WO2012091471A2 - Compound and organic electronic element using same, and electronic device comprising the organic electronic element - Google Patents

Abstract

The present invention relates to a compound and to an organic electronic element using same, and to a terminal comprising the organic electronic element.

Description

Compound, organic electric element using same, electronic device thereof

The present invention relates to a compound, an organic electronic 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. In this case, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electric 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.

On the other hand, when only one material is used as the light emitting material, the maximum emission wavelength is shifted to a long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the 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 a 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 forming 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 element has not yet been made sufficiently, and therefore, the development of new materials is continuously required.

The present invention for solving the above problems of the background provides a compound in which a linking group having a substituent is bonded to a triphenyl derivative having a phenyl group substituted with deuterium. Therefore, the compound can be used as a hole injection, hole transport, electron injection, electron transport, light emitting material and passivation (kepping) material in organic electronic devices, in particular can be used alone or as a host or dopant in the light emitting material and host / dopant It can be used as a hole injection, hole transport layer.

Accordingly, the present invention provides a compound having a form in which a linking group having a substituent is bonded to a triphenyl derivative connected to a phenyl group substituted with deuterium, an organic electronic device using the same, and an electronic device including the organic electronic device. For the purpose of

In one aspect, the present invention provides a compound of the formula:

Accordingly, the present invention can provide a compound in which a linking group having a substituent is bonded to a triphenyl derivative having a phenyl group substituted with deuterium, an organic electronic device using the same, and an electronic device including the organic electronic device.

The present invention provides a compound in which a linking group having a substituent is bonded to a triphenyl derivative connected to a phenyl group substituted with deuterium, and an organic compound using the same, and shows an effect of increasing efficiency, lowering driving voltage, increasing lifetime, and increasing stability of an organic electronic device. It was.

1 to 6 show examples of the organic light emitting display device to which the compound of the present invention can be applied.

[Description of the code]

101: substrate 102: anode

103: hole injection layer 104: hole transport layer

105: light emitting layer 106: electron injection layer

107: electron transport layer 108: cathode

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".

The present invention can provide a compound represented by the following formula (1).

[Formula 1]

In this case, D represents deuterium and a may be an integer of 1 to 5.

In addition, R ₁ to R ₂ which may be substituted with a phenyl group are the same as or different from each other, and each independently a hydrogen atom; Substituted or unsubstituted aryl group having 5 to 60 carbon atoms, Substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, Substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, Substituted or unsubstituted carbon atoms 1 to 60 Alkoxy group, substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, substituted or unsubstituted alkoxycarbonyl group having 5 to 60 carbon atoms, substituted Or one or more selected from the group consisting of an amino group substituted with an unsubstituted aryl group having 5 to 60 carbon atoms, a halogen atom, a cyano group, a nitro group, a hydroxyl group, or a carboxyl group. Meanwhile, R ₁ to R ₂ may be bonded to groups adjacent to each other to form a substituted or unsubstituted saturated or unsaturated ring. For example, R ₁ to R ₂ may combine with groups adjacent to each other to form an aliphatic or hetero ring. In this case, b to c may be an integer of 1 to 4.

L is selected from a substituted or unsubstituted arylene group having 5 to 40 carbon atoms, a substituted or unsubstituted hetero arylene group having 5 to 60 nuclear atoms, and a divalent or trivalent substituted or unsubstituted aliphatic hydrocarbon. It may be, but is not limited to. On the other hand, d may be an integer of 0 to 3. For example, L may be one or more selected from the group consisting of phenyl group, biphenyl group, 1-naphthalyl group, 2-naphthyl group, pyridyl group, stilbene, anthracenyl group, phenanthrene group, pyrenyl group.

Meanwhile, in Chemical Formula 1, Y may be a derivative represented by Chemical Formula 2.

[Formula 2]

In this case, Ar ₁ ~ Ar ₃ may be the same as or different from each other, each independently represent a substituted or unsubstituted aryl group having 1 to 60 nuclear atoms, or a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, but It is not limited. For example, Ar ₂ to Ar ₃ may be a substituted or unsubstituted alkyl group. M may be an integer of 0 to 2.

Meanwhile, Ar ₁ may be one or one or more selected from the group consisting of a substituted or unsubstituted phenyl group, biphenyl group, 1-naphthyl group, 2-naphthyl group, thiophene group, pyrrole group, furan group, and pyridyl group have.

Ar ₂ and Ar ₃ may be one or more than one selected from the group consisting of functional groups in Table 1 below, but is not limited thereto.

TABLE 1

Meanwhile, the compound having the structural formula may be used in a solution process. In other words, the compound may form an organic material layer of an organic electric device, which will be described later, by a soluble process. In other words, when the compound is used as an organic material layer, the organic material layer may be formed by using various polymer materials, rather than a solution process or a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be produced in fewer layers by the method.

The present invention may provide a compound represented by one of the following Chemical Formulas 3 to 13.

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

Wherein D in formula 3 to 10 represents deuterium where a is an integer of 1 to 5,

R ₁ ~ R _4, which may be substituted on the phenyl group R1 ~ R ₂ described in the formulas (2) and (3) may be the same, but is not limited thereto. For example, R ₁ to R ₄ are the same as or different from each other, and are each independently of the other hydrogen, deuterium, tritium; Substituted or unsubstituted aryl group having 5 to 60 carbon atoms, Substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, Substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, Substituted or unsubstituted carbon atoms 1 to 60 Alkoxy group, substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, substituted or unsubstituted alkoxycarbonyl group having 5 to 60 carbon atoms, substituted Or an amino group substituted with an unsubstituted aryl group having 5 to 60 nuclear carbon atoms, a halogen atom, a cyano group, a nitro group, a hydroxyl group, or a carboxyl group, but is not limited thereto. Meanwhile, b to e may be integers of 0 to 4. In this case, R ₁ to R ₄ may be bonded to adjacent groups, respectively, to form a substituted or unsubstituted saturated or unsaturated ring. For example, R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₄ and R ₁ may each combine with an adjacent group to form a substituted or unsubstituted saturated or unsaturated ring.

