WO2018026197A1 - Compound for organic electric element, organic electric element using same, and electronic apparatus comprising same - Google Patents

Abstract

A mixture of compounds according to the present invention is used as a phosphorescent host material, thereby achieving the high light emitting efficiency and low driving voltage of an organic electric element; and providing an organic electric element capable of significantly improving element lifespan and an electronic apparatus employing the same.

Description

Compound for organic electric device, organic electric device using same and electronic device thereof

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

In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic electric element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. In this case, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electric device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.

The material used as the organic material layer in the organic electric element may be classified into a light emitting material and a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function.

In the case of polycyclic cyclic compounds containing heteroatoms, the difference in characteristics depending on the material structure is very large and applied to various layers as a material of an organic electric device. In particular, band gaps (HOMO, LUMO), electrical properties, chemical properties, and physical properties are different depending on the number of rings, the fused position, and the type and arrangement of heteroatoms. This has been going on.

As a representative example, Patent Documents 1 to 5 report the performance according to hetero type and arrangement, substituent type, fused position, etc. with respect to the 5-ring cyclic compound in the polycyclic cyclic compound.

[Patent Document 1]: US Patent 5843607

[Patent Document 2]: Japanese Patent Laid-Open No. 1999-162650

[Patent Document 3]: Korean Laid-Open Patent 2008-0085000

[Patent Document 4]: US Patent Publication 2010-0187977

[Patent Document 5]: Korean Laid-Open Patent 2011-0018340

[Patent Document 6]: Korean Laid-Open Patent 2009-0057711

Patent Literature 1 and Patent Literature 2 use indolocarbazole cores in which the heteroatoms in the 5-membered cyclic compound consist only of nitrogen (N), and report examples using an aryl group substituted or unsubstituted with N of indolocarbazole. have. However, in the case of the preceding invention 1, there is only a simple aryl group in which an alkyl group, an amino group, an alkoxy group, etc. are substituted or unsubstituted, and thus it is very insufficient to prove the substituent effect of the polycyclic cyclic compound, and only the use as a hole transport material is described. The use as a phosphorescent host material is not described.

PTLs 3 and 4 are substituted with pyridine, pyrimidine, triazine, etc. containing an aryl group and N in an indolocarbazole core having N heteroatoms in the same 5-membered cyclic compound as Patent Documents 1 and 2 Although the described compounds are described, only examples of use for phosphorescent green host materials are described, and no performance is described for other heterocyclic compounds substituted in the indolocarbazole core.

Patent Document 5 describes nitrogen (N), oxygen (O), sulfur (S), carbon, etc. as heteroatoms in the 5-ring cyclic compound, but in the performance measurement data, only the examples using the same isotype heteroatoms are present. The performance characteristics of the 5-membered cyclic compound containing hetero hetero atoms could not be confirmed.

Therefore, the above patent document does not describe a solution for low charge carrier mobility and low oxidative stability of the 5-ring cyclic compound including isotype heteroatoms.

When 5-cyclic cyclic molecules are generally stacked, they have strong electrical interactions with more adjacent π-electrons, which are closely related to charge carrier mobility, especially the NN-type homocyclic cyclic compounds. When the molecules are stacked, the order of intermolecular arrangement has an edge-to-face shape, whereas heterocyclic heterocyclic compounds having different heteroatoms have a pi-stacking structure in which molecular packing structures face each other in reverse directions. structure) has the face-to-face arrangement order between molecules. It has been reported that due to the steric effect of the substituents substituted on the asymmetrically arranged heteroatoms N, which is the cause of the lamination structure, it causes relatively high carrier mobility and high oxidative stability. ( Org. Lett. 2008, 10, 1199)

In Patent Document 6, examples of using as a fluorescent host material for various polycyclic cyclic compounds having 7 or more rings have been reported.

As described above, development of the fused position, the number of rings, the arrangement of heteroatoms, and the characteristics of the polycyclic cyclic compound have not been sufficiently developed.

In particular, in the phosphorescent organic EL device using the phosphorescent dopant material, the LUMO and HOMO levels of the host material have a great influence on the efficiency and the lifetime of the organic EL device. Is it possible to efficiently control electron and hole injection in the emission layer? This is because it is possible to prevent the decrease in efficiency and the lifespan due to charge balance control, dopant quenching, and light emission at the hole transport layer interface in the light emitting layer.

In the case of fluorescence and phosphorescence emitting materials, researches on increasing the efficiency and lifespan of organic electric devices using TADF (Thermal Activated Delayed Fluorescence) and Exciplex have been conducted. There is a lot of research going on.

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

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

As such, there are various factors that affect efficiency and lifespan depending on the way energy is transferred from the host material to the dopant material, and the energy transfer method differs depending on the material. This is not enough. Therefore, the development of new materials is continuously required, and in particular, the development of the host material of the light emitting layer is urgently required.

The present invention has been proposed to solve the problems of the phosphorescent host material as described above, the charge balance control, efficiency and lifetime in the light emitting layer by adjusting the HOMO level for the host material of the phosphorescent organic electroluminescent device comprising a phosphorescent dopant It is an object to provide a compound which can be improved, an organic electric element using the same, and an electronic device thereof.

The present invention combines a specific first host material with a specific second host material as a main component to control efficient hole injection in the light emitting layer of the phosphorescent organic electroluminescent device, thereby reducing the energy barrier between the light emitting layer and the adjacent layer. It is possible to maximize the charge balance in the light emitting layer to provide high efficiency and long life of the organic electric element.

The present invention provides an organic electroluminescent device comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes a light emitting layer, and the light emitting layer is represented by the following Chemical Formula 1. Provided is an organic electric device comprising a first host compound and a second host compound represented by the following Chemical Formula 2.

        Formula 1 Formula 2

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

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

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

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)

Hereinafter, with reference to the embodiment of the present invention will be described in detail. In describing the present invention, when it is determined that the detailed description of the related well-known configuration or function may obscure the gist of the present invention, the detailed description thereof will be omitted.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

As used herein, the term “heteroalkyl” means an alkyl including one or more heteroatoms unless otherwise indicated. As used herein, the term "heteroaryl group" or "heteroarylene group" means an aryl group or arylene group having 2 to 60 carbon atoms, each containing one or more heteroatoms, unless otherwise specified. It may include at least one of a single ring and multiple rings, and may be formed by combining adjacent functional groups.

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

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

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

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

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

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

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

Unless otherwise specified, the term "ether" as used herein is represented by -RO-R ', wherein R or R' are each independently of each other hydrogen, an alkyl group having 1 to 20 carbon atoms, It is an aryl group, a C3-C30 cycloalkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, or a combination thereof.

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

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

Herein, when a is an integer of 0, the substituent R ¹ is absent, when a is an integer of 1, one substituent R ¹ is bonded to any one of carbons forming the benzene ring, and a is an integer of 2 or 3 Are each bonded as follows, where R ¹ may be the same or different from each other, and when a is an integer from 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while the indication of hydrogen bonded to the carbon forming the benzene ring Is omitted.

Also, unless stated otherwise, the terms "ortho", "meta", "para" used in the present invention means the substitution position of all substituents, the ortho position is a substituent The position of represents a neighboring compound, for example, in the case of benzene means 1, 2 digits, and the meta (meta) position represents the next substitution position of the immediate substitution position and benzene is 1, 3 digits as an example The para position means 1 or 4 digits when benzene is used as the next substitution position of the meta position. A more detailed description of the substitution positions is as follows. Ortho- and meta- positions are non-linear types and para- positions are substituted by linear types. have.

[example of ortho-position]

[example of meta-location]

[example of para-position]

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

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

        Formula 1 Formula 2

{In Formula 1 and 2,

1) X ¹ is CR ^a R ^b or the following Chemical Formula 1-a,

  Formula 1-a

In Formula 1-a, the dotted line represents a bond from X ¹ ,

2) X ² and X ³ are independently of each other NL ³ -Ar ⁴ , O, S, CR ^a R ^b or the formula 1-a, wherein the dotted line in the formula 1-a is a bond from X ² or X ³ Indicates

3) R ^a and R ^b are independently of each other hydrogen; C ₆ -C ₆₀ aryl group; Fluorenyl groups; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; An alkyl group of C ₁ -C ₅₀ ; C ₂ -C ₂₀ Alkenyl group; It is selected from the group consisting of,

4) h and i are integers of 0 or 1, provided that h + i is 1 or more, where h or i is 0 means a direct bond,

5) Ar ¹ , Ar ² , Ar ³ and Ar ⁴ are each independently a C ₆ -C ₆₀ aryl group; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; Fluorenyl groups; A fused ring group of an aromatic ring of C ₆ -C ₆₀ and an aliphatic ring of C ₃ -C ₆₀ ; An alkyl group of C ₁ -C ₅₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; C ₆ -C ₃₀ aryloxy group; And -L ^a -N (R ^c ) (R ^d ); wherein L ^a is a single bond; C ₆ -C ₆₀ arylene group; fluorenylene group; O, N, S A C ₂ -C ₆₀ heterocyclic group including at least one hetero atom of Si and P, a fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ , and an aliphatic hydrocarbon group; is selected from the group consisting of, wherein R ^c and R ^d are independently an aryl group of c ₆ -C ₆₀ with each other; fluorene group; O, N, S, at least one heteroatom selected from the group consisting of Si and P Heterocyclic group containing C ₂ -C ₆₀ ; fused ring group of C ₃ -C ₆₀ aliphatic ring and C ₆ -C ₆₀ aromatic ring;

6) Ar ¹ and Ar ² may be bonded to each other to form a ring,

7) n is an integer of 1 or 2, when n is 2, two Ar ¹ is the same or different, and two Ar ² is the same or different,

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

9) a, b, c, e and g are each independently an integer from 0 to 10, d is an integer from 0 to 5, f is an integer from 0 to 2,

10) R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently hydrogen; heavy hydrogen; Tritium; halogen; Cyano group; Nitro group; C ₆ -C ₆₀ aryl group; Fluorenyl groups; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; An alkyl group of C ₁ -C ₅₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; C ₆ -C ₃₀ aryloxy group; And -L ^a -N (R ^c ) (R ^d ); or when a, b, c, d, e and g are 2 or more and f is 2, respectively, as a plurality Are the same or different, and a plurality of R ¹ or a plurality of R ² or a plurality of R ³ or a plurality of R ⁴ or a plurality of R ⁵ or a plurality of R ⁶ or a plurality of R ⁷ are bonded to each other Can be formed,

11) A, B, C, D, E and F are independently of each other an aryl group of C ₆ -C ₂₀ or a heterocyclic group of C ₂ -C ₂₀ ,

However, when both E and F is a substituted or unsubstituted C ₆ aryl group (phenyl group), f is an integer of 2, and R ⁶ may be bonded to each other to form a ring to form an aromatic or heterocyclic ring,

Here, the aryl group, fluorenyl group, arylene group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkoxy group, aryloxy group are each deuterium; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; -L ^a -N (R ^c ) (R ^d ); Import alkylthio of C ₁ -C _20; An alkoxyl group of C ₁ -C ₂₀ ; An alkyl group of C ₁ -C ₂₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; Aryl group of C ₆ -C ₂₀ ; C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl groups; C ₂ -C ₂₀ heterocyclic group; A cycloalkyl group of C ₃ -C ₂₀ ; C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of, and these substituents may be bonded to each other to form a ring, wherein the “ring” means 3 to 60 carbon atoms. Fused ring consisting of an aliphatic ring or an aromatic ring having 6 to 60 carbon atoms or a hetero ring having 2 to 60 carbon atoms or a combination thereof, and includes a saturated or unsaturated ring.}

In addition, the present invention provides a compound represented by Chemical Formulas 1 and 2.

In addition, L ¹ , L ^2, and L ³ of Formulas 1 and 2 provide organic electroluminescent devices, wherein the compound is any one of Formulas A-1 to A-13.

A-1 A-2 A-3 A-4 A-5 A-6

 A-7 A-8 A-9 A-10

A-11 A-12 A-13

{In Chemical Formulas A-1 to A-13,

1) Y is NL ⁴ -Ar ⁵ , O, S, CR ^e R ^f or the following Chemical Formula 1-b,

Formula 1-b

In Formula 1-b, the dotted line represents a bond from Y,

2) L ⁴ is the same as the definition of L ³ ,

3) Ar ⁵ is the same as the definition of Ar ⁴ ,

4) R ^e and R ^f are the same as defined above for R ^a ,

5) R ¹¹ and R ¹² are as defined for the R ^1,

6) G and H are the same as the definition of A above,

7) j and k are the same as the definition of a above,

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

9) R ⁸ , R ⁹ and R ¹⁰ are each independently hydrogen; heavy hydrogen; Tritium; halogen; Cyano group; Nitro group; C ₆ -C ₆₀ aryl group; Fluorenyl groups; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; An alkyl group of C ₁ -C ₅₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; C ₆ -C ₃₀ aryloxy group; And -L ^a -N (R ^c ) (R ^d ); or when a ', b', c ', d', e ', f' and g 'are 2 or more and h '' Is 2, each being the same or different from each other, and a plurality of R ⁸ or a plurality of R ⁹ or a plurality of R ¹⁰ or a neighboring R ⁸ and R ⁹ or R ⁹ and R ¹⁰ are bonded to each other aromatic Can form a ring or a heteroaromatic ring,

10) L ^a is the same as the definition of L ^a , R ^c and R ^d are the same as the definition of R ^c and R ^d ,

11) Z ¹ , Z ² and Z ³ are independently of each other CR ¹³ or N, at least one of Z ¹ , Z ² and Z ³ is N,

12) R ¹³ is hydrogen; heavy hydrogen; Tritium; halogen; Cyano group; Nitro group; C ₆ -C ₆₀ aryl group; Fluorenyl groups; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; An alkyl group of C ₁ -C ₅₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; C ₆ -C ₃₀ aryloxy group; And -L ^a -N (R ^c ) (R ^d ); and adjacent R ⁸ and R ¹³ may combine with each other to form an aromatic ring or a heteroaromatic ring.}

In another aspect, the present invention provides an organic electroluminescent device comprising a compound wherein the first host compound represented by Formula 1 is any one of the following Formula 1-1 to Formula 1-5.

Chemical Formula 1-1 Chemical Formula 1-2 Chemical Formula 1-3

Formula 1-4 Formula 1-5

{In Formula 1-1 to Formula 1-5,

1) X ^1, C, D, R ^3, R ^4, c, d, Ar ¹ and Ar ² are as defined above,

2) Y is NL ⁴ -Ar ⁵ , O, S, CR ^e R ^f or the following Chemical Formula 1-b,

  Formula 1-b

In Formula 1-b, the dotted line represents a bond from Y,

3) L ⁴ are as defined in the L ^3,

4) Ar ⁵ is the same as the definition of Ar ⁴ ,

5) R ^e and R ^f are the same as defined above for R ^a ,

6) R ¹¹ and R ¹² are the same as defined above R ¹ ,

7) G and H are the same as the definition of A above,

8) j and k are the same as the definition of a above,

9) a ', c' and d 'are independently of each other an integer from 0 to 4, f' and g 'are independently of each other an integer from 0 to 3 and h' is an integer from 0 to 2,

10) R ⁸ and R ⁹ are independently of each other hydrogen; heavy hydrogen; Tritium; halogen; Cyano group; Nitro group; C ₆ -C ₆₀ aryl group; Fluorenyl groups; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; An alkyl group of C ₁ -C ₅₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; C ₆ -C ₃₀ aryloxy group; And -L ^a -N (R ^c ) (R ^d ); or when a ', c', d ', f' and g 'are 2 or more and h' is 2 A plurality of R ⁸ 's may be the same as or different from each other, and a plurality of R ^{8 s} or a plurality of R ^{9 s} or adjacent R ⁸ and R ⁹ may be bonded to each other to form an aromatic ring or a heteroaromatic ring.}

The present invention also includes a compound in which the first host compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-6 to 1-20.

    Chemical Formula 1-6 Chemical Formula 1-7 Chemical Formula 1-8

    Chemical Formula 1-9 Chemical Formula 1-10 Chemical Formula 1-11

    Chemical Formula 1-12 Chemical Formula 1-13 Chemical Formula 1-14

     Chemical Formula 1-15 Chemical Formula 1-16 Chemical Formula 1-17

    Formula 1-18 Formula 1-19 Formula 1-20

{In Chemical Formulas 1-6 to 1-20,

1) R ^a , R ^b , R ¹ , R ² , R ³ , R ⁴ , a, b, c, d, L ¹ , Ar ¹ , Ar ² and n are as defined above,

2) A, B, C and D are C ₁₀ aryl groups.}

In addition, the first host compound represented by Formula 1 of the present invention includes a compound represented by any one of the following formula 1-21 to formula 1-23.

   Chemical Formula 1-21 Chemical Formula 1-22 Chemical Formula 1-23

{In Formula 1-21 to Formula 1-23,

(1) C, D, R ³ , R ⁴ , c, d, L ¹ , Ar ¹ and Ar ² are as defined above,

(2) W is NL ⁵ -Ar ⁶ , O, S, CR ^g R ^h or the following Chemical Formula 1-c,

  Formula 1-c

In Formula 1-c, the dotted line represents a bond from W,

(3) L ⁵ are as defined in the L ^3, Ar ⁶ is the same as the definition of Ar ^4,

(4) R ^g and R ^h are the same as defined above for R ^a ,

(5) R ¹⁵ and R ¹⁶ are the same as defined above in R ¹ ,

(6) I and J are the same as the definition of A above,

(7) o and p are the same as the definition of a above,

(8) l is an integer of 0 to 3, m is an integer of 0 to 4,

(9) R ¹³ and R ¹⁴ are each independently hydrogen; heavy hydrogen; Tritium; halogen; Cyano group; Nitro group; C ₆ -C ₆₀ aryl group; Fluorenyl groups; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; An alkyl group of C ₁ -C ₅₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; C ₆ -C ₃₀ aryloxy group; And -L ^a -N (R ^c ) (R ^d ); and a plurality of R ¹³ or a plurality of R ¹⁴ or neighboring R ¹³ and R ¹⁴ are bonded to each other to form an aromatic ring or heteroaromatic. Can form a ring,

(10) L ^a is the same as the definition of L ^a , R ^c and R ^d are the same as the definition of R ^c and R ^d ,

(11) two Ar ² are each the same or different, two Ws are each the same or different, and a plurality of R ¹³ and a plurality of R ¹⁴ are the same or different from each other.

In addition, in one embodiment of the present invention, in the general formula (1) it provides an organic electroluminescent device comprising a compound when n is 1. In addition, in the general formula (1) provides an organic electric device comprising a compound when n is 2.

In one embodiment of the present invention, A, B, C, D, E and F provides an organic electric device comprising a compound represented by any one of the following formulas B-1 to B-7.

Chemical Formula B-1 Chemical Formula B-2 Chemical Formula B-3 Chemical Formula B-4

    Chemical Formula B-5 Chemical Formula B-6 Chemical Formula B-7

{In Formula B-1 to Formula B-7,

(1) Z ⁴ to Z ⁵¹ are CR ⁱ or N,

(2) R ⁱ is the same as defined above for R ^a ,

(3) * indicates the position to be condensed}

In another aspect, the present invention includes a compound in which the second host compound represented by Chemical Formula 2 is represented by the following Chemical Formula 3 or Chemical Formula 4.

      Formula 3 Formula 4

{In Chemical Formulas 3 and 4,

E, F, R ⁵ , R ⁶ , R ⁷ , e, f, g, L ² , Ar ³ , X ² and X ³ are as defined above.}

In another aspect, the present invention provides an organic electroluminescent device, characterized in that R ⁶ of Formula 2 necessarily forms an aromatic ring or heteroaromatic ring.

The present invention also includes a compound in which the second host compound represented by Formula 2 is represented by any one of the following Formulas 5-1 to 5-40.

