KR102094237B1 - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

By using the mixture of the compound according to the present invention as a phosphorescent host material, it is possible to achieve high luminous efficiency and low driving voltage of an organic electrical device, and also an organic electrical device and its electronic device that can significantly improve the life of the device. to provide.

Description

Compound for organic electric element, organic electric element using the same, and its electronic device {COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF}

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

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

Materials used as the organic material layer in the organic electric device may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on their function.

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

As a typical example, Patent Documents 1 to 4 below report the performances of heterocyclic rings and polycyclic rings among polycyclic ring compounds according to hetero type and arrangement, substituent type, and fused position.

[Patent Document 1]: U.S. Patent Registration No. 5843607

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

[Patent Document 3]: Korean Patent Publication 2008-0085000

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

[Patent Document 5]: Korea Patent Publication 2011-0018340

[Patent Document 6]: Korean Patent Publication 2009-0057711

Patent Document 1 and Patent Document 2 used an indolocarbazole core composed of only nitrogen (N) in a 5-membered ring compound, and reported an example 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 it is very insufficient to prove the effect of the substitution of the polycyclic ring compound. And use as a phosphorescent host material is not described.

Patent Document 3 and Patent Document 4 are pyridine, pyrimidine, triazine, etc., each containing an aryl group and N in the indolocarbazole foam core having a heteroatom N in the same 5-membered ring compound as in Patent Document 1 and Patent Document 2 above. Although substituted compounds are described, only examples of use for phosphorescent green host materials are described, and performance for other heterocyclic compounds substituted for indolocarbazole cores is not described.

Patent Document 5 describes nitrogen (N), oxygen (O), sulfur (S), carbon, etc. in the heteroatom in the 5-ring cyclic compound, but only examples in which performance heterogeneous heteroatoms are used in the performance measurement data are all present. Thus, it was not possible to confirm the performance characteristics of the 5-membered ring compound containing hetero heteroatoms.

Therefore, the patent document does not describe a solution to the low charge carrier mobility and low oxidation stability of the 5-ring cyclic compound containing the same heteroatom.

When a 5-membered ring compound molecule is generally stacked, it has a strong electrical interaction as the number of adjacent π-electrons increases, which is closely related to the charge carrier mobility. When is stacked, the order of the intermolecular molecules has an edge-to-face shape, whereas the heterocyclic 5-membered cyclic compound has an antiparallelcofacial π-stacking in which the packing structure of the molecules faces in the opposite direction. structure), and the order of arrangement between molecules becomes face-to-face. In the hetero atom N arranged asymmetrically, which is the cause of the laminated structure, It has been reported that the steric effect of the substituted substituents causes relatively high carrier mobility and high oxidation stability. ( Org . Lett . 2008, 10 , 1199)

Patent Document 6 reports an example of using as a fluorescent host material for various polycyclic ring compounds of 7 or more rings.

As described above, the development of the fused position and the number of rings for the polycyclic ring compound, the arrangement of heteroatoms, and the characteristics of each type has not been sufficiently developed.

In particular, in a phosphorescent organic electric device using a phosphorescent dopant material, the LUIMO and HOMO levels of the host material have a great influence on the efficiency and lifetime of the organic electrical device, which can efficiently control electron and hole injection in the light emitting layer. This is because it is possible to prevent the reduction of the efficiency and the lifespan due to charge balance control in the light emitting layer, quenching of the dopant, and emission of light at the interface of the hole transport layer depending on the one.

In the case of host materials for fluorescence and phosphorescence emission, recently, the efficiency and lifespan of organic electric devices using TADF (Thermal activatied delayed fluorescent), Exciplex, etc., are being studied. There is a lot of research going on.

Although there are various methods for examining the energy transfer in the light emitting layer for TADF (Thermal activatied delayed fluorescent), exciplex, it can be easily confirmed by PL lifetime (TRTP) measurement.

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

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

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

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

The present invention is 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 the following formula (1 It provides an organic electric device comprising a first host compound represented by) and a second host compound represented by the following formula (2).

Formula (1) Formula (2)

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

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

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

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

In addition, in describing the components of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are only for distinguishing the component from other components, and the nature, order, or order of the component is not limited by the term. When a component is described as being "connected", "coupled" or "connected" to another component, that component may be directly connected to or connected to the other component, but another component between each component It should be understood that elements may be "connected", "coupled" or "connected".

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

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

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

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

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

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

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

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

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

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

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

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

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

As used herein, the term "heteroalkyl" means alkyl containing one or more heteroatoms, unless otherwise specified. As used herein, the term "heteroaryl group" or "heteroarylene group" means an aryl group or an arylene group having 2 to 60 carbon atoms, each of which contains one or more heteroatoms, unless otherwise specified. No, it includes at least one of a single ring and multiple rings, and may be formed by combining adjacent functional devices.

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

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

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

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

Unless otherwise specified, the term "ring" used in the present invention refers to an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a heterocyclic ring having 2 to 60 carbon atoms or a combination thereof, and It contains a saturated or unsaturated ring.

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

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

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

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

In addition, unless otherwise specified, the formula used in the present invention is applied in the same manner as the substituent definition by the exponent definition of the following formula.

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

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

[Example of ortho-location]

[Example of meta-position]

[Example of meta-position]

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

The present invention is 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 following formula (1) and a second host compound represented by the following formula (2).

   Formula (1) Formula (2)

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

1) aryl groups of Ar ^{1 ~ 4} is independently C ₆ ~ C ₆₀ to each other; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; And C ₆ ~ C ₃₀ Aryloxy group; It is selected from the group consisting of,

2) c and e are integers of 0 to 10, d is an integer of 0 to 2, and R ^{3 to 5} are the same or different from each other, and independently deuterium; halogen; C ₆ ~ C ₆₀ Aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And -L'-N (R _a ) (R _b ); (where L 'is a single bond; C ₆ ~ C ₆₀ arylene group; fluorenylene group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ A fused ring group of an aromatic ring; And C ₂ ~ C ₆₀ heterocyclic group; is selected from the group consisting of, wherein R _a and R _b independently of each other C ₆ ~ C ₆₀ aryl group; fluorenyl group ; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ fused ring group of the aromatic ring; And O, N, S, Si and P containing at least one heteroatom of C ₂ ~ C ₆₀ heterocycle Group; selected from the group consisting of), or selected from the group consisting of, or when c, d and e are 2 or more, each of the same as or different from each other as a plurality of R ³ or a plurality of R ⁴ or a plurality of R ⁵ can be combined with each other to form a ring,

3) L ¹ , L ² , L ³ and L ⁴ are Single bond; C ₆ ~ C ₆₀ Arylene group; Fluorylene group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; And C ₂ ~ C ₆₀ heterocyclic group; is selected from the group consisting of,

4) A and B are C ₆ to C ₂₀ aryl groups or C ₂ to C ₂₀ heterocyclic groups,

However, when A or B is a substituted or unsubstituted C ₆ aryl group (phenyl group), d is 2 and R ^{4 is} bonded to each other to form a ring to form an aromatic or heterocyclic ring,

5) i, j are 0 or 1,

However, i + j is 1 or more, where i or j is 0 means a direct bond,

6) X ^{1, 2} are NR ', O, S, or CR'R ";

R ', R "are hydrogen; C ₆ ~ C ₆₀ aryl group; fluorenyl group; C ₃ ~ C ₆₀ heterocyclic group; or C ₁ ~ C ₅₀ alkyl group ;,

R 'and R "may combine with each other to form a ring as a spy,

(Wherein, the aryl group, fluorenyl group, arylene group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkoxy group, aryloxy group, each deuterium; halogen; C ₁ -C ₂₀ alkyl group or C ₆ -C Silane group unsubstituted or substituted with aryl group of ₂₀ ; siloxane group; boron group; germanium group; cyano group; nitro group; -L ^a -N (R ^a ) (R ^b ); C ₁ -C ₂₀ alkylthio ; C ₁ -C ₂₀ alkoxyl group; C ₁ -C ₂₀ alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ aryl group; C substituted with deuterium _6- C ₂₀ aryl group; fluorenyl group; C ₂ -C ₂₀ heterocyclic group; C ₃ -C ₂₀ cycloalkyl group; C ₇ -C ₂₀ arylalkyl group and C ₈ -C ₂₀ arylalkenyl group It may be further substituted with one or more substituents selected from the group consisting of, and also these substituents may combine with each other to form a ring, wherein 'ring' is an aliphatic ring having 3 to 60 carbon atoms or Refers to a fused ring consisting of heterocyclic, or a combination thereof having 6 to 60 ring carbon atoms, or 2 to 60, and a saturated or unsaturated ring.)}

In addition, the compounds represented by the formulas (1) and (2) are provided.

In addition, the present invention provides an organic electroluminescent device characterized in that the first host compound represented by the formula (1) is represented by any one of the following formulas (3) to (5).

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

{In the above formulas (3) to (5),

1) L ^{1, 3, 4} and Ar ^{2 to 3} are as defined in the above formula (1),

2) X ³ is O or S,

3) a is an integer from 0 to 4, b is an integer from 0 to 3, R ^{1 and 2} are the same or different from each other, and independently deuterium; halogen; C ₆ ~ C ₆₀ Aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And -L'-N (R _a ) (R _b ); or when a and b are 2 or more, they are the same as or different from each other, and a plurality of R ¹ or a plurality of R ² They can combine with each other to form a ring.}

In addition, the present invention provides an organic electric device in which the compound represented by the formula (1) includes a compound represented by any one of the following formulas (6) to (14).

Formula (6) Formula (7) Formula (8)

Formula (9) Formula (10) Formula (11)

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

{In the formulas (6) to (14), L ^{1, 3, 4} , Ar ^{2 ~ 3} , R ^1,2 , a, b are as defined in the formula (1).}

In another embodiment, the present invention provides an organic electric device comprising a compound represented by any one of the following formulas (15) to (23), the first host compound represented by the formula (1).

Formula (15) Formula (16) Formula (17)

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

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

{In the formulas (15) to (23), L ^{1 , 3, 4} , Ar ^{2 ~ 3} , R ^1,2 , a, b are as defined in the formula (1).}

As another example, an organic electroluminescent device comprising a compound represented by any one of the following formulas (24) to (26) is provided.

Formula (24) Formula (25) Formula (26)

{In the above formulas (24) to (26),

1) L ^{1, 3, 4} , Ar ^{2 ~ 3} are as defined in the above formula (1),

2) Ar ^{5 and 6} are independently of each other C ₆ ~ C ₆₀ aryl group; O, N, S, Si and P, at least one hetero atom of the heterocyclic C ₂ ~ C ₆₀ group comprising a fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C ₆₀ of the; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And -L'-N (R _a ) (R _b ) ;.)

In the present invention, L ^{1, 3, 4} in the formula (1) also provides an organic electric device comprising a compound of any one of the following formulas (A-1) to (A-12).

