WO2019172623A1 - Compound for organic electric device, organic electric device using same, and electronic device thereof - Google Patents

Abstract

The present invention provides a novel mixture capable of improving luminous efficiency, stability, and lifetime of a device, an organic electric device using same, and an electronic device thereof.

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.

Materials used as the organic material layer in the organic electric element may be classified into light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like according to their functions.

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

In the phosphorescent organic EL device using the phosphorescent dopant material, the LUMO and HOMO levels of the host material have a great influence on the efficiency and lifespan of the organic EL device. As a result, it is possible to prevent efficiency degradation and lifespan reduction 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 fluorescent and phosphorescent light emitting materials, researches on increasing efficiency and lifespan of organic electric devices using thermally activated delayed fluorescent (TADF) and Exciplex have recently been conducted. Especially, the method of energy transfer from host materials to dopant materials has been investigated. There is a lot of research going on.

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

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

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

Reference KR101170666 B1 was used as the prior art document.

The present invention has been proposed to solve the problems of the phosphorescent host material as described above, the charge balance control, efficiency and lifetime in the light emitting layer by adjusting the HOMO level for the host material of the phosphorescent organic electroluminescent device comprising a phosphorescent dopant Compound which can improve It aims at providing the organic electric element using this and its electronic device.

The present invention 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 device.

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

                   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 to distinguish the components from other components, and the nature, order or order of the components are not limited by the terms. If a component is described as being "connected", "coupled" or "connected" to another component, that component may be directly connected to or connected to that other component, but there may be another configuration between each component. It is to be understood that the elements may be "connected", "coupled" or "connected".

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

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

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

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

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

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

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

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

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

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

As used herein, the terms "aryl group" and "arylene group" 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 a single ring and multiple rings, heteroaliphatic rings and hetero Aromatic rings. Adjacent functional groups may be formed in combination.

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

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

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

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

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

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

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

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

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

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

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

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

                  Formula 1 Formula 2

   Formula 1-1 Formula 2-1

{In Formula 1 and Formula 2,

1) M is an arylene group of C ₆ -C ₆₀ or Formula 1-1,

2) A, B, C and D are each independently an aryl group of C ₆ -C ₂₀ or a heterocyclic group of C ₂ -C ₂₀ , C is bonded to L ³ , D is bonded to L ⁴ ,

3) X ¹ is S or O,

X ² is NL ⁶ -Ar ⁷ , O, S or CR'R ",

X ³ and X ⁴ are each independently a single bond, NL ⁷ -Ar ⁸ , O, S or CR'R ",

Except that X ³ and X ⁴ are both single bonds,

R 'and R "are each independently hydrogen; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₃ ~ C ₆₀ Heterocyclic group; C ₁ ~ C ₅₀ Alkyl group; and -L'-N (R ^a ) (R ^b ), and

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

4) L 'is a single bond; C ₆ -C ₆₀ arylene group; Fluorenylene groups; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; And a C ₂ -C ₆₀ heterocyclic group; selected from the group consisting of R ^a and R ^b independently of each other an C ₆ -C ₆₀ aryl group; Fluorenyl groups; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; And a C ₂ -C ₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si, and P, and

5) In Formula 2, a pair of * 1 and * 2, * 2 and * 3, and * 3 and * 4 binds to * 5 and * 6 of Formula 2-1, respectively.

6) Ar ¹ , Ar ² , Ar ³ , Ar ⁴ , Ar ⁵ , Ar ⁶ , Ar ⁷ And Ar ⁸ are each independently of the other C ₆ -C ₆₀ aryl group; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; Fluorenyl groups; A fused ring group of an aromatic ring of C ₆ -C ₆₀ and an aliphatic ring of C ₃ -C ₆₀ ; An alkyl group of C ₁ -C ₅₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; And an aryloxy group of C ₆ -C ₃₀ , and also Ar ¹ Ar ⁵ may combine with each other to form a ring,

7) L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ and L ⁷ 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; Fused ring group of C ₃ -C ₆₀ aliphatic ring and C ₆ -C ₆₀ aromatic ring; And aliphatic hydrocarbon groups,

8) l and n are integers of 0 to 4, m is an integer of 0 to 2, R ⁴ , R ⁵ and R ⁶ are each independently of the C ₆ ~ C ₆₀ aryl group; Fluorenyl groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ -C ₃₀ alkoxyl group; C ₆ -C ₃₀ aryloxy group; And -L'-N (R ^a ) (R ^b ); Is selected from the group consisting of

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

In another aspect, the present invention provides an organic electroluminescent device comprising a compound represented by any one of the following formulas A-1 to A-7 in Formula 1 independently of each other.

a-1 a-2 a-3 a-4

      a-5 a-6 a-7

{In Chemical Formulas a-1 to a-7,

1) Z ¹ to Z ⁴⁸ are independently of each other CR ^c or N,

Provided that Z ¹ to Z ⁴⁸ bonded to L ¹ to L ³ are carbon (C),

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

3) * indicates the location of condensation}

Specifically, the present invention provides an organic electroluminescent device comprising a compound represented by any one of L ¹ to L ⁷ in Formula 1 or Formula 2 below.

 b-1 b-2 b-3 b-4 b-5 b-6

 b-7 b-8 b-9 b-10

 b-11 b-12 b-13

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

1) Y is NL ⁸ -Ar ⁹ , O, S or CR'R ",

2) L ⁸ is the same as defined above in L ¹ ,

3) Ar ⁹ is the same as defined in Ar ¹ above,

4) R 'and R "are the same as defined above,

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

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

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

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

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

As another example, the present invention provides an organic electric device including at least one of Ar ¹ to Ar ⁵ including a compound represented by the following Chemical Formula 1-2.

Formula 1-2

{In Formula 1-2,

1) E and F are the same as the definition of A,

2) X ⁵ is NL ¹⁰ -Ar ¹⁰ , O, S or CR'R ",

3) L ⁹ and L ¹⁰ are the same as the above definition of L ¹ ,

4) Ar ¹⁰ is the same as the definition of Ar ¹ ,

5) R 'and R "are the same as defined above.}

The present invention provides an organic electric device, for example, the first host compound represented by Formula 1 includes a compound represented by the following Formula 3.

Formula 3

{In Formula 3,

X ¹ , X ² , Ar ¹ to Ar ⁵ are the same as defined above,

Z ¹ to Z ⁴ are each independently CR ^c or N,

R ^c is as defined above.}

More specifically, the present invention provides an organic electroluminescent device comprising a compound in which X ¹ , X ² of Formula 1 are independently O or S.

On the other hand, the present invention provides an organic electroluminescent device comprising a compound represented by any one of the following formula 4 to formula 6 the second host compound represented by the formula (2).

        Formula 4 Formula 5 Formula 6

{In Formulas 4 to 6, R ⁴ , R ⁵ , R ⁶ , X ³ , X ⁴ , L ⁵ , L ⁷ , Ar ⁶ , Ar ⁸ , l, m and n are as defined above.}

The present invention provides an organic electroluminescent device comprising, for example, a second host compound represented by Formula 2 including a compound represented by any one of Formulas 7 to 12.

       Formula 7 Formula 8 Formula 9

       Chemical Formula 10 Chemical Formula 11 Chemical Formula 12

{In Formula 7 to Formula 12,

R ⁴ , R ⁵ , R ⁶ , L ⁵ , L ⁷ , Ar ⁶ , Ar ⁸ , l, m and n are as defined above,

X is selected from NL ⁷ -Ar ⁸ , O, S or CR'R ".

More specifically, in the present invention, the first host compound represented by Chemical Formula 1 includes the following Compounds 1-1 to 1-265.

In addition, the second host compound represented by Formula 2 in the present invention includes a compound represented by the following compound 2-1 to compound 2-128.

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

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

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

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

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

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

In addition, the present invention provides an organic electroluminescent device included in the light emitting layer by mixing the compound represented by Formula 1 and Formula 2 in any one ratio of 1: 9 to 9: 1, preferably 1: 9 to 5: 5, more preferably, it is mixed in a ratio of 2: 8 or 3: 7 and included in the light emitting layer.

The organic electroluminescent device further includes a light efficiency improvement layer formed on at least one of one side of the first electrode opposite to the organic material layer or one side of the second electrode opposite to the organic material layer. An organic electric device is provided.

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

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

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

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

In another aspect, the organic electronic device provides an electronic device according to the present invention, wherein the organic electroluminescent device is at least one of an organic electroluminescent device, an organic solar cell, an organic photoconductor, an organic transistor, and a monochrome or white light emitting 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 1

The compound represented by Formula 1 according to the present invention (final product 1) is disclosed in Korean Patent Registration No. 10-1614739 (Registration date of April 18, 2016), Korean Patent Application No. 2016-0110817 (application date of August 30, 2016) It was prepared by the disclosed synthesis method. X ¹ , A, B, L ¹ to L ⁴ , M, Ar ¹ to Ar ⁵ are the same as defined above.

<Scheme 1>

I. Final Product 1 Synthesis

Sub1 (1 equiv) was dissolved in toluene in a round bottom flask, then Sub2 (1 equiv), Pd ₂ (dba) ₃ (0.03 equiv), ( t -Bu) ₃ P (1 equiv), NaO t -Bu (2 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.

