KR20200081771A - 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 mixture capable of increasing light emitting efficiency, stability, and lifespan of an element, an organic electronic element using the same, and an electronic device thereof. The organic electronic element comprises: a first electrode; a second electrode; and an organic material layer formed between the first electrode and the second electrode.

Description

Compound for organic electric element, organic electric element using the same, and its electronic device {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 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 their function.

In the case of a bis-type cyclic compound containing a hetero atom, the difference in properties according to the material structure is very large, and thus it is applied to various layers as a material for an organic electric device. In particular, the band gap (HOMO, LUMO), electrical properties, chemical properties, physical properties, etc. have different characteristics depending on the number of rings, fused positions, and the type and arrangement of heteroatoms. This has been going on.

In a phosphorescent organic electric device using a phosphorescent dopant material, the LUMO and HOMO levels of the host material are factors influencing the efficiency and lifespan of the organic electric device. Accordingly, it is possible to control the charge balance in the light emitting layer, the quenching of the dopant, and the reduction in efficiency and life due to light emission at the interface of the hole transport layer can be prevented.

In the case of host materials for fluorescence and phosphorescence, recently, research has been conducted on increasing the efficiency and lifetime of organic electric devices using thermal activatied delayed fluorescent (TADF), exciplex, etc., and in particular, identifying energy transfer methods from host materials to dopant materials There is a lot of research going on.

Although there are several methods for identifying energy transfer in the light emitting layer for TADF (Thermal Activated Delayed Fluorescence), exciplex, it can be easily confirmed by PL lifetime (TRTP) measurement.

The TRTP (Time resolved transient PL) measurement method is a method of observing the decay time of a spectrum over time after irradiating a pulsed light source to a host thin film. It is a measurement method. The TRTP measurement is a measurement method capable of distinguishing between fluorescence and phosphorescence, energy transfer method in mixed host material, exciplex energy transfer method, and TADF energy transfer method.

As described above, there are various factors affecting efficiency and lifespan depending on the manner in which energy is transferred from the host material to the dopant material, and the energy transmission method is different according to the material, so that the development of a stable and efficient host material for an organic electric device This is not done enough. Therefore, the development of new materials continues to be required, and in particular, the development of the host material of the light emitting layer is urgently required.

KR 101170666 B1

The present invention has been proposed to solve the problems of the phosphorescent host material as described above, the charge balance in the light emitting layer through the HOMO level control for the host material of the phosphorescent light-emitting organic electroluminescent device containing a phosphorescent dopant, and the efficiency, life span It is an object of the present invention to provide an organic electric device using the same compound and an electronic device thereof.

The present invention is to reduce the energy barrier between the light emitting layer and the adjacent layer by containing a specific first host material in combination with a specific first host material as a main component in order to control efficient hole injection in the light emitting layer of the phosphorescent organic electroluminescent device. It is possible to maximize the charge balance in the light emitting layer to provide high efficiency and high lifespan of the organic electric device.

In an organic electric device comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, the organic material layer includes a light emitting layer, and the light emitting layer is a phosphorescent light emitting layer represented by the following formula (1). It provides an organic electric device comprising a first host compound represented by a) and a second host compound represented by the following formula (2).

Formula (1) Formula (2)

In addition, the present invention provides an organic electric device using the compound represented by the above formulas and an electronic device thereof.

By using the mixture according to the present invention as a phosphorescent host material, it is possible to achieve high luminous efficiency and low driving voltage of the organic electric device, and also to significantly improve the life of the device.

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

Hereinafter, with reference to the embodiment of the present invention will be described in detail. In describing the present invention, when it is determined that detailed descriptions of related known configurations or functions may obscure the subject matter of the present invention, detailed descriptions thereof will be omitted.

In addition, 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 elements may be "connected", "coupled" or "connected".

As used in this specification and the appended claims, unless otherwise stated, the meaning of the following terms is as follows:

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

The term "alkyl" or "alkyl group" used in the present invention has a single bond of 1 to 60 carbon atoms, unless otherwise specified, a straight chain alkyl group, branched chain alkyl group, cycloalkyl (alicyclic) group, alkyl-substituted cyclo By radicals of saturated aliphatic functional groups, including alkyl groups, cycloalkyl-substituted alkyl groups.

The term "haloalkyl group" or "halogenalkyl group" as used in the present invention means an alkyl group substituted with halogen unless otherwise specified.

The term "heteroalkyl group" used in the present invention means that at least one of the carbon atoms constituting the alkyl group is replaced with a heteroatom.

The terms "alkenyl group", "alkenyl group" or "alkynyl group" used in the present invention have a double or triple bond of 2 to 60 carbon atoms, unless otherwise specified, and include straight or branched chain groups. , But is not limited to this.

As used herein, the term "cycloalkyl" means an alkyl forming a ring having 3 to 60 carbon atoms, unless otherwise specified, and is not limited thereto.

The term "alkoxyl group", "alkoxy group", or "alkyloxy group" used in the present invention means an alkyl group to which an oxygen radical is attached, and has a carbon number of 1 to 60 unless otherwise specified, and is limited thereto. It is not.

As used herein, the terms "alkenoxyl group", "alkenoxy group", "alkenyloxyl group", or "alkenyloxy group" means an alkenyl group to which an oxygen radical is attached, and 2 to 60 unless otherwise specified. It has a carbon number, and is not limited thereto.

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

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 means a single ring or multi-ring aromatic, and includes an aromatic ring formed by adjacent substituents participating in a bond or reaction. For example, the aryl group may be a phenyl group, biphenyl group, fluorene group, dimethylfluorene group, diphenylfluorene group, or spirofluorene group.

The prefix "aryl" or "ar" means 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 a radical substituted with an aryl group has a carbon number described herein.

Also, when the prefix is named in succession, it means that the substituents are listed in the order described first. For example, in the case of an arylalkoxy group, it means an alkoxy group substituted with an aryl group, in the case of an alkoxycarbonyl group, it means a carbonyl group substituted with an alkoxyl group, and in the case of an arylcarbonyl alkenyl group, it means an alkenyl group substituted with an arylcarbonyl group. Wherein the arylcarbonyl group is a carbonyl group substituted with an aryl group.

As used herein, the term "heteroalkyl" means alkyl containing one or more heteroatoms, unless otherwise specified. As used herein, the term "heteroaryl group" or "heteroarylene group" means an aryl group or an arylene group having 2 to 60 carbon atoms each containing at least one heteroatom, unless otherwise specified, and is not limited thereto. No, it includes at least one of a single ring and multiple rings, and may be formed by combining adjacent functional devices.

The term "heterocyclic group" used in the present invention includes at least one heteroatom, has 2 to 60 carbon atoms, includes at least one of a single ring and multiple rings, heteroaliphatic ring and hetero, unless otherwise specified. Aromatic rings. Adjacent functional groups may also be formed by bonding.

The term “heteroatom” as used herein refers to N, O, S, P or Si, unless otherwise stated.

In addition, the "heterocyclic group" may include a ring containing SO ₂ instead of carbon forming a ring. For example, "heterocyclic group" includes the following compounds.

Unless otherwise stated, the term "aliphatic" used in the present invention 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 specified, the term "ring" used in the present invention refers to 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 It contains a saturated or unsaturated ring.

Other hetero compounds or hetero radicals other than the above-described hetero compounds include one or more hetero atoms, but are not limited thereto.

Unless otherwise specified, the term "carbonyl" used in the present invention is represented by -COR', where R'is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, 3 to 30 carbon atoms. Is a cycloalkyl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.

Unless otherwise specified, the term "ether" used in the present invention is represented by -RO-R', wherein R or R'are each independently of each other hydrogen, an alkyl group having 1 to 20 carbon atoms, or 6 to 30 carbon atoms. It is an aryl group, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.

Also, unless expressly stated, the term "substituted" in the term "substituted or unsubstituted" as used in the present invention is deuterium, halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxyl group, C ₁ ~ C ₂₀ alkylamine group, C ₁ ~ C ₂₀ alkylthiophene group, C ₆ ~ C ₂₀ arylthiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl group, substituted with deuterium C ₆ ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ aryl alkenyl group, silane group, boron Means a group, a germanium group, and one or more substituents selected from the group consisting of C ₂ to C ₂₀ heterocyclic groups, and is not limited to these substituents.

In addition, unless explicitly stated, the formula used in the present invention is applied in the same manner as the substituent definition by the exponent 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 of the carbons forming the benzene ring. The formula or compound may be omitted. 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, each of them is bonded as follows, where R ¹ may be the same or different from each other. When a is an integer of 4 to 6, it binds to the carbon of the benzene ring in a similar manner, while the indication of hydrogen bound to the carbon forming the benzene ring is omitted.

Also, unless expressly stated, the terms "ortho", "meta", and "para" used in the present invention mean the position of substitution of all substituents, and the position of ortho is the substituent The position of represents a neighboring compound, for example, in the case of benzene, means 1 or 2 digits, and the meta position represents the next substitution position in the immediate substitution position, and when benzene is used as an example, 1 or 3 digits are indicated. Meaning, the para position means 1 or 4 digits when benzene is an example as the next substitution position of the meta position. The description of a more detailed substitution position example is as follows, and it can be confirmed that the ortho- or meta- position is replaced with a non-linear type, and the para-(para-) position is replaced with a linear type. have.

[Example of ortho-location]

[Example of meta-position]

[Example of para-position]

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

In an organic electric device comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, the organic material layer includes a light emitting layer, and the light emitting layer is a phosphorescent light emitting layer (1) It provides an organic electroluminescent device comprising a first host compound represented by and a second host compound represented by the formula (2).

Formula (1) Formula (2)

{In the formulas (1) and (2) above,

1) Ar ¹ , Ar ² , Ar ³ , Ar ⁴ and Ar ⁵ are each independently hydrogen; heavy hydrogen; C ₆ ~ C ₆₀ Aryl group; Alkyl groups; C ₂ ~ C ₆₀ heteroaryl group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~C ₃₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And -L'-N(R _a )(R _b ); Ar ⁴ and Ar ⁵ may be bonded to each other to form a ring,

2) L ¹ , L ² and L'are each independently a single bond; C ₆ ~ C ₆₀ Arylene group; Or C ₂ ~ C ₆₀ heteroarylene group; is,

3) n is 1 or 2,

4) a is an integer from 0 to 6; b, c and e are each independently an integer from 0 to 4; d is an integer from 0 to 3,

5) R ¹ to R ⁵ are each independently 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 and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~C ₃₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And -L'-N (R _a ) (R _b ); is selected from the group consisting of,

When a, b, c, d and e are 2 or more, they are the same as or different from each other, and a plurality of R ¹ , a plurality of R ² , a plurality of R ³ , a plurality of R ⁴ , and a plurality of R ⁵ They may combine with each other to form an aromatic and heteroaromatic ring,

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 C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom; is selected from the group consisting of,

Here, the aryl group, fluorenyl group, arylene group, heterocyclic group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group each deuterium; halogen; Silane group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio; Alkoxyl group of C ₁ -C ₂₀ ; C ₁ -C ₂₀ alkyl group; Alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ Aryl group; A C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl group; C ₂ -C ₂₀ heterocyclic group; C ₃ -C ₂₀ cycloalkyl group; C ₇ -C ₂₀ arylalkyl group and C ₈ -C ₂₀ arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of, also, these substituents may combine with each other to form a ring, wherein ''Cycle' refers to a C ₃ -C ₆₀ aliphatic ring or a C ₆ -C ₆₀ aromatic ring or a C ₂ -C ₆₀ heterocycle or a fused ring thereof, and includes a saturated or unsaturated ring.}

As another example, the present invention provides an organic electric device comprising a compound in which at least one of R ¹ and R ² of the compound represented by Formula (1) is an aryl group of C ₆ to C ₆₀ .

