KR20190127554A - 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 light emitting efficiency, stability, and life of an element, an organic electronic element using the same, and an electronic device of the organic electronic element. The organic electronic element comprises: a first electrode; a second electrode; and an organic material layer formed between the first and second electrodes.

Description

COMPONENT FOR ORGANIC ELECTRONIC ELEMENT USING THE SAME AND AND EL 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, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic electric element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. In this case, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electric device, for example, it may be made of 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 element may be classified into light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like according to their functions.

In the case of bis type cyclic compounds containing heteroatoms, the difference in characteristics depending on the material structure is so great that they are applied to various layers as materials of organic electric devices. In particular, the band gap (HOMO, LUMO), electrical properties, chemical properties, and physical properties are different depending on the number of rings, the fused position, and the type and arrangement of heteroatoms. This has been going on.

In the phosphorescent organic EL device using the phosphorescent dopant material, the LUMO and HOMO levels of the host material have a great influence on the efficiency and the lifetime of the organic EL device. Accordingly, efficiency reduction and lifetime degradation due to charge balance control, dopant quenching, and light emission at the hole transport layer interface in the light emitting layer can be prevented.

In the case of fluorescent and phosphorescent light emitting materials, researches on increasing efficiency and lifespan of organic electric devices using thermally activated delayed fluorescent (TADF) and Exciplex have recently been conducted. Especially, the method of energy transfer from host materials to dopant materials has been investigated. There is a lot of research going on.

The energy transfer in the light emitting layer for thermal activated delayed fluorescent (TADF) and exciplex can be identified by the PL lifetime (TRTP) method.

The time resolved transient PL (TRTP) method is a method of observing a decay time of a spectrum after a pulsed light source is irradiated to a host thin film. It is a measuring method. The TRTP measurement is a measurement method that can distinguish between fluorescence and phosphorescence, and energy transfer method, exciplex energy transfer method, and TADF energy transfer method within a mixed host material.

As such, there are various factors that affect efficiency and lifespan depending on the way energy is transferred from the host material to the dopant material, and the energy transfer method differs depending on the material. This is not enough. Therefore, the development of new materials is continuously 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 control, efficiency and lifetime in the light emitting layer by adjusting the HOMO level for the host material of the phosphorescent organic electroluminescent device comprising a phosphorescent dopant Compound which can improve It aims at providing the organic electric element using this and its electronic device.

The present invention provides 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, wherein the organic material layer includes a light emitting layer, and the light emitting layer is a phosphorescent light emitting layer. Provided is an organic electric device comprising a first host compound represented by 1 and a second host compound represented by Formula 2 below.

In addition, the present invention provides an organic electronic device using the compound represented by the above formula 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 element, and also to greatly improve the life of the element.

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 the detailed description of the related well-known configuration or function may obscure the gist of the present invention, the detailed description thereof will be omitted.

In addition, in describing the component of this invention, terms, such as 1st, 2nd, A, B, (a), (b), can be used. These terms are only to distinguish the components from other components, and the nature, order or order of the components are not limited by the terms. If a component is described as being "connected", "coupled" or "connected" to another component, that component may be directly connected to or connected to that other component, but there may be another configuration between each component. It is to be understood that the elements may be "connected", "coupled" or "connected".

As used in this specification and the appended claims, unless otherwise indicated, the meanings of the following terms are as follows:

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

As used herein, the term "alkyl" or "alkyl group" has a single bond of 1 to 60 carbon atoms, unless otherwise indicated, and is a straight chain alkyl group, branched chain alkyl group, cycloalkyl (alicyclic) group, alkyl-substituted cyclo Radicals of saturated aliphatic functional groups, including alkyl groups, cycloalkyl-substituted alkyl groups.

As used herein, the term "haloalkyl group" or "halogenalkyl group" means an alkyl group substituted with halogen unless otherwise specified.

The term "heteroalkyl group" as used herein means that at least one of the carbon atoms constituting the alkyl group has been replaced with a heteroatom.

As used herein, the terms "alkenyl group", "alkenyl group" or "alkynyl group" have a double or triple bond of 2 to 60 carbon atoms, respectively, unless otherwise stated, and include straight or branched chain groups. It is not limited to this.

The term "cycloalkyl" as used herein, unless otherwise stated, refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto.

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

As used herein, the term "alkenoxyl group", "alkenoxy group", "alkenyloxyl group", or "alkenyloxy group" means an alkenyl group to which an oxygen radical is attached, and unless otherwise stated, it is 2 to 60 It has carbon number of, It is not limited to this.

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

As used herein, the terms "aryl group" and "arylene group" each have a carbon number of 6 to 60 unless otherwise stated, it is not limited thereto. In the present invention, an aryl group or an arylene group means an aromatic of a single ring or multiple rings, and includes an aromatic ring formed by neighboring substituents participating in a bond or a reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, a 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 the radical substituted with an aryl group has the carbon number described herein.

Also, when prefixes are named consecutively, it means that the substituents are listed in the order described first. For example, an arylalkoxy group means an alkoxy group substituted with an aryl group, an alkoxylcarbonyl group means a carbonyl group substituted with an alkoxyl group, and an arylcarbonylalkenyl group 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 an alkyl including one or more heteroatoms unless otherwise indicated. As used herein, the term "heteroaryl group" or "heteroarylene group" means an aryl group or arylene group having 2 to 60 carbon atoms, each containing one or more heteroatoms, unless otherwise specified. It may include at least one of a single ring and multiple rings, and may be formed by combining adjacent functional groups.

As used herein, the term “heterocyclic group” includes one or more heteroatoms, unless otherwise indicated, and has from 2 to 60 carbon atoms, and includes at least one of single and multiple rings, heteroaliphatic rings and hetero Aromatic rings. Adjacent functional groups may be formed in combination.

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

"Heterocyclic groups" may also include rings comprising SO ₂ instead of carbon forming the ring. For example, a "heterocyclic group" includes the following compounds.

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

Unless otherwise stated, the term "ring" as used herein refers to a fused ring consisting of an aliphatic ring having 3 to 60 carbon atoms or an aromatic ring having 6 to 60 carbon atoms or a hetero ring having 2 to 60 carbon atoms or a combination thereof. Saturated or unsaturated rings.

Other heterocompounds or heteroradicals other than the aforementioned heterocompounds include, but are not limited to, one or more heteroatoms.

Unless otherwise stated, the term "carbonyl" used in the present invention is represented by -COR ', wherein R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and 3 to 30 carbon atoms. 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" as used herein 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, It is an aryl group, a C3-C30 cycloalkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, or a combination thereof.

Also, unless stated otherwise, 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, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, a C ₈ ~ C ₂₀ aryl alkenyl group, a silane group, a boron Group, germanium group, and C ₂ ~ C _{20 It} is meant to be substituted with one or more substituents selected from the group consisting of, but not limited to these substituents.

In addition, unless otherwise specified, the formulas used in the present invention apply in the same manner as the substituent definitions by the exponential definition of the following formula.

Herein, when a is an integer of 0, the substituent R ¹ is absent, that is, when a is 0, it means that all of the carbons forming the benzene ring are bonded to hydrogen. Omitted formulas and compounds may be omitted. When a is an integer of 1, one substituent R ¹ is bonded to any one of carbons forming a benzene ring, and when a is an integer of 2 or 3, each of them is bonded as follows, and R ¹ may be the same or different from each other. And when a is an integer of 4 to 6, is bonded to the carbon of the benzene ring in a similar manner, while the indication of hydrogen bonded to the carbon forming the benzene ring is omitted.

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

The present invention provides 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, wherein the organic material layer includes a light emitting layer, and the light emitting layer is a phosphorescent light emitting layer. Provided is an organic electric device comprising a first host compound represented by 1 and a second host compound represented by Formula 2 below.

{In Formula 1 and Formula 2,

1) Ar ¹ , Ar ² and Ar ³ are each independently a C ₆ -C ₆₀ aryl group; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; Fluorenyl groups; A fused ring group of an aromatic ring of C ₆ -C ₆₀ and an aliphatic ring of C ₃ -C ₆₀ ; An alkyl group of C ₁ -C ₅₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; And an aryloxy group of C ₆ -C ₃₀ , and also Ar ² And Ar ³ may combine with each other to form a ring,

2) n is 1 or 2,

3) L ¹ or L ² is a single bond independently of each other; C ₆ -C ₆₀ arylene group; Fluorenylene groups; A C ₂ -C ₆₀ heterocyclic group comprising at least one hetero atom of O, N, S, Si, and P; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; And an aliphatic hydrocarbon group; selected from the group consisting of,

4) Ar ⁴ is an aryl group of C ₆ -C ₆₀ or a heterocyclic group of C ₂ -C ₆₀ ,

5) p, r or t is 0-4, q or s is 0-3,

6) R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ are independently of each other hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ ~ C ₆₀ Aryl group; Fluorenyl groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ -C ₃₀ alkoxyl group; C ₆ -C ₃₀ aryloxy group; And -L'-N (R ^a ) (R ^b ); When p, q, r, s and t are 2 or more, a plurality of adjacent R ⁴ , a plurality of adjacent R ⁵ , a plurality of adjacent R ⁶ , a plurality of adjacent R ⁷ , and a plurality of adjacent R ⁸ may be bonded to each other to form a saturated or unsaturated ring,

7) R ^a and R ^b are each independently of the C ₆ -C ₆₀ aryl group; Fluorenyl groups; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; And a C ₂ -C ₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si, and P, and

8) X is O or S,

Here, the aryl group, fluorenyl group, arylene group, heterocyclic group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group are each deuterium; halogen; Silane group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; Import alkylthio of C ₁ -C _20; An alkoxyl group of C ₁ -C ₂₀ ; An alkyl group of C ₁ -C ₂₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; Aryl group of C ₆ -C ₂₀ ; C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl groups; C ₂ -C ₂₀ heterocyclic group; A cycloalkyl group of C ₃ -C ₂₀ ; C ₇ -C ₂₀ arylalkyl group and C ₈ -C ₂₀ arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of, these substituents may be bonded to each other to form a ring, wherein ' Ring 'means a fused ring consisting of an aliphatic ring of C ₃ -C ₆₀ or an aromatic ring of C ₆ -C ₆₀ or a hetero ring of C ₂ -C ₆₀ or a combination thereof, and includes a saturated or unsaturated ring.}

In addition, the present invention provides an organic electroluminescence device comprising a compound represented by any one among the L ¹ or L ² has the formula b-1 to b-13 in the formula (1) or (2).

{In Chemical Formula b-1 to Chemical Formula b-13,

1) Y is NL ³ -Ar ⁵ , O, S or CR'R ",

2) L ³ is the same as the definition of L ¹ ,

3) Ar ⁵ is the same as the definition of Ar ¹ ,

4) R 'and R "are independently of each other hydrogen; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₃ ~ C ₆₀ Heterocyclic group; C ₁ ~ C ₅₀ Alkyl group; and -L'-N (R ^a ) (R ^b ) and R ′ and R ″ may combine with each other to form a spiro ring,

5) a, c, d, and e are independently of each other an integer from 0 to 4, b is an integer from 0 to 6, f and g are independently from each other an integer from 0 to 3, h is an integer from 0 to 2 , i is an integer of 0 or 1,

6) R ¹ , R ² and R ³ are independently of each other hydrogen; heavy hydrogen; Tritium; halogen; Cyano group; Nitro group; C ₆ -C ₆₀ aryl group; Fluorenyl groups; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; An alkyl group of C ₁ -C ₅₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; When selected from the group consisting of C ₆ -C ₃₀ aryloxy group and -L ^a -N (R ^d ) (R ^e ), or wherein a, b, c, d, e, f and g are 2 or more, And when h is 2 or more, each is the same or different from each other, and a plurality of R ¹ or a plurality of R ² or a plurality of R ³ or neighboring R ¹ and R ² or R ² and R ³ are bonded to each other Can form an aromatic ring or a heteroaromatic ring,

Wherein L ^a is a single bond; C ₆ -C ₆₀ arylene group; Fluorenylene groups; A C ₂ -C ₆₀ heterocyclic group comprising at least one hetero atom of O, N, S, Si, and P; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; And C ₃ -C ₆₀ aliphatic hydrocarbon group, wherein R ^d and R ^e are each independently of the C ₆ -C ₆₀ aryl group; Fluorenyl groups; C ₂ -C ₆₀ heterocyclic group including at least one hetero atom selected from the group consisting of O, N, S, Si and P; And a fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ .

7) Z ⁴⁹ , Z ⁵⁰ and Z ⁵¹ are independently of each other CR ^f or N, at least one of Z ⁴⁹ , Z ⁵⁰ and Z ⁵¹ is N,

R ^f is hydrogen; heavy hydrogen; Tritium; halogen; Cyano group; Nitro group; C ₆ -C ₆₀ aryl group; Fluorenyl groups; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; An alkyl group of C ₁ -C ₅₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; And an aryloxy group of C ₆ -C ₃₀ , and adjacent R ¹ and R ^f may combine with each other to form an aromatic ring or a heteroaromatic ring.}

Specifically, the present invention provides an organic electric device comprising at least one of Ar ² and Ar ³ includes a compound represented by the following Chemical Formula 1-1.

{In Formula 1-1,

A and B are independently of each other a C ₆ ~ C ₂₄ aryl group or C ₂ ~ C ₂₄ heterocyclic group,

X ¹ is NL ⁵ -Ar ⁶ , O, S or CR'R ",

L ⁴ and L ⁵ are the same as defined above L ¹

Ar ⁶ is the same as defined in Ar ¹

R 'and R "are independently of each other hydrogen; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₃ ~ C ₆₀ heterocyclic group; C ₁ ~ C ₅₀ Alkyl group; and -L'-N (R ^a ) (R ^b ) and R ′ and R ″ may be bonded to each other to form a spiro ring.}

As another example, the present invention provides an organic electric device comprising a compound represented by any one of the following Chemical Formula 1 to the first host compound represented by Chemical Formula 1.

{In Formula 3 to Formula 6,

Ar ¹ , Ar ² , Ar ³ , R ⁴ , R ⁵ , L ¹ , p, q are as defined above

Ar ⁷ or Ar ⁸ is as defined the above Ar ^1.}

As another example, the present invention provides an organic electric device in which the second host compound represented by Formula 2 includes a compound represented by Formula 7 or Formula 8 below.

{In Formula 7 or Formula 8, R ⁶ , R ⁷ , R ⁸ , L ² , Ar ⁴ , r, s, and t are as defined above.}

On the other hand, the present invention provides an organic electric device comprising a compound represented by the following formula (9) to the second host compound represented by the formula (2).

