KR20190078040A - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention relates to a novel compound which can improve luminous efficiency, stability and service life of an element, an organic electric element using the same, and an electronic device thereof. The organic electric device comprises: a first electrode; a second electrode; and an organic material layer formed between the first electrode and the second electrode.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a compound for organic electroluminescent devices, an organic electroluminescent device using the same, and an electronic device using the same. BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescent (EL)

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

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic electric device using an organic light emitting phenomenon generally has a structure including an anode, an anode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic electronic device, the organic material layer is often formed of a multi-layered structure made of different materials, and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

A material used as an organic material layer in an organic electric device may be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions.

In the case of the cyclic compounds of the vicinal structure containing heteroatoms, the difference in properties depending on the material structure is very large and is applied to various layers of organic electronic devices. Especially, it has various characteristics such as band gap (HOMO, LUMO), electrical characteristic, chemical property, physical properties depending on the number of rings and fused position and heteroatom type and arrangement, Has progressed.

The LUMO and HOMO levels of the host material in the phosphorescent organic electroluminescent device using the phosphorescent dopant material have a great influence on the efficiency and lifetime of the organic electroluminescent device, It is possible to prevent deterioration in efficiency and lifetime due to charge balance control, dopant quenching in the light emitting layer, and light emission at the interface of the hole transporting layer.

In the case of host materials for fluorescence and phosphorescent luminescence, the efficiency and lifetime increase of organic electronic devices using TADF (Thermal Activated Delayed Fluorescent) and Exciplex have been studied. Especially, the method of energy transfer from a host material to a dopant material Many studies are underway.

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

The TRTP (Time Resolved Transient PL) measurement method is a method of observing a decay time of a pulse light source on a host thin film, and observing energy transmission and emission delay time, It is a measurement method. The TRTP measurement is a method of distinguishing between fluorescence and phosphorescence, energy transfer in a mixed host material, exciplex energy transfer, and TADF energy transfer.

There are various factors affecting the efficiency and lifetime depending on the manner in which the energy is transferred from the host material to the dopant material, and the energy transfer method differs depending on the material, so that the stable and efficient host material for the organic electric device Is not sufficiently achieved. Therefore, development of new materials is continuously required, and development of a host material for a light emitting layer is urgently required.

KR 10-1170666 B1

The present invention has been proposed in order to solve the problems of the above-mentioned phosphorescent host material, and it is an object of the present invention to provide a phosphorescent light emitting organic electroluminescent device including a phosphorescent dopant by controlling the HOMO level of the host material, An organic electronic device using the same, and an electronic device therefor.

In order to control the efficient hole injection in the light emitting layer of the phosphorescence emitting organic electroluminescent device, the present invention includes a specific first host material in combination with a specific second host material as a main component, thereby reducing the energy barrier of the light emitting layer and the adjacent layer And maximize the charge balance in the light emitting layer, thereby providing high efficiency and long life of the organic electric device.

The organic electroluminescent device includes a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, wherein the organic layer includes a light emitting layer, And a second host compound represented by the following general formula (2): < EMI ID = 2.0 >

The present invention also provides organic electronic devices using the compounds represented by the above formulas and electronic devices thereof.

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

BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is an illustration of an organic electroluminescent device according to the present invention. FIG.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

The "heterocyclic group" may also include a ring containing SO ₂ in place of the carbon forming the ring. For example, the "heterocyclic group" includes the following compounds.

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

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

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

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

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

One also no explicit description, the terms in the "unsubstituted or substituted", "substituted" is heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C for use in the present invention ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl amine group, C ₁ ~ C ₂₀ alkyl thiophene group, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C of ₂₀ alkynyl, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, a C ₈ ~ C ₂₀ aryl alkenyl group, a silane group, a boron Means a group substituted with at least one substituent selected from the group consisting of a halogen atom, a halogen atom, a cyano group, a germanium group, and a C ₂ to C ₂₀ heterocyclic group.

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

When a is an integer of 0, 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. In this case, And the chemical formula or compound may be described. When a is an integer of 1, one substituent R < ¹ > is bonded to any one of carbon atoms forming a benzene ring, and when a is an integer of 2 or 3, R < ¹ > And when a is an integer of 4 to 6, it bonds to the carbon of the benzene ring in a similar manner, while the indication of the hydrogen bonded to the carbon forming the benzene ring is omitted.

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

The organic electroluminescent device includes 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, 1 < / RTI > and a second host compound represented by the general formula (2).

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

M is a C ₆ -C ₆₀ arylene group or the above formula (1-1)

X < ¹ > is S or O,

X ² is NL ⁵ -Ar ⁶ , O, S or CR ^a R ^b ,

X ³ is NL ⁸ -Ar ⁸ , O, S or CR ^c R ^d ,

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

C is bonded to L ³ , D is bonded to L ⁴ ,

R ^a , R ^b , R ^c and R ^d independently of one another are hydrogen, deuterium; Tritium; halogen; Cyano; A nitro group; An aryl group of C ₆ -C ₆₀ ; A fluorenyl group; Heterocyclic group of _{O, N, S, C 2} -C 60 containing at least one heteroatom selected from the group consisting of Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₁ -C ₃₀ alkoxyl group and a C ₆ -C ₃₀ aryloxy group; R ^a and R ^b may combine with each other to form a spiro compound;

Ar ¹ , Ar ² , Ar ³ , Ar ⁴ , Ar ⁵ , Ar ⁶ , Ar ⁷ and Ar ⁸ are each independently a C ₆ -C ₆₀ aryl group; Heterocyclic group of _{O, N, S, C 2} -C 60 containing at least one heteroatom selected from the group consisting of Si and P; A fluorenyl group; A fused ring group of a C ₆ -C ₆₀ aromatic ring and a C ₃ -C ₆₀ aliphatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₁ -C ₃₀ alkoxyl group; And a C ₆ -C ₃₀ aryloxy group; and Ar ¹ is selected from the group consisting of Ar ¹ To Ar ⁸ may combine with each other to form a ring,

L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , L ⁷ and L ⁸ independently of one another are a single bond; C ₆ -C ₆₀ arylene groups; A fluorenylene group; A C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; And a C ₃ -C ₆₀ aliphatic hydrocarbon group,

The aryl group, the fluorenyl group, the arylene group, the heterocyclic group, the fluorenylene group, the aliphatic cyclic group, the fused ring group, the alkyl group, the alkenyl group, the alkoxy group and the aryloxy group are respectively deuterium; halogen; A silane group; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; An alkyl thio group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkoxyl group; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₆ -C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted by deuterium; A fluorenyl group; A C ₂ -C ₂₀ heterocyclic group; A C ₃ -C ₂₀ cycloalkyl group; An arylalkyl group having _{7 to 20} carbon atoms, an arylalkyl group having _{7 to 20} carbon atoms and an arylalkenyl group having _{8 to 20} carbon atoms, and these substituents may be further bonded to each other to form a ring, Ring " refers to a fused ring consisting of a C ₃ -C ₆₀ aliphatic ring or a C ₆ -C ₆₀ aromatic ring or a C ₂ -C ₆₀ heterocyclic ring or a combination thereof, including saturated or unsaturated rings.

Specifically, the present invention includes compounds wherein A, B, C, D, E and F are independently selected from the group consisting of the following formulas a-1 to a-7.

(In formulas (a-1) to (a-7)

Z ¹ to Z ⁴⁸ are CR ^e or N,

Provided that Z ¹ to Z ⁴⁸ bonded to L ¹ to L ⁶ are carbon (C)

R ^e is the same as defined above for R ^a ,

* Indicates the position to be condensed.

The present invention further provides that the above-mentioned L ¹ to L ⁶ are any one of the following formulas (b-1) to (b-13).

Formula b-11 Formula b-12 Formula b-13

(In the formulas (b-1) to (b-13)

Y is NL ⁹ -Ar ⁹ , O, S or CR ^f R ^g ,

L ⁹ is the same as defined in L ⁵ above,

Ar ⁹ has the same definition as Ar ⁶ above,

R ^f and R ^g are as defined above for R ^a ,

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

R ¹ to R ³ independently of one another are hydrogen; heavy hydrogen; Tritium; halogen; Cyano; A nitro group; An aryl group of C ₆ -C ₆₀ ; A fluorenyl group; Heterocyclic group of _{O, N, S, C 2} -C 60 containing at least one heteroatom selected from the group consisting of Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₁ -C ₃₀ alkoxyl group; A C ₆ -C ₃₀ aryloxy group; And ^{-L a -N (R h) (} R i); if is selected from the group consisting of or wherein a, b, c, d, e, f and g is not less than 2, and h is 2 are each A plurality of R ^{1 s} or a plurality of R ^{2 s} or a plurality of R ^{3 s} or adjacent R ^{1 s} and R ^{2 s} or R ^{2 s} and R ^{3 s} are bonded to each other to form an aromatic ring or a heteroaromatic ring You can,

Wherein L ^a is a single bond; C ₆ -C ₆₀ arylene groups; A fluorenylene group; A C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; And C ₃ -C ₆₀ aliphatic hydrocarbon groups; and R ^h and R ⁱ are independently selected from the group consisting of C ₆ -C ₆₀ aryl groups; A fluorenyl group; Heterocyclic group of _{O, N, S, C 2} -C 60 containing at least one heteroatom selected from the group consisting of Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring,

Z ⁴⁹ , Z ⁵⁰ and Z ⁵¹ independently of one another are CR ^j or N, and at least one of Z ⁴⁹ , Z ⁵⁰ and Z ⁵¹ is N,

R ^j is hydrogen; heavy hydrogen; Tritium; halogen; Cyano; A nitro group; An aryl group of C ₆ -C ₆₀ ; A fluorenyl group; Heterocyclic group of _{O, N, S, C 2} -C 60 containing at least one heteroatom selected from the group consisting of Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₁ -C ₃₀ alkoxyl group; And a C ₆ -C ₃₀ aryloxy group, and adjacent R ¹ and R ^h may be bonded to each other to form an aromatic ring or a heteroaromatic ring.

As another example, the present invention provides an organic electroluminescent device wherein at least one of Ar ¹ to Ar ⁵ in Formula 1 includes a compound represented by Formula 1-2.

{In Formula 1-2,

I and J are the same as defined in the above A,

X ⁴ is NL ¹¹ -Ar ¹⁰ , O, S or CR ^k R ¹ ,

L ¹⁰ and L ¹¹ are the same as defined for L ⁵ above,

Ar ¹⁰ has the same definition as Ar ⁶ ,

R ^k and R ¹ are as defined above for R ^a .

The first host compound represented by Formula 1 includes a compound represented by Formula 3 below.

{In the above formula (3)

X ¹ , X ² , Ar ¹ to Ar ⁵ , and Z ¹ to Z ⁴ are as defined above.

Preferably, in the present invention, X ¹ and X ² in Formula 1 are independently O or S.

The present invention also relates to a compound represented by any one of the following general formulas (4) to (7), wherein the second host compound represented by general formula (2)

{In the above Chemical Formulas 4 to 7,

E, F, G, H, L ⁶ , L ⁷ , L ⁸ , Ar ⁷ , Ar ⁸ , R ^c and R ^d are as defined above.

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

In the present invention, the second host compound represented by Formula 2 includes the following Compounds 2-1 to 2-135.

1, an organic electroluminescent device 100 according to the present invention includes a first electrode 120, a second electrode 180 and a first electrode 120 formed on a substrate 110, (180), an organic material layer containing a compound represented by the general formula (1). In this case, the first electrode 120 may be an anode and the second electrode 180 may be a cathode (cathode). In case of an inverting type, the first electrode may be a cathode and the second electrode may be an anode.

The organic layer includes a hole injecting layer 130, a hole transporting layer 140, a light emitting layer 150, a light emitting auxiliary layer 151, an electron transporting layer 160, and an electron injecting layer 170 sequentially on the first electrode 120 . At this time, the remaining layers except the light emitting layer 150 may not be formed. The electron blocking layer, the electron blocking layer, the emission auxiliary layer 151, the electron transporting auxiliary layer, and the buffer layer 141. The electron transporting layer 160 may serve as a hole blocking layer.

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

On the other hand, since the band gap, the electrical characteristics, the interface characteristics, and the like can be changed depending on which substituent is bonded at any position even in the same core, the selection of the core and the combination of the sub- Especially when energy level and T1 value between each organic material layer, and the intrinsic characteristics (mobility, interfacial characteristics, etc.) of the material are optimized, long life and high efficiency can be achieved at the same time.

The organic electroluminescent device according to an embodiment of the present invention can be manufactured using a physical vapor deposition (PVD) method. For example, a positive hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron transport layer 160 are formed on a substrate by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate, Forming an organic material layer including the electron injection layer 170, and then depositing a material usable as a cathode thereon. A light emitting auxiliary layer 151 may be further formed between the hole transporting layer 140 and the light emitting layer 150 and an electron transporting auxiliary layer may be further formed between the light emitting layer 150 and the electron transporting layer 160.

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

Also, the present invention provides an organic electroluminescent device wherein the compound represented by Formula 1 and the compound represented by Formula 2 are mixed in a ratio of 1: 9 to 9: 1 and included in the light emitting layer, : 5, more preferably in a ratio of 2: 8 or 3: 7 and contained in the light emitting layer.