Meanwhile, X in Chemical Formulas 7 to 10 may be C (R ₁ ) (R ₂ ), N (R ₃ ) (R ₄ ), S, O, Si, but is not limited thereto. On the other hand, f-i are integers of 0-1.

Compounds represented by Formulas 1 to 10 are specifically represented by the compound shown in Formula 11 below, but is not limited thereto.

[Formula 11]

In addition, the substituents in Chemical Formulas 1 to 11 may be substituted or unsubstituted even if not mentioned above, so that the substituents may be substituted with other substituents or substituents.

Various organic electric devices exist in which compounds in which a linking group is bonded to a triphenyl derivative having a phenyl group substituted with deuterium, described with reference to Chemical Formulas 1 to 11, are used as the organic material layer. Examples of the organic electric device in which the compounds described with reference to Chemical Formulas 1 to 11 may be used include an organic light emitting diode (OLED), an organic solar cell, an organic photoconductor (OPC) drum, and an organic transistor (organic TFT). .

As an example of an organic electroluminescent device (OLED) to which the compounds described with reference to Formulas 1 to 11 may be applied, the present invention is not limited thereto, and the compounds described above may be applied to various organic electroluminescent devices. .

Another embodiment of the present invention is an organic electric device comprising a first electrode, a second electrode and an organic material layer disposed between these electrodes, wherein at least one layer of the organic material layer comprises an organic electric field comprising the compounds of Formulas 1 to 11 Provided is a light emitting device.

1 to 6 show examples of the organic light emitting display device to which the compound of the present invention can be applied.

The organic light emitting device according to another embodiment of the present invention, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer And a structure known in the art using conventional manufacturing methods and materials in the art, except that at least one layer of the organic material layer including the electron injection layer is formed to include the compounds of Formulas 1 to 11. It can be prepared as.

The structure of the organic light emitting display device according to another embodiment of the present invention is illustrated in FIGS. 1 to 6, but is not limited thereto. In this case, reference numeral 101 denotes a substrate, 102 an anode, 103 a hole injection layer (HIL), 104 a hole transport layer (HTL), 105 a light emitting layer (EML), 106 an electron injection layer (EIL), 107 an electron transport layer ( ETL), 108 represents a negative electrode. Although not shown, the organic light emitting diode further includes a hole blocking layer (HBL) that blocks hole movement, an electron blocking layer (EBL) that blocks electrons from moving, a light emitting auxiliary layer that helps or assists light emission, and a protective layer. It may be located. The protective layer may be formed to protect the organic material layer or the cathode at the uppermost layer.

In this case, the compound described with reference to Formulas 1 to 11 may be included in one or more of an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer. Specifically, the compounds described with reference to Formulas 1 to 11 may be used in place of one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer, and a protective layer. Or may be used in combination with them. Of course, the organic layer may be used not only in one layer but also in two or more layers.

In particular, it can be used as a hole injection material, a hole transport material, an electron injection material, an electron transport material, a light emitting material and a passivation (kepping) material according to the compounds described with reference to the formulas (1) to 11, in particular a light emitting material and a host / It can be used as a host or dopant in a dopant, and can be used as a hole injection and hole transport layer.

For example, the organic light emitting device according to another embodiment of the present invention is a metal having a metal or conductivity on a substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation An oxide or an alloy thereof is deposited to form an anode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer is formed thereon, and then a material that can be used as a cathode is deposited thereon. Can be prepared.

In addition to the above method, an organic electronic device may be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate. The organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, but is not limited thereto and may have a single layer structure. In addition, the organic layer may be formed 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 made with a small number of layers.

The organic light emitting device according to another embodiment of the present invention may be used in a solution process such as spin coating or ink jet process.

The substrate is a support of the organic light emitting device, and a silicon wafer, quartz or glass plate, metal plate, plastic film or sheet, or the like can be used.

An anode is positioned over the substrate. This anode injects holes into the hole injection layer located thereon. As the anode material, a material having a large work function is usually preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline, and the like, but are not limited thereto.

The hole injection layer is located on the anode. The conditions required for the material of the hole injection layer are high hole injection efficiency from the anode, it should be able to transport the injected holes efficiently. This requires a small ionization potential, high transparency to visible light, and excellent hole stability.

The hole injection material is a material capable of well injecting holes from the anode at low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene, quinacridone-based organics, perylene-based organics, Anthraquinone, polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is positioned on the hole injection layer. The hole transport layer receives holes from the hole injection layer and transports the holes to the organic light emitting layer located thereon, and serves to prevent high hole mobility, hole stability, and electrons. In addition to these general requirements, when applied for vehicle body display, heat resistance to the device is required, and a material having a glass transition temperature (Tg) of 70 ° C. or higher is preferable. Materials satisfying these conditions include NPD (or NPB), spiro-arylamine compounds, perylene-arylamine compounds, azacycloheptatriene compounds, bis (diphenylvinylphenyl) anthracene and silicon germanium oxide. Compound, a silicon-based arylamine compound, and the like.

The organic light emitting layer is positioned on the hole transport layer. The organic light emitting layer is a layer for emitting light by recombination of holes and electrons injected from the anode and the cathode, respectively, and is made of a material having high quantum efficiency. 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.

