WO2020130378A1 - Compound for organic electric element, organic electric element using same, and electronic device comprising same - Google Patents

Abstract

The present invention provides an organic electric element and an electronic device comprising same, the organic electric element comprising:: a compound represented by chemical formula 1; a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, and an electronic device comprising the organic electrical element. As the compound represented by chemical formula 1 is included in the organic layer, the drive voltage of the organic electric element can be lowered and the luminous efficiency and life can be improved.

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 element, an organic electric element using the same, and an electronic device thereof.

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 made, and among them, development of a host material of a light emitting layer is further required.

An object of the present invention is to provide a compound capable of lowering the driving voltage of a device and improving the luminous efficiency and life of the device, an organic electrical 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 using the compound represented by the formula and an electronic device thereof.

By using the compound according to the embodiment of the present invention, the driving voltage of the device can be lowered, and the luminous efficiency and lifetime of the device can be greatly improved.

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

4 shows a chemical formula according to an aspect of the present invention.

[Description of codes]

100, 200, 300: organic electric element 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 improving layer 210: buffer layer

220: light-emitting auxiliary layer 320: the first hole injection layer

330: first hole transport layer 340: first light emitting 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 light emitting 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 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" used in the present invention means a substituted or unsubstituted fluorenyl group, and "fluorenylene group" means a substituted unsubstituted fluorenylene group unless otherwise specified. Unsubstituted fluorenyl group or unsubstituted fluorenylene group means 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 a 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 addition, the term "fluorenyl group" or "fluorenylene group" used in the present invention includes the case where R and R'are bonded to each other in the following structure to form a spy compound together with the carbon to which they are attached.

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 in the two rings are called'spyro atoms', and these are'monospyro-','dispiro-','trispyro' depending on the number of spy atoms in a compound, respectively. 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. Further, instead of carbon forming a ring, a compound containing a heteroatom group such as SO ₂ , P=O, etc. may also be included in the heterocyclic group.

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 indicated in the present specification, when indicating a condensed ring, the number in the'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, and benzoquinazoline, may be represented by a 3-condensed ring.

In addition, unless otherwise described herein, when the ring is expressed in the form of a'numeric resource' such as a 5-membered ring or a 6-membered ring, the number in the'number-atom' represents the number of elements forming the ring. For example, thiophene or furan may correspond to a 5-atom ring, and benzene or pyridine may correspond to a 6-atom ring.

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

At this time, unless otherwise described herein,'neighborhood between each other' is, for example, the following formula, R ₁ and R ₂ between, R ₂ and R ₃ between, R ₃ and R ₄ between, R ₅ and R ₆ , as well as R ₇ and R _8, which share one carbon, include R ₁ and R ₇ , R ₁ and R _8, or R ₄ and R _{5, which} are not immediately adjacent. Substituents bound to ring constituent elements (such as carbon or nitrogen) may also be included. That is, if there are substituents on a ring constituent element such as carbon or nitrogen immediately adjacent to each other, they may be adjacent groups, but if no substituents are attached to the ring constituent element of the immediately adjacent position, it is bound to the next ring constituent element. The substituted groups may be adjacent groups, and the substituents bonded to the same ring-constituting carbon may also be referred to as adjacent groups.

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

,

In addition, in the present specification, the expression'neighborhood groups may combine with each other to form a ring' is used in the same sense as'neighborhood groups combined with each other to selectively form a ring', and at least a pair of It means the case where adjacent groups combine with each other to form a ring.

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

It should be noted that in adding reference numerals to the components of each drawing, the same components have the same reference numerals as possible even though they are displayed on different drawings. In addition, in describing the present invention, when it is determined that detailed descriptions of related well-known structures or functions may obscure the subject matter of the present invention, detailed descriptions thereof will be omitted.

In describing the components of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are only for distinguishing 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, the component may be directly connected to or connected to the other component, but another component between each component It should be understood that the element may be "connected", "coupled" or "connected".

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

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

The first electrode 110 may be an anode (anode), the second electrode 170 may be a cathode (cathode), and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

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

Preferably, the light efficiency improving layer 180 may be formed on one surface of the first electrode 110 or the second electrode 170 that does not contact the organic material layer, and when the light efficiency improving layer 180 is formed The light efficiency of the organic electric device can be improved.