The organic electroluminescent device may further include a light efficiency improvement layer formed on at least one side of the one side of the first electrode opposite to the organic layer or one side of the one side of the second electrode opposite to the organic layer, Thereby providing an organic electric device.

In the present invention, the organic material layer may be 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. Therefore, the scope of the present invention is not limited by the forming method.

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

WOLED (White Organic Light Emitting Device) has advantages of high resolution realization and fairness, and can be manufactured using existing color filter technology of LCD. Various structures for a white organic light emitting device mainly used as a backlight device have been proposed and patented. Typically, a stacking method in which R (Red), G (Green) and B (Blue) light emitting parts are arranged side by side, and 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 from the electroluminescent material. Can be applied to such WOLED.

The present invention also relates to a display device including the above organic electroluminescent device; And a control unit for driving the display device.

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

Hereinafter, the synthesis examples of the compounds represented by the formulas (1) and (2) and the production example of the organic electronic device of the present invention will be described in detail with reference to examples, but the present invention is not limited thereto .

[ Synthetic example  One]

The final product 1 represented by formula (1) according to the present invention can be obtained by the method described in Korean Patent No. 10-1614739 (registered in the date of April 18, 2018) and Korean Patent Application No. 2016-0110817 (filed on August 20, 2013) Was prepared by the disclosed synthetic method. X ¹ , A, B, L ¹ to L ⁴ , M, Ar ¹ to Ar ⁵ are the same as defined in Formula 1 above.

<Reaction Scheme 1>

[ Synthetic example  2]

The final product 2 represented by formula 2 according to the present invention is synthesized by reacting Sub 3 with Sub 4 as shown in the following reaction formula 2, but is not limited thereto. X ³ , E, F, G, H, L ⁶ , L ⁷ and Ar ⁷ are the same as defined in Formula 2 and Hal ² is Br or Cl.

<Reaction Scheme 2>

I. Synthesis of Sub 3

Sub 3 of Reaction Scheme 2 is synthesized by the reaction path of the following Reaction Scheme 3, but is not limited thereto.

<Reaction Scheme 3>

The carbazole derivative, which is a starting material used in the synthesis of Sub 3, is disclosed in Korean Patent No. 10-1535606 (Registration Notice dated Jul. 5, 2013), Korean Patent Application No. 2012-0152002 (filed on December 24, 2012) Was prepared by the synthetic method disclosed in patent 2016-0025426 (filed March 23, 2013).

The dibenzothiophene derivative or the dibenzofuran, which is the starting material used in the synthesis of Sub 3, was prepared by the synthetic method disclosed in Korean Patent Application No. 2014-0074261 (filed on Apr. 18, 2014) of the present applicant.

The fluorene derivative, which is a starting material used in the synthesis of Sub 3, can be produced by the synthesizing method disclosed in Korean Patent Application No. 2013-0056221 (filed on May 20, 201) and Korean Patent Application No. 2015-0083505 (filed on June 20, 2015) .

1. Sub 3-1 Synthetic example

The starting material, 3-bromo-9 H -carbazole ( 47.03 g, 191.09 mmol) was dissolved in a THF (850 ml) in a round bottom flask, 9-phenyl-3- (4,4,5,5 -tetramethyl-1 , 3,2-dioxaborolan-2-yl ) -9 H -carbazole (70.57 g, 191.09 mmol), Pd (PPh 3) 4 (6.62 g, 5.73 mmol), K 2 CO 3 (79.23 g, 573.28 mmol), Water (425 ml) was added and stirred at 80 &lt; 0 &gt; C. After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 64.79 g (yield: 83%) of the product.

2. Sub 3-19 Synthetic example

The starting material, 4-bromo-9 H -carbazole ( 16.11 g, 65.46 mmol) in 9 - ([1,1'-biphenyl] -4-yl) -3- (4,4,5,5-tetramethyl-1 , 3,2-dioxaborolan-2-yl ) -9 H -carbazole (29.15 g, 65.46 mmol), Pd (PPh 3) 4 (2.27 g, 1.96 mmol), K 2 CO 3 (27.14 g, 196.38 mmol), THF (290 ml) and water (145 ml) were added, and 24.43 g of the product (yield: 77%) was obtained using the above Sub 3-1 synthesis method.

3. Sub 3-44 Synthetic example

The starting material, 4-bromo-9 H -carbazole ( 16.57 g, 67.33 mmol) to 9- (4- (2,6-diphenylpyridin- 4-yl) phenyl) -2- (4,4,5,5-tetramethyl -1,3,2-dioxaborolan-2-yl) -9 H -carbazole (40.30 g, 67.33 mmol), Pd (PPh 3) 4 (2.33 g, 2.02 mmol), K 2 CO 3 (27.91 g, 201.98 mmol ), THF (300 ml) and water (150 ml) were added, and 26.62 g (Yield: 62%) of the product was obtained using the Sub 3-1 synthesis method.

4. Sub 3-46 Synthetic example

To the starting material, 1-bromo-9 H -carbazole (17.21 g, 69.93 mmol) was added 9- (naphthalen-2-yl) -1- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl) -9 H -carbazole ( 29.32 g, 69.93 mmol), Pd (PPh 3) 4 (2.42 g, 2.10 mmol), K 2 CO 3 (28.99 g, 209.78 mmol), THF (300 ml), water (150 ml) was added, and 18.60 g (yield: 58%) of the product was obtained using the Sub 3-1 synthesis method.

5. Sub 3-57 Synthetic example

To the starting material, 3-bromo-9 H -carbazole (20.53 g, 83.42 mmol) was added 9 - ([1,1'-biphenyl] -3-yl) -1- (4,4,5,5-tetramethyl- , 3,2-dioxaborolan-2-yl ) -9 H -carbazole (37.15 g, 83.42 mmol), Pd (PPh 3) 4 (2.89 g, 2.50 mmol), K 2 CO 3 (34.59 g, 250.25 mmol), THF (370 ml) and water (185 ml) were added, and 21.83 g of the product (yield: 54%) was obtained using the above Sub 3-1 synthesis method.

6. Sub 3-62 Synthetic example

The starting material, 2-bromo-9 H -carbazole ( 13.78 g, 55.99 mmol) in 9 - ([1,1'-biphenyl] -4-yl) -2- (4,4,5,5-tetramethyl-1 , 3,2-dioxaborolan-2-yl ) -9 H -carbazole (24.94 g, 55.99 mmol), Pd (PPh 3) 4 (1.94 g, 1.68 mmol), K 2 CO 3 (23.21 g, 167.97 mmol), THF (250 ml) and water (125 ml) were added, and 23.06 g (Yield: 85%) of the product was obtained using the above Sub 3-1 synthesis method.

7. Sub 3-74 Synthetic example

The starting material, 2-bromo-9 H -carbazole ( 19.10 g, 77.61 mmol) in 9 - ([1,1'-biphenyl] -3-yl) -3- (4,4,5,5-tetramethyl-1 , 3,2-dioxaborolan-2-yl ) -9 H -carbazole (34.56 g, 77.61 mmol), Pd (PPh 3) 4 (2.69 g, 2.33 mmol), K 2 CO 3 (32.18 g, 232.82 mmol), THF (340 ml) and water (170 ml) were added, and 33.10 g (Yield: 88%) of the product was obtained using the Sub 3-1 synthesis method.

8. Sub 3-92 Synthetic example

The starting material, 4-bromo-9 H -carbazole 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [4,5] in (15.12 g, 61.44 mmol) thieno [2,3-c] pyridine ( 19.12 g, 61.44 mmol), Pd (PPh 3) 4 (2.13 g, 1.84 mmol), K 2 CO 3 (25.47 g, 184.31 mmol), THF (270 ml), water (140 ml) was added, and 14.86 g (yield: 69%) of the product was obtained using the above Sub 3-1 synthesis method.

9. Sub 3-96 Synthetic example

The starting material, 1-bromo-9 H -carbazole ( 16.61 g, 67.49 mmol) 2- (9,9-diphenyl-9 H -fluoren-4-yl) to -4,4,5,5-tetramethyl-1, 3,2-dioxaborolane (29.99 g, 67.49 mmol), Pd (PPh 3) 4 (2.34 g, 2.02 mmol), K 2 CO 3 (27.98 g, 202.47 mmol), THF (300 ml), water (150 ml) And 24.81 g (yield: 76%) of the product was obtained using the above Sub 3-1 synthesis method.

10. Sub 3-112 Synthetic example

The starting material, 3-bromo-9 H -carbazole ( 18.40 g, 74.76 mmol) in 2- (dibenzo [b, d] thiophen-3-yl) -4,4,5,5-tetramethyl-1,3,2 -dioxaborolane (23.19 g, 74.76 mmol) , Pd (PPh 3) 4 (2.59 g, 2.24 mmol), K 2 CO 3 (31.00 g, 224.29 mmol), was added to THF (320 ml), water (160 ml) and 21.42 g (yield: 82%) of the product was obtained using the above Sub 3-1 synthesis method.

11. Sub 3-113 Synthetic example

The starting material, 3-bromo-9 H -carbazole ( 17.19 g, 69.85 mmol) in 2- (dibenzo [b, d] furan-3-yl) -4,4,5,5-tetramethyl-1,3,2 -dioxaborolane (20.55 g, 69.85 mmol) , Pd (PPh 3) 4 (2.42 g, 2.10 mmol), K 2 CO 3 (28.96 g, 209.54 mmol), was added to THF (300 ml), water (150 ml) and 18.63 g (Yield: 80%) of the product was obtained using the above Sub 3-1 synthesis method.

The compound belonging to Sub 3 may be, but not limited to, the following compounds, and Table 1 shows FD-MS (Field Desorption-Mass Spectrometry) values of some compounds belonging to Sub 3.