      <Formula 9> <Formula 10> <Formula 11>

      <Formula 12> <Formula 13>

{In Formula 9 to Formula 13,

1) R ⁶ , R ⁷ , R ⁸ , L ² , X, r, s and t are as defined above,

2) R ⁹ is an aryl group of C ₆ ~ C ₁₀ ,

3) R ¹⁰ to R ¹² are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ ~ C ₆₀ Aryl group; Fluorenyl groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ -C ₃₀ alkoxyl group; C ₆ -C ₃₀ aryloxy group; And -L'-N (R ^a ) (R ^b ); Is selected from the group consisting of

4) Ar ⁷ and Ar ⁸ are each independently of the other C ₆ -C ₆₀ aryl group; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; Fluorenyl groups; A fused ring group of an aromatic ring of C ₆ -C ₆₀ and an aliphatic ring of C ₃ -C ₆₀ ; An alkyl group of C ₁ -C ₅₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; And C ₆ -C ₃₀ An aryloxy group; selected from the group consisting of,

5) L ⁶ is a single bond; C ₆ -C ₆₀ arylene group; Fluorenylene groups; A C ₂ -C ₆₀ heterocyclic group comprising at least one hetero atom of O, N, S, Si, and P; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; And an aliphatic hydrocarbon group; selected from the group consisting of,

6) Z is O or S,

7) u is from 0 to 3; v or w are 0 to 4 independently of each other.

Specifically, the present invention provides an organic electric device comprising at least one of Ar ⁷ or Ar ⁸ includes a compound represented by the following Chemical Formula 1-2.

  <Formula 1-2>

{In Formula 1-2,

C and D are independently of each other a C ₆ ~ C ₂₄ aryl group or C ₂ ~ C ₂₄ heterocyclic group,

X ² is NL ⁸ -Ar ⁹ , O, S or CR'R '',

L ⁷ and L ⁸ are the same as the definition of L ⁶ above,

Ar ⁹ is an aryl group of C ₆ -C ₆₀ ; Or a C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si, and P; ego,

R 'and R''are independently of each other hydrogen; C ₆ ~ C ₆₀ Aryl group; Fluorenyl groups; C ₃ ~ C ₆₀ Heterocyclic group; And C ₁ ~ C ₅₀ Alkyl group; It is selected from the group consisting of.}

In one embodiment, the first host compound represented by Chemical Formula 1 includes the following Compounds 1-1 to 1-132.

In addition, in the present invention, the second host compound represented by Chemical Formula 2 includes the following Compounds 2-1 to 2-131.

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 a substrate 110. An organic material layer including a 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 may sequentially include the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, the light emitting auxiliary layer 151, the electron transport layer 160, and the electron injection layer 170 on the first electrode 120. It may include. At this time, the remaining layers except for the light emitting layer 150 may not be formed. The hole blocking layer, the electron blocking layer, the light emitting auxiliary layer 151, the electron transport auxiliary layer, the buffer layer 141 may be further included, and the electron transport layer 160 may serve as the hole blocking layer.

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

Meanwhile, even in the same core, band gaps, electrical characteristics, and interface characteristics may vary depending on which substituents are bonded at which positions. Therefore, the selection of cores and the combination of sub-substituents bound thereto are also very significant. Importantly, long life and high efficiency can be achieved at the same time when an optimal combination of energy level and T1 value and intrinsic properties (mobility, interfacial properties, etc.) of each organic material layer is achieved.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using a PVD method. For example, a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode, and the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, the electron transport layer 160 are disposed thereon. After forming the organic material layer including the electron injection layer 170, it can be prepared 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 an electron transport auxiliary layer may be further formed between the light emitting layer 150 and the electron transport layer 160.

Accordingly, the present invention includes at least one hole transport band layer between the first electrode and the light emitting layer, the hole transport band layer includes a hole transport layer, a light emitting auxiliary layer or both, the hole transport band layer It provides an organic electric device comprising the compound represented by the formula (1).

In addition, the present invention provides an organic electroluminescent device included in the light emitting layer by mixing the compound represented by Formula 1 and Formula 2 in any one of 1: 9 to 9: 1, preferably 1: 9 to 5: 5, More preferably, it is mixed in the ratio of 2: 8-4: 6, and is contained in the said light emitting layer.

The organic electroluminescent device further includes a light efficiency improvement 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. 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, the organic material layer according to the present invention can be formed in various ways Therefore, the scope of the present invention is not limited by the formation method.

The organic electric element according to an embodiment of the present invention may be a top emission type, a bottom emission type or a double-sided emission type according to the material used.

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

In another aspect, the present invention is a display device including the above-described organic electric element; And a controller for driving the display device.

In another aspect, the organic electronic device provides an electronic device according to the present invention, wherein the organic electroluminescent device is at least one of an organic electroluminescent device, an organic solar cell, an organic photoconductor, an organic transistor, and a monochromatic or white illumination device. In this case, the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.

Hereinafter, the synthesis examples of the compounds represented by Chemical Formulas 1 and 2 of the present invention and the production examples of the organic electric device of the present invention will be described in detail with reference to Examples, but are not limited to the following Examples of the present invention. .

[ Synthesis Example  One]

Compound represented by the formula (1) according to the present invention (final product 1) is synthesized by reacting Sub 1 and Sub 2 as shown in Scheme 1, but is not limited thereto. Ar ¹ to Ar ³ , R ⁴ , R ⁵ , L ¹ , p, q and n are the same as defined in Formula 1.

<Scheme 1>

I. Synthesis of Sub 3

Sub 1 of Scheme 1 is synthesized by the reaction route of Scheme 2, but is not limited thereto. Ar ¹ , R ⁴ , R ⁵ , L ¹ , p, q and n are the same as defined in formula (1).

<Scheme 2>

Sub 1-III-1 Synthesis Example

(1) Sub 1-III-1 Synthesis

After dissolving 3-bromo-9-phenyl-9H-carbazole (45.1 g, 140 mmol) in 980 mL of DMF, Bispinacolborate (39.1 g, 154 mmol), PdCl ₂ (dppf) catalyst (3.43 g, 4.2 mmol), KOAc (41.3 g, 420 mmol) was added sequentially, followed by stirring for 24 hours to synthesize the borate compound, and then the obtained compound was separated through Silicagel Column and recrystallization, and 35.2 g of product Sub1-III-1 (yield 68%) Got it.

2.Sub 1-III-2 Synthesis Example

(1) Synthesis of Sub 1-III-2

2-bromo-9-phenyl-9H-carbazole (76.78 g, 238.3 mmol), Bispinacolborate (66.57 g, 262.1 mmol), PdCl ₂ (dppf) catalyst (5.84 g, 7.1 mmol), KOAc (70.16 g, 714.9 mmol) The product Sub1-III-2 was obtained 73.92 g (yield 84%) using the synthesis method of Sub1-III-1.

3.Sub 1-10 Synthesis Example

(1) Sub 1-10 Synthesis

9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole (29.5 g, 80 mmol) was dissolved in 360 mL of THF, then 3- bromo-3'-iodo-1,1'-biphenyl (30.16 g, 84 mmol), Pd (PPh ₃ ) ₄ catalyst (2.8 g, 2.4 mmol), NaOH (9.6 g, 240 mmol), 180 mL water added After stirring, the mixture was refluxed. After completion of the reaction, the mixture was extracted with ether and water, the organic layer was dried over MgSO ₄ , concentrated, and the resulting organic material was purified by Silicagel Column and recrystallized to give 26.56 g (70%) of Sub 1-10.

4.Sub 1-3 Synthesis Example

(1) Sub 1-3 synthesis

9-phenyl-2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole (29.5 g, 80 mmol), THF 360 mL, 1-bromo-4 180 mL of -iodobenzene (23.8 g, 84 mmol), Pd (PPh ₃ ) ₄ catalyst (2.8 g, 2.4 mmol), NaOH (9.6 g, 240 mmol), and water were synthesized using the Sub 1-10 synthesis method. 22.9 g (72%) were obtained.

5.Sub 1-5 Synthesis Example

(1) Sub 1-5 synthesis

9-phenyl-2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole (73.92 g, 200.2 mmol) was dissolved in a round bottom flask with 880 mL of THF. After that, 1-bromo-2-iodobenzene (85.0 g, 300.3 mmol), Pd (PPh ₃ ) ₄ (11.6 g, 10 mmol), K ₂ CO ₃ (83 g, 600.6 mmol), and 440 mL of water were added to Sub 1 55.8 g (70% yield) of product Sub 1-5 were obtained using the synthesis method of -10.

6.Sub 1-15 Synthesis Example

(1) Sub 1-15 Synthesis

9-phenyl-2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole (73.92 g, 200.2 mmol) was dissolved in a round bottom flask with 880 mL of THF. Later, 2-bromo-7-iododibenzo [b, d] furan (112.0 g, 300.3 mmol), Pd (PPh ₃ ) ₄ (11.6 g, 10 mmol), K ₂ CO ₃ (83 g, 600.6 mmol), water 440 mL of 72.4 g (74% yield) of product Sub 1-15 was obtained using the synthesis method of Sub 1-10.

7.Sub 1-22 Synthesis Example

(1) Sub 1-22 Synthesis

9-phenyl-2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole (73.92 g, 200.2 mmol) was dissolved in a round bottom flask with 880 mL of THF. Then, 1,3-dibromo-5-iodobenzene (108.65 g, 300.3 mmol), Pd (PPh ₃ ) ₄ (11.6 g, 10 mmol), K ₂ CO ₃ (83 g, 600.6 mmol), 440 mL of water 69.7 g (73% yield) of product Sub 1-22 were obtained using the synthesis method of Sub 1-10.

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

compound FD-MS compound FD-MS Sub1-1 m / z = 321.02 (C ₁₈ H ₁₂ BrN = 322.21) Sub1-2 m / z = 321.02 (C ₁₈ H ₁₂ BrN = 322.21) Sub1-3 m / z = 397.05 (C ₂₄ H ₁₆ BrN = 398.30) Sub1-4 m / z = 563.12 (C ₃₇ H ₂₆ BrN = 564.53) Sub1-5 m / z = 397.05 (C ₂₄ H ₁₆ BrN = 398.30) Sub1-6 m / z = 397.05 (C ₂₄ H ₁₆ BrN = 398.30) Sub1-7 m / z = 473.08 (C ₃₀ H ₂₀ BrN = 474.40) Sub1-8 m / z = 473.08 (C ₃₀ H ₂₀ BrN = 474.40) Sub1-9 m / z = 473.08 (C ₃₀ H ₂₀ BrN = 474.40) Sub1-10 m / z = 473.08 (C ₃₀ H ₂₀ BrN = 474.40) Sub1-11 m / z = 473.08 (C ₃₀ H ₂₀ BrN = 474.40) Sub1-12 m / z = 473.08 (C ₃₀ H ₂₀ BrN = 474.40) Sub1-13 m / z = 497.08 (C ₃₂ H ₂₀ BrN = 498.42) Sub1-14 m / z = 503.03 (C ₃₀ H ₁₈ BrNS = 504.45) Sub1-15 m / z = 487.06 (C ₃₀ H ₁₈ BrNO = 488.38) Sub1-16 m / z = 513.11 (C ₃₃ H ₂₄ BrN = 514.47) Sub1-17 m / z = 473.08 (C ₃₀ H ₂₀ BrN = 474.40) Sub1-18 m / z = 628.13 (C ₃₉ H ₂₅ BrN ₄ = 629.56) Sub1-19 m / z = 589.14 (C ₃₉ H ₂₈ BrN = 890.56) Sub1-20 m / z = 627.13 (C ₄ H ₂₆ BrN ₃ = 628.57) Sub1-21 m / z = 473.08 (C ₃₀ H ₂₀ BrN = 474.40) Sub1-22 m / z = 474.96 (C ₂₄ H ₁₅ Br ₂ N = 477.20) Sub1-23 m / z = 550.99 (C ₃₀ H ₁₉ Br ₂ N = 553.30) Sub1-24 m / z = 580.94 (C ₃₀ H ₁₇ Br ₂ NS = 583.34) Sub1-25 m / z = 477.94 (C ₂₁ H ₁₂ Br ₂ N ₄ = 480.16) Sub1-26 m / z = 630.01 (C ₃₃ H ₂₀ Br ₂ N ₄ = 632.36) Sub1-27 m / z = 574.99 (C ₃₂ H ₁₉ Br ₂ N = 577.32) Sub1-28 m / z = 550.99 (C ₃₀ H ₁₉ Br ₂ N = 553.30) Sub1-29 m / z = 524.97 (C ₂₈ H ₁₇ Br ₂ N = 527.26) Sub1-30 m / z = 524.97 (C ₂₈ H ₁₇ Br ₂ N = 527.26) Sub1-31 m / z = 574.99 (C ₃₂ H ₁₉ Br ₂ N = 577.32) Sub1-32 m / z = 513.11 (C ₃₃ H ₂₄ BrN = 514.47)

II. Synthesis of Sub 2

Sub 2 of Scheme 3 may be synthesized by the reaction route of Scheme 3 below, which may be disclosed in Korean Patent Registration No. 10-1251451 (published on April 5, 2013) of the present applicant, but is not limited thereto.