{In the formulas (A-1) to (A-12),

1) a ', c', d ', e' are integers from 0 to 4; b 'is an integer of 0-6; f ', g' are integers from 0 to 3, and h 'is an integer from 0 or 1,

2) R ^6-8 are the same as or different from each other, and independently of each other deuterium; halogen; C ₆ ~ C ₆₀ Aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And _{-L'-N (R a) (} R b); is selected from the group consisting of, or the f ', g' is 2 or more the same or different from each other, respectively, and a plurality of a plurality of R ⁶ or a plurality of each other R ⁷ or adjacent R ⁶ and R ⁷ may combine with each other to form an aromatic ring or a heteroaromatic ring,

2) Y is NR ', O, S or CR'R ", R', R" are as defined in Formula (1) above,

3) Z ^1-3 are CR 'or N, and at least one is N.}

In one embodiment of the present invention, in Formula (1), at least one of L ^{1, 3, and 4} is a phenyl group, and provides an organic electric device including a compound characterized in that it is substituted with the m (meth) -position. .

In another aspect, the present invention provides an organic electric device in which the second host compound represented by the formula (2) includes a compound represented by the following formula (27) or formula (28).

Formula (27) Formula (28)

{In the formulas (27) and (28), R ^{3 to 5} , Ar ⁴ , L ² , c, d, e, A, B, X ^{1, 2} are as defined in the formula (2).}

In addition, in one embodiment of the present invention, A and B of the formula (2) provides an organic electric device comprising a compound selected from the group consisting of the following formulas (B-1) to (B-7).

{In the formulas B-1 to B-7,

1) Z ^4-50 is CR 'or N,

2) R 'is as defined above,

3) * indicates the condensed position.}

In addition, the present invention provides an organic electric device in which the second host compound represented by the formula (2) includes a compound represented by any one of the following formulas (29) to (48).

Formula (29) Formula (30) Formula (31)

Formula (32) Formula (33) Formula (34)

Formula (35) Formula (36) Formula (37)

Formula (38) Formula (39) Formula (40)

Formula (41) Formula (42) Formula (43)

Formula (44) Formula (45) Formula (46)

Formula (47) Formula (48)

{In the formulas (29) to (48), Ar ⁴ , X ^1,2 , R ^{3 to 5} , c, d, e are as defined above.}

In one aspect of the present invention, the second host compound represented by the formula (2) provides an organic electric device including a compound represented by any one of the following formulas (49) to (55).

Formula (49) Formula (50) Formula (51) Formula (52)

Formula (53) Formula (54) Formula (55)

{In the formulas (49) to (55), R ^{3 to 5} , Ar ⁴ , c, d, e, A, B, C, R 'are as defined above.}

In the present invention, the first host compound represented by the formula (1) includes the following compounds 1-1 'to 1-82'.

In addition, the present invention, the second host compound represented by the formula (2) includes the following compounds 3-1 to 3-100.

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

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

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

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

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

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

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

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

As another specific example, the present invention provides an organic electric device in which the light emitting layer in the organic material layer is a phosphorescent light emitting layer.

In addition, the present invention provides an organic electric device included in the light emitting layer by mixing the compound represented by the formula (1) and the formula (2) in the ratio of any one of 1: 9 to 9: 1 in the light emitting layer of the organic material layer.

In addition, the present invention is an organic electroluminescence 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 to 5: 5 and used in the light emitting layer. The device is provided. More preferably, the mixing ratio of the compound represented by the formula (1) and the formula (2) is included in the light emitting layer at 2: 8 or 3: 7.

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

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

In addition, the present invention is a display device comprising the above-described organic electric element; And a control unit for driving the display device.

In another aspect, the present invention provides an electronic device characterized in that the organic electroluminescent device is at least one of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, and a monochromatic or white lighting device. At this time, the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation, game machines, various TVs, and various computers.

Hereinafter, the synthesis examples of the compounds represented by the formulas (1) and (2) of the present invention and the production examples of the organic electroluminescent device of the present invention will be specifically described with reference to examples, It is not limited.

[ Synthetic example  One]

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

<Scheme 1>

Sub 1 of  example

Examples of Sub 1 of Scheme 1 are as follows and are not limited thereto.

Synthesis example of Sub 2

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

<Reaction Scheme 2>

[Example of Sub 2-1]

Round bottom flask Aniline (15 g, 161.1 mmol), 1-bromonaphthalene (36.7 g, 177.2 mmol), Pd ₂ (dba) ₃ (7.37 g, 8.05 mmol), P (t-Bu) ₃ (3.26 g, 16.1 mmol), NaOt-Bu (51.08 g, 531.5 mmol), toluene (1690 mL) was added, and the reaction proceeded at 100 ° C. After the reaction was completed, extracted with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and then the resulting organic material was silicagel column and recrystallized to obtain 25.4 g of Sub 2-1. (Yield: 72%)

[Example of Sub 2-26]

Round bottom flask [1,1'-biphenyl] -4-amine (15 g, 88.6 mmol), 2- (4-bromophenyl) -9,9-diphenyl-9H-fluorene (46.2 g, 97.5 mmol), Pd ₂ (dba) ₃ (4.06 g, 4.43 mmol), P (t-Bu) ₃ (1.8 g, 8.86 mmol), NaOt-Bu (28.1 g, 292.5 mmol), toluene (931 mL) above Sub 2-1 Experiment was conducted in the same manner as Sub 2-26 to obtain 34.9 g.

(Yield: 70%)

[Example of Sub 2-40]

Naphthalen-1-amine (15 g, 104.8 mmol), 2-bromodibenzo [b, d] thiophene (30.3 g, 115.2 mmol), Pd ₂ (dba) ₃ (4.8 g, 5.24 mmol), P ( t-Bu) ₃ (2.12 g, 10.48 mmol), NaOt-Bu (33.22 g, 345.7 mmol), and toluene (1100 mL) were tested in the same manner as in Sub 2-1 to obtain 24.9 g of Sub 2-40.

(Yield: 73%)

[Example of Sub 2-51]

4- (dibenzo [b, d] furan-2-yl) aniline (15 g, 57.85 mmol), 2-bromodibenzo [b, d] furan (15.7 g, 63.63 mmol), Pd ₂ (dba) in a round bottom flask ₃ (2.65 g, 2.89 mmol), P (t-Bu) ₃ (1.17 g, 5.78 mmol), NaOt-Bu (18.35 g, 190.9 mmol), toluene (607 mL) in the same manner as in Sub 2-1 above. By experiment, 17.2 g of Sub 2-51 was obtained. (Yield: 70%)

Sub 2-1 to Sub 2-52 were synthesized in the same manner as the synthesis method, and Sub 2 is not limited thereto.

compound FD-MS compound FD-MS Sub 2-1 m / z = 219.10 (C ₁₆ H ₁₃ N = 219.28) Sub 2-2 m / z = 295.14 (C ₂₂ H ₁₇ N = 295.38) Sub 2-3 m / z = 269.12 (C ₂₀ H ₁₅ N = 269.34) Sub 2-4 m / z = 169.09 (C ₁₂ H ₁₁ N = 169.22) Sub 2-5 m / z = 245.12 (C ₁₈ H ₁₅ N = 245.32) Sub 2-6 m / z = 321.15 (C ₂₄ H ₁₉ N = 321.41) Sub 2-7 m / z = 269.12 (C ₂₀ H ₁₅ N = 269.34) Sub 2-8 m / z = 345.15 (C ₂₆ H ₁₉ N = 345.44) Sub 2-9 m / z = 345.15 (C ₂₆ H ₁₉ N = 345.44) Sub 2-10 m / z = 325.18 (C ₂₄ H ₂₃ N = 325.45) Sub 2-11 m / z = 397.18 (C ₃₀ H ₂₃ N = 397.51) Sub 2-12 m / z = 447.20 (C ₃₄ H ₂₅ N = 447.57) Sub 2-13 m / z = 371.17 (C ₂₈ H ₂₁ N = 371.47) Sub 2-14 m / z = 421.18 (C ₃₂ H ₂₃ N = 421.53) Sub 2-15 m / z = 295.14 (C ₂₂ H ₁₇ N = 295.38) Sub 2-16 m / z = 397.18 (C ₃₀ H ₂₃ N = 397.51) Sub 2-17 m / z = 321.15 (C ₂₄ H ₁₉ N = 321.41) Sub 2-18 m / z = 245.12 (C ₁₈ H ₁₅ N = 245.32) Sub 2-19 m / z = 321.15 (C ₂₄ H ₁₉ N = 321.41) Sub 2-20 m / z = 321.15 (C ₂₄ H ₁₉ N = 321.41) Sub 2-21 m / z = 371.17 (C ₂₈ H ₂₁ N = 371.47) Sub 2-22 m / z = 421.18 (C ₃₂ H ₂₃ N = 421.53) Sub 2-23 m / z = 395.17 (C ₃₀ H ₂₁ N = 395.49) Sub 2-24 m / z = 473.21 (C ₃₆ H ₂₇ N = 473.61) Sub 2-25 m / z = 369.15 (C ₂₈ H ₁₉ N = 369.46) Sub 2-26 m / z = 561.25 (C ₄₃ H ₃₁ N = 561.71) Sub 2-27 m / z = 411.20 (C ₃₁ H ₂₅ N = 411.54) Sub 2-28 m / z = 459.20 (C ₃₅ H ₂₅ N = 459.58) Sub 2-29 m / z = 483.20 (C ₃₇ H ₂₅ N = 483.60) Sub 2-30 m / z = 375.16 (C ₂₇ H ₂₁ NO = 375.46) Sub 2-31 m / z = 475.19 (C ₃₅ H ₂₅ NO = 475.58) Sub 2-32 m / z = 575.22 (C ₄₃ H ₂₉ NO = 575.70) Sub 2-33 m / z = 533.21 (C ₄₁ H ₂₇ N = 533.66) Sub 2-34 m / z = 485.21 (C ₃₇ H ₂₇ N = 485.62) Sub 2-35 m / z = 361.18 (C ₂₇ H ₂₃ N = 361.48) Sub 2-36 m / z = 485.21 (C ₃₇ H ₂₇ N = 485.62) Sub 2-37 m / z = 499.19 (C ₃₇ H ₂₅ NO = 499.60) Sub 2-38 m / z = 439.19 (C ₃₂ H ₂₅ NO = 439.55) Sub 2-39 m / z = 335.13 (C ₂₄ H ₁₇ NO = 335.40) Sub 2-40 m / z = 325.09 (C ₂₂ H ₁₅ NS = 325.43) Sub 2-41 m / z = 427.14 (C ₃₀ H ₂₁ NS = 427.56) Sub 2-42 m / z = 461.18 (C ₃₄ H ₂₃ NO = 461.55) Sub 2-43 m / z = 349.11 (C ₂₄ H ₁₅ NO ₂ = 349.38) Sub 2-44 m / z = 381.06 (C ₂₄ H ₁₅ NS ₂ = 381.51) Sub 2-45 m / z = 457.10 (C ₃₀ H ₁₉ NS ₂ = 457.61) Sub 2-46 m / z = 533.13 (C ₃₆ H ₂₃ NS ₂ = 533.70) Sub 2-47 m / z = 353.10 (C ₂₂ H ₁₅ N ₃ S = 353.44) Sub 2-48 m / z = 327.0 (C ₂₀ H ₁₃ N ₃ S = 327.40) Sub 2-49 m / z = 375.11 (C ₂₆ H ₁₇ NS = 375.48) Sub 2-50 m / z = 411.16 (C ₃₀ H ₂₁ NO = 411.49) Sub 2-51 m / z = 425.14 (C ₃₀ H ₁₉ NO ₂ = 425.48) Sub 2-52 m / z = 475.16 (C ₃₄ H ₂₁ NO ₂ = 475.54)