compound FD-MS compound FD-MS Sub 3-1 _{m / z = 408.16 (C 30} H 20 N 2 = 408.50) Sub 3-2 m / z = 427.15 (C ₂₉ H ₁₈ FN ₃ = 427.48) Sub 3-3 _{m / z = 458.18 (C 34} H 22 N 2 = 458.56) Sub 3-4 _{m / z = 458.18 (C 34} H 22 N 2 = 458.56) Sub 3-5 _{m / z = 484.19 (C 36} H 24 N 2 = 484.60 Sub 3-6 _{m / z = 484.19 (C 36} H 24 N 2 = 484.60 Sub 3-7 m / z = 534.21 (C ₄₀ H ₂₆ N ₂ = 534.66) Sub 3-8 m / z = 524.23 (C ₃₉ H ₂₈ N ₂ = 524.67) Sub 3-9 _{m / z = 514.15 (C 36} H 22 N 2 S = 514.65) Sub 3-10 _{m / z = 484.19 (C 36} H 24 N 2 = 484.60 Sub 3-11 _{m / z = 485.19 (C 35} H 23 N 3 = 485.59) Sub 3-12 m / z = 561.22 (C ₄₁ H ₂₇ N ₃ = 561.69) Sub 3-13 _{m / z = 458.18 (C 34} H 22 N 2 = 458.56) Sub 3-14 m / z = 513.23 (C ₃₈ H ₁₉ D ₅ N ₂ = 513.65) Sub 3-15 m / z = 598.20 (C ₄₄ H ₂₆ N ₂ O = 598.71) Sub 3-16 m / z = 534.21 (C ₄₀ H ₂₆ N ₂ = 534.66) Sub 3-17 _{m / z = 408.16 (C 30} H 20 N 2 = 408.50) Sub 3-18 _{m / z = 458.18 (C 34} H 22 N 2 = 458.56) Sub 3-19 _{m / z = 484.19 (C 36} H 24 N 2 = 484.60 Sub 3-20 m / z = 574.20 (C ₄₂ H ₂₆ N ₂ O = 574.68) Sub 3-21 m / z = 561.22 (C ₄₁ H ₂₇ N ₃ = 561.69) Sub 3-22 m / z = 558.21 (C ₄₂ H ₂₆ N ₂ = 558.68) Sub 3-23 m / z = 690.34 (C ₄₉ H ₄₆ N ₂ Si = 691.01) Sub 3-24 m / z = 644.20 (C ₄₄ H ₂₈ N ₄ S = 644.80) Sub 3-25 _{m / z = 408.16 (C 30} H 20 N 2 = 408.50) Sub 3-26 m / z = 534.21 (C ₄₀ H ₂₆ N ₂ = 534.66) Sub 3-27 m / z = 558.21 (C ₄₂ H ₂₆ N ₂ = 558.68) Sub 3-28 _{m / z = 408.16 (C 30} H 20 N 2 = 408.50) Sub 3-29 _{m / z = 458.18 (C 34} H 22 N 2 = 458.56) Sub 3-30 _{m / z = 509.19 (C 37} H 23 N 3 = 509.61) Sub 3-31 m / z 514.15 (C ₃₆ H ₂₂ N ₂ S = 514.65) Sub 3-32 m / z = 584.23 (C ₄₄ H ₂₈ N ₂ = 584.72) Sub 3-33 m / z = 590.18 (C ₄₂ H ₂₆ N ₂ S = 590.74) Sub 3-34 m / z = 590.18 (C ₄₂ H ₂₆ N ₂ S = 590.74) Sub 3-35 m / z = 646.24 (C ₄₉ H ₃₀ N ₂ = 646.79) Sub 3-36 m / z = 534.21 (C ₄₀ H ₂₆ N ₂ = 534.66) Sub 3-37 m / z = 561.22 (C ₄₁ H ₂₇ N ₃ = 561.69) Sub 3-38 _{m / z = 458.18 (C 34} H 22 N 2 = 458.56) Sub 3-39 m / z = 558.21 (C ₄₂ H ₂₆ N ₂ = 558.68) Sub 3-40 m / z = 560.23 (C ₄₂ H ₂₈ N ₂ = 560.70) Sub 3-41 _{m / z = 408.16 (C 30} H 20 N 2 = 408.50) Sub 3-42 _{m / z = 413.19 (C 30} H 15 D 5 N 2 = 413.53) Sub 3-43 _{m / z = 408.16 (C 30} H 20 N 2 = 408.50) Sub 3-44 m / z = 637.25 (C ₄₇ H ₃₁ N ₃ = 637.79) Sub 3-45 m / z = 586.22 (C ₄₂ H ₂₆ N ₄ = 586.70) Sub 3-46 _{m / z = 458.18 (C 34} H 22 N 2 = 458.56) Sub 3-47 _{m / z = 484.19 (C 36} H 24 N 2 = 484.60 Sub 3-48 m / z = 534.21 (C ₄₀ H ₂₆ N ₂ = 534.66) Sub 3-49 m / z = 650.24 (C ₄₈ H ₃₀ N ₂ O = 650.78) Sub 3-50 m / z = 610.24 (C ₄₆ H ₃₀ N ₂ = 610.76) Sub 3-51 _{m / z = 408.16 (C 30} H 20 N 2 = 408.50) Sub 3-52 m / z = 534.21 (C ₄₀ H ₂₆ N ₂ = 534.66) Sub 3-53 m / z = 635.24 (C ₄₇ H ₂₉ N ₃ = 635.77) Sub 3-54 _{m / z = 537.20 (C 37} H 23 N 5 = 537.63) Sub 3-55 _{m / z = 458.18 (C 34} H 22 N 2 = 458.56) Sub 3-56 _{m / z = 408.16 (C 30} H 20 N 2 = 408.50) Sub 3-57 _{m / z = 484.19 (C 36} H 24 N 2 = 484.60 Sub 3-58 m / z = 508.19 (C ₃₈ H ₂₄ N ₂ = 508.62) Sub 3-59 _{m / z = 484.19 (C 36} H 24 N 2 = 484.60 Sub 3-60 m / z = 638.25 (C ₄₆ H ₃₀ N ₄ = 638.77) Sub 3-61 _{m / z = 408.16 (C 30} H 20 N 2 = 408.50) Sub 3-62 _{m / z = 484.19 (C 36} H 24 N 2 = 484.60 Sub 3-63 m / z = 508.19 (C ₃₈ H ₂₄ N ₂ = 508.62) Sub 3-64 m / z = 560.23 (C ₄₂ H ₂₈ N ₂ = 560.70) Sub 3-65 m / z = 818.25 (C ₅₈ H ₃₄ N ₄ S = 819.00) Sub 3-66 _{m / z = 408.16 (C 30} H 20 N 2 = 408.50) Sub 3-67 _{m / z = 458.18 (C 34} H 22 N 2 = 458.56) Sub 3-68 _{m / z = 484.19 (C 36} H 24 N 2 = 484.60 Sub 3-69 _{m / z = 484.19 (C 36} H 24 N 2 = 484.60 Sub 3-70 m / z = 534.21 (C ₄₀ H ₂₆ N ₂ = 534.66) Sub 3-71 m / z = 548.19 (C ₄₀ H ₂₄ N ₂ O = 548.65) Sub 3-72 m / z = 715.27 (C ₅₁ H ₃₃ N ₅ = 715.86) Sub 3-73 _{m / z = 408.16 (C 30} H 20 N 2 = 408.50) Sub 3-74 _{m / z = 484.19 (C 36} H 24 N 2 = 484.60 Sub 3-75 _{m / z = 459.17 (C 33} H 21 N 3 = 459.55) Sub 3-76 m / z = 610.24 (C ₄₆ H ₃₀ N ₂ = 610.76) Sub 3-77 m / z = 638.25 (C ₄₆ H ₃₀ N ₄ = 638.77) Sub 3-78 _{m / z = 459.17 (C 33} H 21 N 3 = 459.55) Sub 3-79 m / z = 508.19 (C ₃₈ H ₂₄ N ₂ = 508.62) Sub 3-80 m / z = 662.25 (C ₄₈ H ₃₀ N ₄ = 662.80) Sub 3-81 _{m / z = 658.24 (C 50} H 30 N 2 = 658.80) Sub 3-82 m / z = 700.29 (C ₅₃ H ₃₆ N ₂ = 700.89) Sub 3-83 m / z = 349.09 (C ₂₄ H ₁₅ NS = 349.45) Sub 3-84 m / z = 333.12 (C ₂₄ H ₁₅ NO = 333.39) Sub 3-85 _{m / z = 409.15 (C 30} H 19 NO = 409.49) Sub 3-86 m / z = 607.23 (C ₄₇ H ₂₉ N = 607.76) Sub 3-87 m / z = 349.09 (C ₂₄ H ₁₅ NS = 349.45) Sub 3-88 _{m / z = 483.20 (C 37} H 25 N = 483.61) Sub 3-89 m / z = 333.12 (C ₂₄ H ₁₅ NO = 333.39) Sub 3-90 m / z = 580.17 (C ₃₉ H ₂₄ N ₄ S = 580.71) Sub 3-91 _{m / z = 399.11 (C 28} H 17 NS = 399.51) Sub 3-92 _{m / z = 350.09 (C 23} H 14 N 2 S = 350.44) Sub 3-93 m / z = 433.15 (C ₃₂ H ₁₉ NO = 433.51) Sub 3-94 _{m / z = 458.18 (C 34} H 22 N 2 = 458.56) Sub 3-95 m / z = 541.19 (C ₃₉ H ₂₇ NS = 541.71) Sub 3-96 _{m / z = 483.20 (C 37} H 25 N = 483.61) Sub 3-97 _{m / z = 399.11 (C 28} H 17 NS = 399.51) Sub 3-98 m / z = 333.12 (C ₂₄ H ₁₅ NO = 333.39) Sub 3-99 _{m / z = 503.15 (C 34} H 21 N 3 S = 503.62) Sub 3-100 _{m / z = 435.14 (C 30} H 17 N 3 O = 435.49) Sub 3-101 _{m / z = 481.18 (C 37} H 23 N = 481.60) Sub 3-102 m / z = 459.16 (C ₃₄ H ₂₁ NO = 459.55) Sub 3-103 m / z = 475.14 (C ₃₄ H ₂₁ NS = 475.61) Sub 3-104 m / z = 359.17 (C ₂₇ H ₂₁ N = 359.47) Sub 3-105 m / z = 428.11 (C ₂₇ H ₁₆ N ₄ S = 428.51) Sub 3-106 m / z = 333.12 (C ₂₄ H ₁₅ NO = 333.39) Sub 3-107 m / z = 349.09 (C ₂₄ H ₁₅ NS = 349.45) Sub 3-108 m / z = 333.12 (C ₂₄ H ₁₅ NO = 333.39) Sub 3-109 m / z = 449.12 (C ₃₂ H ₁₉ NS = 449.57) Sub 3-110 m / z = 359.17 (C ₂₇ H ₂₁ N = 359.47) Sub 3-111 m / z = 483.16 (C ₃₆ H ₂₁ NO = 483.57) Sub 3-112 m / z = 349.09 (C ₂₄ H ₁₅ NS = 349.45) Sub 3-113 m / z = 333.12 (C ₂₄ H ₁₅ NO = 333.39) Sub 3-114 _{m / z = 459.20 (C 35} H 25 N = 459.59) Sub 3-115 m / z = 656.20 (C ₄₅ H ₂₈ N ₄ S = 656.81) Sub 3-116 m / z = 533.21 (C ₄₁ H ₂₇ N = 533.67)

II. Synthesis of Sub 4

Sub 4 of Reaction Scheme 2 is synthesized by the reaction path of Reaction Scheme 4 below, but is not limited thereto. Wherein Hal ¹ and Hal ² are Br or Cl.

<Reaction Scheme 4>

1. Sub 4-37 Synthetic example

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

2. Sub 4-46 Synthetic example

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

3. Sub 4-68 Synthetic example

(1) Sub 4-I-68 synthesis

The starting material, 1-amino-2-naphthoic acid (CAS Registry Number: 4919-43-1) (75.11 g, 401.25 mmol) was added to a round bottom flask with urea (CAS Registry Number: 57-13-6) 2808.75 mmol) and stirred at 160 &lt; 0 &gt; C. After confirming the reaction by TLC, the reaction mixture was cooled to 100 DEG C, water (200 ml) was added, and the mixture was stirred for 1 hour. After completion of the reaction, the resulting solid was filtered under reduced pressure, washed with water, and then dried to obtain 63.86 g (yield: 75%) of the product.

(2) Sub 4-II-68 Synthesis

N , N- Diisopropylethylamine (97.23 g, 752.36 mmol) was slowly added dropwise to the round bottom flask of Sub 4-I-68 (63.86 g, 300.94 mmol) obtained in the above synthesis by dissolving POCl ₃ Then, the mixture was stirred at 90 ° C. After completion of the reaction, the reaction mixture was concentrated, and then ice water (500 ml) was added thereto, followed by stirring at room temperature for 1 hour. The resulting solid was filtered under reduced pressure and dried to obtain 67.47 g (yield: 90%) of the product.

(3) Sub 4-68 Synthesis

4,4,5,5-tetramethyl-2- (naphthalen-1-yl) -1,3,2-dioxaborolane (CAS Registry Number: 68716-52-9) (30.36 g, 119.45 mmol ), Pd (PPh 3) 4 (5.02 g, 4.34 mmol), K ₂ CO ₃ (45.03 g, 325.79 mmol), THF (380 ml) and water (190 ml) %).

4. Sub 4-86 Synthetic example

The starting material, 2,4-dichlorobenzo [4,5] thieno [3,2- d ] pyrimidine (CAS Registry Number: 160199-05-3) (38.00 g, 148.95 mmol) -2-phenyl-1,3,2-dioxaborolane ( CAS Registry Number: 24388-23-6) (33.44 g, 163.84 mmol), Pd (PPh 3) 4 (6.88 g, 5.96 mmol), K 2 CO 3 ( 61.76 g, 446.85 mmol), THF (520 ml) and water (260 ml) were added, and 17.68 g (Yield: 40%) of the product was obtained using the Sub 4-37 synthesis method.

5. Sub 4-88 Synthetic example

(Dibenzo [b, d] pyrimidin-2-one) was added to the starting material 2,4-dichlorobenzo [4,5] thieno [3,2- d ] pyrimidine (CAS Registry Number: 160199-05-3) (35.15 g, 137.78 mmol) (CAS Registry furan-2-yl ) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane Number: 947770-80-1) (44.58 g, 151.56 mmol), Pd (PPh 3) 4 (6.37 g, 5.51 mmol), K 2 CO 3 (57.13 g, 413.33 mmol), THF (480 ml), was added water (240 ml) and the product 22.92 using the Sub 4-37 Synthesis g (yield: 43 %).

6. Sub 4-92 Synthetic example

4,4,5,5-tetramethyl-2-phenyl-1 (4,4,5,5-tetramethylpiperidine) was added to the starting material, 2,4- dichlorobenzofuro [2,3-d] pyrimidine (CAS Registry Number: 1801325-92-7) , 3,2-dioxaborolane (CAS Registry Number : 24388-23-6) (38.90 g, 190.63 mmol), Pd (PPh 3) 4 (8.01 g, 6.93 mmol), K 2 CO 3 (71.86 g, 519.91 mmol) , THF (600 ml) and water (300 ml) were added, and 18.49 g (yield: 38%) of the product was obtained using the Sub 4-37 synthesis method described above.

