KR20200119503A - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention provides: a compound represented by chemical formula 1; an organic electric element comprising a first electrode, a second electrode, and an organic material layer disposed between the first electrode and the second electrode; and an electronic device comprising the organic electric element. By comprising the compound represented by chemical formula 1 in the organic material layer, it is possible to lower a driving voltage, and improve luminous efficiency and a lifespan of the organic electric element.

Description

Compound for organic electric device, organic electric device using the same, and electronic device thereof {COMPOUND FOR ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN 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, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic electric device using an organic light emission phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electric device, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

Materials used as an organic material layer in an organic electric device can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, according to their functions. In addition, the light-emitting material may be classified into a high molecular type and a low molecular type according to its molecular weight, and according to a light emitting mechanism, it may be classified into a fluorescent material derived from the singlet excited state of the electron and a phosphorescent material derived from the triplet excited state of the electron. have. In addition, the light-emitting material may be classified into blue, green, and red light-emitting materials and yellow and orange light-emitting materials necessary for realizing better natural colors according to the light-emitting color.

On the other hand, when only one material is used as a light-emitting material, the maximum emission wavelength shifts to a long wavelength due to intermolecular interactions, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect.Therefore, the increase in color purity and energy transfer A host/dopant system may be used as a light emitting material in order to increase the luminous efficiency through. The principle is that when a small amount of a 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 to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant used.

Currently, the portable display market is increasing in size as a large-area display, and for this reason, more power consumption than the power consumption required by the existing portable display is required. Therefore, power consumption has become an important factor for portable displays that have a limited power supply source, such as a battery, and efficiency and life problems are also important factors that must be solved.

Efficiency, lifespan, and driving voltage are related to each other, and when the efficiency is increased, the driving voltage decreases relatively, and as the driving voltage decreases, crystallization of organic materials by Joule heating generated during driving decreases. It shows a tendency to increase the lifespan. However, simply improving the organic material layer cannot maximize efficiency. This is because long life and high efficiency can be achieved at the same time when the energy level and T1 value between each organic material layer and the intrinsic properties of materials (mobility, interfacial properties, etc.) are optimally combined.

In addition, in recent years, in order to solve the problem of light emission in the hole transport layer in organic electroluminescent devices, a method of using a light emitting auxiliary layer between the hole transport layer and the light emitting layer is being studied, and desired according to each light emitting layer (R, G, B). Since material properties are different, it is time to develop a light emitting auxiliary layer for each light emitting layer.

In general, electrons are transferred from the electron transport layer to the light emitting layer, and holes are transferred from the hole transport layer to the light emitting layer, thereby generating excitons through recombination.

However, in the case of the material used for the hole transport layer, since it must have a low HOMO value, most have a low T ₁ value, and as a result, excitons generated in the light-emitting layer pass to the hole transport layer interface or the hole transport layer, resulting in the hole transport layer. Light emission at the interface or charge unbalance in the light-emitting layer is caused to emit light at the hole transport layer interface.

When light is emitted at the hole transport layer interface, the color purity and efficiency of the organic electronic device are deteriorated, and the lifespan is shortened. Therefore, it must be a material having a HOMO level between the HOMO energy level of the hole transport layer and the HOMO energy level of the light emitting layer, has a high T1 value, and has a suitable driving voltage range (within the range of the driving voltage of the blue device of the full device) There is an urgent need to develop a light-emitting auxiliary layer having mobility).

However, this cannot be achieved simply with the structural characteristics of the core of the light-emitting auxiliary layer material, and the characteristics of the core and sub-substituents of the light-emitting auxiliary layer material, and the proper combination between the light-emitting auxiliary layer and the hole transport layer, and the light-emitting auxiliary layer and the light-emitting layer are made When it is lost, a high-efficiency and long-life device can be implemented.

Meanwhile, development of materials for a light-emitting layer and a light-emitting auxiliary layer having a stable characteristic, that is, a high glass transition temperature, against Joule heating generated when the device is driven is also required. The low glass transition temperature of the light emitting layer and the light emitting auxiliary layer material decreases the uniformity of the thin film surface when the device is driven, and the material may be deformed due to heat generated when the device is driven, which has been reported to have a great effect on the life of the device.

Therefore, it is necessary to develop a material that can withstand a long time during deposition, that is, a material with strong heat resistance, and materials that form the organic material layer in the device, such as hole injection material, hole transport material, and light emission, are required to fully exhibit the excellent characteristics of organic electronic devices. A material, an electron transport material, an electron injection material, a light-emitting auxiliary layer material, etc. must be supported by a stable and efficient material. In particular, development of materials used for a light-emitting auxiliary layer and a light-emitting layer is required.

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

In one aspect, the present invention provides a compound represented by the following formula.

In another aspect, the present invention provides an organic electric device and an electronic device using the compound represented by the above formula.

By using the compound according to an exemplary embodiment of the present invention, not only can the driving voltage of the device be lowered, but also the luminous efficiency and lifetime of the device can be greatly improved.

1 to 3 are exemplary views of an organic electroluminescent device according to the present invention.
4 shows a chemical formula according to an aspect of the present invention.

The terms "aryl group" and "arylene group" used in the present invention each have 6 to 60 carbon atoms, and are not limited thereto. In the present invention, the aryl group or the arylene group may include a monocyclic type, a ring aggregate, a conjugated ring system, a spiro compound, and the like. In addition, unless otherwise stated in the specification, a fluorenyl group may be included in the aryl group, and a fluorenylene group may be included in the arylene group.

The terms "fluorenyl group", "fluorenylene group" and "fluorentriyl group" used in the present invention are monovalent, 2 in which R, R'and R" are all hydrogen in the following structures, respectively, unless otherwise specified It means a valence or trivalent functional group, and "substituted fluorenyl group", "substituted fluorenylene group" or "substituted fluorentriyl group" means that at least one of the substituents R, R', R" is other than hydrogen It means that it is a substituent, and includes the case where R and R'are bonded to each other to form a spy compound with the carbon to which they are bonded. In the present specification, a fluorenyl group, a fluorenylene group, and a fluorenetriyl group may all be referred to as fluorene groups regardless of valence such as monovalent, divalent, or trivalent.

The term "spyro compound" as used in the present invention has a'spyro linkage', and the spyro linkage refers to a linkage made by two rings sharing only one atom. At this time, the atoms shared in the two rings are referred to as'spiro atoms', and these are respectively referred to as'monospiro-','dispiro-', and'trispyro-' depending on the number of spiro atoms in a compound. 'It is called a compound.

The term "heterocyclic group" as used in the present invention includes not only an aromatic ring such as a "heteroaryl group" or a "heteroarylene group", but also a non-aromatic ring, and unless otherwise stated, each carbon number including one or more heteroatoms It means a ring of 2 to 60, but is not limited thereto. The term "heteroatom" as used herein refers to N, O, S, P, or Si unless otherwise specified, and the heterocyclic group is a monocyclic type containing a heteroatom, a ring aggregate, a conjugated ring system, spy It means a compound and the like.

The term "heterocyclic group" as used herein refers to a ring in which a heteroatom such as N, O, S, P, or Si is included instead of carbon forming the ring, and "heteroaryl group" or "heteroarylene group" A non-aromatic ring is included as well as an aromatic ring such as, and a compound including a heteroatom group such as SO ₂ , P=O and the like may be included instead of carbon forming the ring.

The term "aliphatic ring group" used in the present invention refers to cyclic hydrocarbons excluding aromatic hydrocarbons, and includes monocyclic, cyclic aggregates, conjugated cyclic systems, spiro compounds, etc., unless otherwise stated, It means a ring of 3 to 60, but is not limited thereto. For example, benzene as an aromatic ring and cyclohexane, a non-aromatic ring, are fused to an aliphatic ring.

In the present specification, the'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc. exemplified as examples of each symbol and its substituent may describe'the name of the group reflecting the number', but it is described as the'parent compound name' You may. For example, in the case of'phenanthrene', which is a kind of aryl group, the monovalent'group' is'phenanthryl' and the divalent group can be labeled with the valence by dividing the valency such as'phenanthrylene'. Regardless, it may be described as the parent compound name'phenanthrene'. Similarly, even in the case of pyrimidine, it may be described as'pyrimidine' regardless of the valence, or in the case of monovalent, it may be described as the'name of the group' of the corresponding valency, such as pyrimidinyl group and in the case of divalent, pyrimidinylene. have.

In addition, in the present specification, when describing the name of the compound or the name of the substituent, numbers or alphabets indicating positions may be omitted. For example, pyrido[4,3-d]pyrimidine to pyridopyrimidine, benzofuro[2,3-d]pyrimidine to benzofuropyrimidine, 9,9-dimethyl-9H-flu Orene can be described as dimethylfluorene or the like. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline can be described as benzoquinoxaline.

