KR20160059609A - Display device using a composition for organic electronic element, and an organic electronic element thereof - Google Patents

Abstract

The present invention provides an organic electronic element, a display device, and an electronic device comprising the same. The organic electronic element has improved light-emitting efficiency, stability and lifespan properties by using a composition consisting of two or more compounds which have different structures as a hole transport layer.

Description

TECHNICAL FIELD [0001] The present invention relates to a display device and an organic electroluminescent device using a composition for an organic electroluminescent device,

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescent device, a display device, and an electronic device using the composition of organic electroluminescent compound. More particularly, the present invention relates to a display device including an organic electroluminescent layer And an organic electric device.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic electroluminescence device using an organic light emitting phenomenon is a self-luminous device using a principle that a light emitting material emits light by a recombination energy of holes injected from an anode and electrons injected from a cathode by applying a current.

The organic electroluminescent device may have a structure in which an anode is formed on a substrate, and a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, and a cathode are sequentially formed on the anode. Here, the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, and the electron injecting layer are organic thin films made of organic compounds.

Currently, the portable display market is increasing in size as a large-area display, which requires more power than the power consumption required by existing portable displays. Therefore, power consumption is an important factor for portable displays, which have a limited power source, such as a battery, and efficiency and lifetime issues as well as drive voltage issues are critical issues to be solved.

Particularly, in the case of driving voltage problem and lifetime problem, there are many problems associated with the thermal deterioration problem of the hole injecting material and the hole transporting material. For example, a method of forming a multilayer structure of a hole transporting layer (US Patent No. 5256945) and a method of using a material having a high glass transition temperature (U.S. Patent No. 5061569) have been proposed.

In addition, when a material having a good hole transport function is used to reduce the driving voltage, although the driving voltage of the device is greatly reduced, the efficiency and lifetime of the device are degraded due to excessive charge injection. There was an attempt.

However, there is a problem that the power consumption of the organic electronic device is increased and the lifetime is lowered due to the increase of the driving voltage of the progressive driving voltage of the blue organic electronic device such as red, green, and blue. In order to solve this problem, a buffer layer is formed between the anode and the hole transporting layer (Korean Patent Publication No. 2006-0032099).

In the present invention, two or more hole transporting materials having different band gaps are mixed in the hole transporting layer to reduce the thermal deterioration occurring at the interface between the hole transporting layer and the hole transporting layer and at the interface between the hole transporting layer and the light emitting layer, And an object of the present invention is to provide an organic electroluminescent device having an excellent luminous efficiency by efficiently controlling the amount of injected charges and increasing the efficiency.

The present invention provides a light emitting device comprising: a first electrode; A second electrode; And an organic layer disposed between the first electrode and the second electrode and including a light emitting layer including at least one hole transport layer and a light emitting compound, wherein the hole transport layer has a different chemical structure And a display device including the organic electroluminescent device.

The present invention also relates to an organic electronic device and an electronic device using the same, and more particularly, to an organic electronic device using the composition of the present invention, There is provided an organic electronic device using a composition in which two or more hole transporting materials having different structures are mixed, and an electronic device including the same is provided.

The organic electroluminescent device and the display device including the organic electroluminescent device provided in the present invention have the advantages that the thermal deterioration occurring at the interface between the hole injection layer and the hole transporting layer and the interface between the hole transporting layer and the light emitting layer is reduced and the lifetime is prolonged, Is efficiently controlled to provide excellent luminous efficiency.

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

Hereinafter, embodiments of the present invention will be described in detail. In the following description of the present invention, a detailed description of known functions and configurations incorporated herein will be omitted when it may make the subject matter of the present invention rather unclear.

In describing the components of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are intended to distinguish the constituent elements from other constituent elements, and the terms do not limit the nature, order or order of the constituent elements. When a component is described as being "connected", "coupled", or "connected" to another component, the component may be directly connected to or connected to the other component, It should be understood that an element may be "connected," "coupled," or "connected."

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

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

As used herein, the term "alkyl" or "alkyl group " refers to a straight or branched Quot; means a radical of a saturated aliphatic group, including an alkyl group, a cycloalkyl-substituted alkyl group.

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

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

The term "alkenyl group "," alkenyl group ", or "alkynyl group ", as used herein, unless otherwise indicated, each have a double bond or triple bond of from 2 to 60 carbon atoms and include straight chain or branched chain groups , But is not limited thereto.

The term "cycloalkyl" as used herein, unless otherwise specified, means alkyl which forms a ring having from 3 to 60 carbon atoms, but is not limited thereto.

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

The term "alkenoyl group "," alkenoyl group ", "alkenyloxy group ", or" alkenyloxy group "as used in the present invention means an alkenyl group to which an oxygen radical is attached, , But is not limited thereto.

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

The terms "aryl group" and "arylene group ", as used herein, unless otherwise specified, each have 6 to 60 carbon atoms, but are not limited thereto. In the present invention, an aryl group or an arylene group means a single ring or a multicyclic aromatic group, and neighboring substituents include aromatic rings formed by bonding or participating in the reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirobifluorene group.

The prefix "aryl" or "ar" means a radical substituted with an aryl group. For example, the arylalkyl group is an alkyl group substituted with an aryl group, the arylalkenyl group is an alkenyl group substituted with an aryl group, and the radical substituted with an aryl group has the carbon number described in the present specification.

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

The term "heteroalkyl ", as used herein, unless otherwise indicated, means an alkyl comprising one or more heteroatoms. The term "heteroaryl group" or "heteroarylene group" as used in the present invention means an aryl or arylene group having 2 to 60 carbon atoms each containing at least one heteroatom unless otherwise specified, And includes at least one of a single ring and a multi-ring, and neighboring functional devices may be formed in combination.

The term "heterocyclic group ", as used herein, unless otherwise specified, includes one or more heteroatoms, has from 2 to 60 carbon atoms, includes at least one of a single ring and multiple rings, Aromatic rings. Adjacent functional groups may be combined and formed.

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

The "heterocyclic group" may also include a ring containing SO ₂ in place of the carbon forming the ring. For example, the "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 an "aliphatic ring" means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

Unless otherwise specified, the term "ring" as used herein refers to a fused ring consisting of an aliphatic ring of 3 to 60 carbon atoms or an aromatic ring of 6 to 60 carbon atoms or a heterocycle of 2 to 60 carbon atoms, or combinations thereof, Saturated or unsaturated ring.

Other hetero-compounds or hetero-radicals other than the above-mentioned hetero-compounds include, but are not limited to, one or more heteroatoms.

Unless otherwise specified, the term "carbonyl" as used herein refers to -COR ', wherein R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, A cycloalkyl group of 2 to 20 carbon atoms, an alkenyl group of 2 to 20 carbon atoms, an alkynyl group of 2 to 20 carbon atoms, or a combination thereof.

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

One also no explicit description, the terms in the "unsubstituted or substituted", "substituted" is heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C for use in the present invention ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl amine group, C ₁ ~ C ₂₀ alkyl thiophene group, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C of 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 Means a group substituted with at least one substituent selected from the group consisting of a halogen atom, a halogen atom, a cyano group, a germanium group, and a C ₂ to C ₂₀ heterocyclic group.

Unless otherwise expressly stated, the formula used in the present invention is applied in the same manner as the definition of the substituent by the definition of the index of the following formula.

When a is an integer of 0, substituent R ¹ is absent. When a is an integer of 1, one substituent R ¹ is bonded to any one of carbon atoms forming a benzene ring, and when a is an integer of 2 or 3 each coupled as follows: and wherein R ¹ may be the same or different from each other, a is the case of 4 to 6 integer, and bonded to the carbon of the benzene ring in a similar way, while the display of the hydrogen bonded to the carbon to form a benzene ring Is omitted.

The organic electroluminescent device according to the present invention may be one of an organic electroluminescent (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a monochromatic or white illumination device.

Another embodiment of the present invention can include an electronic device including a display device including the above-described organic electronic device of the present invention and a control unit for controlling the display device. At this time, the electronic device may be a current or a 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, a display device and an organic electroluminescent device according to aspects of the present invention will be described.

The present invention relates to a plasma display panel comprising a first electrode; A second electrode; And an organic layer disposed between the first electrode and the second electrode and including a hole transporting layer and a light emitting layer, wherein the hole transporting layer comprises two kinds of compounds having different structures from each other, Wherein the organic material layer is formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, or a roll-to-roll process, wherein the organic material layer is formed by mixing a compound and an aryldiamine- Lt; / RTI >

According to another aspect of the present invention, there is provided a plasma display panel comprising: a first electrode; A second electrode; And an organic layer disposed between the first electrode and the second electrode and including a light emitting layer including at least one hole transport layer and a light emitting compound, wherein the hole transport layer comprises a compound represented by the following Formula 1 And a compound represented by the following general formula (2).

&Lt; Formula 1 > < EMI ID =

(1) Ar ¹ to Ar ⁶ independently represent a C _{6 to} C ₆₀ aryl group; Heterocyclic group of _{O, N, S, C 2} ~ 60 containing at least one hetero atom of Si and P; A fluorenyl group; And a fused ring group of an aromatic ring of C _{6 to} C _{60 and} an aliphatic ring of C _{3 to} C ₆₀ ; and 2) L ¹ to L ⁸ are independently selected from the group consisting of a single bond; An arylene group having _{6 to 60} carbon atoms; Heterocyclic group of O, N, S, Si and P of the divalent C _{2 ~ 60} containing at least one heteroatom; A fluorenylene group; And a divalent fused ring group of an aliphatic ring of C _{3 to 60} and an aromatic ring of C _{6 to 60} ; and 3) a to h are independently selected from the integers of 1 to 4, each of which is selected from the group consisting of 2 , L ¹ to L ⁸ are the same as or different from each other, and 4) R ¹ and R ² independently of one another are deuterium; Tritium; halogen; Cyano; A nitro group; An aryl group of _{6 to 60} carbon atoms; A fluorenyl group; Heterocyclic group of _{O, N, S, C 2} ~ 60 containing at least one hetero atom of Si and P; Fused ring group of an aromatic ring of C _{3 ~ 60} alicyclic and C _{6 ~ 60} of the; A C1 _{to C50} alkyl group; An alkenyl group having _{2 to 20} carbon atoms; An alkynyl group having _{2 to 20} carbon atoms; An alkoxyl group having _{1 to 30} carbon atoms; An aryloxy group having _{6 to 30} carbon atoms; And -L'-N (R ^a ) (R ^b ), wherein L 'is a single bond; An arylene group having _{6 to 60} carbon atoms; Heterocyclic group of O, N, S, Si and P of the divalent C _{2 ~ 60} containing at least one heteroatom; A fluorenylene group; And a divalent fused ring group of an aliphatic ring of C _{3 to} C _{60 and} an aromatic ring of C _{6 to} C ₆₀ , and R ^a and R ^b are each independently a C _{6 to} C ₆₀ aryl group; A fluorenyl group; Heterocyclic group of _{O, N, S, C 2} ~ 60 containing at least one hetero atom of Si and P; And selected from the group consisting of a fused ring of an aromatic ring of C _{3 ~ 60} alicyclic and C _{6 ~ 60} of or, or a plurality of R ¹ and R ² are adjacent R ¹ together, or R ² combine with each other to at least one to each other, if present (Provided that R ¹ and R ² which do not form a ring are the same as defined above), 5) l and m are each independently selected from the integers from 0 to 4, Is an integer of 2 or more, R ¹ and R ² are the same as or different from each other. A heterocyclic group, a fused ring group, an alkyl group, an alkenyl group, an alkoxy group, and an aryloxy group, each of which is independently selected from the group consisting of a halogen, a silane group, a siloxane group, a boron group, a germanium group, a cyano group; a nitro ^{group; -L'-N (R a)} (R b); an alkyl group of _{C 1 ~ 20;; C 1} ~ 20 alkyl import of Im; C _{1 ~ 20} alkoxy group of C _{2 ~ 20} alkene group; alkynyl of _{C 2 ~ 20; C 6 ~} 20 aryl group; in the C _{6 ~ 20} substituted by deuterium aryl group; fluorene group; a heterocyclic group of C _{2 ~ 20;} a cycloalkyl group of C _{3 ~ 20} , An arylalkyl group having _{7 to 20} carbon atoms and an arylalkenyl group having _{8 to 20} carbon atoms, and these substituents may be further bonded to each other to form a ring, wherein the 'ring' It is those that have a fused ring consisting of a heterocyclic or a combination of C _{3 ~ 60} aliphatic ring or a C _{6 ~ 60} aromatic ring or C _{2 ~ 60} of, Saturated or unsaturated ring).

More specifically, the present invention provides an organic electroluminescent device comprising a composition comprising the compound represented by Formula 1-2 or Formula 1-3.

&Lt; General Formula 1-2 >

(1), R ¹ , R ² , Ar ² , L ¹ to L ³ , a to c, l and m are the same as defined above, and 2) X ¹ and X ² is independently of each other S, O or CR'R "and R 'and R" are independently of each other a C _6-24 aryl group, a C _1-20 alkyl group, a C _2-20 alkenyl, C ₁ is selected from the group consisting of a _{~ 20} alkoxy, R 'and R "are bonded to can form a spy, 3) R ¹ to R ⁶ are independently deuterium each other; tritium; halogen; a cyano group; a nitro group; an aryl group of C _{6 ~ 60;} fluorene group; O, N, S, Si and P of the at least one heterocyclic group of C _{2 ~ 60} containing a hetero atom; an aliphatic ring of C _{3 ~ 60} and C _{6 ~} fused ring group of ₆₀ aromatic ring; C alkyl group of _{1 to 50;} consisting of a aryloxy and _{C 6 ~ 30; C 2 ~} 20 alkenyl group of; alkynyl of C _{2 ~ 20;} an alkoxy group of C _{1 ~ 30} or selected from the group, or be present around the plurality of R ¹ to R ⁶ Between the adjacent R ^1, R ² together, R ³ together, R ⁴ together, R ⁵ each other, R ⁶ each other and bonded to each other may form at least one ring (where, R ¹ to R ⁶ do not form a ring 4) n and p are independently selected from integers of 0 to 3, and when each of these is an integer of 2 or more, R ³ and R ⁵ are the same as or different from each other, and 5) o , and q are independently selected from the integers of 0 to 4, and when each of these is an integer of 2 or more, R ⁴ and R ⁶ are the same or different from each other.

In another specific example of the present invention, the formula (2) provides an organic electroluminescent device comprising a composition including a compound represented by one of the following formulas (2-2) to (2-5).

&Lt; Formula 2-2 > < Formula 2-3 >

&Lt; Formula 2-4 > < Formula 2-5 >

Wherein Ar ¹ to Ar ⁶ , L ⁴ to L ⁸ and d to h are the same as defined above, and 2) X ³ to X ⁶ independently represent S , O or CR'R &quot;, and R 'and R "are independently selected from the group consisting of C _6-24 aryl, C _1-20 alkyl, C _2-20 alkenyl and C _1-20 alkoxy groups 3) R ⁷ to R ¹⁴ are, independently of each other, selected from the group consisting of deuterium, tritium, halogen, cyano, nitro, C _{6 to} C ₆₀ aryl ; fluorene group; O, N, S, Si and P of the at least one hetero atom heterocyclic group of C _{2 ~ 60} containing; fused ring of an aromatic ring of C _{3 ~ 60} alicyclic and C _{6 ~ 60} of the groups; C _{2 ~ 20} alkenyl group of;; C _{2 ~ 20} alkynyl of; C _{1 ~ 30} alkoxyl group; C _{1 ~ 50} alkyl group, and being selected from an aryloxy group the group consisting of a C _{6 ~ 30,} or more If the R ⁷ to R ¹⁴ is present Adjacent R ⁷ together with each other, R ^8, R ⁹ to each other, R ¹⁰ together, R ¹² together, R ¹³ together, R ¹⁴ with each other can be formed at least one collar connected to each other (however, R do not form a ring ⁷ to R ¹⁴ are the same as defined above.) in case 4), r, t, v, x is independently selected from an integer from 0 to 3 to each other, two or more integer, each of them, R ^7, R ^9, when R ¹¹ and R ¹³ are each the same or different from each other and, 5) s, u, w, y is independently selected from an integer from 0 to 4 with each other, two or more integer, each of them, R ^8, R ^10, R ¹² and R &lt; ¹⁴ &gt; are the same or different from each other.