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

compound FD-MS compound FD-MS Sub 4-1 _{m / z = 155.96 (C 6} H 5 Br = 157.01) Sub 4-2 _{m / z = 312.09 (C 15} H 25 BrSi = 313.35) Sub 4-3 _{m / z = 173.95 (C 6} H 4 BrF = 175.00) Sub 4-4 m / z = 160.99 (C ₆ D ₅ Br = 162.04) Sub 4-5 _{m / z = 205.97 (C 10} H 7 Br = 207.07) Sub 4-6 _{m / z = 205.97 (C 10} H 7 Br = 207.07) Sub 4-7 m / z = 231.99 (C ₁₂ H ₉ Br = 233.11) Sub 4-8 m / z = 241.05 (C ₁₂ D ₉ Br = 242.16) Sub 4-9 m / z = 231.99 (C ₁₂ H ₉ Br = 233.11) Sub 4-10 _{m / z = 308.02 (C 18} H 13 Br = 309.21) Sub 4-11 _{m / z = 308.02 (C 18} H 13 Br = 309.21) Sub 4-12 m / z = 282.00 (C ₁₆ H ₁₁ Br = 283.17) Sub 4-13 m / z = 282.00 (C ₁₆ H ₁₁ Br = 283.17) Sub 4-14 m / z = 282.00 (C ₁₆ H ₁₁ Br = 283.17) Sub 4-15 m / z = 282.00 (C ₁₆ H ₁₁ Br = 283.17) Sub 4-16 m / z = 282.00 (C ₁₆ H ₁₁ Br = 283.17) Sub 4-17 _{m / z = 255.99 (C 14} H 9 Br = 257.13) Sub 4-18 _{m / z = 255.99 (C 14} H 9 Br = 257.13) Sub 4-19 _{m / z = 306.00 (C 18} H 11 Br = 307.19) Sub 4-20 m / z = 279.99 (C ₁₆ H ₉ Br = 281.15) Sub 4-21 m / z = 245.97 (C ₁₂ H ₇ BrO = 247.09) Sub 4-22 m / z = 261.95 (C ₁₂ H ₇ BrS = 263.15) Sub 4-23 m / z = 261.95 (C ₁₂ H ₇ BrS = 263.15) Sub 4-24 _{m / z = 295.98 (C 16} H 9 BrO = 297.15) Sub 4-25 _{m / z = 322.00 (C 18} H 11 BrO = 323.19) Sub 4-26 _{m / z = 272.02 (C 15} H 13 Br = 273.17) Sub 4-27 _{m / z = 396.05 (C 25} H 17 Br = 397.32) Sub 4-28 _{m / z = 394.04 (C 25} H 15 Br = 395.30) Sub 4-29 _{m / z = 322.04 (C 19} H 15 Br = 322.04) Sub 4-30 _{m / z = 321.02 (C 18} H 12 BrN = 322.21) Sub 4-31 _{m / z = 319.00 (C 18} H 10 BrN = 320.19) Sub 4-32 _{m / z = 309.02 (C 17} H 12 BrN = 310.19) Sub 4-33 _{m / z = 309.02 (C 17} H 12 BrN = 310.19) Sub 4-34 m / z = 385.05 (C ₂₃ H ₁₆ BrN = 386.29) Sub 4-35 _{m / z = 371.94 (C 16} H 9 BrN 2 S 2 = 373.29) Sub 4-36 m / z = 310.01 (C ₁₆ H ₁₁ BrN ₂ = 311.18) Sub 4-37 m / z = 360.03 (C ₂₀ H ₁₃ BrN ₂ = 361.24) Sub 4-38 _{m / z = 386.04 (C 22} H 15 BrN 2 = 387.28) Sub 4-39 _{m / z = 526.10 (C 33} H 23 BrN 2 = 527.47) Sub 4-40 _{m / z = 416.00 (C 22} H 13 BrN 2 S = 417.32) Sub 4-41 _{m / z = 387.04 (C 21} H 14 BrN 3 = 388.27) Sub 4-42 m / z = 310.01 (C ₁₆ H ₁₁ BrN ₂ = 311.18) Sub 4-43 _{m / z = 562.10 (C 36} H 23 BrN 2 = 563.50) Sub 4-44 m / z = 360.03 (C ₂₀ H ₁₃ BrN ₂ = 361.24) Sub 4-45 _{m / z = 386.04 (C 22} H 15 BrN 2 = 387.28) Sub 4-46 _{m / z = 386.04 (C 22} H 15 BrN 2 = 387.28) Sub 4-47 m / z = 310.01 (C ₁₆ H ₁₁ BrN ₂ = 311.18) Sub 4-48 m / z = 240.02 (C ₁₂ H ₅ ClN ₄ = 240.65) Sub 4-49 _{m / z = 284.99 (C 13} H 8 BrN 3 = 286.13) Sub 4-50 _{m / z = 311.01 (C 15} H 10 BrN 3 = 312.17) Sub 4-51 _{m / z = 361.02 (C 19} H 12 BrN 3 = 362.23) Sub 4-52 _{m / z = 411.04 (C 23} H 14 BrN 3 = 412.29) Sub 4-53 _{m / z = 411.04 (C 23} H 14 BrN 3 = 412.29) Sub 4-54 _{m / z = 397.10 (C 21} H 4 D 10 BrN 3 = 398.33) Sub 4-55 _{m / z = 437.05 (C 25} H 16 BrN 3 = 438.33) Sub 4-56 m / z = 511.07 (C ₃₁ H ₁₈ BrN ₃ = 512.41) Sub 4-57 _{m / z = 416.99 (C 21} H 12 BrN 3 S = 418.31) Sub 4-58 _{m / z = 451.03 (C 25} H 14 BrN 3 O = 452.31) Sub 4-59 m / z = 507.00 (C ₂₇ H ₁₄ BrN ₃ OS = 508.39) Sub 4-60 _{m / z = 387.04 (C 21} H 14 BrN 3 = 388.27) Sub 4-61 _{m / z = 240.05 (C 14} H 9 ClN 2 = 240.69) Sub 4-62 m / z = 297.11 (C ₁₈ H ₄ D ₇ ClN ₂ = 297.79) Sub 4-63 _{m / z = 291.06 (C 17} H 10 ClN 3 = 291.74) Sub 4-64 _{m / z = 316.08 (C 20} H 13 ClN 2 = 316.79) Sub 4-65 _{m / z = 346.03 (C 20} H 11 ClN 2 S = 346.83) Sub 4-66 _{m / z = 341.07 (C 21} H 12 ClN 3 = 341.80) Sub 4-67 _{m / z = 290.06 (C 18} H 11 ClN 2 = 290.75) Sub 4-68 _{m / z = 340.08 (C 22} H 13 ClN 2 = 340.81) Sub 4-69 m / z = 366.09 (C ₂₄ H ₁₅ ClN ₂ = 366.85) Sub 4-70 m / z = 396.05 (C ₂₄ H ₁₃ ClN ₂ S = 396.89) Sub 4-71 m / z = 406.09 (C ₂₆ H ₁₅ ClN ₂ O = 406.87) Sub 4-72 m / z = 360.03 (C ₂₀ H ₁₃ BrN ₂ = 361.24) Sub 4-73 m / z = 182.00 (C ₈ H ₄ ClFN ₂ = 182.58) Sub 4-74 _{m / z = 240.05 (C 14} H 9 ClN 2 = 240.69) Sub 4-75 _{m / z = 290.06 (C 18} H 11 ClN 2 = 290.75) Sub 4-76 _{m / z = 316.08 (C 20} H 13 ClN 2 = 316.79) Sub 4-77 _{m / z = 346.03 (C 20} H 11 ClN 2 S = 346.83) Sub 4-78 m / z = 406.09 (C ₂₆ H ₁₅ ClN ₂ O = 406.87) Sub 4-79 _{m / z = 340.08 (C 22} H 13 ClN 2 = 340.81) Sub 4-80 m / z = 366.09 (C ₂₄ H ₁₅ ClN ₂ = 366.85) Sub 4-81 _{m / z = 340.08 (C 22} H 13 ClN 2 = 340.81) Sub 4-82 m / z = 390.09 (C ₂₆ H ₁₅ ClN ₂ = 390.87) Sub 4-83 m / z = 360.03 (C ₂₀ H ₁₃ BrN ₂ = 361.24) Sub 4-84 m / z = 360.03 (C ₂₀ H ₁₃ BrN ₂ = 361.24) Sub 4-85 _{m / z = 240.05 (C 14} H 9 ClN 2 = 240.69) Sub 4-86 m / z = 296.02 (C ₁₆ H ₉ ClN ₂ S = 296.77) Sub 4-87 _{m / z = 346.03 (C 20} H 11 ClN 2 S = 346.83) Sub 4-88 _{m / z = 386.03 (C 22} H 11 ClN 2 OS = 386.85) Sub 4-89 _{m / z = 386.03 (C 22} H 11 ClN 2 OS = 386.85) Sub 4-90 _{m / z = 357.07 (C 21} H 12 ClN 3 O = 357.80) Sub 4-91 m / z = 396.05 (C ₂₄ H ₁₃ ClN ₂ S = 396.89) Sub 4-92 m / z = 280.04 (C ₁₆ H ₉ ClN ₂ O = 280.71) Sub 4-93 _{m / z = 330.06 (C 20} H 11 ClN 2 O = 330.77) Sub 4-94 _{m / z = 396.10 (C 25} H 17 ClN 2 O = 396.87) Sub 4-95 _{m / z = 356.11 (C 23} H 17 ClN 2 = 356.85) Sub 4-96 m / z = 270.00 (C14H7ClN2S = 270.73) Sub 4-97 _{m / z = 456.10 (C 30} H 17 ClN 2 O = 456.93) Sub 4-98 _{m / z = 421.03 (C 22} H 8 D 5 BrN 2 S = 422.35) Sub 4-99 _{m / z = 416.00 (C 22} H 13 BrN 2 S = 417.32) Sub4-100 _{m / z = 350.04 (C 19} H 15 BrN 2 = 351.25) Sub4-101 _{m / z = 386.03 (C 22} H 11 ClN 2 OS = 386.85) Sub4-102 m / z = 296.02 (C ₁₆ H ₉ ClN ₂ S = 296.77) Sub4-103 m / z = 280.04 (C ₁₆ H ₉ ClN ₂ O = 280.71) Sub4-104 m / z = 280.04 (C ₁₆ H ₉ ClN ₂ O = 280.71) Sub4-105 m / z = 380.07 (C ₂₄ H ₁₃ ClN ₂ O = 380.83) Sub4-106 _{m / z = 219.99 (C 10} H 5 ClN 2 S = 220.67) Sub4-107 _{m / z = 306.06 (C 18} H 11 ClN 2 O = 306.75) Sub4-108 m / z = 237.95 (C ₁₀ H ₇ BrS = 239.13) Sub4-109 m / z = 297.02 (C ₁₆ H ₁₂ BrN = 298.18) Sub4-110 _{m / z = 228.05 (C 13} H 9 ClN 2 = 228.68) Sub4-111 m / z = 257.98 (C ₁₂ H ₇ BrN ₂ = 259.11)

III. Final Product 2 Composite

After Sub 3 (1 eq.) Was dissolved in toluene in a round bottom flask, Sub 4 (1.1 eq.), Pd ₂ (dba) ₃ (0.03 eq.), ( T- Bu) ₃ P (0.06 eq.) And NaO t- Bu (3 eq.) Were stirred at 100 &lt; 0 &gt; C. After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain final product 2.

1. 2-2 Synthetic example

The Sub 3-1 (8.62 g, 21.10 mmol) obtained in the above synthesis was dissolved in toluene (220 ml) in a round bottom flask and Sub 4-11 (CAS Registry Number: 1762-84-1) (7.18 g, 23.21 mmol ), Pd ₂ (dba) ₃ (0.58 g, 0.63 mmol), P ( t- Bu) ₃ (0.26 g, 1.27 mmol) and NaO t- Bu (6.08 g, 63.30 mmol) . After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 10.62 g (yield: 79%) of the product.

2. 2-3 Synthetic example

Sub 4-30 (CAS Registry Number: 94994-62-4) (6.50 g, 20.17 mmol) and Pd ₂ (dba) ₃ (0.50 g, 0.55 mmol) were added to Sub 3-1 (7.49 g, 18.34 mmol) mmol), P ( t- Bu) ₃ (0.22 g, 1.10 mmol), NaO t- Bu (5.29 g, 55.01 mmol) and toluene (195 ml) : 84%).

3. 2-4 Synthetic example

Sub-4-50 (CAS Registry Number: 80984-79-8) (6.35 g, 20.33 mmol), Pd ₂ (dba) ₃ (0.51 g, 0.55 mmol) P ( t- Bu) ₃ (0.22 g, 1.11 mmol), NaO t- Bu (5.33 g, 55.45 mmol) and toluene (195 ml) were added and 10.17 g : 86%).

4. 2-10 Synthetic example

(CAS Registry Number: 29874-83-7) (5.25 g, 21.81 mmol), Pd ₂ (dba) ₃ (0.54 g, 0.59 mmol) was added to Sub 3-1 (8.10 g, 19.83 mmol) mmol) P ( t- Bu) ₃ (0.24 g, 1.19 mmol), NaO t- Bu (5.72 g, 59.49 mmol) and toluene (210 ml) : 81%).

5. 2-14 Synthetic example

Sub-4-74 (CAS Registry Number: 7065-92-1) (6.44 g, 26.74 mmol) and Pd ₂ (dba) ₃ (0.67 g, 0.73 mmol) were added to Sub 3-1 (9.93 g, 24.31 mmol) _{mmol) P (t -Bu) 3} (0.30 g, 1.46 mmol), NaO t -Bu (7.01 g, 72.93 mmol), toluene ( 255 ml was added) and the product using the synthetic method 2-2 9.98 g (yield : 67%).

6. 2-19 Synthetic example

Obtained in the above Synthesis Sub 3-1 (6.44 g, 15.76 mmol ) in Sub 4-86 (5.15 g, 17.34 mmol ), Pd 2 (dba) 3 (0.43 g, 0.47 mmol) P (t -Bu) 3 (0.19 g, 0.95 mmol), NaO t- Bu (4.55 g, 47.29 mmol) and toluene (165 ml) were added and the product was obtained by the above 2-2 synthesis method to obtain 8.96 g (yield: 85%).

