has a carbon number of 1 to 60 unless otherwise specified, but is not limited thereto.

As used herein, the term "alkenyl" or "alkynyl" has a double bond or a triple bond having 2 to 60 carbon atoms, respectively, unless otherwise specified, but is not limited thereto.

The term "cycloalkyl" as used herein, unless otherwise stated, refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto.

The term "alkoxy group" used in the present invention has a carbon number of 1 to 60 unless otherwise stated, it is not limited thereto.

As used herein, the terms "aryl group" and "arylene group" have a carbon number of 6 to 60 unless otherwise stated, but is not limited thereto.

In the present invention, an aryl group or an arylene group means a monocyclic or heterocyclic aromatic, and includes an aromatic ring formed by neighboring substituents participating in a bond or a reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, a spirofluorene group.

As used herein, the term “heteroalkyl” means an alkyl including one or more heteroatoms unless otherwise indicated. As used herein, the term "heteroaryl group" or "heteroarylene group" means an aryl group or arylene group having 3 to 60 carbon atoms, each of which includes one or more heteroatoms, unless otherwise specified. In addition, it includes not only a single ring but also a heterocycle, and adjacent groups may be formed by bonding.

As used herein, the terms "heterocycloalkyl" and "heterocyclic group" include one or more heteroatoms, unless otherwise specified, have a carbon number from 2 to 60, and include heterocycles as well as monocycles. Adjacent groups may be formed in combination. In addition, "heterocyclic group" may mean an alicyclic and / or aromatic including a heteroatom.

As used herein, the term “heteroatom” refers to N, O, S, P, and Si unless otherwise indicated.

Unless otherwise stated, the term "aliphatic" as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms, and the "aliphatic ring" means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

Unless otherwise stated, the term "saturated or unsaturated ring" as used herein means a saturated or unsaturated aliphatic ring or an aromatic ring or heterocyclic ring having 6 to 60 carbon atoms.

Other heterocompounds or heteroradicals other than the aforementioned heterocompounds include, but are not limited to, one or more heteroatoms.

Also, unless stated otherwise, the term "substituted" in the term "substituted or unsubstituted" as used in the present invention is deuterium, halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy groups, C ₁ to C ₂₀ alkylamine groups, C ₁ to C ₂₀ alkylthiophene groups, C ₆ to C ₂₀ arylthiophene groups, C ₂ to C ₂₀ alkenyl groups, C ₂ to C ₂₀ alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₆₀ aryl group, C ₆ ~ C ₂₀ aryl group substituted with deuterium, C ₈ ~ C ₂₀ aryl alkenyl group, silane group, boron Group, germanium group, and C ₅ ~ C _{20 It} is meant to be substituted with one or more substituents selected from the group consisting of, but not limited to these substituents.

1 is an exemplary view of an organic electric device according to an embodiment of the present invention.

Referring to FIG. 1, the organic electric device 100 according to the present invention includes a first electrode 120, a second electrode 180, a first electrode 110, and a second electrode 180 formed on a substrate 110. An organic material layer containing a compound represented by the formula (1) between) is provided. In this case, the first electrode 120 may be an anode (anode), the second electrode 180 may be a cathode (cathode), and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

The organic layer may include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170 on the first electrode 120 in sequence. At this time, the remaining layers except for the light emitting layer 150 may not be formed. The hole blocking layer, the electron blocking layer, the light emitting auxiliary layer 151, the buffer layer 141 may be further included, and the electron transport layer 160 may serve as the hole blocking layer.

In addition, although not shown, the organic electronic device according to the present invention may further include a protective layer formed on one surface of the first electrode and the second electrode opposite to the organic material layer.

The compound according to the present invention applied to the organic material layer is a hole injection layer 130, a hole transport layer 140, an electron transport layer 160, the electron injection layer 170, the host of the light emitting layer 150 or the material of the dopant or capping layer Can be used as Preferably, the compound according to the present invention may be used as a host material of the light emitting layer 150 or a material for forming the hole transport layer 140.

On the other hand, the organic electroluminescent device according to an embodiment of the present invention can be manufactured using a PVD (physical vapor deposition) method. For example, the anode 120 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, and the electron transport layer are formed thereon. After forming the organic material layer including the 160 and the electron injection layer 170, it can be prepared by depositing a material that can be used as the cathode 180 thereon.

