KR102800166B1 - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention provides a novel compound capable of improving the luminous efficiency, stability and lifespan of a device, and an organic electric device and an electronic device using the same.

Description

COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF

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

In general, the organic luminescence phenomenon refers to a phenomenon that converts electrical energy into light energy using organic materials. An organic electric device utilizing the organic luminescence phenomenon usually has a structure including an anode, a cathode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic electric device, and can be composed 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 organic layers in organic electronic devices can be classified according to their function into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials.

The most problematic issues for organic light-emitting diodes are their lifespan and efficiency. As displays become larger, these efficiency and lifespan issues must be resolved. Efficiency, lifespan, and driving voltage are interrelated. As efficiency increases, the driving voltage decreases relatively, and as the driving voltage decreases, the crystallization of organic materials due to Joule heating generated during driving decreases, which results in a tendency for the lifespan to increase.

However, simply improving the organic layer above does not maximize efficiency. This is because long life and high efficiency can be achieved simultaneously when the energy level and T1 value between each organic layer and the intrinsic properties of the material (mobility, interface properties, etc.) are optimally combined.

In addition, in order to solve the problem of luminescence in the hole transport layer in recent organic light emitting devices, a luminescence auxiliary layer must exist between the hole transport layer and the luminescence layer, and it is time to develop different luminescence auxiliary layers for each luminescence layer (R, G, B).

Typically, electrons are transferred from the electron transport layer to the light-emitting layer, and holes are transferred from the hole transport layer to the light-emitting layer, and excitons are generated through recombination.

However, since the material used in the hole transport layer must have a low HOMO value, most of them have a low T1 value, which causes excitons generated in the emitting layer to move to the hole transport layer, resulting in charge unbalance within the emitting layer and causing light emission at the hole transport layer interface.

If light is emitted at the interface of the hole transport layer, the color purity and efficiency of the organic electronic device deteriorate and the lifespan becomes shorter. Therefore, there is an urgent need for the development of a light-emitting auxiliary layer having a high T1 value and a HOMO level between the HOMO energy level of the hole transport layer and the HOMO energy level of the light-emitting layer.

Meanwhile, it is necessary to develop a hole injection layer material that has stable properties, that is, a high glass transition temperature, against Joule heating generated when the device is operated while delaying the penetration and diffusion of metal oxide from the anode electrode (ITO), which is one of the causes of the shortened lifespan of organic electric devices, into the organic layer. The low glass transition temperature of the hole transport layer material has the property of reducing the uniformity of the thin film surface when the device is operated, and this has been reported to have a significant impact on the device lifespan. In addition, OLED devices are mainly formed by a deposition method, and there is a need to develop materials that can withstand the deposition for a long time, that is, materials with strong heat resistance.

That is, in order to fully demonstrate the excellent characteristics of organic electric devices, it is necessary that the materials forming the organic layer within the device, such as hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials, and luminescent auxiliary layer materials, be supported by stable and efficient materials. However, stable and efficient organic layer materials for organic electric devices have not yet been sufficiently developed. Therefore, the development of new materials continues to be required.

In order to solve the problems of the above-described background technology, the present invention has discovered a compound having a novel structure, and has also discovered that when this compound is applied to an organic electric device, the luminous efficiency, stability, and lifespan of the device can be greatly improved.

Accordingly, the present invention aims to provide a novel compound, an organic electric element using the same, and an electronic device thereof.

The present invention provides a compound represented by the following chemical formula 1.

Chemical formula 1

In another aspect, the present invention provides an organic electric element and an electronic device thereof comprising a compound represented by the chemical formula 1.

By using the compound according to the present invention, high luminous efficiency, low driving voltage, and high heat resistance of the device can be achieved, and the color purity and lifespan of the device can be greatly improved.

Figures 1 to 3 are exemplary diagrams of organic electroluminescent devices according to the present invention.
Figure 4 shows a chemical formula according to one aspect of the present invention.

Hereinafter, the present invention will be described in detail with reference to embodiments. In describing the present invention, if it is judged that a detailed description of a related known configuration or function may obscure the gist of the present invention, the detailed description will be omitted.

Also, in describing components of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used. These terms are only intended to distinguish the components from other components, and the nature, order, or sequence of the components are not limited by the terms. When it is described that a component is "connected," "coupled," or "connected" to another component, it should be understood that the component may be directly connected or connected to the other component, but another component may also be "connected," "coupled," or "connected" between each component.

As used in this specification and the appended claims, unless otherwise stated, the following terms have the following meanings:

The term "halo" or "halogen" as used herein, unless otherwise stated, means fluorine (F), bromine (Br), chlorine (Cl), or iodine (I).

The term "alkyl" or "alkyl group" as used in the present invention, unless otherwise stated, means a radical of a saturated aliphatic functional group having a single bond of 1 to 60 carbon atoms, including a straight-chain alkyl group, a branched-chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted cycloalkyl group, and a cycloalkyl-substituted alkyl group.

The terms “alkenyl group,” “alkenyl group,” or “alkynyl group,” as used in the present invention, unless otherwise stated, include, but are not limited to, straight-chain or branched-chain groups each having a double bond or triple bond of 2 to 60 carbon atoms.

The term "cycloalkyl" as used in the present invention, unless otherwise stated, means alkyl forming a ring having 3 to 60 carbon atoms, but is not limited thereto.

The term “alkoxyl group,” “alkoxy group,” or “alkyloxy group” as used in the present invention means an alkyl group having an oxygen radical attached thereto, and unless otherwise specified, has 1 to 60 carbon atoms, but is not limited thereto.

The term "aryloxyl group" or "aryloxy group" as used in the present invention means an aryl group having an oxygen radical attached thereto, and unless otherwise specified, has 6 to 60 carbon atoms, but is not limited thereto.

The terms "aryl group" and "arylene group" used in the present invention, unless otherwise stated, each have 6 to 60 carbon atoms, but are not limited thereto. In the present invention, the aryl group or arylene group means a single ring or multi-ring aromatic, and includes an aromatic ring formed by the participation of adjacent substituents in a bond or reaction. For example, the aryl group can be a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.

The prefix "aryl" or "ar" refers to a radical substituted with an aryl group. For example, an arylalkyl group is an alkyl group substituted with an aryl group, an arylalkenyl group is an alkenyl group substituted with an aryl group, and the aryl substituted radical has the carbon numbers described herein.

Also, when prefixes are named consecutively, it means that the substituents are listed in the order they were first described. For example, in the case of an arylalkoxy group, it means an alkoxy group substituted with an aryl group, in the case of an alkoxylcarbonyl group, it means a carbonyl group substituted with an alkoxyl group, and in the case of an arylcarbonylalkenyl group, it means an alkenyl group substituted with an arylcarbonyl group, where the arylcarbonyl group is a carbonyl group substituted with an aryl group.

The term "heterocyclic group" used in the present invention, unless otherwise stated, includes one or more heteroatoms, has 2 to 60 carbon atoms, includes at least one of a single ring and a multiple ring, and includes a heteroaliphatic ring and a heteroaromatic ring. It may also be formed by bonding adjacent functional groups.

The term "heteroatom" as used herein, unless otherwise stated, represents N, O, S, P or Si.

Additionally, a "heterocyclic group" may also include a ring containing SO ₂ instead of ring-forming carbon. For example, a "heterocyclic group" includes the following compounds:

The term "fluorenyl group" or "fluorenylene group" as used in the present invention, unless otherwise stated, means a monovalent or divalent functional group wherein R, R' and R" in the following structures are all hydrogen, respectively, and a "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 includes a case where R and R' are bonded to each other to form a spiro compound together with the carbon to which they are bonded.

The term "spiro compound" used in the present invention has a 'spiro union', and a spiro union means a connection formed by two rings sharing only one atom. At this time, the atom shared between the two rings is called a 'spiro atom', and depending on the number of spiro atoms contained in a compound, they are called 'monospiro-', 'dicepiro-', and 'trispiro-' compounds, respectively.

Unless otherwise stated, the term "aliphatic" as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms, and "aliphatic ring" means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

Unless otherwise stated, the term "ring" as used in the present invention refers to a fused ring composed of an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a heterocyclic ring having 2 to 60 carbon atoms, or a combination thereof, and includes a saturated or unsaturated ring.

Other heterocyclic compounds or heteroradicals other than the aforementioned heterocyclic compounds contain one or more heteroatoms, but are not limited thereto.

In addition, unless explicitly stated otherwise, "substituted" in the term "substituted or unsubstituted" used in the present invention means a deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C ₁ to C ₂₀ alkyl group, a C ₁ to C ₂₀ alkoxyl group, a C ₁ to C ₂₀ alkylamine group, a C ₁ to C ₂₀ alkylthiophene group, a C ₆ to C ₂₀ arylthiophene group, a C ₂ to C ₂₀ alkenyl group, a C ₂ to C ₂₀ alkynyl group, a C ₃ to C ₂₀ cycloalkyl group, a C ₆ to C ₂₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, a C ₈ to C ₂₀ arylalkenyl group, a silane group, a boron group, a germanium group, and a C ₂ to C It means being substituted with one or more substituents selected from the group consisting of ₂₀ heterocyclic groups, but is not limited to these substituents.