As another specific example, the present invention provides an organic electric device in which the compounds represented by the formula (1) include compounds represented by the following formulas (3) to (16).

Formula (3) Formula (4) Formula (5) Formula (6)

Formula (7) Formula (8) Formula (9) Formula (10)

Formula (11) Formula (12) Formula (13) Formula (14)

Formula (15) Formula (16)

{In the formulas (3) to (16), Ar ¹ , Ar ² , L ¹ , R ¹ , R ² , a, b are the same as defined above,

1) R ⁶ and R ⁷ are each independently hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₄₈ aryl group; Fluorenyl group; C ₂ ~ C ₄₈ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₄₈ aliphatic ring and C ₆ ~ C ₄₈ aromatic ring fused 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,

When f or g is 2 or more, a plurality of R ^{6 s} or a plurality of R ^{7 s may} combine with each other to form an aromatic and heteroaromatic ring,

2) f and g are any integers from 0 to 5.}

In addition, the present invention provides an organic electric device comprising at least one of Ar ¹ and Ar ² represented by the following formula (1-1).

Formula (1-1)

{In the above formula (1-1),

1) X is O, S, CR'R", SiR'R", Se, or NR',

2) R'and R" are each independently selected from the group consisting of hydrogen; C ₁ ~C ₂₀ alkyl group; C ₆ ~ C ₂₀ aryl group; and C ₂ ~ C ₂₀ heteroaryl group; or R 'And R" form a ring with each other to form a spiro ring,

3) R ⁸ and R ⁹ are each independently hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring and C ₆ ~ C ₂₀ aromatic ring fused ring group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~C ₃₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And -L'-N(R _a )(R _b ); when h and i are 2 or more, they are the same or different from each other as a plurality, and a plurality of R ^8s and a plurality of R ^9s are bonded to each other To form an aromatic and heteroaromatic ring, L', R _a and R _b are the same as defined above,

4) h is an integer from 0 to 4, and i is an integer from 0 to 3.}

In addition, in the present invention, the compounds represented by the formula (1) include the following formulas (17) to (20).

Formula (17) Formula (18) Formula (19) Formula (20)

{In the formulas (17) to (20), R ¹ , R ² , Ar ¹ , R ⁸ , R ⁹ , a, b, h, and i are the same as defined above.}

In the present invention, there is provided an organic electric device comprising a compound when a and b are both 0 of the compound represented by the formula (1).

As another example, the present invention is an organic compound containing a compound in which at least one of R ¹ and R ² of the compound represented by Chemical Formula (1) has two or more adjacent pairs of each other to form a ring when a or b is 2 or more. An electrical device is provided.

The compound of Formula (1) includes, but is not limited to the following compounds.

As another example, the present invention provides an organic electric device in which the compound represented by the formula (2) includes a compound represented by any one of the following formulas (21) to (24).

Formula (21) Formula (22) Formula (23) Formula (24)

{In the above formulas (21) to (24),

R ³ , R ⁴ , R ⁵ , Ar ³ , Ar ⁴ , Ar ⁵ , L ² , c, d, e and n are the same as defined above.}

In addition, the present invention provides an organic electric device comprising a compound represented by any one of the following formulas (25) to (33).

Formula (25) Formula (26) Formula (27)

Formula (28) Formula (29) Formula (30)

Formula (31) Formula (32) Formula (33)

{In the formulas (25) to (33) above,

R ³ , R ⁴ , R ⁵ , Ar ³ , Ar ⁴ , Ar ⁵ , L ² , c, d, e are the same as defined above,

Ar ⁶ and Ar ⁷ are each independently hydrogen; heavy hydrogen; C ₆ ~ C ₆₀ Aryl group; Alkyl groups; C ₂ ~ C ₆₀ heteroaryl group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~C ₃₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And -L'-N(R _a )(R _b ); Ar ⁶ and Ar ⁷ may be bonded to each other to form a ring,

L', R _a and R _b are the same as defined above.}

As another example, the present invention provides an organic electric device comprising at least one of Ar ⁴ and Ar ⁵ represented by the following formula (2-1).

Formula (2-1)

{In the above formula (2-1),

1) Y is O, S, CR'R", SiR'R", Se, or NR',

2) R'and R” each independently hydrogen; C ₁ ~ C ₂₀ alkyl group; C ₆ ~ C ₂₀ aryl group; And C ₂ ~ C ₂₀ heteroaryl group; is selected from the group consisting of, or R'and R" to form a ring with each other to form a spiro (spiro) ring,

3) R ¹⁰ and R ¹¹ are each independently hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring and C ₆ ~ C ₂₀ aromatic ring fused ring group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₂₀ alkoxyl group; C ₆ ~ C ₂₀ Aryloxy group; And _{-L'-N (R a) (} R b); is selected from the group, j and the same or different from each other and bonded to each other a plurality of R ¹¹ among the plurality of R ^10, together as a plurality respectively not less than k is 2, consisting of To form an aromatic and heteroaromatic ring,

4) j is an integer from 0 to 4, k is an integer from 0 to 3,

5) L', R _a and R _b are the same as defined above.}

As another example, the present invention provides an organic electric device comprising a compound when c, d and e of the compound represented by the formula (2) are all zero.

In one embodiment, the present invention is at least any one of R ³ , R ⁴ and R ⁵ of the compound represented by the formula (2), when c, d or e is 2 or more, two or more neighboring pairs combine with each other to form a ring. It provides an organic electrical device comprising a compound.

As a specific example, the formula (2) includes the following compounds, but is not limited thereto.

Referring to FIG. 1, the organic electric device 100 according to the present invention includes a first electrode 120, a second electrode 180 and a first electrode 120 and a second electrode formed on the substrate 110. An organic material layer including the compound represented by Chemical Formula 1 is provided between (180). In this case, the first electrode 120 may be an anode (anode), the second electrode 180 may be a cathode (cathode), and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

The organic material layer sequentially comprises a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, a light emitting auxiliary layer 151, an electron transport layer 160 and an electron injection layer 170 on the first electrode 120 It can contain. At this time, layers other than the emission layer 150 may not be formed. A hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151, an electron transport auxiliary layer, a buffer layer 141, and the like may be further included, and the electron transport layer 160, etc. may also serve as a hole blocking layer.

In addition, although not shown, the organic electric device according to the present invention may further include a protective layer formed on one surface opposite to the organic material layer among at least one surface of the first electrode and the second electrode.

On the other hand, even in the same core, the band gap, electrical properties, and interfacial properties may vary depending on which substituents are attached at which positions, so the selection of the core and the combination of sub-substituents coupled thereto are also very good. It is important, and long life and high efficiency can be achieved at the same time when the energy level and T1 value between each organic material layer and the intrinsic properties of materials (mobility, interfacial properties, etc.) are optimally combined.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using a physical vapor deposition (PVD) method. For example, a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode, and a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, and an electron transport layer 160 are formed thereon. After forming an organic material layer including the electron injection layer 170, it can be manufactured by depositing a material that can be used as a cathode thereon. In addition, the light emitting auxiliary layer 151 may be further formed between the hole transport layer 140 and the light emitting layer 150, and the electron transport auxiliary layer may be further formed between the light emitting layer 150 and the electron transport layer 160.

Accordingly, the present invention provides the organic electroluminescent device included in the light emitting layer by mixing the compound represented by the formula (1) and the formula (2) in a ratio of any one of 1:9 to 9:1, preferably Is 1:9 to 5:5, more preferably mixed in a ratio of 2:8 to 3:7 and included in the light emitting layer.

The present invention further comprises a light efficiency improving layer formed on at least one of one side of the first electrode opposite to the organic material layer or one side of the second electrode opposite to the organic material layer from one side of the first electrode in the organic electric device. An organic electric device is provided.

In addition, in the present invention, the organic material layer is formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process and a roll-to-roll process, and the organic material layer according to the present invention can be formed by various methods Therefore, the scope of the present invention is not limited by the forming method.

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

WOLED (White Organic Light Emitting Device) has the advantage of being easy to realize high resolution and excellent processability, and can be manufactured using the color filter technology of the existing LCD. Various structures for white organic light emitting devices mainly used as backlight devices have been proposed and patented. Typically, the R (Red), G (Green), and B (Blue) light emitting units are mutually planar in a side-by-side manner, and the stacking method in which the R, G, and B light emitting layers are stacked up and down. There is a color conversion material (CCM) method using electroluminescence by the blue (B) organic light-emitting layer and photo-luminescence of the inorganic phosphor using light therefrom. May be applied to such WOLED.

In addition, the present invention is a display device comprising 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 device is at least one of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, and a monochromatic or white illumination device. At this time, the electronic device may be a current or future wired/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, examples of the synthesis of the compounds represented by the formulas (1) and (2) of the present invention and the production examples of the organic electroluminescent device of the present invention will be specifically described with reference to the following examples of the present invention. It is not limited.

[ Synthetic example One]

The compound represented by Chemical Formula (1) according to the present invention (final product 1) is prepared by reacting Sub 1 and Sub 2 as shown in Reaction Scheme 1 below.

<Scheme 1>

Sub 1 synthesis example

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

<Reaction Scheme 2>

1. Sub 1-1 Synthetic example

(1) Sub 1-1a synthesis

1-bromo-2-nitronaphthalene (50g, 198.4mmol), 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (40.5g, 198.4mmol), K ₂ CO ₃ (82.2g , 595.1mmol), Pd(PPh ₃ ) ₄ (13.75g, 11.9mmol) was put in a round bottom flask, dissolved in THF (990mL) and water (490mL), and refluxed at 80°C for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ and wiped with water. After drying and concentrating the organic layer with MgSO ₄ , the resulting organic material was separated using a silicagel column to obtain the desired product (41 g, 83%).

(2) Sub 1-1 synthesis

Sub 1-1a (41 g, 164.5 mmol) and triphenylphosphine (107.9 g, 411.2 mmol) obtained above were dissolved in o-dichlorobenzene (820 mL) and refluxed at 200° C. for 24 hours. After the reaction was completed, the solvent was removed using distillation under reduced pressure, and the concentrated product was silicagel column and recrystallized to obtain a desired product (28.9 g, 71%).

2. Sub 1-2 Synthetic example

(1) Sub 1-2a synthesis

1-bromo-2-nitro-4-phenylnaphthalene (50g, 152.4mmol), 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (31.1g, 152.4mmol), K ₂ CO ₃ (63.2g, 457.1mmol), Pd(PPh ₃ ) ₄ (10.56g, 9.14mmol), THF (760mL), and water (380mL) were carried out in the same manner as in Sub 1-1a, and the product (40.2g, 81%).

(2) Sub 1-2 synthesis

Sub 1-2a (40.2g, 123.6mmol) and triphenylphosphine (81g, 308.9mmol) obtained above were subjected to o-dichlorobenzene (620mL) in the same way as the experimental method for Sub 1-1, resulting in product (25.4g, 70%). ).

3. Sub 1-3 Synthetic example

(1) Sub 1-3a synthesis

1-bromo-2-nitro-4-phenylnaphthalene (50g, 152.4mmol), 2-([1,1'-biphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2 -dioxaborolane (42.7g, 152.4mmol), K ₂ CO ₃ (63.2g, 457.1mmol), Pd(PPh ₃ ) ₄ (10.56g, 9.14mmol), THF (760mL), water (380mL) Sub 1-1a Proceeding in the same manner as the experimental method of to obtain the product (48.9g, 80%).

(2) Sub 1-3 synthesis

Sub 1-3a (48.9g, 121.8mmol), triphenylphosphine (80g, 304.5mmol) obtained above were subjected to o-dichlorobenzene (610mL) in the same way as the experiment method for Sub 1-1, resulting in product (31.5g, 70%). ).

