KR20180116822A - Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof - Google Patents

Abstract

Disclosed are: a compound represented by chemical formula 1; an organic electronic element including a first electrode, a second electrode, and an organic material layer between the first and second electrodes; and an electronic device including the organic electronic element. By including the compound represented by the chemical formula 1 in the organic material layer, the organic electronic element can have decreased driving voltage, and improved luminous efficiency and lifetime.

Description

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

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 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.

Currently, the portable display market is increasing in size as a large-area display, which requires more power than the power consumption required by existing portable displays. Therefore, power consumption is an important factor for portable displays, which have a limited power source, such as a battery, and efficiency and longevity are also important factors to 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, Indicating a tendency for the lifetime to increase. However, simply improving the organic material layer can not maximize the efficiency. This is because, when the optimum combination of the energy level and the T ₁ value between the respective organic layers, and the intrinsic properties (mobility, interface characteristics, etc.) of the materials are achieved, long life and high efficiency can be achieved at the same time.

In order to solve the problem of luminescence in the hole transporting layer in a general organic electroluminescent device of recent years, it is preferable that a luminescent auxiliary layer exists between the hole transporting layer and the luminescent layer, and the luminescent layer (R, G, B) It is necessary to develop another light-emitting auxiliary layer.

In order to sufficiently exhibit the excellent characteristics of the organic electronic device, a material constituting the organic material layer in the device, for example, a hole injecting material, a hole transporting material, a light emitting auxiliary material, a light emitting layer material, an electron transporting material, an electron transporting auxiliary material, The organic material layer for organic electroluminescent devices has not been sufficiently developed yet. Therefore, the development of new materials is continuously required, and in particular, the development of materials for the light-emitting auxiliary layer and the light emitting layer is urgently required, and in particular, development of a host material for the light emitting layer is demanded.

An object of the present invention is to provide a compound capable of lowering the driving voltage of a device and improving the luminous efficiency, color purity and lifetime of the device, an organic electric device using the same, and an electronic device therefor.

In one aspect, the present invention provides a compound represented by the following general formula (1).

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

By using the compound according to the embodiment of the present invention, not only the driving voltage of the device can be lowered, but also the luminous efficiency, color purity and lifetime of the device can be greatly improved.

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, the terms first, second, A, B, (a), (b), and the like can 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."

In addition, when an element such as a layer, film, region, plate, or the like is referred to as being "on" or "on" another element, And the like. On the contrary, when an element is referred to as being " directly on " another element, it should be understood that it does not have another element in the middle.

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 " 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.

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 term " fluorenyl group " or " fluorenylene group " used in the present invention means a monovalent or divalent functional group in which R, R 'and R & Substituted fluorenyl group "or" substituted fluorenylene group "means that at least one of the substituents R, R 'and R" is a substituent other than hydrogen, and R and R' Together with a spy compound.

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, the aryl group or the arylene group includes a single ring, a ring group, a plurality of ring systems bonded together, a spiro compound and the like.

The term " heterocyclic group " as used herein includes not only aromatic rings such as " heteroaryl group " or " heteroarylene group ", but also nonaromatic rings, Means a ring of 2 to 60 rings, but is not limited thereto. The term " heteroatom ", as used herein, unless otherwise indicated, refers to N, O, S, P, or Si, wherein the heterocyclic group includes single ring, ring, And the like.

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.

As used herein, the term " ring " includes monocyclic and polycyclic rings, including hydrocarbon rings as well as heterocycles containing at least one heteroatom and including aromatic and non-aromatic rings.

As used herein, the term " polycyclic " includes ring assemblies such as biphenyl, terphenyl, and the like, as well as various fused ring systems and spiro compounds, including aromatic as well as non- The ring includes, of course, a heterocycle containing at least one heteroatom.

As used herein, the term " ring assemblies " means that two or more ring systems (a single ring or a fused ring system) are directly connected to each other through a single bond or a double bond, Means that the number of linkages is one less than the total number of rings in the compound. The ring assemblies may be directly connected to each other through a single bond or a double bond.

As used herein, the term " conjugated ring system " refers to a fused ring form shared by at least two atoms, in which the ring system of two or more hydrocarbons is conjugated and contains at least one heteroatom And at least one hetero ring system bonded thereto. Such conjugated ring systems may be aromatic rings, heteroaromatic rings, aliphatic rings or a combination of these rings.

The term " spiro compound " used in the present invention has a 'spiro union', and a spiro connection means a connection in which two rings share only one atom. At this time, atoms shared in two rings are called 'spyro atoms', and they are referred to as 'monospyros,' 'di spyroses,' and 'tri-spyros', depending on the number of spyro atoms contained in a compound. 'Compounds.