Substances or compounds that satisfy these conditions include Alq3 for green, Balq (8-hydroxyquinoline beryllium salt) for blue, DPVBi (4,4'-bis (2,2-diphenylethenyl) -1,1'- biphenyl) series, Spiro material, Spiro-DPVBi (Spiro-4,4'-bis (2,2-diphenylethenyl) -1,1'-biphenyl), LiPBO (2- (2-benzoxazoyl) -phenol lithium salt), bis (diphenylvinylphenylvinyl) benzene, aluminum-quinoline metal complex, metal complexes of imidazole, thiazole and oxazole, and the like, perylene, and BczVBi (3,3 ') to increase blue light emission efficiency. [(1,1'-biphenyl) -4,4'-diyldi-2,1-ethenediyl] bis (9-ethyl) -9H-carbazole; DSA (distrylamine) can be used by doping in small amounts. In the case of red, DCJTB ([2- (1,1-dimethylethyl) -6- [2- (2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H, 5H Small amounts of doping such as -benzo (ij) quinolizin-9-yl) ethenyl] -4H-pyran-4-ylidene] -propanedinitrile) can be used. When the light emitting layer is formed using a process such as inkjet printing, roll coating, or spin coating, an organic light emitting layer is formed of a polymer of polyphenylene vinylene (PPV) or a polymer such as poly fluorene. Can be used for

The electron transport layer is positioned on the organic light emitting layer. Such an electron transport layer requires a material having high electron injection efficiency and efficiently transporting injected electrons from a cathode positioned thereon. To this end, it must be made of a material having high electron affinity and electron transfer speed and excellent stability to electrons. Examples of the electron transport material that satisfies such conditions 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 injection layer is stacked on the electron transport layer. The electron injection layer is a metal complex compound such as Balq, Alq3, Be (bq) 2, Zn (BTZ) 2, Zn (phq) 2, PBD, spiro-PBD, TPBI, Tf-6P, aromatic compound with imidazole ring, It can be produced using a low molecular weight material containing boron compounds and the like. At this time, the electron injection layer may be formed in a thickness range of 100 ~ 300Å.

The cathode is positioned on the electron injection layer. This cathode serves to inject electrons. As the material used as the cathode, it is possible to use the material used for the anode, and a metal having a low work function is more preferable for efficient electron injection. In particular, a suitable metal such as tin, magnesium, indium, calcium, sodium, lithium, aluminum, silver, or a suitable alloy thereof can be used. In addition, electrodes having a two-layer structure such as lithium fluoride and aluminum, lithium oxide and aluminum, strontium oxide and aluminum having a thickness of 100 μm or less may also be used.

As described above, hole injection materials, hole transport materials, light emitting materials, electron transport materials and electron injection materials suitable for fluorescent and phosphorescent devices of all colors, such as red, green, blue, and white, according to the compounds described with reference to Chemical Formulas 1 to 11 It can be used as a host or dopant material of various colors.

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 according to the material used.

Meanwhile, the present invention includes a display device including the organic electric element described above, and a terminal including a control unit for driving the display device. This terminal means a current or future wired or wireless communication terminal. The terminal according to the present invention described above may be a mobile communication terminal such as a mobile phone, and includes all terminals such as a PDA, an electronic dictionary, a PMP, a remote control, a navigation device, a game machine, various TVs, various computers, and the like.

Example

Hereinafter, the present invention will be described in more detail with reference to Preparation Examples and Experimental Examples. However, the following Preparation Examples and Experimental Examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

Production Example

Hereinafter, the preparation or synthesis examples of the compounds belonging to the formula (1) to 11 will be described.

However, some of the compounds belonging to the formula 1 to 11 because of the large number of compounds belonging to the formula (1) to 11 will be described by way of example. Those skilled in the art to which the present invention pertains, that is, those skilled in the art can prepare the compounds belonging to the present invention which are not illustrated through the preparation examples described below.

Hereinafter, the compounds were synthesized according to the synthesis method described above, and the examples in which the compounds were applied to an organic material layer of an organic electroluminescent device, for example, an organic electroluminescent device, were compared with those of commonly used compounds.

1) General Synthesis Method of Chemical Formulas 3, 4, 5

 Scheme 1

Starting material synthesis example

Synthesis of Starting Material S _1-1 (4-Bromo-P-terphenyl-d5)

Scheme 2

Phenyl-d5-boronic acid (43.8 g, 345 mmol), THF (700 mL), H ₂ O (350 mL) was added to a ₂ L round bottom flask, and 4,4 'Dibromo-biphenyl (161 g, 518 mmol), NaOH (42 g, 1035 mmol) and Pd (PPh ₃ ) ₄ (20 g, 17.3 mmol) were added in this order, and the reaction was performed at 80 ° C. for 24 hours.

After completion of the reaction, the mixture was extracted using methylene chloride, water and brine, and the organic layer was dried over MgSO ₄ .

The obtained organic layer was subjected to silicagel column to obtain 65.05 g (60%) of a product.

Synthesis of Starting Material S ₁ -2 (3-Bromo-P-terphenyl-d5)

 Scheme 3

Phenyl-d5-boronic acid (43.8 g, 345 mmol), THF (700 mL), H ₂ O (350 mL) was added to a ₂ L round bottom flask, and 1,4-Dibromobenzene (122.2 g, 518 mmol) and NaOH were dissolved. (42 g, 1035 mmol) and Pd (PPh ₃ ) ₄ (20 g, 17.3 mmol) were added sequentially, and the reaction proceeds at 80 ° C. for 24 hours.

After completion of the reaction, the mixture was extracted using methylene chloride, water and brine, and the organic layer was dried over MgSO ₄ .