4. Sub 1-4 Synthetic example

(1) Sub 1-4a synthesis

1-bromo-2-nitronaphthalene (50g, 198.4mmol), 4,4,5,5-tetramethyl-2-(naphthalen-2-yl)-1,3,2-dioxaborolane (50.4g, 198.4mmol), K ₂ CO ₃ (82.2g, 595.1mmol), Pd(PPh ₃ ) ₄ (13.75g, 11.9mmol), THF (990mL), and water (490mL) were carried out in the same manner as in Sub 1-1a, and the product (48.7 g, 82%).

(2) Sub 1-4 synthesis

Sub 1-4a (48.7g, 162.7mmol) and triphenylphosphine (106.7g, 406.7mmol) obtained above were subjected to o-dichlorobenzene (810mL) in the same manner as the experiment method for Sub 1-1 to obtain the product (30.9g, 71). %).

5. Sub 1-5 Synthetic example

(1) Sub 1-5a synthesis

After dissolving 10-chlorophenanthren-9-amine (50.0g, 219.6mmol) in a round bottom flask with Toluene (1000mL), 2-bromo-1,1'-biphenyl (51.2g, 219.6mmol), Pd ₂ (dba) ₃ (6.03 g, 6.59 mmol), P(t-Bu) ₃ (2.67 g, 13.18 mmol), NaOt-Bu (42.2 g, 439.2 mmol) was added 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 resulting compound was recrystallized after applying a silica gel column to obtain a product (57.6 g, 69%).

(2) Sub 1-5 synthesis

Sub 1-5a (57.6 g, 151.6 mmol) obtained above was added to DMA (760 mL) and then Pd(OAc) ₂ (1.02 g, 4.55 mmol), K ₂ CO ₃ (62.9 g, 455 mmol), P(t -Bu) 3H·BF ₄ (11.4 mL, 9.1 mmol) was added and stirred at 90°C. 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 resulting compound was recrystallized after applying a silica gel column to obtain a product (34.9g, 67%).

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

compound FD-MS compound FD-MS Sub 1-1 m/z=217.09 (C ₁₆ H ₁₁ N=217.27) Sub 1-2 m/z=293.12 (C ₂₂ H ₁₅ N=293.37) Sub 1-3 m/z=369.15 (C ₂₈ H ₁₉ N=369.47) Sub 1-4 m/z=267.1 (C ₂₀ H ₁₃ N=267.33) Sub 1-5 m/z=343.14 (C ₂₆ H ₁₇ N=343.43) Sub 1-6 m/z=293.12 (C ₂₂ H ₁₅ N=293.37) Sub 1-7 m/z=293.12 (C ₂₂ H ₁₅ N=293.37) Sub 1-8 m/z=293.12 (C ₂₂ H ₁₅ N=293.37) Sub 1-9 m/z=293.12 (C ₂₂ H ₁₅ N=293.37) Sub 1-10 m/z=369.15 (C ₂₈ H ₁₉ N=369.47) Sub 1-11 m/z=369.15 (C ₂₈ H ₁₉ N=369.47) Sub 1-12 m/z=293.12 (C ₂₂ H ₁₅ N=293.37) Sub 1-13 m/z=293.12 (C ₂₂ H ₁₅ N=293.37) Sub 1-14 m/z=293.12 (C ₂₂ H ₁₅ N=293.37) Sub 1-15 m/z=369.15 (C ₂₈ H ₁₉ N=369.47) Sub 1-16 m/z=369.15 (C ₂₈ H ₁₉ N=369.47) Sub 1-17 m/z=369.15 (C ₂₈ H ₁₉ N=369.47) Sub 1-18 m/z=369.15 (C ₂₈ H ₁₉ N=369.47) Sub 1-19 m/z=369.15 (C ₂₈ H ₁₉ N=369.47) Sub 1-20 m/z=369.15 (C ₂₈ H ₁₉ N=369.47) Sub 1-21 m/z=293.12 (C ₂₂ H ₁₅ N=293.37) Sub 1-22 m/z=369.15 (C ₂₈ H ₁₉ N=369.47) Sub 1-23 m/z=369.15 (C ₂₈ H ₁₉ N=369.47) Sub 1-24 m/z=419.17 (C ₃₂ H ₂₁ N=419.53) Sub 1-25 m/z=343.14 (C ₂₆ H ₁₇ N=343.43) Sub 1-26 m/z=343.14 (C ₂₆ H ₁₇ N=343.43) Sub 1-27 m/z=369.15 (C ₂₈ H ₁₉ N=369.47) Sub 1-28 m/z=267.1 (C ₂₀ H ₁₃ N=267.33) Sub 1-29 m/z=267.1 (C ₂₀ H ₁₃ N=267.33) Sub 1-30 m/z=317.12 (C ₂₄ H ₁₅ N=317.39) Sub 1-31 m/z=317.12 (C ₂₄ H ₁₅ N=317.39) Sub 1-32 m/z=267.1 (C ₂₀ H ₁₃ N=267.33) Sub 1-33 m/z=267.1 (C ₂₀ H ₁₃ N=267.33) Sub 1-34 m/z=267.1 (C ₂₀ H ₁₃ N=267.33) Sub 1-35 m/z=267.1 (C ₂₀ H ₁₃ N=267.33) Sub 1-36 m/z=267.1 (C ₂₀ H ₁₃ N=267.33) Sub 1-37 m/z=317.12 (C ₂₄ H ₁₅ N=317.39) Sub 1-38 m/z=317.12 (C ₂₄ H ₁₅ N=317.39) Sub 1-39 m/z=317.12 (C ₂₄ H ₁₅ N=317.39) Sub 1-40 m/z=317.12 (C ₂₄ H ₁₅ N=317.39) Sub 1-41 m/z=317.12 (C ₂₄ H ₁₅ N=317.39) Sub 1-42 m/z=497.19 (C ₃₆ H ₂₃ N ₃ =497.6) Sub 1-43 m/z=448.17 (C ₃₁ H ₂₀ N ₄ =448.53) Sub 1-44 m/z=421.16 (C ₃₀ H ₁₉ N ₃ =421.5) Sub 1-45 m/z=294.12 (C ₂₁ H ₁₄ N ₂ =294.36) Sub 1-46 m/z=343.14 (C ₂₆ H ₁₇ N=343.43) Sub 1-47 m/z=343.14 (C ₂₆ H ₁₇ N=343.43) Sub 1-48 m/z=419.17 (C ₃₂ H ₂₁ N=419.53) Sub 1-49 m/z=393.15 (C ₃₀ H ₁₉ N=393.49) Sub 1-50 m/z=393.15 (C ₃₀ H ₁₉ N=393.49) Sub 1-51 m/z=343.14 (C ₂₆ H ₁₇ N=343.43) Sub 1-52 m/z=343.14 (C ₂₆ H ₁₇ N=343.43) Sub 1-53 m/z=343.14 (C ₂₆ H ₁₇ N=343.43) Sub 1-54 m/z=419.17 (C ₃₂ H ₂₁ N=419.53) Sub 1-55 m/z=343.14 (C ₂₆ H ₁₇ N=343.43) Sub 1-56 m/z=393.15 (C ₃₀ H ₁₉ N=393.49) Sub 1-57 m/z=393.15 (C ₃₀ H ₁₉ N=393.49) Sub 1-58 m/z=393.15 (C ₃₀ H ₁₉ N=393.49) Sub 1-59 m/z=393.15 (C ₃₀ H ₁₉ N=393.49) Sub 1-60 m/z=393.15 (C ₃₀ H ₁₉ N=393.49) Sub 1-61 m/z=477.13 (C ₃₂ H ₁₉ N ₃ S=477.59) Sub 1-62 m/z=383.13 (C ₂₈ H ₁₇ NO=383.45) Sub 1-63 m/z=399.11 (C ₂₈ H ₁₇ NS=399.51) Sub 1-64 m/z=383.13 (C ₂₈ H ₁₇ NO=383.45) Sub 1-65 m/z=475.14 (C ₃₄ H ₂₁ NS=475.61) Sub 1-66 m/z=459.16 (C ₃₄ H ₂₁ NO=459.55)

Sub 2 example

Examples of Sub 2 of Scheme 1 are as follows, but are not limited thereto, and Table 2 shows the field desorption-mass spectrometry (FD-MS) values of compounds belonging to Sub 2.

compound FD-MS compound FD-MS Sub 2-1 m/z=267.06 (C ₁₅ H ₁₀ ClN ₃ =267.72) Sub 2-2 m/z=317.07 (C ₁₉ H ₁₂ ClN ₃ =317.78) Sub 2-3 m/z=317.07 (C ₁₉ H ₁₂ ClN ₃ =317.78) Sub 2-4 m/z=367.09 (C ₂₃ H ₁₄ ClN ₃ =367.84) Sub 2-5 m/z=367.09 (C ₂₃ H ₁₄ ClN ₃ =367.84) Sub 2-6 m/z=343.09 (C ₂₁ H ₁₄ ClN ₃ =343.81) Sub 2-7 m/z=343.09 (C ₂₁ H ₁₄ ClN ₃ =343.81) Sub 2-8 m/z=419.12 (C ₂₇ H ₁₈ ClN ₃ =419.91) Sub 2-9 m/z=419.12 (C ₂₇ H ₁₈ ClN ₃ =419.91) Sub 2-10 m/z=393.1 (C ₂₅ H ₁₆ ClN ₃ =393.87) Sub 2-11 m/z=367.09 (C ₂₃ H ₁₄ ClN ₃ =367.84) Sub 2-12 m/z=443.12 (C ₂₉ H ₁₈ ClN ₃ =443.93) Sub 2-13 m/z=383.12 (C ₂₄ H ₁₈ ClN ₃ =383.88) Sub 2-14 m/z=507.15 (C ₃₄ H ₂₂ ClN ₃ =508.02) Sub 2-15 m/z=357.07 (C ₂₁ H ₁₂ ClN ₃ O=357.8) Sub 2-16 m/z=373.04 (C ₂₁ H ₁₂ ClN ₃ S=373.86) Sub 2-17 m/z=357.07 (C ₂₁ H ₁₂ ClN ₃ O=357.8) Sub 2-18 m/z=449.08 (C ₂₇ H ₁₆ ClN ₃ S=449.96) Sub 2-19 m/z=407.08 (C ₂₅ H ₁₄ ClN ₃ O=407.86) Sub 2-20 m/z=489.11 (C ₃₀ H ₂₀ ClN ₃ S=490.02) Sub 2-21 m/z=423.06 (C ₂₅ H ₁₄ ClN ₃ S=423.92) Sub 2-22 m/z=447.08 (C ₂₇ H ₁₄ ClN ₃ O ₂ =447.88) Sub 2-23 m/z=463.05 (C ₂₇ H ₁₄ ClN ₃ OS=463.94) Sub 2-24 m/z=463.05 (C ₂₇ H ₁₄ ClN ₃ OS=463.94) Sub 2-25 m/z=277.12 (C ₁₅ D ₁₀ ClN ₃ =277.78) Sub 2-26 m/z=367.09 (C ₂₃ H ₁₄ ClN ₃ =367.84) Sub 2-27 m/z=419.12 (C ₂₇ H ₁₈ ClN ₃ =419.91) Sub 2-28 m/z=357.07 (C ₂₁ H ₁₂ ClN ₃ O=357.8) Sub 2-29 m/z=373.04 (C ₂₁ H ₁₂ ClN ₃ S=373.86) Sub 2-30 m/z=343.09 (C ₂₁ H ₁₄ ClN ₃ =343.81) Sub 2-31 m/z=505.13 (C ₃₄ H ₂₀ ClN ₃ =506.01) Sub 2-32 m/z=373.04 (C ₂₁ H ₁₂ ClN ₃ S=373.86) Sub 2-33 m/z=407.08 (C ₂₅ H ₁₄ ClN ₃ O=407.86) Sub 2-34 m/z=479.03 (C ₂₇ H ₁₄ ClN ₃ S ₂ =480) Sub 2-35 m/z=487.07 (C ₂₉ H ₁₈ BrN ₃ =488.39) Sub 2-36 m/z=387.04 (C ₂₁ H ₁₄ BrN ₃ =388.27) Sub 2-37 m/z=487.07 (C ₂₉ H ₁₈ BrN ₃ =488.39) Sub 2-38 m/z=437.05 (C ₂₅ H ₁₆ BrN ₃ =438.33) Sub 2-39 m/z=543.04 (C ₃₁ H ₁₈ BrN ₃ S=544.47)

Formula ( 1) of Synthesis of Product

After dissolving Sub 1 (1 eq) in a round bottom flask with Toluene, Sub 2 (1 eq), Pd ₂ (dba) ₃ (0.03 eq), P(t-Bu) ₃ (0.06 eq), NaOt-Bu ( 2 equivalents) and stirred at 100°C. 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, and then the resulting compound was obtained by silicagel column and recrystallization.