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

In addition, a no explicit description, the terms used in this invention in the "unsubstituted or substituted", "substituted" is an alkyl group of deuterium, a halogen, an amino group, a nitrile group, a nitro _{group, C 1 -C 20, C 1} -C 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, C ₂ -C of ₂₀ alkynyl, C ₃ -C ₂₀ cycloalkyl group, C ₆ -C ₂₀ aryl group, of a C ₆ -C ₂₀ aryl group substituted with a heavy hydrogen, C ₈ -C ₂₀ aryl alkenyl group, a silane group, a boron And a C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, with the proviso that at least one substituent And is not limited to these substituents.

In the present specification, the 'group name' corresponding to the aryl group, the arylene group, the heterocyclic group and the like exemplified as the examples of the respective symbols and substituents thereof may be described as 'the name of the group reflecting the singer' You may. For example, in the case of phenanthrene, which is a kind of aryl group, a monovalent 'group' may be named 'phenanthryl' and a bivalent group may be named 'phenanthrylene' It may be described as "phenanthrene" which is the name of the parent compound. Similarly, in the case of pyrimidine, it may also be described as 'pyrimidine' irrespective of the valence number, or may be described as the 'name of the group' of the corresponding singer, such as pyrimidine di have.

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, for example, , R < ¹ > may be the same or different from each other when a is an integer of 2 or more.

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

1, an organic electroluminescent device 100 according to an embodiment of the present invention includes a first electrode 120, a second electrode 180 and a first electrode 120 formed on a substrate 110, And an organic material layer containing a compound according to the present invention is provided between the two electrodes 180. 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 includes 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 stacked on the first electrode 120, At least one of the layers may be omitted and may further include a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151, an electron transporting auxiliary layer, a buffer layer 141, and the like. At this time, the electron transport layer 160 and the like may serve as a hole blocking layer, and the hole transport layer 140 and the electron transport layer 160 may be formed of one or more layers.

Also, although not shown, the organic electroluminescent device according to an embodiment of the present invention further includes 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 can do.

The compound according to one embodiment of the present invention applied to the organic layer includes a hole injecting layer 130, a hole transporting layer 140, a light emitting auxiliary layer 151, an electron transporting auxiliary layer, an electron transporting layer 160, 170), a host or a dopant material of the light emitting layer 150, or a material of the light efficiency improving layer. For example, the compound of the present invention can be used as a material for the light emitting layer 150, the hole transporting layer 140 and / or the light emitting auxiliary layer 151, and preferably the host material of the light emitting layer 150 or the light emitting auxiliary layer 151, Can be used as the material of

On the other hand, even if the core is the same core, since the band gap, the electrical characteristics, the interface characteristics, and the like can be changed depending on which substituent is bonded at which position, the selection of the core and the combination of the sub- In particular, when the optimal combination of the energy level and T ₁ value between the organic layers, and the intrinsic properties (mobility, interface characteristics, etc.) of the materials are achieved, long life and high efficiency can be achieved at the same time.

Accordingly, in the present invention, by forming the light emitting layer 150 or the light emitting auxiliary layer 151 using the compound represented by Chemical Formula 1, the energy level and T ₁ value between the organic layers, the intrinsic properties (mobility, interface characteristics, etc.) The life and efficiency of the organic electronic device can be improved at the same time.

An organic electroluminescent device according to an embodiment of the present invention may be manufactured using various deposition methods. For example, a metal or a metal oxide having conductivity or an alloy thereof may be deposited on a substrate to form a cathode 120, and a hole injection layer 130 may be formed thereon. A hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170, and then depositing a material that can be used as a cathode 180 on the organic layer. have. 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.

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 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 organic electroluminescent device according to an embodiment of the present invention may be one of an organic electroluminescent device, an organic solar cell, an organophotoreceptor, an organic transistor, or a device for monochromatic or white illumination.

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, the compound according to one aspect of the present invention will be described.

A compound according to one aspect of the present invention is represented by the following formula (1).

≪ Formula 1 >

In the above formula (1), each symbol may be defined as follows.

R ¹ to R ⁵ independently from each other are 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'-N (R _a ) (R _b ); and R ¹ and R ² may be bonded to each other or R ³ and R ⁴ may bond to each other to form a ring. The rings formed by bonding R ¹ and R ² or R ³ and R ^{4 to} each other may be benzene, naphthalene, phenanthrene, fluorene, and the like.

m and n are each an integer of 1 to 6;

When m is an integer of 2 or more, plural R ¹ to R ⁵ and L ¹ are the same or different from each other. When n is an integer of 2 or more, a plurality of R ^{5 s} are the same or different, and adjacent R ^{5 s may} be bonded to each other to form a ring. In this case, the ring formed by bonding adjacent R ^{5 s to} each other may be benzene, Naphthalene, phenanthrene, fluorene, and the like.