In addition, the organic layer may be prepared by using a variety of polymer materials, but not by a deposition process or a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing or thermal transfer. It can be prepared in a number of layers. Since the organic material layer according to the present invention may be formed in various ways, the scope of the present invention is not limited by the forming method.

The organic electric element 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.

In addition, the organic electroluminescent device according to the present invention may be one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), a monochromatic or white illumination device.

Another embodiment of the present invention may include a display device including the organic electric element of the present invention described above, and an electronic device including a control unit for controlling the display device. In this case, the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.

Hereinafter, the compound contained in the organic material layer of the organic electric device according to an aspect of the present invention will be described in detail.

An organic electric device according to an aspect of the present invention includes an anode, a cathode, and an organic material layer formed between the anode and the cathode. In this case, the emission layer may be formed of a compound represented by the following Chemical Formula 1.

<Formula 1>

In Formula 1, A ring is C ₆ ~ C ₆₀ A single or polycyclic aromatic or heterocyclic ring, n is 1 or 2.

And, in the formula 1, Y is a direct bond (only when n = 2); Hydrogen, deuterium, halogen, nitrile group, nitro group, -LN (Ar ₁ ) (Ar ₂ ), C ₆ ~ C ₆₀ aryl group, fluorenyl group, C ₂ ~ C ₆₀ heterocyclic group, C ₁ ~ C ₃₀ alkoxy group, C ₆ ~ C ₃₀ aryloxy and C ₁ ~ C ₅₀ monovalent substituent selected from the group consisting of an alkyl group or a; Or a C ₆ to C ₆₀ arylene group, a fluorenylene group, a C ₆ to C ₆₀ aromatic ring and a C ₃ to C ₆₀ alicyclic fused ring, a C ₂ to C ₆₀ heterocyclic group or a divalent aliphatic hydrocarbon May be selected from the group of divalent substituents consisting of groups,

R ₁ to R ₁₁ are each independently hydrogen, deuterium, halogen, nitrile group, nitro group, -LN (Ar ₁ ) (Ar ₂ ), C ₆ ~ C ₆₀ aryl group, fluorenyl group, C ₂ ~ C ₆₀ heterocyclic group, C ₁ ~ C ₃₀ Alkoxy group, C ₆ ~ C _{30 It} may be selected from the group consisting of aryloxy group and C ₁ ~ C ₅₀ Alkyl group, X is S, SO or SO ₂ to be.

In this case, in -LN (Ar ₁ ) (Ar ₂ ), L is a direct bond (that is, absent), C ₆ ~ C ₆₀ arylene group, fluorenylene group, C ₆ ~ C ₆₀ aromatic ring and C ₃ ~ C ₆₀ of aliphatic and may be selected from the group consisting of fused rings, C ₂ ~ C ₆₀ heterocyclic group or a divalent aliphatic hydrocarbon group,

Ar ₁ and Ar ₂ are each independently of the C ₆ ~ C ₆₀ aryl group, C ₂ ~ C ₆₀ heterocyclic group, fluorenyl group, C ₁ ~ C ₃₀ alkoxy group, C ₆ ~ C ₃₀ aryloxy group And it is selected from the group consisting of C ₁ ~ C ₅₀ Alkyl group.

Meanwhile, Y, R ₁ to R ₁₁ , L, Ar _1, and Ar ₂ may be further substituted with specific substituents.

By way of example, when Y, R ₁ to R ₁₁ , Ar ₁ and Ar ₂ is a C ₆ ~ C ₆₀ aryl group, and when Y, R ₁ to R ₁₁ , Ar ₁ and Ar ₂ is a fluorenyl group and In the case of the arylene group of the Y and L, and the Y and L is a fluorenylene group, these are deuterium, halogen, silane group, boron group, germanium group, C ₁ ~ C ₂₀ Alkylthio group, C ₆ ~ C ₂₀ arylthio group, C ₁ -C ₂₀ alkoxy group, -N (Ar ₁ ) (Ar ₂ ), C ₁ -C ₂₀ alkyl group, C7-C20 arylalkyl group, C ₂ -C ₂₀ alkenyl group , C ₈ ~ C ₂₀ aryl alkenyl group, C ₂ ~ C ₂₀ alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl group substituted with deuterium and C ₂ ~ C ₂₀ heterocyclic ring It may be substituted with one or more substituents selected from the group consisting of groups.