For example, the light efficiency improving layer 180 may be formed on the second electrode 170. In the case of a top emission organic light emitting device, the second electrode 170 is formed by forming the light efficiency improving layer 180. ) Can reduce optical energy loss due to SPPs (surface plasmon polaritons), and in the case of a bottom emission organic light emitting device, the light efficiency improving layer 180 serves as a buffer for the second electrode 170 can do.

A buffer layer or an auxiliary light emitting layer may be further formed between the hole transport layer 130 and the light emitting layer 140, which will be described with reference to FIG. 2.

Referring to FIG. 2, the organic electric device 200 according to another embodiment of the present invention includes a hole injection layer 120, a hole transport layer 130, and 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, may include an electron injection layer 160, a second electrode 170, the light efficiency improving layer 180 is formed on the second electrode Can be.

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

Further, 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, a light emitting layer, and an electron transport layer are formed. This will be described with reference to FIG. 3.

Referring to FIG. 3, the organic electrical device 300 according to another embodiment of the present invention includes two stacks of organic material layers (ST1, ST2) formed of a multilayer between the first electrode 110 and the second electrode 170. More than one set may be formed, and a charge generating layer (CGL) may be formed between stacks of organic material layers.

Specifically, the organic electric device according to an 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 improving layer 180.

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 light emitting 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 lamination structure, but may also be organic material layers of different lamination 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 generating layer CGL is formed between the first light emitting layer 340 and the second light emitting layer 440 to increase the current efficiency generated in each light emitting layer, and serves to distribute charges smoothly.

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

In FIG. 3, n may be an integer from 1 to 5, and when n is 2, a charge generating layer CGL and a third stack may be additionally stacked on the second stack ST2.

When a plurality of light-emitting layers are formed by a multi-layer stack structure as shown in FIG. 3, it is possible not only to manufacture an organic electroluminescent device in which white light is emitted by the mixing effect of light emitted from each light-emitting layer, but also to produce 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 emitting 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 of the light efficiency improving layer 180, but preferably the light emitting layer (140, 340, 440) and / or light efficiency improving layer It can be used as a material of (180).

Since the band gap, electrical properties, and interfacial properties may vary depending on which substituents are attached to which positions even in the same core, research on the selection of the core and the combination of sub-substituents coupled thereto In particular, it is possible to achieve long life and high efficiency 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 the formula (1) as the material of the light emitting layer (140, 340, 440) and / or light efficiency improving layer 180, the energy level and T ₁ value between each organic layer, the unique properties of the material ( Mobility, interfacial characteristics, 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 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, can be prepared by depositing a material that can be used as the cathode 170 thereon have. In addition, an electron transport auxiliary layer 220 (not shown) may be further formed between the hole transport layer 130 and the light emitting layer 140 and the electron transport auxiliary layer (not shown) between the light emitting layer 140 and the electron transport layer 150. It can also be formed as a stack structure.

In addition, the organic material layer is a solution process or a solvent process (e.g., spin coating process), nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor blade using various polymer materials It can be produced with fewer layers by a method such as a ding process, a screen printing process, or a thermal transfer method. 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, a compound according to an aspect of the present invention will be described.

The compound according to an aspect of the present invention is represented by Formula 1 below.

<Formula 1> <Formula 1-A>

In the above formula, each symbol can be defined as follows.

R ¹ to R ⁴ are independently of each other hydrogen; heavy hydrogen; halogen; 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 ₁ ~ C ₃₀ alkyl group; C ₂ ~ C ₃₀ alkenyl group; C ₂ ~ C ₃₀ 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. However, at least one pair of neighboring R ¹ , neighboring R ² , and neighboring R ^{3 may} be bonded to each other to form a ring represented by Chemical Formula 1-A. At this time, * in Formula 1-A represents a position bonded to Formula 1, and * in Formula 1-A is preferably bonded to the carbon of the neighboring * portion in Formula 1 below.

In addition, since at least one pair of neighboring R ¹ , neighboring R ² , and neighboring R ³ is bound to each other to form a ring represented by Formula 1-A, neighboring R ¹ and neighboring R ² , When two pairs of neighboring R ³ are bonded to each other to form a ring, both rings may be of Formula 1-A, one of Formula 1-A, and the other may be an aromatic ring.

<Formula 1>

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

When adjacent groups are combined with each other to form an aromatic ring, preferably an aromatic ring of C ₆ to C ₂₀ , more preferably an aromatic ring of C ₆ to C ₁₄ , such as benzene, naphthalene, phenanthrene, or the like , May form a ring containing a benzene moiety.

a, c and d are each integers of 0 to 4, b is an integer of 0 to 5, and when each of them is an integer of 2 or more, each of a plurality of R ^1, each of a plurality of R ^2, each of a plurality of R ³ , a plurality of R ⁴ Each is the same or different.