1-37 Synthetic example

Sub 1-3 (15g, 40.6mmol), Toluene (200mL), Sub 2-2 (12.9g, 40.6mmol), Pd ₂ (dba) ₃ (1.12g, 1.22mmol), P(t-Bu) ₃ ( 0.49 g, 2.44 mmol), NaOt-Bu (7.8 g, 81.2 mmol) was added and stirred at 100°C. 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, and then the resulting compound was silicagel column and recrystallized to obtain the product (19 g, 72%).

1-30 Synthetic example

Sub 1-2 (15g, 51.1mmol), Toluene (250mL), Sub 2-2 (16.2g, 51.1mmol), Pd ₂ (dba) ₃ (1.4g, 1.53mmol), P(t-Bu) ₃ ( 0.62g, 3.07mmol), NaOt-Bu (9.8g, 102.3mmol) was added and stirred at 100 °C. After the reaction was completed, the organic layer was extracted with CH ₂ Cl ₂ and water, dried over MgSO ₄ and concentrated, and then the resulting compound was silicagel column and recrystallized to obtain the product (21.5 g, 73%).

1-51 Synthetic example

Sub 1-3 (15g, 40.6mmol), Toluene (200mL), Sub 2-28 (14.5g, 40.6mmol), Pd ₂ (dba) ₃ (1.12g, 1.22mmol), P(t-Bu) ₃ ( 0.49g, 2.44mmol), NaOt-Bu (7.8g, 81.2mmol) was added and stirred at 100 °C. 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, and then the resulting compound was silicagel column and recrystallized to obtain the product (20.2 g, 72%).

Table 3 shows FD-MS (Field Desorption-Mass Spectrometry) values of compounds belonging to Formula (1).

compound FD-MS compound FD-MS 1-1 m/z=448.17 (C ₃₁ H ₂₀ N ₄ =448.53) 1-2 m/z=498.18 (C ₃₅ H ₂₂ N ₄ =498.59) 1-3 m/z=498.18 (C ₃₅ H ₂₂ N ₄ =498.59) 1-4 m/z=548.2 (C ₃₉ H ₂₄ N ₄ =548.65) 1-5 m/z=548.2 (C ₃₉ H ₂₄ N ₄ =548.65) 1-6 m/z=524.2 (C ₃₇ H ₂₄ N ₄ =524.63) 1-7 m/z=524.2 (C ₃₇ H ₂₄ N ₄ =524.63) 1-8 m/z=600.23 (C ₄₃ H ₂₈ N ₄ =600.73) 1-9 m/z=600.23 (C ₄₃ H ₂₈ N ₄ =600.73) 1-10 m/z=574.22 (C ₄₁ H ₂₆ N ₄ =574.69) 1-11 m/z=548.2 (C ₃₉ H ₂₄ N ₄ =548.65) 1-12 m/z=624.23 (C ₄₅ H ₂₈ N ₄ =624.75) 1-13 m/z=564.23 (C ₄₀ H ₂₈ N ₄ =564.69) 1-14 m/z=688.26 (C ₅₀ H ₃₂ N ₄ =688.83) 1-15 m/z=538.18 (C ₃₇ H ₂₂ N ₄ O=538.61) 1-16 m/z=554.16 (C ₃₇ H ₂₂ N ₄ S=554.67) 1-17 m/z=538.18 (C ₃₇ H ₂₂ N ₄ O=538.61) 1-18 m/z=630.19 (C ₄₃ H ₂₆ N ₄ S=630.77) 1-19 m/z=588.2 (C ₄₁ H ₂₄ N ₄ O=588.67) 1-20 m/z=670.22 (C ₄₆ H ₃₀ N ₄ S=670.83) 1-21 m/z=604.17 (C ₄₁ H ₂₄ N ₄ S=604.73) 1-22 m/z=628.19 (C ₄₃ H ₂₄ N ₄ O ₂ =628.69) 1-23 m/z=644.17 (C ₄₃ H ₂₄ N ₄ OS=644.75) 1-24 m/z=644.17 (C ₄₃ H ₂₄ N ₄ OS=644.75) 1-25 m/z=458.23 (C ₃₁ H ₁₀ D ₁₀ N ₄ =458.59) 1-26 m/z=524.2 (C ₃₇ H ₂₄ N ₄ =524.63) 1-27 m/z=524.2 (C ₃₇ H ₂₄ N ₄ =524.63) 1-28 m/z=524.2 (C ₃₇ H ₂₄ N ₄ =524.63) 1-29 m/z=524.2 (C ₃₇ H ₂₄ N ₄ =524.63) 1-30 m/z=574.22 (C ₄₁ H ₂₆ N ₄ =574.69) 1-31 m/z=600.23 (C ₄₃ H ₂₈ N ₄ =600.73) 1-32 m/z=690.24 (C ₄₉ H ₃₀ N ₄ O=690.81) 1-33 m/z=574.22 (C ₄₁ H ₂₆ N ₄ =574.69) 1-34 m/z=600.23 (C ₄₃ H ₂₈ N ₄ =600.73) 1-35 m/z=624.23 (C ₄₅ H ₂₈ N ₄ =624.75) 1-36 m/z=600.23 (C ₄₃ H ₂₈ N ₄ =600.73) 1-37 m/z=650.25 (C ₄₇ H ₃₀ N ₄ =650.79) 1-38 m/z=650.25 (C ₄₇ H ₃₀ N ₄ =650.79) 1-39 m/z=700.26 (C ₅₁ H ₃₂ N ₄ =700.85) 1-40 m/z=700.26 (C ₅₁ H ₃₂ N ₄ =700.85) 1-41 m/z=600.23 (C ₄₃ H ₂₈ N ₄ =600.73) 1-42 m/z=676.26 (C ₄₉ H ₃₂ N ₄ =676.82) 1-43 m/z=676.26 (C ₄₉ H ₃₂ N ₄ =676.82) 1-44 m/z=752.29 (C ₅₅ H ₃₆ N ₄ =752.92) 1-45 m/z=726.28 (C ₅₃ H ₃₄ N ₄ =726.88) 1-46 m/z=700.26 (C ₅₁ H ₃₂ N ₄ =700.85) 1-47 m/z=700.26 (C ₅₁ H ₃₂ N ₄ =700.85) 1-48 m/z=766.31 (C ₅₆ H ₃₈ N ₄ =766.95) 1-49 m/z=764.29 (C ₅₆ H ₃₆ N ₄ =764.93) 1-50 m/z=690.24 (C ₄₉ H ₃₀ N ₄ O=690.81) 1-51 m/z=690.24 (C ₄₉ H ₃₀ N ₄ O=690.81) 1-52 m/z=614.21 (C ₄₃ H ₂₆ N ₄ O=614.71) 1-53 m/z=756.23 (C ₅₃ H ₃₂ N ₄ S=756.93) 1-54 m/z=740.26 (C ₅₃ H ₃₂ N ₄ O=740.87) 1-55 m/z=796.27 (C ₅₆ H ₃₆ N ₄ S=796.99) 1-56 m/z=756.23 (C ₅₃ H ₃₂ N ₄ S=756.93) 1-57 m/z=704.22 (C ₄₉ H ₂₈ N ₄ O ₂ =704.79) 1-58 m/z=720.2 (C ₄₉ H ₂₈ N ₄ OS=720.85) 1-59 m/z=796.23 (C ₅₅ H ₃₂ N ₄ OS=796.95) 1-60 m/z=610.29 (C ₄₃ H ₁₈ D ₁₀ N ₄ =610.79) 1-61 m/z=498.18 (C ₃₅ H ₂₂ N ₄ =498.59) 1-62 m/z=604.17 (C ₄₁ H ₂₄ N ₄ S=604.73) 1-63 m/z=548.2 (C ₃₉ H ₂₄ N ₄ =548.65) 1-64 m/z=638.21 (C ₄₅ H ₂₆ N ₄ O=638.73) 1-65 m/z=624.23 (C ₄₅ H ₂₈ N ₄ =624.75) 1-66 m/z=574.22 (C ₄₁ H ₂₆ N ₄ =574.69) 1-67 m/z=588.2 (C ₄₁ H ₂₄ N ₄ O=588.67) 1-68 m/z=548.2 (C ₃₉ H ₂₄ N ₄ =548.65) 1-69 m/z=498.18 (C ₃₅ H ₂₂ N ₄ =498.59) 1-70 m/z=786.28 (C ₅₈ H ₃₄ N ₄ =786.94) 1-71 m/z=654.19 (C ₄₅ H ₂₆ N ₄ S=654.79) 1-72 m/z=688.23 (C ₄₉ H ₂₈ N ₄ O=688.79) 1-73 m/z=760.18 (C ₅₁ H ₂₈ N ₄ S ₂ =760.93) 1-74 m/z=598.22 (C ₄₃ H ₂₆ N ₄ =598.71) 1-75 m/z=624.23 (C ₄₅ H ₂₈ N ₄ =624.75) 1-76 m/z=574.22 (C ₄₁ H ₂₆ N ₄ =574.69) 1-77 m/z=680.2 (C ₄₇ H ₂₈ N ₄ S=680.83) 1-78 m/z=700.26 (C ₅₁ H ₃₂ N ₄ =700.85) 1-79 m/z=714.24 (C ₅₁ H ₃₀ N ₄ O=714.83) 1-80 m/z=700.26 (C ₅₁ H ₃₂ N ₄ =700.85) 1-81 m/z=650.25 (C ₄₇ H ₃₀ N ₄ =650.79) 1-82 m/z=664.23 (C ₄₇ H ₂₈ N ₄ O=664.77) 1-83 m/z=624.23 (C ₄₅ H ₂₈ N ₄ =624.75) 1-84 m/z=650.25 (C ₄₇ H ₃₀ N ₄ =650.79) 1-85 m/z=812.29 (C ₆₀ H ₃₆ N ₄ =812.98) 1-86 m/z=730.22 (C ₅₁ H ₃₀ N ₄ S=730.89) 1-87 m/z=764.26 (C ₅₅ H ₃₂ N ₄ O=764.89) 1-88 m/z=836.21 (C ₅₇ H ₃₂ N ₄ S ₂ =837.03) 1-89 m/z=674.25 (C ₄₉ H ₃₀ N ₄ =674.81) 1-90 m/z=700.26 (C ₅₁ H ₃₂ N ₄ =700.85) 1-91 m/z=708.21 (C ₄₇ H ₂₈ N ₆ S=708.84) 1-92 m/z=778.28 (C ₅₅ H ₃₄ N ₆ =778.92) 1-93 m/z=769.26 (C ₅₂ H ₃₁ N ₇ O=769.87) 1-94 m/z=758.23 (C ₅₁ H ₃₀ N ₆ S=758.9) 1-95 m/z=575.21 (C ₄₀ H ₂₅ N ₅ =575.68) 1-96 m/z=664.23 (C ₄₇ H ₂₈ N ₄ O=664.77) 1-97 m/z=680.2 (C ₄₇ H ₂₈ N ₄ S=680.83) 1-98 m/z=704.22 (C ₄₉ H ₂₈ N ₄ O ₂ =704.79) 1-99 m/z=756.23 (C ₅₃ H ₃₂ N ₄ S=756.93) 1-100 m/z=740.26 (C ₅₃ H ₃₂ N ₄ O=740.87) 1-101 m/z=524.2 (C ₃₇ H ₂₄ N ₄ =524.63) 1-102 m/z=624.23 (C ₄₅ H ₂₈ N ₄ =624.75) 1-103 m/z=650.25 (C ₄₇ H ₃₀ N ₄ =650.79) 1-104 m/z=730.22 (C ₅₁ H ₃₀ N ₄ S=730.89) 1-105 m/z=776.29 (C ₅₇ H ₃₆ N ₄ =776.94) 1-106 m/z=604.26 (C ₄₃ H ₃₂ N ₄ =604.76) 1-107 m/z=831.3 (C ₅₉ H ₃₇ N ₅ O=831.98) 1-108 m/z=680.29 (C ₄₉ H ₃₆ N ₄ =680.86) 1-109 m/z=880.36 (C ₆₅ H ₄₄ N ₄ =881.1) 1-110 m/z=707.25 (C ₄₉ H ₃₀ FN ₅ =707.81)

[ Synthetic example 2]

The compound represented by the formula (2) according to the present invention (final product 2) is prepared by reacting Sub 3 and Sub 4 as shown in Reaction Scheme 3 below.

