KR20200077203A - An organic electronic element comprising compound for organic electronic element and an electronic device thereof - Google Patents

Abstract

The present invention provides an organic electronic element and an electronic device including the same. The organic electronic element includes a first electrode, a second electrode, and an organic material layer between the first and second electrodes. By including a compound represented by chemical formula 1 and chemical formula 2 in the organic material layer, a driving voltage of the organic electronic device may be lowered, and luminous efficiency and lifespan may be improved.

Description

An organic electrical element and an electronic device containing the compound for an organic electrical element TECHNICAL FIELD OF THE INVENTION ORANNIC ELECTRONIC ELEMENT COMPRISING COMPOUND FOR ORGANIC ELECTRONIC ELEMENT AND AN ELECTRONIC DEVICE THEREOF}

The present invention relates to an organic electric element comprising a compound for an organic electric element and its electronic device.

In general, the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material. An organic electric device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic material layer is often composed 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 the organic material layer in the organic electric device may 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, depending on the function. In addition, the luminescent material may be classified into a high molecular weight type and a low molecular weight type according to the molecular weight, and 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 according to the light emission mechanism. have. In addition, the luminescent material may be divided into blue, green, and red luminescent materials and yellow and orange luminescent materials necessary for realizing a better natural color according to the luminous color.

On the other hand, when only one material is used as the light emitting material, the problem of the maximum light emission wavelength shifting to a long wavelength due to intermolecular interaction and a decrease in color purity or a decrease in the efficiency of the device due to the light emission attenuation effect, increases color purity and energy transfer. To increase the luminous efficiency through, a host/dopant system may be used as a luminescent material. The principle is that when a small amount of the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with the light emitting layer, excitons generated in the light emitting layer are transported to the dopant to produce light with high efficiency. At this time, since the wavelength of the host moves to the wavelength of the dopant, light of a desired wavelength can be obtained according to the type of dopant used.

Currently, the size of the portable display market is increasing as a large-area display, and accordingly, power consumption greater than that required in the existing portable display is required. Therefore, power consumption has become a very important factor for portable displays that have a limited power supply, such as batteries, and the efficiency and lifespan problems must also be solved.

Efficiency, life, and driving voltage are related to each other. When the efficiency increases, the driving voltage decreases relatively, and as the driving voltage decreases, crystallization of organic substances due to Joule heating generated during driving decreases, and as a result, It shows a tendency to increase life. However, simply improving the organic layer does not maximize efficiency. This is because 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, there is a need to develop a light emitting material having high thermal stability and efficiently achieving charge balance in the light emitting layer. That is, in order to sufficiently exhibit the excellent characteristics of the organic electric device, materials constituting an organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, are supported by stable and efficient materials It should be preceded, but the development of a stable and efficient organic material layer material for an organic electric device has not been sufficiently performed, and among them, development of a host material of a light emitting layer is urgently required.

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

In one aspect, the present invention provides an organic electric device comprising a first compound represented by the following formula (1) and a second compound represented by the following formula (2) in the light emitting layer.

<Formula 1> <Formula 2>

In another aspect, the present invention provides an electronic device including the organic electric element.

By using the mixture of the compound represented by Formula 1 and the compound represented by Formula 2 as the material of the light emitting layer of the present invention, the driving voltage of the device can be lowered, and the luminous efficiency and lifetime of the device can be improved.

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

The terms "aryl group" and "arylene group" used in the present invention have 6 to 60 carbon atoms, respectively, and are not limited thereto unless otherwise specified. In the present invention, an aryl group or an arylene group may include a monocyclic, ring aggregate, several conjugated ring systems, spiro compounds, and the like. In addition, unless otherwise specified herein, the aryl group may include a fluorenyl group and the arylene group may include a fluorenylene group.

The term "fluorenyl group" or "fluorenylene group" used in the present invention means a monovalent or divalent functional group in which R, R'and R" are both hydrogen in the following structures, unless otherwise specified. Substituted fluorenyl group" or "substituted fluorenylene group" means that at least one of the substituents R, R', R" is a substituent other than hydrogen, and R and R'are bonded to each other to form a bonded carbon. It includes the case where a compound was formed as a spy together.

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

The term "heterocyclic group" used in the present invention includes aromatic rings such as "heteroaryl group" or "heteroarylene group", as well as non-aromatic rings, and each carbon number containing one or more heteroatoms unless otherwise specified. 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, ring aggregate, heterozygous multiple ring system, spy containing heteroatoms. Means a compound and the like.

The term "heterocyclic group" used in the present invention means a ring containing a heteroatom such as N, O, S, P or Si instead of carbon forming a ring, and "heteroaryl group" or "heteroarylene group" It includes not only aromatic rings such as non-aromatic rings, but also compounds containing heteroatom groups such as SO ₂ , P=O, and the like, instead of carbon forming a ring.

The term "aliphatic ring group" used in the present invention means a cyclic hydrocarbon excluding aromatic hydrocarbons, and includes monocyclic, ring aggregates, conjugated multiple ring systems, spiro compounds, and the like, unless otherwise indicated. It means a 3 to 60 ring, but is not limited thereto. For example, even when the aromatic ring benzene and the non-aromatic ring cyclohexane are fused, it corresponds to the aliphatic ring.

In the present specification, the'group name' corresponding to an aryl group, an arylene group, a heterocyclic group, etc. exemplified as an example of each symbol and its substituent may describe'the name of a group reflecting a singer', but is described as a'parent compound name' You may. For example, in the case of'phenanthrene', which is a type of aryl group, the monovalent'group' is'phenanthryl', and the divalent group can be classified as a singer such as'phenanthrylene', etc. Regardless, the parent compound name may be described as'phenanthrene'. Similarly, in the case of pyrimidine, it can be described as'pyrimidine' regardless of the singer, or in the case of monovalent pyrimidinyl group, in the case of divalent pyrimidineylene, etc., as the'group name' of the corresponding singer. have.

In addition, in this specification, in describing a compound name or a substituent name, a number, an alphabet, etc. indicating a position may be omitted. For example, pyrido[4,3-d]pyrimidine as pyridopyrimidine, benzofuro[2,3-d]pyrimidine as benzofuropyrimidine, 9,9-dimethyl-9H-flu Oren 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 explicitly stated, the formula used in the present invention is applied in the same manner as the definition of a substituent based on the index definition of the following formula.

Here, when a is an integer of 0, the substituent R ¹ means non-existent, that is, when a is 0, it means that hydrogen is bonded to all the carbons forming the benzene ring. The formula or compound may be omitted. In addition, when a is an integer of 1, one substituent R ¹ is bound to any one of carbons forming a benzene ring, and when a is an integer of 2 or 3, for example, it can be bonded as follows, and a is 4 to 6 Even in the case of an integer, 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.

In addition, unless otherwise specified in the present specification, the rings formed by bonding with adjacent groups are C ₆ ~ C ₆₀ aromatic ring groups; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; And combinations thereof.

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

In describing the present invention, when it is determined that detailed descriptions of related known configurations or functions may obscure the subject matter of the present invention, detailed descriptions thereof will be omitted.

