KR20140141951A - An organic electronic element using compound for organic electronic element, and an electronic device thereof - Google Patents

Abstract

The present invention relates to a novel compound which improves light emission efficiency, stability, and lifetime of a device, an organic electric element using the same, and an electronic device thereof. The organic electric element using the compound for an organic electric element includes a first electrode, a second electrode, and an organic layer which is located between the first electrode and the second electrode. The organic layer includes a light emitting layer which includes a dopant and host material, respectively.

Description

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

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescent device using an organic electroluminescent compound 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 multilayer structure composed of different materials, and may be formed of 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. The light emitting material may be classified into a polymer type and a low molecular type depending on the molecular weight, and may be classified into a phosphorescent material derived from singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons . Further, the light emitting material can be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural color depending on the luminescent color.

On the other hand, when only one material is used as a light emitting material, there arises a problem that the maximum light emission wavelength shifts to a long wavelength due to intermolecular interaction, the color purity decreases, or the efficiency of the device decreases due to the light emission attenuating effect. A host / dopant system may be used as a light emitting material in order to increase the light emitting efficiency through the light emitting layer. When the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with a small amount of the light emitting layer, the excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, the desired wavelength light can be obtained depending on the type of the dopant used.

In organic electroluminescent devices, the most problematic is the lifetime and the efficiency. As the display becomes larger, such efficiency and life time problems must be solved. The efficiency, lifetime, and driving voltage are related to each other. As the efficiency increases, the driving voltage decreases. As the driving voltage decreases, the crystallization of the organic material due to Joule heating, which occurs during driving, And the lifetime tends to increase.

However, it is impossible to maximize the efficiency by merely improving the organic material layer. The energy level and T1 value of each organic material layer, the intrinsic properties (mobility, interface characteristics, etc.) It can achieve long life and high efficiency at the same time. Therefore, it is necessary to develop a light emitting material having high thermal stability and achieving a charge balance in the light emitting layer efficiently. That is, in order to fully exhibit the excellent characteristics of the organic electronic device, a material constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material and an electron injecting material is supported by a stable and efficient material However, development of a stable and efficient organic material layer for an organic electric device has not yet been sufficiently developed. Particularly, development of a dopant and a host material of the light emitting layer is urgently required.

An object of the present invention is to provide an organic electronic device and an electronic device thereof capable of improving the device's high luminous efficiency, low driving voltage, high heat resistance, color purity, and service life.

In one aspect, the present invention provides an organic electronic device and its electronic device, wherein the organic electronic device includes the first electrode, the second electrode, and an organic layer positioned between the first electrode and the second electrode, Wherein the organic material layer comprises a light emitting layer containing a dopant material and a host material, respectively, and the dopant material comprises a compound represented by the following formula (1), wherein the host material is a compound represented by the following formulas (2) to Or the like.

(1) " (2) "

     Formula (3)

By using the compound according to the present invention, it is possible to achieve a high luminous efficiency, a low driving voltage, and a high heat resistance of the device, and can greatly improve the color purity and 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.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings.

It should be noted that, in adding reference numerals to the constituent elements of the drawings, the same constituent elements are denoted by the same reference symbols as possible even if they are shown in different drawings. 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" 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, It is not.

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.

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 indicated, the term "saturated or unsaturated ring" as used herein refers to a saturated or unsaturated aliphatic ring or an aromatic ring or hetero ring having 6 to 60 carbon atoms.

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 term < RTI ID = 0.0 >

When a is an integer of 0, a substituent R ¹ is absent. When a is an integer of 1, one substituent R ¹ is bonded to any one of carbon atoms forming a benzene ring. When a is an integer of 2 or 3, Wherein R ¹ may be the same or different and is bonded to the carbon of the benzene ring in a similar manner when a is an integer from 4 to 6 and the indication of hydrogen bonded to the carbon forming the benzene ring is omitted do.

1 is an illustration of an organic electroluminescent device according to an embodiment of the present invention.

1, an organic electroluminescent device 100 according to the present invention includes a first electrode 120, a second electrode 180, a first electrode 110, and a second electrode 180 formed on a substrate 110, ) Comprising an organic compound layer comprising a compound according to the present invention. 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 material layer may include a hole injecting layer 130, a hole transporting layer 140, a light emitting layer 150, 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. An electron blocking layer, a light emitting auxiliary layer 151, a buffer layer 141, and the like, and the electron transport layer 160 may serve as a hole blocking layer.

Also, although not shown, the organic electroluminescent device according to the present invention may further include a protective layer or a light-efficiency-improving layer formed on at least one surface of the first electrode and the second electrode opposite to the organic material layer.