7. 2-31 Synthetic example

Sub-4-74 (CAS Registry Number: 7065-92-1) (5.62 g, 23.33 mmol) and Pd ₂ (dba) ₃ (0.58 g, 0.64 mmol) were added to Sub 3-19 (10.28 g, 21.21 mmol) mmol) P ( t- Bu) ₃ (0.26 g, 1.27 mmol), NaO t- Bu (6.12 g, 63.64 mmol) and toluene (225 ml) were added and 9.35 g : 64%).

8. 2-54 Synthetic example

Sub-4-36 (CAS Registry Number: 56181-49-8) (4.89 g, 15.73 mmol) and Pd ₂ (dba) ₃ (0.39 g, 0.43 mmol) were added to Sub 3-44 mmol) P ( t- Bu) ₃ (0.17 g, 0.86 mmol), NaO t- Bu (4.12 g, 42.90 mmol) and toluene (150 ml) : 70%).

9. 2-60 Synthetic example

P ( t- Bu) ₃ (0.25 g, 0.62 mmol) and Pd ₂ (dba) ₃ (6.36 g, 22.67 mmol) were added to Sub 3-46 (9.45 g, 20.61 mmol) g, 1.24 mmol), NaO t- Bu (5.94 g, 61.82 mmol) and toluene (215 ml) were added and the product was obtained using 9.2 g (yield: 63%).

10. 2-67 Synthetic example

Sub-4-51 (CAS Registry Number: 2011776-79-5) (6.82 g, 18.84 mmol) and Pd ₂ (dba) ₃ (0.47 g, 0.51 mmol) were added to Sub 3-57 (8.30 g, 17.13 mmol) _{mmol) P (t -Bu) 3} (0.21 g, 1.03 mmol), NaO t -Bu (4.94 g, 51.38 mmol), toluene ( addition of 180 ml) and the product using the 2-2 synthesis 10.36 g (yield: : 79%).

11. 2-73 Synthetic example

Sub-53 (CAS Registry Number: 1646152-18-2) (10.30 g, 24.99 mmol) and Pd ₂ (dba) ₃ (0.62 g, 0.68 mmol) were added to Sub 3-62 (11.01 g, 22.72 mmol) mmol), P ( t- Bu) ₃ (0.28 g, 1.36 mmol), NaO t- Bu (6.55 g, 68.16 mmol) and toluene (240 ml) : 68%).

12. 2-84 Synthetic example

Obtained in the above Synthesis Sub 3-74 (9.03 g, 18.63 mmol ) in Sub 4-37 (7.40 g, 20.50 mmol ), Pd 2 (dba) 3 (0.51 g, 0.56 mmol) P (t -Bu) 3 (0.23 g, 1.12 mmol), NaO t- Bu (5.37 g, 55.90 mmol) and toluene (195 ml) were added to the reaction mixture to obtain 12.40 g of the product (yield: 87%).

13. 2-112 Synthetic example

P ( t- Bu) ₃ (0.25 g, 0.62 mmol), Sub 4-68 (7.79 g, 22.85 mmol), Pd ₂ (dba) ₃ (0.57 g, 0.62 mmol) was added to Sub 3-92 (7.28 g, 20.77 mmol) g, 1.25 mmol), NaO t- Bu (5.99 g, 62.32 mmol) and toluene (220 ml) were added and the product 2.4 was used to obtain 8.43 g of the product (yield: 62%).

14. 2-116 Synthetic example

Sub-4-61 (CAS Registry Number: 29874-83-7) (5.51 g, 22.90 mmol) and Pd ₂ (dba) ₃ (0.57 g, 0.62 mmol) were added to Sub 3-96 (10.07 g, 20.82 mmol) mmol), P ( t- Bu) ₃ (0.25 g, 1.25 mmol), NaO t- Bu (6.00 g, 62.47 mmol) and toluene (220 ml) : 65%).

15. 2-131 Synthetic example

Obtained in the above Synthesis Sub 3-112 (8.83 g, 25.27 mmol ) in Sub 4-88 (10.75 g, 27.80 mmol ), Pd 2 (dba) 3 (0.69 g, 0.76 mmol) P (t -Bu) 3 (0.31 g, 1.52 mmol), NaO t- Bu (7.29 g, 75.80 mmol) and toluene (265 ml) were added and the product 2-2 was synthesized to obtain 12.73 g (yield: 72%) of the product.

16. 2-133 Synthetic example

P ( t- Bu) ₃ (0.25 g, 0.62 mmol) and Pd ₂ (dba) ₃ (8.74 g, 22.57 mmol) were added to Sub 3-113 (6.84 g, 20.52 mmol) g, 1.23 mmol), NaO t- Bu (5.92 g, 61.55 mmol) and toluene (215 ml) were added and the product 2.11 was used to obtain 10.11 g of the product (yield: 77%).

Meanwhile, the FD-MS values of the compounds 2-1 to 2-135 of the present invention prepared according to the above synthesis examples are shown in Table 3 below.

compound FD-MS compound FD-MS 2-1 m / z = 636.26 (C ₄₈ H ₃₂ N ₂ = 636.80) 2-2 m / z = 636.26 (C ₄₈ H ₃₂ N ₂ = 636.80) 2-3 m / z = 649.25 (C ₄₈ H ₃₁ N ₃ = 649.80) 2-4 m / z = 639.24 (C ₄₅ H ₂₉ N ₅ = 639.76) 2-5 m / z = 739.27 (C ₅₃ H ₃₃ N ₅ = 739.88) 2-6 m / z = 821.26 (C ₅₇ H ₃₅ N ₅ S = 822.00) 2-7 m / z = 854.34 (C ₆₃ H ₄₂ N ₄ = 855.06) 2-8 m / z = 909.33 (C ₆₅ H ₄₀ FN ₅ = 910.07) 2-9 m / z = 728.27 (C ₅₁ H ₃₂ N ₆ = 728.86) 2-10 m / z = 612.23 (C ₄₄ H ₂₈ N ₄ = 612.74) 2-11 m / z = 774.35 (C ₅₆ H ₂₂ D ₁₂ N ₄ = 774.99) 2-12 m / z = 908.26 (C ₆₄ H ₃₆ N ₄ OS = 909.08) 2-13 m / z = 738.28 (C ₅₄ H ₃₄ N ₄ = 738.89) 2-14 m / z = 612.23 (C ₄₄ H ₂₈ N ₄ = 612.74) 2-15 m / z = 738.28 (C ₅₄ H ₃₄ N ₄ = 738.89) 2-16 m / z = 868.27 (C ₆₂ H ₃₆ N ₄ S = 869.06) 2-17 m / z = 738.28 (C ₅₄ H ₃₄ N ₄ = 738.89) 2-18 m / z = 854.30 (C ₆₂ H ₃₈ N ₄ O = 855.01) 2-19 m / z = 668.20 (C ₄₆ H ₂₈ N ₄ S = 668.82) 2-20 m / z = 794.25 (C ₅₆ H ₃₄ N ₄ S = 794.98) 2-21 m / z = 845.32 (C ₆₀ H ₃₉ N ₅ O = 846.01) 2-22 m / z = 749.27 (C ₅₂ H ₂₇ D ₅ N ₄ S = 749.95) 2-23 m / z = 881.35 (C ₆₄ H ₄₃ N ₅ = 882.08) 2-24 m / z = 794.25 (C ₅₆ H ₃₄ N ₄ S = 794.98) 2-25 m / z = 765.29 (C ₅₅ H ₃₅ N ₅ = 765.92) 2-26 m / z = 874.33 (C ₆₇ H ₄₂ N ₂ = 875.09) 2-27 m / z = 897.29 (C ₆₃ H ₃₉ N ₅ S = 898.10) 2-28 m / z = 639.24 (C ₄₅ H ₂₉ N ₅ = 639.76) 2-29 m / z = 815.30 (C ₅₉ H ₃₇ N ₅ = 815.98) 2-30 m / z = 863.30 (C ₆₃ H ₃₇ N ₅ = 864.02) 2-31 m / z = 688.26 (C ₅₀ H ₃₂ N ₄ = 688.83) 2-32 m / z = 758.21 (C ₅₂ H ₃₀ N ₄ OS = 758.90) 2-33 m / z = 778.27 (C ₅₆ H ₃₄ N ₄ O = 778.92) 2-34 m / z = 715.27 (C ₅₁ H ₃₃ N ₅ = 715.86) 2-35 m / z = 924.30 (C ₆₄ H ₄₀ N ₆ S = 925.13) 2-36 m / z = 844.32 (C ₆₁ H ₄₀ N ₄ O = 845.02) 2-37 m / z = 882.41 (C ₆₂ H ₅₄ N ₄ Si = 883.23) 2-38 m / z = 736.29 (C ₅₆ H ₃₆ N ₂ = 736.92) 2-39 m / z = 739.27 (C ₅₃ H ₃₃ N ₅ = 739.88) 2-40 m / z = 820.27 (C ₅₈ H ₃₆ N ₄ S = 821.01) 2-41 m / z = 839.30 (C ₆₁ H ₃₇ N ₅ = 840.00) 2-42 m / z = 762.28 (C ₅₆ H ₃₄ N ₄ = 762.92) 2-43 _{m / z = 860.26 (C 60} H 36 N 4 OS = 861.04) 2-44 m / z = 824.21 (C ₅₆ H ₃₂ N ₄ S2 = 825.02) 2-45 m / z = 786.30 (C ₆₀ H ₃₈ N ₂ = 786.98) 2-46 m / z = 689.26 (C ₄₉ H ₃₁ N ₅ = 689.82) 2-47 m / z = 850.31 (C ₆₃ H ₃₈ N ₄ = 851.03) 2-48 m / z = 855.30 (C ₆₁ H ₃₇ N ₅ O = 856.00) 2-49 m / z = 791.30 (C ₅₇ H ₃₇ N ₅ = 791.96) 2-50 m / z = 870.28 (C ₆₂ H ₃₈ N ₄ S = 871.07) 2-51 m / z = 839.30 (C ₆₁ H ₃₇ N ₅ = 840.00) 2-52 m / z = 717.29 (C ₅₂ H ₂₇ D ₅ N ₄ = 717.89) 2-53 m / z = 828.29 (C ₆₀ H ₃₆ N ₄ O = 828.98) 2-54 m / z = 867.34 (C ₆₃ H ₄₁ N ₅ = 868.06) 2-55 m / z = 828.33 (C ₆₁ H ₄₀ N ₄ = 829.02) 2-56 _{m / z = 816.28 (C 60} H 36 N 2 O 2 = 816.96) 2-57 m / z = 739.27 (C ₅₃ H ₃₃ N ₅ = 739.88) 2-58 m / z = 890.34 (C ₆₆ H ₄₂ N ₄ = 891.09) 2-59 m / z = 844.27 (C ₆₀ H ₃₆ N ₄ S = 845.04) 2-60 m / z = 702.24 (C ₅₀ H ₃₀ N ₄ O = 702.82) 2-61 m / z = 698.31 (C ₄₉ H ₂₂ D ₉ N ₅ = 698.88) 2-62 m / z = 642.19 (C ₄₄ H ₂₆ N ₄ S = 642.78) 2-63 m / z = 835.24 (C ₅₇ H ₃₃ N ₅ OS = 835.99) 2-64 m / z = 826.22 (C ₅₆ H ₃₄ N ₄ S ₂ = 827.04) 2-65 m / z = 839.30 (C ₆₁ H ₃₇ N ₅ = 840.00) 2-66 m / z = 684.26 (C ₅₂ H ₃₂ N ₂ = 684.84) 2-67 m / z = 765.29 (C ₅₅ H ₃₅ N ₅ = 765.92) 2-68 m / z = 654.22 (C ₄₆ H ₂₇ FN ₄ = 654.75) 2-69 m / z = 758.21 (C ₅₂ H ₃₀ N ₄ OS = 758.90) 2-70 m / z = 855.34 (C ₆₂ H ₄₁ N ₅ = 856.05) 2-71 m / z = 684.26 (C ₅₂ H ₃₂ N ₂ = 684.84) 2-72 m / z = 778.27 (C ₅₆ H ₃₄ N ₄ O = 778.92) 2-73 m / z = 815.30 (C ₅₉ H ₃₇ N ₅ = 815.98) 2-74 m / z = 764.29 (C ₅₆ H ₃₆ N ₄ = 764.93) 2-75 m / z = 996.30 (C ₇₀ H ₄₀ N ₆ S = 997.19) 2-76 m / z = 560.23 (C ₄₂ H ₂₈ N ₂ = 560.70) 2-77 m / z = 714.28 (C ₅₂ H ₃₄ N ₄ = 714.87) 2-78 m / z = 647.24 (C ₄₈ H ₂₉ N ₃ = 647.78) 2-79 m / z = 814.31 (C ₆₀ H ₃₈ N ₄ = 814.99) 2-80 m / z = 790.31 (C ₅₈ H ₃₈ N ₄ = 790.97) 2-81 m / z = 639.24 (C ₄₅ H ₂₉ N ₅ = 639.76) 2-82 m / z = 801.37 (C ₅₇ H ₂₇ D ₁₀ N ₅ = 802.02) 2-83 m / z = 639.24 (C ₄₅ H ₂₉ N ₅ = 639.76) 2-84 m / z = 764.29 (C ₅₆ H ₃₆ N ₄ = 764.93) 2-85 m / z = 830.28 (C ₅₈ H ₃₄ N ₆ O = 830.95) 2-86 m / z = 738.28 (C ₅₄ H ₃₄ N ₄ = 738.89) 2-87 m / z = 612.23 (C ₄₄ H ₂₈ N ₄ = 612.74) 2-88 m / z = 712.26 (C ₅₂ H ₃₂ N ₄ = 712.86) 2-89 _{m / z = 718.22 (C 50} H 30 N 4 S = 718.88) 2-90 m / z = 764.29 (C ₅₆ H ₃₆ N ₄ = 764.93) 2-91 _{m / z = 718.22 (C 50} H 30 N 4 S = 718.88) 2-92 m / z = 844.27 (C ₆₀ H ₃₆ N ₄ S = 845.04) 2-93 m / z = 892.28 (C ₆₄ H ₃₆ N ₄ O ₂ = 893.02) 2-94 m / z = 791.30 (C ₅₇ H ₃₇ N ₅ = 791.96) 2-95 m / z = 854.30 (C ₆₂ H ₃₈ N ₄ O = 855.01) 2-96 m / z = 690.25 (C ₄₈ H ₃₀ N ₆ = 690.81) 2-97 m / z = 815.30 (C ₅₉ H ₃₇ N ₅ = 815.98) 2-98 m / z = 893.33 (C ₆₃ H ₃₉ N ₇ = 894.05) 2-99 m / z = 913.32 (C ₆₇ H ₃₉ N ₅ = 914.08) 2-100 m / z = 930.37 (C ₆₉ H ₄₆ N ₄ = 931.16) 2-101 m / z = 501.16 (C ₃₆ H ₂₃ NS = 501.65) 2-102 m / z = 580.17 (C ₃₉ H ₂₄ N ₄ S = 580.71) 2-103 m / z = 643.17 (C ₄₄ H ₂₅ N ₃ OS = 643.76) 2-104 m / z = 838.31 (C ₆₂ H ₃₈ N ₄ = 839.01) 2-105 m / z = 779.26 (C ₅₆ H ₃₃ N ₃ O ₂ = 779.90) 2-106 m / z = 709.28 (C ₅₅ H ₃₅ N = 709.89) 2-107 m / z = 685.16 (C ₄₆ H ₂₇ N ₃ S ₂ = 685.86) 2-108 m / z = 577.18 (C ₄₀ H ₂₃ N ₃ O ₂ = 577.64) 2-109 m / z = 738.19 (C ₄₉ H ₃₀ N ₄ S ₂ = 738.93) 2-110 m / z = 662.25 (C ₄₈ H ₃₀ N ₄ = 662.80) 2-111 m / z = 630.19 (C ₄₃ H ₂₆ N ₄ S = 630.77) 2-112 m / z = 654.19 (C ₄₅ H ₂₆ N ₄ S = 654.79) 2-113 m / z = 737.25 (C ₅₄ H ₃₁ N ₃ O = 737.86) 2-114 m / z = 775.21 (C ₅₃ H ₃₃ N ₃ S ₂ = 775.99) 2-115 m / z = 561.21 (C ₄₂ H ₂₇ NO = 561.68) 2-116 m / z = 687.27 (C ₅₁ H ₃₃ N ₃ = 687.85) 2-117 m / z = 720.20 (C ₄₉ H ₂₈ N ₄ OS = 720.85) 2-118 m / z = 579.18 (C ₄₀ H ₂₅ N ₃ S = 579.72) 2-119 m / z = 912.33 (C ₆₈ H ₄₀ N ₄ = 913.10) 2-120 m / z = 677.25 (C ₄₉ H ₃₁ N ₃ O = 677.81) 2-121 m / z = 664.23 (C ₄₇ H ₂₈ N ₄ O = 664.77) 2-122 m / z = 755.24 (C ₅₄ H ₃₃ N ₃ S = 755.94) 2-123 m / z = 653.25 (C ₄₇ H ₃₁ N ₃ O = 653.79) 2-124 m / z = 589.23 (C ₃₉ H ₁₅ D ₉ N ₄ S = 589.76) 2-125 _{m / z = 517.12 (C 34} H 19 N 3 OS = 517.61) 2-126 m / z = 549.16 (C ₄₀ H ₂₃ NS = 549.69) 2-127 m / z = 614.21 (C ₄₃ H ₂₆ N ₄ O = 614.71) 2-128 m / z = 595.15 (C ₄₀ H ₂₂ FN ₃ S = 595.70) 2-129 m / z = 729.28 (C 53 H 35 N 3 O = 729.88) 2-130 m / z = 819.23 (C ₅₈ H ₃₃ N ₃ OS = 819.98) 2-131 m / z = 699.14 (C ₄₆ H ₂₅ N ₃ OS ₂ = 699.85) 2-132 m / z = 739.30 (C ₅₅ H ₃₇ N ₃ = 739.92) 2-133 m / z = 639.23 (C ₄₆ H ₂₉ N 3 O = 639.76) 2-134 m / z = 732.23 (C ₅₁ H ₃₂ N ₄ S = 732.91) 2-135 m / z = 777.28 (C ₅₇ H ₃₅ N ₃ O = 777.93)