1.1-59 Synthesis Example

Sub2-59 (5.30 g, 11.97 mmol) was dissolved in Toluene (120 mL) in a round flask, then Sub1-59 (5.15 g, 11.97 mmol), Pd ₂ (dba) ₃ (0.33 g, 0.36 mmol), P ( t -Bu) ₃ (0.4 mL, 0.72 mmol), NaO t -Bu (3.45 g, 35.90 mmol) was 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 1-59 (7.96 g, yield: 84%).

2. 1-195 Synthesis Example

Sub1-195 (4.10 g, 7.47 mmol), Sub2-195 (2.42 g, 7.47 mmol), Pd ₂ (dba) ₃ (0.21 g, 0.22 mmol), P ( t -Bu) ₃ (0.2 mL, 0.45 mmol) , NaO t -Bu (2.15 g, 22.42 mmol) 1-59 (7.96 g, yield: 84%) was obtained using the above 1-59 synthesis, to obtain product 1-195 (5.33 g, yield: 90%).

Synthesis Example 2

Compound represented by Formula 2 (final product 2) according to the present invention is synthesized by reacting Sub 3 and Sub 4, as shown in Scheme 2, but is not limited thereto. X ³ , X ⁴ , L ⁵ , Ar ⁶ are the same as defined in Formula 2, Hal ² is Br or Cl.

<Scheme 2>

I. Synthesis of Sub3

Sub3 of Scheme 2 is synthesized by the reaction route of Scheme 3, but is not limited thereto.

<Scheme 3>

1. Synthesis Example of Sub 3-1, Sub3-17

(1) Sub 3-b-1 synthesis method

The starting material Sub 3-a-1 (50 g, 155 mmol) was dissolved in DMF (1 L), followed by bis (pinacolato) diboron (43 g, 171 mmol), KOAc (46 g, 466 mmol), PdCl ₂ (dppf) (3.4 g, 4.65 mmol) was added and stirred at 120 ° 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 recrystallized from a Silicagel column to give 49 g (yield: 85%) of the product Sub 3-b-1.

(2) Sub 3-d-1 synthesis method

Sub 3-b-1 (48 g, 130 mmol) obtained in the above synthesis was dissolved in THF (600 mL), and then Sub 3-c-1 (1-bromo-2-nitrobenzene, CAS Registry Number: 577-19- 5) (32 g, 156 mmol), K ₂ CO ₃ (54 g, 390 mmol), Pd (PPh ₃ ) ₄ (9.0 g, 7.8 mmol), water (300 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 recrystallization to obtain 34 g (yield: 72%) of the product Sub3-d-1.

(3) Sub3-1, Sub3-17 synthesis method

Sub3-d-1 (33 g, 90.6 mmol) obtained in the above synthesis was dissolved with o -dichlorobenzene (450 mL), triphenylphosphine (59 g, 226 mmol) was added 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 purified by Silicagel column and recrystallized to give the product Sub3-1 (11 g, yield: 37%) and Sub3-17 (15 g, yield: 50%).

2. Synthesis Example of Sub 3-2, Sub3-18

(1) Sub 3-b-2 synthesis method

Sub3-a-2 (50 g, 190 mmol), bis (pinacolato) diboron (53 g, 209 mol), KOAc (56 g, 570 mmol), PdCl ₂ (dppf) (4.2 g, 5.7 mmol) 48 g (yield: 81%) of product Sub 3-b-2 was obtained using the synthesis method of Sub3-b-1.

(2) Sub 3-d-2 synthesis method

Sub 3-b-2 (47 g, 151.5 mmol) obtained in the above synthesis, Sub 3-c-1 (37 g, 182 mmol), K ₂ CO ₃ (63 g, 454.5 mmol), Pd (PPh ₃ ) ₄ (11 g, 9.1 mmol) was obtained using the synthesis method of Sub3-d-1 to obtain 33 g (yield: 72%) of the product Sub3-d-2.

(3) Sub3-2, Sub3-18 synthesis method

Sub3-d-1 (33 g, 108 mmol) and triphenylphosphine (71 g, 270 mmol) obtained in the synthesis were prepared using Sub3-2 (10 g, yield: 35%) and Sub3- using the synthesis method of Sub3-1. 18 (14 g, yield: 47%) was obtained.

3.Sub 3-3, Sub3 -19 Synthesis Example

(1) Sub 3-b-3 synthesis method

Sub3-a-3 (50 g, 202 mmol), bis (pinacolato) diboron (57 g, 223 mmol), KOAc (60 g, 607 mmol), PdCl ₂ (dppf) (4.4 g, 6.1 mmol) 49 g (yield: 82%) of product Sub 3-b-3 was obtained using the synthesis method of -b-1.

(2) Sub 3-d-3 synthesis method

Sub 3-b-3 (49 g, 166 mmol) obtained in the above synthesis, Sub 3-c-1 (40 g, 199 mmol), K ₂ CO ₃ (69 g, 498 mmol), Pd (PPh ₃ ) ₄ (12 g, 9.96 mmol) was obtained 34 g (yield: 69%) of the product Sub3-d-3 by using the synthesis method of Sub3-d-1.

(3) Sub3-3, Sub3-19 synthesis method

Sub3-d-3 (33 g, 114 mmol) and triphenylphosphine (75 g, 285 mmol) obtained in the synthesis were synthesized using Sub3-3 (10 g, yield: 34%) and Sub3- using the synthesis method of Sub3-1. 19 (15 g, yield: 52%) was obtained.

4. Sub 3-5, Sub3-21 Synthesis Example

(1) Sub 3-b-5 synthesis method

Sub3-a-5 (50 g, 155 mmol), bis (pinacolato) diboron (43 g, 171 mmol), KOAc (46 g, 466 mmol), PdCl ₂ (dppf) (3.4 g, 4.65 mmol) 48 g (yield: 84%) of product Sub 3-b-5 was obtained using the synthesis method of -b-1.

(2) Sub 3-d-5 synthesis method

Sub 3-b-5 (48 g, 130 mmol), Sub 3-c-1 (32 g, 156 mmol) obtained in the above synthesis, K ₂ CO ₃ (54 g, 390 mmol), Pd (PPh ₃ ) ₄ (9.0 g, 7.8 mmol) was obtained using the synthesis method of Sub3-d-1 as 36 g (yield: 75%) of the product Sub3-d-5.

(3) Sub3-5, Sub3-21 synthesis method

Sub3-d-5 (36 g, 96 mmol) and triphenylphosphine (63 g, 240 mmol) obtained in the synthesis were synthesized using Sub3-5 (16 g, yield: 51%) and Sub3- using the synthesis method of Sub3-1. 21 (12 g, yield: 37%) was obtained.

5. Sub 3-6, Sub3-22 Synthesis Example

(1) Sub 3-b-6 synthesis method

Sub3-a-6 (50 g, 190 mmol), bis (pinacolato) diboron (53 g, 209 mmol), KOAc (56 g, 570 mmol), PdCl ₂ (dppf) (4.2 g, 5.7 mmol) 49 g (yield: 83%) of product Sub 3-b-6 was obtained using the synthesis method of -b-1.

(2) Sub 3-d-6 synthesis method

Sub 3-b-6 (49 g, 157 mmol), Sub 3-c-1 (38 g, 189 mmol) obtained in the above synthesis, K ₂ CO ₃ (65 g, 472 mmol), Pd (PPh ₃ ) ₄ 34 g (yield: 71%) of product Sub3-d-6 was obtained by using the synthesis method of Sub3-d-1 (11 g, 9.42 mmol).

(3) Sub3-6, Sub3-22 synthesis method

Sub3-d-6 (34 g, 111 mmol) and triphenylphosphine (73 g, 279 mmol) obtained in the above synthesis were synthesized using Sub3-6 (15 g, yield: 49%) and Sub3- using the synthesis method of Sub3-1. 22 (12 g, yield: 40%) was obtained.

6. Sub 3-8, Sub3-23 Synthesis Example

(1) Sub 3-b-8 synthesis method

Sub3-a-8 (50 g, 183 mmol), bis (pinacolato) diboron (51 g, 201 mmol), KOAc (54 g, 549 mmol), PdCl ₂ (dppf) (4.0 g, 5.49 mmol) 48 g (yield: 82%) of product Sub 3-b-8 was obtained using the synthesis method of -b-1.

(2) Sub 3-d-8 synthesis method

Sub 3-b-8 (48 g, 150 mmol), Sub 3-c-1 (36 g, 180 mmol) obtained in the above synthesis, K ₂ CO ₃ (62 g, 450 mmol), Pd (PPh ₃ ) ₄ 34 g (yield: 71%) of product Sub3-d-8 was obtained by using the synthesis method of Sub3-d-1.

(3) Sub3-8, Sub3-23 synthesis method

Sub3-d-8 (34 g, 106 mmol) and triphenylphosphine (70 g, 265 mmol) obtained in the synthesis were synthesized using Sub3-8 (14 g, yield: 48%) and Sub3- using the synthesis method of Sub3-1. 23 (11 g, yield: 36%) was obtained.

7.Sub 3-9 Synthesis Example

(1) Sub 3-b-9 synthesis method

Sub3-a-9 (50 g, 155 mmol), bis (pinacolato) diboron (43 g, 171 mmol), KOAc (46 g, 466 mmol), PdCl ₂ (dppf) (3.4 g, 4.7 mmol) 45 g (yield: 78%) of product Sub 3-b-9 was obtained using the synthesis method of -b-1.