When R ¹ to R ⁵ are aryl groups, they may preferably be C ₆ -C ₃₀ aryl groups, more preferably C ₆ -C ₁₈ aryl groups, and illustratively include phenyl, naphthyl, phenanthrene, triphenyl Len, and the like. When R ¹ to R ⁵ are a heterocyclic group, they may preferably be a C ₂ -C ₃₀ heterocyclic group, more preferably a C ₂ -C ₁₆ heterocyclic group, and illustratively include triazine, dibenzothiophene , Benzonaphthofuran, and the like. When R ¹ to R ⁵ are fluorenyl groups, they may be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene and the like. When R ¹ to R ⁵ are alkyl groups, they may preferably be a C ₁ -C ₁₀ alkyl group, more preferably a C ₁ -C ₄ alkyl group, and may be exemplified by a methyl group and a t-butyl group.

L ¹ is a single bond; An arylene group having ₆ to ₆₀ carbon atoms; A fluorenylene group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; And fused ring groups of the aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; may be selected from the group consisting of.

When L ¹ is an arylene group, it is preferably a C ₆ -C ₃₀ arylene group, more preferably a C ₆ -C ₁₈ arylene group, and examples thereof include phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, Triphenylene, and the like. When L ¹ is a heterocyclic group, it is preferably a C ₂ -C ₃₀ heterocyclic group, more preferably a C ₂ -C ₁₆ heterocyclic group, and examples thereof include pyridine, pyrimidine, triazine, quinazoline, Benzoquinazoline, dibenzoquinazoline, carbazole, benzothienopyrimidine, benzopuropyrimidine, dibenzothiophene, dibenzofurane and the like. When L ¹ is a fluorenylene group, it may be 9,9-dimethyl-9H-fluorene or the like.

Ar ¹ is 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'-N (R _a ) (R _b );

When Ar ¹ is an aryl group, it may preferably be an aryl group of C _{6 to} C ₃₀ , more preferably a C _{6 to} C ₁₈ aryl group, and is exemplified by phenyl, naphthalene, biphenyl, phenanthrene, triphenylene , Terphenyl, and the like. When Ar ¹ is a heterocyclic group, it may preferably be a C ₂ -C ₃₀ heterocyclic group, more preferably a C ₂ -C ₁₆ heterocyclic group, and is exemplified by pyridine, pyrimidine, triazine, quinazoline , Benzoquinazoline, dibenzoquinazoline, quinoxaline, isoquinoline, imidazopyridine barazole, benzoimidazole, dibenzothiophene, dibenzofuran, benzothienopyrimidine, benzopurpyrimidine, and the like.

L 'is a single bond; An arylene group having ₆ to ₆₀ carbon atoms; A fluorenylene group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; And fused ring groups of the aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; may be selected from the group consisting of.

When L 'is an arylene group, it is preferably a C ₆ -C ₃₀ arylene group, more preferably a C ₆ -C ₁₈ arylene group, and may be exemplified by phenyl, biphenyl, terphenyl, naphthalene, and the like.

R _a and R _b 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; And fused ring groups of the aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; may be selected from the group consisting of.

When R _a and R _b are aryl groups, they may preferably be C ₆ -C ₃₀ aryl groups, more preferably C ₆ -C ₁₂ aryl groups, and may be illustratively phenyl, biphenyl, and the like. When R _a and R _b are a heterocyclic group, they may preferably be a C ₂ -C ₃₀ heterocyclic group, more preferably a C ₂ -C ₁₆ heterocyclic group, and illustratively include carbazole, dibenzothiophene , Benzonaphthofuran, and the like, and when R _a and R _b are fluorenyl groups, it may be 9,9-dimethyl-9H-fluorene.

A ring formed by combining R ¹ to R ⁵ , L ¹ , Ar ¹ , L ', R _a , R _b , R ¹ and R ² , a ring formed by bonding R ³ and R ^{4 to} each other, ^The rings formed by bonding ^{5 to} each other are deuterium; halogen; A silane group substituted or unsubstituted with an alkyl group having _{1 to 20} carbon atoms or an aryl group having _{6 to 20} carbon atoms; 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 containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A C ₃ -C ₂₀ cycloalkyl group; An arylalkyl group of C ₇ -C ₂₀ ; Aryl alkenyl group of C ₈ -C _20; And a combination of these.

The formula (1) may be represented by one of the following formulas (2) to (4).

 &Lt; Formula 2 > < EMI ID =

In the above Chemical Formulas 2 to 4, R ⁵ , L ¹ , Ar ¹ , m and n are as defined in Chemical Formula 1.

In the above formula, Ar ¹ may be one of the following formulas (a) to (j).

 <Formula a> <Formula b> <Formula c> <Formula d> <Formula e>

<Formula f> <Formula g> <Formula h> <Formula i> <Formula j>

In Formulas (a) to (j), X ¹ to X ⁷ are N or C (R ') and Y is O, S or N (Ar ³ ).

Ar ² and Ar ³ are each independently a C ₆ to C ₆₀ aryl group; A fluorenyl group; A fused ring group of a C ₂ to C ₆₀ heterocyclic group C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring containing at least one heteroatom selected from O, N, S, Si and P; 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'-N (R _a ) (R _b );

R 'is 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'-N (R a) (} R b); is selected from the group consisting of, "may be bonded to each other to each other to form a ring, it said L 'a neighborhood R, R ^a and R ^b in formula (1) is It is the same as defined.