Additionally, unless explicitly stated otherwise, the chemical formulas used in the present invention are applied in the same manner as the substituent definitions by the index definitions of the chemical formulas below.

Here, when a is an integer of 0, the substituent R ¹ is absent, and when a is an integer of 1, one substituent R ¹ is bonded to any one of the carbons forming the benzene ring, and when a is an integer of 2 or 3, they are bonded as follows, wherein R ¹ may be the same or different, and when a is an integer of 4 to 6, they are bonded to the carbon of the benzene ring in a similar manner, and meanwhile, the indication of the hydrogen bonded to the carbon forming the benzene ring is omitted.

The term "nonexistent" as used herein, unless otherwise stated, means not combined.

Hereinafter, a compound according to one aspect of the present invention and an organic electric device comprising the same will be described.

The present invention provides a compound represented by the following chemical formula 1.

Chemical Formula 1 Chemical Formula 1-1

In the above chemical formula 1 and chemical formula 1-1, each symbol can be defined as follows.

1) Ar ¹ and Ar ² are independently selected from the group consisting of a C ₆ to C ₆₀ aryl group; a fluorenyl group; a C ₂ to C ₆₀ heterocyclic group including at least one heteroatom selected from O, N, S, Si and P; and a fused ring group of a C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring.

When Ar ¹ and Ar ² are aryl groups, they may be preferably C ₆ to C ₃₀ aryl groups, more preferably C ₆ to C ₂₄ aryl groups, such as phenylene, biphenyl, naphthalene, terphenyl, and the like.

Ar ¹ and Ar ² , when they are heterocyclic groups, are preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₂₄ heterocyclic groups, and examples thereof include pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazolin, carbazole, dibenzoquinazole, dibenzofuran, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, and the like.

When Ar ¹ and Ar ² are fused ring groups, they may be preferably fused ring groups of an aliphatic ring having C ₃ to C ₃₀ and an aromatic ring having C ₆ to C ₃₀ , more preferably fused ring groups of an aliphatic ring having C ₃ to C ₂₄ and an aromatic ring having C ₆ to C ₂₄ .

2) L ₁ and L ₂ are independently selected from the group consisting of a single bond; a C ₆ to C ₆₀ arylene group; a fluorenylene group; a C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; and a C ₃ to C ₆₀ aliphatic ring group.

L and L ₂ may be an arylene group, preferably a C ₆ to C ₃₀ arylene group, more preferably a C ₆ to C ₂₄ arylene group, and may be, for example, phenylene, biphenyl, naphthalene, terphenyl, or the like.

L and L ₂ are preferably heterocyclic groups, preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₂₄ heterocyclic groups, and examples thereof include pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazolin, carbazole, dibenzoquinazole, dibenzofuran, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, and the like.

When L and L ₂ are an aliphatic ring group, they may be preferably an aliphatic ring group having C ₃ to C ₃₀ , more preferably an aliphatic ring group having C ₃ to C ₂₄ .

3) X ₁ and X ₂ are independently a single bond, O, S, or CR'R".

4) The R' and R" are each independently selected from the group consisting of hydrogen; deuterium; a C ₁ to C ₆₀ alkyl group; a C ₂ to C ₆₀ alkenyl group; _{a C 2 to} C ₆₀ alkynyl group; a C ₁ to C ₆₀ alkoxy group; a C 6 to C ₆₀ aryloxy group; a C ₆ to C ₆₀ aryl group; a fluorenyl group; a C ₂ to C ₆₀ heterocyclic group including at least one heteroatom selected from O, N, S, Si and P; and a fused ring group of a C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring; or R' and R" may be bonded to each other to form a spiro ring.

When R' and R" are alkyl groups, they may preferably be C ₁ to C ₃₀ alkyl groups, and more preferably C ₁ to C ₂₄ alkyl groups.

When R' and R" are alkenyl groups, they may preferably be C ₂ to C ₃₀ alkenyl groups, and more preferably C ₂ to C ₂₄ alkenyl groups.

When R' and R" are alkynyl groups, they may preferably be C ₂ to C ₃₀ alkynyl groups, and more preferably C ₂ to C ₂₄ alkynyl groups.

When R' and R" are an alkoxy group, they may preferably be an alkoxy group having C ₁ to C ₃₀ , and more preferably an alkoxy group having C ₁ to C ₂₄ .

When R' and R" are aryloxy groups, they may preferably be C ₆ to C ₃₀ aryloxy groups, and more preferably C ₆ to C ₂₄ aryloxy groups.

When R' and R" are aryl groups, they are preferably _C6 to _C30 aryl groups, more preferably _C6 to _C24 aryl groups, such as phenylene, biphenyl, naphthalene, terphenyl, and the like.

When R' and R" are heterocyclic groups, they are preferably _C2 to _C30 heterocyclic groups, more preferably _C2 to _C24 heterocyclic groups, and examples thereof include pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazolin, carbazole, dibenzoquinazole, dibenzofuran, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, and the like.

When R' and R" are fused ring groups, they may preferably be fused ring groups of an aliphatic ring having C ₃ to C ₃₀ and an aromatic ring having C ₆ to C ₃₀ , and more preferably, they may be fused ring groups of an aliphatic ring having C ₃ to C ₂₄ and an aromatic ring having C ₆ to C ₂₄ .

5) m and n are independently 0 or 1, and when m and n are 0, X ₁ and X ₂ do not exist, and l is an integer from 0 to 3.

6) T ₁ , T ₂ , T ₃ and T ₄ are independently selected from the group consisting of a C ₆ ~C ₆₀ aromatic ring group; a C ₃ ~C ₆₀ aliphatic ring group; a C ₂ ~C ₆₀ heterocyclic group including at least one heteroatom selected from O, N, S, Si and P; and a fused ring group of a C ₃ ~C ₆₀ aliphatic ring and a C ₆ ~C ₆₀ aromatic ring; provided that at least one of T ₁ , T ₂ , T ₃ and T ₄ is a substituent represented by the chemical formula 1-1.

6) Y ₁ and Y ₂ are independently a single bond, O, S or CR'R", except when both Y ₁ and Y ₂ are single bonds.

7) R _a and R _b are each the same or different, and are independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; nitro group; C ₆ to C ₆₀ aryl group; fluorenyl group; C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; a fused ring group of a C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring; _{a C 1 to} C ₆₀ alkyl group; a C ₂ to C ₆₀ alkenyl group; a C ₂ to C ₆₀ alkynyl group; _a C ₁ to C 60 alkoxy group; a C 6 to C ₆₀ aryloxy group; and -L'-NR ^c R ^d ;, or a plurality of adjacent R _{a groups} may be bonded to each other to form a ring.

When R _a and R _b are aryl groups, they may be preferably C ₆ to C ₃₀ aryl groups, more preferably C ₆ to C ₂₄ aryl groups, such as phenylene, biphenyl, naphthalene, terphenyl, and the like.

R _a and R _b may be a heterocyclic group, preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₂₄ heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazolin, carbazole, dibenzoquinazole, dibenzofuran, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, and the like.

When R _a and R _b are fused ring groups, they may be preferably fused ring groups of an aliphatic ring having C ₃ to C ₃₀ and an aromatic ring having C ₆ to C ₃₀ , more preferably fused ring groups of an aliphatic ring having C ₃ to C ₂₄ and an aromatic ring having C ₆ to C ₂₄ .

When R _a and R _b are alkyl groups, they may be preferably C ₁ to C ₃₀ alkyl groups, and more preferably C ₁ to C ₂₄ alkyl groups.

When R _a and R _b are alkenyl groups, they may be preferably C ₂ to C ₃₀ alkenyl groups, and more preferably C ₂ to C ₂₄ alkenyl groups.

When R _a and R _b are an alkynyl group, they may be preferably a C ₂ to C ₃₀ alkynyl group, and more preferably a C ₂ to C ₂₄ alkynyl group.

When R _a and R _b are an alkoxy group, they may be preferably an alkoxy group having C ₁ to C ₃₀ , and more preferably an alkoxy group having C ₁ to C ₂₄ .

When R _a and R _b are aryloxy groups, they may be preferably C ₆ to C ₃₀ aryloxy groups, and more preferably C ₆ to C ₂₄ aryloxy groups.

8) The L' is selected from the group consisting of a single bond; a C ₆ to C ₆₀ arylene group; a fluorenylene group; a C ₂ to C ₆₀ heterocyclic group including at least one heteroatom among O, N, S, Si, and P; and a C ₃ to C ₆₀ aliphatic ring group; and the R ^c and R ^d are each independently selected from the group consisting of a C ₆ to C ₆₀ aryl group; a fluorenyl group; a C ₂ to C ₆₀ heterocyclic group including at least one heteroatom among O, N, S, Si, and P; and a fused ring group of a C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring.