In addition, the C ₆ ~ C ₆₀ heterocyclic group of the Y, R ₁ to R ₁₁ , L, Ar ₁ and Ar ₂ includes at least one hetero atom of O, N, S, Si and P, deuterium, halogen Group, -N (Ar ₁ ) (Ar ₂ ), C ₁ -C ₂₀ alkyl group, C ₇ -C ₂₀ arylalkyl group, C ₂ -C ₂₀ alkenyl group, C ₈ -C ₂₀ arylalkenyl group, C It may be substituted with one or more substituents selected from the group consisting of ₁ to C ₂₀ alkoxy group, C ₆ ~ C ₆₀ aryl group, C ₆ ~ C ₂₀ aryl group substituted with deuterium, a nitrile group and an acetylene group.

Further, the C ₁ to C ₃₀ alkoxy group and the C ₆ to C ₃₀ aryloxy group of the Y, R ₁ to R ₁₁ , Ar ₁ and Ar ₂ may be deuterium, halogen, amino, nitrile, nitro or C _1. ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₃ ~ C ₃₀ cycloalkyl group, C ₆ ~ C ₆₀ aryl group, a C ₆ ~ C substituted with deuterium It may be substituted with one or more substituents selected from the group consisting of an aryl group of _{20 and} a heterocyclic group of C ₂ ~ C ₆₀ .

In addition, the C ₁ to C ₅₀ alkyl group of Y, R ₁ to R ₁₁ , r _1, and Ar ₂ may be C ₂ to C ₂₀ alkenyl group, C ₁ to C ₂₀ alkoxy group, C ₆ to C ₂₀ aryl A C ₆ to C ₂₀ aryl group, a C ₇ to C ₂₀ arylalkyl group, a C ₈ to C ₂₀ arylalkenyl group, a C ₂ to C ₂₀ heterocyclic group, a nitrile group and an acetylene group It may be substituted with one or more substituents selected from the group.

Specifically, Formula 1 may be represented by one of the following formula. Formula 2 corresponds to the case of n = 1 in Formula 1, and Formula 3 corresponds to the case of n = 2. In addition, Formula 4 corresponds to the case where n = 1 in Formula 1 and Y is -L-N (Ar1) (Ar2) among monovalent substituents.

<Formula 2>

<Formula 3>

<Formula 4>

In Formula 2 to Formula 4, A ring, R ₁ ~ R ₁₁ and X are as defined in formula (1). In Formula 2, Y may be selected from the group of monovalent substituents in the definition of Y in Formula 1, and in Formula 3, Y may be a direct bond or may be selected from the group of divalent substituents in the definition of Y in Formula 1. In addition, in Chemical Formula 4, L, Ar ₁ and Ar ₂ are the same as defined in Chemical Formula 1.

In addition, when A ring is a benzene ring, Formula 1 may be represented by one of the following Formulas 5 to 7.

<Formula 5>

<Formula 6>

<Formula 7>

In Chemical Formulas 5 to 7, R ₁ to R ₈ and X are the same as defined in Chemical Formula 1. In addition, Y in Formula 5 may be selected from the group of monovalent substituents in the Y definition of Formula 1, Y in Formula 6 may be a direct bond, or may be selected from a divalent substituent group in the Y definition of Formula 1, Formula 7 L, Ar ₁ and Ar ₂ are as defined in formula (1).

More specifically, Formula 1 may be one of the following compounds, but is not limited to these compounds, any compound satisfying Formula 1 will belong to the present invention.

Hereinafter, the synthesis examples of the compounds represented by the general formula (1) of the present invention and the production examples of the organic electric device will be described in detail with reference to Examples, but the present invention is not limited to the following Examples.

In exemplary embodiments, Chemical Formula 1 may be synthesized by the following Chemical Formula 1.

<Scheme 1>

In Scheme 1, Sub 1-6 may be synthesized by Scheme 2 below.

<Scheme 2>

Sub 1-1 to Sub 1-6 of Scheme 2 may be synthesized by the following synthesis method, but is not limited thereto.

