WO2021020799A1 - Compound for organic electric element, organic electric element using same, and electronic device comprising same organic electric element - 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 layer placed between the first electrode and the second electrode; and an electronic device comprising the organic electric element. The compound represented by chemical formula 1 is contained in the organic layer, whereby the organic electric element can have low driving voltage, improved luminous efficiency, and increased service life.

Description

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

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

In general, 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 a better natural color 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 the long life and high efficiency can be achieved at the same time when the energy level and T1 value between the organic material layers, the intrinsic properties of the material (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 driving voltage range of the blue device of the full device). Mobility) is required to develop an auxiliary light emitting layer.

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.

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 embodiment of the present invention, not only can the driving voltage of the device be lowered, but also the luminous efficiency, color purity, stability, and lifespan of the device can be greatly improved.

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

[Explanation of code]

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

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" and "fluorenylene group" used in the present invention mean a substituted or unsubstituted fluorenyl group and a substituted unsubstituted fluorenylene group, respectively, unless otherwise specified, and R and R'includes a compound formed by bonding to each other. Unsubstituted fluorenyl group or unsubstituted fluorenylene group refers to a monovalent or divalent functional group in which R, R'and R" are all hydrogen in the following structure, and a substituted fluorenyl group or substituted fluorenylene group In the following structure, it means that at least one of R, R', and R" is a substituent other than hydrogen. In the present specification, a fluorenyl group, a fluorenylene group, and the like may all be referred to as fluorene groups regardless of the valence.

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. In addition, a compound including a heteroatom group such as SO ₂ , P=O, etc. instead of carbon forming a ring may be included in the heterocyclic group.

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, a compound in which benzene as an aromatic ring and cyclohexane, which is a non-aromatic ring, are fused is also an aliphatic ring.

The term'group name' such as an aryl group, an arylene group, and a heterocyclic group as used herein may describe the'name of the group reflecting the number', but may also be described as the'parent compound name'. 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 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 specified in the present specification, when indicating a condensed ring, a number in'number-condensed ring' indicates the number of condensed rings. For example, a form in which three rings are condensed with each other, such as anthracene, phenanthrene, benzoquinazoline, etc., may be expressed as a 3-condensed ring.

In addition, unless otherwise specified in the specification, when a ring is expressed in the form of a'numeric resource' such as a five-membered ring or a six-membered ring, the number in'number-atomic' indicates the number of elements forming the ring. For example, thiophene or furan may correspond to a five-membered ring, and benzene or pyridine may correspond to a six-membered ring.

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; And C ₃ ~ C ₆₀ aliphatic ring group; may be selected from the group consisting of.

At this time, unless otherwise described in the specification, the term'neighboring groups' refers to the following formula as an example, between R ₁ and R _2, between R ₂ and R _3, between R ₃ and R ₄ , Not only R ₅ and R ₆ but also R ₇ and R ₈ sharing one carbon are included, and are not immediately adjacent, such as between R ₁ and R ₇ , R ₁ and R ₈ or R ₄ and R ₅ Substituents bonded to ring elements (such as carbon or nitrogen) may also be included. In other words, if there are substituents on a ring element such as carbon or nitrogen immediately adjacent to each other, they can be neighboring groups, but if no substituent is bonded to the ring element at the immediately adjacent position, it is bonded to the next ring element. It may be a group adjacent to the substituted substituent, and also the substituents bonded to the carbon constituting the same ring may be referred to as adjacent groups.

In the following formula, when substituents bonded to the same carbon as R ₇ and R ₈ are bonded to each other to form a ring, a compound containing a spiro moiety may be formed.

,

In addition, in the present specification, the expression'neighboring groups can be bonded to each other to form a ring' is used in the same meaning as'neighboring groups are selectively bonded to each other to form a ring', and at least one pair of It refers to a case where neighboring groups are bonded to each other to form a ring.

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, a 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.

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 layer 140, 340, 440, or may be used as a material for the light efficiency improvement layer 180, but preferably, the light emitting layer 140, 340, 440, the light emitting auxiliary layer 220 ) 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 emitting layer 140, 340, 440, the light emitting auxiliary layer 220, 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 spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, 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 a top emission type, a bottom emission type, or a double-sided 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.

R ¹ to R ⁵ are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro 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; C ₆ ~ C ₃₀ arylthio group; L ¹ -Ar ¹ ; And L ² -N (L ³ -Ar ² ) (L ⁴ -Ar ³ ) It is selected from the group consisting of, neighboring groups may be bonded to each other to selectively form a ring.

The ring formed by bonding adjacent groups 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; And C ₃ ~ C ₆₀ aliphatic ring group; may be selected from the group consisting of.

When adjacent groups are bonded to each other to form an aromatic ring, preferably a C ₆ ~ C ₂₀ aromatic ring, more preferably a C ₆ ~ C ₁₄ aromatic ring, such as benzene, naphthalene, phenanthrene, etc. , It can form a ring containing a benzene moiety.