   Chemical Formula 5-1 Chemical Formula 5-2 Chemical Formula 5-3 Chemical Formula 5-4

   Chemical Formula 5-5 Chemical Formula 5-6 Chemical Formula 5-7 Chemical Formula 5-8

    Chemical Formula 5-9 Chemical Formula 5-10 Chemical Formula 5-11 Chemical Formula 5-12

 Formula 5-13 Formula 5-14 Formula 5-15 Formula 5-16

  Formula 5-17 Formula 5-18 Formula 5-19 Formula 5-20

 Formula 5-21 Formula 5-22 Formula 5-23 Formula 5-24

 Chemical Formula 5-25 Chemical Formula 5-26 Chemical Formula 5-27 Chemical Formula 5-28

Formula 5-29 Formula 5-30 Formula 5-31 Formula 5-32

 Chemical Formula 5-33 Chemical Formula 5-34 Chemical Formula 5-35 Chemical Formula 5-36

Chemical Formula 5-37 Chemical Formula 5-38 Chemical Formula 5-39 Chemical Formula 5-40

{In Formula 5-1 to Formula 5-40,

(1) R ⁵ , R ⁶ , R ⁷ , e, f, g, L ² , Ar ³ , X ² and X ³ are as defined above,

(2) q is an integer of 0 to 4,

(3) R ¹⁷ is hydrogen; heavy hydrogen; Tritium; halogen; Cyano group; Nitro group; C ₆ -C ₆₀ aryl group; Fluorenyl groups; Heterocyclic group of _{O, N, S, C 2} -C 60 containing at least one heteroatom selected from the group consisting of Si and P; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; An alkyl group of C ₁ -C ₅₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; An aryloxy group of C ₆ -C ₃₀ ; and q is 2, each of which is the same or different from each other.}

The present invention, the second host compound represented by the formula (2) includes a compound selected from the group consisting of the following formulas 6-1 to 6-8.

  Chemical Formula 6-1 Chemical Formula 6-2 Chemical Formula 6-3 Chemical Formula 6-4

   Chemical Formula 6-5 Chemical Formula 6-6 Chemical Formula 6-7 Chemical Formula 6-8

{In Chemical Formulas 6-1 to 6-8,

E, F, R ⁵ , R ⁶ , R ⁷ , R ^a , R ^b , e, f, g, L ² , L ³ , Ar ³ and Ar ⁴ are as defined above.}

In the present invention, the first host compound represented by Chemical Formula 1 includes a compound represented by any one of the following Compounds 1-1 to 1-70 and Compounds 2-1 to 2-115.

In addition, in the present invention, the second host compound represented by Chemical Formula 2 includes a compound represented by any one of the following Compounds 3-1 to 3-115.

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

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

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

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

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

In addition, the light emitting auxiliary layer 151 may be further formed between the hole transport layer 140 and the light emitting layer 150, and an electron transport auxiliary layer may be further formed between the light emitting layer 150 and the electron transport layer 160.

In addition, at least one hole transport band layer between the first electrode and the light emitting layer, the hole transport band layer includes a hole transport layer, a light emitting auxiliary layer or both, the hole transport band layer is represented by Formula 1 It is possible to provide an organic electric device comprising a compound represented by.

Accordingly, the present invention provides an optical efficiency improvement layer formed on at least one side of the one side of the first electrode opposite to the organic material layer or one side of the second electrode opposite to the organic material layer in the organic electric device. It provides an organic electric element further comprising.

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

In another aspect, the present invention provides an organic electroluminescent device included in the light emitting layer by mixing the compound represented by Formula 1 and Formula 2 in any one ratio of 1: 9 to 9: 1 in the light emitting layer of the organic material layer.

In another aspect, the present invention provides an organic electroluminescent device, characterized in that the compound represented by the formula (1) and the formula (2) in the light emitting layer of the organic material layer is mixed in any one ratio of 1: 9 or 5: 5 used in the light emitting layer. . More preferably, the mixing ratio of the compound represented by Formula 1 and Formula 2 is included in the light emitting layer at 2: 8 or 3: 7.

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

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

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

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

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

[ Synthesis Example  One]

Compound represented by Formula 1 according to the present invention (final product 1) is synthesized by reacting Sub 1 and Sub 2, as shown in Scheme 1, but is not limited thereto. X ¹ , C, D, R ³ , R ⁴ , c, d, Ar ¹ , Ar ² , L ¹ and n are the same as defined in Formula 1 above, Hal ¹ is Br or Cl.

<Scheme 1>

I. Synthesis of Sub 1

The synthesis method for Sub 1 of Scheme 1 is Korean Patent Registration No. 10-1520955 (Registration date of May 11, 2015), Korean Patent Registration No. 10-1530885 (Registration date of June 17, 2015), Korea Patent Registration 10 of the applicant -1530886 (Registration date of June 17, 2015), Korea Patent Registration No. 10-1614740 (Registration date of April 18, 2016), Korea Application Patent 2013-0056221 (Application dated May 20, 2013), Korea Application Patent 2015-0035780 (2015.03 .16 dated), the Korean Patent Application 2015-0083505 (application dated June 12, 2015) was used in the synthesis method. When L ¹ is not a single bond, it may be synthesized by the reaction route of Scheme 2, but is not limited thereto, and Hal ¹ is Br or Cl.

<Scheme 2>

Synthesis examples of specific compounds belonging to Sub 1 are as follows.

Sub 1-26 Synthesis Example

(1) Sub 1-I-26 Synthesis

Sub 1-23 (CAS Registry Number: 171408-76-7) (38.80 g, 98.15 mmol) was dissolved in DMF (490 ml) in a round bottom flask, followed by Bis (pinacolato) diboron (27.42 g, 107.97 mmol), Pd (dppf) Cl ₂ (2.40 g, 2.94 mmol), KOAc (28.90 g, 294.46 mmol) was added and stirred at 90 ° C. After the reaction was completed, DMF was removed by distillation and extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ , concentrated and the resulting compound was silicagel column and recrystallized to give the product 32.13 g (yield: 74%).

(2) Sub 1-26 synthesis

Sub 1-I-26 (32.13 g, 72.63 mmol) obtained in the above synthesis was dissolved in THF (370 ml) in a round bottom flask, followed by 1,4-dibromobenzene (CAS Registry Number: 106-37-6) (22.27 g , 94.42 mmol), Pd (PPh ₃ ) ₄ (2.52 g, 2.18 mmol), NaOH (8.72 g, 217.89 mmol), water (185 ml) were added and stirred at 80 ° C. After the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was purified by silicagel column and recrystallized to give the product 23.97 g (yield: 70%).

2.Sub 1-73 Synthesis Example

(1) Synthesis of Sub 1-I-73

Sub 1-36 (CAS Registry Number: 1800333-62-3) (50.31 g, 125.49 mmol) in Bis (pinacolato) diboron (35.05 g, 138.04 mmol), Pd (dppf) Cl ₂ (3.07 g, 3.76 mmol), KOAc (36.95 g, 376.47 mmol), DMF (630 ml) were added and 37.69 g (yield: 61%) of product was obtained using the Sub 1-I-26 synthesis method.

(2) Sub 1-73 Synthesis

Sub 1-I-73 (37.69 g, 76.54 mmol) obtained in the above synthesis was converted into 1-bromo-2,4-dichlorobenzene (CAS Registry Number: 1193-72-2) (22.48 g, 99.50 mmol) and Pd (PPh _3). ) ₄ (2.65 g, 2.30 mmol), NaOH (9.18 g, 229.62 mmol), THF (390 ml), water (195 ml) was added and the product 24.66 g (yield: 63%) using the Sub 1-26 synthesis )

3.Sub 1-75 Synthesis Example

(1) Sub 1-I-75 Synthesis

Sub 1-63 (CAS Registry Number: 1793062-76-6) (46.40 g, 115.74 mmol) in Bis (pinacolato) diboron (32.33 g, 127.31 mmol), Pd (dppf) Cl ₂ (2.84 g, 3.47 mmol), KOAc (34.08 g, 347.21 mmol), DMF (580 ml) were added and 37.04 g (yield: 65%) of product was obtained using the Sub 1-I-26 synthesis method.

(2) Sub 1-75 Synthesis

Sub 1-I-75 (37.04 g, 75.22 mmol) obtained in the above synthesis was converted to 2,8-dibromodibenzo [b, d] thiophene (CAS Registry Number: 31574-87-5) (33.45 g, 97.78 mmol), Pd ( PPh ₃ ) ₄ (2.61 g, 2.26 mmol), NaOH (9.03 g, 225.66 mmol), THF (380 ml), water (190 ml) were added and the product 32.10 g (yield: 68%).

4.Sub 1-76 Synthesis Example

(1) Sub 1-I-76 Synthesis

Sub 1-46 (CAS Registry Number: 1800298-96-7) (39.31 g, 98.05 mmol) in Bis (pinacolato) diboron (27.39 g, 107.86 mmol), Pd (dppf) Cl ₂ (2.40 g, 2.94 mmol), KOAc (28.87 g, 294.16 mmol), DMF (490 ml) were added and the product 33.80 g (yield: 70%) was obtained using the Sub 1-I-26 synthesis method.

(2) Sub 1-76 Synthesis

2,7-dibromo-9,9-dimethyl-9H-fluorene (CAS Registry Number: 28320-32-3) (31.42 g, 89.23 mmol) in Sub 1-I-76 (33.80 g, 68.64 mmol) obtained in the above synthesis. ), Pd (PPh ₃ ) ₄ (2.38 g, 2.06 mmol), NaOH (8.24 g, 205.92 mmol), THF (350 ml), water (175 ml) were added and the product 28.89 was synthesized using the Sub 1-26 synthesis above. g (yield: 66%) was obtained.

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

compound	FD-MS	compound	FD-MS
Sub 1-1	m / z = 228.07 (C 15 H 13 Cl = 228.72)	Sub 1-2	m / z = 228.07 (C 15 H 13 Cl = 228.72)
Sub 1-3	m / z = 228.07 (C 15 H 13 Cl = 228.72)	Sub 1-4	m / z = 380.13 (C 27 H 21 Cl = 380.92)
Sub 1-5	m / z = 348.05 (C 21 H 17 Br = 349.27)	Sub 1-6	m / z 424.08 (C 27 H 21 Br = 425.37)
Sub 1-7	m / z = 500.11 (C 33 H 25 Br = 501.47)	Sub 1-8	m / z = 348.05 (C 21 H 17 Br = 349.27)
Sub 1-9	m / z = 500.11 (C 33 H 25 Br = 501.47)	Sub 1-10	m / z = 464.11 (C 30 H 25 Br = 465.43)
Sub 1-11	m / z = 448.08 (C 29 H 21 Br = 449.39)	Sub 1-12	m / z = 352.10 (C 25 H 17 Cl = 352.86)
Sub 1-13	m / z = 462.09 (C 31 H 20 Cl 2 = 463.40)	Sub 1-14	m / z = 352.10 (C 25 H 17 Cl = 352.86)
Sub 1-15	m / z = 352.10 (C 25 H 17 Cl = 352.86)	Sub 1-16	m / z = 402.12 (C29H19Cl = 402.92)
Sub 1-17	m / z = 352.10 (C 25 H 17 Cl = 352.86)	Sub 1-18	m / z = 472.08 (C 31 H 21 Br = 473.41)
Sub 1-19	m / z = 550.13 (C 37 H 27 Br = 551.53)	Sub 1-20	m / z = 548.11 (C 37 H 25 Br = 549.51)
Sub 1-21	m / z = 472.08 (C 31 H 21 Br = 473.41)	Sub 1-22	m / z = 585.09 (C 36 H 22 BrF 2 N = 586.48)
Sub 1-23	m / z = 394.04 (C 25 H 15 Br = 395.30)	Sub 1-24	m / z = 350.09 (C 25 H 15 Cl = 350.85)
Sub 1-25	m / z = 350.09 (C 25 H 15 Cl = 350.85)	Sub 1-26	m / z = 470.07 (C 31 H 19 Br = 471.40)
Sub 1-27	m / z = 470.07 (C 31 H 19 Br = 471.40)	Sub 1-28	m / z = 470.07 (C 31 H 19 Br = 471.40)
Sub 1-29	m / z = 470.07 (C 31 H 19 Br = 471.40)	Sub 1-30	m / z = 504.03 (C 31 H 18 BrCl = 505.84)
Sub 1-31	m / z = 470.07 (C 31 H 19 Br = 471.40)	Sub 1-32	m / z = 546.10 (C 37 H 23 Br = 547.50)
Sub 1-33	m / z = 400.10 (C 29 H 17 Cl = 400.91)	Sub 1-34	m / z = 476.13 (C 35 H 21 Cl = 477.00)
Sub 1-35	m / z = 400.10 (C 29 H 17 Cl = 400.91)	Sub 1-36	m / z = 400.10 (C 29 H 17 Cl = 400.91)
Sub 1-37	m / z = 400.10 (C 29 H 17 Cl = 400.91)	Sub 1-38	m / z = 400.10 (C 29 H 17 Cl = 400.91)
Sub 1-39	m / z = 400.10 (C 29 H 17 Cl = 400.91)	Sub 1-40	m / z = 400.10 (C 29 H 17 Cl = 400.91)
Sub 1-41	m / z = 478.12 (C 33 H 19 ClN 2 = 478.98)	Sub 1-42	m / z = 400.10 (C 29 H 17 Cl = 400.91)
Sub 1-43	m / z = 400.10 (C 29 H 17 Cl = 400.91)	Sub 1-44	m / z = 400.10 (C 29 H 17 Cl = 400.91)
Sub 1-45	m / z = 400.10 (C 29 H 17 Cl = 400.91)	Sub 1-46	m / z = 400.10 (C 29 H 17 Cl = 400.91)
Sub 1-47	m / z = 526.15 (C 39 H 23 Cl = 527.06)	Sub 1-48	m / z = 400.10 (C 29 H 17 Cl = 400.91)
Sub 1-49	m / z = 400.10 (C 29 H 17 Cl = 400.91)	Sub 1-50	m / z = 400.10 (C 29 H 17 Cl = 400.91)
Sub 1-51	m / z = 566.14 (C 41 H 23 ClO = 567.08)	Sub 1-52	m / z = 400.10 (C 29 H 17 Cl = 400.91)
Sub 1-53	m / z = 400.10 (C 29 H 17 Cl = 400.91)	Sub 1-54	m / z = 400.10 (C 29 H 17 Cl = 400.91)
Sub 1-55	m / z = 400.10 (C 29 H 17 Cl = 400.91)	Sub 1-56	m / z = 400.10 (C 29 H 17 Cl = 400.91)
Sub 1-57	m / z = 400.10 (C 29 H 17 Cl = 400.91)	Sub 1-58	m / z = 400.10 (C 29 H 17 Cl = 400.91)
Sub 1-59	m / z = 400.10 (C 29 H 17 Cl = 400.91)	Sub 1-60	m / z = 400.10 (C 29 H 17 Cl = 400.91)
Sub 1-61	m / z = 425.10 (C 30 H 16 ClN = 425.92)	Sub 1-62	m / z = 400.10 (C 29 H 17 Cl = 400.91)
Sub 1-63	m / z = 400.10 (C 29 H 17 Cl = 400.91)	Sub 1-64	m / z = 400.10 (C 29 H 17 Cl = 400.91)
Sub 1-65	m / z = 400.10 (C 29 H 17 Cl = 400.91)	Sub 1-66	m / z = 400.10 (C 29 H 17 Cl = 400.91)
Sub 1-67	m / z = 400.10 (C 29 H 17 Cl = 400.91)	Sub 1-68	m / z = 400.10 (C 29 H 17 Cl = 400.91)
Sub 1-69	m / z = 400.10 (C 29 H 17 Cl = 400.91)	Sub 1-70	m / z = 520.08 (C 35 H 21 Br = 521.46)
Sub 1-71	m / z = 520.08 (C 35 H 21 Br = 521.46)	Sub 1-72	m / z = 520.08 (C 35 H 21 Br = 521.46)
Sub 1-73	m / z = 510.09 (C 35 H 20 Cl 2 = 511.45)	Sub 1-74	m / z = 610.09 (C 41 H 23 BrO = 611.54)
Sub 1-75	m / z = 626.07 (C 41 H 23 BrS = 627.60)	Sub 1-76	m / z = 636.15 (C 44 H 29 Br = 637.62)
Sub 1-77	m / z = 450.12 (C 33 H 19 Cl = 450.97)	Sub 1-78	m / z = 450.12 (C 33 H 19 Cl = 450.97)
Sub 1-79	m / z = 500.13 (C 37 H 21 Cl = 501.03)	Sub 1-80	m / z = 450.12 (C 33 H 19 Cl = 450.97)
Sub 1-81	m / z = 450.12 (C 33 H 19 Cl = 450.97)	Sub 1-82	m / z = 670.13 (C 47 H 27 Br = 671.64)
Sub 1-83	m / z = 696.15 (C 49 H 29 Br = 697.68)	Sub 1-84	m / z = 772.15 (C 53 H 29 BrN 2 = 773.73)

II. Synthesis of Sub 2

The synthesis method for Sub 2 of Scheme 1 used the synthesis method disclosed in the applicant's Korean Patent No. 10-1251451 (Registration date of April 5, 2013). It may be synthesized by the reaction route of Scheme 3, but is not limited thereto.

<Scheme 3>

Synthesis examples of specific compounds belonging to Sub 2 are as follows.

Sub 2-11 Synthesis Example

The starting material 3-bromo-1,1'-biphenyl (CAS Registry Number: 2113-57-7) (10.99 g, 47.15 mmol) was dissolved in toluene (330 ml) in a round bottom flask, followed by naphthalen-2-amine (CAS Registry Number: 91-59-8) (7.43 g, 51.86 mmol), Pd ₂ (dba) ₃ (1.30 g, 1.41 mmol), P ( t -Bu) ₃ (0.76 g, 3.77 mmol), NaO t -Bu (13.59 g, 141.44 mmol) was added and stirred at 80 ° C. After the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was purified by silicagel column and recrystallized to give the product 11.14 g (yield: 80%).

2.Sub 2-17 Synthesis Example

[1,1'-biphenyl] -4-amine (CAS Registry Number: 92-67) to starting material 1- (4-bromophenyl) naphthalene (CAS Registry Number: 204530-94-9) (20.23 g, 71.44 mmol) -1) (13.30 g, 78.59 mmol), Pd ₂ (dba) ₃ (1.96 g, 2.14 mmol), P ( t -Bu) ₃ (1.16 g, 5.72 mmol), NaO t -Bu (20.60 g, 214.33 mmol ), toluene (500 ml) was added and the product 22.29 g (yield: 84%) was obtained using the Sub 2-11 synthesis.

3.Sub 2-35 Synthesis Example

4- (tert-butyl) aniline (CAS Registry Number: 769-92-6) in 2-chlorodibenzo [f, h] quinoline (CAS Registry Number: 1417779-49-7) (20.60 g, 78.11 mmol) as starting material (12.82 g, 85.92 mmol), Pd ₂ (dba) ₃ (2.15 g, 2.34 mmol), P ( t -Bu) ₃ (1.26 g, 6.25 mmol), NaO t -Bu (22.52 g, 234.34 mmol), toluene (550 ml) was added and 15.88 g (yield: 54%) of product was obtained using the Sub 2-11 synthesis.

4.Sub 2-82 Synthesis Example

[1,1'-biphenyl] -4-amine (CAS Registry Number: 92-) as starting material 2-bromodibenzo [b, d] furan (CAS Registry Number: 86-76-0) (15.52 g, 62.81 mmol) 67-1) (11.69 g, 69.09 mmol), Pd ₂ (dba) ₃ (1.73 g, 1.88 mmol), P ( t -Bu) ₃ (1.02 g, 5.02 mmol), NaO t -Bu (18.11 g, 188.43 mmol), toluene (440 ml) was added and 16.22 g (yield: 77%) of product was obtained using the Sub 2-11 synthesis.