<Scheme 3>

Sub 3 synthesis example

Sub 3 of Scheme 3 may be synthesized by the reaction route of Scheme 4 below, but is not limited thereto.

<Reaction Scheme 4>

1. Sub 3-1 Synthetic example

9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (50g, 135.4mmol), 1-bromo-4-iodobenzene (38.3g , 135.4mmol), K ₂ CO ₃ (56.1g, 406.2mmol), Pd(PPh ₃ ) ₄ (9.39g, 8.12mmol) in a round bottom flask, and then THF (670mL) and water (340mL). It was refluxed at 80°C for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ and wiped with water. After drying and concentrating the organic layer with MgSO ₄ , the resulting organic material was separated using a silicagel column to obtain the desired product (44.8g, 83%).

2. Sub 3-2 Synthetic example

9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (50g, 135.4mmol), 1,3-dibromo-5-iodobenzene ( 49g, 135.4mmol), K ₂ CO ₃ (56.1g, 406.2mmol), Pd(PPh ₃ ) ₄ (9.39g, 8.12mmol), THF (670mL), water (340mL) and Sub 3-1 The same procedure was carried out to obtain the product (51 g, 79%).

3. Sub 3-3 Synthetic example

9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (50g, 135.4mmol), 4-bromo-4'-iodo-1 ,1'-biphenyl (48.6g, 135.4mmol), K ₂ CO ₃ (56.1g, 406.2mmol), Pd(PPh ₃ ) ₄ (9.39g, 8.12mmol), THF (670mL), water (340mL) Sub The same procedure as in 3-1 was carried out to obtain the product (50.7 g, 79%).

4. Sub 3-4 Synthetic example

9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (50g, 135.4mmol), 2-bromo-4-iododibenzo[b, d]furan (50.5g, 135.4mmol), K ₂ CO ₃ (56.1g, 406.2mmol), Pd(PPh ₃ ) ₄ (9.39g, 8.12mmol), THF (670mL), water (340mL) Sub 3- The same procedure as in Experiment 1 was carried out to obtain the product (47.6 g, 72%).

5. Sub 3-5 Synthetic example

9-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (50g, 135.4mmol), 1-bromo-4-iodonaphthalene (45.1g , 135.4mmol), K ₂ CO ₃ (56.1g, 406.2mmol), Pd(PPh ₃ ) ₄ (9.39g, 8.12mmol), THF (670mL), and water (340mL) are the same as the experiment method of Sub 3-1. Proceed to give the product (49.8g, 82%).

Examples of Sub 3 are as follows, but are not limited thereto, and Table 4 shows FD-MS (Field Desorption-Mass Spectrometry) values of compounds belonging to Sub 3.

compound FD-MS compound FD-MS Sub 3-1 m/z=397.05 (C ₂₄ H ₁₆ BrN=398.3) Sub 3-2 m/z=474.96 (C ₂₄ H ₁₅ Br ₂ N=477.2) Sub 3-3 m/z=473.08 (C ₃₀ H ₂₀ BrN=474.4) Sub 3-4 m/z=487.06 (C ₃₀ H ₁₈ BrNO=488.38) Sub 3-5 m/z=447.06 (C ₂₈ H ₁₈ BrN=448.36) Sub 3-6 m/z=397.05 (C ₂₄ H ₁₆ BrN=398.3) Sub 3-7 m/z=398.04 (C ₂₃ H ₁₅ BrN ₂ =399.29) Sub 3-8 m/z=549.11 (C ₃₆ H ₂₄ BrN=550.5) Sub 3-9 m/z=397.05 (C ₂₄ H ₁₆ BrN=398.3) Sub 3-10 m/z=397.05 (C ₂₄ H ₁₆ BrN=398.3) Sub 3-11 m/z=397.05 (C ₂₄ H ₁₆ BrN=398.3) Sub 3-12 m/z=447.06 (C ₂₈ H ₁₈ BrN=448.36) Sub 3-13 m/z=447.06 (C ₂₈ H ₁₈ BrN=448.36) Sub 3-14 m/z=497.08 (C ₃₂ H ₂₀ BrN=498.42) Sub 3-15 m/z=473.08 (C ₃₀ H ₂₀ BrN=474.4) Sub 3-16 m/z=473.08 (C ₃₀ H ₂₀ BrN=474.4) Sub 3-17 m/z=552.09 (C ₃₃ H ₂₁ BrN ₄ =553.46) Sub 3-18 m/z=562.1 (C ₃₆ H ₂₃ BrN ₂ =563.5) Sub 3-19 m/z=553.05 (C ₃₄ H ₂₀ BrNS=554.51) Sub 3-20 m/z=473.08 (C ₃₀ H ₂₀ BrN=474.4) Sub 3-21 m/z=487.06 (C ₃₀ H ₁₈ BrNO=488.38) Sub 3-22 m/z=563.12 (C ₃₇ H ₂₆ BrN=564.53) Sub 3-23 m/z=447.06 (C ₂₈ H ₁₈ BrN=448.36) Sub 3-24 m/z=473.08 (C ₃₀ H ₂₀ BrN=474.4) Sub 3-25 m/z=473.08 (C ₃₀ H ₂₀ BrN=474.4) Sub 3-26 m/z=523.09 (C ₃₄ H ₂₂ BrN=524.46) Sub 3-27 m/z=487.06 (C ₃₀ H ₁₈ BrNO=488.38) Sub 3-28 m/z=513.11 (C ₃₃ H ₂₄ BrN=514.47) Sub 3-29 m/z=523.09 (C ₃₄ H ₂₂ BrN=524.46) Sub 3-30 m/z=503.03 (C ₃₀ H ₁₈ BrNS=504.45) Sub 3-31 m/z=447.06 (C ₂₈ H ₁₈ BrN=448.36) Sub 3-32 m/z=447.06 (C ₂₈ H ₁₈ BrN=448.36) Sub 3-33 m/z=447.06 (C ₂₈ H ₁₈ BrN=448.36) Sub 3-34 m/z=473.08 (C ₃₀ H ₂₀ BrN=474.4) Sub 3-35 m/z=579.07 (C ₃₆ H ₂₂ BrNS=580.54) Sub 3-36 m/z=628.13 (C ₃₉ H ₂₅ BrN ₄ =629.56) Sub 3-37 m/z=589.14 (C ₃₉ H ₂₈ BrN=590.56) Sub 3-38 m/z=627.13 (C ₄₀ H ₂₆ BrN ₃ =628.57) Sub 3-39 m/z=523.09 (C ₃₄ H ₂₂ BrN=524.46) Sub 3-40 m/z=553.05 (C ₃₄ H ₂₀ BrNS=554.51) Sub 3-41 m/z=513.11 (C ₃₃ H ₂₄ BrN=514.47) Sub 3-42 m/z=552.09 (C ₃₃ H ₂₁ BrN ₄ =553.46) Sub 3-43 m/z=562.1 (C ₃₆ H ₂₃ BrN ₂ =563.5) Sub 3-44 m/z=549.11 (C ₃₆ H ₂₄ BrN=550.5) Sub 3-45 m/z=563.09 (C ₃₆ H ₂₂ BrNO=564.48) Sub 3-46 m/z=563.09 (C ₃₆ H ₂₂ BrNO=564.48) Sub 3-47 m/z=639.16 (C ₄₃ H ₃₀ BrN=640.62) Sub 3-48 m/z=474.96 (C ₂₄ H ₁₅ Br ₂ N=477.2) Sub 3-49 m/z=550.99 (C ₃₀ H ₁₉ Br ₂ N=553.3) Sub 3-50 m/z=580.94 (C ₃₀ H ₁₇ Br ₂ NS=583.34) Sub 3-51 m/z=630.01 (C ₃₃ H ₂₀ Br ₂ N ₄ =632.36) Sub 3-52 m/z=524.97 (C ₂₈ H ₁₇ Br ₂ N=527.26) Sub 3-53 m/z=574.99 (C ₃₂ H ₁₉ Br ₂ N=577.32) Sub 3-54 m/z=524.97 (C ₂₈ H ₁₇ Br ₂ N=527.26) Sub 3-55 m/z=524.97 (C ₂₈ H ₁₇ Br ₂ N=527.26) Sub 3-56 m/z=474.96 (C ₂₄ H ₁₅ Br ₂ N=477.2) Sub 3-57 m/z=550.99 (C ₃₀ H ₁₉ Br ₂ N=553.3) Sub 3-58 m/z=580.94 (C ₃₀ H ₁₇ Br ₂ NS=583.34) Sub 3-59 m/z=524.97 (C ₂₈ H ₁₇ Br ₂ N=527.26) Sub 3-60 m/z=630.01 (C ₃₃ H ₂₀ Br ₂ N ₄ =632.36) Sub 3-61 m/z=574.99 (C ₃₂ H ₁₉ Br ₂ N=577.32) Sub 3-62 m/z=550.99 (C ₃₀ H ₁₉ Br ₂ N=553.3) Sub 3-63 m/z=524.97 (C ₂₈ H ₁₇ Br ₂ N=527.26) Sub 3-64 m/z=574.99 (C ₃₂ H ₁₉ Br ₂ N=577.32) Sub 3-65 m/z=474.96 (C ₂₄ H ₁₅ Br ₂ N=477.2) Sub 3-66 m/z=474.96 (C ₂₄ H ₁₅ Br ₂ N=477.2) Sub 3-67 m/z=474.96 (C ₂₄ H ₁₅ Br ₂ N=477.2) Sub 3-68 m/z=641 (C ₃₆ H ₂₁ Br ₂ NO=643.38) Sub 3-69 m/z=474.96 (C ₂₄ H ₁₅ Br ₂ N=477.2) Sub 3-70 m/z=474.96 (C ₂₄ H ₁₅ Br ₂ N=477.2) Sub 3-71 m/z=474.96 (C ₂₄ H ₁₅ Br ₂ N=477.2) Sub 3-72 m/z=656.98 (C ₃₆ H ₂₁ Br ₂ NS=659.44) Sub 3-73 m/z=641 (C ₃₆ H ₂₁ Br ₂ NO=643.38) Sub 3-74 m/z=717.03 (C ₄₂ H ₂₅ Br ₂ NO=719.48) Sub 3-75 m/z=552.98 (C ₂₈ H ₁₇ Br ₂ N ₃ =555.27) Sub 3-76 m/z=677.04 (C ₄₀ H ₂₅ Br ₂ N=679.46) Sub 3-77 m/z=564.97 (C ₃₀ H ₁₇ Br ₂ NO=567.28) Sub 3-78 m/z=733.01 (C ₄₂ H ₂₅ Br ₂ NS=735.54) Sub 3-79 m/z=677.04 (C ₄₀ H ₂₅ Br ₂ N=679.46) Sub 3-80 m/z=656.98 (C ₃₆ H ₂₁ Br ₂ NS=659.44)

Sub 4 synthesis example

Sub 4 of Reaction Scheme 3 may be synthesized by the reaction route of Reaction Scheme 5 below, but is not limited thereto.