In addition, when neighboring groups are bonded to each other to form a heterocycle, preferably a C ₂ to C ₃₀ heterocyclic group containing at least one heteroatom of O, N, S, more preferably O, N , S C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom, such as indole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, heterocycle containing a carbazole moiety, etc. Can be

In addition, when adjacent groups are bonded to each other to form an aliphatic ring, preferably a C ₃ to C ₃₀ aliphatic ring group, more preferably a C ₃ to C ₂₀ aliphatic ring group, such as 2,3 -Dihydro-1,1-dimethyl-1 H -may be indene.

a and e are each an integer of 0 to 4, b is an integer of 0 to 3, c and d are each an integer of 0 to 2, and when each is an integer of 2 or more, each of R ^1, each of R ^{2, and} each of R ³ , Each of R ^{4 and} each of R ⁵ are the same as or different from each other.

L ¹ to L ⁴ 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 may be selected from the group consisting of a C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom.

When L ¹ is an arylene group, preferably a C ₆ ~ C ₃₀ arylene group, more preferably a C ₆ ~ C ₁₈ arylene group, such as phenylene, biphenylene, naphthalene, terphenyl, etc. .

When L ¹ is a heterocyclic group, preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₂₃ heterocyclic group, such as pyridine, pyrimidine, triazine, quinoline, isoquinoline , Quinazoline, benzoquinazoline, dibenzoquinazoline, quinoxaline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine, benzofuropyrazole, benzimidazole, carbazole , Phenylcarbazole, spiro[fluorene-9,9'-indenopyrimidine], and the like.

When the L ² to L ⁴ 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 phenylene, biphenylene, naphthalene, terphenyl Etc.

When the L ² to L ⁴ is a heterocyclic group, preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₁₂ heterocyclic group such as dibenzofuran, dibenzothiophene, It may be carbazole and the like.

When the L ² to L ⁴ is a fluorenyl group, it may be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, and the like. .

Ar ¹ to Ar ³ are each independently a C ₆ to C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; And C ₃ ~ C ₆₀ It may be selected from the group consisting of an aliphatic ring group.

When Ar ¹ to Ar ³ are 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 , Pyrene, anthracene, and the like.

When Ar ¹ to Ar ³ are fluorenyl groups, 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, spiro[ Benzo[ b ]fluorene-11,9'-fluorene], benzo[ b ]fluorene, 11,11-diphenyl-11 H -benzo[ b ]fluorene, 9-(naphthalen-2-yl)9 -phenyl -9 H-fluorene, and the like.

When Ar ¹ to Ar ³ is a heterocyclic group, preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₂₅ heterocyclic group such as pyrimidine, triazine, quinoline, isoquinoline, Quinazoline, benzoquinazoline, dibenzoquinazoline, quinoxaline, benzothienopyrimidine, benzofuropyrimidine, benzofuropyrazole, benzimidazole, carbazole, phenylcarbazole, spiro[fluorene -9,9'-indenopyrimidine], naphthobenzofuran, naphthobenzothiophene, benzocarbazole, benzophenylcarbazole, spiro[fluorene-9,9'-xanthene], and the like.

The R ¹ to R ⁵ , L ¹ to L ⁴ , Ar ¹ to Ar ³ , and the rings formed by bonding of adjacent groups to each other are 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; Phosphine oxide 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 aryloxy group; C ₆ -C ₂₀ arylthio 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.

Formula 1 may be represented by one of Formulas 1-1 to 1-5 below.

<Formula 1-1> <Formula 1-2> <Formula 1-3> <Formula 1-4> <Formula 1-5>

In Formulas 1-1 to 1-5, R ¹ to R ⁵ , a to e, L ¹ and Ar ¹ are the same as defined in Formula 1 above.

In addition, Formula 1 may be represented by one of Formulas 1-6 to 1-10 below.

<Formula 1-6> <Formula 1-7> <Formula 1-8> <Formula 1-9> <Formula 1-10>

In Formulas 1-6 to 1-10, R ¹ to R ⁵ , a to e, L ² to L ⁴ , Ar ² and Ar ³ are the same as defined in Chemical Formula 1.

Wherein among the formula R ¹ a neighboring one, the adjacent R ² to each other, to have the R ³ formed with each other, bonded to each other between the adjacent R ⁴ or adjacent R ⁵ together neighboring rings in the formula A-1) to (A-5 It may be selected from the group consisting of.

<Formula A-1> <Formula A-2> <Formula A-3> <Formula A-4> <Formula A-5>

In Formulas A-1 to A-5, * represents a condensation position, and each symbol may be defined as follows.

X ¹ and X ² are each independently a single bond, C(R')(R"), N-(L ⁵ -Ar ⁴ ), O or S, except when both X ¹ and X ² are single bonds do.

R ⁶ , R ⁷ , R'and R" are each independently hydrogen; deuterium; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; C ₁ -C ₂₀ Phosphine oxide unsubstituted or substituted with an alkyl group of or 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 an alkoxy group; alkynyl of _{C 2 -C 20; C 6 -C} 20 aryloxy; C ₆ -C ₂₀ aryl import of Im; C ₂ -C ₂₀ alkenyl group of; C ₁ -C ₂₀ alkyl group; C ₆ -C ₂₀ aryl group; fluorenyl group; C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ It is selected from the group consisting of an aliphatic ring group; C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ arylalkenyl group, and neighboring groups may be bonded to each other to form a ring.

f is an integer of 0 to 4, when f is an integer of 2 or more, each of R ⁶ is the same as or different from each other, g is an integer of 0 to 2, and when g is an integer of 2, each of R ⁷ is the same or different from each other.

L ⁵ is a single bond; 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 It may be selected from the group consisting of an aliphatic ring group.