Final product synthesis example

One- 1 'of  synthesis

Round bottom flask with di ([1,1'-biphenyl] -4-yl) amine (10 g, 31.1 mmol), 4-bromo-1,1'-biphenyl (8 g, 34.2 mmol), Pd ₂ (dba ) ₃ (1.42 g, 1.56 mmol), P (t-Bu) ₃ (0.63 g, 3.11 mmol), NaOt-Bu (9.87 g, 102.7 mmol), toluene (330 mL) was added and the reaction proceeded at 100 ° C. do. After the reaction was completed, after extracting with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and then the resulting organic material was silicagel column and recrystallized to obtain 11.3 g of Product 1-1 '. (Yield: 77%)

One- 4 'of  synthesis

Round bottom flask with bis (4- (naphthalen-1-yl) phenyl) amine (10 g, 23.7 mmol), 1- (4-bromophenyl) naphthalene (7.4 g, 26.1 mmol), Pd ₂ (dba) ₃ (1.09 g, 1.19 mmol), P (t-Bu) ₃ (0.5 g, 2.4 mmol), NaOt-Bu (7.52 g, 78.3 mmol), toluene (250 mL) was tested in the same manner as 1-1 'above. 11.5 'was obtained. (Yield: 78%)

Synthesis of 1-10 '

N-([1,1'-biphenyl] -4-yl)-[1,1 ': 3', 1 ''-terphenyl] -5'-amine (10 g, 25.2 mmol), 5 in a round bottom flask '-bromo-1,1': 3 ', 1''-terphenyl (8.56 g, 27.7 mmol), Pd ₂ (dba) ₃ (1.15 g, 1.26 mmol), P (t-Bu) ₃ (0.51 g, 2.52 mmol), NaOt-Bu (7.98 g, 83.02 mmol), and toluene (264 mL) were tested in the same manner as 1-1 'above to obtain 11.8 g of Product 1-10'. (Yield: 75%)

Synthesis of 1-19 '

N-([1,1'-biphenyl] -4-yl) naphthalen-1-amine (10 g, 33.6 mmol), 2-bromodibenzo [b, d] thiophene (9.8 g, 37.2 mmol) in a round bottom flask, Pd ₂ (dba) ₃ (1.55 g, 1.7 mmol), P (t-Bu) ₃ (0.68 g, 3.38 mmol), NaOt-Bu (10.76 g, 112 mmol), toluene (355 mL) is 1-1. 12.3 g of Product 1-19 was obtained by experimenting in the same manner as'. (Yield: 76%)

Synthesis of 1-20 '

Round bottom flask with di ([1,1'-biphenyl] -3-yl) amine (10 g, 31.1 mmol), 2-bromodibenzo [b, d] thiophene (9 g, 34.2 mmol), Pd ₂ (dba) ₃ (1.42 g, 1.56 mmol), P (t-Bu) ₃ (0.63 g, 3.11 mmol), NaOt-Bu (9.87 g, 102.7 mmol), toluene (327 mL) in the same manner as 1-1 'above. By experiment, 12.2 g of Product 1-20 'was obtained. (Yield: 78%)

Synthesis of 1-23 '

N- (naphthalen-1-yl) -9,9-diphenyl-9H-fluoren-2-amine (10 g, 21.8 mmol), 2-bromodibenzo [b, d] thiophene (6.3 g, 23.9 mmol) in a round bottom flask ), Pd ₂ (dba) ₃ (1 g, 1.09 mmol), P (t-Bu) ₃ (0.44 g, 2.2 mmol), NaOt-Bu (6.9 g, 71.8 mmol), toluene (230 mL) above 1 Experiment was conducted in the same manner as -1 'to obtain 10.2 g of Product 1-23'. (Yield: 73%)

Synthesis of 1-24 '

N-([1,1'-biphenyl] -4-yl) -9,9'-spirobi [fluoren] -2-amine (10 g, 20.7 mmol), 2-bromodibenzo [b, d] in a round bottom flask thiophene (6 g, 22.7 mmol), Pd ₂ (dba) ₃ (0.95 g, 1.03 mmol), P (t-Bu) ₃ (0.42 g, 2.07 mmol), NaOt-Bu (6.55 g, 68.2 mmol), toluene (220 mL) was tested in the same manner as 1-1 'above to obtain 10.2 g of Product 1-24'. (Yield: 74%)

Synthesis of 1-29 '

N- (naphthalen-1-yl) dibenzo [b, d] thiophen-2-amine (10 g, 30.7 mmol), 2- (4-bromophenyl) dibenzo [b, d] thiophene (11.5 g, 33.8 mmol), Pd ₂ (dba) ₃ (1.41 g, 1.54 mmol), P (t-Bu) ₃ (0.62 g, 3.07 mmol), NaOt-Bu (9.75 g, 101.4 mmol), toluene (325 mL) Experiment was conducted in the same manner as 1-1 'to obtain 12.9 g of Product 1-29'. (Yield: 72%)

Synthesis of 1-30 '

N-([1,1'-biphenyl] -4-yl)-[1,1'-biphenyl] -3-amine (10 g, 31.1 mmol), 2- (3-bromophenyl) dibenzo [ b, d] thiophene (11.6 g, 34.2 mmol), Pd ₂ (dba) ₃ (1.42 g, 1.55 mmol), P (t-Bu) ₃ (0.63 g, 3.11 mmol), NaOt-Bu (9.9 g, 103 mmol), toluene (330 mL) was tested in the same manner as in 1-1 'above to obtain 12.8 g of Product 1-30'. (Yield: 71%)

Synthesis of 1-36 '

Round bottom flask with bis (dibenzo [b, d] thiophen-2-yl) amine (10 g, 26.2 mmol), 2-bromodibenzo [b, d] thiophene (7.59 g, 28.8 mmol), Pd ₂ (dba) ₃ (1.2 g, 1.31 mmol), P (t-Bu) ₃ (0.53 g, 2.62 mmol), NaOt-Bu (8.31 g, 86.5 mmol), toluene (275 mL) were tested in the same manner as 1-1 'above. To obtain 11.4 g of Product 1-36 '. (Yield: 77%)

Synthesis of 1-49 '

Di ([1,1'-biphenyl] -4-yl) amine (10 g, 31.1 mmol), 2- (3-bromophenyl) dibenzo [b, d] furan (11.1 g, 34.2 mmol) in a round bottom flask, Pd ₂ (dba) ₃ (1.42 g, 1.56 mmol), P (t-Bu) ₃ (0.63 g, 3.11 mmol), NaOt-Bu (9.9 g, 103 mmol), toluene (330 mL) is 1-1. 13.3 g of Product 1-49 was obtained by experimenting in the same manner as'. (Yield: 76%)

Synthesis of 1-51 '

N- (4- (naphthalen-1-yl) phenyl) naphthalen-2-amine (10 g, 28.9 mmol), 2- (7-bromo-9,9-dimethyl-9H-fluoren-2- yl) dibenzo [b, d] furan (14 g, 32 mmol), Pd ₂ (dba) ₃ (1.33 g, 1.45 mmol), P (t-Bu) ₃ (0.59 g, 2.9 mmol), NaOt-Bu ( 9.2 g, 95.5 mmol) and toluene (310 mL) were tested in the same manner as 1-1 'above to obtain 14.5 g of Product 1-51'. (Yield: 71%)

Synthesis of 1-59 '

N-([1,1'-biphenyl] -4-yl) benzo [4,5] thieno [3,2-d] pyrimidin-2-amine (10 g, 28.3 mmol), 4- ( 4-bromophenyl) dibenzo [b, d] furan (10.1 g, 31.1 mmol), Pd ₂ (dba) ₃ (1.3 g, 1.41 mmol), P (t-Bu) ₃ (0.57 g, 2.83 mmol), NaOt- Bu (8.98 g, 93.4 mmol) and toluene (300 mL) were tested in the same manner as 1-1 'above to obtain 12.3 g of Product 1-59'. (Yield: 73%)

Synthesis of 1-71 '

Round bottom flask with di ([1,1'-biphenyl] -4-yl) amine (10 g, 31.1 mmol), 2- (4-bromophenyl) -9,9'-spirobi [fluorene] (16.1 g, 34.2 mmol), Pd ₂ (dba) ₃ (1.42 g, 1.56 mmol), P (t-Bu) ₃ (0.63 g, 3.11 mmol), NaOt-Bu (9.87 g, 102.7 mmol), toluene (330 mL) above Experiment was performed in the same manner as 1-1 'to obtain 15.5 g of Product 1-71'. (Yield: 70%)

Synthesis of 1-75 '