When L' is an arylene group, it may be preferably an arylene group having C ₆ to C ₃₀ , more preferably an arylene group having C ₆ to C ₂₄ , and may be, for example, phenylene, biphenyl, naphthalene, terphenyl, or the like.

When L' is a heterocyclic group, it may be preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₂₄ heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazolin, carbazole, dibenzoquinazole, dibenzofuran, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, and the like.

When L' is an aliphatic ring group, it is preferably an aliphatic ring group having C ₃ to C ₃₀ , and more preferably an aliphatic ring group having C ₃ to C ₂₄ .

When R ^c and R ^d are aryl groups, it is preferable that they are C ₆ to C ₃₀ aryl groups, and most preferably, they may be C ₆ to C ₂₅ aryl groups, and examples thereof include phenyl, biphenyl, naphthyl, phenanthrene, terphenyl, and the like.

When R ^c and R ^d are heterocyclic groups, they are preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₂₄ heterocyclic groups, and examples thereof include pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazolin, carbazole, dibenzoquinazole, dibenzofuran, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, and the like.

When R ^c and R ^d are fused ring groups, they are preferably fused ring groups of an aliphatic ring having C ₃ to C ₃₀ and an aromatic ring having C ₆ to C ₃₀ , and more preferably fused ring groups of an aliphatic ring having C ₃ to C ₂₄ and an aromatic ring having C ₆ to C ₂₄ .

9) a is an integer from 0 to 2, b is an integer from 0 to 4,

10) * indicates the binding position.

Here, the aryl group, the arylene group, the heterocyclic group, the fluorenyl group, the fluorenylene group, the aliphatic ring group, the fused ring group, the alkyl group, the alkenyl group, the alkoxy group and the aryloxy group are each independently selected from deuterium; halogen; a silane group; a siloxane group; a boron group; a germanium group; a cyano group; a nitro group; a C ₁ to C ₂₀ alkylthio group; _{a C 1 to} C ₂₀ alkoxy group; _a C ₁ to C ₂₀ alkyl group; a C ₂ to C ₂₀ alkenyl group; a C ₂ to C ₂₀ alkynyl group; a C 6 to C 20 aryl group; a C ₆ to C ₂₀ aryl group substituted with deuterium; a fluorenyl group; a C ₂ to C ₂₀ heterocyclic group; A C ₃ to C ₂₀ cycloalkyl group; a C ₇ to C ₂₀ arylalkyl group; and a C _{8 to C 20 arylalkenyl group may be further substituted with one or more substituents selected from the group consisting of a C 3 to C 20 cycloalkyl group; a C 7 to C 20} arylalkyl group; and a C 8 to C ₂₀ arylalkenyl group; and further, these substituents may be combined with each other to form a ring, wherein the 'ring' refers to a fused ring formed of a C ₃ to C ₆₀ aliphatic ring, a C ₆ to C 60 aromatic ring, a C ₂ to C ₆₀ heterocycle, or a combination thereof, and includes a saturated or unsaturated ring.

In addition, the present invention provides a compound represented by the chemical formula 1, which is represented by the following chemical formula 2 or chemical formula 3.

Chemical Formula 2 Chemical Formula 3

{In the above chemical formula 2 and chemical formula 3,

1) Ar ¹ , Ar ² , L ₁ , L ₂ , X ₁ and X ₂ are as defined in the above chemical formula 1,

2) R ₁ , R ₂ and R ₃ are the same as the definition of R _a in the above chemical formula 2,

3) c, d, e and f are independently integers from 0 to 4.

In addition, the present invention provides a compound represented by the chemical formula 1, wherein the compound is represented by any one of the following chemical formulas 4 to 12.

Chemical Formula 4 Chemical Formula 5 Chemical Formula 6

Chemical Formula 7 Chemical Formula 8 Chemical Formula 9

Chemical Formula 10 Chemical Formula 11 Chemical Formula 12

{In the chemical formulas 4 to 12 above,

1) Ar ¹ , Ar ² , L ₁ , L ₂ , X ₁ are the same as defined in the chemical formula 1 above,

2) Y ₁ , Y ₂ , R _a , R _b , a and b are the same as defined in the chemical formula 1-1 above,

2) R ₁ , R ₂ , R ₃ , c, d and e are the same as defined in the chemical formula 2 above,

3) L ₂ and Ar ₂ can be further substituted with R _a of the above chemical formula 1-1.

In addition, the present invention provides a compound represented by the chemical formula 1, wherein the compound is represented by any one of the following compounds P-1 to P-86.

Referring to FIG. 1, an organic electric element (100) according to the present invention comprises a first electrode (110), a second electrode (170), and an organic layer comprising a single compound or two or more compounds represented by Chemical Formula 1 between the first electrode (110) and the second electrode (170). At this time, the first electrode (110) may be an anode or positive electrode, and the second electrode (170) may be a cathode or negative electrode, 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 layer may sequentially include a hole injection layer (120), a hole transport layer (130), an emission layer (140), an electron transport layer (150), and an electron injection layer (160) on the first electrode (110). At this time, the remaining layers except for the emission layer (140) may not be formed. A hole blocking layer, an electron blocking layer, an emission auxiliary layer (220), a buffer layer (210), etc. may be further included, and the electron transport layer (150), etc. may play the role of a hole blocking layer. (See FIG. 2)

In addition, the organic electric device according to one embodiment of the present invention may further include a protective layer or a light efficiency improvement layer (180). This light efficiency improvement layer may be formed on a surface of both sides of the first electrode that is not in contact with the organic layer or on a surface of both sides of the second electrode that is not in contact with the organic layer. The compound according to one embodiment of the present invention applied to the organic layer may be used as a host or dopant of a hole injection layer (120), a hole transport layer (130), a light emitting auxiliary layer (220), an electron transport auxiliary layer, an electron transport layer (150), an electron injection layer (160), a light emitting layer (140), or a material of a light efficiency improvement layer. Preferably, for example, the compound according to Chemical Formula 1 of the present invention may be used as a material of a light emitting auxiliary layer or a light emitting layer.

The above organic layer may include two or more stacks including a hole transport layer, a light-emitting layer, and an electron transport layer sequentially formed on the anode, and may further include a charge generation layer formed between the two or more stacks. (See FIG. 3)

Meanwhile, since even with the same core, the band gap, electrical characteristics, and interface characteristics can vary depending on which substituent is bonded at which position, the selection of the core and the combination of sub-substituents bonded to it are also very important, and in particular, when the energy level and T1 value between each organic layer, and the intrinsic characteristics of the material (mobility, interface characteristics, etc.) are optimally combined, both a long lifespan and high efficiency can be achieved.

An organic light emitting device according to one embodiment of the present invention can be manufactured using a PVD (physical vapor deposition) method. For example, a metal or a conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode, and an organic layer including 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) is formed thereon, and then a material that can be used as a cathode is deposited thereon.

In addition, the present invention provides an organic electric device characterized in that the organic layer is formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a deep coating process, and a roll-to-roll process, and the organic layer includes the compound as an electron transport material.

As another specific example, the present invention provides an organic electric device characterized in that a compound of the same or different types represented by the chemical formula 1 is mixed and used in the organic layer.

In addition, the present invention provides a light-emitting auxiliary layer composition comprising a compound represented by the chemical formula 1, and provides an organic electric device comprising the light-emitting auxiliary layer.

In addition, the present invention provides a hole transport layer composition comprising a compound represented by the chemical formula 1, and provides an organic electric device comprising the hole transport layer.

In addition, the present invention provides an electronic device including a display device including the above-described organic electric element; and a control unit for driving the display device.

In another aspect, the present invention provides an electronic device characterized in that the organic electroluminescent element is at least one of an organic light-emitting element, an organic solar cell, an organic photoconductor, an organic transistor, and a monochrome or white lighting element. 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 systems, game consoles, various TVs, and various computers.

Hereinafter, examples of synthesis of the compound represented by the chemical formula 1 of the present invention and examples of manufacturing the organic electric device of the present invention will be described in detail by way of examples, but the present invention is not limited to the following examples.

[ Synthetic example 1]

Synthesis of chemical formula 1

The compound (final product) represented by chemical formula 1 according to the present invention is synthesized as in the following reaction scheme 1, but is not limited thereto.

<Reaction Formula 1>

In the above reaction formula 1, each symbol can be defined as follows.

1) Q is independently H, Br, Cl or I, and may be singular or plural depending on the number of carbon atoms in the rings of T ₂ and T ₃ . For example, when T ₂ and T ₃ are aryl groups of C ₆ , Q may be an integer from 0 to 4.