In a more specific embodiment, the compound represented by Formula 1 is one of the following compounds, and provides an organic electric device including the composition comprising the compound.

As another specific example, the organic electroluminescent device is characterized in that the compound represented by Formula 2 mixed with the compound represented by Formula 1 is one of the following compounds.

In another embodiment of the present invention, the composition of the present invention comprises a compound wherein Ar ¹ and Ar ² of the compound represented by the formula (1) and Ar ³ to Ar ⁶ of the compound represented by the formula (2) are both C _{6 to} C ₂₄ aryl groups Thereby providing an organic electric device.

According to another aspect of the present invention, there is provided a composition comprising at least one of Ar ¹ and Ar ² of the compound represented by Formula ¹ and Ar ³ to Ar ⁶ of the compound represented by Formula 2 as dibenzothiophene or dibenzofuran And an organic electroluminescent device.

In another specific embodiment, Ar ¹ and Ar ² of the compound represented by Formula 1 are all C _{6 to} C ₂₄ aryl groups, and at least one of Ar ³ to Ar ⁶ of the compound represented by Formula 2 is dibenzothiophene or dibenzofuran &lt; / RTI &gt; phosphorus compound.

In another specific example of the present invention, at least one of Ar ¹ and Ar ² of the compound represented by Formula 1 is dibenzothiophene or dibenzofuran, and Ar ³ to Ar ⁶ of the compound represented by Formula 2 are all C _{6 to 24} An aryl group, and the like.

The composition of the present invention is a composition in which the weight ratio of the compound represented by the formula (1) is 10% to 90% when the compound represented by the formula (1) and the compound represented by the formula (2) are mixed, And a display device including the same.

In another example of the present invention, when the compound represented by Formula 1 and the compound represented by Formula 2 are mixed, the mixing ratio is 5: 5 or 6: 4 or 7: 3 or 8: 2 Or 9: 1, and a display device including the same.

As another example presented in one example of the present invention, there is provided a process for preparing a compound represented by the general formula (1), wherein the compound represented by the general formula (1) or the compound represented by the general formula (2) And at least one organic electroluminescent device and a display device including the same.

The organic electroluminescent device further comprises an emission auxiliary layer between the hole transport layer and the light emitting layer, the organic electroluminescent device comprising a mixture of the compound represented by the formula (1) and the compound represented by the formula (2) And a light-efficiency-improvement layer formed on at least one side of the one surface of the second electrode opposite to the organic material layer. Wherein the organic material layer is formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process or a roll-to-roll process.

The present invention provides an electronic device including a display device including the organic electronic devices of various examples described above and a control unit for driving the display device. The organic electroluminescent device may be an organic electroluminescent device, an organic photovoltaic cell, an organophotoreceptor, an organic transistor, or an element for monochromatic or white illumination.

Hereinafter, the synthesis examples of the compounds represented by the formulas (1) and (2) included in the organic electronic device of the present invention and the production example of the organic electronic device of the present invention will be specifically described. The present invention is not limited thereto.

[Synthesis Example]

I. Synthesis of Formula 1

The compounds represented by formula (1) according to the present invention are synthesized by reacting Sub 1 and Sub 2 as shown in Reaction Scheme 1 below, but are not limited thereto.

<Reaction Scheme 1>

Wherein Hal ² is Br or Cl, the same as that in the above reaction scheme ^{1, R 1, R 2,} Ar 1, Ar 2, L 1 to ^{L 3, a, b, c} , l , and m are defined in formula (I) Do.

1. Synthesis of Sub 1

Sub 1 of Reaction Scheme 1 can be synthesized by the reaction path of Reaction Scheme 2, but is not limited thereto.

<Reaction Scheme 2>

Hal ¹ is I or Br; Hal ² is Br or Cl, and specific examples of the compound belonging to Sub 1 are as follows.

(1) Sub 1-2 Synthesis Example

<Reaction Scheme 3>

Sub 1-I-2 Synthetic Example

Bromo-2-nitrobenzene (119.29 g, 590.5 mmol) and Pd (PPh ₃ ) ₄ (28.43 g, 24.6 mmol) were dissolved in THF (1800 ml) , K ₂ CO ₃ (204.03 g, 1476.3 mmol) and water (900 ml) were added and stirred at 90 ° C. After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 90.19 g of the product (yield: 92%).

Sub 1-II-2 Synthesis Example

Sub-1-I-2 (90.19 g, 452.7 mmol) obtained in the above synthesis was dissolved in o- dichlorobenzene (2260 ml) and then triphenylphosphine (296.87 g, 1131.8 mmol) was added to a round bottom flask and stirred at 200 ° C. When the reaction was complete, o- dichlorobenzene was removed by distillation and extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 60.56 g (yield: 80%) of the product.

Sub 1-2 Synthesis Example

Sub 1-II-2 (12 g, 71.8 mmol) obtained in the above synthesis was dissolved in nitrobenzene (450 ml) and then 4-bromo-4'-iodo-1,1'-biphenyl (38.65 g, 107.6 Na ₂ SO ₄ (10.19 g, 71.8 mmol), K ₂ CO ₃ (9.92 g, 71.8 mmol) and Cu (1.37 g, 21.5 mmol) were added and stirred at 200 ° C. When the reaction was complete, nitrobenzene was removed by distillation and extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 21.15 g (yield: 74%) of the product.

(2) Sub 1-7 Synthetic Example

<Reaction Scheme 4>

Sub 1-I-7 Synthetic Example

naphthalen-1-ylboronic acid (10 g, 58.1 mmol) 1-bromo-2-nitrobenzene in (14.09 g, 69.8 mmol), Pd (PPh 3) 4 (3.36 g, 2.9 mmol), K 2 CO 3 (24.11 g , 174.4 mmol), THF (210 ml) and water (105 ml) were subjected to the synthesis of Sub 1-I-2 to obtain 12.9 g of the product (yield: 89%).

Sub 1-II-7 Synthesis Example

Triphenylphosphine (33.94 g, 129.4 mmol) and o- dichlorobenzene (450 ml) were added to Sub 1-I-7 obtained in the above synthesis (12.9 g, 51.8 mmol) Yield: 77%).

Sub 1-7 Synthetic Example

4-bromo-4'-iodo-1,1'-biphenyl (21.46 g, 59.8 mmol), Na ₂ SO ₄ (5.66 g, 39.9 mmol) was added to Sub 1-II- 12.51 g (yield: 70%) of the product was obtained using Sub 1-2 synthesis method using K ₂ CO ₃ (5.51 g, 39.9 mmol), Cu (0.76 g, 12 mmol) and nitrobenzene (250 ml) .

(3) Sub 1-8 Synthetic Example

<Reaction Scheme 5>

Sub 1-I-8 Synthetic Example

phenylboronic acid (15 g, 123 mmol ) for 2-bromo-1-nitronaphthalene ( 37.21 g, 147.6 mmol), Pd (PPh 3) 4 (7.11 g, 6.2 mmol), K 2 CO 3 (51.01 g, 369.1 mmol) 26.37 g (yield: 86%) of the product was obtained by using Sub 1-I-2 synthesis method, THF (450 ml) and water (225 ml).

Sub 1-II-8 Synthesis Example

Triphenylphosphine (69.37 g, 264.5 mmol) and o- dichlorobenzene (926 ml) were added to Sub 1-I-8 (26.37 g, 105.8 mmol) obtained in the above synthesis in 17.01 g Yield: 74%).

Sub 1-8 Synthetic Example

4-bromo-4'-iodo-1,1'-biphenyl (42.16 g, 117.4 mmol), Na ₂ SO ₄ (11.12 g, 78.3 mmol) was added to Sub 1-II-8 (17.01 g, 78.3 mmol) 24.22 g (Yield: 69%) of the product was obtained using Sub 1-2 synthesis method using K ₂ CO ₃ (10.82 g, 78.3 mmol), Cu (1.49 g, 23.5 mmol) and nitrobenzene (490 ml) .

(4) Sub 1-24 Synthetic Example

<Reaction Scheme 6>

3-bromo-6-iodophenanthrene (34.36 g, 89.7 mmol), Na ₂ SO ₄ (8.49 g, 59.8 mmol) and K ₂ CO ₃ (10 g, 59.8 mmol) were added to Sub 1-II- 16.42 g (Yield: 65%) of the product was obtained by using the sub 1-2 synthesis method, 8.27 g, 59.8 mmol), Cu (1.14 g, 17.9 mmol) and nitrobenzene (370 ml).

(5) Sub 1-29 Synthesis Example

<Reaction Scheme 7>

3-bromo-7-iododibenzo [b, d] thiophene (34.9 g, 89.7 mmol) and Na ₂ SO ₄ (8.49 g, 59.8 mmol) were added to Sub 1-II- 17.68 g (Yield: 69%) of product was obtained using Sub 1-2 synthesis method, K ₂ CO ₃ (8.27 g, 59.8 mmol), Cu (1.14 g, 17.9 mmol) and nitrobenzene (370 ml).

(6) Sub 1-35 Synthesis Example

<Reaction Scheme 8>

The Sub 1-II-2 (7 g, 41.9 mmol) obtained in the Synthesis 2-bromo-7-iodo- 9,9-dimethyl-9H-fluorene (25.06 g, 62.8 mmol), Na 2 SO 4 (5.95 g 12.3 g (Yield: 67%) of the product was obtained by using the Sub 1-2 synthesis method, K ₂ CO ₃ (5.79 g, 41.9 mmol), Cu (0.8 g, 12.6 mmol) and nitrobenzene (260 ml) .

(7) Sub 1-44 Synthetic Example

<Reaction Scheme 9>

Obtained in the above Synthesis Sub 1-II-2 (10 g, 59.8 mmol) 2-bromo-7-iodo-9,9-diphenyl-9H-fluorene in (46.93 g, 89.7 mmol), Na 2 SO 4 (8.49 g 21.19 g (yield: 63%) of the product was obtained by using the Sub 1-2 synthesis method, K ₂ CO ₃ (8.27 g, 59.8 mmol), Cu (1.14 g, 17.9 mmol) and nitrobenzene (370 ml) .

(8) Sub 1-47 Synthetic Example

<Reaction formula 10>

2-bromo-7-iodo-9,9'-spirobi [fluorene] (46.75 g, 89.7 mmol) and Na ₂ SO ₄ (8.49 g, 59.8 mmol) were added to Sub 1-II- 20.45 g (Yield: 61%) of the product was obtained by using the Sub 1-2 synthesis method using K ₂ CO ₃ (8.27 g, 59.8 mmol), Cu (1.14 g, 17.9 mmol) and nitrobenzene (370 ml) .

On the other hand, the compound belonging to Sub 1 may be, but not limited to, the following compounds, and Table 1 shows the FD-MS value of the compound belonging to Sub 1.

compound FD-MS compound FD-MS Sub 1-1 _{m / z = 321.02 (C 18} H 12 BrN = 322.20) Sub 1-2 m / z = 397.05 (C ₂₄ H ₁₆ BrN = 398.29) Sub 1-3 m / z = 549.11 (C ₃₆ H ₂₄ BrN = 550.49) Sub 1-4 _{m / z = 550.10 (C 35} H 23 BrN 2 = 551.47) Sub 1-5 _{m / z = 473.08 (C 30} H 20 BrN = 474.39) Sub 1-6 m / z = 474.07 (C ₂₉ H ₁₉ BrN ₂ = 475.38) Sub 1-7 _{m / z = 447.06 (C 28} H 18 BrN = 448.35) Sub 1-8 _{m / z = 447.06 (C 28} H 18 BrN = 448.35) Sub 1-9 _{m / z = 447.06 (C 28} H 18 BrN = 448.35) Sub 1-10 m / z = 497.08 (C ₃₂ H ₂₀ BrN = 498.41) Sub 1-11 m / z = 497.08 (C ₃₂ H ₂₀ BrN = 498.41) Sub 1-12 m / z = 397.05 (C ₂₄ H ₁₆ BrN = 398.29) Sub 1-13 m / z = 638.14 (C ₄₂ H ₂₇ BrN ₂ = 639.58) Sub 1-14 m / z = 579.07 (C ₃₆ H ₂₂ BrNS = 580.54) Sub 1-15 _{m / z = 451.09 (C 28} H 22 BrN = 452.38) Sub 1-16 _{m / z = 564.12 (C 36} H 25 BrN 2 = 565.50) Sub 1-17 _{m / z = 447.06 (C 28} H 18 BrN = 448.35) Sub 1-18 m / z = 397.05 (C ₂₄ H ₁₆ BrN = 398.29) Sub 1-19 m / z = 397.05 (C ₂₄ H ₁₆ BrN = 398.29) Sub 1-20 _{m / z = 447.06 (C 28} H 18 BrN = 448.35) Sub 1-21 m / z = 497.08 (C ₃₂ H ₂₀ BrN = 498.41) Sub 1-22 m / z = 397.05 (C ₂₄ H ₁₆ BrN = 398.29) Sub 1-23 m / z = 397.05 (C ₂₄ H ₁₆ BrN = 398.29) Sub 1-24 m / z = 421.05 (C ₂₆ H ₁₆ BrN = 422.32) Sub 1-25 _{m / z = 447.06 (C 28} H 18 BrN = 448.35) Sub 1-26 _{m / z = 473.08 (C 30} H 20 BrN = 474.39) Sub 1-27 m / z = 625.14 (C ₄₂ H ₂₈ BrN = 626.58) Sub 1-28 _{m / z = 548.09 (C 35} H 21 BrN 2 = 549.46) Sub 1-29 m / z = 427.00 (C ₂₄ H ₁₄ BrNS = 428.34) Sub 1-30 m / z = 527.03 (C ₃₂ H ₁₈ BrNS = 528.46) Sub 1-31 m / z = 427.00 (C ₂₄ H ₁₄ BrNS = 428.34) Sub 1-32 m / z = 427.00 (C ₂₄ H ₁₄ BrNS = 428.34) Sub 1-33 m / z = 411.03 (C ₂₄ H ₁₄ BrNO = 412.28) Sub 1-34 m / z = 411.03 (C ₂₄ H ₁₄ BrNO = 412.28) Sub 1-35 m / z = 437.08 (C ₂₇ H ₂₀ BrN = 438.36) Sub 1-36 _{m / z = 563.12 (C 37} H 26 BrN = 564.51) Sub 1-37 m / z = 590.14 (C ₃₈ H ₂₇ BrN ₂ = 591.54) Sub 1-38 m / z = 487.09 (C ₃₁ H ₂₂ BrN = 488.42) Sub 1-39 m / z = 487.09 (C ₃₁ H ₂₂ BrN = 488.42) Sub 1-40 m / z = 487.09 (C ₃₁ H ₂₂ BrN = 488.42) Sub 1-41 _{m / z = 537.11 (C 35} H 24 BrN = 538.48) Sub 1-42 _{m / z = 537.11 (C 35} H 24 BrN = 538.48) Sub 1-43 m / z = 437.08 (C ₂₇ H ₂₀ BrN = 438.36) Sub 1-44 _{m / z = 561.11 (C 37} H 24 BrN = 562.50) Sub 1-45 _{m / z = 561.11 (C 37} H 24 BrN = 562.50) Sub 1-46 _{m / z = 559.09 (C 37} H 22 BrN = 560.48) Sub 1-47 _{m / z = 559.09 (C 37} H 22 BrN = 560.48) Sub 1-48 m / z = 762.17 (C ₅₂ H ₃₁ BrN ₂ = 763.72)

2. Synthesis of Sub 2

Sub 2 of Reaction Scheme 1 may be synthesized by the reaction route of Reaction Scheme 11, but is not limited thereto.