In addition, unless there is an explicit explanation, the formula used in the present invention is applied in the same way as the definition of the substituent group defined by the index definition of the following formula.

Here, when a is an integer of 0, the substituent R ¹ means that the substituent R ¹ does not exist, that is, when a is 0, it means that all hydrogens are bonded to the carbon forming the benzene ring. It may be omitted and the formula or compound may be described. In addition, when a is an integer of 1, one substituent R ¹ is bonded to any one of carbons forming a benzene ring, and when a is an integer of 2 or 3, it may be bonded, for example, as follows, and a is 4 to 6 In the case of an integer of, it is bonded to the carbon of the benzene ring in a similar manner, and when a is an integer of 2 or more, R ¹ may be the same or different from each other.

In addition, unless otherwise described in the specification, the ring formed by bonding of adjacent groups to each other is a C ₆ ~ C ₆₀ aromatic ring group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; C ₃ ~ C ₆₀ aliphatic ring group; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; And it may be selected from the group consisting of a combination thereof.

Hereinafter, a laminated structure of an organic electric device including the compound of the present invention will be described with reference to FIGS. 1 to 3.

In adding reference numerals to elements of each drawing, it should be noted that the same elements are assigned the same numerals as possible even if they are indicated on different drawings. In addition, in describing the present invention, if it is determined that a detailed description of a related known configuration or function may obscure the subject matter of the present invention, a detailed description thereof will be omitted.

In describing the constituent elements of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are only used to distinguish the component from other components, and the nature, order, or order of the component is not limited by the term. When a component is described as being "connected", "coupled" or "connected" to another component, that component may be directly connected or connected to that other component, but another component between each component It should be understood that elements may be “connected”, “coupled” or “connected”.

In addition, when a component such as a layer, film, region, or plate is said to be "on" or "on" another component, it is not only "directly over" another component, as well as another component in the middle. It should be understood that cases may also be included. Conversely, it should be understood that when an element is "directly above" another part, it means that there is no other part in the middle.

1 to 3 are exemplary views of an organic electric device according to an embodiment of the present invention.

Referring to FIG. 1, an organic electric device 100 according to an embodiment of the present invention includes a first electrode 110, a second electrode 170, and a first electrode 110 formed on a substrate (not shown). ) And an organic material layer formed between the second electrode 170.

The first electrode 110 may be an anode (anode), the second electrode 170 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 material layer may include a hole injection layer 120, a hole transport layer 130, a light emitting layer 140, an electron transport layer 150, and an electron injection layer 160. Specifically, the hole injection layer 120, the hole transport layer 130, the light emitting layer 140, the electron transport layer 150, and the electron injection layer 160 may be sequentially formed on the first electrode 110.

Preferably, the light efficiency improvement layer 180 may be formed on one side of both surfaces of the first electrode 110 or the second electrode 170 not in contact with the organic material layer, and when the light efficiency improvement layer 180 is formed The light efficiency of the organic electric device can be improved.

For example, the light efficiency improvement layer 180 may be formed on the second electrode 170. In the case of a top emission organic light emitting device, the light efficiency improvement layer 180 is formed to form the second electrode 170. ), optical energy loss due to SPPs (surface plasmon polaritons) can be reduced, and in the case of a bottom emission organic light emitting device, the light efficiency improvement layer 180 performs a buffering role for the second electrode 170 can do.

Meanwhile, a buffer layer 210 or a light emission auxiliary layer 220 may be further formed between the hole transport layer 130 and the emission layer 140, which will be described with reference to FIG. 2.

Referring to FIG. 2, an organic electric device 200 according to another embodiment of the present invention includes a hole injection layer 120, a hole transport layer 130, a buffer layer 210 sequentially formed on the first electrode 110, A light-emitting auxiliary layer 220, a light-emitting layer 140, an electron transport layer 150, an electron injection layer 160, and a second electrode 170 may be included, and a light efficiency improvement layer 180 is formed on the second electrode. Can be.

Although not shown in FIG. 2, an electron transport auxiliary layer may be further formed between the light emitting layer 140 and the electron transport layer 150.

In addition, according to another embodiment of the present invention, the organic material layer may have a form in which a plurality of stacks including a hole transport layer, an emission layer, and an electron transport layer are formed. This will be described with reference to FIG. 3.

Referring to FIG. 3, in an organic electric device 300 according to another embodiment of the present invention, two stacks ST1 and ST2 formed of a multi-layered organic material layer are formed between the first electrode 110 and the second electrode 170. A set or more may be formed, and a charge generation layer CGL may be formed between the stacks of organic material layers.

Specifically, the organic electric device according to the embodiment of the present invention includes a first electrode 110, a first stack ST1, a charge generation layer (CGL), a second stack ST2, and a second electrode. 170 and a light efficiency improvement layer 180 may be included.

The first stack ST1 is an organic material layer formed on the first electrode 110, which is a first hole injection layer 320, a first hole transport layer 330, a first emission layer 340, and a first electron transport layer 350. ), and the second stack ST2 may include a second hole injection layer 420, a second hole transport layer 430, a second emission layer 440, and a second electron transport layer 450. . As described above, the first stack and the second stack may be organic material layers having the same laminated structure, but may be organic material layers having different laminated structures.

A charge generation layer CGL may be formed between the first stack ST1 and the second stack ST2. The charge generation layer CGL may include a first charge generation layer 360 and a second charge generation layer 361. The charge generation layer CGL is formed between the first emission layer 340 and the second emission layer 440 to increase current efficiency generated in each emission layer and smoothly distribute electric charges.

The first emission layer 340 may include a light-emitting material including a blue fluorescent dopant in a blue host, and the second emission layer 440 includes a material doped with a greenish yellow dopant and a red dopant in a green host. It may be included, but the material of the first emission layer 340 and the second emission layer 440 according to an embodiment of the present invention is not limited thereto.

In FIG. 3, n may be an integer of 1-5. When n is 2, a charge generation layer CGL and a third stack may be additionally stacked on the second stack ST2.

When a plurality of emission layers are formed by the multilayer stack structure method as shown in FIG. 3, it is possible to manufacture an organic electroluminescent device in which white light is emitted by the mixing effect of light emitted from each emission layer, as well as various colors of light. It is also possible to manufacture an organic electroluminescent device that emits light.

The compound represented by Formula 1 of the present invention is a hole injection layer (120, 320, 420), a hole transport layer (130, 330, 430), a buffer layer (210), a light emission auxiliary layer (220), an electron transport layer (150, 350). , 450), the electron injection layer 160, the light emitting layers 140, 340, 440, or the light efficiency improvement layer 180 may be used as a material, but preferably, the light emitting auxiliary layer 220, the light emitting layers 140, 340, 440 ) And/or the light efficiency improvement layer 180 may be used as a material.

Since the band gap, electrical properties, and interfacial properties may vary depending on which substituent is bonded to any position of the same and similar core, a study on the selection of the core and the combination of sub-substituents bonded thereto In particular, long life and high efficiency can be achieved at the same time when the energy level and T ₁ value between each organic material layer and the intrinsic properties of materials (mobility, interfacial properties, etc.) are optimally combined.

Therefore, in the present invention, by using the compound represented by Formula 1 as a material for the light emission auxiliary layer 220, the light emission layers 140, 340, 440, and/or the light efficiency improvement layer 180, the energy level and T ₁ between each organic material layer By optimizing the value and intrinsic properties of the material (mobility, interfacial properties, etc.), it is possible to simultaneously improve the life and efficiency of organic electric devices.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD or CVD. For example, a metal or a conductive metal oxide or an alloy thereof is deposited on a substrate to form the anode 110, and a hole injection layer 120 thereon , After forming an organic material layer including the hole transport layer 130, the light emitting layer 140, the electron transport layer 150 and the electron injection layer 160, it can be prepared by depositing a material that can be used as the cathode 170 thereon. have. In addition, a light emitting auxiliary layer 220 between the hole transport layer 130 and the light emitting layer 140, and an electron transport auxiliary layer (not shown) between the light emitting layer 140 and the electron transport layer 150 may be further formed. It can also be formed in a stack structure as shown.

In addition, the organic material layer is a solution process or a solvent process other than a vapor deposition method using various polymer materials, such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, a roll-to-roll process, and a doctor blaze. It can be manufactured with fewer layers by a method such as a printing process, a screen printing process, or a thermal transfer method. Since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the forming method.

The organic electric device according to an embodiment of the present invention may be of a top emission type, a bottom emission type, or a double side emission type depending on the material used.

In addition, the organic electric device according to an embodiment of the present invention may be selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a monochromatic lighting device, and a quantum dot display device.

Another embodiment of the present invention may include a display device including the organic electric device of the present invention described above, and an electronic device including a control unit for controlling the display device. At this time, the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation, game consoles, various TVs, and various computers.