2) Ar ¹ , Ar ² , L ₁ , L ₂ , X ₁ , X ₂ , T ₁ , T ₂ , T ₃ , T ₄ , m, n and l are as defined above.

I. Synthesis of Sub 1

Sub 1 of the above reaction scheme 1 is synthesized by the reaction path of the following reaction scheme 2, but is not limited thereto. Here, n is 1 or 2, and Q, Ar ¹ , Ar ² , L ₁ , L ₂ and T ₁ are as defined above.

<Reaction Formula 2>

1. Sub 1-6 Synthesis

(1) Synthesis of Sub 1-II-6

Sub 1-I-6 (50 g, 162.5 mmol) was dissolved in toluene (1,666 ml) in a round-bottomed flask, and [1,1'-biphenyl]-2-amine (28.9 g, 170.7 mmol), Pd ₂ (dba) ₃ (0.03 equiv.), P(t-Bu) ₃ (0.06 equiv.), and NaOt-Bu (3 equiv.) were added, and the mixture was stirred at 100°C. Upon completion of the reaction, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silica gel column chromatography and recrystallized to obtain 58.2 g (yield: 81.3%) of Sub 1-II-6.

(2) Synthesis of Sub 1-6

To Sub 1-II-6 (58.2 g, 132.2 mmol), aniline (12.9 g, 138.8 mmol), Pd ₂ (dba) ₃ (0.03 equiv.), P( t -Bu) ₃ (0.06 equiv.), NaO t -Bu (3 equiv.), and toluene (1,355 ml) were added, and using the above Sub 1-II-6 synthesis method, Sub 1-6 48.2 g (yield: 80.6%) was obtained.

2. Sub 1-13 Synthesis

(1) Synthesis of Sub 1-II-13

Sub 1-I-13 (46 g, 163.4 mmol), aniline (16 g, 171.6 mmol), Pd ₂ (dba) ₃ (0.03 equiv.), P( t -Bu) ₃ (0.06 equiv.), NaO t -Bu (3 equiv.), and toluene (1,675 ml) were added and using the above Sub 1-6 synthesis method, Sub 1-II-13 44.26 g (yield: 80.1%) was obtained.

(2) Synthesis of Sub 1-13

To Sub 1-II-13 (44.3 g, 131 mmol), 3-(9,9-dimethyl-9H-fluoren-4-yl)aniline (39.3 g, 137.5 mmol), Pd ₂ (dba) ₃ (0.03 equiv.), P( t -Bu) ₃ (0.06 equiv.), NaO t -Bu (3 equiv.), and toluene (1,343 ml) were added, and using the above Sub 1-6 synthesis method, Sub 1-13 56.3 g (yield: 79.2%) was obtained.

3. Sub 1-31 Synthesis

Sub 1-I-31 (33 g, 89.7 mmol), aniline (8.8 g, 94.1 mmol), Pd ₂ (dba) ₃ (0.03 equiv.), P( t -Bu) ₃ (0.06 equiv.), NaO t -Bu (3 equiv.), and toluene (919 ml) were added and Sub 1-31 27.3 g (yield: 77.6%) was obtained using the above Sub 1-6 synthesis method.

4. Sub 1-36 Synthesis

To Sub 1-I-36 (42 g, 178 mmol), aniline (17.4 g, 186.9 mmol), Pd ₂ (dba) ₃ (0.03 equiv.), P( t -Bu) ₃ (0.06 equiv.), NaO t -Bu (3 equiv.), and toluene (1,825 ml) were added, and Sub 1-36 40 g (yield: 86.4%) was obtained using the above Sub 1-6 synthesis method.

5. Sub 1-69 Synthesis

(1) Synthesis of Sub 1-II-69

Sub 1-I-69 (37 g, 120.3 mmol), aniline (11.8 g, 126.3 mmol), Pd ₂ (dba) ₃ (0.03 equiv.), P( t -Bu) ₃ (0.06 equiv.), NaO t -Bu (3 equiv.), and toluene (1,233 ml) were added and Sub 1-II-69 31.2 g (yield: 71.1%) was obtained using the above Sub 1-6 synthesis method.

(2) Synthesis of Sub 1-69

To Sub 1-II-69 (31.2 g, 85.7 mmol), 3-(benzo[b]naphtho[1,2-d]thiophen-1-yl)aniline (29.3 g, 89.9 mmol), Pd ₂ (dba) ₃ (0.03 equiv.), P( t -Bu) ₃ (0.06 equiv.), NaO t -Bu (3 equiv.), toluene (878 ml) were added, and Sub 1-69 36.1 g (yield: 69.2%) was obtained using the above Sub 1-6 synthesis method.

6. Sub 1-72 Synthesis

Sub 1-I-72 (43 g, 110.8 mmol), aniline (10.8 g, 116.3 mmol), Pd ₂ (dba) ₃ (0.03 equiv.), P( t -Bu) ₃ (0.06 equiv.), NaO t -Bu (3 equiv.), and toluene (1,136 ml) were added and Sub 1-72 39.4 g (yield: 86.2%) was obtained using the above Sub 1-6 synthesis method.

Examples of the above Sub 1 are as follows, but are not limited thereto. In addition, Table 1 below shows FD-MS (Field Desorption-Mass Spectrometry) values of some compounds belonging to the above Sub 1.