<Reaction Scheme 11>

Hal ² is Br or Cl

Examples of the synthesis of specific compounds belonging to Sub 2 are as follows.

(1) Sub 2-1 Synthesis Example

<Reaction Scheme 12>

To a round bottom flask was added aniline (40 g, 429.5 mmol) was dissolved in toluene (3000 ml), bromobenzene ( 74.18 g, 472.5 mmol), Pd 2 (dba) 3 (19.66 g, 21.5 mmol), 50% P (t -Bu) ₃ (20.9 ml, 43 mmol) and NaO t- Bu (136.22 g, 1417.4 mmol) were added and stirred at 100 ° C. After completion of the reaction, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was subjected to silicagel column and recrystallization to obtain 54.51 g of the product (yield: 75%).

(2) Sub 2-3 Synthesis Example

<Reaction Scheme 13>

aniline (40 g, 429.5 mmol) , 1-bromonaphthalene (97.83 g, 472.5 mmol), Pd 2 (dba) 3 (19.66 g, 21.5 mmol), 50% P (t -Bu) 3 (20.9 ml, 43 mmol) , NaO t- Bu (136.22 g, 1417.4 mmol) and toluene (3000 ml) were subjected to the synthesis of Sub 2-1 to obtain 67.81 g of the product (yield: 72%).

(3) Sub 2-26 Synthesis Example

<Reaction Scheme 14>

4-bromo-1,1'-biphenyl (45.46 g, 195 mmol), Pd ₂ (dba) ₃ (8.12 g, 8.9 mmol) ), 50.0% P ( t- Bu) ₃ (8.6 ml, 17.7 mmol), NaO t- Bu (56.23 g, 585 mmol) and toluene (1860 ml) Yield: 79%).

(4) Sub 2-40 Synthetic Example

<Reaction Scheme 15>

aniline (15 g, 161.1 mmol) , 2-bromodibenzo [b, d] thiophene (46.62 g, 177.2 mmol), Pd 2 (dba) 3 (7.37 g, 8.1 mmol), 50% P (t -Bu) 3 ( (Yield: 77%) of the product was obtained by using Sub 2-1 synthesis method described above, 7.9 ml, 16.1 mmol), NaO t- Bu (51.08 g, 531.5 mmol) and toluene (1690 ml).

(5) Sub 2-44 Synthetic Example

<Reaction Scheme 16>

dibenzo [b, d] thiophen- 2-amine (20 g, 100.4 mmol), 6-bromoisoquinoline (22.97 g, 110.4 mmol), Pd 2 (dba) 3 (4.6 g, 5 mmol), 50% P (t - Bu) ₃ (4.9 ml, 10 mmol), NaO t- Bu (31.83 g, 331.2 mmol) and toluene (1050 ml) were used to synthesize 20.64 g of the product (63% yield).

(6) Sub 2-76 Synthetic Example

<Reaction Scheme 17>

(49.65 g, 153.6 mmol), Pd ₂ (dba) ₃ (6.39 g, 7 mmol), 4- (4-bromophenyl) dibenzo [b, 40.38 g (Yield: 75%) of the product was obtained by using Sub 2-1 synthesis method described above,% P ( t- Bu) ₃ (6.8 ml, 14 mmol), NaO t- Bu (44.3 g, 460.9 mmol) %).

(7) Sub 2-96 Synthesis Example

<Reaction Scheme 18>

Pd ₂ (dba) ₃ (4.8 g, 5.2 mmol), 50% of naphthalen-1-amine (15 g, 104.8 mmol), 2-bromo-9,9- 34.18 g (Yield: 71%) of P ( t- Bu) ₃ (5.1 ml, 10.5 mmol), NaO t- Bu (33.22 g, 345.7 mmol) and toluene (1100 ml) ).

(8) Sub 2-102 Synthesis Example

<Reaction Scheme 19>

Pd ₂ (dba) ₃ (4.92 g, 5.4 mmol), 50% P ( t -butyl) aniline (10 g, 107.4 mmol), 2-bromo-9,9'-spirobi [fluorene] (46.69 g, 118.1 mmol) 28.44 g (Yield: 65%) of product ( ₃ ) (5.2 ml, 10.7 mmol), NaO t- Bu (34.06 g, 354.3 mmol) and toluene (1130 ml) were obtained using the Sub 2-1 synthesis method described above.

(9) Sub 2-113 Synthetic Example

<Reaction Scheme 20>

aniline (15 g, 161.1 mmol) , 2-bromo-9-phenyl-9H-carbazole (57.08 g, 177.2 mmol), Pd 2 (dba) 3 (7.37 g, 8.1 mmol), 50% P (t -Bu) ₃ (7.9 ml, 16.1 mmol), NaO t- Bu (51.08 g, 531.5 mmol) and toluene (1690 ml) were used to obtain 36.63 g of the product (yield: 68%).

(10) Sub 2-121 Synthesis Example

<Reaction Scheme 21>

naphthalen-1-amine (20 g , 139.7 mmol), 1-bromo-4-vinylbenzene (28.12 g, 153.6 mmol), Pd 2 (dba) 3 (6.39 g, 7 mmol), 50% P (t -Bu) 17.82 g (yield: 52%) of the product was obtained by using Sub 2-1 synthesis method described above, ₃ (6.8 ml, 14 mmol), NaO t- Bu (44.3 g, 460.9 mmol) and toluene

On the other hand, the compound belonging to Sub 2 may be, but not limited to, the following compound, and Table 2 shows the FD-MS value of the compound belonging to Sub 2.

compound FD-MS compound FD-MS Sub 2-1 m / z = 169.09 (C ₁₂ H ₁₁ N = 169.22) Sub 2-2 m / z = 225.15 (C ₁₆ H ₁₉ N = 225.33) Sub 2-3 m / z = 219.10 (C ₁₆ H ₁₃ N = 219.28) Sub 2-4 _{m / z = 220.10 (C 15} H 12 N 2 = 220.27) Sub 2-5 _{m / z = 220.10 (C 15} H 12 N 2 = 220.27) Sub 2-6 m / z = 219.10 (C ₁₆ H ₁₃ N = 219.28) Sub 2-7 _{m / z = 269.12 (C 20} H 15 N = 269.34) Sub 2-8 _{m / z = 269.12 (C 20} H 15 N = 269.34) Sub 2-9 _{m / z = 293.12 (C 22} H 15 N = 293.36) Sub 2-10 _{m / z = 245.12 (C 18} H 15 N = 245.32) Sub 2-11 _{m / z = 250.15 (C 18} H 10 D 5 N = 250.35) Sub 2-12 _{m / z = 250.15 (C 18} H 10 D 5 N = 250.35) Sub 2-13 _{m / z = 246.12 (C 17} H 14 N 2 = 246.31) Sub 2-14 _{m / z = 245.12 (C 18} H 15 N = 245.32) Sub 2-15 _{m / z = 295.14 (C 22} H 17 N = 295.38) Sub 2-16 _{m / z = 295.14 (C 22} H 17 N = 295.38) Sub 2-17 _{m / z = 269.12 (C 20} H 15 N = 269.34) Sub 2-18 _{m / z = 295.14 (C 22} H 17 N = 295.38) Sub 2-19 _{m / z = 300.17 (C 22} H 12 D 5 N = 300.41) Sub 2-20 _{m / z = 295.14 (C 22} H 17 N = 295.38) Sub 2-21 _{m / z = 295.14 (C 22} H 17 N = 295.38) Sub 2-22 _{m / z = 269.12 (C 20} H 15 N = 269.34) Sub 2-23 m / z = 345.15 (C ₂₆ H ₁₉ N = 345.44) Sub 2-24 _{m / z = 296.13 (C 21} H 16 N 2 = 296.37) Sub 2-25 _{m / z = 346.15 (C 25} H 18 N 2 = 346.42) Sub 2-26 m / z = 321.15 (C ₂₄ H ₁₉ N = 321.41) Sub 2-27 m / z = 321.15 (C ₂₄ H ₁₉ N = 321.41) Sub 2-28 m / z = 321.15 (C ₂₄ H ₁₉ N = 321.41) Sub 2-29 m / z = 321.15 (C ₂₄ H ₁₉ N = 321.41) Sub 2-30 m / z = 421.18 (C ₃₂ H ₂₃ N = 421.53) Sub 2-31 _{m / z = 300.17 (C 22} H 12 D 5 N = 300.41) Sub 2-32 m / z = 421.18 (C ₃₂ H ₂₃ N = 421.53) Sub 2-33 m / z = 321.15 (C ₂₄ H ₁₉ N = 321.41) Sub 2-34 _{m / z = 371.17 (C 28} H 21 N = 371.47) Sub 2-35 m / z = 319.14 (C ₂₄ H ₁₇ N = 319.40) Sub 2-36 _{m / z = 293.12 (C 22} H 15 N = 293.36) Sub 2-37 _{m / z = 395.17 (C 30} H 21 N = 395.49) Sub 2-38 _{m / z = 386.18 (C 28} H 22 N 2 = 386.49) Sub 2-39 m / z = 224.14 (C ₁₆ H ₈ D ₅ N = 224.31) Sub 2-40 _{m / z = 275.08 (C 18} H 13 NS = 275.37) Sub 2-41 _{m / z = 325.09 (C 22} H 15 NS = 325.43) Sub 2-42 _{m / z = 325.09 (C 22} H 15 NS = 325.43) Sub 2-43 m / z = 351.11 (C ₂₄ H ₁₇ NS = 351.46) Sub 2-44 _{m / z = 326.09 (C 21} H 14 N 2 S = 326.41) Sub 2-45 m / z = 351.11 (C ₂₄ H ₁₇ NS = 351.46) Sub 2-46 _{m / z = 275.08 (C 18} H 13 NS = 275.37) Sub 2-47 _{m / z = 290.09 (C 18} H 14 N 2 S = 290.38) Sub 2-48 _{m / z = 325.09 (C 22} H 15 NS = 325.43) Sub 2-49 m / z = 351.11 (C ₂₄ H ₁₇ NS = 351.46) Sub 2-50 m / z = 381.06 (C ₂₄ H ₁₅ NS ₂ = 381.51) Sub 2-51 _{m / z = 401.12 (C 28} H 19 NS = 401.52) Sub 2-52 _{m / z = 275.08 (C 18} H 13 NS = 275.37) Sub 2-53 m / z = 351.11 (C ₂₄ H ₁₇ NS = 351.46) Sub 2-54 _{m / z = 325.09 (C 22} H 15 NS = 325.43) Sub 2-55 _{m / z = 401.12 (C 28} H 19 NS = 401.52) Sub 2-56 m / z = 351.11 (C ₂₄ H ₁₇ NS = 351.46) Sub 2-57 _{m / z = 352.10 (C 23} H 16 N 2 S = 352.45) Sub 2-58 _{m / z = 440.13 (C 30} H 20 N 2 S = 440.56) Sub 2-59 m / z = 375.11 (C ₂₆ H ₁₇ NS = 375.48) Sub 2-60 m / z = 381.06 (C ₂₄ H ₁₅ NS ₂ = 381.51) Sub 2-61 m / z = 351.11 (C ₂₄ H ₁₇ NS = 351.46) Sub 2-62 _{m / z = 309.12 (C 22} H 15 NO = 309.36) Sub 2-63 _{m / z = 259.10 (C 18} H 13 NO = 259.30) Sub 2-64 _{m / z = 309.12 (C 22} H 15 NO = 309.36) Sub 2-65 m / z = 335.13 (C ₂₄ H ₁₇ NO = 335.40) Sub 2-66 m / z = 349.11 (C ₂₄ H ₁₅ NO ₂ = 349.38) Sub 2-67 _{m / z = 309.12 (C 22} H 15 NO = 309.36) Sub 2-68 _{m / z = 259.10 (C 18} H 13 NO = 259.30) Sub 2-69 m / z = 335.13 (C ₂₄ H ₁₇ NO = 335.40) Sub 2-70 _{m / z = 259.10 (C 18} H 13 NO = 259.30) Sub 2-71 m / z = 335.13 (C ₂₄ H ₁₇ NO = 335.40) Sub 2-72 _{m / z = 461.18 (C 34} H 23 NO = 461.55) Sub 2-73 m / z = 335.13 (C ₂₄ H ₁₇ NO = 335.40) Sub 2-74 m / z = 335.13 (C ₂₄ H ₁₇ NO = 335.40) Sub 2-75 m / z = 335.13 (C ₂₄ H ₁₇ NO = 335.40) Sub 2-76 _{m / z = 385.15 (C 28} H 19 NO = 385.46) Sub 2-77 _{m / z = 411.16 (C 30} H 21 NO = 411.49) Sub 2-78 _{m / z = 411.16 (C 30} H 21 NO = 411.49) Sub 2-79 _{m / z = 285.15 (C 21} H 19 N = 285.38) Sub 2-80 _{m / z = 290.18 (C 21} H 14 D 5 N = 290.41) Sub 2-81 _{m / z = 335.17 (C 25} H 21 N = 335.44) Sub 2-82 m / z = 361.18 (C ₂₇ H ₂₃ N = 361.48) Sub 2-83 m / z = 391.14 (C ₂₇ H ₂₁ NS = 391.53) Sub 2-84 _{m / z = 401.21 (C 30} H 27 N = 401.54) Sub 2-85 _{m / z = 335.17 (C 25} H 21 N = 335.44) Sub 2-86 _{m / z = 335.17 (C 25} H 21 N = 335.44) Sub 2-87 m / z = 385.18 (C ₂₉ H ₂₃ N = 385.50) Sub 2-88 m / z = 361.18 (C ₂₇ H ₂₃ N = 361.48) Sub 2-89 _{m / z = 299.17 (C 22} H 21 N = 299.41) Sub 2-90 m / z = 385.18 (C ₂₉ H ₂₃ N = 385.50) Sub 2-91 m / z = 409.18 (C ₃₁ H ₂₃ N = 409.52) Sub 2-92 m / z = 525.25 (C ₄₀ H ₃₁ N = 525.68) Sub 2-93 m / z = 409.18 (C ₃₁ H ₂₃ N = 409.52) Sub 2-94 m / z = 423.20 (C ₃₂ H ₂₅ N = 423.55) Sub 2-95 m / z = 439.19 (C ₃₂ H ₂₅ NO = 439.55) Sub 2-96 _{m / z = 459.20 (C 35} H 25 N = 459.58) Sub 2-97 _{m / z = 485.21 (C 37} H 27 N = 485.62) Sub 2-98 m / z = 562.24 (C ₄₂ H ₃₀ N ₂ = 562.70) Sub 2-99 _{m / z = 485.21 (C 37} H 27 N = 485.62) Sub 2-100 m / z = 523.23 (C ₄₀ H ₂₉ N = 523.66) Sub 2-101 m / z = 407.17 (C ₃₁ H ₂₁ N = 407.51) Sub 2-102 m / z = 407.17 (C ₃₁ H ₂₁ N = 407.51) Sub 2-103 _{m / z = 483.20 (C 37} H 25 N = 483.60) Sub 2-104 _{m / z = 457.18 (C 35} H 23 N = 457.56) Sub 2-105 m / z = 334.15 (C ₂₄ H ₁₈ N ₂ = 334.41) Sub 2-106 _{m / z = 384.16 (C 28} H 20 N 2 = 384.47) Sub 2-107 _{m / z = 410.18 (C 30} H 22 N 2 = 410.51) Sub 2-108 _{m / z = 384.16 (C 28} H 20 N 2 = 384.47) Sub 2-109 _{m / z = 384.16 (C 28} H 20 N 2 = 384.47) Sub 2-110 _{m / z = 410.18 (C 30} H 22 N 2 = 410.51) Sub 2-111 m / z = 450.21 (C ₃₃ H ₂₆ N ₂ = 450.57) Sub 2-112 _{m / z = 384.16 (C 28} H 20 N 2 = 384.47) Sub 2-113 m / z = 334.15 (C ₂₄ H ₁₈ N ₂ = 334.41) Sub 2-114 _{m / z = 225.06 (C 14} H 11 NS = 225.31) Sub 2-115 _{m / z = 225.06 (C 14} H 11 NS = 225.31) Sub 2-116 _{m / z = 284.13 (C 20} H 16 N 2 = 284.35) Sub 2-117 m / z = 334.15 (C ₂₄ H ₁₈ N ₂ = 334.41) Sub 2-118 _{m / z = 293.07 (C 18} H 12 FNS = 293.36) Sub 2-119 _{m / z = 220.10 (C 15} H 12 N 2 = 220.27) Sub 2-120 _{m / z = 297.13 (C 20} H 15 N 3 = 297.35) Sub 2-121 _{m / z = 245.12 (C 18} H 15 N = 245.32) Sub 2-122 m / z = 321.15 (C ₂₄ H ₁₉ N = 321.41) Sub 2-123 _{m / z = 270.12 (C 19} H 14 N 2 = 270.33) Sub 2-124 m / z = 336.16 (C ₂₄ H ₂₀ N ₂ = 336.43) Sub 2-125 m / z = 503.24 (C ₃₆ H ₂₉ N ₃ = 503.64) Sub 2-126 m / z = 486.21 (C ₃₆ H ₂₆ N ₂ = 486.61) Sub 2-127 m / z = 359.13 (C ₂₆ H ₁₇ NO = 359.42) Sub 2-128 _{m / z = 336.13 (C 23} H 16 N 2 O = 336.39) Sub 2-129 _{m / z = 517.15 (C 36} H 23 NOS = 517.64) Sub 2-130 m / z = 349.11 (C ₂₄ H ₁₅ NO ₂ = 349.38) Sub 2-131 m / z = 365.09 (C ₂₄ H ₁₅ NOS = 365.45) Sub 2-132 m / z = 365.09 (C ₂₄ H ₁₅ NOS = 365.45) Sub 2-133 m / z = 365.09 (C ₂₄ H ₁₅ NOS = 365.45) Sub 2-134 m / z = 365.09 (C ₂₄ H ₁₅ NOS = 365.45) Sub 2-135 _{m / z = 415.10 (C 28} H 17 NOS = 415.51) Sub 2-136 m / z = 365.09 (C ₂₄ H ₁₅ NOS = 365.45) Sub 2-137 _{m / z = 465.12 (C 32} H 19 NOS = 465.56) Sub 2-138 m / z = 391.14 (C ₂₇ H ₂₁ NS = 391.53) Sub 2-139 m / z = 391.14 (C ₂₇ H ₂₁ NS = 391.53) Sub 2-140 m / z = 515.17 (C ₃₇ H ₂₅ NS = 515.67) Sub 2-141 _{m / z = 513.16 (C 37} H 23 NS = 513.65) Sub 2-142 m / z = 375.16 (C ₂₇ H ₂₁ NO = 375.46) Sub 2-143 _{m / z = 497.18 (C 37} H 23 NO = 497.58) Sub 2-144 _{m / z = 477.25 (C 36} H 31 N = 477.64)