Hereinafter, a compound according to an aspect of the present invention will be described.

A compound according to an aspect of the present invention is represented by the following formula (1).

<Formula 1>

In Formula 1, each symbol may be defined as follows.

A ring, B ring, and C ring are each independently a C ₆ ~ C ₆₀ aromatic ring group; Fluorene group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; And C ₃ ~ C ₆₀ aliphatic ring group; is selected from the group consisting of.

When the A ring, the B ring and the C ring are each an aromatic ring group, preferably a C ₆ ~ C ₃₀ aromatic ring group, a C ₆ ~ C ₁₄ aromatic ring group, such as benzene, naphthalene, phenanthrene, and the like.

When the A ring, the B ring and the C ring are each a hetero ring, preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₂₂ heterocyclic group such as dibenzothiophene, dibenzofuran , Benzonaphthothiophene, benzonaphthofuran, benzocarbazole, phenyl-benzocarbazole, naphthonaphthothiophene, and the like.

When ring A, ring B, and ring C are each a fluorene group, 9,9-dimethylfluorene, 9,9-diphenylfluorene, 9,9'-spirobifluorene, dimethylbenzofluorene, di Phenylbenzofluorene and the like.

Each of the A ring, B ring and C ring may be substituted with one or more of the same or different R ₁ , R ₂ , and R ₃ . That is, ring A may be further substituted with one or more R ₁ that is the same or different, ring B with one or more R ₂ that is the same or different, and ring C may be further substituted with one or more R ₃ that are the same or different.

R ¹ , wherein R ₁ to R ₃ are each independently hydrogen; Deuterium, tritium; halogen; Cyano group; Nitro group; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; C ₃ ~ C ₆₀ aliphatic ring group; C ₁ ~ C ₃₀ alkyl group; C ₂ ~ C ₃₀ Alkenyl group; Alkynyl group of C ₂ to C ₃₀ ; An alkoxyl group of C ₁ to C ₃₀ ; C ₆ ~ C ₃₀ aryloxy group; And -L'-[N(R _a )(R _b )] _c is selected from the group consisting of, and neighboring R ₁ and R ₂ can be bonded to each other to form a ring, and c is an integer of 1-5 .

a is an integer of 0 to 2, and when a is 2, each of R ¹ is the same as or different from each other.

When R ¹ , R ₁ to R ₃ are each an aryl group, preferably a C ₆ to C ₃₀ aryl group, more preferably a C ₆ to C ₁₈ aryl group such as phenyl, naphthyl, biphenyl, terphenyl , Phenanthrene, and the like.

When R ¹ , R ₁ to R ₃ are each a heterocyclic group, preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₁₈ heterocyclic group such as pyridine, pyrimidine, triazine , Quinazoline, quinoxaline, benzoquinoxaline, benzoquinazoline, dibenzoquinoxaline, dibenzoquinazoline, benzothienopyrimidine, dihydro-dimethylindenopyrimidine, indolopyrimidine, carbazole, Phenylcarbazole, dibenzothiophene, dibenzofuran, benzonaphthofuran, benzonaphthothiophene, benzofuroquinazine, benzothienoquinazine, phenanthroline, and the like.

When R ¹ , R ₁ to R ₃ are each an aliphatic ring group, preferably a C ₃ to C ₂₀ alicyclic group, more preferably a C ₃ to C ₁₈ aliphatic ring group, such as cyclopentane, cyclohexane, etc. have.

When R ¹ , R ₁ to R ₃ are each fluorenyl group, 9,9-dimethylfluorene, 9,9-diphenylfluorene, 9,9'-spirobifluorene, dimethylbenzofluorene , Diphenylbenzofluorene, and the like.

When each of R ¹ , R ₁ to R ₃ is an alkyl group, it may be preferably a C ₁ to C ₂₀ alkyl group, more preferably a C ₁ to C ₁₀ alkyl group such as ethyl, propyl, t-butyl and the like.

When each of R ¹ , R ₁ to R ₃ is an alkenyl group, it may be preferably an alkenyl group of C ₂ to C ₂₀ , more preferably an alkenyl group of C ₂ to C ₁₀ , such as ethene and propene.

When R ¹ , R ₁ to R ₃ are each alkoxy group, preferably a C ₁ to C ₂₀ alkoxyl group, more preferably a C ₁ to C ₁₀ alkoxyl group such as methoxy, ethoxy, t-butoxy Etc.

The ring formed by bonding of adjacent R ₁ and R _{2 to} each other is an aromatic ring group of C ₆ ~ C ₆₀ ; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; Alternatively, it may be a C ₃ ~ C ₆₀ aliphatic ring group. In particular, when neighboring R ₁ and R ₂ are bonded to each other to form a hetero ring, a hetero ring including N may be formed.

L'is a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene group; C ₃ ~ C ₆₀ aliphatic ring group; And O, N, S, Si, and a C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; It may be selected from the group consisting of.

When L'is an arylene group, preferably a C ₆ to C ₃₀ arylene group, more preferably a C ₆ to C ₁₈ arylene group such as phenyl, naphthylene, biphenyl, terphenyl, triphenylene, phenane It could be Tren, etc.

R _a and R _b are each independently a C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₃ ~ C ₆₀ aliphatic ring group; And O, N, S, Si, and a C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; It may be selected from the group consisting of. -L'-[N(R _a )(R _b )] Since _c in c is an integer of 1 to 5, when L'is a phenylene group, N(R _a )(R _b ) is 1 to L' Up to 5 can be combined.

When each of R _a and R _b is an aryl group, preferably a C ₆ to C ₃₀ aryl group, more preferably a C ₆ to C ₁₈ aryl group, such as phenyl, naphthyl, biphenyl, terphenyl, etc. .

When R _a and R _b are heterocyclic groups, preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₁₈ heterocyclic group such as dibenzothiophene, benzoxazole, benzothi Azole, dibenzofuran, benzonaphthofuran, benzonaphthothiophene, benzothienopyrimidine, carbazole, phenylcarbazole, and the like.

When R _a and R _b are fluorenyl groups, they may be 9,9-dimethylfluorene, 9,9-diphenylfluorene, 9,9'-spirobifluorene, and the like.

The R ¹ , R ₁ to R ₃ , L', R _a , R _b , and adjacent R ₁ and R ₂ rings are bonded to each other to form deuterium, respectively; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio group; C ₁ -C ₂₀ alkoxy group; A C ₆ -C ₂₀ arylalkoxy group; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; C ₃ -C ₂₀ aliphatic ring group; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ may be further substituted with one or more substituents selected from the group consisting of arylalkenyl group.

The A ring and B ring may each independently be one of the following formulas F-1 to F-6.

<Formula F-1> <Formula F-2> <Formula F-3>

<Formula F-4> <Formula F-5> <Formula F-6>

In Formulas F-1 to F-6, * represents a condensation position with a neighboring N-containing ring.

R ² to R ⁵ are the same as or different from each other and are defined the same as R ₁ or R ₂ in Formula 1, and neighboring groups may be bonded to each other to form a ring.

b and e are each an integer of 0 to 4, c is an integer of 0 to 6, d is an integer of 0 to 2, and when each is an integer of 2 or more, each R ² , each R ³ , each R ⁴ , each R ⁵ may be the same or different.

Y is C(R')(R"), N(R _c ), O or S.

R′ and R” are independently of each other hydrogen; deuterium; halogen; cyano group; nitro group; C ₁ -C ₂₀ alkoxy group; C ₆ -C ₂₀ arylalkoxy group; C ₁ -C ₂₀ alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ aryl group; fluorenyl group; At least one heteroatom selected from the group consisting of O, N, S, Si and P It is selected from the group consisting of C ₂ -C ₂₀ heterocyclic group; And C ₃ -C ₂₀ aliphatic ring group; and R′ and R” may be bonded to each other to form a ring. When R'and R" are bonded to each other to form a ring, a compound may be formed as a spy together with C to which they are bonded.

R _c is a C ₆ -C ₂₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; And C ₃ -C ₂₀ aliphatic ring group; is selected from the group consisting of.

The C ring may be one of the following formulas F-7 to F-10.

<Formula F-7> <Formula F-8> <Formula F-9> <Formula F-10>

In the above Formulas F-7 to F-10, * represents a position at which each N-containing ring (seven-membered ring and pentagonal ring) is condensed.

R ₃ is the same as defined in Formula 1, f is an integer of 0-3, g is an integer of 0-5, h is an integer of 0 or 1, i is an integer of 0-4, f, g, and i respectively In the case of an integer of 2 or more, each of R ³ is the same as or different from each other.

Y is C(R')(R"), N(R _c ), O or S.