When R ¹ to R ⁴ are an aryl group, preferably an aryl group of C ₆ to C ₃₀ , more preferably a C ₆ to C ₁₈ aryl group, such as phenyl, naphthyl, biphenyl, terphenyl, and the like.

When R ¹ to R ⁴ are heterocyclic groups, preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₁₈ heterocyclic groups, such as pyridine, pyrimidine, triazine, carbazole, It may be phenyl-carbazole, quinoline, isoquinoline, quinazoline, benzoquinazoline, dibenzothiophene, dibenzofuran, benzothienopyrimidine, and the like.

When R ¹ to R ⁴ are alkenyl groups, preferably C ₂ to C ₁₀ alkenyl groups, such as ethene and propene.

X is N-(L-Ar ¹ ), O, S or C(R')(R").

Ar ¹ is a 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; And C ₃ ~ C ₆₀ It may be selected from the group consisting of an aliphatic ring group.

When Ar 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, biphenyl, naphthyl, terphenyl, phenanthrene, triphenylene , Pyrene, and the like.

When Ar ¹ is a heterocyclic group, preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₁₈ heterocyclic group, for example, imidazole, pyridine, pyrimidine, triazine, tetra Gin, dibenzofuran, dibenzothiophene, benzonaphthofuran, benzonaphthothiophene, carbazole, phenylcarbazole, quinazoline, benzoquinazoline, dibenzoquinazoline, quinoxaline, benzoquinoxaline, quinoline, Isoquinoline, pyridopyrimidine, benzothienopyrimidine, benzofuropyrimidine, benzoindenopyrimidine, naphthofuropyrimidine, naphthothienopyrimidine, indolopyrimidine, phenylindolopyri It may be midine, benzothienopyridine, thiarene, indolocarbazole, and the like.

When Ar ¹ is a fluorenyl group, it may be 9,9-dimethyl-9 H -fluorene, 9,9-diphenyl-9 H -fluorene, 9,9'-spirobifluorene, and the like.

L and L'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 and L'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, naphthalene, biphenyl, and the like.

When L and L'are heterocyclic groups, it is preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₁₈ heterocyclic group, for example, imidazole, pyridine, pyrimidine , Triazine, tetrazine, quinazoline, benzoquinazoline, dibenzoquinazoline, quinoxaline, benzoquinoxaline, isoquinoline, benzothienopyrimidine, benzofuropyrimidine, benzoindenopyrimidine, benzothiazole It may be enopyridine, naphthofuropyrimidine, naphthocyenopyrimidine, pyridopyrimidine, and the like.

R _a and R _b are independently of each other C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; And C ₂ to C ₆₀ heterocyclic groups including at least one hetero atom among O, N, S, Si, and P.

R'and R" are independently of each other hydrogen; deuterium; halogen; C ₆ ~ C ₆₀ aryl group; fluorenyl group; C ₂ ~ containing at least one hetero atom of O, N, S, Si and P a heterocyclic group of C _60; C ₃ ~ C ₆₀ alicyclic group; C ₁ ~ C ₃₀ alkyl; C ₂ ~ C ₃₀ alkenyl group a; C ₂ ~ C ₃₀ alkynyl of; of C ₁ ~ C ₃₀ alkoxy group; and C ~ ₆ is selected from the group consisting of an aryloxy group of C _30, may bond to one another to form a ring together R 'and R ".

When R'and R" are alkyl groups, they may preferably be C ₁ to C ₁₀ alkyl groups, such as methyl, propyl, and the like.

When R'and R" are aryl groups, it may be preferably an aryl group of C ₆ to C ₃₀ , more preferably an aryl group of C ₆ to C ₁₈ , such as phenyl, biphenyl, naphthyl, terphenyl, and the like.

The R ¹ ~ R ⁴ , L, L', Ar ¹ , R _a , R _b , R', R", a ring formed by combining adjacent groups with each other, and a ring formed by combining R'and R" with each other 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; Phosphine oxide unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio; C ₁ -C ₂₀ Alkoxy group; C ₆ -C ₂₀ Arylalkoxy 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; C ₃ -C ₂₀ aliphatic ring group; C ₇ -C ₂₀ Arylalkyl group; C ₈ -C ₂₀ Arylalkenyl group; -L'-N(R _a )(R _b ); And one or more substituents selected from the group consisting of and combinations thereof. Where L', R _a and R _b are as defined above.