3. Product Synthesis

Sub 1 (1.1 eq.), Pd ₂ (dba) ₃ (0.05 eq.), P ( t- Bu) ₃ (0.1 eq.), NaO t- Bu (3.3 eq.) Was added and stirred at 100 &lt; 0 &gt; C. After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was subjected to silicagel column and recrystallization to obtain final product.

(1) 1-9 Synthesis Example

<Reaction Formula 22>

Sub 2-26 (7 g, 21.8 mmol) was dissolved in toluene (230 ml) and then Sub 1-2 (9.54 g, 24 mmol) and Pd ₂ (dba) ₃ (1 g, 1.1 mmol) 50% P ( t- Bu) ₃ (1.1 ml, 2.2 mmol) and NaO t- Bu (6.91 g, 71.9 mmol) were added and stirred at 100 ° C. After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 11.69 g (yield: 84%) of the product.

(2) 1-38 Synthesis Example

<Reaction Scheme 23>

Sub-1-22 (10.75 g, 27 mmol), Pd ₂ (dba) ₃ (1.12 g, 1.2 mmol), 50% P ( t- Bu) ₃ (1.2 mL 13.34 g (yield: 75%) of the product was obtained by using the 1-9 synthesis method described above, 2.50 mmol), NaO t- Bu (7.78 g, 81 mmol) and toluene (260 ml).

(3) 1-62 Synthesis Example

<Reaction Scheme 24>

Sub 2-44 (10 g, 30.6 mmol ), Sub 1-24 (14.23 g, 33.7 mmol), Pd 2 (dba) 3 (1.4 g, 1.5 mmol), 50% P (t -Bu) 3 (1.5 ml , 3.1 mmol), NaO t- Bu (9.72 g, 101.1 mmol) and toluene (320 ml) were used to obtain 12.48 g of the product (yield: 61%).

(4) 1-64 Synthesis Example

<Reaction Scheme 25>

Sub 2-1 (7 g, 31.9 mmol ), Sub 1-29 (15.04 g, 35.1 mmol), Pd 2 (dba) 3 (1.46 g, 1.6 mmol), 50% P (t -Bu) 3 (1.6 ml , 3.2 mmol), NaO t- Bu (10.12 g, 105.3 mmol) and toluene (340 ml) were used to obtain 13.93 g of the product (yield: 77%).

(5) 1-70 Synthesis Example

<Reaction Scheme 26>

Sub 2-26 (7 g, 21.8 mmol ), Sub 1-35 (10.5 g, 24 mmol), Pd 2 (dba) 3 (1 g, 1.1 mmol), 50% P (t -Bu) 3 (1.1 ml , 2.2 mmol), NaO t- Bu (6.91 g, 71.9 mmol) and toluene (230 ml) were used to obtain 12.12 g of the product (yield: 82%).

(6) 1-87 Synthesis Example

<Reaction Scheme 27>

Pd ₂ (dba) ₃ (1.16 g, 1.3 mmol), 50% P ( t- Bu) ₃ (1.2 mL, 15.73 g, 28 mmol) (Yield: 68%) was obtained by using the above 1-9 synthesis method, and NaO t- Bu (8.06 g, 83.9 mmol) and toluene (270 ml) were obtained.

(7) 1-93 Synthesis Example

<Reaction Scheme 28>

Pd ₂ (dBA) ₃ (1.19 g, 1.3 mmol), 50% P ( t- Bu) ₃ (1.3 mL, 25 mmol), Sub 2-76 (10 g, 25.9 mmol) , 2.6 mmol), NaO t- Bu (8.23 g, 85.6 mmol) and toluene (270 ml) were used to obtain 13.46 g of the product (yield: 60%).

(8) 1-100 Synthetic Example

<Reaction Scheme 29>

Sub 2-96 (10 g, 21.8 mmol ), Sub 1-7 (10.73 g, 23.9 mmol), Pd 2 (dba) 3 (1 g, 1.1 mmol), 50% P (t -Bu) 3 (1.1 ml 13.68 g (Yield: 76%) of the product was obtained by using the 1-9 synthesis method described above, 2.2 mmol), NaO t- Bu (6.9 g, 71.8 mmol) and toluene (230 ml).

(9) 1-121 Synthesis Example

<Reaction Scheme 30>

Sub 2-121 (10 g, 40.8 mmol ), Sub 1-8 (20.1 g, 44.8 mmol), Pd 2 (dba) 3 (1.87 g, 2 mmol), 50% P (t -Bu) 3 (2 ml , 13.74 g (yield: 55%) of the product was obtained by using the above 1-9 synthesis method using 4.1 mmol, NaO t- Bu (12.93 g, 134.5 mmol) and toluene (430 ml).

The FD-MS values of the compounds 1-1 to 1-124 of the present invention prepared according to the above Synthesis Examples are shown in Table 3 below.

compound FD-MS compound FD-MS 1-1 m / z = 486.21 (C ₃₆ H ₂₆ N ₂ = 486.61) 1-2 m / z = 541.26 (C ₄₀ H ₂₃ D ₅ N ₂ = 541.69) 1-3 m / z = 612.26 (C ₄₆ H ₃₂ N ₂ = 612.76) 1-4 m / z = 562.24 (C ₄₂ H ₃₀ N ₂ = 562.70) 1-5 m / z = 636.26 (C ₄₈ H ₃₂ N ₂ = 636.78) 1-6 m / z = 586.24 (C ₄₄ H ₃₀ N ₂ = 586.72) 1-7 m / z = 712.29 (C ₅₄ H ₃₆ N ₂ = 712.88) 1-8 m / z = 638.27 (C ₄₈ H ₃₄ N ₂ = 638.80) 1-9 m / z = 638.27 (C ₄₈ H ₃₄ N ₂ = 638.80) 1-10 m / z = 638.27 (C ₄₈ H ₃₄ N ₂ = 638.80) 1-11 m / z = 638.27 (C ₄₈ H ₃₄ N ₂ = 638.80) 1-12 m / z = 738.30 (C ₅₆ H ₃₈ N ₂ = 738.91) 1-13 m / z = 653.28 (C ₄₈ H ₃₅ N ₃ = 653.81) 1-14 m / z = 820.36 (C ₆₀ H ₄₄ N ₄ = 821.02) 1-15 m / z = 651.27 (C ₄₈ H ₃₃ N ₃ = 651.80) 1-16 m / z = 642.21 (C ₄₆ H ₃₀ N ₂ S = 642.81) 1-17 m / z = 668.23 (C ₄₈ H ₃₂ N ₂ S = 668.85) 1-18 m / z = 668.23 (C ₄₈ H ₃₂ N ₂ S = 668.85) 1-19 m / z = 692.23 (C ₅₀ H ₃₂ N ₂ S = 692.87) 1-20 m / z = 708.26 (C ₅₁ H ₃₆ N ₂ S = 708.91) 1-21 m / z = 794.28 (C ₅₈ H ₃₈ N ₂ S = 795.00) 1-22 m / z = 698.19 (C ₄₈ H ₃₀ N ₂ S ₂ = 698.90) 1-23 m / z = 652.25 (C ₄₈ H ₃₂ N ₂ O = 652.78) 1-24 m / z = 778.30 (C ₅₈ H ₃₈ N ₂ O = 778.94) 1-25 m / z = 753.28 (C ₅₅ H ₃₅ N ₃ O = 753.89) 1-26 m / z = 666.23 (C ₄₈ H ₃₀ N ₂ O ₂ = 666.76) 1-27 m / z = 682.21 (C ₄₈ H ₃₀ N ₂ OS = 682.83) 1-28 m / z = 682.21 (C ₄₈ H ₃₀ N ₂ OS = 682.83) 1-29 m / z = 678.30 (C ₅₁ H ₃₈ N ₂ = 678.86) 1-30 m / z = 702.30 (C ₅₃ H ₃₈ N ₂ = 702.88) 1-31 m / z = 692.28 (C ₅₁ H ₃₆ N ₂ O = 692.84) 1-32 m / z = 708.26 (C ₅₁ H ₃₆ N ₂ S = 708.91) 1-33 m / z = 794.37 (C ₆₀ H ₄₆ N ₂ = 795.02) 1-34 m / z = 802.33 (C ₆₁ H ₄₂ N ₂ = 803.00) 1-35 m / z = 879.36 (C ₆₆ H ₄₅ N ₃ = 880.08) 1-36 m / z = 842.37 (C ₆₄ H ₄₆ N ₂ = 843.06) 1-37 m / z = 832.29 (C ₆₁ H ₄₀ N ₂ S = 833.05) 1-38 m / z = 724.29 (C ₅₅ H ₃₆ N ₂ = 724.89) 1-39 m / z = 800.32 (C ₆₁ H ₄₀ N ₂ = 800.98) 1-40 m / z = 840.35 (C ₆₄ H ₄₄ N ₂ = 841.05) 1-41 m / z = 830.28 (C ₆₁ H ₃₈ N ₂ S = 831.03) 1-42 m / z = 814.30 (C ₆₁ H ₃₈ N ₂ O = 814.97) 1-43 m / z = 638.27 (C ₄₈ H ₃₄ N ₂ = 638.80) 1-44 m / z = 803.33 (C ₆₀ H ₄₁ N ₃ = 803.99) 1-45 m / z = 638.27 (C ₄₈ H ₃₄ N ₂ = 638.80) 1-46 m / z = 668.23 (C ₄₈ H ₃₂ N ₂ S = 668.85) 1-47 m / z = 678.30 (C ₅₁ H ₃₈ N ₂ = 678.86) 1-48 m / z = 835.30 (C ₆₀ H ₄₁ N ₃ S = 836.05) 1-49 m / z = 682.21 (C ₄₈ H ₃₀ N ₂ OS = 682.83) 1-50 m / z = 668.23 (C ₄₈ H ₃₂ N ₂ S = 668.85) 1-51 m / z = 612.26 (C ₄₆ H ₃₂ N ₂ = 612.76) 1-52 m / z = 638.27 (C ₄₈ H ₃₄ N ₂ = 638.80) 1-53 m / z = 782.24 (C ₅₆ H ₃₄ N ₂ OS = 782.95) 1-54 m / z = 790.33 (C ₆₀ H ₄₂ N ₂ = 790.99) 1-55 m / z = 805.31 (C ₅₉ H ₃₉ N ₃ O = 805.96) 1-56 _{m / z = 664.29 (C 50} H 36 N 2 = 664.83) 1-57 m / z = 803.33 (C ₆₀ H ₄₁ N ₃ = 803.99) 1-58 m / z = 768.26 (C ₅₆ H ₃₆ N ₂ S = 768.96) 1-59 m / z = 650.27 (C ₄₉ H ₃₄ N ₂ = 650.81) 1-60 m / z = 688.29 (C ₅₂ H ₃₆ N ₂ = 688.86) 1-61 m / z = 744.26 (C ₅₄ H ₃₆ N ₂ S = 744.94) 1-62 m / z = 667.21 (C ₄₇ H ₂₉ N ₃ S = 667.82) 1-63 m / z = 642.21 (C ₄₆ H ₃₀ N ₂ S = 642.81) 1-64 m / z = 566.18 (C ₄₀ H ₂₆ N ₂ S = 566.71) 1-65 m / z = 699.18 (C ₄₇ H ₂₉ N ₃ S ₂ = 699.88) 1-66 m / z = 682.21 (C ₄₈ H ₃₀ N ₂ OS = 682.83) 1-67 m / z = 742.24 (C ₅₄ H ₃₄ N ₂ S = 742.93) 1-68 m / z = 652.25 (C ₄₈ H ₃₂ N ₂ O = 652.78) 1-69 m / z = 652.25 (C ₄₈ H ₃₂ N ₂ O = 652.78) 1-70 m / z = 678.30 (C ₅₁ H ₃₈ N ₂ = 678.86) 1-71 m / z = 657.32 (C ₄₉ H ₃₁ D ₅ N ₂ = 657.85) 1-72 m / z = 576.26 (C ₄₃ H ₃₂ N ₂ = 576.73) 1-73 m / z = 642.30 (C ₄₈ H ₃₈ N ₂ = 642.83) 1-74 m / z = 766.33 (C ₅₈ H ₄₂ N ₂ = 766.97) 1-75 m / z = 767.33 (C ₅₇ H ₄₁ N ₃ = 767.96) 1-76 m / z = 708.26 (C ₅₁ H ₃₆ N ₂ S = 708.91) 1-77 m / z = 692.28 (C ₅₁ H ₃₆ N ₂ O = 692.84) 1-78 m / z = 706.26 (C ₅₁ H ₃₄ N ₂ O ₂ = 706.83) 1-79 m / z = 722.24 (C ₅₁ H ₃₄ N ₂ OS = 722.89) 1-80 m / z = 666.27 (C ₄₉ H ₃₄ N ₂ O = 666.81) 1-81 m / z = 603.27 (C ₄₄ H ₃₃ N ₃ = 603.75) 1-82 m / z = 778.33 (C ₅₉ H ₄₂ N ₂ = 778.98) 1-83 m / z = 755.33 (C ₅₆ H ₄₁ N ₃ = 755.94) 1-84 m / z = 802.33 (C ₆₁ H ₄₂ N ₂ = 803.00) 1-85 m / z = 778.31 (C ₅₇ H ₃₈ N ₄ = 778.94) 1-86 m / z = 890.37 (C ₆₈ H ₄₆ N ₂ = 891.11) 1-87 m / z = 756.26 (C ₅₅ H ₃₆ N ₂ S = 756.95) 1-88 m / z = 846.27 (C ₆₁ H ₃₈ N ₂ OS = 847.03) 1-89 m / z = 776.32 (C ₅₉ H ₄₀ N ₂ = 776.96) 1-90 m / z = 648.26 (C ₄₉ H ₃₂ N ₂ = 648.79) 1-91 m / z = 800.32 (C ₆₁ H ₄₀ N ₂ = 800.98) 1-92 m / z = 830.28 (C ₆₁ H ₃₈ N ₂ S = 831.03) 1-93 m / z = 864.31 (C ₆₅ H ₄₀ N ₂ O = 865.03) 1-94 m / z = 840.35 (C ₆₄ H ₄₄ N ₂ = 841.05) 1-95 m / z = 936.35 (C ₇₂ H ₄₄ N ₂ = 937.13) 1-96 m / z = 844.25 (C ₆₁ H ₃₆ N ₂ OS = 845.02) 1-97 m / z = 927.36 (C ₇₀ H ₄₅ N ₃ = 928.13) 1-98 m / z = 688.29 (C ₅₂ H ₃₆ N ₂ = 688.86) 1-99 m / z = 652.29 (C ₄₉ H ₃₆ N ₂ = 652.82) 1-100 m / z = 826.33 (C ₆₃ H ₄₂ N ₂ = 827.02) 1-101 m / z = 702.27 (C ₅₂ H ₃₄ N ₂ O = 702.84) 1-102 m / z = 688.29 (C ₅₂ H ₃₆ N ₂ = 688.86) 1-103 m / z = 728.32 (C ₅₅ H ₄₀ N ₂ = 728.92) 1-104 m / z = 884.29 (C ₆₄ H ₄₀ N ₂ OS = 885.08) 1-105 m / z = 586.24 (C ₄₄ H ₃₀ N ₂ = 586.72) 1-106 m / z = 718.24 (C ₅₂ H ₃₄ N ₂ S = 718.90) 1-107 m / z = 732.22 (C ₅₂ H ₃₂ N ₂ OS = 732.89) 1-108 m / z = 702.30 (C ₅₃ H ₃₈ N ₂ = 702.88) 1-109 m / z = 688.29 (C ₅₂ H ₃₆ N ₂ = 688.86) 1-110 m / z = 702.27 (C ₅₂ H ₃₄ N ₂ O = 702.84) 1-111 m / z = 692.23 (C ₅₀ H ₃₂ N ₂ S = 692.87) 1-112 m / z = 782.24 (C ₅₆ H ₃₄ N ₂ OS = 782.95) 1-113 m / z = 738.30 (C ₅₆ H ₃₈ N ₂ = 738.91) 1-114 m / z = 768.26 (C ₅₆ H ₃₆ N ₂ S = 768.96) 1-115 m / z = 716.32 (C ₅₄ H ₄₀ N ₂ = 716.91) 1-116 m / z = 857.29 (C ₆₂ H ₃₉ N ₃ S = 858.06) 1-117 m / z = 738.30 (C ₅₆ H ₃₈ N ₂ = 738.91) 1-118 m / z = 753.28 (C ₅₅ H ₃₅ N ₃ O = 753.89) 1-119 m / z = 677.28 (C ₅₀ H ₃₅ N ₃ = 677.83) 1-120 m / z = 879.32 (C ₆₅ H ₄₁ N ₃ O = 880.04) 1-121 m / z = 612.26 (C ₄₆ H ₃₂ N ₂ = 612.76) 1-122 m / z = 756.31 (C ₅₆ H ₄₀ N ₂ O = 756.93) 1-123 m / z = 727.30 (C ₅₄ H ₃₇ N ₃ = 727.89) 1-124 m / z = 866.37 (C ₆₆ H ₄₆ N ₂ = 867.08)