The compound according to the present invention applied to the organic material layer may be a host or dopant of the hole injection layer 130, the hole transport layer 140, the electron transport layer 160, the electron injection layer 170, the light emitting layer 150, It can be used as a material.

The organic electroluminescent device according to an embodiment of the present invention can be manufactured using a physical vapor deposition (PVD) method. For example, the anode 120 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and a hole injecting layer 130, a hole transporting layer 140, a light emitting layer 150, and an electron transporting layer 160 and an electron injection layer 170, and then depositing a material usable as the cathode 180 on the organic layer.

In addition, the organic material layer may be formed using a variety of polymer materials, not a vapor deposition method, or a solution process or a solvent process such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, It is possible to produce a smaller number of layers by a method such as a dipping process, a screen printing process, or a thermal transfer process. Since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the forming method.

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

Another embodiment of the present invention can include an electronic device including a display device including the above-described organic electronic device of the present invention and a control unit for controlling the display device. 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, an organic electroluminescent device according to one aspect of the present invention will be described.

According to an embodiment of the present invention, there is provided an organic electroluminescent device comprising a first electrode, a second electrode, and an organic material layer disposed between the first electrode and the second electrode,

Wherein the organic material layer comprises a light emitting layer containing a dopant material and a host material, respectively, and the dopant material comprises a compound represented by the following formula (1), wherein the host material is represented by the following formulas (2) to Organic electroluminescent device according to the present invention.

    (1) " (2) "

     Formula (3)

In the above formulas,

a and b are each independently an integer of 0 or 1 (provided that a + b = 1 or more)

m and n are each independently an integer of 1 or 2,

q and o are each independently an integer of 1 to 4,

M is a metal selected from transition metals,

으로 표현되며, A is

Lt; / RTI >

A substituted or unsubstituted heterocyclic group of C ₂ ~ C ₂₀ ring containing the P ring is N (nitrogen), and said Q ring is C (carbon), a substituted or unsubstituted C ₆ ~ C ₂₀ aryl group containing, where , N (nitrogen) of the P ring forms a coordination bond (indicated by a dotted line) with the M, C (carbon) of the Q ring forms a covalent bond (indicated by a solid line) with the M,

When the P ring and the Q ring are each substituted, i) each substituent is independently selected from the group consisting of hydrogen; heavy hydrogen; halogen; A C ₆ to C ₆₀ aryl group; A C ₁ to C ₅₀ alkyl group; O, N, S, Si and P, A heterocyclic group of C ₂ ~ C _60; Florene diarrhea; And a C ₁ to C ₃₀ alkoxyl group, or ii) when each substituent is plural, neighboring substituents may be bonded to each other to form a ring, or iii) a substituent of the P ring and a substituent of the Q ring Can bond to each other to form a ring,

L ¹ And L < ² > are independently a single bond; An arylene group having ₆ to ₆₀ carbon atoms; A fluorenylene group; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; An alkylene group of C ₁ -C _60, and C ₂ ~ C ₆₀ alkenyl group of; is selected from the group consisting of,

Ar ¹ and Ar ² are each independently a C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; And an aryloxy group having from ₆ to ₃₀ carbon atoms,

R ¹ to R ³ are the same or different from each other when q, m and o are 2 or more, i) independently of one another, deuterium; halogen; A C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₃₀ ; And L ³ -N (R _a ) (R _b ), wherein L ³ is a single bond, a C ₆ to C ₆₀ arylene group, a fluorenedylene group, a C ₃ to C ₆₀ A fused ring group of an aliphatic ring of C ₆ to C ₆₀ aromatic rings, and a heterocyclic group of C ₂ to C ₆₀ , wherein R _a and R _b are independently selected from the group consisting of C ₆ to C ₆₀ aryl group; fluorene group; C ₃ ~ C a fused ring of an aromatic ring of an aliphatic ring and a C ₆ ~ C ₆₀ groups of _60; and O, N, S, Si and C containing at least one hetero atom of the P A heterocyclic group having ₂ to ₆₀ carbon atoms, or ii) a neighboring group may combine with each other to form a ring (wherein the group which does not form a ring is the same as defined in (i)),

R ⁴ to R ¹⁵ independently of one another are i) hydrogen; heavy hydrogen; halogen; A C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₃₀ ; And -L ⁴ -N (R _c ) (R _d ), wherein L ⁴ , R _c and R _d are each as defined above for L ³ , R _a and R _b ; Or ii) a neighboring group may combine with each other to form a ring, wherein the group which does not form a ring is the same as defined in (i)),

At least two of X ¹ to X ⁶ are N and the others are CR ¹⁶ ,

Z ¹ to Z ¹⁶ independently of one another are CR ¹⁷ or N,

X and Y are independently of each other S, O, NR ¹⁸ , CR ¹⁸ R ¹⁹ or SiR ¹⁸ R ¹⁹ ,