The Chemical Formula 1 may be represented by one of the following Chemical Formulas 2 to 5.

<Formula 2> <Formula 3>

<Formula 4> <Formula 5>

In the ^{formula, R 1 ~ R 4, X} , a ~ d is were the same as those defined in Formula ^{1, R 1 '~ R 3} ' is the same as the definition of R ¹ ~ R ⁴ as defined in formula (I), respectively, a 'And c'are each an integer from 0 to 2, and b'is an integer from 0 to 3.

<Formula 1-1>

In Chemical Formula 1-1, R ¹ to R ⁴ , Ar ¹ , L, a, b, and d are the same as defined in Chemical Formula 1, and c is an integer of 0 to 2.

Preferably, R ¹ to R ⁴ are independently of each other hydrogen; heavy hydrogen; halogen; 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 ₁ ~ C ₃₀ 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. Where L', R _a and R _b are as defined in Formula 1.

The Chemical Formula 1-1 may be represented by one of the following Chemical Formulas 1-1-A to 1-1-F.

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

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

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

In Formula 1-1-A to Formula 1-1-F, R ¹ to R ⁴ , L, Ar ¹ , and a to d are as defined in Formula 1-1.

Specifically, 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 electric device including 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 is represented by Chemical Formula 1 It includes one single compound or two or more compounds.

The organic material layer includes at least one layer of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer, preferably the compound is included in the light emitting layer, more preferably It is used as a host material for the light emitting layer.

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

Hereinafter, examples of the synthesis of the compound represented by Chemical Formula 1 according to the present invention and the manufacturing example 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

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

<Scheme 1>

(Y is independently of each other Cl, Br or I, n', m', o'are each an integer of 0-2, n'+m'+o'≥1, n, m, o are 0-2 And n+m+o≥1, provided that m'is 1 and n', o'is 0, the synthesis of the final compound can be obtained through the synthesis of Sub1.)

I. Synthesis Example of Sub 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>

1. Sub1-1 Synthesis Example

(1) Sub 1b-1 synthesis

Sub 1a-1 (20 g, 67.5 mmol) to Sub1a'-1 (25.9 g, 135.1 mmol), Cu powder (5.1 g, 81.0 mmol), K ₂ CO ₃ (56.0 g, 405.2 mmol), 18-Crown- 6 (2.1 g, 8.1 mmol), nitrobenzene (135 ml) was added and refluxed for 12 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature and nitrobenzene is removed. Extracted with methyl chloride and washed with water. Thereafter, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was separated by a silica gel column to obtain 21 g of product (yield: 76.5%).

(2) Sub 1-1 synthesis

Pd(OAc) ₂ (0.29 g, 1.29 mmol), P(t-Bu) ₃ (0.52 g, 2.58 mmol), K ₂ CO ₃ (41.0 g, 155.0 mmol) to Sub1b-1 (21 g, 51.7 mmol) , DMA (103 ml) was added and refluxed at 170°C for 12 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with methyl chloride, 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 16.8 g of product (yield: 88%).

2. Sub 1-9 Synthesis Example

(1) Sub 1a-9 synthesis

Sub 1'a-9 (30 g, 71.1 mmol) was dissolved in THF (355 ml), then Sub 1" (25.3 g, 71.1 mmol), Pd(PPh ₃ ) ₄ (4.9 g, 4.3 mmol), NaOH ( 8.5 g, 213.2 mmol), water (178 ml) is added and the reaction proceeds at 80° C. When the reaction is complete, the mixture is extracted with CH ₂ Cl ₂ and water, and the organic layer is dried over MgSO ₄ and concentrated. After separation by silica gel column and recrystallization to give the product 35.4 g (yield: 82.0%).

(2) Sub 1b-9 synthesis

Sub 1a-9 (35.4 g, 58.4 mmol) to Sub1a'-9 (28.2 g, 116.7 mmol), Cu powder (4.5 g, 70.0 mmol), K ₂ CO ₃ (48.4 g, 350.2 mmol), 18-Crown- 6 (1.9 g, 7.0 mmol), nitrobenzene (117 ml) was added, and then proceeded in the same manner as the synthesis method of Sub 1b-1 to obtain 33.8 g of product (yield: 75.6%).