II. Synthesis of Formula 2

The compounds of formula (2) according to the present invention are synthesized using the following reaction scheme 31 and scheme 32, but are not limited thereto.

<Reaction Scheme 31>

When h is an integer of 2 or more and L ⁸ is not a single bond

In Reaction Formula 31 and Reaction Formula 32, Ar ³ to Ar ⁶ , L ⁴ to L ^8, and d to h are the same as defined in Formula 2 above. Hal ² is Br or Cl.

In Scheme 32, z is an integer from 1 to 4. (Note that the difference hz between h and z is an integer of 1 or more)

1. Synthesis of Sub 2

Sub 2 of Scheme 31 is synthesized in the same manner as Sub 2 of Scheme 1, as shown in the reaction path of Scheme 33 below.

<Reaction Scheme 33>

A is Ar ¹ , Ar ³ , Ar ⁵ ; B is Ar ² , Ar ⁴ , Ar ⁶ ; C is (L ² ) _b , (L ⁴ ) _d , (L ⁶ ) _f ; D is (L ³ ) _c , (L ⁵ ) _e , (L ⁷ ) _g ; Hal ² = Br or Cl

2. Synthesis of Sub 3

The above Reaction Scheme 31 and Sub 3 of Scheme 32 can be synthesized by the reaction path of the following reaction scheme 34, but are not limited thereto.

<Reaction formula 34>

Hal ¹ is I or Br; Hal ² is Br or Cl

Examples of the synthesis of specific compounds belonging to Sub 3 are as follows.

(1) Sub 3-1 Synthesis Example

<Reaction Scheme 35>

2-bromo-6-iodonaphthalene (59.03 g, 177.3 mmol) and Pd ₂ (dba) ₃ (3.25 g, 3.5 mmol) were dissolved in toluene (740 ml) mmol), 50% P ( t- Bu) ₃ (4.6 ml, 9.5 mmol) and NaO t- Bu (34.08 g, 354.6 mmol) were added and stirred at 70 ° C. After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 30.08 g (yield: 68%) of the product.

(2) Sub 3-9 Synthetic Example

<Reaction Formula 36>

Sub2-1 (20 g, 118.2 mmol), 4-bromo-4'-iodo-1,1'-biphenyl (63.64 g, 177.3 mmol), Pd ₂ (dba) ₃ (3.25 g, _{% P (t -Bu) 3 (} 4.6 ml, 9.5 mmol), NaO t -Bu (34.08 g, 354.6 mmol), 30.75 product using a toluene (740 ml) the Sub 3-1 synthesis g (yield: 65 %).

(3) Sub 3-10 Synthetic Example

(Reaction Scheme 37)

Sub 2-3 (25 g, 114 mmol ), 4-bromo-4'-iodo-1,1'-biphenyl (61.39 g, 171 mmol), Pd 2 (dba) 3 (3.13 g, 3.4 mmol), 50 (32.87 g, 342 mmol) and toluene (715 ml) were reacted with 33.89 g (Yield: 66%) of the product P ( t- Bu) ₃ (4.4 ml, 9.1 mmol), NaO t- %).

(4) Sub 3-45 Synthetic Example

<Reaction Formula 38>

Sub 2-40 (20 g, 72.6 mmol ), 4-bromo-4'-iodo-1,1'-biphenyl (39.11 g, 108.9 mmol), Pd 2 (dba) 3 (2 g, 2.2 mmol), 50 24.65 g (Yield: 67%) of the product was obtained by using the above Sub 3-1 synthesis method using ₂ % P ( t- Bu) ₃ (2.8 ml, 5.8 mmol), NaO t- Bu (20.94 g, 217.9 mmol) %).

(5) Sub 3-61 Synthetic Example

<Reaction Scheme 39>

Sub-2-76 (20 g, 51.9 mmol), 4-bromo-4'-iodo-1,1'-biphenyl (27.94 g, 77.8 mmol), Pd ₂ (dba) ₃ (1.43 g, 20.15 g (Yield: 63%) of the product was obtained by using the above Sub 3-1 synthesis method using 2% (Pd ( t- Bu) ₃ (2 ml, 4.2 mmol), NaO t- Bu (14.96 g, 155.7 mmol) %).

(6) Sub 3-79 Synthesis Example

<Reaction formula 40>

Sub2-113 (20 g, 59.8 mmol), 4-bromo-4'-iodo-1,1'-biphenyl (32.21 g, 89.7 mmol), Pd ₂ (dba) ₃ (1.64 g, 20.63 g (Yield: 61%) of the product was obtained by using the above Sub 3-1 synthesis method using ₃ % (Pd ( t- Bu) ₃ (2.3 ml, 4.8 mmol), NaO t- Bu (17.24 g, 179.4 mmol) %).

(7) Sub 3-85 Synthesis Example

<Reaction Scheme 41>

Sub 2-3 (20 g, 91.2 mmol ), 3,7-dibromodibenzo [b, d] thiophene (46.8 g, 136.8 mmol), Pd 2 (dba) 3 (2.51 g, 2.7 mmol), 50% P (t 28.04 g (Yield: 64%) of the product was obtained by using the above Sub 3-1 synthesis method using _3- chloro- _3- nitrobenzoic acid (3.6 ml, 7.3 mmol), NaO t- Bu (26.3 g, 273.6 mmol) .

On the other hand, the compounds belonging to Sub 3 may be, but not limited to, the following compounds, and Table 4 shows FD-MS values of the compounds belonging to Sub 3.

compound FD-MS compound FD-MS Sub 3-1 _{m / z = 373.05 (C 22} H 16 BrN = 374.27) Sub 3-2 m / z = 575.12 (C ₃₈ H ₂₆ BrN = 576.52) Sub 3-3 _{m / z = 473.08 (C 30} H 20 BrN = 474.39) Sub 3-4 m / z = 549.11 (C ₃₆ H ₂₄ BrN = 550.49) Sub 3-5 m / z = 625.14 (C ₄₂ H ₂₈ BrN = 626.58) Sub 3-6 m / z = 725.17 (C ₅₀ H ₃₂ BrN = 726.70) Sub 3-7 m / z = 503.12 (C ₃₂ H ₂₆ BrN = 504.46) Sub 3-8 m / z = 497.08 (C ₃₂ H ₂₀ BrN = 498.41) Sub 3-9 m / z = 399.06 (C ₂₄ H ₁₈ BrN = 400.31) Sub 3-10 _{m / z = 449.08 (C 28} H 20 BrN = 450.37) Sub 3-11 m / z = 499.09 (C ₃₂ H ₂₂ BrN = 500.43) Sub 3-12 _{m / z = 475.09 (C 30} H 22 BrN = 476.41) Sub 3-13 _{m / z = 480.12 (C 30} H 17 D 5 BrN = 481.44) Sub 3-14 _{m / z = 525.11 (C 34} H 24 BrN = 526.47) Sub 3-15 m / z = 575.12 (C ₃₈ H ₂₆ BrN = 576.52) Sub 3-16 m / z = 499.09 (C ₃₂ H ₂₂ BrN = 500.43) Sub 3-17 m / z = 551.12 (C ₃₆ H ₂₆ BrN = 552.50) Sub 3-18 m / z = 523.09 (C ₃₄ H ₂₂ BrN = 524.45) Sub 3-19 m / z = 551.12 (C ₃₆ H ₂₆ BrN = 552.50) Sub 3-20 m / z = 616.15 (C ₄₀ H ₂₉ BrN ₂ = 617.58) Sub 3-21 _{m / z = 480.12 (C 30} H 17 D 5 BrN = 481.44) Sub 3-22 _{m / z = 449.08 (C 28} H 20 BrN = 450.37) Sub 3-23 m / z = 499.09 (C ₃₂ H ₂₂ BrN = 500.43) Sub 3-24 m / z = 499.09 (C ₃₂ H ₂₂ BrN = 500.43) Sub 3-25 m / z = 499.09 (C ₃₂ H ₂₂ BrN = 500.43) Sub 3-26 _{m / z = 475.09 (C 30} H 22 BrN = 476.41) Sub 3-27 _{m / z = 525.11 (C 34} H 24 BrN = 526.47) Sub 3-28 _{m / z = 525.11 (C 34} H 24 BrN = 526.47) Sub 3-29 _{m / z = 525.11 (C 34} H 24 BrN = 526.47) Sub 3-30 _{m / z = 525.11 (C 34} H 24 BrN = 526.47) Sub 3-31 m / z = 627.16 (C ₄₂ H ₃₀ BrN = 628.60) Sub 3-32 _{m / z = 525.11 (C 34} H 24 BrN = 526.47) Sub 3-33 _{m / z = 525.11 (C 34} H 24 BrN = 526.47) Sub 3-34 _{m / z = 525.11 (C 34} H 24 BrN = 526.47) Sub 3-35 _{m / z = 489.07 (C 30} H 20 BrNO = 490.39) Sub 3-36 m / z = 627.16 (C ₄₂ H ₃₀ BrN = 628.60) Sub 3-37 m / z = 555.07 (C ₃₄ H ₂₂ BrNS = 556.51) Sub 3-38 m / z = 657.11 (C ₄₂ H ₂₈ BrNS = 658.65) Sub 3-39 m / z = 591.16 (C ₃₉ H ₃₀ BrN = 592.57) Sub 3-40 m / z = 631.19 (C ₄₂ H ₃₄ BrN = 632.63) Sub 3-41 m / z = 538.10 (C ₃₄ H ₂₃ BrN ₂ = 539.46) Sub 3-42 m / z = 740.18 (C ₅₀ H ₃₃ BrN ₂ = 741.71) Sub 3-43 m / z = 765.17 (C ₅₂ H ₃₂ BrNO = 766.72) Sub 3-44 m / z = 787.10 (C ₅₀ H ₃₀ BrNS ₂ = 788.81) Sub 3-45 m / z = 505.05 (C ₃₀ H ₂₀ BrNS 506.46 =) Sub 3-46 m / z = 555.07 (C ₃₄ H ₂₂ BrNS = 556.51) Sub 3-47 m / z = 581.08 (C ₃₆ H ₂₄ BrNS 582.55 =) Sub 3-48 m / z = 505.05 (C ₃₀ H ₂₀ BrNS 506.46 =) Sub 3-49 m / z = 581.08 (C ₃₆ H ₂₄ BrNS 582.55 =) Sub 3-50 _{m / z = 611.04 (C 36} H 22 BrNS 2 = 612.60) Sub 3-51 m / z = 631.10 (C ₄₀ H ₂₆ BrNS = 632.61) Sub 3-52 m / z = 581.08 (C ₃₆ H ₂₄ BrNS 582.55 =) Sub 3-53 m / z = 555.07 (C ₃₄ H ₂₂ BrNS = 556.51) Sub 3-54 m / z = 581.08 (C ₃₆ H ₂₄ BrNS 582.55 =) Sub 3-55 m / z = 581.08 (C ₃₆ H ₂₄ BrNS 582.55 =) Sub 3-56 m / z = 631.10 (C ₄₀ H ₂₆ BrNS = 632.61) Sub 3-57 m / z = 581.08 (C ₃₆ H ₂₄ BrNS 582.55 =) Sub 3-58 _{m / z = 489.07 (C 30} H 20 BrNO = 490.39) Sub 3-59 m / z = 539.09 (C ₃₄ H ₂₂ BrNO = 540.45) Sub 3-60 _{m / z = 489.07 (C 30} H 20 BrNO = 490.39) Sub 3-61 m / z = 615.12 (C ₄₀ H ₂₆ BrNO = 616.54) Sub 3-62 _{m / z = 565.10 (C 36} H 24 BrNO = 566.49) Sub 3-63 m / z = 615.12 (C ₄₀ H ₂₆ BrNO = 616.54) Sub 3-64 m / z = 641.14 (C ₄₂ H ₂₈ BrNO = 642.58) Sub 3-65 m / z = 615.12 (C ₄₀ H ₂₆ BrNO = 616.54) Sub 3-66 m / z = 565.14 (C ₃₇ H ₂₈ BrN = 566.53) Sub 3-67 m / z = 591.16 (C ₃₉ H ₃₀ BrN = 592.57) Sub 3-68 m / z = 631.19 (C ₄₂ H ₃₄ BrN = 632.63) Sub 3-69 m / z = 639.16 (C ₄₃ H ₃₀ BrN = 640.61) Sub 3-70 m / z = 653.17 (C ₄₄ H ₃₂ BrN = 654.64) Sub 3-71 m / z = 639.16 (C ₄₃ H ₃₀ BrN = 640.61) Sub 3-72 m / z = 715.19 (C ₄₉ H ₃₄ BrN = 716.70) Sub 3-73 m / z = 665.17 (C ₄₅ H ₃₂ BrN = 666.65) Sub 3-74 m / z = 692.18 (C ₄₆ H ₃₃ BrN ₂ = 693.67) Sub 3-75 _{m / z = 564.12 (C 36} H 25 BrN 2 = 565.50) Sub 3-76 m / z = 614.14 (C ₄₀ H ₂₇ BrN ₂ = 615.56) Sub 3-77 m / z = 680.18 (C ₄₅ H ₃₃ BrN ₂ = 681.66) Sub 3-78 m / z = 614.14 (C ₄₀ H ₂₇ BrN ₂ = 615.56) Sub 3-79 _{m / z = 564.12 (C 36} H 25 BrN 2 = 565.50) Sub 3-80 _{m / z = 564.12 (C 36} H 25 BrN 2 = 565.50) Sub 3-81 _{m / z = 564.12 (C 36} H 25 BrN 2 = 565.50) Sub 3-82 m / z = 640.15 (C ₄₂ H ₂₉ BrN ₂ = 641.60) Sub 3-83 m / z = 690.17 (C ₄₆ H ₃₁ BrN ₂ = 691.66) Sub 3-84 _{m / z = 564.12 (C 36} H 25 BrN 2 = 565.50) Sub 3-85 m / z = 479.03 (C ₂₈ H ₁₈ BrNS 480.42 =) Sub 3-86 m / z = 479.03 (C ₂₈ H ₁₈ BrNS 480.42 =) Sub 3-87 m / z = 581.08 (C ₃₆ H ₂₄ BrNS 582.55 =) Sub 3-88 m / z = 594.08 (C ₃₆ H ₂₃ BrN ₂ S = 595.55) Sub 3-89 m / z = 544.06 (C ₃₂ H ₂₁ BrN ₂ S = 545.49) Sub 3-90 m / z = 479.03 (C ₂₈ H ₁₈ BrNS 480.42 =) Sub 3-91 _{m / z = 463.06 (C 28} H 18 BrNO = 464.35) Sub 3-92 m / z = 569.04 (C ₃₄ H ₂₀ BrNOS = 570.50) Sub 3-93 m / z = 538.10 (C ₃₄ H ₂₃ BrN ₂ = 539.46) Sub 3-94 m / z = 594.08 (C ₃₆ H ₂₃ BrN ₂ S = 595.55) Sub 3-95 m / z = 538.10 (C ₃₄ H ₂₃ BrN ₂ = 539.46) Sub 3-96 m / z = 555.07 (C ₃₄ H ₂₂ BrNS = 556.51) Sub 3-97 m / z = 605.08 (C ₃₈ H ₂₄ BrNS = 606.57) Sub 3-98 m / z = 539.09 (C ₃₄ H ₂₂ BrNO = 540.45) Sub 3-99 m / z = 681.20 (C ₄₆ H ₃₆ BrN = 682.69) Sub 3-100 m / z = 614.14 (C ₄₀ H ₂₇ BrN ₂ = 615.56) Sub 3-101 m / z = 640.15 (C ₄₂ H ₂₉ BrN ₂ = 641.60) Sub 3-102 m / z = 505.05 (C ₃₀ H ₂₀ BrNS 506.46 =) Sub 3-103 _{m / z = 611.04 (C 36} H 22 BrNS 2 = 612.60) Sub 3-104 _{m / z = 519.03 (C 30} H 18 BrNOS = 520.44) Sub 3-105 m / z = 595.10 (C ₃₇ H ₂₆ BrNS 596.58 =) Sub 3-106 _{m / z = 565.10 (C 36} H 24 BrNO = 566.49) Sub 3-107 m / z = 616.12 (C ₃₉ H ₂₅ BrN ₂ O = 617.53) Sub 3-108 m / z = 595.10 (C ₃₇ H ₂₆ BrNS 596.58 =) Sub 3-109 m / z = 566.14 (C ₃₆ H ₂₇ BrN ₂ = 567.52) Sub 3-110 _{m / z = 475.09 (C 30} H 22 BrN = 476.41) Sub 3-111 _{m / z = 523.04 (C 30} H 19 BrFNS = 524.45) Sub 3-112 m / z = 615.12 (C ₄₀ H ₂₆ BrNO = 616.54)