(2) Sub 3-d-9 synthesis method

Sub 3-b-9 (45 g, 121 mmol), Sub 3-c-1 (29 g, 145 mmol) obtained in the above synthesis, K ₂ CO ₃ (50 g, 363 mmol), Pd (PPh ₃ ) ₄ (8.4 g, 7.26 mmol) was obtained by the synthesis method of Sub3-d-1. 30 g of the product Sub3-d-9 (yield: 67%) was obtained.

(3) Sub3-9 synthesis method

Sub3-d-9 (30 g, 81 mmol) and triphenylphosphine (53 g, 203 mmol) obtained in the above synthesis were obtained by using the synthesis method of Sub3-1, to obtain Sub3-9 (23 g, yield: 84%).

8. Sub 3-10 Synthesis Example

(1) Sub 3-b-10 synthesis method

Sub3-a-10 (50 g, 190 mmol), bis (pinacolato) diboron (53 g, 209 mmol), KOAc (56 g, 570 mmol), PdCl ₂ (dppf) (4.2 g, 5.7 mmol) 38 g (yield: 65%) of product Sub 3-b-10 were obtained using the synthesis method of -b-1.

(2) Sub 3-d-10 synthesis method

Sub 3-b-10 (38 g, 124 mmol), Sub 3-c-1 (30 g, 148 mmol) obtained in the above synthesis, K ₂ CO ₃ (51 g, 371 mmol), Pd (PPh ₃ ) ₄ (8.6 g, 7.4 mmol) was obtained using the synthesis method of Sub3-d-1, 22 g (yield: 58%) of the product Sub3-d-10.

(3) Sub3-10 synthesis method

Sub3-d-10 (22 g, 71 mmol) and triphenylphosphine (47 g, 178 mmol) obtained in the above synthesis were obtained using the synthesis method of Sub3-1, to obtain Sub3-10 (17 g, yield: 86%).

9. Sub 3-11 Synthesis Example

(1) Sub 3-b-11 synthesis method

Sub3-a-11 (50 g, 202 mmol), bis (pinacolato) diboron (57 g, 223 mmol), KOAc (59 g, 606 mmol), PdCl ₂ (dppf) (4.4 g, 6.06 mmol) 40 g (yield: 68%) of product Sub 3-b-11 was obtained using the synthesis method of -b-1.

(2) Sub 3-d-11 synthesis method

Sub 3-b-11 (40 g, 137 mmol), Sub 3-c-1 (33 g, 164 mmol) obtained in the above synthesis, K ₂ CO ₃ (57 g, 411 mmol), Pd (PPh ₃ ) ₄ (9.5 g, 8.2 mmol) was obtained using the synthesis method of Sub3-d-1 (23 g, yield: 57%).

(3) Sub3-11 synthesis method

Sub3-d-11 (23 g, 78 mmol) and triphenylphosphine (51 g, 195 mmol) obtained in the above synthesis were obtained using the synthesis method of Sub3-1, to obtain Sub3-11 (17 g, yield: 87%).

10.Sub 3-13 Synthesis Example

(1) Sub 3-b-13 synthesis method

Sub3-a-13 (50 g, 155 mmol), bis (pinacolato) diboron (43 g, 171 mmol), KOAc (46 g, 465 mmol), PdCl ₂ (dppf) (3.4 g, 4.65 mmol) 43 g (yield: 75%) of product Sub 3-b-13 was obtained using the synthesis method of -b-1.

(2) Sub 3-d-13 synthesis method

Sub 3-b-13 (43 g, 116 mmol), Sub 3-c-1 (28 g, 139 mmol) obtained in the above synthesis, K ₂ CO ₃ (34 g, 348 mmol), Pd (PPh ₃ ) ₄ (8.0 g, 6.96 mmol) was obtained by 19 g (yield: 45%) of the product Sub3-d-13 using the above synthesis method of Sub3-d-1.

(3) Sub3-13 synthesis method

Sub3-d-13 (19 g, 52.2 mmol) and triphenylphosphine (34 g, 131 mmol) obtained in the above synthesis were obtained using Sub3-1 (14 g, yield: 79%) using the synthesis method of Sub3-1.

11.Synthesis Example of Sub 3-14

(1) Sub 3-b-14 synthesis method

Sub3-a-14 (50 g, 190 mmol), bis (pinacolato) diboron (53 g, 209 mmol), KOAc (56 g, 570 mmol), PdCl ₂ (dppf) (4.2 g, 5.7 mmol) 34.2 g (yield: 58%) of product Sub 3-b-14 were obtained using the synthesis method of -b-1.

(2) Sub 3-d-14 synthesis method

Sub 3-b-14 (34 g, 110 mmol) obtained in the above synthesis, Sub 3-c-1 (26.7 g, 132 mmol), K ₂ CO ₃ (45 g, 331 mmol), Pd (PPh ₃ ) ₄ (7.6 g, 6.61 mmol) was obtained 15 g (yield: 45%) of the product Sub3-d-14 using the synthesis method of Sub3-d-1.

(3) Sub3-14 synthesis method

Sub3-d-14 (15 g, 49.6 mmol) and triphenylphosphine (33 g, 124 mmol) obtained in the above synthesis were obtained using Sub3-1 (11 g, yield: 82%) using the synthesis method of Sub3-1.

12.Sub 3-15 Synthesis Example

(1) Sub 3-b-15 synthesis method

Sub3-a-15 (50 g, 202 mmol), bis (pinacolato) diboron (57 g, 223 mmol), KOAc (59 g, 606 mmol), PdCl ₂ (dppf) (4.4 g, 6.06 mmol) 25 g (yield: 42%) of product Sub 3-b-15 was obtained using the synthesis method of -b-1.

(2) Sub 3-d-15 synthesis method

Sub 3-b-15 (25 g, 84.8 mmol) obtained in the above synthesis, Sub 3-c-1 (21 g, 102 mmol), K ₂ CO ₃ (35 g, 254 mmol), Pd (PPh ₃ ) ₄ (5.9 g, 5.09 mmol) was obtained using the synthesis method of Sub3-d-1 to give 9.8 g (yield: 40%) of the product Sub3-d-15.

(3) Sub3-15 synthesis method

Sub3-d-15 (9.8 g, 33.9 mmol) and triphenylphosphine (22 g, 84.8 mmol) obtained in the above synthesis were used to obtain Sub3-15 (7.6 g, yield: 87%) using the synthesis method of Sub3-1.

The compound belonging to Sub 3 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 3.

compound	FD-MS	compound	FD-MS
Sub3-1	m / z = 332.13 (C 24 H 16 N 2 = 332.41)	Sub3-2	m / z = 273.06 (C 18 H 11 NS = 273.35)
Sub3-3	m / z = 257.08 (C 18 H 11 NO = 257.29)	Sub3-4	m / z = 283.13 (C 21 H 17 N = 283.37)
Sub3-5	m / z = 332.13 (C 24 H 16 N 2 = 332.41)	Sub3-6	m / z = 273.06 (C 18 H 11 NS = 273.35)
Sub3-7	m / z = 257.08 (C 18 H 11 NO = 257.29)	Sub3-8	m / z = 283.13 (C 21 H 17 N = 283.37)
Sub3-9	m / z = 332.13 (C 24 H 16 N 2 = 332.41)	Sub3-10	m / z = 273.06 (C 18 H 11 NS = 273.35)
Sub3-11	m / z = 257.08 (C 18 H 11 NO = 257.29)	Sub3-12	m / z = 283.13 (C 21 H 17 N = 283.37)
Sub3-13	m / z = 332.13 (C 24 H 16 N 2 = 332.41)	Sub3-14	m / z = 273.06 (C 18 H 11 NS = 273.35)
Sub3-15	m / z = 257.08 (C 18 H 11 NO = 257.29)	Sub3-16	m / z = 283.13 (C 21 H 17 N = 283.37)
Sub3-17	m / z = 332.13 (C 24 H 16 N 2 = 332.41)	Sub3-18	m / z = 273.06 (C 18 H 11 NS = 273.35)
Sub3-19	m / z = 257.08 (C 18 H 11 NO = 257.29)	Sub3-20	m / z = 283.13 (C 21 H 17 N = 283.37)
Sub3-21	m / z = 332.13 (C 24 H 16 N 2 = 332.41)	Sub3-22	m / z = 273.06 (C 18 H 11 NS = 273.35)
Sub3-23	m / z = 257.08 (C 18 H 11 NO = 257.29)	Sub3-24	m / z = 283.13 (C 21 H 17 N = 283.37)
Sub3-25	m / z = 358.15 (C 25 H 18 N 2 = 358.44)	Sub3-26	m / z = 367.07 (C 24 H 14 ClNO = 367.83)
Sub3-27	m / z = 408.16 (C 30 H 20 N 2 = 408.50)	Sub3-28	m / z = 383.05 (C 24 H 14 ClNS = 383.89)
Sub3-29	m / z = 383.05 (C 24 H 14 ClNS = 383.89)	Sub3-30	m / z = 367.07 (C 24 H 14 ClNO = 367.83)
Sub3-31	m / z = 313.15 (C 22 H 19 NO = 313.40)	Sub3-32	m / z = 408.16 (C 30 H 20 N 2 = 408.50)
Sub3-33	m / z = 297.06 (C 20 H 11 NS = 297.38)	Sub3-34	m / z = 333.12 (C 24 H 15 NO = 333.39)
Sub3-35	m / z = 317.10 (C 21 H 16 ClN = 317.82)	Sub3-36	m / z = 405.15 (C 31 H 19 N = 405.50)
Sub3-37	m / z = 407.17 (C 31 H 21 N = 407.52)	Sub3-38	m / z = 367.07 (C 24 H 14 ClNO = 367.83)
Sub3-39	m / z = 405.15 (C 31 H 19 N = 405.50)	Sub3-40	m / z = 382.15 (C 28 H 18 N 2 = 382.47)
Sub3-41	m / z = 382.15 (C 28 H 18 N 2 = 382.47)	Sub3-42	m / z = 287.08 (C 19 H 13 NS = 287.38)
Sub3-43	m / z = 291.05 (C 18 H 10 FNS = 291.34)	Sub3-44	m / z = 405.15 (C 31 H 19 N = 405.50)