(2) Sub 1-9 synthesis

Pd(OAc) ₂ (0.25 g, 1.10 mmol), P(t-Bu) ₃ (0.45 g, 2.21 mmol), K ₂ CO ₃ (35.0 g, 132.4 mmol) to Sub1b-9 (33.8 g, 44.1 mmol) , DMA (55 ml) was added, and then proceeded in the same manner as the synthesis method of Sub 1-1 to obtain 26.2 g (yield: 81.4%) of the product.

3. Sub 1-29 Synthesis Example

(1) Sub 1b-29 synthesis

Sub 1a-29 (20 g, 67.5 mmol) to Sub1a'-29 (38.0 g, 135.1 mmol), Cu powder (5.1 g, 81.0 mmol), K ₂ CO ₃ (56.0 g, 405.2 mmol), 18-Crown- 6 (2.1 g, 8.1 mmol), nitrobenzene (135 ml) was added, and then proceeded in the same manner as the synthesis method of Sub 1b-1 to obtain 26.2 g of product (yield: 78.1%).

(2) Sub 1-29 synthesis

P1(OAc) ₂ (0.30 g, 1.32 mmol), P(t-Bu) ₃ (0.53 g, 2.64 mmol), K ₂ CO ₃ (41.8 g, 158.2 mmol) to Sub1b-29 (26.2 g, 52.7 mmol) , DMA (105 ml) was added, and then proceeded in the same manner as the synthesis method of Sub 1-1 to obtain 19.4 g (yield: 79.9%) of the product.

4. Sub 1-31 Synthesis Example

(1) Sub 1b-31 synthesis

Sub 1a-31 (20 g, 47.4 mmol) to Sub1a'-31 (26.7 g, 94.8 mmol), Cu powder (3.6 g, 56.9 mmol), K ₂ CO ₃ (39.3 g, 284.3 mmol), 18-Crown- 6 (1.5 g, 5.7 mmol), nitrobenzene (95 ml) was added, and then proceeded in the same manner as the synthesis method of Sub 1b-1 to obtain 22.6 g of product (yield: 76.5%).

(2) Sub 1-31 synthesis

P1(OAc) ₂ (0.20 g, 0.91 mmol), P(t-Bu) ₃ (0.37 g, 1.81 mmol), K ₂ CO ₃ (28.7 g, 108.8 mmol) to Sub1b-31 (22.6 g, 36.3 mmol) , DMA (73 ml) was added, and then proceeded in the same manner as the synthesis method of Sub 1-1 to obtain 16.4 g (yield: 77.2%) of the product.

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

[Table 1]

II. Synthesis example of Sub 2

Compounds belonging to Sub 2 of Scheme 1 are as follows, and FD-MS values of the following compounds are shown in Table 2.

[Table 2]

III. Synthesis Example of Final Compound

1. Synthesis of P-5

(1) P-5a synthesis

Sub 1-3 (10 g, 16.6 mmol) was dissolved in THF (83 ml), Sub 2-8 (3.0 g, 16.6 mmol), Pd(PPh ₃ ) ₄ (1.2 g, 1.0 mmol), NaOH (2.0 g, 49.9 mmol), water (42 ml) was added and the reaction was allowed to proceed at 80°C. When the reaction is completed, the mixture is extracted with CH ₂ Cl ₂ and water, and the organic layer is dried over MgSO ₄ and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 8.9 g (yield: 75.3%) of the product.

(2) P-5 synthesis

After dissolving P-5a (8.2 g, 12.5 mmol) in THF (600 ml), Mehtylmagnesium bromide 1.0 M in THF (25 ml) was titrated and reacted at room temperature. Then, add acetic acid (70 ml), HCl (1 ml) and stir at room temperature for 24 hours, add water and pyridine (5:1) and reflux for 30 minutes. After the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 5.7 g of product. (Yield: 71.8%)

2. Synthesis Example of P-9

(1) P-9a synthesis

Sub 1-1 (10 g, 27.0 mmol) was dissolved in THF (135 ml), Sub 2-1 (4.5 g, 27.0 mmol), Pd(PPh ₃ ) ₄ (1.9 g, 1.62 mmol), NaOH (3.2 g, 81.0 mmol), water (68 ml) was added and the same method as for the synthesis of P-5a was carried out to obtain 9.0 g of product (yield: 81.2%).