3. Product Synthesis

<Method 1>

(1.1 eq.), Pd ₂ (dba) ₃ (0.05 eq.), P (t-Bu) ₃ (0.1 eq.), NaO t -Bu (3.3 eq.) Was added and stirred at 100 &lt; 0 &gt; C. After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain final products.

<Method 2>

B (OH) ₂ (L ⁸ ) _z N ((L ⁶ ) _f Ar ⁵ ) ((L ⁷ ) _g Ar ⁶ ) (1 eq.) As the starting material was dissolved in toluene in a round bottom flask. Sub 3 equiv.), Pd (PPh _{3) 4} was added (0.05 eq), K ₂ CO ₃ (3 eq.), water, and the mixture was stirred at 90 ℃. After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain final products.

(1) 2-1 Synthesis Example

<Reaction Scheme 42>

Sub 3-1 (14.64 g, 32.5 mmol), Pd ₂ (dba) ₃ (1.35 g, 1.5 mmol) was added to the round bottom flask after dissolving Sub 2-1 (5 g, 29.5 mmol) 50% P ( t- Bu) ₃ (1.4 ml, 3 mmol) and NaO t- Bu (9.37 g, 97.5 mmol) were added and stirred at 100 ° C. After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 12.89 g of the product (yield: 81%).

(2) Synthesis Example 2-12

<Reaction Scheme 43>

Sub 2-113 (7 g, 20.9 mmol ), Sub 3-79 (13.02 g, 23 mmol), Pd 2 (dba) 3 (0.96 g, 1 mmol), 50% P (t -Bu) 3 (1 ml , 2.1 mmol), NaO t- Bu (6.64 g, 69.1 mmol) and toluene (220 ml) were used to obtain 13.2 g of the product (yield: 77%).

(3) 2-50 Synthetic Example

<Reaction Scheme 44>

Sub-3-1 (15.89 g, 42.5 mmol) and Pd (PPh) were prepared by dissolving (6- (diphenylamino) naphthalen-2-yl) boronic acid (12 g, 35.4 mmol) ₃ ) ₄ (2.04 g, 1.8 mmol), K ₂ CO ₃ (14.67 g, 106.1 mmol) and water (70 ml) were added and stirred at 90 ° C. After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 12.29 g (yield: 59%) of the product.

(4) 2-51 Synthesis Example

<Reaction Scheme 45>

(4 '- (diphenylamino) - [1,1'-biphenyl] -4-yl) boronic acid (12 g, 32.9 mmol) in Sub 3-9 (15.78 g, 39.4 mmol ), Pd (PPh 3) 4 ( 11.37 g (Yield: 54%) of the product was obtained using the above 2-50 synthesis method, 1.9 g, 1.6 mmol), K ₂ CO ₃ (13.62 g, 98.6 mmol), toluene (120 ml) and water (60 ml).

(5) 2-78 Synthesis Example

<Reaction Formula 46>

Sub 2-96 (10 g, 21.8 mmol ), Sub 3-10 (10.78 g, 23.9 mmol), Pd 2 (dba) 3 (1 g, 1.1 mmol), 50% P (t -Bu) 3 (1.1 ml , 2.2 mmol), NaO t- Bu (6.9 g, 71.8 mmol) and toluene (230 ml) were used to synthesize 13.17 g (yield: 73%) of the product.

(6) 2-95 Synthetic Example

<Reaction Scheme 47>

Sub 2-40 (7 g, 25.4 mmol ), Sub 3-45 (14.16 g, 28 mmol), Pd 2 (dba) 3 (1.16 g, 1.3 mmol), 50% P (t -Bu) 3 (1.2 ml , 2.5 mmol), NaO t- Bu (8.06 g, 83.9 mmol) and toluene (270 ml) were used to synthesize 13.54 g of the product (yield: 76%).

(7) 2-103 Synthesis Example

<Reaction Scheme 48>

Sub 2-76 (7 g, 18.2 mmol ), Sub 3-61 (12.32 g, 20 mmol), Pd 2 (dba) 3 (0.83 g, 0.9 mmol), 50% P (t -Bu) 3 (0.9 ml , 1.2 mmol), NaO t- Bu (5.76 g, 59.9 mmol) and toluene (190 ml) were used to synthesize 12.04 g (yield: 72%) of the product.

(8) 2-130 Synthesis Example

<Reaction Scheme 49>

Sub 2-26 (7 g, 21.8 mmol ), Sub 3-85 (11.51 g, 24 mmol), Pd 2 (dba) 3 (1 g, 1.1 mmol), 50% P (t -Bu) 3 (1.1 ml , 2.2 mmol), NaO t- Bu (6.91 g, 71.9 mmol) and toluene (230 ml) were used to obtain the product 12.25 g (yield: 78%).

Meanwhile, FD-MS values of the compounds 2-1 to 2-140 of the present invention prepared according to the above synthesis examples are shown in Table 5 below.