When m = 2 in Formula (1), Formula (1) may be represented by Formula (5).

&Lt; Formula 5 >

In Formula 5, R ¹ to R ⁵ , L ¹ , Ar ¹ , m and n are as defined in Formula (1).

In Formula 1, Ar ¹ is _{-L'-N (R a) (} R b) of the case, the formula (1) may be represented by the following Chemical Formula 6, R ⁵ is _{-L'-N (R a) (} R _b ), the formula (1) may be represented by the following formula (7).

       &Lt; Formula 6 > < EMI ID =

Wherein R ¹ to R ⁵ , L ¹ , Ar ¹ , m, n, L ', R _a and R _b are as defined in formula (1).

Specifically, the compound represented by Formula 1 may be one of the following compounds.

.

.

In another aspect of the present invention, there is provided 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 is a compound .

The compound is contained in at least one layer of the hole injection layer, the hole transport layer, the light emission assisting layer, the light emitting layer, the electron transport assisting layer, the electron transport layer and the electron injection layer of the organic material layer, And preferably the compound represented by the above formula (1) can be used as a material for the host material and / or the luminescent auxiliary layer of the luminescent layer.

In another aspect of the present invention, there is provided an electronic device including a display device including the organic electronic device of claim 7 and a control unit for driving the display device.

Hereinafter, the synthesis examples of the compound represented by the formula (1) according to the present invention and the production examples of the organic electric device will be specifically described with reference to examples, but the present invention is not limited to the following examples.

Synthetic example

Illustratively, the final product of Formula 1 according to the present invention can be prepared by reacting Sub 1 with Sub 2 or Sub 3 as shown in Scheme 1 below.

<Reaction Scheme 1>

Sub 1 synthesis  example

Sub 1 of Reaction Scheme 1 can be synthesized by the reaction path of Reaction Schemes 2 to 4 below, but is not limited thereto.

<Reaction Scheme 2>

Sub 1-1-1 Synthetic Example

2-Bromo-1,1'-biphenyl (177.32 g, 760.7 mmol) was dissolved in THF (2,500 mL), the temperature of the reaction solution was lowered to -78 ° C, and n-BuLi (324.56 mL, 2.5 M in hexane) Slowly added dropwise, the reaction was stirred for 1 hour. 1,8-naphthalimide (100.0 g, 507.1 mmol) was dissolved in THF, and the mixture was stirred at room temperature for 4 hours. After completion of the reaction, water was added to the reaction mixture to quench water, and the water in the reaction mixture was removed. After the filtration under reduced pressure, the organic layer was dried over MgSO ₄ and concentrated to obtain 160.39 g of product (yield: 90%).

Sub 1-2-1 Synthetic Example

Sub 1-1-1 (160.39 g, 456.4 mmol) obtained in the above synthesis was placed in a round bottom flask and dissolved in acetic acid (2,000 mL). A few drops of HCl were slowly added and stirred at 80 &lt; 0 &gt; C. After the reaction was completed, the reaction mixture was neutralized with an aqueous Na ₂ SO ₄ solution and 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 132.38 g of product (yield: 87%

Sub 1-3-1 Synthetic Example

Sub 1-2-1 (132.38 g, 397.1 mmol) obtained in the above synthesis was dissolved in THF (2,000 mL), the temperature of the reaction was lowered to -78 ° C, and 2-biphenylmagnesium bromide solution (122.65 g, 476.5 mmol) After slow dropwise addition, the reaction was stirred for 1 hour and stirred at ambient temperature for 4 hours. After the reaction was completed, the reaction product was quenched by adding water, and water in the reaction product was removed. After filtration under reduced pressure, the product was dried with MgSO 4 and concentrated to obtain 162.63 g (yield: 84%) of the product.

Sub 1 (21) Synthetic example

Sub 1-3-1 (162.63 g, 333.5 mmol) obtained in the above synthesis was placed in a round bottom flask and dissolved in acetic acid (1,500 mL). A few drops of HCl were slowly added and stirred at 80 &lt; 0 &gt; C. After the reaction was completed, the reaction mixture was neutralized with Na ₂ SO ₄ aqueous solution, 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 126.86 g (yield: 81%

<Reaction Scheme 3>

Sub 1-1-2 Synthetic Example

(100.0 g, 507.1 mmol), potassium hydroxide (142.27 g, 2,535.6 mmol), hydrazine monohydrate (761.60 g, 15,213.8 mmol) and ethylene glycol (2,500 mL) were placed in a round bottom flask, And the mixture was stirred for 24 hours. After the completion of the reaction, the reaction product was quenched with water, and the water in the reaction product was removed. After filtration under reduced pressure, the compound was subjected to silicagel column and recrystallization to obtain 52.35 g of the product (yield: 61%)