<Scheme 3>

Compounds belonging to Sub 2 may be the following compounds, but are not limited thereto, and Table 2 shows Field Desorption-Mass Spectrometry (FD-MS) values of some compounds belonging to Sub 2.

compound FD-MS compound FD-MS Sub2-1 m / z = 169.09 (C ₁₂ H ₁₁ N = 169.22) Sub2-2 m / z = 245.12 (C ₁₈ H ₁₅ N = 245.32) Sub2-3 m / z = 245.12 (C ₁₈ H ₁₅ N = 245.32) Sub2-4 m / z = 321.15 (C ₂₄ H ₁₉ N = 321.41) Sub2-5 m / z = 321.15 (C ₂₄ H ₁₉ N = 321.41) Sub2-6 m / z = 269.12 (C ₂₀ H ₁₅ N = 269.34) Sub2-7 m / z = 269.12 (C ₂₀ H ₁₅ N = 269.34) Sub2-8 m / z = 295.14 (C ₂₂ H ₁₇ N = 295.38) Sub2-9 m / z = 409.18 (C ₃₁ H ₂₃ N = 409.52) Sub2-10 m / z = 483.20 (C ₃₇ H ₂₅ N = 483.60) Sub2-11 m / z = 459.20 (C ₃₅ H ₂₅ N = 459.58) Sub2-12 m / z = 485.21 (C ₃₇ H ₂₅ N = 485.62) Sub2-13 m / z = 275.08 (C ₁₈ H ₁₃ NS = 275.37) Sub2-14 m / z = 335.13 (C ₂₄ H ₁₇ NO = 335.40) Sub2-15 m / z = 297.13 (C ₂₀ H ₁₅ N ₃ = 297.13) Sub2-16 m / z = 219.10 (C ₁₆ H ₁₃ N = 219.28) Sub2-17 m / z = 249.12 (C ₁₇ H ₁₅ NO = 249.31) Sub2-18 m / z = 197.12 (C ₁₄ H ₁₅ N = 197.28) Sub2-19 m / z = 229.11 (C ₁₄ H ₁₅ NO ₂ = 229.27) Sub2-20 m / z = 174.12 (C ₁₂ H ₆ D ₅ N = 174.25) Sub2-21 m / z = 281.21 (C ₂₀ H ₂₇ N = 281.44) Sub2-22 m / z = 321.15 (C ₂₄ H ₁₉ N = 321.41) Sub2-23 m / z = 321.15 (C ₂₄ H ₁₉ N = 321.41) Sub2-24 m / z = 321.15 (C ₂₄ H ₁₉ N = 321.41) Sub2-25 m / z = 321.15 (C ₂₄ H ₁₉ N = 321.41) Sub2-26 m / z = 321.15 (C ₂₄ H ₁₉ N = 321.41) Sub2-27 m / z = 297.13 (C ₂₀ H ₁₅ N ₃ = 297.13) Sub2-28 m / z = 499.20 (C ₃₆ H ₂₅ N ₃ = 499.60) Sub2-29 m / z = 410.18 (C ₃₀ H ₂₂ N ₂ = 410.52) Sub2-30 m / z = 424.16 (C ₃₀ H ₂₀ N ₂ O = 424.49) Sub2-31 m / z = 440.13 (C ₃₀ H ₂₀ N ₂ S = 440.56) Sub2-32 m / z = 384.16 (C ₂₈ H ₂₀ N ₂ = 384.47) Sub2-33 m / z = 334.15 (C ₂₄ H ₁₈ N ₂ = 334.41) Sub2-34 m / z = 450.21 (C ₃₃ H ₂₆ N ₂ = 450.57) Sub2-35 m / z = 410.18 (C ₃₀ H ₂₂ N ₂ = 410.52) Sub2-36 m / z = 410.18 (C ₃₀ H ₂₂ N ₂ = 410.52) Sub2-37 m / z = 575.24 (C ₄₂ H ₂₉ N ₃ = 575.70) Sub2-38 m / z = 575.24 (C ₄₂ H ₂₉ N ₃ = 575.70) Sub2-39 m / z = 460.19 (C ₃₄ H ₂₄ N ₂ = 460.57) Sub2-40 m / z = 460.19 (C ₃₄ H ₂₄ N ₂ = 460.57) Sub2-41 m / z = 461.19 (C ₃₃ H ₂₃ N ₃ = 461.56) Sub2-42 m / z = 626.27 (C ₄₇ H ₃₄ N ₂ = 626.79) Sub2-43 m / z = 565.23 (C ₃₉ H ₂₇ N ₅ = 565.67) Sub2-44 m / z = 415.21 (C ₃₀ H ₁₇ D ₅ N ₂ = 415.54) Sub2-45 m / z = 486.21 (C ₃₆ H ₂₆ N ₂ = 486.61) Sub2-46 m / z = 415.21 (C ₃₀ H ₁₇ D ₅ N ₂ = 415.54)

III. Final Product 1 Synthesis

1-3-7 Synthesis Example

(1) 1-37 synthesis method

Sub2-1 (8.0 g, 47.3 mmol) was added to a round bottom flask and dissolved with Toluene (500 mL), then Sub1-6 (20.7 g, 52.0 mmol), Pd ₂ (dba) ₃ (2.4 g, 2.6 mmol) P ( t -Bu) ₃ (1.05 g, 5.2 mmol) and NaO t -Bu (13.6 g, 141.8 mmol) were added and stirred at 100 ° C. After the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was purified by Silicagel Column and recrystallization to give 16.1 g (yield 70%) of product 1-37.

2. 1-10 Synthesis Example

(1) 1-10 synthesis method

Sub2-35 (19.4 g, 47.3 mmol), toluene (500 mL), Sub1-5 (20.7 g, 52.0 mmol), Pd ₂ (dba) ₃ (2.4 g, 2.6 mmol), P ( t -Bu) ₃ ( 1.05 g, 5.2 mmol) and NaO t -Bu (13.6 g, 141.8 mmol) were obtained using the synthesis method 1-37 to give 24.1 g (yield 70%) of product 1-10.

3. 1-54 Synthesis Example

(1) Inter_A-1 synthesis method

Sub2-2 (11.6 g, 47.3 mmol), toluene (500 mL), Sub1-22 (24.8 g, 52.0 mmol), Pd ₂ (dba) ₃ (2.4 g, 2.6 mmol), P ( t -Bu) ₃ ( 1.05 g, 5.2 mmol) and NaO t -Bu (13.6 g, 141.8 mmol) were obtained using the above 1-37 synthesis method to give 22.8 g (yield 75%) of product Inter_A-1.

(2) 1-54 synthesis method

Sub2-13 (8 g, 29.05 mmol), toluene (305 mL), Inter_A-1 (20.5 g, 32 mmol), Pd ₂ (dba) ₃ (1.5 g, 1.6 mmol), P ( t -Bu) ₃ (0.65 g, 3.2 mmol) and NaO t -Bu (8.4 g, 87.2 mmol) were obtained using the above 1-37 synthesis method to give 18 g (yield 74%) of product 1-54.

4. 1-69 Synthesis Example

(1) 1-69 synthesis method

Sub2-46 (7.2 g, 20 mmol), toluene (210 mL), Sub1-33 (8.73 g, 22 mmol), Pd ₂ (dba) ₃ (1 g, 1.1 mmol), P ( t -Bu) ₃ ( 0.4 g, 2.2 mmol) and NaO t -Bu (5.74 g, 60 mmol) were obtained using the above-mentioned 1-37 synthesis method to obtain 11.5 g (yield 85%) of product 1-69.

5. 1-82 Synthesis Example

(1) 1-82 Synthesis

Sub2-12 (9.7 g, 20 mmol), toluene (210 mL), Sub1-34 (12.2 g, 22 mmol), Pd ₂ (dba) ₃ (1 g, 1.1 mmol), P ( t -Bu) ₃ ( 0.4 g, 2.2 mmol) and NaO t -Bu (5.74 g, 60 mmol) were obtained using the above 1-37 synthesis method to give 15.5 g (yield 81%) of product 1-82.

6. 1-124 Synthesis Example

(1) 1-124 Synthesis

Sub2-16 (6.3 g, 28.9 mmol), toluene (260 mL), Sub1-35 (13.9 g, 24.1 mmol), Pd ₂ (dba) ₃ (2.2 g, 2.4 mmol), P ( t -Bu) ₃ ( 1 g, 4.8 mmol) and NaO t -Bu (8.3 g, 86.7 mmol) were obtained using the synthesis method 1-37 to give 16.5 g (yield 80%) of product 1-124.

On the other hand, FD-MS values of the compounds 1-1 to 1-132 of the present invention prepared according to the synthesis examples as described above are shown in Table 3.

compound FD-MS compound FD-MS 1-1 m / z = 562.24 (C ₄₂ H ₃₀ N ₂ = 562.72) 1-2 m / z = 602.27 (C ₄₅ H ₃₄ N ₂ = 602.78) 1-3 m / z = 563.24 (C ₄₁ H ₂₉ N ₃ = 563.70) 1-4 m / z = 714.30 (C ₅₄ H ₃₈ N ₂ = 714.91) 1-5 m / z = 678.30 (C ₅₁ H ₃₈ N ₂ = 678.88) 1-6 m / z = 802.33 (C ₆₁ H ₄₂ N ₂ = 803.02) 1-7 m / z = 800.32 (C ₆₁ H ₄₀ N ₂ = 801.01) 1-8 m / z = 563.24 (C ₄₁ H ₂₉ N ₃ = 563.70) 1-9 m / z = 668.23 (C ₄₈ H ₃₂ N ₂ S = 668.86) 1-10 m / z = 727.30 (C ₅₄ H ₃₇ N ₃ = 727.91) 1-11 m / z = 652.25 (C ₄₈ H ₃₂ N ₂ O = 652.80) 1-12 m / z = 662.27 (C ₅₀ H ₃₄ N ₂ = 662.84) 1-13 m / z = 536.23 (C ₄₀ H ₂₈ N ₂ = 536.68) 1-14 m / z = 586.24 (C ₄₄ H ₃₀ N ₂ = 586.74) 1-15 m / z = 712.29 (C ₅₄ H ₃₆ N ₂ = 712.90) 1-16 m / z = 714.30 (C ₅₄ H ₃₈ N ₂ = 714.91) 1-17 m / z = 754.33 (C ₅₇ H ₄₂ N ₂ = 754.98) 1-18 m / z = 957.38 (C ₇₀ H ₄₇ N ₅ = 958.18) 1-19 m / z = 965.38 (C ₇₃ H ₄₇ N ₃ = 966.20) 1-20 m / z = 719.24 (C ₅₁ H ₃₃ N ₃ S = 719.91) 1-21 m / z = 758.24 (C ₅₄ H ₃₄ N ₂ OS = 758.94) 1-22 m / z = 893.38 (C ₆₇ H ₄₇ N ₃ = 894.13) 1-23 m / z = 652.25 (C ₄₈ H ₃₂ N ₂ O = 652.80) 1-24 m / z = 662.27 (C ₅₀ H ₃₄ N ₂ = 662.84) 1-25 m / z = 562.24 (C ₄₂ H ₃₀ N ₂ = 562.72) 1-26 m / z = 612.26 (C ₄₆ H ₃₂ N ₂ = 612.78) 1-27 m / z = 688.29 (C ₅₂ H ₃₆ N ₂ = 688.87) 1-28 m / z = 714.30 (C ₅₄ H ₃₈ N ₂ = 714.91) 1-29 m / z = 754.33 (C ₅₇ H ₄₂ N ₂ = 754.98) 1-30 m / z = 833.29 (C ₆₀ H ₃₉ N ₃ S = 834.05) 1-31 m / z = 742.26 (C ₅₄ H ₃₄ N ₂ O ₂ = 742.88) 1-32 m / z = 778.33 (C ₅₉ H ₄₂ N ₂ = 779.00) 1-33 m / z = 486.21 (C ₃₆ H ₂₆ N ₂ = 486.62) 1-34 m / z = 536.23 (C ₄₀ H ₂₈ N ₂ = 536.68) 1-35 m / z = 612.26 (C ₄₆ H ₃₂ N ₂ = 612.78) 1-36 m / z = 638.27 (C ₄₈ H ₃₄ N ₂ = 638.81) 1-37 m / z = 491.24 (C ₃₆ H ₂₁ D ₅ N ₂ = 491.65) 1-38 m / z = 612.26 (C ₄₆ H ₃₂ N ₂ = 612.78) 1-39 m / z = 794.28 (C ₅₈ H ₃₈ N ₂ S = 795.02) 1-40 m / z = 656.26 (C ₄₈ H ₃₃ FN ₂ = 656.80) 1-41 m / z = 717.29 (C ₅₁ H ₃₅ N ₅ = 717.88) 1-42 m / z = 728.32 (C ₅₅ H ₄₀ N ₂ = 728.94) 1-43 m / z = 842.34 (C ₆₂ H ₄₂ N ₄ = 843.05) 1-44 m / z = 714.30 (C ₅₄ H ₃₈ N ₂ = 714.91) 1-45 m / z = 653.28 (C ₄₈ H ₃₅ N ₃ = 653.83) 1-46 m / z = 703.30 (C ₅₂ H ₃₇ N ₃ = 703.89) 1-47 m / z = 805.35 (C ₆₀ H ₄₃ N ₃ = 806.03) 1-48 m / z = 753.31 (C ₅₆ H ₃₉ N ₃ = 753.95) 1-49 m / z = 818.34 (C ₆₀ H ₄₂ N ₄ = 819.02) 1-50 m / z = 835.30 (C ₆₀ H ₄₁ N ₃ S = 836.07) 1-51 m / z = 655.27 (C ₄₆ H ₃₃ N ₅ = 655.81) 1-52 m / z = 885.32 (C ₆₄ H ₄₃ N ₃ S = 886.13) 1-53 m / z = 759.27 (C ₅₄ H ₃₇ N ₃ S = 759.97) 1-54 m / z = 656.27 (C ₄₅ H ₃₂ N ₆ = 656.79) 1-55 m / z = 960.39 (C ₆₉ H ₄₈ N ₆ = 961.19) 1-56 m / z = 853.35 (C ₆₄ H ₄₃ N ₃ = 854.07) 1-57 m / z = 894.37 (C ₆₆ H ₄₆ N ₄ = 895.12) 1-58 m / z = 834.38 (C ₆₂ H ₃₈ D ₅ N ₃ = 835.08) 1-59 m / z = 855.36 (C ₆₄ H ₄₅ N ₃ = 856.09) 1-60 m / z = 853.35 (C ₆₄ H ₄₃ N ₃ = 854.07) 1-61 m / z = 794.37 (C ₆₀ H ₄₆ N ₂ = 795.04) 1-62 m / z = 987.39 (C ₇₁ H ₄₉ N ₅ O = 988.21) 1-63 m / z = 1021.44 (C ₇₇ H ₅₅ N ₃ = 1022.31) 1-64 m / z = 737.23 (C ₅₁ H ₃₂ FN ₃ S = 737.90) 1-65 m / z = 562.24 (C ₄₂ H ₃₀ N ₂ = 562.72) 1-66 m / z = 602.27 (C ₄₅ H ₃₄ N ₂ = 602.78) 1-67 m / z = 563.24 (C ₄₁ H ₂₉ N ₃ = 563.70) 1-68 m / z = 714.30 (C ₅₄ H ₃₈ N ₂ = 714.91) 1-69 m / z = 678.30 (C ₅₁ H ₃₈ N ₂ = 678.88) 1-70 m / z = 802.33 (C ₆₁ H ₄₂ N ₂ = 803.02) 1-71 m / z = 800.32 (C ₆₁ H ₄₀ N ₂ = 801.01) 1-72 m / z = 563.24 (C ₄₁ H ₂₉ N ₃ = 563.70) 1-73 m / z = 668.23 (C ₄₈ H ₃₂ N ₂ S = 668.86) 1-74 m / z = 727.30 (C ₅₄ H ₃₇ N ₃ = 727.91) 1-75 m / z = 652.25 (C ₄₈ H ₃₂ N ₂ O = 652.80) 1-76 m / z = 662.27 (C ₅₀ H ₃₄ N ₂ = 662.84) 1-77 m / z = 536.23 (C ₄₀ H ₂₈ N ₂ = 536.68) 1-78 m / z = 586.24 (C ₄₄ H ₃₀ N ₂ = 586.74) 1-79 m / z = 712.29 (C ₅₄ H ₃₆ N ₂ = 712.90) 1-80 m / z = 714.30 (C ₅₄ H ₃₈ N ₂ = 714.91) 1-81 m / z = 754.33 (C ₅₇ H ₄₂ N ₂ = 754.98) 1-82 m / z = 957.38 (C ₇₀ H ₄₇ N ₅ = 958.18) 1-83 m / z = 965.38 (C ₇₃ H ₄₇ N ₃ = 966.20) 1-84 m / z = 719.24 (C ₅₁ H ₃₃ N ₃ S = 719.91) 1-85 m / z = 758.24 (C ₅₄ H ₃₄ N ₂ OS = 758.94) 1-86 m / z = 893.38 (C ₆₇ H ₄₇ N ₃ = 894.13) 1-87 m / z = 652.25 (C ₄₈ H ₃₂ N ₂ O = 652.80) 1-88 m / z = 662.27 (C ₅₀ H ₃₄ N ₂ = 662.84) 1-89 m / z = 562.24 (C ₄₂ H ₃₀ N ₂ = 562.72) 1-90 m / z = 612.26 (C ₄₆ H ₃₂ N ₂ = 612.78) 1-91 m / z = 688.29 (C ₅₂ H ₃₆ N ₂ = 688.87) 1-92 m / z = 714.30 (C ₅₄ H ₃₈ N ₂ = 714.91) 1-93 m / z = 754.33 (C ₅₇ H ₄₂ N ₂ = 754.98) 1-94 m / z = 878.37 (C ₆₇ H ₄₆ N ₂ = 879.12) 1-95 m / z = 876.35 (C ₆₇ H ₄₄ N ₂ = 877.10) 1-96 m / z = 639.27 (C ₄₇ H ₃₃ N ₃ = 639.80) 1-97 m / z = 768.26 (C ₅₆ H ₃₆ N ₂ S = 768.98) 1-98 m / z = 833.29 (C ₆₀ H ₃₉ N ₃ S = 834.05) 1-99 m / z = 742.26 (C ₅₄ H ₃₄ N ₂ O ₂ = 742.88) 1-100 m / z = 778.33 (C ₅₉ H ₄₂ N ₂ = 779.00) 1-101 m / z = 486.21 (C ₃₆ H ₂₆ N ₂ = 486.62) 1-102 m / z = 536.23 (C ₄₀ H ₂₈ N ₂ = 536.68) 1-103 m / z = 612.26 (C ₄₆ H ₃₂ N ₂ = 612.78) 1-104 m / z = 638.27 (C ₄₈ H ₃₄ N ₂ = 638.81) 1-105 m / z = 491.24 (C ₃₆ H ₂₁ D ₅ N ₂ = 491.65) 1-106 m / z = 612.26 (C ₄₆ H ₃₂ N ₂ = 612.78) 1-107 m / z = 794.28 (C ₅₈ H ₃₈ N ₂ S = 795.02) 1-108 m / z = 656.26 (C ₄₈ H ₃₃ FN ₂ = 656.80) 1-109 m / z = 717.29 (C ₅₁ H ₃₅ N ₅ = 717.88) 1-110 m / z = 728.32 (C ₅₅ H ₄₀ N ₂ = 728.94) 1-111 m / z = 842.34 (C ₆₂ H ₄₂ N ₄ = 843.05) 1-112 m / z = 714.30 (C ₅₄ H ₃₈ N ₂ = 714.91) 1-113 m / z = 653.28 (C ₄₈ H ₃₅ N ₃ = 653.83) 1-114 m / z = 703.30 (C ₅₂ H ₃₇ N ₃ = 703.89) 1-115 m / z = 805.35 (C ₆₀ H ₄₃ N ₃ = 806.03) 1-116 m / z = 753.31 (C ₅₆ H ₃₉ N ₃ = 753.95) 1-117 m / z = 818.34 (C ₆₀ H ₄₂ N ₄ = 819.02) 1-118 m / z = 835.30 (C ₆₀ H ₄₁ N ₃ S = 836.07) 1-119 m / z = 655.27 (C ₄₆ H ₃₃ N ₅ = 655.81) 1-120 m / z = 885.32 (C ₆₄ H ₄₃ N ₃ S = 886.13) 1-121 m / z = 759.27 (C ₅₄ H ₃₇ N ₃ S = 759.97) 1-122 m / z = 706.28 (C ₄₉ H ₃₄ N ₆ = 706.85) 1-123 m / z = 960.39 (C ₆₉ H ₄₈ N ₆ = 961.19) 1-124 m / z = 853.35 (C ₆₄ H ₄₃ N ₃ = 854.07) 1-125 m / z = 894.37 (C ₆₆ H ₄₆ N ₄ = 895.12) 1-126 m / z = 784.36 (C ₅₈ H ₃₆ D ₅ N ₃ = 785.02) 1-127 m / z = 855.36 (C ₆₄ H ₄₅ N ₃ = 856.09) 1-128 m / z = 853.35 (C ₆₄ H ₄₃ N ₃ = 854.07) 1-129 m / z = 794.37 (C ₆₀ H ₄₆ N ₂ = 795.04) 1-130 m / z = 957.38 (C ₇₀ H ₄₇ N ₅ = 958.18) 1-131 m / z = 1021.44 (C ₇₇ H ₅₅ N ₃ = 1022.31) 1-132 m / z = 737.23 (C ₅₁ H ₃₂ FN ₃ S = 737.90)