compound FD-MS compound FD-MS 2-1 m / z = 538.24 (C ₄₀ H ₃₀ N ₂ = 538.68) 2-2 m / z = 588.26 (C ₄₄ H ₃₂ N ₂ = 588.74) 2-3 m / z = 688.29 (C ₅₂ H ₃₆ N ₂ = 688.86) 2-4 m / z = 736.29 (C ₅₆ H ₃₆ N ₂ = 736.90) 2-5 m / z = 640.29 (C ₄₈ H ₃₆ N ₂ = 640.81) 2-6 m / z = 691.30 (C ₅₁ H ₃₇ N ₃ = 691.86) 2-7 _{m / z = 694.24 (C 50} H 34 N 2 S = 694.88) 2-8 m / z = 753.31 (C ₅₆ H ₃₉ N ₃ = 753.93) 2-9 m / z = 730.30 (C ₅₄ H ₃₈ N ₂ O = 730.89) 2-10 m / z = 818.34 (C ₆₀ H ₄₂ N ₄ = 819.00) 2-11 m / z = 918.37 (C ₆₈ H ₄₆ N ₄ = 919.12) 2-12 m / z = 818.34 (C ₆₀ H ₄₂ N ₄ = 819.00) 2-13 m / z = 668.25 (C ₄₈ H ₃₂ N ₂ O ₂ = 668.78) 2-14 m / z = 700.20 (C ₄₈ H ₃₂ N ₂ S ₂ = 700.91) 2-15 m / z = 818.34 (C ₆₀ H ₄₂ N ₄ = 819.00) 2-16 m / z = 818.34 (C ₆₀ H ₄₂ N ₄ = 819.00) 2-17 m / z = 618.21 (C ₄₄ H ₃₀ N ₂ S = 618.79) 2-18 m / z = 618.21 (C ₄₄ H ₃₀ N ₂ S = 618.79) 2-19 m / z = 848.30 (C ₆₀ H ₄₀ N ₄ S = 849.05) 2-20 m / z = 618.21 (C ₄₄ H ₃₀ N ₂ S = 618.79) 2-21 m / z = 677.28 (C ₅₀ H ₃₅ N ₃ = 677.83) 2-22 m / z = 627.27 (C ₄₆ H ₃₃ N ₃ = 627.77) 2-23 m / z = 602.24 (C ₄₄ H ₃₀ N ₂ O = 602.72) 2-24 m / z = 564.26 (C ₄₂ H ₃₂ N ₂ = 564.72) 2-25 _{m / z = 664.29 (C 50} H 36 N 2 = 664.83) 2-26 m / z = 776.23 (C ₅₄ H ₃₆ N ₂ S ₂ = 777.01) 2-27 m / z = 744.28 (C ₅₄ H ₃₆ N ₂ O ₂ = 744.88) 2-28 m / z = 894.37 (C ₆₆ H ₄₆ N ₄ = 895.10) 2-29 m / z = 881.38 (C ₆₆ H ₄₇ N ₃ = 882.10) 2-30 m / z = 764.32 (C ₅₈ H ₄₀ N ₂ = 764.95) 2-31 m / z = 864.35 (C ₆₆ H ₄₄ N ₂ = 865.07) 2-32 m / z = 994.40 (C ₇₄ H ₅₀ N ₄ = 995.22) 2-33 m / z = 876.26 (C ₆₂ H ₄₀ N ₂ S ₂ = 877.12) 2-34 m / z = 648.35 (C ₄₈ H ₄₄ N ₂ = 648.88) 2-35 m / z = 636.26 (C ₄₈ H ₃₂ N ₂ = 636.78) 2-36 m / z = 792.33 (C ₅₈ H ₄₀ N ₄ = 792.96) 2-37 m / z = 538.24 (C ₄₀ H ₃₀ N ₂ = 538.68) 2-38 m / z = 612.26 (C ₄₆ H ₃₂ N ₂ = 612.76) 2-39 m / z = 764.32 (C ₅₈ H ₄₀ N ₂ = 764.95) 2-40 _{m / z = 694.24 (C 50} H 34 N 2 S = 694.88) 2-41 m / z = 678.27 (C ₅₀ H ₃₄ N ₂ O = 678.82) 2-42 m / z = 703.30 (C ₅₂ H ₃₇ N ₃ = 703.87) 2-43 _{m / z = 664.29 (C 50} H 36 N 2 = 664.83) 2-44 _{m / z = 664.29 (C 50} H 36 N 2 = 664.83) 2-45 m / z = 588.26 (C ₄₄ H ₃₂ N ₂ = 588.74) 2-46 _{m / z = 694.24 (C 50} H 34 N 2 S = 694.88) 2-47 m / z = 588.26 (C ₄₄ H ₃₂ N ₂ = 588.74) 2-48 m / z = 944.34 (C ₇₀ H ₄₄ N ₂ O ₂ = 945.11) 2-49 m / z = 866.37 (C ₆₆ H ₄₆ N ₂ = 867.08) 2-50 m / z = 588.26 (C ₄₄ H ₃₂ N ₂ = 588.74) 2-51 m / z = 640.29 (C ₄₈ H ₃₆ N ₂ = 640.81) 2-52 m / z = 789.23 (C ₅₄ H ₃₅ N ₃ S ₂ = 790.01) 2-53 m / z = 814.21 (C ₅₆ H ₃₄ N ₂ OS ₂ = 815.01) 2-54 m / z = 744.26 (C ₅₄ H ₃₆ N ₂ S = 744.94) 2-55 m / z = 918.37 (C ₆₈ H ₄₆ N ₄ = 919.12) 2-56 m / z = 800.23 (C ₅₆ H ₃₆ N ₂ S ₂ = 801.03) 2-57 m / z = 818.34 (C ₆₀ H ₄₂ N ₄ = 819.00) 2-58 m / z = 748.27 (C ₅₂ H ₃₆ N ₄ S = 748.93) 2-59 m / z = 744.28 (C ₅₄ H ₃₆ N ₂ O ₂ = 744.88) 2-60 m / z = 792.35 (C ₆₀ H ₄₄ N ₂ = 793.00) 2-61 m / z = 690.30 (C ₅₂ H ₃₈ N ₂ = 690.87) 2-62 m / z = 790.33 (C ₆₀ H ₄₂ N ₂ = 790.99) 2-63 m / z = 740.32 (C ₅₆ H ₄₀ N ₂ = 740.93) 2-64 m / z = 840.35 (C ₆₄ H ₄₄ N ₂ = 841.05) 2-65 m / z = 691.30 (C ₅₁ H ₃₇ N ₃ = 691.86) 2-66 m / z = 688.29 (C ₅₂ H ₃₆ N ₂ = 688.86) 2-67 m / z = 700.37 (C ₅₂ H ₂₈ D ₁₀ N ₂ = 700.93) 2-68 m / z = 650.35 (C ₄₈ H ₂₆ D ₁₀ N ₂ = 650.87) 2-69 m / z = 922.40 (C ₆₈ H ₅₀ N ₄ = 923.15) 2-70 m / z = 730.33 (C ₅₅ H ₄₂ N ₂ = 730.94) 2-71 m / z = 832.38 (C ₆₃ H ₄₈ N ₂ = 833.07) 2-72 m / z = 761.38 (C ₅₇ H ₃₉ D ₅ N ₂ = 762.00) 2-73 m / z = 806.37 (C ₆₁ H ₄₆ N ₂ = 807.03) 2-74 m / z = 876.35 (C ₆₄ H ₄₈ N ₂ S = 877.14) 2-75 m / z = 872.41 (C ₆₆ H ₅₂ N ₂ = 873.13) 2-76 m / z = 770.37 (C ₅₈ H ₄₆ N ₂ = 771.00) 2-77 m / z = 952.48 (C ₇₂ H ₆₀ N ₂ = 953.26) 2-78 m / z = 828.35 (C ₆₃ H ₄₄ N ₂ = 829.04) 2-79 m / z = 910.34 (C ₆₇ H ₄₆ N ₂ S = 911.16) 2-80 m / z = 863.33 (C ₆₂ H ₄₅ N ₃ S = 864.11) 2-81 m / z = 804.35 (C ₆₁ H ₄₄ N ₂ = 805.02) 2-82 m / z = 970.39 (C ₇₃ H ₅₀ N ₂ O = 971.19) 2-83 m / z = 981.41 (C ₇₄ H ₅₁ N ₃ = 982.22) 2-84 m / z = 968.41 (C ₇₄ H ₅₂ N ₂ = 969.22) 2-85 m / z = 878.37 (C ₆₇ H ₄₆ N ₂ = 879.10) 2-86 m / z = 816.31 (C ₆₁ H ₄₀ N ₂ O = 816.98) 2-87 m / z = 805.35 (C ₆₀ H ₄₃ N ₃ = 806.00) 2-88 m / z = 885.32 (C ₆₄ H ₄₃ N ₃ S = 886.11) 2-89 m / z = 805.35 (C ₆₀ H ₄₃ N ₃ = 806.00) 2-90 m / z = 1050.47 (C ₇₈ H ₅₈ N ₄ = 1051.32) 2-91 _{m / z = 696.26 (C 50} H 36 N 2 S = 696.90) 2-92 _{m / z = 696.26 (C 50} H 36 N 2 S = 696.90) 2-93 m / z = 822.31 (C ₆₀ H ₄₂ N ₂ S = 823.05) 2-94 m / z = 746.28 (C ₅₄ H ₃₈ N ₂ S = 746.96) 2-95 m / z = 700.20 (C ₄₈ H ₃₂ N ₂ S ₂ = 700.91) 2-96 m / z = 800.23 (C ₅₆ H ₃₆ N ₂ S ₂ = 801.03) 2-97 m / z = 852.26 (C ₆₀ H ₄₀ N ₂ S ₂ = 853.10) 2-98 m / z = 952.29 (C ₆₈ H ₄₄ N ₂ S ₂ = 953.22) 2-99 m / z = 912.18 (C ₆₀ H ₃₆ N ₂ S ₄ = 913.20) 2-100 m / z = 852.26 (C ₆₀ H ₄₀ N ₂ S ₂ = 853.10) 2-101 m / z = 806.33 (C ₆₀ H ₄₂ N ₂ O = 806.99) 2-102 m / z = 768.28 (C ₅₆ H ₃₆ N ₂ O ₂ = 768.90) 2-103 m / z = 920.34 (C ₆₈ H ₄₄ N ₂ O ₂ = 921.09) 2-104 m / z = 684.22 (C ₄₈ H ₃₂ N ₂ OS = 684.85) 2-105 m / z = 970.43 (C ₇₄ H ₅₄ N ₂ = 971.23) 2-106 m / z = 947.42 (C ₇₁ H ₅₃ N ₃ = 948.20) 2-107 m / z = 829.35 (C ₆₂ H ₄₃ N ₃ = 830.02) 2-108 m / z = 860.29 (C ₆₂ H ₄₀ N ₂ OS = 861.06) 2-109 _{m / z = 664.29 (C 50} H 36 N 2 = 664.83) 2-110 m / z = 956.41 (C ₇₃ H ₅₂ N ₂ = 957.21) 2-111 m / z = 829.35 (C ₆₂ H ₄₃ N ₃ = 830.02) 2-112 m / z = 911.33 (C ₆₆ H ₄₅ N ₃ S = 912.15) 2-113 m / z = 776.23 (C ₅₄ H ₃₆ N ₂ S ₂ = 777.01) 2-114 _{m / z = 844.31 (C 62} H 40 N 2 O 2 = 844.99) 2-115 _{m / z = 664.29 (C 50} H 36 N 2 = 664.83) 2-116 _{m / z = 844.31 (C 62} H 40 N 2 O 2 = 844.99) 2-117 _{m / z = 664.29 (C 50} H 36 N 2 = 664.83) 2-118 _{m / z = 664.29 (C 50} H 36 N 2 = 664.83) 2-119 m / z = 774.27 (C ₅₅ H ₃₈ N ₂ OS = 774.97) 2-120 m / z = 731.33 (C ₅₄ H ₄₁ N ₃ = 731.92) 2-121 m / z = 670.24 (C ₄₈ H ₃₄ N ₂ S = 670.86) 2-122 m / z = 882.22 (C ₆₀ H ₃₈ N ₂ S ₃ = 883.15) 2-123 m / z = 698.20 (C ₄₈ H ₃₀ N ₂ O ₂ S = 698.83) 2-124 m / z = 850.34 (C ₆₂ H ₄₆ N ₂ S = 851.11) 2-125 m / z = 806.33 (C ₆₀ H ₄₂ N ₂ O = 806.99) 2-126 m / z = 782.30 (C ₅₆ H ₃₈ N ₄ O = 782.93) 2-127 m / z = 729.31 (C ₅₄ H ₃₉ N ₃ = 729.91) 2-128 m / z = 936.44 (C ₇₁ H ₅₆ N ₂ = 937.22) 2-129 m / z = 822.31 (C ₆₀ H ₄₂ N ₂ S = 823.05) 2-130 m / z = 720.26 (C ₅₂ H ₃₆ N ₂ S = 720.92) 2-131 m / z = 792.35 (C ₆₀ H ₄₄ N ₂ = 793.00) 2-132 m / z = 756.35 (C ₅₇ H ₄₄ N ₂ = 756.97) 2-133 m / z = 836.41 (C ₆₃ H ₅₂ N ₂ = 837.10) 2-134 _{m / z = 694.24 (C 50} H 34 N 2 S = 694.88) 2-135 m / z = 852.26 (C ₆₀ H ₄₀ N ₂ S ₂ = 853.10) 2-136 m / z = 820.31 (C ₆₀ H ₄₀ N ₂ O ₂ = 820.97) 2-137 m / z = 640.29 (C ₄₈ H ₃₆ N ₂ = 640.81) 2-138 m / z = 736.18 (C ₄₈ H ₃₀ F ₂ N ₂ S ₂ = 736.89) 2-139 m / z = 805.31 (C ₅₉ H ₃₉ N ₃ O = 805.96) 2-140 m / z = 868.38 (C ₆₆ H ₄₈ N ₂ = 869.10)

On the other hand, the above has been described in an illustrative synthesis of the present invention represented by Formula 1 and Formula 2, all of Suzuki cross-coupling reaction, PPh ₃ -mediated reductive cyclization reaction (J. Org. Chem. 2005, 70, 5014 (R ¹ , R ² , Ar ¹ to Ar ⁶ , L ¹ to L ⁸ , a to L ⁸ , and the like) defined in Chemical Formulas 1 and 2, in addition to the substituents specified in the specific Synthesis Examples. h, l, and m), the above reaction can be easily understood by those skilled in the art. For example, the starting material -> Sub 1-I reaction in Scheme 2 and the Sub 3 -> Final Products reaction in Scheme 32 are based on the Suzuki cross-coupling reaction and the Sub 1 -I -> Sub 1-II reaction in Scheme 2 PPh ₃ -mediated reductive cyclization reaction. Sub 1 -> Sub 1 reaction in Scheme 2, starting material -> Sub 2 reaction in Scheme 11 and Scheme 33, Sub 2 -> Sub 3 reaction in Scheme 34, Sub 1 -> Final Products reaction in Scheme 1 And in Scheme 31, the Sub 3 -> Final Products reaction is based on the Buchwald-Hartwig cross coupling reaction. Even if a substituent not specifically mentioned in these groups is bonded, the above reactions will proceed.

Evaluation of manufacturing of organic electric device

[Example 1] A blue organic electroluminescent device (hole transport layer)

An organic electroluminescent device was fabricated according to a conventional method using the compound of the present invention as a hole transport layer material.

First, 4,4 ', 4 "-tris [2-naphthyl (phenyl) amino] triphenylamine (hereinafter abbreviated as" 2-TNATA ") was deposited on the ITO layer (anode) (Compound A) of the present invention and the compound 2-2 (Compound B) of the present invention, which are the mixture of the present invention, were deposited on the hole injection layer by vacuum deposition to a thickness of 60 nm To form a hole transporting layer. Subsequently, a light-emitting layer with a thickness of 30 nm was deposited on the hole transport layer by doping 9,10-di (naphthalen-2-yl) anthracene on the hole transport layer and BD-052X (Idemitsu kosan) . Subsequently, aluminum (1,1-bisphenyl) -4-oleato) bis (2-methyl-8-quinolinolato) aluminum forming a blocking layer, and a tris (8-quinolinol) aluminum (hereinafter referred to as "Alq _3" abbreviated as) on the hole blocking layer to form an electron transport layer was vacuum deposited to a thickness of 40 nm. Thereafter, LiF as an alkali metal halide was deposited to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode. Thus, an organic electroluminescent device was manufactured.

[Examples 2 to 54] Blue organic electroluminescent device (hole transport layer)

The same procedure as in Example 1 was carried out except that one of the mixtures of the present invention described in the following Table 6 was used instead of the compound of the present invention 1-9 as the mixture of the present invention and the compound 2-2 of the present invention as the hole transport layer material To prepare an organic electroluminescent device.

[Comparative Example 1]

As a hole transport layer material, organic electroluminescent devices were produced in the same manner as in Example 1, except that the compound 1-9 of the present invention, which was a mixture of the present invention, and the compound 1-9 of the present invention were used alone instead of the compound 2-2 of the present invention Thereby preparing a light emitting device.

[Comparative Example 2]

As a hole transport layer material, organic electroluminescent devices were prepared in the same manner as in Example 1, except that the compound of the present invention 1-33 was used instead of the compounds 1-9 of the present invention and the compound 1-2-2 of the present invention, Thereby preparing a light emitting device.

[Comparative Example 3]

As a hole transport layer material, organic electroluminescent devices were produced in the same manner as in Example 1, except that the compound of the present invention 2-2 was used alone instead of the compound of the present invention 1-9 of the present invention and the present compound 2-2. Thereby preparing a light emitting device.

[Comparative Example 4]

As a hole transport layer material, organic electroluminescent devices were prepared in the same manner as in Example 1, except that the compound of the present invention 1-13 was used alone instead of the compounds of the present invention 1-9 and 2-2 of the present invention, Thereby preparing a light emitting device.

[Comparative Example 5]

The same procedure as in Example 1 was repeated except that the compound of the present invention 1-9 and the compound of the present invention 2-2 were used alone as the hole transport layer material, Thereby preparing a light emitting device.

Electruminescence (EL) characteristics were measured with a photoresearch PR-650 by applying a forward bias DC voltage to the organic electroluminescent devices manufactured in Examples 1 to 45 and Comparative Examples 1 to 5 of the present invention And the T95 lifetime was measured using a life measuring apparatus manufactured by Mac Science Inc. at a reference luminance of 500 cd / m ^2. The measurement results are shown in Table 6 below.

Mixing ratio Compound A Compound B Driving
Voltage (V) electric current
(mA / cm ₂ ) Luminance
(cd / m ₂ ) efficiency
(cd / A) Luminous color T (95) Comparative Example (1) Single compound compound
1-9 none 4.7 10.0 500 5.0 blue 98.6 Comparative Example (2) Single compound compound
1-23 none 4.7 11.4 500 4.4 blue 94.9 Comparative Example (3) Single compound compound
2-2 none 4.5 15.2 500 3.3 blue 83.1 Comparative Example (4) Single compound compound
2-13 none 4.6 9.8 500 5.1 blue 97.4 Comparative Example (5) Single compound compound
2-95 none 4.6 10.2 500 4.9 blue 95.9 Example (1) A (2): B (8) compound
1-9 compound
2-2 4.5 9.3 500 5.4 blue 103.8 Example (2) A (2): B (8) compound
1-9 compound
2-7 4.6 8.5 500 5.8 blue 106.4 Example (3) A (2): B (8) compound
1-9 compound
2-13 4.5 8.5 500 5.9 blue 107.8 Example (4) A (2): B (8) compound
1-9 compound
2-23 4.5 9.4 500 5.3 blue 107.7 Example (5) A (2): B (8) compound
1-9 compound
2-56 4.6 8.6 500 5.8 blue 107.2 Example (6) A (2): B (8) compound
1-9 compound
2-60 4.5 8.0 500 6.3 blue 107.7 Example (7) A (2): B (8) compound
1-9 compound
2-61 4.6 8.0 500 6.2 blue 107.5 Example (8) A (2): B (8) compound
1-9 compound
2-67 4.6 9.4 500 5.3 blue 103.8 Example (9) A (2): B (8) compound
1-9 compound
2-78 4.6 9.6 500 5.2 blue 104.5 Example (10) A (2): B (8) compound
1-9 compound
2-95 4.5 8.1 500 6.2 blue 108.3 Example (11) A (2): B (8) compound
1-9 compound
2-103 4.5 9.4 500 5.3 blue 102.3 Example (12) A (2): B (8) compound
1-9 compound
2-129 4.6 9.6 500 5.2 blue 107.2 Example (13) A (3): B (7) compound
1-9 compound
2-2 4.5 8.2 500 6.1 blue 116.1 Example (14) A (3): B (7) compound
1-9 compound
2-13 4.6 7.9 500 6.3 blue 117.5 Example (15) A (3): B (7) compound
1-9 compound
2-60 4.6 7.5 500 6.6 blue 122.2 Example (16) A (3): B (7) compound
1-9 compound
2-61 4.6 7.5 500 6.6 blue 123.4 Example (17) A (3): B (7) compound
1-9 compound
2-78 4.6 8.2 500 6.1 blue 116.9 Example (18) A (3): B (7) compound
1-9 compound
2-95 4.6 7.6 500 6.6 blue 123.7 Example (19) A (4): B (6) compound
1-9 compound
2-2 4.6 8.1 500 6.2 blue 117.6 Example (20) A (4): B (6) compound
1-9 compound
2-13 4.5 7.6 500 6.6 blue 119.0 Example (21) A (4): B (6) compound
1-9 compound
2-60 4.5 7.3 500 6.8 blue 125.6 Example (22) A (4): B (6) compound
1-9 compound
2-61 4.5 7.3 500 6.8 blue 125.7 Example (23) A (4): B (6) compound
1-9 compound
2-78 4.6 8.1 500 6.2 blue 117.3 Example (24) A (4): B (6) compound
1-9 compound
2-95 4.6 7.3 500 6.9 blue 125.1 Example (25) A (5): B (5) compound
1-9 compound
2-2 4.5 7.9 500 6.3 blue 123.6 Example (26) A (5): B (5) compound
1-9 compound
2-13 4.5 7.4 500 6.7 blue 126.7 Example (27) A (5): B (5) compound
1-9 compound
2-60 4.5 7.0 500 7.1 blue 129.2 Example (28) A (5): B (5) compound
1-9 compound
2-61 4.6 7.0 500 7.1 blue 130.0 Example (29) A (5): B (5) compound
1-9 compound
2-78 4.5 7.9 500 6.4 blue 123.8 Example (30) A (5): B (5) compound
1-9 compound
2-95 4.6 6.9 500 7.2 blue 130.2 Example (31) A (7): B (3) compound
1-9 compound
2-2 4.7 8.5 500 5.9 blue 106.6 Example (32) A (7): B (3) compound
1-9 compound
2-13 4.6 8.2 500 6.1 blue 108.6 Example (33) A (7): B (3) compound
1-9 compound
2-60 4.6 8.1 500 6.1 blue 108.5 Example (34) A (7): B (3) compound
1-9 compound
2-61 4.5 8.2 500 6.1 blue 107.1 Example (35) A (7): B (3) compound
1-9 compound
2-78 4.6 8.6 500 5.8 blue 106.6 Example (36) A (7): B (3) compound
1-9 compound
2-95 4.6 8.3 500 6.0 blue 109.2 Example (37) A (5): B (5) compound
1-23 compound
2-2 4.6 7.3 500 6.8 blue 126.6 Example (38) A (5): B (5) compound
1-23 compound
2-9 4.5 7.1 500 7.1 blue 129.4 Example (39) A (5): B (5) compound
1-23 compound
2-13 4.5 7.1 500 7.0 blue 129.3 Example (40) A (5): B (5) compound
1-23 compound
2-60 4.6 6.9 500 7.3 blue 135.5 Example (41) A (5): B (5) compound
1-23 compound
2-61 4.6 6.9 500 7.3 blue 135.6 Example (42) A (5): B (5) compound
1-23 compound
2-67 4.7 7.3 500 6.8 blue 127.0 Example (43) A (5): B (5) compound
1-23 compound
2-78 4.6 7.3 500 6.9 blue 126.8 Example (44) A (5): B (5) compound
1-23 compound
2-93 4.5 6.9 500 7.2 blue 129.1 Example (45) A (5): B (5) compound
1-23 compound
2-95 4.5 6.8 500 7.4 blue 137.2