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

compound	FD-MS	compound	FD-MS
Sub 2-1	m / z = 169.09 (C 12 H 11 N = 169.23)	Sub 2-2	m / z = 221.12 (C 16 H 15 N = 221.30)
Sub 2-3	m / z = 219.10 (C 16 H 13 N = 219.29)	Sub 2-4	m / z = 219.10 (C 16 H 13 N = 219.29)
Sub 2-5	m / z = 269.12 (C 20 H 15 N = 269.35)	Sub 2-6	m / z = 297.15 (C 22 H 19 N = 297.40)
Sub 2-7	m / z = 245.12 (C 18 H 15 N = 245.33)	Sub 2-8	m / z = 270.12 (C 19 H 14 N 2 = 270.34)
Sub 2-9	m / z = 295.14 (C 22 H 17 N = 295.39)	Sub 2-10	m / z = 300.17 (C 22 H 12 D 5 N = 300.42)
Sub 2-11	m / z = 295.14 (C 22 H 17 N = 295.39)	Sub 2-12	m / z = 295.14 (C 22 H 17 N = 295.39)
Sub 2-13	m / z = 295.14 (C 22 H 17 N = 295.39)	Sub 2-14	m / z = 321.15 (C 24 H 19 N = 321.42)
Sub 2-15	m / z = 326.18 (C 24 H 14 D 5 N = 326.45)	Sub 2-16	m / z = 349.18 (C 26 H 23 N = 349.48)
Sub 2-17	m / z = 371.17 (C 28 H 21 N = 371.48)	Sub 2-18	m / z = 421.18 (C 32 H 23 N = 421.54)
Sub 2-19	m / z = 421.18 (C 32 H 23 N = 421.54)	Sub 2-20	m / z = 421.18 (C 32 H 23 N = 421.54)
Sub 2-21	m / z = 421.18 (C 32 H 23 N = 421.54)	Sub 2-22	m / z = 397.18 (C 30 H 23 N = 397.52)
Sub 2-23	m / z = 397.18 (C 30 H 23 N = 397.52)	Sub 2-24	m / z = 473.21 (C 36 H 27 N = 473.62)
Sub 2-25	m / z = 269.12 (C 20 H 15 N = 269.35)	Sub 2-26	m / z = 341.16 (C 23 H 23 NSi = 341.53)
Sub 2-27	m / z = 345.15 (C 26 H 19 N = 345.45)	Sub 2-28	m / z = 319.14 (C 24 H 17 N = 319.41)
Sub 2-29	m / z = 167.07 (C 12 H 9 N = 167.21)	Sub 2-30	m / z = 293.12 (C 22 H 15 N = 293.37)
Sub 2-31	m / z = 329.20 (C 24 H 7 D 10 N = 329.47)	Sub 2-32	m / z = 220.10 (C 15 H 12 N 2 = 220.28)
Sub 2-33	m / z = 246.12 (C 17 H 14 N 2 = 246.31)	Sub 2-34	m / z = 220.10 (C 15 H 12 N 2 = 220.28)
Sub 2-35	m / z = 376.19 (C 27 H 24 N 2 = 376.50)	Sub 2-36	m / z = 285.15 (C 21 H 19 N = 285.39)
Sub 2-37	m / z = 335.17 (C 25 H 21 N = 335.45)	Sub 2-38	m / z = 335.17 (C 25 H 21 N = 335.45)
Sub 2-39	m / z = 361.18 (C 27 H 23 N = 361.49)	Sub 2-40	m / z = 375.20 (C 28 H 25 N = 375.52)
Sub 2-41	m / z = 366.21 (C 27 H 18 D 5 N = 366.52)	Sub 2-42	m / z = 361.18 (C 27 H 23 N = 361.49)
Sub 2-43	m / z = 361.18 (C 27 H 23 N = 361.49)	Sub 2-44	m / z = 411.20 (C 31 H 25 N = 411.55)
Sub 2-45	m / z = 411.20 (C 31 H 25 N = 411.55)	Sub 2-46	m / z = 411.20 (C 31 H 25 N = 411.55)
Sub 2-47	m / z = 437.21 (C 33 H 27 N = 437.59)	Sub 2-48	m / z = 513.25 (C 39 H 31 N = 513.68)
Sub 2-49	m / z = 437.21 (C 33 H 27 N = 437.59)	Sub 2-50	m / z = 385.18 (C 29 H 23 N = 385.51)
Sub 2-51	m / z = 401.21 (C 30 H 27 N = 401.55)	Sub 2-52	m / z = 411.20 (C 31 H 25 N = 411.55)
Sub 2-53	m / z = 361.18 (C 27 H 23 N = 361.49)	Sub 2-54	m / z = 335.17 (C 25 H 21 N = 335.45)
Sub 2-55	m / z = 335.17 (C 25 H 21 N = 335.45)	Sub 2-56	m / z = 361.18 (C 27 H 23 N = 361.49)
Sub 2-57	m / z = 411.20 (C 31 H 25 N = 411.55)	Sub 2-58	m / z = 361.18 (C 27 H 23 N = 361.49)
Sub 2-59	m / z = 361.18 (C 27 H 23 N = 361.49)	Sub 2-60	m / z = 409.18 (C 31 H 23 N = 409.53)
Sub 2-61	m / z = 459.20 (C 35 H 25 N = 459.59)	Sub 2-62	m / z = 485.21 (C 37 H 27 N = 485.63)
Sub 2-63	m / z = 649.28 (C 50 H 35 N = 649.84)	Sub 2-64	m / z = 485.21 (C 37 H 27 N = 485.63))
Sub 2-65	m / z = 407.17 (C 31 H 21 N = 407.52)	Sub 2-66	m / z = 483.20 (C 37 H 25 N = 483.61)
Sub 2-67	m / z = 645.25 (C 50 H 31 N = 645.81)	Sub 2-68	m / z = 457.18 (C 35 H 23 N = 457.58)
Sub 2-69	m / z = 483.20 (C 37 H 25 N = 483.61)	Sub 2-70	m / z = 334.15 (C 24 H 18 N 2 = 334.42)
Sub 2-71	m / z = 410.18 (C 30 H 22 N 2 = 410.52)	Sub 2-72	m / z = 486.21 (C 36 H 26 N 2 = 486.62)
Sub 2-73	m / z = 486.21 (C 36 H 26 N 2 = 486.62)	Sub 2-74	m / z = 332.13 (C 24 H 16 N 2 = 332.41)
Sub 2-75	m / z = 325.09 (C 22 H 15 NS = 325.43)	Sub 2-76	m / z = 351.11 (C 24 H 17 NS = 351.47)
Sub 2-77	m / z = 275.08 (C 18 H 13 NS = 275.37)	Sub 2-78	m / z = 351.11 (C 24 H 17 NS = 351.47)
Sub 2-79	m / z = 351.11 (C 24 H 17 NS = 351.47)	Sub 2-80	m / z = 335.13 (C 24 H 17 NO = 335.41)
Sub 2-81	m / z = 259.10 (C 18 H 13 NO = 259.31)	Sub 2-82	m / z = 335.13 (C 24 H 17 NO = 335.41)
Sub 2-83	m / z = 375.16 (C 27 H 21 NO = 375.47)	Sub 2-84	m / z = 411.16 (C 30 H 21 NO = 411.50)
Sub 2-85	m / z = 411.16 (C 30 H 21 NO = 411.50)	Sub 2-86	m / z = 461.18 (C 34 H 23 NO = 461.56)
Sub 2-87	m / z = 365.09 (C 24 H 15 NOS = 365.45)	Sub 2-88	m / z = 501.17 (C 36 H 23 NO 2 = 501.59)

III. Final product 1 synthesis

Sub 1 (1 equivalent) is dissolved in toluene in a round bottom flask, Sub 2 (1 equivalent), Pd ₂ (dba) ₃ (0.03 equiv), (t-Bu) 3 P (0.06 equiv) and NaOt-Bu (3 equiv) were stirred at 100 ° C. After completion of the reaction, the mixture was extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was purified by silicagel column and recrystallized to obtain Final product 1.

1.1-1 Synthesis Example

Sub 1-1 (9.70 g, 42.41 mmol) obtained in the above synthesis was dissolved in toluene (445 ml) in a round bottom flask, and then Sub 2-14 (14.99 g, 46.65 mmol) and Pd ₂ (dba) ₃ (1.17 g) , 1.27 mmol), P ( t -Bu) ₃ (0.51 g, 2.54 mmol), NaO t -Bu (12.23 g, 127.23 mmol) were added and stirred at 100 ° C. After the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was purified by silicagel column and recrystallized to give the product 16.34 g (yield: 75%).

2. 1-23 Synthesis Example

To Sub 1-12 (10.00 g, 28.34 mmol) obtained in the above synthesis, Sub 2-62 (15.14 g, 31.17 mmol), Pd ₂ (dba) ₃ (0.78 g, 0.85 mmol), P ( t -Bu) ₃ ( 0.34 g, 1.70 mmol), NaO t -Bu (8.17 g, 85.02 mmol), toluene (300 ml) were added and 15.46 g (yield: 68%) of the product was obtained using the 1-1 synthesis method.

3. 1-56 Synthesis Example

To Sub 1-25 (9.90 g, 28.22 mmol) obtained in the above synthesis, Sub 2-17 (11.53 g, 31.04 mmol), Pd ₂ (dba) ₃ (0.78 g, 0.85 mmol), P ( t -Bu) ₃ ( 0.34 g, 1.69 mmol), NaO t -Bu (8.14 g, 84.65 mmol) and toluene (300 ml) were added and the product 15.10 g (yield: 78%) was obtained using the 1-1 synthesis method.

4. 1-62 Synthesis Example

To Sub 1-26 (11.00 g, 23.33 mmol) obtained in the above synthesis, Sub 2-43 (9.28 g, 25.67 mmol), Pd ₂ (dba) ₃ (0.64 g, 0.70 mmol), P ( t -Bu) ₃ ( 0.28 g, 1.40 mmol), NaO t -Bu (6.73 g, 70.00 mmol) and toluene (245 ml) were added and the product 12.46 g (yield: 71%) was obtained using the 1-1 synthesis method.

5. 2-10 Synthesis Example

To Sub 1-33 (12.60 g, 31.43 mmol) obtained in the above synthesis, Sub 2-38 (11.60 g, 34.57 mmol), Pd ₂ (dba) ₃ (0.86 g, 0.94 mmol), P ( t -Bu) ₃ ( 0.38 g, 1.89 mmol), NaO t -Bu (9.06 g, 94.29 mmol), toluene (330 ml) were added and 13.86 g (yield: 63%) of the product was obtained using the above 1-1 synthesis method.

6. 2-31 Synthesis Example

To Sub 1-38 (11.90 g, 29.68 mmol) obtained in the above synthesis, Sub 2-43 (11.80 g, 32.65 mmol), Pd ₂ (dba) ₃ (0.82 g, 0.89 mmol), P ( t -Bu) ₃ ( 0.36 g, 1.78 mmol), NaO t -Bu (8.56 g, 89.05 mmol), toluene (310 ml) were added and the product 1 .65 g (yield: 68%) was obtained using the 1-1 synthesis method.

7. 2-41 Synthesis Example

To Sub 1-42 (12.00 g, 29.93 mmol) obtained in the above synthesis, Sub 2-14 (10.58 g, 32.93 mmol), Pd ₂ (dba) ₃ (0.82 g, 0.90 mmol), P ( t -Bu) ₃ ( 0.36 g, 1.80 mmol), NaO t -Bu (8.63 g, 89.80 mmol), toluene (315 ml) were added and the product 1 .78 g (yield: 72%) was obtained using the 1-1 synthesis method.

8. 2-48 Synthesis Example

To Sub 1-43 (11.30 g, 28.19 mmol) obtained in the above synthesis, Sub 2-39 (11.21 g, 31.00 mmol), Pd ₂ (dba) ₃ (0.77 g, 0.85 mmol), P ( t -Bu) ₃ ( 0.34 g, 1.69 mmol), NaO t -Bu (8.13 g, 84.56 mmol), toluene (295 ml) were added and the product 1 .32 g (yield: 70%) was obtained using the 1-1 synthesis method.

9. 2-55 Synthesis Example

To Sub 1-45 (13.00 g, 32.43 mmol) obtained in the above synthesis, Sub 2-79 (12.54 g, 35.67 mmol), Pd ₂ (dba) ₃ (0.89 g, 0.97 mmol), P ( t -Bu) ₃ ( 0.39 g, 1.95 mmol), NaO t -Bu (9.35 g, 97.28 mmol), toluene (340 ml) were added and the product 1,84 g (yield: 51%) was obtained using the 1-1 synthesis method.

10. 2-79 Synthesis Example

To Sub 1-61 (12.80 g, 30.05 mmol) obtained in the above synthesis, Sub 2-35 (12.45 g, 33.06 mmol), Pd ₂ (dba) ₃ (0.83 g, 0.90 mmol), P ( t -Bu) ₃ ( 0.36 g, 1.80 mmol), NaO t -Bu (8.67 g, 90.16 mmol), toluene (315 ml) were added and the product 10.59 g (yield: 46%) was obtained using the 1-1 synthesis method.

11. 2-98 Synthesis Example

To Sub 1-66 (12.70 g, 31.68 mmol) obtained in the above synthesis, Sub 2-82 (11.69 g, 34.85 mmol), Pd ₂ (dba) ₃ (0.87 g, 0.95 mmol), P ( t -Bu) ₃ ( 0.38 g, 1.90 mmol), NaO t -Bu (9.13 g, 95.03 mmol), toluene (330 ml) were added and the product 1 .41 g (yield: 65%) was obtained using the 1-1 synthesis method.

12. 2-102 Synthesis Example

To Sub 1-78 (12.40 g, 27.50 mmol) obtained in the above synthesis, Sub 2-38 (10.15 g, 30.25 mmol), Pd ₂ (dba) ₃ (0.76 g, 0.82 mmol), P ( t -Bu) ₃ ( 0.33 g, 1.65 mmol), NaO t -Bu (7.93 g, 82.49 mmol), toluene (290 ml) were added and the product 1 .23 g (yield: 69%) was obtained using the 1-1 synthesis method.

13. 2-109 Synthesis Example

To Sub 1-73 (13.25 g, 25.91 mmol) obtained in the above synthesis, Sub 2-7 (13.98 g, 56.99 mmol), Pd ₂ (dba) ₃ (1.42 g, 1.55 mmol), P ( t -Bu) ₃ ( 0.06 g, 0.31 mmol), NaO t -Bu (14.94 g, 155.44 mmol) and toluene (415 ml) were added and 13.72 g (yield: 57%) of product was obtained using the above 1-1 synthesis method.

14.2-114 Synthesis Example

To Sub 1-75 (15.00 g, 23.90 mmol) obtained in the above synthesis, Sub 2-11 (7.77 g, 26.29 mmol), Pd ₂ (dba) ₃ (0.66 g, 0.72 mmol), P ( t -Bu) ₃ ( 0.29 g, 1.43 mmol), NaO t -Bu (6.89 g, 71.70 mmol), toluene (250 ml) were added and the product 12.28 g (yield: 61%) was obtained using the 1-1 synthesis method.

15. 2-115 Synthesis Example

To Sub 1-76 (14.65 g, 22.98 mmol) obtained in the above synthesis, Sub 2-14 (8.12 g, 25.27 mmol), Pd ₂ (dba) ₃ (0.63 g, 0.69 mmol), P ( t -Bu) ₃ ( 0.28 g, 1.38 mmol), NaO t -Bu (6.62 g, 68.93 mmol), toluene (240 ml) were added and the product 12.91 g (yield: 64%) was obtained using the 1-1 synthesis method.