R′ and R” are independently of each other hydrogen; deuterium; halogen; cyano group; nitro group; C ₁ -C ₂₀ alkoxy group; C ₆ -C ₂₀ arylalkoxy group; C ₁ -C ₂₀ alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ aryl group; fluorenyl group; At least one heteroatom selected from the group consisting of O, N, S, Si and P It is selected from the group consisting of C ₂ -C ₂₀ heterocyclic group; And C ₃ -C ₂₀ aliphatic ring group; and R′ and R” may be bonded to each other to form a ring. When R'and R" are bonded to each other to form a ring, a compound may be formed as a spy together with C to which they are bonded.

R _c is a C ₆ -C ₂₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; And C ₃ -C ₂₀ aliphatic ring group; is selected from the group consisting of.

Preferably, Formula 1 may be represented by one of the following Formulas 1-A to 1-I.

<Formula 1-A> <Formula 1-B> <Formula 1-C>

<Formula 1-D> <Formula 1-E> <Formula 1-F>

<Formula 1-G> <Formula 1-H> <Formula 1-I>

In Formula 1-A to Formula 1-I, R ¹ , R ₁ , R ₂ , R ₃ , a are the same as defined in Formula 1, b is an integer of 0-4, c is an integer of 0-5, d is an integer of 0-6, e is an integer of 0-3, h is an integer of 0-7, i is an integer of 0-8, and when each is an integer of 2 or more, each of R ₁ , R ₂ , and R ₃ Each of them is the same as or different from each other, and neighboring groups may combine with each other to form a ring.

Y is C(R')(R"), N(R _c ), O or S.

R′ and R” are independently of each other hydrogen; deuterium; halogen; cyano group; nitro group; C ₁ -C ₂₀ alkoxy group; C ₆ -C ₂₀ arylalkoxy group; C ₁ -C ₂₀ alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ aryl group; fluorenyl group; At least one heteroatom selected from the group consisting of O, N, S, Si and P It is selected from the group consisting of C ₂ -C ₂₀ heterocyclic group; And C ₃ -C ₂₀ aliphatic ring group; and R′ and R” may be bonded to each other to form a ring. When R'and R" are bonded to each other to form a ring, a compound may be formed as a spy together with C to which they are bonded.

R _c is a C ₆ -C ₂₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; And C ₃ -C ₂₀ aliphatic ring group; is selected from the group consisting of.

Exemplarily, at least one of R ₁ to R ₃ may be -L'-N(R _a )(R _b ), or the following Formula 3-1 or Formula 3-2.

<Formula 3-1> <Formula 3-2>

In Formulas 3-1 and 3-2, each symbol may be defined as follows.

Q ¹ to Q ⁴ are each independently N, C, or C(R _d ), and Q ⁵ to Q ⁹ are each independently N or C(R _d ).

L _a and L _b are each independently a single bond; C ₆ -C ₆₀ arylene group; Fluorenylene group; A C ₂ -C ₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si and P; And C ₃ -C ₆₀ aliphatic ring group; may be selected from the group consisting of.

The Z ring may be selected from the following structures, but is not limited thereto.

In the structure of the Z ring, * represents a condensation position with a ring including Q ¹ to Q ⁴ .

W ¹ and W ² are each independently a single bond, N-(L ³ -Ar ³ ), S, O, C or C (R _e ) (R _f ), and V is independently of each other N, C or C ( R _g ).

R _d , R _e , R _f , R _g and Ar ³ are each independently hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio group; An alkoxyl group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; A C ₃ -C ₂₀ cycloalkyl group; A C ₇ -C ₂₀ arylalkyl group; And it is selected from the group consisting of C ₈ -C ₂₀ arylalkenyl group, neighboring groups may be bonded to each other to form a ring, and R _e and R _{f may} also be bonded to each other to form a ring. When R _e and R _f are bonded to each other to form a ring, a spy compound may be formed together with C to which they are bonded.

L ³ is a single bond; C ₆ -C ₆₀ arylene group; Fluorenylene group; A C ₂ -C ₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si and P; And C ₃ -C ₆₀ is selected from the group consisting of an aliphatic ring group.

Illustratively, Formula 1 may be represented by one of the following formulas.

In the above formula, Y may be defined in the same manner as Y defined in Formula F-4.

Specifically, the compound represented by Formula 1 may be one of the following compounds.

.

.

In another aspect of the present invention, the present invention provides an organic electrical device comprising an anode, a cathode, and an organic material layer formed between the anode and the cathode, wherein the organic material layer is one single compound or two or more Contains compounds.

In yet another aspect of the present invention, the present invention provides an organic electric device including an anode, a cathode, an organic material layer formed between the anode and the cathode, and a light efficiency improvement layer. In this case, the light efficiency improvement layer is formed on one side of both surfaces of the anode or the cathode that is not in contact with the organic material layer, and the organic material layer or the light efficiency improvement layer includes the compound represented by Formula 1 above.

The organic material layer includes at least one of a hole injection layer, a hole transport layer, a light emission auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer, and preferably, the compound is included in the emission layer and/or the emission auxiliary layer. Can be included.

The organic material layer may include two or more stacks including a hole transport layer, an emission layer, and an electron transport layer sequentially formed on the anode, and may further include a charge generation layer formed between the two or more stacks.

In yet another aspect of the present invention, the present invention provides an electronic device including a display device including an organic electric element represented by Formula 1 and a control unit for driving the display device.

Hereinafter, examples for synthesizing the compound represented by Chemical Formula 1 according to the present invention and an example for preparing an organic electric device will be described in detail, but the present invention is not limited to the following examples.

Synthesis example

The compound represented by Formula 1 according to the present invention (final product 1, final product 2) is synthesized as shown in Scheme 1 below, but is not limited thereto.

<Reaction Scheme 1>

I. Synthesis of Sub 1

Sub 1 of Scheme 1 is synthesized by the reaction route of Scheme 2 below, but is not limited thereto.

<Scheme 2> (Hal is I, Br or Cl)

1. Sub 1-1 synthesis example

(1) Sub 1-1-a synthesis example

After dissolving 9H-carbazole (100 g, 598.1 mmol) with xylene (1196 mL) under nitrogen atmosphere at room temperature, N-([1,1'-biphenyl]-4-yl)-N-(3-bromo-4- iodophenyl)-[1,1'-biphenyl]-4-amine (396.2 g, 657.9 mmol), CuI (74.03 g, 388.73 mmol), and K ₂ CO ₃ (242 g, 1196.10 mmol) were added and stirred for 1 hour while stirring. Reflux. When the reaction is complete, the mixture is cooled to room temperature, extracted with CH ₂ Cl ₂ and water, and the organic layer is dried with Na ₂ SO ₄ and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 272.4 g (yield: 71%) of the product.

(2) Synthesis example of Sub 1-1-b and Sub 1-1

After dissolving Sub1-1-a (272.4 g, 424.6 mmol) with triethylamine (1061 ml) at room temperature under a nitrogen atmosphere, ethynyltrimethylsilane (45.9 g, 467.0 mmol), PdCl ₂ (PPh ₃ ) ₂ (23.84 g, 33.96 mmol) , CuI (7.28 g, 38.21 mmol) was added, stirred for 24 hours, and heated to 80°C. When the reaction is complete, cool to room temperature, remove the solvent, and dissolve the obtained Sub 1-1-b with THF (306 ml) at 0℃, and then add 1M in THF tetrabutylammonium fluoride (TBAF, 306ml, 306 mmol) at room temperature. Stir for 1 hour. When the reaction is complete, the mixture is extracted with water and ethyl acetate, and the organic layer is dried over Na ₂ SO ₄ and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 121.9 g (yield: 68%) of the product.

2. Sub 1-14 synthesis

(1) Synthesis example of Sub 1-14-a

N-([1,1'-biphenyl]-2-yl)-N-(naphthalen-1-yl)-9H-carbazol-2-amine (100 g, 217.1 mmol) was added to xylene (434) at room temperature under a nitrogen atmosphere. mL), 1,2-diiodobenzene (78.8 g, 238.8 mmol), CuI (26.88 g, 141.13 mmol), K ₂ CO ₃ (87.85 g, 434.24 mmol) was added thereto, and the method for synthesizing Sub 1-1-a. Proceeding in the same manner as the product 118.0 g (yield: 82%) was obtained.

(2) Example of Sub 1-14 synthesis

After dissolving Sub1-14-a (118.0 g, 178.1 mmol) with triethylamine (445 ml) at room temperature under a nitrogen atmosphere, ethynylbenzene (20 g, 195.9 mmol), PdCl ₂ (PPh ₃ ) ₂ (10 g, 14.25 mmol) , CuI (3.05 g, 16.03 mmol) was added, stirred for 24 hours, and heated to 80°C. When the reaction is complete, cool to room temperature, add 1N HCl (323.81 ml), extract with CH ₂ Cl2, dry the organic layer with Na ₂ SO ₄ and concentrate. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 87.3 g (yield: 77%) of the product.