The resulting organic layer was purified by silica gel short column and concentrated to recrystallize with methylene chloride and hexane to give 68.3 g (63%) of S ₁ -2-1. S ₁ -2-1 (68.3 g, 293 mmol), THF ( 600 mL), H ₂ O (300 mL), and then dissolved. 3-bromophenylboronic acid (39.2 g, 195 mmol), NaOH (35.7 g, 879 mmol) and Pd (PPh ₃ ) ₄ (17 g, 14.7 mmol) Insert as it is and proceed with the reaction for 24 hours at 80 ℃.

After completion of the reaction, the mixture was extracted using methylene chloride, water and brine, and the organic layer was dried over MgSO ₄ .

The obtained organic layer was concentrated after silica gel short column and recrystallized with methylene chloride and hexane to obtain 40 g (65%) of S ₁ -2-1.

Synthesis of Starting Material S _2-1 (2-Bromo-7-phnely-d5-9-phenyl-carbazole)

 Scheme 4

Phenyl-d5-boronic acid (43.8 g, 345 mmol), THF (700 mL), H ₂ O (350 mL) was added to a ₂ L round bottom flask, and 2,7-Dibromo-9-phenyl-carbazole (207g, 518 mmol), NaOH (42 g, 1035 mmol) and Pd (PPh ₃ ) ₄ (20 g, 17.3 mmol) were added in this order and the reaction proceeds at 80 ° C. for 24 hours.

After completion of the reaction, the mixture was extracted using methylene chloride, water and brine, and the organic layer was dried over MgSO ₄ .

The obtained organic layer was silicagel column to give 92.1 g (67%) of the product.

Synthesis of Starting Material S ₂ -2 [3-Bromo-9- (naphthalene1-yl) -7-phnely-d5-carbazole]

Step 1) 9- (Biphenyl-4-yl) -2-phenyl-d5-carbazole

 Scheme 5

Phenyl-d5-boronic acid (43.8 g, 345 mmol), THF (700 mL), H ₂ O (350 mL) was added to a ₂ L round bottom flask, and then 2-bromo-9- (naphthalene-1-yl)- Carbazole (193g, 518 mmol), NaOH (42 g, 1035 mmol) and Pd (PPh ₃ ) ₄ (20 g, 17.3 mmol) were added in this order and the reaction proceeds at 80 ° C. for 24 hours. After completion of the reaction, the mixture was extracted using methylene chloride, water and brine, and the organic layer was dried over MgSO ₄ . The obtained organic layer was silicagel column to give 87.9 g (68%) of the product.

Step 2) [3-Bromo-9- (naphthalene1-yl) -7-phnely-d5-carbazole]

 Scheme 6

9- (naphthalene-1-yl) -2-phenyl-d5-carbazole (30.4g, 82.2 mmol), NBS (15.36g, 86.31 mmol) and methylene chloride (200 mL) were added to a 500 mL reaction flask at room temperature. The reaction proceeds for a time.

After the reaction was completed, the mixture was extracted with an aqueous solution of methylene chloride and Na ₂ CO ₃ , dried over MgSO ₄ , concentrated, and the resulting compound was recrystallized from methylene chloride and hexane to give 31.3 g (85%) after a short phase column.

Synthesis of Starting Material S ₃ -1 [3-Bromo-9- (naphthalene1-yl) -7-phnely-d5-carbazole]

 Scheme 7

Synthesis of B (methyl 2- (9-phenyl-9H-carbazol-2-yl) benzoate)

In a 1 L 2-neck round bottom flask, starting material (36.9 g, 100 mmol), 2-bromomethylbenzoate (21.5 g, 100 mmol), Pd (PPh ₃ ) ₄ (3.47 g, 3 mmol), K ₂ CO ₃ (41.5 g , 300 mmol) was added, and THF (400 mL) and water (100 mL) were added as a solvent, followed by stirring at 80 ° C. for 6 hours. The reaction solution was cooled to room temperature and extracted with methylene chloride and water. The extract was dried over MgSO ₄ and dried under reduced pressure to obtain a crude product. The crude product was separated and purified through a silica gel column to obtain 26.0 g (yield: 69%) of an intermediate B as a yellow solid.

Synthesis of C (5-phenylindeno [1,2-b] carbazol-11 (5H) -one)

B (18.9 g, 50 mmol), methanesulfonic acid (4.8 g, 50 mmol) and poly-phosphoric acid (100 mL, 0.5M) were added to a 250 mL 2-neck round bottom flask and refluxed at 200 ° C. for 48 hours. . The reaction solution was cooled to room temperature and extracted with diethylether. The obtained extract was dried over MgSO ₄ and dried under reduced pressure to obtain a crude product, which was purified by silica gel column to obtain 5.87 g (yield: 34%) of intermediate C as a yellow solid. (C and D are obtained in similar yields.)

Synthesis of E (5-phenyl-5,11-dihydroindeno [1,2-b] carbazole)

Intermediate C (17.3 g, 50 mmol) and LiAlH ₄ (5.69 g, 150 mmol) were added to a 500 mL 2-neck round bottom flask, and 150 mL of THF was added as a solvent, followed by stirring at room temperature for 6 hours. After the reaction was completed, an appropriate amount of hydrochloric acid was added, and the reaction solution was extracted with diethylether. The obtained extract was dried under reduced pressure with MgSO ₄ to obtain a crude product, which was purified by silica gel column to obtain 11.4 g (yield: 69%) of intermediate E as a yellow solid.