Ar ⁴ 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 It may be selected from the group consisting of an aliphatic ring group.

At least one of R ¹ to R ⁵ in Formula 1 is selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a carbazolyl group, the following formula B-1, the following formula B-2, and the following formula B-3 Can be.

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

In Formulas B-1 to B-3, L is defined in the same manner as L 1 of claim ^1, and Y ¹ to Y ¹⁶ are each independently C (R _c ) or N, and X ³ and X ⁴ are each Independently, it is a single bond, C(R _d )(R _e ), N-(L ⁵ -Ar ⁴ ), O or S, except when both X ³ and X ⁴ are single bonds.

R _c , R _d and R _e 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; Phosphine oxide 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 aryloxy group; C ₆ -C ₂₀ arylthio 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 is selected from the group consisting of arylalkenyl group, neighboring groups may be bonded to each other to form a ring.

L ⁵ is a single bond; 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 It may be selected from the group consisting of an aliphatic ring group.

Ar ⁴ 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 It may be selected from the group consisting of an aliphatic ring group.

At least one of Ar ² and Ar ³ in Formula 1 may be represented by the following Formula C.

<Formula C>

In Formula C, L ⁷ is defined the same as L ^{1 in} Formula 1, and ring A and ring B are independently of each other C ₆ ~ C ₂₀ aromatic ring group or at least one of O, N, S, Si and P It is a C ₄ ~ C ₂₀ heterocyclic group containing a hetero atom of, and X ⁵ is C(R')(R"), N-(L ⁵ -Ar ⁴ ), O or S.

The R′ and R” are independently of each other hydrogen; deuterium; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; a siloxane group; a boron group; a germanium group; a cyanide group; group; a C ₁ -C _20; a nitro group; C ₁ -C ₂₀ coming of the alkylthio; C ₁ -C ₂₀ alkoxy group; Im coming aryl of C ₆ -C _20; C ₆ -C ₂₀ aryloxy group 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 selected from the group consisting of O, N, S, Si and P C ₂ -C ₂₀ heterocyclic group including a hetero atom; C ₃ -C ₂₀ aliphatic ring group; C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ selected from the group consisting of arylalkenyl group , R'and R" may be bonded to each other to form a ring.

L ⁵ is a single bond; 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 It may be selected from the group consisting of an aliphatic ring group.

Ar ⁴ 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 It may be selected from the group consisting of an aliphatic ring group.

The compound represented by Formula 1 may be one of the following compounds, but is not limited thereto.

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 (final product) represented by Formula 1 according to the present invention may be synthesized by reacting Sub 1 and Sub 2 or Sub 1 and Sub 3 as shown in Scheme 1 below, but is not limited thereto.

<Scheme 1> (Hal is I, Br, OTf, Cl or F, b1 and b5 are each an integer of 0-4, b2 is an integer of 0-3, b3 and b4 are each an integer of 0-2, b1 at least one of ~b5 is 1)

I. of Sub 1 Synthesis example

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

<Reaction Scheme 2> (a1 is an integer of 0-3, a2 and a3 are integers of 0-5, respectively)

One. Sub1 -2 Synthesis example

(One) Sub1 -2b synthesis

Sub1-2a (20 g, 77.8 mmol), 2-chloroaniline (11.4 g, 89.5 mmol), Pd ₂ (dba) ₃ (3.6 g, 3.9 mmol), P( t -Bu) ₃ (1.6 g, 7.8 mmol) , NaO t -Bu (22.4 g, 233.4 mmol) was added to toluene (400ml) and stirred at 90°C. When the reaction is completed, the temperature of the reactant is cooled to room temperature and toluene is removed. Extracted with MC and washed with water. The organic layer was dried over MgSO ₄ , concentrated, and the resulting organic material was separated by a silica gel column to obtain 19.4 g (82%) of the product.

(2) Sub1 -2c synthesis

Sub1-2b (19 g, 62.5 mmol) Pd(OAc) ₂ (0.7 g, 3.1 mmol), P(t-Bu) ₃ (1.3 g, 6.3 mmol), K ₂ CO ₃ (25.9 g, 187.6 mmol) , DMA (380 ml) was added and refluxed at 170° C. for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, DMA was removed, extracted with MC, and washed with water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was separated through a silica gel column to obtain 14 g (84%) of the product.

(3) Sub1 -2d synthesis

Sub1-2c (13 g, 48.6 mmol), 1-bromo-4-chloro-2-iodobenzene (17.8 g, 55.9 mmol), Pd ₂ (dba) ₃ (2.2 g, 2.4 mmol), P( t -Bu) ₃ (1 g, 4.9 mmol), NaO t -Bu (14 g, 145.9 mmol) was added to toluene (300ml) and stirred at 90°C. When the reaction is completed, the temperature of the reactant is cooled to room temperature and toluene is removed. Extracted with MC and washed with water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was separated through a silica gel column to obtain 19.1 g (86%) of the product.

(4) Sub1 -2 synthesis

Sub1-2d (18 g, 39.4 mmol) Pd(OAc) ₂ (0.4 g, 2 mmol), P(t-Bu) ₃ (0.8 g, 3.9 mmol), K ₂ CO ₃ (16.3 g, 118.2 mmol) , DMA (200 ml) was added and refluxed at 170°C for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, DMA was removed, extracted with MC, and washed with water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was separated by a silica gel column to obtain 11.7 g (79%) of the product.