[ Synthesis Example  2]

The compound represented by Chemical Formula 2 according to the present invention (final product 2) is synthesized by reacting Sub 3 and Sub 4, as shown in Scheme 4 below, but is not limited thereto. X, R ⁶ to R ⁸ , L ² , Ar ⁴ , r, s and t are the same as defined in the formula (2).

<Scheme 4>

I. Synthesis of Sub 3

Sub 3 of Scheme 4 is synthesized by the reaction route of Scheme 5, but is not limited thereto. X, R ⁶ to R ⁸ , L ² , r, s and t are the same as defined in the formula (2).

Scheme 5

Sub 3-1 Synthesis Example

(1) Sub 3-I-1 Synthesis

2-aminobenzoic acid (50 g, 365 mmol) as a starting material was added together with Urea (153 g, 2552 mmol) in a round bottom flask and stirred at 160 ° C. After the reaction was completed, the reaction mixture was cooled to 100 ° C., and water (180 mL) was added thereto, followed by stirring for 1 hour. When the reaction was completed, the resulting solid was filtered under reduced pressure, washed with water and dried to give the product 45.5 g (yield 77%).

(2) Sub 3-II-1 Synthesis

Sub-I-1 (45.5 g, 281 mmol) obtained in the above synthesis was dissolved in a round bottom flask with POCl ₃ (190 mL) at room temperature, and then slowly added with N, N -Diisopropylethylamine (90.7 g, 702 mmol). Stir at 90 ° C. After the reaction was concentrated, iced water (470 mL) was added thereto, and the mixture was stirred at room temperature for 1 hour. The resulting solid was filtered under reduced pressure and dried to give 49.7 g (89% yield) of the product.

(3) Sub 3-1 synthesis method

Sub 3-II-1 (49.7 g, 250 mmol) obtained in the above synthesis was dissolved in THF (500 mL) in a round bottom flask, followed by 2- (dibenzo [b, d] thiophen-4-yl) -4,4 , 5,5-tetramethyl-1,3,2-dioxaborolane (77.5 g, 250 mmol), Pd (PPh ₃ ) ₄ (8.66 g, 7.50 mmol), K ₂ CO ₃ (69.1 g, 500 mmol), water ( 250 mL) was added and stirred at 80 ° C. After the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was purified by Silicagel Column and recrystallized to give the product 62.4 g (72% yield).

2.Sub 3-3 Synthesis Example

(1) Sub 3-I-2 Synthesis

3-amino- [1,1'-biphenyl] -4-carboxylic acid (50 g, 234 mmol) and Urea (98.6 g, 1641 mmol) were prepared using 41.9 g ( Yield 75%).

(2) Sub 3-II-2 Synthesis

Sub 3-I-2 (41.9 g, 176 mmol), POCl ₃ (120 mL), N, N- Diisopropylethylamine (56.8 g, 440 mmol) was prepared using 41.1 g of the product using the synthesis method of Sub 3-II-1. Yield 85%).

(3) Sub 3-3 synthesis method

Sub 3-II-2 (41.1 g, 149 mmol), 2- (dibenzo [b, d] thiophen-4-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (46.4 g , 149 mmol), Pd (PPh ₃ ) ₄ (5.18 g, 4.48 mmol), and K ₂ CO ₃ (41.3 g, 299 mmol) were obtained using 44.9 g (yield 71%) of the product using the synthesis method of Sub 3-1. Got it.

3.Sub 3-16 Synthesis Example

(1) Sub 3-16 Synthesis

Sub 3-II-1 (40 g, 201 mmol), 2- (dibenzo [b, d] furan-3-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (59.1 g , 201 mmol), Pd (PPh ₃ ) ₄ (6.97 g, 6.03 mmol), K ₂ CO ₃ (55.5 g, 402 mmol) using the synthesis method of Sub 3-1 to give 50.0 g (yield 75%) of the product. Got it.

4.Sub 3-23 Synthesis Example

(1) Sub 3-I-3 Synthesis

4-amino- [1,1'-biphenyl] -3-carboxylic acid (50 g, 234 mmol) and Urea (98.6 g, 1641 mmol) were prepared using 40.2 g of the product using the synthesis method of Sub 3-I-1 ( Yield 72%).

(2) Sub 3-II-3 Synthesis

Sub 3-I-3 (40.2 g, 169 mmol), POCl ₃ (110 mL), N, N- Diisopropylethylamine (54.6 g, 422 mmol) was prepared using 40.9 g of the product using the synthesis method of Sub 3-II-1. Yield 88%).

(3) Sub 3-23 synthesis method

Sub 3-II-3 (40.9 g, 149 mmol), 2- (dibenzo [b, d] furan-3-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (43.7 g , 149 mmol), Pd (PPh ₃ ) ₄ (5.15 g, 4.46 mmol), K ₂ CO ₃ (41.1 g, 297 mmol) using the synthesis method of Sub 3-1 to give 41.7 g (69% yield) of the product. Got it.

5.Sub 3-26 Synthesis Example

(1) Sub 3-26 synthesis method

Sub 3-II-1 (40 g, 201 mmol), 2- (benzo [b] naphtho [1,2-d] thiophen-5-yl) -4,4,5,5-tetramethyl-1,3, 2-dioxaborolane (72.4 g, 201 mmol), Pd (PPh ₃ ) ₄ (6.97 g, 6.03 mmol), K ₂ CO ₃ (55.5 g, 402 mmol) was synthesized using the synthesis method of Sub 3-1. (Yield 54%) was obtained.

6.Sub 3-33 Synthesis Example

(1) Sub 3-I-4 Synthesis

2-amino-5-methoxybenzoic acid (50 g, 299 mmol) and Urea (126 g, 2094 mmol) were obtained using the synthesis method of Sub 3-I-1 to give 37.0 g (54% yield) of the product.

(2) Sub 3-II-4 Synthesis

Sub 3-I-4 (37.0 g, 162 mmol), POCl ₃ (110 mL), N, N- Diisopropylethylamine (52.2 g, 404 mmol) was synthesized using 36.0 g of the product using the synthesis method of Sub 3-II-1. Yield 81%).

(3) Sub 3-33 synthesis method

Sub 3-II-4 (36.0 g, 131 mmol), 2- (dibenzo [b, d] furan-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (38.5 g , 131 mmol), Pd (PPh ₃ ) ₄ (4.54 g, 3.92 mmol), K ₂ CO ₃ (36.2 g, 262 mmol) using the synthesis method of Sub 3-1 to give 34.5 g (73% yield) of the product. Got it.

7.Sub 3-43 Synthesis Example

(1) Sub 3-43 synthesis method

Sub 3-II-1 (40 g, 201 mmol), 2- (4- (dibenzo [b, d] thiophen-1-yl) phenyl) -4,4,5,5-tetramethyl-1,3,2 -dioxaborolane (77.6 g, 201 mmol), Pd (PPh ₃ ) ₄ (6.97 g, 6.03 mmol), K ₂ CO ₃ (55.5 g, 402 mmol) was prepared using 70.5 g of the product using the synthesis method of Sub 3-1. Yield 83%).

8.Sub 3-47 Synthesis Example

(1) Synthesis of Sub 3-I-7

2-amino-3-bromobenzoic acid (50 g, 231 mmol) and Urea (97.3 g, 1620 mmol) were obtained using the synthesis method of Sub 3-I-1 to obtain 41.3 g (yield 74%) of the product.

(2) Sub 3-I-7-1 synthesis method

Sub 3-I-7 (41.3 g, 171 mmol) obtained in the above synthesis was dissolved in THF in a round flask, followed by (2- (methylthio) phenyl) boronic acid (28.8 g, 171 mmol), Pd (PPh ₃ ) ₄ (5.94 g, 5.14 mmol), K ₂ CO ₃ (47.3 g, 343 mmol), water were added and stirred at 80 ° C. After the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was purified by Silicagel Column and recrystallized to give the product 33.6 g (69% yield).

(3) Sub 3-I-7-2 synthesis method

To Sub 3-I-7-1 (33.6 g, 118 mmol) obtained in the above synthesis was added acetic acid (340 mL), 35% Hydrogen Peroxide (H ₂ O ₂ ) (12.1 g) was added and stirred at room temperature. After the reaction was completed, the mixture was neutralized with NaOH aqueous solution, and extracted with EA (ethylacetate) and water. The organic layer was dried over MgSO ₄ , concentrated, and the resulting compound was purified by Silicagel Column and recrystallized to give 29.5 g (83% yield) of the product.

(4) Sub 3-I-7-3 Synthesis Method

Sulfuric acid (H ₂ SO ₄ ) (14.7 mL) was added to Sub 3-I-7-2 (29.5 g, 98.1 mmol) obtained in the above synthesis, and stirred at room temperature. After the reaction was completed, the mixture was neutralized with NaOH aqueous solution, and extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ , concentrated, and the resulting compound was recrystallized from a Silicagel Column to give 20.0 g (yield 76%) of the product.

(5) Sub 3-II-7 Synthesis

Sub 3-I-7-3 (20.0 g, 74.5 mmol), POCl ₃ (49.7 mL), N, N- Diisopropylethylamine (24.1 g, 186 mmol) was synthesized using the synthesis method of Sub 3-II-1 to obtain 20.0. g (yield 88%) was obtained.

(6) Sub 3-47 synthesis method

Sub 3-II-7 (20.0 g, 65.6 mmol), 2- (dibenzo [b, d] thiophen-1-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (20.4 g , 65.6 mmol), Pd (PPh ₃ ) ₄ (2.27 g, 1.97 mmol), and K ₂ CO ₃ (18.1 g, 131 mmol) were obtained using 19.3 g (yield 65%) of the product using the synthesis method of Sub 3-1. Got it.

9.Sub 3-56 Synthesis Example

(1) Sub 3-I-9 Synthesis

1-amino-2-naphthoic acid (50 g, 267.1 mmol) and Urea (112 g, 1870 mmol) were obtained using the synthesis method of Sub 3-I-1 to obtain 40.8 g (yield 72%) of the product.

(2) Sub 3-II-9 Synthesis

Sub 3-I-9 (40.8 g, 192 mmol), POCl ₃ (130 mL), N, N- Diisopropylethylamine (62.1 g, 481 mmol) was prepared using the synthesis method of Sub 3-II-1. Yield 86%).