N- (4- (9,9-diphenyl-9H-fluoren-2-yl) phenyl)-[1,1'-biphenyl] -4-amine (10 g, 17.8 mmol), 3-bromo in a round bottom flask -9,9-diphenyl-9H-fluorene (7.78 g, 19.6 mmol), Pd ₂ (dba) ₃ (0.82 g, 0.89 mmol), P (t-Bu) ₃ (0.36 g, 1.78 mmol), NaOt-Bu (5.65 g, 58.75 mmol) and toluene (190 mL) were tested in the same manner as in 1-1 'above to obtain 11.3 g of Product 1-75'. (Yield: 72%)

compound FD-MS compound FD-MS 1-1 ’ m / z = 473.21 (C ₃₆ H ₂₇ N = 473.61) 1-2 ’ m / z = 523.23 (C ₄₀ H ₂₉ N = 523.66) 1-3 ’ m / z = 573.25 (C ₄₄ H ₃₁ N = 573.72) 1-4 ’ m / z = 623.26 (C ₄₈ H ₃₃ N = 623.78) 1-5 ’ m / z = 447.20 (C ₃₄ H ₂₅ N = 447.57) 1-6 ’ m / z = 371.17 (C ₂₈ H ₂₁ N = 371.47) 1-7 ’ m / z = 471.20 (C ₃₆ H ₂₅ N = 471.59) 1-8 ’ m / z = 521.21 (C ₄₀ H ₂₇ N = 521.65) 1-9 ’ m / z = 549.25 (C ₄₂ H ₃₁ N = 549.70) 1-10 ’ m / z = 625.28 (C ₄₈ H ₃₅ N = 625.80) 1-11 ’ m / z = 675.29 (C ₅₂ H ₃₇ N = 675.86) 1-12 ’ m / z = 473.21 (C ₃₆ H ₂₇ N = 473.61) 1-13 ’ m / z = 523.23 (C ₄₀ H ₂₉ N = 523.66) 1-14 ’ m / z = 623.26 (C ₄₈ H ₃₃ N = 623.78) 1-15 ’ m / z = 549.25 (C ₄₂ H ₃₁ N = 549.70) 1-16 ’ m / z = 625.28 (C ₄₈ H ₃₅ N = 625.80) 1-17 ’ m / z = 503.17 (C ₃₆ H ₂₅ NS = 503.66) 1-18 ’ m / z = 603.20 (C ₄₄ H ₂₉ NS = 603.77) 1-19 ’ m / z = 477.16 (C ₃₄ H ₂₃ NS = 477.62) 1-20 ’ m / z = 503.17 (C ₃₆ H ₂₅ NS = 503.66) 1-21 ’ m / z = 451.14 (C ₃₂ H ₂₁ NS = 451.58) 1-22 ’ m / z = 593.22 (C ₄₃ H ₃₁ NS = 593.78) 1-23 ’ m / z = 641.22 (C ₄₇ H ₃₁ NS = 641.82) 1-24 ’ m / z = 665.22 (C ₄₉ H ₃₁ NS = 665.84) 1-25 ’ m / z = 503.17 (C ₃₆ H ₂₅ NS = 503.66) 1-26 ’ m / z = 655.23 (C ₄₈ H ₃₃ NS = 655.85) 1-27 ’ m / z = 695.26 (C ₅₁ H ₃₇ NS = 695.91) 1-28 ’ m / z = 593.18 (C ₄₂ H ₂₇ NOS = 593.73) 1-29 ’ m / z = 583.14 (C ₄₀ H ₂₅ NS ₂ = 583.76) 1-30 ’ m / z = 579.20 (C ₄₂ H ₂₉ NS = 579.75) 1-31 ’ m / z = 685.19 (C ₄₈ H ₃₁ NS ₂ = 685.90) 1-32 ’ m / z = 719.23 (C ₅₂ H ₃₃ NOS = 719.89) 1-33 ’ m / z = 629.22 (C ₄₆ H ₃₁ NS = 629.81) 1-34 ’ m / z = 629.22 (C ₄₆ H ₃₁ NS = 629.81) 1-35 ’ m / z = 603.20 (C ₄₄ H ₂₉ NS = 603.77) 1-36 ’ m / z = 563.08 (C ₃₆ H ₂₁ NS ₃ = 563.75) 1-37 ’ m / z = 639.11 (C ₄₂ H ₂₅ NS ₃ = 639.85) 1-38 ’ m / z = 715.15 (C ₄₈ H ₂₉ NS ₃ = 715.95) 1-39 ’ m / z = 791.18 (C ₅₄ H ₃₃ NS ₃ = 792.04) 1-40 ’ m / z = 607.16 (C ₄₂ H ₂₅ NO ₂ S = 607.72) 1-41 ’ m / z = 633.21 (C ₄₅ H ₃₁ NOS = 633.80) 1-42 ’ m / z = 733.24 (C ₅₃ H ₃₅ NOS = 733.92) 1-43 ’ m / z = 883.29 (C ₆₅ H ₄₁ NOS = 884.09) 1-44 ’ m / z = 585.13 (C ₃₈ H ₂₃ N ₃ S ₂ = 585.74) 1-45 ’ m / z = 553.19 (C ₄₀ H ₂₇ NS = 553.71) 1-46 ’ m / z = 603.20 (C ₄₄ H ₂₉ NS = 603.77) 1-47 ’ m / z = 841.28 (C ₆₃ H ₃₉ NS = 842.06) 1-48 ’ m / z = 563.22 (C ₄₂ H ₂₉ NO = 563.69) 1-49 ’ m / z = 563.22 (C ₄₂ H ₂₉ NO = 563.69) 1-50 ’ m / z = 613.24 (C ₄₆ H ₃₁ NO = 613.76) 1-51 ’ m / z = 703.29 (C ₅₃ H ₃₇ NO = 703.87) 1-52 ’ m / z = 587.22 (C ₄₄ H ₂₉ NO = 587.71) 1-53 ’ m / z = 639.26 (C ₄₈ H ₃₃ NO = 639.78) 1-54 ’ m / z = 639.26 (C ₄₈ H ₃₃ NO = 639.78) 1-55 ’ m / z = 653.24 (C ₄₈ H ₃₁ NO ₂ = 653.77) 1-56 ’ m / z = 603.26 (C ₄₅ H ₃₃ NO = 603.75) 1-57 ’ m / z = 727.29 (C ₅₅ H ₃₇ NO = 727.89) 1-58 ’ m / z = 725.27 (C ₅₅ H ₃₅ NO = 725.87) 1-59 ’ m / z = 595.17 (C ₄₀ H ₂₅ N ₃ OS = 595.71) 1-60 ’ m / z = 567.26 (C ₄₂ H ₃₃ NO = 567.72) 1-61 ’ m / z = 611.22 (C ₄₆ H ₂₉ NO = 611.73) 1-62 ’ m / z = 617.18 (C ₄₄ H ₂₇ NOS = 617.76) 1-63 ’ m / z = 637.24 (C ₄₈ H ₃₁ NO = 637.77) 1-64 ’ m / z = 667.21 (C ₄₈ H ₂₉ NO ₃ = 667.75) 1-65 ’ m / z = 767.25 (C ₅₆ H ₃₃ NO ₃ = 767.87) 1-66 ’ m / z = 681.27 (C ₅₀ H ₃₅ NO ₂ = 681.82) 1-67 ’ m / z = 658.22 (C ₄₅ H ₃₀ N ₄ S = 658.82) 1-68 ’ m / z = 655.23 (C ₄₈ H ₃₃ NS = 655.86) 1-69 ’ m / z = 744.26 (C ₅₄ H ₃₆ N ₂ S = 744.96) 1-70 ’ m / z = 784.27 (C ₅₅ H ₃₆ N ₄ S = 784.98) 1-71 ’ m / z = 553.19 (C ₄₀ H ₂₇ NS = 553.72) 1-72 ’ m / z = 553.19 (C ₄₀ H ₂₇ NS = 553.72) 1-73 ’ m / z = 543.20 (C ₃₉ H ₂₉ NS = 543.73) 1-74 ’ m / z = 671.21 (C ₄₈ H ₃₀ FNS = 671.83) 1-75 ’ m / z = 641.25 (C ₄₆ H ₃₁ N ₃ O = 641.77) 1-76 ’ m / z = 639.26 (C ₄₈ H ₃₃ NO = 639.80) 1-77 ’ m / z = 652.25 (C ₄₈ H ₃₂ N ₂ O = 652.80) 1-78 ’ m / z = 614.24 (C ₄₅ H ₃₀ N ₂ O = 614.75) 1-79 ’ m / z = 587.22 (C ₄₄ H ₂₉ NO = 587.72) 1-80 ’ m / z = 613.24 (C ₄₆ H ₃₁ NO = 613.76) 1-81 ’ m / z = 543.26 (C ₄₀ H ₃₃ NO = 543.71) 1-82 ’ m / z = 667.25 (C ₄₉ H ₃₃ NO ₂ = 667.81)

[ Synthetic example  2]

The compound represented by Chemical Formula (2) according to the present invention (final product 1) is prepared by reacting Sub 3 and Sub 4 as shown in Reaction Scheme 1 below.

<Reaction Scheme 4>

Sub 3 Synthesis  example

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

<Scheme 5>

Synthesis example of Sub 3 (1)

Sub 3-2-1 synthesis method

Sub 3-1-1 (48.5 g, 155 mmol), bis (pinacolato) diboron (43.4 g, 171 mmol), KOAc (46 g, 466 mmol), PdCl ₂ (dppf) (3.8 g, 4.7 mmol) in DMF (980 mL) After dissolving in a solvent, it was refluxed at 120 ° C. for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ and wiped with water. After drying and concentrating the organic layer with MgSO ₄ , the resulting organic material was recrystallized using CH ₂ Cl ₂ and methanol solvent to obtain the desired Sub 3-2-1 (41.9g, 75%).

Sub 3-4-1 synthesis method

Sub 3-2-1 (40.0 g, 111 mmol) obtained above, bromo-2-nitrobenzene (26.91 g, 133 mmol), K ₂ CO ₃ (46.03 g, 333 mmol), Pd (PPh ₃ ) ₄ (7.7 g, 6.66 mmol) was put in a round bottom flask, THF (490 mL) and water (245 mL) were added and dissolved, and the mixture was refluxed at 80 ° C. for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ and wiped with water. After drying and concentrating the organic layer with MgSO ₄ , the resulting organic material was separated using a silicagel column to obtain the desired Sub 3-4-1 (30.8g, 78%).

Sub 3 (1) synthesis method

Sub 3-4-1 (20 g, 56.3 mmol) and triphenylphosphine (37 g, 141 mmol) obtained above were dissolved in o- dichlorobenzene (235 mL) and refluxed for 24 hours. After the reaction was completed, the solvent was removed using distillation under reduced pressure, and the concentrated product was silicagel column and recrystallized to obtain desired Sub 3 (1) (14.4 g, 79%).

Sub 3 (2) synthesis example

Sub 3-2-2 synthesis method

Sub 3-1-2 (48.5 g, 155 mmol) was obtained using the synthesis method of Sub 3-2-1 to obtain the desired Sub 3-2-2 (44.7 g, 80%).

Sub 3-4-2 synthesis method

Sub 3-2-2 (40.0 g, 111 mmol) was obtained using the synthesis method of Sub 3-4-1 to obtain the desired Sub 3-4-2 (31.2 g, 79%).

Sub 3 (2) synthesis method

Sub 3-4-2 (20 g, 56.3 mmol) was obtained using the synthesis method of Sub 3 (1) to obtain the desired Sub 3 (2) (14.9 g, 82%).

Sub 3 (7) synthesis example

Sub 3-2-3 synthesis method

Sub 3-1-3 (57.7 g, 155 mmol) was obtained using the synthesis method of Sub 3-2-1 to obtain the desired Sub 3-2-3 (49.4 g, 76%).

Sub 3-4-3 synthesis method

Sub 3-2-3 (46.5 g, 111 mmol) was obtained using the synthesis method of Sub 3-4-1 to obtain the desired Sub 3-4-3 (35.9 g, 79%).