2. Sub1 -13 Synthesis example

(One) Sub1 -13b synthesis

Sub1-13a (30 g, 116.7 mmol), 2,4-dichloroaniline (21.7 g, 134.2 mmol), Pd ₂ (dba) ₃ (5.3 g, 5.8 mmol), P( t -Bu) ₃ (2.4 g, 11.7 mmol), NaO t -Bu (33.6 g, 350 mmol) was added to toluene (600ml), and then proceeded in the same manner as for the synthesis of Sub1-2b to obtain 34.7 g (88%) of the product.

(2) Sub1 -13c synthesis

Sub1-13b (30 g, 88.7 mmol) Pd(OAc) ₂ (1 g, 4.4 mmol), P(t-Bu) ₃ (1.8 g, 8.9 mmol), K ₂ CO ₃ (36.8 g, 266.1 mmol) , DMA (600 ml) was added, followed by the same method as the synthesis method of Sub1-2c to obtain 21.7 g (81%) of the product.

(3) Sub1 -13d synthesis

Sub1-13c (20 g, 66.3 mmol), 1,2-dibromobenzene (18 g, 76.2 mmol), Pd ₂ (dba) ₃ (3 g, 3.3 mmol), P( t -Bu) ₃ (1.3 g, 6.6 mmol), NaO t -Bu (19.1 g, 198.8 mmol) was added to toluene (400ml), and then proceeded in the same manner as for the synthesis of Sub1-2d to obtain 26 g (86%) of the product.

(4) Sub1 -13 synthesis

Sub1-13d (20 g, 43.8 mmol) Pd(OAc) ₂ (0.5 g, 2.2 mmol), P(t-Bu) ₃ (0.9 g, 4.4 mmol), K ₂ CO ₃ (18.2 g, 131.4 mmol) , DMA (400 ml) was added, followed by the same method as for the synthesis of Sub1-2 to obtain 13.5 g (82%) of the product.

3. Sub1 -16 Synthesis example

(One) Sub1 -16b synthesis

Sub1-16a (25 g, 97.2 mmol), 3,4-dichloronaphthalen-2-amine (23.7 g, 111.8 mmol), Pd ₂ (dba) ₃ (4.5 g, 4.9 mmol), P( t -Bu) ₃ ( 2 g, 9.7 mmol), NaO t -Bu (28 g, 291.7 mmol) was added to toluene (500ml), and then proceeded in the same manner as for the synthesis of Sub1-2b to obtain 34.3 g (91%) of the product.

(2) Sub1 -16c synthesis

Sub1-16b (30 g, 77.3 mmol) Pd(OAc) ₂ (0.9 g, 3.9 mmol), P(t-Bu) ₃ (1.6 g, 7.7 mmol), K ₂ CO ₃ (32 g, 231.8 mmol) , DMA (600 ml) was added, followed by the same method as for the synthesis of Sub1-2c to obtain 23 g (85%) of the product.

(3) Sub1 -16d synthesis

Sub1-16c (20 g, 56.9 mmol), 1,2-dibromobenzene (15.4 g, 65.4 mmol), Pd ₂ (dba) ₃ (2.6 g, 2.8 mmol), P( t -Bu) ₃ (1.2 g, 5.7 mmol), NaO t -Bu (16.4 g, 170.5 mmol) was added to toluene (400ml), and then proceeded in the same manner as for the synthesis of Sub1-2d to obtain 20.7 g (72%) of the product.

(4) Sub1 -16 synthesis

Sub1-16d (15 g, 29.6 mmol) Pd(OAc) ₂ (0.4 g, 2 mmol), P(t-Bu) ₃ (0.8 g, 3.9 mmol), K ₂ CO ₃ (12.3 g, 88.8 mmol) , DMA (300 ml) was added, followed by the same method as for the synthesis of Sub1-2 to obtain 10.5 g (83%) of the product.

4. Sub1 -29 Synthesis example

(One) Sub1 -29b synthesis

Sub1-29a (23 g, 89.5 mmol), 2-chlorodibenzo[b,d]furan-3-amine (22.4 g, 102.9 mmol), Pd ₂ (dba) ₃ (4.1 g, 4.5 mmol), P( t- Bu) ₃ (1.8 g, 8.9 mmol), NaO t -Bu (25.8 g, 268.4 mmol) was added to toluene (500ml), and then proceeded in the same manner as the synthesis method of Sub1-2b, and the product 28.5 g (81% ).

(2) Sub1 -29c synthesis

Sub1-29b (20 g, 50.8 mmol) in Pd(OAc) ₂ (0.6 g, 2.9 mmol), P(t-Bu) ₃ (1.2 g, 5.8 mmol), K ₂ CO ₃ (21.1 g, 152.3 mmol) , DMA (540 ml) was added and proceeded in the same manner as for the synthesis of Sub1-2c to obtain 13.6 g (75%) of the product.

(3) Sub1 -29d synthesis

Sub1-29c (10 g, 27.9 mmol), 2-bromo-4-chloro-1-iodobenzene (10.2 g, 32.2 mmol), Pd ₂ (dba) ₃ (1.6 g, 1.73 mmol), P( t -Bu) ₃ (0.7 g, 3.5 mmol), NaO t -Bu (8.1 g, 83.9 mmol) was added to toluene (300ml) and then proceeded in the same manner as for the synthesis of Sub1-2d to obtain 10.9 g (71%) of the product. .