compound	FD-MS	compound	FD-MS
1-1	m / z = 513.25 (C 39 H 31 N = 513.68)	1-2	m / z = 613.28 (C 47 H 35 N = 613.80)
1-3	m / z = 665.31 (C 51 H 39 N = 665.88)	1-4	m / z = 705.34 (C 54 H 43 N = 705.95)
1-5	m / z = 593.31 (C 45 H 39 N = 593.81)	1-6	m / z = 589.28 (C 45 H 35 N = 589.78)
1-7	m / z = 513.25 (C 39 H 31 N = 513.68)	1-8	m / z = 639.29 (C 49 H 37 N = 639.84)
1-9	m / z = 589.28 (C 45 H 35 N = 589.78)	1-10	m / z = 665.31 (C 51 H 39 N = 665.88)
1-11	m / z = 553.28 (C 42 H 35 N = 553.75)	1-12	m / z = 669.34 (C 51 H 43 N = 669.91)
1-13	m / z = 779.36 (C 60 H 45 N = 780.03)	1-14	m / z = 761.35 (C 56 H 47 NSi = 762.08)
1-15	m / z = 705.34 (C 54 H 43 N = 705.95)	1-16	m / z = 589.28 (C 45 H 35 N = 589.78)
1-17	m / z = 665.31 (C 51 H 39 N = 665.88)	1-18	m / z = 728.32 (C 55 H 40 N2 = 728.94)
1-19	m / z = 637.28 (C 49 H 35 N = 637.83)	1-20	m / z = 789.34 (C 61 H 43 N = 790.02)
1-21	m / z = 677.31 (C 52 H 39 N = 677.89)	1-22	m / z = 775.32 (C 60 H 41 N = 776.00)
1-23	m / z = 801.34 (C 62 H 43 N = 802.03)	1-24	m / z = 799.32 (C 62 H 41 N = 800.02)
1-25	m / z = 965.40 (C 75 H 51 N = 966.24)	1-26	m / z = 637.28 (C 49 H 35 N = 637.83)
1-27	m / z = 635.26 (C 49 H 33 N = 635.81)	1-28	m / z = 616.29 (C 47 H 28 D 5 N = 616.82)
1-29	m / z = 727.32 (C 56 H 41 N = 727.95)	1-30	m / z = 687.29 (C 53 H 37 N = 687.89)
1-31	m / z = 877.37 (C 68 H 47 N = 878.13)	1-32	m / z = 753.34 (C 58 H 43 N = 753.99)
1-33	m / z = 689.31 (C 53 H 39 N = 689.90)	1-34	m / z = 637.28 (C 49 H 35 N = 637.83)
1-35	m / z = 850.32 (C 62 H 40 F 2 N 2 = 851.01)	1-36	m / z = 559.23 (C 43 H 29 N = 559.71)
1-37	m / z = 635.26 (C 49 H 33 N = 635.81)	1-38	m / z = 663.29 (C 51 H 37 N = 663.86)
1-39	m / z = 735.29 (C 57 H 37 N = 735.93)	1-40	m / z = 735.29 (C 57 H 37 N = 735.93)
1-41	m / z = 725.31 (C 56 H 39 N = 725.94)	1-42	m / z = 735.29 (C 57 H 37 N = 735.93)
1-43	m / z = 751.32 (C 58 H 41 N = 751.97)	1-44	m / z = 725.31 (C 56 H 39 N = 725.94)
1-45	m / z = 675.29 (C 52 H 37 N = 675.88)	1-46	m / z = 675.29 (C 52 H 37 N = 675.88)
1-47	m / z = 751.32 (C 58 H 41 N = 751.97)	1-48	m / z = 675.29 (C 52 H 37 N = 675.88)
1-49	m / z = 721.28 (C 56 H 35 N = 721.90)	1-50	m / z = 797.31 (C 62 H 39 N = 798.00)
1-51	m / z = 959.36 (C 75 H 45 N = 960.19)	1-52	m / z = 607.23 (C 47 H 29 N = 607.76)
1-53	m / z = 675.29 (C 52 H 37 N = 675.88)	1-54	m / z = 635.26 (C 49 H 33 N = 635.81)
1-55	m / z = 640.29 (C 49 H 28 D 5 N = 640.84)	1-56	m / z = 685.28 (C 53 H 35 N = 685.87)
1-57	m / z = 735.29 (C 57 H 37 N = 735.93)	1-58	m / z = 583.23 (C 45 H 29 N = 583.73)
1-59	m / z = 725.31 (C 56 H 39 N = 725.94)	1-60	m / z = 725.31 (C 56 H 39 N = 725.94)
1-61	m / z = 635.26 (C 49 H 33 N = 635.81)	1-62	m / z = 751.32 (C 58 H 41 N = 751.97)
1-63	m / z = 751.32 (C 58 H 41 N = 751.97)	1-64	m / z = 751.32 (C 58 H 41 N = 751.97)
1-65	m / z = 842.37 (C 64 H 46 N2 = 843.09)	1-66	m / z = 751.32 (C 58 H 41 N = 751.97)
1-67	m / z = 873.34 (C 68 H 43 N = 874.10)	1-68	m / z = 711.29 (C 55 H 37 N = 711.91)
1-69	m / z = 751.32 (C 58 H 41 N = 751.97)	1-70	m / z = 787.32 (C 61 H 41 N = 788.01)
2-1	m / z = 583.23 (C 45 H 29 N = 583.73)	2-2	m / z = 609.25 (C 47 H 31 N = 609.77)
2-3	m / z = 685.28 (C 53 H 35 N = 685.87)	2-4	m / z = 659.26 (C 51 H 33 N = 659.83)
2-5	m / z = 607.23 (C 47 H 29 N = 607.76)	2-6	m / z = 685.28 (C 53 H 35 N = 685.87)
2-7	m / z = 664.29 (C 51 H 28 D 5 N = 664.86)	2-8	m / z = 649.28 (C 50 H 35 N = 649.84)
2-9	m / z = 699.29 (C 54 H 37 N = 699.90)	2-10	m / z = 699.29 (C 54 H 37 N = 699.90)
2-11	m / z = 725.31 (C 56 H 39 N = 725.94)	2-12	m / z = 739.32 (C 57 H 41 N = 739.96)
2-13	m / z = 730.34 (C 56 H 34 D 5 N = 730.97)	2-14	m / z = 775.32 (C 60 H 41 N = 776.00)
2-15	m / z = 775.32 (C 60 H 41 N = 776.00)	2-16	m / z = 775.32 (C 60 H 41 N = 776.00)
2-17	m / z = 725.31 (C 56 H 39 N = 725.94)	2-18	m / z = 773.31 (C 60 H 39 N = 773.98)
2-19	m / z = 725.31 (C 56 H 39 N = 725.94)	2-20	m / z = 774.30 (C 59 H 38 N 2 = 774.97)
2-21	m / z = 639.20 (C 47 H 29 NS = 639.82)	2-22	m / z = 699.26 (C 53 H 33 NO = 699.85)
2-23	m / z = 775.29 (C 59 H 37 NO = 775.95)	2-24	m / z = 775.29 (C 59 H 37 NO = 775.95)
2-25	m / z = 865.30 (C 65 H 39 NO 2 = 866.03)	2-26	m / z = 583.23 (C 45 H 29 N = 583.73)
2-27	m / z = 685.28 (C 53 H 35 N = 685.87)	2-28	m / z = 649.28 (C 50 H 35 N = 649.84)
2-29	m / z = 699.29 (C 54 H 37 N = 699.90)	2-30	m / z = 725.31 (C 56 H 39 N = 725.94)
2-31	m / z = 725.31 (C 56 H 39 N = 725.94)	2-32	m / z = 775.32 (C 60 H 41 N = 776.00)
2-33	m / z = 775.32 (C 60 H 41 N = 776.00)	2-34	m / z = 775.32 (C 60 H 41 N = 776.00)
2-35	m / z = 699.29 (C 54 H 37 N = 699.90)	2-36	m / z = 773.31 (C 60 H 39 N = 773.98)
2-37	m / z = 715.23 (C 53 H 33 NS = 715.91)	2-38	m / z = 739.29 (C 56 H 37 NO = 739.92)
2-39	m / z = 699.26 (C 53 H 33 NO = 699.85)	2-40	m / z = 662.25 (C 48 H 30 N 4 = 662.80)
2-41	m / z = 685.28 (C 53 H 35 N = 685.87)	2-42	m / z = 685.28 (C 53 H 35 N = 685.87)
2-43	m / z 633.25 (C 49 H 31 N = 633.79)	2-44	m / z = 649.28 (C 50 H 35 N = 649.84)
2-45	m / z = 725.31 (C 56 H 39 N = 725.94)	2-46	m / z = 725.31 (C 56 H 39 N = 725.94)
2-47	m / z = 801.34 (C 62 H 43 N = 802.03)	2-48	m / z = 725.31 (C 56 H 39 N = 725.94)
2-49	m / z = 849.34 (C 66 H 43 N = 850.08)	2-50	m / z = 850.33 (C 65 H 42 N 2 = 851.07)
2-51	m / z = 689.22 (C 51 H 31 NS = 689.88)	2-52	m / z = 623.22 (C 47 H 29 NO = 623.76)
2-53	m / z = 775.29 (C 59 H 37 NO = 775.95)	2-54	m / z = 699.26 (C 53 H 33 NO = 699.85)
2-55	m / z = 715.23 (C 53 H 33 NS = 715.91)	2-56	m / z = 690.31 (C 53 H 30 D 5 N = 690.90)
2-57	m / z = 787.32 (C 61 H 41 N = 788.01)	2-58	m / z = 699.29 (C 54 H 37 N = 699.90)
2-59	m / z = 725.31 (C 56 H 39 N = 725.94)	2-60	m / z = 715.23 (C 53 H 33 NS = 715.91)
2-61	m / z = 633.25 (C 49 H 31 N = 633.79)	2-62	m / z = 583.23 (C 45 H 29 N = 583.73)
2-63	m / z = 865.33 (C 66 H 43 NO = 866.08)	2-64	m / z = 821.31 (C 64 H 39 N = 822.02)
2-65	m / z = 698.27 (C 53 H 34 N 2 = 698.87)	2-66	m / z = 659.26 (C 51 H 33 N = 659.83)
2-67	m / z = 649.28 (C 50 H 35 N = 649.84)	2-68	m / z = 849.34 (C 66 H 43 N = 850.08)
2-69	m / z = 850.33 (C 65 H 42 N 2 = 851.07)	2-70	m / z = 825.30 (C 63 H 39 NO = 826.01)
2-71	m / z = 583.23 (C 45 H 29 N = 583.73)	2-72	m / z = 685.28 (C 53 H 35 N = 685.87)
2-73	m / z = 693.32 (C 53 H 23 D 10 N = 693.92)	2-74	m / z = 699.29 (C 54 H 37 N = 699.90)
2-75	m / z = 725.31 (C 56 H 39 N = 725.94)	2-76	m / z = 775.32 (C 60 H 41 N = 776.00)
2-77	m / z = 725.31 (C 56 H 39 N = 725.94)	2-78	m / z = 849.34 (C 66 H 43 N = 850.08)
2-79	m / z = 765.31 (C 57 H 39 N 3 = 765.96)	2-80	m / z = 775.29 (C 59 H 37 NO = 775.95)
2-81	m / z = 685.28 (C 53 H 35 N = 685.87)	2-82	m / z = 609.25 (C 47 H 31 N = 609.77)
2-83	m / z = 785.31 (C 61 H 39 N = 785.99)	2-84	m / z = 725.31 (C 56 H 39 N = 725.94)
2-85	m / z = 729.21 (C 53 H 31 NOS = 729.90)	2-86	m / z = 583.23 (C 45 H 29 N = 583.73)
2-87	m / z = 685.28 (C 53 H 35 N = 685.87)	2-88	m / z = 735.29 (C57H37N =)
2-89	m / z = 685.28 (C 53 H 35 N = 685.87)	2-90	m / z = 685.28 (C 53 H 35 N = 685.87)
2-91	m / z = 725.31 (C 56 H 39 N = 725.94)	2-92	m / z = 749.31 (C 58 H 39 N = 749.96)
2-93	m / z = 725.31 (C 56 H 39 N = 725.94)	2-94	m / z = 725.31 (C 56 H 39 N = 725.94)
2-95	m / z = 725.31 (C 56 H 39 N = 725.94)	2-96	m / z = 773.31 (C 60 H 39 N = 773.98)
2-97	m / z = 850.33 (C 65 H 42 N 2 = 851.07)	2-98	m / z = 699.26 (C 53 H 33 NO = 699.85)
2-99	m / z = 715.23 (C 53 H 33 NS = 715.91)	2-100	m / z = 739.29 (C 56 H 37 NO = 739.92)
2-101	m / z = 709.28 (C 55 H 35 N = 709.89)	2-102	m / z = 749.31 (C 58 H 39 N = 749.96)
2-103	m / z = 901.37 (C 70 H 47 N = 902.15)	2-104	m / z = 660.26 (C 50 H 32 N 2 = 660.82)
2-105	m / z = 673.24 (C 51 H 31 NO = 673.82)	2-106	m / z = 685.28 (C 53 H 35 N = 685.87)
2-107	m / z = 775.32 (C 60 H 41 N = 776.00)	2-108	m / z = 772.29 (C59H36N2 = 772.95)
2-109	m / z = 928.38 (C 71 H 48 N 2 = 929.18)	2-110	m / z = 941.31 (C 71 H 43 NS = 942.19)
2-111	m / z = 836.32 (C 64 H 40 N 2 = 837.04)	2-112	m / z = 913.35 (C 69 H 43 N 3 = 914.12)
2-113	m / z = 800.28 (C 60 H 36 N 2 O = 800.96)	2-114	m / z = 841.28 (C 63 H 39 NS = 842.07)
2-115	m / z = 877.37 (C 68 H 47 N = 878.13)

[ Synthesis Example  2]

The compound represented by Chemical Formula 2 according to the present invention (final product 2) is synthesized by reacting Sub 3 and Sub 4, as shown in Scheme 4 below, but is not limited thereto. E, F, R ⁵ , R ⁶ , R ⁷ , e, f, g, h, i, L ² , Ar ³ , X ² and X ³ are the same as defined in Formula 2, Hal ¹ is Br or Cl to be.

<Scheme 4>

I. Synthesis of Sub 3

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

Scheme 5

Carbazole derivatives, which are starting materials used in the synthesis of Sub 3-I-1, were prepared by the synthesis method disclosed in Korean Patent Registration No. 10-1535606 (registered date of July 3, 2015).

Dibenzothiophene derivative or dibenzofuran, which is a starting material used in the synthesis of Sub 3-I-1, was prepared by the synthesis method disclosed in Korean Patent Application No. 2014-0074261 (filed on June 18, 2014) of the present applicant.

Fluorene derivatives, which are starting materials used in the synthesis of Sub 3-I-1, are disclosed in Korean Patent Application No. 2013-0056221 (filed May 20, 2013) and Korean Patent Application No. 2015-0083505 (filed June 12, 2015). It was prepared by the synthetic method.

Synthesis examples of specific compounds belonging to Sub 3 are as follows.

Sub 3-1 Synthesis Example

(1) Sub 3-I-1 Synthesis

The starting material 9-bromo-11-phenyl-11H-benzo [a] carbazole (55.00 g, 147.74 mmol) was dissolved in DMF (740 ml) in a round bottom flask, followed by Bis (pinacolato) diboron (41.27 g, 162.52 mmol). ), Pd (dppf) Cl₂ (3.62 g, 4.43 mmol), KOAc (43.50 g, 443.23 mmol) was added and stirred at 120 ° C. When the reaction is complete, remove DMF by distillation₂Cl₂And extracted with water. MgSO organic layer₄After drying and concentration, the resulting compound was silicagel column and recrystallized to give 51.42 g (yield: 83%) of the product.

(2) Sub 3-II-1 Synthesis

Sub 3-I-1 (51.42 g, 122.62 mmol) obtained in the above synthesis was dissolved in THF (540 ml) in a round bottom flask, followed by 1-bromo-2-nitrobenzene (CAS Registry Number: 577-19-5) ( 24.77 g, 122.62 mmol), Pd (PPh ₃ ) ₄ (4.25 g, 3.68 mmol), K ₂ CO ₃ (50.84 g, 367.87 mmol), water (270 ml) were added and stirred at 80 ° C. After completion of the reaction, the mixture was extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was purified by silicagel column and recrystallized to obtain a product 38.63 g (yield: 76%).

(3) Sub 3-1 synthesis

3-II-1 (38.63 g, 93.21 mmol) obtained in the above synthesis was dissolved in o- dichlorobenzene (466 ml) in a round bottom flask, followed by addition of triphenylphosphine (61.12 g, 233.01 mmol) and stirred at 200 ° C. After the reaction was completed, o -dichlorobenzene was removed by distillation and extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ , concentrated and the resulting compound was silicagel column and recrystallized to give 14.97 g (yield: 42%) of the product.

2.Sub 3-15 Synthesis Example

(1) Sub 3-I-15 Synthesis

Bis (pinacolato) diboron (145.82 g, 574.22 mmol) and Pd (dppf) Cl _{2 in the} starting material 5-bromobenzo [b] naphtho [1,2-d] thiophene (163.50 g, 522.01 mmol) (12.79 g, 15.66 mmol), KOAc (153.69 g, 1566.04 mmol), DMF (2610 ml) were added and 150.46 g (yield: 80%) of product was obtained using the Sub 3-I-1 synthesis method.

(2) Sub 3-II-15 Synthesis

Sub 3-I-15 (92.02 g, 255.41 mmol) obtained in the above synthesis was converted into 1-bromo-2-nitrobenzene (CAS Registry Number: 577-19-5) (51.60 g, 255.41 mmol), Pd (PPh ₃ ) ₄ (8.85 g, 7.66 mmol), K ₂ CO ₃ (105.89 g, 766.24 mmol), THF (1130 ml), water (565 ml) were added and the product 63.54 g (yield) was obtained using the Sub 3-II-1 synthesis. : 70%).

(3) Sub 3-15 synthesis

To the Sub 3-II-15 (63.54 g, 178.78 mmol) obtained in the above synthesis, triphenylphosphine (117.23 g, 446.95 mmol) and o -dichlorobenzene (894 ml) were added and the product 42.21 g ( Yield: 73%).

3.Sub 3-16 Synthesis Example

(1) Sub 3-II-16 Synthesis

Sub 3-I-15 (40.00 g, 111.02 mmol) obtained in the above synthesis 3-bromo-4-nitro-1,1'-biphenyl (CAS Registry Number: 27721-82-0) (30.88 g, 111.02 mmol) , Pd (PPh ₃ ) ₄ (3.85 g, 3.33 mmol), K ₂ CO ₃ (46.03 g, 333.07 mmol), THF (490 ml), water (245 ml) were added and the above Sub 3-II-1 synthesis was carried out. To give 34.97 g (yield: 73%) of product.

(2) Sub 3-16 synthesis

Triphenylphosphine (53.14 g, 202.60 mmol) and o -dichlorobenzene (405 ml) were added to Sub 3-II-16 (34.97 g, 81.04 mmol) obtained in the above synthesis, and 21.69 g of the product was obtained using the Sub 3-1 synthesis method. Yield: 67%).

4.Sub 3-19 Synthesis Example

(1) Sub 3-II-19 Synthesis

3- (4-bromo-3-nitrophenyl) -9-phenyl-9H-carbazole (CAS Registry Number: 1526986-96-8) (49.22) in Sub 3-I-15 (40.00 g, 111.02 mmol) obtained in the above synthesis. g, 111.02 mmol), Pd (PPh ₃ ) ₄ (3.85 g, 3.33 mmol), K ₂ CO ₃ (46.03 g, 333.07 mmol), THF (490 ml), water (245 ml) were added and the Sub 3- 42.40 g (yield: 64%) of product were obtained using II-1 synthesis.

(2) Sub 3-19 synthesis

To the Sub 3-II-19 (42.40 g, 71.06 mmol) obtained in the above synthesis, triphenylphosphine (46.59 g, 177.64 mmol) and o -dichlorobenzene (355 ml) were added and the product 24.48 g ( Yield: 61%).

5.Sub 3-22 Synthesis Example

(1) Sub 3-II-22 Synthesis

Sub 3-I-15 (57.17 g, 158.68 mmol) obtained in the synthesis of 2-bromo-1-nitronaphthalene (CAS Registry Number: 4185-62-0) (40.00 g, 158.68 mmol), Pd (PPh ₃ ) ₄ (5.50 g, 4.76 mmol), K ₂ CO ₃ (65.79 g, 476.05 mmol), THF (700 ml), water (350 ml) were added and the product 47.61 g (yield) was obtained using the Sub 3-II-1 synthesis. : 74%).

(2) Sub 3-22 synthesis

To the Sub 3-II-22 (47.61 g, 117.42 mmol) obtained in the above synthesis, triphenylphosphine (76.99 g, 293.55 mmol) and o -dichlorobenzene (587 ml) were added and the product 28.07 g ( Yield: 64%).

6.Sub 3-33 Synthesis Example

(1) Sub 3-I-33 Synthesis

Bis (pinacolato) diboron (48.27 g, 190.09 mmol), Pd (dppf) Cl ₂ in 11-bromophenanthro [9,10-b] benzofuran (60.00 g, 172.81 mmol) (4.23 g, 5.18 mmol), KOAc (50.88 g, 518.42 mmol), DMF (864 ml) were added and 52.46 g (yield: 77%) of product was obtained using the Sub 3-I-1 synthesis method.

(2) Sub 3-II-33 Synthesis

Sub 3-I-33 (52.46 g, 133.05 mmol) obtained in the above synthesis was converted into 1-bromo-2-nitrobenzene (CAS Registry Number: 577-19-5) (26.88 g, 133.05 mmol) and Pd (PPh ₃ ) ₄ (4.61 g, 3.99 mmol), K ₂ CO ₃ (55.16 g, 399.16 mmol), THF (580 ml), water (290 ml) were added and the product 40.93 g (yield) was obtained using the Sub 3-II-1 synthesis. : 79%).

(3) Sub 3-33 synthesis

To the Sub 3-II-33 (40.93 g, 105.11 mmol) obtained in the above synthesis, triphenylphosphine (68.92 g, 262.77 mmol) and o -dichlorobenzene (526 ml) were added and the product 15.03 g ( Yield: 40%).

7.Sub 3-41 Synthesis Example

(1) Sub 3-I-41 Synthesis

Bis (pinacolato) diboron (56.24 g, 221.47 mmol), Pd (dppf) Cl ₂ in 2-bromo-9,9-dimethyl-9H-fluorene (55.00 g, 201.34 mmol) (4.93 g, 6.04 mmol), KOAc (59.28 g, 604.02 mmol), DMF (1000 ml) were added and 50.94 g (yield: 79%) of product was obtained using the Sub 3-I-1 synthesis method.

(2) Sub 3-II-41 Synthesis

Sub 3-I-41 (50.94 g, 159.07 mmol) obtained in the above synthesis was converted into 1-bromo-2-nitronaphthalene (CAS Registry Number: 4185-55-1) (40.10 g, 159.07 mmol) and Pd (PPh ₃ ) ₄ (5.51 g, 4.77 mmol), K ₂ CO ₃ (65.95 g, 477.20 mmol), THF (700 ml), water (350 ml) were added and the product 47.67 g (yield) was obtained using the Sub 3-II-1 synthesis. : 82%).

(3) Sub 3-41 synthesis

To the Sub 3-II-41 (47.67 g, 130.45 mmol) obtained in the above synthesis, triphenylphosphine (85.54 g, 326.12 mmol) and o -dichlorobenzene (652 ml) were added and the product 15.66 g ( Yield: 36%).

8.Sub 3-57 Synthesis Example

(1) Sub 3-I-57 Synthesis

Bis (pinacolato) diboron (39.02 g, 153.65 mmol), Pd (dppf) Cl _{2 in} starting 6-bromo-7-phenyl-7H-benzo [c] carbazole (52.00 g, 139.68 mmol) (3.42 g, 4.19 mmol), KOAc (41.13 g, 419.05 mmol), DMF (698 ml) were added and the product 42.76 g (yield: 73%) was obtained using the Sub 3-I-1 synthesis method.