Sub 3 (7) synthesis method

Sub 3-4-3. (23.3 g, 56.3 mmol) was obtained using the synthesis method of Sub 3 (1) to obtain the desired Sub 3 (7) (17.2 g, 82%).

Synthesis example of Sub 3 (13)

Sub 3-2-4 synthesis method

Sub 3-1-4 (53.8 g, 155 mmol) was obtained using the synthesis method of Sub 3-2-1 to obtain the desired Sub 3-2-4 (45.2 g, 74%).

Sub 3-4-4 synthesis method

Sub 3-2-4 (43.8 g, 111 mmol) was obtained using the synthesis method of Sub 3-4-1 to obtain the desired Sub 3-4-4 (33.7 g, 78%).

Synthesis of Sub 3 (13)

Sub 3-4-4. (21.9 g, 56.3 mmol) was obtained using the synthesis method of Sub 3 (1) to obtain the desired Sub 3 (13) (16.1 g, 80%).

Synthesis of Sub 3 (26)

Sub 3-2-5 synthesis method

Sub 3-1-5 (50.1 g, 155 mmol) was obtained using the synthesis method of Sub 3-2-1 to obtain the desired Sub 3-2-5 (43.6 g, 76%).

Sub 3-4-5 synthesis method

Sub 3-2-5 (41.1 g, 111 mmol), Sub 3-3-1 (33.5 g, 133 mmol), was obtained by using the synthesis method of Sub 3-4-1. g, 80%).

Sub 3 (26) synthesis method

Sub 3-4-5. (23.4 g, 56.3 mmol) was obtained using the synthesis method of Sub 3 (1) to obtain the desired Sub 3 (26) (17.5 g, 80%).

Synthesis of Sub 3 (39)

Sub 3-2-6 Synthesis

Sub 3-1-6 (57.7 g, 155 mmol) was obtained using the synthesis method of Sub 3-2-1 to obtain the desired Sub 3-2-6 (50.7 g, 78%).

Sub 3-4-6 Synthesis

Sub 3-2-6 (46.5 g, 111 mmol), Sub 3-3-2 (33.5 g, 133 mmol), was obtained by using the synthesis method of Sub 3-4-1, Sub 3-4-6 (47.8 g, 81%).

Sub 3 (39) synthesis method

Sub 3-4-6. (26.2 g, 56.3 mmol) was obtained using the synthesis method of Sub 3 (1) to obtain the desired Sub 3 (39) (19.2 g, 79%).

Sub 3 (45) synthesis example

Sub 3-2-7 Synthesis

Sub 3-1-7 (46.1 g, 155 mmol) was obtained using the synthesis method of Sub 3-2-1 to obtain the desired Sub 3-2-7 (43.8 g, 82%).

Sub 3-4-7 Synthesis

Sub 3-2-7 (38.2 g, 111 mmol), Sub 3-3-1 (33.5 g, 133 mmol), was obtained using the synthesis method of Sub 3-4-1, Sub 3-4-7 (35.9 g, 83%).

Sub 3 (45) synthesis method

Sub 3-4-7. (21.9 g, 56.3 mmol) was obtained using the synthesis method of Sub 3 (1) to obtain the desired Sub 3 (45) (16.1 g, 80%).

Synthesis of Sub 3 (66)

Sub 3-2-8 synthesis method

Sub 3-1-8 (42.3 g, 155 mmol) was obtained using the synthesis method of Sub 3-2-1 to obtain the desired Sub 3-2-8 (40.2 g, 81%).

Sub 3-4-8 synthesis method

Sub 3-2-8 (35.5 g, 111 mmol), Sub 3-3-3 (40.2 g, 133 mmol), is obtained by using the synthesis method of Sub 3-4-1, Sub 3-4-8 (37.8 g, 82%).

Sub 3 (66) synthesis method

Sub 3-4-8. (23.4 g, 56.3 mmol) was obtained using the synthesis method of Sub 3 (1) to obtain the desired Sub 3 (66) (17.5 g, 80%).

Examples of Sub 3 are as follows, but are not limited thereto.

compound FD-MS compound FD-MS Sub 3 (1) m / z = 323.08 (C ₂₂ H ₁₃ NS = 323.41) Sub 3 (2) m / z = 323.08 (C ₂₂ H ₁₃ NS = 323.41) Sub 3 (3) m / z = 307.10 (C ₂₂ H ₁₃ NO = 307.34) Sub 3 (4) m / z = 307.10 (C ₂₂ H ₁₃ NO = 307.34) Sub 3 (5) m / z = 333.15 (C ₂₅ H ₁₉ N = 333.43) Sub 3 (6) m / z = 382.15 (C ₂₈ H ₁₈ N ₂ = 382.46) Sub 3 (7) m / z = 382.15 (C ₂₈ H ₁₈ N ₂ = 382.47) Sub 3 (8) m / z = 323.08 (C ₂₂ H ₁₃ NS = 323.41) Sub 3 (9) m / z = 307.10 (C ₂₂ H ₁₃ NO = 307.35) Sub 3 (10) m / z = 383.17 (C ₂₉ H ₂₁ N = 383.49) Sub 3 (11) m / z = 373.09 (C ₂₆ H ₁₅ NS = 373.47) Sub 3 (12) m / z = 323.08 (C ₂₂ H ₁₃ NS = 323.41) Sub 3 (13) m / z = 357.12 (C ₂₆ H ₁₅ NO = 357.41) Sub 3 (14) m / z = 333.15 (C ₂₅ H ₁₉ N = 333.43) Sub 3 (15) m / z = 373.09 (C ₂₆ H ₁₅ NS = 373.47) Sub 3 (16) m / z = 357.12 (C ₂₆ H ₁₅ NO = 357.41) Sub 3 (17) m / z = 383.17 (C ₂₉ H ₂₁ N = 383.49) Sub 3 (18) m / z = 373.09 (C ₂₆ H ₁₅ NS = 373.47) Sub 3 (19) m / z = 407.13 (C ₃₀ H ₁₇ NO = 407.47) Sub 3 (20) m / z = 433.18 (C ₃₃ H ₂₃ N = 433.55) Sub 3 (21) m / z = 373.09 (C ₂₆ H ₁₅ NS = 373.47) Sub 3 (22) m / z = 357.12 (C ₂₆ H ₁₅ NO = 357.41) Sub 3 (23) m / z = 662.25 (C ₄₈ H ₃₀ N ₄ = 662.80) Sub 3 (24) m / z = 373.09 (C ₂₆ H ₁₅ NS = 373.47) Sub 3 (25) m / z = 357.12 (C ₂₆ H ₁₅ NO = 357.41) Sub 3 (26) m / z = 383.17 (C ₂₉ H ₂₁ N = 383.49) Sub 3 (27) m / z = 432.16 (C ₃₂ H ₂₀ N ₂ = 432.53) Sub 3 (28) m / z = 323.08 (C ₂₂ H ₁₃ NS = 323.41) Sub 3 (29) m / z = 307.10 (C ₂₂ H ₁₃ NO = 307.35) Sub 3 (30) m / z = 455.17 (C ₃₅ H ₂₁ N = 455.56) Sub 3 (31) m / z = 432.16 (C ₃₂ H ₂₀ N ₂ = 432.53) Sub 3 (32) m / z = 323.08 (C ₂₂ H ₁₃ NS = 323.41) Sub 3 (33) m / z = 307.10 (C ₂₂ H ₁₃ NO = 307.35) Sub 3 (34) m / z = 383.17 (C ₂₉ H ₂₁ N = 383.49) Sub 3 (35) m / z = 432.16 (C ₃₂ H ₂₀ N ₂ = 439.53) Sub 3 (36) m / z = 373.09 (C ₂₆ H ₁₅ NS = 373.47) Sub 3 (37) m / z = 357.12 (C ₂₆ H ₁₅ NO = 357.41) Sub 3 (38) m / z = 383.17 (C ₂₉ H ₂₁ N = 383.49) Sub 3 (39) m / z = 432.16 (C ₃₂ H ₂₀ N ₂ = 432.53) Sub 3 (40) m / z = 373.09 (C ₂₆ H ₁₅ NS = 373.47) Sub 3 (41) m / z = 357.12 (C ₂₆ H ₁₅ NO = 357.41) Sub 3 (42) m / z = 383.17 (C ₂₉ H ₂₁ N = 383.49) Sub 3 (43) m / z = 432.16 (C ₃₂ H ₂₀ N ₂ = 432.53) Sub 3 (44) m / z = 373.09 (C ₂₆ H ₁₅ NS = 373.47) Sub 3 (45) m / z = 357.12 (C ₂₆ H ₁₅ NO = 357.41) Sub 3 (46) m / z = 505.18 (C ₃₉ H ₂₃ N = 505.62) Sub 3 (47) m / z = 382.15 (C ₂₈ H ₁₈ N ₂ = 382.47) Sub 3 (48) m / z = 323.08 (C ₂₂ H ₁₃ NS = 323.41) Sub 3 (49) m / z = 307.10 (C ₂₂ H ₁₃ NO = 307.35) Sub 3 (50) m / z = 333.15 (C ₂₅ H ₁₉ N = 333.43) Sub 3 (51) m / z = 432.16 (C ₃₂ H ₂₀ N ₂ = 432.53) Sub 3 (52) m / z = 323.08 (C ₂₂ H ₁₃ NS = 323.41) Sub 3 (53) m / z = 307.10 (C ₂₂ H ₁₃ NO = 307.35) Sub 3 (54) m / z = 457.18 (C ₃₅ H ₂₃ N = 457.58) Sub 3 (55) m / z = 432.16 (C ₃₂ H ₂₀ N ₂ = 432.53) Sub 3 (56) m / z = 373.09 (C ₂₆ H ₁₅ NS = 373.47) Sub 3 (57) m / z = 357.12 (C ₂₆ H ₁₅ NO = 357.41) Sub 3 (58) m / z = 383.17 (C ₂₉ H ₂₁ N = 383.49) Sub 3 (59) m / z = 616.17 (C ₄₂ H ₂₄ N ₄ S = 616.74) Sub 3 (60) m / z = 323.08 (C ₂₂ H ₁₃ NS = 323.41) Sub 3 (61) m / z = 307.10 (C ₂₂ H ₁₃ NO = 307.35) Sub 3 (62) m / z = 373.09 (C ₂₆ H ₁₅ NS = 373.47) Sub 3 (63) m / z = 432.16 (C ₃₂ H ₂₀ N ₂ = 432.53) Sub 3 (64) m / z = 373.09 (C ₂₆ H ₁₅ NS = 373.47) Sub 3 (65) m / z = 357.12 (C ₂₆ H ₁₅ NO = 357.41) Sub 3 (66) m / z = 383.17 (C ₂₉ H ₂₁ N = 383.49)

Sub 4 example

Examples of Sub 4 are as follows, but are not limited thereto.