Sub 1 (1) Synthetic example

Sub 1-1-2 (52.35 g, 309.3 mmol) obtained in the above synthesis was added to a round bottom flask and iodomethane (263.43 g, 1,856.1 mmol), KO (t-Bu) (208.27 g, 1,856.1 mmol), dimethylsulfoxide mL) was added, and the mixture was heated to 140 DEG C and stirred for 24 hours. When the reaction is completed, 3 L of water is added to each of the two 5 L beakers, and the reaction is solidified while stirring. Thereafter, the precipitated reaction product was filtered, and only the filtered solid was collected and purified by silicagel column and recrystallized to obtain 89.72 g (yield: 87%) of the product

<Reaction Scheme 4>

Sub 1-1-3 synthesis example

1,8-naphththalimide (100 g, 507.1 mmol) was dissolved in THF (2,500 mL), the temperature of the reaction solution was lowered to -78 ° C. and phenylmagnesium bromide solution (183.89 g, 1,014.3 mmol) , And the mixture was stirred at room temperature for 4 hours. After the reaction was completed, water was added to the reaction mixture to quench water. The water in the reaction mixture was removed, and the organic layer was dried over MgSO ₄ and concentrated to obtain 128.45 g of the product (yield: 92%).

Sub 1-2-2 Synthetic Example

Sub 1-1-3 (128.45 g, 466.6 mmol) obtained in the above synthesis was dissolved in THF (2,000 mL), the temperature of the reaction was lowered to -78 ° C, and phenylmagnesium bromide solution (169.19 g, 933.1 mmol) The reaction was stirred for 1 hour and then at room temperature for 4 hours. After the reaction was completed, water was added to the reaction mixture to quench the reaction mixture, and water in the reaction mixture was removed. After the filtration under reduced pressure, the organic layer was dried over MgSO ₄ and concentrated to obtain 145.11 g of the product (yield: 88%).

Sub 1 (11) Synthetic example

Sub 1-2-2 (145.11 g, 410.6 mmol) obtained in the above synthesis is put into a round bottom flask, and Benzene (1,500 mL) is added and dissolved by heating at 50 ° C. Trifluoromethanesulfonic acid (67.78 g, 451.6 mmol) was slowly added and stirred for 2 hours. After the reaction was completed, the reaction mixture was neutralized by pouring it into an aqueous solution of sodium bicarbonate. The organic layer was separated and 138.07 g of Sub 3 product (yield: 71%) was obtained through a column.

Examples of Sub 1 include, but are not limited to, FD-MS values for these compounds are shown in Table 1.

[Table 1]

Example of Sub 2

Examples of compounds belonging to Sub 2 include, but are not limited to, the following FD-MS values for these compounds.

[Table 2]

Sub 3 Synthetic example

Sub 3 of Reaction Scheme 1 can be synthesized by the reaction path of Reaction Scheme 3 below, but is not limited thereto.

<Reaction Scheme 3>

Sub 3 (2) Synthetic example

Sub 1 (21) (22.2g, 47.3 mmol) were placed in a round bottom flask was dissolved in toluene (500 mL), 1- bromo-4-iodobenzene (14.7g, 52.0 mmol), Pd 2 (dba) 3 (2.4 g, 2.6 mmol), P ( t- Bu) ₃ (1.1 g, 5.2 mmol) and NaO t- Bu (15 g, 156.1 mmol) were added and stirred at 100 ° 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 19.5 g of the product (yield: 66%).

Sub 3 Synthetic example

Examples of compounds belonging to Sub 3 include, but are not limited to, the following FD-MS values for these compounds.

[Table 3]

The final compound Synthetic example

Synthesis Example of Compound 1-1

Sub 2-1 (8.2 g, 52.0 mmol) and Pd ₂ (dba) ₃ (2.4 g, 2.6 mmol) were dissolved in toluene (500 mL) mmol), P ( t- Bu) ₃ (1.1 g, 5.2 mmol) and NaO t- Bu (15 g, 156.1 mmol) were added and stirred at 100 ° 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 11.7 g (yield: 65%) of the product.

Synthesis Example of Compound 1-11

24.1 g (Yield: 66%) of the product was obtained by the same synthesis method as in Synthesis Example 1-1 using Sub 1 (4) (21.6 g, 47.3 mmol) and Sub 2-63 (18.3 g, 52.0 mmol).

Synthesis Example of Compound 1-18

17.3 g (Yield: 69%) of the product was obtained by the same synthesis method as in Synthesis Example 1-1, using Sub 1 (1) (10.7 g, 47.3 mmol) and Sub 2-54 (17.7 g, 52.0 mmol).

Compound 1-36 Synthesis Example

21.3 g (Yield: 68%) of the product was obtained by the same synthesis method as in Synthesis Example 1-1 using Sub 1 (1) (10.7 g, 47.3 mmol) and Sub 2-58 (26.9 g, 52.0 mmol).

Compound 1-41 Synthesis Example

20.4 g (Yield: 63%) of Sub 1 (31) (26.4 g, 47.3 mmol) and Sub 2-2 (10.8 g, 52.0 mmol) were obtained by the same synthesis method as in Synthesis Example 1-1.