(4) Sub1 -29 synthesis

Sub1-29d (10 g, 18.3 mmol) Pd(OAc) ₂ (0.2 g, 0.9 mmol), P(t-Bu) ₃ (0.4 g, 1.8 mmol), K ₂ CO ₃ (7.6 g, 54.9 mmol) , DMA (200 ml) was added and proceeded in the same manner as for the synthesis of Sub1-2 to obtain 5.5 g (64%) of the product.

5. Sub1 -32 Synthesis example

(One) Sub1 -32b synthesis

Sub1-32a (25 g, 97.2 mmol), 2,4-dichloroaniline (18.1 g, 111.8 mmol), Pd ₂ (dba) ₃ (4.5 g, 4.9 mmol), P( t -Bu) ₃ (2 g, 9.7 mmol), NaO t -Bu (28 g, 291.7 mmol) was added to toluene (400ml), and then proceeded in the same manner as for the synthesis of Sub1-2b to obtain 29.3 g (89%) of the product.

(2) Sub1 -32c synthesis

Sub1-32b (25 g, 73.9 mmol) in Pd(OAc) ₂ (0.8 g, 3.7 mmol), P(t-Bu) ₃ (1.5 g, 7.4 mmol), K ₂ CO ₃ (30.7 g, 221.7 mmol) , DMA (500 ml) was added, and the product 18.3 g (82%) was obtained by proceeding in the same manner as in the synthesis method of Sub1-2c.

(3) Sub1 -32d synthesis

Sub1-32c (15 g, 49.7 mmol), 3-bromo-4-iodo-N,N-diphenylaniline (25.7 g, 57.2 mmol), Pd ₂ (dba) ₃ (2.3 g, 2.5 mmol), P( t- Bu) ₃ (1 g, 4.9 mmol), NaO t -Bu (14.3 g, 149.1 mmol) was added to toluene (300ml), and then proceeded in the same manner as the synthesis method of Sub1-2d, and the product 26.7 g (86% ).

(4) Sub1 -32 synthesis

Pd(OAc) ₂ (0.4 g, 2 mmol), P(t-Bu) ₃ (0.8 g, 3.9 mmol), K ₂ CO ₃ (13.3 g, 96.2 mmol) in Sub1-32d (20 g, 32.1 mmol) , DMA (300 ml) was added, followed by the same method as for the synthesis of Sub1-2 to obtain 14.5 g (83%) of the product.

6. Sub1 -34 Synthesis example

(One) Sub1 -34b synthesis

Sub1-34a (20 g, 77.8 mmol), 2-chloro-4-(dibenzo[b,d]furan-2-yl)aniline (26.3 g, 89.5 mmol), Pd ₂ (dba) ₃ (3.6 g, 3.9 mmol), P( t -Bu) ₃ (1.6 g, 7.8 mmol), NaO t -Bu (22.4 g, 233.4 mmol) was added to toluene (400ml), and then proceeded in the same manner as for the synthesis of Sub1-2b. This gave 31 g (85%) of the product.

(2) Sub1 -34c synthesis

Sub1-34b (27 g, 57.5 mmol) Pd(OAc) ₂ (0.6 g, 2.9 mmol), P(t-Bu) ₃ (1.2 g, 5.8 mmol), K ₂ CO ₃ (23.8g, 172.4 mmol) , DMA (540 ml) was added, followed by the same method as for the synthesis of Sub1-2c to obtain 19.7 g (79%) of the product.

(3) Sub1 -34d synthesis

Sub1-34c (15 g, 34.6 mmol), 2-bromo-1,4-dichlorobenzene (9 g, 39.8 mmol), Pd ₂ (dba) ₃ (1.6 g, 1.73 mmol), P( t -Bu) ₃ ( 0.7 g, 3.5 mmol), NaO t -Bu (10 g, 103.8 mmol) was added to toluene (300ml), and then proceeded in the same manner as the synthesis method of Sub1-2d to obtain 16.8 g (84%) of the product.

(4) Sub1 -34 synthesis

Sub1-34d (15 g, 25.9 mmol) Pd(OAc) ₂ (0.3 g, 1.3 mmol), P(t-Bu) ₃ (0.5 g, 2.6 mmol), K ₂ CO ₃ (10.8 g, 77.8 mmol) , DMA (300 ml) was added, and the product 11.4 g (81%) was obtained by proceeding in the same manner as in the synthesis method of Sub1-2.

The compounds belonging to Sub 1 may be the following compounds, but are not limited thereto, and Table 1 shows the FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds.

[Table 1]

II. Synthesis of Sub 2

Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 3 below, but is not limited thereto.

<Scheme 3> (Hal ¹ is I, Br or Cl)

1.Sub 2-2 Synthesis example

4-bromo-1,1'-biphenyl (5 g, 21.45 mmol) bis(pinacolato)diboron (7.1 g, 27.89 mmol), PdCl ₂ (dppf) _, (0.78 g, 1.07 mmol), KOAc (6.3 g, 64.35 mmol) and DMF (270 ml) were added and stirred at 120°C to reflux. When the reaction is completed, the temperature of the reactant is cooled to room temperature, water is added to precipitate a compound, and the resulting organic material is recrystallized. ㅇ Thereafter, the product was separated by a silica gel column to obtain 4.8 g (80%) of the product.