(2) Sub 3-II-57 Synthesis

Sub 3-I-57 (42.76 g, 101.97 mmol) obtained in the above synthesis was subjected to 2-bromo-3-nitronaphthalene (CAS Registry Number: 67116-33-0) (25.70 g, 101.97 mmol), Pd (PPh ₃ ) ₄ (3.54 g, 3.06 mmol), K ₂ CO ₃ (42.28 g, 305.92 mmol), THF (450 ml), water (225 ml) were added and the product 28.89 g (yield) using the Sub 3-II-1 synthesis : 61%).

(3) Sub 3-57 synthesis

To sub 3-II-57 (28.89 g, 62.19 mmol) obtained in the above synthesis, triphenylphosphine (40.78 g, 155.48 mmol) and o -dichlorobenzene (311 ml) were added and the product 16.14 g ( Yield: 60%).

9.Sub 3-64 Synthesis Example

(1) Sub 3-I-64 Synthesis

Bis (pinacolato) diboron (34.78 g, 136.97 mmol) and Pd (dppf) Cl _{2 in the} starting material 5-bromobenzo [b] naphtho [2,1-d] thiophene (39.00 g, 124.52 mmol) (3.05 g, 3.74 mmol), KOAc (36.66 g, 373.55 mmol), DMF (620 ml) were added and the product 34.99 g (yield: 78%) were obtained using the Sub 3-I-1 synthesis method.

(2) Sub 3-II-64 Synthesis

Sub 3-I-64 (34.99 g, 97.12 mmol) obtained in the synthesis of 2-bromo-1-nitronaphthalene (CAS Registry Number: 4185-62-0) (24.48 g, 97.12 mmol), Pd (PPh ₃ ) ₄ (3.37 g, 2.91 mmol), K ₂ CO ₃ (40.27 g, 291.36 mmol), THF (430 ml), water (215 ml) were added and 27.17 g (yield) of the product using the above Sub 3-II-1 synthesis : 69%).

(3) Sub 3-64 synthesis

To Sub 3-II-64 (27.17 g, 67.01 mmol) obtained in the above synthesis, triphenylphosphine (43.94 g, 167.52 mmol) and o -dichlorobenzene (335 ml) were added and the product 16.52 g ( Yield: 66%).

10.Sub 3-75 Synthesis Example

(1) Sub 3-I-75 Synthesis

Bis (pinacolato) diboron (51.70 g, 203.60 mmol), Pd (dppf) Cl ₂ in 2-bromonaphtho [2,3-b] benzofuran (55.00 g, 185.09 mmol) (4.53 g, 5.55 mmol), KOAc (54.49 g, 555.28 mmol), DMF (925 ml) were added and 50.97 g (yield: 80%) of product was obtained using the Sub 3-I-1 synthesis method.

(2) Sub 3-II-75 Synthesis

Sub 3-I-75 (50.97 g, 148.07 mmol) obtained in the above synthesis was subjected to 2-bromo-1-nitronaphthalene (CAS Registry Number: 4185-62-0) (37.32 g, 148.07 mmol), Pd (PPh ₃ ) ₄ (5.13 g, 4.44 mmol), K ₂ CO ₃ (61.39 g, 444.22 mmol), THF (660 ml), water (330 ml) were added and the product 42.67 g (yield) was obtained using the Sub 3-II-1 synthesis method. : 74%).

(3) Sub 3-75 synthesis

To Sub 3-II-75 (42.67 g, 109.58 mmol) obtained in the above synthesis, triphenylphosphine (71.85 g, 273.94 mmol) and o -dichlorobenzene (548 ml) were added, and the product was analyzed using 14.88 g ( Yield: 38%).

11.Sub 3-90 Synthesis Example

(1) Sub 3-I-90 Synthesis

Bis (pinacolato) diboron (36.59 g, 144.10 mmol), Pd (dppf) Cl ₂ in 5-bromo-13,13-dimethyl-13H-dibenzo [a, i] fluorene (48.90 g, 131.00 mmol) (3.12 g, 3.93 mmol), KOAc (38.57 g, 392.99 mmol), DMF (655 ml) were added and the product 40.75 g (yield: 74%) were obtained using the Sub 3-I-1 synthesis method.

(2) Sub 3-II-90 Synthesis

Sub 3-I-90 (40.75 g, 96.94 mmol) obtained in the above synthesis was converted into 1-bromo-2-nitrobenzene (CAS Registry Number: 577-19-5) (19.58 g, 96.94 mmol) and Pd (PPh ₃ ) ₄ (3.36 g, 2.91 mmol), K ₂ CO ₃ (40.19 g, 290.82 mmol), THF (430 ml), water (215 ml) were added and the product 27.39 g (yield) using the Sub 3-II-1 synthesis : 68%).

(3) Sub 3-90 Synthesis

Triphenylphosphine (43.23 g, 164.81 mmol) and o -dichlorobenzene (330 ml) were added to Sub 3-II-90 (27.39 g, 65.92 mmol) obtained in the above synthesis, and the product was obtained using 14.92 g ( Yield: 59%).

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

compound	FD-MS	compound	FD-MS
Sub 3-1	m / z = 382.15 (C 28 H 18 N 2 = 382.47)	Sub 3-2	m / z = 382.15 (C 28 H 18 N 2 = 382.47)
Sub 3-3	m / z = 432.16 (C 32 H 20 N 2 = 432.53)	Sub 3-4	m / z = 432.16 (C 32 H 20 N 2 = 432.53)
Sub 3-5	m / z = 432.16 (C 32 H 20 N 2 = 432.53)	Sub 3-6	m / z = 432.16 (C 32 H 20 N 2 = 432.53)
Sub 3-7	m / z = 482.18 (C 36 H 22 N 2 = 482.59)	Sub 3-8	m / z = 323.08 (C 22 H 13 NS = 323.41)
Sub 3-9	m / z = 323.08 (C 22 H 13 NS = 323.41)	Sub 3-10	m / z = 323.08 (C 22 H 13 NS = 323.41)
Sub 3-11	m / z = 323.08 (C 22 H 13 NS = 323.41)	Sub 3-12	m / z = 323.08 (C 22 H 13 NS = 323.41)
Sub 3-13	m / z = 373.09 (C 26 H 15 NS = 373.47)	Sub 3-14	m / z = 373.09 (C 26 H 15 NS = 373.47)
Sub 3-15	m / z = 323.08 (C 22 H 13 NS = 323.41)	Sub 3-16	m / z = 399.11 (C 28 H 17 NS = 399.51)
Sub 3-17	m / z = 555.11 (C 38 H 21 NS 2 = 555.71)	Sub 3-18	m / z = 692.20 (C 48 H 28 N 4 S = 692.84)
Sub 3-19	m / z = 564.17 (C 40 H 24 N 2 S = 564.71)	Sub 3-20	m / z = 490.15 (C 34 H 22 N 2 S = 490.62)
Sub 3-21	m / z = 468.11 (C 31 H 17 FN 2 S = 468.55)	Sub 3-22	m / z = 373.09 (C 26 H 15 NS = 373.47)
Sub 3-23	m / z = 373.09 (C 26 H 15 NS = 373.47)	Sub 3-24	m / z = 373.09 (C 26 H 15 NS = 373.47)
Sub 3-25	m / z = 373.09 (C 26 H 15 NS = 373.47)	Sub 3-26	m / z = 373.09 (C 26 H 15 NS = 373.47)
Sub 3-27	m / z = 373.09 (C 26 H 15 NS = 373.47)	Sub 3-28	m / z = 423.11 (C 30 H 17 NS = 423.53)
Sub 3-29	m / z = 307.10 (C 22 H 13 NO = 307.35)	Sub 3-30	m / z = 307.10 (C 22 H 13 NO = 307.35)
Sub 3-31	m / z = 307.10 (C 22 H 13 NO = 307.35)	Sub 3-32	m / z = 307.10 (C 22 H 13 NO = 307.35)
Sub 3-33	m / z = 357.12 (C 26 H 15 NO = 357.41)	Sub 3-34	m / z = 357.12 (C 26 H 15 NO = 357.41)
Sub 3-35	m / z = 357.12 (C 26 H 15 NO = 357.41)	Sub 3-36	m / z = 307.10 (C 22 H 13 NO = 307.35)
Sub 3-37	m / z = 357.12 (C 26 H 15 NO = 357.41)	Sub 3-38	m / z = 433.15 (C 32 H 19 NO = 433.51)
Sub 3-39	m / z = 358.11 (C 25 H 14 N 2 O = 358.40)	Sub 3-40	m / z = 437.14 (C 31 H 19 NO 2 = 437.50)
Sub 3-41	m / z = 333.15 (C 25 H 19 N = 333.43)	Sub 3-42	m / z = 383.17 (C 29 H 21 N = 383.49)
Sub 3-43	m / z = 455.17 (C 35 H 21 N = 455.56)	Sub 3-44	m / z = 333.15 (C 25 H 19 N = 333.43)
Sub 3-45	m / z = 574.24 (C 43 H 30 N 2 = 574.73)	Sub 3-46	m / z = 457.18 (C 35 H 23 N = 457.58)
Sub 3-47	m / z = 383.17 (C 29 H 21 N = 383.49)	Sub 3-48	m / z = 383.17 (C 29 H 21 N = 383.49)
Sub 3-49	m / z = 433.18 (C 33 H 23 N = 433.55)	Sub 3-50	m / z = 383.17 (C 29 H 21 N = 383.49)
Sub 3-51	m / z = 382.15 (C 28 H 18 N 2 = 382.47)	Sub 3-52	m / z = 432.16 (C 32 H 20 N 2 = 432.53)
Sub 3-53	m / z = 432.16 (C 32 H 20 N 2 = 432.53)	Sub 3-54	m / z = 432.16 (C 32 H 20 N 2 = 432.53)
Sub 3-55	m / z = 432.16 (C 32 H 20 N 2 = 432.53)	Sub 3-56	m / z = 432.16 (C 32 H 20 N 2 = 432.53)
Sub 3-57	m / z = 432.16 (C 32 H 20 N 2 = 432.53)	Sub 3-58	m / z = 323.08 (C 22 H 13 NS = 323.41)
Sub 3-59	m / z = 373.09 (C 26 H 15 NS = 373.47)	Sub 3-60	m / z = 373.09 (C 26 H 15 NS = 373.47)
Sub 3-61	m / z = 373.09 (C 26 H 15 NS = 373.47)	Sub 3-62	m / z = 373.09 (C 26 H 15 NS = 373.47)
Sub 3-63	m / z = 323.08 (C 22 H 13 NS = 323.41)	Sub 3-64	m / z = 373.09 (C 26 H 15 NS = 373.47)
Sub 3-65	m / z = 373.09 (C 26 H 15 NS = 373.47)	Sub 3-66	m / z = 373.09 (C 26 H 15 NS = 373.47)
Sub 3-67	m / z = 423.11 (C 30 H 17 NS = 423.53)	Sub 3-68	m / z = 373.09 (C 26 H 15 NS = 373.47)
Sub 3-69	m / z = 423.11 (C 30 H 17 NS = 423.53)	Sub 3-70	m / z = 423.11 (C 30 H 17 NS = 423.53)
Sub 3-71	m / z = 307.10 (C 22 H 13 NO = 307.35)	Sub 3-72	m / z = 357.12 (C 26 H 15 NO = 357.41)
Sub 3-73	m / z = 307.10 (C 22 H 13 NO = 307.35)	Sub 3-74	m / z = 307.10 (C 22 H 13 NO = 307.35)
Sub 3-75	m / z = 357.12 (C 26 H 15 NO = 357.41)	Sub 3-76	m / z = 357.12 (C 26 H 15 NO = 357.41)
Sub 3-77	m / z = 357.12 (C 26 H 15 NO = 357.41)	Sub 3-78	m / z = 407.13 (C 30 H 17 NO = 407.47)
Sub 3-79	m / z = 357.12 (C 26 H 15 NO = 357.41)	Sub 3-80	m / z = 357.12 (C 26 H 15 NO = 357.41)
Sub 3-81	m / z = 648.22 (C 48 H 28 N 2 O = 648.77)	Sub 3-82	m / z = 407.13 (C 30 H 17 NO = 407.47)
Sub 3-83	m / z = 333.15 (C 25 H 19 N = 333.43)	Sub 3-84	m / z = 383.17 (C 29 H 21 N = 383.49)
Sub 3-85	m / z = 699.23 (C 51 H 29 N 3 O = 699.81)	Sub 3-86	m / z = 383.17 (C 29 H 21 N = 383.49)
Sub 3-87	m / z = 383.17 (C 29 H 21 N = 383.49)	Sub 3-88	m / z = 507.20 (C 39 H 25 N = 507.64)
Sub 3-89	m / z = 505.18 (C 39 H 23 N = 505.62)	Sub 3-90	m / z = 383.17 (C 29 H 21 N = 383.49)
Sub 3-91	m / z = 433.18 (C 33 H 23 N = 433.55)

II. Synthesis of Sub 4

Sub 4 of Scheme 4 may be synthesized by the reaction route of Scheme 6, but is not limited thereto. At this time, Hal ¹ and Hal ² are Br or Cl.

<Scheme 6>

Synthesis examples of specific compounds belonging to Sub 4 are as follows.

Sub 4-20 Synthesis Example

After starting material 4-bromo-2-chloro-6-phenylpyrimidine (CAS Registry Number: 1412955-57-7) (21.85 g, 81.07 mmol) was dissolved in THF (280 ml) in a round bottom flask, 4,4, 5,5-tetramethyl-2- (naphthalen-2-yl) -1,3,2-dioxaborolane (CAS Registry Number: 256652-04-7) (22.66 g, 89.17 mmol), Pd (PPh ₃ ) ₄ (3.75 g, 3.24 mmol), K ₂ CO ₃ (33.61 g, 243.20 mmol), water (140 ml) were added and stirred at 90 ° C. When the reaction was complete, CH ₂ Cl ₂ and after drying the organic layer extracted with water, MgSO _4, and concentrated The resulting compound silicagel column and the product was recrystallized from 19.52 g (yield: 76%) was obtained.

2.Sub 4-32 Synthesis Example

Starting material 1,4-dibromobenzene (CAS Registry Number: 106-37-6) (17.80 g, 75.45 mmol) in 2,4-diphenyl-6- (4,4,5,5-tetramethyl-1,3, 2-dioxaborolan-2-yl) pyrimidine (CAS Registry Number: 1402237-88-0) (29.73 g, 83.00 mmol), Pd (PPh ₃ ) ₄ (3.49 g, 3.02 mmol), K ₂ CO ₃ (31.28 g, 226.36 mmol), THF (260 ml), water (130 ml) were added and 21.33 g (yield: 73%) of product was obtained using the Sub 4-20 synthesis method.

3.Sub 4-46, Sub 4-48 Synthesis Example

(1) Sub 4-I-46 Synthesis

Starting material 1-amino-2-naphthoic acid (CAS Registry Number: 4919-43-1) (75.11 g, 401.25 mmol) was added to a round bottom flask with urea (CAS Registry Number: 57-13-6) (168.69 g, 2808.75 mmol) and stirred at 160 ° C. After confirming the reaction by TLC, it was cooled to 100 ℃ and water (200 ml) was added and stirred for 1 hour. When the reaction was completed, the resulting solid was filtered under reduced pressure, washed with water and dried to give 63.86 g (yield: 75%) of the product.

(2) Sub 4-II-46 Synthesis

Sub 4-I-46 (63.86 g, 300.94 mmol) obtained in the above synthesis was dissolved in a round bottom flask with POCl ₃ (200 ml) at room temperature, and then N , N- Diisopropylethylamine (97.23 g, 752.36 mmol) was slowly added dropwise. Then, it stirred at 90 degreeC. After the reaction was concentrated, ice water (500 ml) was added thereto, and the mixture was stirred at room temperature for 1 hour. The resulting solid was filtered under reduced pressure and dried to give 67.47 g (yield: 90%) of product.

(3) Sub 4-46 synthesis

Sub 4-II-46 (33.60 g, 134.89 mmol) obtained in the above synthesis with 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (CAS Registry Number: 24388-23-6) (30.28 g, 148.38 mmol), Pd (PPh ₃ ) ₄ (6.23 g, 5.40 mmol), K ₂ CO ₃ (55.93 g, 404.67 mmol), THF (470 ml), water (235 ml) were added and the product 22.36 g (Yield: 57) was obtained using the Sub 4-20 synthesis method. %) Was obtained.

(4) Sub 4-48 synthesis

To Sub 4-II-46 (27.05 g, 108.60 mmol) obtained in the above synthesis, 4,4,5,5-tetramethyl-2- (naphthalen-1-yl) -1,3,2-dioxaborolane (CAS Registry Number: 68716-52-9) (30.36 g, 119.45 mmol), Pd (PPh ₃ ) ₄ (5.02 g, 4.34 mmol), K ₂ CO ₃ (45.03 g, 325.79 mmol), THF (380 ml), water (190 ml) were added and the product 22.21 g (yield: 60) was obtained using the Sub 4-20 synthesis method. %) Was obtained.

4.Sub 4-59 Synthesis Example

Starting material 2,4-dichlorobenzo [4,5] thieno [3,2- d ] pyrimidine (CAS Registry Number: 160199-05-3) (38.00 g, 148.95 mmol) was obtained as 4,4,5,5-tetramethyl -2-phenyl-1,3,2-dioxaborolane ( CAS Registry Number: 24388-23-6) (33.44 g, 163.84 mmol), Pd (PPh 3) 4 (6.88 g, 5.96 mmol), K 2 CO 3 ( 61.76 g, 446.85 mmol), THF (520 ml), water (260 ml) were added and 17.68 g (yield: 40%) of product was obtained using the Sub 4-20 synthesis method.

5.Sub 4-64 Synthesis Example

The starting material 2,4-dichlorobenzo [4,5] thieno [3,2- d ] pyrimidine (CAS Registry Number: 160199-05-3) (35.15 g, 137.78 mmol) in 2- (dibenzo [b, d] furan-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS Registry Number: 947770-80-1) (44.58 g, 151.56 mmol), Pd (PPh ₃ ) ₄ (6.37 g, 5.51 mmol), K ₂ CO ₃ (57.13 g, 413.33 mmol), THF (480 ml), water (240 ml) were added and the product 22.92 g (yield: 43) was obtained using the Sub 4-20 synthesis method. %) Was obtained.

6.Sub 4-71 Synthesis Example

Starting material 2,4-dichlorobenzofuro [2,3-d] pyrimidine (CAS Registry Number: 1801325-92-7) (41.43 g, 173.30 mmol) to 4,4,5,5-tetramethyl-2-phenyl-1 , 3,2-dioxaborolane (CAS Registry Number: 24388-23-6) (38.90 g, 190.63 mmol), Pd (PPh ₃ ) ₄ (8.01 g, 6.93 mmol), K ₂ CO ₃ (71.86 g, 519.91 mmol) , THF (600 ml), water (300 ml) were added and 18.49 g (yield: 38%) of product was obtained using the Sub 4-20 synthesis.