On the other hand, the In been described an exemplary composite of the present invention represented by Formula 1 and Formula 2, all of Buchwald-Hartwig cross coupling reaction, Miyaura boration reaction, Suzuki cross-coupling reaction, Intramolecular acid-induced cyclization reaction (J . mater. Chem. 1999, 9 , 2095.), Pd (II) -catalyzed oxidative cyclization reaction (Org. Lett. 2011, 13 , 5504) , and PPh ₃ -mediated reductive cyclization reaction (J. Org. Chem. 2005, 70 , 5014.), and other substituents (X ¹ to X ³ , L ¹ to L ⁸ , Ar ¹ to Ar ⁸ , A, B, C, D, E, F, G, and H) are bonded to each other, it will be understood by those skilled in the art.

Evaluation of manufacturing of organic electric device

[ Example  1] to [ Example  158] Red organic electroluminescent device  ( The light-  Mixed phosphorescent host)

First, a 4,4 ', 4 "-Tris [2-naphthyl (phenyl) amino] triphenylamine (abbreviated as 2-TNATA) film was vacuum deposited on the ITO layer (anode) (1-naphthalenyl) -N, N'-bis-phenyl- (1,1'-biphenyl) -4,4'-diamine (hereinafter abbreviated as NPB) (Shown in Table 4) represented by Formula 1 (first host) and Formula 2 (second host) as a host were immersed in a 3: 7 was doped with 5 wt% of (piq) ₂ Ir (acac) [bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate] as a dopant to form a 30 nm thick light emitting layer on the hole transport layer (2-methyl-8-quinolinolato) aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm as a hole blocking layer , Electronic To the songcheung Bis (10-hydroxybenzo [h] quinolinato) beryllium ( hereinafter referred to as BeBq ₂₎ it was formed in 50 nm thick, and since, depositing a halogenated alkali metal, LiF to the electron injection layer to 0.2 nm thickness, Subsequently, Al was deposited to a thickness of 150 nm and used as a cathode to produce an organic electroluminescent device.

[ Comparative Example  1] to [ Comparative Example  3]

An organic electroluminescence device was prepared in the same manner as in Example 1 except that the compound of the present invention represented by Formula 2 (described in Table 4) was used as a host alone.

[ Comparative Example  4]

An organic electroluminescence device was fabricated in the same manner as in Example 1 except that Comparative Compound v1 and Compound 2-4 of the present invention were mixed and used as a host.

Electruminescence (EL) characteristics were measured with a photoresearch PR-650 by applying a forward bias DC voltage to the organic electroluminescent devices manufactured in Examples 1 to 158 and Comparative Examples 1 to 4 of the present invention And the T95 lifetime was measured using a Mac Science longevity measuring instrument at a reference luminance of 2500 cd / m ^2. The measurement results are shown in Table 4 below.