2.Sub 2-37 Synthesis example

2-bromodibenzo[b,d]furan (10 g, 40.47 mmol) bis(pinacolato)diboron (13.3 g, 52.61 mmol), PdCl ₂ (dppf) _, (0.05 eq), KOAc (3 eq), anhydrous DMF were added And proceeded in the same manner as the Sub 4-2 synthesis method to synthesize 9.7 g of the product. (Yield 82%)

The compound belonging to Sub 2 may be the following compound, but is not limited thereto, and Table 2 shows the FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds. In the following compounds, Bpin is boronic acid pinacol ester,

Means ).

[Table 2]

III. Of Sub 3 Synthesis example

Sub 3 of Scheme 1 may be synthesized by the reaction path of Scheme 4 below (initiated in Korean Patent Registration No. 10-1251451 (published on April 5, 2013)), but is not limited thereto.

<Reaction Scheme 4>

The compound belonging to Sub 3 may be the following compound, but is not limited thereto, and Table 3 shows the FD-MS values of the following compounds.

[Table 3]

IV. Synthesis of the final compound

1.1-1 Synthesis example

Sub1-12 (10 g, 26.6 mmol) in Sub2-87 (11.5 g, 31.9 mmol), Pd(PPh ₃ ) ₄ (1.5 g, 1.3 mmol), K ₂ CO ₃ (11 g, 79.8 mmol), THF ( 52mL), water (15mL) was added and reacted for 6 hours. After the reaction is completed, the temperature of the reactant is cooled to room temperature, and THF and H ₂ O are removed. After extraction with MC and washing with water, the organic layer was dried over MgSO ₄ and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 12.6 g (83%) of the product.

2. 1-9 Synthesis example

Sub1-11 (10 g, 26.6 mmol) to Sub2-24 (10.6 g, 31.9 mmol), Pd(PPh ₃ ) ₄ (1.5 g, 1.3 mmol), K ₂ CO ₃ (11 g, 79.8 mmol), THF (52 mL), and water (15 mL) were added and proceeded in the same manner as in the synthesis method of 1-1 to obtain 12.5 g (86%) of the product. Got it.

3. 1-33 Synthesis example

Sub1-25 (10 g, 23.5 mmol) in Sub2-20 (10.7 g, 28.2 mmol), Pd(PPh ₃ ) ₄ (1.4 g, 1.2 mmol), K ₂ CO ₃ (9.7 g, 70.4 mmol), THF ( 52 mL) and water (15 mL) were added and proceeded in the same manner as in the synthesis method of 1-1 to obtain 12 g (81%) of the product.

4. 1-76 Synthesis example

Sub1-9 (10 g, 26.6 mmol) Sub2-99 (9.2 g, 31.9 mmol), Pd(PPh ₃ ) ₄ (1.5 g, 1.3 mmol), K ₂ CO ₃ (11 g, 79.8 mmol), THF ( 120 mL) and water (60 mL) were added, and the procedure was carried out in the same manner as in the synthesis method of 1-1 to obtain 13.2 g (85%) of the product.

5. 1-110 Synthesis example

Sub1-11 (10 g, 26.6 mmol) to Sub3-1 (5.2 g, 30.6 mmol), Pd ₂ (dba) ₃ (1.2 g, 1.3 mmol), P( t -Bu) ₃ (0.5 g, 2.7 mmol) , NaO t -Bu (7.7 g, 79.8 mmol), toluene (200ml) was added and reacted for 6 hours. Thereafter, when the reaction is completed, the temperature of the reactant is cooled to room temperature, and toluene is removed. After extraction with MC and washing with water, the organic layer was dried over MgSO ₄ and concentrated. Then, the concentrate was separated on a silica gel column and recrystallized to obtain 11.5 g (85%) of the product.

The FD-MS values of the compounds 1-1 to 1-110 of the present invention prepared according to the synthesis example as described above are shown in Table 4 below.

[Table 4]

Manufacturing evaluation of organic electric devices

[ Example One] Red organic light emitting device (Phosphorescent host)

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 having 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.

Thereafter, on the hole transport layer, compound 1-1 of the present invention is used as a host material, and bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate (hereinafter abbreviated as "(piq) ₂ Ir(acac)") is used 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 tris(8-quinolinol)aluminum (hereinafter abbreviated as Alq ₃ ) was deposited to a thickness of 40 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 2] to [ Example 15]

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 5 was used instead of the compound 1-1 of the present invention as a host material.

[ Comparative example 1] and [ Comparative example 2]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound A or Comparative Compound B was used as a host material.

<Comparative compound 1> <Comparative compound 2>

By applying a forward bias DC voltage to the organic electroluminescent devices of Examples 1 to 15 and Comparative Examples 1 and 2 of the present invention prepared as described above, electroluminescence (EL) characteristics were measured with PR-650 of photoresearch, and , T95 life was measured with a life measurement equipment manufactured by McScience at a reference luminance 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, when the compound of the present invention is used as a light emitting layer material, the driving voltage is lowered and the efficiency and lifespan are lower than when Comparative Compound 1 or Comparative Compound 2 is used (Comparative Examples 1 to 2). It can be seen that there is a significant improvement.