R ¹⁶ to R ¹⁹ independently of one another are i) hydrogen; heavy hydrogen; halogen; A C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₃₀ ; And L ⁵ -N (R _e ) (R _f ), wherein L ⁵ , R _e and R _f are each as defined above for L ³ , R _a and R _b , Or ii) a neighboring R ¹⁶ group, or a neighboring R ¹⁷ group, may combine with each other to form a ring, wherein the ring-forming group is the same as defined in (i)

W is NAr ⁵ , O or S,

Ar ³ to Ar ⁵ independently represent a C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₃₀ ; And -L ⁶ -N (R _g ) (R _h ), wherein L ⁶ , R _g and R _h are each as defined above for L ³ , R _a and R _b ,

The aryl group may be substituted with at least one substituent selected from the group consisting of an aryl group, a fluorenyl group, a heterocyclic group, a fused ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyl group, , (which is the same as where L ^7, R _i and R _j is the definition of L ^3, R _a and R _b, respectively), a germanium group, a cyano group, a nitro group, -L ⁷ -N (R _i) (R _j) , C ₁ ~ Import alkylthio of C _20, C ₁ ~ C ₂₀ alkoxy group, a C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ of the alkenyl group, C ₂ ~ C ₂₀ alkynyl, C ₆ ~ C of group of ₂₀ aryl, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, fluorene group, C of ₂ ~ C ₂₀ heterocyclic group, C ₃ ~ C ₂₀ cycloalkyl group, C ₇ ~ C ₂₀ of the arylalkyl group and with one or more substituents selected from the group consisting of aryl alkenyl group of C ₈ ~ C ₂₀ may be further substituted.

According to another embodiment of the present invention, A in the formula (1) may be one represented by one of the following formulas.

In another embodiment of the present invention, the compound represented by the formula (1) may be one selected from the group consisting of the following formulas (5) to (12).

In the above formulas,

Ar ¹ , Ar ² , A, M and n are the same as Ar ¹ , Ar ² , A, M and n defined in the above formula (1)

In another embodiment of the present invention, the compound represented by the formula (1) may be represented by the following formula.

In another embodiment of the present invention, the compound represented by the formula (2) may be any one represented by the following formula.

In another embodiment of the present invention, the compound represented by the formula (4) may be any of those represented by the following formulas.

In another embodiment of the present invention, the present invention provides a light emitting device wherein the dopant of the light emitting layer of the organic electronic device contains the compound represented by the above formula (1), and the host of the light emitting layer comprises the compound represented by the above formula And a compound represented by the following general formula (3).

In another embodiment of the present invention, the present invention provides a light emitting device wherein the dopant of the light emitting layer of the organic electronic device contains the compound represented by the above formula (1), and the host of the light emitting layer comprises the compound represented by the above formula And a compound represented by the following general formula (4).

In a further embodiment of the present invention, the dopant of the organic electroluminescent device contains the compound represented by the formula (1), and the host of the emitting layer comprises the compound represented by the formula (3) ) ≪ / RTI > in an organic electroluminescent device.

In another embodiment of the present invention, an organic electroluminescence device includes a light-efficiency improvement layer on at least one side of one side of the first electrode opposite to the organic material layer or one side of the one side of the second electrode opposite to the organic material layer, Device.

In another embodiment of 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 do.

In another embodiment of the present invention, the present invention provides an organic electronic device comprising a first electrode, a second electrode, and an organic material layer disposed between the first electrode and the second electrode, wherein the organic material layer comprises a dopant and a host material (2) to (4) as a dopant material, wherein the dopant material includes a compound represented by the following chemical formula (1) as the host material: A display device including a device; And a control unit for driving the display device.

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

Hereinafter, the synthesis examples of the formulas according to the present invention and the production examples of the organic electric devices will be specifically described with reference to examples, but the present invention is not limited to the following examples.

Synthetic example

Synthesis of the compound was carried out as follows.

The final product ( Final Product )

The compounds according to the present invention were prepared by reacting Sub 1 and Sub 2 as shown in Reaction Scheme 1 below.

<Reaction Scheme 1>

One. Sub  Synthesis of 1

Sub 1 of Scheme 1 can be synthesized by the following Reaction Scheme 2, and Sub 1-1 of Scheme 2 can be synthesized by the reaction path of Scheme 3 and Scheme 4, but is not limited thereto.