(3) Sub 3-56 synthesis method

Sub 3-II-9 (41.2 g, 165 mmol), 4,4,5,5-tetramethyl-2- (7-phenyldibenzo [b, d] thiophen-3-yl) -1,3,2-dioxaborolane ( 63.9 g, 165 mmol), Pd (PPh ₃ ) ₄ (5.73 g, 4.96 mmol), K ₂ CO ₃ (45.7 g, 331 mmol) was purified using the synthesis method of Sub 3-1, and the product 48.5 g (yield 62%). )

10.Sub 3-62 Synthesis Example

(1) Sub 3-I-10 Synthesis

2-amino-1-naphthoic acid (50 g, 267 mmol) and Urea (112 g, 1870 mmol) were obtained using the synthesis method of Sub 3-I-1 to obtain 43.6 g (yield 77%) of the product.

(2) Sub 3-II-10 Synthesis

Sub 3-I-10 (43.6 g, 206 mmol), POCl ₃ (140 mL), N, N- Diisopropylethylamine (66.5 g, 514 mmol) was prepared using the synthesis method of Sub 3-II-1. Yield 82%).

(3) Sub 3-62 synthesis method

Sub 3-II-10 (42.0 g, 169 mmol), 4- (7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) dibenzo [b, d] furan- 3-yl) pyridine (62.6 g, 169 mmol), Pd (PPh ₃ ) ₄ (5.84 g, 5.06 mmol), K ₂ CO ₃ (46.6 g, 337 mmol) was synthesized using the synthesis method of Sub 3-1. 45.6 g (59% yield) were obtained.

Compounds belonging to Sub 3 may be the following compounds, but are not limited thereto, and Table 4 shows FD-MS (Field Desorption-Mass Spectrometry) values of some compounds belonging to Sub 3.

compound FD-MS compound FD-MS Sub3-1 m / z = 346.03 (C ₂₀ H ₁₁ ClN ₂ S = 346.83) Sub3-2 m / z = 330.06 (C ₂₀ H ₁₁ ClN ₂ O = 330.77) Sub3-3 m / z = 422.06 (C ₂₆ H ₁₅ ClN ₂ S = 422.93) Sub3-4 m / z = 430.09 (C ₂₈ H ₁₅ ClN ₂ O = 430.89) Sub3-5 m / z = 380.07 (C ₂₄ H ₁₃ ClN ₂ O = 380.83) Sub3-6 m / z = 380.07 (C ₂₄ H ₁₃ ClN ₂ O = 380.83) Sub3-7 m / z = 396.05 (C ₂₄ H ₁₃ ClN ₂ S = 396.89) Sub3-8 m / z = 396.05 (C ₂₄ H ₁₃ ClN ₂ S = 396.89) Sub3-9 m / z = 380.07 (C ₂₄ H ₁₃ ClN ₂ O = 380.83) Sub3-10 m / z = 422.06 (C ₂₆ H ₁₅ ClN ₂ S = 422.93) Sub3-11 m / z = 406.09 (C ₂₆ H ₁₅ ClN ₂ O = 406.87) Sub3-12 m / z = 360.05 (C ₂₁ H ₁₃ ClN ₂ S = 360.86) Sub3-13 m / z = 348.05 (C ₂₀ H ₁₀ ClFN ₂ O = 348.76) Sub3-14 m / z = 360.05 (C ₂₁ H ₁₃ ClN ₂ S = 360.86) Sub3-15 m / z = 346.03 (C ₂₀ H ₁₁ ClN ₂ S = 346.83) Sub3-16 m / z = 330.06 (C ₂₀ H ₁₁ ClN ₂ O = 330.77) Sub3-17 m / z = 528.05 (C ₃₂ H ₁₇ ClN ₂ S ₂ = 529.07) Sub3-18 m / z = 407.08 (C ₂₅ H ₁₄ ClN ₃ O = 407.86) Sub3-19 m / z = 380.07 (C ₂₄ H ₁₃ ClN ₂ O = 380.83) Sub3-20 m / z = 396.05 (C ₂₄ H ₁₃ ClN ₂ S = 396.89) Sub3-21 m / z = 380.07 (C ₂₄ H ₁₃ ClN ₂ O = 380.83) Sub3-22 m / z = 380.07 (C ₂₄ H ₁₃ ClN ₂ O = 380.83) Sub3-23 m / z = 406.09 (C ₂₆ H ₁₅ ClN ₂ O = 406.87) Sub3-24 m / z = 422.06 (C ₂₆ H ₁₅ ClN ₂ S = 422.93) Sub3-25 m / z = 422.06 (C ₂₆ H ₁₅ ClN ₂ S = 422.93) Sub3-26 m / z = 396.05 (C ₂₄ H ₁₃ ClN ₂ S = 396.89) Sub3-27 m / z = 346.03 (C ₂₀ H ₁₁ ClN ₂ S = 346.83) Sub3-28 m / z = 330.06 (C ₂₀ H ₁₁ ClN ₂ O = 330.77) Sub3-29 m / z = 380.07 (C ₂₄ H ₁₃ ClN ₂ O = 380.83) Sub3-30 m / z = 396.05 (C ₂₄ H ₁₃ ClN ₂ S = 396.89) Sub3-31 m / z = 396.05 (C ₂₄ H ₁₃ ClN ₂ S = 396.89) Sub3-32 m / z = 380.07 (C ₂₄ H ₁₃ ClN ₂ O = 380.83) Sub3-33 m / z = 360.07 (C ₂₁ H ₁₃ ClN ₂ O ₂ = 360.80) Sub3-34 m / z = 371.03 (C ₂₁ H ₁₃ ClN ₃ S = 371.84) Sub3-35 m / z = 513.11 (C ₃₂ H ₂₀ ClN ₃ S = 514.04) Sub3-36 m / z = 346.03 (C ₂₀ H ₁₁ ClN ₂ S = 346.83) Sub3-37 m / z = 330.06 (C ₂₀ H ₁₁ ClN ₂ O = 330.77) Sub3-38 m / z = 396.05 (C ₂₄ H ₁₃ ClN ₂ S = 396.89) Sub3-39 m / z = 396.05 (C ₂₄ H ₁₃ ClN ₂ S = 396.89) Sub3-40 m / z = 380.07 (C ₂₄ H ₁₃ ClN ₂ O = 380.83) Sub3-41 m / z = 380.07 (C ₂₄ H ₁₃ ClN ₂ O = 380.83) Sub3-42 m / z = 380.07 (C ₂₄ H ₁₃ ClN ₂ O = 380.83) Sub3-43 m / z = 422.06 (C ₂₆ H ₁₅ ClN ₂ S = 422.93) Sub3-44 m / z = 422.06 (C ₂₆ H ₁₅ ClN ₂ S = 422.93) Sub3-45 m / z = 422.06 (C ₂₆ H ₁₅ ClN ₂ S = 422.93) Sub3-46 m / z = 436.04 (C ₂₆ H ₁₃ ClN ₂ OS = 436.91) Sub3-47 m / z = 452.02 (C ₂₆ H ₁₃ ClN ₂ S ₂ = 452.97) Sub3-48 m / z = 436.04 (C ₂₆ H ₁₃ ClN ₂ OS = 436.91) Sub3-49 m / z = 420.07 (C ₂₆ H ₁₃ ClN ₂ O ₂ = 420.85) Sub3-50 m / z = 396.05 (C ₂₄ H ₁₃ ClN ₂ S = 396.89) Sub3-51 m / z = 396.05 (C ₂₄ H ₁₃ ClN ₂ S = 396.89) Sub3-52 m / z = 396.05 (C ₂₄ H ₁₃ ClN ₂ S = 396.89) Sub3-53 m / z = 396.05 (C ₂₄ H ₁₃ ClN ₂ S = 396.89) Sub3-54 m / z = 380.07 (C ₂₄ H ₁₃ ClN ₂ O = 380.83) Sub3-55 m / z = 472.08 (C ₃₀ H ₁₇ ClN ₂ S = 472.99) Sub3-56 m / z = 472.08 (C ₃₀ H ₁₇ ClN ₂ S = 472.99) Sub3-57 m / z = 380.07 (C ₂₄ H ₁₃ ClN ₂ O = 380.83) Sub3-58 m / z = 394.09 (C ₂₅ H ₁₅ ClN ₂ O = 394.86) Sub3-59 m / z = 398.06 (C ₂₄ H ₁₂ ClFN ₂ O = 398.82) Sub3-60 m / z = 405.07 (C ₂₅ H ₁₂ ClN ₃ O = 405.84) Sub3-61 m / z = 456.10 (C ₃₀ H ₁₇ ClN ₂ O = 456.93) Sub3-62 m / z = 457.10 (C ₂₉ H ₁₆ ClN ₃ O = 457.92) Sub3-63 m / z = 506.12 (C ₃₄ H ₁₉ ClN ₂ O = 506.99) Sub3-64 m / z = 396.05 (C ₂₄ H ₁₃ ClN ₂ S = 396.89) Sub3-65 m / z = 396.05 (C ₂₄ H ₁₃ ClN ₂ S = 396.89) Sub3-66 m / z = 446.06 (C ₂₈ H ₁₅ ClN ₂ S = 446.95) Sub3-67 m / z = 380.07 (C ₂₄ H ₁₃ ClN ₂ O = 380.83) Sub3-68 m / z = 380.07 (C ₂₄ H ₁₃ ClN ₂ O = 380.83) Sub3-69 m / z = 472.08 (C ₃₀ H ₁₇ ClN ₂ S = 472.99) Sub3-70 m / z = 622.14 (C ₄₂ H ₂₃ ClN ₂ O ₂ = 623.11) Sub3-71 m / z = 548.11 (C ₃₆ H ₂₁ ClN ₂ S = 549.09) Sub3-72 m / z = 549.11 (C ₃₅ H ₂₀ ClN ₃ S = 550.08) Sub3-73 m / z = 396.05 (C ₂₄ H ₁₃ ClN ₂ S = 396.89) Sub3-74 m / z = 396.05 (C ₂₄ H ₁₃ ClN ₂ S = 396.89) Sub3-75 m / z = 380.07 (C ₂₄ H ₁₃ ClN ₂ O = 380.83) Sub3-76 m / z = 406.09 (C ₂₆ H ₁₅ ClN ₂ O = 406.87) Sub3-77 m / z = 380.07 (C ₂₄ H ₁₃ ClN ₂ O = 380.83)

II. Synthesis of Sub 4

Compounds belonging to Sub 4 may be the following compounds, but are not limited thereto. Table 5 shows Field Desorption-Mass Spectrometry (FD-MS) values of some compounds belonging to Sub 4.

compound FD-MS compound FD-MS Sub4-1 m / z = 204.13 (C ₁₂ H ₁₇ BO ₂ = 204.08) Sub4-2 m / z = 280.16 (C ₁₈ H ₂₁ BO ₂ = 280.17) Sub4-3 m / z = 280.16 (C ₁₈ H ₂₁ BO ₂ = 280.17) Sub4-4 m / z = 280.16 (C ₁₈ H ₂₁ BO ₂ = 280.17) Sub4-5 m / z = 254.15 (C ₁₆ H ₁₉ BO ₂ = 254.14) Sub4-6 m / z = 254.15 (C ₁₆ H ₁₉ BO ₂ = 254.14) Sub4-7 m / z = 356.19 (C ₂₄ H ₂₅ BO ₂ = 356.27) Sub4-8 m / z = 356.19 (C ₂₄ H ₂₅ BO ₂ = 356.27) Sub4-9 m / z = 356.19 (C ₂₄ H ₂₅ BO ₂ = 356.27) Sub4-10 m / z = 432.23 (C ₃₀ H ₂₉ BO ₂ = 432.37) Sub4-11 m / z = 406.21 (C ₂₈ H ₂₇ BO ₂ = 406.33) Sub4-12 m / z = 456.23 (C ₃₂ H ₂₉ BO ₂ = 456.39) Sub4-13 m / z = 406.21 (C ₂₈ H ₂₇ BO ₂ = 406.33) Sub4-14 m / z = 456.23 (C ₃₂ H ₂₉ BO ₂ = 456.39) Sub4-15 m / z = 406.21 (C ₂₈ H ₂₇ BO ₂ = 406.33) Sub4-16 m / z = 456.23 (C ₃₂ H ₂₉ BO ₂ = 456.39) Sub4-17 m / z = 456.23 (C ₃₂ H ₂₉ BO ₂ = 456.39) Sub4-18 m / z = 406.21 (C ₂₈ H ₂₇ BO ₂ = 406.33) Sub4-19 m / z = 456.23 (C ₃₂ H ₂₉ BO ₂ = 456.39) Sub4-20 m / z = 456.23 (C ₃₂ H ₂₉ BO ₂ = 456.39) Sub4-21 m / z = 406.21 (C ₂₈ H ₂₇ BO ₂ = 406.33) Sub4-22 m / z = 456.23 (C ₃₂ H ₂₉ BO ₂ = 456.39) Sub4-23 m / z = 456.23 (C ₃₂ H ₂₉ BO ₂ = 456.39) Sub4-24 m / z = 406.21 (C ₂₈ H ₂₇ BO ₂ = 406.33) Sub4-25 m / z = 456.23 (C ₃₂ H ₂₉ BO ₂ = 456.39) Sub4-26 m / z = 456.23 (C ₃₂ H ₂₉ BO ₂ = 456.39) Sub4-27 m / z = 330.18 (C ₂₂ H ₂₃ BO ₂ = 330.23) Sub4-28 m / z = 330.18 (C ₂₂ H ₂₃ BO ₂ = 330.23) Sub4-29 m / z = 330.18 (C ₂₂ H ₂₃ BO ₂ = 330.23) Sub4-30 m / z = 330.18 (C ₂₂ H ₂₃ BO ₂ = 330.23) Sub4-31 m / z = 330.18 (C ₂₂ H ₂₃ BO ₂ = 330.23) Sub4-32 m / z = 330.18 (C ₂₂ H ₂₃ BO ₂ = 330.23) Sub4-33 m / z = 380.19 (C ₂₆ H ₂₅ BO ₂ = 380.29) Sub4-34 m / z = 254.15 (C ₁₆ H ₁₉ BO ₂ = 254.14) Sub4-35 m / z = 330.18 (C ₂₂ H ₂₃ BO ₂ = 330.23) Sub4-36 m / z = 330.18 (C ₂₂ H ₂₃ BO ₂ = 330.23) Sub4-37 m / z = 330.18 (C ₂₂ H ₂₃ BO ₂ = 330.23) Sub4-38 m / z = 310.12 (C ₁₈ H ₁₉ BO ₂ S = 310.22) Sub4-39 m / z = 294.14 (C ₁₈ H ₁₉ BO ₃ = 294.16) Sub4-40 m / z = 386.15 (C ₂₄ H ₂₃ BO ₂ S = 386.32) Sub4-41 m / z = 420.19 (C ₂₈ H ₂₅ BO ₃ = 420.32) Sub4-42 m / z = 435.21 (C ₂₇ H ₂₆ BN ₃ O ₂ = 435.33) Sub4-43 m / z = 511.24 (C ₃₃ H ₃₀ BN ₃ O ₂ = 511.43) Sub4-44 m / z = 511.24 (C ₃₃ H ₃₀ BN ₃ O ₂ = 511.43) Sub4-45 m / z = 485.23 (C ₃₁ H ₂₈ BN ₃ O ₂ = 485.39) Sub4-46 m / z = 535.24 (C ₃₅ H ₃₀ BN ₃ O ₂ = 535.45) Sub4-47 m / z = 541.20 (C ₃₃ H ₂₈ BN ₃ O ₂ S = 541.48) Sub4-48 m / z = 601.25 (C ₃₉ H ₃₂ BN ₃ O ₃ = 601.51) Sub4-49 m / z = 601.25 (C ₃₉ H ₃₂ BN ₃ O ₃ = 601.51) Sub4-50 m / z = 575.24 (C ₃₇ H ₃₀ BN ₃ O ₃ = 575.48) Sub4-51 m / z = 515.18 (C ₃₁ H ₂₆ BN ₃ O ₂ S = 515.44) Sub4-52 m / z = 449.19 (C ₂₇ H ₂₄ BN ₃ O ₃ = 449.32) Sub4-53 m / z = 541.20 (C ₃₃ H ₂₈ BN ₃ O ₂ S = 541.48) Sub4-54 m / z = 420.19 (C ₂₈ H ₂₅ BO ₃ = 420.32) Sub4-55 m / z = 310.12 (C ₁₈ H ₁₉ BO ₂ S = 310.22) Sub4-56 m / z = 436.17 (C ₂₈ H ₂₅ BO ₂ S = 436.38) Sub4-57 m / z = 408.20 (C ₂₆ H ₂₅ BN ₂ O ₂ = 408.31) Sub4-58 m / z = 381.19 (C ₂₅ H ₂₄ BNO ₂ = 381.28) Sub4-59 m / z = 331.17 (C ₂₁ H ₂₂ BNO ₂ = 331.22) Sub4-60 m / z = 408.20 (C ₂₆ H ₂₅ BN ₂ O ₂ = 408.31) Sub4-61 m / z = 525.22 (C ₃₃ H ₂₈ BN ₃ O ₃ = 525.42) Sub4-62 m / z = 484.23 (C ₃₂ H ₂₉ BN ₂ O ₂ = 484.41) Sub4-63 m / z = 464.17 (C ₂₈ H ₂₅ BN ₂ O ₂ S = 464.39)