Compound 2-4 Synthetic Example

20.1 g (Yield: 68%) of Sub 1 (11) (22.4 g, 47.3 mmol) and Sub 2-4 (12.1 g, 52.0 mmol) were obtained in the same manner as in Synthesis Example 1-1.

Compound 2-10 Synthetic Example

21.1 g (Yield: 67%) of the product was obtained by the same synthesis method as in Synthesis Example 1-1 using Sub 1 (11) (22.4 g, 47.3 mmol) and Sub 2-64 (14.2 g, 52.0 mmol).

Synthesis Example of Compound 2-25

23.1 g (Yield: 62%) of the product was obtained by the same synthesis method as in Synthesis Example 1-1, using Sub 1 (19) (22.7 g, 47.3 mmol) and Sub 2-10 (10.2 g, 52.0 mmol).

Compound 2-39 Synthesis Example

28.2 g (Yield: 64%) of the product was obtained by the same synthesis method as in Synthesis Example 1-1, using Sub 1 (11) (22.4 g, 47.3 mmol) and Sub 2-61 (28.1 g, 52.0 mmol).

Compound 2-43 Synthetic Example

27.9 g (Yield: 60%) of the product was obtained by the same synthesis method as in Synthesis Example 1-1, using Sub 1 (32) (31.7 g, 47.3 mmol) and Sub 2-65 (18.2 g, 52.0 mmol).

Compound 3-3 Synthetic Example

19.4 g (Yield: 69%) of the product was obtained by the same synthesis method as in Synthesis Example 1-1 using Sub 1 (21) (22.2 g, 47.3 mmol) and Sub 2-3 (10.8 g, 52.0 mmol).

Synthesis Example of Compound 3-7

22.9 g (Yield: 65%) of the product was obtained by the same synthesis method as in Synthesis Example 1-1, using Sub 1 (21) (22.2 g, 47.3 mmol) and Sub 2-66 (16.8 g, 52.0 mmol).

Compound 3-13 Synthetic Example

22.0 g (Yield: 69%) of the product was obtained by the same synthesis method as in Synthesis Example 1-1, using Sub 1 (21) (22.2 g, 47.3 mmol) and Sub 2-15 (14.8 g, 52.0 mmol).

Compound 3-16 Synthetic Example

23.1 g (Yield: 67%) of the product was obtained by the same synthesis method as in Synthesis Example 1-1 using Sub 1 (21) (22.2 g, 47.3 mmol) and Sub 2-67 (15.4 g, 52.0 mmol).

Compound 3-36 Synthesis Example

27.8 g (Yield: 65%) of the product was obtained by the same synthesis method as in Synthesis Example 1-1 using Sub 1 (21) (22.2 g, 47.3 mmol) and Sub 2-58 (26.9 g, 52.0 mmol).

Compound 3-44 Synthetic Example

28.8 g (Yield: 63%) of the product was obtained by the same synthesis method as in Synthesis Example 1-1, using Sub 1 (33) (38.5 g, 47.3 mmol) and Sub 2-4 (12.1 g, 52.0 mmol).

Compound 4-4 Synthetic Example

30.4 g (Yield: 59%) of the product was obtained by the same synthesis method as in Synthesis Example 1-1, using Sub 1 (21) (22.2 g, 47.3 mmol) and Sub 2-68 (36.4 g, 52.0 mmol).

The FD-MS values of the compounds 1-1 to 4-12 of the present invention prepared according to the above synthesis examples are shown in Table 4 below.

[Table 4]

Evaluation of manufacturing of organic electric device

[ Example  1] Green organic electroluminescent device (phosphorescent host)

First, ITO layer (anode) formed on the glass substrate over the N ¹ - (naphthalen-2-yl) -N 4, N 4 -bis (4- (amino naphthalen-2-yl (phenyl)) phenyl) -N 1 - phenylbenzene-1,4-diamine (hereinafter abbreviated as '2-TNATA') was vacuum-deposited to form a 60 nm thick hole injection layer.

Thereafter, a 4,4-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (hereinafter abbreviated as NPD) film was vacuum deposited on the hole injection layer to a thickness of 60 nm to form a hole transport layer .

Next, the compound 1-6 of the present invention was used as a dopant material in tris (2-phenylpyridine) -iridium (hereinafter referred to as "Ir (ppy) ₃ ") as a host material on the hole transport layer, : 5 weight ratio to form a light emitting layer having a thickness of 30 nm.

Next, aluminum (1,1'-biphenyl) -4-oleato) bis (2-methyl-8-quinolinolato) aluminum (hereinafter abbreviated as BAlq) was vacuum deposited on the light emitting layer to a thickness of 10 nm (8-quinolinol) aluminum (hereinafter abbreviated as Alq ₃ ) was deposited on the hole blocking layer to a thickness of 40 nm to form an electron transporting layer.