Also, if a component such as a layer, film, region, plate, etc. is said to be "above" or "on" another component, it is not only when the other component is "directly above", but also with another component in the middle. It should be understood that the case may be included. Conversely, it should be understood that when a component is said to be “just above” another part, it means that there is no other part in between.

1 is an exemplary view 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 120, a second electrode 180, and a first electrode 120 formed on a substrate 110. Between the second electrode 180 includes an organic material layer containing the compound according to the present invention. In this case, the first electrode 120 may be an anode (anode), the second electrode 180 may be a cathode (cathode), and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

The organic material layer may include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170 sequentially stacked on the first electrode 120. . At this time, at least one of these layers may be omitted, or may further include a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151, an electron transport auxiliary layer, a buffer layer 141, etc., and the electron transport layer 160, etc. It can also serve as a hole blocking layer.

In addition, although not shown, the organic electric device according to an embodiment of the present invention may further include a protective layer or a light efficiency improving layer. The light efficiency improving layer may be formed on a surface of both surfaces of the first electrode that does not contact the organic material layer or a surface of both surfaces of the second electrode that does not contact the organic material layer.

The compound according to an embodiment of the present invention applied to the organic layer is a hole injection layer 130, a hole transport layer 140, a light emitting auxiliary layer 151, an electron transport auxiliary layer, an electron transport layer 160, an electron injection layer ( 170), a host or a dopant of the light emitting layer 150, or may be used as a material for a light efficiency improving layer, but preferably a mixture of a compound represented by Formula 1 and a compound represented by Formula 2 of the present invention of the light emitting layer Used as a host.

On the other hand, even in the case of the same core, the band gap, electrical characteristics, and interfacial characteristics may vary depending on which substituent is attached to which position, and thus, the selection of the core and the combination of sub-substituents coupled thereto. It is necessary to study, especially 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, long life and high efficiency can be achieved simultaneously.

Therefore, in the present invention, by using a mixture of a compound represented by Formula 1 and a compound represented by Formula 2 as a host of a light emitting layer, the energy level and T ₁ value between each organic material layer and the intrinsic properties of the material (mobility, interfacial properties) Etc.) to optimize the lifespan and efficiency of organic electric devices at the same time.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using various deposition methods. It may be manufactured using a deposition method such as PVD or CVD, for example, by depositing a metal or conductive metal oxide or an alloy thereof on a substrate to form the anode 120, and a hole injection layer 130 thereon , After forming an organic material layer including the hole transport layer 140, the light emitting layer 150, the electron transport layer 160 and the electron injection layer 170, it can be prepared by depositing a material that can be used as the cathode 180 thereon. have. In addition, the light emitting auxiliary layer 151 may be further formed between the hole transport layer 140 and the light emitting layer 150, and the electron transport auxiliary layer may be further formed between the light emitting layer 150 and the electron transport layer 160.

In addition, the organic material layer is a solution process or a solvent process that is not a 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, a doctor blading process, a screen It can be produced with fewer layers by a printing process or a method such as thermal transfer. Since the organic material layer according to the present invention can be formed in various ways, the scope of the present invention is not limited by the formation method.

The organic electric device according to an embodiment of the present invention may be a front emission type, a back emission type, or a double-sided emission type depending on the material used.

In addition, the organic electroluminescent 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 an electronic device including a display device including the above-described organic electric element of the present invention and 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 machines, various TVs, and various computers.

Hereinafter, an organic electric device according to an aspect of the present invention will be described.

The organic electric device according to an aspect of the present invention includes a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes a phosphorescent emission layer, and the phosphorescent emission layer The host of the first compound represented by the following formula (1) and the second compound represented by the following formula (2).

<Formula 1> <Formula 2>

First, Formula 1 will be described.

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

X ₁ is O or S.

Ar ¹ and Ar ² are independently of each other C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; And C ₆ ~ C ₃₀ It may be selected from the group consisting of an aryloxy group.

When Ar ¹ and Ar ² are aryl groups, preferably C ₆ to C ₃₀ aryl groups, more preferably C ₆ to C ₁₈ aryl groups, such as phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, Pyrene, triphenylene, and the like. When Ar ¹ and Ar ² are heterocyclic groups, preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₁₆ heterocyclic groups, such as pyridine, quinoline, isoquinoline, carbazole, phenyl Carbazole, dibenzothiophene, dibenzofuran, dibenzodioxin, and the like. When Ar ¹ and Ar ² are fluorenyl groups, it may be 9,9-diphenylfluorene, 9,9-dimethylfluorene, and the like. When Ar ¹ and Ar ² are an aliphatic ring group, preferably an aliphatic ring of C ₃ to C ₃₀ , more preferably an aliphatic ring of C ₃ to C ₁₂ , such as cyclohexane, cyclohexylcyclohexane, and the like. When Ar ¹ and Ar ² are alkyl groups, it may be preferably an alkynyl group of C ₂ to C ₁₀ such as methyl, t-butyl, and the like. When Ar ¹ and Ar ² are alkenyl groups, preferably a C ₂ to C ₁₀ alkenyl group, for example, ethene, propene, or the like.

L ¹ to L ³ are each independently a single bond; C ₆ ~ C ₆₀ Arylene group; Fluorylene group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; And it may be selected from the group consisting of a fused ring of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60.

When L ¹ to L ³ are arylene groups, preferably an arylene group of C ₆ to C ₃₀ , more preferably an arylene group of C ₆ to C ₁₈ , such as phenyl, biphenyl, naphthyl, terphenyl, etc. . When L ¹ to L ³ are heterocyclic groups, preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₁₆ heterocyclic groups, such as carbazole, phenylcarbazole, dibenzofuran, Dibenzothiophene, and the like.

R ¹ is hydrogen; heavy hydrogen; halogen; Cyano group; C ₆ ~ C ₆₀ Aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And -L'-N (R _a ) (R _b ); is selected from the group consisting of, adjacent groups may be bonded to each other to form a ring.

a is an integer of 0-9, and when a is an integer of 2 or more, a plurality of R ^{1 s} are the same as or different from each other.

Rings formed by bonding adjacent R ^{1 to} each other include an aromatic ring group of C ₆ to C ₆₀ ; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; Or it may be a fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60. When adjacent R ^{1 is} bonded to each other to form an aromatic ring, preferably an aromatic ring of C ₆ ~ C ₃₀ , more preferably an aromatic ring of C ₆ ~ C ₁₄ , such as benzene, naphthalene, phenanthrene, etc. The same aromatic ring can be formed.

When R ¹ is an aryl group, preferably an aryl group of C ₆ to C ₃₀ , more preferably an aryl group of C ₆ to C ₁₈ , such as phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, etc. .

L'is independently of each other a single bond; C ₆ ~ C ₆₀ Arylene group; Fluorylene group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; And fused ring groups of the aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; may be selected from the group consisting of.

R _a and R _b are independently of each other C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; And fused ring groups of the aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; may be selected from the group consisting of.

Preferably, the compound derived from Formula 1-1 below in Formula 1 may be excluded.