<Reaction Scheme 2>

One equivalent of Sub 1-1 compound (Ligand) was dissolved in 2-methoxy ethanol, IrCl ₃ (0.5 equivalent) was added, and the mixture was refluxed for 24 hours. When the reaction was completed, it was cooled to room temperature and the precipitate was filtered. The obtained solid was washed with water and methanol, and recrystallized from a nucleic acid. The obtained compound (1 equivalent) was dissolved in 2-methoxy ethanol, acac (3 eq.) And Na ₂ CO ₃ were added, and the mixture was refluxed for 5 hours. When the reaction was completed, the solid precipitate was filtered and then separated and purified by silica gel column chromatography to obtain Sub 1 compound.

One) Sub  Synthetic examples of 1-1

Sub  1-1-1 Synthetic example

<Reaction Scheme 3>

                                        Sub 1-1-1

2-chloropyridine (1 eq.) Was dissolved in THF, and then phenylboronic acid (1 equivalent), Pd (PPh ₃ ) ₄ (0.05 eq.), K ₂ CO ₃ Respectively. 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 a product.

Sub  1-1-34 of Synthetic example

<Reaction Scheme 4>

                                                             Sub 1-1-34

2- (thiophen-2-yl) ethanamine (1 eq.), 4- (tert-butyl) benzoyl chloride (1 eq.), 20% NaOH (3 eq.) And water were added and stirred at 0 ° 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 4- (tert-butyl) -N- (2- (thiophen- ) ethyl) benzamide. POCl ₃ and toluene were added to 4- (tert-butyl) -N- (2- (thiophen-2-yl) ethyl) benzamide and the mixture was refluxed at 0 ° 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 4- (tert-butyl) phenyl) -6,7-dihydrothieno [ 3,2-c] pyridine. 10% Pd / C catalyst and toluene were added to 4- (4- (tert-butyl) phenyl) -6,7-dihydrothieno [3,2- c] pyridine and the mixture was refluxed for 18 hours. 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 4- (tert-butyl) phenyl thieno [3,2-c ] pyridine.

Examples of Sub 1 include, but are not limited to, the following FD-MSs.

2. Sub  Synthesis of 2

Examples of Sub 2 include, but are not limited to, the following FD-MSs.

3. Final product ( Final Products ) Synthesis of

1) Synthesis of the formula (1)

The ligand Sub 1 (2.5 eq.) and the ancillary ligand Sub 2 (1 eq.) were added and microwaved with glycerol for 20 min. After the completion of the reaction, the obtained solid substance was filtered, purified through column chromatography, and dried under a vacuum pump for 3 hours to obtain a final compound.

The final product 1-1 Synthetic example

2,5-diphenylpyrazine (0.5 g, 2 mmol), an ancillary ligand, was added to the ligand Ir compound (3.0 g, 5 mmol) and microwaves were applied at 240 ° C for 20 minutes with glycerol. After the reaction was completed, the obtained solid substance was filtered, purified through column chromatography, and dried under a vacuum pump for 3 hours to obtain 3.45 g (yield: 56%) of the final compound.

The final product 1-17 Synthetic example

The ancillary ligand, 2,5-di (naphthalen-2-yl) pyrazine (0.6 g, 2 mmol) was added to the ligand Ir compound (3.6 g, 5 mmol) and microwaves were applied at 240 ° C for 20 minutes with glycerol. After the reaction was completed, the obtained solid substance was filtered, purified through column chromatography, and dried under a vacuum pump for 3 hours to obtain 4.5 g (yield: 58%) of the final compound.

The final product 2-3 Synthetic example

2,3-diphenylquinoxaline (0.6 g, 2 mmol), an ancillary ligand, was added to the ligand Ir compound (3.0 g, 5 mmol) and microwave was given at 240 ° C for 20 minutes with glycerol. After the reaction was completed, the obtained solid substance was filtered, purified through column chromatography, and dried under vacuum pump for 3 hours to obtain 3.5 g (yield: 55%) of the final compound.

The final product 2-7 Synthetic example

2,4-diphenylquinazoline (0.6 g, 2 mmol), an ancillary ligand, was added to the ligand Ir compound (3.9 g, 5 mmol) and microwave was applied at 240 ° C for 20 minutes with glycerol. After the reaction was completed, the obtained solid substance was filtered, purified through column chromatography, and dried under a vacuum pump for 3 hours to obtain 6.0 g (yield: 54%) of the final compound.

2) Synthesis of the formula (2)

The final product 3-9 Synthetic example

Synthetic examples of the final products 3-9 according to the present invention are shown in the following Reaction Scheme 5.

<Reaction Scheme 5>

Sub  3-2 Synthetic method

Sub 3-1 was dissolved in anhydrous THF, the temperature of the reaction was lowered to -78 ° C, n-BuLi (2.5 M in hexane) was slowly added dropwise, and then the reaction was stirred at 0 ° C for 1 hour. Then, the temperature of the reaction was lowered to -78 ° C, trimethyl borate was added dropwise, and the mixture was stirred at room temperature for 12 hours. When the reaction was completed, 2N-HCl aqueous solution was added, stirred for 30 minutes, and extracted with ether. Water in the reaction mixture was removed with anhydrous MgSO ₄ , filtered under reduced pressure, and the organic solvent was concentrated. The resulting product was separated by column chromatography to obtain the desired Sub 3-2.