Thereafter, LiF was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and then Al was deposited to a thickness of 150 nm on the electron injection layer to form a cathode.

[ Example  2] to [ Example  8] green organic electroluminescent device

An organic electroluminescent device was prepared in the same manner as in Example 1, except that the compound of the present invention described in Table 4 was used instead of the compound 1-1 of the present invention as a host material of the light emitting layer.

[ Comparative Example  One]

An organic electroluminescent device was prepared in the same manner as in Example 1, except that the following compound 1 was used instead of the compound 1-1 of the present invention as a host material in the light emitting layer.

<Comparative Compound 1>

Electroluminescence (EL) characteristics of the organic electroluminescent devices prepared in Examples 1 to 8 and Comparative Example 1 of the present invention were measured by applying a forward bias DC voltage to PR-650 of a photoresearch company, The T95 lifetime was measured by a life measuring apparatus manufactured by Mac Science Co., Ltd. at a reference luminance of 5000 cd / m ² , and the measurement results are shown in Table 5 below.

[Table 5]

[ Example  9] Red  Organic electroluminescent device (phosphorescent host)

2-TNATA was vacuum deposited on the ITO layer (anode) formed on the glass substrate 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 NPB) was vacuum-deposited to a thickness of 60 nm to form a hole transport layer. Subsequently, the compound 1-14 of the present invention was used as a host material and bis- ( 1-phenylisoquinoline) iridium (III) acetylacetonate (hereinafter referred to as "(piq) ₂ Ir (acac)") was doped as a dopant at a weight ratio of 95: 5 to form a 30 nm thick light emitting layer.

Next, BAlq was vacuum deposited on the light emitting layer to form a hole blocking layer to a thickness of 10 nm, and Alq ₃ was formed to a thickness of 40 nm on the hole blocking layer to form an electron transporting layer.

Then, LiF was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and Al was deposited to a thickness of 150 nm on the electron injection layer to form a cathode.

[ Example  10] to [ Example  19] green organic electroluminescent device

An organic electroluminescent device was prepared in the same manner as in Example 9, except that the compound of the present invention described in Table 6 was used instead of the compound 1-14 of the present invention as a host material in the light emitting layer.

[ Comparative Example  2]

An organic electroluminescent device was prepared in the same manner as in Example 9, except that the compound 1 was used instead of the compound 1-14 of the present invention as a host material in the light emitting layer.

Electroluminescence (EL) characteristics of the organic electroluminescent devices prepared in Examples 9 to 19 and Comparative Example 2 were measured by applying a forward bias DC voltage to PR-650 of a photoresearch company, The T95 lifetime was measured by a lifetime measuring apparatus manufactured by Mac Science Inc. at a reference luminance of 2500 cd / m ² , and the measurement results were as shown in Table 6 below.

[Table 6]

[ Example  20] green organic electroluminescent device The light- )

2-TNATA was vacuum deposited on the ITO layer (anode) formed on the glass substrate to form a hole injection layer having a thickness of 60 nm. Then, NPD was vacuum-deposited to a thickness of 60 nm on the hole injection layer to form a hole transport layer, Subsequently, the compound 1-33 of the present invention was vacuum deposited on the hole transport layer to a thickness of 20 nm to form an emission assist layer.

Next, using 4,4'-N, N'-dicarbazole-biphenyl (hereinafter abbreviated as CBP) as a host material and Ir (ppy) ₃ as a dopant material on the light- : 5 weight ratio to form a light emitting layer with a thickness of 30 nm.

Next, BAlq was vacuum deposited on the light emitting layer to form a hole blocking layer to a thickness of 10 nm, and Alq ₃ was formed to a thickness of 40 nm on the hole blocking layer to form an electron transporting layer.

Then, LiF was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and Al was deposited to a thickness of 150 nm on the electron injection layer to form a cathode.

[ Example  21] to [ Example  31] green organic electroluminescent device The light- )

An organic electroluminescent device was prepared in the same manner as in Example 20, except that the compound of the present invention described in Table 7 was used instead of the compound of the present invention 1-33 as a material of the luminescent auxiliary layer.

[ Comparative Example  3]

An organic electroluminescent device was prepared in the same manner as in Example 20 except that no light-emitting auxiliary layer was formed.

Electroluminescence (EL) characteristics of the organic electroluminescent devices prepared in Examples 20 to 31 and Comparative Example 3 of the present invention were measured by applying a forward bias DC voltage and using PR-650 of a photoresearch company, The T95 lifetime was measured at a lifetime of 5,000 cd / m ^{2 at a} reference luminance manufactured by Mac Science Inc., and the measurement results were as shown in Table 7 below.

[Table 7]

From Table 5 to Table 7, the luminous efficiency and lifetime of the organic electroluminescent device according to the embodiment of the present invention using the organic electroluminescent device material of the present invention as a phosphorescent host or a light emitting auxiliary layer material are shown in Table 1, , And the driving voltage is lowered.