<Formula 1-1>

In Chemical Formula 1-1, each symbol is the same as defined in Chemical Formula 1. Preferably, Ar ¹ and Ar ² are independently of each other C ₆ ~ C ₁₈ aryl group; Fluorenyl group; C ₂ ~ C ₁₆ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; And C ₆ ~ C _{30 It} is selected from the group consisting of an aryloxy group.

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

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

<Formula 1-C> <Formula 1-D>

<Formula 1-E>

In Chemical Formulas 1-A to 1-E, each symbol may be defined as follows.

Ar ¹ , Ar ² , L ¹ to L ³ , X ₁ , R ¹ , a are as defined in Formula 1.

X ₂ and X ₃ are each independently O or S.

R ₄ , R ⁸ and R ⁹ are independently of each other hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; C ₃ ~ C ₂₀ aliphatic ring and C ₆ ~ C ₂₀ aromatic ring fused ring group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₂₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And -L ^a -N(R ^a )(R ^b ); and adjacent groups may combine with each other to form a ring.

d1 is an integer from 0 to 7, i and j are integers from 0 to 6, and when each of them is an integer of 2 or more, each of a plurality of R _4, each of a plurality of R ^{8, and} each of a plurality of R ⁹ are the same or different from each other Do.

L ^a is ^a single bond independently of each other; C ₆ ~ C ₂₀ Arylene group; Fluorylene group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof.

R ^a and R ^b are independently of each other C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof.

Preferably, the formula 1-A may be represented by one of the following formulas 1-A-1 to 1-A-6.

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

<Formula 1-A-4> <Formula 1-A-5> <Formula 1-A-6>

In Chemical Formulas 1-A-1 to 1-A-6, Ar ¹ , Ar ² , L ¹ to L ³ , X ₁ , R ¹ , a are as defined in Chemical Formula 1-A.

Each symbol in Formula 1, Formula 1-A to 1-E, and Formula 1-A-1 to 1-A-6 may be further substituted. For example, Ar ¹ , Ar ² , L ¹ ~L ³ , L', L ^a , R ¹ , R ₄ , R ⁸ , R ⁹ , R _a , R _b , R ^a , R ^b , and adjacent groups are bonded to each other Rings formed by deuterium, respectively; halogen; A silane group unsubstituted or substituted with an alkyl group of C ₁ -C ₂₀ or an aryl group of C ₆ -C ₂₀ ; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio; C ₁ -C ₂₀ Alkoxy group; C ₆ -C ₂₀ Aryloxy group; C ₁ -C ₂₀ alkyl group; Alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ Aryl group; A C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl group; A 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 Aryl alkenyl group; It may be further substituted with one or more substituents selected from the group consisting of.

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

.

.

Next, the following Chemical Formula 2 will be described.

<Formula 2>

In Chemical Formula 2, each symbol may be defined as follows.

Ar ⁴ to Ar ⁶ are independently of each other C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; And C ₆ ~ C ₃₀ It may be selected from the group consisting of an aryloxy group.

When Ar ⁴ to Ar ⁶ are aryl groups, preferably, C ₆ to C ₃₀ aryl groups, more preferably C ₆ to C ₁₈ aryl groups, such as phenyl, biphenyl, naphthyl, terphenyl, phenanthrene Etc.

When Ar ⁴ to Ar ⁶ are heterocyclic groups, preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₂₀ heterocyclic groups, such as dibenzothiophene, dibenzofuran, benzo Thienopyrimidine, carbazole, phenylcarbazole, benzonaphthothiophene, benzofurothiophene, dynaphthothiophene, dynaphthofuran, and the like.

When Ar ⁴ to Ar ⁶ are fluorenyl groups, it may be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirofluorene, or the like.

L ⁴ to L ⁶ are each independently a single bond; C ₆ ~ C ₆₀ Arylene group; Fluorylene group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; And combinations thereof.

When L ⁴ to L ⁶ are arylene groups, preferably C ₆ to C ₃₀ arylene groups, more preferably C ₆ to C ₁₈ arylene groups, such as phenylene, biphenyl, naphthyl, terphenyl, etc. Can.

When L ⁴ to L ⁶ are a fluorenyl group, it may be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirofluorene, or the like.

The Chemical Formula 2 may be represented by one of the following Chemical Formulas 2-A to 2-I.

<Formula 2-A> <Formula 2-B>

<Formula 2-C>

<Formula 2-D> <Formula 2-E> <Formula 2-F>

<Formula 2-G> <Formula 2-H> <Formula 2-I>

<Formula 2-G> <Formula 2-H> <Formula 2-I>

In Formulas 2-A to 2-I, Ar ⁵ , Ar ⁶ , L ⁴ to L ⁶ are the same as defined in Formula 2, and Y ₁ to Y ₃ are each independently O, S, C(R') (R").

R ¹¹ to R ¹⁶ , R'and R" are independently of each other hydrogen; deuterium; halogen; C ₁ -C ₂₀ alkyl group or C ₆ -C ₂₀ aryl group unsubstituted or substituted silane group; cyano group; nitro group ; C ₁ -C ₂₀ alkoxy group; C ₆ -C ₂₀ aryloxy group; C ₁ -C ₂₀ alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C Aryl group of ₂₀ ; 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; and aliphatic ring of C ₃ -C ₂₀ Group; selected from the group consisting of, adjacent groups may combine with each other to form a ring.

Rings formed by bonding adjacent groups to each other include an aromatic ring group of C ₆ ~C ₆₀ ; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; Or it may be a fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60. For example, neighboring R ¹ , neighboring R ¹² , neighboring R ¹³ , neighboring R ¹⁴ , neighboring R ¹⁵ , neighboring R ^16, or R'and R" are bonded to each other to form an aromatic ring. When forming, preferably, an aromatic ring of C ₆ to C ₃₀ , more preferably an aromatic ring of C ₆ to C ₁₄ , for example, an aromatic ring such as benzene, naphthalene, and phenanthrene can be formed.

b is an integer from 0 to 4, and when b is an integer of 2 or more, each of a plurality of R ^11, each of a plurality of R ^{13, and} each of a plurality of R ¹⁵ are the same or different from each other, c is an integer from 0 to 3, c is In the case of an integer of 2 or more, each of the plurality of R ^12, each of the plurality of R ^{14, and} each of the plurality of R ¹⁶ are the same or different from each other.

The Ar ⁴ ~ Ar ⁶ , L ⁴ ~ L ⁶ , R ¹¹ ~ R ¹⁶ , R', R" and the ring formed by bonding adjacent groups are each deuterium; halogen; C ₁ -C ₂₀ alkyl group or C _6- Silane group unsubstituted or substituted with 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; C _6- C ₂₀ -C20 aryloxy 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; C ₆ -C substituted with deuterium Aryl group of ₂₀ ; 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; aliphatic ring group of C ₃ -C ₂₀ C ₇ -C ₂₀ arylalkyl group; and C ₈ -C ₂₀ arylalkenyl group may be further substituted with one or more substituents selected from the group consisting of.

Specifically, the compound represented by Formula 2 may be one of the following compounds, but is not limited thereto.

.

.

Preferably, in Formulas 1 and 2, L ¹ to L ⁶ may be each independently one of the following Formulas b-1 to b-13.