3. Sub 1-35 synthesis

(1) Example of Sub 1-35-a synthesis

After dissolving 7H-benzo[c]carbazole (100 g, 460.3 mmol) with xylene (921 mL) at room temperature under a nitrogen atmosphere, 3-bromo-9-(4,6-diphenyl-1,3,5-triazin- 2-yl)-2-iodo-9H-carbazole (305.4 g, 506.3 mmol), CuI (56.98 g, 299.17 mmol), K ₂ CO ₃ (186.24 g, 920.51 mmol) was added to the Sub 1-1-a. Proceeding in the same manner as the synthesis method, the product 204.0 g (yield: 64%) was obtained.

(2) Synthesis example of Sub 1-35-b and Sub 1-35

After dissolving Sub1-35-a (204.0 g, 294.5 mmol) with triethylamine (736 ml) at room temperature under a nitrogen atmosphere, ethynyltrimethylsilane (31.8 g, 324 mmol), PdCl ₂ (PPh ₃ ) ₂ (16.54 g, 23.56 mmol) , CuI (5.05 g, 26.51 mmol) was added and proceeded in the same manner as in the synthesis method of Sub 1-1-b. Thereafter, when the reaction is complete, cool to room temperature, remove the solvent, and dissolve the obtained Sub 1-35-b with THF (200 ml) at 0°C. Thereafter, 1M in THF tetrabutylammonium fluoride (TBAF, 220.3 ml, 220.3 mmol) was carried out in the same manner as in the synthesis method of Sub 1-1 to obtain 83.0 g (yield: 65%) of the product.

4. Sub 1-50 synthesis

(1) Sub 1-50-a synthesis example

After dissolving 3-fluoro-6-(3-phenylquinoxalin-2-yl)-9H-carbazole (100 g, 256.8 mmol) with xylene (514 mL) at room temperature under a nitrogen atmosphere, 1,2-diiodobenzene (93.2 g, 282.5 mmol), CuI (31.79 g, 166.91 mmol), K ₂ CO ₃ (103.91 g, 513.57 mmol) was added and proceeded in the same manner as the synthesis method of Sub 1-1-a, and the product 121.5 g (yield: 80%) Got it.

(2) Example of Sub 1-50 synthesis

After dissolving Sub1-50-a (121.5 g, 591.4 mmol) with triethylamine (514 ml) at room temperature under a nitrogen atmosphere, ethynylbenzene (23.1 g, 226.0 mmol), PdCl ₂ (PPh ₃ ) ₂ (11.54 g, 16.43 mmol) , CuI (3.52 g, 18.49 mmol) was added, stirred for 24 hours, and heated to 80°C. When the reaction is complete, cool to room temperature, add 1N HCl (373.52 ml) and extract with CH ₂ Cl ₂ . The extracted organic layer was dried with Na ₂ SO ₄ and concentrated. Thereafter, the concentrate was separated with a silica gel column and recrystallized to obtain 86.0 g (yield: 74%) of the product.

5. Sub 1-61 synthesis

(1) Synthesis example of Sub 1-61-a

After dissolving Sub 1-61-st (100 g, 94.1 mmol) with xylene (188 mL) at room temperature under a nitrogen atmosphere, 1-bromo-2-iodobenzene (29.3 g, 103.5 mmol), CuI (11.65 g, 61.19 mmol) ), K ₂ CO ₃ (38.09 g, 188.27 mmol) was added and proceeded in the same manner as for the synthesis of Sub 1-1-a to obtain 84.5 g (yield: 71%) of the product.

(2) Example of Sub 1-61-b and Sub 1-61 synthesis

After dissolving Sub1-61-a (84.5 g, 66.8 mmol) with triethylamine (167 ml) at room temperature under a nitrogen atmosphere, ethynyltrimethylsilane (7.2 g, 73.5 mmol), PdCl ₂ (PPh ₃ ) ₂ (3.75 g, 5.35 mmol) , CuI (1.15 g, 6.02 mmol) was added and proceeded in the same manner as in the synthesis method of Sub 1-1-b. Then, when the reaction is complete, cool to room temperature, remove the solvent, and dissolve the obtained Sub 1-61-b in THF (51 ml) at 0°C. Thereafter, 1M in THF tetrabutylammonium fluoride (TBAF, 55.9 ml, 55.9 mmol) was carried out in the same manner as in the synthesis method of Sub 1-1 to obtain 41.3 g of a product (yield: 70%).

6. Sub 1-69 synthesis

(1) Synthesis example of Sub 1-61-a

Sub 1-61-st (100 g, 141.9 mmol) was dissolved in xylene (284 mL) at room temperature under a nitrogen atmosphere, and then 1-bromo-2-iodobenzene (44.2 g, 156.1 mmol), CuI (17.56 g, 92.23 mmol) ), K ₂ CO ₃ (57.41 g, 283.77 mmol) was added and proceeded in the same manner as for the synthesis of Sub 1-1-a to obtain 93.9 g (yield: 77%) of the product.

(2) Example of Sub 1-61-b and Sub 1-61 synthesis

Sub1-61-a (93.9 g, 109.2 mmol) was dissolved in triethylamine (273 ml) at room temperature under a nitrogen atmosphere, and then ethynyltrimethylsilane (11.8 g, 120.1 mmol), PdCl ₂ (PPh ₃ ) ₂ (6.13 g, 8.74 mmol) , CuI (1.87 g, 9.83 mmol) was added and proceeded in the same manner as for the synthesis of Sub 1-1-b. Thereafter, when the reaction is complete, cool to room temperature, remove the solvent, and dissolve the obtained Sub 1-61-b with THF (81 ml) at 0°C. Thereafter, 1M in THF tetrabutylammonium fluoride (TBAF, 88.9 ml, 88.9 mmol) was carried out in the same manner as in the synthesis method of Sub 1-1 to obtain 51.4 g (yield: 79%) of the product.

7. Sub 1-105 synthesis

(1) Example of Sub 1-105-a synthesis

After dissolving 14H-benzo[2,3]benzofuro[6,5-a]carbazole (100 g, 325.4 mmol) with xylene (651 mL) at room temperature under a nitrogen atmosphere, 2-(2-bromo-3-iodophenyl) -3-(pyridin-3-yl)quinoxaline (174.7 g, 357.9 mmol), CuI (40.28 g, 211.49 mmol), K ₂ CO ₃ (131.65 g, 650.72 mmol) was added thereto, and the method for synthesizing Sub 1-1-a. Proceeding in the same manner as the product 156.4 g (yield: 72%) was obtained.

(2) Synthesis example of Sub 1-105-b and Sub 1-105

After dissolving Sub1-105-a (156.4 g, 234.3 mmol) with triethylamine (586 ml) at room temperature under a nitrogen atmosphere, ethynyltrimethylsilane (25.3 g, 257.7 mmol), PdCl ₂ (PPh ₃ ) ₂ (13.16 g, 18.74 mmol) , CuI (4.02 g, 21.09 mmol) was added and proceeded in the same manner as in the synthesis method of Sub 1-1-b. Thereafter, when the reaction is complete, cool to room temperature, remove the solvent, and dissolve the obtained Sub 1-105-b in THF (183 ml) at 0°C. Thereafter, 1M in THF tetrabutylammonium fluoride (TBAF, 201.1 ml, 201.1 mmol) was carried out in the same manner as in the synthesis method of Sub 1-1 to obtain 88.5 g of a product (yield: 79%).

8. Sub 1-110 synthesis

(1) Example of Sub 1-110-a synthesis

After dissolving 9H-carbazole (43 g, 257.2 mmol) with xylene (514 mL) at room temperature under a nitrogen atmosphere, 4-(3-bromo-4-iododinaphtho[1,2-b:2',3'-d] thiophen-1-yl)-6-phenylpyrimidine (182.0 g, 282.9 mmol), CuI (31.83 g, 167.16 mmol), K ₂ CO ₃ (104.06 g, 514.32 mmol) was added to the synthesis method of Sub 1-1-a and Proceeding in the same way, the product 140.4 g (yield: 80%) was obtained.

(2) Synthesis example of Sub 1-110-b and Sub 1-110

After dissolving Sub1-110-a (140.4 g, 682.64 mmol) with triethylamine (514 ml) at room temperature under a nitrogen atmosphere, ethynyltrimethylsilane (22.2 g, 226.2 mmol), PdCl ₂ (PPh ₃ ) ₂ (11.55 g, 16.45 mmol) , CuI (3.53 g, 18.51 mmol) was added and proceeded in the same manner as for the synthesis of Sub 1-1-b. Thereafter, when the reaction is complete, cool to room temperature, remove the solvent, and dissolve the obtained Sub 1-110-b with THF (158 ml) at 0°C. Thereafter, 1M in THF tetrabutylammonium fluoride (TBAF, 174.1 ml, 174.1 mmol) was carried out in the same manner as in the synthesis method of Sub 1-1 to obtain 81.5 g (yield: 82%) of the product.