Sub  3-3 Synthetic method

Sub 3-2, 1-iodo-2-nitrobenzene, Pd (PPh ₃ ) ₄ and K ₂ CO ₃ obtained in the above synthesis were dissolved in anhydrous THF and a small amount of water and refluxed for 24 hours. When the reaction was completed, the temperature of the reaction mixture was cooled to room temperature, extracted with CH ₂ Cl ₂ and wiped with water. A small amount of water was removed with anhydrous MgSO ₄ , filtered under reduced pressure, and the organic solvent was concentrated. The resulting product was separated by column chromatography to obtain the desired Sub 3-3.

Sub  3-4 Synthetic method

Sub 5-3 and triphenylphosphine obtained in the above synthesis were dissolved in o-dichlorobenzene and refluxed for 24 hours. When the reaction was completed, the solvent was removed by distillation under reduced pressure, and the concentrated product was separated by column chromatography to obtain the desired Sub 3-4.

The final product ( final product ) 3-9 Synthetic method

Sub 3-4 (1 eq.) And Sub 5-6 (1.1 eq.) Were added to toluene and Pd ₂ (dba) ₃ (0.05 eq.), PPh ₃ (0.1 eq.) And NaO t- Bu (3 eq.), Respectively, and the mixture is refluxed at 100 ° C for 24 hours. ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallized to obtain Product 3-9 (yield 68%).

Examples of the compound represented by the formula (3) are the compounds 3-1 to 3-32, but not limited thereto, and their FD-MS are shown in Table 3 below.

3) Synthesis of the formula (3)

The final product 4-1 Synthetic example

The synthetic example of the final product 4-1 according to the present invention is shown in the following Reaction Scheme 6.

<Reaction Scheme 6>

3-bromo-9-phenyl-9H-carbazole (6.4 g, 20 mmol) was dissolved in THF and then 9- (4,6-diphenyl-1,3,5-triazin- 3-yl) boronic acid (8.8 g, 20 mmol), Pd (PPh ₃ ) ₄ (0.03 eq.), K ₂ CO ₃ (3 eq.) And water. After completion of the reaction, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 9.2 g (yield: 72%) of the product

Examples of the compound represented by the formula (3) are compounds 4-1 to 4-24, but not limited thereto, and their FD-MS are shown in Table 4 below.

4) Synthesis of the formula (4)

The final product 5-6 Synthetic example

Synthetic examples of the final products 5-6 according to the present invention are shown in the following Reaction Scheme 7.

<Reaction Scheme 7>

2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (7.8 g, 20 mmol), Pd (PPh ₃ ) ₄ (0.03 eq.), K ₂ CO ₃ (3 eq.) And water are added, and the mixture is refluxed with stirring. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 7.5 g (yield: 70%) of the product.

Examples of the compound represented by the formula (4) are compounds 5-1 to 5-12, but not limited thereto, and their FD-MS are shown in Table 5 below.

Evaluation of manufacturing of organic electric device

[ Experimental Example  1] to [ Experimental Example  9] Red  Organic light emitting devices (phosphorescence Dopant )

An organic electroluminescent device was fabricated according to a conventional method by using the compounds (2-1 to 2-9) obtained through synthesis as a luminescent dopant material in the light emitting layer. First, N ¹ on the ITO layer (anode) formed on the glass substrate - (naphthalen-2-yl) -N 4, N 4 -bis (4- (naphthalen-2-yl (phenyl) amino) phenyl) -N 1 -benzyl-1,4-diamine (abbreviated as 2-TNATA) was vacuum deposited to form a hole injection layer having a thickness of 60 nm. Then, 4,4-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (hereinafter abbreviated as -NPD) was vacuum-deposited to a thickness of 60 nm to form a hole transport layer. The compound (3-5) of the present invention was used as a host on the hole transport layer, doped with a compound of the present invention (one of 2-1 to 2-9) of the present invention as a dopant at a weight ratio of 95: 5, Respectively. Subsequently, aluminum (1,1'-biphenyl) -4-oleato) bis (2-methyl-8-quinolinolato) aluminum (hereinafter abbreviated as BAlq) was vacuum deposited as a hole blocking layer to a thickness of 10 nm, Tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was deposited to a thickness of 40 nm as a transport layer. Then, LiF, an alkali metal halide serving as an electron injecting layer, was deposited to a thickness of 0.2 nm, and then Al was deposited to a thickness of 150 nm as an anode to produce an organic electroluminescent device

[ Comparative Example  One]

An organic electroluminescent device was fabricated in the same manner as in Experimental Example 1, except that the dopant material of the light emitting layer was formed using the following Comparative Compound 1 instead of the compound of the present invention.