Sub 1-1 Synthesis

After dissolving Phenanthrene (35.65 g, 200 mmol) in 600 mL of methylene chloride, 0.05 equivalent of BPO (Benzoyl peroxide) and NBS (N-bromosuccinimide) (35.60 g, 200 mmol) were slowly added, followed by stirring at room temperature for 24 hours. . After the reaction was completed, 300 mL of 5% HCl was added, followed by 300 mL of water to remove residual NBS, and extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. Thereafter, the resultant organic material was recrystallized from a silicagel column to obtain 38.57 g (75%) of Sub 1-1.

Sub 1-2 synthesis

Sub 1-1 (36.0 g, 140 mmol) obtained in the above synthesis was dissolved in 980 mL of DMF, followed by bispinacolborate (39.1 g, 154 mmol), PdCl ₂ (dppf) catalyst (3.43 g, 4.2 mmol), KOAc (41.3 g, 420 mmol) was added sequentially, followed by stirring for 24 hours to synthesize the borate compound. The obtained compound was separated through a silica gel column and recrystallized, and then the borate compound was 29.81 g (70%) of Sub 1-2. Get

Sub 1-3 Synthesis

After dissolving 1 equivalent of Sub 1-2 obtained in the synthesis and 1 equivalent of 2-bromothioanisole in 200 ml of THF, 1.1 equivalent of Tetrakis (triphenylphosphine) palladium and 2M aqueous sodium carbonate solution were added thereto, and the mixture was stirred at 70 ° C for 18 hours. After the reaction was completed, extracted with diethyl ehter and water, the organic layer was dried, silicagel column and recrystallization to obtain Sub 1-3 80%.

Sub 1-4 Synthesis

Sub 1-3 was dissolved in dichloromethane, 30% aqueous hydroxyperoxide solution and acetic acid were added, followed by stirring at 30 ° C. for 4 hours. After the reaction was completed, extracted with chloroform and water, the organic layer was dried, silicagel column and recrystallization to obtain Sub 1-4 76%.

Sub 1-5 synthesis

Add triflic acid to Sub 1-4 and stir at room temperature for 72 hours. After the reaction was completed, diethyl ehter was added, and the resulting white solid precipitate was filtered and dried to obtain 78% of Sub 1-5.

Sub 1-6 Synthesis

Sub 1-5 was dissolved in 600 mL of methylene chloride, and then 0.05 equivalent of BPO (Benzoyl peroxide) and NBS (N-bromosuccinimide) (35.60 g, 200 mmol) were added slowly, followed by stirring at room temperature for 24 hours. After the reaction was completed, 300 mL of 5% HCl was added, followed by 300 mL of water to remove residual NBS, and extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was silicagel column and recrystallized to obtain Sub 1-6 78%.

Meanwhile, Sub 2 in Scheme 1 may be one of the following compounds, but is not limited thereto.

The FD-MS values of Sub 2-1 to Sub 2-24 are shown in Table 1 below.

Table 1

< EXAMPLE  1> final compound ( Product  Synthesis example of 1)

Compounds of Sub 1-6 (1 equiv), Sub 2 compounds (1 equiv), Pd ₂ (dba) ₃ (0.03-0.5 mmol), PPh ₃ (0.1 equiv), NaO t -Bu (3 equiv. ), add toluene (10.5 mL / 1 mmol) and proceed with the reaction at 100 ° C. After the reaction was completed, the mixture was extracted with ether and water, and the organic layer was dried over MgSO ₄ , concentrated, and the resulting organic material was silicagel column and recrystallized. FD-MS of the resulting final compound is shown in Table 2 below.

TABLE 2

As another example, the final compound of the present invention can be prepared by the following scheme 3.

<Scheme 3>

In Scheme 3, Sub 3 may be one of the following compounds, but is not necessarily limited thereto.

The FD-MS of Sub 3-1 to Sub 3-66 is shown in Table 3 below.