Compounds belonging to Sub 1 are as follows, but are not limited thereto, and FD-MS (Field Desorption-Mass Spectrometry) values for the following compounds are shown in Table 1 below.

[Table 1]

II. Of the final compound Synthesis example

1. Synthesis Example of P-1

After dissolving Sub 1-1 (50 g, 85.2 mmol) with 1,2-dichloroethane martial art (852 ml) under nitrogen atmosphere at room temperature, AuCl (PPh ₃ ) (4.22 g, 8.52 mmol), AgSbF ₆ (2.93 g, 8.52 mmol) and reacted at 80° C. for 24 hours while stirring. When the reaction is complete, the mixture is cooled to room temperature, extracted with CH ₂ Cl ₂ and water, the organic layer is dried over Na ₂ SO ₄ and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 37.5 g (yield: 75%) of the product.

2. Synthesis Example of P-5

(1) Synthesis example of Inter P-5-a

After dissolving Sub 1-5 (50 g, 59.2 mmol) with 1,2-dichloroethane martial arts (592 ml) under nitrogen atmosphere at room temperature, AuCl (PPh ₃ ) (2.93 g, 5.92 mmol), AgSbF ₆ (2.03 g, 5.92 mmol) was added and proceeded in the same manner as in the synthesis method of P-1 to obtain 41 g (yield: 82%) of the product.

(2) Synthesis example of Inter P-5-b

After dissolving Inter P-5-a (41 g, 49 mmol) with dichloromethane (243 ml), N-bromosuccinimide (8.6 g, 49 mmol) was added and reacted with stirring at 80° C. for 24 hours. When the reaction is complete, the mixture is cooled to room temperature, extracted with CH ₂ Cl ₂ and water, the organic layer is dried over Na ₂ SO ₄ and concentrated. Thereafter, the concentrate was recrystallized with dichloromethane and hexane to obtain 34.1 g (yield: 76%) of the product.

(3) Synthesis example of P-5

Inter P-5-b (34.1 g, 36.9 mmol) was dissolved in THF (185 ml)/H ₂ O (92 ml), and then phenylboronic acid (4.5 g, 36.9 mmol), Pd(PPh ₃ ) ₄ (2.56 g , 2.21 mmol) and NaOH (4.4 g, 110.7 mmol) were added and then refluxed while stirring at 80° C. for 24 hours. When the reaction was completed, the reaction mixture was cooled to room temperature, extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over Na ₂ SO ₄ and concentrated to recrystallize the resulting compound with dichloromethane and hexane to obtain 27.2 g (yield: 80%) of the product.

3. Synthesis Example of P-11

After dissolving Sub 1-11 (61 g, 95.8 mmol) with 1,2-dichloroethane martial arts (958 ml) at room temperature under a nitrogen atmosphere, AuCl (PPh3) (4.74 g, 9.58 mmol), AgSbF ₆ (3.29 g, 9.58 mmol) was obtained by using the synthesis method of P-1 to obtain 51.9 g (yield: 85%) of the product.

4. Synthesis Example of P-45

After dissolving Sub 1-45 (55 g, 93.6 mmol) with 1,2-dichloroethane martial arts (936 ml) under nitrogen atmosphere at room temperature, AuCl (PPh ₃ ) (4.63 g, 9.36 mmol), AgSbF ₆ (3.22 g, 9.36 mmol) was added and proceeded in the same manner as in the synthesis method of P-1 to obtain 45.7 g (yield: 83%) of the product.

5. Synthesis Example of P-79

(1) Synthesis example of Inter P-79-a

After dissolving Sub 1-79 (42 g, 41.6 mmol) with 1,2-dichloroethane martial arts (416 ml) in nitrogen atmosphere at room temperature, AuCl (PPh ₃ ) (2.06 g, 4.16 mmol), AgSbF ₆ (1.43 g, 4.16 mmol) and proceeded in the same manner as in the synthesis method of P-1 to obtain 29.8 g (yield: 71%) of the product.

(2) Synthesis example of Inter P-79-b

After dissolving Inter P-79-a (29.8 g, 30 mmol) with dichloromethane (243 ml), N-bromosuccinimide (5.3 g, 30 mmol) was added and reacted with stirring at 80° C. for 24 hours. When the reaction was completed, the reaction mixture was cooled to room temperature, extracted with CH ₂ Cl ₂ and water, and the organic layer was dried with Na ₂ SO ₄ and concentrated to recrystallize the resulting compound with dichloromethane and hexane to obtain 23.5 g (yield: 73%) of the product.

(3) Synthesis example of P-79

Inter P-79-b (23.5 g, 21.6 mmol) was dissolved in THF (108 ml)/H ₂ O (54 ml), and then phenylboronic acid (2.6 g, 21.6 mmol), Pd(PPh ₃ ) ₄ (1.50 g , 1.30 mmol) and NaOH (2.6 g, 64.8 mmol) were added and stirred at 80° C. for 24 hours to reflux. When the reaction was completed, the reaction mixture was cooled to room temperature, extracted with CH ₂ Cl ₂ and water, and the organic layer was dried with Na ₂ SO ₄ and concentrated. The resulting compound was recrystallized with dichloromethane and hexane to obtain 16.4 g (yield: 70%) of the product.

6. Synthesis Example of P-105

After dissolving Sub 1-105 (57 g, 93 mmol) with 1,2-dichloroethane martial arts (930 ml) under nitrogen atmosphere at room temperature, AuCl (PPh ₃ ) (4.60 g, 9.30 mmol), AgSbF ₆ (3.20 g, 9.30 mmol) and proceeded in the same manner as in the synthesis method of P-1 to obtain 44.5 g (yield: 78%) of the product.

7. Synthesis Example of P-111

After dissolving Sub 1-111 (46 g, 68.9 mmol) with 1,2-dichloroethane martial arts (689 ml) under nitrogen atmosphere at room temperature, AuCl (PPh ₃ ) (3.41 g, 6.89 mmol), AgSbF ₆ (2.37 g, 6.89 mmol) was added and proceeded in the same manner as in the synthesis method of P-1 to obtain 34.5 g (yield: 75%) of the product.

8. Synthesis Example of P-115

After dissolving Sub 1-115 (58 g, 92.2 mmol) in 1,2-dichloroethane martial arts (922 ml) under nitrogen atmosphere at room temperature, AuCl (PPh ₃ ) (4.56 g, 9.22 mmol), AgSbF ₆ (3.17 g, 9.22 mmol) was added and proceeded in the same manner as in the synthesis method of P-1 to obtain 38.9 g (yield: 67%) of the product.

9. Synthesis Example of P-118

(1) Synthesis example of Inter P-118-a

After dissolving Sub 1-118 (58 g, 120.2 mmol) with 1,2-dichloroethane martial arts (1202 ml) under nitrogen atmosphere at room temperature, AuCl (PPh ₃ ) (5.95 g, 12.02 mmol), AgSbF ₆ (4.13 g, 12.02 mmol) was added and proceeded in the same manner as in the synthesis method of P-1 to obtain 43.5 g (yield: 75%) of the product.

(2) Synthesis example of Inter P-118-b

After dissolving Inter P-79-a (43.5 g, 65 mmol) with dichloromethane (243 ml), N-bromosuccinimide (11.6 g, 65 mmol) was added and reacted with stirring at 80° C. for 24 hours. When the reaction was completed, the reaction mixture was cooled to room temperature, extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over Na ₂ SO ₄ and concentrated to recrystallize the resulting compound with dichloromethane and hexane to obtain 28.2 g (yield: 77%) of the product.

(3) Synthesis example of P-118

Inter P-79-b (23.5 g, 21.6 mmol) was dissolved in THF (108 ml)/H ₂ O (54 ml), and then phenylboronic acid (2.6 g, 21.6 mmol), Pd(PPh ₃ ) ₄ (1.50 g , 1.30 mmol) and NaOH (2.6 g, 64.8 mmol) were added and stirred at 80° C. for 24 hours to reflux. When the reaction was completed, the reaction mixture was cooled to room temperature, extracted with CH ₂ Cl ₂ and water, and the organic layer was dried with Na ₂ SO ₄ and concentrated. The resulting compound was recrystallized with dichloromethane and hexane to obtain 16.4 g (yield: 70%) of the product.

The FD-MS values of compounds 1-1 to 1-120 of the present invention prepared according to the synthesis example as described above are shown in Table 2 below.