Synthesis of G (3-Bromo-9- (naphthalene1-yl) -7-phnely-d5-carbazole)

Intermediate E (16.6 g, 50 mmol), iodomethane (15.6 g, 110 mmol), potassium hydroxide (8.42 g, 150 mmol) was added to a 500 mL 2-neck round bottom flask, and 150 mL methanol was added as a solvent. Stir for 3 hours. After the reaction was completed, the solvent methanol was removed by a concentrator, and then water and diethylether were added and extracted. The extract was dried over MgSO ₄ and dried under reduced pressure to obtain a Crude product, which was purified by silica gel column to obtain 12.9 g (yield: 72%) of intermediate G as a yellow solid.

Synthesis of Intermediate 2-1, 2-2

Scheme 8

Synthesis method of 2-1

1 compound (1 equiv), amine compound (1 equiv), Pd ₂ (dba) ₃ (0.05 mmol), PPh ₃ (0.1 equiv), NaO t -Bu (3 equiv), toluene (10.5 mL) in a round bottom flask / 1 mmol) and then proceed with the reaction at 100 ° C. After the reaction was completed, the mixture was extracted with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was silicagel column and recrystallized to obtain a product.

Synthesis method of 2-2

2-1 compound (1 equiv), Bis (pinacolato) diboron (1 equiv), Pd (dppf) Cl ₂ (0.03 equiv) in a round bottom flask. KOAc (3 equiv), DMF (6.3 mL / 1 mmol) were added, followed by heating to reflux at 130 ° C.

After completion of the reaction, the mixture was extracted with ether and water, and the obtained organic layer was dried over MgSO ₄ , concentrated, and silicagel column and recrystallized to obtain a product.

2-3 synthesis

2-2 compound (1 equiv), Br-L-Br (1.1 equiv), Pd (PPh ₃ ) ₄ (0.03-0.05 equiv), NaOH (3 equiv), THF (3 mL / 1 mmol) in a round bottom flask ), Add water (1.5 mL / 1 mmol).

Thereafter, the mixture is heated to reflux at 80 ° C to 90 ° C. After the reaction is completed, distilled water is diluted at room temperature. Then, the mixture was extracted with methylene chloride and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was purified by silicagel column and recrystallized to obtain a product.

Intermediate Synthesis Example

4-Bromo-N, N-diphenylaniline

Synthesis of

1,4-dibromobenzene (11.8 g, 50 mmol), diphenylamine (8.5 g, 50 mmol), Pd ₂ (dba) ₃ (2.3 g, 2.5 mmol), P Ph ₃ (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to obtain 11.3 g (yield: 70%) of product.

5-Bromo-N ¹ , N ¹ , N ³ , N ³ -tetraphenylbenzene-1,3-diamine

Synthesis of

1,3,5-tribromobenzene (15.74 g, 50 mmol), diphenylamine (17 g, 100 mmol), Pd ₂ (dba) ₃ (4.6 g, 5 mmol), PPh ₃ (2.62 g, 10 mmol), NaOt- Bu (28.83 g, 300 mmol) and toluene (525 mL) were obtained using 16.2 g (yield: 66%) of the product using the above synthesis method.

2-Bromo-N ¹ , N ⁴ -diphenyl-N ¹ , N ⁴ -dip-tolylbenzene-1,4-diamine

Synthesis of

1,2,5-tribromobenzene (15.74 g, 50 mmol), 4-methyl-N-phenylaniline (18.33 g, 100 mmol), Pd ₂ (dba) ₃ (4.6 g, 5 mmol), PPh ₃ (2.62 g, 10 mmol), NaOt-Bu (28.83 g, 300 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 to obtain 16.4 g (yield: 63%) of product.

N- (4-bromophenyl) -N-phenylnaphthalen-2-amine

Synthesis of

1,4-dibromobenzene (11.8 g, 50 mmol), N-phenylnaphthalen-2-amine (11g, 50 mmol), Pd ₂ (dba) ₃ (2.3g, 2.5 mmol), PPh ₃ (1.31 g, 5 mmol) , NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to obtain 13 g (yield: 69%) of product.

N- (4-bromophenyl) -N- (naphthalen-2-yl) naphthalen-2-amine

Synthesis of

1,4-dibromobenzene (11.8 g, 50 mmol), dinaphthalen-2-ylamine (13.5 g, 50 mmol), Pd ₂ (dba) ₃ (2.3 g, 2.5 mmol), PPh ₃ (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to obtain 15.3 g (yield: 72%) of product.

N- (4-bromophenyl) -N-phenylnaphthalen-1-amine

Synthesis of

1,4-dibromobenzene (11.8 g, 50 mmol), N-phenylnaphthalen-1-amine (11 g, 50 mmol), Pd ₂ (dba) ₃ (2.3g, 2.5 mmol), PPh ₃ (1.31 g, 5 mmol ), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to obtain 13.3 g (yield: 71%) of product.

N- (4-bromophenyl) -N- (naphthalen-1-yl) naphthalen-1-amine

Synthesis of

1,4-dibromobenzene (11.8 g, 50 mmol), dinaphthalen-1-ylamine (13.5 g, 50 mmol), Pd ₂ (dba) ₃ (2.3 g, 2.5 mmol), PPh ₃ (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to obtain 15.5 g (yield: 73%) of product.

4-Bromo-N- (4-methoxyphenyl) -N-phenylaniline

Synthesis of

1,4-dibromobenzene (11.8 g, 50 mmol), 4-methoxy-N-phenylaniline (10 g, 50 mmol), Pd ₂ (dba) ₃ (2.3g, 2.5 mmol), PPh ₃ (1.31 g, 5 mmol ), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to obtain 13.3 g (yield: 75%) of product.

N- (4-bromophenyl) -N- (4-fluorophenyl) naphthalen-2-amine

Synthesis of

1,4-dibromobenzene (11.8 g, 50 mmol), N- (4-fluorophenyl) naphthalen-2-amine (11.9g, 50 mmol), Pd ₂ (dba) ₃ (2.3g, 2.5 mmol), PPh ₃ ( 1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to obtain 12.7 g (yield: 65%) of product.