The first host Second host Driving voltage
(V) electric current
(mA / cm ² ) Luminance
(cd / m ² ) efficiency
(cd / A) life span
T (95) CIE x y Comparative Example (1) - 2-1 6.9 21.9 2500 11.4 73.9 0.67 0.32 Comparative Example (2) - 2-4 5.8 19.7 2500 12.7 98.4 0.66 0.34 Comparative Example (3) - 2-111 6.0 20.7 2500 12.1 87.2 0.66 0.33 Comparative Example (4) v1 2-4 5.8 18.7 2500 13.3 95.5 0.66 0.34 Example (1) 1-1 2-4 5.3 7.8 2500 32.1 139.4 0.66 0.35 Example (2) 1-16 2-4 5.1 7.3 2500 34.5 144.8 0.66 0.34 Example (3) 1-53 2-4 5.1 7.9 2500 31.6 140.0 0.66 0.35 Example (4) 1-59 2-4 5.0 7.1 2500 35.0 145.5 0.66 0.35 Example (5) 1-65 2-4 5.1 7.6 2500 32.8 139.4 0.66 0.35 Example (6) 1-66 2-4 5.0 7.3 2500 34.1 144.7 0.66 0.35 Example (7) 1-76 2-4 5.0 7.3 2500 34.5 144.9 0.66 0.34 Example (8) 1-116 2-4 5.1 7.8 2500 31.9 139.4 0.66 0.34 Example (9) 1-117 2-4 5.3 7.8 2500 32.2 139.8 0.66 0.34 Example (10) 1-119 2-4 5.2 8.2 2500 30.7 138.4 0.66 0.35 Example (11) 1-125 2-4 5.2 8.2 2500 30.7 138.3 0.66 0.35 Example (12) 1-139 2-4 5.2 7.7 2500 32.5 140.0 0.66 0.34 Example (13) 1-182 2-4 5.1 7.5 2500 33.4 140.6 0.66 0.34 Example (14) 1-186 2-4 5.3 7.4 2500 33.6 142.8 0.66 0.34 Example (15) 1-188 2-4 5.2 7.6 2500 32.8 139.9 0.66 0.34 Example (16) 1-190 2-4 5.1 7.6 2500 32.8 139.8 0.66 0.35 Example (17) 1-195 2-4 5.2 7.9 2500 31.7 139.7 0.66 0.34 Example (18) 1-201 2-4 5.2 7.9 2500 31.5 139.4 0.66 0.34 Example (19) 1-205 2-4 5.2 8.1 2500 30.8 138.4 0.66 0.35 Example (20) 1-258 2-4 5.3 8.1 2500 30.8 138.1 0.66 0.35 Example (21) 1-1 2-10 5.3 9.2 2500 27.2 134.0 0.66 0.35 Example (22) 1-16 2-10 5.2 8.8 2500 28.4 136.5 0.66 0.35 Example (23) 1-53 2-10 5.3 9.2 2500 27.2 134.2 0.66 0.35 Example (24) 1-59 2-10 5.2 8.6 2500 29.1 138.3 0.66 0.34 Example (25) 1-65 2-10 5.3 9.1 2500 27.4 134.6 0.66 0.34 Example (26) 1-66 2-10 5.3 8.8 2500 28.3 136.1 0.66 0.35 Example (27) 1-76 2-10 5.2 8.7 2500 28.6 137.9 0.66 0.34 Example (28) 1-116 2-10 5.3 9.2 2500 27.0 134.1 0.66 0.34 Example (29) 1-117 2-10 5.3 9.2 2500 27.1 134.2 0.66 0.35 Example (30) 1-119 2-10 5.3 9.4 2500 26.6 133.5 0.66 0.35 Example (31) 1-125 2-10 5.3 9.3 2500 26.7 133.6 0.66 0.35 Example (32) 1-139 2-10 5.3 9.1 2500 27.5 134.4 0.66 0.35 Example (33) 1-182 2-10 5.3 9.0 2500 27.8 135.8 0.66 0.35 Example (34) 1-186 2-10 5.4 8.9 2500 27.9 135.2 0.66 0.34 Example (35) 1-188 2-10 5.3 9.1 2500 27.4 135.4 0.66 0.35 Example (36) 1-190 2-10 5.3 9.1 2500 27.5 134.8 0.66 0.34 Example (37) 1-195 2-10 5.4 9.2 2500 27.1 134.2 0.66 0.34 Example (38) 1-201 2-10 5.3 9.2 2500 27.1 134.0 0.66 0.34 Example (39) 1-205 2-10 5.3 9.4 2500 26.6 133.5 0.66 0.35 Example (40) 1-258 2-10 5.3 9.3 2500 26.9 133.0 0.66 0.34 Example (41) 1-1 2-15 5.3 8.8 2500 28.3 136.7 0.66 0.34 Example (42) 1-16 2-15 5.2 7.8 2500 31.9 139.2 0.66 0.34 Example (43) 1-53 2-15 5.3 8.8 2500 28.5 137.1 0.66 0.35 Example (44) 1-59 2-15 5.1 7.6 2500 32.8 139.3 0.66 0.34 Example (45) 1-65 2-15 5.2 8.6 2500 29.1 136.5 0.66 0.34 Example (46) 1-66 2-15 5.2 8.1 2500 30.7 138.1 0.66 0.34 Example (47) 1-76 2-15 5.2 8.0 2500 31.4 139.6 0.66 0.35 Example (48) 1-116 2-15 5.3 8.7 2500 28.7 136.2 0.66 0.34 Example (49) 1-117 2-15 5.3 8.8 2500 28.5 137.1 0.66 0.35 Example (50) 1-119 2-15 5.3 8.9 2500 28.2 136.4 0.66 0.35 Example (51) 1-125 2-15 5.4 8.9 2500 28.2 136.5 0.66 0.34 Example (52) 1-139 2-15 5.2 8.6 2500 29.2 137.7 0.66 0.34 Example (53) 1-182 2-15 5.2 8.5 2500 29.5 137.4 0.66 0.34 Example (54) 1-186 2-15 5.2 8.4 2500 29.7 136.6 0.66 0.35 Example (55) 1-188 2-15 5.2 8.6 2500 29.2 136.9 0.66 0.35 Example (56) 1-190 2-15 5.2 8.6 2500 29.2 137.0 0.66 0.34 Example (57) 1-195 2-15 5.3 8.7 2500 28.6 136.2 0.66 0.34 Example (58) 1-201 2-15 5.2 8.8 2500 28.4 137.4 0.66 0.34 Example (59) 1-205 2-15 5.2 8.9 2500 28.1 136.2 0.66 0.35 Example (60) 1-258 2-15 5.2 8.9 2500 28.2 136.3 0.66 0.35 Example (61) 1-1 2-19 5.4 9.2 2500 27.1 133.9 0.66 0.35 Example (62) 1-16 2-19 5.3 8.8 2500 28.5 136.7 0.66 0.35 Example (63) 1-53 2-19 5.2 9.2 2500 27.2 134.0 0.66 0.34 Example (64) 1-59 2-19 5.2 8.6 2500 29.1 138.3 0.66 0.35 Example (65) 1-65 2-19 5.2 9.1 2500 27.4 134.5 0.66 0.34 Example (66) 1-66 2-19 5.2 8.8 2500 28.3 136.3 0.66 0.35 Example (67) 1-76 2-19 5.3 8.8 2500 28.4 136.6 0.66 0.35 Example (68) 1-116 2-19 5.2 9.2 2500 27.1 133.9 0.66 0.34 Example (69) 1-117 2-19 5.3 9.2 2500 27.1 133.8 0.66 0.34 Example (70) 1-119 2-19 5.3 9.4 2500 26.7 133.6 0.66 0.35 Example (71) 1-125 2-19 5.3 9.3 2500 26.9 133.7 0.66 0.35 Example (72) 1-139 2-19 5.2 9.1 2500 27.4 134.9 0.66 0.35 Example (73) 1-182 2-19 5.4 8.9 2500 28.0 135.1 0.66 0.35 Example (74) 1-186 2-19 5.4 9.0 2500 27.8 134.7 0.66 0.34 Example (75) 1-188 2-19 5.4 9.1 2500 27.4 134.7 0.66 0.34 Example (76) 1-190 2-19 5.2 9.1 2500 27.4 134.3 0.66 0.34 Example (77) 1-195 2-19 5.3 9.2 2500 27.2 134.1 0.66 0.34 Example (78) 1-201 2-19 5.3 9.2 2500 27.3 133.9 0.66 0.34 Example (79) 1-205 2-19 5.3 9.3 2500 27.0 133.5 0.66 0.35 Example (80) 1-258 2-19 5.3 9.3 2500 26.9 133.6 0.66 0.35 Example (81) 1-16 2-28 5.2 9.7 2500 25.7 131.9 0.66 0.35 Example (82) 1-59 2-28 5.3 9.6 2500 25.9 132.7 0.66 0.34 Example (83) 1-65 2-28 5.4 10.0 2500 24.9 130.6 0.66 0.34 Example (84) 1-66 2-28 5.4 9.9 2500 25.2 131.2 0.66 0.34 Example (85) 1-76 2-28 5.4 9.8 2500 25.6 132.7 0.66 0.35 Example (86) 1-139 2-28 5.4 10.1 2500 24.8 130.1 0.66 0.34 Example (87) 1-182 2-28 5.4 10.0 2500 25.0 130.9 0.66 0.35 Example (88) 1-186 2-28 5.5 10.0 2500 25.0 130.2 0.66 0.35 Example (89) 1-188 2-28 5.5 10.1 2500 24.8 130.7 0.66 0.34 Example (90) 1-190 2-28 5.4 10.1 2500 24.8 130.2 0.66 0.35 Example (91) 1-16 2-46 5.3 9.8 2500 25.6 132.6 0.66 0.34 Example (92) 1-59 2-46 5.4 9.7 2500 25.9 132.6 0.66 0.34 Example (93) 1-65 2-46 5.5 10.1 2500 24.9 130.6 0.66 0.34 Example (94) 1-66 2-46 5.4 9.9 2500 25.3 131.6 0.66 0.34 Example (95) 1-76 2-46 5.3 9.8 2500 25.6 132.4 0.66 0.34 Example (96) 1-139 2-46 5.4 10.1 2500 24.8 130.5 0.66 0.34 Example (97) 1-182 2-46 5.4 10.0 2500 25.1 130.4 0.66 0.35 Example (98) 1-186 2-46 5.5 10.0 2500 25.0 130.1 0.66 0.34 Example (99) 1-188 2-46 5.4 10.1 2500 24.8 130.1 0.66 0.35 Example (100) 1-190 2-46 5.4 10.1 2500 24.8 130.5 0.66 0.35 Example (101) 1-16 2-74 5.3 9.8 2500 25.5 131.9 0.66 0.35 Example (102) 1-59 2-74 5.3 9.6 2500 25.9 132.8 0.66 0.34 Example (103) 1-65 2-74 5.5 10.1 2500 24.8 130.4 0.66 0.34 Example (104) 1-66 2-74 5.3 9.9 2500 25.3 131.1 0.66 0.35 Example (105) 1-76 2-74 5.2 9.8 2500 25.4 131.8 0.66 0.35 Example (106) 1-139 2-74 5.4 10.1 2500 24.9 130.8 0.66 0.35 Example (107) 1-182 2-74 5.5 10.0 2500 25.0 130.9 0.66 0.35 Example (108) 1-186 2-74 5.4 10.0 2500 25.1 130.8 0.66 0.34 Example (109) 1-188 2-74 5.5 10.1 2500 24.8 131.0 0.66 0.34 Example (110) 1-190 2-74 5.4 10.1 2500 24.9 130.5 0.66 0.34 Example (111) 1-1 2-81 5.3 9.8 2500 25.5 131.8 0.66 0.34 Example (112) 1-16 2-81 5.2 9.2 2500 27.2 134.1 0.66 0.34 Example (113) 1-53 2-81 5.3 9.8 2500 25.5 131.7 0.66 0.34 Example (114) 1-59 2-81 5.2 9.1 2500 27.4 134.5 0.66 0.34 Example (115) 1-65 2-81 5.4 9.6 2500 26.0 132.2 0.66 0.34 Example (116) 1-66 2-81 5.2 9.4 2500 26.7 133.6 0.66 0.35 Example (117) 1-76 2-81 5.3 9.2 2500 27.2 134.1 0.66 0.35 Example (118) 1-116 2-81 5.3 9.8 2500 25.5 131.7 0.66 0.35 Example (119) 1-117 2-81 5.3 9.7 2500 25.7 131.7 0.66 0.35 Example (120) 1-139 2-81 5.2 9.6 2500 25.9 132.5 0.66 0.35 Example (121) 1-182 2-81 5.2 9.5 2500 26.3 131.9 0.66 0.35 Example (122) 1-186 2-81 5.2 9.5 2500 26.4 131.7 0.66 0.34 Example (123) 1-188 2-81 5.4 9.7 2500 25.9 132.5 0.66 0.34 Example (124) 1-190 2-81 5.3 9.6 2500 25.9 132.1 0.66 0.34 Example (125) 1-195 2-81 5.3 9.8 2500 25.6 132.7 0.66 0.35 Example (126) 1-201 2-81 5.4 9.8 2500 25.5 131.7 0.66 0.34 Example (127) 1-1 2-83 5.3 9.8 2500 25.5 132.8 0.66 0.34 Example (128) 1-16 2-83 5.3 9.2 2500 27.3 133.8 0.66 0.35 Example (129) 1-53 2-83 5.3 9.8 2500 25.4 132.3 0.66 0.35 Example (130) 1-59 2-83 5.3 9.1 2500 27.4 134.3 0.66 0.34 Example (131) 1-65 2-83 5.3 9.7 2500 25.9 131.8 0.66 0.35 Example (132) 1-66 2-83 5.2 9.3 2500 26.8 133.2 0.66 0.35 Example (133) 1-76 2-83 5.3 9.2 2500 27.2 134.0 0.66 0.35 Example (134) 1-116 2-83 5.2 9.8 2500 25.5 131.9 0.66 0.34 Example (135) 1-117 2-83 5.3 9.8 2500 25.5 132.7 0.66 0.34 Example (136) 1-139 2-83 5.3 9.7 2500 25.9 132.7 0.66 0.35 Example (137) 1-182 2-83 5.2 9.5 2500 26.4 132.4 0.66 0.34 Example (138) 1-186 2-83 5.3 9.5 2500 26.3 131.9 0.66 0.35 Example (139) 1-188 2-83 5.3 9.7 2500 25.8 132.3 0.66 0.34 Example (140) 1-190 2-83 5.2 9.6 2500 25.9 132.0 0.66 0.35 Example (141) 1-195 2-83 5.2 9.8 2500 25.5 132.8 0.66 0.34 Example (142) 1-201 2-83 5.3 9.8 2500 25.5 132.2 0.66 0.34 Example (143) 1-1 2-111 5.3 9.7 2500 25.7 131.8 0.66 0.35 Example (144) 1-16 2-111 5.3 9.2 2500 27.2 134.1 0.66 0.34 Example (145) 1-53 2-111 5.4 9.8 2500 25.5 132.1 0.66 0.35 Example (146) 1-59 2-111 5.3 9.1 2500 27.5 135.3 0.66 0.34 Example (147) 1-65 2-111 5.4 9.6 2500 26.0 131.8 0.66 0.35 Example (148) 1-66 2-111 5.4 9.3 2500 26.8 133.6 0.66 0.34 Example (149) 1-76 2-111 5.4 9.2 2500 27.2 133.8 0.66 0.34 Example (150) 1-116 2-111 5.4 9.8 2500 25.6 131.8 0.66 0.34 Example (151) 1-117 2-111 5.3 9.8 2500 25.6 132.2 0.66 0.35 Example (152) 1-139 2-111 5.3 9.7 2500 25.9 132.2 0.66 0.34 Example (153) 1-182 2-111 5.3 9.5 2500 26.4 132.5 0.66 0.35 Example (154) 1-186 2-111 5.4 9.5 2500 26.4 132.0 0.66 0.34 Example (155) 1-188 2-111 5.4 9.7 2500 25.9 131.6 0.66 0.34 Example (156) 1-190 2-111 5.3 9.7 2500 25.9 132.4 0.66 0.35 Example (157) 1-195 2-111 5.2 9.7 2500 25.7 132.6 0.66 0.35 Example (158) 1-201 2-111 5.2 9.8 2500 25.5 131.8 0.66 0.35

As can be seen from the results of Table 4, when organic electroluminescence device materials of the present invention represented by Formulas 1 and 2 were mixed and used as a phosphorescent host (Examples 1 to 158) (Comparative example 1 to comparative example 3), or the comparative compound v1 and the compound of the present invention 2-4 were mixed to remarkably improve the driving voltage, efficiency and lifetime, compared with the device using as a phosphorescent host (comparative example 4).

Particularly, it can be confirmed that Comparative Example 4 using Comparative Compound v1 and Compound 2-4 of the present invention as a phosphorescent host showed a higher efficiency than Comparative Examples 1 to 3 using a single substance, It can be confirmed that Examples 1 to 158 using the compounds of the present invention as a host by mixing the compounds of the formulas (1) and (2) with the compounds of the present invention exhibited remarkably high efficiency and long life.

On the basis of the above experimental results, the inventors of the present invention have found that a substance obtained by mixing a substance of the formula (1) and a substance of the formula (2) has novel characteristics other than those of the substance, , And the mixture of the present invention was used to measure PL lifetime. As a result, it was confirmed that a new PL wavelength was formed when the compounds of the present invention were combined with the compounds of the formulas (1) and (2), and the newly formed PL wavelength was reduced and the decay time was Decrease and decay time from about 60 times to about 360 times. When mixed with the compound of the present invention, not only electrons and holes are moved through the energy level of each substance, but also electrons, holes, or energy (exciplex) due to exciplex in a new region having a new energy level It is considered that the efficiency and life span of the transmission line are increased. As a result, when the mixture of the present invention is used, the mixed thin film is an important example showing the exciplex energy transfer and light emitting process.