TABLE 3

< EXAMPLE  2> final compound ( Product  2) Synthesis Example

Sub 1-7 compound (1 equivalent) was added to a round bottom flask, and the amine compound Sub 3 (1.1 equivalent), Pd (PPh ₃ ) ₄ (0.03 to 0.05 equivalent), NaOH (3 equivalent), THF (3 mL / 1 mmol), water (1.5 mL / 1 mmol) is added. Thereafter, the mixture is heated to reflux at 80 ° C to 90 ° C. When the reaction is complete, distilled water is diluted at room temperature and extracted with methylene chloride and water. The organic layer was dried over MgSO ₄ , concentrated, and the resulting compound was recrystallized from a silicagel column. FD-MS of the final compound thus synthesized is shown in Table 4 below.

Table 4

On the other hand, each of the substituents of the compounds represented by the formula (1) has a broad relationship, exemplarily described the synthesis examples of the representative compounds, the compounds represented by the formula (1) not illustrated by way of example as a synthesis example Can be configured.

Moreover, the compound which has the intrinsic property of the introduced substituent can be synthesize | combined by introducing various substituents into the core structure of the above structure. For example, by introducing substituents used in the hole injection layer material, the hole transport layer material, the light emitting layer material, and the electron transport layer material used in the manufacture of the organic electric device, including the organic light emitting device to satisfy the conditions required for each organic material layer Materials can be prepared.

The compound according to the present invention may be used in various applications in the organic electroluminescent device according to the type and nature of the substituent. That is, the compound of the present invention can be applied to various layers other than the host of the phosphorescent or fluorescent light emitting layer because it is free to be controlled by the core and the substituent.

Manufacturing Evaluation of Organic Electrical Device

< Experimental Example  1>

First, a copper phthalocyanine (CuPc) film was vacuum deposited on an ITO layer (anode) formed on a glass substrate to form a hole injection layer having a thickness of 10 nm. Subsequently, 4,4-bis [ N- (1-naphthyl) -N -phenylamino] biphenyl was vacuum deposited to a thickness of 30 nm on the hole injection layer to form a hole transport layer. In addition, a light emitting layer having a thickness of 30 nm was formed on the hole transport layer by doping at 95: 5 weight using a compound of the present invention as a host material and Ir (ppy) ₃ [tris (2-phenylpyridine) -iridium] as a dopant material. . Subsequently, ((1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer, Tris (8-quinolinol) aluminum was deposited to a thickness of 40 nm on the hole blocking layer to form an electron injection layer. Subsequently, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm, Al was deposited to a thickness of 150 nm, and an organic light emitting diode was manufactured by forming an Al / LiF cathode.

< Comparative example  1>

An organic electroluminescent device was manufactured in the same manner as in Experiment 1, except that the compound represented by Comparative Compound 2 was used as a host material instead of the compound of the present invention when forming the emission layer.

          <Comparative Compound 1>

Measurement results of device performance, that is, driving voltage, current density, brightness, efficiency, lifetime, and color coordinates of the organic light emitting diodes manufactured by Experimental Example 1 and Comparative Example 1 of the present invention are shown in Table 5 below. In Table 5, the organic light emitting display device manufactured according to the experimental example of the present invention is represented by Examples 1 to 145.

Table 5

< Experimental Example  2>

First, a 4,4'4 "-tris (N- (2-naphthyl) -N-phenylamino) -triphenylamine (hereinafter abbreviated as 2T-NATA) film was formed on an ITO layer (anode) formed on a glass substrate. Vacuum deposition was performed to form a 10 nm thick hole injection layer. Subsequently, the compound of the present invention was vacuum deposited on the hole injection layer to form a hole transport layer having a thickness of 30 nm. In addition, a 45 nm-thick light emitting layer doped with BD-052X (Idemitus, Inc.) 7% was formed on the hole transport layer. 2-anthracene (AND))). Subsequently, ((1,1'-bisphenyl) -4-oleato) bis (2-methyl-8-quinolinolato) aluminum was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer, Tris (8-quinolinol) aluminum was deposited to a thickness of 40 nm on the hole blocking layer to form an electron injection layer. Thereafter, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm, Al was deposited to a thickness of 150 nm, and an organic light emitting display device was fabricated by forming an Al / LiF cathode.

< Comparative example  2>

An organic light emitting display device was manufactured in the same manner as in Experiment 2, except that the compound represented by Comparative Compound 2 was used instead of the compound of the present invention when forming the hole injection layer.