compound FD-MS compound FD-MS Sub 1-1 m/z=452.23(C ₃₃ H ₂₈ N ₂ =452.6) Sub 1-2 m/z=400.16(C ₂₈ H ₂₀ N ₂ O=400.48) Sub 1-3 m/z=518.18(C ₃₆ H ₂₆ N ₂ S=518.68) Sub 1-4 m/z=528.26(C ₃₉ H ₃₂ N ₂ =528.7) Sub 1-5 m/z=450.17(C ₃₂ H ₂₂ N ₂ O=450.54) Sub 1-6 m/z=452.23(C ₃₃ H ₂₈ N ₂ =452.6) Sub 1-7 m/z=502.24(C ₃₇ H ₃₀ N ₂ =502.66) Sub 1-8 m/z=366.12(C ₂₄ H ₁₈ N ₂ S=366.48) Sub 1-9 m/z=426.21(C ₃₁ H ₂₆ N ₂ =426.56) Sub 1-10 m/z=376.19(C ₂₇ H ₂₄ N ₂ =376.5) Sub 1-11 m/z=350.14(C ₂₄ H ₁₈ N ₂ O=350.42) Sub 1-12 m/z=482.18(C ₃₃ H ₂₆ N ₂ S=482.65) Sub 1-13 m/z=542.24(C ₃₉ H ₃₀ N ₂ O=542.68) Sub 1-14 m/z=394.15(C ₂₆ H ₂₂ N ₂ S=394.54) Sub 1-15 m/z=516.22(C ₃₇ H ₂₈ N ₂ O=516.64) Sub 1-16 m/z=528.22(C ₃₈ H ₂₈ N ₂ O=528.66) Sub 1-17 m/z=550.24(C ₄₁ H ₃₀ N ₂ =550.71) Sub 1-18 m/z=498.21(C ₃₇ H ₂₆ N ₂ =498.63) Sub 1-19 m/z=594.21(C ₄₂ H ₃₀ N ₂ S=594.78) Sub 1-20 m/z=612.13(C ₄₀ H ₂₄ N ₂ O S ₂ =612.77) Sub 1-21 m/z=541.25(C ₃₉ H ₃₁ N ₃ =541.7) Sub 1-22 m/z=534.3(C ₃₉ H ₃₈ N ₂ =534.75) Sub 1-23 m/z=630.3(C ₄₇ H ₃₈ N ₂ =630.84) Sub 1-24 m/z=316.19(C ₂₂ H ₂₄ N ₂ =316.45) Sub 1-25 m/z=564.26(C ₄₂ H ₃₂ N ₂ =564.73) Sub 1-26 m/z=412.19(C ₃₀ H ₂₄ N ₂ =412.54) Sub 1-27 m/z=627.27(C ₄₆ H ₃₃ N ₃ =627.79) Sub 1-28 m/z=454.2(C ₃₂ H ₂₆ N ₂ O=454.57) Sub 1-29 m/z=398.09(C ₂₄ H ₁₈ N ₂ S ₂ =398.54) Sub 1-30 m/z=382.11(C ₂₄ H ₁₈ N ₂ OS=382.48) Sub 1-31 m/z=392.19(C ₂₇ H ₂₄ N ₂ O=392.5) Sub 1-32 m/z=558.21(C ₃₈ H ₃₀ N ₂ OSi=558.76) Sub 1-33 m/z=450.17(C ₃₂ H ₂₂ N ₂ O=450.54) Sub 1-34 m/z=505.26(C ₃₇ H ₂₃ D ₅ N ₂ =505.68) Sub 1-35 m/z=366.12(C ₂₄ H ₁₈ N ₂ S=366.48) Sub 1-36 m/z=260.13(C ₁₈ H ₁₆ N ₂ =260.34) Sub 1-37 m/z=336.16(C ₂₄ H ₂₀ N ₂ =336.44) Sub 1-38 m/z=386.18(C ₂₈ H ₂₂ N ₂ =386.5) Sub 1-39 m/z=381.23(C ₂₇ H ₁₉ D ₅ N ₂ =381.53) Sub 1-40 m/z=368.13(C ₂₄ H ₁₇ FN ₂ O=368.41) Sub 1-41 m/z=472.11(C ₃₀ H ₂₀ N ₂ S ₂ =472.62) Sub 1-42 m/z=564.13(C ₃₆ H ₂₄ N ₂ O S ₂ =564.72) Sub 1-43 m/z=488.23(C ₃₆ H ₂₈ N ₂ =488.63) Sub 1-44 m/z=438.21(C ₃₂ H ₂₆ N ₂ =438.57) Sub 1-45 m/z=704.28(C ₅₂ H ₃₆ N ₂ O=704.87) Sub 1-46 m/z=620.19(C ₄₃ H ₂₈ N ₂ OS=620.77) Sub 1-47 m/z=792.26(C ₅₅ H ₄₀ N ₂ S ₂ =793.06) Sub 1-48 m/z=516.22(C ₃₇ H ₂₈ N ₂ O=516.64) Sub 1-49 m/z=452.23(C ₃₃ H ₂₈ N ₂ =452.6) Sub 1-50 m/z=400.16(C ₂₈ H ₂₀ N ₂ O=400.48) Sub 1-51 m/z=366.14(C ₂₄ H ₁₈ N ₂ O ₂ =366.42) Sub 1-52 m/z=744.17(C ₄₉ H ₃₂ N ₂ S ₃ =744.99) Sub 1-53 m/z=543.23(C ₃₈ H ₂₉ N ₃ O=543.67) Sub 1-54 m/z=578.27(C ₄₃ H ₃₄ N ₂ =578.76) Sub 1-55 m/z=518.18(C ₃₆ H ₂₆ N ₂ S=518.68) Sub 1-56 m/z=506.15(C ₃₄ H ₂₂ N ₂ OS=506.62) Sub 1-57 m/z=528.26(C ₃₉ H ₃₂ N ₂ =528.7) Sub 1-58 m/z=394.18(C ₂₇ H ₂₃ F N ₂ =394.49) Sub 1-59 m/z=492.17(C ₃₄ H ₂₄ N ₂ S=492.64) Sub 1-60 m/z=502.24(C ₃₇ H ₃₀ N ₂ =502.66) Sub 1-61 m/z=466.2(C ₃₃ H ₂₆ N ₂ O=466.58) Sub 1-62 m/z=667.3(C ₄₉ H ₃₇ N ₃ =667.86) Sub 1-63 m/z=350.14(C ₂₄ H ₁₈ N ₂ O=350.42) Sub 1-64 m/z=556.2(C ₃₉ H ₂₈ N ₂ S=556.73) Sub 1-65 m/z=528.26(C ₃₉ H ₃₂ N ₂ =528.7) Sub 1-66 m/z=462.21(C ₃₄ H ₂₆ N ₂ =462.6) Sub 1-67 m/z=468.18(C ₃₂ H ₂₄ N ₂ O ₂ =468.56) Sub 1-68 m/z=492.17(C ₃₄ H ₂₄ N ₂ S=492.64) Sub 1-69 m/z=608.23(C ₄₃ H ₃₂ N ₂ S=608.8) Sub 1-70 m/z=378.17(C ₂₆ H ₂₂ N ₂ O=378.48) Sub 1-71 m/z=416.15(C ₂₈ H ₂₀ N ₂ O ₂ =416.48) Sub 1-72 m/z=412.19(C ₃₀ H ₂₄ N ₂ =412.54) Sub 1-73 m/z=310.15(C ₂₂ H ₁₈ N ₂ =310.4) Sub 1-74 m/z=310.15(C ₂₂ H ₁₈ N ₂ =310.4) Sub 1-75 m/z=400.16(C ₂₈ H ₂₀ N ₂ O=400.48)

Meanwhile, examples of the above Sub 2 are as follows, but are not limited thereto. In addition, Table 2 below shows FD-MS values of some compounds belonging to the above Sub 2.

compound FD-MS compound FD-MS Sub 2-1 CAS NO: 13029-09-9 Sub 2-2 CAS NO: 2306157-06-0 Sub 2-3 m/z=390.96(C ₁₈ H ₇ D ₅ Br ₂ =393.13) Sub 2-4 m/z=461.96(C ₂₄ H ₁₆ Br ₂ =464.2) Sub 2-5 m/z=511.98(C ₂₈ H ₁₈ Br ₂ =514.26) Sub 2-6 m/z=461.96(C ₂₄ H ₁₆ Br ₂ =464.2) Sub 2-7 m/z=327.89(C ₁₂ H ₇ Br ₂ F=329.99) Sub 2-8 m/z=425.96(C ₂₁ H ₁₆ Br ₂ =428.17) Sub 2-9 m/z=399.91(C ₁₈ H ₁₀ Br ₂ O=402.09) Sub 2-10 m/z=415.89(C ₁₈ H ₁₀ Br ₂ S=418.15) Sub 2-11 m/z=425.96(C ₂₁ H ₁₆ Br ₂ =428.17) Sub 2-12 CAS NO: 16400-51-4 Sub 2-13 m/z=435.95(C ₂₂ H ₁₄ Br ₂ =438.16) Sub 2-14 m/z=485.96(C ₂₆ H ₁₆ Br ₂ =488.22) Sub 2-15 m/z=399.91(C ₁₈ H ₁₀ Br ₂ O=402.09) Sub 2-16 m/z=549.99(C ₃₁ H ₂₀ Br ₂ =552.31) Sub 2-17 m/z=415.89(C ₁₈ H ₁₀ Br ₂ S=418.15) Sub 2-18 m/z=425.96(C ₂₁ H ₁₆ Br ₂ =428.17) Sub 2-19 CAS NO: 2350272-28-3 Sub 2-20 m/z=670.09(C ₄₀ H ₃₂ Br ₂ =672.5) Sub 2-21 m/z=511.98(C ₂₈ H ₁₈ Br ₂ =514.26) Sub 2-22 m/z=461.96(C ₂₄ H ₁₆ Br ₂ =464.2) Sub 2-23 m/z=359.91(C ₁₆ H ₁₀ Br ₂ =362.06) Sub 2-24 m/z=588.01(C ₃₄ H ₂₂ Br ₂ =590.36) Sub 2-25 CAS NO: 21848-84-0 Sub 2-26 m/z=477.96(C ₂₄ H ₁₆ Br ₂ O=480.2) Sub 2-27 m/z=427.98(C ₂₁ H ₁₈ Br ₂ =430.18) Sub 2-28 CAS NO: 51452-87-0 Sub 2-29 m/z=517.99(C ₂₇ H ₂₀ Br ₂ O=520.26) Sub 2-30 m/z=369.9(C ₁₄ H ₁₂ Br ₂ S=372.12) Sub 2-31 CAS NO: 1948277-36-8 Sub 2-32 m/z=656(C ₃₇ H ₂₂ Br ₂ O ₂ =658.39) Sub 2-33 m/z=563.94(C ₂₇ H ₁₈ Br ₂ O ₂ S=566.31) Sub 2-34 m/z=441.96(C ₂₁ H ₁₆ Br ₂ O=444.17) Sub 2-35 m/z=431.88(C ₁₈ H ₁₀ Br ₂ OS=434.15) Sub 2-36 m/z=461.96(C ₂₄ H ₁₆ Br ₂ =464.2) Sub 2-37 m/z=359.91(C ₁₆ H ₁₀ Br ₂ =362.06) Sub 2-38 CAS NO: 6903-63-5 Sub 2-39 m/z=431.92(C ₁₉ H ₁₄ Br ₂ S=434.19) Sub 2-40 m/z=473.96(C ₂₅ H ₁₆ Br ₂ =476.21) Sub 2-41 m/z=391.89(C ₁₆ H ₁₀ Br ₂ S=394.12) Sub 2-42 m/z=565.99(C ₃₁ H ₂₀ Br ₂ O=568.31) Sub 2-43 m/z=521.89(C ₂₄ H ₁₂ Br ₂ O ₂ S=524.23) Sub 2-44 m/z=631.98(C ₃₅ H ₂₂ Br ₂ S=634.43) Sub 2-45 m/z=443.97(C ₂₁ H ₁₈ Br ₂ O=446.18) Sub 2-46 m/z=523.91(C ₂₄ H ₁₄ Br ₂ O ₂ S=526.24) Sub 2-47 m/z=682.02(C ₃₆ H ₂₈ Br ₂ O ₂ S=684.49)

II. Final products synthesis example

1. P-4 Synthetic example

Sub 1-4 (32 g, 84.9 mmol) obtained in the above synthesis was added to toluene (871 ml), and Sub 2-4 (41.4 g, 89.2 mmol), Pd ₂ (dba) ₃ (0.03 equivalent), P (t-Bu) ₃ (0.06 equivalent), and NaOt-Bu (3 equivalent) were added, and stirred at 100°C. When 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. The resulting compound was purified by silica gel column and recrystallized to obtain 49.7 g of the product P-4. (Yield: 86.2%)

2. P-14 Synthetic example

To Sub 1-13 (30 g, 55.3 mmol), Sub 2-1 (18.1 g, 58.1 mmol), Pd ₂ (dba) ₃ (0.03 equiv.), P( t -Bu) ₃ (0.06 equiv.), NaO t -Bu (3 equiv.), Toluene (567 ml) were added, and using the above P-4 synthesis method, product P-14 31.7 g (yield: 82.7%) was obtained.