&Lt; Comparative Compound 1 > (piq) ₂ Ir (acac)

Electroluminescence (EL) characteristics of the organic electroluminescent device manufactured in Experimental Examples 1 to 9 and Comparative Example 1 thus prepared were measured by PR-650 of photoresearch by applying a forward bias DC voltage. The measured T90 lifetime was measured by a lifetime measuring device manufactured by Mac Science Inc. at a reference luminance of 300 cd / m 2.

Table 6 below shows device fabrication and evaluation results for Experimental Examples 1 to 9 and Comparative Example 1 to which the inventive compounds were applied.

As can be seen from the results of Table 6 above, when the compound according to the present invention is used as a red light emitting layer material of an organic electroluminescent device, higher luminous efficiency is obtained than in Comparative Compound 1, .

In other words, it showed about 11% lower driving voltage and about 71% higher efficiency than the comparative compound 1 (piq) ₂ Ir (acac). In general, the light of the phosphorescent dopant is generated by two mechanisms: metal-to-ligand charge-transfer (MLCT) and ligand-to-ligand charge-transfer It is predicted that the compounds could theoretically have high efficiency since MLCT and LLCT can be generated in two metal complexes.

[ Experimental Example  10] to [ Experimental Example  27] Green organic light emitting device (phosphorescence Dopant )

Organic electroluminescent devices were fabricated according to a conventional method using the compounds (1-1 to 1-18) obtained through synthesis as a luminescent dopant material in the light emitting layer. First, N ¹ on the ITO layer (anode) formed on the glass substrate - (naphthalen-2-yl) -N 4, N 4 -bis (4- (naphthalen-2-yl (phenyl) amino) phenyl) -N 1 -benzyl-1,4-diamine (abbreviated as 2-TNATA) was vacuum deposited to form a hole injection layer having a thickness of 60 nm. Then, 4,4-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (hereinafter abbreviated as -NPD) was vacuum-deposited to a thickness of 60 nm to form a hole transport layer. The compound (3-9) of the present invention was used as a host on the hole transport layer, and the compound of the present invention was doped with a dopant compound in a ratio of 95: 5 by weight to deposit a light emitting layer with a thickness of 30 nm. (2-methyl-8-quinolinolato) aluminum (hereinafter abbreviated as BAlq) was vacuum deposited to a thickness of 10 nm to form a tris (8-quinolinolato) (Hereinafter abbreviated as &quot; Alq3 &quot;) was deposited to a thickness of 40 nm. Then, LiF, an alkali metal halide serving as an electron injecting layer, was deposited to a thickness of 0.2 nm, and then Al was deposited to a thickness of 150 nm as an anode to produce an organic electroluminescent device.

[ Comparative Example  2]

An organic electroluminescent device was fabricated in the same manner as in Experimental Example 10 except that the compound of the present invention was used instead of the compound of the following Comparative Compound 2 to form a dopant material for the light emitting layer.

&Lt; Comparative Compound 2 > Ir (ppy) ₃

Electroluminescence (EL) characteristics of the organic electroluminescent device manufactured in Experimental Examples 10 to 27 and Comparative Example 2 thus prepared were measured by PR-650 of photoresearch by applying a forward bias DC voltage to the organic electroluminescent device manufactured by Experiments 10 to 27 and Comparative Example 2, The measured T90 lifetime was measured by a lifetime measuring device manufactured by Mac Science Inc. at a reference luminance of 300 cd / m 2.

Table 7 below shows the device fabrication and evaluation results for Experiments 10 to 27 and Comparative Example 2 to which the compound according to the invention was applied.

As can be seen from the results of Table 7, when the compound according to the present invention is used as a green light emitting layer material of an organic electroluminescent device, it is possible to obtain a higher luminescence efficiency than the case of using the comparative compound 2, .

In other words, the driving voltage was about 12% lower than that of the comparative compound 2 Ir (ppy) ₃ , and the efficiency was about 57% higher. It can also be explained that MLCT and LLCT can be generated in two metal complexes and thus have high efficiency.