N- (4-bromophenyl) -N-phenylbiphenyl-4-amine

Synthesis of

1,4-dibromobenzene (11.8 g, 50 mmol), N-phenylbiphenyl-4-amine (12.3g, 50 mmol), Pd ₂ (dba) ₃ (2.3g, 2.5 mmol), PPh ₃ (1.31 g, 5 mmol ), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to obtain 14.8 g (yield: 74%) of product.

N- (biphenyl-4-yl) -N- (4-bromophenyl) naphthalen-1-amine

Synthesis of

1,4-dibromobenzene (11.8 g, 50 mmol), N- (biphenyl-4-yl) naphthalen-1-amine (14.8g, 50 mmol), Pd ₂ (dba) ₃ (2.3g, 2.5 mmol), PPh ₃ (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using 16.2 g (yield: 72%) of the product using the above synthesis method.

N- (biphenyl-4-yl) -N- (4-bromophenyl) biphenyl-4-amine

Synthesis of

1,4-dibromobenzene (11.8 g, 50 mmol), dibiphenyl-4-ylamine (16.1 g, 50 mmol), Pd ₂ (dba) ₃ (2.3 g, 2.5 mmol), PPh ₃ (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to give 17.4 g (yield: 73%) of product.

N- (biphenyl-4-yl) -N- (4-bromophenyl) -9,9-dimethyl-9H-fluoren-2-amine

Synthesis of

1,4-dibromobenzene (11.8 g, 50 mmol), N- (biphenyl-4-yl) -9,9-dimethyl-9H-fluoren-2-amine (18.1g, 50 mmol), Pd ₂ (dba) ₃ (2.3 g, 2.5 mmol), PPh ₃ (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol), toluene (525 mL) using the synthesis method of 2-1 above, 19.1 g (yield: 74 Product)

N- (4-bromophenyl) -N- (9,9-dimethyl-9H-fluoren-2-yl) -9,9-dimethyl-9H-fluoren-2-amine

Synthesis of

1,4-dibromobenzene (11.8 g, 50 mmol), bis (9,9-dimethyl-9H-fluoren-2-yl) amine (20.1g, 50 mmol), Pd ₂ (dba) ₃ (2.3g, 2.5 mmol ), PPh ₃ (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to give 19.1 g (yield: 74%) of product.

N- (4-bromophenyl) -9,9-dimethyl-N- (naphthalen-1-yl) -9H-fluoren-2-amine

Synthesis of

1,4-dibromobenzene (11.8 g, 50 mmol), 9,9-dimethyl-N- (naphthalen-1-yl) -9H-fluoren-2-amine (16.8g, 50 mmol), Pd ₂ (dba) ₃ (2.3 g, 2.5 mmol), PPh ₃ (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol), toluene (525 mL) using the synthesis method of 2-1 above, 16.7 g (yield: 68 Product)

N- (4-bromophenyl) -N, N-di-m-terphenyl-amine

Synthesis of

1,4-dibromobenzene (11.8 g, 50 mmol), N, N-di-m-terphenyl amine (23.7 g, 50 mmol), Pd ₂ (dba) ₃ (2.3 g, 2.5 mmol), PPh ₃ (1.31 g , 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 to give 21.1 g (yield: 67%) of product.

N- (4-bromophenyl) -N-phenyl-Nm-terphenyl-amine

Synthesis of

1,4-dibromobenzene (11.8 g, 50 mmol), N-phenyl-Nm-terphenyl amine (16.1 g, 50 mmol), Pd ₂ (dba) ₃ (2.3 g, 2.5 mmol), PPh ₃ (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to obtain 16.4 g (yield: 69%) of product.

4-bromo-N- (4- (naphthalen-1-yl) phenyl) -N-phenylaniline

Synthesis of

1,4-dibromobenzene (11.8 g, 50 mmol), 4- (naphthalen-1-yl) -N-phenylaniline (14.8g, 50 mmol), Pd ₂ (dba) ₃ (2.3g, 2.5 mmol), PPh ₃ (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to give 15.1 g (yield: 67%) of product.

4-Bromo-N- (4- (naphthalen-2-yl) phenyl) -N-phenylaniline

Synthesis of

1,4-dibromobenzene (11.8 g, 50 mmol), 4- (naphthalen-2-yl) -N-phenylaniline (14.8g, 50 mmol), Pd ₂ (dba) ₃ (2.3g, 2.5 mmol), PPh ₃ (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using 14.2 g (yield: 66%) of the product using the synthesis method 2-1 above.

N- (4-bromophenyl) -N, 9,9-triphenyl-9H-fluoren-2-amine

Synthesis of

1,4-dibromobenzene (11.8 g, 50 mmol), N, 9,9-triphenyl-9H-fluoren-2-amine (20.5 g, 50 mmol), Pd ₂ (dba) ₃ (2.3 g, 2.5 mmol), PPh ₃ (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to obtain 20 g (yield: 71%) of product.

N- (4-bromophenyl) -N-phenyl-9,9'-spirobi [fluoren] -2-amine

Synthesis of

1,4-dibromobenzene (11.8 g, 50 mmol), N-phenyl-9,9'-spirobi [fluoren] -2-amine (20.4 g, 50 mmol), Pd ₂ (dba) ₃ (2.3 g, 2.5 mmol ), PPh ₃ (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to obtain 19.7 g (yield: 70%) of product.