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 = 233.10) Sub 4-5 m / z = 309.02 (C ₁₇ H ₁₂ BrN = 310.19) Sub 4-6 m / z = 311.01 (C ₁₅ H ₁₀ BrN ₃ = 312.16) Sub 4-7 m / z = 310.01 (C ₁₆ H ₁₁ BrN ₂ = 311.18) Sub 4-8 m / z = 310.01 (C ₁₆ H ₁₁ BrN ₂ = 311.18) Sub 4-9 m / z = 310.01 (C ₁₆ H ₁₁ BrN ₂ = 311.18) Sub 4-10 m / z = 387.04 (C ₂₁ H ₁₄ BrN ₃ = 388.26) Sub 4-11 m / z = 386.04 (C ₂₂ H ₁₅ BrN ₂ = 387.27) Sub 4-12 m / z = 386.04 (C ₂₂ H ₁₅ BrN ₂ = 387.27) Sub 4-13 m / z = 348.03 (C ₁₉ H ₁₃ BrN ₂ = 349.22) Sub 4-14 m / z = 271.99 (C ₁₃ H ₉ BrN ₂ = 273.13) Sub 4-15 m / z = 283.99 (C ₁₄ H ₉ BrN ₂ = 285.14) Sub 4-16 m / z = 374.01 (C ₂₀ H ₁₁ BrN ₂ O = 375.22) Sub 4-17 m / z = 400.06 (C ₂₃ H ₁₇ BrN ₂ = 401.30) Sub 4-18 m / z = 360.03 (C ₂₀ H ₁₃ BrN ₂ = 361.23) Sub 4-19 m / z = 476.09 (C ₂₉ H ₂₁ BrN ₂ = 477.39) Sub 4-20 m / z = 284.99 (C ₁₃ H ₈ BrN ₃ = 286.13) Sub 4-21 m / z = 289.03 (C ₁₄ H ₄ D ₅ BrN ₂ = 290.2) Sub 4-22 m / z = 284.99 (C ₁₃ H ₈ BrN ₃ = 286.13) Sub 4-23 m / z = 375.00 (C ₁₉ H ₁₀ BrN ₃ O = 376.2) Sub 4-24 m / z = 401.05 (C ₂₂ H ₁₆ BrN ₃ = 402.29) Sub 4-25 m / z = 296.02 (C ₁₆ H ₉ ClN ₂ S = 296.77) Sub 4-26 m / z = 322.03 (C ₁₈ H ₁₁ ClN ₂ S = 322.81) Sub 4-27 m / z = 322.03 (C ₁₈ H ₁₁ ClN ₂ S = 322.81) Sub 4-28 m / z = 168.98 (C ₇ H ₄ ClNS = 169.63) Sub 4-29 m / z = 168.98 (C ₇ H ₄ ClNS = 169.63)) Sub 4-30 m / z = 169.97 (C ₆ H ₃ ClN ₂ S = 170.62) Sub 4-31 m / z = 246.00 (C ₁₂ H ₇ ClN ₂ S = 246.72) Sub 4-32 m / z = 322.03 (C ₁₈ H ₁₁ ClN ₂ S = 322.81) Sub 4-33 m / z = 322.03 (C ₁₈ H ₁₁ ClN ₂ S = 322.81) Sub 4-34 m / z = 168.98 (C ₇ H ₄ ClNS = 169.63) Sub 4-35 m / z = 168.98 (C ₇ H ₄ ClNS = 169.63)) Sub 4-36 m / z = 169.97 (C ₆ H ₃ ClN ₂ S = 170.62) Sub 4-37 m / z = 229.04 (C ₁₂ H ₈ ClN ₃ = 229.67) Sub 4-38 m / z = 279.06 (C ₁₆ H ₁₀ ClN ₃ = 279.72) Sub 4-39 m / z = 305.07 (C ₁₈ H ₁₂ ClN ₃ = 305.76) Sub 4-40 m / z = 228.05 (C ₁₃ H ₉ ClN ₂ = 228.68) Sub 4-41 m / z = 228.05 (C ₁₃ H ₉ ClN ₂ = 228.68) Sub 4-42 m / z = 229.04 (C ₁₂ H ₈ ClN ₃ = 229.67) Sub 4-43 m / z = 229.04 (C ₁₂ H ₈ ClN ₃ = 229.67) Sub 4-44 m / z = 279.06 (C ₁₆ H ₁₀ ClN ₃ = 279.72) Sub 4-45 m / z = 305.07 (C ₁₈ H ₁₂ ClN ₃ = 305.76) Sub 4-46 m / z = 228.05 (C ₁₃ H ₉ ClN ₂ = 228.68) Sub 4-47 m / z = 228.05 (C ₁₃ H ₉ ClN ₂ = 228.68) Sub 4-48 m / z = 229.04 (C ₁₂ H ₈ ClN ₃ = 229.67) Sub 4-49 m / z = 330.1 (C ₂₀ H ₁₁ ClN ₂ O = 330.77) Sub 4-50 m / z = 372.05 (C ₂₂ H ₁₃ ClN ₂ S = 372.87) Sub 4-51 m / z = 366.09 (C ₂₄ H ₁₅ ClN ₂ = 366.85) Sub 4-52 m / z = 340.08 (C ₂₂ H ₁₃ ClN ₂ = 340.81) Sub 4-53 m / z = 290.06 (C ₁₈ H ₁₁ ClN ₂ = 290.75) Sub 4-54 m / z = 340.08 (C ₂₂ H ₁₃ ClN ₂ = 340.81)

Final products 2 Synthesis  example

3-6 Synthetic Example

Sub 3 (1) (15.3g, 47.3 mmol) was put in a round bottom flask and dissolved in toluene (500 mL), then Sub 4-15 (14.8g, 52.0 mmol), Pd ₂ (dba) ₃ (2.4 g, 2.6 mmol), P ( t -Bu) ₃ (1.1 g, 5.2 mmol), NaO t -Bu (15 g, 156.1 mmol) was added and stirred at 100 ° C. After the reaction was completed, the organic layer was extracted with CH ₂ Cl ₂ and water, dried over MgSO ₄ and concentrated, and then the resulting compound was silicagel column and recrystallized to obtain 18.5 g of product (yield: 74%).

3-1 Synthetic Example

Sub 3 (7) (18.1 g, 47.3 mmol), toluene (500 mL), Sub 4-1 (8.2 g, 52.0 mmol), Pd ₂ (dba) ₃ (2.0 g, 2.2 mmol), P ( t -Bu ) ₃ (0.9 g, 4.4 mmol), NaO t -Bu (12.7 g, 132 mmol) was obtained using the synthesis method of 3-6 to obtain a final product 16.9 g (yield: 78%).

3-7 Synthetic Example

Sub 3 (1) (15.3 g, 47.3 mmol) and Sub 4-25 (15.4 g, 52.0 mmol) were obtained using the synthesis method of 3-6 to obtain a final product 20.4 g (yield: 74%).

3-8 Synthetic Example

Sub 3 (1) (15.3 g, 47.3 mmol) and Sub 4-53 (15.1 g, 52 mmol) obtained 19.7 g (yield: 72%) of the final product using the synthesis method of 3-6.

3- 11 Synthetic Example

Sub 3 (13) (16.9 g, 47.3 mmol) and Sub 4-55 (16.1 g, 52.0 mmol) were obtained using the synthesis method of 3-6 to obtain a final product 19.7 g (yield: 71%).

3-16 Synthetic Example

Sub 3 (17) (18.1 g, 47.2 mmol) and Sub 4-56 (16.7 g, 52.0 mmol) were obtained using the synthesis method of 3-6 to obtain 19.5 g of the final product (yield: 66%).

3-17 Synthetic Example

Sub 3 (59) (20.5 g, 47.4 mmol), Sub 4-57 (13.7 g, 52.0 mmol) was obtained using the synthesis method of 3-6 to obtain a final product 20.4 g (yield: 70%).

3-47 Synthetic Example

Sub 3 (45) (16.9 g, 47.3 mmol) and Sub 4-58 (14.6 g, 52.0 mmol) were obtained using the synthesis method of 3-6 to obtain a final product 19.6 g (yield: 69%).

3-52 Synthetic Example

Sub 3 (50) (15.8 g, 47.4 mmol), Sub 4-12 (20.2 g, 52.0 mmol) was obtained using the synthesis method of 3-6 to obtain a final product 21.2 g (yield: 70%).

3-70 Synthetic Example

Sub 3 (60) (17.7 g, 47.4 mmol), Sub 4-59 (17.8 g, 52.0 mmol) was obtained using the synthesis method of 3-6 to obtain a final product 23.4 g (yield: 73%).

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 = 603.18 (C ₄₂ H ₂₅ N ₃ S = 603.74) 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 = 589.22 (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 / z613.25 (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 = 511.17 (C ₃₆ H ₂₁ N ₃ O = 511.58) 3-64 m / z = 587.24 (C ₄₃ H ₂₉ N ₃ = 587.73) 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 = 687.23 (C ₅₀ H ₂₉ N ₃ O = 687.80) 3-72 m / z = 743.24 (C ₅₃ H ₃₃ N ₃ S = 743.93) 3-73 m / z = 703.21 (C ₅₀ H ₂₉ N ₃ S = 703.86) 3-74 m / z = 603.18 (C ₄₂ H ₂₅ N ₃ S = 603.74) 3-75 m / z = 735.18 (C ₅₀ H ₂₉ N ₃ S ₂ = 735.92) 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 = 710.16 (C ₄₇ H ₂₆ N ₄ S ₂ = 710.87) 3-80 m / z = 818.25 (C ₅₈ H ₃₄ N ₄ S = 819.00) 3-81 m / z = 844.27 (C ₆₀ H ₃₆ N ₄ S = 845.04) 3-82 m / z = 667.17 (C ₄₆ H ₂₅ N ₃ OS = 667.79) 3-83 m / z = 703.80 (C ₅₀ H ₂₉ N ₃ O ₂ = 703.80) 3-84 m / z = 629.21 (C ₄₄ H ₂₇ N ₃ O ₂ = 629.72)

On the other hand, although the exemplary synthetic examples of the present invention represented by Formulas 1 and 2 have been described, they are all Buchwald-Hartwig cross coupling reactions, Suzuki cross-coupling reactions, Intramolecular acid-induced cyclization reactions (J. mater. Chem. 1999 , 9, 2095.), Pd (II) -catalyzed oxidative cyclization reaction (Org. Lett. 2011, 13, 5504), Grignard reaction, Cyclic Dehydration reaction and PPh3-mediated reductive cyclization reaction (J. Org. Chem. 2005, 70, 5014.) and other substituents defined in Chemical Formulas 1 and 2 (R ¹ to R ¹ , Ar1 to Ar4, L1 to L2, X1 to X2) are combined in addition to the substituents specified in the specific synthesis examples. It will be easily understood by those skilled in the art. For example, in Reaction 1, Sub 1 + Sub 2-> Final Product 1 reaction, Reaction 2 synthesizes Sub 2, Reaction 3 in Sub 3 + Sub 4-> Final Product 2 reaction, all for Buchwald-Hartwig cross coupling reaction Based on the scheme, the reaction of Sub 3-2 + Sub 3-3-> Sub 3-4 in Scheme 4 is based on the Suzuki cross-coupling reaction, and the reaction of Sub 3-4-> Sub 3 in Scheme 4 is the PPh3-mediated reductivecyclization reaction. (J. Org. Chem. 2005, 70, 5014.). The above reactions will proceed even if a substituent not specifically specified is bound.