[ Experimental Example  28] to [ Experimental Example  45] green organic light emitting device (mixed host + phosphorescence Dopant )

Organic electroluminescent devices were fabricated according to a conventional method using the compounds (1-1 to 1-18) obtained through synthesis as a luminescent dopant material in the light emitting layer. First, N ¹ on the ITO layer (anode) formed on the glass substrate - (naphthalen-2-yl) -N 4, N 4 -bis (4- (naphthalen-2-yl (phenyl) amino) phenyl) -N 1 -benzyl-1,4-diamine (abbreviated as 2-TNATA) was vacuum deposited to form a hole injection layer having a thickness of 60 nm. Then, 4,4-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (hereinafter abbreviated as -NPD) was vacuum-deposited to a thickness of 60 nm to form a hole transport layer. The compound (3-9) of the present invention and the compound (5-6) of the present invention were mixed and used as a host on the hole transport layer. As a dopant substance, a compound of the present invention (one of 1-1 to 1-18) (1, 1'-biphenyl) -4-oleate) bis (2-methyl-8-quinolinolato) aluminum (Hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm, and tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was formed to a thickness of 40 nm as an electron transport layer. Then, LiF, an alkali metal halide serving as an electron injecting layer, was deposited to a thickness of 0.2 nm, and then Al was deposited to a thickness of 150 nm as an anode to produce an organic electroluminescent device.

Electroluminescence (EL) characteristics of the organic electroluminescent device manufactured by Experimental Examples 28 to 45 thus prepared were measured by PR-650 of photoresearch by applying a forward bias DC voltage, and the electroluminescence (EL) / RTI &gt; &lt; RTI ID = 0.0 &gt; m / s &lt; / RTI &gt;

Table 8 below shows device fabrication and evaluation results for Experiments 28 to 45 to which the inventive compounds were applied.

As can be seen from the results of Table 8, the compound of the present invention (2) and the compound of the formula (4), which are the compounds of the present invention, are mixed with each other as compared with the case where the comparative compound 2 is used as a single host as the host material of the green light emitting layer of the organic electroluminescent device. , It is found that higher luminous efficiency is obtained, and the driving voltage and lifetime are remarkably improved. It is considered that the bandgap is wider and the charge balance in the light emitting layer is higher than that of the single host due to the two mixed hosts, thereby increasing the efficiency and lifetime.

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 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

Claims (15)

An organic electroluminescent device comprising a first electrode, a second electrode, and an organic material layer disposed between the first electrode and the second electrode,
Wherein the organic material layer comprises a light emitting layer containing a dopant and a host material, respectively, wherein the dopant material comprises a compound represented by the following formula (1), and the host material is a compound represented by any one of the following formulas (2) And at least one organic electroluminescent element.
(1) &quot; (2) &quot;

Formula (3)

[In the formula,
a and b are each independently an integer of 0 or 1 (provided that a + b = 1 or more)
m and n are each independently an integer of 1 or 2,
q and o are each independently an integer of 1 to 4,
M is a metal selected from transition metals,
A is