III. Final Product 2 Synthesis

Sub 3 (1 equiv) was dissolved in THF in a round bottom flask, then Sub 4 (1 equiv), K ₂ CO ₃ (2 equiv), Pd (PPh ₃ ) ₄ (0.03 equiv), water was added and stirred at 80 ° C. After completion of the reaction, the mixture was extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was purified by a Silicagel column and recrystallized to obtain Final product 2.

1.2-1 Synthesis Example

Sub 3-1 (62.4 g, 180 mmol) was dissolved in THF (620 mL) in a round bottom flask, then Sub 4-1 (36.7 g, 180 mmol), K ₂ CO ₃ (49.7 g, 360 mmol), Pd (PPh ₃ ) ₄ (6.24 g, 5.40 mmol), water (310 mL) were added and stirred at 80 ° C. After the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was purified by Silicagel column and recrystallized to give 45.5 g (yield 75%) of the product 2-1.

2. 2-12 Synthesis Example

Sub 3-3 (44.9 g, 106 mmol), Sub 4-7 (37.8 g, 106 mmol), K ₂ CO ₃ (29.3 g, 212 mmol), Pd (PPh ₃ ) ₄ (3.68 g, 3.18 mmol) was obtained by the synthesis method of 2-1 to 47.0 g (72% yield) of product 2-12.

3. 2-28 Synthesis Example

Sub 3-16 (50 g, 151 mmol), Sub 4-4 (42.4 g, 151 mmol), K ₂ CO ₃ (41.9 g, 303 mmol), Pd (PPh ₃ ) ₄ (5.25 g, 4.54 mmol) was obtained using 54.2 g (yield 80%) of the product 2-28 using the above synthesis method.

4. 2-43 Synthesis Example

Sub 3-23 (41.7 g, 102 mmol), Sub 4-7 (36.5 g, 102 mmol), K ₂ CO ₃ (28.3 g, 205 mmol), Pd (PPh ₃ ) ₄ (3.55 g, 3.07 mmol) was obtained using the synthesis method of 2-1 to obtain 46.6 g (76% yield) of product 2-43.

5. 2-46 Synthesis Example

Sub 3-26 (43.1 g, 109 mmol), Sub 4-7 (38.7 g, 109 mmol), K ₂ CO ₃ (30.0 g, 217 mmol), Pd (PPh ₃ ) ₄ (3.76 g, 3.26 mmol) was obtained by the synthesis method of 2-1 to obtain 48.1 g (yield 75%) of product 2-46.

6. 2-57 Synthesis Example

Sub 3-33 (34.5 g, 95.8 mmol), Sub 4-2 (26.8 g, 95.8 mmol), K ₂ CO ₃ (26.5 g, 192 mmol), Pd (PPh ₃ ) ₄ (3.32 g, 2.87 mmol) was obtained using the synthesis method of 2-1 to obtain 32.7 g (71% yield) of product 2-57.

7. 2-74 Synthesis Example

Sub 3-43 (70.5 g, 167 mmol), Sub 4-1 (34.0 g, 167 mmol), K ₂ CO ₃ (46.1 g, 333 mmol), Pd (PPh ₃ ) ₄ (5.78 g, 5.00 mmol) was obtained using the synthesis method of 2-1 to give 59.5 g (77% yield) of product 2-74.

8. 2-78 Synthesis Example

Sub 3-47 (19.3 g, 42.6 mmol), Sub 4-1 (8.70 g, 42.6 mmol), K ₂ CO ₃ (11.8 g, 85.2 mmol), Pd (PPh ₃ ) ₄ (1.48 g, 1.28 mmol) was obtained using the synthesis method of 2-1 to give 16.7 g (yield 79%) of product 2-78.

9. 2-88 Synthesis Example

Sub 3-56 (48.5 g, 103 mmol), Sub 4-7 (36.5 g, 103 mmol), K ₂ CO ₃ (28.3 g, 205 mmol), Pd (PPh ₃ ) ₄ (3.55 g, 3.08 mmol) was obtained using 48.4 g (yield 71%) of the product 2-88 using the above synthesis method.

10. 2-94 Synthesis Example

Sub 3-62 (45.6 g, 99.6 mmol), Sub 4-1 (20.3 g, 99.6 mmol), K ₂ CO ₃ (27.5 g, 199 mmol), Pd (PPh ₃ ) ₄ (3.45 g, 2.99 mmol) was obtained using the synthesis method of 2-1 to obtain 34.9 g (yield 70%) of product 2-94.

11.2-105 Synthesis Example

Sub 3-16 (10.0 g, 30.2 mmol), Sub 4-38 (9.4 g, 30.2 mmol), K ₂ CO ₃ (12.5 g, 90.7 mmol), Pd (PPh ₃ ) ₄ (2.10 g, 1.81 mmol) was obtained using the synthesis method of 2-1 to obtain 11.9 g (yield 82%) of product 2-105.

12. 2-108 Synthesis Example

Sub 3-1 (10.0 g, 28.8 mmol), Sub 4-41 (12.1 g, 28.8 mmol), K ₂ CO ₃ (12.0 g, 86.5 mmol), Pd (PPh ₃ ) ₄ (2.00 g, 1.73 mmol) was prepared using the synthesis method of 2-1 to obtain 14.8 g (yield 85%) of product 2-108.

13. 2-115 Synthesis Example

Sub 3-15 (10.0 g, 28.8 mmol), Sub 4-48 (17.3 g, 28.8 mmol), K ₂ CO ₃ (12.0 g, 86.5 mmol), Pd (PPh ₃ ) ₄ (2.00 g, 1.73 mmol) was obtained using the synthesis method of 2-1 to obtain 17.7 g (yield 78%) of product 2-115.

14. 2-125 Synthesis Example

Sub 3-16 (10.0 g, 30.2 mmol), Sub 4-57 (12.3 g, 30.2 mmol), K ₂ CO ₃ (12.5 g, 90.7 mmol), Pd (PPh ₃ ) ₄ (2.10 g, 1.81 mmol) was obtained using the synthesis method of 2-1 to obtain 12.9 g (yield 74%) of product 2-125.

15. 2-131 Synthesis Example

Sub 3-28 (10.0 g, 30.2 mmol), Sub 4-63 (14.0 g, 30.2 mmol), K ₂ CO ₃ (12.5 g, 90.7 mmol), Pd (PPh ₃ ) ₄ (2.10 g, 1.81 mmol) was obtained using the synthesis method of 2-1 to give 15.3 g (yield 80%) of product 2-131.

On the other hand, FD-MS values of the compounds 2-1 to 2-131 of the present invention prepared according to the synthesis examples as described above are shown in Table 6.