(2) P-9b synthesis

Triphenylphosphine oxide (14.3 g, 54.6 mmol) and o-DCB (109 ml) were added to P-9a (9.0 g, 21.8 mmol) and refluxed at 240° C. for 12 hours. Upon completion of the reaction, the temperature of the intermediate product was cooled to room temperature and concentrated. after. The concentrated organic material was separated by a silica gel column to obtain 6.9 g of product (yield: 83.5%).

(3) P-9 synthesis

E-1 (4.4 g, 18.1 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.54 mmol), t -BuONa (3.5 g, 36.3 mmol), P( t -bu) ₃ (0.2 g, 1.09 mmol) and toluene (91 ml) were added and refluxed for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with methyl chloride, 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 8.3 g of product (yield: 78.2%).

3. Synthesis of P-20

(1) P-20a synthesis

Sub 1-9 (20 g, 27.4 mmol) was dissolved in THF (137 ml), Sub 2-5 (3.8 g, 27.4 mmol), Pd(PPh ₃ ) ₄ (1.9 g, 1.6 mmol), NaOH (3.3 g, 82.1 mmol), water (68 ml) was added and proceeded in the same manner as in the synthesis method of P-5a to obtain 15.6 g (yield: 76.8%) of the product.

(2) P-20 synthesis

After dissolving P-20a (15.6 g, 21.0 mmol) in C ₆ F ₆ (31 ml) and DMI (21 ml), Pd(OAc) ₂ (0.3 g, 1.1 mmol), 3-nitropyridine (0.1 g, 1.1 mmol) and tert- butyl peroxybenzoate (8.2 g, 42.0 mmol) are added in sequence and the reaction is allowed to proceed at 90°C. When the reaction is completed, the mixture is extracted with CH ₂ Cl ₂ and water, and the organic layer is dried over MgSO ₄ and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 9.8 g of product (yield: 62.7%).

4. Synthesis of P-31

(1) Synthesis of P-31a

Sub 2-4 (15.8 g, 124.2 mmol), Pd ₂ (dba) ₃ (1.7 g, 1.9 mmol), 50% P( t -Bu) ₃ (1.5 ml) to Sub 1-22 (23 g, 62.1 mmol) , 3.7 mol), NaO t -Bu (12 g, 124.2 mol) was added to toluene (311 ml) and stirred at 100°C. When the reaction is completed, the mixture is extracted with CH ₂ Cl ₂ and water, and the organic layer is dried over MgSO ₄ and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 22 g of product (yield: 85.0%).

(2) P-31b synthesis

P-31a (22 g, 52.8 mmol) to Pd(OAc) ₂ (0.2 g, 1.6 mmol), P(t-Bu) ₃ (0.9 g, 3.2 mmol), K ₂ CO ₃ (21.9 g, 158.3 mmol) , DMA (264 ml) was added and refluxed at 170°C for 12 hours. When the reaction is over, the temperature of the reactant is cooled to room temperature, extracted with MC 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 15.1 g of product (yield: 75.0%).

(3) P-31 synthesis

P-31b (15.1 g, 39.7 mmol) to E-2 (13.8 g, 39.7 mmol), Pd ₂ (dba) ₃ (1.1 g, 1.2 mmol), t -BuONa (7.6 g, 79.4 mmol), P( t -bu) ₃ (0.48 g, 2.4 mmol), toluene (198 ml) was added, and then proceeded in the same manner as the synthesis method of P-9 to obtain 28.0 g (yield: 72.5%) of the product.

5. P-90 synthesis

(1) P-90a synthesis

Sub 1-32 (20 g, 40.3 mmol) was dissolved in THF (202 ml), Sub 2-7 (7.4 g, 40.3 mmol), Pd(PPh ₃ ) ₄ (2.8 g, 2.4 mmol), NaOH (4.8 g, 120.9 mmol), water (101 ml) was added, and the same method as for the synthesis of P-5a was carried out to obtain 11.5 g of product (yield: 81.3%).

(2) Synthesis of P-90b

P-90a (11.5 g, 32.8 mmol) was added with an excess of trifluoromethane-sulfonic acid, stirred at room temperature for 24 hours, water and pyridine (8:1) were added and refluxed for 30 minutes. After cooling to room temperature, extract with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was separated by a silica gel column and recrystallized to obtain 13.8 g of product (yield: 88.2%).