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

<Formula b-5> <Formula b-6> <Formula b-7> <Formula b-8>

<Formula b-9> <Formula b-10>

<Formula b-11> <Formula b-12> <Formula b-13>

In the formulas b-1 to b-13, each symbol may be defined as follows.

R ⁵ to R ⁷ are independently of each other hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; C ₃ ~ C ₂₀ aliphatic ring and C ₆ ~ C ₂₀ aromatic ring fused ring group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₂₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And -L ^a -N(R ^a )(R ^b ); and adjacent groups may combine with each other to form a ring.

When neighboring R ⁵ , neighboring R ⁶ , or neighboring R ⁷ are bonded to each other to form an aromatic ring, preferably C ₆ ~ C ₃₀ aromatic ring, more preferably C ₆ ~ C ₁₄ Aromatic rings such as benzene, naphthalene, and phenanthrene can be formed.

Y is N-(L ^a -Ar ^a ), O, S or C(R')(R").

Z ¹ to Z ³ are each independently C, C(R') or N, and at least one of Z ¹ to Z ³ is N.

f is an integer from 0 to 6, e, g, h, and i are integers from 0 to 4, j, k are integers from 0 to 3, l is an integer from 0 to 2, and m is from 0 to It is an integer of 3, and when each of these is an integer of 2 or more, each of the plurality of R ^5, each of the plurality of R ^{6, and} each of the plurality of R ⁷ may be the same or different from each other.

R'and R" are independently of each other hydrogen; deuterium; halogen; cyano group; nitro group; C ₆ ~ C ₂₀ aryl group; fluorenyl group; O, N, S, Si and P at least one heteroatom C ₂ ~ C ₂₀ heterocyclic group containing; C ₃ ~ C ₂₀ aliphatic ring group; C ₃ ~ C ₂₀ aliphatic ring and C ₆ ~ C ₂₀ aromatic ring fused ring group; C ₁ ~ C ₂₀ Alkyl group of; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₂₀ alkoxy group; C ₆ ~ C ₃₀ aryloxy group; and -L ^a -N (R ^a ) (R ^b ); may be selected from the group consisting of.

In C(R')(R"), R'and R" may combine with each other to form a ring, and in C(R'), adjacent R's may combine with each other to form a ring.

The Ar ^a is C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof.

L ^a is ^a single bond independently of each other; C ₆ ~ C ₂₀ Arylene group; Fluorylene group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof.

R ^a and R ^b are independently of each other C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof.

The R ⁵ to R ⁷ , L ^a , Ar ^a , R', R", R ^a , R ^b , and rings formed by bonding adjacent groups are each deuterium; halogen; alkyl group of C ₁ -C ₂₀ or C Silane group unsubstituted or substituted with _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; C _6- C ₂₀ aryloxy 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; C ₆ substituted with deuterium -C ₂₀ aryl group; fluorenyl group; C ₂ -C ₂₀ heterocyclic group containing at least one hetero atom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ aliphatic It may be further substituted with one or more substituents selected from the group consisting of a cyclic group; C ₇ -C ₂₀ arylalkyl group; and C ₈ -C ₂₀ arylalkenyl group.

The weight ratio of the first compound and the second compound is 1:9 to 9:1, preferably 3:7 to 7:3, and more preferably 3:7 to 5:5.

Hereinafter, examples of the synthesis of the compounds represented by Chemical Formulas 1 and 2 according to the present invention and manufacturing examples of the organic electric device will be specifically described with reference to Examples, but the present invention is not limited to the following Examples.

[ Synthetic example 1] Formula 1

The compound represented by Chemical Formula 1 according to the present invention may be prepared by reacting Sub 1 and Sub 2 as shown in Reaction Scheme 1 below, but is not limited thereto.

<Scheme 1>

1.Example compounds of Sub 1 and Synthetic example

The compound belonging to Sub 1 of Reaction Scheme 1 may be the following compound, but is not limited thereto.

The FD-MS values of the compounds belonging to Sub 1 are shown in Table 1 below.

[Table 1]

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

<Reaction Scheme 2>

Synthesis Example of Sub 1-7

2-(9,9-diphenyl-9H-fluoren-2-yl)-4,4,5,5 to 2,4-dichloro-6-phenyl-1,3,5-triazine (30 g, 132.71 mmol) -tetramethyl-1,3,2-dioxaborolane (70.77 g, 159.25 mmol), Pd(PPh ₃ ) ₄ (7.67 g, 6.64 mmol), K ₂ CO ₃ (55.02 g, 398.12 mmol), THF (600 ml), water (300 ml) was added, followed by reflux with stirring. After the reaction was completed, the organic layer was concentrated after extraction with ether and water, and then dried over MgSO ₄ and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 51.24 g (yield: 76%) of the product.

Synthesis Example of Sub 1-29

After adding 2,4-dichloro-6-(dibenzo[b,d]furan-4-yl)-1,3,5-triazine (20 g, 63.26 mmol) to a round bottom flask and dissolving in 450 mL of THF, 2 -(4-(dibenzo[b,d]furan-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (28.11 g, 75.92 mmol), Pd(PPh ₃ ) ₄ (3.66 g, 3.16 mmol), K ₂ CO ₃ (26.23 g, 189.79 mmol), 150 mL of water was added, and the same procedure as in Sub 1-7 was performed to obtain 69.7 g of product (yield: 73%).

Synthesis Example of Sub 1-39

2-([1,1':3',1''-terphenyl]-5'-yl)-4,6-dichloro-1,3,5-triazine (17 g, 44.94 mmol) in a round bottom flask After adding and dissolving in THF 340 mL, 2-(dibenzo[b,d]thiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (16.73 g, 53.93 mmol), Pd (PPh ₃ ) ₄ (2.6 g, 2.25 mmol), K ₂ CO ₃ (18.63 g, 134.83 mmol), 170 mL of water was added, and the same procedure as in Sub 1-7 was performed to obtain 69.7 g of product (yield: 73%).

2. Exemplary compounds of Sub 2 and Synthetic example

The compound belonging to Sub 2 of Reaction Scheme 1 may be the following compound, but is not limited thereto.

The FD-MS value of the compound belonging to Sub 2 is shown in Table 2 below.

[Table 2]

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

<Scheme 3>

Sub 2-4 Synthesis Example

Bis(pinacolato)diboron (CAS Registry Number: 73183-34-3) (11.7 g, 46.07 mmol) in 6-(4-bromonaphthalen-2-yl)naphtho[1,2-b]benzofuran (15 g, 35.44 mmol) ), PdCl ₂ (dppf) (1.3 g, 1.77 mmol), KOAc (10.4 g, 106.31 mmol), DMF (300 ml) was added, followed by reflux with stirring. When the reaction is completed, the organic layer is extracted with CH ₂ Cl ₂ and water, then dried over MgSO ₄ and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 12.83 g of product (yield: 77%).

Sub 2-25 Synthesis Example

8-bromobenzo[b]naphtho[2,1-d]thiophene (25 g, 79.82 mmol) with bis(pinacolato)diboron (CAS registry number, 73183-34-3) (26.35 g, 103.76 mmol), PdCl ₂ ( dppf) (3.08 g, 4.21 mmol), KOAc (24.77 g, 252.4 mmol), DMF (500 ml) was added, followed by reflux with stirring. When the reaction is completed, the organic layer is extracted with CH ₂ Cl ₂ and water, then dried over MgSO ₄ and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 24 g of product (yield: 83%).