3. P-21 Synthetic example

Sub 2-1 (9 g, 28.8 mmol), Pd ₂ (dba) ₃ (0.03 equiv.), P( t -Bu) ₃ (0.06 equiv.), NaO t -Bu (3 equiv.), and toluene (281 ml) were added to Sub 1-20 (16.8 g, 27.4 mmol), and 16.2 g (yield: 77.5%) of the product P-21 was obtained using the above P-4 synthesis method.

4. P-26 Synthetic example

To Sub 1-25 (14 g, 24.8 mmol), Sub 2-9 (10.5 g, 26.0 mmol), Pd ₂ (dba) ₃ (0.03 equiv.), P( t -Bu) ₃ (0.06 equiv.), NaO t -Bu (3 equiv.), toluene (254 ml) were added, and 14.9 g (yield: 74.6%) of the product P-26 was obtained using the above P-4 synthesis method.

5. P-34 Synthetic example

Sub 2-12 (18.9 g, 60.6 mmol), Pd ₂ (dba) ₃ (0.03 equiv.), P( t -Bu) ₃ (0.06 equiv.), NaO t -Bu (3 equiv.), toluene (592 ml) were added to Sub 1-33 (26 g, 57.7 mmol), and the product P-34 24.2 g (yield: 69.8%) was obtained using the above P-4 synthesis method.

6. P-52 Synthetic example

Sub 1-75 (20 g, 49.9 mmol), Sub 2-19 (19 g, 52.4 mmol), Pd ₂ (dba) ₃ (0.03 equiv.), P( t -Bu) ₃ (0.06 equiv.), NaO t -Bu (3 equiv.), Toluene (512 ml) were added and the product P-52 22.9 g (yield: 76.2%) was obtained using the above P-4 synthesis method.

7. P-57 Synthetic example

Sub 1-54 (17 g, 29.4 mmol), Sub 2-8 (13.2 g, 30.8 mmol), Pd ₂ (dba) ₃ (0.03 equiv.), P( t -Bu) ₃ (0.06 equiv.), NaO t -Bu (3 equiv.), Toluene (301 ml) were added and the product P-57 15.2 g (yield: 61.3%) was obtained using the above P-4 synthesis method.

8. P-65 Synthetic example

Sub 2-25 (15.5 g, 45.0 mmol), Pd ₂ (dba) ₃ (0.03 equiv.), P( t -Bu) ₃ (0.06 equiv.), NaO t -Bu (3 equiv.), and toluene (439 ml) were added to Sub 1-61 (20 g, 42.9 mmol), and the product P-65 (19 g, 68.4%) was obtained using the above P-4 synthesis method.

9. P-75 Synthetic example

Sub 1-67 (23 g, 49.1 mmol), Sub 2-37 (18.7 g, 51.5 mmol), Pd ₂ (dba) ₃ (0.03 equiv.), P( t -Bu) ₃ (0.06 equiv.), NaO t -Bu (3 equiv.), Toluene (503 ml) were added and the product P-75 20.4 g (yield: 62.2%) was obtained using the above P-4 synthesis method.

10. P-82 Synthetic example

Sub 2-43 (33.8 g, 64.5 mmol), Pd ₂ (dba) ₃ (0.03 equiv.), P( t -Bu) ₃ (0.06 equiv.), NaO t -Bu (3 equiv.), toluene (630 ml) were added to Sub 1-36 (16 g, 61.5 mmol), and the product P-82 22.9 g (yield: 59.8%) was obtained using the above P-4 synthesis method.

Table 3 below shows the FD-MS values of some compounds belonging to the Final Products.

compound FD-MS compound FD-MS P-1 m/z=602.27(C ₄₅ H ₃₄ N ₂ =602.78) P-2 m/z=550.2(C ₄₀ H ₂₆ N ₂ O=550.66) P-3 m/z=668.23(C ₄₈ H ₃₂ N ₂ S=668.86) P-4 m/z=678.3(C ₅₁ H ₃₈ N ₂ =678.88) P-5 m/z=600.22(C ₄₄ H ₂₈ N ₂ O=600.72) P-6 m/z=678.3(C ₅₁ H ₃₈ N ₂ =678.88) P-7 m/z=728.32(C ₅₅ H ₄₀ N ₂ =728.94) P-8 m/z=597.23(C ₄₂ H ₂₃ D ₅ N ₂ S=597.79) P-9 m/z=728.32(C ₅₅ H ₄₀ N ₂ =728.94) P-10 m/z=668.23(C ₄₈ H ₃₂ N ₂ S=668.86) P-11 m/z=728.32(C ₅₅ H ₄₀ N ₂ =728.94) P-12 m/z=652.25(C ₄₈ H ₃₂ N ₂ O=652.8) P-13 m/z=632.23(C ₄₅ H ₃₂ N ₂ S=632.83) P-14 m/z=692.28(C ₅₁ H ₃₆ N ₂ O=692.86) P-15 m/z=544.2(C ₃₈ H ₂₈ N ₂ S=544.72) P-16 m/z=666.27(C ₄₉ H ₃₄ N ₂ O=666.82) P-17 m/z=678.27(C ₅₀ H ₃₄ N ₂ O=678.84) P-18 m/z=700.29(C ₅₃ H ₃₆ N ₂ =700.89) P-19 m/z=666.25(C ₄₉ H ₃₁ F N ₂ =666.8) P-20 m/z=744.26(C ₅₄ H ₃₆ N ₂ S=744.96) P-21 m/z=762.18(C ₅₂ H ₃₀ N ₂ O S ₂ =762.95) P-22 m/z=843.36(C ₆₃ H ₄₅ N ₃ =844.07) P-23 m/z=1114.71(C ₈₃ H ₉₀ N ₂ =1115.65) P-24 m/z=780.35(C ₅₉ H ₄₄ N ₂ =781.02) P-25 m/z=582.3(C ₄₃ H ₃₈ N ₂ =582.79) P-26 m/z=804.31(C ₆₀ H ₄₀ N ₂ O=804.99) P-27 m/z=668.23(C ₄₈ H ₃₂ N ₂ S=668.86) P-28 m/z=893.38(C ₆₇ H ₄₇ N ₃ =894.13) P-29 m/z=756.31(C ₅₆ H ₄₀ N ₂ O=756.95) P-30 m/z=700.2(C ₄₈ H ₃₂ N ₂ S ₂ =700.92) P-31 m/z=684.22(C ₄₈ H ₃₂ N ₂ OS=684.86) P-32 m/z=694.3(C ₅₁ H ₃₈ N ₂ O=694.88) P-33 m/z=708.26(C ₅₀ H ₃₆ N ₂ OSi=708.94) P-34 m/z=600.22(C ₄₄ H ₂₈ N ₂ O=600.72) P-35 m/z=781.35(C ₅₉ H ₃₅ D ₅ N ₂ =782.01) P-36 m/z=692.23(C ₅₀ H ₃₂ N ₂ S=692.88) P-37 m/z=500.19(C ₃₆ H ₂₄ N ₂ O=500.6) P-38 m/z=650.27(C ₄₉ H ₃₄ N ₂ =650.83) P-39 m/z=592.2(C ₄₂ H ₂₈ N ₂ S=592.76) P-40 m/z=652.29(C ₄₉ H ₃₆ N ₂ =652.84) P-41 m/z=531.27(C ₃₉ H ₂₅ D ₅ N ₂ =531.71) P-42 m/z=518.18(C ₃₆ H ₂₃ FN ₂ O=518.59) P-43 m/z=622.15(C ₄₂ H ₂₆ N ₂ S ₂ =622.8) P-44 m/z=714.18(C ₄₈ H ₃₀ N ₂ OS ₂ =714.9) P-45 m/z=638.27(C ₄₈ H ₃₄ N ₂ =638.81) P-46 m/z=952.48(C ₇₂ H ₆₀ N ₂ =953.29) P-47 m/z=854.33(C ₆₄ H ₄₂ N ₂ O=855.05) P-48 m/z=770.24(C ₅₅ H ₃₄ N ₂ OS=770.95) P-49 m/z=942.31(C ₆₇ H ₄₆ N ₂ S ₂ =943.24) P-50 m/z=666.27(C ₄₉ H ₃₄ N ₂ O=666.82) P-51 m/z=652.29(C ₄₉ H ₃₆ N ₂ =652.84) P-52 m/z=600.22(C ₄₄ H ₂₈ N ₂ O=600.72) P-53 m/z=892.35(C ₆₄ H ₄₈ N ₂ OS=893.16) P-54 m/z=894.22(C ₆₁ H ₃₈ N ₂ S ₃ =895.17) P-55 m/z=718.26(C ₅₂ H ₃₄ N ₂ O ₂ =718.86) P-56 m/z=845.34(C ₆₂ H ₄₃ N ₃ O=846.05) P-57 m/z=844.38(C ₆₄ H ₄₈ N ₂ =845.1) P-58 m/z=718.24(C ₅₂ H ₃₄ N ₂ S=718.92) P-59 m/z=790.3(C ₅₆ H ₄₂ N ₂ OS=791.03) P-60 m/z=956.41(C ₇₃ H ₅₂ N ₂ =957.23) P-61 m/z=582.18(C ₄₀ H ₂₆ N ₂ OS=582.72) P-62 m/z=712.29(C ₅₁ H ₃₇ FN ₂ O=712.87) P-63 m/z=760.29(C ₅₅ H ₄₀ N ₂ S=761) P-64 m/z=668.28(C ₄₉ H ₃₆ N ₂ O=668.84) P-65 m/z=648.22(C ₄₅ H ₃₂ N ₂ OS=648.82) P-66 m/z=708.28(C ₅₁ H ₃₆ N ₂ O ₂ =708.86) P-67 m/z=576.17(C ₃₈ H ₂₈ N ₂ S ₂ =576.78) P-68 m/z=859.39(C ₆₄ H ₄₉ N ₃ =860.12) P-69 m/z=756.28(C ₅₅ H ₃₆ N ₂ O ₂ =756.91) P-70 m/z=932.28(C ₆₃ H ₄₀ F ₄ N ₂ S=933.08) P-71 m/z=664.22(C ₄₅ H ₃₂ N ₂ O ₂ S=664.82) P-72 m/z=810.36(C ₆₀ H ₄₆ N ₂ O=811.04) P-73 m/z=734.24(C ₅₂ H ₃₄ N ₂ OS=734.92) P-74 m/z=694.3(C ₅₁ H ₃₈ N ₂ O=694.88) P-75 m/z=668.25(C ₄₈ H ₃₂ N ₂ O ₂ =668.8) P-76 m/z=658.21(C ₄₆ H ₃₀ N ₂ OS=658.82) P-77 m/z=774.27(C ₅₅ H ₃₈ N ₂ OS=774.98) P-78 m/z=650.24(C ₄₅ H ₃₄ N ₂ OS=650.84) P-79 m/z=690.3(C ₅₂ H ₃₈ N ₂ =690.89) P-80 m/z=648.19(C ₄₄ H ₂₈ N ₂ O ₂ S=648.78) P-81 m/z=818.33(C ₆₁ H ₄₂ N ₂ O=819.02) P-82 m/z=622.17(C ₄₂ H ₂₆ N ₂ O ₂ S=622.74) P-83 m/z=782.28(C ₅₇ H ₃₈ N ₂ S=783.01) P-84 m/z=660.31(C ₄₈ H ₄₀ N ₂ O=660.86) P-85 m/z=674.2(C ₄₆ H ₃₀ N ₂ O ₂ S=674.82) P-86 m/z=832.31(C ₅₈ H ₄₄ N ₂ O ₂ S=833.06)