As can be seen from the results of Table 6, the organic electroluminescent device using the mixture of the present invention (the compound represented by the formula (1) and the compound represented by the formula (2)) as the hole transport layer material can be applied to organic electroluminescent It can be confirmed that the light emitting device exhibits higher efficiency and longer lifetime than Comparative Examples 1 to 5 which are light emitting devices.

First, the carbazole-based compound 1-9 in which all the amine substituents are substituted with an aryl group, biphenyl, and the compounds (2-2, 2-7, 2-13, 2 -23, 2-56, 2-60, 2-61, 2-67, 2-78, 2-95, 2-103 and 2-129) were mixed in a ratio of 2: 8 (mixing ratio) The efficiency and lifetime of Examples 1 to 12 were higher than those of Comparative Examples 1 to 5 using a single compound as a hole transport layer, and the driving voltage was decreased. For example, when a mixture of Compound 1-9 and Compound 2-95 is used as the hole transport layer, the efficiency is increased by 124% and the lifetime is increased by 110% when Compound 1-9, in which all the amine substituents are aryl groups, is used as the hole transport layer .

As a result of proceeding from Examples 1 to 45, it was found that when the mixing ratio was 5: 5, the highest efficiency was increased and the life was increased. When the mixing ratio was 5: 5, it can be confirmed that a mixture of the compound 1-23 containing a heterocycle (dibenzofuran) and the compound represented by the formula 2 shows the most improved result in efficiency and lifetime.

The foregoing description is merely illustrative of the present invention, and various modifications may be made without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed herein are intended to be illustrative rather than limiting, and the spirit and scope of the present invention is not limited by these embodiments. The scope of protection of the present invention should be construed according to the following claims, and all techniques within the scope of the same should be construed 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 (18)

A first electrode; A second electrode; And an organic layer disposed between the first electrode and the second electrode and including a hole transport layer and a light emitting layer including a light emitting compound,
The hole transport layer comprises a mixture of a carbazole compound and an aryldiamine compound, wherein the carbazole compound and the aryldiamine compound are different from each other in structure. The organic compound layer may be formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, Or a roll-to-roll process. A first electrode; A second electrode; And an organic layer disposed between the first electrode and the second electrode and including a light emitting layer including at least one hole transport layer and a light emitting compound,
Wherein the hole transport layer comprises a mixture of a compound represented by the following formula (1) and a compound represented by the following formula (2)
&Lt; Formula 1 >< EMI ID =

{In the above Chemical Formulas 1 and 2,
1) Ar ¹ to Ar ⁶ independently represent a C _{6 to} C ₆₀ aryl group; Heterocyclic group of _{O, N, S, C 2} ~ 60 containing at least one hetero atom of Si and P; A fluorenyl group; And a fused ring group of an aromatic ring of C _{6 to} C _{60 and} an aliphatic ring of C _{3 to} C ₆₀ ,
2) L ¹ to L ⁸ independently represent a single bond; An arylene group having _{6 to 60} carbon atoms; Heterocyclic group of O, N, S, Si and P of the divalent C _{2 ~ 60} containing at least one heteroatom; A fluorenylene group; And a divalent fused ring group of an aliphatic ring having _{3 to 60} carbon atoms and an aromatic ring having _{6 to 60} carbon atoms,
3) a to h are independently selected from integers of 1 to 4, and when each of these is an integer of 2 or more, L ¹ to L ⁸ are the same or different from each other,
4) R ¹ and R ² independently of one another are deuterium; Tritium; halogen; Cyano; A nitro group; An aryl group of _{6 to 60} carbon atoms; A fluorenyl group; Heterocyclic group of _{O, N, S, C 2} ~ 60 containing at least one hetero atom of Si and P; Fused ring group of an aromatic ring of C _{3 ~ 60} alicyclic and C _{6 ~ 60} of the; A C1 _{to C50} alkyl group; An alkenyl group having _{2 to 20} carbon atoms; An alkynyl group having _{2 to 20} carbon atoms; An alkoxyl group having _{1 to 30} carbon atoms; An aryloxy group having _{6 to 30} carbon atoms; And -L'-N (R ^a ) (R ^b ), wherein L 'is a single bond; An arylene group having _{6 to 60} carbon atoms; Heterocyclic group of O, N, S, Si and P of the divalent C _{2 ~ 60} containing at least one heteroatom; A fluorenylene group; And a divalent fused ring group of an aliphatic ring of C _{3 to} C _{60 and} an aromatic ring of C _{6 to} C ₆₀ , and R ^a and R ^b are each independently a C _{6 to} C ₆₀ aryl group; A fluorenyl group; Heterocyclic group of _{O, N, S, C 2} ~ 60 containing at least one hetero atom of Si and P; And selected from the group consisting of a fused ring of an aromatic ring of C _{3 ~ 60} alicyclic and C _{6 ~ 60} of or, or a plurality of R ¹ and R ² are adjacent R ¹ together, or R ² combine with each other to at least one to each other, if present (Provided that R ¹ and R ² which do not form a ring are the same as defined above),
5) l and m are independently selected from the integers of 0 to 4, and when each of these is an integer of 2 or more, R ¹ and R ² are the same or different from each other.
A heterocyclic group, a fused ring group, an alkyl group, an alkenyl group, an alkoxy group, and an aryloxy group, each of which is independently selected from the group consisting of a halogen, a silane group, a siloxane group, a boron group, a germanium group, a cyano group; a nitro ^{group; -L'-N (R a)} (R b); an alkyl group of _{C 1 ~ 20;; C 1} ~ 20 alkyl import of Im; C _{1 ~ 20} alkoxy group of C _{2 ~ 20} alkene group; alkynyl of _{C 2 ~ 20; C 6 ~} 20 aryl group; in the C _{6 ~ 20} substituted by deuterium aryl group; fluorene group; a heterocyclic group of C _{2 ~ 20;} a cycloalkyl group of C _{3 ~ 20} , An arylalkyl group having _{7 to 20} carbon atoms and an arylalkenyl group having _{8 to 20} carbon atoms, and these substituents may be further bonded to each other to form a ring, wherein the 'ring' It is those that have a fused ring consisting of a heterocyclic or a combination of C _{3 ~ 60} aliphatic ring or a C _{6 ~ 60} aromatic ring or C _{2 ~ 60} of, Saturated or unsaturated ring). The organic electroluminescent device according to claim 2, wherein the compound represented by Formula 1 is represented by Formula 1-2 or Formula 1-3.
&Lt; General Formula 1-2 >

In Formulas 1-2 to 1-3,
1) R ¹ , R ² , Ar ² , L ¹ to L ³ , a to c, l and m are the same as defined in claim 2,
A 2) X ¹ and X ² is "a, R ', R" independently represents S, O, or CR'R each independently C _{6 ~ 24} aryl group, C _{1 ~ 20} alkyl group, C _{2 ~ 20} of each other Alkenyl, C _1-20 alkoxy group, R 'and R "may combine to form a spy,
3) R ¹ to R ⁶ independently of one another are deuterium; Tritium; halogen; Cyano; A nitro group; An aryl group of _{6 to 60} carbon atoms; A fluorenyl group; Heterocyclic group of _{O, N, S, C 2} ~ 60 containing at least one hetero atom of Si and P; Fused ring group of an aromatic ring of C _{3 ~ 60} alicyclic and C _{6 ~ 60} of the; A C1 _{to C50} alkyl group; An alkenyl group having _{2 to 20} carbon atoms; An alkynyl group having _{2 to 20} carbon atoms; An alkoxyl group having _{1 to 30} carbon atoms; Or an aryloxy group having _{6 to 30} carbon atoms, or when a plurality of R ¹ to R ⁶ are present, adjacent R ^{1 s} , R ^{2 s} , R ^{3 s} , R ^{4 s} , R ^{5 s} , R ^{6 s} And may combine with each other to form at least one ring (provided that R ¹ to R ⁶ which do not form a ring are the same as defined above).
4) n and p are independently selected from the integers of 0 to 3, and when each of these is an integer of 2 or more, R ³ and R ⁵ are the same or different from each other,
5) o and q are independently selected from integers of 0 to 4, and when each of these is an integer of 2 or more, R ⁴ and R ⁶ are the same or different from each other. The organic electroluminescent device according to claim 2, wherein the formula (2) is represented by one of the following formulas (2-2) to (2-5).
&Lt; Formula 2-2 >< Formula 2-3 >

&Lt; Formula 2-4 >< Formula 2-5 >

In the above Chemical Formulas 2-2 to 2-5,
1) Ar ⁴ to Ar ⁶ , L ⁴ to L ⁸ , d to h are the same as defined in claim 2,
A 2) X ³ to X ⁶ is "a, R ', R" independently represents S, O, or CR'R each independently C _{6 ~ 24} aryl group, C _{1 ~ 20} alkyl group, C _{2 ~ 20} of each other Alkenyl, C _1-20 alkoxy group, R 'and R "may combine to form a spy,
3) R ⁷ to R ¹⁴ independently of one another are deuterium; Tritium; halogen; Cyano; A nitro group; An aryl group of _{6 to 60} carbon atoms; A fluorenyl group; Heterocyclic group of _{O, N, S, C 2} ~ 60 containing at least one hetero atom of Si and P; Fused ring group of an aromatic ring of C _{3 ~ 60} alicyclic and C _{6 ~ 60} of the; A C1 _{to C50} alkyl group; An alkenyl group having _{2 to 20} carbon atoms; An alkynyl group having _{2 to 20} carbon atoms; An alkoxyl group having _{1 to 30} carbon atoms; And each other selected from an aryloxy group the group consisting of a C _{6 ~ 30,} or, or if there is a plurality of R ⁷ to R ¹⁴ adjacent to R ⁷ each other, R ⁸ each other, each other R ^9, R ¹⁰ together, R ^12, R ¹³ together , R ¹⁴ with each other can be formed at least one collar connected to each other (note that, R ⁷ to R ¹⁴ do not form the ring are the same as defined above.)
4) r, t, v and x are independently selected from integers of 0 to 3, and when each of these is an integer of 2 or more, R ⁷ , R ⁹ , R ¹¹ and R ¹³ are the same as or different from each other,
5) s, u, w and y are independently selected from integers of 0 to 4, and when each of these is an integer of 2 or more, R ⁸ , R ¹⁰ , R ¹² and R ¹⁴ are the same or different from each other. The organic electroluminescent device according to claim 2, wherein the compound represented by Formula 1 is one of the following compounds.

The organic electroluminescent device according to claim 2, wherein the compound represented by Formula 2 is one of the following compounds.

The organic electroluminescent device according to claim 2, wherein Ar ¹ and Ar ² of the compound represented by the formula (1) and Ar ³ to Ar ⁶ of the compound represented by the formula (2) are both C _6-24 aryl groups. The organic electroluminescent device according to claim 2, wherein at least one of Ar ¹ and Ar ² of the compound represented by the formula (1) and Ar ³ to Ar ⁶ of the compound represented by the formula (2) is dibenzothiophene or dibenzofuran. The compound according to claim 2, wherein Ar ¹ and Ar ² in the compound represented by Formula 1 are all C _{6 to} C ₂₄ aryl groups, and at least one of Ar ³ to Ar ⁶ in the compound represented by Formula 2 is dibenzothiophene or dibenzofuran Wherein the organic electroluminescent element is a compound represented by formula The compound according to claim 2, wherein at least one of Ar ¹ and Ar ² of the compound represented by Formula (1) is dibenzothiophene or dibenzofuran, and Ar ³ to Ar ⁶ in the compound represented by Formula (2) are all C _{6 to} C ₂₄ aryl groups An organic electric device characterized by: The organic electroluminescent device according to claim 2, wherein the weight ratio of the compound represented by the general formula (1) is 10% to 90% when the compound represented by the general formula (1) is mixed with the compound represented by the general formula (2). The method according to claim 2, wherein when the compound represented by Formula 1 and the compound represented by Formula 2 are mixed, the mixing ratio is at least 5: 5 or 6: 4 or 7: 3 or 8: 2 or 9: Wherein the organic electroluminescent element is one organic electroluminescent element. The composition of claim 2, further comprising at least one compound selected from the group consisting of compounds represented by formula (1) and compounds represented by formula (2) in a mixture of the compound represented by formula (1) Wherein the organic electroluminescent element is a compound represented by formula The organic electroluminescent device according to claim 2, further comprising a light-emission-assisting layer between the hole transport layer and the light-emitting layer, the composition including a compound represented by the formula (1) and a compound represented by the formula (2). 3. The organic electroluminescent device according to claim 2, further comprising a light-efficiency-improvement layer formed on at least one surface of the one surface of the first electrode and the second electrode opposite to the organic material layer. The organic electroluminescent device according to claim 2, wherein the organic material layer is formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process or a roll-to-roll process. A display device including the organic electroluminescent device according to claim 2; And a controller for driving the display device. &Lt; / RTI &gt; 18. The electronic device according to claim 17, wherein the organic electronic device is one of an organic electroluminescent device, an organic solar cell, an organophotoreceptor, an organic transistor and an element for monochromatic or white illumination.

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