II. Synthesis of Sub4

Compounds belonging to Sub 4 may be the following compounds, but are not limited thereto. Table 2 shows Field Desorption-Mass Spectrometry (FD-MS) values of some compounds belonging to Sub 4.

compound	FD-MS	compound	FD-MS
Sub4-1	m / z = 155.96 (C 6 H 5 Br = 157.01)	Sub4-2	m / z = 156.95 (C 5 H 4 BrN = 158.00)
Sub4-3	m / z = 156.95 (C 5 H 4 BrN = 158.00)	Sub4-4	m / z = 156.95 (C 5 H 4 BrN = 158.00)
Sub4-5	m / z = 157.95 (C 4 H 3 BrN 2 = 158.99)	Sub4-6	m / z = 157.95 (C 4 H 3 BrN 2 = 158.99)
Sub4-7	m / z = 157.95 (C 4 H 3 BrN 2 = 158.99)	Sub4-8	m / z = 157.95 (C 4 H 3 BrN 2 = 158.99)
Sub4-9	m / z = 158.94 (C 3 H 2 BrN 3 = 159.97)	Sub4-10	m / z = 311.01 (C 15 H 10 BrN 3 = 312.17)
Sub4-11	m / z = 387.04 (C 21 H 14 BrN 3 = 388.27)	Sub4-12	m / z = 387.04 (C 21 H 14 BrN 3 = 388.27)
Sub4-13	m / z = 361.02 (C 19 H 12 BrN 3 = 362.23)	Sub4-14	m / z = 361.02 (C 19 H 12 BrN 3 = 362.23)
Sub4-15	m / z = 411.04 (C 23 H 14 BrN 3 = 412.29)	Sub4-16	m / z = 545.06 (C 31 H 20 BrN 3 S = 546.49)
Sub4-17	m / z = 493.02 (C 27 H 16 BrN 3 S = 494.41)	Sub4-18	m / z = 310.01 (C 16 H 11 BrN 2 = 311.18)
Sub4-19	m / z = 283.00 (C 15 H 10 BrN = 284.16)	Sub4-20	m / z = 462.07 (C 28 H 19 BrN 2 = 463.38)
Sub4-21	m / z = 175.94 (C 4 H 2 BrFN 2 = 176.98)	Sub4-22	m / z = 283.99 (C 14 H 9 BrN 2 = 285.14)
Sub4-23	m / z = 168.98 (C 7 H 4 ClNS = 169.63)	Sub4-24	m / z = 256.98 (C 13 H 8 BrN = 258.12)
Sub4-25	m / z = 202.03 (C 11 H 7 ClN 2 = 202.64)	Sub4-26	m / z = 281.04 (C 15 H 8 ClN 3 O = 281.70)
Sub4-27	m / z = 310.01 (C 16 H 11 BrN 2 = 311.18)	Sub4-28	m / z = 228.05 (C 13 H 9 ClN 2 = 228.68)
Sub4-29	m / z = 240.05 (C 14 H 9 ClN 2 = 240.69)	Sub4-30	m / z = 254.06 (C 15 H 11 ClN 2 = 254.72)
Sub4-31	m / z = 290.06 (C 18 H 11 ClN 2 = 290.75)	Sub4-32	m / z = 378.01 (C 20 H 11 ClN 2 S 2 = 378.89)
Sub4-33	m / z = 360.03 (C 20 H 13 BrN 2 = 361.24)	Sub4-34	m / z = 410.04 (C 24 H 15 BrN 2 = 411.30)
Sub4-35	m / z = 240.05 (C 14 H 9 ClN 2 = 240.69)	Sub4-36	m / z = 428.03 (C 24 H 14 BrFN 2 = 429.29)
Sub4-37	m / z = 330.06 (C 20 H 11 ClN 2 O = 330.77)	Sub4-38	m / z = 290.06 (C 18 H 11 ClN 2 = 290.75)
Sub4-39	m / z = 405.10 (C 26 H 16 ClN 3 = 405.89)	Sub4-40	m / z = 360.03 (C 20 H 13 BrN 2 = 361.24)
Sub4-41	m / z = 245.08 (C 14 H 4 D 5 ClN 2 = 245.72)	Sub4-42	m / z = 330.06 (C 20 H 11 ClN 2 O = 330.77)
Sub4-43	m / z = 245.08 (C 14 H 4 D 5 ClN 2 = 245.72)	Sub4-44	m / z = 366.09 (C 24 H 15 ClN 2 = 366.85)
Sub4-45	m / z = 390.09 (C 26 H 15 ClN 2 = 390.87)	Sub4-46	m / z = 356.07 (C 22 H 13 ClN 2 O = 356.81)
Sub4-47	m / z = 360.02 (C 20 H 13 BrN 2 = 361.24)	Sub4-48	m / z = 330.00 (C 14 H 4 ClF 5 N 2 = 330.64)
Sub4-49	m / z = 290.06 (C 18 H 11 ClN 2 = 290.75)	Sub4-50	m / z = 396.05 (C 24 H 13 ClN 2 S = 396.89)
Sub4-51	m / z = 340.08 (C 22 H 13 ClN 2 = 340.81)	Sub4-52	m / z = 366.09 (C 24 H 15 ClN 2 = 366.85)
Sub4-53	m / z = 290.06 (C 18 H 11 ClN 2 = 290.75)	Sub4-54	m / z = 516.03 (C 30 H 17 BrN 2 S = 517.44)
Sub4-55	m / z = 346.03 (C 20 H 11 ClN 2 S = 346.83)	Sub4-56	m / z = 410.04 (C 24 H 15 BrN 2 = 411.30)
Sub4-57	m / z = 440.11 (C 30 H 17 ClN 2 = 440.93)	Sub4-58	m / z = 346.03 (C 20 H 11 ClN 2 S = 346.83)
Sub4-59	m / z = 330.06 (C 20 H 11 ClN 2 O = 330.77)	Sub4-60	m / z = 290.06 (C 18 H 11 ClN 2 = 290.75)
Sub4-61	m / z = 258.09 (C 15 H 15 ClN 2 = 258.75)	Sub4-62	m / z = 296.02 (C 16 H 9 ClN 2 S = 296.77)
Sub4-63	m / z = 280.04 (C 16 H 9 ClN 2 O = 280.71)	Sub4-64	m / z = 402.01 (C 22 H 11 ClN 2 S 2 = 402.91)
Sub4-65	m / z = 386.03 (C 22 H 11 ClN 2 OS = 386.85)	Sub4-66	m / z = 377.08 (C 22 H 8 D 5 ClN 2 S = 377.90)
Sub4-67	m / z = 301.05 (C 16 H 4 D 5 ClN 2 S = 301.80)	Sub4-68	m / z = 396.05 (C 24 H 13 ClN 2 S = 396.89)
Sub4-69	m / z = 518.12 (C 35 H 19 ClN 2 O = 519.00)	Sub4-70	m / z = 372.05 (C 22 H 13 ClN 2 S = 372.87)
Sub4-71	m / z = 400.02 (C 22 H 13 BrN 2 O = 401.26)	Sub4-72	m / z = 431.08 (C 27 H 14 ClN 3 O = 431.88)
Sub4-73	m / z = 555.06 (C 33 H 18 ClN 3 S 2 = 556.10)	Sub4-74	m / z = 548.15 (C 34 H 21 ClN 6 = 549.03)
Sub4-75	m / z = 383.08 (C 23 H 14 ClN 3 O = 383.84)	Sub4-76	m / z = 398.06 (C 24 H 15 ClN 2 S = 398.91)
Sub4-77	m / z = 528.12 (C 33 H 25 BrN 2 = 529.48)	Sub4-78	m / z = 240.05 (C 14 H 9 ClN 2 = 240.69)
Sub4-79	m / z = 290.06 (C 18 H 11 ClN 2 = 290.75)	Sub4-80	m / z = 290.06 (C 18 H 11 ClN 2 = 290.75)
Sub4-81	m / z = 360.03 (C 20 H 13 BrN 2 = 361.24)	Sub4-82	m / z = 316.08 (C 20 H 13 ClN 2 = 316.79)
Sub4-83	m / z = 450.04 (C 26 H 15 BrN 2 O = 451.32)	Sub4-84	m / z = 457.11 (C 28 H 16 ClN 5 = 457.92)
Sub4-85	m / z = 430.10 (C 27 H 15 ClN 4 = 430.90)	Sub4-86	m / z = 280.04 (C 16 H 9 ClN 2 O = 280.71)
Sub4-87	m / z = 305.04 (C 17 H 8 ClN 3 O = 305.72)	Sub4-88	m / z = 298.03 (C 16 H 9 FClN 2 O = 298.70)
Sub4-89	m / z = 416.00 (C 22 H 13 BrN 2 S = 417.32)	Sub4-90	m / z = 356.07 (C 22 H 13 ClN 2 O = 356.81)
Sub4-91	m / z = 396.10 (C 25 H 17 ClN 2 O = 396.87)	Sub4-92	m / z = 513.07 (C 31 H 16 ClN 3 OS = 514.00)

III. Final Product 2 Synthesis

Sub3 (1 equiv) was dissolved in toluene in a round bottom flask, then Sub4 (1 equiv), Pd ₂ (dba) ₃ (0.03 equiv), ( t -Bu) ₃ P (1 equiv), NaO t -Bu (2 equiv) were stirred at 120 ° 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.