(3) P-90c synthesis

After dissolving P-90b (13.8 g, 29.0 mmol) with THF (145 ml), Sub 2-9 (8.8 g, 29.0 mmol), Pd(PPh ₃ ) ₄ (2.0 g, 1.7 mmol), NaOH (3.5 g , 86.9 mmol), and water (72 ml) were added and proceeded in the same manner as in the synthesis method of P-5a to obtain 13.9 g (yield: 73.1%) of the product.

(4) P-90 synthesis

Add acetic acid (53 mL) and sulfuric acid (8 mL) to P-90c (13.9 g, 21.2 mmol) and stir at 120°C for 12 hours. After the reaction is completed, the mixture is extracted with CH ₂ Cl ₂ and water, and the organic layer is dried over MgSO ₄ and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 4.1 g of product (yield: 30.6).

The FD-MS values of the compounds P-1 to P-100 of the present invention prepared according to the above synthesis examples are shown in Table 3 below.

[Table 3]

Manufacturing evaluation of organic electric devices

[Example 1] Red organic electroluminescent device (host)

N ¹ -(naphthalen-2-yl)-N ⁴ ,N ⁴ -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N ¹ -phenylbenzene on ITO layer (anode) formed on glass substrate After forming a hole injection layer by vacuum deposition of -1,4-diamine (hereinafter abbreviated as "2-TNATA") to a thickness of 60 nm, 4,4-bis[N-(1) on the hole injection layer. -Naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as "NPB") was vacuum-deposited to a thickness of 60 nm to form a hole transport layer.

Then, on the hole transport layer, dopant the compound P-9 of the present invention as a host material, bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate (hereinafter abbreviated as "(piq) ₂ Ir(acac)"). It was used as a material, but a dopant was doped so that the weight ratio was 95:5, and a 30 nm-thick light emitting layer was deposited.

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 Was formed, and a tris (8-quinolinol) aluminum (hereinafter abbreviated as 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 on the electron transport layer to a thickness of 0.2 nm 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 20]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound of the present invention shown in Table 4 below was used instead of the compound P-9 as the host material of the light emitting layer.

[Comparative Example 1]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound A was used instead of Compound P-9 of the present invention as a host material for the light emitting layer.

<Comparative Compound A>

Electroluminescence (EL) characteristics were measured with PR-650 of photoresearch by applying a direct bias DC voltage to the organic electroluminescent devices manufactured by Examples 1 to 20 and Comparative Example 1 of the present invention, 2500 cd T95 lifespan was measured using the life measurement equipment of Max Science at /m ² standard luminance. The measurement results are shown in Table 4 below.

[Table 4]

As can be seen from the results of Table 4, when the material for an organic electroluminescent device of the present invention is used as a phosphorescent host, the driving voltage of the organic electroluminescent device can be lowered as well as the luminous efficiency compared to Comparative Example 1 using Comparative Compound A. It can significantly improve the life span.

Comparative Compound A and the compound of the present invention are identical in that they contain a benzo[mn]indolo[3,2,1-de]acridine moiety, but the compound of the present invention is additionally condensed with indole, indene, benzothiophene, and benzofuran There is a difference in that there is.

As described above, since the compound of the present invention is structurally different from Comparative Compound A, chemical and physical properties such as HOMO, LUMO, T1, charge balance of holes and electrons, hole mobility, and electron mobility are significantly different, and accordingly, the present invention When the organic electroluminescent device was manufactured using the compound of, the driving voltage, luminous efficiency and lifespan were significantly improved.

Above, the present invention has been exemplarily described, and those having ordinary knowledge in the technical field to which the present invention pertains will be capable of various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed herein are not intended to limit the present invention, but to 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 equivalent range should be interpreted as being included in the scope of the present invention.

CROSS-REFERENCE TO RELATED APPLICATION

This patent application is filed in US Patent Law 119 for patent application No. 10-2018-0164779 filed in Korea on December 19, 2018 and patent application No. 10-2019-0150771 filed in Korea on November 21, 2019. Priority is claimed pursuant to Articles 121 to 365 (35 USC §19 to §121, §365), all of which are incorporated herein by reference. In addition, if this patent application claims priority for the same reasons as above for countries other than the United States, all of the contents are incorporated into this patent application as a reference.