compound FD-MS compound FD-MS 2-1 m / z = 388.10 (C ₂₆ H ₁₆ N ₂ S = 388.49) 2-2 m / z = 372.13 (C ₂₆ H ₁₆ N ₂ O = 172.43) 2-3 m / z = 438.12 (C ₃₀ H ₁₈ N ₂ S = 438.55) 2-4 m / z = 422.14 (C ₃₀ H ₁₈ N ₂ O = 422.49) 2-5 m / z = 448.16 (C ₃₂ H ₂₀ N ₂ O = 448.53) 2-6 m / z = 464.13 (C ₃₂ H ₂₀ N ₂ S = 464.59) 2-7 m / z = 464.13 (C ₃₂ H ₂₀ N ₂ S = 464.59) 2-8 m / z = 524.19 (C ₃₈ H ₂₄ N ₂ O = 524.62) 2-9 m / z = 540.17 (C ₃₈ H ₂₄ N ₂ S = 540.68) 2-10 m / z = 540.17 (C ₃₈ H ₂₄ N ₂ S = 540.68) 2-11 m / z = 540.17 (C ₃₈ H ₂₄ N ₂ S = 540.68) 2-12 m / z = 616.20 (C ₄₄ H ₂₈ N ₂ S = 616.78) 2-13 m / z = 624.22 (C ₄₆ H ₂₈ N ₂ O = 624.74) 2-14 m / z = 574.20 (C ₄₂ H ₂₆ N ₂ O = 574.68) 2-15 m / z = 574.20 (C ₄₂ H ₂₆ N ₂ O = 574.68) 2-16 m / z = 590.18 (C ₄₂ H ₂₆ N ₂ S = 590.74) 2-17 m / z = 590.18 (C ₄₂ H ₂₆ N ₂ S = 590.74) 2-18 m / z = 574.20 (C ₄₂ H ₂₆ N ₂ O = 574.68) 2-19 m / z = 666.21 (C ₄₈ H ₃₀ N ₂ S = 666.84) 2-20 m / z = 650.24 (C ₄₈ H ₃₀ N ₂ O = 650.78) 2-21 m / z = 604.20 (C ₄₃ H ₂₈ N ₂ S = 604.77) 2-22 m / z = 592.20 (C ₄₂ H ₂₅ FN ₂ O = 592.67) 2-23 m / z = 624.22 (C ₄₆ H ₂₈ N ₂ O = 624.74) 2-24 m / z = 554.18 (C ₃₉ H ₂₆ N ₂ S = 554.71) 2-25 m / z = 388.10 (C ₂₆ H ₁₆ N ₂ S = 388.49) 2-26 m / z = 372.13 (C ₂₆ H ₁₆ N ₂ O = 172.43) 2-27 m / z = 448.16 (C ₃₂ H ₂₀ N ₂ O = 448.53) 2-28 m / z = 448.16 (C ₃₂ H ₂₀ N ₂ O = 448.53) 2-29 m / z = 464.13 (C ₃₂ H ₂₀ N ₂ S = 464.59) 2-30 m / z = 540.17 (C ₃₈ H ₂₄ N ₂ S = 540.68) 2-31 m / z = 524.19 (C ₃₈ H ₂₄ N ₂ O = 524.62) 2-32 m / z = 540.17 (C ₃₈ H ₂₄ N ₂ S = 540.68) 2-33 m / z = 524.19 (C ₃₈ H ₂₄ N ₂ O = 524.62) 2-34 m / z = 540.17 (C ₃₈ H ₂₄ N ₂ S = 540.68) 2-35 m / z = 574.20 (C ₄₂ H ₂₆ N ₂ O = 574.68) 2-36 m / z = 570.12 (C ₃₈ H ₂₂ N ₂ S ₂ = 570.73) 2-37 m / z = 449.15 (C ₃₁ H ₁₉ N ₃ O = 449.51) 2-38 m / z = 498.17 (C ₃₆ H ₂₂ N ₂ O = 498.59) 2-39 m / z = 574.20 (C ₄₂ H ₂₆ N ₂ O = 574.68) 2-40 m / z = 640.20 (C ₄₆ H ₂₈ N ₂ S = 640.80) 2-41 m / z = 674.24 (C ₅₀ H ₃₀ N ₂ O = 674.80) 2-42 m / z = 624.22 (C ₄₆ H ₂₈ N ₂ O = 624.74) 2-43 m / z = 600.22 (C ₄₄ H ₂₈ N ₂ O = 600.72) 2-44 m / z = 616.20 (C ₄₄ H ₂₈ N ₂ S = 616.78) 2-45 m / z = 616.20 (C ₄₄ H ₂₈ N ₂ S = 616.78) 2-46 m / z = 590.18 (C ₄₂ H ₂₆ N ₂ S = 590.74) 2-47 m / z = 388.10 (C ₂₆ H ₁₆ N ₂ S = 388.49) 2-48 m / z = 372.13 (C ₂₆ H ₁₆ N ₂ O = 172.43) 2-49 m / z = 448.16 (C ₃₂ H ₂₀ N ₂ O = 448.53) 2-50 m / z = 464.13 (C ₃₂ H ₂₀ N ₂ S = 464.59) 2-51 m / z = 540.17 (C ₃₈ H ₂₄ N ₂ S = 540.68) 2-52 m / z = 448.16 (C ₃₂ H ₂₀ N ₂ O = 448.53) 2-53 m / z = 422.14 (C ₃₀ H ₁₈ N ₂ O = 422.49) 2-54 m / z = 438.12 (C ₃₀ H ₁₈ N ₂ S = 438.55) 2-55 m / z = 438.12 (C ₃₀ H ₁₈ N ₂ S = 438.55) 2-56 m / z = 422.14 (C ₃₀ H ₁₈ N ₂ O = 422.49) 2-57 m / z = 478.17 (C ₃₃ H ₂₂ N ₂ O ₂ = 478.55) 2-58 m / z = 489.13 (C ₃₃ H ₁₉ N ₃ S = 489.60) 2-59 m / z = 555.18 (C ₃₈ H ₂₅ N ₃ S = 555.70) 2-60 m / z = 548.19 (C ₄₀ H ₂₄ N ₂ O = 548.65) 2-61 m / z = 388.10 (C ₂₆ H ₁₆ N ₂ S = 388.49) 2-62 m / z = 372.13 (C ₂₆ H ₁₆ N ₂ O = 172.43) 2-63 m / z = 464.13 (C ₃₂ H ₂₀ N ₂ S = 464.59) 2-64 m / z = 464.13 (C ₃₂ H ₂₀ N ₂ S = 464.59) 2-65 m / z = 464.13 (C ₃₂ H ₂₀ N ₂ S = 464.59) 2-66 m / z = 524.19 (C ₃₈ H ₂₄ N ₂ O = 524.62) 2-67 m / z = 524.19 (C ₃₈ H ₂₄ N ₂ O = 524.62) 2-68 m / z = 524.19 (C ₃₈ H ₂₄ N ₂ O = 524.62) 2-69 m / z = 438.12 (C ₃₀ H ₁₈ N ₂ S = 438.55) 2-70 m / z = 438.12 (C ₃₀ H ₁₈ N ₂ S = 438.55) 2-71 m / z = 422.14 (C ₃₀ H ₁₈ N ₂ O = 422.49) 2-72 m / z = 422.14 (C ₃₀ H ₁₈ N ₂ O = 422.49) 2-73 m / z = 422.14 (C ₃₀ H ₁₈ N ₂ O = 422.49) 2-74 m / z = 464.13 (C ₃₂ H ₂₀ N ₂ S = 464.59) 2-75 m / z = 464.13 (C ₃₂ H ₂₀ N ₂ S = 464.59) 2-76 m / z = 464.13 (C ₃₂ H ₂₀ N ₂ S = 464.59) 2-77 m / z = 478.11 (C ₃₂ H ₁₈ N ₂ OS = 478.57) 2-78 m / z = 494.09 (C ₃₂ H ₁₈ N ₂ S ₂ = 494.63) 2-79 m / z = 478.11 (C ₃₂ H ₁₈ N ₂ OS = 478.57) 2-80 m / z = 462.14 (C ₃₂ H ₁₈ N ₂ O ₂ = 462.51) 2-81 m / z = 438.12 (C ₃₀ H ₁₈ N ₂ S = 438.55) 2-82 m / z = 438.12 (C ₃₀ H ₁₈ N ₂ S = 438.55) 2-83 m / z = 438.12 (C ₃₀ H ₁₈ N ₂ S = 438.55) 2-84 m / z = 438.12 (C ₃₀ H ₁₈ N ₂ S = 438.55) 2-85 m / z = 590.18 (C ₄₂ H ₂₆ N ₂ S = 590.74) 2-86 m / z = 598.20 (C ₄₄ H ₂₆ N ₂ O = 598.71) 2-87 m / z = 666.21 (C ₄₈ H ₃₀ N ₂ S = 666.84) 2-88 m / z = 666.21 (C ₄₈ H ₃₀ N ₂ S = 666.84) 2-89 m / z = 422.14 (C ₃₀ H ₁₈ N ₂ O = 422.49) 2-90 m / z = 436.16 (C ₃₁ H ₂₀ N ₂ O = 436.51) 2-91 m / z = 440.13 (C ₃₀ H ₁₇ FN ₂ O = 440.48) 2-92 m / z = 447.14 (C ₃₁ H ₁₇ N ₃ O = 447.50) 2-93 m / z = 498.17 (C ₃₆ H ₂₂ N ₂ O = 498.59) 2-94 m / z = 499.17 (C ₃₅ H ₂₁ N ₃ O = 499.57) 2-95 m / z = 548.19 (C ₄₀ H ₂₄ N ₂ O = 548.65) 2-96 m / z = 438.12 (C ₃₀ H ₁₈ N ₂ S = 438.55) 2-97 m / z = 590.18 (C ₄₂ H ₂₆ N ₂ S = 590.74) 2-98 m / z = 564.17 (C ₄₀ H ₂₄ N ₂ S = 564.71) 2-99 m / z = 574.20 (C ₄₂ H ₂₆ N ₂ O = 574.68) 2-100 m / z = 498.17 (C ₃₆ H ₂₂ N ₂ O = 498.59) 2-101 m / z = 590.18 (C ₄₂ H ₂₆ N ₂ S = 590.74) 2-102 m / z = 664.22 (C ₄₈ H ₂₈ N ₂ O ₂ = 664.76) 2-103 m / z = 590.18 (C ₄₂ H ₂₆ N ₂ S = 590.74) 2-104 m / z = 667.21 (C ₄₇ H ₂₉ N ₃ S = 667.83) 2-105 m / z = 478.11 (C ₃₂ H ₁₈ N ₂ OS = 478.57) 2-106 m / z = 478.11 (C ₃₂ H ₁₈ N ₂ OS = 478.57) 2-107 m / z = 554.15 (C ₃₈ H ₂₂ N ₂ OS = 554.67) 2-108 m / z = 604.16 (C ₄₂ H ₂₄ N ₂ OS = 604.73) 2-109 m / z = 619.18 (C ₄₁ H ₂₅ N ₅ S = 619.75) 2-110 m / z = 729.25 (C ₅₁ H ₃₁ N ₅ O = 729.84) 2-111 m / z = 745.23 (C ₅₁ H ₃₁ N ₅ S = 745.90) 2-112 m / z = 653.22 (C ₄₅ H ₂₇ N ₅ O = 653.75) 2-113 m / z = 703.24 (C ₄₉ H ₂₉ N ₅ O = 703.81) 2-114 m / z = 785.22 (C ₅₃ H ₃₁ N ₅ OS = 785.93) 2-115 m / z = 775.19 (C ₅₁ H ₂₉ N ₅ S ₂ = 775.95) 2-116 m / z = 769.25 (C ₅₃ H ₃₁ N ₅ O ₂ = 769.86) 2-117 m / z = 759.21 (C ₅₁ H ₂₉ N ₅ OS = 759.89) 2-118 m / z = 733.19 (C ₄₉ H ₂₇ N ₅ OS = 733.85) 2-119 m / z = 693.22 (C ₄₇ H ₂₇ N ₅ O ₂ = 693.77) 2-120 m / z = 759.21 (C ₅₁ H ₂₉ N ₅ OS = 759.89) 2-121 m / z = 588.18 (C ₄₂ H ₂₄ N ₂ O ₂ = 588.67) 2-122 m / z = 478.11 (C ₃₂ H ₁₈ N ₂ OS = 478.57) 2-123 m / z = 604.16 (C ₄₂ H ₂₄ N ₂ OS = 604.73) 2-124 m / z = 603.21 (C ₄₁ H ₂₅ N ₅ O = 603.69) 2-125 m / z = 576.20 (C ₄₀ H ₂₄ N ₄ O = 576.66) 2-126 m / z = 549.18 (C ₃₉ H ₂₃ N ₃ O = 549.63) 2-127 m / z = 499.17 (C ₃₅ H ₂₁ N ₃ O = 499.57) 2-128 m / z = 576.20 (C ₄₀ H ₂₄ N ₄ O = 576.66) 2-129 m / z = 693.22 (C ₄₇ H ₂₇ N ₅ O ₂ = 693.77) 2-130 m / z = 652.23 (C ₄₆ H ₂₈ N ₄ O = 652.76) 2-131 m / z = 632.17 (C ₄₂ H ₂₄ N ₄ OS = 632.74)

Manufacturing Evaluation of Organic Electrical Device

Experimental Example  One) Red  Fabrication and Test of Organic Light-Emitting Device

First, on the ITO layer (anode) formed on the glass substrate, N ^1- (naphthalen-2-yl) -N ⁴ , N ⁴ -bis (4- (naphthalen-2-yl (phenyl) amino) phenyl ) -N ¹ -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) membrane 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. Vacuum deposition was performed to form a hole transport layer. A mixture of a compound represented by the formula (1) and a compound of the present invention represented by the formula (2) at 50:50 was used as a host on the hole transport layer, and as a dopant, (piq) ₂ Ir (acac) [bis A light emitting layer having a thickness of 30 nm was deposited on the hole transport layer by doping-(1-phenylisoquinolyl) iridium (III) acetylacetonate] at a weight of 95: 5. As a hole blocking layer, (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum (hereinafter abbreviated as BAlq) was vacuum deposited to a thickness of 10 nm, and tris ( 8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was deposited to a thickness of 45 nm to form an electron transport layer. Subsequently, LiF, which is an alkali metal halide, was deposited to a thickness of 0.2 nm as an electron injection layer, and then, Al was deposited to a thickness of 150 nm to prepare an organic electroluminescent device.

[ Comparative example  1 to Comparative example  4]

An organic electroluminescent device was manufactured in the same manner as in Experimental Example 1, except that Comparative Compounds A to D were used alone.

[ Comparative example  5]

An organic electroluminescent device was manufactured by the same method as Experimental Example 1, except that compound (1-9) represented by Formula 1 was used alone as a host.

[ Comparative example  6]

An organic electroluminescent device was manufactured in the same manner as in Experimental Example 1, except for using Compound (2-30) represented by Formula 2 alone as a host.

[ Comparative example  7]

An organic electroluminescent device was manufactured by the same method as Experimental Example 1, except that Comparative Compound A and Compound (2-30) represented by Formula 2 were used as a host.

[ Comparative example  8 to Comparative example  10]

An organic electroluminescent device was manufactured by the same method as Experimental Example 1, except that Compound (1-9) represented by Formula 1 and Comparative Compounds B to D were used as a host.

The electroluminescent (EL) characteristics of the Example and Comparative Example organic electroluminescent devices manufactured as described above were applied to the PR-650 of photoresearch by applying a forward bias DC voltage, and the measurement result was 2500 cd / m ^2. The T95 life was measured using a life measurement instrument manufactured by McScience Inc. Table 7 shows the results of device fabrication and evaluation.

First compound Second compound Driving voltage Current (mA / cm2) Luminance (cd / m2) Efficiency (cd / A) T (95) Comparative Example 1 - Comparative Compound A 7.6 33.3 2500 7.5 50.3 Comparative Example 2 - Comparative Compound B 6.6 23.1 2500 10.8 66.7 Comparative Example 3 - Comparative Compound C 6.8 19.7 2500 12.7 63.2 Comparative Example 4 - Comparative Compound D 6.9 23.4 2500 10.7 63.3 Comparative Example 5 - Compound (1-9) 7.5 29.8 2500 8.4 50.6 Comparative Example 6 - Compound (2-30) 6.4 18.7 2500 13.4 75.1 Comparative Example 7 Comparative Compound A Compound (2-30) 6.1 12.3 2500 20.3 95.3 Comparative Example 8 Compound (1-9) Comparative Compound B 5.8 12.8 2500 19.6 93.8 Comparative Example 9 Compound (1-9) Comparative Compound C 5.6 12.0 2500 20.8 94.2 Comparative Example 10 Compound (1-9) Comparative Compound D 5.7 13.1 2500 19.1 92.1 Example 1 Compound (1-9) Compound (2-30) 5.1 8.7 2500 28.8 147.1 Example 2 Compound (1-50) Compound (2-30) 4.9 8.8 2500 28.3 134.1 Example 3 Compound (1-69) Compound (2-30) 5.0 9.1 2500 27.5 143.2 Example 4 Compound (1-118) Compound (2-30) 4.9 9.5 2500 26.2 130.2 Example 5 Compound (1-9) Compound (2-72) 5.1 8.3 2500 30.3 143.2 Example 6 Compound (1-50) Compound (2-72) 5.0 8.4 2500 29.7 130.5 Example 7 Compound (1-69) Compound (2-72) 5.0 8.7 2500 28.9 139.4 Example 8 Compound (1-118) Compound (2-72) 4.8 9.1 2500 27.5 126.7 Example 9 Compound (1-9) Compound (2-85) 5.1 8.0 2500 31.1 141.9 Example 10 Compound (1-50) Compound (2-85) 4.9 8.2 2500 30.6 129.3 Example 11 Compound (1-69) Compound (2-85) 5.0 8.4 2500 29.7 138.1 Example 12 Compound (1-118) Compound (2-85) 4.8 8.8 2500 28.3 125.6 Example 13 Compound (1-9) Compound (2-105) 5.1 8.2 2500 30.5 145.8 Example 14 Compound (1-50) Compound (2-105) 4.9 8.3 2500 30.0 132.9 Example 15 Compound (1-69) Compound (2-105) 5.0 8.6 2500 29.2 141.9 Example 16 Compound (1-118) Compound (2-105) 4.8 9.0 2500 27.8 129.0 Example 17 Compound (1-9) Compound (2-112) 4.9 7.9 2500 31.7 130.2 Example 18 Compound (1-50) Compound (2-112) 4.7 8.0 2500 31.1 118.7 Example 19 Compound (1-69) Compound (2-112) 4.9 8.3 2500 30.3 126.7 Example 20 Compound (1-118) Compound (2-112) 4.6 8.7 2500 28.8 115.2 Example 21 Compound (1-9) Compound (2-116) 5.0 7.2 2500 34.6 136.7 Example 22 Compound (1-50) Compound (2-116) 4.7 7.4 2500 34.0 124.6 Example 23 Compound (1-69) Compound (2-116) 4.8 7.6 2500 33.0 133.1 Example 24 Compound (1-118) Compound (2-116) 4.6 8.0 2500 31.4 121.0 Example 25 Compound (1-9) Compound (2-128) 5.0 8.4 2500 29.7 140.6 Example 26 Compound (1-50) Compound (2-128) 4.8 8.6 2500 29.1 128.1 Example 27 Compound (1-69) Compound (2-128) 4.9 8.8 2500 28.3 136.9 Example 28 Compound (1-118) Compound (2-128) 4.7 9.3 2500 27.0 124.4 Example 29 Compound (1-9) Compound (2-129) 4.9 7.4 2500 34.0 134.1 Example 30 Compound (1-50) Compound (2-129) 4.7 7.5 2500 33.4 122.2 Example 31 Compound (1-69) Compound (2-129) 4.8 7.7 2500 32.5 130.5 Example 32 Compound (1-118) Compound (2-129) 4.6 8.1 2500 30.9 118.7

As can be seen from the results of Table 7, when the organic electroluminescent device material of the present invention represented by Formula 1 and Formula 2 is mixed and used as a phosphorescent host (Examples 1 to 32), a device using a single material Compared with (Comparative Examples 1 to 10), it was confirmed that the driving voltage, efficiency, and lifespan were remarkably improved.

In detail, the compound of the present invention represented by the formula (1), the compound of the present invention represented by the formula (2) and Comparative Compound A to Comparative Compound A using Comparative Compound A alone with the phosphorescent host alone compared to Comparative Examples 1 to 6 And Compound (2-30) of the present invention represented by Formula 2 and used as a phosphorescent host, Comparative Example 7 or Compound (1-9) of the present invention and Comparative Compounds B to D were used as a phosphorescent host It was confirmed that Comparative Examples 8 to 10 exhibited higher efficiency and lifetime and lower driving voltage.