Lt; / RTI &gt;
A substituted or unsubstituted heterocyclic group of C ₂ ~ C ₂₀ ring containing the P ring is N (nitrogen), and said Q ring is C (carbon), a substituted or unsubstituted C ₆ ~ C ₂₀ aryl group containing, where , N (nitrogen) of the P ring forms a coordination bond (indicated by a dotted line) with the M, C (carbon) of the Q ring forms a covalent bond (indicated by a solid line) with the M,
When the P ring and the Q ring are each substituted, i) each substituent is independently selected from the group consisting of hydrogen; heavy hydrogen; halogen; A C ₆ to C ₆₀ aryl group; A C ₁ to C ₅₀ alkyl group; O, N, S, Si and P, A heterocyclic group of C ₂ ~ C _60; Florene diarrhea; And a C ₁ to C ₃₀ alkoxyl group, or ii) when each substituent is plural, neighboring substituents may be bonded to each other to form a ring, or iii) a substituent of the P ring and a substituent of the Q ring Can bond to each other to form a ring,
L ¹ And L &lt; ² &gt; are independently a single bond; An arylene group having ₆ to ₆₀ carbon atoms; A fluorenylene group; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; An alkylene group of C ₁ -C _60, and C ₂ ~ C ₆₀ alkenyl group of; is selected from the group consisting of,
Ar ¹ and Ar ² are each independently a C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; And an aryloxy group having from ₆ to ₃₀ carbon atoms,
R ¹ to R ³ are the same or different from each other when q, m and o are 2 or more, i) independently of one another, deuterium; halogen; A C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₃₀ ; And L ³ -N (R _a ) (R _b ), wherein L ³ is a single bond, a C ₆ to C ₆₀ arylene group, a fluorenedylene group, a C ₃ to C ₆₀ A fused ring group of an aliphatic ring of C ₆ to C ₆₀ aromatic rings, and a heterocyclic group of C ₂ to C ₆₀ , wherein R _a and R _b are independently selected from the group consisting of C ₆ to C ₆₀ aryl group; fluorene group; C ₃ ~ C a fused ring of an aromatic ring of an aliphatic ring and a C ₆ ~ C ₆₀ groups of _60; and O, N, S, Si and C containing at least one hetero atom of the P A heterocyclic group having ₂ to ₆₀ carbon atoms, or ii) a neighboring group may combine with each other to form a ring (wherein the group which does not form a ring is the same as defined in (i)),
R ⁴ to R ¹⁵ independently of one another are i) hydrogen; heavy hydrogen; halogen; A C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₃₀ ; And -L ⁴ -N (R _c ) (R _d ), wherein L ⁴ , R _c and R _d are each as defined above for L ³ , R _a and R _b ; Or ii) a neighboring group may combine with each other to form a ring, wherein the group which does not form a ring is the same as defined in (i)),
At least two of X ¹ to X ⁶ are N and the others are CR ¹⁶ ,
Z ¹ to Z ¹⁶ independently of one another are CR ¹⁷ or N,
X and Y are independently of each other S, O, NR ¹⁸ , CR ¹⁸ R ¹⁹ or SiR ¹⁸ R ¹⁹ ,
R ¹⁶ to R ¹⁹ independently of one another are i) hydrogen; heavy hydrogen; halogen; A C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₃₀ ; And L ⁵ -N (R _e ) (R _f ), wherein L ⁵ , R _e and R _f are each as defined above for L ³ , R _a and R _b , Or ii) a neighboring R ¹⁶ group, or a neighboring R ¹⁷ group, may combine with each other to form a ring, wherein the ring-forming group is the same as defined in (i)
W is NAr ⁵ , O or S,
Ar ³ to Ar ⁵ independently represent a C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₃₀ ; And -L ⁶ -N (R _g ) (R _h ), wherein L ⁶ , R _g and R _h are each as defined above for L ³ , R _a and R _b ,
The aryl group may be substituted with at least one substituent selected from the group consisting of an aryl group, a fluorenyl group, a heterocyclic group, a fused ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyl group, , (which is the same as where L ^7, R _i and R _j is the definition of L ^3, R _a and R _b, respectively), a germanium group, a cyano group, a nitro group, -L ⁷ -N (R _i) (R _j) , C ₁ ~ Import alkylthio of C _20, C ₁ ~ C ₂₀ alkoxy group, a C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ of the alkenyl group, C ₂ ~ C ₂₀ alkynyl, C ₆ ~ C of group of ₂₀ aryl, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, fluorene group, C of ₂ ~ C ₂₀ heterocyclic group, C ₃ ~ C ₂₀ cycloalkyl group, C ₇ ~ C ₂₀ of the arylalkyl group and An arylalkenyl group having from ₈ to ₂₀ carbon atoms, or an arylalkenyl group having from ₈ to ₂₀ carbon atoms, The method according to claim 1,
Wherein M in the formula (1) is selected from the group consisting of Ir, Pt, Rh, Re and Os. The method according to claim 1,
Wherein A in the formula (1) is any one of the following formulas.

The method according to claim 1,
Wherein the compound represented by the formula (1) is any one of the following formulas (5) to (12).

[In the formula,
Ar ¹ , Ar ² , A, M and n are the same as Ar ¹ , Ar ² , A, M and n defined in the above formula (1) The method according to claim 1,
The organic electroluminescent device according to claim 1, wherein the compound represented by the formula (1) is represented by the following formula.

The method according to claim 1,
The organic electroluminescent device according to claim 1, wherein the compound represented by the formula (2) is any one of the following formulas.

The method according to claim 1,
Wherein the compound represented by the formula (3) is any one of those represented by the following formulas.

The method according to claim 1,
The organic electroluminescent device according to claim 1, wherein the compound represented by the formula (4) is any one of the following formulas.

The method according to claim 1,
The dopant of the light emitting layer contains a compound represented by the formula (1), and the host of the light emitting layer contains a mixture of the compound represented by the formula (2) and the compound represented by the formula (3) Lt; / RTI &gt; The method according to claim 1,
The dopant of the light-emitting layer contains the compound represented by the formula (1), and the host of the light-emitting layer contains the compound represented by the formula (2) and the compound represented by the formula (4) Lt; / RTI &gt; The method according to claim 1,
The dopant of the light emitting layer contains the compound represented by the formula (1), and the host of the light emitting layer contains the compound represented by the formula (3) and the compound represented by the formula (4) Lt; / RTI &gt; The method according to claim 1,
Wherein at least one of the one side of the first electrode opposite to the organic material layer or one side of the second electrode opposite to the organic material layer includes a light-efficiency-improvement layer. The method according to claim 1,
Wherein 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. A display device including the organic electroluminescent device of claim 1; And
And a control unit for driving the display device. 15. The method of claim 14,
Wherein the organic electronic device is at least one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a monochromatic or white illumination device.

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