Manufacturing evaluation of organic electric devices

Example 1) Red  Fabrication and testing of organic light emitting devices

First, N ^1- (naphthalen-2-yl) -N ⁴ , N ⁴ -bis (4- (naphthalen-2-yl (phenyl) amino) phenyl as a hole injection layer first on the ITO layer (anode) formed on the glass substrate. ) -N ¹ -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) film was vacuum deposited to form a thickness of 60 nm. Subsequently, N, N'-Bis (1-naphthalenyl) -N, N'-bis-phenyl- (1,1'-biphenyl) -4,4'-diamine (hereinafter abbreviated as NPB) is 60 nm thick. Vacuum-deposited to form a hole transport layer. As a host on the hole transport layer, a mixture of the above-described compound represented by Chemical Formula (1) and Chemical Formula (2) in a ratio of 3: 7 was used, and as a dopant, (piq) ₂ Ir (acac) [bis- (1 -phenylisoquinolyl) iridium (III) acetylacetonate] was doped to a weight of 95: 5 to deposit a 30 nm thick light emitting layer on the hole transport layer. As the hole blocking layer, (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinolineoleito) aluminum (hereinafter abbreviated as BAlq) is vacuum deposited to a thickness of 10 nm, and the electron transport layer Tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was deposited to a thickness of 40 nm. Then, an organic electroluminescent device was manufactured by depositing LiF, a halogenated alkali metal, as an electron injection layer to a thickness of 0.2 nm, and then depositing Al to a thickness of 150 nm to use as a cathode.

The electroluminescence (EL) characteristics were measured by PR-650 of photoresearch by applying a direct bias DC voltage to the organic electroluminescent elements of the Examples and Comparative Examples prepared as described above, and the measurement result showed a luminance of 2500 cd / m2. T95 life was measured by a life measurement equipment manufactured by Max Science. The following table shows the results of device fabrication and evaluation.

[ Comparative example  1 ~ 3]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound represented by Formula 2 was used alone 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 as a host.

[ 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 as a host.

[ 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 as a host.

[ Comparative example  8]

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

[ Comparative example  9]

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

[Comparative compound 1] [Comparative compound 2] [Comparative compound 3] [Comparative compound 4]

Host 1 Host 2 Voltage Current Density Brightness
(cd / m2) Efficiency Lifetime
T (95) Comparative Example (1) - Compound (3-6) 6.3 17.9 2500.0 14.0 105.7 Comparative Example (2) - Compound (3-61) 6.5 18.2 2500.0 13.7 104.2 Comparative Example (3) - Compound (3-74) 6.6 18.9 2500.0 13.2 101.6 Comparative Example (4) - Comparative Compound 1 7.1 20.4 2500.0 12.3 80.3 Comparative Example (5) - Comparative Compound 2 7.0 20.0 2500.0 12.5 81.9 Comparative Example (6) - Comparative Compound 3 6.9 19.5 2500.0 12.8 85.4 Comparative Example (7) - Comparative Compound 4 7.1 20.2 2500.0 12.4 80.9 Comparative Example (8) Comparative Compound 1 Comparative Compound 2 6.2 13.0 2500.0 19.3 102.8 Comparative Example (9) Comparative Compound 3 Comparative Compound 4 6.0 12.4 2500.0 20.1 105.9 Example (1) Compound (1-4 ') Compound (3-6) 5.3 8.2 2500.0 30.5 131.1 Example (2) Compound (1-10 ') Compound (3-6) 5.3 7.8 2500.0 31.9 130.6 Example (3) Compound (1-16 ') Compound (3-6) 5.1 8.3 2500.0 30.2 131.6 Example (4) Compound (1-21 ') Compound (3-6) 5.3 7.7 2500.0 32.4 132.4 Example (5) Compound (1-33 ') Compound (3-6) 5.5 7.6 2500.0 32.7 132.9 Example (6) Compound (1-45 ') Compound (3-6) 5.1 7.8 2500.0 32.1 132.7 Example (7) Compound (1-48 ') Compound (3-6) 5.4 7.4 2500.0 33.9 134.6 Example (8) Compound (1-50 ') Compound (3-6) 5.4 7.3 2500.0 34.1 133.5 Example (9) Compound (1-55 ') Compound (3-6) 5.1 7.3 2500.0 34.2 134.3 Example (10) Compound (1-56 ') Compound (3-6) 5.2 7.4 2500.0 33.9 133.2 Example (11) Compound (1-4 ') Compound (3-7) 5.3 9.8 2500.0 25.6 120.7 Example (12) Compound (1-10 ') Compound (3-7) 5.3 9.9 2500.0 25.3 120.5 Example (13) Compound (1-16 ') Compound (3-7) 5.2 9.7 2500.0 25.7 120.7 Example (14) Compound (1-21 ') Compound (3-7) 5.1 9.4 2500.0 26.5 122.7 Example (15) Compound (1-33 ') Compound (3-7) 5.1 9.4 2500.0 26.5 121.7 Example (16) Compound (1-45 ') Compound (3-7) 5.4 9.5 2500.0 26.4 121.8 Example (17) Compound (1-48 ') Compound (3-7) 5.1 9.2 2500.0 27.1 123.5 Example (18) Compound (1-50 ') Compound (3-7) 5.4 9.0 2500.0 27.8 124.8 Example (19) Compound (1-55 ') Compound (3-7) 5.3 9.1 2500.0 27.6 123.0 Example (20) Compound (1-56 ') Compound (3-7) 5.1 9.2 2500.0 27.2 124.2 Example (21) Compound (1-4 ') Compound (3-8) 5.2 9.6 2500.0 25.9 120.2 Example (22) Compound (1-10 ') Compound (3-8) 5.5 9.8 2500.0 25.6 120.6 Example (23) Compound (1-16 ') Compound (3-8) 5.4 9.8 2500.0 25.5 120.5 Example (24) Compound (1-21 ') Compound (3-8) 5.2 9.5 2500.0 26.3 122.1 Example (25) Compound (1-33 ') Compound (3-8) 5.4 9.6 2500.0 26.1 121.2 Example (26) Compound (1-45 ') Compound (3-8) 5.3 9.5 2500.0 26.4 121.0 Example (27) Compound (1-48 ') Compound (3-8) 5.3 9.1 2500.0 27.6 124.4 Example (28) Compound (1-50 ') Compound (3-8) 5.2 9.0 2500.0 27.7 123.1 Example (29) Compound (1-55 ') Compound (3-8) 5.3 9.2 2500.0 27.2 124.6 Example (30) Compound (1-56 ') Compound (3-8) 5.3 9.0 2500.0 27.6 124.3 Example (31) Compound (1-4 ') Compound (3-9) 5.4 10.0 2500.0 25.1 120.1 Example (32) Compound (1-10 ') Compound (3-9) 5.2 9.8 2500.0 25.5 120.8 Example (33) Compound (1-16 ') Compound (3-9) 5.1 10.0 2500.0 25.0 120.3 Example (34) Compound (1-21 ') Compound (3-9) 5.4 9.3 2500.0 26.9 121.8 Example (35) Compound (1-33 ') Compound (3-9) 5.4 9.6 2500.0 26.1 122.5 Example (36) Compound (1-45 ') Compound (3-9) 5.1 9.4 2500.0 26.5 122.2 Example (37) Compound (1-48 ') Compound (3-9) 5.0 9.2 2500.0 27.2 123.3 Example (38) Compound (1-50 ') Compound (3-9) 5.2 9.0 2500.0 27.9 125.0 Example (39) Compound (1-55 ') Compound (3-9) 5.5 9.1 2500.0 27.4 124.0 Example (40) Compound (1-56 ') Compound (3-9) 5.3 9.2 2500.0 27.3 124.9 Example (41) Compound (1-4 ') Compound (3-15) 5.4 9.9 2500.0 25.2 120.5 Example (42) Compound (1-10 ') Compound (3-15) 5.0 9.8 2500.0 25.4 120.3 Example (43) Compound (1-16 ') Compound (3-15) 5.0 9.9 2500.0 25.2 120.5 Example (44) Compound (1-21 ') Compound (3-15) 5.2 9.6 2500.0 26.1 121.7 Example (45) Compound (1-33 ') Compound (3-15) 5.4 9.4 2500.0 26.7 121.9 Example (46) Compound (1-45 ') Compound (3-15) 5.5 9.3 2500.0 26.8 121.6 Example (47) Compound (1-48 ') Compound (3-15) 5.3 9.2 2500.0 27.3 123.4 Example (48) Compound (1-50 ') Compound (3-15) 5.1 9.3 2500.0 27.0 124.3 Example (49) Compound (1-55 ') Compound (3-15) 5.4 9.1 2500.0 27.5 124.5 Example (50) Compound (1-56 ') Compound (3-15) 5.1 9.0 2500.0 27.8 124.0 Example (51) Compound (1-4 ') Compound (3-37) 5.0 9.8 2500.0 25.6 120.8 Example (52) Compound (1-10 ') Compound (3-37) 5.2 9.9 2500.0 25.2 120.3 Example (53) Compound (1-16 ') Compound (3-37) 5.4 9.9 2500.0 25.4 120.2 Example (54) Compound (1-21 ') Compound (3-37) 5.5 9.4 2500.0 26.6 122.2 Example (55) Compound (1-33 ') Compound (3-37) 5.3 9.5 2500.0 26.4 121.7 Example (56) Compound (1-45 ') Compound (3-37) 5.3 9.5 2500.0 26.3 122.5 Example (57) Compound (1-48 ') Compound (3-37) 5.2 8.9 2500.0 28.0 124.6 Example (58) Compound (1-50 ') Compound (3-37) 5.4 9.1 2500.0 27.4 123.9 Example (59) Compound (1-55 ') Compound (3-37) 5.3 8.9 2500.0 28.0 123.7 Example (60) Compound (1-56 ') Compound (3-37) 5.1 9.0 2500.0 27.6 123.5 Example (61) Compound (1-4 ') Compound (3-46) 5.3 9.6 2500.0 25.9 120.9 Example (62) Compound (1-10 ') Compound (3-46) 5.2 9.9 2500.0 25.4 120.9 Example (63) Compound (1-16 ') Compound (3-46) 5.3 9.8 2500.0 25.6 120.5 Example (64) Compound (1-21 ') Compound (3-46) 5.0 9.3 2500.0 26.7 121.0 Example (65) Compound (1-33 ') Compound (3-46) 5.3 9.6 2500.0 26.2 122.5 Example (66) Compound (1-45 ') Compound (3-46) 5.2 9.5 2500.0 26.4 121.4 Example (67) Compound (1-48 ') Compound (3-46) 5.2 9.2 2500.0 27.3 123.0 Example (68) Compound (1-50 ') Compound (3-46) 5.4 9.1 2500.0 27.4 124.7 Example (69) Compound (1-55 ') Compound (3-46) 5.0 9.3 2500.0 27.0 124.8 Example (70) Compound (1-56 ') Compound (3-46) 5.2 8.9 2500.0 27.9 123.3 Example (71) Compound (1-4 ') Compound (3-50) 5.4 9.9 2500.0 25.3 120.6 Example (72) Compound (1-10 ') Compound (3-50) 5.4 9.9 2500.0 25.1 120.5 Example (73) Compound (1-16 ') Compound (3-50) 5.2 10.0 2500.0 25.1 120.4 Example (74) Compound (1-21 ') Compound (3-50) 5.3 9.5 2500.0 26.2 122.6 Example (75) Compound (1-33 ') Compound (3-50) 5.5 9.3 2500.0 26.9 121.5 Example (76) Compound (1-45 ') Compound (3-50) 5.3 9.4 2500.0 26.5 121.2 Example (77) Compound (1-48 ') Compound (3-50) 5.3 8.9 2500.0 28.0 123.6 Example (78) Compound (1-50 ') Compound (3-50) 5.1 9.0 2500.0 27.9 124.3 Example (79) Compound (1-55 ') Compound (3-50) 5.0 9.0 2500.0 27.8 124.2 Example (80) Compound (1-56 ') Compound (3-50) 5.4 9.0 2500.0 27.9 124.7 Example (81) Compound (1-4 ') Compound (3-61) 5.1 8.6 2500.0 28.9 125.0 Example (82) Compound (1-10 ') Compound (3-61) 5.3 8.9 2500.0 28.2 126.5 Example (83) Compound (1-16 ') Compound (3-61) 5.1 8.8 2500.0 28.3 126.3 Example (84) Compound (1-21 ') Compound (3-61) 5.2 8.4 2500.0 29.6 127.3 Example (85) Compound (1-33 ') Compound (3-61) 5.5 8.5 2500.0 29.4 127.5 Example (86) Compound (1-45 ') Compound (3-61) 5.0 8.3 2500.0 30.0 127.4 Example (87) Compound (1-48 ') Compound (3-61) 5.4 8.1 2500.0 30.8 129.5 Example (88) Compound (1-50 ') Compound (3-61) 5.3 8.2 2500.0 30.3 128.7 Example (89) Compound (1-55 ') Compound (3-61) 5.4 8.1 2500.0 30.9 128.1 Example (90) Compound (1-56 ') Compound (3-61) 5.4 8.1 2500.0 30.9 129.6 Example (91) Compound (1-4 ') Compound (3-74) 5.1 9.8 2500.0 25.4 120.6 Example (92) Compound (1-10 ') Compound (3-74) 5.2 9.8 2500.0 25.4 120.4 Example (93) Compound (1-16 ') Compound (3-74) 5.2 9.6 2500.0 26.0 120.8 Example (94) Compound (1-21 ') Compound (3-74) 5.4 9.4 2500.0 26.5 122.7 Example (95) Compound (1-33 ') Compound (3-74) 5.5 9.5 2500.0 26.4 122.9 Example (96) Compound (1-45 ') Compound (3-74) 5.0 9.6 2500.0 26.1 122.8 Example (97) Compound (1-48 ') Compound (3-74) 5.0 9.2 2500.0 27.3 124.4 Example (98) Compound (1-50 ') Compound (3-74) 5.4 9.0 2500.0 27.7 123.5 Example (99) Compound (1-55 ') Compound (3-74) 5.3 9.0 2500.0 27.8 124.9 Example (100) Compound (1-56 ') Compound (3-74) 5.5 9.2 2500.0 27.1 124.3