N- (biphenyl-4-yl) -N- (4-bromophenyl) phenanthren-9-amine

Synthesis of

1,4-dibromobenzene (11.8 g, 50 mmol), N- (biphenyl-4-yl) phenanthren-9-amine (17.3 g, 50 mmol), Pd ₂ (dba) ₃ (2.3 g, 2.5 mmol), PPh ₃ (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 to obtain 17.8 g (yield: 71%) of product.

N- (biphenyl-4-yl) -N- (4-bromophenyl) dibenzo [b, d] furan-3-amine

Synthesis of

1,4-dibromobenzene (11.8 g, 50 mmol), N- (biphenyl-4-yl) dibenzo [b, d] furan-3-amine (16.8 g, 50 mmol), Pd ₂ (dba) ₃ (2.3 g , 2.5 mmol), PPh ₃ (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were prepared using 17.9 g (yield: 73%) of the above synthesis method. Obtained the product

N- (biphenyl-4-yl) -N- (4-bromophenyl) dibenzo [b, d] thiophen-3-amine

Synthesis of

1,4-dibromobenzene (11.8 g, 50 mmol), N- (biphenyl-4-yl) dibenzo [b, d] thiophen-3-amine (17.6g, 50 mmol), Pd ₂ (dba) ₃ (2.3g , 2.5 mmol), PPh ₃ (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol), toluene (525 mL) were prepared using the synthesis method of 2-1 above in 17.5 g (yield: 69%). Obtained the product

N- (biphenyl-4-yl) -N- (4-bromophenyl) pyren-4-amine

Synthesis of

1,4-dibromobenzene (11.8 g, 50 mmol), N- (biphenyl-4-yl) pyren-4-amine (18.5g, 50 mmol), Pd ₂ (dba) ₃ (2.3g, 2.5 mmol), PPh ₃ (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to obtain 19.1 g (yield: 73%) of product.

N- (4-bromophenyl) -N- (naphthalen-1-yl) -4-phenylnaphthalen-1-amine

Synthesis of

1,4-dibromobenzene (11.8 g, 50 mmol), N- (naphthalen-1-yl) -4-phenylnaphthalen-1-amine (17.3g, 50 mmol), Pd ₂ (dba) ₃ (2.3g, 2.5 mmol ), PPh ₃ (1.31 g, 5 mmol), NaOt-Bu (14.42 g, 150 mmol) and toluene (525 mL) were obtained using the synthesis method of 2-1 above to obtain 18.5 g (yield: 74%) of product.

N- (4-bromophenyl) -N- (6-phenylnaphthalen-2-yl) naphthalen-1-amine

Synthesis of

1,4-dibromobenzene (11.8 g, 50 mmol), N- (6-phenylnaphthalen-2-yl) naphthalen-1-amine (17.3g, 50 mmol), Pd ₂ (dba) ₃ (2.3g, 2.5 mmol) , PPh ₃ (1.31 g, 5 mmol), NaO t -Bu (14.42 g, 150 mmol) and toluene (525 mL) were prepared using 17.8 g (yield: 71%) of the above-mentioned synthesis method.

Obtained the product

Final compound synthesis

 Scheme 9

3a-B (OH) ₂ , or 4a-B (OH) ₂ or 5a-B (OH) ₂ (1 equivalent), 2-1 or 2-3 compounds (1.1 equivalent) in a round bottom flask, Add Pd (PPh ₃ ) ₄ (0.03-0.05 equiv), NaOH (3 equiv), THF (3 mL / 1 mmol), and water (1.5 mL / 1 mmol).

After that, the mixture is heated to reflux at 80 ° C to 90 ° C. After the reaction is completed, distilled water is diluted at room temperature. Then, the mixture was extracted with methylene chloride and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was purified by silicagel column and recrystallized to obtain a product by FD-MS as shown in the table below.

TABLE 2

Manufacturing Evaluation of Organic Light Emitting Diode

Various compounds obtained through synthesis were used as light emitting host materials or hole transporting layers of the light emitting layer, respectively, to fabricate an organic light emitting device according to a conventional method.

First, a copper phthalocyanine (hereinafter abbreviated as CuPc) film was vacuum-deposited on the ITO layer (anode) formed on the organic substrate to form a thickness of 10 nm. Subsequently, when the compounds of the present invention are used as a host of the light emitting layer, 4,4-bis [ N- (1-naphthyl) -N -phenylamino] biphenyl (hereinafter abbreviated as α-NPD) is used as a hole transporting layer compound on the film. Was vacuum deposited to a thickness of 30 nm to form a hole transport layer. A light emitting layer in which 45% thick BD-052X (Idemitsu Co., Ltd.) is doped with a 7% doped layer, wherein BD-052X is a blue fluorescent dopant, and the light emitting host material is the compound of the invention or 9, 10-di- (naphthalene- 2-anthracene) = AND].

When measuring the invention compounds as a phosphorescent host material, the phosphorescent material is deposited to form a light emitting layer and at the same time abbreviated as tris (2-phenylpyridine) iridium (hereinafter Ir (ppy) ₃ ) as a phosphorescent Ir metal complex dopant. ) Was added. At this time, the concentration of Ir (ppy) _{3 in} the light emitting layer was 10% by weight. {(1,1'bisphenyl) -4-oleito} bis (2-methyl-8-quinolineoleito) aluminum (hereinafter abbreviated as BAlq) was vacuum deposited to a thickness of 10 nm into the hole blocking layer, and then Tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was formed into an electron injection layer to a thickness of 40 nm. Subsequently, LiF, an alkyl halide metal, was deposited to a thickness of 0.2 nm, and then Al was deposited to a thickness of 150 nm to use an Al / LiF as a cathode to prepare an organic light emitting device.