<Reaction Scheme 5>

Examples of Sub 4 are as follows, but are not limited thereto, and Table 5 shows FD-MS (Field Desorption-Mass Spectrometry) values of compounds belonging to Sub 4.

compound FD-MS compound FD-MS Sub 4-1 m/z=321.15 (C ₂₄ H ₁₉ N=321.42) Sub 4-2 m/z=361.18 (C ₂₇ H ₂₃ N=361.49) Sub 4-3 m/z=391.14 (C ₂₇ H ₂₁ NS=391.53) Sub 4-4 m/z=485.21 (C ₃₇ H ₂₇ N=485.63) Sub 4-5 m/z=483.2 (C ₃₇ H ₂₅ N=483.61) Sub 4-6 m/z=246.12 (C ₁₇ H ₁₄ N ₂ =246.31) Sub 4-7 m/z=351.11 (C ₂₄ H ₁₇ NS=351.47) Sub 4-8 m/z=410.18 (C ₃₀ H ₂₂ N ₂ =410.52) Sub 4-9 m/z=335.13 (C ₂₄ H ₁₇ NO=335.41) Sub 4-10 m/z=345.15 (C ₂₆ H ₁₉ N=345.45) Sub 4-11 m/z=169.09 (C ₁₂ H ₁₁ N=169.23) Sub 4-12 m/z=219.1 (C ₁₆ H ₁₃ N=219.29) Sub 4-13 m/z=295.14 (C ₂₂ H ₁₇ N=295.39) Sub 4-14 m/z=485.21 (C ₃₇ H ₂₇ N=485.63) Sub 4-15 m/z=407.17 (C ₃₁ H ₂₁ N=407.52) Sub 4-16 m/z=351.11 (C ₂₄ H ₁₇ NS=351.47) Sub 4-17 m/z=269.12 (C ₂₀ H ₁₅ N=269.35) Sub 4-18 m/z=174.12 (C ₁₂ H ₆ D ₅ N=174.26) Sub 4-19 m/z=264.11 (C ₁₇ H ₁₃ FN ₂ =264.3) Sub 4-20 m/z=285.15 (C ₂₁ H ₁₉ N=285.39) Sub 4-21 m/z=295.14 (C ₂₂ H ₁₇ N=295.39) Sub 4-22 m/z=245.12 (C ₁₈ H ₁₅ N=245.33) Sub 4-23 m/z=245.12 (C ₁₈ H ₁₅ N=245.33) Sub 4-24 m/z=275.08 (C ₁₈ H ₁₃ NS=275.37) Sub 4-25 m/z=334.15 (C ₂₄ H ₁₈ N ₂ =334.42) Sub 4-26 m/z=170.08 (C ₁₁ H ₁₀ N ₂ =170.22) Sub 4-27 m/z=275.08 (C ₁₈ H ₁₃ NS=275.37) Sub 4-28 m/z=259.1(C ₁₈ H ₁₃ NO=259.31) Sub 4-29 m/z=285.15 (C ₂₁ H ₁₉ N=285.39) Sub 4-30 m/z=334.15 (C ₂₄ H ₁₈ N ₂ =334.42) Sub 4-31 m/z=250.15 (C ₁₈ H ₁₀ D ₅ N=250.36) Sub 4-32 m/z=410.18 (C ₃₀ H ₂₂ N ₂ =410.52) Sub 4-33 m/z=275.08 (C ₁₈ H ₁₃ NS=275.37) Sub 4-34 m/z=409.18 (C ₃₁ H ₂₃ N=409.53) Sub 4-35 m/z=269.12 (C ₂₀ H ₁₅ N=269.35) Sub 4-36 m/z=407.17 (C ₃₁ H ₂₁ N=407.52) Sub 4-37 m/z=351.11 (C ₂₄ H ₁₇ NS=351.47) Sub 4-38 m/z=219.1 (C ₁₆ H ₁₃ N=219.29) Sub 4-39 m/z=269.12 (C ₂₀ H ₁₅ N=269.35) Sub 4-40 m/z=250.15 (C ₁₈ H ₁₀ D ₅ N=250.36)

Formula ( 2) of Synthesis of Product

2-2 Synthetic example

Sub 4-2 (13.6g, 37.7mmol) was put in a round bottom flask and dissolved in toluene (190mL), Sub 3-1 (15g, 37.7mmol), Pd ₂ (dba) ₃ (1.03g, 1.13mmol), P(t-Bu) ₃ (0.46 g, 2.26 mmol), NaOt-Bu (7.2 g, 75.3 mmol) was added and stirred at 100°C. 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.

2-58 Synthetic example

(1) 2-58a synthesis

Sub 4-2 (7.7g, 31.4mmol), toluene (160mL), Sub 3-48 (15g, 31.4mmol), Pd ₂ (dba) ₃ (0.86g, 0.94mmol), P(t-Bu) ₃ ( 0.38g, 1.89mmol), NaOt-Bu (6g, 62.9mmol) was obtained using the 2-2 synthesis method to obtain the product (14.7g, 73%).

(2) 2-58 synthesis

Sub 4-24 (6.3g, 22.9mmol), toluene (120mL), 2-58a (14.7g, 22.9mmol), Pd ₂ (dba) ₃ (0.63g, 0.69 mmol), P(t-Bu) ₃ (0.28 g, 1.37 mmol), NaOt-Bu (4.4 g, 45.8 mmol) was obtained using the 2-2 synthesis method to obtain the product (14.2 g, 74%).

2-64 Synthetic example

Sub 4-38 (12.4g, 56.8mmol), toluene (210mL), Sub 3-52 (15g, 28.4mmol), Pd ₂ (dba) ₃ (0.78g, 0.85mmol), P(t-Bu) ₃ ( 0.35g, 1.71mmol) and NaOt-Bu (5.5g, 56.9mmol) were obtained using the 2-2 synthesis method to obtain the product (17.8g, 78%).

Table 6 shows FD-MS (Field Desorption-Mass Spectrometry) values of compounds belonging to Formula (2).

compound FD-MS compound FD-MS 2-1 m/z=638.27 (C ₄₈ H ₃₄ N ₂ =638.81) 2-2 m/z=678.3 (C ₅₁ H ₃₈ N ₂ =678.88) 2-3 m/z=639.27 (C ₄₇ H ₃₃ N ₃ =639.8) 2-4 m/z=790.33 (C ₆₀ H ₄₂ N ₂ =791.01) 2-5 m/z=708.26 (C ₅₁ H ₃₆ N ₂ S=708.92) 2-6 m/z=802.33 (C ₆₁ H ₄₂ N ₂ =803.02) 2-7 m/z=800.32 (C ₆₁ H ₄₀ N ₂ =801.01) 2-8 m/z=563.24 (C ₄₁ H ₂₉ N ₃ =563.7) 2-9 m/z=668.23 (C ₄₈ H ₃₂ N ₂ S=668.86) 2-10 m/z=727.3 (C ₅₄ H ₃₇ N ₃ =727.91) 2-11 m/z=652.25 (C ₄₈ H ₃₂ N ₂ O=652.8) 2-12 m/z=662.27 (C ₅₀ H ₃₄ N ₂ =662.84) 2-13 m/z=536.23 (C ₄₀ H ₂₈ N ₂ =536.68) 2-14 m/z=586.24 (C ₄₄ H ₃₀ N ₂ =586.74) 2-15 m/z=712.29 (C ₅₄ H ₃₆ N ₂ =712.9) 2-16 m/z=714.3 (C ₅₄ H ₃₈ N ₂ =714.91) 2-17 m/z=754.33 (C ₅₇ H ₄₂ N ₂ =754.98) 2-18 m/z=957.38 (C ₇₀ H ₄₇ N ₅ =958.18) 2-19 m/z=889.35 (C ₆₇ H ₄₃ N ₃ =890.1) 2-20 m/z=719.24 (C ₅₁ H ₃₃ N ₃ S=719.91) 2-21 m/z=758.24 (C ₅₄ H ₃₄ N ₂ OS=758.94) 2-22 m/z=893.38 (C ₆₇ H ₄₇ N ₃ =894.13) 2-23 m/z=702.27 (C ₅₂ H ₃₄ N ₂ O=702.86) 2-24 m/z=662.27 (C ₅₀ H ₃₄ N ₂ =662.84) 2-25 m/z=678.3 (C ₅₁ H ₃₈ N ₂ =678.88) 2-26 m/z=662.27 (C ₅₀ H ₃₄ N ₂ =662.84) 2-27 m/z=688.29 (C ₅₂ H ₃₆ N ₂ =688.87) 2-28 m/z=714.3 (C ₅₄ H ₃₈ N ₂ =714.91) 2-29 m/z=804.35 (C ₆₁ H ₄₄ N ₂ =805.04) 2-30 m/z=833.29 (C ₆₀ H ₃₉ N ₃ S=834.05) 2-31 m/z=742.26 (C ₅₄ H ₃₄ N ₂ O ₂ =742.88) 2-32 m/z=778.33 (C ₅₉ H ₄₂ N ₂ =779) 2-33 m/z=486.21 (C ₃₆ H ₂₆ N ₂ =486.62) 2-34 m/z=586.24 (C ₄₄ H ₃₀ N ₂ =586.74) 2-35 m/z=662.27 (C ₅₀ H ₃₄ N ₂ =662.84) 2-36 m/z=688.29 (C ₅₂ H ₃₆ N ₂ =688.87) 2-37 m/z=491.24 (C ₃₆ H ₂₁ D ₅ N ₂ =491.65) 2-38 m/z=612.26 (C ₄₆ H ₃₂ N ₂ =612.78) 2-39 m/z=794.28 (C ₅₈ H ₃₈ N ₂ S=795.02) 2-40 m/z=656.26 (C ₄₈ H ₃₃ FN ₂ =656.8) 2-41 m/z=717.29 (C ₅₁ H ₃₅ N ₅ =717.88) 2-42 m/z=728.32 (C ₅₅ H ₄₀ N ₂ =728.94) 2-43 m/z=842.34 (C ₆₂ H ₄₂ N ₄ =843.05) 2-44 m/z=764.32 (C ₅₈ H ₄₀ N ₂ =764.97) 2-45 m/z=794.37 (C ₆₀ H ₄₆ N ₂ =795.04) 2-46 m/z=987.39 (C ₇₁ H ₄₉ N ₅ O=988.21) 2-47 m/z=1021.44 (C ₇₇ H ₅₅ N ₃ =1022.31) 2-48 m/z=737.23 (C ₅₁ H ₃₂ FN ₃ S=737.9) 2-49 m/z=652.25 (C ₄₈ H ₃₂ N ₂ O=652.8) 2-50 m/z=778.33 (C ₅₉ H ₄₂ N ₂ =779) 2-51 m/z=764.32 (C ₅₈ H ₄₀ N ₂ =764.97) 2-52 m/z=778.3 (C ₅₈ H ₃₈ N ₂ O=778.96) 2-53 m/z=653.28 (C ₄₈ H ₃₅ N ₃ =653.83) 2-54 m/z=703.3 (C ₅₂ H ₃₇ N ₃ =703.89) 2-55 m/z=805.35 (C ₆₀ H ₄₃ N ₃ =806.03) 2-56 m/z=919.36 (C ₆₈ H ₄₅ N ₃ O=920.13) 2-57 m/z=818.34 (C ₆₀ H ₄₂ N ₄ =819.02) 2-58 m/z=835.3 (C ₆₀ H ₄₁ N ₃ S=836.07) 2-59 m/z=655.27 (C ₄₆ H ₃₃ N ₅ =655.81) 2-60 m/z=885.32 (C ₆₄ H ₄₃ N ₃ S=886.13) 2-61 m/z=965.34 (C ₆₉ H ₄₇ N ₃ OS=966.22) 2-62 m/z=743.29 (C ₅₄ H ₃₇ N ₃ O=743.91) 2-63 m/z=960.39 (C ₆₉ H ₄₈ N ₆ =961.19) 2-64 m/z=803.33 (C ₆₀ H ₄₁ N ₃ =804.01) 2-65 m/z=894.37 (C ₆₆ H ₄₆ N ₄ =895.12) 2-66 m/z=834.38 (C ₆₂ H ₃₈ D ₅ N ₃ =835.08) 2-67 m/z=895.39 (C ₆₇ H ₄₉ N ₃ =896.15) 2-68 m/z=944.39 (C ₇₀ H ₄₈ N ₄ =945.18) 2-69 m/z=893.38 (C ₆₇ H ₄₇ N ₃ =894.13) 2-70 m/z=803.33 (C ₆₀ H ₄₁ N ₃ =804.01) 2-71 m/z=805.35 (C ₆₀ H ₄₃ N ₃ =806.03) 2-72 m/z=849.28 (C ₆₀ H ₃₉ N ₃ OS=850.05) 2-73 m/z=818.34 (C ₆₀ H ₄₂ N ₄ =819.02) 2-74 m/z=835.3 (C ₆₀ H ₄₁ N ₃ S=836.07) 2-75 m/z=655.27 (C ₄₆ H ₃₃ N ₅ =655.81) 2-76 m/z=885.32 (C ₆₄ H ₄₃ N ₃ S=886.13) 2-77 m/z=997.35 (C ₇₃ H ₄₇ N ₃ S=998.26) 2-78 m/z=753.31 (C ₅₆ H ₃₉ N ₃ =753.95) 2-79 m/z=960.39 (C ₆₉ H ₄₈ N ₆ =961.19) 2-80 m/z=935.33 (C ₆₈ H ₄₅ N ₃ S=936.19) 2-81 m/z=894.37 (C ₆₆ H ₄₆ N ₄ =895.12) 2-82 m/z=784.36 (C ₅₈ H ₃₆ D ₅ N ₃ =785.02) 2-83 m/z=855.36 (C ₆₄ H ₄₅ N ₃ =856.09) 2-84 m/z=853.35 (C ₆₄ H ₄₃ N ₃ =854.07) 2-85 m/z=653.28 (C ₄₈ H ₃₅ N ₃ =653.83) 2-86 m/z=703.3 (C ₅₂ H ₃₇ N ₃ =703.89) 2-87 m/z=729.31 (C ₅₄ H ₃₉ N ₃ =729.93) 2-88 m/z=869.34 (C ₆₄ H ₄₃ N ₃ O=870.07) 2-89 m/z=653.28 (C ₄₈ H ₃₅ N ₃ =653.83) 2-90 m/z=703.3 (C ₅₂ H ₃₇ N ₃ =703.89) 2-91 m/z=845.38 (C ₆₃ H ₄₇ N ₃ =846.09) 2-92 m/z=835.3 (C ₆₀ H ₄₁ N ₃ S=836.07) 2-93 m/z=855.36 (C ₆₄ H ₄₅ N ₃ =856.09) 2-94 m/z=925.31 (C ₆₆ H ₄₃ N ₃ OS=926.15) 2-95 m/z=895.36 (C ₆₆ H ₄₅ N ₃ O=896.11) 2-96 m/z=831.34 (C ₆₀ H ₄₁ N ₅ =832.02) 2-97 m/z=983.39 (C ₇₃ H ₄₉ N ₃ O=984.22) 2-98 m/z=961.35 (C ₇₀ H ₄₇ N ₃ S=962.23) 2-99 m/z=855.36 (C ₆₄ H ₄₅ N ₃ =856.09) 2-100 m/z=1017.32 (C ₇₂ H ₄₇ N ₃ S ₂ =1018.31) 2-101 m/z=885.32 (C ₆₄ H ₄₃ N ₃ S=886.13) 2-102 m/z=485.19 (C ₃₅ H ₂₃ N ₃ =485.59) 2-103 m/z=636.26 (C ₄₈ H ₃₂ N ₂ =636.8) 2-104 m/z=754.33 (C ₅₇ H ₄₂ N ₂ =754.98)