The reason why the combination of the present invention is superior is that when a compound represented by the general formula (1) having a hole property stronger than that of the bis-type heterocyclic compound represented by the general formula (2) , The electron blocking ability is improved due to the high T1 and high LUMO energy value, and more holes are moved to the emissive layer quickly and easily. As a result, 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 at the interface of the hole transporting layer, and deterioration in the HTL interface is also reduced, thereby maximizing the driving voltage, efficiency and lifetime of the device . That is, it is concluded that the combination of the formula (1) and the formula (2) is electrochemically synergistic to improve the performance of the device as a whole.

[ Example  159] to [ Example  161] by mixing ratio Red organic electroluminescent device  ( The light-  Mixed phosphorescent host)

An organic electroluminescence device was fabricated in the same manner as in Example 4, except that the mixing ratios of the materials were changed as shown in Table 5.

[ Example  162] to [ Example  164] by mixing ratio Red organic electroluminescent device  ( The light-  Mixed phosphorescent host)

An organic electroluminescence device was fabricated in the same manner as in Example 153 except that the mixing cost of the materials was changed as shown in Table 5. [

Electruminescence (EL) characteristics were measured with a photoresearch PR-650 by applying a forward bias DC voltage to the organic electroluminescent devices manufactured in Example 4, Example 153, and Examples 159 to 164, And the T95 lifetime was measured using a Mac Science longevity measuring apparatus at a reference luminance of 2500 cd / m ^2. The measurement results are shown in Table 5 below.

The first host Second host Mixing ratio
(First host:
Second host) Driving
Voltage
(V) electric current
(mA / cm ² ) Luminance
(cd / m ² ) efficiency
(cd / A) life span
T (95) CIE x y Example (159) 1-59 2-4 2: 8 5.1 7.2 2500 34.6 144.1 0.66 0.35 Example (4) 1-59 2-4 3: 7 5.0 7.1 2500 35.0 145.5 0.66 0.35 Example (160) 1-59 2-4 4: 6 5.4 7.5 2500 33.4 138.0 0.66 0.35 Example (161) 1-59 2-4 5: 5 5.6 8.0 2500 31.2 130.3 0.66 0.35 Example (162) 1-182 2-111 2: 8 5.3 9.3 2500 26.9 133.1 0.66 0.35 Example (153) 1-182 2-111 3: 7 5.3 9.5 2500 26.4 132.5 0.66 0.35 Example (163) 1-182 2-111 4: 6 5.5 10.1 2500 24.8 129.4 0.66 0.35 Example (164) 1-182 2-111 5: 5 5.8 10.9 2500 23.0 123.6 0.66 0.35

As shown in Table 5, a mixture of the compound of the present invention was measured by fabricating the device at a ratio of 2: 8, 3: 7, 4: 6, 5: 5. As a result of the mixture of Compound 1-59 and Compound 2-4, the results of mixing with 2: 8 and 3: 7 showed similar results in terms of driving voltage, efficiency and lifetime, but in the case of mixing ratios of 4: 6 and 5: 5 The efficiency of the driving voltage, the efficiency and the lifetime are gradually decreased as the ratio of the first host increases. These results were also the same when Compound 1-182 and Compound 2-111 were mixed. It is considered that this is because the charge balance in the light emitting layer is maximized when an appropriate amount of the compound represented by the formula (1) having strong hole properties such as 2: 8 and 3: 7 is mixed.

While the present invention has been described with reference to exemplary embodiments, it is to be understood that the invention is not limited to the disclosed exemplary embodiments. Accordingly, the embodiments disclosed herein are intended to be illustrative rather than limiting, and the spirit and scope of the present invention is not limited by these embodiments. The scope of protection of the present invention should be construed according to the following claims, and all the techniques within the scope of the same should be construed as being included in the scope of the present invention.

100: organic electric element 110: substrate
120: First electrode (anode) 130: Hole injection layer
140: Hole transport layer 141: Buffer layer
150: light emitting layer 151: light emitting auxiliary layer
160: electron transport layer 170: electron injection layer
180: second electrode (cathode)

Claims (15)

1. An organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, wherein the organic layer includes a light emitting layer, And a second host compound represented by the general formula (2).

{In the above formulas (1), (1-1) and (2)
M is a C ₆ -C ₆₀ arylene group or the above formula (1-1)
X &lt; ¹ &gt; is S or O,
X ² is NL ⁵ -Ar ⁶ , O, S or CR ^a R ^b ,
X ³ is NL ⁸ -Ar ⁸ , O, S or CR ^c R ^d ,
A, B, C, D, E, F, G, and H are independently of each other a C ₆ -C ₂₀ aryl group or a C ₂ -C ₂₀ heterocyclic group,
C is bonded to L ³ , D is bonded to L ⁴ ,
R ^a , R ^b , R ^c and R ^d independently of one another are hydrogen, deuterium; Tritium; halogen; Cyano; A nitro group; An aryl group of C ₆ -C ₆₀ ; A fluorenyl group; Heterocyclic group of _{O, N, S, C 2} -C 60 containing at least one heteroatom selected from the group consisting of Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₁ -C ₃₀ alkoxyl group and a C ₆ -C ₃₀ aryloxy group; R ^a and R ^b may combine with each other to form a spiro compound;
Ar ¹ , Ar ² , Ar ³ , Ar ⁴ , Ar ⁵ , Ar ⁶ , Ar ⁷ and Ar ⁸ are each independently a C ₆ -C ₆₀ aryl group; Heterocyclic group of _{O, N, S, C 2} -C 60 containing at least one heteroatom selected from the group consisting of Si and P; A fluorenyl group; A fused ring group of a C ₆ -C ₆₀ aromatic ring and a C ₃ -C ₆₀ aliphatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₁ -C ₃₀ alkoxyl group; And a C ₆ -C ₃₀ aryloxy group; and Ar ¹ is selected from the group consisting of Ar ¹ To Ar ⁸ may combine with each other to form a ring,
L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , L ⁷ and L ⁸ independently of one another are a single bond; C ₆ -C ₆₀ arylene groups; A fluorenylene group; A C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; And an aliphatic hydrocarbon group,
Here, the aryl group, the fluorenyl group, the arylene group, the heterocyclic group, the fluorenylene group, the fused ring group, the alkyl group, the alkenyl group, the alkoxy group and the aryloxy group each may be substituted with deuterium; halogen; A silane group; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; An alkyl thio group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkoxyl group; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₆ -C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted by deuterium; A fluorenyl group; A C ₂ -C ₂₀ heterocyclic group; A C ₃ -C ₂₀ cycloalkyl group; An arylalkyl group having _{7 to 20} carbon atoms, an arylalkyl group having _{7 to 20} carbon atoms and an arylalkenyl group having _{8 to 20} carbon atoms, and these substituents may be further bonded to each other to form a ring, Ring &quot; refers to a fused ring consisting of a C ₃ -C ₆₀ aliphatic ring or a C ₆ -C ₆₀ aromatic ring or a C ₂ -C ₆₀ heterocyclic ring or a combination thereof, including saturated or unsaturated rings.
The compound according to claim 1, wherein A, B, C, D, E, and F in Formula 1, Formula 1-1 or Formula 2 are independently selected from the group consisting of the following Formulas a- Wherein the organic electroluminescent device is one of the organic electroluminescent devices.

(In formulas (a-1) to (a-7)
Z ¹ to Z ⁴⁸ are CR ^e or N,
Provided that Z ¹ to Z ⁴⁸ bonded to L ¹ to L ⁶ are carbon (C)
R ^e is the same as defined in R ^a in claim 1,
* Indicates the position to be condensed.
The organic electroluminescent device according to claim 1, wherein L ¹ to L ⁶ in any one of formulas (1), (1-1) and (2) are any of the following formulas (b-1) to (b-13).

Formula b-11 Formula b-12 Formula b-13

(In the formulas (b-1) to (b-13)
Y is NL ⁹ -Ar ⁹ , O, S or CR ^f R ^g ,
L ⁹ is the same as L ⁵ in claim 1,
Ar ⁹ is the same as defined in Ar ⁶ in claim 1,
R ^f and R ^g are as defined in R ^a in claim 1,
a, c, d and e are each independently an integer of 0 to 4, b is an integer of 0 to 6, f and g are independently an integer of 0 to 3, h is an integer of 0 to 2, i is an integer of 0 or 1,
R ¹ to R ³ independently of one another are hydrogen; heavy hydrogen; Tritium; halogen; Cyano; A nitro group; An aryl group of C ₆ -C ₆₀ ; A fluorenyl group; Heterocyclic group of _{O, N, S, C 2} -C 60 containing at least one heteroatom selected from the group consisting of Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₁ -C ₃₀ alkoxyl group; A C ₆ -C ₃₀ aryloxy group; And ^{-L a -N (R h) (} R i); if is selected from the group consisting of or wherein a, b, c, d, e, f and g is not less than 2, and h is 2 are each A plurality of R ^{1 s} or a plurality of R ^{2 s} or a plurality of R ^{3 s} or adjacent R ^{1 s} and R ^{2 s} or R ^{2 s} and R ^{3 s} are bonded to each other to form an aromatic ring or a heteroaromatic ring You can,
Wherein L ^a is a single bond; C ₆ -C ₆₀ arylene groups; A fluorenylene group; A C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; And C ₃ -C ₆₀ aliphatic hydrocarbon groups; and R ^h and R ⁱ are independently selected from the group consisting of C ₆ -C ₆₀ aryl groups; A fluorenyl group; Heterocyclic group of _{O, N, S, C 2} -C 60 containing at least one heteroatom selected from the group consisting of Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring,
Z ⁴⁹ , Z ⁵⁰ and Z ⁵¹ independently of one another are CR ^j or N, and at least one of Z ⁴⁹ , Z ⁵⁰ and Z ⁵¹ is N,
R ^j is hydrogen; heavy hydrogen; Tritium; halogen; Cyano; A nitro group; An aryl group of C ₆ -C ₆₀ ; A fluorenyl group; Heterocyclic group of _{O, N, S, C 2} -C 60 containing at least one heteroatom selected from the group consisting of Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₁ -C ₃₀ alkoxyl group; And a C ₆ -C ₃₀ aryloxy group, and adjacent R ¹ and R ^h may be bonded to each other to form an aromatic ring or a heteroaromatic ring.
The organic electroluminescent device according to claim 1, wherein at least one of Ar ¹ to Ar ⁵ in Formula 1 is represented by Formula 1-2.

{In Formula 1-2,
I and J are the same as defined in claim 1 above,
X ⁴ is NL ¹¹ -Ar ¹⁰ , O, S or CR ^k R ¹ ,
L ¹⁰ and L ¹¹ have the same definitions as L ⁵ in claim 1,
Ar ¹⁰ has the same definition as Ar ⁶ in claim 1,
R ^k and R ¹ are as defined in R ^a in claim 1.
The organic electroluminescent device according to claim 4, wherein the first host compound represented by Formula 1 is represented by Formula 3 below.

{In the above formula (3)
X ¹ , X ² , Ar ¹ to Ar ⁵ are as defined in claim 1,
Z ¹ to Z ⁴ independently of one another are CR ^e or N,
Provided that Z ¹ to Z ⁴ bonded to N are carbon (C)
R ^e is the same as defined in R ^a in claim 1 above.
The organic electroluminescent device according to claim 1, wherein X ¹ and X ² in Formula 1 are independently O or S.
The organic electroluminescent device according to claim 1, wherein the second host compound represented by the formula (2) is represented by any one of the following formulas (4) to (7).

{In the above Chemical Formulas 4 to 7,
E, F, G, H, L ⁶ , L ⁷ , L ⁸ , Ar ⁷ , Ar ⁸ , R ^c and R ^d are as defined in claim 1.
The organic electroluminescent device according to claim 1, wherein the first host compound represented by Formula 1 is any one of the following Compounds 1-1 to 1-265.

The organic electroluminescent device according to claim 1, wherein the second host compound represented by Formula 2 is any one of the following Compounds 2-1 to 2-135.

The organic electroluminescent device of claim 1, further comprising at least one hole transporting band layer between the first electrode and the light emitting layer, wherein the hole transporting band layer comprises a hole transporting layer, a light emitting auxiliary layer or both, The organic electroluminescent device according to claim 1, wherein the organic electroluminescent device comprises a compound represented by the general formula (1).
The organic electroluminescent device according to claim 1, wherein the organic electroluminescent layer is mixed in a ratio of 1: 9 to 9: 1 of the compound represented by the formula (1) and the compound represented by the formula (2)
The organic electroluminescent device according to claim 1, wherein the organic electroluminescent layer is mixed with the compound represented by the formula (1) and the compound represented by the formula (2) in a ratio of 1: 9 to 5: 5.
The organic electroluminescent device according to claim 1, wherein the compound represented by the general formula (1) and the compound represented by the general formula (2) are mixed in a ratio of 2: 8 or 3: 7.
A display device comprising the organic electroluminescent device according to claim 1, and a control unit for driving the display device.
15. The electronic device according to claim 14, wherein the organic electronic device is at least one of an organic electroluminescent device, an organic solar cell, an organophotoreceptor, an organic transistor, and a monochromatic or white illumination device.

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