3. Final compound synthesis example

Synthesis example of 1-13

Sub 1-11 (34.7 g, 80 mmol), Sub 2-25 (30.9 g, 80 mmol), K ₂ CO ₃ (19.3 g, 140 mmol), Pd(PPh ₃ ) ₄ (2.8 g, 2.4 mmol) After putting it in a round bottom flask and adding THF and water, it was refluxed at 80°C for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ and wiped 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 the product (37.4 g, 71%).

Synthesis example of 1-27

Sub 1-13 (44.6 g, 80 mmol) and Sub 2-43 (30.9 g, 80 mmol) were processed in the same manner as the synthesis method of 1-13 to obtain a product (43.2 g, 69%).

Synthesis example of 1-34

Sub 1-34 (42.7 g, 80 mmol) and Sub 2-18 (34.9 g, 80 mmol) were obtained using the synthesis method of 1-13 (42.7 g, 66%).

Synthesis example of 1-45

Sub 1-37 (40.8 g, 80 mmol) and Sub 2-49 (43.1 g, 80 mmol) obtained the product (51.0 g, 72%) using the synthesis method of 1-13.

Synthesis example of 1-53

Sub 1-1 (40.8 g, 80 mmol) and Sub 2-51 (37.0 g, 80 mmol) were obtained using the synthesis method of 1-13 (45.4 g, 70%).

Synthesis example of 1-88

Sub 1-4 (44.0 g, 80 mmol) and Sub 2-16 (29.6 g, 80 mmol) obtained the product (41.2 g, 68%) using the synthesis method of 1-13.

FD-MS values of the compounds 1-1 to 1-124 of the present invention synthesized in the same manner as in the synthesis example are shown in Table 3 below.

[Table 3]

[ Synthetic example 2] Formula 2

The compound represented by Formula 2 of the present invention (Final product 2) may be prepared by reacting Sub 3 and Sub 4 as shown in Reaction Scheme 4 below, but is not limited thereto.

<Reaction Scheme 4>

1. Exemplary compounds of Sub 3

Sub 3 of Reaction Scheme 4 may be synthesized as in Reaction Scheme 5 below, but is not limited thereto.

<Reaction Scheme 5>

The compounds belonging to Sub 3 of Scheme 4 are as follows, but are not limited thereto.

The FD-MS values of the compounds belonging to Sub 3 are shown in Table 4 below.

[Table 4]

2. Exemplary compounds of Sub 4 and Synthetic example

The FD-MS values of the compounds belonging to Sub 4 are shown in Table 5 below.

[Table 5]

<Scheme 6>

Sub 4-1 Synthetic example

Round bottom flask with aniline (15 g, 161.1 mmol), 1-bromonaphthalene (36.7 g, 177.2 mmol), Pd ₂ (dba) ₃ (7.37 g, 8.05 mmol), P(t-Bu) ₃ (3.26 g, 16.1 mmol), NaOt-Bu (51.08 g, 531.5 mmol), toluene (1690 mL) was added and the reaction proceeded at 100°C. After the reaction was completed, extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated to separate the produced organic material with a silica gel column and recrystallized to obtain 25.4 g of Sub 4-1. (Yield: 72%)

Sub 4-30 Synthetic example

Round bottom flask [1,1'-biphenyl]-4-amine (15 g, 88.6 mmol), 2-(4-bromophenyl)-9,9-diphenyl-9H-fluorene (46.2 g, 97.5 mmol), Pd ₂ (dba) ₃ (4.06 g, 4.43 mmol), P(t-Bu) ₃ (1.8 g, 8.86 mmol), NaOt-Bu (28.1 g, 292.5 mmol), toluene (931 mL), and Sub 4 By proceeding in the same manner as in the synthesis method of -1, Sub 4-30 was obtained 34.9 g. (Yield: 70%)

Sub 4-46 Synthetic example

Naphthalen-1-amine (15 g, 104.8 mmol), 2-bromodibenzo[b,d]thiophene (30.3 g, 115.2 mmol), Pd ₂ (dba) ₃ (4.8 g, 5.24 mmol), P( After adding t-Bu) ₃ (2.12 g, 10.48 mmol), NaOt-Bu (33.22 g, 345.7 mmol), toluene (1100 mL), proceed in the same way as in the synthesis method for Sub 4-1 to perform Sub 4-46. 24.9 g. (Yield: 73%)

Sub 4-49 Synthetic example

[1,1'-biphenyl]-4-amine (15 g, 88.64 mmol), 2-bromodibenzo[b,d]thiophene (23.32 g, 88.64 mmol), Pd ₂ (dba) ₃ (2.43 g) , 2.66 mmol), P(t-Bu) ₃ (17.93 g, 88.64 mmol), NaOt-Bu (17.04 g, 177.27 mmol), toluene (886 mL), and then in the same manner as in the synthesis method of Sub 4-1. Advances to obtain 24.61 g of Sub 4-49. (Yield: 79%)

Sub 4-56 Synthetic example

Round bottom flask with 4-(dibenzo[b,d]furan-2-yl)aniline (15 g, 57.85 mmol), 2-bromodibenzo[b,d]furan (15.7 g, 63.63 mmol), Pd ₂ (dba) Synthesis of Sub 4-1 after adding ₃ (2.65 g, 2.89 mmol), P(t-Bu) ₃ (1.17 g, 5.78 mmol), NaOt-Bu (18.35 g, 190.9 mmol), toluene (607 mL) Proceed in the same way to obtain Sub 4-56 17.2 g. (Yield: 70%)

3. Final compound Synthetic example

2- 1 of synthesis

Round bottom flask sub 3-1 (10 g, 42.9 mmol), Sub 4-21 (13.79 g, 42.9 mmol), Pd ₂ (dba) ₃ (1.18 g, 1.29 mmol), P(t-Bu) ₃ ( 8.68 g, 42.9 mmol), NaOt-Bu (8.25 g, 85.80 mmol) and toluene (429 mL) were added and then the reaction was carried out at 100°C. After the reaction was completed, the organic layer was extracted with CH ₂ Cl ₂ and water, dried over MgSO ₄ and concentrated, and the resulting organic material was separated by a silica gel column and recrystallized to obtain 15.6 g of product 2-1. (Yield: 77%)

2- 4 of synthesis

In a round bottom flask, Sub 3-2 (10 g, 35.3 mmol), Sub 4-27 (14.8 g, 35.31 mmol), Pd ₂ (dba) ₃ (0.97 g, 1.06 mmol), P(t-Bu) ₃ ( 7.14 g, 35.31 mmol), NaOt-Bu (6.79 g, 70.63 mmol), and toluene (353 mL) were added, followed by the same method as in the synthesis of 2-1 to obtain 16.9 g of product 2-4. (Yield: 78%)