Manufacturing and Evaluation of Organic Electronics

[ Example 1] Red organic electroluminescent device ( Luminescent auxiliary layer )

An organic electroluminescent device was manufactured using the compound of the present invention as a light-emitting auxiliary layer material according to a conventional method. First, N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine (hereinafter, abbreviated as 2-TNATA) was vacuum-deposited to a thickness of 60 nm on an ITO layer (anode) formed on a glass substrate to form a hole injection layer. 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter, abbreviated as NPB) as a hole transport compound was vacuum-deposited to a thickness of 60 nm on the hole injection layer to form a hole transport layer.

Thereafter, the compound P-1 of the present invention was vacuum-deposited to a thickness of 20 nm on the hole transport layer to form a light-emitting auxiliary layer. On the light-emitting auxiliary layer, CBP [4,4'-N,N'-dicarbazole-biphenyl] was used as a host material, and bis-(1-phenylisoquinolyl)iridium(Ⅲ)acetylacetonate (hereinafter, abbreviated as (piq)2Ir(acac)) was used as a dopant material, doping at a weight ratio of 95:5, thereby depositing a light-emitting layer to a thickness of 30 nm on the light-emitting auxiliary layer.

Next, (1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 5 nm on the light-emitting layer to form a hole-blocking layer. Bis(10-hydroxybenzo[h]quinolinato)beryllium (hereinafter abbreviated as BeBq2) was vacuum-deposited to a thickness of 40 nm on the hole-blocking layer to form an electron-transport layer.

Afterwards, LiF, a halogenated alkali metal, was deposited to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic light-emitting device.

[ Example 2] to [ Example 16]

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

[ Comparative example 1]

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

[ Comparative example 2] to [ Comparative example 4]

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Comparative Compounds 1 to 3 were used as light-emitting auxiliary layer materials, respectively.

Comparative compound 1 Comparative compound 2 Comparative compound 3

The electroluminescence (EL) characteristics were measured using PR-650 of Photoresearch by applying a forward bias DC voltage to the organic electroluminescent devices manufactured in this manner and the comparative examples, and the T95 lifespan was measured using a lifespan measuring device manufactured by Maxscience at a standard luminance of 2500 cd/m ² . Table 4 below shows the results of device fabrication and evaluation.

compound Driving voltage Current (mA/cm ² ) Luminance (cd/m ² ) Efficiency
(cd/A) T(95) CIE X Y Comparative example (1) - 6.5 33.3 2500 7.5 64.2 0.66 0.32 Comparative example (2) Comparative compound 1 6.2 21.6 2500 11.6 82.7 0.66 0.33 Comparative example (3) Comparative compound 2 5.9 13.7 2500 18.2 86.1 0.66 0.33 Comparative example (4) Comparative compound 3 5.9 16.1 2500 15.5 89.4 0.66 0.32 Example (1) P-2 4.8 8.4 2500 29.6 131.8 0.66 0.32 Example (2) P-4 4.8 8.5 2500 29.4 133.1 0.66 0.33 Example (3) P-14 4.9 8.7 2500 28.8 129.2 0.66 0.33 Example (4) P-15 4.9 8.8 2500 28.5 130.0 0.66 0.33 Example (5) P-27 4.8 8.6 2500 29.0 133.9 0.66 0.33 Example (6) P-29 5.0 8.9 2500 28.2 127.5 0.66 0.33 Example (7) P-32 5.0 8.9 2500 28.0 128.2 0.66 0.33 Example (8) P-35 5.3 9.7 2500 25.9 116.7 0.66 0.33 Example (9) P-37 5.1 9.3 2500 27.0 125.3 0.66 0.32 Example (10) P-41 5.2 9.4 2500 26.7 123.1 0.66 0.32 Example (11) P-53 5.2 9.5 2500 26.3 121.5 0.66 0.32 Example (12) P-65 5.1 9.1 2500 27.6 126.8 0.66 0.32 Example (13) P-73 5.1 9.2 2500 27.3 124.2 0.66 0.32 Example (14) P-84 5.6 10.1 2500 24.7 110.6 0.66 0.33 Example (15) P-85 5.5 10.3 2500 24.3 111.0 0.66 0.32 Example (16) P-86 5.6 10.4 2500 24.0 112.4 0.66 0.33

As can be seen from the results in Table 4 above, when a red organic electroluminescent device is manufactured using the material for an organic electroluminescent device of the present invention as a light-emitting auxiliary layer material, the electrical characteristics of the organic electroluminescent device can be improved compared to the comparative examples in which the light-emitting auxiliary layer is not formed or in which comparative compounds 1 to 3 are used.

That is, in Comparative Examples 2 to 4 using Comparative Compounds 1 to 3 as light-emitting auxiliary layers, the driving voltage, efficiency, and lifespan of the device were improved compared to Comparative Example 1 in which the light-emitting auxiliary layer was not formed, and it could be confirmed that the device results of Examples 1 to 16 using the compound represented by Chemical Formula 1 of the present invention as the light-emitting auxiliary layer material were significantly improved compared to Comparative Examples 1 to 4.

This is because the compound represented by the chemical formula 1 of the present invention has a structure different from that of comparative compounds, and thus the energy level (e.g., HOMO, LUMO, T1) of the compound has properties suitable as a light-emitting auxiliary layer material, and thus acts as a major factor (charge balance of holes and electrons, hole mobility, electron mobility, Hole characteristics) in improving device performance during device deposition, resulting in improved driving voltage, efficiency, and lifespan.