1.2-1 Synthesis Example

Sub3-1 (3.0 g, 9.02 mmol) obtained in the synthesis was dissolved in toluene (100 mL) in a round bottom flask, then Sub4-1 (1.4 g, 9.02 mmol), Pd ₂ (dba) ₃ (0.25 g, 0.271 mmol ), P ( t -Bu) ₃ (1.8 g, 9.02 mmol), NaO t -Bu (1.7 g, 18.0 mmol) was added and stirred at 120 ° 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 recrystallization to obtain 2.4 g (yield: 65%) of product 2-1.

2. 2-9 Synthesis Example

Sub3-2 (3.0 g, 11.0 mmol), Sub4-30 (2.8 g, 11.0 mmol), Pd ₂ (dba) ₃ (0.30 g, 0.33 mmol), P ( t -Bu) ₃ (2.2 g, 11.0 mmol) , NaO t -Bu (2.1 g, 22.0 mmol) was obtained in the amount of 3.6 g (yield: 67%) of the product 2-9 using the synthesis method of 2-1.

3. 2-24 Synthesis Example

Sub3-3 (3.0 g, 11.7 mmol), Sub4-78 (2.8 g, 11.7 mmol), Pd ₂ (dba) ₃ (0.32 g, 0.35 mmol), P ( t -Bu) ₃ (2.4 g, 11.7 mmol) , NaO t -Bu (2.2 g, 23.3 mmol) was obtained 2.4 g (yield: 45%) of the product 2-24 using the synthesis method of 2-1.

4. 2-34 Synthesis Example

Sub3-5 (3.0 g, 9.02 mmol), Sub4-49 (2.6 g, 9.02 mmol), Pd ₂ (dba) ₃ (0.25 g, 0.271 mmol), P ( t -Bu) ₃ (1.8 g, 9.02 mmol) , NaO t -Bu (17 g, 18.0 mmol) was obtained by 3.3 g (yield: 63%) of the product 2-34 using the above synthesis method.

5. 2-49 Synthesis Example

Sub3-7 (3.0 g, 11.7 mmol), Sub4-62 (3.5 g, 11.7 mmol), Pd ₂ (dba) ₃ (0.32 g, 0.350 mmol), P ( t -Bu) ₃ (2.4 g, 11.7 mmol) , NaO t -Bu (2.2 g, 23.3 mmol) was obtained by 4.3 g (yield: 72%) of the product 2-49 using the above synthesis method.

6. 2-61 Synthesis Example

Sub3-9 (3.0 g, 9.02 mmol), Sub4-49 (2.6 g, 9.02 mmol), Pd ₂ (dba) ₃ (0.25 g, 0.271 mol), P ( t -Bu) ₃ (1.8 g, 9.02 mmol) , NaO t -Bu (17 g, 18.0 mmol) was obtained using the synthesis method of 2-1 to obtain 3.9 g (yield: 73%) of the product 2-61.

7. 2-77 Synthesis Example

Sub3-12 (3.0 g, 10.6 mmol), Sub4-83 (4.8 g, 10.6 mmol), Pd ₂ (dba) ₃ (0.29 g, 0.318 mmol), P ( t -Bu) ₃ (2.1 g, 10.6 mmol) , NaO t -Bu (2.0 g, 21.2 mmol) was obtained using the synthesis method of 2-1 to obtain 5.4 g (yield: 78%) of the product 2-77.

8. 2-84 Synthesis Example

Sub3-13 (3.0 g, 9.02 mmol), Sub4-15 (3.7 g, 9.02 mmol), Pd ₂ (dba) ₃ (0.25 g, 0.271 mmol), P ( t -Bu) ₃ (1.8 g, 9.02 mmol) , NaO t -Bu (1.7 g, 18.0 mmol) was obtained by 4.3 g (yield: 71%) of the product 2-84 using the above synthesis method.

9. Synthesis Example 2-101

Sub3-18 (3.0 g, 11.0 mmol), Sub4-44 (4.0 g, 11.0 mmol), Pd ₂ (dba) ₃ (0.30 g, 0.329 mmol), P ( t -Bu) ₃ (2.2 g, 11.0 mmol) , NaO t -Bu (2.1 g, 21.9 mmol) was obtained 4.5 g (yield: 68%) of product 2-101 using the synthesis method of 2-1.

10.122 Example

Sub3-15 (3.0 g, 11.7 mmol), Sub4-48 (3.9 g, 11.7 mmol), Pd ₂ (dba) ₃ (0.32 g, 0.350 mmol), P ( t -Bu) ₃ (2.4 g, 11.7 mmol) , NaO t -Bu (2.2 g, 23.3 mmol) was obtained using the synthesis method of 2-1 to obtain 3.7 g (yield: 58%) of the product 2-122.

On the other hand, FD-MS values of the compounds 2-1 to 2-128 of the present invention prepared according to the synthesis examples as described above are shown in Table 3.