Manufacturing evaluation of organic electric devices

[Example 1] Red organic light emitting device fabrication and test (light emitting layer mixed phosphorescent host)

First, N ¹ -(naphthalen-2-yl)-N ⁴ ,N ⁴ -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl) as a hole injection layer on the ITO layer (anode) formed on the glass substrate. )-N ¹ -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) The film was vacuum-deposited to form a thickness of 60 nm. Subsequently, N,N'-Bis(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter abbreviated as NPB) is 60 nm thick. A hole transport layer was formed by vacuum deposition. A mixture of a compound (1-51) and a compound (2-2) in a 50:50 weight ratio on the hole transport layer was used as a host (piq) ₂ Ir(acac)[bis-(1-phenylisoquinolyl)iridium (III)acetylacetonate] was used as a dopant to deposit a 30nm light emitting layer. At this time, the weight ratio of the host and the dopant was formed at 95:5. Vacuum deposition of (1,1'-bisphenyl)-4-oleito)bis(2-methyl-8-quinolinoleito)aluminum (hereinafter abbreviated as BAlq) to a thickness of 10 nm as a hole blocking layer on top of the light emitting layer Then, bis(10-hydroxybenzo[h]quinolinato)beryllium (hereinafter abbreviated as Bebq2) was deposited as an electron transport layer to a thickness of 40 nm. Thereafter, an organic electroluminescent device was manufactured by depositing LiF, a halogenated alkali metal, as an electron injection layer to a thickness of 0.2 nm, and then depositing Al to a thickness of 150 nm to use as a cathode.

[Example 2] to [Example 20]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that a mixture of the first host compound and the second host compound shown in Table 7 was used as the host material of the light emitting layer.

[Comparative Example 1] and [Comparative Example 2]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound represented by Formula 1 was used alone as a host.

[Comparative Example 3] to [Comparative Example 6]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compounds 1 to 4 were used alone as a host.

[Comparative Example 7]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 1 and Comparative Compound 3 were mixed and used as a host.

[Comparative Example 8]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 1 and Comparative Compound 4 were mixed and used as a host.

[Comparative Example 9]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 2 and Comparative Compound 4 were mixed and used as a host.

[Comparative Example 10]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound represented by Chemical Formula 1 and Comparative Compound 4 were mixed and used as a host.

[Comparative Example 11]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 2 and the compound represented by Chemical Formula 2 were mixed and used as a host.

Comparative Compound 1 Comparative Compound 2 Comparative Compound 3 Comparative Compound 4

Electro-luminescence (EL) characteristics of the organic electroluminescent device manufactured by Examples 1 to 20 and Comparative Examples 1 to 10 of the present invention were applied to the PR-650 of photoresearch by applying a direct bias DC voltage. The T95 life was measured through a life measurement equipment manufactured by Max Science at a reference luminance of 2500 cd/m2. Measurement results are shown in Table 7 below.

Host 1 Host 2 Driving voltage (V) Current density
(mA/cm ² ) Luminance
(cd/m ² ) efficiency
(cd/A) life span
T(95) Comparative Example (1) - Compound (1-30) 6.3 15.8 2500 15.8 97.4 Comparative Example (2) - Compound (1-17) 6.4 16.6 2500 15.1 95.9 Comparative Example (3) - Comparative Compound 1 6.6 16.2 2500 15.4 95.3 Comparative Example (4) - Comparative Compound 2 6.8 18.2 2500 13.7 84.6 Comparative Example (5) - Comparative Compound 3 6.7 19.3 2500 12.9 81.7 Comparative Example (6) - Comparative Compound 4 6.9 18.4 2500 13.6 82.9 Comparative Example (7) Comparative Compound 1 Comparative Compound 3 5.6 9.8 2500 25.5 110.5 Comparative Example (8) Comparative Compound 1 Comparative Compound 4 5.6 10.8 2500 23.2 109.1 Comparative Example (9) Comparative Compound 2 Comparative Compound 4 5.7 11.0 2500 22.6 113.7 Comparative Example (10) Compound (1-17) Comparative Compound 4 5.4 10.0 2500 25.1 112.2 Comparative Example (11) Comparative Compound 2 Compound (2-101) 5.1 8.7 2500 28.9 115.5 Example (1) Compound (1-51) Compound (2-2) 4.4 6.6 2500 37.9 132.6 Example (2) Compound (1-51) Compound (2-104) 4.4 6.7 2500 37.2 132.3 Example (3) Compound (1-51) Compound (2-58) 4.5 6.3 2500 39.7 134.7 Example (4) Compound (1-51) Compound (2-101) 4.5 6.4 2500 39.0 133.9 Example (5) Compound (1-52) Compound (2-2) 4.5 7.6 2500 33.1 122.6 Example (6) Compound (1-52) Compound (2-104) 4.5 7.6 2500 32.7 122.0 Example (7) Compound (1-52) Compound (2-58) 4.6 7.2 2500 34.6 124.9 Example (8) Compound (1-52) Compound (2-101) 4.6 7.3 2500 34.3 123.5 Example (9) Compound (1-30) Compound (2-2) 4.5 7.9 2500 31.8 124.6 Example (10) Compound (1-30) Compound (2-104) 4.6 8.0 2500 31.2 124.3 Example (11) Compound (1-30) Compound (2-58) 4.7 7.7 2500 32.6 125.7 Example (12) Compound (1-30) Compound (2-101) 4.7 7.7 2500 32.3 124.8 Example (13) Compound (1-63) Compound (2-2) 4.3 6.8 2500 36.9 128.6 Example (14) Compound (1-63) Compound (2-104) 4.4 6.9 2500 36.2 127.6 Example (15) Compound (1-63) Compound (2-58) 4.4 6.5 2500 38.5 130.4 Example (16) Compound (1-63) Compound (2-101) 4.5 6.6 2500 38.1 129.1 Example (17) Compound (1-17) Compound (2-2) 4.7 8.6 2500 29.2. 119.7 Example (18) Compound (1-17) Compound (2-104) 4.7 8.8 2500 28.5 119.3 Example (19) Compound (1-17) Compound (2-58) 4.7 8.2 2500 30.6 121.4 Example (20) Compound (1-17) Compound (2-101) 4.8 8.4 2500 29.9 120.6

As can be seen from the results of Table 7, when the material for the organic electroluminescent device of the present invention represented by Formula 1 and Formula 2 is mixed and used as a phosphorescent host (Examples 1 to 20), a device using a single material (Comparative Examples 1 to 6) It was confirmed that the driving voltage, efficiency and lifespan were significantly improved compared to the devices (Comparative Examples 7 to 11) used by mixing the comparative compounds.

In addition, in Comparative Examples 1 to 6 in which the compounds of the present invention represented by Formula 1 or Comparative Compounds 1 to 4 were used alone as phosphorescent hosts, Comparative Examples using compounds of the present invention (1-30, 1-17) It was confirmed that 1 and Comparative Example 2 showed higher efficiency and higher lifespan than Comparative Examples 3 to 6 using comparative compounds.

In addition, Comparative Examples 7 to 9 using Comparative Compounds 1 to 4 as a phosphorescent host by mixing Comparative Compounds 1 to 6 compared to Comparative Examples 1 to 6 using the single material showed a higher efficiency, higher lifetime, and lower driving voltage. I could confirm.