Comparative Experiment

When the compounds of the present invention were measured by a fluorescent host and a hole transport layer, α-NPD (Formula 12) was used as the hole transport layer instead of the compounds of the present invention, and AND [9,10-di (naphthalene-2-yl) for comparison. ) anthracene (13) was used as a fluorescent host material to fabricate an organic light emitting display device having the same structure as that of the experimental example.

[Formula 12]

[Formula 13]

TABLE 3

As can be seen from the results of Table 3, the organic electroluminescent device using the above-described compounds of the present invention as a material for an organic electroluminescent device has a high efficiency and a blue color light emission with improved color purity, so that the light emitting host and hole transport of the organic electroluminescent device are obtained. Used as a material, it can significantly improve low driving voltage, high luminous efficiency and lifespan.

When 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.

Although the embodiments of the present invention have been described above with reference to the accompanying drawings, the technical configuration of the present invention described above may be modified in other specific forms by those skilled in the art to which the present invention pertains without changing its technical spirit or essential features. It will be appreciated that it may be practiced. Therefore, the embodiments described above are to be understood as illustrative and not restrictive in all aspects. In addition, the scope of the present invention is shown by the claims below, rather than the above detailed description. Also, it is to be construed that all changes or modifications derived from the meaning and scope of the claims and their equivalent concepts are included in the scope of the present invention.

CROSS-REFERENCE TO RELATED APPLICATION

This patent application claims priority pursuant to US Patent Law Section 119 (a) (35 USC § 119 (a)) of Patent Application No. 10-2010-0136323, filed with Korea on December 28, 2010. All content is incorporated by reference in this patent application. In addition, if this patent application claims priority to a country other than the United States for the same reason, all its contents are incorporated into this patent application by reference.

Claims (13)

1. Compound represented by the following formula.

   

   Wherein D represents deuterium, a is an integer of 1 to 5, and R ₁ to R ₂ are the same as or different from each other, and are each independently a hydrogen atom; Substituted or unsubstituted aryl group having 5 to 60 carbon atoms, Substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, Substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, Substituted or unsubstituted carbon atoms 1 to 60 Alkoxy group, substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, substituted or unsubstituted alkoxycarbonyl group having 5 to 60 carbon atoms, substituted Or one or one or more selected from the group consisting of an unsubstituted amino group substituted with an aryl group having 5 to 60 carbon atoms, a halogen atom, a cyano group, a nitro group, a hydroxyl group or a carboxyl group, wherein b to c are 1 to Is an integer of 4, wherein L is a substituted or unsubstituted arylene group having 5 to 40 carbon atoms, a substituted or unsubstituted hetero arylene group having 5 to 60 nuclear atoms, and a divalent or trivalent substituted or unsubstituted aliphatic group. Group selected from hydrocarbons, d is an integer from 0 to 3, wherein Y is a derivative represented by the formula below.

    [Formula 2]

   

   Wherein Ar ₁ to Ar ₃ are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group having 1 to 60 nuclear atoms, or a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, M is an integer of 0-2.
2. The method of claim 1,

   Ar ₁ is one or one or more selected from the group consisting of a substituted or unsubstituted phenyl group, biphenyl group, 1-naphthyl group, 2-naphthyl group, thiophene group, pyrrole group, furan group, pyridyl group

   Ar ₂ and Ar ₃ is one or more compounds selected from the group consisting of the functional groups of the table below.

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   
3. The compound of claim 1, wherein the compound represented by the formula is represented by one of the following formulas.

   

   

   

   

   

   

   

   

   R ₃ to R ₄ are the same as or different from each other, and each independently of each other, a hydrogen atom, deuterium, or tritium; Substituted or unsubstituted aryl group having 5 to 60 carbon atoms, Substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, Substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, Substituted or unsubstituted carbon atoms 1 to 60 Alkoxy group, substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, substituted or unsubstituted alkoxycarbonyl group having 5 to 60 carbon atoms, substituted Or one or one or more selected from the group consisting of an amino group, a halogen atom, a cyano group, a nitro group, a hydroxyl group or a carboxyl group substituted with an unsubstituted aryl group having 5 to 60 nuclear carbon atoms, wherein d to e are 0 to Is an integer of 4, and X ₁ to X ₄ are C (R ₁ ) (R ₂ ), N (R ₃ ) (R ₄ ), S, O, Si, and f to i are integers of 0 to 1. .
4. The method of claim 1,

   The L is a compound characterized in that one or more selected from the group consisting of phenyl group, biphenyl group, 1- naphthal group, 2-naphthyl group, pyridyl group, stilbene, anthracenyl group, phenanthrene group, pyrenyl group.
5. The method of claim 3,

   R ₁ , R ₂ , R ₃ and R ₄ are each combined with an adjacent group to form a substituted or unsubstituted saturated or unsaturated ring.
6. The method of claim 3,

   Compound represented by the formula is a compound represented by one of the following formula.

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   
7. An organic electric device comprising at least one organic material layer comprising a compound of any one of claims 1 to 6.
8. The method of claim 7, wherein

   The organic electroluminescent device according to claim 1, wherein the organic layer is formed by a solution process.
9. The method of claim 7, wherein

   The organic electroluminescent device is an organic electroluminescent device comprising a first electrode, the at least one organic material layer and the second electrode in a stacked form sequentially.
10. The method of claim 9,

    The organic material layer is an organic electric device, characterized in that any one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, a light emitting layer.
11. The method of claim 10,

    And the light emitting layer comprises the compound as a light emitting host material or the hole transport layer comprises the compound.
12. A display device comprising the organic electric element of claim 11;

    And a controller for driving the display device.
13. The method of claim 12,

    The organic electronic device is one of an organic light emitting diode (OLED), an organic solar cell, an organic photoconductor (OPC) drum, and an organic transistor (organic TFT).

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