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

compound	FD-MS	compound	FD-MS
Sub 4-1	m / z = 155.96 (C 6 H 5 Br = 157.01)	Sub 4-2	m / z = 205.97 (C 10 H 7 Br = 207.07)
Sub 4-3	m / z = 205.97 (C 10 H 7 Br = 207.07)	Sub 4-4	m / z = 231.99 (C 12 H 9 Br = 233.11)
Sub 4-5	m / z = 231.99 (C 12 H 9 Br = 233.11)	Sub 4-6	m / z = 308.02 (C 18 H 13 Br = 309.21)
Sub 4-7	m / z = 255.99 (C 14 H 9 Br = 257.13)	Sub 4-8	m / z = 306.00 (C 18 H 11 Br = 307.19)
Sub 4-9	m / z = 272.02 (C 15 H 13 Br = 273.17)	Sub 4-10	m / z = 310.01 (C 16 H 11 BrN 2 = 311.18)
Sub 4-11	m / z = 321.02 (C 18 H 12 BrN = 322.21)	Sub 4-12	m / z = 261.95 (C 12 H 7 BrS = 263.15)
Sub 4-13	m / z = 245.97 (C 12 H 7 BrO = 247.09)	Sub 4-14	m / z = 156.95 (C 5 H 4 BrN = 158.00)
Sub 4-15	m / z = 156.95 (C 5 H 4 BrN = 158.00)	Sub 4-16	m / z = 311.01 (C 15 H 10 BrN 3 = 312.17)
Sub 4-17	m / z = 157.95 (C 4 H 3 BrN 2 = 158.99)	Sub 4-18	m / z = 283.99 (C 14 H 9 BrN 2 = 285.14)
Sub 4-19	m / z = 310.01 (C 16 H 11 BrN 2 = 311.18)	Sub 4-20	m / z = 316.08 (C 20 H 13 ClN 2 = 316.79)
Sub 4-21	m / z = 366.09 (C 24 H 15 ClN 2 = 366.85)	Sub 4-22	m / z = 328.00 (C 16 H 10 BrFN 2 = 329.17)
Sub 4-23	m / z = 386.04 (C 22 H 15 BrN 2 = 387.28)	Sub 4-24	m / z = 310.01 (C 16 H 11 BrN 2 = 311.18)
Sub 4-25	m / z = 310.01 (C 16 H 11 BrN 2 = 311.18)	Sub 4-26	m / z = 348.99 (C 17 H 8 BrN 3 O = 350.18)
Sub 4-27	m / z = 311.01 (C 15 H 10 BrN 3 = 312.17)	Sub 4-28	m / z = 361.02 (C 19 H 12 BrN 3 = 362.23)
Sub 4-29	m / z = 361.02 (C 19 H 12 BrN 3 = 362.23)	Sub 4-30	m / z = 387.04 (C 21 H 14 BrN 3 = 388.27)
Sub 4-31	m / z = 386.04 (C 22 H 15 BrN 2 = 387.28)	Sub 4-32	m / z = 386.04 (C 22 H 15 BrN 2 = 387.28)
Sub 4-33	m / z = 387.04 (C 21 H 14 BrN 3 = 388.27)	Sub 4-34	m / z = 387.04 (C 21 H 14 BrN 3 = 388.27)
Sub 4-35	m / z = 348.03 (C 19 H 13 BrN 2 = 349.23)	Sub 4-36	m / z = 271.99 (C 13 H 9 BrN 2 = 273.13)
Sub 4-37	m / z = 240.05 (C 14 H 9 ClN 2 = 240.69)	Sub 4-38	m / z = 245.08 (C 14 H 4 D 5 ClN 2 = 245.72)
Sub 4-39	m / z = 296.11 (C 18 H 17 ClN 2 = 296.80)	Sub 4-40	m / z = 290.06 (C 18 H 11 ClN 2 = 290.75)
Sub 4-41	m / z = 290.06 (C 18 H 11 ClN 2 = 290.75)	Sub 4-42	m / z = 316.08 (C 20 H 13 ClN 2 = 316.79)
Sub 4-43	m / z = 396.05 (C 24 H 13 ClN 2 S = 396.89)	Sub 4-44	m / z = 360.03 (C 20 H 13 BrN 2 = 361.24)
Sub 4-45	m / z = 360.03 (C 20 H 13 BrN 2 = 361.24)	Sub 4-46	m / z = 290.06 (C 18 H 11 ClN 2 = 290.75)
Sub 4-47	m / z = 308.05 (C 18 H 10 ClFN 2 = 308.74)	Sub 4-48	m / z = 340.08 (C 22 H 13 ClN 2 = 340.81)
Sub 4-49	m / z = 340.08 (C 22 H 13 ClN 2 = 340.81)	Sub 4-50	m / z = 371.12 (C 24 H 10 D 5 ClN 2 = 371.88)
Sub 4-51	m / z = 396.05 (C 24 H 13 ClN 2 S = 396.89)	Sub 4-52	m / z = 380.07 (C 24 H 13 ClN 2 O = 380.83)
Sub 4-53	m / z = 516.03 (C 30 H 17 BrN 2 S = 517.44)	Sub 4-54	m / z = 290.06 (C 18 H 11 ClN 2 = 290.75)
Sub 4-55	m / z = 295.09 (C 18 H 6 D 5 ClN 2 = 295.78)	Sub 4-56	m / z = 340.08 (C 22 H 13 ClN 2 = 340.81)
Sub 4-57	m / z = 460.06 (C 28 H 17 BrN 2 = 461.36)	Sub 4-58	m / z = 262.03 (C 13 H 11 ClN 2 S = 262.76)
Sub 4-59	m / z = 296.02 (C 16 H 9 ClN 2 S = 296.77)	Sub 4-60	m / z = 346.03 (C 20 H 11 ClN 2 S = 346.83)
Sub 4-61	m / z = 346.03 (C 20 H 11 ClN 2 S = 346.83)	Sub 4-62	m / z = 372.05 (C 22 H 13 ClN 2 S = 372.87)
Sub 4-63	m / z = 386.06 (C 23 H 15 ClN 2 S = 386.90)	Sub 4-64	m / z = 386.03 (C 22 H 11 ClN 2 OS = 386.85)
Sub 4-65	m / z = 346.03 (C 20 H 11 ClN 2 S = 346.83)	Sub 4-66	m / z = 416.00 (C 22 H 13 BrN 2 S = 417.32)
Sub 4-67	m / z = 416.00 (C 22 H 13 BrN 2 S = 417.32)	Sub 4-68	m / z = 280.04 (C 16 H 9 ClN 2 O = 280.71)
Sub 4-69	m / z = 432.10 (C 28 H 17 ClN 2 O = 432.91)	Sub 4-70	m / z = 331.05 (C 19 H 10 ClN 3 O = 331.76)
Sub 4-71	m / z = 280.04 (C 16 H 9 ClN 2 O = 280.71)	Sub 4-72	m / z = 358.09 (C 22 H 15 ClN 2 O = 358.83)

III. Final Product 2 Synthesis

Sub 3 (1 equiv) is dissolved in toluene in a round bottom flask, then Sub 4 (1.1 equiv), Pd ₂ (dba) ₃ (0.03 equiv), (t-Bu) 3 P (0.06 equiv) and NaOt-Bu (3 equiv) were stirred at 100 ° C. After completion of the reaction, the mixture was extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was purified by silicagel column and recrystallized to obtain Final product 2.

1.3-1 Synthesis Example

Sub 3-1 (10.00 g, 26.15 mmol) obtained in the above synthesis was dissolved in toluene (275 ml) in a round bottom flask, and then Sub 4-1 (CAS Registry Number: 108-86-1) (4.52 g, 28.76 mmol) ), Pd ₂ (dba) ₃ (0.72 g, 0.78 mmol), P ( t -Bu) ₃ (0.32 g, 1.57 mmol), NaO t -Bu (7.54 g, 78.44 mmol) were added and stirred at 100 ° C. . After the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was purified by silicagel column and recrystallized to give the product 8.63 g (yield: 72%).

2. 3-6 Synthesis Example

To Sub 3-15 (10.00 g, 30.92 mmol) obtained in the above synthesis, Sub 4-37 (CAS Registry Number: 29874-83-7) (8.19 g, 34.01 mmol), Pd ₂ (dba) ₃ (0.85 g, 0.93 mmol) P ( t -Bu) ₃ (0.38 g, 1.86 mmol), NaO t -Bu (8.92 g, 92.76 mmol), toluene (325 ml) were added and the product 10.93 g (yield) was obtained using the above 3-1 synthesis method. : 67%).

3. 3-7 Synthesis Example

To Sub 3-15 (10.00 g, 30.92 mmol) obtained in the above synthesis, Sub 4-59 (10.09 g, 34.01 mmol), Pd ₂ (dba) ₃ (0.85 g, 0.93 mmol) P ( t -Bu) ₃ (0.38 g, 1.86 mmol), NaO t -Bu (8.92 g, 92.76 mmol), toluene (325 ml) were added and 12.81 g (yield: 71%) of the product was obtained using the 3-1 synthesis method.

4. 3-8 Synthesis Example

To Sub 3-15 (10.00 g, 30.92 mmol) obtained in the above synthesis, Sub 4-46 (9.89 g, 34.01 mmol), Pd ₂ (dba) ₃ (0.85 g, 0.93 mmol) P ( t- Bu) ₃ (0.38 g, 1.86 mmol), NaO t -Bu (8.92 g, 92.76 mmol), toluene (325 ml) were added and 13.04 g (yield: 73%) of product was obtained using the 3-1 synthesis method.

5. 3-11 Synthesis Example

To Sub 3-33 (10.00 g, 27.98 mmol) obtained in the above synthesis, Sub 4-6 (CAS Registry Number: 103068-20-8) (9.52 g, 30.78 mmol), Pd ₂ (dba) ₃ (0.77 g, 0.84 mmol) P ( t -Bu) ₃ (0.34 g, 1.68 mmol), NaO t -Bu (8.07 g, 83.94 mmol), toluene (294 ml) were added and the product 12.45 g (yield) was obtained using the above 3-1 synthesis method. : 76%).

6. 3-16 Synthesis Example

To Sub 3-90 (10.00 g, 26.08 mmol) obtained in the above synthesis Sub 4-11 (CAS Registry Number: 1153-85-1) (9.24 g, 28.68 mmol), Pd ₂ (dba) ₃ (0.72 g, 0.78 mmol) P ( t -Bu) ₃ (0.32 g, 1.56 mmol), NaO t -Bu (7.52 g, 78.23 mmol), toluene (274 ml) were added and the product 1 .08 g (yield) was synthesized using the above 3-1 synthesis. : 68%).

7. 3-17 Synthesis Example

To Sub 3-57 (10.00 g, 23.12 mmol) obtained in the above synthesis, Sub 4-12 (CAS Registry Number: 97511-04-1) (6.69 g, 25.43 mmol), Pd ₂ (dba) ₃ (0.64 g, 0.69 mmol) P ( t -Bu) ₃ (0.28 g, 1.39 mmol), NaO t -Bu (6.67 g, 69.36 mmol), toluene (243 ml) were added and the product 11.80 g (yield) was obtained using the above 3-1 synthesis method. : 83%).

8. 3-47 Synthesis Example

To Sub 3-75 (10.00 g, 27.98 mmol) obtained in the above synthesis, Sub 4-71 (8.64 g, 30.78 mmol), Pd ₂ (dba) ₃ (0.77 g, 0.84 mmol) P ( t- Bu) ₃ (0.34 g, 1.68 mmol), NaO t -Bu (8.07 g, 83.94 mmol), toluene (294 ml) were added and the product 1 .45 g (yield: 68%) was obtained using the 3-1 synthesis method.

9. 3-52 Synthesis Example

To Sub 3-41 (10.00 g, 29.99 mmol) obtained in the above synthesis, Sub 4-32 (12.78 g, 32.99 mmol), Pd ₂ (dba) ₃ (0.82 g, 0.90 mmol) P ( t- Bu) ₃ (0.36 g, 1.80 mmol), NaO t -Bu (8.65 g, 89.97 mmol), toluene (500 ml) were added and 13.82 g (yield: 72%) of the product was obtained using the above 3-1 synthesis method.

10. 3-70 Synthesis Example

To Sub 3-64 (10.00 g, 26.78 mmol) obtained in the above synthesis, Sub 4-48 (10.04 g, 29.45 mmol), Pd ₂ (dba) ₃ (0.74 g, 0.80 mmol) P ( t -Bu) ₃ (0.33 g, 1.61 mmol), NaO t -Bu (7.72 g, 80.33 mmol) and toluene (281 ml) were added and the product 12.16 g (yield: 67%) was obtained using the 3-1 synthesis method.

11.3-81 Synthesis Example

To Sub 3-15 (10.00 g, 30.92 mmol) obtained in the above synthesis, Sub 4-20 (10.77 g, 34.01 mmol), Pd ₂ (dba) ₃ (0.85 g, 0.93 mmol) P ( t- Bu) ₃ (0.38 g, 1.86 mmol), NaO t -Bu (8.92 g, 92.76 mmol), toluene (325 ml) were added and 13.44 g (yield: 72%) of product was obtained using the 3-1 synthesis method.

12. 3-93 Synthesis Example

Sub 3-22 (10.00 g, 26.78 mmol) obtained in the above synthesis in Sub 4-27 (CAS Registry Number: 80984-79-8) (9.19 g, 29.45 mmol), Pd ₂ (dba) ₃ (0.74 g, 0.80 mmol) P ( t -Bu) ₃ (0.33 g, 1.61 mmol), NaO t -Bu (7.72 g, 80.33 mmol), toluene (281 ml) were added and the product 11.33 g (yield) was obtained using the above 3-1 synthesis method. : 70%).

compound	FD-MS	compound	FD-MS
3-1	m / z = 458.18 (C 34 H 22 N 2 = 458.56)	3-2	m / z = 449.12 (C 32 H 19 NS = 449.57)
3-3	m / z = 433.15 (C 32 H 19 NO = 433.51)	3-4	m / z = 535.23 (C 41 H 29 N = 535.69)
3-5	m / z = 399.11 (C 28 H 17 NS = 399.51)	3-6	m / z = 527.15 (C 36 H 21 N 3 S = 527.65)
3-7	m / z = 583.12 (C 38 H 21 N 3 S 2 = 583.73)	3-8	m / z = 577.16 (C 40 H 23 N 3 S = 577.71)
3-9	m / z = 627.18 (C 44 H 25 N 3 S = 627.77)	3-10	m / z = 475.14 (C 34 H 21 NS = 475.61)
3-11	m / z = 585.21 (C 44 H 27 NO = 585.71)	3-12	m / z = 509.21 (C 39 H 27 N = 509.65)
3-13	m / z = 509.19 (C 37 H 23 N 3 = 509.61)	3-14	m / z = 451.11 (C 30 H 17 N 3 S = 451.55)
3-15	m / z = 588.20 (C 41 H 24 N 4 O = 588.67)	3-16	m / z = 624.26 (C 47 H 32 N 2 = 624.79)
3-17	m / z = 614.18 (C 44 H 26 N 2 S = 614.77)	3-18	m / z = 449.12 (C 32 H 19 NS = 449.57)
3-19	m / z = 573.17 (C 42 H 23 NO 2 = 573.65)	3-20	m / z = 664.26 (C 48 H 32 N 4 = 664.81)
3-21	m / z = 624.26 (C 47 H 32 N 2 = 624.79)	3-22	m / z = 577.16 (C 40 H 23 N 3 S = 577.71)
3-23	m / z = 664.23 (C 47 H 28 N 4 O = 664.77)	3-24	m / z = 737.28 (C 55 H 35 N 3 = 737.91)
3-25	m / z = 738.28 (C 54 H 34 N 4 = 738.89)	3-26	m / z = 679.21 (C 48 H 29 N 3 S = 679.84)
3-27	m / z = 625.22 (C 45 H 27 N 3 O = 625.73)	3-28	m / z = 575.24 (C 42 H 29 N 3 = 575.72)
3-29	m / z = 508.19 (C 38 H 24 N 2 = 508.62)	3-30	m / z = 449.12 (C 32 H 19 NS = 449.57)
3-31	m / z = 433.15 (C 32 H 19 NO = 433.51)	3-32	m / z = 531.20 (C 41 H 25 N = 531.66)
3-33	m / z = 608.23 (C 46 H 28 N 2 = 608.74)	3-34	m / z = 475.14 (C 34 H 21 NS = 475.61)
3-35	m / z = 384.13 (C 27 H 16 N 2 O = 384.44)	3-36	m / z = 614.25 (C 44 H 30 N 4 = 614.75)
3-37	m / z = 508.19 (C 38 H 24 N 2 = 508.62)	3-38	m / z = 449.12 (C 32 H 19 NS = 449.57)
3-39	m / z = 433.15 (C 32 H 19 NO = 433.51)	3-40	m / z = 459.20 (C 35 H 25 N = 459.59)
3-41	m / z = 663.24 (C 47 H 29 N 5 = 663.78)	3-42	m / z = 603.18 (C 42 H 25 N 3 S = 603.74)
3-43	m / z = 587.20 (C 42 H 25 N 3 O = 587.68)	3-44	m / z = 613.25 (C 45 H 31 N 3 = 613.76)
3-45	m / z = 662.25 (C 48 H 30 N 4 = 662.80)	3-46	m / z = 577.16 (C 40 H 23 N 3 S = 577.71)
3-47	m / z = 601.18 (C 42 H 23 N 3 O 2 = 601.67)	3-48	m / z = 759.27 (C 57 H 33 N 3 = 759.91)
3-49	m / z = 586.22 (C 42 H 26 N 4 = 586.70)	3-50	m / z = 630.19 (C 43 H 26 N 4 S = 630.77)
3-51	m / z = 613.22 (C 44 H 27 N 3 O = 613.72)	3-52	m / z = 639.27 (C 47 H 33 N 3 = 639.80)
3-53	m / z = 508.19 (C 38 H 24 N 2 = 508.62)	3-54	m / z = 449.12 (C 32 H 19 NS = 449.57)
3-55	m / z = 433.15 (C 32 H 19 NO = 433.51)	3-56	m / z = 609.25 (C 47 H 31 N = 609.77)
3-57	m / z = 663.24 (C 47 H 29 N 5 = 663.78)	3-58	m / z = 604.17 (C 41 H 24 N 4 S = 604.73)
3-59	m / z = 587.20 (C 42 H 25 N 3 O = 587.68)	3-60	m / z = 613.25 (C 45 H 31 N 3 = 613.76)
3-61	m / z = 527.15 (C 36 H 21 N 3 S = 527.65)	3-62	m / z = 603.18 (C 42 H 25 N 3 S = 603.74)
3-63	m / z = 516.20 (C 36 H 16 D 5 N 3 O = 516.61)	3-64	m / z = 605.23 (C 43 H 28 FN 3 = 605.72)
3-65	m / z = 692.20 (C 48 H 28 N 4 S = 692.84)	3-66	m / z = 577.16 (C 40 H 23 N 3 S = 577.71)
3-67	m / z = 561.18 (C 40 H 23 N 3 O = 561.64)	3-68	m / z = 653.19 (C 46 H 27 N 3 S = 653.80)
3-69	m / z = 736.26 (C 54 H 32 N 4 = 736.88)	3-70	m / z = 677.19 (C 48 H 27 N 3 S = 677.83)
3-71	m / z = 742.28 (C 54 H 26 D 5 N 3 O = 742.89)	3-72	m / z = 743.24 (C 53 H 33 N 3 S = 743.93)
3-73	m / z = 753.22 (C 54 H 31 N 3 S = 753.92)	3-74	m / z = 603.18 (C 42 H 25 N 3 S = 603.74)
3-75	m / z = 659.15 (C 44 H 25 N 3 S 2 = 659.83)	3-76	m / z = 759.18 (C 52 H 29 N 3 S 2 = 759.95)
3-77	m / z = 475.14 (C 34 H 21 NS = 475.61)	3-78	m / z = 616.20 (C 44 H 28 N 2 S = 616.78)
3-79	m / z = 818.16 (C 53 H 27 FN 4 OS 2 = 818.94)	3-80	m / z = 818.25 (C 58 H 34 N 4 S = 819.00)
3-81	m / z = 603.18 (C 42 H 25 N 3 S = 603.74)	3-82	m / z = 809.20 (C 56 H 31 N 3 S 2 = 810.01)
3-83	m / z = 659.15 (C 44 H 25 N 3 S 2 = 659.83)	3-84	m / z = 633.22 (C 44 H 31 N 3 S = 633.81)
3-85	m / z = 844.27 (C 60 H 36 N 4 S = 845.04)	3-86	m / z = 667.17 (C 46 H 25 N 3 OS = 667.79)
3-87	m / z = 703.23 (C 50 H 29 N 3 O = 703.80)	3-88	m / z = 759.25 (C 53 H 33 N 3 O 3 = 759.87)
3-89	m / z = 677.19 (C 48 H 27 N 3 S = 677.83)	3-90	m / z = 683.15 (C 46 H 25 N 3 S 2 = 683.85)
3-91	m / z = 668.17 (C 45 H 24 N 4 OS = 668.77)	3-92	m / z = 653.19 (C 46 H 27 N 3 S = 653.80)
3-93	m / z = 604.17 (C 41 H 24 N 4 S = 604.73)	3-94	m / z = 650.27 (C 49 H 34 N 2 = 650.83)
3-95	m / z = 878.30 (C 64 H 38 N 4 O = 879.04)	3-96	m / z = 775.26 (C 57 H 33 N 3 O = 775.91)
3-97	m / z = 588.20 (C 41 H 24 N 4 O = 588.67)	3-98	m / z = 561.18 (C 40 H 23 N 3 O = 561.64)
3-99	m / z = 602.17 (C 41 H 22 N 4 O 2 = 602.65)	3-100	m / z = 664.23 (C 47 H 28 N 4 O = 664.77)
3-101	m / z = 653.19 (C 46 H 27 N 3 S = 653.80)	3-102	m / z = 617.16 (C 42 H 23 N 3 OS = 617.73)
3-103	m / z = 654.19 (C 45 H 26 N 4 S = 654.79)	3-104	m / z = 740.26 (C53H32N4O = 740.87)
3-105	m / z = 680.20 (C 47 H 28 N 4 S = 680.83)	3-106	m / z = 681.26 (C 49 H 32 FN 3 = 681.81)
3-107	m / z = 649.16 (C 43 H 27 N 3 S 2 = 649.83)	3-108	m / z = 832.27 (C 59 H 36 N 4 S = 833.03)
3-109	m / z = 587.20 (C 42 H 25 N 3 O = 587.68)	3-110	m / z = 654.19 (C 45 H 26 N 4 S = 654.79)
3-111	m / z = 667.17 (C 46 H 25 N 3 OS = 667.79)	3-112	m / z = 616.23 (C 44 H 20 D 5 N 3 O = 616.73)
3-113	m / z = 692.17 (C 47 H 24 N 4 OS = 692.80)	3-114	m / z = 729.22 (C 52 H 31 N 3 S = 729.90)
3-115	m / z = 759.18 (C 52 H 29 N 3 S 2 = 759.95)