[Table 2]

Manufacturing evaluation of organic electric devices

[Example 1] Green organic electroluminescent device (light emission auxiliary layer)

On the ITO layer (anode) formed on the glass substrate, N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4 -Diamine (hereinafter abbreviated as "2-TNATA") film was vacuum-deposited to form a hole injection layer with a thickness of 60 nm, and then N,N'-Bis(1-naphthalenyl)-N,N'-bis-phenyl- (1,1'-biphenyl)-4,4'-diamine (hereinafter abbreviated as "NPB") was vacuum deposited to a thickness of 60 nm to form a hole transport layer. Subsequently, the compound P-1 of the present invention was vacuum-deposited to a thickness of 20 nm on the hole transport layer to form a light emission auxiliary layer.

Next, on the light-emitting auxiliary layer, 4,4'-N,N'-dicarbazole-biphenyl (hereinafter referred to as "CBP") as a host material, tris(2-phenylpyridine)-iridium (hereinafter, referred to as a dopant material) "Ir(ppy) ₃ ) was used in a weight ratio of 95:5 to form a light emitting layer having a thickness of 30 nm.

Then, (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as "BAlq") was vacuum-deposited to a thickness of 10 nm as a hole blocking layer on the emission layer. , BeBq ₂ was vacuum deposited on the hole blocking layer to a thickness of 50 nm to form an electron transport layer.

Thereafter, LiF was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and Al was deposited on the electron injection layer to a thickness of 150 nm to form a cathode.

[ Example 2] to [ Example 17]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound of the present invention described in Table 3 was used instead of the compound P-1 of the present invention as the light emitting auxiliary layer material.

[Comparative Example 1]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the light emission auxiliary layer was not formed.

[ Comparative example 2] to [ Comparative example 4]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound A to Comparative Compound C were used as the light emitting auxiliary layer material.

<Comparative Compound A> <Comparative Compound B> <Comparative Compound C>

By applying a forward bias DC voltage to the organic electroluminescent devices prepared according to Examples 1 to 17 and Comparative Examples 1 to 4 of the present invention, electroluminescence (EL) characteristics were obtained with PR-650 of photoresearch. It was measured, and the T95 life was measured using a life measurement equipment of McScience at 5000 cd/m ² standard luminance. The measurement results are shown in Table 3 below.

[Table 3]

As can be seen from the results in Table 3, when a green organic electroluminescent device is manufactured using the material for an organic electroluminescent device of the present invention as a light emitting auxiliary layer material, no light emitting auxiliary layer is formed or the compound of the invention and the basic skeleton The electrical properties of the organic electroluminescent device can be improved compared to the comparative example using the similar comparative compounds A to C.

In the case of Comparative Examples 2 to 4 in which the light-emitting auxiliary layer was formed using one of Comparative Compounds A to C, rather than Comparative Example 1 in which the light-emitting auxiliary layer was not formed, the driving voltage, efficiency, and lifetime of the device were improved. Among them, Comparative Example 4 using a dibenzoazepinocarbazole-type comparative compound C, which formed a ring containing N atoms in dibenzoazepine, as a material for the light emission auxiliary layer, compared to Comparative Examples 2 and 3 It was confirmed that the characteristics were improved.

Meanwhile, the compound according to Formula 1 of the present invention has a structure having a benzoazepinocarbazole moiety in which one phenyl is excluded from dibenzoazepinocarbazole. Comparing the compound of the present invention with the comparative compound C, it is the same as having azepinocarbazole, but the driving voltage of the device including the compound of the present invention is lowered, and the efficiency and It showed the result of improving the lifespan.

As can be seen from Table 4 below, since Compound P-1 of the present invention exhibits a deeper HOMO value than Comparative Compound C, it is possible to effectively transfer holes coming from the hole transport layer to the light emitting layer. There is also a significant difference in the results.

[Table 4]

This result is that even if the compound has a similar basic skeleton, such as Comparative Compound C and the compound of the present invention, the physical properties (HOMO, LUMO, band gap, and T1) of the compound vary depending on the number of rings constituting the compound, and this difference in physical properties. It is believed that this is because it acts as a major factor affecting the device characteristics when depositing a compound for forming a light emitting auxiliary layer in the manufacturing process of the device.

[Example 18] Red organic electroluminescent device (phosphorescent host)

A 2-TNATA film was vacuum-deposited on the ITO layer (anode) formed on the glass substrate to form a hole injection layer with a thickness of 60 nm, and then NPB was vacuum evaporated to form a hole transport layer having a thickness of 60 nm.

Thereafter, the compound P-30 of the present invention as a host material on the hole transport layer, bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate (hereinafter, abbreviated as "(piq) ₂ Ir(acac)") as a dopant Although used as a material, a light emitting layer having a thickness of 30 nm was deposited by doping with a dopant so that the weight ratio was 95:5.

Next, (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as "BAlq") was vacuum-deposited to a thickness of 10 nm on the emission layer to form a hole blocking layer. And BeBq ₂ was deposited to a thickness of 45 nm on the hole blocking layer to form an electron transport layer.

Thereafter, LiF was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and Al was deposited on the electron injection layer to a thickness of 150 nm to form a cathode.

[ Example 19] to [ Example 35]

An organic electroluminescent device was manufactured in the same manner as in Example 18, except that the compound of the present invention described in Table 5 was used instead of the compound P-30 of the present invention as a host material.

[Comparative Example 5] to [Comparative Example 8]

An organic electroluminescent device was manufactured in the same manner as in Example 18, except that one of the following Comparative Compound D to Comparative Compound G was used instead of the compound P-30 of the present invention as a host material.

<Comparative Compound D> <Comparative Compound E> <Comparative Compound F> <Comparative Compound G>

By applying a forward bias DC voltage to the organic electroluminescent devices prepared according to Examples 18 to 35 and Comparative Examples 5 to 8 of the present invention, electroluminescence (EL) characteristics were obtained with PR-650 of photoresearch. It was measured, and the T95 life was measured using a life measurement equipment of McScience at a reference brightness of 2500 cd/m ² . The measurement results are shown in Table 5 below.

[Table 5]

As can be seen from the results of Table 5 above, when a red organic electroluminescent device is manufactured using the material for an organic electroluminescent device of the present invention as a phosphorescent host material, a comparison similar to the comparative compound D or the compound of the present invention and the basic skeleton It is possible to improve the luminous efficiency and lifetime of the organic electroluminescent device compared to the comparative example using the compound E to the comparative compound G.

Comparative compound E, which has a dibenzoazepine moiety, showed relatively better results in driving voltage, efficiency, and life than comparative compound D, which is widely used as a host material, and in dibenzoazepine rather than comparative compound E. When using the comparative compound F of the dibenzoazepinocarbazole type, which formed a ring including N atoms, the efficiency was slightly improved, and when the comparative compound G was used, both the efficiency and lifespan were improved.

Meanwhile, the compound according to Formula 1 of the present invention has a structure having a benzoazepinocarbazole moiety in which one phenyl is excluded from dibenzoazepinocarbazole. Comparing the compound of the present invention with the comparative compound F and the comparative compound G, it is the same as having an azepinocarbazole skeleton, but driving a device containing the compound of the present invention with one number of benzene fused to azepinocarbazole The voltage was lowered, and the efficiency and life were improved.

These results can be explained by the energy band gaps of the compounds P-30 and P-120 of the present invention, and comparative compounds E and G.

Referring to Table 6 below, when comparing the HOMO values of Compound P-30 and Comparative Compound E having structures corresponding to each other, it can be seen that Compound P-30 of the present invention has a lower value, Similarly, when comparing the compound P-120 of the present invention with the comparative compound G, it can be seen that the compound P-120 of the present invention has a deeper HOMO value.

[Table 6]

From Table 6 above, it can be seen that the physical properties of the compound (HOMO, LUMO, bandgap and T1) vary depending on the number of benzene rings fused to azepinocarbazole, and this difference in physical properties is the device It acts as a major factor affecting the characteristics, suggesting that when used as a host of the light emitting layer, improved device results can be derived compared to the comparative example.

The above description is only illustrative of the present invention, and those of ordinary skill in the art to which the present invention pertains will be able to make various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed in the present specification are not intended to limit the present invention, but to explain the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The scope of protection of the present invention should be interpreted by the claims below, and all technologies within the scope equivalent thereto should be construed as being included in the scope of the present invention.