This is because the compound of the present invention having a wide band gap has properties suitable as a phosphorescent host or a light emitting auxiliary layer material, that is, a proper energy level (e.g., HOMO, LUMO, T1) It seems to be due to the fact that it acts as a major factor (eg energy balance, hole mobility, electron mobility).

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 (13)

A compound represented by the following formula (1):
&Lt; Formula 1 >

In Formula 1,
R ¹ to R ⁵ independently from each other are 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'-N (R _a ) (R _b ); R ¹ and R ² or R ³ and R ⁴ may be bonded to each other to form a ring,
m and n are each an integer of 1 to 6,
When m is an integer of 2 or more, plural R ¹ to R ⁵ and L ¹ are the same or different from each other,
When n is an integer of 2 or more, a plurality of R ^{5 s} are the same or different, and adjacent R ^{5 s} may combine with each other to form a ring,
L ¹ is a single bond; An arylene group having ₆ to ₆₀ carbon atoms; A fluorenylene group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; And C ₃ ~ fused ring group of an aromatic ring of C ₆₀ of aliphatic rings and C ₆ ~ C _60; is selected from the group consisting of,
Ar ¹ is 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'-N (R _a ) (R _b );
L 'is a single bond; An arylene group having ₆ to ₆₀ carbon atoms; A fluorenylene group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; And C ₃ ~ fused ring group of an aromatic ring of C ₆₀ of aliphatic rings and C ₆ ~ C _60; is selected from the group consisting of,
R _a and R _b 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; And C ₃ ~ fused ring group of an aromatic ring of C ₆₀ of aliphatic rings and C ₆ ~ C _60; is selected from the group consisting of,
A ring formed by combining R ¹ to R ⁵ , L ¹ , Ar ¹ , L ', R _a , R _b , R ¹ and R ² , a ring formed by bonding R ³ and R ^{4 to} each other, ^The rings formed by bonding ^{5 to} each other are deuterium; halogen; A silane group substituted or unsubstituted with an alkyl group having _{1 to 20} carbon atoms or an aryl group having _{6 to 20} carbon atoms; 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 containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A C ₃ -C ₂₀ cycloalkyl group; An arylalkyl group of C ₇ -C ₂₀ ; Aryl alkenyl group of C ₈ -C _20; And a combination of these. The method according to claim 1,
(1) is represented by one of the following Chemical Formulas (2) to (4):
&Lt; Formula 2 >< EMI ID =

In the general formulas (2) to (4), R ⁵ , L ¹ , Ar ¹ , m and n are as defined in claim 1. The method according to claim 1,
Wherein Ar < ¹ > is ^one of the following formulas a to j:
<Formula a><Formulab><Formulac><Formulad><Formulae>

<Formula f><Formulag><Formulah><Formulai><Formulaj>

In the above formulas (a) to (j)
X ¹ to X ⁷ are N or C (R '), Y is O, S or N (Ar ³ )
Ar ² and Ar ³ are each independently a C ₆ to C ₆₀ aryl group; A fluorenyl group; A fused ring group of a C ₂ to C ₆₀ heterocyclic group C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring containing at least one heteroatom selected from O, N, S, Si and P; 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'-N (R _a ) (R _b );
R 'is 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'-N (R _a ) (R _b ); adjacent R 's may be bonded to each other to form a ring,
Wherein L ', R ^a and R ^b are as defined in claim 1. The method according to claim 1,
(1) is represented by the following formula (5): < EMI ID =
&Lt; Formula 5 &gt;

In Formula 5,
R ¹ to R ⁵ , L ¹ , Ar ¹ , m and n are the same as defined in claim 1. The method according to claim 1,
The compound represented by the formula (1) is represented by the following formula (6) or (7):
&Lt; Formula 6 >< EMI ID =

Wherein R ¹ to R ⁵ , L ¹ , Ar ¹ , m, n, L ', R _a and R _b are the same as defined in claim 1. The method according to claim 1,
Wherein the compound of formula (I) is one of the following compounds:

. 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 comprises a compound according to any one of claims 1 to 6. 8. The method of claim 7,
The compound is contained in at least one layer of the hole injection layer, the hole transport layer, the light emission assisting layer, the light emitting layer, the electron transport assisting layer, the electron transport layer and the electron injection layer of the organic material layer, Organic electroluminescent device. 9. The method of claim 8,
Wherein the compound is used as a host material of the light-emitting layer or a material of the light-emission-assisting layer. 8. The method of claim 7,
Wherein the organic material layer is formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process or a roll-to-roll process. 8. The method of claim 7,
Further comprising a light-efficiency-improvement layer formed on at least one side of the one surface of the first electrode and the second electrode opposite to the organic material layer. A display device including the organic electroluminescent device of claim 7; And
And a control unit for driving the display device. 13. The method of claim 12,
Wherein the organic electroluminescent device is one of an organic electroluminescent device, an organic solar cell, an organophotoreceptor, an organic transistor and a monochromatic illumination device.

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