In addition, the evaluation results of the above-described device fabrication explained the device characteristics in which the compound of the present invention was applied only to the light-emitting auxiliary layer, but the compound of the present invention can be used by applying it to the hole transport layer or by applying it to both the hole transport layer and the light-emitting auxiliary layer.

The above description is merely an example of the present invention, and those skilled in the art will appreciate that various modifications may be made without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed in this specification are not intended to limit the present invention but to explain it, 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 techniques within a scope equivalent thereto should be interpreted as being included in the scope of the rights of the present invention.

100, 200, 300: Organic electric element 110: First electrode
120: Hole injection layer 130: Hole transport layer
140: Emitting layer 150: Electron transport layer
160: Electron injection layer 170: Second electrode
180: Light efficiency improvement layer 210: Buffer layer
220: Light-emitting auxiliary layer 320: First hole injection layer
330: First hole transport layer 340: First light emitting layer
350: 1st electron transport layer 360: 1st 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: 1st stack ST2: 2nd stack

Claims (14)

A compound represented by the following chemical formula 1
Chemical Formula 1 Chemical Formula 1-1

{In the above chemical formula 1,
1) Ar ¹ and Ar ² are independently selected from the group consisting of a C ₆ to C ₆₀ aryl group; a fluorenyl group; a C ₂ to C ₆₀ heterocyclic group including at least one heteroatom selected from O, N, S, Si and P; and a fused ring group of a C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring;
2) L ₁ and L ₂ are independently selected from the group consisting of a single bond; a C ₆ to C ₆₀ arylene group; a fluorenylene group; a C ₂ to C ₆₀ heterocyclic group including at least one heteroatom among O, N, S, Si and P; and a C ₃ to C ₆₀ aliphatic ring group;
3) X ₁ and X ₂ are independently a single bond, O, S or CR'R",
4) The R' and R" are independently selected from the group _consisting of hydrogen; deuterium; a C ₁ to C ₆₀ alkyl group; a C ₂ to C ₆₀ alkenyl group; a C ₂ to C ₆₀ alkynyl group; a C ₁ to C ₆₀ alkoxy group; a C ₆ to C 60 aryloxy group; a C ₆ to C ₆₀ aryl group; a fluorenyl group; a C ₂ to C ₆₀ heterocyclic group including at least one heteroatom selected from O, N, S, Si and P; and a fused ring group of a C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring; or R' and R" may be combined with each other to form a spiro ring,
5) m and n are independently 0 or 1, and when m and n are 0, X ₁ and X ₂ do not exist, and l is an integer from 0 to 3,
6) T ₁ , T ₂ , T ₃ and T ₄ are independently selected from the group consisting of a C ₆ ~ C ₆₀ aromatic ring group; a C ₃ ~ C ₆₀ aliphatic ring group; a C ₂ ~ C ₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si and P; and a fused ring group of a C ₃ ~ C ₆₀ aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring; provided that at least one of T ₁ , T ₂ , T ₃ and T ₄ is a substituent represented by the chemical formula 1-1,
In the above chemical formula 1-1,
6) Y ₁ and Y ₂ are independently a single bond, O, S or CR'R", except in the case where both Y ₁ and Y ₂ are single bonds.
7) R _a and R _b are each the same or different, and are independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; nitro group; C ₆ to C ₆₀ aryl group; fluorenyl group; C ₂ to C ₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si and P; a fused ring group of a C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring; _{a C 1 to} C ₆₀ alkyl group; a C ₂ to C ₆₀ alkenyl group; a C ₂ to C ₆₀ alkynyl group; _a C ₁ to C 60 alkoxy group; a C 6 to C ₆₀ aryloxy group; and -L'-NR ^c R ^d ;, or a plurality of adjacent R _{a groups} can be bonded to each other to form a ring,
8) The L' is selected from the group consisting of a single bond; a C ₆ ~C ₆₀ arylene group; a fluorenyl group; a C ₂ ~C ₆₀ heterocyclic group including at least one heteroatom among O, N, S, Si and P; and a C ₃ ~C ₆₀ aliphatic ring group; and the R ^c and R ^d are each independently selected from the group consisting of a C ₆ ~C ₆₀ aryl group; a fluorenyl group; a C ₂ ~C ₆₀ heterocyclic group including at least one heteroatom among O, N, S, Si and P; and a fused ring group of a C ₃ ~C ₆₀ aliphatic ring and a C ₆ ~C ₆₀ aromatic ring;
9) a is an integer from 0 to 2, b is an integer from 0 to 4,
10) * indicates the binding position,
Here, the aryl group, the arylene group, the heterocyclic group, the fluorenyl group, the fluorenylene group, the aliphatic ring group, the fused ring group, the alkyl group, the alkenyl group, the alkoxy group and the aryloxy group are each independently selected from deuterium; halogen; a silane group; a siloxane group; a boron group; a germanium group; a cyano group; a nitro group; a C ₁ to C ₂₀ alkylthio group; _{a C 1 to} C ₂₀ alkoxy group; _a C ₁ to C ₂₀ alkyl group; a C ₂ to C ₂₀ alkenyl group; a C ₂ to C ₂₀ alkynyl group; a C 6 to C 20 aryl group; a C ₆ to C ₂₀ aryl group substituted with deuterium; a fluorenyl group; a C ₂ to C ₂₀ heterocyclic group; {It may be further substituted with one or more substituents selected from the group consisting of a C ₃ ~C ₂₀ cycloalkyl group; a C ₇ ~C ₂₀ arylalkyl group; and a C ₈ ~C ₂₀ arylalkenyl group; and further, these substituents may be combined with each other to form a ring, wherein the 'ring' refers to a fused ring formed by a C ₃ ~C ₆₀ aliphatic ring, a C ₆ ~C ₆₀ aromatic ring, a C ₂ ~C ₆₀ heterocycle, or a combination thereof, and includes a saturated or unsaturated ring.}
delete In the first paragraph, the chemical formula 1 is a compound represented by any one of the following chemical formulas 4 to 12.
Chemical Formula 4 Chemical Formula 5 Chemical Formula 6

Chemical Formula 7 Chemical Formula 8 Chemical Formula 9

Chemical Formula 10 Chemical Formula 11 Chemical Formula 12

{In the chemical formulas 4 to 12 above,
1) Ar ¹ , Ar ² , L ₁ , L ₂ , X ₁ , Y ₁ , Y ₂ , R _a , R _b , a and b are as defined in claim 1,
2) R ₁ , R ₂ and R ₃ are independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; nitro group; C ₆ to C ₂₀ aryl group; fluorenyl group; C ₂ to C ₂₀ heterocyclic group containing at least one heteroatom among O, N, S, Si and P; C ₁ to C ₂₀ alkyl group; C ₂ to C ₂₀ alkenyl group; C ₂ to C ₂₀ alkynyl group; and C ₁ to C ₂₀ alkoxy group;
c, d and e are independently integers from 0 to 4,
3) L ₂ and Ar ₂ may be further substituted independently by a group selected from hydrogen; deuterium; halogen; cyano group; nitro group; C ₆ to C ₂₀ aryl group; fluorenyl group; C ₂ to C ₂₀ heterocyclic group containing at least one heteroatom among O, N, S, Si and P; C ₁ to C ₂₀ alkyl group; C ₂ to C ₂₀ alkenyl group; C ₂ to C ₂₀ alkynyl group; and C ₁ to C ₂₀ alkoxy group.
In the first paragraph, the compound represented by the chemical formula 1 is characterized by being one of the following compounds:

An organic electric device comprising an anode, a cathode, and an organic layer formed between the anode and the cathode, characterized in that the organic layer comprises a single compound or two or more compounds represented by the chemical formula 1 of claim 1.
In the fifth paragraph, an organic electric device characterized in that the organic layer includes at least one 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.
In the fifth paragraph, an organic electric device characterized in that the organic material layer is a light-emitting auxiliary layer.
In the fifth paragraph, an organic electric device characterized in that the organic layer is a hole transport layer.
In the fifth paragraph, an organic electric device further comprising a light efficiency improvement layer formed on at least one surface of the anode and cathode opposite to the organic layer.
In the fifth paragraph, an organic electric device characterized in that the organic material layer is a light efficiency improvement layer.
In the fifth paragraph, an organic electric device characterized in that the organic layer includes two or more stacks including a hole transport layer, a light-emitting layer, and an electron transport layer sequentially formed on an anode.
In the 11th paragraph, an organic electric device characterized in that the organic material layer further includes a charge generation layer formed between the two or more stacks.
An electronic device comprising a display device including an organic electric element of clause 5; and a control unit for driving the display device.
In claim 13, the organic electric element is an electronic device characterized in that it is at least one of an organic light-emitting diode (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a monochrome or white lighting element.