In more detail, compared to Comparative Compounds 1 and 2, the compounds represented by Formula 1 of the present invention condensate one more benzene ring, resulting in a deeper T1 level (a smaller value), and energy transfer to a dopant. ) As the effect increases, the luminous efficiency seems to be greatly improved. In addition, the compound of the present invention has increased planarity and a high Tg value compared to the comparative compounds, and thus the lifespan seems to be significantly improved.

[ Example 16] Red organic electroluminescent device ( Light-emitting auxiliary layer )

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. Subsequently, the compound 1-75 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.

Thereafter, on the light-emitting auxiliary layer, 4,4'-N,N'-dicarbazole-biphenyl (hereinafter referred to as "CBP") as a host material, and (piq) ₂ Ir (acac) as a dopant material are used. Dopant was doped so that the weight ratio was 95:5 to form a light emitting layer having a thickness of 30 nm.

Next, BAlq was vacuum deposited on the emission layer to a thickness of 10 nm to form a hole blocking layer, and Alq ₃ was deposited on the hole blocking layer to a thickness of 40 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 17] to [ Example 27 ]

An organic electroluminescent device was manufactured in the same manner as in Example 16, except that the compound of the present invention described in Table 6 was used instead of the compound of the present invention 1-75 as the light emitting auxiliary layer material.

[ Comparative example 3]

An organic electroluminescent device was manufactured in the same manner as in Example 16, except that the light emission auxiliary layer was not formed.

[ Comparative example 4] to [ Comparative example 6]

An organic electroluminescent device was manufactured in the same manner as in Example 16, except that Comparative Compounds 3 to 5 below were used instead of Compound 1-75 of the present invention as a material for the auxiliary layer.

<Comparative compound 3> <Comparative compound 4> <Comparative compound 5>

By applying a forward bias DC voltage to the organic electroluminescent devices prepared according to Examples 16 to 27 and Comparative Examples 3 to 6, electroluminescence (EL) characteristics were measured with a PR-650 of Photoresearch, and 2500 cd/m ^{2 At the} reference luminance, the T95 life was measured with a life measurement equipment manufactured by McScience. The measurement results are shown in Table 6 below.

[Table 6]

As can be seen from the results of Table 6, the device result was superior when one of Comparative Compounds 3 to 5 (Comparative Examples 4 to 6) was used rather than when the light emission auxiliary layer was not formed (Comparative Example 3), Compared to Comparative Examples 4 to 6, the driving voltage of the device in which the compound of the present invention is used as a light emitting auxiliary layer material is lower, and efficiency and lifespan are significantly improved.

This is because the compound of the present invention in which one more benzene ring is condensed has improved planarity and glass transition temperature than Comparative Compounds 3 to 5, and thus the characteristics of the device are improved, and thermal stability is also increased.

These results suggest that even if the basic skeleton is a similar compound, as the ring is condensed as in the present invention, the physical properties of the compound such as hole characteristics, light efficiency characteristics, energy level, etc. are changed, and this may lead to device results that are difficult to predict. Are doing.

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 following claims, and all technologies within the scope equivalent thereto should be interpreted as being included in the scope of the present invention.

CROSS-REFERENCE TO RELATED APPLICATION

This patent application is for patent application No. 10-2019-0092462 filed in Korea on July 30, 2019, in the U.S. Patent Law Articles 119 to 121, 365 (35 USC §119 to §121, §365) ), and all the contents are incorporated into this patent application by reference. In addition, if this patent application claims priority for countries other than the United States for the same reason as above, all the contents are incorporated into this patent application as references.

Claims (15)

1. Compound represented by the following formula (1):

   <Formula 1>

   

   In Formula 1,

   R ¹ to R ⁵ are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro 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; C ₆ ~ C ₃₀ arylthio group; L ¹ -Ar ¹ ; And L ² -N (L ³ -Ar ² ) (L ⁴ -Ar ³ ) It is selected from the group consisting of, neighboring groups can be bonded to each other to form a ring,

   a and e are each an integer of 0 to 4, b is an integer of 0 to 3, c and d are each an integer of 0 to 2, and when each is an integer of 2 or more, each of R ^1, each of R ^{2, and} each of R ³ , Each of R ^4, each of R ⁵ is the same as or different from each other,

   L ¹ to L ⁴ 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 is selected from the group consisting of a heterocyclic group of C ₂ ~ C ₆₀ containing at least one heteroatom,

   Ar ¹ to Ar ³ are each independently a C ₆ to C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; And C ₃ ~ C ₆₀ is selected from the group consisting of an aliphatic ring group,

   The R ¹ to R ⁵ , L ¹ to L ⁴ , Ar ¹ to Ar ³ , and the rings formed by bonding of adjacent groups to each other are 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; Phosphine oxide 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 aryloxy group; C ₆ -C ₂₀ arylthio 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.
2. The method of claim 1,

   Formula 1 is a compound characterized in that represented by one of the following formulas 1-1 to 1-5:

   <Formula 1-1> <Formula 1-2> <Formula 1-3> <Formula 1-4> <Formula 1-5>

   

   In Formulas 1-1 to 1-5, R ¹ to R ⁵ , a to e, L ¹ and Ar ¹ are as defined in claim ¹ .
3. The method of claim 1,

   Formula 1 is a compound characterized in that represented by one of the following formulas 1-6 to 1-10:

   <Formula 1-6> <Formula 1-7> <Formula 1-8> <Formula 1-9> <Formula 1-10>

   