On the other hand, in the above described exemplary synthetic examples of the present invention represented by the formula (1) and (2), these are all Buchwald-Hartwig cross coupling reaction, Miyaura boration reaction, Suzuki cross-coupling reaction, Intramolecular acid-induced cyclization reaction ( J . mater. Chem. 1999, 9 , 2095.), Pd (II) -catalyzed oxidative cyclization reaction (Org. Lett. 2011, 13 , 5504), Grignard reaction, Cyclic Dehydration reaction and PPh ₃ -mediated reductive cyclization reaction (J . Org. Chem. 2005, 70 , 5014.) the other substituents defined or the like in addition to the substituents specifically set forth in synthesis example 1 in the general formula and general formula (2) based (Ar ¹ to Ar ^3, L ¹ to L ^2, R ¹ to R ⁷ It will be readily understood by those skilled in the art that the reaction proceeds even when the substituents (X ¹ , X ² , X ³ , A, B, C, D, E, F, etc.) are combined.

Manufacturing Evaluation of Organic Electrical Device

[ Example  1] to [ Example  95] Red organic electroluminescent device  ( Light emitting layer  Mixed phosphorescent host)

First, a 4,4 ', 4 "-Tris [2-naphthyl (phenyl) amino] triphenylamine (abbreviated as 2-TNATA) film was vacuum deposited on the ITO layer (anode) formed on the glass substrate as a hole injection layer. And then N, N'-Bis (1-naphthalenyl) -N, N'-bis-phenyl- (1,1'-biphenyl) -4,4'-diamine (hereinafter abbreviated as NPB). The hole transport layer was formed by vacuum deposition to a thickness of 60 nm, and a mixture of the compound of the present invention represented by Formula 1 and Formula 2 (described in Table 7) 3: 7 was used as a host on the hole transport layer. 30 nm thick light emitting layer was deposited on the hole transport layer by doping (piq) ₂ Ir (acac) [bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate] at 5% by weight. (1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinolineoleito) aluminum (hereinafter abbreviated as BAlq) was vacuum deposited to a thickness of 10 nm and tris (8-quinol) as an electron transport layer. NOR) aluminum (hereinafter abbreviated as Alq3) was deposited to a thickness of 40 nm, followed by deposition of LiF, an alkali metal halide, to a thickness of 0.2 nm, followed by deposition of Al to a thickness of 150 nm as an electron injection layer. By using the organic electroluminescent device was prepared.

[ Comparative example  1] to [ Comparative example  3]

An organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound of the present invention represented by Formula 2 as a host.

[ Comparative example  4]

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

[ Comparative example  5]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 2 was used alone.

[ Comparative example  6]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 3 was used alone.

[ Comparative example  7]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 4 was used alone.

[ Comparative example  8]

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

[ Comparative example  9]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 3 and Comparative Compound 4 were used as a host.

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

Electroluminescence (EL) characteristics by PR-650 of photoresearch by applying a forward bias DC voltage to the organic electroluminescent devices prepared in Examples 1 to 95 and Comparative Examples 1 to 9 of the present invention The T95 life was measured using a McScience Lifetime Measurement Equipment at 2500 cd / m ² reference luminance, and the measurement results are shown in Table 7 below.

	Host 1	Host 2	Driving voltage (V)	Current (mA / cm 2)	Luminance (cd / m 2 )	Efficiency (cd / A)	T (95)
Comparative Example (1)	-	Compound (3-6)	6.1	15.7	2500	15.9	108.9
Comparative Example (2)	-	Compound (3-61)	6.3	16.2	2500	15.5	104.2
Comparative Example (3)	-	Compound (3-74)	6.4	16.2	2500	15.4	103.2
Comparative Example (4)	-	Comparative Compound 1	6.9	18.6	2500	13.4	84.3
Comparative Example (5)	-	Comparative Compound 2	6.8	18.3	2500	13.7	83.3
Comparative Example (6)	-	Comparative Compound 3	6.7	17.5	2500	14.3	87.4
Comparative Example (7)	-	Comparative Compound 4	6.9	18.4	2500	13.6	82.9
Comparative Example (8)	Comparative Compound 1	Comparative Compound 2	5.9	13	2500	19.3	103.8
Comparative Example (9)	Comparative Compound 3	Comparative Compound 4	5.6	10.5	2500	23.9	108.9
Example (1)	Compound 1-10	Compound 3-6	4.6	7.0	2500	35.9	137.9
Example (2)	Compound 1-23	Compound 3-6	4.7	7.1	2500	35.2	137.6
Example (3)	Compound 1-56	Compound 3-6	4.8	6.7	2500	37.4	137.6
Example (4)	Compound 2-3	Compound 3-6	4.6	6.8	2500	36.9	136.2
Example (5)	Compound 2-11	Compound 3-6	4.6	6.2	2500	40.6	138.4
Example (6)	Compound 2-27	Compound 3-6	4.7	6.6	2500	37.7	138.3
Example (7)	Compound 2-31	Compound 3-6	4.5	6.1	2500	41.3	139.3
Example (8)	Compound 2-41	Compound 3-6	4.7	6.8	2500	36.5	137.5
Example (9)	Compound 2-48	Compound 3-6	4.5	5.8	2500	43.2	142.2
Example (10)	Compound 2-98	Compound 3-6	4.8	6.6	2500	37.8	139.0
Example (11)	Compound 1-10	Compound 3-7	4.7	8.4	2500	29.8	126.5
Example (12)	Compound 1-23	Compound 3-7	4.8	8.4	2500	29.7	126.0
Example (13)	Compound 1-56	Compound 3-7	4.8	8.2	2500	30.5	127.4
Example (14)	Compound 2-3	Compound 3-7	4.8	8.3	2500	30.2	127.0
Example (15)	Compound 2-11	Compound 3-7	4.8	8.1	2500	30.9	130.5
Example (16)	Compound 2-27	Compound 3-7	4.8	8.2	2500	30.5	126.8
Example (17)	Compound 2-31	Compound 3-7	4.8	8.1	2500	30.9	129.6
Example (18)	Compound 2-41	Compound 3-7	4.7	8.3	2500	30.0	127.7
Example (19)	Compound 2-48	Compound 3-7	4.7	8.1	2500	30.9	130.9
Example (20)	Compound 2-98	Compound 3-7	4.9	8.2	2500	30.6	126.5
Example (21)	Compound 1-10	Compound 3-8	4.8	8.5	2500	29.5	127.3
Example (22)	Compound 1-23	Compound 3-8	4.7	8.5	2500	29.6	126.6
Example (23)	Compound 1-56	Compound 3-8	4.7	8.2	2500	30.6	126.4
Example (24)	Compound 2-3	Compound 3-8	4.9	8.3	2500	30.1	126.8
Example (25)	Compound 2-11	Compound 3-8	4.7	8.1	2500	31.0	129.7
Example (26)	Compound 2-27	Compound 3-8	4.7	8.1	2500	30.7	126.7
Example (27)	Compound 2-31	Compound 3-8	4.8	8.1	2500	30.8	129.8
Example (28)	Compound 2-41	Compound 3-8	4.8	8.3	2500	30.1	126.5
Example (29)	Compound 2-48	Compound 3-8	4.7	8.1	2500	31.0	131.0
Example (30)	Compound 2-98	Compound 3-8	4.8	8.2	2500	30.4	126.5
Example (31)	Compound 1-70	Compound 3-9	4.8	8.7	2500	28.7	126.2
Example (32)	Compound 2-23	Compound 3-9	4.9	8.4	2500	29.9	128.0
Example (33)	Compound 2-24	Compound 3-9	4.8	8.4	2500	29.7	128.7
Example (34)	Compound 2-53	Compound 3-9	4.7	8.6	2500	29.2	126.5
Example (35)	Compound 2-80	Compound 3-9	4.9	8.5	2500	29.3	127.3
Example (36)	Compound 1-10	Compound 3-15	4.8	8.7	2500	28.6	126.9
Example (37)	Compound 1-23	Compound 3-15	4.7	8.8	2500	28.3	126.9
Example (38)	Compound 1-56	Compound 3-15	4.8	8.5	2500	29.3	127.5
Example (39)	Compound 2-3	Compound 3-15	4.8	8.6	2500	29.0	128.0
Example (40)	Compound 2-11	Compound 3-15	4.8	8.4	2500	29.9	128.4
Example (41)	Compound 2-27	Compound 3-15	4.7	8.5	2500	29.3	126.6
Example (42)	Compound 2-31	Compound 3-15	4.8	8.5	2500	29.6	128.7
Example (43)	Compound 2-41	Compound 3-15	4.8	8.6	2500	28.9	127.9
Example (44)	Compound 2-48	Compound 3-15	4.7	8.3	2500	30.0	129.1
Example (45)	Compound 2-98	Compound 3-15	4.9	8.6	2500	29.1	127.2
Example (46)	Compound 1-10	Compound 3-37	5.0	9.2	2500	27.2	123.6
Example (47)	Compound 1-23	Compound 3-37	5.0	9.3	2500	27.0	123.5
Example (48)	Compound 1-56	Compound 3-37	4.8	9.0	2500	27.8	124.6
Example (49)	Compound 2-3	Compound 3-37	4.9	9.1	2500	27.4	124.8
Example (50)	Compound 2-11	Compound 3-37	4.8	8.9	2500	28.2	126.4
Example (51)	Compound 2-27	Compound 3-37	4.9	9.0	2500	27.8	124.1
Example (52)	Compound 2-31	Compound 3-37	4.9	8.9	2500	28.2	126.2
Example (53)	Compound 2-41	Compound 3-37	4.9	9.1	2500	27.4	124.5
Example (54)	Compound 2-48	Compound 3-37	4.9	8.8	2500	28.4	126.4
Example (55)	Compound 2-98	Compound 3-37	4.9	8.9	2500	28.0	124.6
Example (56)	Compound 1-39	Compound 3-46	4.7	8.2	2500	30.5	128.6
Example (57)	Compound 1-68	Compound 3-46	4.7	8.5	2500	29.5	127.1
Example (58)	Compound 2-15	Compound 3-46	4.8	8.0	2500	31.4	130.8
Example (59)	Compound 2-33	Compound 3-46	4.7	8.0	2500	31.3	130.8
Example (60)	Compound 2-49	Compound 3-46	4.7	8.1	2500	31.0	129.9
Example (61)	Compound 1-39	Compound 3-50	4.9	8.3	2500	30.2	127.3
Example (62)	Compound 1-68	Compound 3-50	4.8	8.4	2500	29.8	127.7
Example (63)	Compound 2-15	Compound 3-50	4.8	8.1	2500	31.0	129.4
Example (64)	Compound 2-33	Compound 3-50	4.8	8.1	2500	30.9	129.3
Example (65)	Compound 2-49	Compound 3-50	4.8	7.9	2500	31.5	130.4
Example (66)	Compound 1-10	Compound 3-61	4.7	7.8	2500	31.9	130.7
Example (67)	Compound 1-23	Compound 3-61	4.8	7.7	2500	32.3	131.7
Example (68)	Compound 1-56	Compound 3-61	4.7	7.4	2500	33.7	130.3
Example (69)	Compound 2-3	Compound 3-61	4.8	7.6	2500	32.8	131.9
Example (70)	Compound 2-11	Compound 3-61	4.6	7.2	2500	34.6	134.7
Example (71)	Compound 2-27	Compound 3-61	4.7	7.4	2500	33.7	131.0
Example (72)	Compound 2-31	Compound 3-61	4.7	7.4	2500	34.0	134.6
Example (73)	Compound 2-41	Compound 3-61	4.7	7.6	2500	33.0	132.6
Example (74)	Compound 2-48	Compound 3-61	4.6	7.2	2500	34.7	136.1
Example (75)	Compound 2-98	Compound 3-61	4.6	7.5	2500	33.4	131.2
Example (76)	Compound 1-39	Compound 3-74	4.9	8.2	2500	30.4	128.4
Example (77)	Compound 1-68	Compound 3-74	4.8	8.5	2500	29.5	126.1
Example (78)	Compound 2-15	Compound 3-74	4.7	8.0	2500	31.4	130.7
Example (79)	Compound 2-33	Compound 3-74	4.7	8.0	2500	31.3	130.6
Example (80)	Compound 2-49	Compound 3-74	4.8	8.1	2500	30.9	130.0
Example (81)	Compound 1-39	Compound 3-81	4.8	8.3	2500	30.1	126.6
Example (82)	Compound 1-68	Compound 3-81	4.7	8.4	2500	29.7	127.9
Example (83)	Compound 2-15	Compound 3-81	4.7	8.0	2500	31.1	129.2
Example (84)	Compound 2-33	Compound 3-81	4.7	8.1	2500	31.0	129.5
Example (85)	Compound 2-49	Compound 3-81	4.7	7.9	2500	31.5	130.9
Example (86)	Compound 1-10	Compound 3-93	4.9	8.4	2500	29.6	126.2
Example (87)	Compound 1-23	Compound 3-93	4.8	8.4	2500	29.7	126.4
Example (88)	Compound 1-56	Compound 3-93	4.8	8.2	2500	30.4	127.2
Example (89)	Compound 2-3	Compound 3-93	4.8	8.3	2500	30.1	127.9
Example (90)	Compound 2-11	Compound 3-93	4.7	8.1	2500	30.8	129.6
Example (91)	Compound 2-27	Compound 3-93	4.8	8.2	2500	30.6	126.4
Example (92)	Compound 2-31	Compound 3-93	4.7	8.1	2500	31.0	130.5
Example (93)	Compound 2-41	Compound 3-93	4.7	8.3	2500	30.2	126.2
Example (94)	Compound 2-48	Compound 3-93	4.8	8.0	2500	31.2	129.8
Example (95)	Compound 2-98	Compound 3-93	4.8	8.2	2500	30.4	127.2

As can be seen from the results of Table 7, when the organic electroluminescent device material of the present invention represented by Formula 1 and Formula 2 is mixed and used as a phosphorescent host (Examples 1 to 95), a device using a single material Compared with (Comparative Examples 1 to 7), it was confirmed that the driving voltage, efficiency, and lifespan were remarkably improved.

In detail, the compounds of the present invention represented by the compounds of the present invention (3-6, 3-61, 3) using the compounds of the present invention represented by the general formula (2) and Comparative Compounds 1 to 4 alone as phosphorescent hosts It was confirmed that Comparative Examples 1 to 3 using -74) showed higher efficiency and higher lifetime than Comparative Examples 4 to 7 using the comparative compound.

In addition, Comparative Examples 8 and 9, which are used as a phosphorescent host by mixing Comparative Compound 1, Comparative Compound 2, or Comparative Compound 3, and Comparative Compound 4 than Comparative Examples 1 to 7 using the single substance, exhibit higher efficiency. I could confirm that. Comparing Comparative Example 8 and Comparative Example 9, a heterocyclic polycyclic compound having heteroatoms (N, S) different from each other in the 5-ring cyclic compound is compared to Comparative Example 8 in which a 5-ring heterocyclic compound having the same nitrogen atom is mixed. It was confirmed that Comparative Example 9 using the mixture included showed a higher efficiency.

And compared to the case of Comparative Examples 1 to 9 it was confirmed that Example 1 to Example 95 used as a host by mixing the compound of the formula 1 and the compound of the present invention exhibits a significantly higher efficiency and life, It was confirmed that the driving voltage was shown.

The inventors of the present invention determine that each of the substances of the compound of Formula 1 and the compound of Formula 2 have new characteristics other than those of the substances, based on the experimental results, the substance of Formula 1, the substance of Formula 2 , PL lifetime was measured using the mixture of the present invention. As a result, when the compound of Formula 1 and Formula 2 of the present invention were mixed, it was confirmed that a new PL wavelength was formed differently from the case of a single compound. It was confirmed that the decrease and disappearance time increased from about 60 times to as much as about 360 times. This means that when the compounds of the present invention are used in combination, not only electrons and holes move through the energy levels of the respective materials, but also electrons, hole movements or energy due to exciplexes having new energy levels formed by mixing. The transmission is believed to increase efficiency and lifetime. This can be said to be an important example that the mixed thin film shows the exciplex energy transfer and light emission process when using the mixture of the present invention as a result.

In addition, the combination of the present invention is superior to Comparative Example 8 to Comparative Compound 9, which is used as a phosphorescent host mixed with a comparative compound, because the polycyclic cyclic compound represented by the formula (2) is characterized by not only electrons but also stability against holes and high T1. When the compound represented by Formula 1 having strong hole properties is mixed, electron blocking ability is improved due to high T1 and high LUMO energy values, and more holes are quickly and easily moved to the light emitting layer. As a result, the charge balance in the light emitting layer of holes and electrons is increased, so that light is emitted inside the light emitting layer rather than at the hole transport layer interface. . In addition, in the compound represented by Formula 1, the compound of the present invention, in which fluorene was substituted with a fused spy amine, showed the best results in terms of driving voltage, efficiency, and lifetime. When dimethyl fluorene is substituted for amine together with fluorene, it was confirmed that the light emission efficiency was further improved. In other words, it is concluded that the combination of Formula 1 and Formula 2 synergistically improves the performance of the entire device.