compound	FD-MS	compound	FD-MS
2-1	m / z = 408.16 (C 30 H 20 N 2 = 408.50)	2-2	m / z = 435.17 (C 31 H 31 N 3 = 435.53)
2-3	m / z = 410.15 (C 28 H 18 N 4 = 410.48)	2-4	m / z = 536.20 (C 38 H 24 N 4 = 536.64)
2-5	m / z = 586.22 (C 42 H 26 N 4 = 586.70)	2-6	m / z = 536.20 (C 38 H 24 N 4 = 536.64)
2-7	m / z = 563.21 (C 39 H 25 N 5 = 563.66)	2-8	m / z = 592.17 (C 40 H 24 N 4 S = 592.72)
2-9	m / z = 491.15 (C 33 H 21 N 3 S = 491.61)	2-10	m / z = 527.15 (C 36 H 21 N 3 S = 527.65)
2-11	m / z = 533.10 (C 34 H 19 N 3 S 2 = 533.67)	2-12	m / z = 580.17 (C 39 H 24 N 4 S = 580.71)
2-13	m / z = 504.14 (C 33 H 20 N 4 S = 504.61)	2-14	m / z = 477.13 (C 33 H 19 N 3 S = 477.59)
2-15	m / z = 477.13 (C 33 H 19 N 3 S = 477.59)	2-16	m / z = 351.08 (C 22 H 13 N 3 S = 351.43)
2-17	m / z = 734.18 (C 49 H 25 N 4 O 2 S = 734.83)	2-18	m / z = 577.18 (C 40 H 23 N 3 O 2 = 577.64)
2-19	m / z = 517.12 (C 34 H 19 N 3 OS = 517.61)	2-20	m / z = 606.18 (C 42 H 26 N 2 OS = 606.74)
2-21	m / z = 488.16 (C 33 H 20 N 4 O = 488.55)	2-22	m / z = 461.15 (C 33 H 19 N 3 S = 477.59)
2-23	m / z = 517.12 (C 34 H 19 N 3 OS = 517.61)	2-24	m / z = 461.15 (C 32 H 19 N 3 O = 461.52)
2-25	m / z = 552.20 (C 38 H 24 N 4 O = 552.64)	2-26	m / z = 619.21 (C 43 H 29 N 3 S = 619.79)
2-27	m / z = 527.20 (C 37 H 25 N 3 O = 527.63)	2-28	m / z = 513.22 (C 37 H 27 N 3 = 513.64)
2-29	m / z = 800.21 (C 54 H 32 N 4 S 2 = 801.00)	2-30	m / z = 485.19 (C 35 H 23 N 3 = 485.59)
2-31	m / z = 586.22 (C 42 H 26 N 4 = 586.70)	2-32	m / z = 536.20 (C 38 H 24 N 4 = 536.64)
2-33	m / z = 592.17 (C 40 H 24 N 4 S = 592.72)	2-34	m / z = 586.22 (C 42 H 26 N 4 = 586.70)
2-35	m / z = 563.21 (C 39 H 25 N 5 = 563.66)	2-36	m / z = 410.15 (C 28 H 18 N 4 = 410.48)
2-37	m / z = 527.15 (C 36 H 21 N 3 S = 527.65)	2-38	m / z = 580.17 (C 39 H 24 N 4 S = 580.71)
2-39	m / z = 553.16 (C 38 H 23 N 3 S = 553.68)	2-40	m / z = 639.09 (C 40 H 21 N 3 S 3 = 639.81)
2-41	m / z = 527.15 (C 36 H 21 N 3 S = 527.65)	2-42	m / z = 527.15 (C 36 H 21 N 3 S = 527.65)
2-43	m / z = 504.14 (C 33 H 20 N 4 S = 504.61)	2-44	m / z = 351.08 (C 22 H 13 N 3 S = 351.43)
2-45	m / z = 511.17 (C 36 H 21 N 3 O = 511.58)	2-46	m / z = 613.22 (C 44 H 27 N 3 O = 613.72)
2-47	m / z = 587.20 (C 42 H 25 N 3 O = 587.68)	2-48	m / z = 538.18 (C 37 H 22 N 4 O = 538.61)
2-49	m / z = 517.12 (C 34 H 19 N 3 OS = 517.61)	2-50	m / z = 511.17 (C 36 H 21 N 3 O = 511.58)
2-51	m / z = 501.15 (C 34 H 19 N 3 O 2 = 501.55)	2-52	m / z = 461.15 (C 32 H 19 N 3 O = 461.52)
2-53	m / z = 643.21 (C 45 H 29 N 3 S = 643.81)	2-54	m / z = 649.22 (C 44 H 31 N 3 OS = 649.81)
2-55	m / z = 630.24 (C 44 H 30 N 4 O = 630.75)	2-56	m / z = 645.22 (C 45 H 31 N 3 S = 645.82)
2-57	m / z = 692.26 (C 49 H 32 N 4 O = 692.82)	2-58	m / z = 680.24 (C 48 H 29 FN 4 = 680.79)
2-59	m / z = 626.21 (C 44 H 26 N 4 O = 626.72)	2-60	m / z = 720.23 (C 50 H 32 N 4 S = 720.89)
2-61	m / z = 586.22 (C 42 H 26 N 4 = 586.70)	2-62	m / z = 536.20 (C 38 H 24 N 4 = 536.64)
2-63	m / z = 592.17 (C 40 H 24 N 4 S = 592.72)	2-64	m / z = 536.20 (C 38 H 24 N 4 = 536.64)
2-65	m / z = 577.16 (C 40 H 23 N 3 S = 577.71)	2-66	m / z = 495.18 (C 33 H 25 N 3 S = 495.64)
2-67	m / z = 603.18 (C 42 H 25 N 3 S = 603.74)	2-68	m / z = 604.17 (C 41 H 24 N 4 S = 604.73)
2-69	m / z = 477.13 (C 32 H 19 N 3 S = 477.59)	2-70	m / z = 527.15 (C 36 H 21 N 3 S = 527.65)
2-71	m / z = 533.10 (C 34 H 19 N 3 S 2 = 533.67)	2-72	m / z = 517.12 (C 34 H 19 N 3 OS = 517.61)
2-73	m / z = 598.19 (C 40 H 18 D 5 N 3 OS = 598.73)	2-74	m / z = 511.17 (C 36 H 21 N 3 O = 511.58)
2-75	m / z = 537.18 (C 38 H 23 N 3 O = 537.62)	2-76	m / z = 563.20 (C 40 H 25 N 3 O = 563.66)
2-77	m / z = 653.45 (C 47 H 31 N 3 O = 653.79)	2-78	m / z = 626.27 (C 47 H 34 N 2 = 626.80)
2-79	m / z = 537.22 (C 39 H 27 N 3 = 537.67)	2-80	m / z = 652.26 (C 47 H 32 N 4 = 652.80)
2-81	m / z = 586.22 (C 42 H 26 N 4 = 586.70)	2-82	m / z = 563.21 (C 39 H 25 N 5 = 563.66)
2-83	m / z = 586.22 (C 42 H 26 N 4 = 586.70)	2-84	m / z = 663.24 (C 47 H 29 N 5 = 663.78)
2-85	m / z = 465.13 (C 31 H 19 N 3 S = 465.57)	2-86	m / z = 554.16 (C 37 H 22 N 4 S = 554.67)
2-87	m / z = 553.16 (C 38 H 23 N 3 S = 553.68)	2-88	m / z = 623.11 (C 40 H 21 N 3 OS 2 = 623.75)
2-89	m / z = 693.19 (C 48 H 27 N 3 OS = 693.82)	2-90	m / z = 466.18 (C 32 H 14 D 5 N 3 O = 466.55)
2-91	m / z = 652.19 (C 45 H 24 N 4 O 2 = 652.71)	2-92	m / z = 593.16 (C 40 H 23 N 3 OS = 593.70)
2-93	m / z = 561.17 (C 37 H 24 FN 3 S = 561.68)	2-94	m / z = 715.21 (C 51 H 29 N 3 S = 715.87)
2-95	m / z = 603.23 (C 43 H 29 N 3 O = 603.73)	2-96	m / z = 610.24 (C 45 H 30 N 2 = 610.76)
2-97	m / z = 753.26 (C 52 H 31 N 7 = 753.87)	2-98	m / z = 597.20 (C 40 H 19 D 5 N 4 S = 597.75)
2-99	m / z = 626.21 (C 44 H 26 N 4 O = 626.72)	2-100	m / z = 541.23 (C 38 H 19 D 5 N 4 = 541.67)
2-101	m / z = 603.18 (C 42 H 25 N 3 S = 603.74)	2-102	m / z = 738.19 (C 49 H 30 N 4 S 2 = 738.93)
2-103	m / z = 655.21 (C 46 H 29 N 3 S = 655.82)	2-104	m / z = 694.22 (C 48 H 30 N 4 S = 694.86)
2-105	m / z = 636.23 (C 43 H 29 FN 4 O = 636.73)	2-106	m / z = 551.16 (C 38 H 21 N 3 O 2 = 551.61)
2-107	m / z = 776.17 (C 51 H 28 N 4 OS 2 = 776.93)	2-108	m / z = 769.26 (C 52 H 31 N 7 O = 769.87)
2-109	m / z = 637.25 (C 47 H 31 N 3 = 637.79)	2-110	m / z = 643.21 (C 45 H 29 N 3 S = 643.81)
2-111	m / z = 609.22 (C 45 H 27 N 3 = 609.73)	2-112	m / z = 603.23 (C 43 H 29 N 3 O = 603.73)
2-113	m / z = 776.27 (C 55 H 32 N 6 = 776.90)	2-114	m / z = 814.27 (C 59 H 34 N 4 O = 814.95)
2-115	m / z = 795.25 (C 55 H 33 N 5 S = 795.96)	2-116	m / z = 662.25 (C 48 H 30 N 4 = 662.80)
2-117	m / z = 541.16 (C 37 H 23 N 3 S = 541.67)	2-118	m / z = 406.06 (C 25 H 14 N 2 S 2 = 406.52)
2-119	m / z = 450.12 (C 31 H 18 N 2 S = 450.56)	2-120	m / z = 439.11 (C 29 H 17 N 3 S = 439.54)
2-121	m / z = 502.14 (C 33 H 18 N 4 O 2 = 502.53)	2-122	m / z = 551.11 (C 32 H 14 F 5 N 3 O = 551.48)
2-123	m / z = 705.28 (C 51 H 35 N 3 O = 705.86)	2-124	m / z = 661.22 (C 48 H 27 N 3 O = 661.76)
2-125	m / z = 603.23 (C 43 H 29 N 3 O = 603.73)	2-126	m / z = 563.24 (C 41 H 29 N 3 = 563.70)
2-127	m / z = 593.19 (C 41 H 27 N 3 S = 593.75)	2-128	m / z = 545.19 (C 37 H 24 FN 3 O = 545.62)

Manufacturing Evaluation of Organic Electrical Device

Example 1 Fabrication and Test of Red Organic Light-Emitting Device

First, on the ITO layer (anode) formed on the glass substrate, N ^1- (naphthalen-2-yl) -N ⁴ , N ⁴ -bis (4- (naphthalen-2-yl (phenyl) amino) phenyl ) -N ¹ -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) membrane was vacuum deposited to form a thickness of 60 nm. Subsequently, N, N'-Bis (1-naphthalenyl) -N, N'-bis-phenyl- (1,1'-biphenyl) -4,4'-diamine (hereinafter abbreviated as NPB) is 60 nm thick. Vacuum deposition was performed to form a hole transport layer. A mixture of 50:50 of the inventive compound represented by Formula 1 and Formula 2 was used as a host on the hole transport layer, and as a dopant, (piq) ₂ Ir (acac) [bis- (1-phenylisoquinolyl) iridium ( III) acetylacetonate] was deposited to a weight of 95: 5 to deposit a 30 nm thick light emitting layer on the hole transport layer. As a hole blocking layer, (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm, and the electron transport layer Tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was formed into a 40 nm thick film. Subsequently, LiF, which is an alkali metal halide, was deposited to a thickness of 0.2 nm as an electron injection layer, and then, Al was deposited to a thickness of 150 nm to prepare an organic electroluminescent device.

The electroluminescent (EL) characteristics of the Example and Comparative Example organic electroluminescent devices prepared as described above were applied to the PR-650 of photoresearch by applying a forward bias DC voltage. The T95 life was measured using a life measurement instrument manufactured by McScience. The following table shows the results of device fabrication and evaluation.

Comparative Example 1

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 2, Comparative Example 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 and Compound 2 were used as a host.