In addition, when the comparative compound was mixed and used as a phosphorescent host (Comparative Examples 7 to 9), the compound (1-17) represented by Chemical Formula 1 and the comparative compound 4 were mixed and used as a phosphorescent host. The result of Comparative Example 11, which was used as a phosphorescent host by mixing 2 and the compound represented by Formula 2 (2-101), was generally excellent in terms of efficiency and life, rather than the compound of the present invention represented by Formula 1 and Formula 2 It was found that the mixed examples 1 to 20 show remarkably excellent effects in terms of driving voltage, efficiency, and life.

The reason why the combination of the present invention is superior to that of Comparative Examples 7 to 9 in which a comparative compound was mixed and used as a phosphorescent host and Comparative Examples 10 and 11 in which a compound of the present invention and a comparative compound were used as a phosphorescent host is electron transfer. When a compound represented by Formula 2 having a strong hole characteristic is mixed with a polycyclic compound represented by Formula 1 having strong characteristics, the electron blocking ability is improved due to the high T1 and high LUMO energy values of the compound represented by Formula 2, It is judged that this is because more holes move quickly and easily in the light emitting layer due to the high HOMO energy value. Accordingly, it is judged that the charge balance in the light emitting layer of holes and electrons is increased, so that light emission is well performed inside the light emitting layer rather than the hole transport layer interface, thereby reducing degradation at the HTL interface, thereby maximizing the driving voltage, efficiency, and lifetime of the entire device . That is, the combination of Formula 1 and Formula 2 is thought to improve the performance of the entire device by synergistically electrochemically.

[Example 21] to [Example 26] Fabrication and test of red organic light emitting device according to mixing ratio

As described in Table 8, the organic electroluminescent device in the same manner as in Example 1, except that the first host compound and the second host compound were used in a weight ratio of 8:2, 7:3 and 6:4 Was produced.

Host 1 Host 2` Mixing ratio
(1st host: 2nd host) Driving voltage (V) Current density
(mA/cm ² ) Luminance
(cd/m2) efficiency
(cd/A) life span
T(95) Example (21) Compound (1-51) Compound (2-104) 8:2 4.1 8.0 2500.0 31.4 126.1 Example (22) Compound (1-51) Compound (2-104) 7:3 4.2 7.2 2500.0 34.9 130.7. Example (23) Compound (1-51) Compound (2-104) 6:4 4.3 6.8 2500.0 36.5 131.4 Example (24) Compound (1-52) Compound (2-101) 8:2 4.4 8.5 2500.0 29.3 120.2 Example (25) Compound (1-52) Compound (2-101) 7:3 4.5 7.6 2500.0 33.1 120.9 Example (26) Compound (1-52) Compound (2-101) 6:4 4.6 7.4 2500.0 33.8 122.2.

As shown in Table 8 above, the mixture of the compounds of the present invention was measured by fabricating devices by ratio (8:2, 7:3, 6:4).

When the results were described in detail, it was confirmed that as the first host ratio increased, the result of the driving voltage was further improved, but on the contrary, it was confirmed that the tendency of the driving voltage was the opposite. Therefore, in the case of a mixture, it is judged that it is a very important task to derive a mixing ratio in which the charge balance in the light emitting layer is maximized because the amount of the mixing ratio affects the properties.

The above description is merely illustrative of the present invention, and those skilled in the art to which the present invention pertains will be capable of various modifications without departing from the essential characteristics of the present invention. Therefore, the embodiments disclosed herein are not intended to limit the present invention, but to explain the present invention, and the spirit and scope of the present invention are not limited by these embodiments.

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

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

Claims (17)

In an organic electric device comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, the organic material layer includes a light emitting layer, and the light emitting layer is a phosphorescent light emitting layer (1) An organic electric device comprising a first host compound represented by and a second host compound represented by the following formula (2)
Formula (1) Formula (2)

{In the formulas (1) and (2) above,
1) Ar ¹ , Ar ² , Ar ³ , Ar ⁴ and Ar ⁵ are each independently hydrogen; heavy hydrogen; C ₆ ~ C ₆₀ Aryl group; Alkyl groups; C ₂ ~ C ₆₀ heteroaryl group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~C ₃₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And -L'-N(R _a )(R _b ), Ar ⁴ and Ar ⁵ may combine with each other to form a ring,
2) L ¹ , L ² and L'are each independently a single bond; C ₆ ~ C ₆₀ Arylene group; Or C ₂ ~ C ₆₀ heteroarylene group; is,
3) n is 1 or 2,
4) a is an integer from 0 to 6; b, c and e are each independently an integer from 0 to 4; d is an integer from 0 to 3,
5) R ¹ to R ⁵ are each independently 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 and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~C ₃₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And -L'-N (R _a ) (R _b ); is selected from the group consisting of,
When a, b, c, d and e are 2 or more, they are the same as or different from each other, and a plurality of R ¹ , a plurality of R ² , a plurality of R ³ , a plurality of R ⁴ , and a plurality of R ⁵ They may combine with each other to form an aromatic and heteroaromatic ring,
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 C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom; is selected from the group consisting of,
Here, the aryl group, fluorenyl group, arylene group, heterocyclic group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group each deuterium; halogen; Silane group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio; Alkoxyl group of C ₁ -C ₂₀ ; C ₁ -C ₂₀ alkyl group; Alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ Aryl group; A C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl group; C ₂ -C ₂₀ heterocyclic group; C ₃ -C ₂₀ cycloalkyl group; C ₇ -C ₂₀ arylalkyl group and C ₈ -C ₂₀ arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of, also, these substituents may combine with each other to form a ring, wherein ''Cycle' refers to a C ₃ -C ₆₀ aliphatic ring or a C ₆ -C ₆₀ aromatic ring or a C ₂ -C ₆₀ heterocycle or a fused ring thereof, and includes a saturated or unsaturated ring.}
The organic electroluminescent device according to claim 1, wherein at least one of R ¹ and R ² of the compound represented by the formula (1) is an aryl group of C ₆ to C ₆₀ .
The organic electroluminescent device according to claim 1, wherein the compound represented by the formula (1) is represented by any one of the following formulas (3) to (6).
Formula (3) Formula (4) Formula (5) Formula (6)

{In the formulas (3) to (6), Ar ¹ , Ar ² , L ¹ , R ¹ , R ² , a, b are the same as defined in claim 1,
1) R ⁶ and R ⁷ are each independently hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₄₈ aryl group; Fluorenyl group; C ₂ ~ C ₄₈ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₄₈ aliphatic ring and C ₆ ~ C ₄₈ aromatic ring fused 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,
f and bonded to each other between a plurality of R ⁶ a plurality of R ⁷ to each other when g is 2 or more, may form an aromatic, and heteroaromatic ring,
2) f and g are any integers from 0 to 5.}
The organic electroluminescent device according to claim 1, wherein Ar ¹ and Ar ² of the compound represented by Formula (1) are different from each other.
The organic electroluminescent device according to claim 1, wherein at least one of Ar ¹ and Ar ² is represented by the following formula (1-1).
Formula (1-1)

{In the above formula (1-1),
1) X is O, S, CR'R", SiR'R", Se, or NR',
2) R'and R" are each independently selected from the group consisting of hydrogen; C ₁ ~C ₂₀ alkyl group; C ₆ ~ C ₂₀ aryl group; and C ₂ ~ C ₂₀ heteroaryl group; or R 'And R" form a ring with each other to form a spiro ring,
3) R ⁸ and R ⁹ are each independently hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring and C ₆ ~ C ₂₀ aromatic ring fused ring group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~C ₃₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And -L'-N(R _a )(R _b ); when h and i are 2 or more, they are the same or different from each other as a plurality, and a plurality of R ^8s and a plurality of R ^9s are bonded to each other To form an aromatic and heteroaromatic ring, L', R _a and R _b are the same as defined in claim 1 above,
4) h is an integer from 0 to 4, and i is an integer from 0 to 3.}
The organic compound according to claim 1, wherein at least one of R ¹ and R ² of the compound represented by the formula (1) has a pair of two or more adjacent to each other to form a ring when a or b is 2 or more. Electrical element
The method of claim 1, wherein the formula (1) is an organic electric device, characterized in that any one of the following compounds

The organic electroluminescent device according to claim 1, wherein the compound represented by the formula (2) is represented by any one of the following formulas (21) to (24).
Formula (21) Formula (22) Formula (23) Formula (24)

{In the above formulas (21) to (24),
R ³ , R ⁴ , R ⁵ , Ar ³ , Ar ⁴ , Ar ⁵ , L ² , c, d, e and n are the same as defined in claim 1 above.}
The organic electroluminescent device according to claim 1, wherein the compound represented by the formula (2) is represented by any one of the following formulas (25) to (33).
Formula (25) Formula (26) Formula (27)

Formula (28) Formula (29) Formula (30)

Formula (31) Formula (32) Formula (33)

{In the formulas (25) to (33) above,
R ³ , R ⁴ , R ⁵ , Ar ³ , Ar ⁴ , Ar ⁵ , L ² , c, d, e are the same as defined in claim 1 above,
Ar ⁶ and Ar ⁷ are each independently hydrogen; heavy hydrogen; C ₆ ~ C ₆₀ Aryl group; Alkyl groups; C ₂ ~ C ₆₀ heteroaryl group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~C ₃₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And -L'-N(R _a )(R _b ); Ar ⁶ and Ar ⁷ may be bonded to each other to form a ring,
L', R _a and R _b are the same as defined in claim 1 above.}
The organic electroluminescent device according to claim 1, wherein at least one of Ar ⁴ and Ar ⁵ is represented by the following formula (2-1).
Formula (2-1)

{In the above formula (2-1),
1) Y is O, S, CR'R", SiR'R", Se, or NR',
2) R'and R” each independently hydrogen; C ₁ ~ C ₂₀ alkyl group; C ₆ ~ C ₂₀ aryl group; And C ₂ ~ C ₂₀ heteroaryl group; is selected from the group consisting of, or R'and R" to form a ring with each other to form a spiro (spiro) ring,
3) R ¹⁰ and R ¹¹ are each independently hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring and C ₆ ~ C ₂₀ aromatic ring fused ring group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₂₀ alkoxyl group; C ₆ ~ C ₂₀ Aryloxy group; And _{-L'-N (R a) (} R b); is selected from the group, j and the same or different from each other and bonded to each other a plurality of R ¹¹ among the plurality of R ^10, together as a plurality respectively not less than k is 2, consisting of To form an aromatic and heteroaromatic ring,
4) j is an integer from 0 to 4, k is an integer from 0 to 3,
5) L', R _a and R _b are the same as defined in claim 1 above.}
The method according to claim 1, wherein at least one of R ³ , R ⁴ and R ⁵ of the compound represented by the formula (2) is c, d or e is 2 or more, a pair of adjacent ones or more combine to form a ring. Organic electric device characterized in that
The method of claim 1, wherein the formula (2) is an organic electric device, characterized in that any one of the following compounds

The organic electroluminescent device according to claim 1, wherein the compounds represented by the formula (1) and the formula (2) are mixed in a ratio of any one of 1:9 to 9:1 by weight.
The organic electroluminescent device according to claim 1, wherein the compounds represented by the formula (1) and the formula (2) are mixed in a weight ratio of 1:9 to 5:5.
The organic electroluminescent device according to claim 1, wherein the compounds represented by the formula (1) and the formula (2) are mixed in a ratio of 2:8 to 3:7.
An electronic device comprising: a display device comprising the organic electroluminescent device according to claim 1 and a control unit driving the display device.
17. The electronic device according to claim 16, wherein the organic electric element is at least one of an organic electroluminescent element, an organic solar cell, an organic photoreceptor, an organic transistor, and a monochrome or white lighting element.

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