Synthesis of 2-10

In a round bottom flask, Sub 3-6 (10 g, 32.34 mmol), Sub 4-12 (12.86 g, 32.34 mmol), Pd ₂ (dba) ₃ (0.89 g, 0.97 mmol), P(t-Bu) ₃ ( 6.54 g, 32.34 mmol), NaOt-Bu (6.22 g, 64.68 mmol) and toluene (323 mL) were added and then proceeded in the same manner as in the synthesis method of 2-1 to obtain 15.1 g of product 2-10. (Yield: 75%)

Synthesis of 2-19

In a round bottom flask, Sub 3-10 (10 g, 38 mmol), Sub 4-16 (11.23 g, 38 mmol), Pd ₂ (dba) ₃ (1.04 g, 1.14 mmol), P(t-Bu) ₃ ( 7.69 g, 38 mmol), NaOt-Bu (7.3 g, 76 mmol) and toluene (380 mL) were added and then proceeded in the same manner as in the synthesis method of 2-1 to obtain 13.7 g of product 2-19. (Yield: 76%)

Synthesis of 2-68

In a round bottom flask, Sub 3-38 (10 g, 33.65 mmol), Sub 4-49 (11.83 g, 33.65 mmol), Pd ₂ (dba) ₃ (0.92 g, 1.01 mmol), P(t-Bu) ₃ ( 6.81 g, 33.65 mmol), NaOt-Bu (6.47 g, 67.31 mmol), and toluene (337 mL) were added, followed by the same method as the synthesis method of 2-1 to obtain 15.28 g of product 2-68. (Yield: 80%)

2- 24 of synthesis

In a round bottom flask, Sub 3-10 (10 g, 38 mmol), Sub 4-33 (18.38 g, 38 mmol), Pd ₂ (dba) ₃ (1.04 g, 1.14 mmol), P(t-Bu) ₃ ( 7.69 g, 38 mmol), NaOt-Bu (7.3 g, 76 mmol) and toluene (380 mL) were added, followed by the same method as in the synthesis method of 2-1 to obtain 18.72 g of product. (Yield: 74%)

Synthesis of 2-29

In a round bottom flask, Sub 3-11 (10 g, 29.48 mmol), Sub 4-46 (9.59 g, 29.48 mmol), Pd ₂ (dba) ₃ (0.81 g, 0.88 mmol), P(t-Bu) ₃ ( 5.96 g, 29.48 mmol), NaOt-Bu (5.67 g, 58.95 mmol), and toluene (295 mL) were added, followed by the same method as in the synthesis method of 2-1 to obtain 12.39 g of product 2-29. (Yield: 72%)

Synthesis of 2-30

In a round bottom flask, Sub 3-14 (10 g, 29.48 mmol), Sub 4-20 (9.47 g, 29.48 mmol), Pd ₂ (dba) ₃ (0.81 g, 0.88 mmol), P(t-Bu) ₃ ( 5.96 g, 29.48 mmol), NaOt-Bu (5.67 g, 58.95 mmol) and toluene (295 mL) were added and then proceeded in the same manner as in the synthesis method of 2-1 to obtain 12.13 g of product 2-30. (Yield: 71%)

Synthesis of 2-36

In a round bottom flask, Sub 3-10 (10 g, 38 mmol), Sub 4-51 (14.5 g, 38 mmol), Pd ₂ (dba) ₃ (1.04 g, 1.14 mmol), P(t-Bu) ₃ ( 7.69 g, 38 mmol), NaOt-Bu (7.30 g, 76 mmol) and toluene (380 mL) were added and then proceeded in the same manner as in the synthesis method of 2-1 to obtain 16.5 g of product 2-36. (Yield: 77%)

Synthesis of 2-50

In a round bottom flask, Sub 3-40 (10 g, 30.94 mmol), Sub 4-21 (9.95 g, 30.94 mmol), Pd ₂ (dba) ₃ (0.85 g, 0.93 mmol), P(t-Bu) ₃ ( 6.26 g, 30.94 mmol), NaOt-Bu (5.95 g, 61.88 mmol) and toluene (309 mL) were added and then proceeded in the same manner as in the synthesis method of 2-1 to obtain 13.26 g of product 2-50. (Yield: 76%)

Synthesis of 2-52

In a round bottom flask, Sub 3-33 (10 g, 22.76 mmol), Sub 4-9 (7.86 g, 22.76 mmol), Pd ₂ (dba) ₃ (0.63 g, 0.68 mmol), P(t-Bu) ₃ ( 4.60 g, 22.76 mmol), NaOt-Bu (4.38 g, 45.52 mmol), and toluene (228 mL) were added, followed by the same method as the synthesis method of 2-1 to obtain 11.38 g of product 2-52. (Yield: 71%)

Synthesis of 2-60

In a round bottom flask, Sub 3-35 (10 g, 30.94 mmol), Sub 4-59 (10.94 g, 30.94 mmol), Pd ₂ (dba) ₃ (0.85 g, 0.93 mmol), P(t-Bu) ₃ ( 6.26 g, 30.94 mmol), NaOt-Bu (5.95 g, 61.88 mmol) and toluene (309 mL) were added and then proceeded in the same manner as in the synthesis method of 2-1 to obtain 13.46 g of product 2-60. (Yield: 73%)

Synthesis of 2-85

In a round bottom flask, Sub 3-49 (10 g, 21.21 mmol), Sub 4-21 (6.82 g, 21.21 mmol), Pd ₂ (dba) ₃ (0.58 g, 0.64 mmol), P(t-Bu) ₃ ( 4.29 g, 21.21 mmol), NaOt-Bu (4.08 g, 42.43 mmol) and toluene (212 mL) were added and then proceeded in the same manner as in the synthesis method of 2-1 to obtain 10.57 g of product 2-85. (Yield: 70%)

2- 89 of synthesis

In a round bottom flask, Sub 3-50 (10 g, 25.17 mmol), Sub 4-30 (14.14 g, 25.17 mmol), Pd ₂ (dba) ₃ (0.69 g, 0.76 mmol), P(t-Bu) ₃ ( After adding 5.09 g, 25.17 mmol), NaOt-Bu (4.84 g, 50.34 mmol), toluene (252 mL), and proceeding in the same manner as in the synthesis method of 2-1, 15.91 g of product 2-89 was obtained. (Yield: 72%)

The FD-MS values of compounds 2-1 to 2-96 prepared according to the above synthesis example are shown in Table 6 below.

[Table 6]

Manufacturing evaluation of organic electric devices

[ Example 1] to [ Example 90] Red organic light emitting device ( Emitting layer Mixed phosphorescent host)

A 60 nm thick hole is deposited by vacuum depositing a 4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter abbreviated as "2-TNATA") film on an ITO layer (anode) formed on a glass substrate. After forming the injection layer, a 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as "NPD") film was vacuum-deposited to a thickness of 55 nm to form a hole transport layer.

Next, a light emitting layer having a thickness of 30 nm was formed on the hole transport layer. At this time, as shown in Table 5 below, the compound represented by Chemical Formula 1 (first host) and the compound represented by Chemical Formula 2 of the present invention (second) The mixture of the host) in a weight ratio of 3:7 is used as a host, and bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate (hereinafter abbreviated as "(piq) ₂ Ir(acac)") is used as a dopant. The host and dopant were used in a 95:5 weight ratio.