The reason why the combination of the present invention is superior to Comparative Example 7 by mixing Comparative Compound A as a phosphorescent host is that when the compound of the present invention represented by Formula 1 having stronger hole characteristics than Comparative Compound A is mixed, High LUMO energy values improve electron blocking capability and allow more holes to move quickly and easily in the emitting layer. As a result, the charge balance in the light emitting layer of holes and electrons is increased, so that light is emitted inside the light emitting layer rather than at the hole transport layer interface. .

In addition, Comparative Example 9 or Comparative Example 9, in which Compound (1-9) and Comparative Compound C of the present invention were used in combination, was used by mixing Compound (1-9) and Comparative Compound B or Comparative Compound D of the present invention. It can be seen that the efficiency is higher than 10. When dibenzothiophene or dibenzofuran is introduced into quinazoline, the refractive index is significantly higher than when the aryl group is substituted, and the Tg is also increased. do.

In addition, the compound (2-30) of the present invention having dibenzothiophene substituted at the 4-position of quinazoline than the comparative compound C having dibenzothiophene substituted at the 2-position of quinazoline has a wider LUMO region. As a result, the electronic stability is increased, thereby increasing the efficiency and lifespan of the device.

Additionally, when comparing the compound (2-30) and the compound (2-112) of the present invention, when the heterocyclic group (eg, triazine moiety) containing nitrogen is substituted than when the general aryl group is substituted, As the injection characteristic is improved, it can be seen that the driving voltage and the efficiency performance are improved.

In conclusion, the combination of Formula 1 and Formula 2 is electrochemically synergistic to improve the performance of the entire device.

Experimental Example  2) Mixed ratio Red  Fabrication and Test of Organic Light-Emitting Device

The organic electroluminescent device was manufactured by the same method as Experimental Example 1, except for using a different mixing ratio of materials as described in Table 8.

First compound Second compound ratio Driving voltage Current (mA / cm2) Luminance (cd / m2) Efficiency (cd / A) T (95) Example 33 Compound (1-50) Compound (2-30) 3: 7 4.6 8.3 2500 30.3 138.2 Example 34 Compound (1-50) Compound (2-30) 4: 6 4.7 8.4 2500 29.9 137.8 Example 35 Compound (1-50) Compound (2-30) 6: 4 5.1 9.1 2500 27.4 131.9 Example 36 Compound (1-50) Compound (2-30) 7: 3 5.4 9.3 2500 26.8 130.5 Example 37 Compound (1-50) Compound (2-116) 3: 7 4.4 7.0 2500 35.8 129.1 Example 38 Compound (1-50) Compound (2-116) 4: 6 4.5 7.1 2500 35.1 128.7 Example 39 Compound (1-50) Compound (2-116) 6: 4 4.9 7.7 2500 32.3 122.6 Example 40 Compound (1-50) Compound (2-116) 7: 3 5.3 8.1 2500 31.0 121.8

As shown in Table 8, the mixture of the compound of the present invention was measured by manufacturing a device by ratio (3: 7, 4: 6, 6: 4, 7: 3).

In detail, the result of the mixture of compound (1-50) and compound (2-30) (Examples 33 to 36) shows the driving voltage while decreasing the ratio of the first host as 3: 7, 4: 6 Although the efficiency and lifespan were excellent, it was confirmed that the result of driving voltage, efficiency and life was inferior as the first host ratio was increased as in 6: 4 and 7: 3. In addition, looking at the result of the mixture of compound (1-50) and compound (2-116) (Examples 37 to 40) similar to the result of the compound (2-30) (Examples 33 to 36) You can see that the performance changes as the percentage of hosts changes. This may be explained because the charge balance in the light emitting layer is maximized when an appropriate amount of the compound represented by Formula 1 having strong hole characteristics is mixed.

The above description is merely illustrative of the present invention, and those skilled in the art to which the present invention pertains may various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed herein are not intended to limit the present invention but to describe the present invention, and the spirit and scope of the present invention are not limited thereto.

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

100: organic electric 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 (15)

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, wherein the organic material layer includes a light emitting layer, and the light emitting layer is represented by Chemical Formula 1 as a phosphorescent light emitting layer. An organic electric device comprising a first host compound and a second host compound represented by the following formula (2)

{In Formula 1 and Formula 2,
1) Ar ¹ , Ar ² and Ar ³ are each independently a C ₆ -C ₆₀ aryl group; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; Fluorenyl groups; A fused ring group of an aromatic ring of C ₆ -C ₆₀ and an aliphatic ring of C ₃ -C ₆₀ ; An alkyl group of C ₁ -C ₅₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; And an aryloxy group of C ₆ -C ₃₀ ; and also Ar ² And Ar ³ may combine with each other to form a ring,
2) n is 1 or 2,
3) L ¹ and L ² are each independently a single bond; C ₆ -C ₆₀ arylene group; Fluorenylene groups; A C ₂ -C ₆₀ heterocyclic group comprising at least one hetero atom of O, N, S, Si, and P; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; And an aliphatic hydrocarbon group; selected from the group consisting of,
4) Ar ⁴ is an aryl group of C ₆ -C ₆₀ or a heterocyclic group of C ₂ -C ₆₀ ,
5) p, r or t is 0-4, q or s is 0-3,
6) R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ are independently of each other hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ ~ C ₆₀ Aryl group; Fluorenyl groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ -C ₃₀ alkoxyl group; C ₆ -C ₃₀ aryloxy group; And -L'-N (R ^a ) (R ^b ); When p, q, r, s, or t is 2 or more, a plurality of adjacent R ⁴ , a plurality of adjacent R ⁵ , a plurality of adjacent R ⁶ , a plurality of adjacent R ⁷ , a plurality of adjacent R ⁸ may be bonded to each other to form a saturated or unsaturated ring,
7) R ^a and R ^b are each independently of the C ₆ -C ₆₀ aryl group; Fluorenyl groups; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; And a C ₂ -C ₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si, and P, and
8) X is O or S,
Here, the aryl group, fluorenyl group, arylene group, heterocyclic group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group are each deuterium; halogen; Silane group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; Import alkylthio of C ₁ -C _20; An alkoxyl group of C ₁ -C ₂₀ ; An alkyl group of C ₁ -C ₂₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; Aryl group of C ₆ -C ₂₀ ; C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl groups; C ₂ -C ₂₀ heterocyclic group; A cycloalkyl group of C ₃ -C ₂₀ ; C ₇ -C ₂₀ arylalkyl group and C ₈ -C ₂₀ arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of, these substituents may be bonded to each other to form a ring, wherein ' Ring 'means a fused ring consisting of an aliphatic ring of C ₃ -C ₆₀ or an aromatic ring of C ₆ -C ₆₀ or a hetero ring of C ₂ -C ₆₀ or a combination thereof, and includes a saturated or unsaturated ring.}
The organic electric device of claim 1, wherein in Formula 1 or Formula 2, L ¹ or L ² is represented by any one of Formulas b-1 to b-13.

{In Chemical Formula b-1 to Chemical Formula b-13,
1) Y is NL ³ -Ar ⁵ , O, S or CR'R ",
2) L ³ is the same as the definition of L ¹ in claim 1,
3) Ar ⁵ is the same as the definition of Ar ¹ in claim 1,
4) R 'and R "are independently of each other hydrogen; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₃ ~ C ₆₀ Heterocyclic group; C ₁ ~ C ₅₀ Alkyl group; and -L'-N (R ^a ) (R ^b ) and R ′ and R ″ may combine with each other to form a spiro ring,
5) a, c, d and e are independently integers from 0 to 4, b is an integer from 0 to 6, f and g are independently integers from 0 to 3, h is an integer from 0 to 2 , i is an integer of 0 or 1,
6) R ¹ , R ² and R ³ are independently of each other hydrogen; heavy hydrogen; Tritium; halogen; Cyano group; Nitro group; C ₆ -C ₆₀ aryl group; Fluorenyl groups; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; An alkyl group of C ₁ -C ₅₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; C ₆ -C ₃₀ aryloxy group; And -L ^a -N (R ^d ) (R ^e ); or when a, b, c, d, e, f and g are 2 or more, and h is 2 or more, respectively A plurality of R1's are the same as or different from each other, and a plurality of R ^{1 's} or a plurality of R ^{2' s} or a plurality of R ^{3 's} or neighboring R ¹ and R ² or R ² and R ³ combine with each other to form an aromatic ring or a heteroaromatic ring Can do it,
Wherein L ^a is a single bond; C ₆ -C ₆₀ arylene group; Fluorenylene groups; A C ₂ -C ₆₀ heterocyclic group comprising at least one hetero atom of O, N, S, Si, and P; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; And an aliphatic hydrocarbon group of C ₃ -C ₆₀ ; wherein R ^d and R ^e are independently of each other an aryl group of C ₆ -C ₆₀ ; Fluorenyl groups; C ₂ -C ₆₀ heterocyclic group including at least one hetero atom selected from the group consisting of O, N, S, Si and P; And a fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ .
7) Z ⁴⁹ , Z ⁵⁰ and Z ⁵¹ are independently of each other CR ^f or N, at least one of Z ⁴⁹ , Z ⁵⁰ and Z ⁵¹ is N,
R ^f is hydrogen; heavy hydrogen; Tritium; halogen; Cyano group; Nitro group; C ₆ -C ₆₀ aryl group; Fluorenyl groups; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; An alkyl group of C ₁ -C ₅₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; And an aryloxy group of C ₆ -C _30. The adjacent R ¹ and R ^f may be bonded to each other to form an aromatic ring or a heteroaromatic ring.}
The organic electronic device of claim 1, wherein at least one of Ar ² and Ar ³ is represented by the following Chemical Formula 1-1:

{In Formula 1-1,
A or B is independently of each other a C ₆ ~ C ₂₄ aryl group or C ₂ ~ C ₂₄ heterocyclic group,
X ¹ is NL ⁵ -Ar ⁶ , O, S or CR'R ",
L ⁴ and L ⁵ are the same as the definition of L ¹ in claim 1
Ar ⁶ is the same as defined in Ar ¹ in claim 1
R 'and R "are independently of each other hydrogen; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₃ ~ C ₆₀ heterocyclic group; C ₁ ~ C ₅₀ Alkyl group; and -L'-N (R ^a ) (R ^b ); and R 'and R "may be bonded to each other to form a spiro ring.}
The organic electric device of claim 1, wherein the first host compound represented by Chemical Formula 1 is represented by one of the following Chemical Formulas 3 to 6.

{In Formula 3 to Formula 6,
Ar ¹ , Ar ² , Ar ³ , R ⁴ , R ⁵ , L ¹ , p, q are as defined in claim 1 above
Ar ⁷ or Ar ⁸ is the same as defined in Ar ¹ of claim 1.
The organic electroluminescence device according to claim 1, wherein the second host compound represented by Chemical Formula 2 is represented by the following Chemical Formula 7 or Chemical Formula 8.

{In Formula 7 or Formula 8, R ⁶ , R ⁷ , R ⁸ , L ² , Ar ⁴ , r, s, and t are as defined in claim 1 above.}
The organic electric device of claim 1, wherein the second host compound represented by Chemical Formula 2 is represented by the following Chemical Formulas 9 to 13.
<Formula 9><Formula10><Formula11>

<Formula 12><Formula13>

{In Formula 9 to Formula 13,
1) R ⁶ , R ⁷ , R ⁸ , L ² , X, r, s and t are as defined in claim 1 above,
2) R ⁹ is an aryl group of C ₆ ~ C ₁₀ ,
3) R ¹⁰ to R ¹² are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ ~ C ₆₀ Aryl group; Fluorenyl groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ -C ₃₀ alkoxyl group; C ₆ -C ₃₀ aryloxy group; And -L'-N (R ^a ) (R ^b ); Is selected from the group consisting of
4) Ar ⁷ and Ar ⁸ are each independently of the other C ₆ -C ₆₀ aryl group; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; Fluorenyl groups; A fused ring group of an aromatic ring of C ₆ -C ₆₀ and an aliphatic ring of C ₃ -C ₆₀ ; An alkyl group of C ₁ -C ₅₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; And C ₆ -C ₃₀ An aryloxy group; selected from the group consisting of,
5) L ⁶ is a single bond; C ₆ -C ₆₀ arylene group; Fluorenylene groups; A C ₂ -C ₆₀ heterocyclic group comprising at least one hetero atom of O, N, S, Si, and P; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; And an aliphatic hydrocarbon group; selected from the group consisting of,
6) Z is O or S,
7) u is an integer of any one of 0 to 3. v and w are each independently an integer of 0 to 4.}
The organic electric device of claim 6, wherein at least one of Ar ⁷ and Ar ⁸ is represented by the following Chemical Formula 1-2.
<Formula 1-2>

{In Formula 1-2,
C or D is independently of each other a C ₆ ~ C ₂₄ aryl group or C ₂ ~ C ₂₄ heterocyclic group,
X ² is NL ⁸ -Ar ⁹ , O, S or CR'R ",
L ⁷ and L ⁸ are the same as the definition of L ⁶ in claim 6,
Ar ⁹ is an aryl group of C ₆ -C ₆₀ ; Or C ₂ -C ₆₀ heterocyclic group; ego,
R ′ and R ″ are each independently selected from the group consisting of hydrogen; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₃ ~ C ₆₀ heterocyclic group; and C ₁ ~ C ₅₀ Alkyl group; }
The organic electroluminescent device according to claim 1, wherein the first host compound represented by Chemical Formula 1 is any one of the following Compounds 1-1 to 1-132:

The organic electric device of claim 1, wherein the second host compound represented by Chemical Formula 2 is any one of the following Compounds 2-1 to 2-131.

The semiconductor device of claim 1, further comprising at least one hole transport band layer between the first electrode and the light emitting layer, wherein the hole transport band layer includes a hole transport layer, a light emitting auxiliary layer, or both. An organic electric device, characterized in that the layer comprises a compound represented by the formula (1). The organic electroluminescence device according to claim 1, wherein the compound represented by Chemical Formula 1 and Chemical Formula 2 is used in a light emitting layer by mixing in a ratio of 1: 9 to 9: 1. The organic electroluminescence device according to claim 1, wherein the compound represented by Chemical Formula 1 and Chemical Formula 2 is used in a light emitting layer by mixing 1: 9 to 5: 5. The organic electroluminescent device according to claim 1, wherein the compound represented by Chemical Formula 1 and Chemical Formula 2 is used in a light emitting layer by mixing 2: 8 to 4: 6. A display device comprising the organic electric element according to claim 1, and a control unit for driving the display device. 15. The electronic device of claim 14, wherein the organic electroluminescent element is at least one of an organic electroluminescent element, an organic solar cell, an organic photoconductor, an organic transistor, and a monochromatic or white illumination element.

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