[Comparative Compound 1]

When the second host is fixed and various first hosts are mixed

	First compound	Second compound	Driving voltage	Current (mA / cm2)	Luminance (cd / m2)	Efficiency (cd / A)	T (95)
Comparative Example 1	Comparative Compound 1	-	7.9	39.1	2500.0	6.4	60.1
Comparative Example 2	-	2-117	7.2	21.7	2500.0	11.5	81.5
Comparative Example 3	-	2-122	7.4	22.3	2500.0	11.2	76.8
Comparative Example 4	Comparative Compound 1	2-117	7.0	20.3	2500.0	12.3	92.8
Example 1	1-1	2-117	5.9	15.8	2500.0	15.8	102.6
Example 2	1-16	2-117	5.5	13.9	2500.0	18.0	113.6
Example 3	1-53	2-117	6.0	15.4	2500.0	16.2	103.6
Example 4	1-59	2-117	5.5	13.2	2500.0	18.9	115.0
Example 5	1-60	2-117	5.8	13.9	2500.0	18.0	112.1
Example 6	1-65	2-117	5.9	14.9	2500.0	16.8	106.3
Example 7	1-76	2-117	5.6	13.5	2500.0	18.5	110.3
Example 8	1-116	2-117	6.1	15.7	2500.0	15.9	101.7
Example 9	1-117	2-117	5.9	16.1	2500.0	15.6	102.0
Example 10	1-119	2-117	6.2	16.4	2500.0	15.3	103.6
Example 11	1-139	2-117	5.8	14.9	2500.0	16.7	103.7
Example 12	1-181	2-117	5.7	14.3	2500.0	17.4	111.2
Example 13	1-186	2-117	5.8	14.3	2500.0	17.5	109.4
Example 14	1-188	2-117	5.9	15.2	2500.0	16.4	101.4
Example 15	1-190	2-117	5.9	14.6	2500.0	17.1	103.0
Example 16	1-205	2-117	6.0	16.0	2500.0	15.6	100.2

When the first host material is mixed with various second host materials

	First compound	Secondary compound	Driving voltage	Current (mA / cm2)	Luminance (cd / m2)	Efficiency (cd / A)	T (95)
Example 17	1-16	2-1	5.8	11.3	2500.0	22.1	114.1
Example 18	1-59	2-1	5.9	12.0	2500.0	20.8	115.8
Example 19	1-60	2-1	5.9	11.4	2500.0	21.9	112.8
Example 20	1-65	2-1	6.0	14.4	2500.0	17.4	105.7
Example 21	1-181	2-1	6.0	13.5	2500.0	18.6	109.3
Example 22	1-186	2-1	6.0	12.5	2500.0	20.0	108.6
Example 23	1-16	2-4	5.1	9.2	2500.0	27.3	123.8
Example 24	1-59	2-4	4.9	9.1	2500.0	27.3	124.5
Example 25	1-60	2-4	5.2	9.2	2500.0	27.1	121.5
Example 26	1-65	2-4	5.4	9.8	2500.0	25.5	118.8
Example 27	1-181	2-4	5.1	9.8	2500.0	25.6	121.7
Example 28	1-186	2-4	5.2	9.6	2500.0	26.1	119.3
Example 29	1-16	2-7	4.6	8.1	2500.0	30.7	128.2
Example 30	1-59	2-7	4.7	8.2	2500.0	30.4	129.9
Example 31	1-60	2-7	5.0	8.4	2500.0	29.6	125.2
Example 32	1-65	2-7	5.1	9.6	2500.0	26.1	122.6
Example 33	1-181	2-7	4.9	9.1	2500.0	27.5	126.0
Example 34	1-186	2-7	5.0	9.1	2500.0	27.6	124.3
Example 35	1-16	2-15	4.8	8.6	2500.0	29.0	127.0
Example 36	1-59	2-15	4.8	8.4	2500.0	29.7	126.6
Example 37	1-60	2-15	4.8	9.0	2500.0	27.9	124.4
Example 38	1-65	2-15	5.1	9.4	2500.0	26.5	120.7
Example 39	1-181	2-15	4.9	8.9	2500.0	28.0	123.7
Example 40	1-186	2-15	5.2	9.4	2500.0	26.5	121.7
Example 41	1-16	2-33	5.0	8.8	2500.0	28.3	124.6
Example 42	1-59	2-33	5.0	8.7	2500.0	28.7	124.6
Example 43	1-60	2-33	4.9	9.4	2500.0	26.6	122.3
Example 44	1-65	2-33	5.3	9.8	2500.0	25.5	118.2
Example 45	1-181	2-33	5.2	9.8	2500.0	25.5	121.5
Example 46	1-186	2-33	5.0	9.6	2500.0	26.1	119.6
Example 47	1-16	2-42	5.3	9.6	2500.0	25.9	121.9
Example 48	1-59	2-42	5.1	9.6	2500.0	26.0	121.9
Example 49	1-60	2-42	5.4	10.3	2500.0	24.3	119.6
Example 50	1-65	2-42	5.5	11.2	2500.0	22.2	116.0
Example 51	1-181	2-42	5.5	10.7	2500.0	23.4	118.7
Example 52	1-186	2-42	5.5	10.2	2500.0	24.5	117.5
Example 53	1-16	2-43	5.1	9.3	2500.0	26.8	124.9
Example 54	1-59	2-43	5.2	9.0	2500.0	27.9	123.3
Example 55	1-60	2-43	5.2	9.5	2500.0	26.3	124.6
Example 56	1-65	2-43	5.4	10.4	2500.0	24.0	120.7
Example 57	1-181	2-43	5.3	9.6	2500.0	26.0	123.3
Example 58	1-186	2-43	5.2	9.8	2500.0	25.4	122.9
Example 59	1-16	2-62	5.3	10.7	2500.0	23.4	120.0
Example 60	1-59	2-62	5.2	10.2	2500.0	24.6	119.3
Example 61	1-60	2-62	5.5	11.3	2500.0	22.2	115.8
Example 62	1-65	2-62	5.6	12.5	2500.0	20.0	111.6
Example 63	1-181	2-62	5.5	10.8	2500.0	23.2	115.1
Example 64	1-186	2-62	5.5	11.9	2500.0	21.0	112.1
Example 65	1-16	2-70	5.3	10.3	2500.0	24.4	119.5
Example 66	1-59	2-70	5.3	10.1	2500.0	24.8	119.2
Example 67	1-60	2-70	5.3	10.8	2500.0	23.0	115.8
Example 68	1-65	2-70	5.5	12.3	2500.0	20.4	113.2
Example 69	1-181	2-70	5.6	10.9	2500.0	22.9	115.5
Example 70	1-186	2-70	5.5	11.5	2500.0	21.8	114.8
Example 71	1-16	2-82	5.5	11.0	2500.0	22.8	117.4
Example 72	1-59	2-82	5.5	10.7	2500.0	23.3	115.0
Example 73	1-60	2-82	5.6	11.5	2500.0	21.7	111.6
Example 74	1-65	2-82	5.8	12.7	2500.0	19.7	107.8
Example 75	1-181	2-82	5.7	11.9	2500.0	21.1	110.6
Example 76	1-186	2-82	5.7	11.8	2500.0	21.2	112.6
Example 77	1-16	2-83	5.4	10.8	2500.0	23.2	115.5
Example 78	1-59	2-83	5.5	10.5	2500.0	23.8	113.2
Example 79	1-60	2-83	5.6	11.1	2500.0	22.6	114.9
Example 80	1-65	2-83	5.8	12.6	2500.0	19.8	110.3
Example 81	1-181	2-83	5.7	11.5	2500.0	21.8	111.2
Example 82	1-186	2-83	5.8	11.4	2500.0	21.9	109.1
Example 83	1-16	2-122	5.6	13.5	2500.0	18.5	111.6
Example 84	1-59	2-122	5.6	13.2	2500.0	19.0	114.5
Example 85	1-60	2-122	5.7	14.0	2500.0	17.9	107.4
Example 86	1-65	2-122	6.0	15.2	2500.0	16.5	104.2
Example 87	1-181	2-122	5.7	14.4	2500.0	17.3	108.9
Example 88	1-186	2-122	5.8	15.1	2500.0	16.5	110.0

As can be seen from the results of Table 4, 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 88), a device using a single material (Comparative Example) Compared with 1 ~ 4) it was confirmed that the driving voltage, efficiency and life significantly improved.

In detail, in Comparative Examples 1 to 4 using the compound of the present invention represented by the formula (2) and Comparative Compound 1 alone as phosphorescent hosts, Comparative Example 2 using the compound of the present invention (2-117, 2-122) And Comparative Example 3 was confirmed to exhibit a higher efficiency and a higher lifetime than Comparative Example 1 using a comparative compound. In addition, it was confirmed that Comparative Example 1 and Compound (2-117) were mixed with Comparative Compound 1 and Comparative Example 4 using the phosphorescent host to show a slightly higher efficiency than Comparative Examples 1 to 3 using the single substance.

It was confirmed that Examples 1 to 88, which were used as a host by mixing the compounds of Formula 1 and Formula 2, which are the compounds of the present invention, than the Comparative Examples 1 to 4, exhibited significantly higher efficiency and lifespan. It was confirmed that the 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 and PL lifetime were measured using the mixture of the present invention, respectively. As a result, when the compounds of the present invention were mixed with Chemical Formula 1 and Chemical Formula 2, it was confirmed that a new PL wavelength was formed differently from the case of a single compound. It was confirmed that the increase and decrease than the disappearance time. 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. As a result, when using the mixture of the present invention it can be said that the mixed thin film is an important example showing the exciplex energy transfer and the light emission process.