   In Formulas 1-6 to 1-10, R ¹ to R ⁵ , a to e, L ² to L ⁴ , Ar ² and Ar ³ are as defined in claim 1.
4. The method of claim 1,

   Adjacent R ¹ together, the adjacent R ² to each other, to a neighbor with each other by R ^3, the adjacent R ⁴ R ⁵ ring formed by at least a bond to each other group a pair neighborhood of from between one to each other and adjacent the formula A-1 to A compound characterized in that it is selected from the group consisting of Formula A-5:

   <Formula A-1> <Formula A-2> <Formula A-3> <Formula A-4> <Formula A-5>

   

   In Formulas A-1 to A-5, * represents a condensation position,

   X ¹ and X ² are each independently a single bond, C(R')(R"), N-(L ⁵ -Ar ⁴ ), O or S, except when both X ¹ and X ² are single bonds And

   R ⁶ , R ⁷ , R'and R" are each independently hydrogen; deuterium; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; C ₁ -C ₂₀ Phosphine oxide unsubstituted or substituted with an alkyl group of or 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 an alkoxy group; alkynyl of _{C 2 -C 20; C 6 -C} 20 aryloxy; C ₆ -C ₂₀ aryl import of Im; C ₂ -C ₂₀ alkenyl group of; C ₁ -C ₂₀ alkyl group; C ₆ -C ₂₀ aryl group; fluorenyl group; C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ An aliphatic ring group of; C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ selected from the group consisting of arylalkenyl groups, and neighboring groups may be bonded to each other to form a ring,

   f is an integer of 0 to 4, and when f is an integer of 2 or more, each of R ⁶ is the same as or different from each other,

   g is an integer of 0-2, and when g is an integer of 2, each of R ⁷ is the same as or different from each other,

   L ⁵ is a single bond; 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 is selected from the group consisting of an aliphatic ring group,

   Ar ⁴ 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 is selected from the group consisting of an aliphatic ring group.
5. The method of claim 1,

   At least one of R ¹ to R ^{5 is} selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a carbazolyl group, the following formula B-1, the following formula B-2, and the following formula B-3. Compound made by:

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

   

   In Formulas B-1 to B-3, L is defined the same as L ¹ in claim ¹ ,

   Y ¹ to Y ¹⁶ are each independently C (R _c ) or N,

   X ³ and X ⁴ are each independently a single bond, C(R _d )(R _e ), N-(L ⁵ -Ar ⁴ ), O or S, except when both X ³ and X ⁴ are single bonds And

   R _c , R _d and R _e 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; Phosphine oxide 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 aryloxy group; C ₆ -C ₂₀ arylthio 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 selected from the group consisting of arylalkenyl groups, and neighboring groups may be bonded to each other to form a ring,

   L ⁵ is a single bond; 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 is selected from the group consisting of an aliphatic ring group,

   Ar ⁴ 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 is selected from the group consisting of an aliphatic ring group.
6. The method of claim 1,

   A compound characterized in that at least one of Ar ² and Ar ³ is represented by the following Formula C:

   <Formula C>

   

   In Formula C, L ⁷ is defined the same as L ¹ in claim ¹ ,

   Ring A and Ring B are independently of each other an aromatic ring group of C ₆ ~ C ₂₀ or a heterocyclic group of C ₄ ~ C ₂₀ containing at least one heteroatom of O, N, S, Si and P,

   X ⁵ is C(R')(R"), N-(L ⁵ -Ar ⁴ ), O or S,

   R′ and R” are independently of each other hydrogen; deuterium; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; a C ₁ -C ₂₀ alkyl group or C ₆ -C ₂₀ aryl group substituted or unsubstituted phosphine oxide; siloxane group; boron group; germanium group; cyano group; nitro group; C ₁ -C ₂₀ alkylthio group; C ₁ -C ₂₀ alkoxy group; C ₆ -C ₂₀ aryloxy group; C ₆ -C ₂₀ arylthio 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 of; Fluorenyl group; C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ aliphatic ring group; C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ selected from the group consisting of arylalkenyl group, R'and R" may be bonded to each other to form a ring,

   L ⁵ is a single bond; 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 is selected from the group consisting of an aliphatic ring group,

   Ar ⁴ 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 is selected from the group consisting of an aliphatic ring group.
7. The method of claim 1,

   The compound represented by Formula 1 is a compound characterized in that one of the following compounds:

   

   

   

   

   .
8. In an organic electric device comprising an anode, a cathode, and an organic material layer formed between the anode and the cathode,

   The organic electroluminescent device, characterized in that the organic material layer comprises a compound represented by the formula (1) of claim 1.
9. The method of claim 8,

   An organic electric device comprising a compound represented by Formula 1 of claim 1, wherein a light efficiency improvement layer is formed on one side of the anode or the cathode that is not in contact with the organic material layer.
10. The method of claim 8,

    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.
11. The method of claim 10,

    The compound is an organic electric device, characterized in that included in at least one of the light emitting layer and the light emitting auxiliary layer.
12. The method of claim 8,

    The organic material layer comprises two or more stacks including a hole transport layer, an emission layer, and an electron transport layer sequentially formed on the anode.
13. The method of claim 12,

    The organic material layer further comprises a charge generation layer formed between the two or more stacks.
14. A display device including the organic electric device of claim 8; And

    Electronic device comprising a; a control unit for driving the display device.
15. 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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