Next, a hole blocking layer by vacuum-depositing (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as "BAlq") on the light emitting layer to a thickness of 10 nm Formed.

Subsequently, tris-(8-hydroxyquinoline)aluminum (hereinafter abbreviated as “Alq ₃ ”) and bis (10-hydroxybenzo[h]quinolinato)beryllium (hereinafter abbreviated as BeBq ₂ ) on the hole blocking layer 1:1. It was mixed to form a film with a thickness of 45 nm to form an electron transport layer. Subsequently, an organic electroluminescent device was manufactured by depositing LiF on the electron transport layer to a thickness of 0.2 nm, and then depositing Al on a thickness of 150 nm to form a cathode.

[Comparative Example 1] to [Comparative Example 4]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound represented by Formula 1 of the present invention was used alone as the host material of the light emitting layer.

[Comparative Example 5] and [Comparative Example 6]

An organic electroluminescent device in the same manner as in Example 1, except that a mixture of Comparative Compound 1 and Comparative Compound 2 and a mixture of Comparative Compound 1 and Comparative Compound 3 were used as the host material of the light emitting layer, as shown in Table 5 below. Was produced.

<Comparative Compound 1> <Comparative Compound 2> <Comparative Compound 3>

Electro-luminescence (EL) characteristics of the organic electroluminescent device manufactured by Examples 1 to 90 and Comparative Examples 1 to 6 of the present invention were applied to a PR-650 manufactured by Photoresearch by applying a direct bias DC voltage. The T95 lifespan was measured through the life measurement equipment of Mac Science at a reference luminance of 2500 cd/m ² , and the measurement results are shown in Table 7 below.

[Table 7]

As can be seen from the results of Table 7, when the compounds represented by Formula 1 and Formula 2 of the present invention are mixed and used as a phosphorescent host (Examples 1 to 90), the compounds represented by Formula 1 may be used alone ( It can be seen that the driving voltage, efficiency and lifespan of the device are significantly improved compared to Comparative Examples 1 to 4) or when the compounds are used in combination (Comparative Examples 5 to 6).

Comparing Comparative Examples 1 to 6, the properties of the device were further improved when the compounds of the present invention were used by mixing two types of comparative compounds (Comparative Examples 5 to 6) than when the compounds of the present invention were used alone (Comparative Examples 1 to 4). .

In addition, when comparing Examples 5 to 6 and Examples of the present invention, when using a host in which a compound according to Formula 1 and a compound according to Formula 2 of the present invention are mixed, rather than two kinds of comparative compounds, the driving voltage is It was lowered and efficiency and lifespan were significantly improved.

From the results, the inventors of the present invention determined that, in the case of a mixture of the substance of Formula 1 and the substance of Formula 2, it has novel characteristics other than those of each substance, and uses each of these substances and mixtures to PL The lifetime was measured. As a result, in the case of the mixture of the present invention formula 1 and formula 2, it was confirmed that a new PL wavelength was formed unlike the single compound.

When the compound of the present invention is used in combination, not only electrons and holes are moved through the energy level of each material, but also electrons and holes are moved by a new exciplex having a new energy level formed due to mixing. Or, it is judged that the efficiency and lifetime have increased due to energy transfer. This can be said to be an important example in which the mixed thin film shows an exciplex energy transfer and luminescence process when using the mixture of the present invention.

In addition, when a compound represented by Chemical Formula 2 having high hole characteristics is mixed with a polycyclic compound represented by Chemical Formula 1 having high stability against holes as well as a high T1 value, high T1 and high LUMO energy values Due to this, the electron blocking ability is improved, and more holes in the light emitting layer are moved quickly and easily. As described above, when the hole moves faster to the light emitting layer and the electron blocking ability is improved, the charge balance in the light emitting layer increases, so that the light emission is performed well inside the light emitting layer rather than the hole transport layer interface, thereby reducing the deterioration of the HTL interface, thereby reducing the entire device. The driving voltage, efficiency and lifetime are maximized. Accordingly, when a compound represented by Chemical Formula 1 and Chemical Formula 2 is used as a mixture, the overall performance of the device is greatly improved due to the electrochemical synergy effect.

[Example 91] to [Example 94]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the first host and the second host were mixed at a predetermined ratio as described in Table 7 below.

The electroluminescence (EL) characteristic was measured by PR-650 of photoresearch by applying a direct bias DC voltage to the organic electroluminescent devices manufactured in Examples 91 to 94 of the present invention, and based on 2500 cd/m ² The T95 life was measured at a luminance through a life measurement equipment of Max Science. The results are shown in Table 8 below. Example 3 and Example 80 is the result of measuring the device characteristics when the first host and the second host are mixed in a ratio of 3:7 as in Table 6.

[Table 8]

Referring to Table 8, it can be seen that when the first host and the second host are mixed at 3:7, the driving voltage, efficiency, and life are the best, and the device characteristics decrease as the ratio of the first host increases. have. This is because the charge balance in the light emitting layer is maximized as the amount of the compound represented by the formula (2), which has a relatively higher hole property than the compound represented by the formula (1), increases.

The above description is merely illustrative of the present invention, and those skilled in the art to which the present invention pertains will be capable of various modifications without departing from the essential characteristics of the present invention. Therefore, the embodiments disclosed herein 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 equivalent range should be interpreted as being included in the scope of the present invention.

100: organic electrical element 110: substrate
120: first electrode 130: hole injection layer
140: hole transport layer 141: buffer layer
150: light-emitting layer 151: light-emitting auxiliary layer
160: electron transport layer 170: electron injection layer
180: second electrode

Claims (11)

In the organic electrical device including a first electrode, a second electrode and an organic material layer formed between the first electrode and the second electrode,
The organic material layer includes a phosphorescent light-emitting layer, the host of the phosphorescent light-emitting layer is an organic electric device comprising a first compound represented by the following formula (1) and a second compound represented by the following formula (2):
<Formula 1><Formula2>

In the above formula,
X ₁ is O or S,
Ar ¹ , Ar ² , Ar ⁴ to Ar ⁶ are independently of each other C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; And C ₆ ~ C _{30 It} is selected from the group consisting of an aryloxy group,
L ¹ to L ⁶ are each independently a single bond; C ₆ ~ C ₆₀ Arylene group; Fluorylene group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; And combinations thereof,
R ¹ is hydrogen; heavy hydrogen; halogen; Cyano group; C ₆ ~ C ₆₀ Aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And -L'-N (R _a ) (R _b ); is selected from the group consisting of, R ¹ adjacent to each other may be bonded to each other to form a ring,
a is an integer from 0 to 9, and when a is an integer of 2 or more, each of the plurality of R ¹ is the same or different from each other,
L'is independently of each other a single bond; C ₆ ~ C ₆₀ Arylene group; Fluorylene group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; And combinations thereof,
R _a and R _b are independently of each other C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; And combinations thereof. According to claim 1,
An organic electrical device characterized in that the compound derived from the following Chemical Formula 1-1 in Chemical Formula 1 is excluded:
<Formula 1-1>