Claims (13)

1. Compound represented by the formula (1):

   <Formula 1> <Formula 1-A>

   

   

   In the above formula,

   R ¹ to R ⁴ are independently of each other hydrogen; heavy hydrogen; halogen; 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 ₁ ~ C ₃₀ alkyl group; C ₂ ~ C ₃₀ alkenyl group; C ₂ ~ C ₃₀ 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,

   However, at least one pair of neighboring R ¹ , neighboring R ² , and neighboring R ³ may combine with each other to form a ring represented by Formula 1-A, and * in Formula 1-A is bonded to Formula 1 Indicates the location,

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

   X is N-(L-Ar ¹ ), O, S or C(R')(R"),

   Ar ¹ is a 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; And C ₃ ~ C _{60 It} is selected from the group consisting of an aliphatic ring group,

   L and L'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 _a and R _b are independently of each other C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused 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,

   R'and R" are independently of each other hydrogen; deuterium; halogen; C ₆ ~ C ₆₀ aryl group; fluorenyl group; C ₂ ~ containing at least one hetero atom of O, N, S, Si and P a heterocyclic group of C _60; C ₃ ~ C ₆₀ alicyclic group; C ₁ ~ C ₃₀ alkyl; C ₂ ~ C ₃₀ alkenyl group a; C ₂ ~ C ₃₀ alkynyl of; of C ₁ ~ C ₃₀ alkoxy group; and C ~ ₆ is selected from the group consisting of an aryloxy group of C _30, R 'and R "together may bond to one another to form a ring,

   The R ¹ ~ R ⁴ , L, L', Ar ¹ , R _a , R _b , R', R", a ring formed by combining adjacent groups with each other, and a ring formed by combining R'and R" with each other 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; Phosphine oxide unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio; C ₁ -C ₂₀ Alkoxy group; C ₆ -C ₂₀ Arylalkoxy 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; C ₃ -C ₂₀ aliphatic ring group; C ₇ -C ₂₀ Arylalkyl group; C ₈ -C ₂₀ Arylalkenyl group; -L'-N(R _a )(R _b ); And it may be further substituted with one or more substituents selected from the group consisting of.
2. According to claim 1,

   Formula 1 is a compound characterized in that represented by one of the following formulas 2 to 5:

   <Formula 2> <Formula 3>

   

   <Formula 4> <Formula 5>

   

   Was in the ^{formula, R 1 ~ R 4, X} , a ~ d are the same as defined in claim 1, R ^{1 '~} R ^3' is the same as the definition of R ¹ ~ R ⁴ defined in claim 1, wherein each , a'and c'are each an integer from 0 to 2, and b'is an integer from 0 to 3.
3. According to claim 1,

   Chemical Formula 1 is a compound characterized in that represented by the following Chemical Formula 1-1:

   <Formula 1-1>

   

   In Chemical Formula 1-1,

   R ¹ to R ⁴ are independently of each other hydrogen; heavy hydrogen; halogen; 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 ₁ ~ C ₃₀ 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,

   c is an integer from 0 to 2,

   Ar ¹ , L, a, b, d, L', R _a and R _b are as defined in claim 1.
4. According to claim 3,

   Formula 1-1 is a compound characterized in that represented by one of the following formula 1-1-A to formula 1-1-F:

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

   

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

   

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

   

   In the above formula, R ¹ to R ⁴ , L, Ar ¹ , a to d are as defined in claim 3.
5. According to claim 1,

   Compounds characterized in that at least two pairs of neighboring R ¹ , neighboring R ² , and neighboring R ³ are bonded to each other to form a ring represented by Formula 1-A.
6. According to claim 1,

   The compound represented by Formula 1 is one of the following compounds:

   

   

   

   

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

   The organic layer is an organic electrical device comprising a compound represented by the formula (1) of claim 1.
8. In the organic electric device comprising an anode, a cathode, an organic material layer formed between the anode and the cathode, and a light efficiency improving layer,

   The light efficiency improving layer is formed on one surface of the anode or cathode that does not contact the organic material layer,

   The organic material layer or the light efficiency improving layer comprises an organic electroluminescent device comprising a compound represented by the formula (1) of claim 1.
9. The method of claim 7 or 8,

   The compound is an organic electric device, characterized in that included in the light emitting layer of the organic layer.
10. The method of claim 7 or 8,

    The organic material layer comprises two or more stacks including a hole transport layer, a light emitting layer and an electron transport layer sequentially formed on the anode.
11. The method of claim 10,

    The organic material layer further comprises a charge generation layer formed between the two or more stacks.
12. A display device comprising the organic electroluminescent element of claim 7 or 8; And

    An electronic device comprising; a control unit for driving the display device.
13. The method of claim 12,

    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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