[ Example  96] to [ Example  98] Mixed ratio Red organic electroluminescent device  ( Light emitting layer  Mixed phosphorescent host)

An organic electroluminescent device was manufactured in the same manner as in Example 68, except for using a different mixing cost of materials as described in Table 8.

[ Example  99] to [ Example  101] Mixed ratio Red organic electroluminescent device  ( Light emitting layer  Mixed phosphorescent host)

An organic electroluminescent device was manufactured according to the same method as Example 9 except for using a different mixing cost of materials as described in Table 8.

Electroluminescence (EL) characteristics by PR-650 of photoresearch by applying a forward bias DC voltage to the organic electroluminescent devices prepared in Examples 9, 68 and 96-101 of the present invention The T95 lifetime was measured using the McScience Lifetime Measurement Equipment at 2500 cd / m ² reference luminance, and the measurement results are shown in Table 8 below.

	First host	2nd host	Mixing ratio (first host: second host)	Driving voltage	Current (mA / cm 2 )	Luminance (cd / m 2 )	Efficiency (cd / A)	T (95)
Example (96)	Compound 1-56	Compound 3-61	2: 8	4.6	7.4	2500	34.0	133.5
Example (68)	Compound 1-56	Chemical 3-61	3: 7	4.7	7.4	2500	33.7	130.3
Example (97)	Compound 1-56	Compound 3-61	4: 6	4.9	8.1	2500	30.8	128.2
Example (98)	Compound 1-56	Compound 3-61	5: 5	5.1	8.7	2500	28.6	125.8
Example (99)	Compound 2-48	Compound 3-6	2: 8	4.5	5.8	2500	42.8	139.7
Example (9)	Compound 2-48	Compound 3-6	3: 7	4.5	5.8	2500	43.2	142.2
Example (100)	Compound 2-48	Compound 3-6	4: 6	4.7	6.5	2500	38.4	138.5
Example (101)	Compound 2-48	Compound 3-6	5: 5	4.9	7.3	2500	34.2	137.9

As shown in Table 8, the mixture of the compound of the present invention was measured by manufacturing a device by ratio (2: 8, 3: 7, 4: 6, 5: 5). In detail, the results of the mixture of compound 1-56 and compound 3-61 showed similarly excellent driving voltage, efficiency and lifetime for 2: 8 and 3: 7. As the ratio of the first host was increased, the results of driving voltage, efficiency, and lifespan were gradually decreased, which was the same in the mixture of Compound 2-48 and Compound 3-6. This may be explained because the charge balance in the light emitting layer is maximized when an appropriate amount of the compound represented by Chemical Formula 1 having strong hole characteristics such as 2: 8 and 3: 7 is mixed.

The above description is merely illustrative of the present invention, and those skilled in the art to which the present invention pertains may various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed herein are not intended to limit the present invention but to describe the present invention, and the spirit and scope of the present invention are not limited thereto. The protection scope of the present invention should be interpreted by the following claims, and all the technologies within the equivalent scope should be interpreted as being included in the scope of the present invention.

Claims (20)

1. An organic electric device comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes a light emitting layer, and the light emitting layer is represented by Chemical Formula 1 as a phosphorescent light emitting layer. An organic electric device comprising a first host compound and a second host compound represented by Formula 2

            Formula 1 Formula 2

   

   {In Formula 1 and 2,

   1) X ¹ is CR ^a R ^b or the following Chemical Formula 1-a,

   Formula 1-a

   

   In Formula 1-a, the dotted line represents a bond from X ¹ ,

   2) X ² and X ³ are independently of each other NL ³ -Ar ⁴ , O, S, CR ^a R ^b or the formula 1-a, wherein the dotted line in the formula 1-a is a bond from X ² or X ³ Indicates

   3) R ^a and R ^b are independently of each other hydrogen; C ₆ -C ₆₀ aryl group; Fluorenyl groups; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; An alkyl group of C ₁ -C ₅₀ ; C ₂ -C ₂₀ Alkenyl group; It is selected from the group consisting of,

   4) h and i are integers of 0 or 1, provided that h + i is 1 or more, where h or i is 0 means a direct bond,

   5) Ar ¹ , Ar ² , Ar ³ and Ar ⁴ are each independently a C ₆ -C ₆₀ aryl group; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; Fluorenyl groups; A fused ring group of an aromatic ring of C ₆ -C ₆₀ and an aliphatic ring of C ₃ -C ₆₀ ; An alkyl group of C ₁ -C ₅₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; C ₆ -C ₃₀ aryloxy group; And -L ^a -N (R ^c ) (R ^d ); wherein L ^a is a single bond; C ₆ -C ₆₀ arylene group; fluorenylene group; O, N, S A C ₂ -C ₆₀ heterocyclic group including at least one hetero atom of Si and P, a fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ , and an aliphatic hydrocarbon group; is selected from the group consisting of, wherein R ^c and R ^d are independently an aryl group of c ₆ -C ₆₀ with each other; fluorene group; O, N, S, at least one heteroatom selected from the group consisting of Si and P Heterocyclic group containing C ₂ -C ₆₀ ; fused ring group of C ₃ -C ₆₀ aliphatic ring and C ₆ -C ₆₀ aromatic ring;

   6) Ar ¹ and Ar ² may be bonded to each other to form a ring,

   7) n is an integer of 1 or 2, when n is 2, two Ar ¹ is the same or different, and two Ar ² is the same or different,

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

   9) a, b, c, e and g are each independently an integer from 0 to 10, d is an integer from 0 to 5, f is an integer from 0 to 2,

   10) R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently hydrogen; heavy hydrogen; Tritium; halogen; Cyano group; Nitro group; C ₆ -C ₆₀ aryl group; Fluorenyl groups; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; An alkyl group of C ₁ -C ₅₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; C ₆ -C ₃₀ aryloxy group; And -L ^a -N (R ^c ) (R ^d ); or when a, b, c, d, e and g are 2 or more and f is 2, respectively, as a plurality Are the same or different, and a plurality of R ¹ or a plurality of R ² or a plurality of R ³ or a plurality of R ⁴ or a plurality of R ⁵ or a plurality of R ⁶ or a plurality of R ⁷ are bonded to each other Can be formed,

   11) A, B, C, D, E and F are independently of each other an aryl group of C ₆ -C ₂₀ or a heterocyclic group of C ₂ -C ₂₀ ,

   However, when both E and F is a substituted or unsubstituted C ₆ aryl group (phenyl group), f is an integer of 2, and R ⁶ may be bonded to each other to form a ring to form an aromatic or heterocyclic ring,

   Here, the aryl group, fluorenyl group, arylene group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkoxy group, aryloxy group are each deuterium; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; -L ^a -N (R ^c ) (R ^d ); Import alkylthio of C ₁ -C _20; An alkoxyl group of C ₁ -C ₂₀ ; An alkyl group of C ₁ -C ₂₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; Aryl group of C ₆ -C ₂₀ ; C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl groups; C ₂ -C ₂₀ heterocyclic group; A cycloalkyl group of C ₃ -C ₂₀ ; C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of, and these substituents may be bonded to each other to form a ring, wherein the “ring” means 3 to 60 carbon atoms. Fused ring consisting of an aliphatic ring or an aromatic ring having 6 to 60 carbon atoms or a hetero ring having 2 to 60 carbon atoms or a combination thereof, and includes a saturated or unsaturated ring.}
2. The organic electric device of claim 1, wherein L ¹ , L ^2, and L ³ of Formulas 1 and 2 are any one of Formulas A-1 to A-13.

     A-1 A-2 A-3 A-4 A-5 A-6

   

    A-7 A-8 A-9 A-10

   

   A-11 A-12 A-13

   

   {In Chemical Formulas A-1 to A-13,

   1) Y is NL ⁴ -Ar ⁵ , O, S, CR ^e R ^f or the following Chemical Formula 1-b,

   Formula 1-b

   

   In Formula 1-b, the dotted line represents a bond from Y,

   2) L ⁴ is the same as the definition of L ³ in claim 1 above,

   3) Ar ⁵ is the same as the definition of Ar ⁴ in claim 1,

   4) R ^e and R ^f are as defined for R ^a in the claims the 1,

   5) R ¹¹ and R ¹² are as defined in R ¹ above in Claim 1,

   6) G and H are the same as the definition of A in claim 1 above,

   7) j and k are the same as the definition of a in claim 1 above,

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

   9) R ⁸ , R ⁹ and R ¹⁰ are each independently hydrogen; heavy hydrogen; Tritium; halogen; Cyano group; Nitro group; C ₆ -C ₆₀ aryl group; Fluorenyl groups; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; An alkyl group of C ₁ -C ₅₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; C ₆ -C ₃₀ aryloxy group; And -L ^a -N (R ^c ) (R ^d ); or when a ', b', c ', d', e ', f' and g 'are 2 or more and h '' Is 2, each being the same or different from each other, and a plurality of R ⁸ or a plurality of R ⁹ or a plurality of R ¹⁰ or a neighboring R ⁸ and R ⁹ or R ⁹ and R ¹⁰ are bonded to each other aromatic Can form a ring or a heteroaromatic ring,

   10) L ^a is the same as defined, and R ^c and R ^d of L ^a in the charge phase 1 is the same as the definition of R ^c and R ^d in the above claim 1,

   11) Z ¹ , Z ² and Z ³ are independently of each other CR ¹³ or N, at least one of Z ¹ , Z ² and Z ³ is N,

   12) R ¹³ is hydrogen; heavy hydrogen; Tritium; halogen; Cyano group; Nitro group; C ₆ -C ₆₀ aryl group; Fluorenyl groups; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; An alkyl group of C ₁ -C ₅₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; C ₆ -C ₃₀ aryloxy group; And -L ^a -N (R ^c ) (R ^d ); and adjacent R ⁸ and R ¹³ may combine with each other to form an aromatic ring or a heteroaromatic ring.}
3. The organic electric device of claim 1, wherein the first host compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-5.

   Chemical Formula 1-1 Chemical Formula 1-2 Chemical Formula 1-3

   

   Formula 1-4 Formula 1-5

   

   {In Formula 1-1 to Formula 1-5,

   1) X ¹ , C, D, R ³ , R ⁴ , c, d, Ar ¹ and Ar ² are as defined in claim 1 above,

   2) Y is NL ⁴ -Ar ⁵ , O, S, CR ^e R ^f or the following Chemical Formula 1-b,

   Formula 1-b

   

   In Formula 1-b, the dotted line represents a bond from Y,

   3) L ⁴ is the same as the definition of L ³ in claim 1,

   4) Ar ⁵ is the same as the definition of Ar ⁴ in claim 1,

   5) R ^e and R ^f are the same as the definitions of R ^a in claim 1,

   6) R ¹¹ and R ¹² are the same as defined in R ¹ in claim 1,

   7) G and H are the same as the definition of A in claim 1,

   8) j and k are the same as the definition of a in claim 1,

   9) a ', c' and d 'are independently of each other an integer from 0 to 4, f' and g 'are independently of each other an integer from 0 to 3 and h' is an integer from 0 to 2,

   10) R ⁸ and R ⁹ are independently of each other hydrogen; heavy hydrogen; Tritium; halogen; Cyano group; Nitro group; C ₆ -C ₆₀ aryl group; Fluorenyl groups; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; An alkyl group of C ₁ -C ₅₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; C ₆ -C ₃₀ aryloxy group; And -L ^a -N (R ^c ) (R ^d ); or when a ', c', d ', f' and g 'are 2 or more and h' is 2 Each of which is the same as or different from each other, and a plurality of R ^{8 s} or a plurality of R ^{9 s} or adjacent R ⁸ and R ⁹ may be bonded to each other to form an aromatic ring or a heteroaromatic ring,

   11) L ^a is as defined in L ^a in the claim 1, and R ^c and R ^d is as defined for R ^c and R ^d in the above claim 1.}
4. The organic electric device of claim 1, wherein the first host compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-6 to 1-20.

       Chemical Formula 1-6 Chemical Formula 1-7 Chemical Formula 1-8

   

        Chemical Formula 1-9 Chemical Formula 1-10 Chemical Formula 1-11

   

       Chemical Formula 1-12 Chemical Formula 1-13 Chemical Formula 1-14

   

       Chemical Formula 1-15 Chemical Formula 1-16 Chemical Formula 1-17

   

       Formula 1-18 Formula 1-19 Formula 1-20

   

   {In Chemical Formulas 1-6 to 1-20,

   1) R ^a , R ^b , R ¹ , R ² , R ³ , R ⁴ , a, b, c, d, L ¹ , Ar ¹ , Ar ² and n are as defined in claim 1 above,

   2) A, B, C and D are C ₁₀ aryl groups.}
5. The organic electroluminescence device according to claim 1, wherein the first host compound represented by Chemical Formula 1 is represented by any one of Chemical Formulas 1-21 to Chemical Formula 1-23.

       Chemical Formula 1-21 Chemical Formula 1-22 Chemical Formula 1-23

   

   {In Formula 1-21 to Formula 1-23,

   (1) C, D, R ³ , R ⁴ , c, d, L ¹ , Ar ¹ and Ar ² are as defined in claim 1 above,

   (2) W is NL ⁵ -Ar ⁶ , O, S, CR ^g R ^h or the following Chemical Formula 1-c,

   Formula 1-c

   

   In Formula 1-c, the dotted line represents a bond from W,

   (3) L ⁵ is the same as the definition of L ³ in claim 1, Ar ⁶ is the same as the definition of Ar ⁴ in claim 1,

   (4) R ^g and R ^h are as defined for R ^a in the above claim 1,

   (5) R ¹⁵ and R ¹⁶ are the same as defined in R ¹ in claim 1,

   (6) I and J are the same as the definition of A in claim 1,

   (7) o and p are the same as the definition of a in claim 1 above,

   (8) l is an integer of 0 to 3, m is an integer of 0 to 4,

   (9) R ¹³ and R ¹⁴ are each independently hydrogen; heavy hydrogen; Tritium; halogen; Cyano group; Nitro group; C ₆ -C ₆₀ aryl group; Fluorenyl groups; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; An alkyl group of C ₁ -C ₅₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; C ₆ -C ₃₀ aryloxy group; And -L ^a -N (R ^c ) (R ^d ); and a plurality of R ¹³ or a plurality of R ¹⁴ or neighboring R ¹³ and R ¹⁴ are bonded to each other to form an aromatic ring or heteroaromatic. Can form a ring,

   (10) L ^a is the same as the definition of R ^c and R ^d as defined in L ^a in the claim 1, and R ^c and R ^d are in the claim 1,

   (11) two Ar ² are each the same or different, two Ws are each the same or different, and a plurality of R ¹³ and a plurality of R ¹⁴ are the same or different from each other.
6. The organic electroluminescence device according to claim 1, wherein n is 1 in the formula (1)
7. The organic electroluminescence device according to claim 1, wherein n is 2 in the formula (1)
8. The organic electroluminescence device according to claim 1, wherein A, B, C, D, E and F in Chemical Formulas 1 and 2 are selected from the group consisting of Chemical Formulas B-1 to B-7.

   Chemical Formula B-1 Chemical Formula B-2 Chemical Formula B-3 Chemical Formula B-4

   

       Chemical Formula B-5 Chemical Formula B-6 Chemical Formula B-7

   

   {In Formula B-1 to Formula B-7,

   (1) Z ⁴ to Z ⁵¹ are CR ⁱ or N,

   (2) R ⁱ is the same as the definition of R ^a in claim 1 above,

   (3) * indicates the position to be condensed}
9. The organic electroluminescence device according to claim 1, wherein the second host compound represented by Chemical Formula 2 is represented by the following Chemical Formula 3 or Chemical Formula 4.

        Formula 3 Formula 4

   

   {In Chemical Formulas 3 and 4,

   E, F, R ⁵ , R ⁶ , R ⁷ , e, f, g, L ² , Ar ³ , X ² and X ³ are as defined in claim 1 above.
10. The organic electroluminescence device according to claim 1, wherein R ^{6 in} Formula 2 necessarily forms an aromatic ring or a heteroaromatic ring.
11. The organic electroluminescence device according to claim 1, wherein the second host compound represented by Chemical Formula 2 is represented by any one of the following Chemical Formulas 5-1 to 5-40.

       Chemical Formula 5-1 Chemical Formula 5-2 Chemical Formula 5-3 Chemical Formula 5-4

    

       Chemical Formula 5-5 Chemical Formula 5-6 Chemical Formula 5-7 Chemical Formula 5-8

    

        Chemical Formula 5-9 Chemical Formula 5-10 Chemical Formula 5-11 Chemical Formula 5-12

    

     Formula 5-13 Formula 5-14 Formula 5-15 Formula 5-16

    

     Formula 5-17 Formula 5-18 Formula 5-19 Formula 5-20

    

      Formula 5-21 Formula 5-22 Formula 5-23 Formula 5-24

    

      Chemical Formula 5-25 Chemical Formula 5-26 Chemical Formula 5-27 Chemical Formula 5-28

    

     Formula 5-29 Formula 5-30 Formula 5-31 Formula 5-32

    

     Chemical Formula 5-33 Chemical Formula 5-34 Chemical Formula 5-35 Chemical Formula 5-36

    

     Chemical Formula 5-37 Chemical Formula 5-38 Chemical Formula 5-39 Chemical Formula 5-40

    

    {In Formula 5-1 to Formula 5-40,

    (1) R ⁵ , R ⁶ , R ⁷ , e, f, g, L ² , Ar ³ , X ² and X ³ are as defined in claim 1 above,

    (2) q is an integer of 0 to 4,

    (3) R ¹⁷ is hydrogen; heavy hydrogen; Tritium; halogen; Cyano group; Nitro group; C ₆ -C ₆₀ aryl group; Fluorenyl groups; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; An alkyl group of C ₁ -C ₅₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; An aryloxy group of C ₆ -C ₃₀ ; and q is 2, each of which is the same or different from each other.}
12. The organic electric device of claim 1, wherein the second host compound represented by Chemical Formula 2 is represented by any one of the following Chemical Formulas 6-1 to 6-8.

      Chemical Formula 6-1 Chemical Formula 6-2 Chemical Formula 6-3 Chemical Formula 6-4

    

        Chemical Formula 6-5 Chemical Formula 6-6 Chemical Formula 6-7 Chemical Formula 6-8

    

    {In Chemical Formulas 6-1 to 6-8,

    E, F, R ⁵ , R ⁶ , R ⁷ , R ^a , R ^b , e, f, g, L ² , L ³ , Ar ³ and Ar ⁴ are as defined in claim 1 above.
13. The organic electroluminescence device according to claim 1, wherein the first host compound represented by Chemical Formula 1 is any one of the following Compounds 1-1 to 1-70 and Compounds 2-1 to 2-115.

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    
14. The organic electroluminescence device according to claim 1, wherein the second host compound represented by Chemical Formula 2 is any one of the following Compounds 3-1 to 3-115.

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    
15. The semiconductor device of claim 1, further comprising at least one hole transport band layer between the first electrode and the light emitting layer, wherein the hole transport band layer includes a hole transport layer, a light emitting auxiliary layer, or both. An organic electric device comprising the compound represented by Formula 1
16. The organic electroluminescence device according to claim 1, wherein the compound represented by Chemical Formula 1 and Chemical Formula 2 is used in a light emitting layer by mixing in a ratio of 1: 9 to 9: 1.
17. The organic electroluminescence device according to claim 1, wherein the compound represented by Chemical Formula 1 and Chemical Formula 2 is used in a light emitting layer by mixing 1: 9 or 5: 5.
18. The organic electroluminescent device according to claim 1, wherein the compound represented by Chemical Formula 1 and Chemical Formula 2 is used in a light emitting layer by mixing 2: 8 or 3: 7.
19. An electronic device comprising: a display device comprising the organic electrical device of claim 1;
20. 20. The electronic device of claim 19, wherein the organic electroluminescent element is at least one of an organic electroluminescent element, an organic solar cell, an organic photoconductor, an organic transistor, and a monochromatic or white illumination element.

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