100, 200, 300: organic electric device 110: first electrode
120: hole injection layer 130: hole transport layer
140: light emitting layer 150: electron transport layer
160: electron injection layer 170: second electrode
180: light efficiency improvement layer 210: buffer layer
220: light emission auxiliary layer 320: first hole injection layer
330: first hole transport layer 340: first emission layer
350: first electron transport layer 360: first charge generation layer
361: second charge generation layer 420: second hole injection layer
430: second hole transport layer 440: second emission layer
450: second electron transport layer CGL: charge generation layer
ST1: first stack ST2: second stack

Claims (15)

Compound represented by the following formula (1):
<Formula 1>

In Formula 1,
A ring, B ring, and C ring are each independently a C ₆ ~ C ₆₀ aromatic ring group; Fluorene group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; And C ₃ ~ C ₆₀ aliphatic ring group; is selected from the group consisting of,
The A ring, B ring and C ring may each be substituted with one or more of the same or different R ₁ , R ₂ , R ₃ ,
R ¹ , wherein R ₁ to R ₃ are each independently hydrogen; Deuterium, tritium; halogen; Cyano group; Nitro group; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; C ₃ ~ C ₆₀ aliphatic ring group; C ₁ ~ C ₃₀ alkyl group; C ₂ ~ C ₃₀ Alkenyl group; Alkynyl group of C ₂ to C ₃₀ ; An alkoxyl group of C ₁ to C ₃₀ ; C ₆ ~ C ₃₀ aryloxy group; And -L'-[N(R _a )(R _b )] is selected from the group consisting of _c , and neighboring R ₁ and R ₂ can be bonded to each other to form a ring, c is an integer of 1-5 ,
a is an integer from 0 to 2, and when a is 2, each of R ¹ is the same as or different from each other,
L'is a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene group; C ₃ ~ C ₆₀ aliphatic ring group; And O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ heterocyclic group; is selected from the group consisting of,
R _a and R _b are each independently a C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₃ ~ C ₆₀ aliphatic ring group; And O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ heterocyclic group; is selected from the group consisting of,
The R ¹ , R ₁ to R ₃ , L', R _a , R _b , and adjacent R ₁ and R ₂ rings are bonded to each other to form deuterium, respectively; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio group; C ₁ -C ₂₀ alkoxy group; A C ₆ -C ₂₀ arylalkoxy group; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; C ₃ -C ₂₀ aliphatic ring group; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ may be further substituted with one or more substituents selected from the group consisting of arylalkenyl group. The method of claim 1,
The A ring and B ring are each independently a compound characterized in that one of the following formulas F-1 to F-6:
<Formula F-1><FormulaF-2><FormulaF-3>

<Formula F-4><FormulaF-5><FormulaF-6>

In Formulas F-1 to F-6, * represents a condensation position with a neighboring N-containing ring,
R ² to R ⁵ are the same or different and are defined the same as R ₁ or R ₂ of claim ₁ , and adjacent groups may be bonded to each other to form a ring,
b and e are each an integer of 0-4, c is an integer of 0-6, d is an integer of 0-2,
Y is C(R')(R"), N(R _c ), O or S,
R′ and R” are independently of each other hydrogen; deuterium; halogen; cyano group; nitro group; C ₁ -C ₂₀ alkoxy group; C ₆ -C ₂₀ arylalkoxy group; C ₁ -C ₂₀ alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ aryl group; fluorenyl group; At least one heteroatom selected from the group consisting of O, N, S, Si and P It is selected from the group consisting of C ₂ -C ₂₀ heterocyclic group; And C ₃ -C ₂₀ aliphatic ring group; and R′ and R” may be bonded to each other to form a ring,
R _c is a C ₆ -C ₂₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; And C ₃ -C ₂₀ aliphatic ring group; is selected from the group consisting of. The method of claim 1,
The C ring is a compound characterized in that one of the following formulas F-7 to F-10:
<Formula F-7><FormulaF-8><FormulaF-9><FormulaF-10>

In Formulas F-7 to F-10, R ₃ is as defined in claim 1,
f is an integer of 0-3, g is an integer of 0-5, h is an integer of 0 or 1, i is an integer of 0-4, and each of R ³ is the same when each of f, g, and i is an integer of 2 or more. Or different,
Y is C(R')(R"), N(R _d ), O or S,
R′ and R” are independently of each other hydrogen; deuterium; halogen; cyano group; nitro group; C ₁ -C ₂₀ alkoxy group; C ₆ -C ₂₀ arylalkoxy group; C ₁ -C ₂₀ alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ aryl group; fluorenyl group; At least one heteroatom selected from the group consisting of O, N, S, Si and P It is selected from the group consisting of C ₂ -C ₂₀ heterocyclic group; And C ₃ -C ₂₀ aliphatic ring group; and R′ and R” may be bonded to each other to form a ring,
R _d is a C ₆ -C ₂₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; And C ₃ -C ₂₀ aliphatic ring group; is selected from the group consisting of. The method of claim 1,
Formula 1 is a compound represented by one of the following Formulas 1-A to 1-I:
<Formula 1-A><Formula1-B><Formula1-C>

<Formula 1-D><Formula1-E><Formula1-F>

<Formula 1-G><Formula1-H><Formula1-I>

In Formula 1-A to Formula 1-I, R ¹ , R ₁ , R ₂ , R ₃ , a are the same as defined in claim 1,
b is an integer of 0-4, c is an integer of 0-5, d is an integer of 0-6, e is an integer of 0-3, h is an integer of 0-7, i is an integer of 0-8, and these When each is an integer of 2 or more, each of R _1, each of R _{2, and} each of R ₃ are the same or different from each other, and neighboring groups may be bonded to each other to form a ring,
Y is C(R')(R"), N(R _c ), O or S,
R′ and R” are independently of each other hydrogen; deuterium; halogen; cyano group; nitro group; C ₁ -C ₂₀ alkoxy group; C ₆ -C ₂₀ arylalkoxy group; C ₁ -C ₂₀ alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ aryl group; fluorenyl group; At least one heteroatom selected from the group consisting of O, N, S, Si and P It is selected from the group consisting of C ₂ -C ₂₀ heterocyclic group; And C ₃ -C ₂₀ aliphatic ring group; and R′ and R” may be bonded to each other to form a ring,
R _c is a C ₆ -C ₂₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; And C ₃ -C ₂₀ aliphatic ring group; is selected from the group consisting of. The method of claim 1,
At least one of the R ₁ to R ₃ is -L'-N(R _a )(R _b ). The method of claim 1,
At least one of the R ₁ to R ₃ is a compound characterized in that the formula 3-1 or 3-2:
<Formula 3-1><Formula3-2>

In Formulas 3-1 and 3-2,
Q ¹ to Q ⁴ are each independently N, C or C (R _d ), Q ⁵ to Q ⁹ are each independently N or C (R _d ),
L _a and L _b are each independently a single bond; C ₆ -C ₆₀ arylene group; Fluorenylene group; A C ₂ -C ₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si and P; And C ₃ -C ₆₀ aliphatic ring group; is selected from the group consisting of,
Z ring is selected from the following structures,

In the above structure, * represents a condensation position with a ring including Q ¹ to Q ⁴ ,
W ¹ and W ² are each independently a single bond, N-(L ³ -Ar ³ ), S, O, C or C(R _e )(R _f ),
V is independently of each other N, C or C (R _g ),
R _d , R _e , R _f , R _g and Ar ³ are each independently hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio group; An alkoxyl group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; A C ₃ -C ₂₀ cycloalkyl group; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ is selected from the group consisting of an arylalkenyl group, and neighboring groups may be bonded to each other to form a ring, and R _d and R _e may be bonded to each other to form a ring,
L ³ is a single bond; C ₆ -C ₆₀ arylene group; Fluorenylene group; A C ₂ -C ₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si and P; And C ₃ -C ₆₀ is selected from the group consisting of an aliphatic ring group. The method of claim 1,
The compound represented by Formula 1 is a compound characterized in that one of the following compounds:

. In an organic electric device comprising an anode, a cathode, and an organic material layer formed between the anode and the cathode,
The organic material layer is an organic electric device comprising a single compound or two or more compounds represented by Formula 1 of claim 1. In an organic electric device comprising an anode, a cathode, an organic material layer formed between the anode and the cathode, and a light efficiency improvement layer,
The light efficiency improvement layer is formed on one side of both sides of the anode or the cathode that is not in contact with the organic material layer,
An organic electric device, characterized in that the organic material layer or the light efficiency improvement layer comprises a compound represented by Formula 1 of claim 1. The method according to claim 8 or 9,
The organic material layer comprises at least one of a hole injection layer, a hole transport layer, a light emission auxiliary layer, a light emission layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer. The method of claim 10,
The organic electric device, characterized in that the compound is included in the light emitting layer or the light emitting auxiliary layer. The method according to claim 8 or 9,
The organic material layer comprises at least two stacks including a hole transport layer, an emission layer, and an electron transport layer sequentially formed on the anode. The method of claim 12,
The organic material layer further comprises a charge generation layer formed between the two or more stacks. A display device comprising the organic electric device of claim 8 or 9; And
Electronic device comprising a; a control unit for driving the display device. The method of claim 14,
The organic electric device is an electronic device, characterized in that selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a monochromatic lighting device, and a quantum dot display device.

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