In Formula 1-1, L ¹ to L ³ , X ₁ , R ¹ , a are the same as defined in claim 1,
Ar ¹ and Ar ² are independently of each other C ₆ ~ C ₁₈ aryl group; Fluorenyl group; C ₂ ~ C ₁₆ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; And C ₆ ~ C _{30 It} is selected from the group consisting of an aryloxy group. According to claim 1,
The L ¹ to L ⁶ are each independently an organic electric device characterized in that one of the following formulas b-1 to b-13:
<Formula b-1><Formulab-2><Formulab-3><Formulab-4>

<Formula b-5><Formulab-6><Formulab-7><Formulab-8>

<Formula b-9><Formulab-10>

<Formula b-11><Formulab-12><Formulab-13>

In the above formula,
R ⁵ to R ⁷ are independently of each other hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; C ₃ ~ C ₂₀ aliphatic ring and C ₆ ~ C ₂₀ aromatic ring fused ring group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₂₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And -L ^a -N (R ^a ) (R ^b ); is selected from the group consisting of, adjacent groups may be bonded to each other to form a ring,
Y is N-(L ^a -Ar ^a ), O, S or C(R')(R"),
Z ¹ to Z ³ are each independently C, C(R') or N, and at least one of Z ¹ to Z ³ is N,
f is an integer from 0 to 6, e, g, h, and i are integers from 0 to 4, j, k are integers from 0 to 3, l is an integer from 0 to 2, and m is 0, respectively. And an integer of 3 to 3, each of which is an integer of 2 or more, each of a plurality of R ^5, each of a plurality of R ^6, each of a plurality of R ⁷ is the same or different from each other,
R'and R" are independently of each other hydrogen; deuterium; halogen; cyano group; nitro group; C ₆ ~ C ₂₀ aryl group; fluorenyl group; O, N, S, Si and at least one heteroatom of P C ₂ ~ C ₂₀ heterocyclic group containing; C ₃ ~ C ₂₀ aliphatic ring group; C ₃ ~ C ₂₀ aliphatic ring and C ₆ ~ C ₂₀ aromatic ring fused ring group; C ₁ ~ C ₂₀ Alkyl group of; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₂₀ alkoxy group; C ₆ ~ C ₃₀ aryloxy group; and -L ^a -N (R ^a ) (R ^b ); is selected from the group consisting of,
In C(R')(R"), R'and R" may combine with each other to form a ring, and in C(R'), adjacent R's may combine with each other to form a ring,
The Ar ^a is C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof,
L ^a is ^a single bond independently of each other; C ₆ ~ C ₂₀ Arylene group; Fluorylene group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof,
R ^a and R ^b are independently of each other C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof. According to claim 1,
The Formula 1 is an organic electric device characterized in that represented by one of the following Formula 1-A to Formula 1-E:
<Formula 1-A><Formula1-B>

<Formula 1-C><Formula1-D>

<Formula 1-E>

In the above formula,
Ar ¹ , Ar ² , L ¹ to L ³ , X ₁ , R ¹ , a are the same as defined in claim 1,
X ₂ and X ₃ are each independently O or S,
R ₄ , R ⁸ and R ⁹ are independently of each other hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; C ₃ ~ C ₂₀ aliphatic ring and C ₆ ~ C ₂₀ aromatic ring fused ring group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₂₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And -L ^a -N (R ^a ) (R ^b ); is selected from the group consisting of, adjacent groups may be bonded to each other to form a ring,
d1 is an integer from 0 to 7, i and j are integers from 0 to 6, and when each of them is an integer of 2 or more, each of a plurality of R _4, each of a plurality of R ^{8, and} each of a plurality of R ⁹ are the same or different from each other And
L ^a is ^a single bond independently of each other; C ₆ ~ C ₂₀ Arylene group; Fluorylene group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof,
R ^a and R ^b are independently of each other C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof. The method of claim 4,
The formula 1-A is an organic electric device characterized in that it can be represented by one of the following formula 1-A-1 to formula 1-A-6:
<Formula 1-A-1><Formula1-A-2><Formula1-A-3>

<Formula 1-A-4><Formula1-A-5><Formula1-A-6>

In the above formula, Ar ¹ , Ar ² , L ¹ ~L ³ , X ₁ , R ¹ , a are as defined in claim 4. According to claim 1,
The formula 2 is an organic electric device, characterized in that represented by one of the following formula 2-A to formula 2-C:
<Formula 2-A><Formula2-B>

<Formula 2-C>

In the above formula, Ar ⁵ , Ar ⁶ , L ⁴ ~L ⁶ is the same as defined in claim 1,
Y ₁ ~ Y ₃ are independently of each other O, S, C(R')(R"),
R ¹¹ to R ¹⁶ , R'and R" are independently of each other hydrogen; deuterium; halogen; C ₁ -C ₂₀ alkyl group or C ₆ -C ₂₀ aryl group unsubstituted or substituted silane group; cyano group; nitro group ; C ₁ -C ₂₀ alkoxy group; C ₆ -C ₂₀ aryloxy group; C ₁ -C ₂₀ alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C Aryl group of ₂₀ ; 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; and aliphatic ring of C ₃ -C ₂₀ Group; selected from the group consisting of, adjacent groups may combine with each other to form a ring,
b is an integer from 0 to 4, and when b is an integer of 2 or more, each of the plurality of R ^11, each of the plurality of R ^{13, and} each of the plurality of R ¹⁵ are the same or different from each other,
c is an integer of 0 to 3, and when c is an integer of 2 or more, each of the plurality of R ^12, each of the plurality of R ^{14, and} each of the plurality of R ¹⁶ are the same or different from each other. According to claim 1,
The formula 2 is an organic electric device, characterized in that represented by one of the following formula 2-D to formula 2-I:
<Formula 2-D><Formula2-E><Formula2-F>

<Formula 2-G><Formula2-H><Formula2-I>

<Formula 2-G><Formula2-H><Formula2-I>

In the above formula, Ar ⁵ , Ar ⁶ , L ⁴ ~L ⁶ is the same as defined in claim 1,
Y ₁ is independently of each other O, S, C(R')(R"),
R ¹¹ and R ¹² are independently of each other hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with an alkyl group of C ₁ -C ₂₀ or an aryl group of C ₆ -C ₂₀ ; Cyano group; Nitro group; C ₁ -C ₂₀ Alkoxy group; C ₆ -C ₂₀ Aryloxy group; C ₁ -C ₂₀ alkyl group; Alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ Aryl group; Fluorenyl group; A C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; And C ₃ -C ₂₀ Aliphatic ring group; It is selected from the group consisting of, adjacent groups may combine with each other to form a ring,
b is an integer from 0 to 4, and when b is an integer of 2 or more, each of the plurality of R ¹¹ is the same or different from each other,
c is an integer of 0 to 3, and when c is an integer of 2 or more, each of the plurality of R ^{12 s} are the same or different. According to claim 1,
The compound represented by Formula 1 is an organic electric device characterized in that one of the following compounds:

. According to claim 1,
The compound represented by Chemical Formula 2 is one of the following compounds:

. A display device comprising the organic electroluminescent device of claim 1; And
An electronic device comprising; a control unit for driving the display device. The method of claim 10,
The organic electric device is an electronic device characterized in that it is 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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