<Comparative Compound 2>

Measurement results of device performance, that is, driving voltage, current density, brightness, efficiency, lifespan, and color coordinates of the organic light emitting diodes manufactured by Experimental Example 2 and Comparative Example 2 of the present invention are shown in Table 6 below. In Table 6 below, the organic light emitting display device manufactured according to Experimental Example 2 of the present invention is represented by Examples 146 to 157.

Table 6

As can be seen in Table 5 and Table 6, when the compound according to the present invention is used as a light emitting host or hole transport layer material, the driving voltage of the organic light emitting device can be lowered, and color purity, luminous efficiency and lifespan can be remarkably improved. Can be. Even if the compounds of the present invention are used in other organic material layers of the organic light emitting device, for example, a light emitting auxiliary layer, an electron injection layer, an electron transport layer, and a hole injection layer, it is obvious that the same effect can be obtained.

The above description is merely illustrative of the present invention, and those skilled in the art to which the present invention pertains may various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed herein are not intended to limit the present invention but to describe the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The protection scope of the present invention should be interpreted by the following claims, and all the technologies within the equivalent scope should be interpreted as being included in the scope of the present invention.

CROSS-REFERENCE TO RELATED APPLICATION

This patent application claims priority under No. 119 (a) (35 USC § 119 (a)) of the Patent Application No. 10-2011-0104787, filed with South Korea on October 13, 2011. All content is incorporated by reference in this patent application. In addition, if this patent application claims priority for the same reason for countries other than the United States, all its contents are incorporated into this patent application by reference.

Claims (9)

1. Compound represented by the following formula.

   

   In the above formula,

   A ring is a C ₆ ~ C ₆₀ single or polycyclic aromatic or heterocyclic ring,

   Y is a direct bond, provided that n = 2; Hydrogen, deuterium, halogen, nitrile group, nitro group, -LN (Ar ₁ ) (Ar ₂ ), C ₆ ~ C ₆₀ aryl group, fluorenyl group, C ₂ ~ C ₆₀ heterocyclic group, C ₁ ~ C ₃₀ alkoxy group, C ₆ ~ C ₃₀ aryloxy and C ₁ ~ C ₅₀ monovalent substituent selected from the group consisting of an alkyl group or a; Or a C ₆ to C ₆₀ arylene group, a fluorenylene group, a C ₆ to C ₆₀ aromatic ring and a C ₃ to C ₆₀ alicyclic fused ring, a C ₂ to C ₆₀ heterocyclic group or a divalent aliphatic hydrocarbon Is selected from the group of divalent substituents consisting of groups, n is 1 or 2,

   R ₁ to R ₁₁ are each independently hydrogen, deuterium, halogen, nitrile group, nitro group, -LN (Ar ₁ ) (Ar ₂ ), C ₆ ~ C ₆₀ aryl group, fluorenyl group, C ₂ ~ C ₆₀ Heterocyclic group, C ₁ ~ C ₃₀ Alkoxy group, C ₆ ~ C _{30 It} is selected from the group consisting of aryloxy group and C ₁ ~ C ₅₀ Alkyl group,

   X is S, SO or SO ₂ ,

   L is a direct bond, C ₆ ~ C ₆₀ arylene group, fluorenylene group, C ₆ ~ C ₆₀ aromatic ring and C ₃ ~ C ₆₀ alicyclic fused ring, C ₂ ~ C ₆₀ heterocyclic group Or divalent aliphatic hydrocarbon, wherein Ar ₁ and Ar ₂ are each independently C ₆ -C ₆₀ aryl group, C ₂ -C ₆₀ heterocyclic group, fluorenyl group, C ₁ -C ₃₀ Is selected from the group consisting of an alkoxy group, a C ₆ -C ₃₀ aryloxy group and a C ₁ -C ₅₀ alkyl group.