In addition, the combination of the present invention is superior to Comparative Example 4, which is used as a phosphorescent host mixed with Comparative Compound 1, because the hole characteristics of the polycyclic ring compound represented by Chemical Formula 2 having characteristics such as electron stability as well as hole, and high T1 When the compound represented by the strong formula 1 is mixed, the electron blocking ability is improved due to the high T1 and the high LUMO energy value, 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 emission is achieved inside the light emitting layer rather than at the hole transport layer interface. . Furthermore, among the compounds represented by Formula 1, compounds in which M is substituted with Dibenzothiophen and Dibenzofuran were confirmed to have better efficiency and lifespan. In conclusion, the combination of Chemical Formula 1 and Chemical Formula 2 is electrochemically synergistic.

In addition, Table 5 is a result obtained by fixing the first host with excellent performance as a result obtained in Table 4 and using a mixture of various second host, the first host is a compound 1-16 excellent in driving voltage, efficiency and lifespan , 1-59, 1-60, 1-65, 1-181 and 1-186 and the second host are compounds 2-1, 2-4, 2-7, 2-15, 2-33, 2-42 , 2-43, 2-62, 2-70, 2-82, 2-83, and 2-122 resulted in a drive voltage when two mixed host materials were used rather than a single host material. In addition, it can be seen that the efficiency and lifespan can be significantly improved.

Example 2 Fabrication and Test of Red Organic Light-Emitting Device by Mixing Ratio

An organic electroluminescent device was manufactured in the same manner as in Example 1, except for using a different mixing ratio of materials as described in Table 6.

	First compound	Secondary compound	ratio	Driving voltage	Current (mA / cm2)	Luminance (cd / m2)	Efficiency (cd / A)	T (95)
Example 89	1-16	2-7	2: 8	4.6	8.3	2500.0	30.2	129.7
Example 90	1-16	2-7	3: 7	4.6	7.9	2500.0	31.5	129.3
Example 91	1-16	2-7	4: 6	4.8	8.3	2500.0	30.1	127.1
Example 92	1-16	2-7	6: 4	5.3	10.2	2500.0	24.5	115.2
Example 93	1-16	2-7	7: 3	5.5	11.0	2500.0	22.8	116.0
Example 94	1-16	2-7	8: 2	5.6	13.0	2500.0	19.2	116.7
Example 95	1-59	2-7	2: 8	4.6	8.0	2500.0	31.1	129.4
Example 96	1-59	2-7	3: 7	4.6	7.9	2500.0	31.6	130.7
Example 97	1-59	2-7	4: 6	4.8	8.3	2500.0	30.2	127.1
Example 98	1-59	2-7	6: 4	5.2	10.4	2500.0	24.0	116.9
Example 99	1-59	2-7	7: 3	5.6	10.5	2500.0	23.7	116.2
Example 100	1-59	2-7	8: 2	5.5	13.4	2500.0	18.7	112.7

As shown in Table 6, the mixture of the compound of the present invention was measured by manufacturing a device by ratio (2: 8, 3: 7, 4: 6, 6: 4, 7: 3, 8: 2). In detail, the results of the mixture of compound 1-16 and compound 2-7 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 reduced, which was the same in the mixture of Compound 1-59 and Compound 2-7. 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.

According to the present invention, it is possible to manufacture an organic device having excellent device characteristics of high brightness, high light emission and long life, and there is industrial applicability.

Claims (16)

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 the following formula (2)

                      Chemical Formula 1 Chemical Formula 2

   

   Formula 1-1 Formula 2-1

   

   

   {In Formula 1 and Formula 2,

   1) M is an arylene group of C ₆ -C ₆₀ or Formula 1-1,

   2) A, B, C and D are each independently an aryl group of C ₆ -C ₂₀ or a heterocyclic group of C ₂ -C ₂₀ , C is bonded to L ³ , D is bonded to L ⁴ ,

   3) X ¹ is S or O,

   X ² is NL ⁶ -Ar ⁷ , O, S or CR'R ",

   X ³ and X ⁴ are each independently a single bond, NL ⁷ -Ar ⁸ , O, S or CR'R ",

   Except that X ³ and X ⁴ are both single bonds,

   R 'and R "are each independently hydrogen; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₃ ~ C ₆₀ Heterocyclic group; C ₁ ~ C ₅₀ Alkyl group; and -L'-N (R ^a ) (R ^b ), and

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

   4) L 'is a single bond; C ₆ -C ₆₀ arylene group; Fluorenylene groups; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; And a C ₂ -C ₆₀ heterocyclic group; selected from the group consisting of R ^a and R ^b independently of each other an C ₆ -C ₆₀ aryl group; Fluorenyl groups; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; And a C ₂ -C ₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si, and P, and

   5) In Formula 2, a pair of * 1 and * 2, * 2 and * 3, and * 3 and * 4 may bind to * 5 and * 6 of Formula 2-1, respectively.

   6) Ar ¹ , Ar ² , Ar ³ , Ar ⁴ , Ar ⁵ , Ar ⁶ , Ar ⁷ And Ar ⁸ are each independently of the other C ₆ -C ₆₀ aryl group; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; Fluorenyl groups; A fused ring group of an aromatic ring of C ₆ -C ₆₀ and an aliphatic ring of C ₃ -C ₆₀ ; An alkyl group of C ₁ -C ₅₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; And an aryloxy group of C ₆ -C ₃₀ , and also Ar ¹ Ar ⁵ may combine with each other to form a ring,

   7) L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ and L ⁷ 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 aliphatic hydrocarbon groups,

   8) l and n are integers of 0 to 4, m is an integer of 0 to 2, R ⁴ , R ⁵ and R ⁶ are each independently of the C ₆ ~ C ₆₀ aryl group; Fluorenyl groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ -C ₃₀ alkoxyl group; C ₆ -C ₃₀ aryloxy group; And -L'-N (R ^a ) (R ^b ); Is selected from the group consisting of

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

   a-1 a-2 a-3 a-4

   

         a-5 a-6 a-7

   

   {In Chemical Formulas a-1 to a-7,

   1) Z ¹ to Z ⁴⁸ are independently of each other CR ^c or N,

   Provided that Z ¹ to Z ⁴⁸ bonded to L ¹ to L ³ are carbon (C),

   2) R ^c is the same as the definition of R ^a in claim 1,

   3) * indicates the location of condensation}
3. The organic electric device of claim 1, wherein in Formula 1 or Formula 2, L ¹ to L ⁷ are represented by any one of Formulas b-1 to b-13.

    b-1 b-2 b-3 b-4 b-5 b-6

   

    b-7 b-8 b-9 b-10

   

    b-11 b-12 b-13

   

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

   1) Y is NL ⁸ -Ar ⁹ , O, S or CR'R ",

   2) L ⁸ is the same as the definition of L ¹ in claim 1,

   3) Ar ⁹ is the same as the definition of Ar ¹ in claim 1,

   4) R 'and R "are the same as defined in claim 1 above,

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

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

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

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

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

   Formula 1-2

   

   {In Formula 1-2,

   1) E and F are the same as the definition of A in claim 1,

   2) X ⁵ is NL ¹⁰ -Ar ¹⁰ , O, S or CR'R ",

   3) L ⁹ and L ¹⁰ are the same as the definition of L ¹ in claim 1,

   4) Ar ¹⁰ is the same as the definition of Ar ¹ in claim 1,

   5) R 'and R "are as defined in claim 1 above.}
5. The organic electric device of claim 1, wherein the first host compound represented by Chemical Formula 1 is represented by the following Chemical Formula 3. 3.

   Formula 3

   

   {In Formula 3,

   X ¹ , X ² , Ar ¹ to Ar ⁵ are the same as defined in claim 1,

   Z ¹ to Z ⁴ are each independently CR ^c or N,

   R ^c is identical to the definition of R ^a in claim 1.
6. The organic electroluminescence device according to claim 1, wherein X ¹ and X ² of Formula 1 are each independently O or S.
7. 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 4 to 6.

           Formula 4 Formula 5 Formula 6

   

   {In Formulas 4 to 6, R ⁴ , R ⁵ , R ⁶ , X ³ , X ⁴ , L ⁵ , L ⁷ , Ar ⁶ , Ar ⁸ , l, m and n are as defined in claim 1 above. }
8. 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 7 to 12.

          Formula 7 Formula 8 Formula 9

   

          Chemical Formula 10 Chemical Formula 11 Chemical Formula 12

   

   {In Formula 7 to Formula 12,

   R ⁴ , R ⁵ , R ⁶ , L ⁵ , L ⁷ , Ar ⁶ , Ar ⁸ , l, m and n are as defined in claim 1 above,

   X is selected from NL ⁷ -Ar ⁸ , O, S or CR'R ".
9. The organic electroluminescent device according to claim 1, wherein the first host compound represented by Chemical Formula 1 is any one of the following Compounds 1-1 to 1-265.

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   
10. The organic electronic device of claim 1, wherein the second host compound represented by Chemical Formula 2 is any one of the following Compounds 2-1 to 2-128.

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    
11. 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 the formula (1).
12. 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.
13. The organic electroluminescence device according to claim 1, wherein the compound represented by Chemical Formula 1 and Chemical Formula 2 is used in a light emitting layer by mixing 1: 9 to 5: 5.
14. The organic electroluminescent device according to claim 1, wherein the compound represented by Chemical Formula 1 and Chemical Formula 2 is used in a light emitting layer by mixing 2: 8 to 3: 7.
15. A display apparatus comprising the organic electric element according to claim 1, and a control unit for driving the display apparatus.
16. The electronic device of claim 15, 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 monochrome or white light emitting element.

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