As can be seen from the results of Table 6, when using the material for the organic electroluminescent device of the present invention represented by Formula 1 and Formula 2 as a phosphorescent host (Examples 1 to 100), a device using a single material (comparative Compared to Examples 1-7), it was confirmed that the driving voltage, efficiency and lifespan were significantly improved. In detail, the compounds of the present invention represented by the formula (2), Comparative Compounds 1 to Comparative Compounds 4 in Comparative Example 1 to Comparative Example 7 alone as a phosphorescent host, the compounds of the present invention (3-6, 3-61, 3 It was confirmed that Comparative Examples 1 to 3 using -74) exhibited higher efficiency and higher lifetime than Comparative Examples 4 to 7 using comparative compounds.

In addition, Comparative Example 8 and Comparative Example 9, which were used as a phosphorescent host by mixing Comparative Compound 1 and Comparative Compound 2, or Comparative Compound 3 and Comparative Compound 4, as compared to Comparative Examples 1 to 7 using the single substance, showed higher efficiency. I could confirm that. When comparing Comparative Example 8 and Comparative Example 9, compared to Comparative Example 8 in which a 5-ring heterocyclic compound having the same nitrogen atom was mixed, a heterocyclic polycyclic ring compound having different heteroatoms (N, S) among 5-cyclic ring compounds was obtained. It was confirmed that Comparative Example 9 using the included mixture exhibited a higher efficiency. And it was confirmed that Examples 1 to 100, which were used as a host by mixing the compounds of Formula 1 and Formula 2, which are compounds of the present invention, as a host, showed significantly higher efficiency and life than Comparative Examples 1 to 9 It was confirmed that the driving voltage was indicated.

Based on the results of the above experiment, the present inventors determined that the substance of the substance of Formula 1 and the substance of Formula 2 has new characteristics other than the characteristics of each substance, and thus the substance of Formula 1 and the substance of Formula 2 , PL lifetime was measured using each mixture of the present invention. As a result, when the compounds of the present invention, Formula 1 and Formula 2 were mixed, it was confirmed that a new PL wavelength was formed, unlike that of a single compound, and the newly formed PL wavelength was reduced and extinction time of each of Formula 1 and Formula 1 materials. It was confirmed that the decrease and the extinction time increased from about 60 times to as much as about 360 times. When the compound of the present invention is used in combination, not only electrons and holes are moved through the energy level of each substance, but also electrons, hole movement or energy due to exciplex of new regions having new energy levels formed due to mixing. It is judged that the efficiency and life of the furnace are increased. As a result, when using the mixture of the present invention, it can be said that the mixed thin film is an important example of exciplex energy transfer and luminescence processes.

In addition, the reason why the combination of the present invention is superior to Comparative Examples 8 to 9 used as a phosphorescent host in which a comparative compound is mixed is a hole characteristic in a polycyclic compound represented by Chemical Formula 2, which is characterized by high electron stability as well as hole stability and high T1. When this strong compound represented by Chemical Formula 1 is mixed, the electron blocking ability is improved due to the high T1 and high LUMO energy values, and more holes are quickly and easily moved in the light emitting layer. Accordingly, it is judged that the charge balance in the light emitting layer of holes and electrons is increased, so that light emission is well performed inside the light emitting layer rather than the hole transport layer interface, thereby reducing deterioration at the HTL interface, thereby maximizing the driving voltage, efficiency, and lifetime of the entire device. . In addition, among the compounds represented by Formula 1, it was confirmed that the compound in which Dibenzofuran was substituted showed the best results in terms of driving voltage, efficiency, and life, and the compound in which Dibenzothiophen was substituted was also excellent in terms of efficiency due to high refractive index. there was. That is, it is concluded that the combination of Chemical Formula 1 and Chemical Formula 2 electrochemically synergistically improves the overall performance of the device.

Example 2) By mixing ratio Red  Fabrication and testing of organic light emitting devices

Host 1 Host 2` Mixing ratio
(1st host: 2nd host) Voltage Current Density Brightness
(cd / m2) Efficiency Lifetime
T (95) Example (101) Compound (1-33 ’) Compound (3-61) 2: 8 5.5 8.5 2500.0 29.4 127.5 Example (102) Compound (1-33 ’) Compound (3-61) 3: 7 5.5 8.3 2500.0 30.1 127.8 Example (103) Compound (1-33 ’) Compound (3-61) 4: 6 5.7 8.8 2500.0 28.5 120.1 Example 104 Compound (1-33 ’) Compound (3-61) 5: 5 5.8 9.4 2500.0 26.7 118.6 Example (105) Compound (1-50 ’) Compound (3-6) 2: 8 5.4 7.3 2500.0 34.1 133.5 Example (106) Compound (1-50 ’) Compound (3-6) 3: 7 5.3 7.2 2500.0 34.9 133.2 Example (107) Compound (1-50 ’) Compound (3-6) 4: 6 5.5 7.6 2500.0 33.1 130.9 Example (108) Compound (1-50 ’) Compound (3-6) 5: 5 5.8 7.7 2500.0 32.4 128.3

As shown in Table 8, the mixture of the compounds of the present invention was measured by fabricating the device by ratio (2: 8, 3: 7, 4: 6, 5: 5). In detail, the results of the mixture of compound 1-33 'and compound 3-61 showed similarly excellent results of driving voltage, efficiency, and lifetime for 2: 8 and 3: 7, but with 4: 6 and 5: 5. Likewise, as the ratio of the first host increased, it was confirmed that the results of the driving voltage, efficiency, and lifetime gradually decreased, and this resulted in the same pattern in the mixture result of Compound 1-50 'and Compound 3-6. This can 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 will be capable of 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 explain the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The scope of protection of the present invention should be interpreted by the following claims, and all technologies within the equivalent range should be interpreted as being included in the scope of the present invention.

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

Claims (7)

delete Compound represented by the following formula (16)
Chemical Formula (16)

{In the above formula (16),
1) Ar² Is C containing a hetero atom of O or S₁₂Is a heterocyclic group of
Ar³Is C containing a heteroatom of O or S₁₂Is a heterocyclic group;
2) L^One, L³ And L⁴Is a single bond independently of each other; Or C₆Is an arylene group;
3) X³Is S.}
delete delete The compound according to claim 2, wherein the compound is used in a phosphorescence emitting layer of an organic electric device.
A display device comprising an organic electrical element containing the compound according to claim 2; And a control unit driving the display device.
The method of claim 6,
The organic electric device is at least one of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, and a monochromatic or white lighting device.

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