   (In the Y, R ₁ to R _11, Ar ₁ and Ar ₂ of C ₆ ~ C ₆₀ aryl group, wherein Y, R ₁ to R _11, a fluorene group, and the Y and L of Ar ₁ and Ar ₂ The arylene group and the Y and L fluorenylene groups are deuterium, halogen, silane group, boron group, germanium group, C ₁ ~ C ₂₀ alkylthio group, C ₆ ~ C ₂₀ arylthio group, C ₁ ~ C ₂₀ alkoxy group, -N (Ar ₁ ) (Ar ₂ ), C ₁ -C ₂₀ alkyl group, C7-C20 arylalkyl group, C ₂ -C ₂₀ alkenyl group, C ₈ -C ₂₀ arylalkenyl group , substituted with one or more substituents selected from the alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, a C ₆ ~ C ₂₀ aryl group, and a hetero group, ring C ₂ ~ C ₂₀ substituted by deuterium of C ₂ ~ C ₂₀ Can be,

   The C ₆ ~ C ₆₀ heterocyclic group of Y, R ₁ to R ₁₁ , L, Ar _1, and Ar ₂ include at least one heteroatom of O, N, S, Si, and P, deuterium, a halogen group, -N (Ar ₁ ) (Ar ₂ ), C ₁ -C ₂₀ alkyl group, C ₇ -C ₂₀ arylalkyl group, C ₂ -C ₂₀ alkenyl group, C ₈ -C ₂₀ arylalkenyl group, C _1- It may be substituted with one or more substituents selected from the group consisting of C ₂₀ alkoxy group, C ₆ ~ C ₆₀ aryl group, C ₆ ~ C ₂₀ aryl group substituted with deuterium, a nitrile group and an acetylene group,

   The C ₁ to C ₃₀ alkoxy group and C ₆ to C ₃₀ aryloxy group of Y, R ₁ to R ₁₁ , Ar ₁ and Ar ₂ are deuterium, halogen, amino, nitrile, nitro, C ₁ to C ₂₀ alkyl groups, C ₂ to C ₂₀ alkenyl groups, C ₁ to C ₂₀ alkoxy groups, C ₃ to C ₃₀ cycloalkyl groups, C ₆ to C ₆₀ aryl groups, deuterium substituted with C ₆ to C ₂₀ It may be substituted with one or more substituents selected from the group consisting of an aryl group and a C ₂ ~ C ₆₀ heterocyclic group,

   The C ₁ to C ₅₀ alkyl group of Y, R ₁ to R ₁₁ , r ₁ and Ar ₂ may be C ₂ to C ₂₀ alkenyl group, C ₁ to C ₂₀ alkoxy group, C ₆ to C ₂₀ aryl group, In the group consisting of C ₆ ~ C ₂₀ aryl group, C ₇ ~ C ₂₀ arylalkyl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₂ ~ C ₂₀ heterocyclic group, nitrile group and acetylene group May be substituted with one or more substituents selected)
2. The method of claim 1,

   Compound represented by one of the following formula.

   <Formula 2>

   

   <Formula 3>

   

   <Formula 4>

   

   (In Formula 2 to Formula 4, A ring, R ₁ to R ₁₁ and X are the same as defined in Formula 1, Y in Formula 2 is selected from the group of monovalent substituents in the Y definition of Formula 1, Y is a direct bond or is selected from the group of divalent substituents in the definition of Y in Formula 1, and L, Ar ₁ and Ar ₂ in Formula 4 are the same as defined in Formula 1)
3. The method of claim 1,

   Compound represented by one of the following formula.

   <Formula 5>

   

   <Formula 6>

   

   <Formula 7>

   

   (R ₁ to R ₈ and X in Formula 5 to Formula 7 are the same as defined in Formula 1, Y in Formula 5 is selected from the monovalent substituent group in the definition of Y in Formula 1, Y in Formula 6 is Or a divalent substituent in the definition of Y in Formula 1, wherein L, Ar ₁ and Ar ₂ in Formula 7 are as defined in Formula 1)
4. The method of claim 1,

   Compound which is one of the following compounds.

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   
5. In an organic electric device comprising a first electrode, one or more organic material layers and a second electrode sequentially stacked,

   The organic material layer is an organic electroluminescent device comprising the compound of claim 1.
6. The method of claim 5,

   An organic electric device, characterized in that to form the compound into the organic material layer by a solution process (soluble process).
7. The method of claim 5,

   The organic material layer includes a light emitting layer and / or a hole transport layer,

   At least one of the light emitting layer and the hole transport layer is formed of the compound.
8. A display device comprising the organic electroluminescent device of claim 5; And

   A controller for driving the display device; Electronic device comprising a.
9. The electronic device of claim 8, wherein the organic electronic device is one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a single color or white light emitting device.

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